Organic electroluminescent material and device thereof

Abstract

The invention discloses an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound with a structure as shown in a formula 1. The novel compounds can be used as a main body material, an electron transport material or a hole blocking material in an organic electroluminescent device, and can greatly improve the comprehensive performance of the device, such as low driving voltage, high device efficiency and greatly prolonged service life of the device. The invention also discloses an organic electroluminescent device and composition containing the compound with the structure shown in the formula 1.

Description

Technical Field

[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a compound having the structure of Formula 1, and an organic electroluminescent device comprising the compound and a composition comprising the compound. Background Art

[0002] Organic electronic devices include but are not limited to the following types: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect quantum dots (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.

[0003] In 1987, Tang and VanSlyke of Eastman Kodak reported a bilayer organic electroluminescent device that included an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters, 1987, 51(12):913-915). Once a bias voltage 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 state-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and the anode. Since OLEDs are a self-emitting solid-state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as fabrication on flexible substrates.

[0004] OLEDs can be classified into three different types according to their light-emitting mechanisms. The OLED invented by Tang and VanSlyke is a fluorescent OLED. It only uses singlet emission. The triplets generated in the device are wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals in complexes as emitters. Therefore, it is able to harvest both singlet and triplet states, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have 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, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of the materials used. Small molecules refer to any organic or organometallic materials that are not polymers. As long as they have a precise structure, the molecular weight of small molecules can be very large. Dendrimers with a well-defined structure are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-group light-emitting groups. If post-polymerization occurs during the manufacturing process, small molecule OLEDs can turn into polymer OLEDs.

[0006] There are various methods for manufacturing OLEDs. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. If the materials can be dissolved or dispersed in a solvent, small molecule OLEDs can also be manufactured by solution methods.

[0007] The emission color of OLEDs can be achieved through the structural design of the light-emitting materials. OLEDs can include one or more light-emitting layers to achieve the desired spectrum. For green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue color unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency, and longer device lifetime.

[0008] Triazine-based organic semiconductor materials are widely used in OLEDs due to their excellent optoelectronic properties, redox properties, stability, etc.

[0009] WO2023153906A1 discloses an organic compound having the following formula structure and an organic light-emitting device comprising the compound: wherein, L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C6-C30 arylene; Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group; R 1 to R 4 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted C6-C30 aryl group; R 5 and R 25 are each independently hydrogen or deuterium. This application discloses compounds etc. in specific structures. This application discloses triazine compounds with an N-carbazole substituent connected to a carbazolyl group and their effects on device performance. This application does not disclose or teach triazine compounds with other structures and their applications in organic electroluminescent devices.

[0010] WO2021040467A1 discloses an organic compound having the following formula structure and an organic light-emitting device comprising the compound: wherein R1 and R2 are each independently a substituted or unsubstituted C 6-60 aryl group, or a substituted or unsubstituted C 5-60 heteroaryl group containing at least one heteroatom selected from N, O, and S; Ar is a substituted or unsubstituted C 6-60 aryl group. This application discloses the following compounds in specific structures: This application discloses triazine compounds with at least two carbazolyl groups in the meta position to the triazine on the phenylene group connected to the triazine and their effects on device performance. This application does not disclose or teach triazine compounds with other structures and their applications in organic electroluminescent devices.

[0011] However, the carrier transport ability and lifetime of currently reported triazine-based organic semiconductor materials in optoelectronic devices have certain limitations. Therefore, the application potential of such materials is worthy of further in-depth research and development. Summary of the Invention

[0012] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least part of the above problems. The compounds can be applied to organic electroluminescent devices, and can significantly improve the comprehensive performance of the devices, such as having a low driving voltage, high device efficiency, and a significantly improved device lifetime.

[0013] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0014]

[0015] Wherein,

[0016] U is the same or different each time it appears and is independently selected from CR u or N;

[0017] V1-V4 are each independently selected from C, CR v or N, and one of V1-V4 is selected from C and is connected to L, and V5-V 12 are each independently selected from CR v or N;

[0018] X is the same or different each time it appears and is independently selected from CR x or N;

[0019] Y is selected from CR y or N;

[0020] Z is the same or different each time it appears and is independently selected from CR z or N;

[0021] Ar is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof;

[0022] L is selected from a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;

[0023] R v 、R x and R zEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a 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 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 alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0024] R u and R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, a 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 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 alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; provided that when the said R u and R y is selected from a heteroaryl group, the heteroatoms in the ring atoms of the heteroaryl group are selected from one or more of O, S, Se, Si, P, Ge, and B;

[0025] Adjacent substituents R u may optionally be connected to form a ring;

[0026] Adjacent substituents R v may optionally be connected to form a ring;

[0027] Adjacent substituents R x , R y may optionally be connected to form a ring;

[0028] Adjacent substituents R z may optionally be connected to form a ring.

[0029] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, and the organic layer contains the compound of Formula 1 described in the foregoing embodiment.

[0030] According to another embodiment of the present invention, a composition is also disclosed, which contains the compound of Formula 1 described in the foregoing embodiment.

[0031] The present invention discloses a series of compounds having the structure of Formula 1. The compounds can be used as host materials, electron transport materials, or hole blocking materials in organic electroluminescent devices, etc., and can greatly improve the comprehensive performance of the devices, such as having a low driving voltage, high device efficiency, and greatly extended device lifetime. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compositions disclosed herein.

[0033] Figure 2 is another schematic diagram of an organic light-emitting device that may contain the compounds and compositions disclosed herein. DETAILED DESCRIPTION

[0034] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is schematically and non-limitingly shown. The figures are not necessarily drawn to scale, and some layer structures in the figures can also be omitted as needed. The 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, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of US Patent US7,279,704B2, and the entire content of the above patent is incorporated herein by reference.

[0035] Each of these layers has more examples. For example, U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes, which include a composite cathode having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer, are disclosed in U.S. Patents Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entireties. The principles and use of a blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated herein by reference in their entireties. Examples of an injection layer are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated herein by reference in its entirety.

[0036] The above-described layered structure is provided by way of non-limiting examples. The function of the OLED can be achieved by combining the various layers described above, or some layers can be completely omitted. It can 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 can include several sub-layers. For example, the light-emitting layer can have two different light-emitting materials to achieve a desired emission spectrum.

[0037] In one embodiment, the OLED can be described as having an "organic layer" disposed between the cathode and the anode. The organic layer can include one or more layers.

[0038] The OLED also requires a encapsulation layer, as Figure 2 schematically and non-limitingly shows an organic light-emitting device 200, which is Figure 1In contrast, a encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin film encapsulation is described in U.S. Patent US7,968,146B2, the entire content of which is incorporated herein by reference.

[0039] Devices manufactured in accordance with embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units) with the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, phablets, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.

[0040] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0041] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers can exist between the first and second layers. For example, even though there are various organic layers between the cathode and the anode, the cathode can still be described as being "disposed on" the anode.

[0042] As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in a liquid medium in the form of a solution or suspension and / or deposited from a liquid medium.

[0043] When a ligand is believed to directly contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "photosensitive". When a ligand is believed not to contribute to the photosensitive properties of an emissive material, the ligand can be referred to as "auxiliary", but an auxiliary ligand can modify the properties of a photosensitive ligand.

