KR20210154904A - Organic electroluminescent device - Google Patents

Abstract

Disclosed is an organic electroluminescent device. The organic electroluminescent device comprises: a positive electrode; a negative electrode; and an organic layer disposed between the positive electrode and the negative electrode. The organic layer contains at least a first metal complex having a ligand structure of a formula 1 and a first host compound having a structure of a formula 2. The organic electroluminescent device of the present invention has clearly improved device performance such as device lifetime. An electronic device comprising the organic electroluminescent device is further disclosed.

Description

Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT DEVICE}

The present invention relates to an organic electroluminescent device. In particular, it relates to an organic electroluminescent device containing a metal complex having a ligand of the structure of Formula 1 and a first host compound having a structure of Formula 2, and an electronic device including the organic electroluminescent device.

Organic electronic devices are 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 multiple 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 emitting 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 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 from the triplet state to the singlet 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 high molecular weight. 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 changed into a high molecular OLED.

Various OLED manufacturing methods already exist. Small molecule OLEDs are typically prepared through vacuum thermal evaporation. Polymeric 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. An 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.

로 표시된 제1 호스트,

로 표시된 제2 호스트를 함유한다. 비록, 해당 출원은 일부 인광 도판트를 예를 들었으나, 해당 출원은 시아노기-치환된 융합고리계 (헤테로)아릴기 구조 리간드를 함유하는 착물을 이러한 호스트 재료에 도핑하는 응용에 대해 주목하지 않았으며, 또한 시아노기-치환된 융합고리계 (헤테로)아릴피리딘 구조를 갖는 착물이 이러한 호스트 재료에 도핑된 소자가 더 우수한 성능을 획득할 수 있음을 개시 및 교시하지 않았다.US20200127213A1 discloses an organic optoelectronic device, the light emitting layer of which is

a first host marked with

contains a second host denoted by Although this application cites some phosphorescent dopants as examples, this application does not focus on the application of doping complexes containing cyano group-substituted fused-ring system (hetero)aryl group structural ligands to such host materials. In addition, it was not disclosed and taught that a device doped with a cyano group-substituted fused-ring system (hetero)arylpyridine structure of a complex having a structure of such a host material can obtain better performance.

로 표시된 제1 호스트,

의 결합으로 형성된 제2 호스트 및

로 표시된 인광 도판트를 함유한다. 그러나, 해당 출원은 시아노기-치환된 융합고리계 (헤테로)아릴기 구조 리간드를 함유하는 착물을 이러한 호스트 재료에 도핑하는 응용에 대해 주목하지 않았으며, 또한 소자에서의 비카바졸(Bicarbazol) 골격을 구비한 화합물의 응용에 대해 주목하지 않았으며, 또한 시아노기-치환된 융합고리계 (헤테로)아릴기 구조 리간드를 갖는 착물이 이러한 호스트 재료에 도핑된 소자가 더 우수한 성능을 획득할 수 있음을 개시 및 교시하지 않았다. WO2019017618A1 discloses an organic optoelectronic device, the light emitting layer of which is

a first host marked with

a second host formed by the combination of

It contains a phosphorescent dopant indicated by . However, the application did not pay attention to the application of doping a complex containing a cyano group-substituted fused-ring system (hetero)aryl group structural ligand to such a host material, and also the Bicarbazol skeleton in the device. No attention was paid to the application of the compound having not initiated and taught.

또는

구조를 갖는 화합물, 및 상기 화합물을 함유하는 전계발광소자를 개시하였고, 해당 유기 전계발광소자는 인광 도판트를 더 함유하지만, 해당 출원은 실시예에서 인광 도판트로서 페닐 피리딘 Ir 및 Pt 착물만 언급하였다. 그러나, 해당 출원은 시아노기-치환된 융합고리계 (헤테로)아릴기 구조 리간드를 함유하는 착물을 이러한 호스트 재료에 도핑하는 응용에 대해 주목하지 않았으며, 또한 시아노기-치환된 융합고리계 (헤테로)아릴기 구조 리간드를 갖는 착물이 이러한 호스트 재료에 도핑된 소자가 더 우수한 성능을 획득할 수 있음을 개시 및 교시하지 않았다. In US20170186965A1

or

Disclosed is a compound having a structure, and an electroluminescent device containing the compound, and the organic electroluminescent device further contains a phosphorescent dopant, but this application mentions only phenylpyridine Ir and Pt complexes as phosphorescent dopants in Examples did However, this application did not pay attention to the application of doping a complex containing a cyano group-substituted fused-ring system (hetero)aryl group structural ligand to such a host material, and also a cyano group-substituted fused-ring system (hetero) group ) did not disclose and teach that devices in which complexes with aryl group structural ligands are doped into such host materials can achieve better performance.

구조를 갖는 화합물, 상기 화합물을 함유하는 전계발광소자를 개시하였고, 해당 유기 전계발광소자는 도판트를 더 함유하지만, 해당 출원은 실시예에서 발광 도판트로서 페닐 피리딘계 Ir 착물만 언급하였다. 해당 출원은 시아노기를 구비한 융합고리계 (헤테로)아릴기 구조 리간드를 갖는 착물이 이러한 호스트 재료에 응용 시 소자가 더 우수한 성능을 획득할 수 있음을 주목하지 않았다.In US20150340618A1

Disclosed is a compound having a structure, an electroluminescent device containing the compound, and the organic electroluminescent device further contains a dopant, but this application only mentions a phenylpyridine-based Ir complex as a light emitting dopant in Examples. The application did not note that a complex having a fused-ring system (hetero)aryl group structural ligand having a cyano group may obtain better performance for a device when applied to such a host material.

Through in-depth research, the present inventors have found that an organic electroluminescent device using a metal complex dopant material having a ligand of Formula 1 structure and a first host compound having a specific structure can clearly improve the overall performance of the organic electroluminescent device. found that it can.

An object of the present invention is to provide a series of organic electroluminescent devices containing a metal complex-based dopant material having a structure of Formula 1 and a first host compound having a structure of Formula 2 in order to solve at least a part of the above problems do it with

According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which comprises:

anode;

cathode; and

an organic layer disposed between the anode and the cathode; wherein the organic layer contains at least a first metal complex and a first host compound;

Here, the first metal complex contains a metal M and a ligand L _a coordinated to the metal M and the ligand L _a has a structure represented by Formula 1,

here,

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

Cy is selected from a substituted or unsubstituted aryl group having 5 to 24 ring atoms or a substituted or unsubstituted heteroaryl group having 5 to 24 ring atoms, identically or differently each time it appears, wherein Cy is a metal- connected to the metal M through a carbon bond or a metal-nitrogen bond;

Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;

X ₁ to X ₈ are identically or differently selected from C, CR _x or N _{whenever they appear, and at least one of X 1} to X ₄ is C and is linked to Cy;

X ₁ , X _{2 ,} X ₃ or X ₄ is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;

R _x and R ₁ 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

at least one of X ₁ to X _{8 is selected from CR x} and R _x is a cyano group;

adjacent substituents R ₁ , R _x may optionally be joined to form a ring;

Here, the first host compound has a structure represented by Formula 2,

here,

E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E at least two of ₆ is equal to N, and at least one of E ₁ ~ E ₆ is C and formula A, formula linked to at least one of B, Formula C, or Formula D;

where, in formula A, formula B, formula C and formula D,

A ₁ and A ₂ , identically or differently each time they appear, are selected from the group consisting of _{O, S, Se, NR n} , CR _n R _n and SiR _n R _{n ;} when two R _n are present simultaneously, the two R _n may be the same or different;

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;

W ₁ and W ₈ are identically or differently selected from CR _w1 or N whenever they appear;

W ₂ to W ₇ are identically or differently selected from CR _w2 or N whenever they appear;

Z ₁ to Z ₈ are identically or differently selected from C, CR _z or N _{whenever they appear, and at least one of Z 1} to Z ₈ is C and is connected to L;

Y ₁ to Y ₁₅ are identically or differently selected from C, CR _{y or N whenever they appear, wherein at least one of Y 1} to Y ₈ in formula C is C and is connected to L; In formula D, _{at least one of Y 1} to Y ₇ is C and at least one of Y ₈ to Y ₁₁ is C, all of which are connected to L;

R _w1 is identically or differently each time it appears is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms ( 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 aral group having 7 to 30 carbon atoms a alkyl 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, 6 to 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, 6 a substituted or unsubstituted arylsilyl group having ˜20 carbon atoms and combinations thereof;

R _z and R _w2 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

R _e , R _n and R _y 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, 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 aryloxy group having 2 to 20 carbon atoms, or unsubstituted alkenyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms A silyl group, a substituted or unsubstituted arylsilyl 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 connection position of formula A, formula B, formula C or formula D and formula 2;

Adjacent substituents R _e , R _n , R _w2 , R _y , R _z may optionally be joined to form a ring.

According to another embodiment of the present invention, an electronic device is further disclosed, which includes the organic electroluminescent device according to the embodiment.

An organic electroluminescent device containing a metal complex dopant material having a ligand of the structure of Formula 1 and a first host compound having a structure of Formula 2 disclosed in the present invention, a special combination of the host compound and the dopant compound is selected By doing so, an energy level matching suitable for the material of the light emitting layer can be obtained, and the concentration of carriers in the light emitting layer can be effectively adjusted to reach a desired balance, and the performance of the organic electroluminescent device such as improvement of device lifespan compared to the prior art is clearly improved did

1 is a schematic diagram of an organic electroluminescent device disclosed by the text;
2 is a schematic diagram of another organic electroluminescent device disclosed by the 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 Patent US7279704B2 columns 6-10, the entire contents of which are incorporated herein by reference.

