CN115207254A

CN115207254A - Organic electroluminescent device and application thereof

Info

Publication number: CN115207254A
Application number: CN202110385108.7A
Authority: CN
Inventors: 王静; 庞惠卿; 崔至皓; 夏传军; 邝志远; 李崇; 王芳; 张兆超
Original assignee: Jiangsu Sunera Technology Co Ltd; Beijing Summer Sprout Technology Co Ltd
Current assignee: Jiangsu Sunera Technology Co Ltd; Beijing Summer Sprout Technology Co Ltd
Priority date: 2021-04-09
Filing date: 2021-04-09
Publication date: 2022-10-18

Abstract

The invention provides an organic electroluminescent device and application thereof, wherein the organic electroluminescent device comprises a cathode, an anode and an organic layer arranged between the cathode and the anode; the organic layer comprises a first organic layer and a second organic layer; the first organic layer includes a first organic compound, and the second organic layer includes a second organic compound. The organic electroluminescent device can obtain better device performance by combining the first organic compound and the second organic compound with specific structures, greatly improve the service life of the device, enable the device to have higher efficiency and have obvious advantages in industry.

Description

Organic electroluminescent device and application thereof

Technical Field

The invention belongs to the technical field of organic electroluminescence, and particularly relates to an organic electroluminescent device and application thereof.

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, organic plasma light emitting devices, and the like.

In 1987, tang and Van Slyke of eastman kodak reported a two-layer organic electroluminescent device including a hole transport layer of arylamine, and an electron transport layer and a light emitting layer of tris-8-hydroxyquinoline-aluminum; upon biasing the device, green light is emitted from the device. The invention lays the foundation for the development of the modern OLED. State-of-the-art 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 OLED is 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, which emit light using only singlet states, the triplet states generated in the device being wasted through non-radiative decay channels; therefore, the Internal Quantum Efficiency (IQE) of the fluorescent OLED is only 25%, which limits the commercialization of the fluorescent OLED. In 1997, forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as the emitter, thus enabling harvesting of singlet and triplet states, 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, and these emitters have a small singlet-triplet gap, making it possible to return excitons from the triplet state to the singlet state. In TADF devices, triplet excitons are capable of generating singlet excitons through reverse intersystem crossing, resulting in high IQE.

OLEDs can also be divided into small molecule OLEDs 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; small molecules can be very large in molecular weight as long as they have a precise structure; dendrimers with well-defined structures are considered small molecules. The polymer OLED comprises a conjugated polymer and a non-conjugated polymer having pendant light-emitting groups. 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.

Organic electroluminescent devices convert electrical energy into light by applying a voltage across the device. In general, an organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the electroluminescent device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. Materials constituting the organic layer may be classified into a hole injection material, a hole transport material, an electron blocking material, a host material, a light emitting material, a hole blocking material, an electron transport material, an electron injection material, and the like according to the function of the material. When bias is applied to the device, holes are injected into the light-emitting layer from the anode, electrons are injected into the light-emitting layer from the cathode, the holes and the electrons meet to form excitons, and the excitons emit light in a combined manner; the hole injection layer and the electron blocking layer are one of important functional layers affecting the performance of the organic electroluminescent device, and the selection and matching of materials seriously affect the driving voltage, the efficiency and the service life of the organic electroluminescent device. It is commercially desirable to obtain an organic electroluminescent device having characteristics of low voltage, high efficiency, long lifetime, etc., and it is very important to develop novel hole injection layer and electron blocking layer materials, and it is also very important to select a suitable combination of hole injection layer and electron blocking layer for achieving the above object.

The hole injection layer may be a single layer of material or the hole transport layer may be doped with a p-type conductivity dopant material in a proportion, typically less than 5%, most typically between 1 and 3%. The p-type doping effect is achieved through the strong electron capturing capacity of the p-type conductive doping material, and the hole injection and the conductivity are improved. A hole injection layer doped with a p-type conductive dopant material in a device generally has a lower voltage than a single layer of material and thus is widely used. The LUMO energy level of a commonly used p-type conductive doping material is about 5.1eV, and the p-type conductive doping material can be matched with a hole transport material with a common HOMO energy level about 5.1 eV. However, the hole transport materials in the industry today are of a wide variety, with a HOMO level of 5.2eV or greater. For these materials with deep HOMO levels, it is necessary to use p-type conductive materials with deeper LUMO levels to achieve more excellent device performance. So as to promote the wide application of p-type conductive doping technology, the development and utilization of p-type conductive doping material with LUMO energy level deeper than 5.05eV are needed

