Organic electroluminescent material and device thereof

Abstract

To provide a novel organic electroluminescent material that, when used in an organic electroluminescent device, improves the performance of the device (lower voltage and higher efficiency) and particularly, can significantly extend the device lifetime, as compared to the conventional art.SOLUTION: The present disclosure provides, for example, 1,3,5-pyrimidine compounds with the following structures.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a compound used in an organic electronic device such as an organic light-emitting device, and in particular to a compound having a structure represented by Formula 1, and an organic electroluminescent device containing the compound. [Background technology]

[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device containing an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transporting and emissive layers (Applied Physics Letters, 1987, 51(12):913-915). Once a bias was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may contain multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emissive layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer tremendous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them highly suitable for specialized applications, such as fabrication on flexible substrates.

[0004] OLEDs are divided into three different types depending on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. Triplets generated in the device are wasted through nonradiative decay pathways, resulting in an internal quantum efficiency (IQE) of only 25%, hindering the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs, which use triplet emission from heavy metal-containing complexes as the emitter. Therefore, singlet and triplet emissions can be harvested, achieving an IQE of 100%. Due to their high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, allowing excitons to transition from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons by triplet excitons threading between reverse systems (reverse intersystem crossing).

[0005] OLEDs can be further divided into small molecule and polymer OLEDs depending on the form of the material used. Small molecules refer to non-polymeric organic or organometallic materials, and as long as they have a precise structure, the molecular weight of the small molecule can be large. Dendrimers, which have a well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emissive groups. Post-polymerization during the manufacturing process can turn small molecule OLEDs into polymer OLEDs.

[0006] Various methods for manufacturing OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution processes if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of an OLED can be achieved by the structural design of the emissive material. An OLED may contain one or more emissive layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized in green, yellow, and red OLEDs, blue phosphorescent devices still suffer from problems such as unsaturated blue, short lifetime, and high operating voltage. Commercially available full-color OLED displays generally use a mixed strategy, employing blue fluorescence and yellow, red, or green phosphorescence. Currently, phosphorescent OLEDs suffer from a rapid decrease in efficiency at high brightness. Furthermore, there is a demand for more saturated emission spectra, higher efficiency, and longer device lifetimes.

[0008] WO2020262861A1 discloses an organic compound having a structure represented by the following formula, and an organic light-emitting device including the compound: [ka] (wherein each R2 is independently 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, and q is an integer of 1 to 8. The application discloses compounds having the following specific structures: [ka] The application discloses compounds that must have at least one of the above-mentioned aryl or heteroaryl group substituents on the carbazole, but does not disclose or teach compounds that do not have an aryl or heteroaryl group substituent on the carbazole, and the application of the compounds in organic electroluminescence devices.

[0009] WO2021040467A1 discloses an organic compound having a structure represented by the following formula, and an organic light-emitting device including the compound: [ka] (where Ar is a substituted or unsubstituted C 6~60 is an aryl group of the formula: The application discloses compounds having the following specific structures: [ka] The application discloses compounds that must have at least two carbazole groups on the phenylene group bonded to the triazine, but does not disclose or teach compounds with only one carbazole group on the phenylene group bonded to the triazine and their application in organic electroluminescent devices.

[0010] WO2017025164A1 discloses an organic compound having a structure represented by the following formula, and an organic light-emitting device including the compound: [ka] (However, A is [ka] wherein B is an aromatic ring having 6 to 30 aromatic ring atoms or an electron-rich heteroaromatic ring having 13 to 30 aromatic ring atoms, and n is 0 or 1. The application discloses compounds having the following specific structures: [ka] The application only discloses compounds having a fluorene indole structure, and does not disclose or teach compounds having a carbazole structure and their application in organic electroluminescence devices.

[0011] KR101926771B1 discloses an organic compound having a structure represented by the following formula, and an organic light-emitting device containing the compound. [ka] (Note that Ar1 to Ar3 may be unsubstituted or may each independently be selected from a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C40 heteroaryl group; furthermore, Ar1 to Ar3 may be unsubstituted or may each independently be selected from a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C40 heteroaryl group. [ka] It may be any one selected from the following structures: The application discloses compounds whose specific structures are as follows: [ka] The application discloses compounds in which Ar1 is unsubstituted, a heteroaryl group, or an aryl group substituted with a heteroaryl group, but does not disclose or teach compounds in which Ar1 is another substituent group or the application of such compounds in organic electroluminescence devices.

[0012] US20220029109A1 discloses compositions of host materials, one of which has a structure represented by Formula 1: [ka] (wherein R1 to R8 are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C6 to C30 aryl group, etc., or the structure of formula 1-1) [ka] (wherein W is O or S), or two adjacent substituents among R1 to R8 are fused to form a structure of formula 1-2 [ka] (wherein Y is O or S), and the compound represented by formula 1 contains at least one structure represented by formula 1-1 or formula 1-2, and when R2 or R7 is formula 1-1, the carbazole group is not bonded to the 1st and 2nd carbon positions in formula 1-1.) The application discloses compounds whose specific structures are as follows: [ka] This application discloses compounds in which the carbazole has a heteroaryl group substituent or in which the carbazole is fused to the structure of Formula 1-2, but does not disclose or teach compounds in which the carbazole has no heteroaryl group substituent or in which the carbazole is not fused, or the application of these compounds in organic electroluminescence devices.

[0013] WO2020149656A1 discloses an organic compound having a structure represented by the following formula, and an organic light-emitting device including the compound: [ka] (wherein X is O or S, Y1 to Y3 are each independently CH or N, and two or more of Y1 to Y3 are N, and Ar1 and Ar2 are each independently substituted or unsubstituted C 6~60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 5~60 and R2 is a substituted or unsubstituted C 6~60 and n is an integer of 1 to 8. The application discloses compounds whose specific structures are as follows: [ka] The application discloses compounds in which all of the groups bonded to the triazine are dibenzofuran or dibenzothiophene groups and the carbazole must have an aryl group substituent, but does not disclose or teach compounds with other structures or their application in organic electroluminescent devices.

[0014] However, the carrier transport capacity and service life of currently reported triazine-based organic semiconductor materials in photovoltaic devices are limited, so the application potential of such materials merits further investigation and development. Summary of the Invention [Problem to be solved by the invention]

[0015] In order to solve at least some of the above-mentioned problems, the present invention aims to provide a series of compounds having the structure of Formula 1. The compounds can be used in organic electroluminescent devices and can provide better device performance, such as lower voltage and higher efficiency, and in particular can significantly improve the service life of the device. [Means for solving the problem]

[0016] In accordance with one embodiment of the present invention, a compound having a structure represented by Formula 1 is disclosed. [ka] (X may be the same or different for each occurrence.) x or N, and Z may be the same or different at each occurrence and be selected from CR z or selected from N, Ar, each occurrence, may be the same or different and is selected from Formula 2, Formula 3, Formula 4, or a combination thereof, wherein Formula 2, Formula 3, and Formula 4 each have the following structure: [ka] R in Equation 2, Equation 3, and Equation 4 tare the same or different at each occurrence and represent mono-, multi- or no substitution; The "*" in the structures of Formula 2, Formula 3, and Formula 4 represents the bonding point between the benzene ring in Formula 1 having the R substituent, Formula 2, Formula 3, or Formula 4, L, each occurrence, may be the same or different and is selected from a single bond, formula 5, formula 6, formula 7, or a combination thereof, wherein formula 5, formula 6, and formula 7 each have the following structure: [ka] V in Equation 5, Equation 6, and Equation 7 may be the same or different for each occurrence, and may be C, CR v or selected from N, e, f and h are, in each occurrence, identically or differently selected from 1, 2 or 3; In Formula 5, Formula 6, and Formula 7, "*" represents a bonding site to the triazine shown in Formula 1, Formula 5, Formula 6, or Formula 7, and "#" represents a bonding site to Ar1, Formula 5, Formula 6, or Formula 7 in Formula 1. Ar1, each occurrence, may be the same or different and is selected from Formula 8, Formula 9, Formula 10, or a combination thereof, wherein Formula 8, Formula 9, and Formula 10 each have the following structure: [ka] U in Equation 8, Equation 9, and Equation 10 may be the same or different for each occurrence, and C, CR u or selected from N, The "*" in Formula 8, Formula 9, and Formula 10 represents the bonding point with L in Formula 1, Formula 8, Formula 9, or Formula 10, R x , R u , R v , R tare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R zare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 ...6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R is the same or different at each occurrence and represents mono-, multi- or no substitution; R, each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; t is selected from 0, 1, 2, 3, 4, or 5, and s is the same or different for each occurrence and is selected from the largest available number of substitutions in the range from 1 to L; In Formula 1, the substituents R xR z Adjacent substituents may be bonded to each other to form a six-membered ring.

[0017] According to another embodiment of the present invention, there is further disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes a compound having the structure of Formula 1 described in the above embodiment.

[0018] According to other embodiments of the present invention, there are further disclosed compound compositions comprising compounds having the structure of Formula 1 as set forth in the preceding embodiments. [Effects of the Invention]

[0019] The present invention discloses a series of compounds having the structure of Formula 1. The compounds may be used as a host material, an electron transport material, or a hole blocking material in an organic electroluminescent device, and can provide better device performance, such as lower voltage and higher efficiency, and in particular can significantly improve the service life of the device. [Brief explanation of the drawings]

[0020] [Figure 1] 1 is a schematic diagram of an organic light emitting device that may include compounds and compound combinations according to the present invention. [Figure 2] 1A-1C are schematic diagrams of other organic light emitting devices that may include compounds and compound combinations according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0021] OLEDs can be fabricated on a variety of substrates, including glass, plastic, and metal. FIG. 1 illustrates, by way of example and not limitation, an organic light-emitting device 100. The drawings are not necessarily drawn to scale, and some layer structures may be omitted from the drawings, if necessary. Device 100 may include a substrate 101, an anode 110, a hole-injection layer 120, a hole-transport layer 130, an electron-blocking layer 140, an emissive layer 150, a hole-blocking layer 160, an electron-transport layer 170, an electron-injection layer 180, and a cathode 190. Device 100 may be fabricated by depositing the layers described, in order. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Pat. No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0022] There are many examples of each of these layers. Illustratively, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., incorporated herein by reference in its entirety. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes, including composite cathodes having a thin metal layer, such as Mg:Ag, coated thereon with a sputter-deposited transparent conductive ITO layer. U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties, describe the principles and use of blocking layers in more detail. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, provides examples of injection layers. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, describes protective layers.

[0023] The above-described split-layer structures are provided by way of non-limiting examples. OLED functions can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may also include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

[0024] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0025] An OLED also requires an encapsulation layer. As shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and not limitation. The difference from FIG. 1 is that an encapsulation layer 102 may be included on the cathode 190 to protect against harmful substances, such as moisture and oxygen, from the outside. Any material capable of providing an encapsulation function, such as glass or an organic-inorganic hybrid layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the exterior of the OLED device. Multilayer thin-film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0026] Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic modules (or units) of the device, including, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lamps, head-up displays, fully or partially transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and tail lights.

[0027] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0028] "Top" means furthest from the substrate, and "bottom" means closest to the substrate. When a first layer is described as being "on" a second layer, the first layer is relatively far from the substrate. Other layers may be present between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may still be described as being "on" the anode, even if various organic layers are present between the cathode and anode.

[0029] "Solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0030] It is believed that if a ligand directly enhances the photosensitizing properties of the emitting material, it may be referred to as "photosensitizing." If a ligand does not enhance the photosensitizing properties of the emitting material, it may be referred to as "auxiliary." However, it is believed that the auxiliary ligand can modify the properties of the photosensitizing ligand.

[0031] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin-statistics limit due to the presence of delayed fluorescence. Delayed fluorescence may be generally divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0032] On the other hand, E-type delayed fluorescence relies on the conversion of triplet and singlet excited states rather than the collision of two triplets. Compounds capable of generating E-type delayed fluorescence must have an extremely small singlet-triplet gap to allow for the energy state conversion. Thermal energy can activate the triplet-to-singlet transition. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of threading between reverse intersystems (RISC) is sufficiently fast, the non-radiative decay from the triplet can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlets can be 100%, far exceeding the 25% spin statistics of the exciton due to electrochemical reactions.

[0033] The characteristics of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited by theory, E-type delayed fluorescence is observed when the emissive material has a small singlet-triplet energy gap (ΔE S-T ) is required. Organic non-metal-containing donor-acceptor emissive materials have the potential to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transition (CT) emission. In these donor-acceptor compounds, the spatial separation between the HOMO and LUMO is generally small, ΔE S-T These states may include CT states. Donor-acceptor emissive materials are typically constructed by combining an electron donor moiety (e.g., an amine group or a carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0034] Definitions of Substituent Terminology

[0035] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0036] As used herein, alkyl groups include straight-chain and branched-chain alkyl groups. The alkyl groups may be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, and more preferably alkyl groups having 1 to 6 carbon atoms. Illustrative examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. The alkyl group may be substituted.

[0037] As used herein, the term "cycloalkyl group" includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and is preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may be substituted.

[0038] As used herein, a heteroalkyl group refers to an alkyl group in which one or more carbon atoms in the alkyl chain are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. 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, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropylsilylethyl. Heteroalkyl groups may also be substituted.

[0039] As used herein, the term "alkenyl group" includes linear, branched, and cyclic olefin groups. The linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propylene, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornylalkenyl groups. The alkenyl groups may be substituted.

[0040] As used herein, the term "alkynyl group" includes straight-chain alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, and phenylpropynyl groups. Of these, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. The alkynyl group may be substituted.

[0041] As used herein, the term "aryl group" or "aromatic group" refers to both non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-dimethylphenyl, mesitylene, and m-tetraphenyl. The aryl group may also be substituted.

[0042] As used herein, the term "heterocyclic group" or "heterocycle" refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, at least one ring atom of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Non-aromatic heterocyclic groups preferably have 3 to 7 ring atoms and contain at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Heterocyclic groups may also be substituted.

