CN113968875A

CN113968875A - Electroluminescent material and device

Info

Publication number: CN113968875A
Application number: CN202010720191.4A
Authority: CN
Inventors: 王乐; 张晗; 王强; 王俊飞; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2020-07-24
Filing date: 2020-07-24
Publication date: 2022-01-25

Abstract

An electroluminescent material and device are disclosed. The electroluminescent material has a structure of H-L-E, is a novel compound formed by connecting indole and pyrrole fused azamacrocycles with azadibenzothiophene, azadibenzofuran, azadibenzoselenophene and similar structures, and can be used as a main body material in an electroluminescent device. The novel compounds can effectively improve the current efficiency and external quantum efficiency of the device and can provide better device performance. An electroluminescent device and compound formulation are also disclosed.

Description

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 formed by connecting indole and pyrrole fused azamacrocycles with azadibenzothiophene, azadibenzofuran, azadibenzoselenophene and similar structures, and an organic electroluminescent device and a compound formula containing the compound.

Background

Organic electronic devices include, but are not limited to, the following classes: 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 plasma light emitting devices.

In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise 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 a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.

OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. 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, which use 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 contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.

Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.

The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.

KR1020150077220A discloses an organic electroluminescent compound, an organic optical compound having the following structure

The general formula compound X disclosed therein₁Can be N (Ar)₁) However, there is no disclosure or teaching of indole fused azamacrocycle building blocks with azabicyclophenes, azabicyclofurans, azabicycloselenophenes andand organic compounds in which structural units having similar structures are connected.

US20180337340a1 discloses an organic electroluminescent compound and an organic electroluminescent device comprising the same, comprising an organic layer comprising one or more hosts, the first host of which is an organic optical compound having the structure:

however, the compounds disclosed therein must have a structural unit of quinazoline or quinoxaline and must be bonded to the 2-position of quinazoline or quinoxaline, and organic compounds in which an indole-fused azamacrocyclic structural unit is linked to a structural unit of azabiphenylthiophene, azabiphenylfuran, azabiphenylselenophene, and the like are not disclosed or taught.

However, there is still room for improvement in the currently reported host materials, and in order to meet the increasing demands of the industry, especially for the requirements of higher device efficiency, longer device lifetime, and lower driving voltage, the new materials still need to be further researched and developed.

Disclosure of Invention

The present invention addresses at least some of the above problems by providing a series of organic compounds having structural units of indole and pyrrole fused azamacrocycles linked to azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, and the like. The compounds are useful as host materials in organic electroluminescent devices. The novel compounds can effectively improve the current efficiency and external quantum efficiency of the device and can provide better device performance.

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

wherein H has a structure represented by formula 1:

in formula 1, A₁、A₂And A₃Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;

R_xthe same or different at each occurrence denotes mono-, poly-or no-substitution;

e has a structure represented by formula 2:

in formula 2, Y₁To Y₈Each independently selected from N, C or CR_yAnd Y is₁To Y₈At least one is selected from N;

z is selected from CR_zR_z，SiR_zR_z，NR_z，BR_z，PR_zO, S or Se; when two R are simultaneously present_zWhen two R are present_zMay be the same or different;

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

wherein R, R_x，R_yAnd R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted having 6 to 20 carbon atomsAn arylsilyl group, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a 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;

wherein H has a structure represented by formula 1:

e has a structure represented by formula 2:

wherein R, R_x，R_yAnd R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

According to one embodiment of the invention, a compound formulation is also disclosed, which comprises the compound having the structure H-L-E.

According to an embodiment of the present invention, there is also disclosed an electronic apparatus including the electroluminescent device including the compound having an H-L-E structure in an organic layer.

The invention discloses a series of organic compounds formed by connecting indole and pyrrole fused azamacrocycles with structural units of azadibenzothiophene, azadibenzofuran, azadibenzoselenophene and similar structures. The compounds are useful as host materials in organic electroluminescent devices. The novel compounds can effectively improve the current efficiency and external quantum efficiency of the device and can provide better device performance.

Drawings

FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.

Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.

Detailed Description

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:1₄TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. 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 U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including cathodes having a metal film such as Mg: AgA composite cathode of a layer and an overlying transparent, conductive, sputter-deposited layer of ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

The above-described hierarchical structure is provided via non-limiting embodiments. The function 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 may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.