Each layer in this layer has more examples. For example, the flexible and transparent substrate-anode combination disclosed in U.S. Patent No. 5844363, 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. United States 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 2003/0230980, which is incorporated by way of 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 may 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 illustrated 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, Smartphones, tablets, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3D displays, vehicle displays and tail lights.

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 non-radiative attenuation due to triplet states, the ratio of back-filled singlet excited states can reach 75%. . The total proportion of singlet states can be 100%, which is well over 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 (ΔE _{ST ).} An organic art object-acceptor luminescent material containing a non-metal has the potential to realize these characteristics. Emissions of these substances are commonly labeled as art-receptor-acceptor charge-transfer (CT)-type emission. Spatial separation of HOMO and LUMO in these co-receptor-type compounds generally produces small ΔE _ST . Such conditions may include CT conditions. In general, an electron acceptor moiety (for example, an amino group or a carbazole derivative) and an electron acceptor moiety (for example, a 6-membered aromatic ring containing N) are formed by connecting an electron-acceptor luminescent material.

Regarding the definition of the term substituent,

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

Alkyl groups as used herein include straight-chain alkyl groups and branched alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, 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. Also, the alkyl group may be optionally substituted. 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, and is preferably a cycloalkyl group having 4 to 10 ring 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.

A heteroalkyl group, as used herein, 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 a plurality of carbons in the chain of the alkyl group contained in the heteroalkyl group It is formed by substitution with a heteroatom. 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, a hydroxymethyl group , hydroxyethyl group, hydroxypropyl group, mercaptomethyl group, mercaptoethyl group, mercaptopropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group group, t-butyldimethylsilyl group, triethylsilyl group, triisopropylsilyl group, trimethylsilylmethyl group, trimethylsilylethyl group, trimethylsilylisopropyl 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, cyclo pentadienyl group, cyclohexenyl group, cycloheptenyl group, cycloheptatrienyl group, cyclooctenyl group, cyclooctatetraenyl group group) and a norbornenyl group. Also, the alkenyl group may be optionally substituted.

Alkynyl groups as used herein include straight-chain alkynyl groups. The alkynyl group is an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 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 include 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 naphthalene group, an anthracene group, a phenalene group, a phenanthrene group, a fluorene group, a pyrene group ( Pyrene), a chrysene group, a perylene group, and an azulene group, preferably a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a fluorene group, and a naphthalene group do. Also, the aryl group may be optionally substituted. 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, includes non-aromatic cyclic groups. Non-aromatic heterocyclic groups contain saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms. Here, at least one ring 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, and a preferred non-aromatic heterocyclic group contains 3 to 7 ring atoms. It contains at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. 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, the 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 are dibenzothiophene group, dibenzofuran group, dibenzoselenophene group, furan group, thiophene group, benzofuran group, benzothiophene group, benzo Selenophene group, carbazole group, indolocarbazole group, pyridine indole group, pyrrolopyridine group, pyrazole group, imidazole group , triazole group, oxazole group, thiazole group, oxadiazole group, oxatriazole group, dioxazole group, thiadiazole group, pyridine group, pyridazine group, pyrimidine group, pyrazine A pyrazine group, a triazine group, an oxazine group, an oxathiazine group, an oxadiazine group, an indole group, a benzimidazole group ), indazole group, indeoxazine group, benzooxazole group, benzisoxazole group, benzothiazole group, quinoline group, isoquinoline group, cinnoline group, quina Zoline group, quinoxaline group, naphthyridine group, phthalazine group, pteridine group, xanthene group, acridine group, phenazine group, phenothiazine group, benzofuranopyridine group (Benzofuranopyridine group), furanodipyridine group (Furanodipyridine group), benzothienopyridine group, thienodipyridine group, benzoselenophenopyridine group (benzose) lenophenopyridine group), including a selenophenodipyridine group, preferably a dibenzothiophene group, a dibenzofuran group, a dibenzoselenophene group, a carbazole group, an indolocarbazole group, an imidazole group, A pyridine group, a triazine group, a benzimidazole group, a 1,2-azaborane group, a 1,3-azaborane group, a 1,4-azaborane group, a borazine group, and aza analogs thereof. Also, the heteroaryl group may be optionally substituted.

Alkoxy group-, as used herein, is represented by an -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group or -O-heterocyclic group. Examples and preferred examples of the alkyl group, 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, tetrahydrofuranox a tetrahydrofuranoxy group, a tetrahydropyranoxy group, a methoxypropyloxy group, an ethoxyethyloxy group, a methoxymethyloxy group and an ethoxymethyloxy group. Also, the alkoxy group may be optionally substituted.

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 aryl substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of 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-α-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.

Alkylsilyl group includes silyl groups substituted with alkyl as used herein. 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 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 alkylsilyl 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. Also, the arylsilyl group may be optionally substituted.

The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic fragment are replaced by 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 amino group, substituted acyl group, substituted carbonyl group, substituted carboxylic acid group, substituted When any one term from the group consisting of an ester group, a substituted sulfinyl group, a substituted sulfonyl group, and a substituted phosphino group is used, it is an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, an aralkyl group, an alkoxy group group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, amino group, acyl group, carbonyl group, carboxylic acid group, ester group, sulfinyl group, sulfonyl group and phosphino group Any one group is deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 to An unsubstituted heteroalkyl group having 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted group having 1 to 20 carbon atoms substituted alkoxy group, unsubstituted aryloxy group having 6 to 30 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, unsubstituted alkynyl group having 2 to 20 carbon atoms, 6 to 30 carbon atoms an unsubstituted aryl group having a group, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted alkylsilyl group having 6 to 20 carbon atoms An arylsilyl group, an 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 mercapto group , sulfinyl group , means that it may be substituted by one or a plurality of sulfonyl groups, phosphino groups, and combinations thereof.

It is to be understood that when a molecular fragment is described with a substituent or linked to other moieties in other forms, whether 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, naphthalene group (naphthalene group, dibenzofuran group) is named according to whether. As used herein, these different ways of designating a substituent or 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 referred to 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.) Substituents present at a plurality of available substitution positions may be of the same structure or of different structures.

In the compounds mentioned in the present invention, for example, adjacent substituents in the compounds cannot be optionally joined to form a ring, unless it is expressly defined that adjacent substituents can be optionally joined to form a ring. In the compounds mentioned in the present invention, that adjacent substituents may be optionally connected 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, an alicyclic ring, a heteroalicyclic ring, an aromatic ring or a heteroaromatic ring. In these expressions, 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 intention 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 exemplified by the formula :

The intention of the expression 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:

In addition, the intention of the expression that adjacent substituents may be optionally connected to form a ring is also intended to mean that when one of the two substituents bonded to a carbon atom directly bonded to each other represents hydrogen, the second substituent is on the side at which the hydrogen atom is bonded It is intended to be considered to have joined to form a ring. This is exemplified through the formula:

According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which comprises:

anode;

cathode; and

an organic layer disposed between the anode and the cathode; wherein the organic layer contains at least a first metal complex and a first host compound;

Here, the first metal complex contains a metal M and a ligand L _a coordinated to the metal M and the ligand L _a has a structure represented by Formula 1,

here,

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

Cy is selected from a substituted or unsubstituted aryl group having 5 to 24 ring atoms or a substituted or unsubstituted heteroaryl group having 5 to 24 ring atoms, identically or differently each time it appears, wherein Cy is a metal- connected to the metal M through a carbon bond or a metal-nitrogen bond;

Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;

X ₁ to X ₈ are identically or differently selected from C, CR _x or N _{whenever they appear, and at least one of X 1} to X ₄ is C and is linked to Cy;

X ₁ , X _{2 ,} X ₃ or X ₄ is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;

R _x and R ₁ 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

at least one of X ₁ to X _{8 is selected from CR x} and R _x is a cyano group;

adjacent substituents R ₁ , R _x may optionally be joined to form a ring;

Here, the first host compound has a structure represented by Formula 2,

here,

E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E at least two of ₆ is equal to N, and at least one of E ₁ ~ E ₆ is C and formula A, formula linked to at least one of B, Formula C, or Formula D;

where, in formula A, formula B, formula C and formula D,

A ₁ and A ₂ , identically or differently each time they appear, are selected from the group consisting of _{O, S, Se, NR n} , CR _n R _n and SiR _n R _{n ;} when two R _n are present simultaneously, the two R _n may be the same or different;

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;

W ₁ and W ₈ are identically or differently selected from CR _w1 or N whenever they appear;

W ₂ to W ₇ are identically or differently selected from CR _w2 or N whenever they appear;

Z ₁ to Z ₈ are identically or differently selected from C, CR _z or N _{whenever they appear, and at least one of Z 1} to Z ₈ is C and is connected to L;

Y ₁ to Y ₁₅ are identically or differently selected from C, CR _{y or N whenever they appear, wherein at least one of Y 1} to Y ₈ in formula C is C and is connected to L; In formula D, _{at least one of Y 1} to Y ₇ is C and at least one of Y ₈ to Y ₁₁ is C, all of which are connected to L;

R _w1 is identically or differently each time it appears is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms ( 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 aral group having 7 to 30 carbon atoms a alkyl 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, 6 to 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, 6 a substituted or unsubstituted arylsilyl group having ˜20 carbon atoms and combinations thereof;

R _z and R _w2 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

R _e , R _n and R _y 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, 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 aryloxy group having 2 to 20 carbon atoms, or unsubstituted alkenyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms A silyl group, a substituted or unsubstituted arylsilyl 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 connection position of formula A, formula B, formula C or formula D and formula 2;

Adjacent substituents R _e , R _n , R _w2 , R _y , R _z may optionally be joined to form a ring.