[0043] As used herein, the term "heteroaryl group" refers to both non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. The term "isoaryl group" also refers to heteroaryl groups. The heteroaryl group may be a heteroaryl group containing 3 to 30 carbon atoms, preferably a heteroaryl group containing 3 to 20 carbon atoms, and more preferably a heteroaryl group containing 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, Heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furandipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably include dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogs. Heteroaryl groups may also be substituted.

[0044] As used herein, the alkoxy group refers to an -O-alkyl group, an -O-cycloalkyl group, an -O-heteroalkyl group, or an -O-heterocyclic group. Examples and preferred examples of the alkyl group, the cycloalkyl group, the heteroalkyl group, and the heterocyclic group are the same as those described 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 the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may be substituted.

[0045] As used herein, the aryloxy group is represented by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. The aryloxy group may be substituted.

[0046] As used herein, the term "aralkyl group" 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 the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o ... Aralkyl groups include chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among these, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. The aralkyl group may also be substituted.

[0047] As used herein, the term "alkylsilyl group" includes silyl groups substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. The alkylsilyl group may also be substituted.

[0048] As used herein, the term "arylsilyl group" refers to 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 the arylsilyl group include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyl dimethylsilyl, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may be substituted.

[0049] As used herein, the term "alkylgermanium group" includes a germanium group substituted with an alkyl group. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, and is preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of the alkylgermanium group include a trimethylgermanium group, a triethylgermanium group, a methyldiethylgermanium group, an ethyldimethylgermanium group, a tripropylgermanium group, a tributylgermanium group, a triisopropylgermanium group, a methyldiisopropylgermanium group, a dimethylisopropylgermanium group, a tri-tert-butylgermanium group, a triisobutylgermanium group, a dimethyl-tert-butylgermanium group, and a methyldi-tert-butylgermanium group. The alkylgermanium group may also be substituted.

[0050] As used herein, the term "arylgermanium group" refers to a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, and preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenyldibiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, and a diphenyl-tert-butylgermanium group. The arylgermanium group may also be substituted.

[0051] The "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the replacement of one or more C—H groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those skilled in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included in the terminology described herein.

[0052] In the present invention, unless otherwise specified, the following groups are included: a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanium group, a substituted arylgermanium group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, a substituted sulfide group, a substituted aryl ... When any of the terms from the group consisting of an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclyl group, an aralkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, an alkylgermanium group, an arylgermanium group, an amino group, an acyl group, a carbonyl group, a carboxyl group, an ester group, a sulfinyl group, a sulfonyl group, and a phosphino group is used, any one of the groups is included. However, deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heterocyclic groups having 3 to 30 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heterocyclic groups having 3 to 30 carbon atoms, unsubstituted aryloxy ... This means that the aryl group may be substituted with one or more groups selected from an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanium group having 3 to 20 carbon atoms, an unsubstituted arylgermanium group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0053] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are considered equivalent.

[0054] In the compounds described herein, hydrogen atoms may be partially or completely replaced with deuterium.Other atoms, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof.In order to improve the efficiency and stability of the device, it may be preferable to replace other stable isotopes in the compound.

[0055] In the compounds referred to herein, multiple substitution refers to a range up to the most available substitution, including double substitution. When a substituent in a compound referred to herein is referred to as multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on the bond structure, and the substituents present at all available substitution positions may be the same structure or different structures.

[0056] Unless specifically limited, adjacent substituents in the compounds mentioned herein may be bonded to form a ring, and adjacent substituents in the compounds may not be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including not only the situation where adjacent substituents may be bonded to form a ring, but also the situation where adjacent substituents are not bonded to form a ring. When adjacent substituents may be bonded to form a ring, the ring formed may be a monocyclic or polycyclic ring, and may be an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a heteroaryl ring. In such descriptions, 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 further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0057] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0058] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms that are directly bonded to each other are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0059] The statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that two substituents bonded to carbon atoms further apart are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0060] In addition, the statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that when one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded to form a ring. An example is shown in the following formula. [ka]

[0061] In accordance with one embodiment of the present invention, a compound having a structure represented by Formula 1 is disclosed. [ka] (X may be the same or different for each occurrence.) x or N, with the proviso that in formula 1, one X is selected from C and has the structure [ka] Z may be identical or different for each occurrence of CR z or selected from N, Ar, each occurrence, may be the same or different and is selected from Formula 2, Formula 3, Formula 4, or a combination thereof, wherein Formula 2, Formula 3, and Formula 4 each have the following structure: [ka] R in Equation 2, Equation 3, and Equation 4 t are the same or different at each occurrence and represent mono-, multi- or no substitution; The "*" in the structures of Formula 2, Formula 3, and Formula 4 represents the bonding point between the benzene ring in Formula 1 having the R substituent, Formula 2, Formula 3, or Formula 4, L, each occurrence, may be the same or different and is selected from a single bond, formula 5, formula 6, formula 7, or a combination thereof, wherein formula 5, formula 6, and formula 7 each have the following structure: [ka] V in Equation 5, Equation 6, and Equation 7 may be the same or different for each occurrence, and may be C, CR v or selected from N, e, f and h are, in each occurrence, identically or differently selected from 1, 2 or 3; In Formula 5, Formula 6, and Formula 7, "*" represents a bonding site to the triazine shown in Formula 1, Formula 5, Formula 6, or Formula 7, and "#" represents a bonding site to Ar1, Formula 5, Formula 6, or Formula 7 in Formula 1. Ar1, each occurrence, may be the same or different and is selected from Formula 8, Formula 9, Formula 10, or a combination thereof, wherein Formula 8, Formula 9, and Formula 10 each have the following structure: [ka] U in Equation 8, Equation 9, and Equation 10 may be the same or different for each occurrence, and C, CR u or selected from N, The "*" in Formula 8, Formula 9, and Formula 10 represents the bonding point with L in Formula 1, Formula 8, Formula 9, or Formula 10, R x , R u , R v , R tare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R zare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 ...6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R is the same or different at each occurrence and represents mono-, multi- or no substitution; R, each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; t is selected from 0, 1, 2, 3, 4, or 5, and s is the same or different for each occurrence and is selected from the largest available number of substitutions in the range from 1 to L; In Formula 1, the substituents R xR z Adjacent substituents may be bonded to each other to form a six-membered ring.

[0062] In this specification, "said Ar, each occurrence being the same or different, is selected from Formula 2, Formula 3, Formula 4, or a combination thereof" means that Ar may be selected from a group represented by any one of Formula 2, Formula 3, and Formula 4 alone. Ar may be selected from any combination of at least two of Formula 2, Formula 3, and Formula 4. For example, when Ar is selected from a combination of two Formula 2 groups, Ar is: [ka] and when Ar is selected from the combined groups of one formula 2 and one formula 3, Ar is [ka] or [ka] and when Ar is selected from the three groups combined in formula 2, Ar is [ka] When Ar is selected from any combination of groups represented by formula 2, formula 3, and formula 4, the situation is similar to that described above, and the structure of the group Ar is obvious to those skilled in the art, so it is not necessary to list them here.

[0063] In this specification, "the '*' in the structures of formula 2, formula 3, and formula 4 represents the bonding position to the benzene ring having the R substituent in formula 1, or to formula 2, formula 3, or formula 4" means that when Ar is selected from a group represented by any one of formula 2, formula 3, and formula 4 alone, the '*' in formula 2, formula 3, and formula 4 represents the bonding position to the benzene ring having the R substituent in formula 1, and when Ar is selected from a group formed by any combination of at least two of formula 2, formula 3, and formula 4, the '*' in formula 2, formula 3, and formula 4 represents the bonding position to another combination of formula 2, formula 3, or formula 4 (the position is any available substitution position on the ring represented by formula 2, formula 3, or formula 4). For example, when Ar is selected from a group formed by a combination of two of formula 2, Ar is [ka] When Ar is selected from any other combination of groups represented by formula 2, formula 3, or formula 4, the situation is similar to that described above, and therefore the structure of group Ar is obvious to those skilled in the art and will not be listed here.

[0064] In this specification, "L is the same or different at each occurrence and is selected from a single bond, formula 5, formula 6, formula 7, or a combination thereof" means that L is selected from a single bond or a group represented by any one of formula 5, formula 6, and formula 7, and L may also be selected from a group representing any combination of at least two of formula 5, formula 6, and formula 7. For example, when L is selected from a group representing two of formula 5, L is [ka] and when L is selected from the combined groups of one formula 5 and one formula 6, L is [ka] or [ka] When L is selected from any combination of groups represented by formula 5, formula 6, and formula 7, the situation is similar to that described above, and the structure of group L is obvious to those skilled in the art, so it is not necessary to list them here.

[0065] In this specification, "in Formula 5, Formula 6, and Formula 7, an * represents a bonding site with the triazine shown in Formula 1, Formula 5, Formula 6, or Formula 7, and an # represents a bonding site with Ar1, Formula 5, Formula 6, or Formula 7 in Formula 1" means that when L is selected from a group independently represented by any one of Formulas 5, 6, and 7, an * in Formula 5, Formula 6, and Formula 7 represents a bonding site with the triazine shown in Formula 1, and an # represents a bonding site with Ar1 in Formula 1. When L is selected from a group formed by any combination of at least two of Formulas 5, Formula 6, and Formula 7, an * or # in Formula 5, Formula 6, and Formula 7 further represents a bonding site with another combination of Formulas 5, Formula 6, or Formula 7 (the position may be any available substitution position in the ring shown in Formula 5, Formula 6, or Formula 7). For example, when L is selected from a group formed by a combination of two of Formulas 5, L is [ka] When L is selected from any combination of groups represented by formula 5, formula 6, and formula 7, the situation is similar to that described above, and the structure of group L is obvious to those skilled in the art, so it is not necessary to list them here.

[0066] In this specification, "Ar1 is the same or different at each occurrence and is selected from formula 8, formula 9, formula 10, or a combination thereof" means that Ar1 may be selected from a group represented by any one of formula 8, formula 9, and formula 10 alone, or Ar1 may be selected from a group represented by any combination of at least two of formula 8, formula 9, and formula 10. For example, when Ar1 is selected from a group represented by two of formula 8, Ar1 is [ka] and when Ar1 is selected from the group consisting of one formula 8 and one formula 9, Ar1 is [ka] or [ka] and when Ar is selected from the three groups combined in formula 8, Ar1 is [ka] When Ar1 is selected from any other combination of groups represented by formula 8, formula 9, or formula 10, the situation is similar to that described above, and therefore the structure of Ar1 in the combination is obvious to those skilled in the art, and is not listed here.

[0067] In this specification, the phrase "the * in formula 8, formula 9, or formula 10 represents the bonding position with L in formula 1, formula 8, formula 9, or formula 10" means that when Ar1 is selected from a group represented solely by any one of formula 8, formula 9, or formula 10, the * in formula 8, formula 9, or formula 10 represents the bonding position with L in formula 1. When Ar1 is selected from a group represented by any combination of at least two of formulas 8, formula 9, and formula 10, the * in formula 8, formula 9, or formula 10 further represents the bonding position with another combination of formula 8, formula 9, or formula 10 (the position may be any available substitution position in the ring shown in formula 8, formula 9, or formula 10). For example, when Ar1 is selected from a group represented by a combination of two formulas 8, Ar1 is [ka] When Ar1 is selected from any other combination of groups represented by formula 8, formula 9, or formula 10, the situation is similar to that described above, and therefore the structure of Ar1 in the combination is obvious to those skilled in the art, and is not listed here one by one.

[0068] As used herein, "t" represents the number of Ar groups substituted on the benzene ring with the R substituent in Formula 1. t is selected from 0, 1, 2, 3, 4, or 5. For example, when t is 2, two Ar groups are substituted on the benzene ring with the R substituent in Formula 1, and the two Ar groups may be the same or different.

[0069] In this specification, "s" represents the number of Ar1 substituted in the structure of L in Formula 1, and "s" is an integer. "S is the same or different at each occurrence and is selected from 1 to the largest number of available substitutions in L" means that there is at least one Ar1 substitution in the structure of L, and at most, there is an Ar1 substitution at every available substitution position in the structure of L. For example, when L is [ka] When L is, the largest available number of substitutions in the structure is 5, where s is selected from an integer of 1 to 5. [ka] where the largest available number of substitutions in the structure is 9, and s is an integer selected from 1 to 9, and L is [ka] or [ka] In the case where L is selected from any other combination of groups of formulas 5, 6, and 7, the maximum number of available substitutions in the structure is 11, where s is selected from an integer of 1 to 11. When L is selected from any other combination of groups of formulas 5, 6, and 7, the situation is similar to that described above, so the maximum number of available substitutions in the other combination of groups, i.e., the selection range of s, is obvious to those skilled in the art and will not be listed here one by one. Note that when s is selected from an integer of 2 or more, the corresponding multiple Ar1 groups may be the same or different. Preferably, s is selected from 1, 2, 3, 4, or 5. Note that in formula 1, when Ar1 is bonded to V in L, V is selected from C.

[0070] In this specification, "substituent R and substituent R x R z The phrase "when only two adjacent substituents R are bonded to each other, the adjacent substituents may be bonded to form a 6-membered ring" means that in Formula 1, two adjacent substituents R may be bonded to each other to form a 6-membered ring, and two adjacent substituents R x may be bonded to each other to form a 6-membered ring, and two adjacent substituents R z They may be bonded to each other to form a six-membered ring, meaning that other adjacent substituents in Formula 1 are not bonded to form a ring. Preferably, the six-membered ring formed by bonding the adjacent substituents is a six-membered aromatic ring or a heteroaromatic ring.

[0071] According to one embodiment of the present invention, the compound having the structure represented by Formula 1 includes only one carbazole structure, azacarbazole structure, carbazole fused ring structure, or azacarbazole fused ring, which is shown in the structure of Formula 1, i.e., the fused ring structure where Z is located.

