KR20240028316A - Organic electroluminescent material and device thereof - Google Patents

Abstract

The present invention discloses organic electroluminescent materials and devices thereof. The organic electroluminescent material is a compound having the structure of Formula 1, and the compound can be used in an organic electroluminescent device as, for example, a host material, a transport material, etc. Applying these compounds to organic electroluminescent devices can provide higher device efficiency, longer device life, and better device performance. An organic electroluminescent device containing the above compound and a compound composition containing the above compound were 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 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).

OLED can be classified into three different types depending on its 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 WO2020262861A1, the formula below: An organic compound having and an organic light-emitting device containing the compound are disclosed, where L is connected to carbon 1, carbon 2, or carbon 3, and L is a single bond, or substituted or unsubstituted C _6-60 of It is an arylene group; Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted aryl group of C _6-60 or a substituted or unsubstituted C _2-60 containing one or more groups selected from N, O and S. It is a heteroaryl group; R ₂ is each independently selected from a substituted or unsubstituted C _6-60 aryl group, a benzoxazole group, a benzothiazole group, a dibenzofuran group, or a benzothiazole group substituted with a phenyl group; q is an integer from 1 to 8. The application covers the following compounds in their specific structures: class started. In the above application, Ar ₁ and Ar ₂ are dibenzofuran groups and a compound linked to a triazine group fragment through the 2-position or 4-position and its effect on device performance were disclosed. The above application does not disclose or teach about compounds in which the 3-position of the dibenzofuran group is connected to a triazine group fragment and their application in organic electroluminescent devices.

In WO2021040467A1, the following chemical structure: Disclosed is an organic compound having and an organic light-emitting device containing the compound, wherein Ar is a substituted or unsubstituted C _6-60 It is an aryl group; R ₁ and R ₂ are each independently substituted or unsubstituted C _6-60 Aryl group, or substituted or unsubstituted C _5-60 containing one or more heteroatoms selected from N, O and S It is a heteroaryl group. The application covers the following compounds in their specific structures: started. The application disclosed a compound having at least two carbazole groups to a phenylene group connected to a triazine group and its effect on device performance. The above application does not disclose or teach about compounds having only one carbazole group with a phenylene group connected to a triazine group and their application in organic electroluminescent devices.

In WO2021080368A1, the following chemical structure: Disclosed is an organic compound having and an organic light-emitting device containing the compound, wherein X is O and S, Y is N or CH, but two or more of Y are N; L is a phenylene group substituted by a phenylene group, biphenyldiyl group, terphenyldiyl group, naphthalenediyl group, or naphthyl group; R ₄ is a substituted or unsubstituted C _6-60 aryl group. In the above application, the following compounds in their specific structures class started. In the above application, a compound in which the 4th position of the dibenzofuran group is linked to a triazine group fragment and a compound in which the 3rd position of the dibenzothiophene group is linked to a triazine group fragment are disclosed, but the 3rd position of the dibenzofuran group is a triazine group. There is no disclosure or teaching about the compounds linked to the fragments and their applications in organic electroluminescent devices.

In WO2020111586A1, the following chemical structure: Disclosed is an organic compound having and an organic light-emitting device containing the compound, wherein X is each independently N or CH, two or more of X are N, and Ar ₁ and Ar ₂ are each independently substituted or an unsubstituted C _6-60 aryl group, a substituted or unsubstituted C _5-60 heteroaryl group containing N, O or S, and L is a single bond, a substituted or unsubstituted C _6-60 An arylene group is a substituted or unsubstituted C _5-60 heteroarylene group containing N, O or S, and E is a substituted or unsubstituted C _5-60 heteroaryl containing one or more N. , D is , , or is selected from In the above application, the following compounds in their specific structures was initiated. The above application does not disclose or teach the compound when the substituent E is an aryl group and its effect on device performance.

US20190341553A1 has the following chemical structure: Disclosed is an organic compound having a and an organic light-emitting device containing the compound, where n is an integer in the range of 0 to 2, and Ar ¹ and Ar ² are each independently substituted or unsubstituted C6 to C30 aryl. It is a group or a group represented by the formula A, and at least one of Ar ¹ and Ar ² is a group represented by the formula A, and the formula A is , where X ¹ is O or S. The application covers the following compounds in their specific structures: class started. The application discloses a compound without a phenyl substituent on the phenylene group linked to the carbazole group fragment, and a compound having a substituent at the meta position of the triazine group fragment in the phenylene group linked to the carbazole group fragment. There was no disclosure or teaching about compounds having a substituent in the para position of the triazine group in the ren group and their application in organic electroluminescent devices.

US2019214570A1 has the following chemical structure: disclosed an organic compound having and an organic light-emitting device containing the compound, where Ar ₁ and Ar ₂ are , , may be selected from; L ₁ , L ₂ and L ₁₁ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₆₀ carbon ring, and a substituted or unsubstituted C ₁ -C ₆₀ heterocycle; a1, a2 and a11 are each independently an integer from 1 to 10; E ₁ is selected from C(R ₂₁ )(R ₂₂ ), Si(R ₂₃ )(R ₂₄ ), N(R ₂₅ ), O and S. The application covers the following compounds in their specific structures: started. The application disclosed a compound in which the 1st position of the dibenzofuran group was linked to a triazine group fragment through a phenylene group, but the compounds and organic electroluminescent devices in which the 3rd position of the dibenzofuran group was linked to the triazine group fragment through a phenylene group. did not disclose or teach its application in .

Triazine-based organic semiconductor materials are widely used in OLEDs due to their excellent photoelectric performance, redox performance, and stability. However, when using the triazine-based organic semiconductor materials reported so far in organic electroluminescent devices, there are still certain limitations in device performance, such as reduced device lifespan. Therefore, the application potential of triazine-based organic semiconductor materials is worthy of further research and development.

The present invention aims to provide a series of compounds having the structure of Formula 1 in order to at least partially solve the above problems. The above compounds can be used in organic electroluminescent devices, for example, as host materials, transport materials, etc. Applying these new compounds to electroluminescent devices can provide better device performance, for example, maintain high device efficiency or further improve device efficiency, and also significantly improve device lifespan.

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

[Equation 1]

,

here,

U is selected from O or Se;

X ₁ and X ₂ are selected identically or differently from C, CR _x or N whenever they appear; One of X ₁ and X ₂ is selected from C and connected to N;

Y ₁ and Y ₂ are selected from CR _y or N identically or differently whenever they appear;

Z ₁ -Z ₄ are selected identically or differently from CR _z or N whenever they appear;

E ₁ -E ₄ are selected identically or differently from CR _e or N whenever they appear;

V ₁ -V ₇ are selected identically or differently from CR _v or N whenever they appear;

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

_{R , R _} or an unsubstituted cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, or a substituted or unsubstituted group having 7 to 30 carbon atoms. Ringed 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 , a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, 3 to 20 Substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms A substituted or unsubstituted aryl germanyl group having a carbon atom, 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, selected from the group consisting of sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, 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 alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, selected from the group consisting of 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;

L is 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 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;

Ar, whenever it appears, is 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 _y may be optionally connected to form a ring;

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

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

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

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

Adjacent substituents R and R _y cannot be 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, and at least one layer of the organic layer is a compound according to the above-described embodiment. Includes.