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

The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.

Devices manufactured according to 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 such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.

The materials and structures described herein may also be used in other organic electronic devices as previously listed.

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 farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present 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 "photoactive" when it is believed that the ligand directly contributes to the photoactive 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 photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).

On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.

The delayed fluorescence characteristic of type E 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 light emitting material to have a small mono-triplet energy gap (Δ Ε)_S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ E_S-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).

Definitions for substituent terms

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

Alkyl-as used herein, includes both straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.

Cycloalkyl-as used herein, comprises a cyclic alkyl group. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl are preferable. In addition, the cycloalkyl group may be optionally substituted.

Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. In addition, heteroalkyl groups may be optionally substituted.

Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 3-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.

Alkynyl-as used herein, straight chain alkynyl groups are contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,

perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.

Heterocyclyl or heterocyclic-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. In addition, the heterocyclic group may be optionally substituted.

Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothiophene bipyridine, benzothiophene, selenophene bipyridine, selenophene bipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.

Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy groups may be optionally substituted.

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

Aralkyl-as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -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, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable. In addition, the aralkyl group may be optionally substituted.

Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.

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

The term "aza" in azabenzofuran, azabenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.

In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.

In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

In the compounds mentioned in the present disclosure, polysubstitution is meant to encompass disubstituted substitutions up to the maximum range of available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.

In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. 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 expression that adjacent substituents can optionally be linked to form a ring is also intended 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 following formula:

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

further, the expression that adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:

according to one embodiment of the present invention, a compound is disclosed having the structure of H-L-E, wherein H has the structure represented by formula 1:

e has a structure represented by formula 2:

z is selected from CR_zR_z，SiR_zR_z，NR_z，BR_z，PR_zO, S or Se; when two R are simultaneously present_zWhen two R are present_zMay be the same or different; for example, when Z is selected from CR_zR_zWhen two R are present_zMay be the same or different; as another example, when Z is selected from SiR_zR_zWhen two R are present_zMay be the same or different;

adjacent substituents R, R_xCan optionally be linked to form a ring;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

In this example, the adjacent substituents R, R_xCan optionally be linked to form a ring, intended to be represented in the structure of HAdjacent substituent groups, e.g. between adjacent substituents R, adjacent substituents R_xIn the formula (II) and (III) are substituted by R and R_xAny one or more of these substituent groups can be linked to form a ring. Obviously, these substituent groups may not be connected to form a ring.

In this context, adjacent substituents R_y，R_zCan optionally be linked to form a ring, is intended to mean that in the structure of E, adjacent substituent groups, for example, adjacent substituents R_yBetween, adjacent substituents R_zAnd a substituent R_yAnd R_zAny one or more of these substituent groups can be linked to form a ring. Obviously, these substituent groups may not be connected to form a ring.

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

According to one embodiment of the present invention, wherein, in formula 1, the ring a, the ring B and the ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, 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 A is₁To A₃Selected, identically or differently, on each occurrence from N or CR, X₁To X₁₀Selected, identically or differently, on each occurrence from N or CR_x；

R，R_xEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atomsA heterocyclic group of 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring.

In this example, the adjacent substituents R, R_xCan optionally be linked to form a ring, is intended to mean that adjacent substituents R can optionally be linked to form a ring, is also intended to mean X₁To X₃In (B) an adjacent substituent R_xCan optionally be linked to form a ring, is also intended to denote X₄To X₆In (B) an adjacent substituent R_xCan optionally be linked to form a ring, is also intended to denote X₇To X₁₀In (B) an adjacent substituent R_xCan optionally be linked to form a ring, and are also intended to represent adjacent substituents R and R_xCan optionally be joined to form a ring, e.g. A₁And X₃And/or A₃And X₁₀And/or X₆And X₇Can be optionally connected into a ring; it is obvious to the person skilled in the art that the adjacent substituents R, R_xOr may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents R_xNor linked to form a ring, and/or adjacent substituents R and R_xNor are they linked to form a ring.

According to an embodiment of the present invention, wherein, in formula 1-a, R_xEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedAn alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring.

