KR20220115780A - Organic electroluminescent material and device thereof - Google Patents

Abstract

In the present invention, an organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material includes a metal complex having an L_a ligand of formula 1, and the metal complex can be used as a light emitting material in the electroluminescent device. By applying new compounds to the electroluminescent device, a driving voltage can be reduced, performances such as a device efficiency, especially, such as EQE can be improved and finally, overall performance of the device can be remarkably improved. In the present invention, the electroluminescent device including the metal complex and a compound combination including the metal complex are further disclosed.

Description

Organic electroluminescent material and its element TECHNICAL FIELD

The present invention relates to compounds such as organic light emitting devices used in organic electronic devices. In particular, it relates to a metal complex including a L _a ligand of Formula 1, and a compound combination with an electroluminescent device including the metal complex.

Organic electronic devices include organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photoelectric devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices, but are not limited thereto.

In 1987, Tang and Van Slyke of Eastman Kodak published a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline aluminum layer as an electron transport layer and a light emitting layer. (Applied Physics Letters, 1987, 51(12): 913-915). When a bias is applied to the device, green light is emitted from the device. The invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as a charge injection and transport layer, a charge and exciton blocking layer, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-luminous solid-state devices, they offer tremendous potential for display and lighting applications. In addition, the intrinsic properties of organic materials (eg their flexibility) make them suitable for special applications (eg manufacturing on flexible substrates).

OLEDs can be classified into three different types according to their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state luminescence. The triplet state generated in the device is wasted through the non-radiative attenuation channel. Therefore, the internal quantum efficiency (IQE) of a fluorescent OLED is only 25%. These limitations hinder the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs using triplet state emission from heavy metals containing complexes as emitters. Therefore, singlet state and triplet state can be obtained, and an IQE of 100% can be achieved. Because of their high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiencies through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet state gap so that excitons can return to the singlet state from the triplet state. In the TADF device, triplet state excitons can generate singlet state excitons through reverse intersystem crossing, thereby achieving high IQE.

OLEDs can also be divided into low-molecular and high-molecular OLEDs according to the type of material used. Low molecular weight refers to any organic or organometallic material that is not a polymer. If an accurate structure is provided, the molecular weight of a low molecule can be very large. Dendritic polymers with a well-defined structure are considered small molecules. Polymeric OLEDs include a conjugated polymer and a non-conjugated polymer having pendant emitting groups. If post polymerization occurs during the manufacturing process, the low molecular weight OLED can be converted into a high molecular OLED.

Various OLED manufacturing methods already exist. Small molecule OLEDs are typically prepared through vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing and nozzle printing. If the material can be dissolved or dispersed in a solvent, low-molecular-weight OLEDs can also be prepared by solution processing.

The emission color of OLED can be realized by designing the structure of the light emitting material. The OLED may include one light emitting layer or a plurality of light emitting layers to realize a desired spectrum. In green, yellow and red OLEDs, phosphorescent materials have already successfully realized commercialization. Blue phosphorescent devices still have problems such as blue desaturation, short device lifespan, and high operating voltage. Commercial full color OLED displays typically use a blending strategy using blue fluorescence and phosphorescent yellow or red and green. At present, there is still a problem that the efficiency of the phosphorescent OLED is rapidly reduced in the case of high luminance. In addition, it is desired to have a more saturated emission spectrum, higher efficiency and longer device lifetime.

를 함유한 금속 착물을 개시하였고, 여기서 X₁~X₈ 중 적어도 하나는 C-CN에서 선택되고, 아래와 같은 구조를 구비하는 이리듐 착물

을 더 개시하였다. 이는 유기 전계발광소자에 적용되어 소자성능 및 색포화도를 향상시킬 수 있으며, 비록 업계에서 비교적 높은 수준에 도달했으나 여전히 향상될 여지가 있다. 해당 출원에서는 R₄가 페닐기인 아릴치환기의 금속 착물 및 소자에서의 이의 응용만 개시하였고, 해당 금속 착물의 특정 위치에 본 출원과 같은 특정된 구조를 갖는 (헤테로)아릴기를 도입함으로써, 소자 성능에 미치는 영향을 개시 및 교시하지 않았다.Ligand structure having the following structure in US20200251666A1, the former applicant of the present applicant

_Disclosed is _a metal complex containing

was further initiated. It can be applied to organic electroluminescent devices to improve device performance and color saturation, and although it has reached a relatively high level in the industry, there is still room for improvement. In this application, only a metal complex of an aryl substituent in which R ₄ is a phenyl group and its application in a device are disclosed, and by introducing a (hetero)aryl group having a specified structure as in the present application at a specific position of the metal complex, the device performance is affected. No effect was disclosed and taught.

를 구비하는 금속 착물을 개시하였고, 아래와 같은 구조를 구비하는 이리듐 착물:

을 더 개시하였다. 해당 출원에서, 불소는 리간드 특정된 위치에서 재료의 성능을 향상시킬 수 있으며, 재료의 성능 향상에는 소자 수명 향상 및 열 안정성 증가 등을 포함하지만, 여전히 향상될 여지가 있다. 해당 출원에서는 R₄가 페닐기인 아릴치환기의 금속 착물 및 소자에서의 이의 응용만 개시하였고, 해당 금속 착물의 특정 위치에 본 출원과 같은 특정된 구조를 갖는 (헤테로)아릴기를 도입함으로써, 소자 성능에 미치는 영향을 개시 및 교시하지 않았다.In US20200091442A1, the former applicant of the present applicant, the ligand structure is as follows:

Disclosed is a metal complex comprising: an iridium complex having the following structure:

was further initiated. In this application, fluorine can improve the performance of the material at the ligand-specified position, and the performance improvement of the material includes improving device lifetime and increasing thermal stability, but there is still room for improvement. In this application, only a metal complex of an aryl substituent in which R ₄ is a phenyl group and its application in a device are disclosed, and by introducing a (hetero)aryl group having a specified structure as in the present application at a specific position of the metal complex, the device performance is affected. No effect was disclosed and taught.

을 개시하였으며, 여기서 R₁-R₄는 수소, 듀테륨, 알킬기, 시클로알킬기, 아릴기, 헤테로아릴기, 및 이들의 조합에서 선택된다. 해당 출원에서는 R₁이 페닐기인 아릴치환기의 금속 착물 및 소자에서의 이의 응용만 개시하였고, 해당 금속 착물의 특정 위치에 본 출원과 같은 특정된 구조를 갖는 (헤테로)아릴기를 도입함으로써, 소자 성능에 미치는 영향을 개시 및 교시하지 않았다.In US2013119354A1, a metal complex having the following general structure:

disclosed, wherein R ₁ -R ₄ is selected from hydrogen, deuterium, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and combinations thereof. In this application, only a metal complex of an aryl substituent in which R ₁ is a phenyl group and its application in a device are disclosed, and by introducing a (hetero)aryl group having a specified structure as in the present application at a specific position of the metal complex, the device performance is affected. No effect was disclosed and taught.

및

를 포함하며, 여기서 X₁은 규소, 게르마늄에서 선택되며, 아래와 같은 일반식 구조를 갖는 이리듐 착물:

을 더 개시하였다. 해당 출원에서는 주로 금속 착물에 실리콘기 또는 게르마닐기를 도입함으로써, 소자 성능에 미치는 영향을 주목하였고, 금속 착물의 특정 위치에 본 출원과 같은 특정된 (헤테로)아릴기를 도입함으로써, 소자 성능에 미치는 영향을 개시 및 교시하지 않았다.US20200287144A1 discloses a metal complex, which has a ligand structure having the structure:

and

wherein X ₁ is selected from silicon and germanium, and an iridium complex having the following general structure:

was further initiated. In this application, mainly by introducing a silicon group or germanyl group into the metal complex, the effect on the device performance was noted, and by introducing the specified (hetero)aryl group as in the present application at a specific position of the metal complex, the effect on the device performance was not disclosed and taught.

An object of the present invention is to provide a series of metal complexes comprising an L _a ligand having the structure of Formula 1 in order to solve at least a part of the above problems.

According to an embodiment of the present invention, a metal complex is disclosed, wherein the metal complex includes a metal M and a ligand L _a coordinated with the metal M, wherein L _a has a structure represented by Formula 1,

In Equation 1,

metal M is selected from metals having a relative atomic mass greater than 40;

Cy is 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, identically or differently each time it appears, ;

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R′ are present simultaneously, the two R′ are the same or different;

X ₁ to X ₅ are identically or differently selected from CR _X or N whenever they appear;

Ar has the structure shown in Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;

R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;

ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;

R', R _x , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms A cyclic cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted 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, 2 substituted or unsubstituted alkynyl group having -20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, 3-20 carbon atoms A substituted or unsubstituted alkylsilyl group having a group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgerma having 3 to 20 carbon atoms A nyl group (alkylgermanyl group), a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

"*" indicates the linkage position of formula 2;

Adjacent substituents R', R _x , R _a1 , R _a2 may optionally be joined to form a ring.

According to another embodiment of the present invention, an electroluminescent device is further disclosed, wherein the electroluminescent device includes:

anode,

cathode, and

and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the metal complex according to the embodiment.

According to another embodiment of the present invention, a compound combination including the metal complex according to the embodiment is further disclosed.

The present invention discloses a series of metal complexes containing an L _a ligand having the structure of Formula 1, and the metal complex can be used as a light emitting material in an electroluminescent device. This novel compound is applied to an electroluminescent device, thereby exhibiting more excellent performance, reducing the driving voltage, improving device efficiency, in particular, EQE, and ultimately improving the overall performance of the device. can

1 is a schematic diagram of an organic light emitting device that may contain the metal complexes and compound combinations disclosed by the present text.
2 is a schematic diagram of another organic light emitting device that may contain the metal complexes and compound combinations disclosed by the present text.

OLEDs can be fabricated on several types of substrates (eg, glass, plastic, and metal). 1 schematically and non-limitingly shows an organic light emitting device 100 . The drawings are not necessarily drawn to scale, and some layer structures in the drawings may be omitted 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 . Device 100 may be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in US Pat. No. 7,279,704B2 columns 6-10, the entire contents of which are incorporated herein by reference.

Each layer in these layers has more examples. Examples are the flexible and transparent substrate-anode combinations disclosed in U.S. Patent No. 5,844,363, incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ in a molar ratio of 50:1, as disclosed in US Patent Application Publication No. 2003/0230980, which is incorporated by way of reference in its entirety. US Patent No. 6303238 (to Thompson et al.), incorporated by reference in its entirety, discloses an example of a host material. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1 as disclosed in U.S. Patent Application Publication No. 2003/0230980, incorporated by reference in its entirety. U.S. Pat. Nos. 5703436 and 5707745, incorporated by reference in their entirety, disclose examples of a cathode, which is a thin layer of metal such as Mg:Ag, overlying a transparent, conductive, sputter-deposited layer. and a composite cathode having an ITO layer deposited thereon. U.S. Patent No. 6097147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entirety, describe the principle and use of the barrier layer in more detail. US Patent Application Publication No. 2004/0174116, incorporated by reference in its entirety, provides an example of an injection layer. A description of the protective layer may be found in US Patent Application Publication No. 2004/0174116, incorporated by reference in its entirety.

The hierarchical structure is provided through a non-limiting example. The function of the OLED can be realized by combining the various types of layers described above, or some layers can be completely omitted. It may further include other layers not explicitly described. Optimal performance can be achieved by using a single material or a mixture of several types of materials within each layer. Any functional layer may include several sub-layers. For example, the light emitting layer may include two different light emitting materials to realize a desired emission spectrum.

In one embodiment, an OLED can be described as having an “organic layer” disposed between a cathode and an anode. The organic layer may include one or a plurality of layers.

