KR20230136057A - Organic electroluminescent material and device thereof - Google Patents

Abstract

Disclosed in the present invention are organic electroluminescent materials and devices thereof. The organic electroluminescent material is a compound with the structure of chemical formula 1, and these novel compounds can be applied to electroluminescent devices. For example, the compounds can be used as host materials, transmission materials, etc., for organic electroluminescent devices to provide better device performance and, in particular, improve device lifespan. Additionally, the organic electroluminescent device containing the compound and a compound composition containing the compound are further disclosed.

Description

Organic electroluminescent material and its device {ORGANIC ELECTROLUMINESCENT MATERIAL AND DEVICE THEREOF}

The present invention relates to compounds used in organic electronic devices, such as organic electroluminescent devices. More specifically, it relates to a heterocyclic compound having the structure of Formula 1, an organic electroluminescent device containing the compound, and a compound composition containing the compound.

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

In 1987, Tang and Van Slyke of Eastman Kodak described a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline aluminum layer as the electron transport layer and the light emitting layer. reported (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). The most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-luminous solid-state devices, they offer tremendous potential for display and lighting applications. Additionally, the inherent 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 depending on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through a non-radiative attenuation channel. Therefore, the internal quantum efficiency (IQE) of fluorescent OLED is only 25%. These limitations hinder the commercialization of OLED. In 1997, Forrest and Thompson reported a phosphorescent OLED using triplet state emission from a heavy metal containing complex as an emitter. Therefore, a singlet state and a triplet state can be obtained and an IQE of 100% can be achieved. Because of its high efficiency, the discovery and development of phosphorescent OLED has directly contributed to the commercialization of active matrix OLED (AMOLED). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. This luminous body has a small singlet-triplet state gap so that the exciton can return from the triplet state to the singlet state. In a TADF device, a triplet exciton can generate a singlet exciton through reverse intersystem crossing, thereby achieving a high IQE.

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

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

OLED's luminous color can be realized by structural design of the luminescent material. OLED may include one light-emitting layer or multiple light-emitting layers to realize a desired spectrum. In green, yellow and red OLEDs, phosphorescent materials have already achieved successful commercialization. Blue phosphorescent devices still have problems such as blue unsaturation, short device life, and high operating voltage. Commercial full-color OLED displays typically use a mixed strategy using blue fluorescence and phosphorescent yellow or red and green. Currently, there is still a problem that the efficiency of phosphorescent OLED is drastically reduced in the case of high brightness. In addition, it is desired to have a more saturated emission spectrum, higher efficiency and longer device lifetime.

In CN113227085A, the structure is as follows: Disclosed is an organic compound having and an organic light-emitting device containing the compound, where Ar ₂ and Ar ₃ are each independently hydrogen or a substituted or unsubstituted C _6-60 aryl group, and L is a phenylene group, It is a phenylene group substituted by a phenyldiyl group, terphenyldiyl group, naphthalenediyl group, or naphthyl group. In this application, the following compounds have specific structures: was initiated. The application necessarily discloses a triazinyl group skeleton compound having a directly connected dibenzothiophene group, but does not disclose or teach the compound having the structure of formula 1 of the present application and its application in an organic electroluminescent device.

In WO2019190101A1, the light emitting layer has the following structural formula: ^Disclosed is ^an organic light-emitting device comprising ^an organic compound having a It was further disclosed that it can have. In this application, the following compounds have specific structures: and started. The application did not disclose a compound having the structure of formula 1 of the present application, and in particular, a compound having a substituted or unsubstituted phenyl substituent at position 1 of the five-membered dibenzo ring connected to the triazinyl group through L ³ or L ⁵ and he did not disclose and teach application in organic electroluminescent devices.

In US20190198775A1, the general formula structure is as follows: A combination comprising a compound having was disclosed, and at least one of Ar ¹ to Ar ³ has the following structure In addition, the compound has the following secondary general formula It was disclosed that it can have, and the specific structure disclosed here is and There is. Although the application disclosed a large number of compounds having both a dibenzo five-membered ring and a triazinyl group structure, the present application did not disclose or teach about the compound having the structure of Formula 1 and its effect on device performance.

CN108250189A has the following structure: Disclosed _is an organic _compound having _a and _an organic _{light -} emitting device _containing the compound, wherein , at least one of R _1a to R _4a is -HAr ₁ ; R _1b to R _4b are each independently L ₂ -HAr ₂ or A ₂ , and at least one of R _1b to R _4b is -HAr ₂ ; HAr ₁ and HAr ₂ are each independently and at least two of X ₁ to X ₃ are selected from N. In this application, in the specific structure and Phosphorus compounds were disclosed. This application did not disclose or teach about compounds having the structure of Formula 1 of the present application, especially compounds where the 1st position of the dibenzofuran group is a substituted or unsubstituted phenyl group, and their effect on device performance.

CN110294703A is a compound represented by a combination of Formula 1 and Formula 2 and an organic light-emitting device containing the compound: was disclosed, where X ¹ and X ² are independently O or S, and two adjacent * in Formula 1 are connected to * in Formula 2. In this application, in the specific structure Phosphorus compounds were disclosed. The application did not disclose or teach the compound having the structure of Formula 1 of the present application and its effect on device performance.

The present invention aims to provide a series of heterocyclic compounds having the structure of Formula 1 in order to at least partially solve the above problems. These new compounds can be applied to organic electroluminescent devices, for example, as host materials and transmission materials for organic electroluminescent devices, and can provide better device performance and, in particular, improve device lifespan.

According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed,

here,

X is selected from O, S or Se;

X ₁ -X ₆ are selected identically or differently from CR _x or N each time they appear;

Z ₁ -Z ₈ are, identically or differently, selected from C, CR _z or N whenever they appear, and one of Z ₁ -Z ₄ is selected from C and is also connected to L ₂ ;

Ar, whenever it appears, is selected identically or differently 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;

L ₁ is selected, identically or differently, from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 16 carbon atoms, or a combination thereof whenever it appears;

L ₂ is selected, identically or differently, from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof whenever it appears. become;

R _y independently or differently represents mono-substitution, poly-substitution or unsubstitution whenever it appears;

_{Whenever R} Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;

Each time R _y appears, it is identically or differently represented by hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 ring carbon atoms. A substituted or unsubstituted heteroalkyl group having a carbon atom, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 2 to 20 carbon atoms, Ringed alkynyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgerma having 6 to 20 carbon atoms selected from the group consisting of a nyl group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

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

Adjacent substituents R _y may be optionally connected to form a ring;

Adjacent substituents R _z may be arbitrarily connected to form a ring.

According to another embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer of the organic layer is according to the above-described embodiment. Includes the following compounds.

According to another embodiment of the present invention, a compound composition is further disclosed, which includes a compound according to the above-described embodiment.

The present invention discloses a series of heterocyclic compounds having the structure of formula 1. These new compounds can be applied to organic electroluminescent devices and can provide better device performance, especially improving device lifespan and significantly improving the overall performance of the device.

1 is a schematic diagram of an organic light emitting device that may contain the compounds and compound compositions disclosed herein.
Figure 2 is a schematic diagram of another organic light emitting device that may contain the compounds and compound compositions disclosed herein.

OLEDs can be manufactured 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 as needed. 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, and an electron transport layer ( 170), an electron injection layer 180, and a cathode 190. Device 100 may be fabricated by sequentially depositing the layers described. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of US Pat. No. 7,279,704B2, the entire contents of which are incorporated by reference in this application.

