Organic electroluminescent material and device thereof

Abstract

Disclosed are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a compound having a structure of Formula 1, which can be used as a host material in an organic electroluminescent device. The novel compounds can provide better device performance, such as higher current efficiency, higher external quantum efficiency, and especially longer device lifetime. Also disclosed are an organic electroluminescent device, a compound composition, and an electronic device comprising the compound.

Description

Technical Field

[0001] This 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 organic electroluminescent devices, compound compositions, and electronic devices comprising the compound. Background Technology

[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 photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both 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. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). 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 anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as fabrication on flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, 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 OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] CN115109051A discloses a compound having the following general formula. Where ring A is a naphthalene ring, and Ar2 is the group shown in Formula 2: X is selected from O or S, and Ar3 is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups with 5-30 carbon atoms. Although its specific structure is not disclosed... The disclosed specific structure must contain a benzo[carbazole] structural unit. There is no disclosure or teaching of compounds formed by linking carbazole and aryl or non-nitrogenous heteroaryl triaryl groups through a linking group and benzo[oxazole].

[0009] However, there is still room for improvement in the main materials currently reported. To meet the industry's ever-increasing demands, especially for higher efficiency and longer device lifespan, new materials still require further research and development. Summary of the Invention

[0010] The present invention aims to provide a series of compounds having the structure of Formula 1 to solve at least some of the above-mentioned problems. These compounds can be used as host materials in organic electroluminescent devices. These novel compounds can provide better device performance.

[0011] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0012]

[0013] in,

[0014] X is selected from O, S, Se, or NR. n ;

[0015] Z1 to Z4 are selected from C and CR each time they appear, either identically or differently. z Or N; and one of Z1 to Z4 is selected from C and connected to L1;

[0016] Y1 to Y8 are selected from CR each time they appear, either identically or differently. y Or N;

[0017] L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0018] Ar and Ar1 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and when the cyclic atom of Ar1 contains a heteroatom, the heteroatom is selected from the group consisting of oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms;

[0019] Rz R n R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0020] According to another 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, the organic layer comprising a compound having a structure of Formula 1, the specific structure of which is shown in the foregoing embodiment.

[0021] According to another embodiment of the present invention, a compound composition comprising the compound having the structure of Formula 1, wherein the specific structure of the compound is as shown in the foregoing embodiments is disclosed.

[0022] According to another embodiment of the present invention, an electronic device is also disclosed, which includes an organic electroluminescent device, the specific structure of which is shown in the foregoing embodiment.

[0023] The novel compounds with the structure of Formula 1 disclosed in this invention can be used as host materials in electroluminescent devices. These novel compounds can provide better device performance, such as higher current efficiency, higher external quantum efficiency, and especially longer device lifetime. Attached Figure Description

[0024] Figure 1 This is a schematic diagram of an organic light-emitting device that may contain the compounds and compound compositions disclosed herein.

[0025] Figure 2This is a schematic diagram of another organic light-emitting device that may contain the compounds and compound compositions disclosed herein. Detailed Implementation

[0026] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. 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. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0027] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 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 are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0028] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0029] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0030] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation 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 on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0031] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such 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, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0032] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0033] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0034] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0035] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0036] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0037] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.

[0038] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0039] Definition of the term "substituent group"

[0040] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0041] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 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 group may optionally be substituted.

[0042] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0043] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.

[0044] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.

[0045] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.

[0046] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-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'-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0047] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0048] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. 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 heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0049] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0050] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0051] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl 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 The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0052] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 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, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0053] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0054] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0055] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0056] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0057] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.

[0058] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0059] In the compounds mentioned in this 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. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0060] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0061] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0062] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:

[0063]

[0064] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:

[0065]

[0066] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0067]

[0068] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0069]

[0070] According to one embodiment of the present invention, a compound having the structure of Formula 1 is disclosed:

[0071]

[0072] in,

[0073] X is selected from O, S, Se, or NR. n ;

[0074] Z1 to Z4 are selected from C and CR each time they appear, either identically or differently. z Or N; and one of Z1 to Z4 is selected from C and connected to L1;

[0075] Y1 to Y8 are selected from CR each time they appear, either identically or differently. y Or N;

[0076] L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0077] Ar and Ar1 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and when the cyclic atom of Ar1 contains a heteroatom, the heteroatom is selected from the group consisting of oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms;