OLED also requires an encapsulation layer, and FIG. 2 schematically and non-limitingly illustrates the organic light emitting device 200 . The difference between this and FIG. 1 is that an encapsulation layer 102 is further included on the anode 190 to prevent harmful substances (eg, moisture and oxygen) from the environment. Any material capable of providing an encapsulation function may be used as the encapsulation layer (eg, glass or an organic-inorganic mixed layer). The encapsulation layer should be disposed directly or indirectly on the outside of the OLED device. Multithin film encapsulation is described in US Patent US7968146B2, the entire contents of which are incorporated herein by reference.

A device manufactured according to an embodiment of the present invention may be integrated into various types of consumer goods having one or a plurality of electronic member modules (or units) of the device. Some examples of such consumer goods include flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signal launch lights, head-up displays, fully transparent or partially transparent displays, flexible displays, Includes smartphones, tablets, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays and tail lights. do.

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

As used herein, "top" means located furthest from the substrate, and "bottom" means located closest to the substrate. When a first layer is described as being “disposed” “on” a second layer, the first layer is disposed relatively remote from the substrate. Other layers may exist between the first layer and the second layer, unless it is specified that the first layer “and” the second layer “contact”. For example, it can be explained that even if there are several kinds of organic layers between the cathode and the anode, the cathode is still "disposed" "on" the anode.

As used herein, “solution treatable” means capable of being dissolved, dispersed or transported in and/or precipitated from a liquid medium in the form of a solution or suspension.

When it is considered that the ligand acts directly on the photosensitive performance of the light emitting material, the ligand can be referred to as a "photosensitive ligand". When it is considered that the ligand does not affect the photosensitive performance of the light emitting material, the ligand may be referred to as an "auxiliary ligand", which may change the properties of the photosensitive ligand.

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the spin statistics limit of 25% via delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet annihilation (TTA).

In another aspect, type E delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet state and the singlet-excited state. A compound capable of generating type E delayed fluorescence must have a very small singlet-triplet gap to allow transitions between energy states. Thermal energy can activate a transition from the triplet state to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A remarkable characteristic of TADF is that the delay factor increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative attenuation caused by the triplet state, the ratio of back-filled singlet excited states can reach 75%. . The total proportion of singlet states can be 100%, which far exceeds 25% of the spin statistics of the excitons generated by the electric field.

Characteristics of type E delayed fluorescence can be found in exciplex systems or single compounds. Without being bound by theory, it is believed that type E delayed fluorescence requires that the luminescent material have a small singlet-triplet energy gap (ΔES-T). An organic art object-acceptor luminescent material containing a non-metal has the potential to realize these characteristics. The release of these materials is commonly labeled as art object-receptor charge-transfer (CT)-type emission. Spatial separation of HOMO and LUMO in these co-receptor-type compounds generally results in small ΔES-T. Such conditions may include CT conditions. In general, an electron acceptor luminescent material is constituted by linking an electron acceptor moiety (eg, an amino group or a carbazole derivative) and an electron acceptor moiety (eg, a 6-membered aromatic ring containing N).

Regarding the definition of the term substituent,

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

Alkyl groups include straight-chain alkyl groups and branched alkyl groups as used herein. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n -heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group Decyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3 -Contains a methylpentyl group. In the above, preferred are methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, t-butyl group, n-pentyl group, neopentyl group and n-hexyl group. Also, the alkyl group may be optionally substituted.

Cycloalkyl groups as used herein include 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 carbon atoms. Examples of the cycloalkyl group include cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4,4-dimethylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group (1-norbornyl), 2-norbornyl group, and the like. In the above, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, and a 4,4-dimethylcyclohexyl group are preferable. In addition, the cycloalkyl group may be optionally substituted.

The heteroalkyl group is as used herein, and the heteroalkyl group is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom in one or more carbons in the chain of the alkyl group It includes those formed by being substituted with a hetero atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of the heteroalkyl group include a methoxymethyl group, an ethoxymethyl group, an ethoxyethyl group, a methylthiomethyl group, an ethylthiomethyl group, an ethylthioethyl group, a methoxymethoxymethyl group, an ethoxymethoxymethyl group, an ethoxyethoxyethyl group, Hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, sulfanylmethyl group, sulfanylethyl group, sulfanylpropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylgermanylmethyl group, trimethylgermanylethyl group, Trimethylgermanylisopropyl group, dimethylethylgermanylmethyl group, dimethylisopropylgermanylmethyl group, tert-butyldimethylgermanylmethyl group, triethylgermanylmethyl group, triethylgermanylethyl group, triisopropylgermanylmethyl group, triisopropyl group a germanylethyl group, a trimethylsilylmethyl group, a trimethylsilylethyl group, a trimethylsilylisopropyl group, a triisopropylsilylmethyl group, and a triisopropylsilylethyl group. Also, the heteroalkyl group may be optionally substituted.

Alkenyl groups, as used herein, include straight chain olefin groups, branched olefin groups and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group containing 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group (1,3-butadienyl), a 1-methylvinyl group, a styryl group, 2,2-diphenylvinyl group, 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-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group, cyclopentenyl group, cyclopentadienyl group, cyclohexenyl group, cycloheptenyl group (cycloheptenyl), cycloheptatrienyl group, cyclooctenyl group, cyclooctatetraenyl group (Cyclooctatetraenyl) and norbornenyl group (norbornenyl). Also, the alkenyl group may be optionally substituted.

Alkynyl groups, as used herein, include straight-chain alkynyl groups. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group containing 2 to 10 carbon atoms. Examples of the alkynyl group include ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3,3-dimethyl-1-butynyl group , 3-ethyl-3-methyl-1-pentynyl group, 3,3-diisopropyl 1-pentynyl group, phenylethynyl group, phenylpropynyl group, and the like. In the above, ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group and phenylethynyl group are preferable. Also, the alkynyl group may be optionally substituted.

Aryl or aromatic groups contemplate condensed and unfused systems as used herein. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a tetraphenylene group, a naphthyl group, an anthracene group, a phenalene group, a phenanthrene group, a fluorene group, a pyrene group, It includes a chrysene group, a perylene group and an azulene group, and preferably includes a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a fluorene group and a naphthalene group. Examples of the non-fused aryl group include a phenyl group, a biphenyl-2-yl group (biphenyl-2-yl), a biphenyl-3-yl group, a biphenyl-4-yl group, a p-terphenyl-4-yl group, and a p-terphenyl group. -3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group , p-tolyl group, p-(2-phenylpropyl)phenyl group, 4'-methylbiphenylyl group, 4''-tertbutyl group-p-terphenyl-4-yl group, o-cumenyl group (o-cumenyl) , m-cumenyl group, p-cumenyl group, 2,3-xylyl group, 3,4-xylyl group, 2,5-xylyl group, mesityl group and m-quaterphenyl group (m-quaterphenyl) ) is included. Also, the aryl group may be optionally substituted.

Heterocyclic group or heterocyclyl, as used herein, contemplates non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is a nitrogen atom or an oxygen atom. , a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and a preferred non-aromatic heterocyclic group is one containing 3 to 7 ring atoms, such as nitrogen, oxygen, silicon or sulfur. at least one heteroatom. Examples of the non-aromatic heterocyclic group include an oxiranyl group, an oxetanyl group, a tetrahydrofuran group, a tetrahydropyran group, a dioxolane group group), dioxane group, aziridinyl group, dihydropyrrole group, tetrahydropyrrole group, piperidine group, oxazolidinyl group group), morpholino group, piperazinyl group, oxepine group, thiepine group, azepine group and tetrahydrosilole group includes Also, the heterocyclic group may be optionally substituted.

Heteroaryl groups, as used herein, include unfused and fused heteroaromatic groups which may contain 1-5 heteroatoms. Here, at least one hetero atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. The isoaryl group also refers to a heteroaryl group. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, and more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzoselenophene group. (benzoselenophene), carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole (oxazole), thiazole group, oxadiazole group, oxatriazole group, dioxazole group, thiadiazole group, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine , oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole , benzothiazole group, quinoline group, isoquinoline group, cinnoline group, quinazoline group, quinoxaline group, naphthyridine group, phthalazine group, pteridine group, xanthene group , acridine group, phenazine group, phenothiazine group, benzothienopyridine group, thienodipyridine group, benzofuranopyridine group (Benzofuranopyridine), furanodipyridine group (Furanodipyridine), benzoselenopheno including a pyridine group (benzoselenophenopyridine), a selenophenodipyridine group, preferably a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a carbazole group, an indolocarbazole group, an imidazole group, Pyridine group, triazine group, benzimidazole group, 1,2-azaborane group, 1,3-azaborane group, 1,4-azaborane group, borazine borazine and their aza analogues. Also, the heteroaryl group may be optionally substituted.

Alkoxy groups are represented as -O-alkyl groups, -O-cycloalkyl groups, -O-heteroalkyl groups or -O-heterocyclic groups as used herein. Examples and preferred examples of the alkyl group, the cycloalkyl group, the heteroalkyl group and the heterocyclic group are as described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, tetrahydrofuranylox group, tetrahydropyranyloxy group, methoxypropyloxy group, ethoxyethyloxy group, methoxymethyloxy group and ethoxymethyloxy group. Also, the alkoxy group may be optionally substituted.

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

Arylalkyl group as used herein includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenylt-butyl group, α-naphthylmethyl group, 1-α-naphthyl group -Ethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-β-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthyl-ethyl group, 2-β- Naphthyl-ethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group (p -chlorobenzyl), m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group (p-bromobenzyl), m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group (p- iodobenzyl), m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group (p-hydroxybenzyl), m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-amino Benzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1- hydroxy-2-phenylisopropyl group and 1-chloro-2-phenylisopropyl group. In the above, the benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group and 2-phenylisopropyl group desirable. In addition, the aralkyl group may be optionally substituted.

The alkylsilyl group as used herein includes a silyl group substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethyl and an isopropylsilyl group, a tri-t-butylsilyl group, a triisobutylsilyl group, a dimethyl-t-butylsilyl group, and a methyl-di-t-butylsilyl group. In addition, the aralkyl group may be optionally substituted.

Arylsilyl group (arylsilyl group) as used herein includes a silyl group substituted with at least one aryl. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include a triphenylsilyl group, a phenyldibiphenylsilyl group, a diphenylbiphenylsilyl group, a phenyldiethylsilyl group, a diphenylethylsilyl group, a phenyldimethylsilyl group, and a diphenylmethylsilyl group. , a phenyldiisopropylsilyl group, a diphenylisopropylsilyl group, a diphenylbutylsilyl group, a diphenylisobutylsilyl group, and a diphenyl-t-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.

Alkylgermanyl group (alkylgermanyl) as used herein includes germanyl group substituted with alkyl. The alkylgermanyl group may be an alkylgermanyl group having 3 to 20 carbon atoms, preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of the alkylgermanyl group include a trimethylgermanyl group, a triethylgermanyl group, a methyldiethylgermanyl group, an ethyldimethylgermanyl group, a tripropylgermanyl group, a tributylgermanyl group, a triisopropylgermanyl group, and a methyldiisopropylgermanyl group, a dimethylisopropylgermanyl group, a trit-butylgermanyl group, a triisobutylgermanyl group, a dimethylt-butylgermanyl group, and a methyldi-t-butylgermanyl group. In addition, the alkylgermanyl group may be optionally substituted.

Arylgermanyl group (arylgermanyl) as used herein includes a germanyl group substituted with at least one aryl or heteroaryl. The arylgermanyl group may be an arylgermanyl group having 6 to 30 carbon atoms, preferably an arylgermanyl group having 8 to 20 carbon atoms. Examples of the arylgermanyl group include a triphenylgermanyl group, a phenyldibiphenylgermanyl group, a diphenylbiphenylgermanyl group, a phenyldiethylgermanyl group, a diphenylethylgermanyl group, a phenyldimethylgermanyl group, and a diphenyl group. and a methylgermanyl group, a phenyldiisopropylgermanyl group, a diphenylisopropylgermanyl group, a diphenylbutylgermanyl group, a diphenylisobutylgermanyl group, and a diphenylt-butylgermanyl group. In addition, the arylgermanyl group may be optionally substituted.