According to one embodiment of the present invention, wherein in said formula 1-a, R and R_xAt least one of which is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to one embodiment of the present invention, wherein in said formula 1-a, R and R_xAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.

According to an embodiment of the present invention, wherein in said formula 1-a, A₁To A₃Adjacent substituents R, X between₁To X₃Adjacent substituent R between_x，X₄To X₆Adjacent substituent R between_xAnd X₇To X₁₀Adjacent substituent R between_xAt least one of these adjacent substituent groups is linked to form a ring.

In this embodiment, at least one of the adjacent substituent groups is linked to form a ring, which is intended to mean that for the adjacent substituent groups present in formula 1-a, for example, A₁And A₂Two adjacent substituents R, A₂And A₃Two adjacent substituents R, X₁And X₂Two adjacent substituents R in_x，X₂And X₃Two adjacent substituents R in_x，X₄And X₅Two adjacent substituents R in_x，X₅And X₆Two adjacent substituents R in_x，X₇And X₈Two adjacent substituents R in_x，X₈And X₉Two adjacent substituents R in_xAnd X₉And X₁₀Two adjacent substituents R in_xAt least one of these substituent groups is linked to form a ring.

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

in the present embodiment, "+" in the structures of H-1 to H-139 denotes a position where the H structure is connected to L.

According to one embodiment of the invention, wherein the hydrogen energy in the structure of H-1 to H-139 is partially or completely substituted with deuterium.

According to one embodiment of the present invention, wherein E has a structure represented by formula 2:

in formula 2, Y₁To Y₈Each independently selected from N, C or CR_yAnd Y is₁To Y₈One or two of which are selected from N;

wherein R is_yAnd R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

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

wherein Y is selected, identically or differently on each occurrence, from C or CR_y；

R_y，R_zeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

According to an embodiment of the present invention, wherein R in the formulas 2-a to 2-l_y，R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof.

According to an embodiment of the present invention, wherein R in the formulas 2-a to 2-l_y，R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.

According to one embodiment of the present invention, wherein in the formulas 2-a to 2-l, Z is selected from O, S or Se.

According to one embodiment of the present invention, wherein in the formulas 2-a to 2-l, Z is selected from O or S.

According to an embodiment of the present invention, wherein in the formulas 2-a to 2-l, Z is S.

According to one embodiment of the invention, wherein, in said formulae 2-a to 2-l, Y is selected, identically or differently on each occurrence, from C or CR_yAt least one Y is selected from CR_yAnd said R is_ySelected from the group consisting of: deuterium, halogen, cyano, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein, in said formulae 2-a to 2-l, Y is selected, identically or differently on each occurrence, from C or CR_yAt least one Y is selected from CR_yAnd R is_ySelected from the group consisting of: deuterium, fluorine, cyano, phenyl, biphenyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, phenylpyridinyl, and combinations thereof.

According to one embodiment of the invention, wherein E is selected from the group consisting of:

in the present embodiment, among the structures of E-1 to E-184

Indicates the position where the E structure is attached to the L.

According to one embodiment of the present invention, wherein the hydrogen in the structures E-1 through E-184 can be partially or fully substituted with deuterium.

According to an embodiment of the invention, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothiophenene, pyridinylene, thiophenylene, and combinations thereof.

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

in the structures of L-1 to L-27And "+" represents the position where the L is connected with the H structure shown in the formula 1,

represents the position where the L is linked to the E structure as shown in formula 2.

According to one embodiment of the present invention, wherein hydrogen in the structure of L-1 to L-27 can be partially or completely substituted with deuterium.

According to one embodiment of the invention, wherein the compound has the structure of H-L-E, and wherein H is selected from any one of the group consisting of H-1 to H-139, L is selected from any one of the group consisting of L-0 to L-27, E is selected from any one of the group consisting of E-1 to E-184; optionally, the hydrogen in the compound can be partially or fully substituted with deuterium.

According to an embodiment of the present invention, wherein the compound is selected from the group consisting of compound 1 to compound 1031, and the specific structures of the compound 1 to compound 1000 are shown in claim 12.

According to an embodiment of the present invention, wherein hydrogen energy in said compounds 1 to 1031 is partially or completely substituted by deuterium.