[0044] It is believed that the internal quantum efficiency (IQE) of a fluorescent OLED can exceed the 25% spin statistics limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0045] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between the triplet state and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap for the energy state conversion. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A remarkable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize the non-radiative decay from the triplet state, the fraction of singlet excited state repopulation can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electro-generated excitons.

[0046] The characteristics of E-type delayed fluorescence can be seen in exciplex systems or single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized as donor-acceptor charge transfer (CT)-type emission. The spatial separation of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in these donor-acceptor type compounds usually results in a small ΔE S-T . These states can include CT states. Generally, donor-acceptor luminescent materials are constructed by connecting an electron donor moiety (such as an amino or carbazole derivative) to an electron acceptor moiety (such as an N-containing six-membered aromatic ring).

[0047] Definition of substituent terms

[0048] Halogen or halide - as used herein, includes fluorine, chlorine, bromine, and iodine.

[0049] Alkyl - as used herein, includes straight-chain and branched-chain alkyls. The alkyl can be an alkyl having 1 to 20 carbon atoms, preferably an alkyl having 1 to 12 carbon atoms, more preferably an alkyl having 1 to 6 carbon atoms. Examples of alkyls 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, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl can be optionally substituted.

[0050] Cycloalkyl - as used herein, cycloalkyl includes cyclic alkyl groups. The cycloalkyl can be a cycloalkyl having 3 to 20 ring carbon atoms, preferably a cycloalkyl having 4 to 10 carbon atoms. Examples of cycloalkyl include cyclobutyl, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, 4,4 - dimethylcyclohexyl, 1 - adamantyl, 2 - adamantyl, 1 - norbornyl, 2 - norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4 - methylcyclohexyl, and 4,4 - dimethylcyclohexyl are preferred. Additionally, the cycloalkyl can be optionally substituted.

[0051] Heteroalkyl - as used herein, heteroalkyl is formed by substituting one or more carbons in an alkyl chain with a heteroatom selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, phosphorus atom, silicon atom, germanium atom, and boron atom. The heteroalkyl can be a heteroalkyl having 1 to 20 carbon atoms, preferably a heteroalkyl having 1 to 10 carbon atoms, more preferably a heteroalkyl having 1 to 6 carbon atoms. Examples of heteroalkyl include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert - butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl can be optionally substituted.

[0052] Alkenyl - as used herein, encompasses straight - chain, branched - chain, and cyclic olefin groups. The alkenyl can be an alkenyl having 2 to 20 carbon atoms, preferably an alkenyl having 2 to 10 carbon atoms. Examples of alkenyl include vinyl, propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, 1,3 - butadienyl, 1 - methylethenyl, styryl, 2,2 - diphenylethenyl, 1,2 - diphenylethenyl, 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 norbornenyl. Additionally, the alkenyl can be optionally substituted.

[0053] Alkynyl - As used herein, it encompasses straight-chain alkynyl. The alkynyl can be an alkynyl having 2 to 20 carbon atoms, preferably an alkynyl having 2 to 10 carbon atoms. Examples of alkynyl 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, phenylacetylenyl, phenylpropargyl, etc. Among the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylacetylenyl are preferred. Additionally, the alkynyl can be optionally substituted.

[0054] Aryl or aromatic group - As used herein, non-fused and fused systems are considered. The aryl can be an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-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'-methylbiphenylyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylenyl, 3,4-xylenyl, 2,5-xylenyl, mesityl and m-quaterphenyl. Additionally, the aryl can be optionally substituted.

[0055] Heterocyclic group or heterocycle - As used herein, non-aromatic cyclic groups are considered. The non-aromatic heterocyclic group includes saturated heterocyclic groups having 3 - 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 - 20 ring atoms, where at least one ring atom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl and tetrahydrothienyl. Additionally, the heterocyclic group can be optionally substituted.

[0056] Heteroaryl - As used herein, it can include non - fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, where at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom, and boron atom. Isoaryl also refers to heteroaryl. The heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryls 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, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2 - azaborolane, 1,3 - azaborolane, 1,4 - azaborolane, borazole and its nitrogen - containing analogs. Additionally, the heteroaryl can be optionally substituted.

[0057] Alkoxy - As used herein, it is represented by -O - alkyl, -O - cycloalkyl, -O - heteroalkyl, or -O - heterocycloalkyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocycloalkyl are the same as those described above. The alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy can be optionally substituted.

[0058] Aryloxy - As used herein, it is represented by -O - aryl or -O - heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy can be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 - 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. Additionally, the aryloxy can be optionally substituted.

[0059] Aralkyl - as used herein, encompasses aryl-substituted alkyl groups. Aralkyl groups may be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 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, substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0060] Alkylsilyl - As used herein, alkyl substituted silicon groups are contemplated. The alkylsilyl group may be an alkylsilyl group having 3-20 carbon atoms, 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, dimethyltert-butylsilyl, methyldi-tert-butylsilyl. In addition, the alkylsilyl group may be optionally substituted.

[0061] Arylsilyl - as used herein, encompasses at least one aryl-substituted silicon group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, the arylsilyl group may be optionally substituted.

[0062] Alkylgermyl – As used herein, it encompasses alkyl-substituted germyl groups. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tritert-butylgermyl, triisobutylgermyl, dimethyltert-butylgermyl, methylditert-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0063] Arylgermyl – As used herein, it encompasses germyl groups substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of the arylgermyl group include triphenylgermyl, phenyldibiphenylgermyl, diphenylbiphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyltert-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0064] The term "aza" in azadibenzofuran, azadibenzothiophene, etc. means that one or more C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by those of ordinary skill in the art, and all such analogs are determined to be included within the terms described herein.

[0065] In the present disclosure, unless otherwise defined, when any one of the terms consisting of the following groups is used: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocycloalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of the groups alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino can be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocycloalkyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermyl having 3-20 carbon atoms, unsubstituted arylgermyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0066] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is the entire molecule (such as benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attached fragment are considered equivalent.

[0067] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Replacement of other stable isotopes in the compounds may be preferred due to their enhanced device efficiency and stability.

[0068] Among the compounds mentioned in the present disclosure, polysubstituted refers to the range including disubstituted up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure indicates polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its connecting structure, and the substituent present at multiple available substitution positions can be of the same structure or different structures.

[0069] Among the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can optionally be connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. Among the compounds mentioned in the present disclosure, adjacent substituents can optionally be connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can optionally be connected to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spiro ring, bridged ring, fused ring, etc.), and an alicyclic ring, heteroalicyclic ring, aromatic ring or heteroaromatic ring. In this expression, adjacent substituents can 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 away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0070] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to the same carbon atom being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0071]

[0072] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms directly bonded to each other being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

[0074] The expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to two substituents bonded to carbon atoms further away being connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0075]

[0076] In addition, the expression that adjacent substituents can optionally be connected to form a ring is also intended to be considered as referring to, in the case where one of the two adjacent substituents represents hydrogen, the second substituent being bonded to the position where the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0077]

[0078] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0079]

[0080] Wherein,

[0081] U is the same or different each time it appears and is independently selected from CR u or N;

[0082] V1-V4 are each independently selected from C, CR v or N, and one of V1-V4 is selected from C and is connected to L, and V5-V 12 are each independently selected from CR v or N;

[0083] X is the same or different each time it appears and is independently selected from CR x or N;

[0084] Y is selected from CR y or N;

[0085] Z is the same or different each time it appears and is independently selected from CR z or N;

[0086] Ar is selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms, or a combination thereof;

[0087] L is selected from a single bond, a substituted or unsubstituted alkylene group having 1-20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3-20 carbon atoms, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;

[0088] R v 、R x and R zEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0089] R u and R y Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; provided that when the said R u and R y is selected from heteroaryl, the heteroatoms in the ring atoms of the heteroaryl are selected from one or more of O, S, Se, Si, P, Ge, and B;

[0090] Adjacent substituents R u can optionally be linked to form a ring;

[0091] Adjacent substituents R v can optionally be linked to form a ring;

[0092] Adjacent substituents R x , R y can optionally be linked to form a ring;

[0093] Adjacent substituents R z can optionally be linked to form a ring.