[0072] According to one embodiment of the present invention, said Ar is selected from the structure represented by formula 2:

[0073] According to one embodiment of the present invention, the Ar may be the same or different for each occurrence. [ka] [ka] [ka] or [ka] Selected from R t may be the same or different at each occurrence and represent mono-, multi- or no substitution.

[0074] According to one embodiment of the present invention, said L, identically or differently at each occurrence, is selected from a single bond.

[0075] According to one embodiment of the present invention, each occurrence of L may be the same or different and is selected from the structure of formula 5.

[0076] According to one embodiment of the present invention, the L may be the same or different for each occurrence. [ka] [ka] [ka] or [ka] Selected from.

[0077] According to one embodiment of the present invention, the Ar1 may be the same or different for each occurrence. [ka] [ka] [ka] or [ka] Selected from.

[0078] According to one embodiment of the present invention, each occurrence of Ar1 may be the same or different and is selected from the structure represented by formula 8.

[0079] According to one embodiment of the present invention, each occurrence of Ar is the same or different and is selected from the structure of formula 2 or formula 3, each occurrence of L is the same or different and is selected from the structure of formula 5 or formula 6, and each occurrence of Ar1 is the same or different and is selected from the structure of formula 8 or formula 9.

[0080] According to one embodiment of the present invention, each occurrence of X may be identical or different and may be C or CR. x Selected from.

[0081] According to one embodiment of the present invention, Z may be the same or different for each occurrence. z Selected from.

[0082] According to one embodiment of the present invention, U may be C or CR, identically or differently for each occurrence. u Selected from.

[0083] According to one embodiment of the present invention, the V may be identical or different for each occurrence and may be C or CR. v Selected from.

[0084] According to one embodiment of the present invention, s is 1.

[0085] According to one embodiment of the present invention, the t is selected from 0 or 1.

[0086] According to one embodiment of the present invention, the R x , R u , R t , R v , R zare the same or different at each occurrence and are selected from the group consisting of 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 a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms.

[0087] According to one embodiment of the present invention, the R x , R u , R t , R v , R z are the same or different at each occurrence and are selected from hydrogen or deuterium.

[0088] According to one embodiment of the present invention, each occurrence of R may be the same or different and may be selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and a substituted or unsubstituted alkenyl group having 2 to 20 ring carbon atoms.

[0089] According to one embodiment of the present invention, said R, identically or differently at each occurrence, is selected from hydrogen or deuterium.

[0090] According to one embodiment of the present invention, the compound of Formula 1 has a structure represented by Formula 1-1. [ka] (X may be the same or different for each occurrence.) x or N, provided that in formula 1-1, one X is selected from C and has the structure [ka] Z may be identical or different for each occurrence of CR z or N, and U may be the same or different in each occurrence and u or N, and V is selected from C, CR, or the like, which may be the same or different for each occurrence. v or selected from N, L1 may be the same or different at each occurrence and may be a single bond or [ka] Selected from e is selected from 1, 2 or 3, and may be the same or different for each occurrence; R x , R u , R v , R t are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R zare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 ...6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R, R t are the same or different at each occurrence and represent mono-, multi- or no substitution; R, each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; t is selected from 0, 1, 2, 3, 4, or 5, and s may be the same or different for each occurrence and may range from 1 to [ka] and preferably s is selected from 1, 2, 3, 4 or 5; In formula 1-1, the substituents R x R z Adjacent substituents may be bonded to each other to form a six-membered ring.

[0091] According to one embodiment of the present invention, the compound is selected from the group consisting of Compound A-1 to Compound A-581, and the specific structures of Compound A-1 to Compound A-581 are set forth in claim 7.

[0092] According to one embodiment of the present invention, the compound is selected from the group consisting of Compounds A-1 to A-584, and specific structures of Compounds A-1 to A-581 are set forth in claim 7. Specific structures of Compounds A-582 to A-584 are as follows: [ka]

[0093] According to one embodiment of the present invention, an anode; A cathode; Further disclosed is an electroluminescent device comprising: an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having Formula 1, and the compound having a structure represented by Formula 1 is described in any one of the above-described examples.

[0094] According to one embodiment of the present invention, the organic layer is an emitting layer and the compound is a host compound.

[0095] According to one embodiment of the present invention, the compound is a green phosphorescent host material, a red phosphorescent host material, or a yellow phosphorescent host material.

[0096] According to one embodiment of the present invention, the organic layer is an electron transport layer and the compound is an electron transport compound.

[0097] According to one embodiment of the present invention, the organic layer is a hole-blocking layer, and the compound is a hole-blocking compound.

[0098] According to one embodiment of the present invention, the light-emitting layer further includes a first metal complex, and the first metal complex is M(L a ) m (L b ) n (L c ) q It has the general formula: (Metal M is selected from metals having a relative atomic mass greater than 40, Ligand L a , L b and L c are the first ligand, the second ligand, and the third ligand, respectively, which coordinate with the metal M, and the ligand L a , L b and L c may be the same or different, Ligand L a , L b and L c may be linked to form multidentate ligands, for example, L a , L b and L c Any two of may be linked to form a tetradentate ligand, and further, for example, L a , L b and L c may be linked together to form a hexadentate ligand, or may further include, for example, L a , L b and L c does not bond to any of them 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 and q is equal to the oxidation state of the metal M, and when m is 2 or more, a plurality of L a may be the same or different, and when n is 2, two L bmay be the same or different, and when q is 2, two L c may be the same or different, Ligand L a has a structure represented by formula 11: [ka] ring C1 and ring C2, each occurrence of which may be the same or different, are selected from an aromatic ring having 5 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; Q1 and Q2 are identical or different at each occurrence and are selected from C or N; R 11 and R 12 are the same or different at each occurrence and represent mono-, multi- or no substitution; R 11 and R 12 are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R 11 , R12 may be bonded to form a ring, Ligand L b and L c are the same or different at each occurrence and are selected from monoanionic bidentate ligands.

[0099] In this example, "adjacent substituents R 11 , R 12 may be bonded to form a ring” means that adjacent substituent groups, for example, two substituents R 11 two substituents R 12 Comrades and R 11 and R 12 This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0100] According to one embodiment of the present invention, the ligand L b and L c is the same or different at each occurrence and is selected from the group consisting of the following structures: [ka] (R a and R b are the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 and CR C1 R C2 selected from the group consisting of X c and X d are O, S, Se and NR, which may be the same or different for each occurrence. N2 selected from the group consisting of R a , R b , R c , R N1 , R N2 , R C1 and R C2are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring.

[0101] In this example, "adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring” means that adjacent substituent groups, for example, two substituents R a two substituents R b R a and R b R aand R c R b and R c R a and R N1 R b and R N1 R a and R C1 R a and R C2 R b and R C1 R b and R C2 Comrades and R C1 and R C2 R a and R N2 R b and R N2 This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0102] According to one embodiment of the present invention, the first metal complex is Ir(L a ) m (L b ) 3-m and has a structure represented by formula 11-1. [ka] (m is 0, 1, 2 or 3, and when m is 2 or 3, a plurality of L a are the same or different, and if m0 or 1 is b are the same or different, T1 to T6 are the same or different CRs for each occurrence. T or selected from N, R a , R b and R d are the same or different at each occurrence and represent mono-, multi- or no substitution; R a , R b , R d and RT are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R a , R b may be bonded to form a ring, Adjacent substituents R d , R T may be bonded to form a ring.

[0103] In this example, "adjacent substituents R a , R b may be bonded to form a ring” means that adjacent substituent groups, for example, two substituents R a two substituents R b and the substituent R a and R b This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0104] In this example, "adjacent substituents R d , R T may be bonded to form a ring” means that adjacent substituent groups, for example, two substituents R T two substituents R d This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0105] According to one embodiment of the present invention, at least one of T1 to T6 is CR T and wherein R T is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0106] According to one embodiment of the present invention, at least one of T1 to T6 is CR T and wherein R T is selected from fluorine and a cyano group.

[0107] According to one embodiment of the present invention, at least two of T1 to T6 are CR T and one of them is R T is selected from fluorine and cyano groups, and one other R T is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 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.

[0108] According to one embodiment of the present invention, the T1 to T6 are the same or different CRs for each occurrence. T Selected from.

[0109] According to one embodiment of the present invention, T1 to T6 may be the same or different for each occurrence. T or N, and at least one of T1 to T6 is selected from N, for example, one or two of T1 to T6 are selected from N.

[0110] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compounds GD1 to GD76, and specific structures of compounds GD1 to GD76 are set forth in claim 12.

[0111] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compounds GD1 to GD77, and specific structures of compounds GD1 to GD76 are shown in claim 12. The specific structure of compound GD77 is: [ka] is.

[0112] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of compounds GD1 to GD78, and specific structures of compounds GD1 to GD78 are shown in claim 12. The specific structure of compound GD77 is: [ka] The specific structure of the compound GD78 is: [ka] is.

[0113] According to one embodiment of the present invention, the hydrogen atoms in the compounds GD1 to GD76 may be partially or completely deuterated.

[0114] According to one embodiment of the present invention, the first metal complex is M(L a1 ) j (L b1 ) kwherein M is selected from metals having a relative atomic mass greater than 40; L a1 , L b1 are a first ligand and a second ligand that coordinate with M, respectively, and L a1 , L b1 may be linked to form a multidentate ligand; j is 1, 2, or 3, and k is 0, 1, or 2. The sum of j and k is equal to the oxidation state of M. When j is 2 or more, a plurality of L a1 may be the same or different, and when k is 2, two L b1 may be the same or different, Said L a1 has the structure represented by formula 11-2, [ka] 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 carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring; ring F and ring E are fused via Y1 and Y2; Y1 and Y2, at each occurrence, are the same or different and are selected from C or N; R f , R e are the same or different at each occurrence and represent mono-, multi- or no substitution; Y may be the same or different for each occurrence. y or selected from N, R f , R e , R yare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R f , R e , R y may be bonded to form a ring, Said ligand L b1 has the structure represented by formula 11-3, [ka] R 21 ~R 27are 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 atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... The alkyl group is selected from the group consisting of an alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0115] In this specification, adjacent substituents R f , R e , R y may be bonded to form a ring, the substituent R f , substituent R e , substituent R y When present, adjacent substituent groups, e.g., adjacent substituents R f adjacent substituents R e adjacent substituents R y adjacent substituents R f and R e adjacent substituents R f and R y each other and adjacent substituents R e and R y It is understood that any one or more of the substituents R may be bonded to each other to form a ring. f , substituent R e , substituent R y When present, none of these substituent groups need to be joined to form a ring.

[0116] According to one embodiment of the present invention, the ligand L b1 has the structure represented by formula 11-3. [ka] (R 21 ~R 23 at least one of which is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or R 24 ~R 26 At least one of the groups is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0117] According to one embodiment of the present invention, the ligand L b1 has the structure represented by formula 11-3. [ka] (R 21 ~R 23 at least two of R are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and / or R 24 ~R 26 At least two of the groups are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

[0118] According to one embodiment of the present invention, the ligand L b1 has the structure represented by formula 11-3. [ka] (R 21 ~R 23 at least two of, each occurrence, are the same or different and are selected from 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, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof; and / or R 24 ~R 26 At least two of, each occurrence, may be the same or different and are selected from 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, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.

[0119] According to one embodiment of the present invention, the first metal complex is Ir(L a1 )2(L b1 ) has the general structure:

[0120] According to one embodiment of the present invention, the first metal complex is an Ir metal complex, and the ligand L a1 and wherein L a1 has a structure represented by formula 11-2 and contains at least one structural unit selected from the group consisting of a 6-6 membered aromatic ring, a 6-6 membered heteroaromatic ring, a 6-5 membered aromatic ring, and a 6-5 membered heteroaromatic ring.

[0121] According to one embodiment of the present invention, the first metal complex is an Ir metal complex, and the ligand L a1 and wherein L a1 has a structure represented by formula 11-2 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline, and azaphenanthrene.

[0122] According to one embodiment of the present invention, the first metal complex is selected from the group consisting of the following structures: [ka]

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[0123] According to one embodiment of the present invention, in the organic electroluminescence device, the light-emitting layer further comprises a second host compound, and the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0124] According to one embodiment of the present invention, in the organic electroluminescent device, the light-emitting layer further comprises a second host compound, and the second host compound comprises at least one chemical group selected from the group consisting of benzene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, fluorene, silicon fluorene, and combinations thereof.

[0125] According to one embodiment of the present invention, the second host compound has a structure represented by Formula 12 or Formula 13: [ka] (L T are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; T may be the same or different for each occurrence, and may be C, CR w or selected from N, Ar 11 are the same or different at each occurrence 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; R ware the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 3 ... a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R w may be bonded to form a ring.

[0126] In the present specification, "adjacent substituents R w may be bonded to form a ring” means that adjacent substituent groups, for example, any two substituents R w This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0127] According to one embodiment of the present invention, the second host compound has a structure represented by formula 12-1. [ka] (L Tare the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; T may be the same or different for each occurrence, and may be C, CR w or selected from N, R w are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar 11 are the same or different at each occurrence 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; Adjacent substituents R w may be bonded to form a ring.

[0128] According to an embodiment of the present invention, in the organic electroluminescence device, the second host compound has a structure represented by formula 12-2. [ka] (G may be identical or different for each occurrence of C(R g )2, NR g , O or S; T may be the same or different for each occurrence, and may be C, CR w or selected from N, L T are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; R w , R gare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar 11 are the same or different at each occurrence 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; Adjacent substituents R w , R g may be bonded to form a ring.

[0129] In the present specification, "adjacent substituents R w , R g may be bonded to form a ring” means that adjacent substituent groups, for example, two substituents R w two substituents R g R w and R gThis means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0130] According to one embodiment of the present invention, the second host compound has a structure represented by formula 12-3. [ka] (L T are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; T may be the same or different for each occurrence, and may be C, CR w or selected from N, R ware the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar 11 are the same or different at each occurrence 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; Adjacent substituents R w may be bonded to form a ring.