In the embodiment, "adjacent substituents R ₁ , R _x may be optionally connected to form a ring" includes any one or a plurality of cases below. Adjacent substituents R _x may be joined to form a ring and adjacent substituents R ₁ may be joined to form a ring. In addition, adjacent substituents R ₁ and R _x may be connected to form a ring. In other cases, adjacent substituents R ₁ , R _x are not connected to each other to form a ring.

In the embodiment, "adjacent substituents R _e , R _n , R _w2 , R _y , R _z may be optionally connected to form a ring" includes any one or a plurality of cases below. Adjacent substituents R _e may be joined to form a ring, adjacent substituents R _n may be joined to form a ring, adjacent substituents R _w2 may be joined to form a ring and adjacent substituents R _y may be joined to form a ring and adjacent substituents R _z may be linked to form a ring. In addition, adjacent substituents R _n and R _y may be connected to form a ring, adjacent substituents R _e and R _y may be connected to form a ring, and adjacent substituents R _e and R _w2 may be connected to form a ring, and Adjacent substituents R _e and R _z may be connected to form a ring, and adjacent substituents R _n and R _z may be connected to form a ring. In other cases, adjacent substituents R _e , R _n , R _w2 , R _y , and R _z are not all connected to form a ring.

를 얻으며; 예를 들어 E₁ 및 E₃이 C인 경우, 각각 2개의 식 B와 연결되고 그중 하나의 식 B의 A₁은 NR_n에서 선택되며, 식 2b와 같은 구조

를 얻는다.In the embodiment, " _{at least one of E 1} to E ₆ is C and is connected to at least one of Formula A, Formula B, Formula C, or Formula D" includes one or more of the following cases. when at least one of E ₁ to E ₆ is C, that one C may be linked to any one of Formula A, Formula B, Formula C, or Formula D; If _{at least two of E 1} to E ₆ are C, then those two Cs may each be linked to any two of formula A, formula B, formula C, or formula D (including structures of two identical formulas and for each associated with two Equations B). For example, when at least E ₁ and E ₃ are C, they are linked with formulas A and B, respectively, so that they have a structure such as formula 2c

to get; For example, when E ₁ and E ₃ are C, each is linked to two formulas B and A ₁ of one of them is selected from NR _n , and has the same structure as formula 2b

to get

According to one embodiment of the invention, E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E ₆ 3 than N of an E ₁ ~ E ₆ at least one of is CR _e and 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, or a combination thereof selected from the group consisting of

According to one embodiment of the invention, E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E ₆ 3 than N of an E ₁ ~ E ₆ at least one of is C or CR _e ; when at least one or two of E ₁ to E ₆ is C, they are each independently linked to Formula A, Formula B, Formula C, or Formula D; When at least one of _{E 1} to E _{6 is CR e} , _{each time R e} is the same or different, each occurrence is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted It is selected from a carbazole group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a combination thereof.

According to one embodiment of the invention, E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E and ₆₃ than N of E ₁ ~ E ₆ of at least 2 dog is C and each is independently linked to Formula A, Formula B, Formula C, or Formula D.

를 얻는다. 예를 들어 E₁ 및 E₃이 C인 경우, 각각 2개의 식 B와 연결되고 그중 하나의 식 B의 A₁은 NR_n에서 선택되며, 식 2b와 같은 구조

를 얻는다.In the present invention, " _{at least two of E 1} to E ₆ are C and are each independently connected to Formula A, Formula B, Formula C or Formula D" means that at least two of _{E 1} to E _{6 are selected as C} where the two C's can each be linked (comprising two identical structures of the formula and e.g. each linked to two formula B's) with any two of formula A, formula B, formula C, or formula D. meaning to indicate For example, when E ₁ and E ₃ are C, they are linked with formulas A and B, respectively, so that they have the same structure as formula 2c

to get For example, when E ₁ and E ₃ are C, each is linked to two formulas B and A ₁ of one of them is selected from NR _n , and has the same structure as formula 2b

to get

According to an embodiment of the present invention, W ₁ and W ₈ are identically or differently selected from _{CR w1 whenever they appear;} W ₂ to W ₇ are identically or differently selected from _{CR w2 whenever they appear;} Z ₁ to Z ₈ are identically or differently selected from C or CR _z whenever they appear; Y ₁ to Y ₁₅ are identically or differently selected from C or CR _y whenever they appear;

Adjacent substituents R _w2 , R _z , R _y may optionally be joined to form a ring.

In the embodiment, "adjacent substituents R _w2 , R _z , R _y may be optionally connected to form a ring" includes any one or a plurality of cases below. Adjacent substituents R _y may be joined to form a ring, adjacent substituents R _w2 may be joined to form a ring, and adjacent substituents R _z may be joined to form a ring. In another case, adjacent substituents R _w2 , R _z , and R _y are not all connected to form a ring.

According to an embodiment of the present invention, _{at least one of R w1} , R _w2 , and R _y is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. 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, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms It is selected from a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a hydroxyl group, and combinations thereof.

According to an embodiment of the present invention, _{at least two of R w1} , R _w2 , R _y is 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 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 3 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 a substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a hydroxyl group, and combinations thereof.

According to an embodiment of the present invention, _{at least one of R w1} , R _w2 , and R _y is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted hetero group having 3 to 30 carbon atoms aryl groups and combinations thereof.

According to an embodiment of the present invention, _{at least two of R w1} , R _w2 , and R _y are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 3 to 30 carbon atoms heteroaryl groups and combinations thereof.

According to an embodiment of the present invention, _{at least one of R z} is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present invention, the first host compound has a structure represented by one of Formulas 2a to 2f,

where in Equation 2a to Equation 2f,

A ₁ , A ₂ are identically or differently each time they appear are selected from the group consisting of _{O, S, Se, NR n} , CR _n R _n and SiR _n R _{n ;} when two R _n are present simultaneously, the two R _n may be the same or different;

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;

Ar is, identically or differently, each occurrence 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;

W ₁ and W ₈ are identically or differently selected from CR _w1 or N whenever they appear;

W ₂ to W ₇ are identically or differently selected from CR _w2 or N whenever they appear;

Z ₁ to Z ₈ are identically or differently selected from C, CR _z or N _{whenever they appear, and at least one of Z 1} to Z ₈ is C and is connected to L;

Y ₁ to Y ₁₅ are identically or differently selected from C, CR _{y or N whenever they appear, wherein at least one of Y 1} to Y ₈ in formula C is C and is connected to L; In formula D, _{at least one of Y 1} to Y ₇ is C and at least one of Y ₈ to Y ₁₁ is C, all of which are connected to L;

R _w1 is identically or differently each time it appears is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms ( 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 aral group having 7 to 30 carbon atoms a alkyl 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, 6 to 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, 6 a substituted or unsubstituted arylsilyl group having ˜20 carbon atoms and combinations thereof;

R _z and R _w2 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

R _n and R _y are identically or differently each time they appear hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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 _n , R _y may optionally be joined to form a ring.

According to an embodiment of the present invention, L is identically or differently each time it appears, a single bond, a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 6 carbon atoms It is selected from a lene group, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof.

According to an embodiment of the present invention, L is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted carbazolylidene group, identically or differently each time it appears. ), a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene 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, Ar each time it appears, identically or differently, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or these is selected from a combination of

According to an embodiment of the present invention, Ar each time it appears, identically or differently, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or these is selected from a combination of

According to an embodiment of the present invention, Ar is the same or different whenever it appears, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted It is selected from a phenyl group, a substituted or unsubstituted biphenyl group.

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2a.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of compounds 2a-1 to 2a-45, wherein the specific structures of compounds 2a-1 to 2a-45 are as shown in claim 8 see

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2b.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of Compound 2b-1 to Compound 2b-63, wherein the specific structure of Compound 2b-1 to Compound 2b-63 is as shown in claim 8 see

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2c.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of Compound 2c-1 to Compound 2c-80, wherein the specific structure of Compound 2c-1 to Compound 2c-80 is as shown in claim 8 see

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2d.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of Compound 2d-1 to Compound 2d-27, wherein the specific structure of Compound 2d-1 to Compound 2d-27 is as shown in claim 8 see

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2e.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of Compound 2e-1 to Compound 2e-27, wherein the specific structure of Compound 2e-1 to Compound 2e-27 is as shown in claim 8 see

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2f.

According to an embodiment of the present invention, the first host compound is selected from the group consisting of Compound 2f-1 to Compound 2f-21, wherein the specific structure of Compound 2f-1 to Compound 2f-21 is as shown in claim 8 see

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2c, at least one of _{Z 5} to Z _{8 is CR z} and R _z is substituted or unsubstituted having 6 to 30 carbon atoms selected from cyclic aryl groups.