The term "aza" in azadibenzofuran, azadibenzothiophene and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced 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. Other nitrogen analogs of the above-described aza derivatives can readily be conceived by those skilled in the art, and all such analogs are intended to be encompassed by the terms set forth herein.

In the present invention, unless otherwise defined, 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 alke group Nyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted alkylgermanyl group, substituted arylgermanyl group, substituted amino group, substituted When any one term from the group consisting of an acyl group, a substituted carbonyl group, a substituted carboxylic acid group, a substituted ester group, and a substituted sulfinyl group is used, it is an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, Aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, alkylgermanyl group, arylgermanyl group, amino group, acyl group, carbonyl group, carboxyl group Any one of an acid group, an ester group, a sulfinyl group, a sulfonyl group and a phosphino group is deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms An unsubstituted cycloalkyl group having a (cycloalkyl group), an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted group having 7 to 30 carbon atoms an aralkyl group, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, 2 to 20 carbon atoms an unsubstituted alkynyl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms ), an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, an unsubstituted arylgermanyl group having 6 to 20 carbon atoms, unsubstituted having 0-20 carbon atoms One or more selected from an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof It means that it can be replaced by a dog.

It is to be understood that when a molecular fragment is described with a substituent or linked to other moieties in other forms, it is a fragment (eg, a phenyl group, a phenylene group, a naphthyl group, a dibenzofuran group) or whether it is the whole molecule (eg , benzene, naphthyl group, dibenzofuran group). As used herein, these different ways of designating a substituent or a fragment linkage are considered equivalent.

In the compounds referred to in the present application, hydrogen atoms may be partially or completely replaced by deuterium. Other elements such as carbon and nitrogen may also be replaced with other stable isotopes thereof. As this improves the efficiency and stability of the device, it may be desirable to substitute other stable isotopes in the compound.

In the compounds mentioned in this application, polysubstitution refers to a range up to the maximum usable substitution including disubstitution. In the compounds mentioned in this application, when any substituent represents polysubstitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it indicates that the substituent may exist at a plurality of available substitution positions in the linking structure, Substituents present at a plurality of available substitution positions may be of the same structure or may be of different structures.

In the compounds mentioned herein, for example, adjacent substituents in the compounds cannot be optionally joined to form a ring, unless it is expressly defined that adjacent substituents may optionally be joined to form a ring. In the compounds mentioned in the present invention, that adjacent substituents may be optionally joined to form a ring includes cases in which adjacent substituents may be joined to form a ring, and also adjacent substituents are not connected to form a ring cases are included. When adjacent substituents are optionally connected to connect the rings, the formed ring may be a monocyclic ring, a polycyclic ring (including a spiro ring, a bridged ring, a condensed ring) an alicyclic ring, a heteroalicyclic ring, It may be an aromatic ring or a heteroaromatic ring. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms bonded directly to each other, or substituents bonded to more distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms bonded directly to each other.

The intent of the expression that adjacent substituents may be optionally linked to form a ring is also intended to contemplate that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which is illustrated by the formula :

.

.

The intent of the statement that adjacent substituents may be optionally linked to form a ring is also intended to contemplate that two substituents bonded to a carbon atom directly bonded to each other are linked to each other by a chemical bond to form a ring, which has the formula It is exemplified through:

.

.

The intent of the expression that adjacent substituents may be optionally linked to form a ring is also intended to contemplate that two substituents bonded to more distant carbon atoms are linked to each other by a chemical bond to form a ring, which is via the formula is exemplified:

.

.

In addition, the intention of the expression that adjacent substituents may be optionally connected to form a ring is also that when one of two substituents adjacent to each other represents hydrogen, the second substituent is bonded to the side at which the hydrogen atom is bonded to form a ring. intend to consider This is exemplified through the formula:

.

.

According to an embodiment of the present invention, a metal complex is disclosed, wherein the metal complex includes a metal M and a ligand L _a coordinated with the metal M, wherein L _a has a structure represented by Formula 1,

In Equation 1,

metal M is selected from metals having a relative atomic mass greater than 40;

Cy is 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, identically or differently each time it appears, ;

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R′ are present simultaneously, the two R′ are the same or different;

X ₁ to X ₅ are identically or differently selected from CR _X or N whenever they appear;

Ar has the structure shown in Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;

R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;

ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;

R', R _x , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms A cyclic cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted 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, 2 substituted or unsubstituted alkynyl group having -20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, 3-20 carbon atoms A substituted or unsubstituted alkylsilyl group having a group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgerma having 3 to 20 carbon atoms nyl group, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocia group selected from the group consisting of no group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

"*" indicates the linkage position of formula 2;

Adjacent substituents R', R _x , R _a1 , R _a2 may optionally be joined to form a ring.

In the present context, "adjacent substituents R', R _x , R _a1 , R _a2 may be optionally connected to form a ring" means that in the adjacent group of substituents, for example, between two substituents R', between two substituents R _x , between two substituents R _a1 , between two substituents R _a2 , between substituents R _a1 and R _a2 , indicating that any one or more of these substituent groups may be linked to form a ring it means Obviously, all of these substituents may not be connected to form a ring.

로 나타내는 구조를 구비하는 것을 나타내며, 이때 "고리 Ar₁ 및 고리 Ar₂의 총 고리원자수는 8보다 크거나 같다"는 것은 고리 Ar₁이 총 고리원자수가 8보다 크거나 같은 방향족 고리 또는 헤테로방향족 고리인 것을 의미하고; 식 2에서 a가 1일 경우, Ar이

로 나타내는 구조를 구비하는 것을 나타내며; 예를 들어 이때 고리 Ar₁ 및 고리 Ar₂가 모두 페닐기이고 R_a1 및 R_a2가 모두 수소일 경우, 고리 Ar₁ 및 고리 Ar₂의 총 고리원자수는 12와 같으며; 또 예를 들어 이때 고리 Ar₁ 및 고리 Ar₂가 모두 페닐기이고 R_a1 이 모두 수소이며, R_a2가 단일 치환이고 또한 페닐기일 경우, 고리 Ar₁ 및 고리 Ar₂의 총 고리원자수는 12와 같다. 기타 상황은 상기의 내용에 따라 유추할 수 있다.In the present context, "ring atom" in aromatic rings and heteroaromatic rings refers to a cyclic structure having aromatic properties bonded by atoms (eg, monocyclic (hetero)aromatic rings, fused ring (hetero)aromatic rings). It represents the atoms constituting the ring itself. All carbon atoms and heteroatoms in the ring (including but not limited to O, S, N, Se or Si, etc.) are included in the number of ring atoms. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the number of ring atoms. For example, the number of ring atoms of a phenyl group, a pyridine group, and a triazine group is 6; The number of ring atoms of the fused dithiophene group and the fused difuran group is 8; Each of the benzothiophenyl group and the benzofuran group has 9 ring atoms, and the naphthyl group, the quinoline group, the isoquinoline group, the quinazoline group and the quinoxaline group each have 10 ring atoms; each of dibenzothiophene, dibenzofuran, fluorene, azadibenzothiophene, azadibenzofuran and azafluorene has 13 ring atoms; Various examples described herein are merely exemplary, and other cases can be inferred accordingly. In Equation 2, when a is 0, Ar is

In this case, "the total number of ring atoms of the ring Ar ₁ and the ring Ar ₂ is greater than or equal to 8" means that the ring Ar ₁ has a total number of ring atoms greater than or equal to 8. ring; In Equation 2, when a is 1, Ar is

represents having a structure represented by ; For example, in this case, when both the ring Ar ₁ and the ring Ar ₂ are phenyl groups and both R _a1 and R _a2 are hydrogen, the total number of ring atoms of the ring Ar ₁ and the ring Ar ₂ is equal to 12; Also, for example, in this case, when both Ring Ar ₁ and Ring Ar ₂ are phenyl groups, R _a1 is both hydrogen, and R _a2 is monosubstituted and a phenyl group, the total number of ring atoms of Ring Ar ₁ and Ring Ar ₂ is equal to 12. . Other circumstances can be inferred according to the above.

According to an embodiment of the present invention, Cy is any one structure selected from the group consisting of the following structures,

;

;

here,

R each occurrence, identically or differently, represents single substitution, multiple substitution or unsubstituted; When a plurality of R is present in any structure, said R are the same or different;

R is identically or differently each time it appears hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1 to 20 carbon atoms A substituted or unsubstituted alkoxy group, 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 group having 2 to 20 carbon atoms an alkynyl 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms (alkylsilyl group), a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted having 6 to 20 carbon atoms or an unsubstituted arylgermanyl group, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, It is selected from the group consisting of a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R may optionally be joined to form a ring;

'은 X₁, X₂, X₃ 또는 X₄에 연결되는 위치를 나타낸다.Here, '#' represents a position connected to the metal M; '

' represents a position connected to X ₁ , X ₂ , X ₃ or X ₄ .

In the present invention, "adjacent substituents R may be optionally connected to form a ring" means that any one or a plurality of substituent groups formed between any two substituents R may be connected to form a ring means to indicate Obviously, all of these substituents may not be connected to form a ring.

According to an embodiment of the present invention, L _a is selected from the group consisting of the same or different structure whenever it appears,

;

;

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R′ are present simultaneously, the two R′ are the same or different;

Ar has the structure shown in Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;

ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;

R, R _x , R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;

R, R', R _x , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms an alkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, 2 to 20 carbon atoms A substituted or unsubstituted alkynyl group having 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 substitution having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 A substituted or unsubstituted arylgermanyl group having ~20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group , is selected from the group consisting of a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R, R′, R _x , R _a1 and R _a2 may optionally be joined to form a ring;

"*" indicates the connection position of Formula 2.

In the present context, "adjacent substituents R, R', R _x , R _a1 and R _a2 may be optionally connected to form a ring" means, among them, in an adjacent group of substituents, for example, between two substituents R , between two substituents R', between two substituents R _x , between two substituents R _a1 , between two substituents R _a2 , between substituents R _a1 and R _a2 , any one or a plurality of these substituent groups are linked It means that it can form a ring. Obviously, all of these substituents may not be connected to form a ring.

According to an embodiment of the present invention, wherein the metal complex has the general formula M(L _a ) _m (L _b ) _n (L _c ) _q ;

here,

M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, identically or differently each time it appears; Preferably, M is selected from Pt or Ir the same or differently each time it appears;

L _a , L _b and L _c are each a first ligand, a second ligand and a third ligand coordinated with the metal M, and L _c is the same as or different from L _a or L _b ; Among them, L _a , L _b and L _c may be optionally linked to form a multidentate ligand; For example, any two of L _a , L _b and L _c may be joined to form a tetradentate ligand; Also for example, L _a , L _b and L _c may be linked to each other to form a hexadentate ligand; or also for example, _{La , L b and} L _c may not all be linked to form a multidentate 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, and the sum of m+n+q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L _a are the same or different, when n is equal to 2, two L _b are the same or different; when q is equal to 2, two L _c are the same or different;

L _b and L _c are the same or different each time they appear is a structure represented by any one selected from the group consisting of:

,

,

,

,

,

,

,

,

,

,

,

;

,

,

,

,

,

,

,

,

,

,

,

;

here,

R _a , R _b each time it appears, identically or differently, represents mono-, poly- or unsubstituted;

X _b , identically or differently each time it appears, is selected from the group consisting of O, S, Se, NR _N1 and CR _C1 R _C2 ;

R _a , R _b , R _c , R _N1 , R _C1 and R _C2 are identically or differently each time they appear hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 rings A substituted or unsubstituted cycloalkyl group having carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, 7 to 30 carbon atoms A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 20 carbon atoms A cyclic alkenyl group, a substituted or unsubstituted 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 , 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 having 3 to 20 carbon atoms An unsubstituted alkylgermanyl group, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group , is selected from the group consisting of a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 may optionally be joined to form a ring.