[0131] According to one embodiment of the present invention, in Formula 12-1, Formula 12-2, and Formula 12-3, T may be the same or different for each occurrence, and may be a C or CR w Selected from.

[0132] According to one embodiment of the present invention, in formulas 12-1, 12-2, and 12-3, T may be the same or different for each occurrence, and may be C, CR w or N, and at least one of them is selected from N, for example one T or two T are selected from N.

[0133] According to an embodiment of the present invention, in the organic electroluminescence device, the second host compound has a structure represented by one of formulas 12-a to 12-j. [ka] (L T are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; T may be the same or different for each occurrence. w or selected from N, R w are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar11 are the same or different at each occurrence 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; Adjacent substituents R w may be bonded to form a ring.

[0134] According to one embodiment of the present invention, in formulas 12-a to 12-j, T may be the same or different for each occurrence. w Selected from.

[0135] According to one embodiment of the present invention, in formulas 12-a to 12-j, T may be the same or different for each occurrence. w or N, and at least one of them is selected from N, for example one T or two T are selected from N.

[0136] According to one embodiment of the present invention, in the organic electroluminescence device, the second host compound has a structure represented by one of formulas 13-a to 13-f. [ka] (G may be identical or different for each occurrence of C(R g )2, NR g , O or S; T may be the same or different for each occurrence. w or selected from N, L T are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; R w , R gare the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar 11 are the same or different at each occurrence 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; Adjacent substituents R w , R g may be bonded to form a ring.

[0137] According to one embodiment of the present invention, in formulas 13-a to 13-f, T may be the same or different for each occurrence, and may be a CR w Selected from.

[0138] According to one embodiment of the present invention, in formulas 13-a to 13-f, T may be the same or different for each occurrence, and may be a CR w or N, and at least one of them is selected from N, for example, one T or two Ts are selected from N.

[0139] According to one embodiment of the present invention, the second host compound is selected from the group consisting of compounds PH-1 to PH-101, and the specific structures of compounds PH-1 to PH-101 are set forth in claim 16.

[0140] According to one embodiment of the present invention, the second host compound is selected from the group consisting of Compounds PH-1 to PH-137, and specific structures of Compounds PH-1 to PH-101 are set forth in claim 16. Specific structures of Compounds PH-102 to PH-137 are as follows: [ka] [ka] [ka] [ka] [ka]

[0141] In manufacturing a device, when two or more host materials are used to form an emitting layer by co-evaporation with an emitting material, the two or more host materials and the emitting material may be placed in different evaporation sources and co-evaporated to form the emitting layer, or the two or more host materials may be pre-mixed and placed in the same evaporation source, and co-evaporated with an emitting material placed in another evaporation source to form the emitting layer. Such a pre-mixing method can further save evaporation sources.

[0142] According to one embodiment of the present invention, the compound of Formula 1, the second host compound, and the first metal complex may be placed in different evaporation sources and co-deposited to form an emitting layer, or a premix of the compound of Formula 1 and the second host compound may be placed in the same evaporation source and co-deposited with the first metal complex placed in another evaporation source to form an emitting layer. The compound of Formula 1 and the second host compound of the present invention can form a stable co-evaporated premix, and are therefore suitable for forming an emitting layer by evaporation in a premixed form.

[0143] According to one embodiment of the present invention, the organic electroluminescent element emits green light.

[0144] According to one embodiment of the present invention, the organic electroluminescent element emits yellow light.

[0145] According to one embodiment of the present invention, the organic electroluminescent element emits red light.

[0146] According to one embodiment of the present invention, the organic electroluminescent element emits white light.

[0147] According to one embodiment of the present invention, the first metal complex is doped into the compound and the second host compound, and the first metal complex is 1% to 30% based on the total weight of the light-emitting layer.

[0148] According to one embodiment of the present invention, the first metal complex is doped into the compound and the second host compound, and the first metal complex is 3% to 13% based on the total weight of the light-emitting layer.

[0149] According to one embodiment of the present invention, there is further disclosed a composition comprising a compound of Formula 1. The compound is shown in any one of the embodiments described above.

[0150] Combination with other materials

[0151] The materials of the specific layers used in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132 to 0161 of U.S. Patent Application No. US2016 / 0359122A1, the contents of which are incorporated herein by reference in their entirety. The materials described or referenced 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 other materials that can be used in combination.

[0152] It is noted herein that specific layer materials used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned 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 other materials that can be used in combination.

[0153] In the material synthesis examples, all reactions were carried out under nitrogen protection unless otherwise specified. All reaction solvents were anhydrous and used as obtained commercially. The synthesized products were subjected to structural confirmation and property testing using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatography, a liquid chromatography / mass spectrometer, a gas chromatography / mass spectrometer, a differential scanning calorimeter, a Shanghai Lingguang Technology fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical work station, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system, a service life test system from Suzhou Fusida, an ellipsometer from Beijing Liangtuo, and the like) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment and test methods, and can reliably and unaffectedly obtain specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification.

[0154] Synthesis Example 1: Synthesis of Compound A-27

[0155] Step 1: Synthesis of intermediate C [ka] Intermediate A (22.2 g, 106.0 mmol), Intermediate B (17.7 g, 106.0 mmol), cerium carbonate (CsCO, 69.1 g, 212.0 mmol), and 200 mL of N,N-dimethylformamide (DMF) were added to a three-neck round-bottom flask in this order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the completion of the reaction, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction solution was poured into a large amount of water and extracted with ethyl acetate. The organic phase was recovered, concentrated under reduced pressure, and the crude product was obtained. The crude product was pulped with absolute ethanol to obtain Intermediate C (26.7 g, 74.9 mmol) as a white solid in 70.7% yield.

[0156] Step 2: Synthesis of intermediate E [ka] A three-neck round-bottom flask was charged with Intermediate C (18.9 g, 53.0 mmol), Intermediate D (9.5 g, 77.9 mmol), Pd(PPh3)4 (2.4 g, 2.1 mmol), K2CO3 (14.6 g, 106.0 mmol), 160 mL of toluene, 40 mL of EtOH, and 40 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 8:1) to obtain Intermediate E (16.8 g, 47.5 mmol) as a white solid in 89.6% yield.

[0157] Step 3: Synthesis of intermediate F [ka] Intermediate E (16.8 g, 47.5 mmol), bis(pinacolato)diboron (18.1 g, 71.3 mmol), Pd2(dba)3 (0.87 g, 0.95 mmol), tricyclohexylphosphine tetrafluoroborate (PCy3·HBF4, 0.87 g, 0.95 mmol), KOAc (9.3 g, 95.0 mmol), and 150 mL of 1,4-dioxane were added to a three-neck round-bottom flask in this order. The mixture was heated to reflux overnight under N2 protection. After TLC showed the reaction was complete, the mixture was turned off and allowed to cool to room temperature. The reaction was filtered through diatomaceous earth, and the solution was concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (PE / DCM=5:1 to 2:1) to obtain a white solid intermediate F (18.0 g, 40.4 mmol), with a yield of 85.0%.

[0158] Step 4: Synthesis of compound A-27 [ka] A three-neck round-bottom flask was charged with intermediate F (7.2 g, 16.2 mmol), intermediate G (5.6 g, 16.2 mmol), Pd(PPh3)4 (0.37 g, 0.32 mmol), K2CO3 (3.2 g, 32.4 mmol), 60 mL of toluene, 15 mL of EtOH, and 15 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The resulting solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain a pale yellow solid (8.4 g, 13.4 mmol), with a yield of 82.7%. The product was identified as the target product A-27 with a molecular weight of 626.2.

[0159] Synthesis Example 2: Synthesis of Compound A-28

[0160] Step 1: Synthesis of Intermediate I [ka] A three-neck round-bottom flask was charged with Intermediate H (3.1 g, 14.4 mmol), Intermediate G (4.9 g, 14.4 mmol), Pd(PPh3)4 (0.33 g, 0.29 mmol), K2CO3 (3.9 g, 28.8 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the completion of the reaction, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain Intermediate I (6.0 g, 12.5 mmol) as a white solid in 86.8% yield.

[0161] Step 2: Synthesis of compound A-28 [ka] Intermediate I (3.6 g, 7.5 mmol), Intermediate J (1.3 g, 7.5 mmol), cerium carbonate (4.9 g, 15.0 mmol), and 60 mL of DMF were added sequentially to a three-neck round-bottom flask. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction solution was poured into a large amount of water, extracted with ethyl acetate, and the organic phase was recovered. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to obtain a pale yellow solid (2.5 g, 3.9 mmol) in 52.0% yield. The product was identified as the target product A-28 with a molecular weight of 634.3.

[0162] Synthesis Example 3: Synthesis of Compound A-49

[0163] Step 1: Synthesis of compound A-49 [ka] A three-neck round-bottom flask was charged with intermediate F (3.6 g, 8.1 mmol), intermediate K (3.4 g, 8.1 mmol), Pd(PPh3)4 (0.19 g, 0.16 mmol), K2CO3 (2.2 g, 16.2 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The resulting solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain a pale yellow solid (4.2 g, 6.0 mmol), with a yield of 74.1%. The product was identified as the target product A-49 with a molecular weight of 702.3.

[0164] Synthesis Example 4: Synthesis of Compound A-50

[0165] Step 1: Synthesis of intermediate L [ka] A three-neck round-bottom flask was charged with Intermediate H (3.1 g, 14.4 mmol), Intermediate K (6.0 g, 14.4 mmol), Pd(PPh3)4 (0.33 g, 0.29 mmol), K2CO3 (3.9 g, 28.8 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the completion of the reaction, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain Intermediate L (5.4 g, 9.7 mmol) as a white solid in 67.4% yield.

[0166] Step 2: Synthesis of compound A-50 [ka] Intermediate L (4.2 g, 7.5 mmol), Intermediate J (1.3 g, 7.5 mmol), cerium carbonate (4.9 g, 15.0 mmol), and 60 mL of DMF were added to a three-neck round-bottom flask in this order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction solution was poured into a large amount of water, extracted with ethyl acetate, and the organic phase was recovered. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to obtain a pale yellow solid (2.5 g, 3.5 mmol) in 46.7% yield. The product was identified as the target product A-50 with a molecular weight of 710.3.

[0167] Synthesis Example 5: Synthesis of Compound A-56

[0168] Step 1: Synthesis of compound A-56 [ka] A three-neck round-bottom flask was charged with Intermediate F (4.0 g, 9.0 mmol), Intermediate M (3.8 g, 9.0 mmol), Pd(PPh3)4 (0.20 g, 0.18 mmol), K2CO3 (2.5 g, 18.0 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The solid was rinsed with water and ethanol to obtain the crude product. The crude product was recrystallized from toluene to obtain a pale yellow solid (3.2 g, 4.6 mmol), with a yield of 51.1%. The product was identified as the target product A-56 with a molecular weight of 702.3.

[0169] Synthesis Example 6: Synthesis of Compound A-163

[0170] Step 1: Synthesis of intermediate O [ka] A three-necked round-bottom flask was charged with Intermediate N (8.8 g, 40.2 mmol), Intermediate G (13.8 g, 40.2 mmol), Pd(PPh3)4 (0.93 g, 0.80 mmol), Na2CO3 (8.5 g, 80.4 mmol), 120 mL of THF, and 30 mL of HO, in that order. Under N2 protection, the mixture was heated to reflux overnight. After TLC confirmed the completion of the reaction, the mixture was cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain Intermediate O (9.5 g, 19.7 mmol) as a white solid in 49.0% yield.

[0171] Step 2: Synthesis of intermediate P [ka] A three-neck round-bottom flask was charged with intermediate O (9.5 g, 19.7 mmol), intermediate D (2.6 g, 21.6 mmol), Pd(PPh3)4 (0.50 g, 0.43 mmol), K2CO3 (5.4 g, 39.4 mmol), 60 mL of toluene, 15 mL of EtOH, and 15 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the completion of the reaction, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain intermediate P (4.8 g, 10.0 mmol) as a white solid in 50.8% yield.

[0172] Step 3: Synthesis of compound A-163 [ka] Intermediate P (3.6 g, 7.5 mmol), Intermediate B (1.3 g, 7.5 mmol), cerium carbonate (4.9 g, 15.0 mmol), and 60 mL of DMF were added sequentially to a three-neck round-bottom flask. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction solution was poured into a large amount of water, extracted with ethyl acetate, and the organic phase was recovered. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to obtain a pale yellow solid (2.5 g, 4.0 mmol) in 53.3% yield. The product was identified as the target product A-163 with a molecular weight of 626.2.

[0173] Synthesis Example 7: Synthesis of Compound A-185

[0174] Step 1: Synthesis of intermediate R [ka] A three-neck round-bottom flask was charged with Intermediate Q (30.0 g, 99.7 mmol), Intermediate D (13.4 g, 109.7 mmol), Pd(PPh3)4 (1.2 g, 1.0 mmol), K2CO3 (27.5 g, 199.4 mmol), 320 mL of toluene, 80 mL of EtOH, and 80 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE) to obtain Intermediate R (22.6 g, 90.0 mmol) as a white solid in 90.3% yield.

[0175] Step 2: Synthesis of intermediate S [ka] Intermediate R (14.5 g, 57.7 mmol), bis(pinacolato)diboron (22.0 g, 86.6 mmol), Pd(dppf)Cl2 (0.84 g, 1.15 mmol), KOAc (11.3 g, 115.4 mmol), and 300 mL of 1,4-dioxane were added sequentially to a three-neck round-bottom flask. The mixture was heated to reflux overnight under N2 protection. After completion of the reaction was confirmed by TLC, heating was stopped and the mixture was allowed to cool to room temperature. The reaction was filtered through diatomaceous earth, and the solution was filtered, reduced pressure, and concentrated to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 2:1) to obtain intermediate S (15.0 g, 50.3 mmol) as a white solid in 87.2% yield.