According to another example of the present invention, a compound composition including the compound according to the above-described example is further disclosed.

The present invention discloses a compound having the structure of Formula 1. The compounds can improve the performance of phosphorescent organic light-emitting devices and provide better device performance, for example, maintain high device efficiency or further improve device efficiency, and also significantly improve device lifespan. .

1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.
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 (ΔES-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-type 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,

[Equation 1]

,

here,

U is selected from O or Se;

X ₁ and X ₂ are selected identically or differently from C, CR _x or N whenever they appear; One of X ₁ and X ₂ is selected from C and connected to N;

Y ₁ and Y ₂ are selected from CR _y or N identically or differently whenever they appear;

Z ₁ -Z ₄ are selected identically or differently from CR _z or N whenever they appear;

E ₁ -E ₄ are selected identically or differently from CR _e or N whenever they appear;

V ₁ -V ₇ are selected identically or differently from CR _v or N whenever they appear;

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

_{R , R _} or an unsubstituted cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, or a substituted or unsubstituted group having 7 to 30 carbon atoms. Ringed 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 , a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, 3 to 20 Substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms A substituted or unsubstituted aryl germanyl group having a carbon atom, 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, selected from the group consisting of sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, 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 alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, selected from the group consisting of 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;

L is 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 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;

Ar, whenever it appears, is 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 _y may be optionally connected to form a ring;

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

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

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

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

Adjacent substituents R and R _y cannot be connected to form a ring.

In this text, “adjacent substituents R _y may be arbitrarily connected to form a ring” means that any two adjacent substituents R _y may be connected to form a ring. Obviously, any adjacent R _y may not be connected and thus may not form a ring.

In this text, “adjacent substituents R may be arbitrarily connected to form a ring” means that any two adjacent substituents R may be connected to form a ring. Obviously, any adjacent R may not all be connected and thus not form a ring.

In the present text, “adjacent substituents R _v may be arbitrarily connected to form a ring” means that any two adjacent substituents R _v may be connected to form a ring. Obviously, any adjacent R _v may not be connected and thus may not form a ring.

In this text, “adjacent substituents R _z may be arbitrarily connected to form a ring” means that any two adjacent substituents R _z may be connected to form a ring. Obviously, any adjacent R _z may not all be connected and thus not form a ring.

In this text, “adjacent substituents R _e may be arbitrarily connected to form a ring” means that any two adjacent substituents R _e may be connected to form a ring. Obviously, any adjacent R _e may not be connected to form a ring.

In the present text, “adjacent substituents R and R _y cannot be connected to form a ring” means that any two adjacent substituents R and R _y are not connected and cannot form a ring. am.

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

According to one embodiment of the present invention, Y ₁ and Y ₂ are selected from CR _y the same or differently each time they appear.

According to one embodiment of the invention, Z ₁ -Z ₄ are selected from CR _z the same or differently each time they appear.

According to one embodiment of the invention, E ₁ -E ₄ are selected from CR _e the same or differently each time they appear.

According to one embodiment of the invention, V ₁ -V ₇ are selected from CR _v identically or differently each time they appear.

According to one embodiment of the invention, X ₁ and X ₂ are selected from C or CR _x each time they appear; One of X ₁ and X ₂ is selected from C and connected to N.

According to one embodiment of the invention, X ₁ is selected from CR _x ; X ₂ is selected from C and connected to N.

According to one embodiment of the present invention, at least one of V ₁ -V ₇ is selected from CR _v , and R _v is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, which is the same or different each time it appears, It is selected from substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof.

According to one embodiment of the present invention, at least one of V ₄ -V ₇ is selected from CR _v , and R _v is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, which is the same or different each time it appears, It is selected from substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof.

According to one embodiment of the present invention, V ₇ is selected from CR _v , and R _v is, the same or differently, each time it appears, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or 3 to 18 carbon atoms. It is selected from a substituted or unsubstituted heteroaryl group, or a combination thereof.

According to one embodiment of the present invention, L is a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof. is selected.

According to one embodiment of the present invention, L 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 unsubstituted pyridylene group, or It is selected from a combination of these.

According to one embodiment of the present invention, L is selected from a single bond or a phenylene group.

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 is the same or differently each time it appears: a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted biphenyl group, Substituted or unsubstituted terphenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted carbazole group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted is selected from the group consisting of pyridine groups and combinations thereof.

According _to one embodiment of the _present invention, _R , _R Substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, 3 to 20 carbon atoms It is selected from the group consisting of substituted or unsubstituted heteroaryl groups having carbon atoms, cyano groups, and combinations thereof.

According to one embodiment _{of the} present invention, _R , _R , 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 dibenzo It is selected from the group consisting of a furan group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted pyridine group, and combinations thereof.

According to one embodiment of the present invention, R _y is the same or different each time it appears, 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. It is selected from the group consisting of a ringed cycloalkyl group, 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 cyano group, and combinations thereof.

According to one embodiment of the present invention, R _y is the same or different each time it appears, such as hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or It is selected from the group consisting of an unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorene group, and combinations thereof.

According to another embodiment of the present invention, the compound is selected from the group consisting of Compound A-1 to Compound A-732, and the specific structures of Compound A-1 to Compound A-732 refer to claim 9.

According to one embodiment of the present invention, hydrogen in the structures of Compounds A-1 to Compounds A-732 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 the organic layer contains a compound according to any of the above-described embodiments. Includes.

According to one embodiment of the present invention, in the organic electroluminescent device, 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, in the organic electroluminescent device, 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 organic layer containing the compound is a hole blocking layer, and the compound is a hole blocking compound.

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

According to one embodiment of the present invention, the second host material contains at least one chemical group selected from the group consisting of a phenyl group, carbazole group, indolocarbazole group, fluorene group, silafluorene group, and combinations thereof. Includes.

According to one embodiment of the present invention, the second host compound has a structure represented by Formula 2 or Formula 3,

[Equation 2]

,

[Equation 3]

;

here,

G is identically or differently selected from C(R _g ) ₂ , NR _g , O or S whenever it appears; If multiple R _g exist at the same time, the multiple R _g may be the same or different;

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 equally or differently from C, CR _T or N whenever it appears;

R _T and R _g are the same or different each time they appear and are 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 A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms. Substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted having 6 to 20 carbon atoms Ringed arylsilyl 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, sulfanyl group, hydroxy group, sulfinyl group, sulfo selected from the group consisting of a nyl group, a phosphino group, and combinations thereof;

Whenever Ar ₁ and Ar ₂ appear, they are the same or different and are 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. become;

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

In the present text, “adjacent substituents R _T and R _g 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 R _g and between adjacent substituents R _T and R _g , any one or more of these substituent groups may be connected to form a ring. As will be apparent to those skilled in the art, such adjacent groups of substituents may not all be linked to form a ring.

According to one embodiment of the present invention, the second host compound has a structure represented by one of Formulas 2-a to 2-j and Formulas 3-a to 3-f;

, , , , , , , , , , , , , , , ;

Here, in Formulas 2-a to 2-j, the definitions of T, L _T , and Ar ₁ are the same as those in Formula 2;

Here, in Equations 3-a to 3-f, the definitions of T, G, L _T , and Ar ₂ are the same as those in Equation 3.

