CN113527316A - Electroluminescent material and device - Google Patents

Abstract

An electroluminescent material and device are disclosed. The electroluminescent material is a compound in which indole and pyrrole condensed aza macrocycles and quinazoline, quinoxaline and similar structures are bonded on a specific ring, and can be used in electroluminescent devices. main material. These new compounds can effectively improve device efficiency, reduce device driving voltage, and provide better device performance. An electroluminescent device and compound formulation are also disclosed.

Description

An electroluminescent material and device

technical field

The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, it relates to a compound in which an indole and pyrrole fused aza macrocycle is bonded to a specific ring with quinazoline, quinoxaline and similar structures, and an organic electroluminescent device comprising the compound and an organic electroluminescent device. Compound formula.

Background technique

Organic electronic devices include but are not limited to the following categories: Organic Light Emitting Diodes (OLEDs), Organic Field Effect Transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), Dye-Sensitized Solar Cells (DSSCs) , organic optical detectors, organic photoreceptors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light-emitting devices.

In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron transport layer and luminescence. Layer (Applied Physics Letters, 1987, 51(12):913-915). Once the device is biased, green light is emitted from the device. 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. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, can make them well suited for special applications, such as in flexible substrate fabrication.

OLEDs can be classified into three different types according to their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It only emits light using singlet states. The triplet states generated in the device are wasted through non-radiative decay paths. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997 Forrest and Thompson reported phosphorescent OLEDs that used triplet emission from complex-containing heavy metals as emitters. Thus, 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). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, enabling the return of excitons from triplet to singlet state. In TADF devices, triplet excitons can generate singlet excitons through inverse intersystem crossing, resulting in high IQE.

OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant light-emitting groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during fabrication.

Various OLED fabrication methods exist. Small molecule OLEDs are usually fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution methods such as spin coating, inkjet printing and nozzle printing. Small-molecule OLEDs can also be fabricated by solution methods if the materials can be dissolved or dispersed in solvents.

The luminescent color of OLED can be realized by structural design of luminescent materials. OLEDs can include one emissive layer or multiple emissive layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from 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. At present, the rapid reduction of the efficiency of phosphorescent OLEDs at high brightness is still a problem. Furthermore, more saturated emission spectra, higher efficiencies and longer device lifetimes are expected.

US20180337340A1 discloses an organic electroluminescent compound and an organic electroluminescent device comprising the same, which comprises an organic layer, the organic layer contains one or more hosts, and the first host is an organic optical compound having the following structure:

但其所公开的化合物必须具有喹唑啉或喹喔啉的结构单元，且必须键合喹唑啉或喹喔啉的2位，并未公开和教导包含键合喹唑啉、喹喔啉及其类似结构的结构单元的其他位点的有机化合物。

However, the disclosed compound must have a structural unit of quinazoline or quinoxaline, and must be bonded to the 2-position of quinazoline or quinoxaline, and it does not disclose and teach that it contains bonded quinazoline, quinoxaline, and quinoxaline. Organic compounds that have similar structures at other sites of the building block.

However, there is still room for improvement for many host materials reported so far. In order to meet the increasing demands of the industry, especially for higher device efficiency, longer device life and lower driving voltage, new materials are still needed. Further research and development is required.

SUMMARY OF THE INVENTION

The present invention aims to solve at least some of the above problems by providing a series of compounds with indole and pyrrole fused azamacrocycles and quinazoline, quinoxaline and similar structures bonded on specific rings. The compounds can be used as host materials in organic electroluminescent devices. These new compounds can effectively improve device efficiency, reduce device driving voltage, and provide better device performance.

According to one embodiment of the present invention, a compound is disclosed, which has the structure of H-L-E,

where H has the structure represented by Equation 1:

wherein, in formula 1, each occurrence of A ₁ , A ₂ and A ₃ is identically or differently selected from N or CR, and each occurrence of Ring A, Ring B and Ring C is identically or differently selected from having 5- A carbocyclic ring of 18 carbon atoms, or a heterocyclic ring of 3-18 carbon atoms;

Each occurrence of R _x represents, identically or differently, monosubstitution, polysubstitution, or no substitution;

where E has the structure represented by Equation 2:

Wherein, in formula 2, any two of Y ₁ to Y ₄ are selected from N, the other two are independently selected from CR _y , and Y ₅ to Y ₈ are each independently selected from N, C or CR _y ;

L is selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;

wherein _R , Rx and _Ry at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amine group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Wherein, adjacent substituents R, R _X can be optionally connected to form a ring;

Among them, adjacent substituents R _y can be optionally connected to form a ring.

According to another embodiment of the present invention, an 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 H-L-E ;

where H has the structure represented by Equation 1:

wherein, in formula 1, each occurrence of A ₁ , A ₂ and A ₃ is identically or differently selected from N or CR, and each occurrence of Ring A, Ring B and Ring C is identically or differently selected from having 5- A carbocyclic ring of 18 carbon atoms, or a heterocyclic ring of 3-18 carbon atoms;

Each occurrence of R _x represents, identically or differently, monosubstitution, polysubstitution, or no substitution;

where E has the structure represented by Equation 2:

Wherein, in formula 2, any two of Y ₁ to Y ₄ are selected from N, and the other two are independently selected from CR _y ; Y ₅ to Y ₈ are each independently selected from N, C or CR _y ;

L is selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;

wherein _R , Rx and _Ry at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amine group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Wherein, adjacent substituents R, R _X can be optionally connected to form a ring;

Among them, adjacent substituents R _y can be optionally connected to form a ring.

According to another embodiment of the present invention, there is also disclosed a compound formulation comprising the compound having the structure of H-L-E.

According to another embodiment of the present invention, a display assembly is also disclosed, which includes the electroluminescent device described in the above embodiments.

The novel compounds with indole and pyrrole fused aza-macrocyclic structures connected with quinazoline, quinoxaline and similar structures disclosed in the invention can be used as host materials in electroluminescent devices. These novel compounds have electron transport units with quinazoline, quinoxaline and similar structures, and hole transport units with indole and pyrrole fused azamacrocyclic structures attached to specific rings of the electron transport unit. This new compound exhibits excellent performance in the balance of hole and electron transport, which can effectively improve device efficiency, reduce device driving voltage, and provide better device performance.