In the present context, "adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 may optionally be joined to form a ring" means that in the adjacent group of substituents, for example, Between two substituents R _a , between two substituents R _b , between two substituents R _c , between substituents R _a and R _b , between substituents R _a and R _c , between substituents R _b and R _c , substituents R _a and R between _N1 , substituents R _b and R _N1 , substituents R _a and R _C1 , substituents R _a and R _C2 , substituents R _b and R _C1 , substituents R _b and R _C2 , and substituents R _C1 and R _C2 Between, any one or a plurality of these substituent groups is meant to indicate that they may be connected to form a ring. Obviously, all of these substituents may not be connected to form a ring.

According to an embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, either identically or differently whenever it appears.

According to one embodiment of the present invention, the metal M is selected from Pt or Ir, either identically or differently, whenever it appears.

According to an embodiment of the present invention, the metal complex Ir(L _a ) _m (L _b ) _3-m has a structure represented by Formula 3,

here,

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R′ are present simultaneously, the two R′ are the same or different;

m is selected from 1, 2 or 3; when m is selected from 1, two L _b are the same or different; when m is selected from 2 or 3, a plurality of L _a are the same or different;

Y ₁ - Y ₄ are identically or differently selected from CR _y or N whenever they appear;

X ₁ to X ₅ are identically or differently selected from CR _x or N whenever they appear;

Ar has the structure shown in Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;

R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;

ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;

"*" indicates the linkage position of formula 2;

R', R _x , R _y , R ₁ -R ₈ , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to A substituted or unsubstituted cycloalkyl group having 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, 7 to 30 substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, 2 to 20 carbon atoms A substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 3 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, 3 to 20 carbon atoms A substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group , an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R′, R _x , R _y , R _a1 , R _a2 may optionally be joined to form a ring;

Adjacent substituents R ₁ to R ₈ may be optionally connected to form a ring.

In this context, "adjacent substituents R', R _x , R _y , R _a1 and R _a2 may optionally be connected to form a ring" means that in the adjacent substituent group, for example, two substituents R ', between two substituents R _x , between two substituents R _y , between two substituents R _a1 , between two substituents R _a2 , between two substituents R _a1 and R _a2 , between two substituents R' and R _x , It means that any one or a plurality of these substituent groups may be connected to form a ring. Obviously, all of these substituents may not be connected to form a ring. “Adjacent substituents R ₁ to R ₈ may be optionally connected to form a ring” means, among them, in a group of adjacent substituents, for example, between adjacent substituents R ₁ and R ₂ , between substituents R ₃ and R ₂ , between substituents R ₃ and R ₄ , substituents R ₅ and R ₄ , substituents R ₅ and R ₆ , substituents R ₇ and R ₆ , substituents R ₇ and R ₈ , any one of these adjacent groups of substituents, or A plurality means that it can be connected to form a ring. Obviously, all of these substituents may not be connected to form a ring.

According to an embodiment of the present 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'; when two R′ are present simultaneously, the two R′ are the same or different;

m is selected from 1, 2 or 3; when m is selected from 1, two L _b are the same or different; when m is selected from 2 or 3, a plurality of L _a are the same or different;

R _x and R _y each time it appears, identically or differently, mono-, poly- and unsubstituted;

Ar has a structure represented by Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;

R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;

ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;

"*" indicates the linkage position of formula 2;

R', R _x , R _y , R ₁ to R ₈ , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to A substituted or unsubstituted cycloalkyl group having 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, 7 to 30 substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, 2 to 20 carbon atoms A substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 3 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, 3 to 20 carbon atoms A substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group , an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R′, R _x , R _y , R _a1 , R _a2 may optionally be joined to form a ring;

Adjacent substituents R ₁ to R ₈ may be optionally connected to form a ring.

According to an embodiment of the present invention, X ₁ -X ₅ is selected from CR _x equally or differently each time it appears.

According to an embodiment of the present invention, Y ₁ -Y ₄ are identically or differently selected from CR _y whenever they appear.

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

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

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

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

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

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

According to an embodiment of the present invention, R _a1 and R _a2 are identically or differently each time they appear, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 ring carbon atoms ( a substituted or unsubstituted cycloalkyl group having ring carbon atoms), a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 3~ A substituted or unsubstituted heteroaryl group having 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, iso It is selected from the group consisting of a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.

According to an embodiment of the present invention, R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 3 to 6 ring carbon atoms atoms) a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, 3 to 15 It is selected from the group consisting of a substituted or unsubstituted alkylsilyl group having two carbon atoms, and combinations thereof.

According to an embodiment of the present invention, R _a1 and R _a2 are the same or different whenever they appear 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 It is selected from the group consisting of a tert-butyl group, a deuterated cyclopentyl group, a deuterated cyclohexyl group, a phenyl group, a pyridine group, a trimethylsilyl group, and combinations thereof.

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are identically or differently each time they appear, an aromatic ring having 6 to 18 ring atoms, a heteroaromatic ring having 5 to 18 ring atoms, or a combination thereof; The total number of ring atoms of the ring Ar ₁ and the ring Ar ₂ is greater than or equal to 8, and less than or equal to 30.

According to an embodiment of the present invention, in Ar, the total number of ring atoms of the ring Ar ₁ and the ring Ar ₂ is greater than or equal to 8 and less than or equal to 24.

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

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are identically or differently each time they appear, an aromatic ring having 6 ring atoms, a heteroaromatic ring having 5 or 6 ring atoms, or selected from combinations thereof.

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are selected from an aromatic ring or heteroaromatic ring having 6 ring atoms, identically or differently each time they appear.

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are identically or differently selected from aromatic rings having 6 ring atoms each time they appear.

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are identically or differently each time they appear, a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a triazine ring, a phenanthrene ring, an anthracene ring , silafluorene ring, quinoline ring, isoquinoline ring, benzofuran ring, fused dithiophene ring, fused difuran ring, benzothiophene ring, indene ring, dibenzofuran ring, dibenzothiophene ring, triphenyl a rene ring, a carbazole ring, an azacarbazole ring, an azadibenzofuran ring, an azadibenzothiophene ring, an azasilafluorene ring, and combinations thereof; The total number of ring atoms of the ring Ar ₁ and the ring Ar ₂ is greater than or equal to 8, and less than or equal to 30.

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, 및 이들의 조합으로 이루어진 군에서 선택되며;According to an embodiment of the present invention, Ar is the same or different each time it appears,

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, and combinations thereof;

optionally, said group is partially or fully substituted by deuterium; Here, "*" indicates the connection position of Ar.

According to an embodiment of the present invention, R _x is identically or differently each time it appears hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms A cyclic 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, a substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms group, cyano group, and combinations thereof.

According to an embodiment of the present invention, where R _x is the same or differently whenever it appears, hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted having 3 to 6 ring carbon atoms or an unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted group having 3 to 6 carbon atoms It is selected from the group consisting of an alkylsilyl group, a cyano group, and combinations thereof.

According to an embodiment of the present invention, at least one of R _x is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, and selected from the group consisting of combinations thereof.

According to an embodiment of the present invention, at least one of R _x is deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, 6 A substituted or unsubstituted aryl group having ˜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, a cyano group, and these It is selected from the group consisting of combinations of.

According to an embodiment of the present invention, at least one of R _x is deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, cya Nogi and combinations thereof.

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

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

According to an embodiment of the present invention, X ₅ is CR _x , wherein R _x is a cyano group or fluorine.

According to one embodiment of the present invention, R _y is the same or different whenever it appears hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 ring carbon atoms ) having a substituted or unsubstituted 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, 3 to 20 carbon atoms It is selected from the group consisting of a substituted or unsubstituted alkylsilyl group having a carbon atom and combinations thereof.

According to an embodiment of the present invention, R _y is the same or differently whenever it appears hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted having 3 to 6 ring carbon atoms A cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 15 carbon atoms, and selected from the group consisting of combinations thereof.

According to an embodiment of the present invention, at least one R _y is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms It is selected from the group consisting of a cyclic 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 combinations thereof.

According to an embodiment of the present invention, wherein at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms , a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and their selected from the group consisting of combinations.

According to an embodiment of the present invention, wherein 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 having 1 to 20 carbon atoms It is selected from the group consisting of an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof.

According to an embodiment of the present invention, wherein at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, a methyl group, an ethyl group, a propyl group, an isopropyl group, n -butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, and combinations thereof; Optionally, hydrogens in these groups may be partially or fully substituted with deuterium.

According to an embodiment of the present invention, wherein R' is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

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

According to an embodiment of the present invention, where R ₇ is identically or differently each time it appears, hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted having 3 to 20 ring carbon atoms or an unsubstituted cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted group having 7 to 30 carbon atoms A substituted 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 , 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group , a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

According to an embodiment of the present invention, L _a is selected from the group consisting of L _a1 to L _a1177 , identically or differently whenever it appears, for specific structures of L _a1 to L _a1177 refer to claim 16 .

According to an embodiment of the present invention, L _b is identically or differently selected from the group consisting of L _b1 to L _b128 whenever it appears, and for specific structures of L _b1 to L _b128 , refer to claim 17 .

According to an embodiment of the present invention, L _c is selected from the group consisting of L _c1 to L _c360 , identically or differently each time it appears, see claim 18 for a specific structure of L _c1 to L _c360 .

According to an embodiment of the present invention, the metal complex has a structure of Ir(L _a ) ₂ (L _b ), and L _a is any 1 from the group consisting of L _a1 to L _a1177 the same or different each time it appears species or any two species, and L _b is selected from any one of the group consisting of L _b1 to L _b128 , of which the specific structure of L _a1 to L _a1177 is referred to in claim 16, and L b1 to L _b1 to For the specific structure of L _b128 , refer to claim 17 .

According to an embodiment of the present invention, the metal complex has a structure of Ir(L _a )(L _b ) ₂ , and L _a is the same or different whenever it appears Any 1 from the group consisting of L _a1 to L _a1177 is selected from species, and L _b is selected from any one or any two of the group consisting of L _b1 to L _b128 , of which the specific structure of L _a1 to L _a1177 is referred to in claim 16 , and L b1 to L _b1 to For the specific structure of L _b128 , refer to claim 17 .

According to an embodiment of the present invention, the metal complex has a structure of _Ir (L _a ) ₃ , and L _a is the same or different whenever it appears Any one or any one of the group consisting of La 1 to _{La 1177} . It is selected from 2 types or any 3 types, and among them, refer to claim 16 for specific structures of L _a1 to L _a1177 .

According to an embodiment of the present invention, the metal complex has a structure of Ir(L _a ) ₂ (L _c ), and L _a is any 1 from the group consisting of L _a1 to L _a1177 the same or different each time it appears. selected from the species or any two, L _c is selected from any one of the group consisting of L _c1 to L _c360 , of which, for specific structures of L _a1 to L _a1177 , see claim 16, and L _c1 to For a specific structure of L _c360 , refer to claim 18 .

According to an embodiment of the present invention, the metal complex has a structure of Ir(L _a )(L _c ) ₂ , and L _a is any 1 from the group consisting of L _a1 to L _a1177 the same or different each time it appears. is selected from species, and L _c is selected from any one or any two of the group consisting of L _c1 to L _c360 , of which the specific structure of L _a1 to L _a1177 refers to claim 16, and L _c1 to L c360 For a specific structure of L _c360 , refer to claim 18 .

According to an embodiment of the present invention, the metal complex has a structure of Ir(L _a )(L _b )(L _c ), wherein L _a is the same or different whenever it appears from the group consisting of L _a1 to L _a1177 L _b is selected from any one of the group consisting of L _b1 to L _b128 and L _c is selected from any one of the group consisting of L _c1 to L _c360 ; Among them, refer to claim 16 for a specific structure of L _a1 to L _a1177 , refer to claim 17 for a specific structure of L _b1 to L _b128 , and refer to claim 18 for a specific structure of L _c1 to L _c360 .