On the other hand, in the OLED device, most of the host material HOMO level of the light-emitting layer is in the range of 5.4eV to 5.6eV, which is far deeper than the material of the general hole transport layer, so that holes encounter a higher potential barrier when entering the light-emitting layer from the transport layer. In order to solve this problem, an electron blocking layer having an HOMO energy level between the hole transport layer and the light emitting layer is usually inserted between the hole transport layer and the light emitting layer, i.e., a multilayer structure is established between the hole injection layer and the light emitting layer, thereby forming a potential-advancing structure. Therefore, if a hole transport material with a deeper HOMO level can be used in combination with an electron blocking layer with a deeper HOMO level, the barrier of holes from the injection layer to the light emitting layer can be reduced at the same time; still further, if a hole transporting material with a deeper HOMO level is used in the hole injection layer, it is necessary to use a p-type conductivity dopant material with a deeper LUMO level to match it, thereby obtaining a device with lower voltage, higher efficiency and longer lifetime.

The applicant previously disclosed in US patent application US20200062778A1 an organic compound, including compounds

The compound is used as a p-type conductive doping material applied to an organic electroluminescent device, but the patent does not limit the matched electronic barrier material.

CN110577511A discloses an organic compound containing a compound

In the patent, it is applied to an organic electroluminescent device as a hole transport material or an electron blocking layer material, but the patent application does not disclose a technical solution that can be used with other materials (especially p-type conductive doped materials).

Although OLED devices including hole injection layers or electron blocking layers have been disclosed in the prior art, there are still disadvantages of low efficiency, short lifetime, and the like. Therefore, the development of a wider variety of higher performance organic electroluminescent devices is a research focus in the art.

Disclosure of Invention

In order to develop more various, higher-performance organic electroluminescent devices, it is an object of the present invention to provide an organic electroluminescent device comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode; the organic layer comprises a first organic layer and a second organic layer; the first organic layer comprises a first organic compound, and the second organic layer comprises a second organic compound;

the first organic compound has a structure as shown in formula I:

in formula I, X, Y are, identically or differently at each occurrence, selected from NR ', CR "R'", O, S or Se;

Z ₁ 、Z ₂ identically or differently on each occurrence is selected from O, S or Se;

r, R ', R ", and R'" are, identically or differently at each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyl group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof;

each R may be the same or different, and at least one of R, R ', R ", and R'" is a group having at least one electron withdrawing group;

adjacent substituents in formula I can optionally be linked to form a ring;

the second organic compound has a structure as shown in formula II:

in formula II, o, p, m are, identically or differently on each occurrence, selected from 0, 1 or 2;

R ₁ 、R _M is selected, identically or differently on each occurrence, from hydrogen, deuterium, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and R ₁ And R _M At least one of which is not a hydrogen atom or a deuterium atom;

ring B, ring C, on each occurrence, are selected, identically or differently, from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms;

R ₃ 、R ₄ each occurrence, identically or differently, is selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

The organic electroluminescent device at least comprises a first organic layer and a second organic layer, wherein the first organic layer comprises a first organic compound with a structure shown in a formula I as a p-type conductive doping material, the second organic layer comprises a second organic compound with a structure shown in a formula II as an electron blocking material, and the organic electroluminescent device has higher luminous efficiency and longer service life through the mutual matching of materials with specific structures and hierarchical structures comprising the materials, and the comprehensive performance of the organic electroluminescent device is remarkably improved compared with that of a conventional organic electroluminescent device.

It is a second object of the present invention to provide a display assembly comprising an organic electroluminescent device as described in the first object.

It is a further object of the present invention to provide a use of the organic electroluminescent device according to one of the objects in an electronic device, an electronic element module, a display device, or a lighting device.

Compared with the prior art, the invention has the following beneficial effects:

the organic electroluminescent device comprises a first organic layer and a second organic layer, wherein the first organic layer comprises a first organic compound as a p-type conductive doping material, the second organic layer comprises a second organic compound as an electron blocking material, and the p-type conductive doping material and the electron blocking material with specific structures are combined for use, so that better device performance can be obtained, the service life of the device can be greatly prolonged, the device has higher efficiency, and the organic electroluminescent device has obvious advantages in industry.

Drawings

Fig. 1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Detailed Description

The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.