Each layer in these layers has more examples. An example is the flexible and transparent substrate-anode combination disclosed in U.S. Patent No. 5,844,363, which is combined in a manner cited in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4 -TCNQ at a molar ratio of 50:1 as disclosed in United States Patent Application Publication No. 2003/0230980, incorporated herein by reference in its entirety. U.S. Patent No. 6303238 (awarded to Thompson et al.), incorporated by reference in its entirety, discloses examples of host materials. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1 as disclosed in US Patent Application Publication No. 2003/0230980, incorporated herein by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entirety, disclose examples of cathodes, which are transparent, conductive, and sputter-deposited, overlying a thin layer of metal, such as Mg:Ag. It includes a composite cathode having an ITO layer deposited. In U.S. Patent No. 6097147 and U.S. Patent Application Publication No. 2003/0230980, which are combined by citing the entire text, the principle and use of the blocking layer are explained in more detail. United States 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 can be found in United States Patent Application Publication No. 2004/0174116, incorporated by reference in its entirety.

The above hierarchical structure is provided through a non-limiting example. The function of OLED can be implemented by combining the various types of layers described above, or some layers can be completely omitted. It may further include other layers that are not clearly 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 multiple sub-layers. For example, the light emitting layer may include two layers of different light emitting materials to implement a desired light emission spectrum.

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

OLED also requires an encapsulation layer, and FIG. 2 schematically and non-limitingly shows the organic light emitting device 200. The difference between this and FIG. 1 is that an encapsulation layer 102 is further included on the cathode 190 to prevent harmful substances (eg, moisture and oxygen) from the environment. Any material that can provide an encapsulation function can be used as the encapsulation layer (eg, glass or an organic-inorganic mixed layer). The encapsulation layer must be placed directly or indirectly on the outside of the OLED device. Multi-thin film encapsulation is described in US Patent US7968146B2, the entire contents of which are hereby incorporated by reference in their entirety.

Devices manufactured according to embodiments of the present invention can be integrated into various types of consumer goods that include one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signaling lights, head-up displays, fully transparent or partially transparent displays, flexible displays, Includes smartphones, tablets, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays and taillights. do.

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

As used in the text, “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 to be located relatively far from the substrate. There may be other layers between the first layer and the second layer, unless the first layer “and” the second layer are specified as being “in contact.” For example, even though several types of organic layers exist between the cathode and the anode, the cathode can still be described as being “placed” “on” the anode.

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

If the ligand is believed to directly affect the light-sensitive performance of the light-emitting material, the ligand may be referred to as a “photosensitive ligand.” If the ligand is believed to have no effect on 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% through 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 generated by triplet-triplet annihilation (TTA).

On the other hand, type E delayed fluorescence does not depend on the collision of two triplet states, but on the transition between a triplet state and a singlet-excited state. Compounds capable of producing E-type delayed fluorescence must have a very small singlet-triplet gap to enable transitions between energy states. Thermal energy can activate the transition from the triplet state to the singlet state. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delay factor increases as the temperature increases. If the rate of reverse intersystem crossing (RISC) is sufficiently fast to minimize non-radiative attenuation by triplet states, the proportion of back-filled singlet excited states can reach 75%. . The total proportion of singlet states can be 100%, which far exceeds 25% of the spin statistics of the excitons generated by the electric field.

The characteristic of type E delayed fluorescence can be found in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (△ES-T). Organic co-receptor luminescent materials containing non-metals have the potential to realize these characteristics. The emission of these materials is generally labeled as co-receptor charge transfer (CT) type emission. The spatial separation of HOMO and LUMO in these co-receptor compounds generally produces a small ΔES-T. These conditions may include CT conditions. Generally, a co-acceptor luminescent material is constructed by linking an electron co-porter moiety (e.g., an amino group or carbazole derivative) and an electron acceptor moiety (e.g., a six-membered aromatic ring containing N).

Regarding the definition of substituent terms,

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, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups 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-hexa Decyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3 -Contains a methylpentyl group. In the above, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, secondary butyl group, isobutyl group, t-butyl group, n-pentyl group, neopentyl group and n-hexyl group are preferred. Additionally, 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 a cycloalkyl group having 4 to 10 carbon atoms is preferred. Examples of cycloalkyl groups include cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4,4-dimethylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, and 1-norbornyl group. (1-norbornyl), 2-norbornyl group, etc. In the above, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, and 4,4-dimethylcyclohexyl group are preferred. Additionally, the cycloalkyl group may be optionally substituted.

The heteroalkyl group is as used herein, and the heteroalkyl group is one or more carbons in the alkyl group chain selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom, and boron atom. It includes those formed by substitution with a hetero atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl group, ethoxymethyl group, ethoxyethyl group, methylthiomethyl group, ethylthiomethyl group, ethylthioethyl group, methoxymethoxymethyl group, ethoxymethoxymethyl group, ethoxyethoxyethyl group, Hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, sulfanylmethyl group, sulfanylethyl group, sulfanylpropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylgermanylmethyl group, trimethylgermanylethyl group, Trimethyl germanyl isopropyl group, dimethyl ethyl germanyl methyl group, dimethyl isopropyl germanyl methyl group, tert-butyl dimethyl germanyl methyl group, triethyl germanyl methyl group, triethyl germanyl ethyl group, triisopropyl germanyl methyl group, triisopropyl It includes a germanyl ethyl group, trimethylsilylmethyl group, trimethylsilylethyl group, trimethylsilylisopropyl group, triisopropylsilylmethyl group, and triisopropylsilylethyl group. Additionally, 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 alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 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-phenyl allyl group, 3,3-diphenyl allyl group, 1,2-dimethyl allyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group, cyclopentenyl group, cyclopentadienyl group, It includes cyclohexenyl group, cycloheptenyl group, cycloheptatrienyl group, cyclooctenyl group, cyclooctatetraenyl group, and norbornenyl group. Additionally, the alkenyl group may be optionally substituted.

Alkynyl groups, as used in the text, include straight-chain alkynyl groups. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, and preferably may be an alkynyl group containing 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, and 3,3-dimethyl-1-butynyl group. , 3-ethyl-3-methyl-1-pentynyl group, 3,3-diisopropyl 1-pentynyl group, phenylethynyl group, phenylpropynyl group, etc. 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 preferred. Additionally, the alkynyl group may be optionally substituted.

Aryl or aromatic groups, as used in the text, are considered condensed and non-condensed systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl group, biphenyl group, terphenyl group, triphenylene group, tetraphenylene group, naphthyl group, anthracene group, phenalene group, phenanthrene group, fluorene group, pyrene group ( pyrene), a chrysene group, a perylene group, and an azulene group, and preferably includes a phenyl group, a biphenyl group, a terphenyl group, a triphenylene group, a fluorene group, and a nathalene group. do. Examples of non-fused aryl groups include phenyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, p-terphenyl-4-yl group, and 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) ) includes. Additionally, the aryl group may be optionally substituted.

Heterocyclic group or heterocyclyl, as used herein, refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, where at least one ring atom is a nitrogen atom or an oxygen atom. , a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom, and the preferred non-aromatic heterocyclic group is one containing 3 to 7 ring atoms, such as nitrogen, oxygen, silicon, or sulfur. Contains at least one heteroatom. Examples of non-aromatic heterocyclic groups include oxiranyl group, oxetanyl group, tetrahydrofuran group, tetrahydropyran group, and 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. Additionally, the heterocyclic group may be optionally substituted.