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2c, W ₁ and W ₈ are identically or differently selected from _{CR w1 whenever they appear, and W 2} to W ₇ are selected from each other when they appear is identically or differently selected from _{CR w2 for each occurrence, Z 1} to Z ₈ is identically or differently selected from C or CR _z whenever it appears, and _{at least one of Z 1} to Z ₄ is C and is connected to L;

At least one of Z ₁ to Z _{8 is CR z} and at least one R _z is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present invention, the first host compound has a structure represented by Formula 2c, wherein _{at least one or two of the substituents R w1} and R _w2 is substituted or unsubstituted having 1 to 20 carbon atoms. Alkyl group, 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, 3 to 30 carbon atoms A substituted or unsubstituted 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, and these is selected from a combination of

According to an embodiment of the present invention, in Formula 1, Cy is any one selected from the group consisting of the following structures,

here,

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

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 (cycloalkyl group), a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms A substituted or unsubstituted heteroaryl group having 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 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group group and combinations thereof;

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

Here, '#' represents a position connected to the metal M;

'*' represents a position connected to _{X 1} , X ₂ , X ₃ or X _{4 in Formula 1.}

인 것을 예로 들면, 2개의 인접한 치환기 R가 존재하는 경우, 즉

인 경우, 식 중의 복수의 치환기 R가 연결되어

와 같이 고리를 형성할 수 있다. 자명한 것은, 복수의 치환기 R가 존재하는 경우, 그중 임의의 인접한 치환기 R은 모두 연결되지 않아 고리를 형성하지 않을 수도 있다. In the present invention, "adjacent substituents R may be optionally joined to form a ring" means that when a plurality of substituents R exist, any adjacent substituents R among them may be connected to form a ring. Cy is

For example, if two adjacent substituents R are present, i.e.

In the case of , a plurality of substituents R in the formula are connected

A ring can be formed as Obviously, when a plurality of substituents R are present, any adjacent substituents R among them may not all be connected to form a ring.

에서 선택되고,According to an embodiment of the present invention, Cy is

is selected from

here,

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

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 (cycloalkyl group), a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms A substituted or unsubstituted heteroaryl group having 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 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group group and combinations thereof;

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

Here, '#' represents a position connected to the metal M;

'*' represents a position connected to _{X 1} , X ₂ , X ₃ or X _{4 in Formula 1.}

According to an embodiment of the present invention, at least one of _{X 1} to X _{8 in Equation 1 is selected as N.}

According to an embodiment of the present invention, in Formula 1, X ₁ to X ₈ are identically or differently selected from C or CR _x whenever they appear.

According to an embodiment of the present invention, the ligand L _a has a structure represented by Formula 1a,

here,

Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;

X ₃ to X ₈ are identically or differently selected from CR _x or N whenever they appear;

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

R _x , R and R ₁ are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 group (alkylsilyl group), a substituted or unsubstituted arylsilyl 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 a 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;

at least one of X ₃ to X _{8 is selected from CR x} and R _x is a cyano group;

Adjacent substituents R _x , R ₁ , R may optionally be joined to form a ring.

In the present invention, "adjacent substituents R _x , R ₁ , R may be optionally connected to form a ring" includes any one or a plurality of cases below. Adjacent substituents R may be linked to form a ring, adjacent substituents R ₁ may be linked to form a ring, and adjacent substituents R _x may be linked to form a ring. Also, adjacent substituents R ₁ and R _x may be connected to form a ring, and adjacent substituents R and R ₁ may be connected to form a ring, and adjacent substituents R and R _x may be connected to form a ring . In other cases, adjacent substituents R, R ₁ , and R _x are not all connected to form a ring.

According to an embodiment of the present invention, the ligand L _a is any one selected from the group consisting of the following structures identically or differently each time it appears,

here,

Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;

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

R _x represents identically or differently each time it appears mono- or multi-substitution;

R, R _x and R ₁ are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 An alkylsilyl group, a substituted or unsubstituted arylsilyl 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 a 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;

at least one R _x is a cyano group;

adjacent substituents R, R _x and R ₁ may optionally be joined to form a ring;

Preferably, at least one R _x is further present in _{the structure, wherein R x} is 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 selected from the group consisting of combinations.

According to an embodiment of the present invention, in Formula 1, at least two of _{X 1} to X _{8 are selected from CR x} , one R _x is a cyano group and the other R _x is deuterium, halogen, 1 to 20 A substituted or unsubstituted alkyl group having carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms , a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a cyano group, and combinations thereof.

According to one embodiment of the present invention, the ligand L _a is any one selected from the following structures identically or differently each time it appears,

here,

Z is identically or differently selected from O, S, Se at each occurrence;

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

R _x represents identically or differently each time it appears mono- or multi-substitution;

R, R _x are identically or differently each time they appear hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted having 3 to 20 ring carbon atoms a 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 heterocyclic group having 7 to 30 carbon atoms, or unsubstituted aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alke group having 2 to 20 carbon atoms A nyl 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 group), a substituted or unsubstituted arylsilyl 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, cya a no group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

at least one R _x is a cyano group;

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

Preferably, at least one R _x is further present in _{the structure, wherein R x} is 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 selected from the group consisting of combinations.

In the embodiment, "adjacent substituents R, R _x may be optionally connected to form a ring" includes any one or a plurality of cases below. Adjacent substituents R may be linked to form a ring, and adjacent substituents R _x may be linked to form a ring. Also, adjacent substituents R and R _x may be connected to form a ring. In other cases, adjacent substituents R and R _x are not connected to form a ring.

According to an embodiment of the present invention, at least two R _{x of the ligand L a} are present, one R _x is a cyano group and the other R _x is 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, at least two R _{x of the ligand L a} are present, at least one R _x is a cyano group, and the other R _x is a substituted or unsubstituted aryl having 6 to 30 carbon atoms. group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an embodiment of the present invention, the ligand L _a is selected from the following structures,

here,

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

R ₃ to R ₈ and R are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 group (alkylsilyl group), a substituted or unsubstituted arylsilyl 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 a group, a cyano group, an isocyano group, a sulfanyl group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

at least one of R ₃ to R ₈ is a cyano group; Adjacent substituents may optionally be joined to form a ring;

Preferably, _{at least one of R 5} to R ₈ is a cyano group;

More preferably, R ₇ or R ₈ is a cyano group.

According to an embodiment of the present invention, the ligand L _a is identically or differently selected from the group consisting of _{L a1} to L _{a84 whenever it appears, wherein the specific structure of L a1} to L _a84 refers to the bar shown in claim 19 .

According to one embodiment of the present invention, the first metal complex has the general formula _{M(L a} ) _m (L _b ) _n (L _c ) _{q ;}

here,

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

the ligands L _a , L _b and L _c may be optionally linked to form a multidentate ligand;

m=1, 2 or 3, n=0, 1 or 2, q=0, 1 or 2 and m+n+q is equal to the oxidation state of metal M; When m is 2 or more, a plurality of L _a may be the same or different, when n is 2, two L _b may be the same or different, and when q is 2, two L _c may be the same or different .

In the embodiment, "the ligands L _a , L _b and L _c may be optionally linked to form a multidentate ligand" includes any one or more of the following cases. L _a, L _b 2 gae any of a and L _c is coupled to which they are attached may form a four-digit ligand, L _a, L _b and L _c may form a six Ligands are connected. In other cases, the ligands L _a , L _b and L _c are all unlinked and do not form a multidentate ligand.

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, identically or differently whenever it appears;

According to an embodiment of the 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 ligands 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 the following structures,

here,

R _a , R _b and R _c each time it appears identically or differently represent 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} , 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 ring 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 a cyclic 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 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, 3 to 20 carbon atoms A substituted or unsubstituted alkylsilyl group having carbon atoms, a substituted or unsubstituted arylsilyl 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 in the ligands L _b and L _c may optionally be joined to form a ring.

In the embodiment, " _{adjacent substituents in ligands L b} and L _c may be optionally connected to form a ring" includes any one or a plurality of cases below. Adjacent substituents R _a may be linked to form a ring, adjacent substituents R _b may be linked to form a ring, and adjacent substituents R _c may be linked to form a ring, and between _{adjacent substituents R a} and R _b may be linked to form a ring, adjacent substituents R _a and R _c may be linked to form a ring, and adjacent substituents R _b and R _c may be linked to form a ring, and adjacent substituents R _C1 and R _C2 may be linked to form a ring, adjacent substituents R _b and R _C1 may be linked to form a ring, and adjacent substituents R _a and R _C1 may be linked to form a ring, and adjacent substituents R _c and R _C1 may be connected to form a ring, adjacent substituents R _b and R _C2 may be connected to form a ring, and adjacent substituents R _a and R _C2 may be connected to form a ring, and adjacent substituents R _c and R _C2 may be linked to form a ring, adjacent substituents R _b and R _N1 may be linked to form a ring, and adjacent substituents R _a and R _N1 may be linked to form a ring, and adjacent substituents R _c and R _N1 may be connected to form a ring. In other cases, adjacent substituents are not all connected to form a ring.

According to an embodiment of the present invention, the ligands L _b and L _c are identically or differently selected from the group consisting of _{L b1} to L _{b195 whenever they appear, wherein the specific structure of L b1} to L _b195 is as shown in claim 21 see

According to an embodiment of the present invention, the first metal complex has a structure represented by Formula 1b,

here,

m is 1, 2 or 3;

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

R ₃ to R ₁₆ and R are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 group (alkylsilyl group), a substituted or unsubstituted arylsilyl 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 a 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;

at least one of R ₃ to R ₈ is a cyano group;

Preferably, R ₇ or R ₈ is a cyano group;

Adjacent substituents may optionally be joined to form a ring.