[0176] Step 3: Synthesis of intermediate T [ka] A three-necked round-bottom flask was charged with Intermediate S (6.0 g, 20.0 mmol), Intermediate K (8.4 g, 20.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), K2CO3 (5.5 g, 40.0 mmol), 60 mL of toluene, 15 mL of EtOH, and 15 mL of H2O, in that order. Under N2 protection, the mixture was heated to reflux overnight. After TLC confirmed the completion of the reaction, the mixture was cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain Intermediate T (10.4 g, 18.7 mmol) as a white solid in 93.5% yield.

[0177] Step 4: Synthesis of compound A-185 [ka] Intermediate T (5.7 g, 10.3 mmol), Intermediate B (1.7 g, 10.3 mmol), cerium carbonate (6.7 g, 20.5 mmol), and 60 mL of DMF were added sequentially to a three-neck round-bottom flask. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was stopped and cooled to room temperature. The reaction solution was poured into a large amount of water and extracted with ethyl acetate. The organic phase was recovered, concentrated under reduced pressure, and the crude product was obtained. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to give a pale yellow solid (5.0 g, 7.1 mmol) in 68.9% yield. The product was identified as the target product A-185 with a molecular weight of 702.3.

[0178] Synthesis Example 8: Synthesis of Compound A-192

[0179] Step 1: Synthesis of intermediate U [ka] A three-neck round-bottom flask was charged with intermediate S (6.0 g, 20.0 mmol), intermediate M (8.4 g, 20.0 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), K2CO3 (5.5 g, 40.0 mmol), 60 mL of toluene, 15 mL of EtOH, and 15 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the completion of the reaction, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol to obtain a crude product. The crude product was recrystallized from toluene and pulped with ethanol to obtain intermediate U (10.4 g, 18.7 mmol) as a white solid in 93.5% yield.

[0180] Step 2: Synthesis of compound A-192 [ka] Intermediate U (5.7 g, 10.3 mmol), Intermediate B (1.7 g, 10.3 mmol), cerium carbonate (6.7 g, 20.5 mmol), and 60 mL of DMF were added sequentially to a three-neck round-bottom flask. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was stopped and cooled to room temperature. The reaction solution was poured into a large amount of water and extracted with ethyl acetate. The organic phase was recovered, concentrated under reduced pressure, and the crude product was obtained. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to give a pale yellow solid (5.0 g, 7.1 mmol) in 68.9% yield. The product was identified as the target product A-192 with a molecular weight of 702.3.

[0181] Synthetic Example 9: Synthesis of Compound A-273

[0182] Step 1: Synthesis of intermediate W [ka] A three-neck round-bottom flask was charged with Intermediate C (6.5 g, 18.2 mmol), Intermediate V (4.0 g, 20.2 mmol), Pd(PPh3)4 (0.42 g, 0.36 mmol), K2CO3 (5.0 g, 36.4 mmol), 60 mL of toluene, 15 mL of EtOH, and 15 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 8:1) to obtain Intermediate W (7.5 g, 17.4 mmol) as a white solid in 95.6% yield.

[0183] Step 2: Synthesis of intermediate X [ka] To a three-neck round-bottom flask was added, in order, intermediate W (7.5 g, 17.4 mmol), bis(pinacolato)diboron (6.6 g, 26.0 mmol), Pd2(dba)3 (0.32 g, 0.35 mmol), tricyclohexylphosphine tetrafluoroborate (PCy3.HBF4, 0.32 g, 0.35 mmol), KOAc (9.3 g, 95.0 mmol), and 80 mL of 1,4-dioxane. The mixture was heated to reflux overnight under N2 protection. After TLC showed the reaction was complete, the mixture was removed from the heat and allowed to cool to room temperature. The reaction was filtered through diatomaceous earth, and the solution was filtered, concentrated under reduced pressure, and the crude product was obtained. The crude product was purified by column chromatography (PE / DCM=5:1 to 2:1) to obtain a white solid intermediate X (7.5 g, 14.4 mmol), with a yield of 82.8%.

[0184] Step 3: Synthesis of compound A-273 [ka] A three-neck round-bottom flask was charged with intermediate X (4.3 g, 8.2 mmol), intermediate Y (2.2 g, 8.2 mmol), Pd(PPh3)4 (0.19 g, 0.16 mmol), K2CO3 (2.3 g, 16.4 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 3:1) to obtain a pale yellow solid (3.5 g, 5.6 mmol) in 68.3% yield. The product was identified as the target product A-273 with a molecular weight of 626.2.

[0185] Synthesis Example 10: Synthesis of Compound A-448

[0186] Step 1: Synthesis of intermediate AC [ka] Intermediate Z (25 g, 170 mmol), Intermediate AB (39 g, 204 mmol), Pd(PPh3)4 (3.93 g, 3.4 mmol), and Na2CO3 (36 g, 340 mmol) were added to a three-neck round-bottom flask in toluene (80 mL), EtOH (20 mL), and HO (20 mL) and the resulting mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 5:1 to 3:1) to obtain Intermediate AC (33.3 g, 155.8 mmol) as a white solid in 91.6% yield.

[0187] Step 2: Synthesis of intermediate AD [ka] Intermediate AC (33.3 g, 155.8 mmol), bis(pinacolato)diboron (59.3 g, 233.7 mmol), Pd(OAc) (0.7 g, 3.1 mmol), 2-dicyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (X-Phos, 3.0 g, 6.2 mmol), and KOAc (31 g, 311.6 mmol) were added to a three-neck round-bottom flask in 1,4-dioxane (300 mL). The mixture was heated to reflux overnight under N protection. After TLC showed the reaction was complete, the mixture was removed from the heat and allowed to cool to room temperature. The reaction was filtered through diatomaceous earth, and the solution was concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (PE / DCM=5:1 to 2:1) to obtain intermediate AD (28.2 g, 92.4 mmol) as a white solid, with a yield of 59.3%.

[0188] Step 3: Synthesis of intermediate AF [ka] Intermediate AD (24.4 g, 80 mmol), Intermediate AE (27.0 g, 120 mmol), Pd(PPh3)4 (1.85 g, 1.6 mmol), and Na2CO3 (25 g, 240 mmol) were added to a three-neck round-bottom flask in a mixture of THF (400 mL) and HO (100 mL). The mixture was heated to reflux overnight under N2 protection. After completion of the reaction was confirmed by TLC, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 5:1 to 1:1) to obtain Intermediate AF (12.2 g, 33.1 mmol) as a white solid in 41.3% yield.

[0189] Step 4: Synthesis of compound A-448 [ka] A three-neck round-bottom flask was charged with intermediate F (3.86 g, 8.68 mmol), intermediate AF (3.2 g, 8.68 mmol), Pd(PPh3)4 (0.30 g, 0.26 mmol), K2CO3 (2.4 g, 17.36 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 4:1 to 1:1) to obtain a pale yellow solid (3.7 g, 5.68 mmol) in 65.4% yield. The product was identified as the target product A-448 with a molecular weight of 651.2.

[0190] Synthesis Example 11: Synthesis of Compound A-525

[0191] Step 1: Synthesis of intermediate AH [ka] Intermediate A (2.8 g, 13.8 mmol), Intermediate AG (2.0 g, 9.2 mmol), cerium carbonate (CsCO, 6.0 g, 18.5 mmol), and 30 mL of N,N-dimethylformamide (DMF) were sequentially added to a three-neck round-bottom flask. Under N2 protection, the mixture was heated to 130 °C. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction solution was poured into a large amount of water and extracted with ethyl acetate. The organic phase was recovered, concentrated under reduced pressure, and the crude product was obtained. The crude product was purified by column chromatography (PE / DCM = 5:1) to obtain Intermediate AH (3.5 g, 8.6 mmol) as a white solid in 93.5% yield.

[0192] Step 2: Synthesis of intermediate AI [ka] In a three-necked round-bottom flask, add Intermediate AH (3.5 g, 8.6 mmol), Intermediate D (1.6 g, 12.9 mmol), Pd(PPh) (0.5 g, 0.4 mmol), and KCO. 3( A solution of 2.4 g (17.2 mmol), 80 mL of toluene, 20 mL of EtOH, and 20 mL of H2O was added in that order. Under N2 protection, the mixture was heated to reflux overnight. After TLC confirmed the completion of the reaction, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 4:1) to obtain intermediate AI (3.2 g, 7.9 mmol) as a white solid in a 91.9% yield.

[0193] Step 3: Synthesis of intermediate AJ [ka] In a three-necked round-bottom flask, intermediate AI (3.2 g, 7.9 mmol), bis(pinacolato)diboron (3.0 g, 11.9 mmol), Pd(OAc) 2( To the reaction mixture were added 2-dicyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (X-phos, 0.09 g, 0.4 mmol), 2-dicyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (X-phos, 0.4 g, 0.8 mmol), KOAc (1.5 g, 15.8 mmol), and 50 mL of 1,4-dioxane, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction mixture was filtered through diatomaceous earth, and the solution was filtered, reduced pressure, and concentrated to obtain the crude product. The crude product was purified by column chromatography (PE / DCM=3:1) to obtain intermediate AJ (3.5 g, 7.1 mmol) as a white solid in 89.9% yield.

[0194] Step 4: Synthesis of compound A-525 [ka] A three-neck round-bottom flask was charged with Intermediate AJ (3.5 g, 7.1 mmol), Intermediate G (2.6 g, 7.7 mmol), Pd(PPh3)4 (0.41 g, 0.35 mmol), K2CO3 (2.0 g, 14.2 mmol), 80 mL of toluene, 20 mL of EtOH, and 20 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the completion of the reaction, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The obtained solid was rinsed with water and ethanol, successively, to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 3:1) to obtain a pale yellow solid (3.0 g, 4.4 mmol) in 62.0% yield. The product was identified as the target product A-525 with a molecular weight of 676.3.

[0195] Synthesis Example 12: Synthesis of Compound A-528 Step 1: Synthesis of intermediate AL [ka] Intermediate A (2.2 g, 10.5 mmol), Intermediate AK (2.8 g, 10.5 mmol), cerium carbonate (CsCO, 10.0 g, 31.5 mmol), and 50 mL of N,N-dimethylformamide (DMF) were sequentially added to a three-neck round-bottom flask. Under N2 protection, the mixture was heated to 140 °C. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction solution was poured into a large amount of water and extracted with ethyl acetate. The organic phase was recovered, concentrated under reduced pressure, and the crude product was obtained. The crude product was purified by column chromatography (PE / DCM = 3:1) to give Intermediate AL (3.0 g, 6.6 mmol) as a white solid in 62.9% yield.

[0196] Step 2: Synthesis of intermediate AM [ka] In a three-necked round-bottom flask, intermediate AL (3.0 g, 6.6 mmol), intermediate D (0.96 g, 7.9 mmol), Pd(PPh) (0.76 g, 0.66 mmol), and KCO3( A solution of 2.7 g (19.8 mmol), 24 mL of toluene, 6 mL of EtOH, and 6 mL of H2O was added in that order. Under N2 protection, the mixture was heated to reflux overnight. After TLC confirmed the completion of the reaction, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 4:1) to obtain intermediate AM (2.2 g, 4.8 mmol) as a white solid in 72.7% yield.

[0197] Step 3: Synthesis of intermediate AN [ka] In a three-necked round-bottom flask, intermediate AM (2.2 g, 4.8 mmol), bis(pinacolato)diboron (1.85 g, 7.3 mmol), Pd(OAc) 2( To the reaction mixture were added 2-dicyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (X-phos, 0.11 g, 0.49 mmol), 2-dicyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (X-phos, 0.46 g, 0.97 mmol), KOAc (1.4 g, 14.6 mmol), and 25 mL of 1,4-dioxane, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the heating was stopped and the mixture was allowed to cool to room temperature. The reaction mixture was filtered through diatomaceous earth, and the solution was filtered, reduced pressure, and concentrated to give the crude product. The crude product was purified by column chromatography (PE / DCM=2:1) ​​to give intermediate AN (2.4 g, 4.4 mmol) as a white solid in 91.7% yield.

[0198] Step 4: Synthesis of compound A-528 [ka] A three-neck round-bottom flask was charged with Intermediate AN (2.4 g, 4.4 mmol), Intermediate G (1.4 g, 4.2 mmol), Pd(PPh3)4 (0.48 g, 0.35 mmol), K2CO3 (1.7 g, 12.0 mmol), 20 mL of toluene, 5 mL of EtOH, and 5 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was stopped and cooled to room temperature. A large amount of solid precipitated from the reaction solution and filtered. The solid was rinsed with water and ethanol to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 6:1) to obtain a white solid (1.0 g, 1.4 mmol) in 31.8% yield. The product was identified as the target product A-528 with a molecular weight of 726.3.

[0199] Synthesis Example 13: Synthesis of Compound A-65

[0200] Step 1: Synthesis of compound A-65 [ka] A three-neck round-bottom flask was charged with intermediate F (6.68 g, 15.0 mmol), intermediate AO (6.3 g, 15.0 mmol), Pd(PPh3)4 (0.52 g, 0.45 mmol), K2CO3 (4.15 g, 30.0 mmol), 72 mL of toluene, 18 mL of EtOH, and 18 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 2:1) to obtain a pale yellow solid (8.3 g, 11.8 mmol) in 78.7% yield. The product was identified as the target product A-65 with a molecular weight of 702.3.

[0201] Synthesis Example 14: Synthesis of Compound A-77

[0202] Step 1: Synthesis of intermediate AP [ka] Intermediate F (17.8 g, 40.0 mmol), Intermediate AE (11.8 g, 52.0 mmol), Pd(PPh3)4 (0.92 g, 0.80 mmol), and Na2CO3 (8.48 g, 80.0 mmol) were added to a three-neck round-bottom flask in a mixture of THF (256 mL) and HO (64 mL). The mixture was heated to reflux under N2 protection. After 7 h, TLC confirmed the reaction was complete. The mixture was then cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 6:1 to 3:1) to obtain Intermediate AP (12.4 g, 24.4 mmol) as a yellow solid in 60.9% yield.