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

The alkoxy group, as used in the text, is represented by -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group, or -O-heterocyclic group. Examples and preferred examples of alkyl groups, cycloalkyl groups, heteroalkyl groups, and heterocyclic groups are as above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and is preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, and tetrahydrofuranyl oxide. It includes tetrahydrofuranyloxy group, tetrahydropyranyloxy group, methoxypropyloxy group, ethoxyethyloxy group, methoxymethyloxy group and ethoxymethyloxy group. Additionally, the alkoxy group may be optionally substituted.

Aryloxy group, as used in the text, is represented by -O-aryl group or -O-heteroaryl group. Illustrative and preferred examples of aryl groups and heteroaryl groups are as above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and is preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy groups and biphenyloxy groups. Additionally, the aryloxy group may be optionally substituted.

Arylalkyl group, as used herein, includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl isopropyl group, 2-phenyl isopropyl group, phenyl t-butyl group, α-naphthylmethyl group, and 1-α-naphthyl group. -Ethyl group, 2-α-naphthylethyl group, 1-α-naphthyl isopropyl group, 2-α-naphthyl isopropyl group, β-naphthylmethyl group, 1-β-naphthyl-ethyl group, 2-β- Naphthyl-ethyl group, 1-β-naphthyl isopropyl group, 2-β-naphthyl isopropyl 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- It includes hydroxy-2-phenylisopropyl group and 1-chloro-2-phenylisopropyl group. In the above, benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl isopropyl group and 2-phenyl isopropyl group. desirable. Additionally, the aralkyl group may be optionally substituted.

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

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

Alkylgermanyl, as used in the text, includes germanyl groups substituted with alkyl groups. The alkylgermanyl group may be an alkylgermanyl group having 3 to 20 carbon atoms, and is preferably an alkylgermanyl group having 3 to 10 carbon atoms. Examples of alkyl germanyl groups include trimethyl germanyl group, triethyl germanyl group, methyldiethyl germanyl group, ethyldimethyl germanyl group, tripropyl germanyl group, tributyl germanyl group, triisopropyl germanyl group, It includes methyl diisopropyl germanyl group, dimethyl isopropyl germanyl group, tri t-butyl germanyl group, triisobutyl germanyl group, dimethyl t-butyl germanyl group, and methyl di-t-butyl germanyl group. Additionally, the alkylgermanyl group may be optionally substituted.

Arylgermanyl, as used in the text, includes a germanyl group substituted with at least one aryl group or heteroaryl group. The aryl germanyl group may be an aryl germanyl group having 6 to 30 carbon atoms, and is preferably an aryl germanyl group having 8 to 20 carbon atoms. Examples of aryl germanyl groups include triphenyl germanyl group, phenyldiviphenyl germanyl group, diphenyl biphenyl germanyl group, phenyl diethyl germanyl group, diphenylethyl germanyl group, phenyl dimethyl germanyl group, and diphenyl germanyl group. It includes methyl germanyl group, phenyl diisopropyl germanyl group, diphenyl isopropyl germanyl group, diphenyl butyl germanyl group, diphenyl isobutyl germanyl group, and diphenyl t-butyl germanyl group. Additionally, the arylgermanyl 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. Those skilled in the art will readily be able to think of other nitrogen analogues of the aza derivatives described above, and all such analogues are hereby confirmed to be included within the terminology used 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 alkyl group. Nyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted alkylgermanyl group, substituted arylgermanyl group, substituted amino group, substituted When any one term from the group consisting of acyl group, substituted carbonyl group, substituted carboxylic acid group, substituted ester group, and substituted sulfinyl group is used, it means an alkyl group, cycloalkyl group, heteroalkyl group, heterocyclic group, Aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, alkylgermanyl group, arylgermanyl group, amino group, acyl group, carbonyl group, carboxyl group Any one of the acid group, ester group, sulfinyl group, sulfonyl group, and phosphino group is deuterium, halogen, unsubstituted alkyl group having 1 to 20 carbon atoms, and 3 to 20 ring carbon atoms. An unsubstituted cycloalkyl group having, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted heterocyclic group having 7 to 30 carbon atoms. aralkyl group, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, and an unsubstituted aryloxy group having 2 to 20 carbon atoms. an unsubstituted alkynyl group, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms. ), unsubstituted arylsilyl group having 6 to 20 carbon atoms, unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, unsubstituted arylgermanyl group having 6 to 20 carbon atoms, Unsubstituted amino group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, mercapto group, sulfinyl group, sulfonyl group, phosphine group having 0 to 20 carbon atoms. This means that it may be substituted by one or more groups selected from pino groups and combinations thereof.

It is to be understood that if a molecular fragment is described by a substituent or otherwise connected to another moiety, is it a fragment (e.g. a phenyl group, phenylene group, naphthyl group, dibenzofuran group) or is it a whole molecule (e.g. , benzene, naphthalene group, or dibenzofuran group). As used in the text, these different ways of designating substituents or fragment linkages are considered equivalent.

In the compounds mentioned 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 by their other stable isotopes. It may be desirable to substitute other stable isotopes in the compound as this improves the efficiency and stability of the device.

In the compounds mentioned in this application, multiple substitutions range up to the maximum possible substitutions, including double substitutions. In the compounds mentioned in the present application, when any substituent represents multiple substitution (including di-, tri-substitution, tetra-substitution, etc.), it indicates that the substituent in question may be present in a plurality of available substitution positions in the linking structure, Substituents present at a plurality of available substitution positions may have the same structure or may have different structures.

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

The intention of saying that adjacent substituents can be arbitrarily connected to form a ring is also to consider that two substituents bonded to the same carbon atom are connected to each other by a chemical bond to form a ring, which is exemplified through the formula below. :

.

The intent of the expression that adjacent substituents can be arbitrarily connected to form a ring is also to consider that two substituents bonded to carbon atoms directly bonded to each other are connected to each other by a chemical bond to form a ring, which is expressed in the formula below: This is illustrated through:

.

The intent of the expression that adjacent substituents can be arbitrarily connected to form a ring is also to consider that two substituents bonded to carbon atoms further apart are connected to each other by a chemical bond to form a ring, which is expressed through the formula below: Illustrative:

.

In addition, the intent of the expression that adjacent substituents can be arbitrarily connected to form a ring also means that when one of two adjacent substituents represents hydrogen, the second substituent is bonded to the position where the hydrogen atom is bonded to form a ring. It is intended to be considered. This is illustrated through the equation:

.

According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed, ,

here,

X is selected from O, S or Se;

X ₁ -X ₆ are selected identically or differently from CR _x or N each time they appear;

Z ₁ -Z ₈ are, identically or differently, selected from C, CR _z or N whenever they appear, and one of Z ₁ -Z ₄ is selected from C and is also connected to L ₂ ;

Ar, whenever it appears, is selected identically or differently 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;

L ₁ is selected, identically or differently, from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 16 carbon atoms, or a combination thereof whenever it appears;

L ₂ is selected, identically or differently, from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof whenever it appears. become;

R _y independently or differently represents mono-substitution, poly-substitution or unsubstitution whenever it appears;

_{Whenever R} Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;

Each time R _y appears, it is identically or differently represented by hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 ring carbon atoms. A substituted or unsubstituted heteroalkyl group having a carbon atom, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 2 to 20 carbon atoms, Ringed alkynyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgerma having 6 to 20 carbon atoms selected from the group consisting of a nyl group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

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

Adjacent substituents R _y may be optionally connected to form a ring;

Adjacent substituents R _z may be arbitrarily connected to form a ring.