According to one embodiment of the present invention, the second host compound is selected from the group consisting of the following compounds.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , .

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;

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

L _a , L _b and L _c can be randomly 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 4,

[Equation 4]

,

Ring A ₁ and Ring A 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;

P ₁ and P ₂ are, identically or differently, selected from O, C or N whenever they appear;

D ₁ and D ₂ are, identically or differently, selected from single bond, O or S whenever they appear;

L ₁ is a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene group, ethynylene group, 6~ selected from the group consisting of a substituted or unsubstituted arylene group having 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; When two R's exist simultaneously, the two R's are either the same or different;

a ₁ is selected from 0 or 1;

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

R ₁₁ , R ₁₂ , and R', each time they appear, are the same or differently represented by hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 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, 2 to 20 carbon atoms Substituted or unsubstituted alkynyl group having carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, or Unsubstituted arylgermanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group , sulfonyl group, phosphino group, and combinations thereof;

Adjacent substituents R ₁₁ , R ₁₂ , and R' 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.

In this embodiment, “adjacent substituents R ₁₁ , R ₁₂ , and R’ may be arbitrarily connected to form a ring” means that, in the group of adjacent substituents, for example, between adjacent substituents R ₁₁ and between adjacent substituents Between R ₁₂ , between adjacent substituents R' and between adjacent substituents R ₁₁ and R ₁₂ , this means that 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 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.

In this embodiment, adjacent substituents R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 may be arbitrarily connected to form a ring, which means that in the adjacent substituent group, for example, , between two adjacent substituents R _a , between two adjacent substituents R _b , between two adjacent substituents R _c , between substituents R _a and R _b , between substituents R _a and R _c , between substituents R _b and R _c , substituents Between R _a and R _N1 , between substituents R _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 , between substituents R _a and R _N2 , between substituents R _b and R _N2 , and between substituents R _C1 and R _C2 , meaning that any one or more of these substituent groups may be connected to form a ring. for example, Adjacent substituents R _a and R _b may be randomly connected to form a ring, which has the following structure: , , , , , , or Including, but not limited to, one or more of the following; Here, W is selected from O, S, Se, NR _w or CR _w R _w , and the definitions of R _w , Ra _' , and R _b ' are the same as for R _a . Obviously, all of these substituents are not connected and may not form a ring.

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

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

According to one embodiment of the present invention, the first metal complex has the general structure M(L _a1 ) _j (L _b1 ) _k , where M is selected from metals with a relative atomic mass greater than 40;

L _a1 and L _b1 are the first and second ligands that coordinate with M, respectively, and L _a1 and L _b1 may be arbitrarily linked to form a multidentate ligand;

j is 1, 2 or 3, k is 0, 1 or 2, the sum of j and k is equal to the oxidation state of M, and when j is greater than or equal to 2, multiple L _a1 may be the same or different. can; When k is 2, the two L _b1 can be the same or different;

The L _a1 has the structure shown in Formula 4-1,

[Equation 4-1]

,

here,

Ring F is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

Ring F and Ring E are fused through U ₁ and U ₂ ;

U ₁ and U ₂ are selected identically or differently from C or N whenever they appear;

R _F , R _E each time they appear identically or differently represent mono-substitution, poly-substitution or unsubstitution;

Y is selected from CR _Y or N, identically or differently, each time it appears;

R _F , R _E , and R _Y are identical or different each time they appear, and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 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. Substituted or unsubstituted arylsilyl 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, sulpi group selected from the group consisting of a nyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R _F , R _E , _RY may be optionally connected to form a ring;

The ligand L _b1 has a structure shown in Formula 4-2,

[Equation 4-2]

,

Here, R ₂₁ to R ₂₇ are each independently 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, and 1 to 20 ring carbon atoms. Substituted or unsubstituted heteroalkyl group having 3 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, 1 to 20 carbon atoms. a substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 6 to 30 carbon atoms, or Unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted having 6 to 20 carbon atoms Arylsilyl 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, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and It is selected from the group consisting of combinations of these.

In the present text, adjacent substituents R _F , R _E , _RY may be optionally connected to form a ring, meaning that when substituents R _F , substituents R _E , and substituents _RY are present, the adjacent substituent group, for example, Between adjacent substituents R _F , between adjacent substituents R _E , between adjacent substituents _RY , between adjacent substituents R _F and R _E , between adjacent substituents R _F and _RY and between adjacent substituents R _E and _RY , among these adjacent substituents This means that any one or more of them can be connected to form a ring. Obviously, when substituents R _F , substituents R _E , and substituents R _Y are present, these substituents may not all be connected and thus not form a ring.

According to one embodiment of the present invention, in Formula 4-2, at least one of R ₂₁ -R ₂₃ 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. selected from a cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and/or at least one of R ₂₄ -R ₂₆ is 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 a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms. or an unsubstituted heteroalkyl group, or a combination thereof.

According to one embodiment of the present invention, in Formula 4-2, at least two of R ₂₁ -R ₂₃ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted alkyl groups having 3 to 20 ring carbon atoms. selected from a ringed cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and/or at least two of R ₂₄ -R ₂₆ are 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 a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms. It is selected from substituted or unsubstituted heteroalkyl groups, or combinations thereof.

According to one embodiment of the present invention, in Formula 4-2, at least two of R ₂₁ -R ₂₃ are identical or different each time they appear, a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, or 3 to 20 carbon atoms. selected from a substituted or unsubstituted cycloalkyl group having a ring carbon atom, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof; and/or at least two of R ₂₄ -R ₂₆ are identical or different each time they appear, a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, It is selected from substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.

According to one embodiment of the present invention, the first metal complex has the general structure of Ir(L _a1 ) ₂ (L _b1 ).

According to one embodiment of the present invention, the first metal complex is an Ir metal complex and includes a ligand L _a1 , wherein L _a1 has a structure represented by Formula 4-1, and has a 6-membered ring and a 6-membered ring. an aromatic ring formed by fusing a 6-membered ring to a 6-membered ring, a heteroaromatic ring formed by fusing a 6-membered ring with a 6-membered ring, a 6-membered ring fused with a 5-membered ring It includes at least one structural unit selected from the group consisting of an aromatic ring formed and a heteroaromatic ring formed by fusing a 6-membered ring and a 5-membered ring.

According to one embodiment of the present invention, the first metal complex is an Ir metal complex and includes a ligand L _a1 , wherein L _a1 has a structure represented by Formula 4-1, and includes a naphthyl group, a phenanthrene group, and quinoline. It contains at least one structural unit selected from the group consisting of a group, an isoquinoline group, and an azaphenanthrene group.