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

an anode, a cathode, a anode and a cathode,

a cathode electrode, which is provided with 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; wherein H has a structure represented by formula 1:

R_xat each occurrenceIdentically or differently, denotes mono-, poly-or unsubstituted;

e has a structure represented by formula 2:

adjacent substitutionRadical R, R_xCan optionally be linked to form a ring;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

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

According to an embodiment of the present invention, wherein, in the electroluminescent device, the organic layer is a light emitting layer, the light emitting layer further comprises at least one host material, the at least one host material is different from the compound, and the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

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

According to an embodiment of the present invention, wherein, in the electroluminescent device, the phosphorescent light-emitting material is a metal complex having M (L)_a)_m(L_b)_n(L_c)_qA general formula (II) of (I);

wherein M is selected from metals having a relative atomic mass greater than 40;

L_a、L_b、L_ca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l is_a、L_b、L_cOptionally linked to form a multidentate ligand; for example, L_a、L_bAnd L_cAny two of which can be linked to form a tetradentate ligand; also for example, L_a、L_bAnd L_cCan be connected with each other to form a hexadentate ligand; or also for example L_a、L_b、L_cAre all not connected therebyForming a polydentate ligand;

L_a、L_b、L_cmay be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of L_aMay be the same or different; when n is 2, two L_bMay be the same or different;

L_ahas a structure as shown in formula 3:

wherein the content of the first and second substances,

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

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

ring D and ring E via U_aAnd U_bFusing;

U_aand U_bSelected from C or N, identically or differently at each occurrence;

R_d，R_ethe same or different at each occurrence denotes mono-, poly-or unsubstituted;

V₁-V₄selected from CR, identically or differently at each occurrence_vOr N;

R_d，R_e，R_veach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atomsUnsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;

adjacent substituents R_d，R_e，R_vCan be optionally connected to form a ring;

L_b、L_ceach occurrence, identically or differently, is selected from any one of the following structures:

wherein the content of the first and second substances,

R_a，R_band R_cThe same or different at each occurrence represents mono-, poly-, or no substitution;

X_beach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NR_N1And CR_C1R_C2；

X_cAnd X_dEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NR_N2；

R_a，R_b，R_c，R_N1，R_N2，R_C1And R_C2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl having 1 to 20 carbon atomsAn alkoxy group, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

the ligand L_b、L_cIn the structure (1), adjacent substituents R_a，R_b，R_c，R_N1，R_N2，R_C1And R_C2Can optionally be linked to form a ring.

In this context, adjacent substituents R_d，R_e，R_vCan optionally be linked to form a ring, is intended to mean when a substituent R is present_dA substituent R_eA substituent R_vIn which adjacent substituent groups, e.g. adjacent substituent groups R_dAdjacent and adjacent substituents R_eAdjacent and adjacent substituents R_vAdjacent and adjacent substituents R_dAnd R_eAdjacent and adjacent substituents R_dAnd R_vThe substituents R between, and adjacent to_eAnd R_vAny one or more of these adjacent substituent groups can be linked to form a ring. Obviously, when the substituent R is present_dA substituent R_eA substituent R_vIn the case of the above, none of these substituent groups may be linked to form a ring.

In this example, the adjacent substituents R_a，R_b，R_c，R_N1，R_N2，R_C1And R_C2Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents R_aIn between, two substituents R_bIn between, two substituents R_cOf a substituent R_aAnd R_bOf a substituent R_aAnd R_cOf a substituent R_bAnd R_cOf a substituent R_aAnd R_N1Of a substituent R_bAnd R_N1Of a substituent R_aAnd R_C1Of a substituent R_aAnd R_C2Of a substituent R_bAnd R_C1Of a substituent R_bAnd R_C2Of a substituent R_aAnd R_N2Of a substituent R_bAnd R_N2And R is_C1And R_C2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other 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 having M (L)_a)_m(L_b)_nA general formula (II) of (I);

m is selected from metals having a relative atomic mass greater than 40;

L_a、L_ba first ligand and a second ligand coordinated to said M, respectively; l is_a、L_bOptionally linked to form a multidentate ligand;

m is 1,2 or 3; n is 0, 1 or 2; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of L_aMay be the same or different; when n is 2, two L_bMay be the same or different;

L_ahas a structure as shown in formula 3:

wherein the content of the first and second substances,

ring D and ring E via U_aAnd U_bFusing;

U_aand U_bSelected from C or N, identically or differently at each occurrence;

V₁-V₄selected from CR, identically or differently at each occurrence_vOr N;

R_d，R_e，R_veach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

wherein said ligand L_bHas the following structure:

wherein R is₁To R₇Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atomsA heteroalkyl group of a subgroup, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a thio group, sulfinyl, sulfonyl, phosphino, and combinations thereof.