As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed on" the 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, the term "OLED device" includes an anode layer, a cathode layer, one or more organic layers disposed between the anode layer and the cathode layer. An "OLED device" can be bottom emitting, i.e. from the substrate side, or top emitting, i.e. from the encapsulation layer side, or a transparent device, i.e. from both the substrate and the encapsulation side. As used herein, the term "OLED lighting panel" includes a substrate, an anode layer, a cathode layer, one or more organic layers disposed between the anode layer and the cathode layer, an encapsulation layer, and at least one anode contact and at least one cathode contact extending outside of the encapsulation layer for external access. As used herein, the term "module" refers to an electronic device having only one set of external electrical drives. As used herein, the term "encapsulation layer" may be a thin film encapsulation having a thickness of less than 100 microns, which includes disposing one or more thin films directly onto the device, or may also be a cover glass (cover glass) adhered to the substrate. As used herein, the term "flexible printed circuit" (FPC) refers to any flexible substrate coated with any one or combination of the following, including but not limited to: conductive lines, resistors, capacitors, inductors, transistors, micro-electro-mechanical systems (MEMS), and the like. The flexible substrate of the flexible printed circuit may be plastic, thin glass, thin metal foil coated with an insulating layer, fabric, leather, paper, etc. A flexible printed circuit board is typically less than 1mm thick, more preferably less than 0.7mm thick. As used herein, the term "light extraction layer" may refer to a light diffusing film, or other microstructure having light extraction effects, or a thin film coating having light outcoupling effects. The light extraction layer can be disposed on the substrate surface of the OLED, or can be in other suitable locations, such as between the substrate and the anode, or between the organic layer and the cathode, between the cathode and the encapsulation layer, on the surface of the encapsulation layer, and so forth. As used herein, the term "independently driven" means that the operating points of two or more light emitting panels are separately controlled. Although the light emitting panels may be connected to the same controller or power line, there may be circuitry to divide the drive lines and power each panel without affecting each other. The terms "first light emitting unit", "second light emitting unit", etc. describe, and should not be limited by these terms. These terms are only used to distinguish one light-emitting unit from another.

The cross-sectional schematic view of the stacked or single-layer organic electroluminescent device provided by the embodiments of the present invention is an illustrative and non-limiting illustration, and the drawings are not necessarily drawn to scale, and some layer structures may be added or omitted as required. The substrate can be fabricated on a variety of substrates such as glass, plastic and metal. Fig. 1 shows schematically, without limitation, an organic electroluminescent device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The organic electroluminescent device 100 may include an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emission layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, a cathode 111, and a capping layer 190. The organic electroluminescent device 100 may be fabricated by sequentially depositing the described layers. The properties and functions of the various layers and exemplary materials are described in more detail in U.S. patent No. 7279704B2, columns 6-10, which is incorporated herein by reference in its entirety.

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, "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 be generally classified 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 singlet-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. The spatial separation of HOMO from LUMO in these donor-acceptor type compounds usually results in a small Δ ES-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 preferred. 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, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. 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 alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. 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 groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl 1-pentynyl, phenylethynyl, 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-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-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, mesitylphenyl 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, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothiophenecopyridine, selenophene bipyridine, selenobenzene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 3236 zxzborane, 5262-azaborine, 3763-oxaborone, 3763-aza-oxazaft analogs 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. 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 a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl tert-butyl group, an α -naphthylmethyl group, a 1- α -naphthyl-ethyl group, a 2- α -naphthylethyl group, a 1- α -naphthylisopropyl group, a 2- α -naphthylisopropyl group, a β -naphthylmethyl group, a 1- β -naphthylethyl group, a 2- β -naphthylethyl group, a 1- β -naphthylisopropyl group, a 2- β -naphthylisopropyl group, a p-methylbenzyl group, a m-methylbenzyl group, an o-methylbenzyl group, a p-chlorobenzyl group, a m-chlorobenzyl group, a p-chlorobenzyl group, a m-bromobenzyl group, an o-bromobenzyl group, a p-iodobenzyl group, a m-iodobenzyl group, a p-hydroxybenzyl group, a m-hydroxybenzyl group, an o-hydroxybenzyl group, a p-aminobenzyl group, an m-aminobenzyl group, a p-nitrobenzyl group, a m-nitrobenzyl group, an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group and a 1-chloro-2-isopropylyl group. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. 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.