According to one embodiment of the present invention, the first metal complex has a structure shown in Equation 4-3,

[Equation 4-3]

,

here,

The metal M is selected, identically or differently, from metals with a relative molecular mass greater than 40 each time it appears;

Rings A ₁ -A ₄ , whenever they appear, are identically or differently selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;

L ₁ -L ₄ are the same or different each time they appear, a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted. selected from the group consisting of a vinylene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; When two R's exist simultaneously, the two R's are either the same or different;

a _1- a ₄ are selected from 0 or 1, identically or differently, each time they appear;

P ₁ -P ₄ are, identically or differently, selected from O, C or N whenever they appear;

D ₁ -D ₄ are, identically or differently, selected from a single bond, O or S whenever they appear;

R ₁₁ -R ₁₄ identically or differently represent mono-substitution, poly-substitution or unsubstitution each time they appear;

R ₁₁ -R ₁₄ , R', each time they appear, are the same or differently represented by hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 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, 2 to 20 carbon atoms Substituted or unsubstituted alkynyl group having carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, or Unsubstituted arylgermanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group , sulfonyl group, phosphino group, and combinations thereof;

Adjacent substituents R ₁₁ -R ₁₄ and R' may be optionally connected to form a ring.

In this embodiment, “adjacent substituents R ₁₁ -R ₁₄ , R’ may be arbitrarily connected to form a ring” means that, in the group of adjacent substituents, for example, between adjacent substituents R ₁₁ and between adjacent substituents Between R ₁₂ , between adjacent substituents R ₁₃ , between adjacent substituents R ₁₄ , and between adjacent substituents R’, this means that 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 Formula 4-4;

[Equation 4-4]

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 and are 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 a fluorine or cyano group.

According to one embodiment of the present invention, at least one of T ₁ -T ₄ is selected from CR _t , and R _t is a 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 R _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 present 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 consisting of the following compounds.

, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , .

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, dopant, transport layer, blocking layer, injection layer, electrode, 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 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 more types of equipment conventional in the field (nuclear magnetic resonance spectroscopy from Bruker, liquid chromatography from Shimadzu, liquid chromatograph-mass spectrometry, gas chromatography-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 compounds of the present invention, and typical examples include, but are not limited to, the following compounds, and their synthetic routes and manufacturing methods are as follows:

<Synthesis Example 1: Synthesis of Compound A-1>

Step 1: Synthesis of Intermediate C

Add 200 mL of A (22.2 g, 106.0 mmol), B (17.7 g, 106.0 mmol), cesium carbonate (Cs ₂ CO ₃ , 69.1 g, 212.0 mmol), and N,N-dimethylformamide (DMF) to a three-neck round bottom flask. Add sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is added to a large amount of water, extracted by adding ethyl acetate, the organic phase is collected, and concentrated under reduced pressure to obtain a crude product. The crude product was beaten with absolute ethanol to obtain intermediate C (26.7 g, 74.9 mmol) as a white solid, with a yield of 70.7%.

Step 2: Synthesis of Intermediate E

In a three-neck round bottom flask, intermediates C (18.9g, 53.0mmol), D (9.5g, 77.9mmol), Pd(PPh ₃ ) ₄ (2.4g, 2.1mmol), K ₂ CO ₃ (14.6g, 106.0mmol) , 160mL of toluene, 40mL of EtOH, and 40mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction liquid is separated, the water phase is extracted with DCM, and the organic phase is combined. Anhydrous Na ₂ SO ₄ was added to the organic phase, dried, reduced pressure and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=10:1 to 8:1) to obtain intermediate E (16.8g, 47.5mmol) as a white solid, with a yield of 89.6%.

Step 3: Synthesis of Intermediate F

In a three-neck round bottom flask, intermediate E (16.8g, 47.5mmol), bis(pinacolato)diborone (18.1g, 71.3mmol), Pd ₂ (dba) ₃ (0.87g, 0.95mmol), tricyclohexylphos Phonium tetrafluoroborate (PCy ₃ ·HBF ₄ , 0.87g, 0.95mmol), KOAc (9.3g, 95.0mmol), and 150mL of 1,4-dioxane are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction system is filtered through Celite, and the filtrate is reduced in pressure and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=5:1 to 2:1) to obtain intermediate F (18.0g, 40.4mmol) as a white solid, with a yield of 85.0%.

Step 4: Synthesis of Compound A-1

In a three-neck round bottom flask, intermediates F (4.0g, 9.0mmol), G (3.2g, 9.0mmol), Pd(PPh ₃ ) ₄ (0.2g, 0.18mmol), K ₂ CO ₃ (2.5g, 18.0mmol) , 40mL of toluene, 10mL of EtOH, and 10mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and beaten with ethanol to obtain a light yellow solid (3.2 g, 5.0 mmol), with a yield of 55.6%. The product was confirmed to be the target product, A-1, with a molecular weight of 640.2.

<Synthesis Example 2: Synthesis of Compound A-192>

Step 1: Synthesis of Intermediate J

In a three-neck round bottom flask, intermediates H (4.38g, 11.83mmol), I (4.01g, 17.74mmol), Pd(PPh ₃ ) ₄ (0.41g, 0.36mmol), KHCO ₃ (2.37g, 23.66mmol), THF Add 80 mL and 20 mL of H ₂ O sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The organic phase is taken, DCM is added to the aqueous phase, extracted several times, the organic phases are combined, dried over anhydrous Na ₂ SO ₄ , filtered and tumble dried. The crude product was purified by silica gel column chromatography (PE/DCM=5:1 to 4:1) to obtain intermediate J (1.1g, 2.54mmol) as a white solid, with a yield of 21.5%.

Step 2: Synthesis of Compound A-192

In a three-neck round bottom flask, intermediates F (1.1g, 2.54mmol), J (1.13g, 2.54mmol), Pd(PPh ₃ ) ₄ (0.09g, 0.08mmol), K ₂ CO ₃ (0.7g, 5.08mmol) , 16 mL of toluene, 4 mL of EtOH, and 4 mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and beaten with ethanol to obtain a light yellow solid (1.3 g, 1.81 mmol), with a yield of 71.3%. The product was confirmed to be the target product, A-192, with a molecular weight of 716.3.

Synthesis Example 3: Synthesis of Compound A-259

Step 1: Synthesis of Intermediate L

In a three-neck round bottom flask, intermediates K (14.8g, 40.0mmol), I (11.8g, 52.0mmol), Pd(PPh ₃ ) ₄ (1.4g, 1.2mmol), Na ₂ CO ₃ (8.5g, 80.0mmol) , 320 mL of THF and 80 mL of H ₂ O are added sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates, it is filtered, the solid is washed with water and ethanol, and recrystallized with toluene to obtain intermediate L (10.1 g, 23.3 mmol) as a white solid, with a yield of 58.3%.

Step 2: Synthesis of Compound A-259

In a three-neck round bottom flask, intermediates F (3.5g, 8.0mmol), L (3.6g, 8.0mmol), Pd(PPh ₃ ) ₄ (0.18g, 0.16mmol), K ₂ CO ₃ (2.2g, 16.0mmol) , 24 mL of toluene, 6 mL of EtOH, and 6 mL of H ₂ O are added sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and beaten with ethanol to obtain a light yellow solid (2.8 g, 3.9 mmol), with a yield of 48.8%. The product was confirmed to be the target product, A-259, with a molecular weight of 716.3.