According to one embodiment of the invention, in the device, wherein the ligand L_bHas the following structure:

wherein R is₁-R₃At least one of which is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R₄-R₆At least one of which is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

wherein R is₁-R₃At least two of which, on each occurrence, are selected from the group consisting ofSubstituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or combinations thereof; and/or R₄-R₆At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

wherein R is₁-R₃At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R₄-R₆At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.

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

According to an embodiment of the present invention, the device, wherein the phosphorescent light emitting material is an Ir complex and has Ir (L)_a)(L_b)(L_c)、Ir(L_a)₂(L_b)、Ir(L_a)₂(L_c) Or Ir (L)_a)(L_c)₂Any of the structures shown.

According to another embodiment of the invention, a compound formulation is also disclosed, comprising the compound having the structure H-L-E. The specific structure of the compound is shown in any one of the embodiments.

According to another embodiment of the present invention, there is also disclosed a display assembly comprising the electroluminescent device comprising the compound having the structure of H-L-E in an organic layer.

In combination with other materials

The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Anttrom engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.

Materials synthesis example:

the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:

synthesis example 1: synthesis of Compound 1

Step 1: synthesis of Compound 1

Intermediate 1(2.5g, 7.6mmol), intermediate 2(2.3g, 7.6mmol), DMAP (4-dimethylaminopyridine, 92.7mg, 0.76mmol), cesium carbonate (4.9g, 15.2mmol), DMF (50mL) were charged to a three-necked flask under nitrogen and reacted at 80 ℃ for 16 h. After the completion of the reaction, it was cooled to room temperature, distilled water was added, a solid was obtained by filtration, and the crude product was recrystallized from toluene to obtain Compound 1(3g, yield: 67%) as a yellow solid. The product was identified as the target product, molecular weight 590.2.

Synthesis example 2: synthesis of Compound 42

Step 1: synthesis of Compound 42

Intermediate 1(3.0g, 9.1mmol), intermediate 3(2.7g, 9.1mmol), DMAP (111mg, 0.9mmol), cesium carbonate (5.9g, 18.2mmol), DMSO (100mL) were added to a three-necked flask under nitrogen and reacted at 150 ℃ for 4 h. After the reaction was complete, it was cooled to room temperature, distilled water was added, the solid was filtered and the crude product was purified by column chromatography eluting with PE/DCM3:1 to give compound 42 as a pale yellow solid (1.8g, 55.8% yield). The product was identified as the target product, molecular weight 590.2.

It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.

Device example 1

First, a glass substrate, having an Indium Tin Oxide (ITO) anode 120nm thick, was cleaned and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was dried in a glove box filled with nitrogen gas to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees^-8In the case of Torr

The rate of (a) was successively evaporated on the ITO anode by thermal vacuum. Compound HI was used as a Hole Injection Layer (HIL) with a thickness of

The compound HT is used as Hole Transport Layer (HTL) with a thickness of

Compound EB was used as an Electron Blocking Layer (EBL) with a thickness of

Then, the compound 1 of the present invention as a host and the compound RD as a dopant were co-evaporated to be used as an emission layer (EML) with a thickness of

The compound HB was used as a hole-blocking layer (HBL) with a thickness of

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

Finally, evaporation

8-hydroxyquinoline-lithium (Liq) as an Electron Injection Layer (EIL) in thickness and evaporation deposited

As a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.

Device comparative example 1

Device comparative example 1 was the same as device example 1 except that compound a was used as a host in place of compound 1 of the present invention in the light emitting layer (EML).

The detailed device layer structure and thickness are shown in the table below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.