[0094] In the present invention, "adjacent substituents R u can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R u can be linked to form a ring. Obviously, any two adjacent substituents R u can also not be linked to form a ring.

[0095] In the present invention, "adjacent substituents R v can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R v can be linked to form a ring. Obviously, any two adjacent substituents R v can also not be linked to form a ring.

[0096] In the present invention, "adjacent substituents R x , R y can optionally be linked to form a ring" is intended to mean that the adjacent substituents R x and R y can be linked to form a ring. Obviously, the adjacent substituents R x and R y can also not be linked to form a ring.

[0097] In the present invention, "adjacent substituents R z can optionally be linked to form a ring" is intended to mean that any two adjacent substituents R z can be linked to form a ring. Obviously, any two adjacent substituents R z can also not be linked to form a ring.

[0098] According to one embodiment of the present invention, wherein said V2 is selected from C and is linked to L.

[0099] According to one embodiment of the present invention, wherein each occurrence of said U is the same or different and is selected from CR u .

[0100] According to one embodiment of the present invention, wherein Y is selected from CR y .

[0101] According to one embodiment of the present invention, the compound of formula 1 structure contains only one carbazole structure or azacarbazole structure or carbazole fused ring structure or azacarbazole fused ring. The carbazole structure or azacarbazole structure or carbazole fused ring structure or azacarbazole fused ring has been shown in the formula 1 structure, that is, the fused ring structure where U is located.

[0102] According to one embodiment of the present invention, wherein the R u and R y do not contain a carbazole structure or a carbazole fused ring structure.

[0103] According to one embodiment of the present invention, wherein the R u and R y are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms, cyano, and combinations thereof; when the R u and R y are selected from heteroaryl, the heteroatoms in the ring atoms of the heteroaryl are selected from one or more of O, S, Se, Si, P, Ge, and B.

[0104] According to one embodiment of the present invention, wherein the R u and R y are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms, cyano, and combinations thereof; when the R u and R y are selected from heteroaryl, the heteroatoms in the ring atoms of the heteroaryl are selected from one or more of O, S, and Se.

[0105] According to one embodiment of the present invention, wherein the R u and R yEach occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

[0106] According to one embodiment of the present invention, wherein said R u At least one of which is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, cyano, and combinations thereof; said R u And R y When selected from heteroaryl, the heteroatom in the ring atoms of the heteroaryl is selected from one or more of O, S, and Se.

[0107] According to one embodiment of the present invention, wherein said R u At least one of which is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, cyano, and combinations thereof; said R u And R y When selected from heteroaryl, the heteroatom in the ring atoms of the heteroaryl is selected from one or more of O, S, and Se.

[0108] According to one embodiment of the present invention, wherein said R u At least one of which is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

[0109] According to one embodiment of the present invention, wherein said X is the same as or different from each occurrence and is selected from CR x .

[0110] According to one embodiment of the present invention, wherein said Z is the same as or different from each occurrence and is selected from CR z .

[0111] According to one embodiment of the present invention, wherein said R x and R z are each independently the same or different and are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, cyano, and combinations thereof.

[0112] According to one embodiment of the present invention, wherein said R x and R z are each independently the same or different and are selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

[0113] According to one embodiment of the present invention, wherein each of V1-V4 is independently selected from C or CR v , and one of V1-V4 is selected from C and is connected to L, and V5-V 12 are each independently selected from CR v .

[0114] According to one embodiment of the present invention, wherein said R v are each independently the same or different and are selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, cyano, and combinations thereof.

[0115] According to one embodiment of the present invention, wherein said R v are each independently the same or different and are selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

[0116] According to one embodiment of the present invention, wherein Ar is selected from substituted or unsubstituted aryl having 6 - 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 20 carbon atoms, or a combination thereof.

[0117] According to one embodiment of the present invention, wherein Ar is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.

[0118] According to one embodiment of the present invention, wherein L is selected from a single bond, substituted or unsubstituted arylene having 6 - 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 - 20 carbon atoms, or a combination thereof.

[0119] According to one embodiment of the present invention, wherein L is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, or a combination thereof.

[0120] According to one embodiment of the present invention, wherein the compound is selected from the group consisting of Compound A - 1 to Compound A - 240, and the specific structures of Compound A - 1 to Compound A - 240 are shown in Claim 8.

[0121] According to one embodiment of the present invention, wherein the hydrogen in Compound A - 1 to Compound A - 240 can be partially or completely replaced by deuterium.

[0122] According to one embodiment of the present invention, an organic electroluminescent device is also disclosed, which includes:

[0123] An anode,

[0124] A cathode,

[0125] And an organic layer disposed between the anode and the cathode, the organic layer contains a compound having the structure of Formula 1, and the specific structure of the compound having the structure of Formula 1 is as shown in any of the above embodiments.

[0126] According to one embodiment of the present invention, wherein the organic layer is a light - emitting layer and the compound is a host compound.

[0127] According to one embodiment of the present invention, wherein the organic layer is an electron - transporting layer and the compound is an electron - transporting compound.

[0128] According to an embodiment of the present invention, wherein the organic layer is a hole blocking layer and the compound is a hole blocking compound.

[0129] According to an embodiment of the present invention, wherein the organic layer is a light-emitting layer, the compound is a host compound, and the light-emitting layer further contains a second host compound and a metal complex.

[0130] According to an embodiment of the present invention, wherein the second host compound contains 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, silicofluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0131] According to an embodiment of the present invention, wherein the second host compound contains at least one chemical group selected from the group consisting of benzene, carbazole, indolocarbazole, fluorene, silicofluorene, and combinations thereof.

[0132] According to an embodiment of the present invention, wherein the second host compound has a structure represented by Formula 2 or Formula 3:

[0133]

[0134] Wherein,

[0135] T is the same or different each time it appears and is selected from C, CR t or N;

[0136] G is the same or different each time it appears and is selected from C(R g )2, NR g , O or S; when multiple Rs g are present simultaneously, the multiple Rs g are the same or different;

[0137] L T is the same or different each time it appears and is selected from a single bond, a substituted or unsubstituted alkylene having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 - 20 carbon atoms, a substituted or unsubstituted arylene having 6 - 20 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 20 carbon atoms, or a combination thereof;

[0138] R t and R gEach occurrence is the same as or different from and is selected from the group consisting of hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl having 1-20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3-20 ring atoms, a substituted or unsubstituted aralkyl having 7-30 carbon atoms, a substituted or unsubstituted alkoxy having 1-20 carbon atoms, a substituted or unsubstituted aryloxy having 6-30 carbon atoms, a substituted or unsubstituted alkenyl having 2-20 carbon atoms, a substituted or unsubstituted alkynyl having 2-20 carbon atoms, a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, a substituted or unsubstituted arylsilyl having 6-20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, a substituted or unsubstituted arylgermyl having 6-20 carbon atoms, a substituted or unsubstituted amino having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a mercapto group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0139] Ar1 and Ar2 are each occurrence the same as or different from and are selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or combinations thereof;

[0140] Adjacent substituents R t and R g can optionally be linked to form a ring.