[0078] R z R n R yEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0079] In this article, "when the ring atoms of Ar1 contain heteroatoms, the heteroatoms are selected from the group consisting of oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms" means that when the atoms in the entire Ar1 ring contain heteroatoms, the heteroatoms are not selected from nitrogen atoms. For example, the ring atoms in nitrogen-substituted aryl groups such as pyridyl, carbazole, benzocarbazole, quinazolinyl, piperidinylbenzocarbazole, and piperazineylbenzocarbazole contain nitrogen. Therefore, the ring atoms of these nitrogen-substituted aryl groups are not within the scope of Ar1. Examples of nitrogen-substituted aryl groups include carbazolephenyl, benzocarbazolephenyl, piperidinylphenyl, and piperazinephenyl. Since the group contains nitrogen, the above-mentioned groups are not within the scope of Ar1. For example, the ring atoms in nitrogen-containing heterocyclic groups or heteroaryl-substituted cycloalkyl groups such as carbazole-containing heterocyclic groups, benzocarbazole-containing heterocyclic groups, piperidine-containing heterocyclic groups, and piperazine-containing heterocyclic groups contain nitrogen. Therefore, the above-mentioned groups are not within the scope of Ar1. Thus, the entire Ar1 is not selected from any nitrogen-containing heterocyclic group or nitrogen-containing heteroaryl group. For example, the nitrogen atom in an amino group is not a ring atom of Ar1. Therefore, Ar1 can be selected from amino-substituted aryl groups with 6-30 carbon atoms, amino-substituted heteroaryl groups with 3-30 carbon atoms, amino-substituted cycloalkyl groups with 3-20 ring carbon atoms, or combinations thereof.

[0080] According to one embodiment of the present invention, the compound has the structure represented by Formula 1-1:

[0081]

[0082] X is selected from O, S, Se, or NR. n ;

[0083] Z1 to Z4 are selected from C and CR each time they appear, either identically or differently. z Or N; and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;

[0084] Y1 to Y8 are selected from CR each time they appear, either identically or differently. y Or N;

[0085] When W1 to W5 appear, they are either identical or different and are selected from C, CR. w Or N; and one of W1 to W5 is selected from C and is attached to N in the amino group shown in Formula 1-1;

[0086] L2 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0087] Ar and Ar1 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and when the cyclic atom of Ar1 contains a heteroatom, the heteroatom is selected from the group consisting of oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms;

[0088] R z R n R y R wEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0089] Adjacent substituent R w They can be arbitrarily connected to form a ring.

[0090] In this paper, adjacent substituents R w They can be optionally linked to form a ring, intended to represent any adjacent substituent R therein. w They can connect to form a ring. It is obvious that any adjacent substituents R... w They can also be left unconnected to form a loop.

[0091] According to one embodiment of the present invention, X is selected from O, S or NR. n .

[0092] According to one embodiment of the present invention, X is selected from O or S.

[0093] According to one embodiment of the present invention, Y1 to Y8 are selected from CR each time they appear, either identically or differently. y .

[0094] According to one embodiment of the invention, Z1 to Z4 are selected from C or CR each time they appear, either identically or differently. z And one of Z1 to Z4 is selected from C and connected to L1.

[0095] According to one embodiment of the invention, W1 to W5 are selected from C or CR each time they appear, either identically or differently. wAnd one of W1 to W5 is selected from C and is attached to N in the amino group shown in Formula 1-1.

[0096] According to one embodiment of the present invention, R y R z R n R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0097] According to one embodiment of the present invention, R y R z R n R w Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, phenyl, pyridyl, pyrimidinyl, vinyl, naphthyl, biphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl. alkyl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.

[0098] According to one embodiment of the present invention, Ar is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, or combinations thereof.

[0099] According to one embodiment of the invention, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted... The group is composed of substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or combinations thereof.

[0100] According to one embodiment of the present invention, Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, silylfluorenyl. alkyl, benzoxazolyl, or combinations thereof.

[0101] According to one embodiment of the present invention, Ar1 is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, or combinations thereof; and when the ring atoms of Ar1 contain heteroatoms, the heteroatoms are selected from the group consisting of oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms and boron atoms.

[0102] According to one embodiment of the present invention, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted... Base, or a combination thereof.