Description of drawings

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

2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

Detailed ways

OLEDs can be fabricated on various substrates such as glass, plastic and metal. FIG. 1 schematically and non-limitingly shows an organic light-emitting device 100 . The figures are not necessarily drawn to scale, and some layer structures in the figures may also be omitted as required. Device 100 may include substrate 101 , anode 110 , hole injection layer 120 , hole transport layer 130 , electron blocking layer 140 , light emitting layer 150 , hole blocking layer 160 , electron transport layer 170 , electron injection layer 180 , and cathode 190 . Device 100 may be fabricated by sequentially depositing the described layers. The properties and functions of the various layers and exemplary materials are described in more detail in US Pat. No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated herein by reference.

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in US Patent No. 5,844,363, which is incorporated 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 in US Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety disclosed in. Examples of host materials are disclosed in US Patent No. 6,303,238 to Thompson et al., which is incorporated 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 US Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes comprising a cathode having a thin layer of metal such as Mg:Ag and an overlying transparent, conductive, sputter deposited ITO layer. Composite cathode. The principles and use of barrier layers are described in more detail in US Patent No. 6,097,147 and US Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in US Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in US Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

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

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

OLEDs also require an encapsulation layer, as shown in FIG. 2 schematically and non-limitingly showing an organic light-emitting device 200, which differs from FIG. 1 in that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in US Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

Devices fabricated in accordance with embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lamps for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, Smartphones, tablets, phablets, wearables, smart watches, laptops, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays and taillights.

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

As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed further from the substrate. Other layers may be present between the first and second layers unless the first layer is specified to be in "contact with" the second layer. For example, the cathode may be described as being "disposed" on" the anode, even though there are various organic layers between the cathode and the anode.

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

A ligand may be referred to as "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photosensitizing properties of the emissive material, but the ancillary ligand may alter the properties of the photosensitizing ligand.

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit by delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet elimination (TTA).

On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between triplet and singlet excited states. Compounds capable of generating E-type delayed fluorescence need to have extremely small singlet-triplet gaps for transitions between energy states. Thermal energy can activate the transition transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as thermally activated delayed fluorescence (TADF). A striking feature of TADF is that the retardation component increases with temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize nonradiative decay from triplet states, the fraction of backfilled singlet excited states may reach 75%. The total singlet fraction can be 100%, well over 25% of the spin statistics of the electro-generated excitons.

E-type delayed fluorescence signatures can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the emissive material to have a small single-triplet energy gap (ΔE _ST ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor charge transfer (CT) type emission. The steric separation of HOMO from LUMO in these donor-acceptor-type compounds typically yields a small _ΔEST . These states may include CT states. Typically, donor-acceptor emissive materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, an N-containing six-membered aromatic ring).

Definition of Substituent Terms

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

Alkyl – includes straight and branched chain alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n- Nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n- Octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Additionally, alkyl groups may be optionally substituted. Carbons in the alkyl chain can be replaced by other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferred.

Cycloalkyl - as used herein includes cyclic alkyl groups. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1- Adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Additionally, cycloalkyl groups may be optionally substituted. Carbons in the ring can be replaced by other heteroatoms.

Alkenyl - as used herein, encompasses straight and branched chain alkene groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 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 and 3-phenyl-1-butenyl. Additionally, alkenyl groups may be optionally substituted.

Alkynyl - as used herein, encompasses straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Additionally, alkynyl groups may be optionally substituted.

苝和薁，优选苯基，联苯，三联苯，三亚苯，芴和萘。另外，芳基可以任选被取代。非稠合芳基的例子包括苯基，联苯-2-基，联苯-3-基，联苯-4-基，对三联苯-4-基，对三联苯-3-基，对三联苯-2-基，间三联苯-4-基，间三联苯-3-基，间三联苯-2-基，邻甲苯基，间甲苯基，对甲苯基，对-(2-苯基丙基)苯基，4'-甲基联二苯基，4”-叔丁基-对三联苯-4-基，邻-枯基，间-枯基，对-枯基，2,3-二甲苯基，3,4-二甲苯基，2,5-二甲苯基，均三甲苯基和间四联苯基。Aryl or aromatic - as used herein, both non-fused and fused systems are contemplated. Preferred aryl groups are those containing 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, hydrazine, phenanthrene, fluorene, pyrene,

Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Additionally, aryl groups may be optionally substituted. 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 Phen-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropane) base) phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-diphenyl Tolyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-tetraphenyl.

Heterocyclyl or Heterocycle - As used herein, both aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing from 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one heteroatom selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.

Heteroaryl - As used herein, non-fused and fused heteroaromatic groups that can contain from 1 to 5 heteroatoms are contemplated. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridineindole , pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline , quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanobipyridine, benzothienopyridine, thienobipyridine, benzene Selenophenopyridine, selenobenzobipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1 , 2-Azaborane, 1,3-Azaborane, 1,4-Azaborane, borazoles and their aza analogs. Additionally, heteroaryl groups may be optionally substituted.

Alkoxy-represented by -O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.

Aryloxy- is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of the aryl group and the heteroaryl group are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include phenoxy and biphenyloxy.

Aralkyl - as used herein, an alkyl group having an aryl substituent. Additionally, aralkyl groups may be optionally substituted. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl base, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1- Beta-naphthyl-ethyl, 2-beta-naphthyl-ethyl, 1-beta-naphthylisopropyl, 2-beta-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, 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, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2- Phenyl isopropyl.

The term "aza" in azadibenzofuran, aza-dibenzothiophene, etc. refers to the replacement of one or more C-H groups in the corresponding aromatic moiety with a nitrogen atom. For example, azatriphenylenes include dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily occur to those of ordinary skill in the art, and all such analogs are intended to be included in the terminology described herein.

In this disclosure, unless otherwise defined, when using any term from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkane Oxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amine, substituted acyl, substituted carbonyl , substituted carboxylic acid group, substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphino group, refers to alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryl Any of oxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amine, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups The group may be one or more selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted cycloalkyl having 1-20 carbon atoms Heteroalkyl groups of carbon atoms, unsubstituted aralkyl groups of 7-30 carbon atoms, unsubstituted alkoxy groups of 1-20 carbon atoms, unsubstituted alkoxy groups of 6-30 carbon atoms Aryloxy, unsubstituted alkenyl with 2-20 carbon atoms, unsubstituted aryl group with 6-30 carbon atoms, unsubstituted heteroaryl group with 3-30 carbon atoms, unsubstituted Alkylsilyl groups with 3-20 carbon atoms, unsubstituted arylsilyl groups with 6-20 carbon atoms, unsubstituted amine groups with 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, Ester group, nitrile group, isonitrile group, mercapto group, sulfinyl group, sulfonyl group, phosphino group and combinations thereof.