[0141] As used herein, "adjacent substituents R t and R g can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, between two substituents R t between two substituents R g between substituent R t and substituent R g any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring with each other.

[0142] According to one embodiment of the present invention, the second host compound has a structure represented by one of Formula 2-a to Formula 2-j, Formula 3-a to Formula 3-f:

[0143]

[0144]

[0145] Wherein,

[0146] T is the same or different each occurrence and is selected from CR t or N;

[0147] G is the same or different each occurrence and is selected from C(R g )2, NR g , O or S; when there are multiple Rs g simultaneously, the multiple Rs g are the same or different;

[0148] L T is the same or different each occurrence and is selected from a single bond, a substituted or unsubstituted alkylene having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 - 20 carbon atoms, a substituted or unsubstituted arylene having 6 - 20 carbon atoms, a substituted or unsubstituted heteroarylene having 3 - 20 carbon atoms, or a combination thereof;

[0149] R t and R g are the same or different each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, a substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, a substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, a substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, a substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, a substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, a substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0150] Ar1 and Ar2 are the same or different each occurrence and are selected from a substituted or unsubstituted aryl having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, or a combination thereof;

[0151] Adjacent substituents R t and R g can optionally be joined to form a ring.

[0152] According to one embodiment of the present invention, the second host compound is selected from the group consisting of compounds PH-1 to compound PH-114, and the specific structures of compounds PH-1 to compound PH-114 are shown in claim 11.

[0153] According to one embodiment of the present invention, the metal complex has the general formula M(L a ) m (L b ) n (L c ) q ;

[0154] The metal M is selected from metals having a relative atomic mass greater than 40;

[0155] L a , L b and L c are the first ligand, the second ligand and the third ligand coordinated with the metal M respectively, and L a , L b , L c can be the same or different;

[0156] L a , L b and L c can optionally be connected to form a polydentate ligand;

[0157] 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; when m is greater than or equal to 2, multiple L a can be the same or different; when n is 2, the two L b can be the same or different; when q is 2, the two L c can be the same or different;

[0158] The ligand L a has the structure shown in Formula 4:

[0159]

[0160] Ring A1 and ring A2 are each independently selected from a substituted or unsubstituted aromatic ring having 5 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof;

[0161] P1 and P2 are each independently selected from C or N;

[0162] D1 and D2 are each independently selected from a single bond, O or S;

[0163] L1 is selected from the group consisting of: a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, a substituted or unsubstituted vinylene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; when two R's are present simultaneously, the two R's are the same or different;

[0164] R 11 and R 12 each occurrence is the same or different and represents mono-substituted, multi-substituted or unsubstituted;

[0165] R 11 ,R 12 ,R' each occurrence is the same or different and is 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, 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 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 alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0166] Adjacent substituents R 11 ,R 12 ,R' can optionally be connected to form a ring;

[0167] Ligand L b and L c each occurrence is the same or different and is selected from monoanionic bidentate ligands.

[0168] In this embodiment, "adjacent substituents R 11 ,R 12 ,R' can optionally be connected to form a ring" is intended to mean the adjacent substituent groups therein. For example, between adjacent substituents R 11 ,between adjacent substituents R 12between adjacent substituents R', between adjacent substituents R 11 and R 12 between, any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be linked to form a ring either.

[0169] According to one embodiment of the present invention, wherein ligand L b and L c are each independently selected, each time they appear, from the group consisting of the following structures:

[0170]

[0171] wherein,

[0172] R a and R b each time they appear, independently represent mono-substitution, multi-substitution, or no substitution;

[0173] X b each time it appears, is independently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0174] X c and X d each time they appear, independently are selected from the group consisting of: O, S, Se and NR N2 ;

[0175] R a , R b , R c , R N1 , R N2 , R C1 and R C2Each occurrence is the same as or different from and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0176] Adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring.

[0177] In this embodiment, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 can optionally be linked to form a ring, which is intended to represent adjacent substituent groups therein. For example, between two substituents R a , between two substituents R b , between two substituents R c , between substituent R a and R b , between substituent R a and R c , between substituent R b and R c , between substituent R a and R N1 , between substituent R b and R N1 , between substituent R a and RC1 between, substituent R a and R C2 between, substituent R b and R C1 between, substituent R b and R C2 between, substituent R a and R N2 between, substituent R b and R N2 between, and R C1 and R C2 between, any one or more of these substituent groups may be linked to form a ring. For example, adjacent substituents R a , R b can optionally be linked to form a ring, which may form one or more of the following structures including but not limited to:

[0178] wherein, W is selected from O, S, Se, NR w or CR w R w ; wherein said R w , R a ’, R b ’ are defined the same as said R a . Obviously, these substituents may also not be linked to form a ring at all.

[0179] According to an embodiment of the present invention, wherein said metal complex has the general formula structure of M(L a1 ) j (L b1 ) k , wherein M is selected from metals with a relative atomic mass greater than 40;

[0180] L a1 , L b1 are respectively the first ligand and the second ligand coordinated with said M; L a1 , L b1 can optionally be linked to form a polydentate ligand;

[0181] j is 1, 2 or 3; k is 0, 1 or 2; the sum of j and k is equal to the oxidation state of said M; when j is greater than or equal to 2, multiple L a1 can be the same or different; when k is 2, two L b1 can be the same or different;

[0182] Said L a1 has the structure shown in Formula 4-1:

[0183]

[0184] Among them,

[0185] ring F is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;

[0186] 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;

[0187] ring F and ring E are fused via U1 and U2;

[0188] U1 and U2 are the same or different each time they appear and are selected from C or N;

[0189] R F , R E each time it appears, it represents mono-substituted, multi-substituted or unsubstituted;

[0190] Q is the same or different each time it appears and is selected from CR Q or N;

[0191] R F , R E , R Q each time it appears, it is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

[0192] Adjacent substituents R F , R E , R Q can optionally be connected to form a ring;

[0193] The ligand L b1 has the structure shown in Formula 4-2:

[0194]

[0195] Among them, R 21 to R 27 each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

[0196] In this article, adjacent substituents R F , R E , R Q can optionally be connected to form a ring, which is intended to mean that when there are substituents R F , substituent R E , substituent R Q , among which adjacent substituent groups, such as between adjacent substituents R F , between adjacent substituents R E , between adjacent substituents R Q , between adjacent substituents R F and R E , between adjacent substituents R F and R Q , and between adjacent substituents R E and R Q , any one or more of these adjacent substituent groups can be connected to form a ring. Obviously, when there are substituents R F , substituent R E , substituent R Q , these substituent groups may also not be connected to form a ring.

[0197] According to one embodiment of the present invention, in Formula 4-2, R21 -R 23 At least one of them 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 them 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.

[0198] According to one embodiment of the present invention, in Formula 4-2, R 21 -R 23 At least two of them 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 them 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.

[0199] According to one embodiment of the present invention, in Formula 4-2, R 21 -R 23 At least two of them are the same or different each time they appear 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 them are the same or different each time they appear 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.