In the embodiment, "adjacent substituents may be optionally connected to form a ring" includes any one or more of the following cases. adjacent substituents R may be linked to form a ring, adjacent substituents R ₃ and R ₄ may be linked to form a ring, and adjacent substituents R ₅ and R ₄ may be linked to form a ring, and adjacent substituents R ₅ and R ₆ may be linked to form a ring, adjacent substituents R ₆ and R ₇ may be linked to form a ring, and adjacent substituents R ₇ and R ₈ may be linked to form a ring, and adjacent substituents R ₉ and R ₁₀ may be linked to form a ring, adjacent substituents R ₁₀ and R ₁₁ may be linked to form a ring, and adjacent substituents R ₁₁ and R ₁₂ may be linked to form a ring, and adjacent substituents R ₁₂ and R ₁₃ may be connected to form a ring, adjacent substituents R ₁₃ and R ₁₄ may be connected to form a ring, and adjacent substituents R ₁₄ and R ₁₅ may be connected to form a ring, and adjacent substituents R ₁₅ and R ₁₆ may be connected to form a ring. Also, adjacent substituents R and R ₃ to R ₁₆ may be connected to form a ring. In other cases, all of the adjacent substituents are not connected to form a ring.

According to an embodiment of the present invention, _{at least one of the substituents R 3} to R ₈ is a cyano group, and _{at least one of the remaining substituents R 3} to R ₈ is deuterium, halogen, substituted or unsubstituted having 1 to 20 carbon atoms. an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, 3 to 20 ring atoms A substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substitution having 6 to 30 carbon atoms or an unsubstituted aryloxy group, 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 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, 0 to 20 carbon atoms A substituted or unsubstituted 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 their selected from the group consisting of combinations.

According to an embodiment of the present invention, _{at least one of the substituents R 3} to R ₈ is a cyano group, and _{at least one of the remaining substituents R 3} to R ₈ is deuterium, halogen, substituted or unsubstituted having 1 to 20 carbon atoms. an alkyl group, 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, 3 to 30 carbon atoms It is selected from the group consisting of a substituted or unsubstituted heteroaryl group, a cyano group, and combinations thereof.

In the present invention, “ _{at least one of the substituents R 3} to R ₈ is a cyano group, and _{the remainder of the substituents R 3} to R ₈ ” is, for example, if the substituent R ₃ is a cyano group, the remainder of the substituents _{R 3} to R _{8 is a substituent} means R ₄ to R ₈ ; When the substituent R ₇ is a cyano group, and the other of the substituents R ₃ ~ R ₈ is a substituent group means that R ₃ ~ R ₆ and R _8, and; When the substituent R ₈ is a cyano group, and the other of the substituents R ₃ ~ R ₈ is a substituent group indicates that the mean R ₃ ~ R _7. Similarly, it can be inferred in this way in other cases as well.

According to an embodiment of the present invention, _{at least one of the substituents R 9} to R ₁₆ is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. A substituted or unsubstituted cycloalkyl group having 1 to 20 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 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 substitution having 2 to 20 carbon atoms or an unsubstituted alkenyl 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 Alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, 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, _{at least one of the substituents R 9} to R ₁₆ is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. A substituted or unsubstituted cycloalkyl group having a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a cyano group, and combinations thereof is selected from the group consisting of

According to an embodiment of the present invention, _{at least one of the substituents R 10} , R ₁₁ , and R ₁₅ is deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. atoms), a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof is selected from the group consisting of

According to an embodiment of the present invention, _{at least one of the substituents R 10} , R ₁₁ , and R ₁₅ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. It is selected from the group consisting of a substituted or unsubstituted cycloalkyl group and combinations thereof.

According to an embodiment of the present invention, _{at least two of the substituents R 10} , R ₁₁ , and R ₁₅ are deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms (ring). A substituted or unsubstituted cycloalkyl 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, and their selected from the group consisting of combinations.

According to an embodiment of the present invention, _{at least two of the substituents R 10} , R ₁₁ , and R ₁₅ are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. It is selected from the group consisting of a substituted or unsubstituted cycloalkyl group having a cycloalkyl group and combinations thereof.

According to an embodiment of the present invention, the first metal complex is selected from the group consisting of Compounds GD1 to GD83, wherein specific structures of Compounds GD1 to GD83 refer to those shown in claim 25 .

According to an embodiment of the present invention, the organic layer further contains a second host compound, and the second host compound includes a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a carbazole group, an azacarbazole group, and an indolocarbazole group. (indolocarbazole group), dibenzothiophene group, azadibenzothiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenyl Rene group, fluorene group, silafluorene group ((silafluorene group), naphthalene group, quinoline group, isoquinoline group, quinazoline group, quinoxaline group, phenanthrene group, azaphenanthrene group, and combinations thereof contains at least one chemical group selected from the group consisting of

According to an embodiment of the present invention, the organic layer further contains at least one second host compound, and the second host material includes a phenyl group, a carbazole group, an indolocarbazole group, a fluorene group, and a silafluorene group. contains at least one chemical group selected from the group consisting of groups and combinations thereof.

According to an embodiment of the present invention, the second host compound has a structure represented by Formula X,

here,

L _x is identically or differently each time it appears 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 C, CR _v or N whenever it appears, at least one of V is C and is linked to _{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 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

Ar ₁ 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 , R _u may be optionally linked to form a ring.

In the present invention, "adjacent substituents R _v , R _u may be optionally connected to form a ring" includes any one or a plurality of the following cases. Adjacent substituents R _v may be optionally linked to form a ring, and adjacent substituents R _u may be optionally linked to form a ring. Also, adjacent substituents R _v and R _u may be optionally connected to form a ring. In other cases, adjacent substituents R _v , R _u are not connected to form a ring.

According to an embodiment of the present invention, the second host compound has a structure represented by one of Formulas X-a to X-j,

V is identically or differently selected from C, CR _v or N whenever it appears, at least one of V is C and is linked to _{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 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;

Ar ₁ 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 , R _u may be optionally linked to form a ring.

According to an embodiment of the present invention, V is identically or differently selected from C or CR _v whenever it appears, and U is identically or differently selected from C or CR _u whenever it appears, wherein R _u and R _v is identical or different whenever 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 ( 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 group having 3 to 20 carbon atoms (alkylsilyl group), is selected from a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms.

According to an embodiment of the present invention, V is identically or differently selected from C or CR _v whenever it appears, and U is identically or differently selected from C or CR _u whenever it appears, wherein R _u and R _v is identically or differently whenever it appears hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted group having 3 to 18 carbon atoms, or It is selected from an unsubstituted heteroaryl group.

According to an embodiment of the present invention, V is identically or differently selected from C or CR _v whenever it appears, and U is identically or differently selected from C or CR _u whenever it appears, wherein R _u and R _v is the same or different whenever it appears hydrogen, deuterium, phenyl group, biphenyl group, naphthyl group, phenanthryl group, triphenylene group, terphenyl group, fluorenyl group, pyridyl group, dibenzofuranyl group, dibenzothienyl group and their selected from combinations.

According to an embodiment of the present invention, Ar ₁ is the same or differently each time it appears, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms or a combination thereof.

According to an embodiment of the present invention, Ar ₁ is the same or differently whenever it appears, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a terphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzo thienyl group and combinations thereof.

According to an embodiment of the present invention, L _x 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 group having 3 to 20 carbon atoms It is selected from a heteroarylene group or a combination thereof.

According to an embodiment of the present invention, each time L _x is the same or differently, a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylidene group ( Carbazolylidene group), a substituted or unsubstituted dibenzofuranylene group, and a substituted or unsubstituted dibenzothiophenylene group.

According to an embodiment of the present invention, L _x is a single bond, a phenylene group, or a biphenylene group.

According to an embodiment of the present invention, the second host compound has a structure represented by Formula X-h.

According to an embodiment of the present invention, the second host compound is selected from the group consisting of Compound X-1 to Compound X-126, wherein the specific structure of Compound X-1 to Compound X-126 is as shown in claim 32. see

According to an embodiment of the present invention, the organic layer is a light emitting layer and the light emitting layer contains a first metal complex, and the total weight of the first host compound, the second host compound, and the first metal complex is 1% to 30% of the weight of the light emitting layer occupy

According to an embodiment of the present invention, the organic layer is a light emitting layer, the light emitting layer contains a first metal complex, and the total weight of the first host compound, the second host compound, and the first metal complex is 3% to 13% of the weight of the light emitting layer occupy

According to an embodiment of the present invention, an electronic device is further disclosed, which includes the organic electroluminescent device according to any one of the above-described 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. The combination of these materials is described in detail in paragraphs 0132 to 0161 of US Patent Application US2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or 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 described that materials usable for a specific layer in an 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. This combination of 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 are carried out under nitrogen 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 LENGGUANG TECH. in Shanghai, electrochemical workstation of CORRTEST in Wuhan and sublimation apparatus of BEQ in Anhui, 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 conventional equipment 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 unaffected, and thus the relevant content is not further described herein.

device embodiment

The manufacturing method of the organic electroluminescent device is not limited, and the manufacturing method of Examples to be described later is only an example and should not be construed as limiting. Those skilled in the art can reasonably improve the manufacturing method of the embodiment to be described later based on the prior art. Illustratively, the mixing ratio of various materials in the light emitting layer is not particularly limited, and those skilled in the art may reasonably select within a specific range based on the prior art. For example, based on the total weight of the light emitting layer material, the first host compound accounts for 10% to 90%, the second host compound accounts for 10% to 90%, and the dopant compound accounts for 1% to 60% and; Or preferably, the dopant compound accounts for 3% to 30%. More preferably, the first host compound accounts for 20% to 65%, the second host compound accounts for 20% to 65%, and the dopant compound accounts for 3% to 30%. The characteristics of the light emitting device manufactured according to the embodiment are measured using a conventional device in the art and a method well known to those skilled in the art. Since all of those skilled in the art know the relevant contents such as the use of the device and the test method, and can reliably acquire the unique data of the sample without being affected, the above related contents will not be further repeated in this patent. The compounds used in the present invention, such as the first metal complex, the first host compound, and the second host compound, can all be easily obtained by those skilled in the art, for example, can be obtained from the market, or a method of the prior art. may be obtained by reference, or may be obtained by reference to the manufacturing method of the Chinese application of application number CN2019100770790 or the US application of US20200127213A1, which is not further repeated herein.