It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, it may be based on whether it is a fragment (eg, phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a The entire molecule (eg, benzene, naphthalene, dibenzofuran) to write its name. As used herein, these various ways of specifying substituents or linking fragments are considered equivalent.

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

In the compounds referred to in this disclosure, multiple substitution refers to a range including double substitution up to the maximum available substitution. When a certain substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may exist in multiple available substitution positions on its connecting structure , the substituents present in multiple available substitution positions may have the same structure or different structures.

In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be connected to form a ring unless explicitly defined, eg, adjacent substituents can be optionally connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the case where adjacent substituents can be connected to form a ring, and the case where adjacent substituents are not connected to form a ring . When adjacent substituents can be optionally linked to form a ring, the formed ring may be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In this expression, adjacent substituents may refer to substituents that are bonded to the same atom, to carbon atoms that are directly bonded to each other, or to carbon atoms that are further distant. base. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.

The statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the formula:

The statement that adjacent substituents can be optionally joined to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are joined to each other by a chemical bond to form a ring, which can be exemplified by the formula:

Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second Substituents are bonded at positions to which hydrogen atoms are bonded, thereby forming a ring. This is exemplified by:

According to one embodiment of the present invention, a compound is disclosed, which has the structure of H-L-E,

where H has the structure represented by Equation 1:

wherein, in formula 1, each occurrence of A ₁ , A ₂ and A ₃ is identically or differently selected from N or CR, and each occurrence of Ring A, Ring B and Ring C is identically or differently selected from having 5- A carbocyclic ring of 18 carbon atoms, or a heterocyclic ring of 3-18 carbon atoms;

Each occurrence of R _x represents, identically or differently, monosubstitution, polysubstitution, or no substitution;

where E has the structure represented by Equation 2:

Wherein, in formula 2, any two of Y ₁ to Y ₄ are selected from N, the other two are independently selected from CR _y , and Y ₅ to Y ₈ are each independently selected from N, C or CR _y ;

L is selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;

wherein _R , Rx and _Ry at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amine group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Wherein, adjacent substituents R, R _X can be optionally connected to form a ring;

Among them, adjacent substituents R _y can be optionally connected to form a ring.

In this embodiment, "*" in Formula 1 represents the position where the structure represented by Formula 1 is connected to the L; "*" in Formula 2 represents the position where the structure represented by Formula 2 is connected to the L.

As used herein, adjacent substituents R, R _X can be optionally joined to form a ring, and is intended to mean between adjacent substituents, for example, between two Rs, between two Rx, _R and R Between _X , it can be optionally connected to form a ring. Obviously, none of these substituents may be connected to form a ring.

Herein, adjacent substituents R _y can be optionally connected to form a ring, and it is intended to mean that any two adjacent R _y can be connected to form a ring. Obviously, adjacent R _y may not be connected to form a ring.

According to an embodiment of the present invention, wherein, in formula 1, said ring A, ring B and ring C are identically or differently selected from 5-membered carbocyclic rings, aromatic rings having 6-18 carbon atoms each time they appear. ring, or a heteroaromatic ring having 3-18 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 1, the ring A, ring B and ring C are identically or differently selected from a 5-membered carbocyclic ring, a benzene ring, and a 5-membered heteroaromatic ring each time they appear, or a 6-membered heteroaromatic ring.

According to an embodiment of the present invention, wherein, the H has a structure represented by formula 1-a:

wherein each occurrence of A ₁ to A ₃ is identically or differently selected from N or CR, and each occurrence of X ₁ to X ₁₀ is identically or differently selected from N or CR _x ;

wherein R, _Rx are selected identically or differently for each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3 -Cycloalkyl with 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted Aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted Arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted amine groups with 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, Sulfinyl, sulfonyl, phosphino, and combinations thereof;

Wherein, adjacent substituents R, _Rx can be optionally connected to form a ring.

In this embodiment, "*" in Formula 1-a represents a position where the structure represented by Formula 1-a is connected to the L.

In this embodiment, adjacent substituents R, Rx can be optionally connected to form a ring, which _is intended to mean that adjacent substituents R can be optionally connected to form a ring, and it is also intended to represent X ₁ to X ₃ Adjacent substituents R _x can be optionally connected to form a ring, and it is also intended to represent that adjacent substituents R _x in X ₄ to X ₆ can be optionally connected to form a ring, and it is also intended to represent X ₇ to X ₁₀ Adjacent substituents R _x can be optionally connected to form a ring, and, also, it is intended to mean that adjacent substituents R _x , R and R _x can be optionally connected to form a ring, for example between A ₁ and X ₃ , And/or between A ₃ and X ₁₀ , and/or between X ₆ and X ₇ can be optionally connected to form a ring; obviously, for those skilled in the art, adjacent substituents R, R _x also Can not be connected to form a ring, in this case, adjacent substituents R are not connected to form a ring, and/or adjacent substituents R _x are not connected to form a ring, and/or adjacent substituents R and R _x are not connected either. connected to form a ring.

According to an embodiment of the invention, wherein each occurrence of R, Rx _is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkanes having 1-20 carbon atoms radicals, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 6-30 carbon atoms Aryloxy, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted hetero group with 3-30 carbon atoms Aryl groups, substituted or unsubstituted amine groups having 0-20 carbon atoms, cyano groups, isocyano groups, mercapto groups, and combinations thereof;

Wherein, adjacent substituents R, _Rx can be optionally connected to form a ring.

In this embodiment, adjacent substituents R, Rx can be optionally connected to form a ring, which _is intended to mean that adjacent substituents R can be optionally connected to form a ring, and it is also intended to represent X ₁ to X ₃ Adjacent substituents R _x can be optionally connected to form a ring, and it is also intended to represent that adjacent substituents R _x in X ₄ to X ₆ can be optionally connected to form a ring, and it is also intended to represent X ₇ to X ₁₀ Adjacent substituents R _x can be optionally connected to form a ring, and, also, it is intended to mean that adjacent substituents R _x , R and R _x can be optionally connected to form a ring, for example between A ₁ and X ₃ , And/or between A ₃ and X ₁₀ , and/or between X ₆ and X ₇ can be optionally connected to form a ring; obviously, for those skilled in the art, adjacent substituents R, R _x also Can not be connected to form a ring, in this case, adjacent substituents R are not connected to form a ring, and/or adjacent substituents R _x are not connected to form a ring, and/or adjacent substituents R and R _x are not connected either. connected to form a ring.

According to an embodiment of the present invention, wherein in the formula 1-a, at least one of R and Rx _is selected from deuterium, substituted or unsubstituted aryl group having 6-30 carbon atoms, or substituted or unsubstituted aryl group of heteroaryl groups having 3-30 carbon atoms.