Alkylgermyl-as used herein, alkyl-substituted germyl is contemplated. The alkylgermyl group may be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include a trimethylgermyl group, a triethylgermyl group, a methyldiethylgermyl group, an ethyldimethylgermyl group, a tripropylgermyl group, a tributylgermyl group, a triisopropylgermyl group, a methyldiisopropylgermyl group, a dimethylisopropylgermyl group, a tri-tert-butylgermyl group, a triisobutylgermyl group, a dimethyl-tert-butylgermyl group, and a methyl-di-tert-butylgermyl group. In addition, the alkylgermyl group may be optionally substituted.

Arylgermyl-as used herein, encompasses at least one aryl or heteroaryl substituted germyl. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenylbiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, a diphenylt-butylgermanium group. In addition, the arylgermyl 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 groups, substituted cycloalkyl groups, substituted heteroalkyl groups, substituted heterocyclyl groups, substituted aralkyl groups, substituted alkoxy groups, substituted aryloxy groups, substituted alkenyl groups, substituted alkynyl groups, substituted aryl groups, substituted heteroaryl groups, substituted alkylsilyl groups, substituted arylsilyl groups, substituted alkylgermyl groups, substituted arylgermyl groups, substituted amino groups, substituted acyl groups, substituted carbonyl groups, substituted carboxylic acid groups, substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups, and refers to alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclyl groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylgermyl groups, amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, sulfinyl groups, sulfonyl groups, and phosphino groups, any one or more of which may be substituted with deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted arylalkyl groups having 3 to 20 carbon atoms, unsubstituted arylalkyl groups having 2 to 6 carbon atoms, unsubstituted aryl groups having 2 to 20 carbon atoms, unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, unsubstituted arylgermyl groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, 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, multiple substitutions are meant to include within the scope of double substitutions up to the maximum 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 optionally be linked to form a ring, both in the case where adjacent substituents may be linked to form a ring and in 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 (including spiro, bridged, fused, etc.), 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:

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

in this context, the work function of a metal refers to the minimum energy required to move an electron from the interior of an object to the surface of the object. All "metal work function" herein is expressed in absolute value (positive), i.e. the higher the value, the greater the energy required to pull an electron to vacuum level, whereas as described herein, reference to "metal work function" is to be taken as large, small, i.e. to mean absolute numerical size. For example, "metal work function greater than 5eV" means that an energy greater than 5eV is required to pull an electron to vacuum level.

Herein, the values of HOMO (highest occupied orbital) and LUMO (lowest unoccupied orbital) are measured by electrochemical cyclic voltammetry, which is the most commonly used method for measuring the energy level of an organic material, and the equipment used is simple and is convenient to operate. In an electrochemical cell, when a certain positive potential is applied to a working electrode relative to a reference electrode potential, organic material molecules adsorbed on the surface of the electrode lose electrons on the valence band of the organic material molecules to generate an electrochemical oxidation-reduction reaction, and when a higher positive potential is applied, the electrochemical reaction on the surface of the electrode continues, and at the moment, the initial potential of the organic material molecules on the working electrode, which generates the electrochemical oxidation reaction, corresponds to the HOMO energy level. Similarly, when a certain negative potential is applied to the working electrode relative to the potential of the reference electrode, the molecules of the organic material adsorbed on the surface of the electrode will get electrons on the conduction band to undergo electrochemical reduction reaction, and when the negative potential is increased further, the electrochemical reaction on the surface of the electrode will continue, and at this time, the initial potential of the molecules of the organic material on the working electrode to undergo electrochemical reduction reaction corresponds to the LUMO level.

In this context, all "HOMO" and "LUMO" energy levels are expressed as absolute values (positive values), and the larger the value, the deeper the energy level.

According to the invention, the p-type conductive doped material with the structure of the formula I and the electron barrier material with the structure of the formula II are matched and combined to obtain the organic electroluminescent device with high efficiency and long service life. By using the p-type conductive doped material with the specific structure and the electronic blocking material with the specific structure, which are disclosed by the invention, in a matching combination manner, the organic electroluminescent device has more excellent performance compared with an organic electroluminescent device using a conventional p-type conductive doped material and an electronic blocking material.