<Synthesis Example 4: Synthesis of Compound A-302>

Step 1: Synthesis of Intermediate N

In a three-neck round bottom flask, intermediates M (6.0g, 20.0mmol), G (7.2g, 20.0mmol), Pd(PPh ₃ ) ₄ (0.46g, 0.4mmol), K ₂ CO ₃ (5.5g, 40.0mmol) , 60mL of toluene, 15mL of EtOH, and 15mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized with toluene and beaten with ethanol to obtain intermediate N (8.0 g, 16.2 mmol) as a white solid, with a yield of 81.1%.

Step 2: Synthesis of Compound A-302

Add intermediates N (4.9g, 10.0mmol), B (1.8g, 10.5mmol), cesium carbonate (6.5g, 20.0mmol), and 60mL of DMF to a three-neck round bottom flask sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is added to a large amount of water, extracted by adding ethyl acetate, the organic phase is collected, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=10:1 to 3:1) to obtain a light yellow solid (5.1g, 7.96mmol), with a yield of 79.6%. The product was confirmed to be the target product, A-302, with a molecular weight of 640.2.

<Synthesis Example 5: Synthesis of Compound A-414>

Step 1: Synthesis of Intermediate O

In a three-neck round bottom flask, intermediates M (4.7g, 15.7mmol), L (6.8g, 15.7mmol), Pd(PPh ₃ ) ₄ (0.36g, 0.3mmol), K ₂ CO ₃ (4.3g, 31.4mmol) , 40mL of toluene, 10mL of EtOH, and 10mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized with toluene and beaten with ethanol to obtain intermediate O (4.8 g, 8.4 mmol) as a white solid, with a yield of 53.5%.

Step 2: Synthesis of Compound A-414

Add intermediate O (4.8g, 8.4mmol), B (1.4g, 8.4mmol), cesium carbonate (5.5g, 16.8mmol), and 80mL of DMF to the three-necked round bottom flask sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is added to a large amount of water, extracted by adding ethyl acetate, the organic phase is collected, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=10:1 to 3:1) to obtain a light yellow solid (4.5g, 6.3mmol), with a yield of 75.0%. The product was confirmed to be the target product, A-414, with a molecular weight of 716.3.

<Synthesis Example 6: Synthesis of Compound A-314>

Step 1: Synthesis of Intermediate Q

In a three-neck round bottom flask, intermediates M (4.1g, 13.7mmol), P (5.4g, 12.4mmol), Pd(PPh ₃ ) ₄ (0.29g, 0.25mmol), K ₂ CO ₃ (3.4g, 24.8mmol) , 40mL of toluene, 10mL of EtOH, and 10mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized with toluene and beaten with ethanol to obtain intermediate Q (5.1 g, 8.95 mmol) as a white solid, with a yield of 72.2%.

Step 2: Synthesis of Compound A-314

Add intermediate Q (5.1g, 8.95mmol), B (1.65g, 9.85mmol), cesium carbonate (5.8g, 17.9mmol), and 50mL of DMF to a three-neck round bottom flask sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is added to a large amount of water, extracted by adding ethyl acetate, the organic phase is collected, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=10:1 to 3:1) to obtain a light yellow solid (5.7g, 7.95mmol), with a yield of 78.8%. The product was confirmed to be the target product, A-314, with a molecular weight of 716.3.

<Synthesis Example 7: Synthesis of Compound A-330>

Step 1: Synthesis of Intermediate S

In a three-neck round bottom flask, intermediates R (3.7g, 10.0mmol), G (3.6g, 10.0mmol), Pd(PPh ₃ ) ₄ (0.23g, 0.2mmol), K ₂ CO ₃ (2.8g, 20.0mmol) , 40mL of toluene, 10mL of EtOH, and 10mL of H ₂ O are sequentially added. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. When a large amount of solid precipitates in the reaction solution, it is filtered, and the obtained solid is washed sequentially with water and ethanol to obtain a crude product. The crude product was recrystallized with toluene and beaten with ethanol to obtain intermediate S (5.2g, 9.13mmol) as a white solid, with a yield of 91.3%.

Step 2: Synthesis of Compound A-330

Add intermediates S (5.2g, 9.13mmol), B (1.7g, 10.1mmol), cesium carbonate (6.0g, 18.4mmol), and 50mL of DMF to a three-neck round bottom flask sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is added to a large amount of water, extracted by adding ethyl acetate, the organic phase is collected, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=10:1 to 3:1) to obtain a light yellow solid (3.8g, 5.3mmol), with a yield of 58.1%. The product was confirmed to be the target product, A-330, with a molecular weight of 716.3.

<Synthesis Example 8: Synthesis of Compound A-530>

Step 1: Synthesis of Compound A-530

Add intermediate N (4.2g, 8.5mmol), T (2.27g, 9.35mmol), cesium carbonate (5.54g, 17.0mmol), and 60mL of DMF to a three-neck round bottom flask sequentially. Under N ₂ protection, heat and reflux and stay overnight. Confirm the completion of the reaction by TLC, stop heating, and cool to room temperature. The reaction solution is added to a large amount of water, extracted by adding ethyl acetate, the organic phase is collected, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE/DCM=10:1 to 3:1) to obtain a light yellow solid (5.0g, 6.98mmol), with a yield of 82.1%. The product was confirmed to be the target product, A-530, with a molecular weight of 716.3.

As those skilled in the art will know, the above production method is only an illustrative example, and those skilled in the art can obtain the structures of other compounds of the present invention by using it.

It should be understood that the manufacturing method of the electroluminescent device is not limited, and the manufacturing method in the following examples is only an example and is not intended to be limiting. A person skilled in the art can reasonably describe the manufacturing method of the following examples according to the prior art. Illustratively, the proportions of various materials in the light emitting layer are not particularly limited, and those skilled in the art can reasonably select them within a certain range according to prior art. For example, based on the total weight of the light-emitting layer material, the host material accounts for 80-99%, the light-emitting material accounts for 1-20%; Alternatively, the host material accounts for 90-99% and the light-emitting material accounts for 1-10%; Alternatively, the host material may account for 95%-99% and the light-emitting material may account for 1%-5%. Additionally, the host material may be one or two materials, where the ratio of the two host materials to the host material is 100:0 to 1:99, or 80:20 to 20:80, or 60: It may be 40 to 40:60.

<Device Example>

<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 via thermal vacuum deposition at a rate of 0.2-2 angstrom/sec at a vacuum degree of approximately 10 ^-8 Torr. Compound HI was used as a hole injection layer (HIL, 100Å). Compound HT is used as a hole transport layer (HTL, 350Å). Compound PH-23 is used as an electron blocking layer (EBL, 50Å). Then, compound GD1 is doped with compound PH-23 and compound A-1 of the present invention, co-deposited, and used as an emitting layer (EML, 400Å, weight ratio is 8:69:23). Compound HB is used as a hole blocking layer (HBL, 50Å). On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) are co-deposited and used as an electron transport layer (ETL, 350 Å, weight ratio is 40:60). Finally, 1 nm thick 8-hydroxyquinoline-lithium (Liq) is deposited to form an electron injection layer, and 120 nm thick aluminum is deposited to use as a cathode. Next, the device is completed by transferring it back to the glove box and encapsulating it using a glass lid.

<Device Example 2>

Except for using Compound A-259 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-302 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 Example 4>

Except for using Compound A-414 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Device Example 4 is the same as Device Example 1.