According to an embodiment of the present invention, in the formula 1-a, at least one of R and R _x is selected from deuterium, phenyl, biphenyl, or pyridyl.

According to an embodiment of the present invention, wherein in the formula 1-a, the adjacent substituents R between A ₁ to A ₃ , the adjacent substituents R _x between X ₁ to X ₃ , and X ₄ to The adjacent substituents R _x between X ₆ and the adjacent substituents R _x between X ₇ to X ₁₀ , at least one group of these adjacent substituent groups is connected to form a ring.

In this embodiment, at least one group of adjacent substituent groups is connected to form a ring, which is intended to indicate that for adjacent substituent groups present in formula 1-a, for example, two of A ₁ and A ₂ adjacent substituents R, two adjacent substituents R in A ₂ and A ₃ , two adjacent substituents R _x in X ₁ and X ₂ , two adjacent substituents in X ₂ and X ₃ Substituents R x , two adjacent substituents R _x in X ₄ and X ₅ , two adjacent substituents R _x in X ₅ and X ₆ , two adjacent substituents in _{X 7} and X ₈ R _x , two adjacent substituent groups R _x in X ₈ and X ₉ , and two adjacent substituent groups R _x in X ₉ and X ₁₀ , at least one group of these substituent groups is connected to form a ring.

According to an embodiment of the present invention, wherein, the H is selected from the group consisting of the following structures:

In this embodiment, "*" represents the position where the structures represented by H-1 to H-130 are connected to the L.

According to an embodiment of the present invention, the hydrogen in the above-mentioned structures of H-1 to H-130 can be partially or completely substituted by deuterium.

According to an embodiment of the present invention, wherein, the E is selected from the structure represented by any one of the group consisting of formula 2-a to formula 2-h:

wherein each occurrence of Y is identically or differently selected from CR _y ;

wherein each occurrence of _Ry is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3-20 cycloalkyl with ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with Alkoxy of 1-20 carbon atoms, substituted or unsubstituted aryloxy of 6-30 carbon atoms, substituted or unsubstituted alkenyl of 2-20 carbon atoms, substituted or unsubstituted with Aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted having Arylsilyl groups of 6-20 carbon atoms, substituted or unsubstituted amine groups of 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups Acyl, sulfonyl, phosphino, and combinations thereof;

Among them, adjacent substituents R _y can be optionally connected to form a ring.

In this embodiment, "*" represents the position where the structures represented by Formula 2-a to Formula 2-h are connected to the L.

In this embodiment, adjacent substituents R can be optionally connected to form a ring, which is intended to mean that when there are multiple R _y , any two adjacent R _y can be connected to form a ring. Obviously, when there are multiple _Ry 's, none of them may be connected to form a ring.

According to an embodiment of the present invention, wherein, in the structures represented by Formula 2-a to Formula 2-h, Y is selected from CR _y identically or differently each time it occurs; R _y is identically or differently selected each time it occurs Selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, cyano, and combinations thereof .

According to an embodiment of the present invention, wherein, in the structures represented by Formula 2-a to Formula 2-h, Y is selected from CR _y identically or differently each time it occurs; R _y is identically or differently selected each time it occurs selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, carbazolyl, pyridyl, Pyrimidyl, 4-cyanophenyl, triphenylene, and combinations thereof.

According to one embodiment of the present invention, in the structures represented by the formulas 2-a to 2-h, Y in the aza six-membered ring is selected from CR _y , and the R _y is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.

According to an embodiment of the present invention, in the structures represented by the formula 2-a to the formula 2-h, Y in the aza six-membered ring is selected from CR _y , and the R _y is selected from phenyl, bi Phenyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9,9-dimethylfluorenyl, pyridine pyrimidinyl, pyrimidinyl or phenylpyridyl.

According to an embodiment of the present invention, wherein, the E is selected from the group consisting of the following structures:

In this embodiment, "*" represents the position where the structures represented by E-1 to E-210 are connected to the L.

According to an embodiment of the present invention, the hydrogen in the structures E-1 to E-210 can be partially or completely substituted by deuterium.

According to an embodiment of the present invention, wherein the L is selected from the group consisting of: single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzophene Furyl, dibenzothienylene, pyridylene, thienylene, and combinations thereof.

According to an embodiment of the present invention, wherein, the L is selected from the group consisting of:

In this embodiment, "*" represents the positions where the structures represented by L-1 to L-26 are connected to the H and E, respectively.

According to an embodiment of the present invention, the hydrogen in the structures of L-1 to L-26 can be partially or completely substituted by deuterium.

According to an embodiment of the present invention, wherein the compound having the structure of H-L-E is selected from the group consisting of compound 1 to compound 1000. The specific structures of the compounds 1 to 1000 refer to claim 12 .

According to an embodiment of the present invention, the hydrogen in the structures of Compound 1 to Compound 1000 can be partially or completely substituted by deuterium.

According to an embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

anode,

cathode,

and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of H-L-E;

where H has the structure represented by Equation 1:

wherein, in formula 1, each occurrence of A ₁ , A ₂ and A ₃ is identically or differently selected from N or CR, and each occurrence of Ring A, Ring B and Ring C is identically or differently selected from having 5- A carbocyclic ring of 18 carbon atoms, or a heterocyclic ring of 3-18 carbon atoms;

Each occurrence of R _x represents, identically or differently, monosubstitution, polysubstitution, or no substitution;

where E has the structure represented by Equation 2:

Wherein, in formula 2, any two of Y ₁ to Y ₄ are selected from N, the other two are independently selected from CR _y , and Y ₅ to Y ₈ are each independently selected from N, C or CR _y ;

L is selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof;

wherein _R , Rx and _Ry at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amine group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Wherein, adjacent substituents R, R _X can be optionally connected to form a ring;

Among them, adjacent substituents R _y can be optionally connected to form a ring.

In this embodiment, "*" in Formula 1 represents the position where the structure represented by Formula 1 is connected to the L; "*" in Formula 2 represents the position where the structure represented by Formula 2 is connected to the L.

According to an embodiment of the present invention, in the device, the organic layer is a light-emitting layer, and the compound is a host material.

According to an embodiment of the present invention, in the device, the light-emitting layer further comprises at least one phosphorescent light-emitting material.