[0200] According to one embodiment of the present invention, wherein the metal complex has a general formula structure of Ir(L a1 )2(L b1 ).

[0201] According to one embodiment of the present invention, wherein the metal complex is an Ir metal complex and contains a ligand L a1 , the L a1Having a structure represented by Formula 4-1 and containing at least one structural unit selected from the group consisting of a 6-membered fused 6-membered aromatic ring, a 6-membered fused 6-membered heteroaromatic ring, a 6-membered fused 5-membered aromatic ring, and a 6-membered fused 5-membered heteroaromatic ring.

[0202] According to one embodiment of the present invention, wherein the metal complex is an Ir metal complex and contains a ligand L a1 , the L a1 Having a structure represented by Formula 4-1 and containing at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline, and aza-phenanthrene.

[0203] According to one embodiment of the present invention, wherein the metal complex has a structure represented by Formula 4-3:

[0204]

[0205] Wherein,

[0206] Metal M is selected from metals having a relative atomic mass greater than 40;

[0207] Ring A1 - Ring A4 are each independently selected, each time they appear, from a substituted or unsubstituted aromatic ring having 6 - 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 - 30 ring atoms, or a combination thereof;

[0208] L1 - L4 are each independently selected, each time they appear, from the group consisting of: a single bond, BR', CR'R', NR', O, SiR'R', PR', S, GeR'R', Se, a substituted or unsubstituted vinylene, an ethynylene, a substituted or unsubstituted arylene having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene having 5 - 30 carbon atoms, and combinations thereof; when two R' are present simultaneously, the two R' are the same or different;

[0209] P1 - P4 are each independently selected, each time they appear, from C or N;

[0210] D1 - D4 are each independently selected, each time they appear, from a single bond, O, or S;

[0211] R 11 -R 14 Each time it appears, it independently represents mono-substituted, multi-substituted, or unsubstituted;

[0212] R 11 -R 14, each occurrence of R' is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0213] Adjacent substituents R 11 -R 14 , and R' can optionally be linked to form a ring.

[0214] In this embodiment, "adjacent substituents R 11 -R 14 , and R' can optionally be linked to form a ring" is intended to mean that among adjacent substituent groups, for example, between adjacent substituents R 11 , between adjacent substituents R 12 , between adjacent substituents R 13 , between adjacent substituents R 14 , and between adjacent substituents R', any one or more of these substituent groups can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring.

[0215] According to one embodiment of the present invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt.

[0216] According to one embodiment of the present invention, the metal M is selected from Pt or Ir.

[0217] According to one embodiment of the present invention, the metal complex has the general formula structure of Ir(L a ) m (L b ) 3-m and is composed of

[0218] Structure represented by Formula 4-4:

[0219]

[0220] Wherein,

[0221] m is 0, 1, 2 or 3; when m is 2 or 3, multiple Ls a are the same or different; when m is 0 or 1, multiple Ls b are the same or different;

[0222] T1 - T6 each occurrence is the same or different and is selected from CR T or N;

[0223] R a , R b and R d each occurrence is the same or different and represents mono - substitution, multi - substitution, or no substitution;

[0224] R a , R b , R d and R T each occurrence is the same or different and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 - 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 - 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 - 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 - 20 ring atoms, substituted or unsubstituted aralkyl having 7 - 30 carbon atoms, substituted or unsubstituted alkoxy having 1 - 20 carbon atoms, substituted or unsubstituted aryloxy having 6 - 30 carbon atoms, substituted or unsubstituted alkenyl having 2 - 20 carbon atoms, substituted or unsubstituted alkynyl having 2 - 20 carbon atoms, substituted or unsubstituted aryl having 6 - 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 - 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 - 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 - 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 - 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 - 20 carbon atoms, substituted or unsubstituted amino having 0 - 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, hydroxy, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0225] Adjacent substituents R a , R b can optionally be linked to form a ring;

[0226] Adjacent substituents R d , R Tcan optionally be linked to form a ring.

[0227] In this embodiment, "adjacent substituents R a , R b can optionally be linked to form a ring" is intended to mean that among the adjacent substituent groups, for example, between two adjacent substituents R a , between two adjacent substituents R b , and between adjacent substituents R a and R b , any one or more of these substituent groups can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring at all.

[0228] In this embodiment, "adjacent substituents R d , R T can optionally be linked to form a ring" is intended to mean that among the adjacent substituent groups, for example, between two adjacent substituents R T , between two adjacent substituents R d , any one or more of these substituent groups can be linked to form a ring. Obviously, these substituents may also not be linked to form a ring at all.

[0229] According to one embodiment of the present invention, wherein at least one of T1-T6 is selected from CR T , and the R T is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0230] According to one embodiment of the present invention, wherein at least one of T1-T6 is selected from CR T , and the R T is fluorine or cyano.

[0231] According to one embodiment of the present invention, wherein at least one of T1-T4 is selected from CR T , and the R T is fluorine or cyano.

[0232] According to one embodiment of the present invention, wherein at least two of T1-T6 are selected from CR T , and one of the R T is fluorine or cyano, and the other R T is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0233] According to one embodiment of the present invention, where each occurrence of T1 - T6 is the same or different and is selected from CR T or N, and at least one of T1 - T6 is selected from N, for example, one or two of T1 - T6 are selected from N.

[0234] According to one embodiment of the present invention, the metal complex is selected from the group consisting of compound GD1 to compound GD77:

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241] According to one embodiment of the present invention, the organic electroluminescent device emits green light.

[0242] According to one embodiment of the present invention, the organic electroluminescent device emits white light.

[0243] According to one embodiment of the present invention, a composition is further disclosed, which comprises a compound represented by formula 1; the compound is as shown in any of the foregoing embodiments.

[0244] In combination with other materials

[0245] The materials for specific layers in the organic light - emitting devices described in the present invention can be used in combination with various other materials present in the devices. The combinations of these materials are described in detail in paragraphs 0132 - 0161 of US Patent Application US2016 / 0359122A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein 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 consult the literature to identify other materials that can be used in combination.

[0246] The materials described herein as being specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the devices. For example, the compounds disclosed herein can be combined with a variety of light-emitting dopants, hosts, transport layers, blocking layers, injection layers, electrodes, and other layers that may be present. The combinations of these materials are described in detail in paragraphs 0080 - 0101 of US Patent Application US2015 / 0349273A1, the entire content of which is incorporated herein by reference. The materials described or mentioned therein 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 consult the literature to identify other materials that can be used in combination.

[0247] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as received from commercial sources. The synthesized products were structurally confirmed and characterized using one or more conventional devices in the art, including but not limited to nuclear magnetic resonance spectrometers from Bruker, liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters from Shimadzu, fluorescence spectrometers from Shanghai Lingguang Technology, electrochemical workstations from Wuhan Koster, sublimators from Anhui Beike, etc., by methods well-known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional devices in the art, including but not limited to evaporation coaters produced by Angstrom Engineering, optical test systems and lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc., by methods well-known to those skilled in the art. Since those skilled in the art are aware of the relevant content such as the use of the above devices and test methods, and can obtain the inherent data of the samples determinately and without interference, the above relevant content will not be elaborated further in this patent.