According to an embodiment of the present invention, the metal complex is selected from the group consisting of metal complex 1 to metal complex 1008; Among them, for specific structures of metal complex 1 to metal complex 1008, refer to claim 19.

According to an embodiment of the present invention, an electroluminescent device is disclosed, comprising:

anode;

cathode, and

and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex according to any of the above embodiments.

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

According to an embodiment of the present invention, the light emitting layer of the electroluminescent device emits green light.

According to an embodiment of the present invention, the light emitting layer of the electroluminescent device emits white light.

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

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

According to an embodiment of the present invention, in the electroluminescent device, at least one of the host compounds is a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a carbazole group, an azacarbazole group, an indolocarbazole group, Dibenzothiophene group, azadibenzothiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenylene group, fluorene group , a silafluorene group, a naphthyl group, a quinoline group, an isoquinoline group, a quinazoline group, a quinoxaline group, a phenanthrene group, an azaphenanthrene group, and combinations thereof. at least one chemical group.

According to an embodiment of the present invention, the first host 1 compound has a structure represented by Formula 4,

here,

E ₁ -E ₆ are identically or differently selected from C, CR _e or N whenever they appear, at least two of E ₁ -E ₆ are N, at least one of E ₁ -E ₆ is C, formula A is connected with;

;

;

here,

Q is, identically or differently, each occurrence selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; two When R″ is present simultaneously, the two R″ can be the same or different;

P is 0 or 1, r is 0 or 1;

when Q is selected from N, p is 0 and r is 1;

when 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 and r is 0;

L is, identically or differently, 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 cycloalkylene group having 6 to 20 carbon atoms a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Q ₁ -Q ₈ are identically or differently selected from C, CR _q or N at each occurrence;

R _e , R" and R _q are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms an alkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, 2 to 20 carbon atoms A substituted or unsubstituted alkynyl group having 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 substitution having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 A substituted or unsubstituted arylgermanyl group having ~20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group , is selected from the group consisting of a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

"*" represents the connection position of to formula A and formula 4;

Adjacent substituents R _e , R″, R _q may optionally be joined to form a ring.

In the present context, "adjacent substituents R _e , R" and R _q may be optionally connected to form a ring" means, among them, in an adjacent group of substituents, for example, between two substituents R _e , two substituents Between R", between two substituents R _q , between substituents R" and R _q , it means that any one or a plurality of these substituent groups may be linked to form a ring. Obviously, between these substituents may not form a ring because they are not all connected.

According to an embodiment of the present invention, E ₁ -E ₆ are identically or differently selected from C, CR _e or N whenever they appear, three of E ₁ -E ₆ are N, and among E ₁ -E ₆ At least one is CR _e , wherein R _e is identically or differently each time it appears, 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 these It is selected from the group consisting of combinations of.

According to an embodiment of the present invention, E ₁ -E ₆ are identically or differently selected from C, CR _e or N whenever they appear, three of E ₁ -E ₆ are N, and among E ₁ -E ₆ At least one is CR _e , wherein R _e is identically or differently whenever it appears, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or an unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted It is selected from the group consisting of a cyclic carbazole group and combinations thereof.

According to one embodiment of the present invention, Q is selected from O, S, N or NR″, either identically or differently each time it appears.

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

According to an embodiment of the present invention, at least one or at least two of Q ₁ -Q ₈ are selected from CR _q , wherein R _q is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted It is selected from a substituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyridine group, or a combination thereof.

According to an embodiment of the present invention, L is the same or differently each time it appears, a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted hetero group having 3 to 20 carbon atoms an arylene group, or a combination thereof.

According to an embodiment of the present invention, L is the same or different whenever it appears a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group, a substituted or It is selected from an unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted fluorenylene group.

According to an embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted phenylene group, and a substituted or unsubstituted biphenylene group, identically or differently each time it appears.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of compounds H-1 to H-243, wherein for specific structures of H-1 to H-243, refer to claim 26.

According to an embodiment of the present invention, the second host compound in the electroluminescent device has a structure represented by Formula 5,

here,

L _x is identically or differently each occurrence represents 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, 6 to 20 carbon atoms a substituted or unsubstituted arylene group having 3-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof;

V is selected from C, CR _v or N, identically or differently each time it appears; at least one of V is C and is connected with L _x ;

U is identically or differently each time it appears is selected from C, CR _u or N, at least one of U is C and is linked to L _x ;

R _v and R _u are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 A substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1~20 A substituted or unsubstituted alkoxy group having 6 to 30 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 A substituted or unsubstituted alkynyl 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, a substituted or unsubstituted group having 3 to 20 carbon atoms an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms A substituted or unsubstituted arylgermanyl group having carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group , is selected from the group consisting of a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Ar ₆ is identically or differently each time it appears 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 optionally be joined to form a ring.

In this embodiment, "adjacent substituents R _v and R _u may be optionally connected to form a ring" means, among them, in a group of adjacent substituents, for example, between two substituents R _v , between two substituents R _u Between, between the substituents R _v and R _u , any one or a plurality of these substituent groups are connected to form a ring. Obviously, all of these substituents may not be connected to form a ring.

According to an embodiment of the present invention, the second host compound in the electroluminescent device has a structure represented by one of Formulas 5-a to 5-j:

,

,

,

,

,

,

,

,

,

.

,

,

,

,

,

,

,

,

,

.

here,

L _x is identically or differently each occurrence represents 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, 6 to 20 carbon atoms a substituted or unsubstituted arylene group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

V is identically or differently selected from CR _v or N whenever it appears;

U is identically or differently selected from CR _u or N whenever it appears,

R _v and R _u are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 A substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1~20 A substituted or unsubstituted alkoxy group having 6 to 30 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 A substituted or unsubstituted alkynyl 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, a substituted or unsubstituted group having 3 to 20 carbon atoms an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms A substituted or unsubstituted arylgermanyl group having carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group , is selected from the group consisting of a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Ar ₆ is identically or differently each time it appears 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 optionally be joined to form a ring.

According to an embodiment of the present invention, the second host compound is selected from the group consisting of compounds X-1 to X-128, wherein for specific structures of compounds X-1 to X-128, refer to claim 28.

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

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

According to another embodiment of the present invention, a compound combination is disclosed, and the compound combination includes the metal complex according to any of the above embodiments.

Combination with other materials

The material used for a specific layer in the organic light emitting device described in the present invention may be used in combination with various other materials present in the device. This combination of materials is described in detail in paragraphs 0132 to 0161 of US Patent Application US2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily refer to the literature to identify combinations and other materials that can be used.

In this text, it is explained that the materials usable for a specific layer in the organic light emitting device can be used in combination with various kinds of other materials present in the device. For example, the light emitting dopant disclosed herein may be used in combination with various types of hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraph 0080-0101 of patent application US2015/0349273A1, the entire contents of which are incorporated herein by reference. The materials described or referenced herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily refer to the literature to identify combinations and other materials that can be used.

In the examples of material synthesis, all reactions proceed under nitrogen gas protection unless otherwise specified. All reaction solvents are anhydrous and used as received from commercial sources. The synthesized product was prepared using one or several types of equipment conventional in the art (BRUKER nuclear magnetic resonance spectroscopy, SHIMADZU liquid chromatography, liquid chromatograph-mass spectrometry, gas chromatograph mass spectrometry) gas chromatograph-mass spectrometry), differential scanning calorimeter, fluorescence spectrophotometer of Shanghai LENGGUANG TECH., electrochemical workstation of Wuhan CORRTEST and sublimation apparatus of Anhui BEQ, etc. ), structures are identified and properties tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device also include equipment conventional in this field (evaporator produced by ANGSTROM ENGINEERING, optical test system and life test system produced by FATAR in Suzhou, ellipsometer produced by ELLITOP in Beijing, etc.) using, but not limited to, methods well known to those skilled in the art. A person skilled in the art is familiar with the relevant information such as the use of the equipment, the test method, and the like, so that the unique data of the sample can be obtained reliably and unaffectedly, and therefore, the relevant content is not further described herein.

Material Synthesis Examples:

The preparation method of the compound of the present invention is not limited, and typical examples include the following compounds, but are not limited thereto, and the synthesis route and preparation method are as follows:

Synthesis Example 1: Synthesis of Metal Complex 127

Step 1:

5-methyl-2-phenylpyridine (10.0 g, 59.2 mmol), iridium trichloride trihydrate (5.0 g, 14.2 mmol), 300 mL 2-ethoxyethanol, and 100 mL water were sequentially added to a 500 mL dry round bottom flask. and then replaced with nitrogen gas three times and heated and stirred at 130° C. for 24 h to protect with nitrogen gas. After cooling, it is filtered, washed 3 times each with methanol and n-hexane, and pumped to dryness to obtain 7.5 g of a yellow solid Intermediate 1 (yield 97%).

Step 2:

Intermediate 1 (7.5 g, 6.8 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (3.8 g, 14.8 mmol) were sequentially added to a 500 mL dry round bottom flask, followed by nitrogen gas was replaced 3 times with nitrogen gas, and stirred at room temperature overnight. Filtration through celite, washing twice with dichloromethane, the following organic phases were collected and concentrated under reduced pressure to obtain 9.2 g of Intermediate 2 (yield 93%).

Step 3:

Add Intermediate 2 (1.3 g, 1.7 mmol), Intermediate 3 (0.9 g, 2.3 mmol), and 250 mL of ethanol to a 500 mL dry round-bottom flask, replace with nitrogen gas 3 times, and protect with nitrogen gas. , and reacted for 18 h by heating at 100 °C. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 127 ( 0.75 g, yield 47.7%) is obtained. The product was identified as the target product with a molecular weight of 925.3.

Synthesis Example 2: Synthesis of Metal Complex 505

Step 1:

5-tert-butyl-2-phenylpyridine (13.2 g, 62.9 mmol), iridium trichloride trihydrate (5.5 g, 15.7 mmol), 300 mL of 2-ethoxyethanol, and 100 mL of water were sequentially added to a dry round-bottom flask of 500 mL. was added, replaced with nitrogen gas 3 times, protected with nitrogen gas, and heated and stirred at 130° C. for 24 h. After cooling, it is filtered, washed 3 times with methanol and n-hexane, respectively, and pumped to dryness to obtain 9.7 g of intermediate 4 (yield 97%).

Step 2:

To a 500 mL dry round bottom flask were sequentially added Intermediate 4 (9.7 g, 7.7 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, silver trifluoromethanesulfonate (4.3 g, 16.7 mmol), and nitrogen gas was replaced 3 times with nitrogen gas, and stirred at room temperature overnight. Filtration with celite, washing with dichloromethane twice, the following organic phases were collected and concentrated under reduced pressure to obtain 13.2 g of a solid intermediate 5 (yield 93%).

Step 3:

Add Intermediate 5 (1.4 g, 1.8 mmol), Intermediate 3 (0.9 g, 2.2 mmol), and 300 mL of ethanol to a 500 mL dry round bottom flask, replace with nitrogen gas 3 times and protect with nitrogen gas, Heat at 100° C. and react for 24 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 505 ( 0.75 g, yield 41.3%). The product was identified as the target product with a molecular weight of 1009.4.

Synthesis Example 3: Synthesis of Metal Complex 520

Step 1:

Intermediate 6 (2.0 g, 4.9 mmol), Intermediate 5 (2.7 g, 3.3 mmol), 50 mL 2-ethoxyethanol and 50 mL N,N-dimethylformamide were sequentially added to a 250 mL dry round bottom flask. and replaced with nitrogen gas three times, protected with nitrogen gas, and heated at 100° C. to react for 96 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 520 ( 1.74 g, yield 51.5%). The product was identified as the target product with a molecular weight of 1023.4.