According to an embodiment of the present invention, in the device, the phosphorescent light-emitting material is a metal complex, the metal complex includes at least one ligand, and the ligand includes any one of the following structures:

in,

Each occurrence of R _a , R _b and R _c , identically or differently, denote monosubstitution, polysubstitution, or no substitution;

Each occurrence of X _b is identically or differently selected from the group consisting of O, S, Se, NR _N1 , CR _C1 R _C2 ;

Each occurrence of _Xc and _Xd is identically or differently selected from the group consisting of: O, S, Se, NR _N2 ;

R _a , R _b , R _c , R _N1 , R _N2 , R _C1 , and R _C2 at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1- Alkyl of 20 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, substituted or unsubstituted of 7 -Aralkyl having 30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted Alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted having Alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6-20 carbon atoms, substituted or unsubstituted amine groups of 0-20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups Acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

In the ligand structure, adjacent substituents can optionally be linked to form a ring.

In this embodiment, adjacent substituents can be optionally connected to form a ring, and are intended to represent groups of adjacent substituents in which, for example, between two substituents R _a , between two substituents R _b , Between two substituents R _c , between substituents R _a and R _b , between substituents R _a and R _c , between substituents R _b and R _c , between substituents R _a and R _N1 , substituted between 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 , substituted Between the radicals R _a and R _N2 , between the substituents R _b and R _N2 , and between R _C1 and R _C2 , any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to form a ring.

According to an embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand, and the ligand has the following structure:

wherein R ₁ to R ₇ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3-20 rings Cycloalkyl of carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with 1- Alkoxy of 20 carbon atoms, substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 carbon atoms, substituted or unsubstituted with 6- Aryl having 30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted having 6- Arylsilyl groups of 20 carbon atoms, substituted or unsubstituted amine groups of 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, Sulfonyl, phosphino, and combinations thereof.

According to an embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand, and the ligand has the following structure:

Wherein, at least one of R ₁ -R ₃ is selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted alkyl groups with 1-20 carbon atoms Unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof; and/or at least one of R ₄ -R ₆ is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof.

According to an embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand, and the ligand has the following structure:

wherein, at least two of R ₁ -R ₃ in each occurrence are identically or differently selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted alkyl groups having 3-20 ring carbon atoms atomic cycloalkyl, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or a combination thereof _; and/or at least two of R4 _- R6 at each occurrence are identically or differently selected from 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 , or a combination thereof.

According to an embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand, and the ligand has the following structure:

wherein, at least two of R ₁ -R ₃ in each occurrence are identically or differently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted alkyl groups having 3-20 ring carbon atoms atomic cycloalkyl, substituted or unsubstituted heteroalkyl having 2 to 20 carbon atoms, or a combination thereof _; and/or at least two of R4 _- R6 at each occurrence are identically or differently selected from Substituted or unsubstituted alkyl having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 2-20 carbon atoms , or a combination thereof.

According to an embodiment of the present invention, in the device, the phosphorescent light-emitting material is an Ir, Pt or Os complex.

According to an embodiment of the present invention, in the device, the phosphorescent light-emitting material is an Ir complex and has a structure of Ir(L _a )(L _b )(L _c );

wherein, each occurrence of _La , _Lb , and _Lc is identically or differently selected from any one of the group consisting of:

in,

Each occurrence of R _a , R _b and R _c , identically or differently, denote monosubstitution, polysubstitution, or no substitution;

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

Each occurrence of X _c and X _d is identically or differently selected from the group consisting of O, S, Se and NR _N2 ;

R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 7- Aralkyl having 30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted having Alkenyl groups of 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted aryl groups of 3-30 carbon atoms -Alkylsilyl groups of 20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6 to 20 carbon atoms, substituted or unsubstituted amine groups of 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acids group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

In the ligand structure, adjacent substituents can optionally be linked to form a ring.

In this embodiment, adjacent substituents can be optionally connected to form a ring, and are intended to represent groups of adjacent substituents in which, for example, between two substituents R _a , between two substituents R _b , Between two substituents R _c , between substituents R _a and R _b , between substituents R _a and R _c , between substituents R _b and R _c , between substituents R _a and R _N1 , substituted between 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 , substituted Between the radicals R _a and R _N2 , between the substituents R _b and R _N2 , and between R _C1 and R _C2 , any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to form a ring.

According to one embodiment of the present invention, in the device, wherein the Ir complex is selected from the group consisting of the following structures:

wherein each occurrence of X _f is identically or differently selected from the group consisting of O, S, Se, NR _N3 and CR _C3 R _C4 ;

wherein each occurrence of X _e is identically or differently selected from CR _d or N;

Each occurrence of _Ra , _Rb , and _Rc , identically or differently, denote monosubstitution, polysubstitution, or no substitution;

R _a , R _b , R _c , R _d , R _N3 , R _C3 and R _C4 at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 7- Aralkyl of 30 carbon atoms, substituted or unsubstituted alkoxy of 1 to 20 carbon atoms, substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, substituted or unsubstituted with 2 -Alkenyl groups of 20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted aryl groups of 3- Alkylsilyl groups of 20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6 to 20 carbon atoms, substituted or unsubstituted amine groups of 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups , ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

According to another embodiment of the present invention, a compound formulation is also disclosed, which comprises a compound of H-L-E structure. The specific structure of the compound is shown in any of the preceding examples.

According to another embodiment of the present invention, a display assembly is also disclosed, which includes the electroluminescent device described in any one of the above embodiments.

Combine with other materials

The materials described herein for particular layers in organic light emitting devices can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in US Patent Application US2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or referred to therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one skilled in the art can readily consult the literature to identify other materials that can be used in combination.

Materials described herein as useful in particular layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in conjunction with a variety of hosts, light emitting dopants, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in US patent application US2015/0349273A1 at paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referred to therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one skilled in the art can readily consult the literature to identify other materials that can be used in combination.

In the examples of material synthesis, all reactions were carried out under nitrogen protection unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. Synthesis products were synthesized using one or more equipment conventional in the art (including but not limited to Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatography, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential Scanning calorimeter, fluorescence spectrophotometer of Shanghai Prism Technology, electrochemical workstation of Wuhan Kesite, sublimation instrument of Anhui Beyike, etc.), the structure confirmation and characteristic test were carried out by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device also use conventional equipment in the field (including but not limited to the evaporation machine produced by Angstrom Engineering, the optical test system and life test system produced by Suzhou Fushida, and the ellipsometry produced by Beijing Liangtuo). Instrument, etc.), to be tested by methods well known to those skilled in the art. Since those skilled in the art are aware of the above-mentioned equipment usage, testing methods and other related contents, and can obtain the inherent data of the sample with certainty and without being affected, the above-mentioned related contents will not be repeated in this patent.