[0248] Examples of compound synthesis:

[0249] The preparation method of the compounds of the present invention is not limited. Typically but not restrictively, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows:

[0250] Synthesis Example 1: Synthesis of Compound A-1

[0251] Step 1: Synthesis of Intermediate C

[0252]

[0253] In a three-necked round-bottom flask, intermediate A (22.2 g, 106.0 mmol), intermediate B (17.7 g, 106.0 mmol), Cs2CO3 (69.1 g, 212.0 mmol) and 200 mL of N,N-dimethylformamide (DMF) were added successively. Under N2 protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC, then heating was stopped and the mixture was cooled to room temperature. The reaction solution was poured into a large amount of water, and ethyl acetate was added for extraction. The organic phase was collected and the solvent was removed by concentration under reduced pressure to obtain a crude product. The crude product was slurried with absolute ethanol to obtain white solid intermediate C (26.7 g, 74.9 mmol) with a yield of 70.7%.

[0254] Step 2: Synthesis of intermediate E

[0255]

[0256] In a three-necked round-bottom flask, 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 H2O were added successively. Under N2 protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC, then heating was stopped and the mixture was cooled to room temperature. The reaction solution was separated, and the aqueous phase was extracted with DCM. The organic phases were combined. The combined organic phase was dried over anhydrous Na2SO4, filtered, and the solvent was removed by concentration under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 10:1 to 8:1) to obtain white solid intermediate E (16.8 g, 47.5 mmol) with a yield of 89.6%.

[0257] Step 3: Synthesis of intermediate F

[0258]

[0259] In a three-necked round-bottom flask, 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, 0.70 g, 1.90 mmol), KOAc (9.3 g, 95.0 mmol) and 150 mL of 1,4-dioxane were added in sequence. Under N2 protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC, then heating was stopped and the mixture was cooled to room temperature. The reaction system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 5:1 to 2:1) to obtain white solid intermediate F (18.0 g, 40.4 mmol) with a yield of 85.0%.

[0260] Step 4: Synthesis of intermediate H

[0261]

[0262] In a three-necked round-bottom flask, intermediate F (15.6 g, 35.0 mmol), intermediate G (10.3 g, 45.5 mmol), Pd(PPh3)4 (0.81 g, 0.70 mmol), Na2CO3 (7.4 g, 70.0 mmol), 280 mL of THF and 70 mL of H2O were added in sequence. Under N2 protection, the mixture was heated to reflux. After 7 h, the reaction was confirmed to be complete by TLC, then heating was stopped and the reaction solution was cooled to room temperature. The layers were separated, the aqueous phase was extracted with DCM, and the organic phases were combined. The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 8:1 to 3:1) to obtain light yellow solid intermediate H (10.5 g, 20.6 mmol) with a yield of 58.9%.

[0263] Step 5: Synthesis of intermediate J

[0264]

[0265] In a three-necked round-bottom flask, intermediate I (10.0 g, 32.55 mmol), bis(pinacolato)diboron (12.4 g, 48.83 mmol), Pd(dppf)Cl2 (0.71 g, 0.98 mmol), and KOAc (6.4 g, 65.1 mmol) were added to 1,4-dioxane (90 mL). Under nitrogen protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC, heating was stopped, and the reaction solution was cooled to room temperature. The reaction system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 10:1 to 2:1) to obtain white solid intermediate J (9.6 g, 27.10 mmol) with a yield of 83.3%.

[0266] Step 6: Synthesis of Compound A-1

[0267]

[0268] In a three-necked round-bottom flask, intermediate H (4.07 g, 8.0 mmol), intermediate J (2.83 g, 8.0 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and K2CO3 (2.21 g, 16.0 mmol) were added to toluene (40 mL), EtOH (10 mL), and H2O (10 mL). Under N2 protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC spotting, heating was stopped, and the reaction solution was cooled to room temperature. The mixture was filtered under reduced pressure, and the obtained solid was washed successively with water and methanol. The solid was recrystallized from toluene to obtain a white solid (4.3 g, 6.14 mmol) with a yield of 76.7%. The product was confirmed to be the target compound A-1 with a molecular weight of 700.3.

[0269] Synthesis Example 2: Synthesis of Compound A-8

[0270] Step 1: Synthesis of Intermediate J

[0271]

[0272] In a three-necked round-bottom flask, intermediate K (6.48 g, 30.0 mmol), intermediate G (8.82 g, 39.0 mmol), Pd(PPh3)4 (0.69 g, 0.60 mmol), Na2CO3 (6.36 g, 60.0 mmol), 192 mL of THF and 48 mL of H2O were successively added. Under N2 protection, it was heated to reflux. After 6 h, the reaction was confirmed to be complete by TLC, the heating was stopped, the reaction solution was cooled to room temperature, separated by liquid, the aqueous phase was extracted with DCM, the organic phases were combined, the organic phase was dried over anhydrous Na2SO4, filtered, and the solvent was removed by concentration under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 12:1 to 8:1) to obtain white solid intermediate L (5.7 g, 15.75 mmol) with a yield of 52.5%.

[0273] Step 2: Synthesis of intermediate M

[0274]

[0275] In a three-necked round-bottom flask, intermediate L (7.6 g, 21.0 mmol), intermediate J (7.44 g, 21.0 mmol), Pd(PPh3)4 (0.73 g, 0.63 mmol), and K2CO3 (5.80 g, 42.0 mmol) were added to toluene (100 mL), EtOH (25 mL), and H2O (25 mL). Under N2 protection, it was heated to reflux overnight. The reaction was confirmed to be complete by TLC, the heating was stopped, the reaction solution was cooled to room temperature, filtered under reduced pressure, and the obtained solid was washed successively with water and methanol. The solid was recrystallized from toluene to obtain white solid intermediate M (10.0 g, 18.1 mmol) with a yield of 86.0%.

[0276] Step 3: Synthesis of compound A-8

[0277]

[0278] In a three-necked round-bottom flask, intermediate M (4.04 g, 7.3 mmol), intermediate N (1.79 g, 10.22 mmol), Cs2CO3 (4.76 g, 14.60 mmol) and 75 mL of N,N-dimethylacetamide (DMAc) were successively added. Under N2 protection, it was heated to reflux overnight. The reaction was confirmed to be complete by TLC, the heating was stopped, and it was cooled to room temperature. The reaction solution was poured into a large amount of water to precipitate a solid, filtered under reduced pressure, and the obtained solid was purified by silica gel column chromatography (PE / DCM = 10:1 to 2:1) to obtain a white solid (3.2 g, 4.51 mmol) with a yield of 61.8%. The product was confirmed to be the target compound A-8 with a molecular weight of 708.3.

[0279] Synthesis Example 3: Synthesis of Compound A-11

[0280] Step 1: Synthesis of Compound A-11

[0281]

[0282] In a three-necked round-bottom flask, intermediate M (3.0 g, 5.42 mmol), intermediate O (1.71 g, 7.0 mmol), Cs2CO3 (3.53 g, 10.84 mmol) and 50 mL of N,N-dimethylacetamide (DMAc) were added successively. Under N2 protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC, the heating was stopped, and the mixture was cooled to room temperature. The reaction solution was poured into a large amount of water, and a solid was precipitated. The solid was filtered under reduced pressure. The obtained solid was purified by silica gel column chromatography (PE / DCM = 10:1 to 3:1) to obtain a pale yellow solid (3.0 g, 3.86 mmol), with a yield of 71.2%. The product was confirmed to be the target compound A-11, with a molecular weight of 776.3.