Synthesis Example 4: Synthesis of metal complex 532

Step 1:

In a dry round bottom flask of 500 mL, add Intermediate 7 (1.8 g, 4.5 mmol), Intermediate 5 (2.5 g, 3.0 mmol), and 300 mL of ethanol, replace with nitrogen gas 3 times and protect with nitrogen gas, Heat at 100° C. and react for 24 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 532 ( 0.55 g, yield 18.2%). The product was identified as the target product with a molecular weight of 1009.4.

Synthesis Example 5: Synthesis of Metal Complex 181

Step 1:

Add Intermediate 2 (2.6 g, 3.5 mmol), Intermediate 8 (2.2 g, 5.3 mmol), and 250 mL of ethanol to a 500 mL dried round-bottom flask, replace with nitrogen gas 3 times, and protect with nitrogen gas. , and reacted for 18 h by heating at 100 °C. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 181 ( 1.1 g, yield 33.3%). The product was identified as the target product with a molecular weight of 943.2.

Synthesis Example 6: Synthesis of Metal Complex 559

Step 1:

Add Intermediate 5 (2.1 g, 2.6 mmol), Intermediate 8 (1.5 g, 3.6 mmol), and 300 mL of ethanol to a 500 mL dry round bottom flask, replace with nitrogen gas 3 times and protect with nitrogen gas, Heat at 100° C. and react for 24 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 559 ( 1.30 g, yield 48.7%) is obtained. The product was identified as the target product with a molecular weight of 1027.3.

Synthesis Example 7: Synthesis of Metal Complex 197

Step 1:

To a 250 mL dry round-bottom flask, sequentially add Intermediate 2 (2.0 g, 2.8 mmol), Intermediate 9 (1.8 g, 3.9 mmol), 50 mL 2-ethoxyethanol and 50 mL N,N-dimethylformamide and replaced with nitrogen gas three times, protected with nitrogen gas, and heated at 100° C. to react for 72 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 197 ( 1.2 g, yield 43.4%) is obtained. The product was identified as the target product with a molecular weight of 1006.3.

Synthesis Example 8: Synthesis of Metal Complex 460

Step 1:

In a 250 mL dry round bottom flask, 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) are added sequentially, protected with nitrogen gas, heated to reflux, and stirred for 24 h. After the reaction was cooled, it was filtered under reduced pressure and suction, and washed 3 times with methanol and n-hexane, respectively, to obtain 4.0 g of a yellow solid intermediate 10 (yield 94.8%).

Step 2:

Intermediate 10 (4.0 g, 3.5 mmol), anhydrous dichloromethane (250 mL), methanol (10 mL), silver trifluoromethanesulfonate (1.9 g, 7.6 mmol) were sequentially added to a 500 mL dry round bottom flask, Replace with nitrogen gas 3 times, protect with nitrogen gas, and stir overnight at room temperature. Filtration through celite (Diatomite), washing twice with dichloromethane, the following organic phases were collected and concentrated under reduced pressure to obtain 5.1 g of intermediate 11 (yield 97.4%).

Step 3:

To a 250 mL dry round bottom flask were sequentially added 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 and, protected with N ₂ , and heated to reflux to react for 96 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 460 ( 0.82 g, yield 40.0%). The product was identified as the target product with a molecular weight of 932.3.

Synthesis Example 9: Synthesis of metal complex 571

Step 1:

To a 250 mL dry round bottom flask were sequentially added Intermediate 13 (1.4 g, 1.7 mmol), Intermediate 5 (1.0 g, 2.4 mmol), 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide. and replaced with nitrogen gas three times, protected with nitrogen gas, and heated at 100° C. to react for 72 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 571 ( 0.5 g, yield 28.4%). The product was identified as the target product with a molecular weight of 1034.3.

Synthesis Example 10: Synthesis of Metal Complex 572

Step 1:

Intermediate 5 (2.4 g, 2.9 mmol), Intermediate 14 (1.5 g, 3.4 mmol), 50 mL of 2-ethoxyethanol and 50 mL of N,N-dimethylformamide were sequentially added to a 250 mL dry round bottom flask. and replaced with nitrogen gas three times, protected with nitrogen gas, and heated at 100° C. to react for 72 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 572 ( 0.7 g, yield 23.0%). The product was identified as the target product with a molecular weight of 1048.4.

Synthesis Example 11: Synthesis of Metal Complex 579

Step 1:

To a 250 mL dry round bottom flask, sequentially add Intermediate 5 (2.2 g, 2.7 mmol), Intermediate 15 (1.5 g, 3.6 mmol), 50 mL 2-ethoxyethanol and 50 mL N,N-dimethylformamide and replaced with nitrogen gas three times, protected with nitrogen gas, and heated at 100° C. to react for 72 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 579 ( 0.8 g, yield 30.7%). The product was identified as the target product with a molecular weight of 1034.3.

Synthesis Example 12: Synthesis of Metal Complex 697

Step 1:

In a dry round bottom flask of 500mL, 5-neopentyl-2-phenylpyridine (13.4g, 59.1mmol), iridium trichloride trihydrate (5.2g, 14.8mmol), 300mL of 2-ethoxyethanol, and 100mL of water were sequentially added. added, replaced with nitrogen gas three times, protected with nitrogen gas, and heated and stirred at 130° C. for 24 h. After cooling, it is filtered, washed 3 times with methanol and n-hexane, and pumped to dryness to obtain 8.5 g of intermediate 16 (yield 88%).

Step 2:

Intermediate 16 (9.7 g, 7.7 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver trifluoromethanesulfonate (4.3 g, 16.7 mmol) were sequentially added to a dry round bottom flask of 500 mL, nitrogen gas was replaced 3 times with nitrogen gas, and stirred at room temperature overnight. Filtration through celite, washing twice with dichloromethane, the following organic phases were collected and concentrated under reduced pressure to obtain 11.8 g of a yellow solid intermediate 17 (yield 100%).

Step 3:

To a 250 mL dry round-bottom flask, sequentially add Intermediate 17 (2.0 g, 2.3 mmol), Intermediate 13 (1.4 g, 3.2 mmol), 50 mL 2-ethoxyethanol and 50 mL N,N-dimethylformamide and replaced with nitrogen gas three times, protected with nitrogen gas, and heated at 100° C. to react for 72 h. After the reaction is cooled, it is filtered through celite. After washing twice with methanol and n-hexane, the yellow solid on celite was dissolved with dichloromethane, the organic phase was collected, concentrated under reduced pressure, and purified by column chromatography, which is a yellow solid product, metal complex 697 ( 0.8 g, yield 32.7%). The product was identified as the target product with a molecular weight of 1062.4.

Those skilled in the art will appreciate that the above preparation method is only one illustrative example, and those skilled in the art will recognize that the structure of other compounds of the present invention can be obtained by practicing it.

Device Example 1-1

First, a glass substrate having an indium tin oxide (ITO) anode having a thickness of 80 nm is cleaned, and then treated using oxygen plasma and UV ozone. After treatment, the substrate is dried in a glove box to remove moisture. Next, the substrate is mounted on the substrate holder and placed in a vacuum chamber. The organic layers specified below are sequentially deposited on the ITO anode through thermal vacuum deposition at a vacuum degree of about 10 ^-8 Torr at a rate of 0.02-2 angstrom/sec. Compound HI is used as the hole injection layer (HIL). The compound HT is used as the hole transport layer (HTL). Compound X-4 is used as the electron blocking layer (EBL). Then, the metal complex 127 of the present invention is doped with the compound X-4 and the compound H-91 to be co-deposited and used as an emission layer (EML). On EML, compound H-1 is used as a hole blocking layer (HBL). On HBL, compound ET and 8-hydroxy quinoline-lithium (Liq) are co-deposited and used as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) having a thickness of 1 nm is deposited as an electron injection layer, and aluminum having a thickness of 120 nm is deposited as a cathode. Next, the device is transferred to a glove box and encapsulated using a glass lid and a desiccant to complete the device.

Device Example 2-1

The embodiment of Device Example 2-1 is the same as that of Device Example 1-1, except for using the metal complex 505 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer.

Device Example 2-2

Except for using the metal complex 520 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 2-2 is the same as that of Device Example 1-1.

Device Example 2-3

Except for using the metal complex 532 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 2-3 is the same as that of Device Example 1-1.

Device Comparative Example 1-1

Except for using the compound GD1 instead of the metal complex 127 of the present invention in the light emitting layer (EML), the embodiment of Device Comparative Example 1-1 is the same as that of Device Example 1-1.

Device Comparative Example 2-1

Except for using the compound GD2 instead of the metal complex 127 of the present invention in the light emitting layer (EML), the embodiment of Device Comparative Example 2-1 is the same as that of Device Example 1-1.

Device Comparative Example 2-2

Except for using the compound GD3 instead of the metal complex 127 of the present invention in the light emitting layer (EML), the embodiment of Device Comparative Example 2-2 is the same as that of Device Example 1-1.

Device Comparative Example 2-3

The embodiment of Device Comparative Example 2-3 is the same as that of Device Example 1-1, except for using the compound GD4 instead of the metal complex 127 of the present invention in the light emitting layer (EML).

Device Comparative Example 2-4

The embodiment of Device Comparative Example 2-4 is the same as that of Device Example 1-1, except that compound GD5 is used instead of the metal complex 127 of the present invention in the light emitting layer (EML).

The detailed device layer structure and thickness are shown in the table below. Here, a layer in which two or more materials are used is obtained by doping different compounds in the weight ratios mentioned therein.

Table 1 Device structures of Examples 1-1 and 2-1 to 2-3 and Comparative Examples 1-1 and 2-1 to 2-4

Device ID HIL HTL EBL EML HBL ETL Example 1-1

)compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 127
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 2-1 compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 505
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 2-2 compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 520 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 2-3 compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 532 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Comparative Example 1-1 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Compound GD1 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Comparative Example 2-1 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Compound GD2 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Comparative Example 2-2 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Compound GD3 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Comparative Example 2-3 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Compound GD4 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Comparative Example 2-4 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Compound GD5 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

)

The material structure used for the device is as follows:

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

.

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

.

Measure the IVL characteristics of the device. 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 under the condition of 1000 cd/m ² were measured. External quantum efficiency (EQE) data, 15mA/cm ² The test was conducted under a constant current condition. These data are recorded and displayed in Table 2.

Table 2 Device data of Examples 1-1 and 2-1 to 2-3 and Comparative Examples 1-1 and 2-1 to 2-4

device ID CIE(x, y) λ _max (nm) FWHM (nm) Voltage (V) CE (cd/A) PE (lm/W) EQE (%) Example 1-1 (0.352, 0.622) 528 60.9 2.82 102 114 24.21 Comparative Example 1-1 (0.352, 0.623) 528 60.3 2.84 95 105 22.36 Example 2-1 (0.351, 0.625) 529 58.3 2.98 103 109 24.09 Example 2-2 (0.355, 0.621) 531 58.5 2.86 101 111 23.64 Example 2-3 (0.349, 0.626) 530 57.8 2.96 99 105 23.31 Comparative Example 2-1 (0.353, 0.623) 531 58.9 3.11 94 95 21.85 Comparative Example 2-2 (0.371, 0.612) 537 48.2 3.05 96 99 21.41 Comparative Example 2-3 (0.357, 0.619) 530 60.7 3.08 78 79 18.57 Comparative Example 2-4 (0.354, 0.622) 530 58.9 3.00 84 88 19.79

debate:

Table 2 shows the device performance of Examples and Comparative Examples. Comparing Example 1-1 with Comparative Example 1-1, Examples 2-1 to 2-3 and Comparative Example 2-1, the distinguishing point is that the phenyl group is replaced by the specified Ar substituent of the metal complex, the half width and In the situation where the maximum emission wavelength is similar and the driving voltage is slightly reduced, the CE, PE, and EQE of the device are all clearly improved. In Example 1-1 compared to 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%. In Examples 2-1 to 2-3 compared to Comparative Example 2-1, EQE was improved by 10.2%, 8.2%, and 6.7%, respectively, PE was improved by 14.7%, 16.8%, and 10.5%, respectively, and CE was improved by 9.6%, respectively %, 7.4% and 5.3%. This explains that the metal complex of the present invention has a specified Ar substituent instead of a phenyl group, so that it is superior to the comparative example in various aspects of performance and clearly improves the overall performance of the device.