Example 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 rate of 0.2 to 2 Å/s at a vacuum degree ^{of about 10 -8 Torr.} 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). The following compound GD59 was doped into the first host 2c-31 and the second host X-4 and co-deposited to be used as an emission layer (EML), and the first host 2c-31 and the second host X-4 were The ratio is 1:1. Compound H1 is used as the hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited to form an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is deposited as an electric injection layer, and aluminum with a thickness of 120 nm is deposited as a cathode. Next, the device is transferred back to the glove box and encapsulated using a glass lid and a moisture getter to complete the device.

Example 2

Preparation of Example 2 was the same as in Example 1, except that Compound 2c-3 was used instead of Compound 2c-31 in the light emitting layer (EML).

Comparative Example 1

Preparation of Comparative Example 1 was the same as in Example 1, except that Compound H1 was used instead of Compound 2c-31 in the emission layer (EML).

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

[Table 1]

Partial device structures of Examples 1, 2 and Comparative Example 1

The material structure used for the device is shown below:

Table 2 shows CIE data measured at a constant current of 15 mA/cm ^{2 , current efficiency;} and device lifetime (LT95) measured at a constant current of 80 mA/cm ^{2 are indicated.}

[Table 2]

Device data of Examples 1, 2 and Comparative Example 1

debate:

In Examples 1 to 2 and Comparative Example 1, Ir complex phosphorescent dopant GD59 containing a cyano group-substituted dibenzofuranylpyridine ligand of the present invention was used, the first host compound 2c of the present invention In the case of doping -31 and 2c-3, compared to using H1 as the first host, the current efficiency of the device was similar to or slightly improved than that of the comparative example, but the device lifetime was improved by about 78.2% and 33.0%, respectively did

Example 3

The preparation of Example 3 was the same as in Example 1, except that Compound GD2 was used instead of Compound GD59 in the light emitting layer (EML).

Comparative Example 2

Preparation of Comparative Example 2 was the same as in Example 3, except that Compound H1 was used instead of Compound 2c-31 in the emission layer (EML).

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

[Table 3]

Partial device structure of Example 3 and Comparative Example 2

The new material structure used for the device is shown below:

Table 4 shows CIE data measured at a constant current of 15 mA/cm ^{2 , current efficiency;} and device lifetime (LT95) measured at a constant current of 80 mA/cm ^{2 are indicated.}

[Table 4]

Device data of Example 3 and Comparative Example 2

debate:

In Example 3 and Comparative Example 2, in using the phosphorescent dopant GD2 of the Ir complex containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, doping the first host compound 2c-31 of the present invention In this case, compared to using H1 as the first host, the current efficiency of the device is the same as that of the comparative example, but the device lifespan is improved by about 40.4%.

Example 4

Preparation of Example 4 was the same as in Example 1, except that Compound 2d-1 was used instead of Compound 2c-31 in the light emitting layer (EML).

Example 5

Preparation of Example 5 is the same as in Example 1, except for using Compound GD60 instead of Compound GD59 and using Compound 2d-1 instead of Compound 2c-31 in the light emitting layer (EML).

Comparative Example 3

Preparation of Comparative Example 3 was the same as in Example 5, except that Compound H1 was used instead of Compound 2d-1 in the light emitting layer (EML).

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

[Table 5]

Partial device structures of Examples 4, 5 and Comparative Example 3

The new material structure used for the device is shown below:

Table 6 shows CIE data measured at a constant current of 15 mA/cm ^{2 , current efficiency;} and device lifetime (LT95) measured at a constant current of 80 mA/cm ^{2 are indicated.}

[Table 6]

Device data of Examples 4 and 5 and Comparative Examples 1 and 3

debate:

The first host compound H1 is currently a commercial host material, and in Example 4 and Comparative Example 1, using Ir complex phosphorescent dopant GD59 containing a cyano group-substituted dibenzofuranylpyridine ligand of the present invention, When doping the first host material 2d-1 of the present invention, compared to using the commercial material H1 as the first host, the current efficiency of the device is similar, but the device lifetime is improved.

In Example 5 and Comparative Example 3, using the phosphorescent dopant GD60 of the Ir complex containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, doping the first host material 2d-1 of the present invention case, compared to using the commercial material H1 as the first host, both the device current efficiency and device lifetime were improved.

The above results indicate that the first host compound 2d-1 can achieve device performance comparable to that of the commercial host material H1, and even slightly improved.

Example 6

Preparation of Example 6 was the same as in Example 1, except that Compound GD12 was used instead of Compound GD59 in the light emitting layer (EML).

Comparative Example 4

Preparation of Comparative Example 4 was the same as in Example 6, except that Compound H1 was used instead of Compound 2c-31 in the emission layer (EML).

Example 7

Preparation of Example 7 was the same as Example 1, except that Compound GD18 was used instead of Compound GD59 in the light emitting layer (EML).

Example 8

Preparation of Example 8 is the same as Example 7, except that Compound 2c-3 is used instead of Compound 2c-31 in the light emitting layer (EML).

Comparative Example 5

Preparation of Comparative Example 5 was the same as in Example 7, except that Compound H1 was used instead of Compound 2c-31 in the light emitting layer (EML).

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

[Table 7]

Partial device structures of Examples 6 to 8 and Comparative Examples 4 to 5

The new material structure used for the device is shown below:

Table 8 shows CIE data measured at a constant current of 15 mA/cm ^{2 , current efficiency;} and device lifetime (LT95) measured at a constant current of 80 mA/cm ^{2 are indicated.}

[Table 8]

Device data of Examples 6 to 8 and Comparative Examples 4 to 5

debate:

In Example 6 and Comparative Example 4, in using the phosphorescent dopant GD12 containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, the first host compound 2c-31 of the present invention is doped In this case, compared to using H1 as the first host, the current efficiency of the device is slightly lower than that of the comparative example, but the device lifespan is improved by about 41.6%.

In Examples 7 to 8 and Comparative Example 5, in using the phosphorescent dopant GD18 of the Ir complex containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, the first host compound 2c of the present invention In the case of doping with -31 and 2c-3, compared to using H1 as the first host, the current efficiency of the device was slightly improved compared to the comparative example, but the device lifetime was improved by about 35% and 22%, respectively.

Example 9

Preparation of Example 9 is the same as in Example 1, except that compound GD43 is used instead of compound GD59 in the light emitting layer (EML).

Comparative Example 6

Preparation of Comparative Example 6 was the same as in Example 9, except that Compound H1 was used instead of Compound 2c-31 in the emission layer (EML).

Comparative Example 7

Preparation of Comparative Example 7 was the same as in Example 9, except that Compound A was used instead of Compound GD43 in the light emitting layer (EML).

Comparative Example 8

Preparation of Comparative Example 8 was the same as in Comparative Example 7, except that Compound H1 was used instead of Compound 2c-31 in the emission layer (EML).

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

[Table 9]

Partial device structures of Example 9 and Comparative Examples 6 to 8

The new material structure used for the device is shown below:

[Table 10]

Device data of Example 9 and Comparative Examples 6 to 8

debate:

As can be seen from Example 9 and Comparative Example 6, in using the phosphorescent dopant GD43 of the Ir complex containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, the first host compound 2c of the present invention Compared to doping -31 and using H1 as the first host, both the current efficiency and the lifetime of the device were improved. In particular, when the first host compound 2c-31 was used, the device lifetime was improved by 54.3%.

As can be seen from Example 9 and Comparative Example 7, in using the phosphorescent dopant GD43 of the Ir complex containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, cyano group-substituted dibenzofura Compared to using the Ir complex phosphorescent dopant compound A containing no nylpyridine ligand, both the current efficiency and the lifetime were improved, and in particular, the lifetime was improved by about 64.8%.

Comparing Comparative Example 7 and Comparative Example 8, in the case of using the phosphorescent dopant compound A not containing a cyano group substituent and doping the first host material 2c-31 of the present invention, the use of H1 as the first host Compared to that, the device lifetime was improved only by 25.8%, and the lifetime improvement was compared to the lifetime improvement (54.3%) when using the phosphorescent dopant GD43 containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention. is reduced by 110%. As can be seen from this, the combination of the Ir complex phosphorescent dopant containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention and the first host compound has an excellent effect in increasing the device lifespan, and the device A very long lifespan can be achieved.

Example 10

Preparation of Example 10 is Example 1, except that compound GD24 is used instead of compound GD59 in the light emitting layer (EML), wherein the ratio of GD24, the first host 2c-31 and the second host X-4 is 6:47:47. same as

Comparative Example 9

Preparation of Comparative Example 9 was the same as in Example 10, except that Compound H1 was used instead of Compound 2c-31 in the light emitting layer (EML).

Example 11

The preparation of Example 11 was the same as in Example 10, except that Compound GD83 was used instead of Compound GD24 in the light emitting layer (EML).

Comparative Example 10

Preparation of Comparative Example 10 was the same as in Example 11, except that Compound H1 was used instead of Compound 2c-31 in the emission layer (EML).