[0203] Step 2: Synthesis of compound A-77 [ka] A three-neck round-bottom flask was charged with Intermediate AP (4.07 g, 8.0 mmol), Intermediate AQ (2.85 g, 8.0 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), K2CO3 (2.21 g, 16.0 mmol), 40 mL of toluene, 10 mL of EtOH, and 10 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature and the reaction solution was decompressed and suction filtered. The resulting solid was rinsed with water and methanol several times to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 2:1) to obtain a pale yellow solid (4.3 g, 6.1 mmol) in 76.5% yield. The product was identified as the target product A-77 with a molecular weight of 702.3.

[0204] Synthesis Example 15: Synthesis of Compound A-434

[0205] Step 1: Synthesis of compound A-434 [ka] A three-neck round-bottom flask was charged with intermediate AR (1.8 g, 4.0 mmol), intermediate K (1.7 g, 4.0 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol), K2CO3 (1.1 g, 8.0 mmol), 24 mL of toluene, 6 mL of EtOH, and 6 mL of H2O, in that order. Under N2 protection, the mixture was heated to reflux overnight. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature and the reaction solution was decompressed and suction filtered. The resulting solid was rinsed with water and ethanol to obtain the crude product. The crude product was recrystallized from a toluene / acetonitrile mixture to obtain a pale yellow solid (2.2 g, 3.1 mmol) in 78.1% yield. The product was identified as the target product A-434 with a molecular weight of 703.3.

[0206] Synthesis Example 16: Synthesis of Compound A-95

[0207] Step 1: Synthesis of compound A-95 [ka] A three-neck round-bottom flask was charged with Intermediate F (5.0 g, 11.2 mmol), Intermediate AS (4.4 g, 11.2 mmol), Pd(PPh3)4 (0.26 g, 0.23 mmol), K2CO3 (3.1 g, 22.4 mmol), 120 mL of toluene, 30 mL of EtOH, and 30 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with ethyl acetate, and the organic phases were combined. The mixture was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 4:1) to give a pale yellow solid (5.0 g, 7.4 mmol) in 66.1% yield. The product was identified as the target product A-95 with a molecular weight of 676.3.

[0208] Synthesis Example 17: Synthesis of Compound A-582

[0209] Step 1: Synthesis of compound A-582 [ka] A three-neck round-bottom flask was charged with intermediate F (4.0 g, 9.0 mmol), intermediate AT (3.78 g, 9.0 mmol), Pd(PPh3)4 (0.31 g, 0.27 mmol), K2CO3 (2.49 g, 18.0 mmol), 48 mL of toluene, 12 mL of EtOH, and 12 mL of HO, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature and the reaction solution was decompressed and suction filtered. The resulting solid was rinsed with water and methanol several times to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 10:1 to 5:2) to obtain a pale yellow solid (4.6 g, 6.54 mmol) in 72.7% yield. The product was identified as the target product A-582 with a molecular weight of 702.3.

[0210] Synthesis Example 18: Synthesis of Compound A-583

[0211] Step 1: Synthesis of intermediate AV [ka] Intermediate A (4.8 g, 22.9 mmol), Intermediate AU (5.0 g, 23.0 mmol), cerium carbonate (18.6 g, 57.5 mmol), and 100 mL of N,N-dimethylformamide (DMF) were sequentially added to a three-neck round-bottom flask. The mixture was heated to 140 °C under N2 protection. After completion of the reaction was confirmed by TLC, heating was stopped and the mixture was allowed to cool to room temperature. The reaction solution was poured into a large amount of water and extracted with DCM. The organic phase was recovered, concentrated under reduced pressure, and the crude product was obtained. The crude product was purified by column chromatography (PE / DCM = 5:1) to give Intermediate AV (5.5 g, 13.6 mmol) as a white solid in a 59.0% yield.

[0212] Step 2: Synthesis of intermediate AW [ka] A three-neck round-bottom flask was charged with Intermediate AV (5.5 g, 13.6 mmol), Intermediate D (1.8 g, 14.9 mmol), Pd(PPh3)4 (1.6 g, 1.4 mmol), K2CO3 (4.3 g, 31.1 mmol), 48 mL of toluene, 12 mL of EtOH, and 12 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 5:1) to obtain Intermediate AW (4.3 g, 10.7 mmol) as a white solid in 78.7% yield.

[0213] Step 3: Synthesis of intermediate AX [ka] To a three-neck round-bottom flask, intermediate AW (4.3 g, 10.7 mmol), bis(pinacolato)diboron (4.0 g, 15.8 mmol), Pd(OAc) (0.22 g, 1.0 mmol), 2-dicyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (X-phos, 1.0 g, 2.1 mmol), KOAc (3.1 g, 32.1 mmol), and 50 mL of 1,4-dioxane were added in that order. The mixture was heated to reflux overnight under N2 protection. After TLC showed the reaction was complete, the mixture was turned off and allowed to cool to room temperature. The reaction was filtered through diatomaceous earth, and the solution was concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (PE / DCM=2:1) ​​to give intermediate AX (3.8 g, 7.7 mmol) as a white solid, with a yield of 72.0%.

[0214] Step 4: Synthesis of compound A-583 [ka] A three-neck round-bottom flask was charged with Intermediate AX (3.8 g, 7.7 mmol), Intermediate G (3.1 g, 7.7 mmol), Pd(PPh3)4 (0.89 g, 0.8 mmol), K2CO3 (3.2 g, 23 mmol), 28 mL of toluene, 7 mL of EtOH, and 7 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with DCM, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 5:1) to give a pale yellow solid (2.1 g, 3.1 mmol) in 40.3% yield. The product was identified as the target product A-583 with a molecular weight of 676.3.

[0215] Synthesis Example 19: Synthesis of Compound A-584

[0216] Step 1: Synthesis of compound A-584 [ka] A three-neck round-bottom flask was charged with Intermediate F (4.1 g, 9.0 mmol), Intermediate AY (3.5 g, 9.0 mmol), Pd(PPh3)4 (0.21 g, 0.17 mmol), K2CO3 (2.5 g, 18.0 mmol), 120 mL of toluene, 30 mL of EtOH, and 30 mL of H2O, in that order. The mixture was heated to reflux overnight under N2 protection. After TLC confirmed the reaction was complete, the mixture was cooled to room temperature. The reaction mixture was separated, the liquid phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE / DCM = 4:1) to give a pale yellow solid (3.5 g, 5.2 mmol) in 57.5% yield. The product was identified as the target product A-584 with a molecular weight of 676.3.

[0217] Those skilled in the art should know that the above preparation methods are merely exemplary and can be modified to obtain the structures of other compounds of the present invention.

[0218] The method for manufacturing an electroluminescent device is not limited. The manufacturing methods in the following examples are merely illustrative and should not be construed as limiting. Those skilled in the art can reasonably improve the manufacturing methods in the following examples based on conventional techniques. For example, the ratio of various materials in the light-emitting layer is not particularly limited, and those skilled in the art can reasonably select it within a certain range based on conventional techniques. For example, based on the total weight of the light-emitting layer materials, the host material may account for 80% to 99% and the light-emitting material may account for 1% to 20%, or the host material may account for 90% to 99% and the light-emitting material may account for 1% to 10%, or the host material may account for 95% to 99% and the light-emitting material may account for 1% to 5%. The host material may also consist of one or two materials. The ratio of the two host materials to the host material may be 100:0 to 1:99, 80:20 to 20:80, or 60:40 to 40:60. In the device examples, the device characteristics were also tested using equipment commonly used in the field (including, but not limited to, an evaporation machine manufactured by Angstrom Engineering, an optical test system and a service life test system manufactured by Suzhou Fusida, an ellipsometer manufactured by Beijing Liangtang, etc.) in a manner familiar to those skilled in the art.

[0219] Example of the element

[0220] Element Example 1

[0221] First, a glass substrate with an 80 nm thick indium tin oxide (ITO) was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8In the case of a 1000-kV OLED, the layers were sequentially deposited on an ITO anode by hot vacuum evaporation at a rate of 0.2 to 2 Å / s. Compound HI was used as a hole injection layer (HIL). Compound HT was used as a hole transport layer (HTL). Compound PH-23 was used as an electron blocking layer (EBL). Compound GD23 was doped into compound PH-23 and compound A-27 of the present invention (compound PH-23:compound A-27:compound GD23=69:23:8) and co-deposited to form an emitting layer (EML). Compound HB was used as a hole blocking layer (HBL). Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the hole blocking layer to form an electron transport layer (ETL). Finally, a 1-nm thick layer of 8-hydroxyquinoline-lithium (Liq) was evaporated as an electron injection layer, and a 120-nm thick layer of aluminum was evaporated as a cathode. The device was then transferred to a glove box and encapsulated with a glass cover to complete the device.

[0222] Comparative Example 1 of the Element

[0223] The preparation of Device Comparative Example 1 was similar to Device Example 1, except that Compound C-1 replaced Compound A-27 in the light-emitting layer (EML).

[0224] Comparative example 2 of the element

[0225] The preparation of Device Comparative Example 2 was similar to Device Example 1, except that Compound C-2 replaced Compound A-27 in the light-emitting layer (EML).

[0226] Comparative Example 3 of the Element

[0227] The preparation of Device Comparative Example 3 was similar to Device Example 1, except that Compound C-3 replaced Compound A-27 in the light-emitting layer (EML).

[0228] Comparative Example 4 of the Element

[0229] The preparation of Device Comparative Example 4 was the same as Device Example 1, except that Compound C-4 replaced Compound A-27 in the light-emitting layer (EML).

[0230] Comparative Example 5 of the Element

[0231] The preparation of Device Comparative Example 5 was the same as Device Example 1, except that Compound C-5 replaced Compound A-27 in the light-emitting layer (EML).

[0232] Comparative Example 6 of the Element

[0233] The preparation of Device Comparative Example 6 was similar to Device Example 1, except that Compound C-6 replaced Compound A-27 in the light-emitting layer (EML).

[0234] Comparative Example 7 of the Element

[0235] The preparation of Device Comparative Example 7 was similar to Device Example 1, except that Compound C-7 replaced Compound A-27 in the light-emitting layer (EML).

[0236] Comparative Example 8 of the Element

[0237] The preparation of Device Comparative Example 8 was similar to Device Example 1, except that Compound C-8 replaced Compound A-27 in the light-emitting layer (EML).

[0238] Comparative Example 9 of the Element

[0239] The preparation of Device Comparative Example 9 was similar to Device Example 1, except that Compound C-9 replaced Compound A-27 in the light-emitting layer (EML).

[0240] Element Example 2

[0241] The fabrication of Device Example 2 is similar to Device Example 1, except that Compound A-28 replaces Compound A-27 in the light-emitting layer (EML).

[0242] Element Example 3

[0243] The fabrication of Device Example 3 is similar to Device Example 1, except that Compound A-49 replaces Compound A-27 in the light-emitting layer (EML).

[0244] Element Example 4

[0245] The fabrication of Device Example 4 is similar to Device Example 1, except that Compound A-56 replaces Compound A-27 in the light-emitting layer (EML).

[0246] Element Example 5

[0247] The preparation of Device Example 5 is similar to Device Example 1, except that Compound A-163 replaces Compound A-27 in the light-emitting layer (EML).

[0248] Element Example 6

[0249] The preparation of Device Example 6 was the same as Device Example 1, except that Compound A-273 replaced Compound A-27 in the light-emitting layer (EML), with a ratio of PH-23:A-273:GD23=64:28:8.

[0250] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0251] [Table 1]

[0252] The structure of the material used in the element is as follows: [ka] [ka] [ka]

[0253] Table 2 shows the 15mA / cm 2 CIE data, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) measured under a constant current of 80 mA / cm 2 The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0254] [Table 2]

[0255] summary:

[0256] In Example 1 and Comparative Example 1, Compound A-27 of the present invention and Compound C-1 outside the present invention were used, respectively. The only difference between Compound A-27 and Compound C-1 is that the phenylene group, which is the bridging group linking carbazole and triazine, lacks a phenyl group substituent. The EQE and CE in Example 1 were comparable to those of Comparative Example 1, but the driving voltage was slightly reduced, while the device life was improved by 16.3%. It has been demonstrated that the compound having the structure of Formula 1 according to the present invention, when applied to an electroluminescent device, can significantly improve the device performance, particularly the device life, compared to a compound lacking an aryl group substituent on the phenylene group, which is the bridging group linking carbazole and triazine.

[0257] In Example 1, Comparative Example 2, and Comparative Example 3, Compound A-27 of the present invention and Compounds C-2 and C-3 other than those of the present invention were used, respectively. Compound A-27 differed from Compounds C-2 and C-3 only in the position of the phenyl group substituent in the phenylene group, which is the bridging group connecting carbazole and triazine. In Compound A-27, the phenyl group and triazine were at the para position, in Compound C-2, the phenyl group and triazine were at the meta position, and in Compound C-3, the phenyl group and triazine were at the ortho position. The EQE and CE in Example 1 were comparable to those in Comparative Example 2, but the driving voltage was slightly reduced and the device life was improved by 36.6%. The driving voltage, EQE, and CE in Example 1 were comparable to those in Comparative Example 3, but the device life was significantly improved by 1043 times. It has been proven that the compound having the structure of Formula 1 according to the present invention, when applied to an electroluminescent device, can significantly improve the performance of the device, and in particular, can unexpectedly improve the service life of the device, compared to a compound in which other positions of the phenylene group, which is the bridging group connecting carbazole and triazine, are substituted with phenyl groups.