Material synthesis example:

The preparation method of the compound of the present invention is not limited, typically but not limitedly, the following compounds are exemplified, and its synthetic route and preparation method are as follows:

Synthesis Example 1: Synthesis of Compound 2

Step 1: Synthesis of Intermediate 1

2-Bromo-3-chloronitrobenzene (100 g, 425.5 mmol), 2-aminobenzeneboronic acid pinacol ester (102 g, 468.1 mmol), tetrakistriphenylphosphine palladium (4.9 g, 4.25 mmol) were mixed under nitrogen protection , potassium carbonate (115 g, 852 mmol), toluene (1000 mL), water (200 mL) and ethanol (200 mL) were added to a three-necked flask, and the reaction was carried out at 100° C. for 48 h. After the reaction was completed, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA=4:1) Intermediate 1 (90 g, yield: 85%) was obtained as a yellow oil.

Step 2: Synthesis of Intermediate 2

Intermediate 1 (90g, 363mmol) and acetonitrile (1000mL) were respectively placed in a there-necked flask, p-toluenesulfonic acid (193.2g, 1088mmol) was added in batches at 0°C and stirred for 30min. Aqueous solution of a mixture of sodium nitrate (69 g, 726 mmol) and potassium iodide (150.6 g, 907 mmol). After the dropwise addition, the temperature was slowly raised to room temperature, and the reaction was carried out for 12 h. After the completion of the reaction, a saturated aqueous solution of sodium thiosulfate was added dropwise to quench the reaction, the reaction solution was concentrated, diluted with water, the mixed solution was extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and the mixture was subjected to column Chromatography (PE/DCM=10/1) gave Intermediate 2 as a yellow solid (85 g, yield: 65%).

Step 3: Synthesis of Intermediate 4

Under nitrogen protection, intermediate 2 (20 g, 55.7 mmol), intermediate 3 (24.5 g, 83.6 mmol), tetrakistriphenylphosphine palladium (1.9 g, 1.67 mmol), potassium carbonate (15.4 g, 111.4 mmol), tetrahydrofuran were mixed (500 mL), water (100 mL), and ethanol (100 mL) were added to the three-necked flask, and the reaction was carried out at 70° C. for 48 h. After the reaction was completed, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA=4:1) Intermediate 4 (12 g, yield: 55%) was obtained as a yellow solid.

Step 4: Synthesis of Intermediate 5

Intermediate 4 (12 g, 30.15 mmol), palladium acetate (338 mg, 1.5 mmol), tri-tert-butylphosphine (606 mg, 3.0 mmol), cesium carbonate (20 g, 60.3 mmol) and xylene (230 mL) were added under nitrogen protection In a three-necked flask, the reaction was carried out at 140 °C for 10 h. After the reaction was completed, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA=6:1) Intermediate 5 (9 g, yield: 80%) was obtained as a yellow solid.

Step 5: Synthesis of Intermediate 6

Under nitrogen protection, intermediate 5 (9 g, 24.9 mmol), triphenylphosphine (19.6 g, 74.7 mmol), o-dichlorobenzene (o-DCB) (100 mL) were added to a three-necked flask and reacted at 200° C. for 12 h. After the reaction was completed, the solvent was removed by concentration, and the crude product was separated by column chromatography to obtain Intermediate 6 (7 g, yield: 85%) as a yellow solid.

Step 6: Synthesis of Compound 2

Under nitrogen protection, intermediate 7 (3.2 g, 10 mmol), intermediate 6 (3 g, 9.1 mmol), palladium acetate (101.9 mg, 0.46 mmol), tri-tert-butylphosphine tetrafluoroborate (266.8 mg, 0.92 mmol) sodium tert-butoxide (1.7 g, 18.2 mmol) and xylene (100 mL) were added to a three-necked flask, and the reaction was carried out at 140° C. overnight. It was cooled to room temperature, then distilled water was added, the mixture was extracted with dichloromethane, the solvent was removed from the organic phase, and the residue was purified by column chromatography (PE/DCM=1:1) to obtain compound 2 (4.0 g, yield: 73%) as a yellow solid ), the product was confirmed to be the target product with a molecular weight of 610.2.

Synthesis Example 2: Synthesis of Compound 70

Under nitrogen protection, intermediate 6 (3 g, 9.1 mmol), intermediate 8 (3.2 g, 9.1 mmol), palladium acetate (101.9 mg, 0.46 mmol), Sphos (369 mg, 0.9 mmol), cesium carbonate (5.9 g, 60.3 mmol) and xylene (100ml) were added into a three-necked flask, and the reaction was carried out at 120° C. for 16h. After the reaction was completed, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA=6:1) A yellow solid compound 70 was obtained (2.9 g, yield: 53%), and the product was confirmed to be the target product with a molecular weight of 610.2.

Those skilled in the art should know that the above preparation method is just an exemplary example, and those skilled in the art can improve it to obtain other compound structures of the present invention.

Device Embodiment

Device Example 1

的速率通过热真空依次在ITO阳极上进行蒸镀。化合物HI用作空穴注入层(HIL)，厚度为

化合物HT用作空穴传输层(HTL)，厚度为

化合物EB用作电子阻挡层(EBL)，厚度为

然后将作为主体的本发明化合物2和作为掺杂剂的化合物RD，共蒸镀用作发光层(EML)，厚度为

使用化合物HB作为空穴阻挡层(HBL)，厚度为

在空穴阻挡层上，化合物ET和8-羟基喹啉-锂(Liq)共蒸镀作为电子传输层(ETL)，厚度为

最后，蒸镀

厚度的8-羟基喹啉-锂(Liq)作为电子注入层(EIL)，并且蒸镀

的铝作为阴极。然后将该器件转移回手套箱，并用玻璃盖封装以完成该器件。First, a glass substrate with a 120 nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After processing, the substrates were dried in a nitrogen-filled glove box to remove moisture, and then mounted on substrate holders and loaded into a vacuum chamber. The organic layers specified below, under vacuum of approximately 10 ^-8 Torr

The rate of evaporation was sequentially performed on the ITO anode by thermal vacuum. Compound HI is used as a hole injection layer (HIL) with a thickness of

Compound HT is used as a hole transport layer (HTL) with a thickness of

Compound EB is used as an electron blocking layer (EBL) with a thickness of

The compound 2 of the present invention as the host and the compound RD as the dopant were then co-evaporated to serve as an emissive layer (EML) with a thickness of

Compound HB is used as hole blocking layer (HBL) with a thickness of

On the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as the electron transport layer (ETL) with a thickness of

Finally, evaporation

thickness of 8-hydroxyquinoline-lithium (Liq) as electron injection layer (EIL), and evaporated

of aluminum as the cathode. The device was then transferred back to the glove box and sealed with a glass lid to complete the device.