[0283] Synthesis Example 4: Synthesis of Compound A-104

[0284] Step 1: Synthesis of Intermediate Q

[0285]

[0286] In a three-necked round-bottom flask, intermediate J (12.4 g, 35.0 mmol), intermediate P (14.9 g, 52.5 mmol), Pd(PPh3)4 (0.81 g, 0.70 mmol), and K2CO3 (9.7 g, 70.0 mmol) were added to toluene (120 mL), EtOH (30 mL), and H2O (30 mL). Under N2 protection, the mixture was heated to reflux overnight. The reaction was confirmed to be complete by TLC, the heating was stopped, and the reaction solution was cooled to room temperature. The layers were separated, the aqueous phase was extracted with DCM, the organic phases were combined, the combined organic phase was dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (from PE to PE / DCM = 20:1) to obtain a white solid intermediate Q (11.2 g, 29.2 mmol), with a yield of 83.5%.

[0287] Step 2: Synthesis of Intermediate R

[0288]

[0289] In a three-necked round-bottom flask, intermediate Q (11.2 g, 29.2 mmol), bis(pinacolato)diboron (11.1 g, 43.8 mmol), Pd(dppf)Cl2 (0.64 g, 0.88 mmol), and KOAc (5.74 g, 58.4 mmol) were added to 1,4-dioxane (120 mL). Under N2 protection, the mixture was heated under reflux overnight. The reaction was confirmed to be complete by TLC, heating was stopped, and the mixture was cooled to room temperature. The reaction system was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (PE / DCM = 5:1 to 2:1) to obtain white solid intermediate R (10.3 g, 23.93 mmol) with a yield of 82.0%.

[0290] Step 3: Synthesis of Compound A-104

[0291]

[0292] In a three-necked round-bottom flask, intermediate H (2.0 g, 3.93 mmol), intermediate R (1.69 g, 3.93 mmol), Pd(PPh3)4 (0.091 g, 0.079 mmol), and K2CO3 (1.1 g, 7.86 mmol) were added to toluene (16 mL), EtOH (4 mL), and H2O (4 mL). Under N2 protection, the mixture was heated under reflux overnight. The reaction was confirmed to be complete by TLC, heating was stopped, and the reaction solution was cooled to room temperature and filtered under reduced pressure. The obtained solid was washed successively with water and methanol. The solid was recrystallized from toluene to obtain a pale yellow solid (2.3 g, 2.96 mmol) with a yield of 75.3%. The product was confirmed to be the target compound A-104 with a molecular weight of 776.3.

[0293] Those skilled in the art should be aware that the above preparation method is only an exemplary example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0294] The preparation method of the electroluminescent device is not limited. The preparation method of the following embodiments is only an example and should not be construed as a limitation. Those skilled in the art can reasonably improve the preparation method of the following embodiments based on the prior art. Exemplarily, the ratio of various materials in the light-emitting layer is not particularly limited, and those skilled in the art can reasonably select within a certain range according to the prior art. For example, based on the total weight of the light-emitting layer materials, the host material can account for 80%-99%, and the light-emitting material can account for 1%-20%; or the host material can account for 90%-99%, and the light-emitting material can account for 1%-10%; or the host material can account for 95%-99%, and the light-emitting material can account for 1%-5%. In addition, the host material can be one or two materials, and the ratio of the two host materials in the host material can be 100:0 to 1:99; or the ratio can be 80:20 to 20:80; or the ratio can be 60:40 to 40:60. In the device embodiments, the characteristics of the device are also tested using conventional equipment in the art (including but not limited to evaporation machines produced by Angstrom Engineering, optical test systems and lifetime test systems produced by Suzhou FushiDa, ellipsometers produced by Beijing Liangtuo, etc.) by methods well-known to those skilled in the art.

[0295] Device Embodiment

[0296] Device Embodiment 1

[0297] First, clean the glass substrate, which has an indium tin oxide (ITO) anode with a thickness of 80 nm, and then treat it with oxygen plasma and UV ozone. After treatment, dry the substrate in a glove box to remove moisture. Then mount the substrate on a substrate holder and load it into a vacuum chamber. The following specified organic layers are deposited on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.1-2 Å / s under a vacuum of about 10 -8 Torr. The co-evaporation of compound HT and compound HT1 is used as the hole injection layer (HIL, weight ratio 97:3), with a thickness of Compound HT is used as the hole transport layer (HTL), with a thickness of Compound PH-1 is used as the electron blocking layer (EBL), with a thickness of Then, compound GD1 is doped and co-evaporated with compound PH-1 and the compound A-1 of the present invention as the light-emitting layer (EML, the weight ratio of compound PH-1: compound A-1: compound GD1 is 56:38:6), with a thickness of Compound HB is used as the hole blocking layer (HBL), with a thickness of On the hole blocking layer, the co-evaporation of compound ET and lithium 8-hydroxyquinoline (Liq) is used as the electron transport layer (ETL, weight ratio 40:60), with a thickness of Finally, 1 nm of 8-hydroxyquinoline-lithium (Liq) was vapor-deposited as the electron injection layer, and 120 nm of aluminum was vapor-deposited as the cathode. Then the device was transferred back to the glove box and encapsulated with a glass cover to complete the device.

[0298] Device Example 2

[0299] The preparation of Device Example 2 was the same as that of Device Example 1, except that Compound A-8 of the present invention was used instead of Compound A-1 of the present invention in the emitting layer (EML).

[0300] Device Example 3

[0301] The preparation of Device Example 3 was the same as that of Device Example 1, except that Compound A-11 of the present invention was used instead of Compound A-1 of the present invention in the emitting layer (EML).

[0302] Device Example 4

[0303] The preparation of Device Example 4 was the same as that of Device Example 1, except that Compound A-104 of the present invention was used instead of Compound A-1 of the present invention in the emitting layer (EML).

[0304] Device Comparative Example 1

[0305] The preparation of Device Comparative Example 1 was the same as that of Device Example 1, except that Compound C-1 was used instead of Compound A-1 of the present invention in the emitting layer (EML).

[0306] Device Comparative Example 2

[0307] The preparation of Device Comparative Example 2 was the same as that of Device Example 1, except that Compound C-2 was used instead of Compound A-1 of the present invention in the emitting layer (EML).

[0308] The detailed device layer structures and thicknesses are shown in the following table. For the layers where more than one material is used, they are doped with different compounds in the recorded weight ratios.

[0309] Table 1 Partial Device Structures of Device Examples 1 to 4 and Comparative Examples 1 and 2

[0310]

[0311]

[0312] The structures of the materials used in the device are shown as follows:

[0313]

[0314]

[0315] Table 2 shows the CIE data, driving voltage (V), external quantum efficiency (EQE), and current efficiency (CE) measured at a constant current density of 15 mA / cm 2 ; and the device lifetime (LT97) measured at a constant current density of 80 mA / cm 2 .