In one embodiment, the present invention provides an organic electroluminescent device comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode; the organic layer comprises a first organic layer and a second organic layer; the first organic layer comprises a first organic compound, and the second organic layer comprises a second organic compound;

the first organic compound has a structure as shown in formula I:

in formula I, X, Y is, identically or differently on each occurrence, selected from NR ', CR "R'", O, S or Se;

Z ₁ 、Z ₂ is selected, identically or differently on each occurrence, from O, S or Se;

r, R ', R "and R'" are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, nitroso group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyloxy group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof;

adjacent substituents in formula I can optionally be linked to form a ring;

the second organic compound has a structure as shown in formula II:

in formula II, o, p, m, on each occurrence, are selected, identically or differently, from 0, 1 or 2;

R ₁ 、R _M is selected, identically or differently on each occurrence, from hydrogen, deuterium, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, and R ₁ And R _M At least one of which is not represented by a hydrogen atom and a deuterium atom;

R ₃ 、R ₄ each occurrence, identically or differently, is selected from hydrogen, deuterium, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms;

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

Herein, "adjacent substituents in formula I can optionally be linked to form a ring" is intended to mean that adjacent substituents R "and R'" in formula I can be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

As used herein, the "adjacent substituent R ₃ Can optionally be linked to form a ring "is intended to mean a ring in which two adjacent substituents R ₃ May be connected to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

As used herein, the "adjacent substituent R ₄ Can optionally be linked to form a ring "is intended to mean a ring in which two adjacent substituents R ₄ May be connected to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.

In one embodiment, said substitution in said "substituted" substituents in formula II is selected from deuterium, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 20 carbon atoms. For example, R ₃ Selected from the group consisting ofWhen the aryl group having 6 to 30 carbon atoms is used, the substituent of the aryl group having 6 to 30 carbon atoms may be one or at least two of the following substituents: deuterium, alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 20 carbon atoms.

In one embodiment, the heteroatom in the heteroaryl group in formula II is selected from one or more of oxygen, sulfur, or nitrogen.

In a specific embodiment, the X, Y are selected, identically or differently at each occurrence, from CR "R '" or NR'; r ', R ' and R ' are groups having at least one electron withdrawing group.

In one embodiment, the X, Y are selected, identically or differently at each occurrence, from O, S or Se, at least one of R being a group having at least one electron withdrawing group.

In a preferred embodiment, each of said R is a group having at least one electron withdrawing group.

In a specific embodiment, the Hammett constant of the electron withdrawing group is 0.05 or more, preferably 0.3 or more, and more preferably 0.5 or more.

In one embodiment, the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ Boryl, sulfinyl, sulfonyl, phosphinoxy, azaaryl, and substituted with halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ One or at least two of the following groups substituted by boryl, sulfinyl, sulfonyl, phosphinyl and azacyclyl: an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atomsAn alkylsilyl group of 6 to 20 carbon atoms, an arylsilyl group of 3 to 20 carbon atoms, an alkylgermanyl group of 6 to 20 carbon atoms, an arylgermanyl group of 6 to 20 carbon atoms, and combinations thereof.

In one embodiment, the electron withdrawing group is selected from the group consisting of: f, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, pyrimidinyl, triazinyl, and combinations thereof.

In a specific embodiment, the X, Y, each occurrence, is selected, identically or differently, from the group consisting of: the concentration of oxygen, sulfur, se,

wherein R is ₂ The same or different at each occurrence is selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyloxy group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atomsSubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl groups having 6 to 20 carbon atoms, and combinations thereof;

preferably, R ₂ The same or different at each occurrence is selected from the group consisting of: f, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazinyl, and combinations thereof;

wherein V and W are selected, identically or differently on each occurrence, from CR _v R _w ，NR _v O, S or Se;

wherein Ar, identically or differently at each occurrence, is selected from 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;

wherein, A, R _a ，R _b ，R _c ，R _d ，R _e ，R _f ，R _g ，R _h ，R _v And R _w The same or different at each occurrence is selected from the group consisting of: hydrogen, deuterium, halogen, nitroso group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyloxy group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 3 to 20 carbon atomsAn arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, and combinations thereof;

wherein A is a group having at least one electron-withdrawing group, and for either structure when R is _a 、R _b 、R _c 、R _d 、R _e 、R _f 、R _g 、R _h 、R _v And R _w When one or at least two of them occur, R _a 、R _b 、R _c 、R _d 、R _e 、R _f 、R _g 、R _h 、R _v And R _w At least one of which is a group having at least one electron-withdrawing group; preferably, the group having at least one electron withdrawing group is selected from the group consisting of: f, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazinyl, and combinations thereof.

Wherein "-" denotes the position at which the X and Y groups are attached to the dehydrobenzodioxazole, dehydrobenzodithiazole or dehydrobenzodiselenazole ring in formula I.

wherein "-" represents a position where the X and Y groups are attached to a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in formula 1.