Device Example 2

Device Example 2 was implemented in the same manner as Device Example 1, except that the inventive compound 70 was used as the host in the emissive layer (EML) instead of the inventive compound 2.

Device Comparative Example 1

Device Comparative Example 1 was implemented in the same manner as Device Example 1, except that Compound A was used instead of Compound 2 of the present invention as the host in the emissive layer (EML).

The detailed device layer structures and thicknesses are shown in the table below. Layers in which more than one material is used are obtained by doping with different compounds in their stated weight ratios.

Table 1 Device structures of device examples and comparative examples

The material structure used in the device is shown below:

Table 2 lists the measured current efficiency (CE), driving voltage (V), maximum wavelength (λ _max ) and external quantum efficiency (EQE) at 15 mA/cm ² .

Table 2 Device Data

discuss:

As shown in Table 2, the maximum wavelengths of the two Examples and Comparative Examples remained substantially unchanged. The EQE of Example 1 measured at a current density of 15 mA/cm ² was 23.8%, which was 5% higher than the EQE (18.8%) of Comparative Example 1, and the improvement range reached 26.6%; CE (19) of Example 1 was compared with The CE (15) of Example 1 is improved by 26.7%; the driving voltage (3.6V) of Example 1 is reduced by 10% compared with the driving voltage (4.0) of Comparative Example 1; the EQE of Example 2 is 20.4% Compared with the EQE (18.8%) of Comparative Example 1, the improvement is 1.6%, and the improvement rate reaches 8.5%; the CE (16) of Example 2 is increased by 6.7% compared with the CE (15) of Comparative Example 1; the driving voltage of Example 2 ( 3.2V) is 20% lower than the driving voltage (4.0V) of Comparative Example 1; the data show that the example has more excellent device performance, that is, it has hole transport formed by indole and pyrrole fused azamacrocycle unit, and the compound of the present invention bound to the specific ring of the electron transport unit of quinoxaline, quinazoline and similar structures is more than the compound A bound to the 2-position of the quinazoline electron transport unit, due to the electron transport unit bond The special selection of the combined position has better stability of electron transport, which can make the hole transport and electron transport in the light-emitting layer reach a more balanced state, so the device can obtain a lower driving voltage. At the same time, the device efficiency is significantly improved, and the device performance is significantly improved. The unique advantages possessed by the compounds of the present invention are demonstrated.

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

Claims (20)

1. A compound having the structure of H-L-E, where H has the structure represented by Equation 1:

wherein, in formula 1, each occurrence of A ₁ , A ₂ and A ₃ is identically or differently selected from N or CR, and each occurrence of Ring A, Ring B and Ring C is identically or differently selected from having 5- A carbocyclic ring of 18 carbon atoms, or a heterocyclic ring of 3-18 carbon atoms; Each occurrence of R _x represents, identically or differently, monosubstitution, polysubstitution, or no substitution; where E has the structure represented by Equation 2:

Wherein, in formula 2, any two of Y ₁ to Y ₄ are selected from N, and the other two are independently selected from CR _y ; Y ₅ to Y ₈ are each independently selected from N, C or CR _y ; L is selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof; wherein _R , Rx and _Ry at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amine group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Wherein, adjacent substituents R, R _X can be optionally connected to form a ring; Among them, adjacent substituents R _y can be optionally connected to form a ring. 2. The compound of claim 1, wherein each occurrence of said Ring A, Ring B and Ring C is identically or differently selected from a 5-membered carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or Heteroaromatic rings having 3-18 carbon atoms; Preferably, each occurrence of said Ring A, Ring B and Ring C is identically or differently selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring. 3. The compound of claim 2, wherein the H has the structure represented by formula 1-a:

wherein each occurrence of A ₁ to A ₃ is identically or differently selected from N or CR, and each occurrence of X ₁ to X ₁₀ is identically or differently selected from N or CR _x ; wherein R, _Rx are selected identically or differently for each occurrence from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3 -Cycloalkyl with 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted Aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted Arylsilyl groups with 6-20 carbon atoms, substituted or unsubstituted amine groups with 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, Sulfinyl, sulfonyl, phosphino, and combinations thereof; Wherein, adjacent substituents R, _Rx can be optionally connected to form a ring. 4. The compound of claim 3, wherein R, R _x each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1-20 carbon atoms Heteroalkyl, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted having 6-30 carbon atoms Atom aryloxy, substituted or unsubstituted alkenyl with 2-20 carbon atoms, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted with 3-30 carbon atoms Heteroaryl groups, substituted or unsubstituted amine groups with 0-20 carbon atoms, cyano groups, isocyano groups, mercapto groups, and combinations thereof; Wherein, adjacent substituents R, _Rx can be optionally connected to form a ring. 5. The compound of claim 3 or 4, wherein at least one of R and Rx _is selected from deuterium, a substituted or unsubstituted aryl group with 6-30 carbon atoms, or a substituted or unsubstituted aryl group with 6-30 carbon atoms. Heteroaryl groups of 3-30 carbon atoms; Preferably, at least one of R and Rx _is selected from deuterium, phenyl, biphenyl, or pyridyl. 6. The compound according to claim 3 or 4, wherein, the adjacent substituent R between A ₁ to A ₃ , the adjacent substituent R _x between X ₁ to X ₃ , and X ₄ to X ₆ Between the adjacent substituents R _x , and the adjacent substituents R _x between X ₇ to X ₁₀ , at least one group of these adjacent substituent groups is connected to form a ring. 7. The compound of any one of claims 1 to 6, wherein the H is selected from the group consisting of:

Wherein, optionally, the hydrogen in the above structure can be partially or completely replaced by deuterium. 8. The compound of any one of claims 1 to 7, wherein the E is selected from the structure represented by any one of the group consisting of formula 2-a to formula 2-h:

wherein each occurrence of Y is identically or differently selected from CR _y ; wherein each occurrence of _Ry is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3-20 cycloalkyl with ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with Alkoxy of 1-20 carbon atoms, substituted or unsubstituted aryloxy of 6-30 carbon atoms, substituted or unsubstituted alkenyl of 2-20 carbon atoms, substituted or unsubstituted with Aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted having Arylsilyl groups of 6-20 carbon atoms, substituted or unsubstituted amine groups of 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups Acyl, sulfonyl, phosphino, and combinations thereof; wherein, adjacent substituents R _y can be optionally connected to form a ring; Preferably, each occurrence of _Ry is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted having 3-30 carbon atoms Heteroaryl groups of carbon atoms, cyano groups, and combinations thereof; More preferably, each occurrence of R _y is identically or differently selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, 9,9 - Dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, triphenylene, and combinations thereof. 9. The compound of claim 8, wherein in the structures represented by the formulas 2-a to 2-h, Y in the aza six-membered ring is selected from CR _y , and R _y is selected from substituted or unsubstituted aryl groups with 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms; Preferably, the R _y is selected from phenyl, biphenyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazole , 9,9-dimethylfluorenyl, pyridyl, pyrimidinyl or phenylpyridyl. 10. The compound of claim 8 or 9, wherein the E is selected from the group consisting of:

Wherein, optionally, the hydrogen in the above structure can be partially or completely replaced by deuterium. 11. The compound of any one of claims 1 to 10, wherein the L is selected from the group consisting of: single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothienylene, pyridylene, thienylene, and combinations thereof; Preferably, the L is selected from the group consisting of:

Wherein, optionally, the hydrogen in the structures of L-1 to L-26 can be partially or completely substituted by deuterium. 12. The compound of claim 11, wherein the compound is selected from the group consisting of compounds 1 to 1000, the compounds 1 to 1000 have the structure of H-L-E, wherein H, L and E are respectively selected from the following table. structure:

Wherein, optionally, the hydrogen in the structure of the above compound can be partially or completely substituted by deuterium. 13. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having an H-L-E structure; where H has the structure represented by Equation 1:

wherein, in formula 1, each occurrence of A ₁ , A ₂ and A ₃ is identically or differently selected from N or CR, and each occurrence of Ring A, Ring B and Ring C is identically or differently selected from having 5- A carbocyclic ring of 18 carbon atoms, or a heterocyclic ring of 3-18 carbon atoms; Each occurrence of R _x represents, identically or differently, monosubstitution, polysubstitution, or no substitution; where E has the structure represented by Equation 2:

Wherein, in formula 2, any two of Y ₁ to Y ₄ are selected from N, and the other two are independently selected from CR _y ; Y ₅ to Y ₈ are each independently selected from N, C or CR _y ; L is selected from a single bond, a substituted or unsubstituted arylene group having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-30 carbon atoms, or a combination thereof; wherein _R , Rx and _Ry at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups of 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted amine group with 0-20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group , mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Wherein, adjacent substituents R, R _X can be optionally connected to form a ring; Among them, adjacent substituents R _y can be optionally connected to form a ring. 14. The electroluminescent device of claim 13, wherein the organic layer is a light-emitting layer and the compound is a host material. 15. The electroluminescent device of claim 14, wherein the light-emitting layer further comprises at least one phosphorescent light-emitting material. 16. The electroluminescent device of claim 15, wherein the phosphorescent light-emitting material is a metal complex comprising at least one ligand comprising the structure of any of the following:

in, Each occurrence of R _a , R _b and R _c , identically or differently, denote monosubstitution, polysubstitution, or no substitution; Each occurrence of X _b is identically or differently selected from the group consisting of O, S, Se, NR _N1 and CR _C1 R _C2 ; Each occurrence of X _c and X _d is identically or differently selected from the group consisting of O, S, Se and NR _N2 ; R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 7- Aralkyl having 30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted having Alkenyl groups of 2-20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted aryl groups of 3-30 carbon atoms -Alkylsilyl groups of 20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6 to 20 carbon atoms, substituted or unsubstituted amine groups of 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acids group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; In the ligand structure, adjacent substituents can optionally be linked to form a ring. 17. The electroluminescent device of claim 15, wherein the phosphorescent light-emitting material is a metal complex comprising at least one ligand having the following structure:

wherein R ₁ to R ₇ are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted having 3-20 rings Cycloalkyl of carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted with 1- Alkoxy of 20 carbon atoms, substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 carbon atoms, substituted or unsubstituted with 6- Aryl having 30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted having 6- Arylsilyl groups of 20 carbon atoms, substituted or unsubstituted amine groups of 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, Sulfonyl, phosphino, and combinations thereof; Preferably, wherein at least one or two of R ₁ -R ₃ are selected from substituted or unsubstituted alkyl groups with 1-20 carbon atoms, substituted or unsubstituted rings with 3-20 ring carbon atoms Alkyl, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, or a combination thereof; and/or at least one or two of R ₄ -R ₆ are selected from substituted or unsubstituted with 1-20 alkyl of 1 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl of 1 to 20 carbon atoms, or a combination thereof; More preferably, at least two of R1 _{- R3} at each occurrence are identically or differently selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted having 3-20 carbon atoms Cycloalkyl of ring carbon atoms, substituted or unsubstituted heteroalkyl of 2 to 20 carbon atoms, or a combination thereof _; and/or at least two of R4 _- R6, the same or different in each occurrence Selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heterocyclic groups having 2-20 carbon atoms alkyl, or a combination thereof. 18. The electroluminescent device of claim 16 or 17, wherein the phosphorescent light-emitting material is an Ir, Pt or Os complex; Preferably, wherein the phosphorescent light-emitting material is an Ir complex and has the structure of Ir(L _a )(L _b )(L _c ); wherein each occurrence of _La , _Lb and _Lc is identically or differently selected from any of the above-mentioned ligands; More preferably, wherein the Ir complex is selected from the group consisting of:

wherein each occurrence of X _f is identically or differently selected from the group consisting of O, S, Se, NR _N3 and CR _C3 R _C4 ; wherein each occurrence of X _e is identically or differently selected from CR _d or N; Each occurrence of _Ra , _Rb , and _Rc , identically or differently, denote monosubstitution, polysubstitution, or no substitution; R _a , R _b , R _c , R _d , R _N3 , R _C3 and R _C4 at each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 7- Aralkyl of 30 carbon atoms, substituted or unsubstituted alkoxy of 1 to 20 carbon atoms, substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, substituted or unsubstituted with 2 -Alkenyl groups of 20 carbon atoms, substituted or unsubstituted aryl groups of 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3-30 carbon atoms, substituted or unsubstituted aryl groups of 3- Alkylsilyl groups of 20 carbon atoms, substituted or unsubstituted arylsilyl groups of 6 to 20 carbon atoms, substituted or unsubstituted amine groups of 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups , ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof. 19. A compound formulation comprising the compound of any one of claims 1-12. 20. A display assembly comprising an electroluminescent device as claimed in any one of claims 13 to 18.

Images