TABLE 1 device structures of device examples and comparative examples

The material structure used in the device is as follows:

table 2 shows the results at a constant current of 15mA/cm²Under the conditions, the maximum emission wavelength (. lamda.) of the device example 1 and the device comparative example 1 was measured_max) Current Efficiency (CE) and External Quantum Efficiency (EQE).

TABLE 2 device data

Discussion:

as shown in table 2, the maximum wavelength of example 1 and comparative example 1 remained substantially unchanged. At 15mA/cm²The current efficiency (18cd/A) of example 1 measured at the current density was 3cd/A higher than that (15cd/A) of comparative example 1, which was an improvement of 20%. The external quantum efficiency (22.4%) of example 1 was 3.6% higher than that (18.8%) of comparative example 1, which was improved by 19.1%. The data show that the examples have more excellent current efficiency and external quantum efficiency than the comparative examples, that is, the compound of the present invention in which a hole transport unit having an indole and pyrrole fused azamacrocyclic structure is connected to an electron transport unit having an azadibenzothiophene, an azadibenzofuran, an azadibenzoselenophene, or the like has more excellent device performance than the compound a in which a hole transport unit is bonded to a quinazoline. The electron transport unit and the hole transport unit of the aza-dibenzothiophene, the aza-dibenzofuran, the aza-dibenzoselenophene and the similar structures have excellent balance property on charges, so that unexpected excellent device effect is shown, the device can obtain higher current efficiency and external quantum efficiency, and the device performance is obviously improved. The unique advantages of the compounds of the present invention are demonstrated.

It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments 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 present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.

Claims

1. A compound having the structure H-L-E, wherein H has the structure represented by formula 1:

e has a structure represented by formula 2:

in formula 2, Y₁To Y₈Each independently selected from N, C or CR_yAnd Y is₁To Y₈At least one of (a) is selected from N;

wherein R, R_x，R_yAnd R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstitutedSubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 ring atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring;

adjacent substituents R_y，R_zCan optionally be linked to form a ring.

2. The compound of claim 1, wherein said ring a, ring B, and ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms;

preferably, said ring a, ring B and ring C, identically or differently at each occurrence, are 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 1 or 2, wherein the H has a structure represented by formula 1-a:

R，R_xEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring;

preferably, wherein R, R_xEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof.

4. The compound of claim 3, wherein R and R_xAt least one of them is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group havingHeteroaryl having 3 to 30 carbon atoms;

preferably, R and R_xAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.

5. The compound of claim 3 or 4, wherein A is₁To A₃Adjacent substituents R, X between₁To X₃Adjacent substituent R between_x，X₄To X₆Adjacent substituent R between_xAnd X₇To X₁₀Adjacent substituent R between_xAt least one of these adjacent substituent groups is linked to form a ring.

6. The compound of any one of claims 1-5, wherein said H is selected from the group consisting of the following structures:

wherein, optionally, the hydrogen in said structures H-1 to H-139 can be partially or fully substituted with deuterium.

7. The compound of any one of claims 1 to 6, wherein E is selected from the structures represented by any one of the groups consisting of formula 2-a to formula 2-l:

R_y，R_zeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl groupA group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R_y，R_zCan optionally be linked to form a ring;

preferably, R_y，R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano, and combinations thereof;

more preferably, R_y，R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, phenyl, biphenyl, naphthyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridinyl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.

8. The compound of claim 7, wherein in the formulae 2-a to 2-l, Z is selected from O, S or Se; preferably, Z is selected from O or S; more preferably, Z is S.

9. The compound of claim 7 or 8, wherein in the formulae 2-a to 2-l, Y is selected from C or CR, the same or different at each occurrence_yAt least one Y is selected from CR_yAnd said R is_ySelected from the group consisting of: deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

preferably, at least one Y is selected from CR_yAnd said R is_ySelected from the group consisting of: deuterium, fluorine, cyano, phenyl, biphenyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothienyl, triphenyleneA group, carbazolyl group, 9-phenylcarbazolyl group, 9, 9-dimethylfluorenyl group, pyridyl group, pyrimidyl group, terphenyl group, 4-cyanophenyl group, phenylpyridyl group, and combinations thereof.