In a specific embodiment, the R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanoBasic group, SCN, OCN, SF ₅ Boryl, sulfinyl, sulfonyl, phosphinoxy, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, and substituted with halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ Any one of the following groups substituted with one or at least two of boryl, sulfinyl, sulfonyl and phosphinyl groups: an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.

In a specific embodiment, the R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO ₂ ，SO ₂ CH ₃ ，SCF ₃ ，C ₂ F ₅ ，OC ₂ F ₅ ，OCH ₃ Diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, optionally substituted with CN or CF ₃ One or at least two substituted vinyl groups of (A) by CN or CF ₃ Substituted ethynyl, dimethylphosphinoxy, diphenylphosphinoxy, F, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis (trifluoromethyl) phenyl, bis (trifluoromethoxy) phenyl, 4-cyanotetrafluorophenyl, substituted by F, CN or CF ₃ Or at least two substituted phenyl or biphenyl groups, a tetrafluoropyridyl group, a pyrimidinyl group, a triazinyl group, a diphenylboryl group, a oxaboro-anthracenyl group, and combinations thereof.

In one embodiment, the X, Y is

In a specific embodiment, the R, on each occurrence, is selected, identically or differently, from the group consisting of:

wherein the content of the first and second substances,

represents the position at which the R group is attached to a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in formula I.

In a preferred embodiment, both R in one compound represented by formula I are the same.

In one embodiment, the first organic compound has a structure represented by formula III:

wherein, two Z are the same, two R structures are the same or different, and Z, X, Y, R is respectively selected from atoms or groups shown in the following table;

compounds having the structure of formula III are selected from the group consisting of compound 1 to compound 1357, wherein the specific structures of compound 1 to compound 1357 are according to claim 10.

In one embodiment, the second organic compound has a structure as shown in formula II-1;

wherein o, p are selected, identically or differently on each occurrence, from 0, 1 or 2;

R ₁ selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl;

R ₃ 、R ₄ each occurrence identically or differently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted carbazolyl;

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

In one embodiment, the substitution in the "substituted" substituent described in formula II-1 is selected from deuterium, phenyl, naphthyl, biphenyl, or dibenzofuranyl. For example, R ₃ Selected from substituted phenyl, in which case the substituents of the phenyl group may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In one embodiment, the second organic compound has a structure as shown in formula II-2;

ring B, ring C, equal or different at each occurrence, is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms;

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

In a particular embodiment, the substitution in the "substituted" substituent described in formula II-2 is selected from deuterium, phenyl, naphthyl, biphenyl, or dibenzofuranyl. For example, R ₃ Selected from substituted phenyl, in which case the substituents of the phenyl group may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In one embodiment, the second organic compound has a structure as shown in formula II-3;

R ₃ 、R ₄ selected, identically or differently on each occurrence, from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstitutedNaphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted carbazolyl;

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

In a particular embodiment, the substitution in the "substituted" substituents described in formula II-3 is selected from deuterium, phenyl, naphthyl, biphenyl, or dibenzofuranyl. For example, R ₃ Selected from substituted phenyl, in which case the substituents of the phenyl group may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In one embodiment, the second organic compound has a structure according to formula II-4:

R _M selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl;

R ₃ 、R ₄ each occurrence identically or differently selected from hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted carbazolyl group;

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

In a particular embodiment, the substitution in the "substituted" substituent described in formula II-4 is selected from deuterium, phenyl, naphthyl, biphenyl, or dibenzofuranyl. For example, R ₃ Selected from substituted phenyl, in which case the substituents of the phenyl group may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In one embodiment, the second organic compound has a structure according to formula II-5:

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

In one embodiment, the substitution in the "substituted" substituent described in formula II-5 is selected from deuterium, phenyl, naphthyl, biphenyl, or dibenzofuranyl. For example, R ₃ Selected from substituted phenyl, in which case the phenyl radical is takenThe substituent may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In a particular embodiment, said ring B, ring C, identically or differently on each occurrence, is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dimethylfluorenyl group.

In a particular embodiment, said ring B, ring C, on each occurrence, are selected, identically or differently, from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dimethylfluorenyl;

wherein said substitution in the "substituted" substituents is selected from deuterium atoms, phenyl, naphthyl, biphenyl or dibenzofuranyl groups, e.g. ring B is selected from substituted phenyl, in which case the substituents of phenyl groups may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In one embodiment, the second organic compound has a structure as shown in any one of formulas II-6 through II-8:

Z ₁ -Z ₈ selected from CR, identically or differently at each occurrence ₅ ，R ₅ Selected from hydrogen, deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl;

R ₃ 、R ₄ each occurrence identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthryl, and substituted or unsubstituted carbazolyl.