[0258] Example 5, Comparative Example 4, and Comparative Example 5 use Compound A-163 of the present invention and Compounds C-4 and C-5 outside the present invention, respectively. In Compound A-163, carbazole is bonded to the ortho position of triazine. The only difference between Compound A-163 and Compound C-4 and C-5 is the position of the phenyl group substituent in the phenylene group, which is the bridging group connecting carbazole and triazine. In Compound A-163, the phenyl group and triazine are in the para position, while in Compound C-4 and C-5, the phenyl group and triazine are both in the meta position. Compared to Comparative Example 4, Example 5 had a 0.3 V decrease in driving voltage, a slight improvement in EQE and CE, and a significant 51.5% improvement in device service life. While Example 5 had the same driving voltage, EQE, and CE as Comparative Example 5, the device service life was significantly improved by 39.0%. Similarly, it has been proven that the compound having the structure of Formula 1 according to the present invention, when applied to an electroluminescent device, can significantly improve the performance of the device, and in particular, can unexpectedly improve the service life of the device, compared to a compound in which other positions of the phenylene group, which is the bridging group connecting the carbazole and triazine, are substituted with phenyl groups.

[0259] In Example 1 and Comparative Example 6, Compound A-27 of the present invention and Compound C-6, which is not of the present invention, were used, respectively. The only difference between Compound A-27 and Compound C-6 was the relative positions of carbazole and triazine. In Compound A-27, carbazole and triazine were in the meta position, while in Compound C-6, carbazole and triazine were in the para position. The driving voltage in Example 1 was slightly lower than in Comparative Example 6, and the EQE and CE were comparable to those of Comparative Example 6, but the device life was improved by 23.4%. It has been demonstrated that the compound having the structure of Formula 1 according to the present invention, when applied to an electroluminescent device, can significantly improve the device performance, particularly the device life, compared to a compound in which carbazole and triazine were in the para position.

[0260] In Example 1 and Comparative Example 7, Compound A-27 of the present invention and Compound C-7 outside the present invention were used. The only difference between Compound A-27 and Compound C-7 was whether or not the carbazole had a phenyl group substitution. The EQE and CE in Example 1 were comparable to those of Comparative Example 7, but the driving voltage was slightly reduced, while the device life was significantly improved by 85.1%. It has been demonstrated that the compound having the structure of Formula 1 according to the present invention, when applied to an electroluminescent device, can significantly improve the device performance, particularly the device life, compared to a compound having an aryl group substitution in the carbazole.

[0261] In Example 1 and Comparative Example 8, Compound A-27 of the present invention and Compound C-8 other than the present invention were used, respectively. The only difference between Compound A-27 and Compound C-8 is whether or not a five-membered ring is also fused to carbazole. Compared to Comparative Example 8, the driving voltage in Example 1 was slightly reduced, while both the EQE and CE were slightly improved, and in particular the device life was significantly improved by 74.0%. It has been proven that the compound having the structure of Formula 1 according to the present invention can significantly improve the device performance, especially the device life, when applied to an electroluminescent device, compared to a compound in which a five-membered ring is also fused to carbazole.

[0262] Example 1 and Comparative Example 9 use Compound A-27 of the present invention and Compound C-9, which is not of the present invention. The only difference between Compound A-27 and Compound C-9 is the number of phenylene carbazoles attached to the triazine. Compound A-27 has only one phenylene carbazole in the triazine, while Compound C-9 has two phenylene carbazoles in the triazine. Compared to Comparative Example 9, Example 1 showed a 0.4 V decrease in driving voltage, slight improvements in EQE and CE, and a 40.3% increase in device life. It has been demonstrated that the compound having the structure of Formula 1 according to the present invention, when applied to an electroluminescent device, can significantly improve device performance, particularly device life, compared to a compound having two phenylene carbazoles substituted in the triazine.

[0263] In Examples 2 to 6, compounds having the structure of Formula 1 according to the present invention, which have different structures, were used, and the devices obtained results comparable to or superior to those of Example 1 in terms of voltage, CE, EQE, and service life. These Examples further demonstrate the superiority of the compound having the structure of Formula 1 according to the present invention.

[0264] Device Example 7

[0265] The fabrication of Device Example 7 is similar to Device Example 3, except that Compound PH-24 replaces Compound PH-23 in the light-emitting layer (EML).

[0266] Device Example 8

[0267] The preparation of Device Example 8 is similar to Device Example 7, except that Compound A-50 replaces Compound A-49 in the light-emitting layer (EML).

[0268] Device Example 9

[0269] The preparation of Device Example 9 was the same as Device Example 7, except that in the light-emitting layer (EML), compound PH-27 replaced compound PH-24, with the ratio of PH-27:A-49:GD23 being 64:28:8.

[0270] Device Example 10

[0271] The preparation of Device Example 10 is similar to Device Example 9, except that Compound A-185 replaces Compound A-49 in the light-emitting layer (EML).

[0272] Device Example 11

[0273] The preparation of Device Example 11 is similar to Device Example 9, except that Compound A-192 replaces Compound A-49 in the light-emitting layer (EML).

[0274] Element Example 20

[0275] The preparation of Device Example 20 was the same as Device Example 1, except that compound PH-104 replaced compound PH-23 in the light-emitting layer (EML), with the ratio of PH-104:A-27:GD23=64:28:8.

[0276] Device Example 21

[0277] The preparation of Device Example 21 is similar to Device Example 20, except that Compound PH-105 replaces Compound PH-104 in the light-emitting layer (EML).

[0278] Device Example 22

[0279] The preparation of Device Example 22 is similar to Device Example 20, except that Compound PH-109 replaces Compound PH-104 in the light-emitting layer (EML).

[0280] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0281] [Table 3]

[0282] The structure of the new material used in the device is as follows: [ka]

[0283] Table 4 shows the 15 mA / cm 2 CIE data, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) measured under a constant current of 80 mA / cm 2 The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0284] [Table 4]

[0285] summary:

[0286] In Examples 7 to 11 and Examples 20 to 22, different compounds of the present invention were used in combination with different second host compounds. The devices exhibited high efficiency and long service life. This demonstrates that the compounds of the present invention can be combined with common second host compounds to achieve excellent device performance.

[0287] Device Example 12

[0288] The preparation of Device Example 12 was the same as Device Example 7, except that compound GD15 replaced compound GD23 in the light-emitting layer (EML), with a ratio of PH-24:A-49:GD15=56:38:6.

[0289] Device Example 13

[0290] The preparation of Device Example 13 was similar to Device Example 12, except that compound GD2 replaced compound GD15 in the light-emitting layer (EML), with a ratio of PH-24:A-49:GD2=61:33:6.

[0291] Device Example 14

[0292] The preparation of Device Example 14 is similar to Device Example 13, except that Compound A-50 replaces Compound A-49 in the light-emitting layer (EML).

[0293] Device Example 15

[0294] The preparation of Device Example 15 was the same as Device Example 9, except that compound GD2 replaced compound GD23 in the light-emitting layer (EML), with a ratio of PH-27:A-49:GD2=66:28:6.

[0295] Device Example 16

[0296] The preparation of Device Example 16 is similar to Device Example 15, except that Compound A-185 replaces Compound A-49 in the light-emitting layer (EML).

[0297] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0298] [Table 5]

[0299] The structure of the new material used in the device is as follows: [ka] Table 6 shows the 15mA / cm 2 CIE data, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) measured under a constant current of 80 mA / cm 2The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0300] [Table 6]

[0301] summary:

[0302] In Examples 12 to 16, different compounds of the present invention were used in combination with common green phosphorescent dopants. The devices all exhibited particularly low driving voltages, high efficiency, and long service life. It has been demonstrated that the compounds having the structure of Formula 1 of the present invention can be combined with common green phosphorescent dopants to achieve excellent device performance.

[0303] Device Example 23

[0304] First, a glass substrate with an 80 nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8In the case of a 1000 Å thick LED, the layers were sequentially deposited on an ITO anode by hot vacuum evaporation at a rate of 0.1 to 2 Å / s. Compound HT and compound HT1 were co-deposited to form a hole injection layer (HIL, with a weight ratio of compound HT:compound HT1 of 97:3) with a thickness of 100 Å. Compound HT was used as a hole transport layer (HTL), with a thickness of 350 Å. Compound PH-23 was used as an electron blocking layer (EBL), with a thickness of 50 Å. Compound GD23 was doped into compound PH-24 and compound A-65 of the present invention, and co-deposited to form an emitting layer (EML, with a weight ratio of compound PH-24:compound A-65:compound GD23 of 64:28:8) with a thickness of 400 Å. Compound HB was used as a hole blocking layer (HBL), with a thickness of 50 Å. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated to form an electron-transporting layer (ETL) with a thickness of 350 Å. Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm was evaporated to form an electron-injection layer, and aluminum with a thickness of 1200 Å was evaporated to form a cathode. The device was then transferred to a glove box and encapsulated with a glass cover to complete the device.

[0305] Device Example 24

[0306] The fabrication of Device Example 24 was the same as Device Example 23, except that in the light-emitting layer (EML), Compound PH-121 was substituted for Compound PH-24, Compound A-56 was substituted for Compound A-65, and Compound GD2 was substituted for Compound GD23, with a PH-121:A-56:GD2 ratio of 66:28:6.

[0307] Device Example 25

[0308] The preparation of Device Example 25 is similar to Device Example 24, except that Compound A-77 replaces Compound A-56 in the light-emitting layer (EML).

[0309] Element Example 26

[0310] The fabrication of Device Example 26 was the same as Device Example 24, except that Compound PH-1 was substituted for Compound PH-23 in the electron blocking layer (EBL), and Compound GD66 was substituted for Compound GD2 in the light-emitting layer (EML), with the ratio of PH-121:A-56:GD66 being 64:28:8.

[0311] Device Example 27

[0312] The fabrication of Device Example 27 was the same as that of Device Example 26, except that Compound HI was substituted for Compound HT and Compound HT1 in the hole-injection layer (HIL), Compound PH-23 was substituted for Compound PH-1 in the electron-blocking layer (EBL), Compound PH-24 was substituted for Compound PH-121 in the light-emitting layer (EML), and Compound A-50 was substituted for Compound A-56, with the ratio of PH-24:A-50:GD66 being 70:24:6.

[0313] Device Example 28

[0314] The preparation of Device Example 28 is similar to Device Example 26, except that Compound PH-104 is substituted for Compound PH-121 and Compound A-49 is substituted for Compound A-56 in the light-emitting layer (EML).

[0315] Device Example 29

[0316] The preparation of Device Example 29 is similar to Device Example 26, except that compound GD77 replaces compound GD66 in the light-emitting layer (EML).

[0317] Element Example 30

[0318] The fabrication of Device Example 30 was the same as Device Example 27, except that in the hole injection layer (HIL), Compound HT and Compound HT1 (the weight ratio of Compound HT:Compound HT1 was 97:3) replaced Compound HI, and in the light-emitting layer (EML), Compound GD77 replaced Compound GD66, with a weight ratio of PH-24:A-50:GD77=64:28:8.

[0319] Element Example 31

[0320] The preparation of Device Example 31 is similar to Device Example 28, except that compound GD77 replaces compound GD66 in the light-emitting layer (EML).

[0321] Element Example 33

[0322] The preparation of Device Example 33 was similar to Device Example 31, except that Compound PH-130 was substituted for Compound PH-104 in the light-emitting layer (EML).

[0323] Element Example 34

[0324] The preparation of Device Example 34 is similar to Device Example 33, except that compound GD66 is substituted for compound GD77 in the light-emitting layer (EML).

[0325] Element Example 35

[0326] The preparation of Device Example 35 was the same as Device Example 33, except that compound GD78 replaced compound GD77 in the light-emitting layer (EML), with a ratio of PH-130:A-49:GD78=66:28:6.

[0327] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0328] [Table 7]

[0329] The structure of the new material used in the device is as follows: [ka] [ka]

[0330] Table 12 shows the results of Examples 23 to 25 at 15 mA / cm 2 CIE data, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) measured under a constant current of 80 mA / cm 2 The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0331] [Table 8]

[0332] In Examples 23 to 25, different compounds having the structure of Formula 1 according to the present invention were combined with different second host compounds and green phosphorescent dopants. All of the devices exhibited low voltages, high efficiency, and long service life. These examples further demonstrate the advantages of the compounds having the structure of Formula 1 according to the present invention.

[0333] Table 13 shows the results of Examples 26 to 31 and Example 33 at 15 mA / cm 2 The CIE data measured under a constant current of 1000 kJ / s, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) are shown.

[0334] [Table 9]

[0335] In Examples 26 to 31 and 33, different compounds having the structure of Formula 1 according to the present invention were combined with different second host compounds and green phosphorescent dopants. The devices all achieved low voltages and high efficiencies. These examples further demonstrate the advantages of the compounds having the structure of Formula 1 according to the present invention.

[0336] Table 14 shows the results of Example 34 and Example 35 at 15 mA / cm 2CIE data, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) measured under a constant current of 80 mA / cm 2 The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0337] [Table 10]

[0338] In Examples 34 and 35, the compound having the structure of Formula 1 according to the present invention was combined with a different second host compound and a green phosphorescent dopant. The devices obtained both exhibited low voltages, high efficiency, and long service life. These examples further demonstrate the advantages of the compound having the structure of Formula 1 according to the present invention.

[0339] Device Example 17

[0340] First, a glass substrate with a 120 nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a glove box filled with nitrogen gas to remove water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8At Torr, deposition was performed sequentially on an ITO anode by hot vacuum evaporation at a rate of 0.01 to 5 Å / s. Compound HT and compound HT1 were co-deposited to form a hole injection layer (HIL, 100 Å). Compound HT was used as a hole transport layer (HTL, 400 Å). Compound HT2 was used as an electron blocking layer (EBL, 50 Å). Compound RD28 was doped into compound PH-44 and compound A-528 of the present invention at a ratio of compound PH-44:compound A-528:compound RD28 = 49:49:2, and co-deposited to form an emitting layer (EML, 400 Å). Compound HB was used as a hole blocking layer (HBL, 50 Å). Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the hole blocking layer to form an electron transport layer (ETL, 350 Å). Finally, a 10 Å thick layer of 8-hydroxyquinoline-lithium (Liq) was evaporated as an electron injection layer (EIL) and a 1200 Å thick layer of aluminum was evaporated as a cathode. The device was then transferred to a glove box and encapsulated with a glass cover to complete the device.