In this document _, “adjacent substituents _R It means that one or more can be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

In this document, “adjacent substituents R _y may be optionally connected to form a ring” means that, in the adjacent substituent group, for example, between any two substituents R _y , any of these substituent groups It means that one or more can be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

In this document, “adjacent substituents R _z may be optionally connected to form a ring” means that, in the adjacent substituent group, for example, between any two substituents R _z , any of these substituent groups It means that one or more can be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

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

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

According to one embodiment of the invention, X ₁ -X ₆ are selected from CR _x the same or differently each time they appear.

According to one embodiment of the present invention, X ₁ -X ₆ is selected from CR _x or N identically or differently each time it appears, and at least one of X ₁ -X ₆ is selected from N; For example, one or two of X ₁ -X ₆ are selected from N.

According to one embodiment of the invention, Z ₁ -Z ₈ are selected from C or CR _z , identically or differently, whenever they appear, and one of Z ₁ -Z ₄ is selected from C and is also connected to L ₂ .

According to one embodiment of the invention, Z ₁ -Z ₈ are selected from C, CR _z or N, identically or differently, whenever they appear, and at least one of Z ₁ -Z ₈ is selected from N; For example, one or two of Z ₁ -Z ₈ are selected from N.

According to one embodiment of the present invention, L ₁ is selected identically or differently from substituted or unsubstituted arylene groups having 6 to 20 carbon atoms each time it appears.

According to one embodiment of the present invention, L ₁ is selected identically or differently from substituted or unsubstituted arylene groups having 6 to 12 carbon atoms each time it appears.

According to one embodiment of the present invention, L ₁ is the same or different each time it appears in a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a combination thereof. is selected.

According to one embodiment of the present invention, L ₂ is identical or different each time it appears, such as a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 20 carbon atoms. It is selected from an arylene group or a combination thereof.

According to one embodiment of the present invention, L ₂ is identical or different each time it appears, such as a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 12 carbon atoms. It is selected from an arylene group or a combination thereof.

According to one embodiment of the present invention, L ₂ is identical or different each time it appears, it is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or It is selected from unsubstituted pyridylene groups, or combinations thereof.

According to one embodiment of the present invention, L ₂ is selected from a single bond or a phenylene group identically or differently each time it appears.

According to one embodiment of the present invention, the compound has the structure of formula 1-1,

,

here,

Ar, whenever it appears, is selected identically or differently 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;

L ₁ is selected, identically or differently, from substituted or unsubstituted arylene groups having 6 to 30 carbon atoms each time it appears;

L ₂ is, whenever it appears, identically or differently selected from a single bond and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;

_{R _ _} Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, 6 to 30 carbon atoms A substituted or unsubstituted aryl group having a carbon atom, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms. A group consisting of a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof. is selected from;

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

Adjacent substituents R _y may be optionally connected to form a ring;

Adjacent substituents R _z may be arbitrarily connected to form a ring.

_{According to} one embodiment of the present invention _, R A substituted or unsubstituted cycloalkyl group having a carbon atom, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted group having 3 to 20 carbon atoms, or It is selected from the group consisting of unsubstituted heteroaryl groups, and combinations thereof.

_{According to} one embodiment of the present invention _, R Tyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorene group, substituted or unsubstituted carbazole group, substituted or unsubstituted di It is selected from the group consisting of a benzofuran group, a substituted or unsubstituted dibenzothiophene group, and combinations thereof.

According to one embodiment of _the present invention, _R It is selected from the group consisting of combinations of these.

According to one embodiment of the present invention, Ar represents, identically or differently, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or It is selected from a combination of these.

According to one embodiment of the present invention, Ar represents, 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 It is selected from a combination of these.

According to one embodiment of the present invention, Ar is the same or different each time it appears, such as a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted phenyl group. or an unsubstituted triphenylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, and combinations thereof. is selected from the group consisting of

According to one embodiment of the present invention, the compound is selected from the group consisting of Compound A-1 to Compound A-262, wherein the specific structures of Compound A-1 to Compound A-262 refer to claim 8.

According to one embodiment of the present invention, hydrogen in Compounds A-1 to Compound A-262 may be partially or completely replaced by deuterium.

According to one embodiment of the present invention, an organic electroluminescent device is disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one layer is any of the above-described embodiments. Includes compounds according to.

According to one embodiment of the present invention, the organic layer including the compound is a light-emitting layer, the compound is a host compound, and the light-emitting layer includes at least a first metal complex.

According to one embodiment of the present invention, the first metal complex has the general structure of M(L _a ) _m (L _b ) _n (L _c ) _q ;

Metal M is selected from metals with a relative atomic mass greater than 40;

Ligands L _a , L _b and L _c are the first, second and third ligands, respectively, coordinated with the metal M, and the ligands L _a , L _b and L _c may be the same or different;

Ligands L _a , L _b and L _c can be randomly linked to form multidentate ligands; For example, any two of L _a , L _b and L _c can be linked to form a tetradentate ligand; Or, for example, L _a , L _b and L _c may be optionally linked to form a hexadentate ligand; Or, for example, L _a , L _b and L _c may not all be linked to form a multidentate ligand;

m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; The sum of m+n+q is equal to the oxidation state of metal M; If m is greater than or equal to 2, multiple L _a may be the same or different; if n is 2, the two L _b may be the same or different; When q is 2, the two L _c can be the same or different;

Ligand L _a has the structure shown in Equation 2,

,

Ring C ₁ and Ring C ₂ , whenever they appear, are identically or differently selected from an aromatic ring having 5 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;

Q ₁ and Q ₂ are the same or different each time they appear. or is selected from N;

R ₁₁ and R ₁₂ identically or differently represent mono-substitution, poly-substitution or unsubstitution whenever they appear;

Whenever R ₁₁ and R ₁₂ appear, they are the same or different and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;

Adjacent substituents R ₁₁ and R ₁₂ may be optionally connected to form a ring;

The ligands L _b and L _c are selected from the same or different monovalent anionic bidentate ligands whenever they appear.

According to one embodiment of the present invention, the ligands L _b and L _c are selected from the group consisting of the following structures identically or differently each time they appear, , , , , , , , , , , ,

here,

R _a and R _b independently represent mono-substitution, poly-substitution or unsubstitution whenever they appear;

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

_{X c and}

R _a , R _b , R _{c ,} R _N1 , R _N2 , R _C1 and R _C2 are the same or different each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 carbon atoms. Substituted or unsubstituted cycloalkyl group having 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, 7 to 30 A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms. Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted group having 3 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylger having 3 to 20 carbon atoms Mannyl group, substituted or unsubstituted arylgermanyl 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, ester group, cyano group, iso is selected from the group consisting of cyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

Adjacent substituents R _a , R _b , R _{c ,} R _N1 , R _N2 , R _C1 and R _C2 may be optionally connected to form a ring.