For comparison, metal complexes GD3, GD4 and GD5 having Ar substitution specified at other positions were synthesized, that is, Comparative Examples 2-2 to 2-4. Comparing Example 2-1 with Comparative Examples 2-2 to 2-4, the distinguishing point is that the biphenyl group of the L _a ligand of the metal complex is in a different substitution position, and in a situation where the driving voltage is similar, the CE, Both PE and EQE were significantly improved. In Example 2-1 compared to Comparative Examples 2-2 to 2-4, EQE was improved by 12.5%, 29.7%, and 21.7%, respectively, PE was improved by 10.1%, 37.9%, and 23.8%, respectively, and CE was improved by 7.2, respectively %, 32% and 22.6% improvement. This explains that the metal complex having the L _a ligand of the Ar substituent specified at a specific position of the present invention is superior to the complex of the comparative example in various aspects of performance, and clearly improves the overall performance of the device. For the compounds of the present invention, the advantages of introducing specified substituents at specified positions are completely unexpected. It is impossible for even a person skilled in the art to predict such a case.

Device Example 3-1

Except for using the metal complex 181 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 3-1 is the same as that of Device Example 1-1.

Device Example 3-2

Except for using the metal complex 559 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 3-2 is the same as that of Device Example 1-1.

Device Example 4-1

Except for using the metal complex 197 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 4-1 is the same as that of Device Example 1-1.

Device Example 4-2

Except for using the metal complex 460 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 4-2 is the same as that of Device Example 1-1.

Device Example 4-3

Except for using the metal complex 571 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 4-3 is the same as that of Device Example 1-1.

Device Example 4-4

Except for using the metal complex 572 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 4-4 is the same as that of Device Example 1-1.

Device Example 4-5

Except for using the metal complex 579 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 4-5 is the same as that of Device Example 1-1.

Device Examples 4-6

Except for using the metal complex 697 of the present invention instead of the metal complex 127 of the present invention in the light emitting layer, the embodiment of Device Example 4-6 is the same as that of Device Example 1-1.

The detailed device layer structure and thickness are shown in the table below. A layer of two or more materials used herein is obtained by doping different compounds in the weight ratios mentioned therein.

Table 3 Device structures of Examples 3-1 to 3-2 and 4-1 to 4-6

Device ID HIL HTL EBL EML HBL ETL Example 3-1

)Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 181 (63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 3-2 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 559
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 4-1 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 197
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 4-2 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 460
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 4-3 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 571
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 4-4 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 572
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 4-5 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 579
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 4-6 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 697
(63:31:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

)

The new material structures used in the device are as follows:

,

,

,

,

,

,

,

;

,

,

,

,

,

,

,

;

Measure the IVL characteristics of the device. 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 under the condition of 1000 cd/m ² were measured. External quantum efficiency (EQE) data, 15mA/cm ² The test was conducted under a constant current condition. These data are recorded and displayed in Table 4.

Table 4 Device data of Examples 3-1 to 3-2 and 4-1 to 4-6

device ID CIE(x, y) λ _max (nm) FWHM (nm) Voltage (V) CE (cd/A) PE (lm/W) EQE (%) Example 3-1 (0.349, 0.625) 528 59.9 2.84 104 115 24.54 Example 3-2 (0.352, 0.624) 531 58.4 2.92 105 114 24.51 Example 4-1 (0.336, 0.639) 530 35.2 2.62 115 138 26.35 Example 4-2 (0.342, 0.635) 531 34.9 2.62 109 130 24.84 Example 4-3 (0.338, 0.638) 531 34.0 2.67 112 132 25.45 Example 4-4 (0.340,0.636) 531 34.8 2.65 115 137 25.86 Example 4-5 (0.344, 0.634) 531 36.1 2.75 110 126 25.06 Example 4-6 (0.339, 0.637) 531 34.9 2.67 109 128 24.77

debate:

Table 4 shows the device performance of Examples 3-1 to 3-2 and 4-1 to 4-6 of the present invention. The metal complexes of Examples 3-1 to 3-2, in addition to having an Ar substituent specified at a specific position of the L _a ligand, further include a fluorine substitution, and Examples 1-1 and 2-2 without fluorine substitution Compared to , EQE, CE and PE were all slightly improved.

In addition, the metal complexes of Examples 4-1 to 4-6 further include a cyano group substitution in addition to having an Ar substituent specified at a specific position of the L _a ligand, Example 1-1 without a cyano group substitution; All showed more clear improvement compared to 2-1 to 2-3, for example, the driving voltage was clearly reduced, the narrowing of the half maximum width was between 21.7 nm and 26.9 nm, and the maximum emission wavelength λ _max was similar. In , narrowing the half width is advantageous in obtaining more saturated light emission. EQE could all reach a level greater than 24%, in particular 26.35% was reached in Example 4-1.

As can be seen from the above results, in the metal complex comprising a specific Ar substituted L _a ligand at a specific position of the present invention, at least one substituent on the L _a ligand, for example, a substituent such as a fluorine or cyano group substitution By further including have.

In addition, the devices of Examples 5-1 to 5-5 were prepared by using the metal complex 505 of the present invention as a light emitting dopant, mixing it with a first host compound having a different structure and applying it to the light emitting layer of an organic electroluminescent device. and characterization of its performance is carried out.

Device Example 5-1

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 (EML) is 66:28:6.

Device Example 5-2

Except for using Compound H-1 instead of Compound H-91 in the light emitting layer, the embodiment of Device Example 5-2 is the same as Device Example 5-1.

Device Example 5-3

Except for using Compound H-141 instead of Compound H-91 in the light emitting layer, the embodiment of Device Example 5-3 is the same as that of Device Example 5-1.

Device Example 5-4

Except for using Compound H-171 instead of Compound H-91 in the light emitting layer, the embodiment of Device Example 5-4 is the same as Device Example 5-1.

Device Example 5-5

Except for using Compound H-172 instead of Compound H-91 in the light emitting layer, the embodiment of Device Example 5-5 is the same as that of Device Example 5-1.

The detailed device layer structure and thickness are shown in the table below. Here, a layer in which two or more materials are used is obtained by doping different compounds in the weight ratios mentioned therein.

Table 5 Device Structures of Device Examples 5-1 to 5-5

Device ID HIL HTL EBL EML HBL ETL Example 5-1

)compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-91: Metal complex 505
(66:28:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 5-2 Compound HI (100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-1: Metal complex 505
(66:28:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 5-3 compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-141: Metal complex 505
(66:28:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 5-4 compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-171: Metal complex 505
(66:28:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

) Example 5-5 compound HI
(100

) compound HT
(350

) compound X-4
(50

) Compound X-4: Compound H-172: Metal complex 505
(66:28:6) (400

) compound
H-1
(50

) Compound ET: Liq (40:60) (350

)

The new material structures used in the device are 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 under the condition of 1000 cd/m ² were measured. External quantum efficiency (EQE) data, 15mA/cm ² The test was conducted under a constant current condition. These data are recorded and displayed in Table 6.

Table 6 Device Data of Device Examples 5-1 to 5-5

device ID CIE(x, y) λ _max (nm) FWHM (nm) Voltage (V) CE (cd/A) PE (lm/W) EQE (%) Example 5-1 (0.350, 0.625) 530 58.2 3.1 103 103 24.25 Example 5-2 (0.346, 0.629) 530 56.4 3.0 109 116 25.03 Example 5-3 (0.351, 0.624) 531 58.2 3.1 104 106 24.42 Example 5-4 (0.348, 0.627) 530 57.0 3.0 105 110 24.18 Example 5-5 (0.351, 0.624) 530 58.3 3.0 104 110 23.78

As can be seen from the above data, the performances of Examples 5-1 to 5-5 and Example 2-1 are similar, where the EQE is also about 24%, and in particular, the EQE of Example 5-2 is 25.03%. is reached According to the above, the metal complex having a specific Ar-substituted L _a ligand of the present invention can be used as a light emitting material in the light emitting layer of an electroluminescent device. It is explained that device performance can be obtained.

In summary, the metal complex of the present invention including an L _a ligand having an Ar substitution specified at a specific position has better performance in a device compared to the existing metal complex having an Ar substituent at another substitution position among the L _a ligands. In this case, the driving voltage can be lowered, the device efficiency can be improved, in particular, the EQE can be improved, and finally, the overall performance of the device can be significantly improved. The advantages observed from the compounds of the present invention are completely unexpected, and it is impossible for a person skilled in the art to foresee such cases.

It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the present invention. Accordingly, it will be apparent to those skilled in the art that the claimed invention may include modifications of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted for other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims (30)

In the metal complex,
It includes a metal M and a ligand L _a coordinated with the metal M, of which L _a has a structure represented by Formula 1,

In Equation 1,
metal M is selected from metals having a relative atomic mass greater than 40;
Cy, identically or differently at each occurrence, is 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'; when two R′ are present simultaneously, the two R′ are the same or different;
X ₁ to X ₅ are identically or differently selected from CR _X or N whenever they appear;
Ar has a structure represented by Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;
R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;
ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;
R', R _x , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms A cyclic cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted 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, 2 A substituted or unsubstituted alkynyl group having -20 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, 3-20 carbon atoms A substituted or unsubstituted alkylsilyl group having a group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms A substituted or unsubstituted arylgermanyl group having 0 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfide It is selected from the group consisting of a nyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"*" indicates the linkage position of formula 2;
A metal complex in which adjacent substituents R', R _x , R _a1 , R _a2 may be optionally joined to form a ring.
The method of claim 1,
Cy is any one structure selected from the group consisting of the following structures,

;
here,
R, identically or differently, each occurrence represents single substitution, multiple substitution or unsubstituted; When a plurality of R is present in any structure, said R are the same or different;
R is identically or differently each time it appears hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 to 20 carbon atoms A substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1 to 20 carbon atoms A substituted or unsubstituted alkoxy group, 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 group having 2 to 20 carbon atoms an alkynyl 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms , a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms , a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and these groups is selected from the group consisting of a combination of;
Adjacent substituents R may optionally be joined to form a ring;
Here, '#' represents a position connected to the metal M; '

' is a metal complex representing a position connected to X ₁ , X ₂ , X ₃ or X ₄ .
3. The method according to claim 1 or 2,
The metal complex has the general formula M(L _a ) _m (L _b ) _n (L _c ) _q ;
here,
M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, identically or differently each time it appears; Preferably, M is selected from Pt or Ir the same or differently each time it appears;
L _a , L _b and L _c are each a first ligand, a second ligand and a third ligand coordinated with the metal M, and L _c is the same as or different from L _a or L _b ; Among them, L _a , L _b and L _c may be optionally linked to form a multidentate 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, and the sum of m+n+q is equal to the oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L _a are the same or different, when n is equal to 2, two L _b are the same or different; when q is equal to 2, two L _c are the same or different;
L _a is selected from the group consisting of the following structures identically or differently each time it appears,

;
X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R′ are present simultaneously, the two R′ 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 , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;
"*" indicates the linkage position of formula 2;
R, R _x , R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;
L _b and L _c are the same or different each time they appear is a structure represented by any one selected from the group consisting of,