[0103] According to one embodiment of the present invention, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted... Base, or a combination thereof.

[0104] According to one embodiment of the present invention, Ar1 is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, silylfluorenyl. Base, or a combination thereof.

[0105] According to one embodiment of the present invention, L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, or combinations thereof.

[0106] According to one embodiment of the present invention, L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-24 carbon atoms.

[0107] According to one embodiment of the present invention, L1 and L2 are each independently selected from phenylene, naphthylene, biphenylene, phenanthrene, or combinations thereof.

[0108] According to one embodiment of the present invention, the L2 is selected from the group consisting of the following structures:

[0109]

[0110] The asterisk (*) indicates the position in the structure of L2 where it is connected to the nitrogen in the amino group. This indicates the position in the structure of L2 that is linked to N in carbazole.

[0111] According to one embodiment of the present invention, the compound is selected from the group consisting of compounds A-1 to A-340, and the specific structures of compounds A-1 to A-340 are given in claim 10.

[0112] According to one embodiment of the present invention, the hydrogen in the structure of compounds A-1 to A-340 is partially or completely replaced by deuterium.

[0113] According to another embodiment of the present invention, an organic electroluminescent device is also disclosed, comprising:

[0114] anode,

[0115] cathode,

[0116] And an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound having a structure of Formula 1, the specific structure of which is as described in any of the foregoing embodiments.

[0117] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, a hole transport layer, or an electron blocking layer.

[0118] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the compound is a host material.

[0119] According to an embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, the light-emitting layer contains a second compound, the second compound is a host material, and the second compound has a structure represented by Formula 2:

[0120]

[0121] In Equation 2,

[0122] L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0123] Ar 21 To Ar 23Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0124] According to one embodiment of the present invention, the second compound has the structure shown in Formula 2-1:

[0125]

[0126] V1-V6 each time they appear, they are either selected from C, N, or CR, either in the same or different ways. v And one of V1-V6 is C and is associated with L. 23 Connected;

[0127] L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0128] Ar 21 and Ar 22 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0129] R v Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0130] Adjacent substituent R v They can be arbitrarily connected to form a ring.

[0131] In this paper, adjacent substituents R v They can be optionally linked to form a ring, intended to represent any adjacent substituent R therein. v They can connect to form a ring. It is obvious that any adjacent substituents R... v They can also be left unconnected to form a loop.

[0132] According to one embodiment of the present invention, the second compound has the structure shown in Formula 2-1-1 or Formula 2-1-2:

[0133]

[0134] In Equation 2-1-1, V1-V5 are selected from C, N, or CR each time they appear, either identically or differently. v V 11 -V 15 Each occurrence is either identically or differently selected from N or CR v1 And one of V1-V5 is C and is associated with L. 23 Connected; in Equation 2-1-2, V1-V4 are selected from C, N, or CR each time they appear, either identically or differently. v V 11 -V 14 Each occurrence is either identically or differently selected from N or CR v1 And one of V1-V4 is C and is associated with L 23 Connected;

[0135] V is selected from O, S, or Se;

[0136] L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0137] Ar 21 and Ar 22 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0138] R v R v1Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0139] Adjacent substituent R v R v1 They can be arbitrarily connected to form a ring.

[0140] In this paper, adjacent substituents R v R v1 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, adjacent substituent R. v Between, adjacent substituents R v1 Between, and adjacent substituents R v and R v1 Between these substituents, any one or more of these substituent groups can connect to form a ring. Obviously, these substituents can also not connect to form a ring.

[0141] According to one embodiment of the present invention, in formula 2-1-2, V is selected from O or S.

[0142] According to one embodiment, V is O in Equation 2-1-2.

[0143] According to one embodiment of the present invention, in formula 2-1-1, V1 to V5 are selected from C or CR each time they appear, either identically or differently. v V 11 To V 15 Each time it appears, it is selected from CR in the same or different ways. v1 In Equation 2-1-2, V1 to V4 are selected from C or CR each time they appear, either identically or differently. v V11 To V 14 Each time it appears, it is selected from CR in the same or different ways. v1 .

[0144] According to one embodiment of the present invention, wherein R v R v1 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

[0145] According to one embodiment of the present invention, in formula 2-1-1, at least one of V1 to V5 is selected from CR. v , or V 11 To V 15 At least one of them is selected from CR v1 In Equation 2-1-2, at least one of V1 to V4 is selected from CR. v , or V 11 To V 14 At least one of them is selected from CR v1 And the R v R v1 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, either identically or differently.