<Device Example 6>

Except for using Compound A-314 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Device Example 6 is the same as Device Example 1.

<Device Example 7>

Except for using Compound A-330 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Device Example 7 is the same as Device Example 1.

<Device Example 8>

Except for using Compound A-530 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Device Example 8 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 was 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 was 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 is the same as Device Example 1.

<Device Comparative Example 7>

Except for using Compound C-7 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 7 was the same as Device Example 1.

<Device Comparative Example 9>

Except for using Compound C-8 instead of Compound A-1 in the emitting layer (EML), the manufacturing method of Comparative Device Example 9 is the same as Device Example 1.

The detailed device layer 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.

Partial device structures of Device Examples 1 to 4 and Examples 6 to 8 and Comparative Examples 1 to 7 and Comparative Example 9 Device ID HIL HTL EBL E.M.L. HBL ETL Example 1 Compound HI
(100Å) compound HT
(350Å ) Compound PH-23
(50Å) Compound PH-23: Compound A-1: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Example 2 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound A-259: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Example 3 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound A-302: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Example 4 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound A-414: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Example 6 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound A-314: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Example 7 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound A-330: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Example 8 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound A-530: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 1 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-1: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 2 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-2: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 3 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-3: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 4 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å ) Compound PH-23: Compound C-4: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 5 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-5: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 6 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-6: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 7 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-7: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å) Comparative Example 9 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-23: Compound C-8: Compound GD1 (69:23:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å)

The material structure used in the device is as follows:

, , , , , , , , , , , , , , , , , , , , , .

Table 2 shows CIE data, driving voltage, external quantum efficiency (EQE), current efficiency (CE) and power efficiency (PE) measured at a constant current of 15 mA/cm ² ; and the device lifetime (LT97) measured at a constant current of 80 mA/cm ² .

Device data of Examples 1 to 4 and Examples 6 to 8 and Comparative Examples 1 to 7 and Comparative Example 9 Device ID E.M.L. CIE (x,y) driving voltage
(V) EQE
(%) C.E.
(cd/A) LT97
(h) Example 1 PH-23:A-1:GD1 (69:23:8) (0.358, 0.617) 4.0 21.5 82 51.3 Example 2 PH-23:A-259:GD1 (69:23:8) (0.359, 0.617) 4.0 21.4 82 54.2 Example 3 PH-23:A-302:GD1 (69:23:8) (0.359, 0.617) 4.0 21.8 83 56.2 Example 4 PH-23:A-414:GD1 (69:23:8) (0.358, 0.618) 4.1 21.7 83 61.5 Example 6 PH-23:A-314:GD1 (69:23:8) (0.358, 0.618) 4.1 21.7 83 59.2 Example 7 PH-23:A-330:GD1 (69:23:8) (0.352, 0.622) 4.1 22.03 84 54.3 Example 8 PH-23:A-530:GD1 (69:23:8) (0.353, 0.621) 4.1 21.7 83 51.3 Comparative Example 1 PH-23:C-1:GD1 (69:23:8) (0.350, 0.624) 4.2 22.0 84 3.2 Comparative Example 2 PH-23:C-2:GD1 (69:23:8) (0.349, 0.624) 4.1 21.9 84 29.8 Comparative Example 3 PH-23:C-3:GD1 (69:23:8) (0.362, 0.615) 4.1 21.1 80 20.5 Comparative Example 4 PH-23:C-4:GD1 (69:23:8) (0.360, 0.616) 4.3 19.1 73 38.5 Comparative Example 5 PH-23:C-5:GD1 (69:23:8) (0.351, 0.621) 4.1 21.9 84 28.0 Comparative Example 6 PH-23:C-6:GD1 (69:23:8) (0.354, 0.621) 4.2 21.1 81 24.7 Comparative Example 7 PH-23:C-7:GD1 (69:23:8) (0.357, 0.618) 4.3 20.7 79 39.2 Comparative Example 9 PH-23:C-8:GD1 (69:23:8) (0.354, 0.620) 4.5 2.0 6.2 90.0

In Example 1, Comparative Example 1, Comparative Example 2, and Comparative Example 7, Compound A-1 of the present invention and Compound C-1, Compound C-2, and Compound C-7, which are not of the present invention, were used, respectively. The difference between Compound A-1 and Compound C-1, Compound C-2 and Compound C-7 is only that the dibenzofuran group is connected to the triazine group through a different linking position. In compound A-1, the 3-position of the dibenzofuran group is connected to a triazine group, and in compound C-1, the 2-position of the dibenzofuran group is connected to a triazine group; In compound C-2, position 4 of the dibenzofuran group is connected to the triazine group; In compound C-7, position 1 of the dibenzofuran group is connected to the triazine group. From the data in Table 2, in terms of driving voltage, EQE and CE, Example 1 remains basically similar to Comparative Example 1 and Comparative Example 2, but in terms of device life, compared to Comparative Example 1 and Comparative Example 2, Example 1 The lifespan of was improved by 15 times and 0.7 times, respectively; Compared to Comparative Example 7, the driving voltage of Example 1 was lowered by 0.3V, EQE was improved by 3.9%, CE was improved by 3.8%, and device life was significantly improved by 31%. This means that the compound having the formula 1 structure of the present invention, when applied to an electroluminescent device, compared to the compound in the existing technology in which the 1st, 2nd, or 4th positions of the dibenzofuran group are connected to a triazine group. Explain that it has the effect of unexpectedly improving lifespan.

In Example 1 and Comparative Example 3, Compound A-1 of the present invention and Compound C-3, which is not of the present invention, were used, respectively. The difference between Compound A-1 and Compound C-3 is that the groups connected to the triazine group are dibenzofuran group and dibenzothiophene group, respectively. From the data in Table 2, it can be seen that the driving voltage, EQE, and CE of Example 1 are similar to Comparative Example 3, but the device lifespan is significantly improved by 1.5 times. This explains that the compound having the structure of Formula 1 of the present invention has the effect of unexpectedly improving device life when applied to an electroluminescent device compared to a compound in which a dibenzothiophene group is connected to a triazine group.

In Example 1 and Comparative Example 4, Compound A-1 of the present invention and Compound C-4, which is not of the present invention, were used, respectively. The difference between Compound A-1 and Compound C-4 lies only in whether or not there is an additional heteroaryl substituent on the phenylene group. The phenylene group of compound A-1 has only one carbazole substituent, and the phenylene group of compound C-4 has another carbazole substituent in addition to the meta position of the carbazole group. Compared to Comparative Example 4, the driving voltage of Example 1 was lowered by 0.3V, EQE was improved by 12.6%, CE was improved by 12.3%, and device lifespan was significantly improved by 33.2%. This explains that the compound having the formula 1 structure of the present invention can significantly improve the device life when applied to an electroluminescent device compared to a compound having an additional heteroaryl substituent on the phenylene group.

In Example 1 and Comparative Example 5, Compound A-1 of the present invention and Compound C-5, which are not of the present invention, were used, respectively. The difference between Compound A-1 and Compound C-5 lies only in whether there is a phenyl substituent on the phenylene group, which is a bridging group connecting the carbazole group and the triazine group. From the data in Table 2, it can be seen that the driving voltage, EQE, and CE of Example 1 are basically similar to Comparative Example 5, but the device lifespan is significantly improved by 83.2%. This shows that the compound having the formula 1 structure of the present invention can significantly improve the device life when applied to an electroluminescent device compared to a compound without an aryl substituent on the phenylene group, which is the linking group connecting the carbazole group and the triazine group. Explain.