,

,

,

,

,

,

,

,

,

,

,

;
here,
X _b , identically or differently each time it appears, is selected from the group consisting of O, S, Se, NR _N1 and CR _C1 R _C2 ;
R _a and R _b , identically or differently each time they appear, represent mono-, poly- or unsubstituted;
R, R', R _x , R _a , R _b , R _c , R _N1 , R _C1 , R _C2 , R _a1 and R _a2 the same or differently each time they appear hydrogen, deuterium, halogen, 1 to 20 carbon sources A substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 3 to 20 ring atoms, or an unsubstituted heterocyclic group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms aryloxy group, 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, 3 A substituted or unsubstituted heteroaryl group having ~30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms (arylsilyl group), a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted group having 0 to 20 carbon atoms selected from the group consisting of an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, R′, R _x , R _a1 and R _a2 may optionally be joined to form a ring;
A metal complex in which adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 may optionally be joined to form a ring.
The method of claim 1,
The metal complex Ir(L _a ) _m (L _b ) _3-m has a structure represented by Formula 3,

here,
X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R'; when two R′ are present simultaneously, the two R′ are the same or different;
m is selected from 1, 2 or 3; when m is selected from 1, two L _b are the same or different; when m is selected from 2 or 3, a plurality of L _a are the same or different;
Y ₁ - Y ₄ are identically or differently selected from CR _y or N whenever they appear;
X ₁ to X ₅ are identically or differently selected from CR _x or N whenever they appear;
Ar has a structure represented by Formula 2,

a is selected from 0, 1, 2, 3, 4 or 5;
R _a1 and R _a2 identically or differently each time they appear represent monosubstituted, polysubstituted or unsubstituted;
ring Ar ₁ and ring Ar ₂ , identically or differently each time they appear, 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; the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8;
R', R _x , R _y , R ₁ -R ₈ , R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to A substituted or unsubstituted cycloalkyl group having 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, 7 to 30 A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, 2 to 20 carbon atoms A substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 3 to 30 carbon atoms A heteroaryl group, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, 3 to 20 carbon atoms A substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group , an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"*" indicates the linkage position of formula 2;
adjacent substituents R′, R _x , R _y , R _a1 , R _a2 may optionally be joined to form a ring;
A metal complex in which adjacent substituents R ₁ to R ₈ may be optionally connected to form a ring.
5. The method of claim 1 or 4,
X ₁ -X ₅ are identically or differently selected from CR _x each time they appear, and/or Y ₁ -Y ₄ are identically or differently selected from CR _y each time they appear.
5. The method of claim 1 or 4,
A metal complex wherein at least one of X ₁ to X ₅ is N, and/or at least one of Y ₁ to Y ₄ is N.
7. The method according to any one of claims 1 to 6,
X is selected from O or S; a is selected from 0, 1, 2 or 3, preferably a is 1;
8. The method according to any one of claims 1 to 7,
R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 7 A substituted or unsubstituted aralkyl group having -30 carbon atoms, a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, 3-20 carbon atoms It is selected from the group consisting of a substituted or unsubstituted alkylsilyl group having a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof;
Preferably, R _a1 and R _a2 are identically or differently each time they appear hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms, 6 A substituted or unsubstituted aryl group having ~18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 15 carbon atoms, and combinations thereof is selected from the group consisting of;
More preferably, R _a1 and R _a2 are identically or differently each time they appear 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, A metal complex selected from the group consisting of a deuterated cyclopentyl group, a deuterated cyclohexyl group, a phenyl group, a pyridine group, a trimethylsilyl group, and combinations thereof.
9. The method according to any one of claims 1 to 8,
In Ar, ring Ar ₁ and ring Ar ₂ are identically or differently each occurrence 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 total number of ring atoms of ring Ar ₁ and ring Ar ₂ is greater than or equal to 8 and less than or equal to 30;
Preferably, in Ar, ring Ar ₁ and ring Ar ₂ each appear identically or differently each time a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a triazine ring, a phenanthrene ring, an anthracene ring, a silafluorene ring, Quinoline ring, isoquinoline ring, benzofuran ring, fused dithiophene ring, fused difuran ring, benzothiophene ring, indene ring, dibenzofuran ring, dibenzothiophene ring, triphenylene ring, carbazole ring , an azacarbazole ring, an azadibenzofuran ring, an azadibenzothiophene ring, an azasilafluorene ring, and combinations thereof; A metal complex in which the total number of ring atoms of the ring Ar ₁ and the ring Ar ₂ is greater than or equal to 8 and less than or equal to 30.
9. The method according to any one of claims 1 to 8,
In Ar, ring Ar ₁ and ring Ar ₂ are identically or differently each occurrence selected from an aromatic ring having 6 ring atoms, a heteroaromatic ring having 5 or 6 ring atoms, or a combination thereof;
Preferably, ring Ar ₁ and ring Ar ₂ are identically or differently at each occurrence selected from aromatic rings or heteroaromatic rings having 6 ring atoms;
More preferably, ring Ar ₁ and ring Ar ₂ are identically or differently at each occurrence selected from aromatic rings having 6 ring atoms.
9. The method according to any one of claims 1 to 8,
Ar is selected from the group consisting of the same or different structure whenever it appears,

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, and combinations thereof;
optionally, said group is partially or fully substituted by deuterium; Here, "*" is a metal complex indicating the connection position of Ar.
12. The method according to any one of claims 1 to 11,
R _x is identically or differently each time it appears hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 6 A substituted or unsubstituted aryl group having ~30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a cyano group, and selected from the group consisting of combinations thereof;
Preferably, at least one of R _x is deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, 6 to 12 carbon atoms From the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof is selected;
More preferably, at least one of R _x is deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a cyano group, and combinations thereof A metal complex selected from the group consisting of.
13. The method according to any one of claims 1 to 12,
at least one of X ₁ -X ₅ is selected from CR _x , wherein R _x is a cyano group or fluorine;
Preferably, at least one of X ₃ to X ₅ is selected from CR _x and R _x is a cyano group or fluorine;
More preferably, X ₅ is CR _x , wherein R _x is a cyano group or fluorine.
5. The method of claim 4,
R _y is identically or differently each time it appears hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 7 to 30 A substituted or unsubstituted aralkyl group having 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 substitution having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof;
Preferably, at least one R _y is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 6 to 30 carbon atoms A metal complex selected from the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.
5. The method of claim 4,
At least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted having 3 to 20 ring carbon atoms or an unsubstituted 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 combinations thereof;
Preferably, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 ring carbon atoms is selected from the group consisting of a substituted or unsubstituted cycloalkyl group having a group, and combinations thereof;
More preferably, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group , a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a neopentyl group, a tert-pentyl group, and a combination thereof; Optionally, hydrogen in said group is partially or fully substituted by deuterium.
The method of claim 1,
L _a is identically or differently each time it appears is a metal complex selected from the group consisting of:

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17. The method of claim 3 or 16,
L _b is the same or different each time it appears a metal complex selected from the group consisting of:

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18. The method of claim 3 or 17,
L _c is identically or differently each time it appears a metal complex selected from the group consisting of:

. 19. The method of claim 18,
The metal complex has the structure Ir(L _a ) ₂ (L _b ) or Ir(L _a )(L _b ) ₂ or Ir(L _a ) ₃ , wherein L _a is the same or different each time it appears L _a1 to L _a1177 is selected from any one, any two, or any three kinds, L _b is selected from any one or any two kinds 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 , of which L _a is the same or different each time it appears L _a1 to L ₁₁₇₇ is selected from any one or any two of the group consisting of, and L _c is selected from any one or any two of the group consisting of L _c1 to L _c360 ;
Alternatively, the metal complex has a structure of Ir(L _a )(L _b )(L _c ), of which L _a is the same or different each time it appears, any one of the group consisting of L _a1 to L ₁₁₇₇ . is selected from, L _b is selected from any one of the group consisting of L _b1 to L _b128 , L _c is selected from any one of the group consisting of L _c1 to L _c360 ;
Preferably, wherein the metal complex is selected from the group consisting of metal complex 1 to metal complex 1008, of which metal complex 1 to metal complex 1008 has a structure of IrL _a (L _b ) ₂ , wherein two L _b are the same, wherein L _a and L _b are each metal complex corresponding to the structure shown in the table below:

anode;
cathode, and
An electroluminescent device comprising an organic layer disposed between an anode and a cathode, wherein the organic layer comprises the metal complex according to any one of claims 1 to 19.
21. The method of claim 20,
The organic layer including the metal complex is a light emitting layer.
21. The method of claim 20,
The electroluminescent device is an electroluminescent device that emits green light or white light.
22. The method of claim 21,
the light emitting layer includes a first host compound;
Preferably, the light emitting layer further comprises a second host compound;
More preferably, the first host compound and/or the second host compound is a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a carbazole group, an azacarbazole group, an indolocarbazole group, a dibenzothiophene group, azadibenzo Thiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenylene group, fluorene group, silafluorene group, naphthyl group, quinoline group, isoquinoline group, quina An electroluminescent device comprising at least one chemical group selected from the group consisting of a sleepy group, a quinoxaline group, a phenanthrene group, an azaphenanthrene group, and combinations thereof.
24. The method of claim 23,
The first host compound has a structure represented by Formula 4,

here,
E ₁ -E ₆ are identically or differently selected from C, CR _e or N whenever they appear, at least two of E ₁ -E ₆ are N, at least one of E ₁ -E ₆ is C, formula A is connected with;

;
here,
Q is, identically or differently, each occurrence selected from the group consisting of O, S, Se, N, NR", CR"R", SiR"R", GeR"R" and R"C=CR"; two When R″ is present simultaneously, the two R″ can be the same or different;
P is 0 or 1, r is 0 or 1;
when Q is selected from N, p is 0 and r is 1;
when 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 and r is 0;
L is, identically or differently, 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 cycloalkylene group having 6 to 20 carbon atoms a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Q ₁ -Q ₈ are identically or differently selected from C, CR _q or N at each occurrence;
R _e , R″ and R _q are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms an alkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, 2 to 20 carbon atoms A substituted or unsubstituted alkynyl group having 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 substitution having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 A substituted or unsubstituted arylgermanyl group having ~20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group , is selected from the group consisting of a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"*" indicates the connection position of formula A and formula 4;
Adjacent substituents R _e , R″, R _q may be optionally connected to form a ring.
25. The method of claim 24,
E ₁ -E ₆ are identically or differently selected from C, CR _e or N whenever they appear, three of E ₁ -E ₆ are N, at least one of E ₁ -E ₆ is CR _e , wherein R _e is, identically or differently, each occurrence selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof;
and/or Q is selected from O, S, N or NR″, identically or differently each time it appears;
and/or at least one or at least two of Q ₁ -Q ₈ are selected from CR _q , wherein R _q is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted having 5 to 30 carbon atoms or an unsubstituted heteroaryl group, or a combination thereof;
and/or L is, identically or differently, each occurrence 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 a combination thereof An electroluminescent device selected from.
25. The method of claim 24,
The first host compound is an electroluminescent device selected from the group consisting of:

24. The method of claim 23,
The second host compound has a structure represented by Formula 5,

here,
L _x , identically or differently each time it appears, represents 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, 6 to 20 carbon atoms; a substituted or unsubstituted arylene group having 3 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, identically or differently each time it appears; at least one of V is C and is connected with L _x ;
U is identically or differently each time it appears is selected from C, CR _u or N, at least one of U is C and is linked to L _x ;
R _v and R _u are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 A substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, 1~20 A substituted or unsubstituted alkoxy group having 6 to 30 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 A substituted or unsubstituted alkynyl 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, a substituted or unsubstituted group having 3 to 20 carbon atoms an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted group having 6 to 20 carbon atoms Arylgermanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphonyl group selected from the group consisting of pino group and combinations thereof;
Ar ₆ is identically or differently each time it appears 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 optionally be joined to form a ring;
Preferably, the second host compound is an electroluminescent device having a structure represented by one of Formulas 5-a to 5-j:

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28. The method of claim 27,
The second host compound is an electroluminescent device selected from the group consisting of:

24. The method of claim 23,
a metal complex is doped into the first host compound and the second host compound, and the weight of the metal complex accounts for 1%-30% of the total weight of the light emitting layer;
Preferably, the weight of the metal complex accounts for 3% to 13% of the total weight of the light emitting layer.
20. A compound combination comprising a metal complex according to any one of claims 1 to 19.

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