[0146] According to one embodiment of the present invention, wherein R v R v1 Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, and combinations thereof.

[0147] According to one embodiment of the present invention, wherein the Ar 21 and Ar 22 At least one of them has a structure with two or three fused rings.

[0148] According to one embodiment of the present invention, Ar 21 and Ar 22 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof, either identically or differently.

[0149] According to one embodiment of the present invention, Ar 21 and Ar 22Each occurrence is selected, either identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted... The group, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted indolocarbazolyl, or combinations thereof.

[0150] According to one embodiment of the present invention, L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0151] According to one embodiment of the present invention, L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, or combinations thereof, either identically or differently.

[0152] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds B-1 to B-262, and the specific structures of compounds B-1 to B-262 are given in claim 13.

[0153] According to one embodiment of the present invention, the hydrogen in the structure of compounds B-1 to B-262 can be partially or completely replaced by deuterium.

[0154] According to one embodiment of the present invention, in the fabrication of the device, when the compound of the present invention and the second compound are co-deposited with the luminescent material to form a luminescent layer, the luminescent layer can be formed by placing the compound of the present invention, the second compound and the luminescent material in different evaporation sources respectively, or by placing a pre-mixed mixture of the compound of the present invention and the second compound in the same evaporation source, and then co-depositing it with the luminescent material placed in another evaporation source to form a luminescent layer. This pre-mixing method can further save evaporation sources.

[0155] According to one embodiment of the present invention, in the organic electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer contains at least one phosphorescent material.

[0156] According to one embodiment of the present invention, the phosphorescent material is a metal complex, and the metal complex has M(L) a) m (L b ) n (L c ) q The general formula;

[0157] M is selected from metals with a relative atomic mass greater than 40;

[0158] L a L b and L c These are the first, second, and third ligands that coordinate with M, respectively; L a L b and L c They can be selectively linked to form multidentate ligands;

[0159] L a L b and L c Same or different; 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 equals the oxidation state of M; when m is greater than or equal to 2, multiple L a Same or different; when n is 2, the two L b Same or different; when q is 2, the two L c Same or different;

[0160] L a Each occurrence is either identical or different from the structure shown in Equation 3:

[0161]

[0162] in,

[0163] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0164] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0165] Rings D and E via U a and U b Condensation;

[0166] U a and U b Each occurrence is either identical or different and is selected from C or N;

[0167] R d and R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0168] V 31 To V 34 Each time it appears, it is selected from CR in the same or different ways. v3Or N;

[0169] R d R e and R v3 Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0170] Adjacent substituent R d R e and R v3 They can be arbitrarily connected to form a loop;

[0171] L b and L c Each occurrence may be selected from any of the following structures, either identically or differently:

[0172]

[0173] R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0174] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;

[0175] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;

[0176] R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0177] The ligand L b L c In the structure, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

[0178] In this paper, adjacent substituents R d R e R v3 The ability to optionally connect to form a ring is intended to indicate the presence of a substituent R. d Substituent R e Substituent R v3 When, adjacent substituent groups, such as adjacent substituent R d Substituents R between and adjacent e Substituents R between and adjacent v3 Substituents R between and adjacent d With R e Substituents R between and adjacentd With R v3 Between and adjacent substituents R e With R v3 Between these adjacent substituent groups, any one or more can connect to form a ring. It is obvious that when substituent R is present... d , substituent R e , substituent R v3 At the same time, these substituent groups may not be connected to form a ring.

[0179] In this paper, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the 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 R C1 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 these substituent groups, one or more of them can be linked to form a ring. For example, adjacent substituents R a R b It can be optionally connected to form a ring, which can form one or more of the following structures, including but not limited to:

[0180] Where W is selected from O, S, Se, NR w1 or CR w1 R w1 ; wherein R w1 R a ', R b The definition of ' and the aforementioned R a The same. Obviously, these substituents can also not be connected to form a ring.

[0181] According to one embodiment of the present invention, in Formula 3, two adjacent substituents R e The connection forms a loop.

[0182] According to one embodiment of the present invention, in Formula 3, two adjacent substituents R e They can be linked to form 5-membered unsaturated carbon rings, 5-membered heteroaromatic rings, or benzene rings.