In one embodiment, the substitution in the "substituted" substituents described in formulas II-6 through II-8 is selected from deuterium, phenyl, naphthyl, biphenyl, or dibenzofuranyl. For example, R ₃ Selected from substituted phenyl, in which case the substituents of the phenyl group may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In one embodiment, the second organic compound has a structure represented by formula II-9 or formula II-10:

R _M selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl;

in one embodiment, the substitution in the "substituted" substituents described in formulas II-9 and II-10 is selected from deuterium, phenyl, naphthyl, biphenyl, or bisA benzofuranyl group. For example, R ₃ Selected from substituted phenyl, in which case the substituents of the phenyl group may be one or at least two of the following substituents: deuterium, phenyl, naphthyl, biphenyl or dibenzofuranyl.

In a specific embodiment, the second organic compound is selected from the group consisting of compound II-1 through compound II-286; the specific structures of the compounds II-1 to II-286 are disclosed in claim 14.

In one embodiment, the first organic compound has a LUMO energy level value greater than 5.05eV and less than or equal to 5.50eV.

In a specific embodiment, the first organic compound has a LUMO level value greater than 5.05eV, for example, the LUMO level value can be 5.06eV, 5.07eV, 5.08eV, 5.09eV, 5.10eV, 5.11eV, 5.12eV, 5.13eV, 5.14eV, 5.15eV, 5.16eV, 5.17eV, 5.18eV, 5.19eV, 5.20eV, 5.21eV, 5.22eV, 5.23eV, 5.24eV, or 5.25 eV.

In one embodiment, the second organic compound has a HOMO energy level value of less than 5.45eV and equal to or greater than 5.0eV.

In one embodiment, the second organic compound has a HOMO level value of less than 5.45eV, for example, the HOMO level value can be 5.22eV, 5.23eV, 5.25eV, 5.27eV, 5.29eV, 5.3eV, 5.31eV, 5.32eV, 5.33eV, 5.34eV, 5.35eV, 5.36eV, 5.37eV, 5.38eV, 5.39eV, 5.4eV, 5.41eV, 5.43eV, or 5.44 eV.

In one embodiment, the first organic layer further comprises a third organic compound comprising any one or at least two chemical building blocks selected from the group consisting of: triarylamines, carbazoles, fluorenes, spirobifluorenes, thiophenes, furans, phenyls, oligophenylenes, oligofluorenes, and combinations thereof.

In one embodiment, the third organic compound has a HOMO energy level value of 5.09eV or greater, such as 5.09eV, 5.1eV, 5.11eV, 5.13eV, 5.15eV, 5.17eV, 5.19eV, 5.2eV, 5.21eV, 5.23eV, 5.25eV, 5.27eV, 5.28eV, 5.29eV, or 5.3 eV.

In one embodiment, a third organic layer is further disposed between the first organic layer and the second organic layer.

In a specific embodiment, the third organic layer comprises a fourth organic compound comprising any one or at least two chemical building blocks selected from the group consisting of: triarylamines, carbazoles, fluorenes, spirobifluorenes, thiophenes, furans, phenyls, oligophenylenes, oligofluorenes, and combinations thereof.

In a specific embodiment, the fourth organic compound and the third organic compound are the same or different.

In a specific embodiment, the fourth organic compound and the third organic compound are the same.

In a specific embodiment, the fourth organic compound and the third organic compound are not the same.

In one embodiment, the first organic layer and the anode are in contact with each other.

In one embodiment, the thickness of the first organic layer is 0.1 to 40nm, and may be, for example, 0.3nm, 0.5nm, 0.8nm, 1nm, 3nm, 5nm, 8nm, 10nm, 12nm, 15nm, 18nm, 20nm, 22nm, 25nm, 28nm, 30nm, 32nm, 35nm or 38nm, and the specific values therebetween are limited by space and for brevity, and the invention is not exhaustive of the specific values included in the range.

In a preferred embodiment, the first organic layer is a hole injection layer.

In one embodiment, the first organic compound is contained in the material of the first organic layer in an amount of 5% by mass or less, for example, 4.8%, 4.5%, 4.2%, 4%, 3.8%, 3.5%, 3.2%, 3%, 2.8%, 2.5%, 2.2%, 2%, 1.8%, 1.5%, 1.2%, 1%, etc., and more preferably 3% by mass or less.