In Example 1 and Comparative Example 6, Compound A-1 of the present invention and Compound C-6, which is not of the present invention, were used, respectively. The difference between Compound A-1 and Compound C-6 is only that the position of the phenyl substituent in the phenylene group, which is the linking group connecting the carbazole group and the triazine group, is different. In compound A-1, the phenyl substituent is in the para position of the triazine group; In compound C-6, the phenyl substituent is in the meta position of the triazine group. From the data in Table 2, it can be seen that the driving voltage, EQE, and CE of Example 1 remain basically similar to Comparative Example 6, but the device lifespan is greatly improved by 1.08 times, which is very rare. This is because the compound having the structure of formula 1 of the present invention, when applied to an electroluminescent device, has a phenyl substituent in a position other than the para position of the triazine group in which the phenylene group, which is a linking group connecting the carbazole group and the triazine group, has a lower Explain that it has the effect of unexpectedly improving lifespan.

In Example 3 and Comparative Example 9, compound A-302 of the present invention and compound C-8, which is not of the present invention, were used, respectively. The difference between Compound A-302 and Compound C-8 is only that the substituents on the phenylene group, which is the linking group connecting the carbazole group and the triazine group, are different. In compound A-302, the substituent on the phenylene group is a benzene ring; On the other hand, in compound C-8, the substituent on the phenylene group is a triazine group. From the data in Table 2, compared to Comparative Example 9, the driving voltage of Example 3 was lowered by 0.5 V, and more importantly, the EQE of Comparative Example 9 was only 2.0% and the CE was only 6.2 cd/A, compared to Compared to Example 9, in Example 3, EQE was significantly improved by 990%, and CE was significantly improved by 1239%. This improvement is very unexpected. What should be noted is that the device efficiency of Comparative Example 9 is very low, that is, the number of photons emitted by the device is very small (the luminance of the device is extremely low), so the device lifespan is naturally relatively long, but the performance of such a device is very limited. and has no commercial application value. This means that the compound having the structure of formula 1 of the present invention shows better overall performance of the device when applied to an electroluminescent device compared to a compound in which a triazine substituent is connected to a phenylene group, which is a linking group connecting a carbazole group and a triazine group. Explain what you have.

As can be seen from the above, Compound A-1 of the present invention used in Example 1 can provide relatively excellent device performance, and based on this, the compound structure was further modified and substituted to produce compounds A-259, A- 302, and A-414, A-314, A-330 and A-530, and on the basis of the excellent device performance of Example 1, Examples 2 to 4 and Examples 6 to 8 are Having the same low driving voltage as 1, the same excellent device efficiency (EQE, CE), and also on the basis of the relatively high device life of Example 1, Examples 2 to 4 and Examples 6 to 8 Device lifespan remained similar or was further improved.

The above results show that the compound of formula 1 structure having a specific substituent at the substitution position specified in the present invention improves device performance, maintains high device efficiency, or improves device efficiency compared to the triazine-based compound in the existing technology. This indicates that the lifespan of the device can be significantly improved while further improving, and ultimately the overall performance of the device can be improved.

<Device Example 5>

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 via thermal vacuum deposition at a rate of 0.2-2 angstrom/sec at a vacuum degree of approximately 10 ^-8 Torr. Compound HI was used as a hole injection layer (HIL, 100Å). Compound HT is used as a hole transport layer (HTL, 350Å). Compound PH-23 is used as an electron blocking layer (EBL, 50Å). Then, compound GD1 is doped with compound PH-1 and compound NH-1, co-deposited, and used as an emission layer (EML, 400 Å, weight ratio is 8:55:37). Compound HB is used as a hole blocking layer (HBL, 50Å). On the hole blocking layer, Compound A-1 of the present invention and 8-hydroxyquinoline-lithium (Liq) are co-deposited and used as an electron transport layer (ETL, 350Å, weight ratio is 40:60). Finally, 1 nm thick 8-hydroxyquinoline-lithium (Liq) is deposited to form an electron injection layer, and 120 nm thick aluminum is deposited to use as a cathode. Next, the device is completed by transferring it back to the glove box and encapsulating it using a glass lid.

<Device Comparative Example 8>

Except for using Compound ET instead of Compound A-1 in the electron transport layer (ETL), the manufacturing method of Comparative Device Example 8 is the same as Device Example 5.

The detailed device layer 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.

Partial device structure of Device Example 5 and Comparative Example 8 Device ID HIL HTL EBL E.M.L. HBL ETL Example 5 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-1: Compound NH-1: Compound GD1 (55:37:8) (400 Å) Compound HB
(50Å) Compound A-1: Liq (40:60) (350 Å) Comparative Example 8 Compound HI
(100Å) compound HT
(350Å) Compound PH-23
(50Å) Compound PH-1: Compound NH-1: Compound GD1 (55:37:8) (400 Å) Compound HB
(50Å) Compound ET: Liq (40:60) (350 Å)

The structure of the metal complex newly used in the device is as follows:

, .

Table 4 shows CIE data, driving voltage (V), external quantum efficiency (EQE) measured at a constant current of 15 mA/cm ² , and device lifetime (LT97) measured at a constant current of 80 mA/cm ² .

Device data of Example 5 and Comparative Example 8 Device ID ETL CIE (x, y) driving voltage
(V) EQE
(%) life span
LT97(h) Example 5 A-1 : Liq (40:60) (0.360, 0.617) 3.7 21.3 46.7 Comparative Example 8 ET:Liq (40:60) (0.361, 0.616) 3.7 20.9 46.3

debate

In Example 5 and Comparative Example 8, compound A-1 of the present invention and compound ET, which is not of the present invention, were used as electron transport materials, respectively. From the data in Table 4, the driving voltage of Example 5 is the same as Comparative Example 8, but from the already very high level of EQE and device life of Comparative Example 8, the EQE and device life of Example 5 are further improved, which is very high. It's rare. It should be noted that compound ET is currently a commercial electron transport material. Compared to compound ET, when the compound of the present invention is applied to an electroluminescent device, a similar or more improved device level can be maintained, and from this, it can be seen that the compound of the present invention is also a type of electron transport material with excellent commercial potential.

In summary, applying the compound of the present invention to an organic electroluminescent device can improve the overall performance of the device, maintain high device efficiency or further improve device efficiency, and especially significantly improve device lifespan, and provide a wider range of benefits. It has application prospects.