[0341] Device Example 18

[0342] The preparation of Device Example 18 was the same as Device Example 17, except that in the light-emitting layer (EML), compound PH-81 replaced compound PH-44, with the ratio of PH-81:A-528:RD28=88:10:2.

[0343] Device Example 32

[0344] The preparation of Device Example 32 was the same as that of Device Example 17, except that in the light-emitting layer (EML), Compound A-95 was substituted for Compound A-528, Compound RD135 was substituted for Compound RD28, and the ratio of PH-44:A-95:RD135 was 39:59:2.

[0345] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0346] [Table 11]

[0347] The structure of the new material used in the device is as follows: [ka]

[0348] Table 8 shows the 15mA / cm 2 CIE data, driving voltage, external quantum efficiency (EQE) and current efficiency (CE) measured under a constant current of 80 mA / cm 2 The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0349] [Table 12]

[0350] summary:

[0351] In Examples 17 and 18, Compound A-528 of the present invention, in which a six-membered ring is fused to carbazole, was used in a red phosphorescent device. In Example 32, Compound A-95 of the present invention, in which triazine is bonded to a phenyl group-naphthalene group structure, was used in a red phosphorescent device. Both devices exhibited low driving voltage, high efficiency, and long service life. The compound having the structure of Formula 1 of the present invention has also been proven to be an excellent red-light host material.

[0352] In summary, when the compound of the present invention is used as a host material in the emissive layer, it can improve the electron-hole transport equilibrium of the material, and compared with the case where a compound other than the present invention is used as a host material in the emissive layer, it can significantly improve the overall performance of the device, while reducing or slightly decreasing the driving voltage and improving or slightly increasing the device efficiency (EQE and CE), thereby significantly improving the device service life, which plays an important role in the industry.

[0353] Device Example 19

[0354] First, a glass substrate with an 80 nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8 In the case of a 1000-kV OLED, the layers were sequentially deposited on an ITO anode by hot vacuum evaporation at a rate of 0.2 to 2 Å / s. Compound HI was used as a hole-injection layer (HIL). Compound HT was used as a hole-transport layer (HTL). Compound PH-23 was used as an electron-blocking layer (EBL). Compound GD23 was doped into compounds PH-23 and NH-1, and the resulting layers were co-deposited to form an emitting layer (EML). Compound HB was used as a hole-blocking layer (HBL). Compound A-27 of the present invention and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the hole-blocking layer to form an electron-transport layer (ETL). Finally, a 1-nm-thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited to form an electron-injection layer, and 120 nm of aluminum was deposited to form a cathode. The device was then transferred to a glove box and encapsulated with a glass cover to complete the device.

[0355] Comparative Example 10 of the Element

[0356] The preparation of Comparative Example Device 10 was similar to that of Device Example 19, except that Compound ET was substituted for Compound A-27 in the electron-transporting layer (ETL).

[0357] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0358] [Table 13]

[0359] The structure of the new material used in the device is as follows: [ka]

[0360] Table 10 shows the 15mA / cm 2 CIE data, driving voltage (V) and external quantum efficiency (EQE) measured under a constant current of 80mA / cm 2 The useful life (LT97) of the element measured under a constant current of 1000 kJ / s is shown.

[0361] [Table 14]

[0362] summary:

[0363] In Example 19 and Comparative Example 10, compound A-27 of the present invention and compound ET, which is not of the present invention, were used as electron-transporting materials, respectively. The driving voltage in Example 19 was similar to that in Comparative Example 10, but both the EQE and the service life of the device were slightly improved. Compound ET is a currently commercially available electron-transporting material, and it was found that the compound of the present invention is also an excellent electron-transporting material.

[0364] It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the present invention. Therefore, it will be apparent to those skilled in the art that the invention sought to be protected includes variations on the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims

1. A compound having a structure represented by formula 1. 【Chemical 1】 wherein X at each occurrence is the same or different and is selected from C or CR x ; Z at each occurrence is the same or different and is selected from CR z ; Ar, each occurrence, may be the same or different and is selected from Formula 2 or Formula 2-1, wherein Formula 2 and Formula 2-1 each have the following structure: 【Chemistry 2】 R in Formula 2 or Formula 2-1 ｔ are the same or different at each occurrence and represent mono-, multi- or no substitution; The "*" in the structure of Formula 2 or Formula 2-1 represents the bonding site to the benzene ring where the R substituent in Formula 1 is located. L, at each occurrence, is the same or different and is selected from a single bond or formula 5, wherein formula 5 has the following structure: 【Chemistry 3】 V in Formula 5 is selected from C or CR v , and may be the same or different at each occurrence; e is the same or different at each occurrence and is selected from 1 or 2; In Formula 5, "*" represents the bonding site to the triazine shown in Formula 1 or Formula 5, and "#" represents the bonding site to Ar 1 in Formula 1 or Formula 5; Ar １ are the same or different at each occurrence and are selected from formula 8, formula 9, or a combination thereof, wherein formula 8 and formula 9 each have the following structure: 【Chemistry 4】 In Formula 8 and Formula 9, U may be the same or different and is selected from C or CR u at each occurrence; The symbol "*" in Formula 8 and Formula 9 represents the bonding site with L in Formula 1, Formula 8, or Formula 9. R ｕ , R ｖ , R ｔ are each occurrence the same or different and are selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups of 1 to 12 carbon atoms, and combinations thereof; R ｘ are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, and combinations thereof; R ｚ are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, and combinations thereof; R is the same or different at each occurrence and represents mono-, multi- or unsubstituted; R, at each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a phosphino group, and combinations thereof; t is selected from 0, 1, or 2; s is selected from 1, 2, or 3; In Formula 1, the substituents R ｘ and the substituent R ｚ adjacent substituents may be joined to form a 6-membered ring, but only to themselves; L is the same at each occurrence and when selected from a single bond, Ar １ is different for each occurrence and is selected from Equation 8, Equation 9, or a combination thereof.

2. The Ar is selected from the structure represented by formula 2, and / or the L is the same or different at each occurrence and is selected from the structure represented by formula 5, and / or the Ar １ The compound of claim 1, wherein each occurrence of is the same or different and is selected from the structure represented by formula 8.

3. The compound of claim 1 , wherein the compound has a structure represented by formula 1-1. 【Chemistry 5】 (X, at each occurrence, is the same or different and is selected from C or CR x , provided that in Formula 1-1, one X is selected from C and has the structure 【Chemistry 6】 and Z, each occurrence of which may be the same or different, binds to CR ｚ wherein U, at each occurrence, is the same or different and is selected from CR u ; and V, at each occurrence, is the same or different and is selected from C or CR v ; L １ is a single bond or 【Chemistry 7】 Selected from e is 1, R x , R ｕ , R ｖ , R ｔ are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl groups of 1 to 6 carbon atoms, and combinations thereof; Rz, at each occurrence, may be the same or different and is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, and combinations thereof; R, R ｔ are the same or different at each occurrence and represent mono-, multi- or no substitution; R, at each occurrence, is the same or different and is selected from the group consisting of hydrogen, deuterium, and combinations thereof; t is selected from 0, 1, or 2; s is 1 or 2; Selected from In formula 1-1, adjacent substituents Rz may be bonded to each other to form a 6-membered ring.

4. Ar may be the same or different at each occurrence. 【Chemistry 8】 The compound of claim 1 selected from:

5. 2. The compound according to claim 1, wherein t is selected from 0 or 1, e is selected from 1, and s is selected from 1 or 2.

6. The R and R ｘ , R ｕ , R ｔ , R ｖ are each occurrence identically or differently selected from the group consisting of hydrogen, deuterium, and combinations thereof; R z at each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, unsubstituted alkenyl groups having 2 to 10 carbon atoms, and combinations thereof; The compound according to claim 1 or 3, wherein in formula 1, adjacent substituents R z may be bonded to each other to form a 6-membered ring.

7. The Ar 1 may be the same or different at each occurrence. 【Chemistry 9】 The compound of claim 1 selected from:

8. A compound selected from the group consisting of the following structures: 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical 26】 【Chemical 27】 【Chemical 28】 【Chemical 29】 【Chemistry 30】 【Chemical 31】 【Chemical 32】 【Chemical Formula 33】 【Chemical 34】 【Chemistry 35】 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemical 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 (The hydrogen atoms in the above compounds may be partially or completely deuterated.)

9. an anode; A cathode; an organic layer provided between the anode and the cathode, An organic electroluminescence device, wherein the organic layer contains the compound according to claim 1 or 8.

10. the organic layer is an emitting layer and the compound is a host compound, or Alternatively, the organic layer is an electron transport layer and the compound is an electron transport compound; Alternatively, the organic layer is a hole-blocking layer, and the compound is a hole-blocking compound. The device of claim 9.

11. The light-emitting layer further includes a first metal complex, and the first metal complex is ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ 11. The device of claim 10 having the general formula: wherein the metal M is selected from metals having a relative atomic mass greater than 40; L ａ , L ｂ , L ｃ are the first ligand, the second ligand, and the third ligand coordinated with the metal M, and the ligand L ａ , L ｂ , L ｃ may be the same or different, Ligand L ａ , L ｂ , L ｃ may be linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, the sum of m, n and q is equal to the oxidation state of the metal M, and when m is 2 or more, a plurality of L ａ may be the same or different, and when n is 2, two L ｂ may be the same or different, and when q is 2, two L ｃ may be the same or different, Ligand L ａ has a structure represented by formula 11: 【Chemical 56】 Ring C １ and ring C ２ are the same or different and are selected from an aromatic ring having 5 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof, Q １ and Q ２ are the same or different at each occurrence and are selected from C or N, R １１ and R １２ are the same or different at each occurrence and represent mono-, multi- or no substitution; R １１ and R １２ are the same or different at each occurrence and represent 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 atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, selected from the group consisting of substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R １１ , R １２ may be bonded to form a ring, Ligand L ｂ and L ｃ are the same or different at each occurrence and are selected from monoanionic bidentate ligands.

12. The ligand L ｂ and L ｃ is selected from the group consisting of the following structures, which may be the same or different at each occurrence: 【Chemical 57】 R ａ and R ｂ are the same or different at each occurrence and represent mono-, multi- or no substitution; X ｂ are the same or different for each occurrence and are O, S, Se, NR Ｎ１ and C.R. Ｃ１ R Ｃ２ selected from the group consisting of X ｃ and X ｄ are O, S, Se and NR, which may be the same or different at each occurrence. Ｎ２ selected from the group consisting of R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｎ２ , R Ｃ１ and R Ｃ２ are the same or different at each occurrence and represent 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 atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｎ２ , R Ｃ１ and R Ｃ２ The device of claim 11 , wherein:

13. The first metal complex is Ir(L ａ ) ｍ (L ｂ ) ３－ｍ The device of claim 11, having a general structure of the formula: and having a structure represented by formula 11-1. 【Chemistry 58】 (m is 0, 1, 2 or 3, and when m is 2 or 3, a plurality of L ａ are the same or different, and when m is 0 or 1, a plurality of L ｂ are the same or different, T １ ~T ６ is the same or different for each occurrence Ｔ or N, R ａ , R ｂ and R ｄ are the same or different at each occurrence and represent mono-, multi- or no substitution; R ａ , R ｂ , R ｄ and R Ｔ are the same or different at each occurrence and represent 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 atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R ａ , R ｂ may be bonded to form a ring, Adjacent substituents R ｄ , R Ｔ may be bonded to form a ring.)

14. 12. The device of claim 11, wherein the first metal complex is selected from the group consisting of the following structures: 【Chemical Formula 59】 【Chemistry 60】 【Hua 61】 【Hua 62】 【Chemistry 63】 【Hua 64】 【Chemistry 65】 (The hydrogen atoms in the above compounds GD1 to GD76 may be partially or completely deuterated.)

15. the light-emitting layer further comprises a second host compound; 12. The device of claim 11, wherein the second host compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

16. 16. The device of claim 15, wherein the second host compound has a structure represented by Formula 12 or Formula 13: 【Hua 66】 (L Ｔ are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; T may be the same or different for each occurrence, and may be C, CR ｗ or N, Ar １１ are the same or different at each occurrence 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; R ｗ are the same or different at each occurrence and represent 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, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituent. a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each having 0 to 20 carbon atoms; Adjacent substituents R ｗ may be bonded to form a ring.)

17. 16. The device according to claim 15, wherein the second host compound has a structure represented by formula 12-1, formula 12-2, or formula 12-3. 【Hua 67】 (L Ｔ are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; T may be the same or different for each occurrence, and may be C, CR ｗ or N, G may be identical or different for each occurrence of C(R ｇ ) ２ , N.R. ｇ , O or S; R ｗ , R ｇ are the same or different at each occurrence and represent 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 atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar １１ are the same or different at each occurrence 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; Adjacent substituents R ｗ , R ｇ may be bonded to form a ring.)

18. 16. The device of claim 15, wherein the second host compound is selected from the group consisting of the following structures: 【Chemistry 68】 【Chemical Formula 69】 【Chemistry 70】 【Chemical 71】 【Chemical Formula 72】 【Chemical Formula 73】 【Chemical 74】 【Chemistry 75】

19. 10. The device of claim 9, wherein the organic electroluminescent device emits green, yellow, red, or white light.

20. 16. The device of claim 15, wherein the first metal complex is doped into the compound and the second host compound, and the first metal complex is 1% to 30% based on the total weight of the light-emitting layer.

21. A composition comprising a compound according to claim 1 or 8.

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