In this example, “adjacent substituents R _a , R _b , R _{c ,} R _N1 , R _N2 , R _C1 and R _C2 may be optionally connected to form a ring” means that in the adjacent substituent group, for example For example, between two substituents R _a , between two substituents R _b , between substituents R _a and R _b , between substituents R _a and R _c , between substituents R _b and R _c , between substituents R _a and R _N1 , between substituents R between _b and R _N1 , between substituents R _a and R _C1 , between substituents R _a and R _C2 , between substituents R _b and R _C1 , between substituents R _b and R _C2 , and between R _C1 and R _C2 , with substituents R _a This means that between R _N2 and between substituents R _b and R _N2 , any one or more of these substituent groups may be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

According to one embodiment of the present invention, the first metal complex has the general formula Ir(L _a ) _m (L _b ) _3-m and has the structure shown in Equation 5;

,

here,

m is 0, 1, 2 or 3; When m is 2 or 3, multiple L _a are the same or different; When m is 0 or 1, multiple L _b are the same or different;

T ₁ -T ₆ are selected identically or differently from CR _T or N whenever they appear;

R _a , R _b and R _d identically or differently represent mono-substitution, poly-substitution or unsubstitution whenever they appear;

R _a , R _b , R _d and R _T are the same or different each time they appear; hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms. Ringed cycloalkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted group having 7 to 30 carbon atoms Aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, 2 Substituted or unsubstituted alkynyl group having ~20 carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, 3-20 carbon atoms a substituted or unsubstituted alkylsilyl group with A substituted or unsubstituted aryl germanyl group, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a sulfanyl group, and a hydroxy group. , sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

Adjacent substituents R _a and R _b may be optionally connected to form a ring;

Adjacent substituents R _d and R _T may be arbitrarily connected to form a ring.

In this embodiment, “adjacent substituents R _a and R _b may be arbitrarily connected to form a ring” means that, in the group of adjacent substituents, for example, between two adjacent substituents R _a , two adjacent substituents This means that between substituents R _b and between adjacent substituents R _a and R _b , any one or more of these substituent groups may be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

In this embodiment, “adjacent substituents R _d and R _T may be arbitrarily connected to form a ring” means that, in the group of adjacent substituents, for example, between two adjacent substituents R _T , two adjacent substituents This means that between the substituents R _d , any one or more of these substituent groups may be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

According to one embodiment of the present invention, at least one of T ₁ -T ₆ is selected from CR _T , wherein R _T is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 20 ring carbon atoms. It is selected from a substituted or unsubstituted cycloalkyl group, 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.

According to one embodiment of the present invention, at least one of T ₁ -T ₆ is selected from CR _T , and R _T is selected from fluorine or cyano group.

According to one embodiment of the present invention, at least two of T ₁ -T ₆ are selected from CR _T , one of them R _T is selected from fluorine or cyano group, and the other RT _T is selected from 1 to 20 groups. A substituted or unsubstituted alkyl group having a carbon atom, 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, or a substituted or unsubstituted aryl group having 3 to 30 carbon atoms. or an unsubstituted heteroaryl group.

According to one embodiment of the invention, T ₁ -T ₆ are selected from CR _T or N identically or differently whenever they appear, and at least one of T ₁ -T ₆ is selected from N, for example T ₁ - One or two of T ₆ are selected from N.

According to one embodiment of the present invention, the first metal complex is selected from the group including, but not limited to, GD1 to GD76, where the specific structures of GD1 to GD76 are as follows:

According to one embodiment of the present invention, the organic layer containing the compound is an electron transport layer, and the compound is an electron transport compound.

According to one embodiment of the present invention, in the organic electroluminescent device, the light emitting layer further includes a second host compound, and the second host compound is a phenyl group, a pyridine group, a pyrimidyl group, a triazine group, a carbazole group, and an azacarbazole group. , indolocarbazole group, dibenzothiophene group, azadibenzothiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenylene group, fluorene group, sila It contains at least one chemical group selected from the group consisting of fluorene group, naphthyl group, quinoline group, isoquinoline group, quinazoline group, quinoxaline group, phenanthrene group, azaphenanthrene group, and combinations thereof.

According to one embodiment of the present invention, in the organic electroluminescent device, the light emitting layer further includes a second host compound, and the second host compound is a phenyl group, a carbazole group, an indolocarbazole group, a fluorene group, and a silafluorene group. and at least one chemical group selected from the group consisting of combinations thereof.

According to one embodiment of the present invention, in the organic electroluminescent device, the second host compound has a structure represented by Formula 3,

,

here,

Whenever L _T appears, it represents, identically or differently, 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, or 6 to 20 carbon atoms. selected from a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

T is selected identically or differently from C, CR _t or N whenever it appears;

Each time R _t appears, it is identically or differently represented by hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 ring carbon atoms. A substituted or unsubstituted heteroalkyl group having a carbon atom, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 2 to 20 carbon atoms, Ringed alkynyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgerma having 6 to 20 carbon atoms Nyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino selected from the group consisting of groups and combinations thereof;

Ar ₁ is, whenever it appears, identically or differently 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 _t may be arbitrarily connected to form a ring.

In this context, “adjacent substituents R _t may be optionally connected to form a ring” means that in a group of adjacent substituents, for example, between any two substituents R _t , any one of this group of substituents or It means that plural numbers can be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

According to one embodiment of the present invention, in the organic electroluminescent device, the second host compound has a structure represented by Formula 4,

,

here,

G is the same or different every time it appears: C(R _g ) ₂ , NR _g , O or is selected from S;

T is selected identically or differently from C, CR _t or N whenever it appears;

Whenever L _T appears, it represents, identically or differently, 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, or 6 to 20 carbon atoms. selected from a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Whenever R _t and R _g appear, they are the same or different and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;

Ar ₁ is, whenever it appears, identically or differently 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 _t and R _g may be arbitrarily connected to form a ring.

In this document, “adjacent substituents R _t and R _g may be optionally connected to form a ring” means between two adjacent substituents R _t , between two adjacent substituents R _g , between adjacent substituents R _t and R _g . , meaning that any one or more of these substituent groups can be connected to form a ring. Obviously, all of these substituents are not connected and may not form a ring.

According to one embodiment of the present invention, in Equations 3 and 4, T is selected from C and CR _t identically or differently each time it appears.

According to one embodiment of the present invention, in Equation 3, T is selected equally or differently from C, CR _t or N whenever it appears, at least one of which is selected from N, for example one T or two T is selected from N.

According to one embodiment of the present invention, in Equation 4, T is selected equally or differently from C, CR _t or N each time it appears, at least one of which is selected from N, for example one T or two T is selected from N.

According to one embodiment of the present invention, in the organic electroluminescent device, the second host compound has a structure represented by one of Formulas 3-a to 3-j,

, , , , , , , , , ;

here,

Whenever L _T appears, it represents, identically or differently, 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, or 6 to 20 carbon atoms. selected from a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

T is selected from CR _t or N, identically or differently, wherever it appears;

Each time R _t appears, it is identically or differently represented by hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 ring carbon atoms. A substituted or unsubstituted heteroalkyl group having a carbon atom, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 2 to 20 carbon atoms, Ringed alkynyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgerma having 6 to 20 carbon atoms Nyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino selected from the group consisting of groups and combinations thereof;

Ar ₁ is, whenever it appears, identically or differently 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 _t may be arbitrarily connected to form a ring.

According to one embodiment of the present invention, in equations 3-a to 3-j, T is selected from CR _t or N identically or differently each time it appears, at least one of which is selected from N, for example One T or two T are selected from N.