[0183] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a benzene ring or a 6-membered heteroaromatic ring.

[0184] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring.

[0185] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, ring E is a benzene ring or a 6-membered heteroaromatic ring, and the two adjacent substituents R e They can be linked to form benzene rings or 6-membered heteroaromatic rings.

[0186] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbide ring, and the two adjacent substituents R e They can be linked to form benzene rings or 6-membered heteroaromatic rings.

[0187] According to one embodiment of the present invention, in formula 3, R d R e R v3 At least one or two sets of adjacent substituents are linked to form a ring. For example, two substituents R d The connection forms a ring, or two substituents R e The connection forms a ring, or two substituents R v3 Linkage to form a ring, or substituent R d With substituent R e The links between them form a ring, or the substituent R d With substituent R v3 The links between them form a ring, or the substituent R e With substituent R v3 The two substituents R are connected to form a ring or a ring.d The two substituents R connect to form a ring. e The connection forms a ring, or two substituents R d The two substituents R connect to form a ring. v3 The connection forms a ring, or two substituents R e The two substituents R connect to form a ring. v3 Linkage forms a ring, substituent R e With substituent R v3 The two substituents R are linked to form a ring. v3 Linkage to form a ring, or substituent R d With substituent R v3 The two substituents R are linked to form a ring. v3 The connection forms a loop; R d R e R v3 A similar situation occurs when more adjacent substituents are linked to form a ring.

[0188] According to an embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is a metal complex, and the metal complex has M(L) a ) m (L b ) n The general formula;

[0189] M is selected from metals with a relative atomic mass greater than 40;

[0190] L a L b The first and second ligands, respectively, coordinate with M; L a L b They can be selectively linked to form multidentate ligands;

[0191] m is 1, 2, or 3; n is 0, 1, or 2; the sum of m and n equals the oxidation state of M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different;

[0192] L a Each occurrence is either identical or different from the structure shown in Equation 3:

[0193]

[0194] in,

[0195] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;

[0196] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;

[0197] Rings D and E via U a and U b Condensation;

[0198] U a and U b Each occurrence is either identical or different and is selected from C or N;

[0199] R d and R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;

[0200] V 31 To V 34 Each time it appears, it is selected from CR in the same or different ways. v3 Or N;

[0201] R d R e and R v3 Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0202] Adjacent substituent R d R e and R v3 They can be arbitrarily connected to form a loop;

[0203] The ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0204]

[0205] R1 to R7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted... Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, thio, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0206] According to an embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0207]

[0208] Wherein, at least one of R1 to R3 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and / or at least one of R4 to R6 is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

[0209] According to an embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0210]

[0211] Wherein, at least two of R1 to R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and / or at least two of R4 to R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

[0212] According to an embodiment of the present invention, in the organic electroluminescent device, wherein the ligand L b Each occurrence is selected from the following structure, either identically or differently:

[0213]

[0214] Wherein, at least two of R1 to R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and / or at least two of R4 to R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.

[0215] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex, a Pt complex, or an Os complex.

[0216] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and has Ir(L) oxidizing properties. a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a (L) b )2、Ir(L a )2(L c ) or Ir(L a (L) c Any of the structures shown in )2.

[0217] According to one embodiment of the present invention, wherein L aIt has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of a 6-membered 6-membered aromatic ring, a 6-membered 6-membered heteroaromatic ring, a 6-membered 5-membered aromatic ring and a 6-membered 5-membered heteroaromatic ring.

[0218] According to an embodiment of the present invention, in the organic electroluminescent device, wherein L a It has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

[0219] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. a The L a Each time it appears, choose either the same or different one from any of the following groups of structures:

[0220]

[0221]

[0222]

[0223]

[0224] In the structure described, TMS represents trimethylsilyl.

[0225] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. b The L b Each time it appears, choose either the same or different one from any of the following groups of structures:

[0226]

[0227] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is selected from the group consisting of the following structures:

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] In the structure described, TMS represents trimethylsilyl.

[0236] According to another embodiment of the present invention, a compound composition comprising a compound having the structure of Formula 1, wherein the specific structure of the compound is as shown in any of the foregoing embodiments.