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

[Table 11]

Partial device structures of Examples 10-11 and Comparative Examples 9-10

The new material structure used for the device is shown below:

Table 12 shows CIE data measured at a constant current of 15 mA/cm ^{2 , current efficiency;} and device lifetime (LT95) measured at a constant current of 80 mA/cm ^{2 are indicated.}

[Table 12]

Device data of Examples 10-11 and Comparative Examples 9-10

debate:

In Example 10 and Comparative Example 9, in using the phosphorescent dopant GD24 of the Ir complex containing the cyano group-substituted dibenzofuranylpyridine ligand of the present invention, doping the first host compound 2c-31 of the present invention In this case, compared to using H1 as the first host, the current efficiency of the device was slightly improved compared to the comparative example, and the device lifetime was improved by about 130.5%.

In Example 11 and Comparative Example 10, Ir complex phosphorescent dopant GD83 containing a cyano group-substituted dibenzofuranylpyridine ligand of the present invention was used, and the first host compound 2c-31 of the present invention was doped. In this case, compared to using H1 as the first host, the current efficiency of the device is slightly improved compared to the comparative example, and the device lifetime is improved by about 126.5%.

Taken together, compared to other devices, when using a metal complex-based dopant containing a ligand structure of the cyano group-substituted Formula 1 structure of the present invention in an organic layer and a first host compound having a specified structure, the device performance is improved. Here, the current efficiency of the device was similar to the comparative example or improved compared to the comparative example, and the lifespan of the device was all improved, and some were significantly improved. This has provided the industry with a good combination of light emitting layer materials.

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 is to be understood that the various theories as to why the present invention works are not limiting.

Claims (34)

anode;
cathode; and
an organic layer disposed between the anode and the cathode; wherein the organic layer contains at least a first metal complex and a first host compound:
Here, the first metal complex contains a metal M and a ligand L _a coordinated to the metal M and the ligand L _a has a structure represented by Formula 1,

here,
metal M is selected from metals having a relative atomic mass greater than 40;
Cy is selected from a substituted or unsubstituted aryl group having 5 to 24 ring atoms or a substituted or unsubstituted heteroaryl group having 5 to 24 ring atoms, identically or differently each time it appears, wherein Cy is a metal- connected to the metal M through a carbon bond or a metal-nitrogen bond;
Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;
X ₁ to X ₈ are identically or differently selected from C, CR _x or N _{whenever they appear, and at least one of X 1} to X ₄ is C and is linked to Cy;
X ₁ , X _{2 ,} X ₃ or X ₄ is connected to the metal M through a metal-carbon bond or a metal-nitrogen bond;
R _x and R ₁ 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;
at least one of X ₁ to X _{8 is selected from CR x} and R _x is a cyano group;
adjacent substituents R ₁ , R _x may optionally be joined to form a ring;
Here, the first host compound has a structure represented by Formula 2,

here,
E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E at least two of ₆ is equal to N, and at least one of E ₁ ~ E ₆ is C and formula A, formula linked to at least one of B, Formula C, or Formula D;

where, in formula A, formula B, formula C and formula D,
A ₁ and A ₂ , identically or differently each time they appear, are selected from the group consisting of _{O, S, Se, NR n} , CR _n R _n and SiR _n R _{n ;} when two R _n are present simultaneously, the two R _n may be the same or different;
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;
W ₁ and W ₈ are identically or differently selected from CR _w1 or N whenever they appear;
W ₂ to W ₇ are identically or differently selected from CR _w2 or N whenever they appear;
Z ₁ to Z ₈ are identically or differently selected from C, CR _z or N _{whenever they appear, and at least one of Z 1} to Z ₈ is C and is connected to L;
Y ₁ to Y ₁₅ are identically or differently selected from C, CR _{y or N whenever they appear, wherein at least one of Y 1} to Y ₈ in formula C is C and is connected to L; In formula D, _{at least one of Y 1} to Y ₇ is C and at least one of Y ₈ to Y ₁₁ is C, all of which are connected to L;
R _w1 is identically or differently each time it appears is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms ( 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 aral group having 7 to 30 carbon atoms a alkyl 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, 6 to 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, 6 a substituted or unsubstituted arylsilyl group having ˜20 carbon atoms and combinations thereof;
R _z and R _w2 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms an alkenyl 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 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;
R _e , R _n and R _y 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, 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 aryloxy group having 2 to 20 carbon atoms, or unsubstituted alkenyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms A silyl group, a substituted or unsubstituted arylsilyl 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 connection position of formula A, formula B, formula C or formula D and formula 2;
Adjacent substituents R _e , R _n , R _w2 , R _y , R _z may be optionally connected to form an organic electroluminescent device.
The method of claim 1,
E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E and ₆₃ than N of at least one of E ₁ ~ E ₆ CR _e and receive is the R _e each time identically or differently 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, or a combination thereof;
Preferably, each time R _e is the same or different from each other, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted phenyl group, a substituted Or an organic electroluminescent device selected from an unsubstituted biphenyl group or a combination thereof.
3. The method of claim 1 or 2,
E ₁ ~ E ₆ are the same or different selected from C, CR _e or N each time receive, E ₁ ~ E and ₆₃ than N and at least two C of E ₁ ~ E ₆ of independently type A, respectively, An organic electroluminescent device connected to Formula B, Formula C or Formula D.
4. The method according to any one of claims 1 to 3,
W ₁ and W ₈ are identically or differently selected from _{CR w1 whenever they appear;} W ₂ to W ₇ are identically or differently selected from _{CR w2 whenever they appear;} Z ₁ to Z ₈ are identically or differently selected from C or CR _z whenever they appear; Y ₁ to Y ₁₅ are identically or differently selected from C or CR _y whenever they appear;
Adjacent substituents R _z , R _w2 , R _y may be optionally connected to form an organic electroluminescent device.
The method of claim 1,
The first host compound has a structure represented by one of Formulas 2a to 2f,

where in Equation 2a to Equation 2f,
A ₁ , A ₂ , L, Z ₁ to Z ₈ , W ₁ to W ₈ and Y ₁ to Y ₁₅ have the same definition as in claim 1 ;
Ar is identically or differently each time it appears, an organic electroluminescent device 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 .
6. The method according to any one of claims 1 to 5,
At least one or two of R _w1 , R _w2 , and R _y is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms A cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms a silyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a hydroxyl group, and combinations thereof;
Preferably, _{at least one or two of R w1} , R _w2 , R _y is 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 An organic electroluminescent device selected from a combination thereof.
7. The method according to any one of claims 1 to 6,
L is, identically or differently, every occurrence of a single bond, a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 6 carbon atoms, a substituted or unsubstituted cycloalkylene group having 6 to 12 carbon atoms; a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof;
Preferably, 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 Carbazolylidene group, a substituted or unsubstituted It is selected from a dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group;
More preferably, 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.
The method of claim 1,
The first host compound is an organic electroluminescent device selected from the group consisting of:

7. The method of claim 6,
The first host compound has a structure represented by Formula 2c, at least one of _{Z 5} to Z _{8 is CR z} and R _z is an organic electroluminescence selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. device.
7. The method of claim 6,
The first host compound has a structure represented by Formula 2c, W ₁ and W ₈ are identically or differently selected from _{CR w1 whenever they appear, and W 2} to W ₇ are identically or differently selected from _{CR w2 whenever they appear} and Z ₁ to Z ₈ are identically or differently selected from C or CR _z whenever they appear, and _{at least one of Z 1} to Z ₄ is C and is connected to L;
At least one of Z ₁ to Z _{8 is CR z} and at least one R _z is an organic electroluminescent device selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
11. The method according to any one of claims 1 to 10,
In Formula 1, Cy is any one selected from the group consisting of:

here,
R each time it appears, identically or differently, mono-, poly- or unsubstituted;
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 (cycloalkyl group), a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 3 to 30 carbon atoms A substituted or unsubstituted heteroaryl group having 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 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 sulfanyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group group and combinations thereof;
Adjacent substituents R may optionally be joined to form a ring;
Preferably, Cy is

ego;
Here, '#' represents a position connected to the metal M;
'*' is an organic electroluminescent device representing a position connected to _{X 1} , X ₂ , X ₃ or X _{4 in Formula 1.}
12. The method according to any one of claims 1 to 11,
In Formula 1, _{at least one of X 1} to X ₈ is an organic electroluminescent device selected as N.
12. The method according to any one of claims 1 to 11,
In Equation 1, X ₁ to X ₈ are the same or differently selected from C or CR _x whenever they appear organic electroluminescent device.
12. The method according to any one of claims 1 to 11,
Ligand L _a has the structure represented by Formula 1a:

here,
Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;
X ₃ to X ₈ are identically or differently selected from CR _x or N whenever they appear;
R each time it appears, identically or differently, represents mono-, poly- or unsubstituted;
R _x , R and R ₁ are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 group (alkylsilyl group), a substituted or unsubstituted arylsilyl 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 a 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;
at least one of X ₃ to X _{8 is selected from CR x} and R _x is a cyano group;
Adjacent substituents R _x , R ₁ , R may be optionally connected to form a ring organic electroluminescent device.
12. The method according to any one of claims 1 to 11,
_A ligand L is any one selected from the group consisting of the same or different and each time receive the following structure:

here,
Z, identically or differently each time it appears, is selected from the group consisting of _{O, S, Se, NR 1 ,} CR ₁ R ₁ and SiR ₁ R _{1 ;} when two R ₁ are present simultaneously, the two R ₁ may be the same or different;
R each time it appears, identically or differently, mono-, poly- or unsubstituted;
R _x represents identically or differently each time it appears mono- or multi-substitution;
R, R _x and R ₁ are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 An alkylsilyl group, a substituted or unsubstituted arylsilyl 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 a 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;
at least one R _x is a cyano group;
adjacent substituents R, R _x and R ₁ may optionally be joined to form a ring;
Preferably, at least one R _x is further present in _{the structure, wherein R x} is 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 An organic electroluminescent device selected from the group consisting of combinations.
16. The method according to any one of claims 1 to 11, 14 and 15,
Ligand L _a is any one selected from the structures below, identically or differently each time it appears:

here,
Z is identically or differently selected from O, S, Se at each occurrence;
R each time it appears, identically or differently, mono-, poly- or unsubstituted;
R _x represents identically or differently each time it appears mono- or multi-substitution;
R, R _x are identically or differently each time they appear hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted having 3 to 20 ring carbon atoms a 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 heterocyclic group having 7 to 30 carbon atoms, or unsubstituted aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alke group having 2 to 20 carbon atoms A nyl 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 group), a substituted or unsubstituted arylsilyl 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, cya a no group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
at least one R _x is a cyano group;
Adjacent substituents R, R _x may optionally be joined to form a ring;
Preferably, at least one R _x is further present in _{the structure, wherein R x} is 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 An organic electroluminescent device selected from the group consisting of combinations.
17. The method according to any one of claims 1 to 16,
At least two R _x of the ligand L _a are present, one R _x is a cyano group and at least the other R _x is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or 3 to 20 ring carbon atoms A substituted or unsubstituted cycloalkyl group having (ring carbon atoms), a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms An organic electroluminescent device selected from.
16. The method according to any one of claims 1 to 11, 14 and 15,
Ligand L _a is selected from the structure below,

here,
R each time it appears, identically or differently, mono-, poly- or unsubstituted;
R ₃ to R ₈ and R are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 group (alkylsilyl group), a substituted or unsubstituted arylsilyl 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 a group, a cyano group, an isocyano group, a sulfanyl group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
at least one of R ₃ to R ₈ is a cyano group; Adjacent substituents may optionally be joined to form a ring;
Preferably, _{at least one of R 5} to R ₈ is a cyano group;
More preferably, R ₇ or R ₈ is an organic electroluminescent device that is a cyano group.
12. The method according to any one of claims 1 to 11,
Ligand L _a is any one selected from the group consisting of the following structures identically or differently each time it appears organic electroluminescent device:

20. The method according to any one of claims 1 to 19,
The first metal complex has the general formula _{M(L a} ) _m (L _b ) _n (L _c ) _{q :}
here,
the metal M, identically or differently whenever it appears, is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; Preferably, M is selected from Pt or Ir, identically or differently each time it appears;
the ligands 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 m+n+q is equal to the oxidation state of the metal M; When m is 2 or more, a plurality of L _a may be the same or different, if n is 2, two L _b may be the same or different, if q is 2, two L _c may be the same or different, ;
Preferably, the ligands L _b and L _c are identically or differently each time they appear is a structure represented by any one selected from the group consisting of the following structures,

here,
R _a , R _b and R _c each time it appears identically or differently represent mono-, poly- or unsubstituted;
X _b is identically or differently each time it appears is selected from the group consisting of _{O, S, Se, NR N1} , CR _C1 R _{C2 ;}
R _a , R _b , R _c , R _N1 , R _C1 and R _C2 are 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 ring 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 a cyclic 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 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, 3 to 20 carbon atoms A substituted or unsubstituted alkylsilyl group having carbon atoms, a substituted or unsubstituted arylsilyl 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;
An organic electroluminescent device in which adjacent substituents in ligands L _b and L _{c may be optionally connected to form a ring.}
21. The method of claim 20,
Ligands L _b and L _c are identical or different whenever they appear organic electroluminescent device selected from the group consisting of:

22. The method according to any one of claims 1 to 21,
The first metal complex has a structure represented by Formula 1b,

here,
m is 1, 2 or 3;
R each time it appears, identically or differently, represents mono-, poly- or unsubstituted;
R ₃ to R ₁₆ and R are identically or differently each time they appear hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substitution 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, 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 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 group (alkylsilyl group), a substituted or unsubstituted arylsilyl 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 a 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;
at least one of R ₃ to R ₈ is a cyano group;
Adjacent substituents may optionally be joined to form a ring;
Preferably, R ₇ or R ₈ is a cyano group organic electroluminescent device.
23. The method of claim 22,
At least one of the substituents R ₃ to R ₈ is a cyano group, and at least one of the substituents R ₃ to R ₈ and at least one of the substituents R ₉ to R ₁₆ are deuterium, halogen, substituted or unsubstituted having 1 to 20 carbon atoms A cyclic alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, 3 to 20 rings A substituted or unsubstituted heterocyclic group having 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, 6 to 30 carbon atoms A substituted or unsubstituted aryloxy group, 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 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, 0 to 20 carbon atoms Substituted or unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group and these selected from the group consisting of a combination of;
Preferably, _{at least one of the substituents R 3} to R ₈ is a cyano group, and at least one of the substituents R ₃ to R ₈ and at least one of the substituents R ₉ to R ₁₆ are deuterium, halogen, having 1 to 20 carbon atoms. A substituted or unsubstituted alkyl group, 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, 3 to An organic electroluminescent device selected from the group consisting of a substituted or unsubstituted heteroaryl group having 30 carbon atoms, a cyano group, and combinations thereof.
24. The method of claim 22 or 23,
At least one or two of the substituents R ₁₀ , R ₁₁ , R ₁₅ is deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group having 3 to 20 ring carbon atoms It is selected from the group consisting of 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 two of the substituents R 10} , R ₁₁ , R ₁₅ is 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 An organic electroluminescent device selected from the group consisting of a cyclic cycloalkyl group and combinations thereof.
21. The method of claim 1 or 20,
The first metal complex is an organic electroluminescent device selected from the group consisting of:

26. The method according to any one of claims 1 to 25,
The organic layer further contains a second host compound, and the second host compound includes a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a carbazole group, an azacarbazole group, an indolocarbazole group, and dibenzothiophene. group, azadibenzothiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenylene group, fluorene group, silafluorene group At least a chemical group selected from the group consisting of a silafluorene group, a naphthalene group, a quinoline group, an isoquinoline group, a quinazoline group, a quinoxaline group, a phenanthrene group, an azaphenanthrene group, and combinations thereof contains one;
Preferably, the second host material is an organic electroluminescent device containing at least one chemical group selected from the group consisting of a phenyl group, a carbazole group, an indolocarbazole group, a fluorene group, a silafluorene group, and combinations thereof.
27. The method of claim 26,
The second host compound has a structure represented by Formula X:

here,
L _x is identically or differently each time it appears 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 C, CR _v or N whenever it appears, at least one of V is C and is linked to _{L x ;}
U is identically or differently selected from C, CR _u or N whenever it appears, 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 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 heterocyclic group having 7 to 30 carbon atoms or an unsubstituted 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 group having 2 to 20 carbon atoms An alkenyl 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 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;
Ar ₁ 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 , R _u may be optionally connected to form an organic electroluminescent device.
28. The method of claim 27,
The second host compound has a structure represented by one of Formulas Xa to Xj,

In formulas Xa to Xj,
V, L _x , U and Ar ₁ An organic electroluminescent device having the same definition as in claim 27 .
29. The method of claim 27 or 28,
wherein V is identically or differently selected from C or CR _v at each occurrence, and U is identically or differently selected from C or CR _u at each occurrence, wherein R _u and R _v are identical or different 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, 6 to 30 carbon atoms A substituted or unsubstituted aryl group having a group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms selected from a substituted or unsubstituted arylsilyl group having carbon atoms;
Preferably, R _u and R _v are identically or differently each time they appear hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, 3 substituted or unsubstituted heteroaryl groups having -18 carbon atoms;
More preferably, R _u and R _v are identically or differently each time they appear hydrogen, deuterium, phenyl group, biphenyl group, naphthyl group, phenanthryl group, triphenylene group, terphenyl group, fluorenyl group, pyridyl group, dibenzofura An organic electroluminescent device selected from a nyl group, a dibenzothienyl group, and combinations thereof.
30. The method according to any one of claims 27 to 29,
Wherein Ar ₁ is identically or differently each time it appears is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof;
Preferably, Ar ₁ is the same or differently each time it appears, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a terphenyl group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, and combinations thereof An organic electroluminescent device selected from.
31. The method according to any one of claims 27 to 30,
L _x is identically 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 heteroarylene group having 3 to 20 carbon atoms, or a combination thereof become;
Preferably, each time L _x is the same or different, each occurrence is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted Carbazolylidene group, a substituted or It is selected from an unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group;
More preferably, the L _x is a single bond, a phenylene group, an organic electroluminescent device of a biphenylene group.
29. The method according to any one of claims 26 to 28,
The second host compound is an organic electroluminescent device selected from the group consisting of:

The method of claim 1,
the organic layer is a light emitting layer and the light emitting layer contains a first metal complex, and the total weight of the first host compound, the second host compound, and the first metal complex accounts for 1% to 30% of the weight of the light emitting layer;
Preferably, the total weight of the first metal complex accounts for 3% to 13% of the total weight of the light emitting layer organic electroluminescent device.
An electronic device comprising the organic electroluminescent device according to any one of claims 1 to 33.

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