According to one embodiment of the present invention, in the organic electroluminescent device, the second host compound has a structure represented by one of Formulas 4-a to 4-f,

, , , , , ;

here,

G is the same or different every time it appears: C(R _g ) ₂ , NR _g , O or is selected from S;

T is selected from CR _t or N, identically or differently, wherever it appears;

Whenever L _T appears, it represents, identically or differently, 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, or 6 to 20 carbon atoms. selected from a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Whenever R _t and R _g appear, they are the same or different and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;

Ar ₁ is, whenever it appears, identically or differently 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 _t and R _g may be arbitrarily connected to form a ring.

According to one embodiment of the present invention, in Equations 3-a to 3-j and Equations 4-a to 4-f, T is selected from CR _t identically or differently each time it appears.

According to one embodiment of the present invention, in equations 4-a to 4-f, T is selected from CR _t or N identically or differently each time it appears, at least one of which is selected from N, for example One T or two T are selected from N.

According to one embodiment of the invention, at least one of all T is selected from N, for example one or two of them are N.

According to one embodiment of the present invention, here, the organic electroluminescent device emits green light.

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

According to one embodiment of the present invention, here, the first metal complex is doped into the compound and the second compound, and the first metal complex accounts for 1% to 30% of the total weight of the first organic layer.

According to one embodiment of the present invention, here, the first metal complex is doped into the compound and the second compound, and the first metal complex accounts for 3% to 13% of the total weight of the first organic layer.

According to one embodiment of the present invention, a compound composition comprising a compound according to any of the above-described embodiments is disclosed.

According to one embodiment of the present invention, an electronic device including an organic electroluminescent device according to any of the above-described embodiments is disclosed.

Combination with other ingredients

The material used for a specific layer in the organic light emitting device described in the present invention may be used in combination with various other materials present in the device. This combination of materials is described in detail in paragraphs 0132 to 0161 of US patent application US2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned 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 easily refer to the literature to identify combinations and other materials that can be used.

In the text, it is explained that materials usable for specific layers in an organic light emitting device can be used in combination with various types of other materials present in the device. For example, the compounds disclosed herein can be used in combination with various types of hosts, dopants, 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 mentioned 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 easily 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 gas protection, unless otherwise noted. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized product can be obtained using one or several types of equipment conventional in the field (nuclear magnetic resonance spectrometer from BRUKER, liquid chromatography from SHIMADZU, liquid chromatograph-mass spectrometry, gas chromatograph-mass spectrometry ( gas chromatograph-mass spectrometry, differential scanning calorimeter, fluorescence spectrophotometer from Shanghai LENGGUANG TECH., electrochemical workstation from Wuhan CORRTEST, and sublimation apparatus from Anhui BEQ. ), the structure is confirmed and the properties are 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 the field (evaporator produced by ANGSTROM ENGINEERING, optical test system and life test system produced by Suzhou FATAR, ellipsometer produced by Beijing ELLITOP, etc.) It is tested by methods well known to those skilled in the art, using, but not limited to, methods well known to those skilled in the art. Those skilled in the art are familiar with the use of the above-mentioned equipment, test methods, etc., and can obtain the unique data of the sample reliably and without being affected. Therefore, the above-mentioned related matters will not be described further herein.

Material synthesis examples

There is no limitation on the manufacturing method of the compound of the present invention, and the following compounds are typically exemplified but are not limited thereto, and the synthetic route and manufacturing method are as follows:

Synthesis Example 1: Synthesis of Compound A-1

Step 1: Synthesis of Intermediate C

A (11.0g, 29.7mmol), B (12.6g, 44.6mmol), Pd(PPh ₃ ) ₄ (0.69g, 0.59mmol), and K ₂ CO ₃ (8.21g, 59.4mmol) were dissolved in toluene in a three-neck round bottom flask. (80mL), EtOH (20mL), and H ₂ O (20mL), protected with N ₂ , heated to reflux, and left overnight. Confirm the end of the reaction by spotting on a TLC plate, stop heating, cool to room temperature, separate liquids, extract the aqueous phase with DCM, combine the organic phases, dry with anhydrous Na ₂ SO ₄ , filter, and reduce pressure. Concentrate. The crude product was subjected to silica gel column chromatography (PE) to obtain intermediate C (11.2 g, 28.05 mmol) as a white solid, with a yield of 94.4%.

Step 2: Synthesis of Intermediate D

C (11.2g, 28.05mmol), bis(pinacolato)diborone (10.7g, 42.07mmol), Pd(dppf)Cl ₂ (0.41g, 0.56mmol), and KOAc (5.51g, 56.1mmol) in a three-neck round bottom flask. mmol) was added to 1,4-dioxane (120 mL), protected with N ₂ , heated to reflux, and left overnight. Confirm the completion of the reaction by spotting on a TLC plate, stop heating, and cool to room temperature. The reaction system was filtered through Celite, the filtrate was concentrated under reduced pressure, and the crude product was purified through silica gel column chromatography (PE/DCM=5:1 to 2:1) as intermediate D (10.3g, 23.08) as a white solid. mmol), and the yield is 82.3%.

Step 3: Synthesis of Compound A-1

D (4.0g, 8.96mmol), E (3.2g, 8.96mmol), Pd(PPh ₃ ) ₄ (0.31g, 0.27mmol), and K ₂ CO ₃ (2.48g, 17.92mmol) were dissolved in toluene in a three-neck round bottom flask. (48mL), EtOH (12mL), and H ₂ O (12mL), protected with N ₂ , heated to reflux, and left overnight. The completion of the reaction is confirmed by spotting on a TLC plate, heating is stopped, cooled to room temperature, reduced pressure and suction filtered, and the obtained solid is washed sequentially with water and methanol. The solid was recrystallized with toluene to obtain Compound A-1 (5.0 g, 7.79 mmol) as a white solid, with a yield of 87.0%. The product was confirmed to be the target product, Compound A-1, and its molecular weight was 641.2.

Synthesis Example 2: Synthesis of Compound A-3

Step 1: Synthesis of Compound A-3

D (4.46g, 10.0mmol), F (3.58g, 10.0mmol), Pd(PPh ₃ ) ₄ (0.35g, 0.30mmol), and K ₂ CO ₃ (2.76g, 20.0mmol) were dissolved in toluene in a three-neck round bottom flask. (48mL), EtOH (12mL), and H ₂ O (12mL), protected with N ₂ , heated to reflux, and left overnight. The completion of the reaction is confirmed by spotting on a TLC plate, heating is stopped, cooled to room temperature, reduced pressure and suction filtered, and the obtained solid is washed sequentially with water and methanol. The solid was recrystallized with toluene to obtain Compound A-3 (5.0 g, 7.79 mmol) as a white solid, with a yield of 77.9%. The product was confirmed to be the target product, Compound A-3, with a molecular weight of 641.2.

Synthesis Example 3: Synthesis of Compound A-4

Step 1: Synthesis of Compound A-4

D (4.46g, 10.0mmol), G (3.58g, 10.0mmol), Pd(PPh ₃ ) ₄ (0.23 g, 0.20 mmol), and K ₂ CO ₃ (2.76g, 20.0mmol) were dissolved in toluene in a three-neck round bottom flask. (40mL), EtOH (10mL), and H ₂ O (10mL), protected with N ₂ , heated to reflux, and left overnight. The completion of the reaction is confirmed by spotting on a TLC plate, heating is stopped, cooled to room temperature, reduced pressure and suction filtered, and the obtained solid is washed sequentially with water and methanol. The solid was recrystallized with toluene to obtain Compound A-4 (5.8 g, 9.04 mmol) as a white solid, with a yield of 90.4%. The product was confirmed to be the target product, Compound A-4, with a molecular weight of 641.2.