[0237] According to one embodiment of the present invention, the compound composition comprises a second compound having a structure represented by Formula 2:

[0238]

[0239] In Equation 2,

[0240] L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof.

[0241] Ar 21 To Ar 23 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.

[0242] According to another embodiment of the present invention, an electronic device is also disclosed, which includes an organic electroluminescent device, wherein the specific structure of the organic electroluminescent device is as shown in any of the foregoing embodiments.

[0243] Combination with other materials

[0244] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0245] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, implantation layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0246] 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 is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0247] Material synthesis examples:

[0248] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0249] Synthesis Example 1: Synthesis of Compound A-10

[0250] Step 1: Synthesis of Intermediate 3

[0251]

[0252] Under nitrogen protection, intermediate 1 (50.00 g, 265.92 mmol), intermediate 2 (31.04 g, 292.50 mmol), and ethanol (500 mL) were added to a three-necked flask and reacted at 80 °C for 16 h. After the reaction was complete, the reaction solution was concentrated to remove the solvent, and the solid was washed three times with petroleum ether and dissolved in dichloromethane (500 mL). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 90.55 g, 398.90 mmol) was added, and the reaction was carried out at room temperature for 12 h. After the reaction was complete, the reaction solution was extracted with dichloromethane, the organic phase was washed with water, and the solvent was removed. The crude product was purified by column chromatography (PE / DCM = 1 / 1) to give a white solid intermediate 3 (50 g, yield: 69%).

[0253] Step 2: Synthesis of Intermediate 5

[0254]

[0255] Under nitrogen protection, intermediates 3 (40.00 g, 145.92 mmol), 4 (25.10 g, 160.52 mmol), tetrakis(triphenylphosphine)palladium (1.69 g, 1.46 mmol), potassium carbonate (40.33 g, 291.80 mmol), toluene (200 mL), ethanol (50 mL), and water (50 mL) were added to a three-necked flask and reacted at 100 °C for 16 h. After the reaction was complete, the mixture was extracted with ethyl acetate, washed with water, and concentrated to remove the solvent. The crude product was purified by column chromatography (PE / DCM = 1 / 1) to give a white solid intermediate 5 (35 g, yield: 78%).

[0256] Step 3: Synthesis of compound A-10

[0257]

[0258] Under nitrogen protection, intermediates 5 (3.00 g, 9.81 mmol), 6 (4.43 g, 10.79 mmol), bis(dibenzylacetone)palladium (111.25 mg, 0.196 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 161.12 mg, 0.392 mmol), sodium tert-butoxide (1.89 g, 19.67 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was complete, the mixture was extracted with dichloromethane, washed with water, and concentrated to remove the solvent. The crude product was purified by column chromatography (PE / DCM = 2 / 1) to give a yellow solid compound A-10 (2.7 g, yield: 40.5%). The product was identified as the target product with a molecular weight of 679.26.

[0259] Synthesis Example 2: Synthesis of Compound A-11

[0260]

[0261] Under nitrogen protection, intermediates 5 (3.00 g, 9.81 mmol), 7 (4.43 g, 10.79 mmol), bis(dibenzylacetone)palladium (111.25 mg, 0.196 mmol), 2-biscyclohexylphosphine-2',6'-dimethoxybiphenyl (Sphos, 161.12 mg, 0.392 mmol), sodium tert-butoxide (1.89 g, 19.67 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was complete, the mixture was extracted with dichloromethane, washed with water, and the solvent was removed by concentration. The crude product was purified by column chromatography (PE / DCM = 2 / 1) to give a yellow solid compound A-11 (3.2 g, yield: 48%). The product was identified as the target product with a molecular weight of 679.26.

[0262] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0263] Device Example 1

[0264] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -6 In the case of Torr, it is 0.01-5 The deposition rate was achieved sequentially on the ITO anode via thermal vacuum. Compounds HT and HI were co-deposited as a hole injection layer (HIL, weight ratio 97:3), with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, compound A-10 (as the first main component), compound B-227 (as the second main component), and compound RD (as a dopant) were co-deposited as an emissive layer (EML, weight ratio 48.5:48.5:3), with a thickness of [missing information]. Compound B-1 was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL, weight ratio 40:60), with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0265] Device Example 2

[0266] The implementation method of Device Example 2 is the same as that of Device Example 1, except that Compound A-11 of the present invention is used instead of Compound A-10 of the present invention as the first host in the light-emitting layer (EML).