[0316] Device data of Examples 1 to 4 and Comparative Examples 1 and 2 in Table 2

[0317]

[0318] Discussion:

[0319] As can be seen from the data in Table 2, the difference between the inventive compound A-1 and the comparative compound C-1 used in Example 1 and Comparative Example 1 lies only in whether there is a carbazole substituent on the carbazole. In terms of driving voltage and device efficiency (EQE and CE), Comparative Example 1 is already at a very high level. Compared with Comparative Example 1, the driving voltage of Example 1 is further reduced by 0.2 V, and the device efficiency (EQE and CE) is basically equivalent or slightly improved. More importantly, the device lifetime of Example 1 is significantly increased by 12.0 times. The difference between the inventive compound A-11 and the comparative compound C-1 used in Example 3 and Comparative Example 1 lies only in the different substituents on the carbazole. The carbazole of compound A-11 has a phenyl substituent, and the carbazole of compound C-1 has a carbazole substituent. Compared with Comparative Example 1, the driving voltage of Example 3 is reduced by 0.1 V, and the device efficiency (EQE and CE) is basically equivalent or slightly improved. More importantly, the device lifetime is significantly increased by 14.4 times. This shows that compared with the compounds having a carbazole substituent on the carbazole in the prior art, the compounds of the specific formula 1 structure of the present invention can improve the comprehensive performance of the device when applied to an electroluminescent device, especially can significantly improve the device lifetime, and it is unexpected that the device lifetime of the compounds of the present invention is so significantly improved due to the specific formula 1 structure.

[0320] The difference between the inventive compound A-1 and the comparative compound C-2 used in Example 1 and Comparative Example 2 lies only in whether there is further a carbazole substituent at the meta-position of the phenyl group which bridges carbazole and triazine with respect to carbazole and triazine. In terms of driving voltage and device efficiency (EQE and CE), Comparative Example 2 is already at a very high level. Compared with Comparative Example 2, the driving voltage of Example 1 is reduced by 0.3 V, the EQE is further increased by 3.2%, and the CE is further increased by 3.0%. More importantly, the device lifetime of Example 1 is significantly increased by 66.0%. This shows that compared with the compounds in the prior art in which there is further a carbazole substituent at the meta-position of the phenyl group which bridges carbazole and triazine with respect to carbazole and triazine, the compound of the specific Formula 1 structure of the present invention can improve the comprehensive performance of the device when applied to an electroluminescent device, especially can significantly improve the device lifetime, and it is unexpected that the device lifetime of the compound of the present invention is increased so significantly due to the specific Formula 1 structure.

[0321] In addition, the inventive compounds A-8 and A-104 with different structures are used in Example 2 and Example 4 respectively. Similar to Example 1 and Example 3, Example 2 and Example 4 have the same low driving voltage, high device efficiency (EQE and CE) and very high device lifetime, and there is a further increase in device efficiency (EQE and CE) and a significant increase in device lifetime compared with Comparative Examples 1-2. This again proves the excellent performance of the compound of the present invention represented by the specific Formula 1.

[0322] In summary, when the compound of Formula 1 of the present invention is used as the host material of the light-emitting layer, it improves the electron and hole transport balance ability of the material, and can significantly improve the comprehensive performance of the device: having a low driving voltage, high device efficiency (EQE and CE), and at the same time having a significantly increased device lifetime unexpectedly. This is of great help to the industry.

[0323] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories regarding why the present invention works are not intended to be limiting.

Claims

1. A compound having the structure of Formula 1: Wherein, U is the same as or different each time it appears and is selected from CR u or N; V1-V4 are each independently selected from C, CR v or N, and one of V1-V4 is selected from C and is connected to L, V5-V 12 are each independently selected from CR v or N; X is the same as or different from each occurrence and is selected from CR x or N; Y is selected from C, R y or N; Z is the same as or different from each other each time it appears and is selected from CR z or N; Ar is selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, or a combination thereof; L is selected from a single bond, a substituted or unsubstituted alkylene group having 1 - 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 - 20 carbon atoms, a substituted or unsubstituted arylene group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 - 30 carbon atoms, or a combination thereof; R v , R x and R z each occurrence is the same or different and is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic group having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermyl having 3-20 carbon atoms, substituted or unsubstituted arylgermyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; R u and R y each occurrence is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; said R u and R y when selected from heteroaryl, the heteroatoms in the ring atoms of the heteroaryl are selected from one or more of O, S, Se, Si, P, Ge, and B; Adjacent substituents R u can optionally be linked to form a ring; Adjacent substituents R v may optionally be linked to form a ring; Adjacent substituents R x , R y may optionally be linked to form a ring; Adjacent substituents R z can optionally be linked to form a ring.

2. The compound according to claim 1, wherein V2 is selected from C and is connected to L.

3. The compound according to claim 1, wherein each occurrence of U is the same or different and is independently selected from CR u , and / or Y is selected from CR y ; Preferably, the R u and R y are each independently selected, each time they appear, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, cyano, and combinations thereof; when the R u and R y are selected from heteroaryl, the heteroatom in the ring atoms of the heteroaryl is selected from one or more of O, S, Se, Si, P, Ge, and B; More preferably, said R u and R y are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

4. The compound according to claim 1, wherein each occurrence of X is the same or different and is independently selected from CR x , and / or each occurrence of Z is the same or different and is independently selected from CR z ; Preferably, said R x and R z are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, cyano, and combinations thereof; More preferably, said R x and R z are each independently selected, each time they appear, from the group consisting of hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

5. The compound according to claim 1, wherein each of V1-V4 is independently selected from C or CR v , and one of V1-V4 is selected from C and is connected to L, and V5-V 12 are each independently selected from CR v ; Preferably, said R v is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-20 carbon atoms, substituted or unsubstituted heteroaryl having 3-20 carbon atoms, cyano, and combinations thereof; More preferably, said R v is the same or different each time it appears and is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, cyano, and combinations thereof.

6. The compound according to claim 1, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 - 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 20 carbon atoms, or a combination thereof; Preferably, Ar is selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, and combinations thereof.

7. The compound according to claim 1, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 - 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 - 20 carbon atoms, or a combination thereof; Preferably, L is selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridylene, or a combination thereof.

8. The compound according to claim 1, wherein the compound is selected from the group consisting of Compound A - 1 to Compound A - 240: Among them, Optionally, the hydrogen in Compound A - 1 to Compound A - 240 can be partially or completely replaced by deuterium.

9. An organic electroluminescent device, comprising: An anode, A cathode, And an organic layer disposed between the anode and the cathode, the organic layer comprising the compound according to any one of claims 1 - 8.

10. The organic electroluminescent device according to claim 9, wherein the organic layer is a light - emitting layer and the compound is a host compound; or the organic layer is an electron - transporting layer and the compound is an electron - transporting compound; or the organic layer is a hole - blocking layer and the compound is a hole - blocking compound.

11. The organic electroluminescent device according to claim 9, wherein the organic layer is a light - emitting layer and the compound is a host compound, and the light - emitting layer further comprises a second host compound and a metal complex; Preferably, wherein the second host compound has a structure represented by Formula 2 or Formula 3: Wherein, T is the same as or different each time it appears and is selected from C, CR t or N; G is the same or different each time it appears and is selected from C(R g )2, NR g , O or S; when there are multiple R g s, the multiple R g s are the same or different; L T Each occurrence is independently selected from a single bond, a substituted or unsubstituted alkylene having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms, or a combination thereof; R t and R g each occurrence of which is the same as or different from one another and is independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, mercapto, hydroxy, sulfinyl, sulfonyl, phosphino, and combinations thereof; Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 - 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 - 30 carbon atoms, or a combination thereof each time they appear; Adjacent substituents R t and R g can optionally be linked to form a ring; More preferably, the second main compound is selected from the group consisting of Compound PH-1 to Compound PH-114:

12. A composition comprising the compound according to any one of claims 1-8.

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