Those skilled in the art will know that the above-described production method is only an illustrative example, and that other compound structures of the present invention can be obtained by improving it.

Device embodiment

Device Example 1

First, a glass substrate equipped with an 80 nm thick indium tin oxide (ITO) anode 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 0.2-2 angstrom/sec at a vacuum degree of approximately 10 ^-8 Torr. Compound HI is used as a hole injection layer (HIL). The compound HT is used as the hole transport layer (HTL). Compound H1 is used as an electron blocking layer (EBL). Then, compound GD23 is doped with compound H1 and compound A-1 of the present invention, co-deposited, and used as an emitting layer (EML). Compound H2 is used as a hole blocking layer (HBL). On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited and used as an electron transport layer (ETL). Lastly, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is deposited and used as an electron injection layer, and aluminum with a thickness of 120 nm is deposited and used as a cathode. Next, the device is moved back to the glove box and encapsulated using a glass lid to complete the device.

Device Example 2

Except for using Compound A-3 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Device Example 2 is the same as Device Example 1.

Device Example 3

Except for using Compound A-4 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Device Example 3 is the same as Device Example 1.

Device Comparative Example 1

Except for using Compound C-1 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 1 is the same as Device Example 1.

Device Comparative Example 2

Except for using Compound C-2 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 2 is the same as Device Example 1.

Device Comparative Example 3

Except for using Compound C-3 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 3 is the same as Device Example 1.

Device Comparative Example 4

Except for using Compound C-4 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 4 is the same as Device Example 1.

Device Comparative Example 5

Except for using Compound C-5 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 5 was the same as Device Example 1.

Device Comparative Example 6

Except for using Compound C-6 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 6 was the same as Device Example 1.

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

[Table 1]

Device structures of Device Examples 1 to 3 and Comparative Examples 1 to 6

The material structure used in the device is as follows:

Table 2 shows CIE data, external quantum efficiency (EQE), and current efficiency (CE) measured at a constant current of 15 mA/cm ² ; and the device lifetime (LT95) measured at a constant current of 80 mA/cm ² . Based on the data of Comparative Example 1, normalization processing was performed.

[Table 2]

Device data of Examples 1 to 3 and Comparative Examples 1 to 6

debate:

In Example 3 and Comparative Example 1, the phosphorescent dopant GD23 was doped into the inventive compound A-4 and the non-inventive compound C-1, respectively. The difference between compounds A-4 and C-1 is that the dibenzofuran group directly bonded to the triazine group is replaced with a dibenzothiophene group. The EQE and CE of Example 3 were similar to Comparative Example 1, but the device lifespan was significantly improved by 61%. This explains that the compound having the structure of Formula 1 of the present invention has a longer device life when applied to an electroluminescent device compared to a compound in which a dibenzothiophene group and a triazine group are directly connected.

In Example 2 and Comparative Example 2, the phosphorescent dopant GD23 was doped into Compound A-3 of the present invention and Compound C-2, which is not of the present invention, respectively. The only difference between compounds A-3 and C-2 is the substitution position of the aryl group in the dibenzofuran group, which is connected to the triazinyl group through the phenylene group. The EQE and CE of Example 2 are similar to Comparative Example 2, but the device lifespan is significantly improved by 136%. This means that the compound having the structure of Formula 1 of the present invention is more effective in an electroluminescent device than a compound having an aryl substituent at a position other than the 1st position of the dibenzo five-membered ring with a bridging group between the triazinyl group. In application, it is explained that the device has a longer lifespan.

In Example 2 and Comparative Example 3, the phosphorescent dopant GD23 was doped into Compound A-3 of the present invention and Compound C-3, which is not of the present invention, respectively. The only difference between compounds A-3 and C-3 is whether the dibenzofuran group connected to the triazinyl group through the phenylene group forms a condensed ring through the phenyl group substituted at position 1. The EQE and CE of Example 2 were slightly improved, and the device lifespan was improved by 53%. This means that the compound having the formula 1 structure of the present invention is more effective in electroluminescence devices than the compound in which the aryl substituent at position 1 of the dibenzo 5-membered ring having a bridging group between the triazinyl group is additionally fused. In application, it is demonstrated that it has higher efficiency and longer device life.

In Example 1 and Comparative Example 4, the phosphorescent dopant GD23 was doped into Compound A-1 of the present invention and Compound C-4, which is not of the present invention, respectively. The difference between compounds A-1 and C-4 is mainly that the phenyl group substituent of the dibenzofuran group connected through the phenylene group is replaced with a substituted triazinyl group. The EQE and CE of Example 1 were improved by about 36%, and the device lifespan was improved by 45.4%. This means that the compound having the structure of Formula 1 of the present invention is an electroluminescent device compared to the compound having a 6-membered heteroaryl group substituted at position 1 of the 5-membered dibenzo ring having a bridging group between the triazinyl group and the triazinyl group. It is explained that it has higher efficiency and longer device life when applied to .

In Example 2 and Comparative Example 5, the phosphorescent dopant GD23 was doped into the inventive compound A-3 and the non-inventive compound C-5, respectively. The main difference between compounds A-3 and C-5 is that the dibenzofuran group with a phenyl group substitution at position 1 is connected to the triazinyl group through a phenylene group. The EQE and CE of Example 2 were improved by about 5%, and the device lifespan was improved by 28.2%. This means that the compound having the formula 1 structure of the present invention can improve the overall performance of the device when applied to an electroluminescent device compared to a compound in which a triazinyl group is directly connected to a dibenzo 5-membered ring having an aryl substituent at position 1. Explain that there is.

In Example 2 and Comparative Example 6, the phosphorescent dopant GD23 was doped into the inventive compound A-3 and the non-inventive compound C-6, respectively. The difference between compounds A-3 and C-6 is that they have an aryl substituent at position 1 of the dibenzofuran group, which is connected to the triazinyl group through the phenylene group. Compared to Comparative Example 6, the EQE and CE of Example 2 were similar, but its device lifespan was improved by 28.7%. This means that the compound having the formula 1 structure of the present invention has a longer device life when applied to an electroluminescent device compared to a compound without an aryl substituent on the five-membered dibenzo ring having a bridging group between the triazinyl group. Explain that it is provided.

In summary, when the compound of the present invention is used as the host material of the light-emitting layer, the electron and hole transport balance ability of the material is improved, and compared to using a compound other than the present invention as the host material of the light-emitting layer, the device efficiency (EQE and CE) is improved. ) is similar or improved to some extent, and at the same time, the lifespan of the device is greatly improved, and the overall performance of the device can be significantly improved. This is a significant help to the industry.