10. The compound of any one of claims 1-9, wherein E is selected from the group consisting of the following structures:

wherein, optionally, the hydrogen in structures E-1 through E-184 can be partially or fully substituted with deuterium.

11. The compound of any one of claims 1 to 10, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothiophenene, pyridinylene, thiophenylene, and combinations thereof;

preferably, said L is selected from the group consisting of the following structures:

wherein, in the structures of L-1 to L-27, "+" indicates the position where L is connected with the H structure shown in formula 1

Represents the position where the L is connected with the E structure shown in the formula 2;

wherein, optionally, the hydrogen in the structures of L-1 to L-27 can be partially or fully substituted with deuterium.

12. The compound of claims 1 to 11, wherein the compound has the structure of H-L-E, and wherein H is selected from any one of the group consisting of H-1 to H-139, L is selected from any one of the group consisting of L-0 to L-27, E is selected from any one of the group consisting of E-1 to E-184; optionally, the hydrogen in the compound can be partially or fully substituted with deuterium;

preferably, wherein said compound is selected from the group consisting of compound 1 to compound 1031; the compounds 1 to 1031 have the structure H-L-E, wherein H, L and E each correspond to a structure selected from the following table:

wherein, optionally, the hydrogen energy in compound 1 to compound 1031 is partially or fully substituted with deuterium.

13. An electroluminescent device, comprising:

an anode, a cathode, a anode and a cathode,

a cathode electrode, which is provided with a cathode,

e has a structure represented by formula 2:

wherein R, R_x，R_yAnd R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkene having 2 to 20 carbon atomsA group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R, R_xCan optionally be linked to form a ring;

adjacent substituents R_y，R_zCan optionally be linked 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;

preferably, the light emitting layer further comprises at least one host material, the at least one host material being different from the compound, and the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

15. The electroluminescent device of claim 14 wherein said 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 having M (L)_a)_m(L_b)_n(L_c)_qA general formula (II) of (I);

m is selected from metals having a relative atomic mass greater than 40;

L_a、L_b、L_ca first ligand, a second ligand and a third ligand which are respectively coordinated with the M; l is_a、L_b、L_cOptionally linked to form a multidentate ligand;

L_ahas a structure as shown in formula 3:

wherein the content of the first and second substances,

ring D and ring E via U_aAnd U_bFusing;

U_aand U_bSelected from C or N, identically or differently at each occurrence;

V₁-V₄selected from CR, identically or differently at each occurrence_vOr N;

R_d，R_e，R_veach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy having 7 to 30 carbon atomsAlkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein the content of the first and second substances,

R_a，R_band R_cThe same or different at each occurrence represents mono-, poly-, or unsubstituted;

R_a，R_b，R_c，R_N1，R_N2，R_C1And R_C2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atomsAryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

17. The electroluminescent device of claim 15, wherein the phosphorescent light-emitting material is a metal complex having M (L)_a)_m(L_b)_nA general formula (II) of (I);

m is selected from metals having a relative atomic mass greater than 40;

m is 1,2 or 3; n is 0, 1 or 2; the sum of M and n is equal to the oxidation state of M; when m is 2 or more, a plurality of L_aMay be the same or different; when n is 2, two L_bMay be the same or different;

L_ahas a structure as shown in formula 3:

wherein the content of the first and second substances,

ring D and ring E via U_aAnd U_bFusing;

U_aand U_bSelected from C or N, identically or differently at each occurrence;

V₁-V₄selected from CR, identically or differently at each occurrence_vOr N;

wherein said ligand L_bHas the following structure:

wherein R is₁To R₇Each independently selected from the group consisting of: hydrogen, deuterium, halogenA substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

preferably, wherein R₁-R₃At least one or two of which are selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R₄-R₆At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof;

more preferably, R₁-R₃At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R₄-R₆At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.

18. An electroluminescent device as claimed in 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 Ir (L)_a)(L_b)(L_c)、Ir(L_a)₂(L_b)、Ir(L_a)₂(L_c) Or Ir (L)_a)(L_c)₂Any of the structures shown.

19. A compound formulation comprising a compound of any one of claims 1 to 12.

20. A display assembly comprising an electroluminescent device as claimed in any one of claims 13 to 18.