[0267] Device Comparison Example 1

[0268] The implementation of Comparative Example 1 is the same as that of Example 1, except that compound C is used instead of compound A-10 of the present invention as the first host in the light-emitting layer (EML), and the doping weight ratio of compound C and compound B-227 is adjusted to 58.2:38.8.

[0269] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.

[0270] Table 1. Partial device structures of device embodiments and comparative examples.

[0271]

[0272] The material structure used in the device is shown below:

[0273]

[0274] Table 2 lists the values ​​at 15 mA / cm 2 The current efficiency CE [cd / A] and external quantum efficiency EQE [%] measured under constant current, and the current efficiency at 80 mA / cm² was measured. 2 The device lifetime LT97 [h] was tested under constant current. Device lifetime (LT97) refers to the time required for the device brightness to decay to 97% of its initial brightness.

[0275] Table 2 Device Data

[0276] Device ID <![CDATA[λ max (nm)]]> CE[cd / A] EQE[%] LT97[h] Example 1 622 27.3 25.8 60 Example 2 621 27.4 25.5 57 Comparative Example 1 622 25.4 23.7 32

[0277] discuss:

[0278] As shown in Table 2, the maximum emission wavelengths of the device examples and comparative examples are basically the same. The main difference between Example 1 and Comparative Example 1 lies in the Ar1 linked to the amino group, specifically the difference between benzoxazole and biphenyl. Compared with Comparative Example 1, Example 1 further improves upon the already high current efficiency and external quantum efficiency of Comparative Example 1. The current efficiency (CE) and external quantum efficiency (EQE) of Example 1 are increased by 7.5% and 8.9%, respectively. Remarkably, while maintaining high efficiency (CE, EQE), the lifetime of Example 1 is unexpectedly improved, with an increase of 87.5%. The above data indicate that compounds formed by linking carbazole and a specific Ar1 to the amino group and then linking them to benzoxazole via phenylene oxide exhibit higher current efficiency and external quantum efficiency, especially a significantly improved device lifetime, when applied to organic electroluminescent devices.

[0279] Example 2, which uses a compound of the present invention with a different structure as the first subject, achieved the same excellent device performance as Example 1. Compared with Comparative Example 1, the current efficiency (CE) and external quantum efficiency (EQE) of Example 2 were improved by 7.9% and 7.6%, respectively. Remarkably, while maintaining high efficiency (CE, EQE), the lifetime of Example 2 was unexpectedly improved by 78%. These results demonstrate that the compound of the present invention with the structure of Formula 1 exhibits higher current efficiency and external quantum efficiency when applied to organic electroluminescent devices, especially with a significantly improved device lifetime, further proving the unique advantages of the compound of the present invention.

[0280] In summary, the compounds with the structure of Formula 1 disclosed in this invention can be used as host materials in organic electroluminescent devices to achieve excellent overall device performance, such as higher current efficiency, higher external quantum efficiency, and especially longer device lifetime. Therefore, they have broad commercial development prospects and application value.

[0281] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the 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 can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. Compounds having the structure of Formula 1: in, X is selected from O, S, Se, or NR. n ; Z1 to Z4 are selected from C and CR each time they appear, either identically or differently. z Or N; and one of Z1 to Z4 is selected from C and connected to L1; Y1 to Y8 are selected from CR each time they appear, either identically or differently. y Or N; L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar and Ar1 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and when the cyclic atom of Ar1 contains a heteroatom, the heteroatom is selected from the group consisting of oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms; R z R n R y Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

2. The compound of claim 1, wherein the compound has the structure represented by formula 1-1: X is selected from O, S, Se, or NR. n ; Z1 to Z4 are selected from C and CR each time they appear, either identically or differently. z Or N; and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5; Y1 to Y8 are selected from CR each time they appear, either identically or differently. y Or N; When W1 to W5 appear, they are either identically or differently selected from C, CR. w Or N; and one of W1 to W5 is selected from C and is attached to N in the amino group shown in Formula 1-1; L2 is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar and Ar1 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and when the cyclic atom of Ar1 contains a heteroatom, the heteroatom is selected from the group consisting of oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron atoms; R z R n R y R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R w They can be arbitrarily connected to form a ring.