It should be understood that the various embodiments described in the text are merely illustrative and are not intended to limit the scope of the present invention. Accordingly, it is obvious to those skilled in the art that the claimed invention may include changes to the specific embodiments and preferred embodiments described in the text. Many of the materials and structures described in the text can be replaced with other materials and structures as long as they do not depart from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims (14)

Compounds having the structure Formula 1:
,
here,
X is selected from O, S or Se;
X ₁ -X ₆ are selected identically or differently from CR _x or N each time they appear;
Z ₁ -Z ₈ are, identically or differently, selected from C, CR _z or N whenever they appear, and one of Z ₁ -Z ₄ is selected from C and is also connected to L ₂ ;
Ar, whenever it appears, is selected identically or differently 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;
L ₁ is selected, identically or differently, from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 16 carbon atoms, or a combination thereof whenever it appears;
L ₂ is selected, identically or differently, from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof whenever it appears. become;
R _y independently or differently represents mono-substitution, poly-substitution or unsubstitution whenever it appears;
_{Whenever R} Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;
Each time R _y appears, it is identically or differently represented by hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or 1 to 20 ring carbon atoms. A substituted or unsubstituted heteroalkyl group having a carbon atom, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 2 to 20 carbon atoms, Ringed alkynyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgerma having 6 to 20 carbon atoms selected from the group consisting of a nyl group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
Adjacent substituents R _x may be optionally connected to form a ring;
Adjacent substituents R _y may be optionally connected to form a ring;
Adjacent substituents R _z may be arbitrarily connected to form a ring. 2. The method of claim 1, wherein X is selected from O or S; Preferably, X is O. 3. The method of claim 1 or 2, wherein X ₁ -X ₆ are selected from CR _x identically or differently each time they appear; and/or Z ₁ -Z ₈ are, identically or differently, selected from C or CR _z whenever they appear, and one of Z ₁ -Z ₄ is selected from C, and is also linked to L ₂ . The method according to any one of claims 1 to 3,
L ₁ is selected, identically or differently, from substituted or unsubstituted arylene groups having 6 to 20 carbon atoms each time it appears;
Preferably, L ₁ is a compound selected, identically or differently, from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a combination thereof whenever it appears. The method according to any one of claims 1 to 4,
L ₂ is selected, identically or differently, from 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 whenever it appears. become;
Preferably, L ₂ is the same or different each time it appears, and represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted pyridylene group. , or a combination thereof;
More preferably, the compound wherein L ₂ is selected identically or differently from a single bond or a phenylene group whenever it appears. The method according to any one of claims 1 to 5,
_{R _ _} Alkyl group, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and these is selected from the group consisting of a combination of;
_{Preferably , R} biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorene group, substituted or unsubstituted carbazole group, substituted or unsubstituted dibenzofuran group, substituted or A compound selected from the group consisting of unsubstituted dibenzothiophene groups, and combinations thereof. According to claim 1,
Ar, whenever it appears, is selected identically or differently from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or a combination thereof;
Preferably, Ar is the same or different each time it appears, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted triphenyl group. selected from the group consisting of a lene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, and combinations thereof. compound. The compound according to claim 1, selected from the group consisting of:





























Optionally, hydrogen in Compounds A-1 to Compound A-262 may be partially or completely replaced by deuterium. An organic electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound according to any one of claims 1 to 8. The organic electroluminescent device of claim 9, wherein the organic layer including the compound is a light-emitting layer, the compound is a host compound, and the light-emitting layer includes at least a first metal complex. The organic electroluminescent device of claim 10, wherein the first metal complex has the general formula M(L _a ) _m (L _b ) _n (L _c ) _q :
Metal M is selected from metals with a relative atomic mass greater than 40;
Ligands L _a , L _b and L _c are the first, second and third ligands, respectively, coordinated with the metal M, and the ligands L _a , L _b and L _c may be the same or different;
Ligands L _a , L _b and L _c can be randomly linked to form multidentate ligands;
m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; The sum of m+n+q is equal to the oxidation state of metal M; If m is greater than or equal to 2, multiple L _a may be the same or different; if n is 2, the two L _b may be the same or different; When q is 2, the two L _c can be the same or different;
Ligand L _a has the structure shown in Equation 2,
,
Ring C ₁ and Ring C ₂ , whenever they appear, are identically or differently selected from an aromatic ring having 5 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;
Q ₁ and Q ₂ are the same or different each time they appear. or is selected from N;
R ₁₁ and R ₁₂ identically or differently represent mono-substitution, poly-substitution or unsubstitution whenever they appear;
Whenever R ₁₁ and R ₁₂ appear, they are the same or different and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 1-20 Substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group, 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 having 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted group having 6 to 20 carbon atoms Aryl germanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group , phosphino groups, and combinations thereof;
Adjacent substituents R ₁₁ and R ₁₂ may be optionally connected to form a ring;
Ligands L _b and L _c are selected from the same or different monovalent anionic bidentate ligands whenever they appear;
Preferably, the ligands L _b and L _c are selected from the group consisting of the following structures identically or differently each time they appear,

here,
R _a and R _b independently represent mono-substitution, poly-substitution or unsubstitution whenever they appear;
X _b is, identically or differently, wherever it appears, selected from the group consisting of O, S, Se, NR _N1 and CR _C1 R _C2 ;
_{X c and}
R _a , R _b , R _{c ,} R _N1 , R _N2 , R _C1 and R _C2 are the same or different each time they appear: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 to 20 carbon atoms. Substituted or unsubstituted cycloalkyl group having 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, 7 to 30 A substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms. Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted group having 3 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylger having 3 to 20 carbon atoms Mannyl group, substituted or unsubstituted arylgermanyl 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, ester group, cyano group, iso is selected from the group consisting of cyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
Adjacent substituents R _a , R _b , R _{c ,} R _N1 , R _N2 , R _C1 and R _C2 may be optionally connected to form a ring. The method of claim 10, wherein the light emitting layer further includes a second host compound, and the second host compound is a phenyl group, a pyridine group, a pyrimidyl group, a triazine group, a carbazole group, an azacarbazole group, an indolocarbazole group, and a dibenzo group. Thiophene group, azadibenzothiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenylene group, fluorene group, silafluorene group, naphthyl group, quinoline It contains at least one chemical group selected from the group consisting of isoquinoline group, quinazoline group, quinoxaline group, phenanthrene group, azaphenanthrene group, and combinations thereof;
Preferably, the second host compound is an organic electroluminescent device comprising at least one chemical group selected from the group consisting of phenyl group, carbazole group, indolocarbazole group, fluorene group, silafluorene group, and combinations thereof. . The organic electroluminescent device of claim 12, wherein the second host compound has a structure represented by Formula 3 or Formula 4:
, ,
here,
G is the same or different every time it appears: C(R _g ) ₂ , NR _g , O or is selected from S;
Whenever L _T appears, it represents, identically or differently, 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, or 6 to 20 carbon atoms. selected from a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
T is selected identically or differently from C, CR _t or N whenever it appears;
Whenever R _t and R _g appear, they are the same or different and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 1 Substituted or unsubstituted heteroalkyl group having ~20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl group having 7-30 carbon atoms, 2-20 A substituted or unsubstituted alkenyl group having 6 to 30 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 a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms. Substituted or unsubstituted alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted having 6 to 20 carbon atoms or an unsubstituted arylgermanyl group, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, and a sulpi group. selected from the group consisting of a nyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Ar ₁ is, whenever it appears, identically or differently 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 _t and R _g may be optionally connected to form a ring;
Preferably, the second host compound has a structure represented by one of Formulas 3-a to 3-j, Formulas 4-a to 4-f,


Here, in Equations 3-a to 3-j, T, L _T , and Ar ₁ have the same definitions as those in Equation 3;
Here, in Equations 4-a to 4-f, T, G, L _T , and Ar ₁ have the same definitions as those in Equation 4. A compound composition comprising a compound according to any one of claims 1 to 8.