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 (15)

Compounds having the structure Formula 1:
[Equation 1]
,
here,
U is selected from O or Se;
X ₁ and X ₂ are selected identically or differently from C, CR _x or N whenever they appear; One of X ₁ and X ₂ is selected from C and connected to N;
Y ₁ and Y ₂ are selected from CR _y or N identically or differently whenever they appear;
Z ₁ -Z ₄ are selected identically or differently from CR _z or N whenever they appear;
E ₁ -E ₄ are selected identically or differently from CR _e or N whenever they appear;
V ₁ -V ₇ are selected identically or differently from CR _v or N whenever they appear;
R, identically or differently, represents mono-substitution, poly-substitution or unsubstitution whenever it appears;
_{R , R _} or an unsubstituted cycloalkyl group, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, or a substituted or unsubstituted group having 7 to 30 carbon atoms. Ringed 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 , a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, 3 to 20 Substituted or unsubstituted alkylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, 6 to 20 carbon atoms A substituted or unsubstituted aryl germanyl group having a carbon atom, 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, selected from the group consisting of sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, 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 alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms group, substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, selected from the group consisting of 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;
L is 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 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;
Ar, whenever it appears, is 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 _y may be optionally connected to form a ring;
Adjacent substituents R may be optionally connected to form a ring;
Adjacent substituents R _v may be optionally connected to form a ring;
Adjacent substituents R _z may be optionally connected to form a ring;
Adjacent substituents R _e may be arbitrarily connected to form a ring. According to paragraph 1,
U is a compound selected from O. According to claim 1 or 2,
Y ₁ and Y ₂ are selected from CR _y each time they appear, either identically or differently; and/or Z ₁ -Z ₄ are selected identically or differently from CR _z whenever they appear, and E ₁ -E ₄ are selected identically or differently from CR _e whenever they appear; and/or V ₁ -V ₇ are selected from CR _v identically or differently each time they appear; and _/ or X _{1 and} A compound in which one of X ₁ and X ₂ is selected from C and is connected to N. According to paragraph 3,
At least one of V ₁ -V ₇ is selected from CR _v , and R _v is, identically or differently, each time it appears, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 3 to 30 carbon atoms, or selected from unsubstituted heteroaryl groups, or combinations thereof;
Preferably, at least one of V ₄ -V ₇ is selected from CR _v , and R _v is the same or different each time it appears, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or 3 to 30 carbon atoms. selected from a substituted or unsubstituted heteroaryl group, or a combination thereof;
More preferably, V ₇ is selected from CR _v , and R _v is, identically or differently, each time it appears, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted aryl group having 3 to 18 carbon atoms. A compound selected from a heteroaryl group, or a combination thereof. According to paragraph 1,
L is selected 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;
Preferably, L is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, or a combination thereof; ;
More preferably, L is a compound selected from a single bond or a phenylene group. According to paragraph 1,
Ar, whenever it appears, is identically or differently selected 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 differently substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted phenanthrene group, substituted or unsubstituted biphenyl group, substituted or unsubstituted group, whenever Ar appears. Phenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted carbazole group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted pyridine group and these A compound selected from the group consisting of combinations. According to paragraph 1,
_{R , R _} or an unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 20 carbon atoms. selected from the group consisting of aryl groups, cyano groups, and combinations thereof;
_{Preferably ,} R _{, 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 unsubstituted A compound selected from the group consisting of a ringed dibenzothiophene group, and combinations thereof. According to paragraph 1,
Each time R _y appears, it is the same or different and represents 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 2 to 20 ring carbon atoms. selected from the group consisting of substituted or unsubstituted alkenyl groups having carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof;
Preferably, R _y is identical or different each time it appears, hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, A compound selected from the group consisting of a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorene group, and combinations thereof. According to paragraph 1,
A compound selected from the group consisting of:
, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ;
Optionally, a compound in which hydrogen in the structures of Compounds A-1 to Compound A-732 may be partially or fully replaced by deuterium. anode,
cathode, and
An organic electroluminescent device comprising an organic layer disposed between the anode and the cathode, and at least one layer of the organic layer comprising the compound according to any one of claims 1 to 9. According to clause 10,
The organic layer containing 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; or the organic layer containing the compound is an electron transport layer, and the compound is an electron transport compound; Or, an organic electroluminescent device in which the organic layer containing the compound is a hole blocking layer, and the compound is a hole blocking compound. According to clause 11,
The light emitting layer further includes a second host compound, and the second host compound includes a phenyl group, a pyridine group, a pyrimidyl group, a triazine group, a carbazole group, an azacarbazole group, an indolocarbazole group, a dibenzothiophene group, and an azadi group. Benzothiophene group, dibenzofuran group, azadibenzofuran group, dibenzoselenophene group, triphenylene group, azatriphenylene group, fluorene group, silafluorene group, naphthyl group, quinoline group, isoquinoline group, Contains at least one chemical group selected from the group consisting of quinazoline group, quinoxaline group, phenanthrene group, azaphenanthrene group, and combinations thereof;
Preferably, the second host material 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. . According to clause 12,
The second host compound is an organic electroluminescent device having a structure represented by Formula 2 or Formula 3:
[Equation 2]
,
[Equation 3]
;
here,
G is identically or differently selected from C(R _g ) ₂ , NR _g , O or S whenever it appears; If multiple R _g exist at the same time, the multiple R _g may be the same or different;
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 equally or differently from C, CR _T or N whenever it appears;
R _T and R _g are the same or different each time they appear and are 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 A substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted alkenyl group having 6 to 30 carbon atoms. Substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted having 6 to 20 carbon atoms Ringed arylsilyl 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, sulfanyl group, hydroxy group, sulfinyl group, sulfo selected from the group consisting of a nyl group, a phosphino group, and combinations thereof;
Whenever Ar ₁ and Ar ₂ appear, they are the same or different and are 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. become;
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 2-a to 2-j and Formulas 3-a to 3-f;
, , , , , , , , , , , , , , , ;
Here, in Equations 2-a to 2-j, the definitions of T, L _T , and Ar ₁ are the same as those in Equation 2;
Here, in Equations 3-a to 3-f, the definitions of T, G, L _T , and Ar ₂ are the same as those in Equation 3. According to clause 11,
The first metal complex is an organic electroluminescent device having 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;
L _a , L _b , and L _c are the first, second, and third ligands, respectively, coordinated with the metal M, and L _a , L _b , and L _c may be the same or different;
L _a , L _b and L _c can be randomly 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 4,
[Equation 4]
,
Ring A ₁ and Ring A 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;
P ₁ and P ₂ are, identically or differently, selected from O, C or N whenever they appear;
D ₁ and D ₂ are, identically or differently, selected from single bond, O or S whenever they appear;
L ₁ is a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, substituted or unsubstituted vinylene group, ethynylene group, 6~ selected from the group consisting of a substituted or unsubstituted arylene group having 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; When two R's exist simultaneously, the two R's are either the same or different;
a ₁ is selected from 0 or 1;
R ₁₁ and R ₁₂ identically or differently represent mono-substitution, poly-substitution or unsubstitution whenever they appear;
R ₁₁ , R ₁₂ , and R', each time they appear, are the same or differently represented by hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or substituted or unsubstituted cyclo having 3 to 20 ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 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, 2 to 20 carbon atoms Substituted or unsubstituted alkynyl group having carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted having 3 to 20 carbon atoms or an unsubstituted alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 6 to 20 carbon atoms, or Unsubstituted arylgermanyl group, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group , sulfonyl group, phosphino group, and combinations thereof;
Adjacent substituents R ₁₁ , R ₁₂ , and R' 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. A compound composition comprising the compound according to any one of claims 1 to 9.