3. The compound of claim 1 or 2, wherein X is selected from O, S, or NR. n ; Preferably, X is selected from O or S.

4. The compound of claim 2, wherein Z1 or Z4 is selected from C and is connected to a six-membered ring comprising W1 to W5; Preferably, Z4 is selected from C and connected to a six-membered ring containing W1 to W5.

5. The compound of claim 2, wherein one of W2 to W4 is selected from C and is attached to N in the amino group; Preferably, W3 is selected from C and is attached to N in the amino group.

6. The compound of claim 2, wherein R y R z R n R w Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Preferably, R y R z R n R w Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, phenyl, pyridyl, pyrimidinyl, vinyl, naphthyl, biphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl. alkyl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.

7. The compound of claim 1 or 2, wherein Ar is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, or combinations thereof. Preferably, Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted... alkyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or combinations thereof; More preferably, Ar is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, silylfluorenyl. alkyl, benzoxazolyl, or combinations thereof.

8. The compound of claim 1 or 2, wherein Ar1 is selected from substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-18 carbon atoms, or combinations thereof; and when the ring atom of Ar1 contains a heteroatom, the heteroatom is selected from the group consisting of oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Preferably, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted... base, or combinations thereof; More preferably, Ar1 is selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, silylfluorenyl. Base, or a combination thereof.

9. The compound of claim 1, wherein L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, or combinations thereof; Preferably, L1 and L2 are each independently selected from substituted or unsubstituted aryl groups having 6-24 carbon atoms; More preferably, L1 and L2 are each independently selected from phenylene, naphthylene, biphenylene, phenanthrene, or combinations thereof.

10. The compound of claim 1, wherein the compound is selected from the group consisting of: Optionally, the hydrogen in the structure of compounds A-1 to A-340 may be partially or completely replaced by deuterium.

11. An organic electroluminescent device, comprising: anode, cathode, An organic layer disposed between the anode and the cathode, the organic layer comprising any one of claims 1 to 10.

12. The organic electroluminescent device of claim 11, wherein the organic layer is a light-emitting layer, a hole transport layer, or an electron blocking layer; Preferably, the organic layer is a light-emitting layer, and the compound is the host material.

13. The organic electroluminescent device of claim 11, wherein the organic layer is a light-emitting layer, and the organic layer further comprises a second compound, the second compound being a host material, the second compound having a structure represented by Formula 2: In Equation 2, L 21 To L 23 Each time it appears, it is selected from single bonds, substituted or unsubstituted alkylene groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3-20 carbon atoms, substituted or unsubstituted arylene groups having 6-30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3-30 carbon atoms, or combinations thereof. Ar 21 To Ar 23 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently. Preferably, the second compound is selected from the group consisting of: Optionally, the hydrogen in the structure of compounds B-1 to B-262 may be partially or completely replaced by deuterium.

14. The organic electroluminescent device of claim 12, wherein the organic layer is a light-emitting layer, and the light-emitting layer comprises at least one phosphorescent material.

15. The organic electroluminescent device of claim 14, wherein the phosphorescent material is a metal complex, said metal complex having M(L) a ) m (L b ) n (L c ) q The general formula; M is selected from metals with a relative atomic mass greater than 40; L a L b and L c These are the first ligand, the second ligand, and the third ligand that coordinate with M, respectively; L a L b and L c They can be selectively linked to form multidentate ligands; L a L b and L c They can be the same or different; 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 equals the oxidation state of M; when m is greater than or equal to 2, multiple L a They can be the same or different; when n is 2, the two Ls b They can be the same or different; when q is 2, the two Ls c They can be the same or different; L a Each occurrence may be selected from the structure shown in Equation 3, either identically or differently: in, Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring; Rings D and E via U a and U b Condensation; U a and U b Each occurrence is either identical or different and is selected from C or N; R d and R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; V 31 To V 34 Each time it appears, it is selected from CR in the same or different ways. v3 Or N; R d R e and R v3 Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having... Alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups with 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups with 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof with 0-20 carbon atoms; Adjacent substituent R d R e and R v3 They can be arbitrarily connected to form a loop; L b and L c Each occurrence may be selected from any of the following structures, either identically or differently: in, R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ; R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.

16. A compound composition comprising the compound of any one of claims 1 to 10.

17. An electronic device comprising the organic electroluminescent device according to any one of claims 11 to 15.

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