In one embodiment, the organic electroluminescent device includes a light emitting layer, and the second organic layer is disposed between the anode and the light emitting layer and in contact with the light emitting layer.

In one embodiment, the thickness of the second organic layer is 1 to 100nm, for example, 5nm, 10nm, 15nm, 20nm, 25nm, 30nm, 35nm, 40nm, 45nm, 50nm, 60nm, 70nm, 80nm, 90nm or 95nm, and specific values therebetween, which are not exhaustive for the invention and for the sake of brevity.

In a preferred embodiment, the second organic layer is an electron blocking layer.

In a specific embodiment, the present invention provides a display assembly comprising an organic electroluminescent device as described above.

In a specific embodiment, the present invention provides a use of the organic electroluminescent device as described above in an electronic device, an electronic element module, a display device, or a lighting device.

In the present invention, all the compounds were measured for their electrochemical properties by Cyclic Voltammetry (CV). The test uses an electrochemical workstation manufactured by the martens koste instruments ltd under the model CorrTest CS120 and uses a three electrode working system: platinum disk electrode as working electrode, ag/AgNO ₃ The electrode is a reference electrode, and the platinum wire electrode is an auxiliary electrode. Preparing a compound to be detected into 10 by taking anhydrous DMF as a solvent and 0.1mol/L tetrabutylammonium hexafluorophosphate as a supporting electrolyte ^-3 And (3) introducing nitrogen into the solution for 10min to remove oxygen before testing. Setting instrument parameters: the scan rate was 100mV/s, the potential separation was 0.5mV, and the test window was 1V to-0.5V.

In one embodiment, table 1 lists the HOMO energy levels of a portion of the third organic compounds:

TABLE 1

Compound numbering	HOMO(eV)
		HT-1	5.09
HT-2	5.21
		HT	5.28

Table 2 lists the LUMO energy levels of some of the first organic compounds:

TABLE 2

Compound numbering	LUMO(eV)
		PD-ref	5.05
Compound 70	5.20
		Compound 56	5.12
Compound 72	5.16
		Compound 68	5.20
Compound 1357	5.17

Table 3 lists the HOMO energy levels of some of the second organic compounds:

TABLE 3

Compound numbering	HOMO(eV)
		GH1	5.45
Compound II-127	5.36
		Compound II-136	5.33
Compound II-210	5.22

The structures of the compounds referred to in tables 1 to 3 are as follows:

as can be seen from Table 1, compound HT has a deeper HOMO level of 5.28eV, while compound HT-1 has a shallower HOMO level of 5.09eV; among the p-type conductivity dopant materials shown in table 2, compound 70 and compound 1357 (first organic compound) have deeper LUMO levels than compound PD-ref, 5.20eV and 5.17eV, respectively; from the above analysis, it is speculated that the use of the deep level hole transport material HT in combination with the deep level p-type conductivity dopant compound 70 results in better device performance. Meanwhile, comparing the electron blocking materials in table 3, the HOMO level (5.36 eV) of compound II-127 (second organic compound), the HOMO level (5.33 eV) of compound II-136 (second organic compound), and the HOMO level (5.22 eV) of compound II-210 (second organic compound) are all closer to the HOMO level (5.28 eV) of the hole transport material HT than the HOMO level (5.36 eV) of compound GH1, and thus it can be assumed that the hole transport material HT doped with the first organic compound of the present invention and the electron blocking material second organic compound are used to produce better device performance.

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, paragraphs 2016/0359122A1, which is hereby incorporated by reference in its entirety. 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 of formula I or formula II 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 US2015/0349273A1, paragraphs 0080-0101, which is incorporated herein by reference in its entirety. 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.

Hereinafter, the present invention will be described in more detail with reference to the following examples. The compounds used in the following examples are readily available to those skilled in the art, and therefore their synthesis methods are not described herein, such as that found in chinese patent CN201911046002.3, which is incorporated herein by reference in its entirety. It is apparent that the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Based on the following examples, a person skilled in the art will be able to derive further embodiments of the invention by modifying them.

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 Angstrom 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 person skilled in the art knows the relevant contents of the above device usage, testing method, etc., and can obtain the inherent data of the sample with certainty and without influence, the above related contents are not further described herein.

Example 1

An organic electroluminescent device, specifically a green organic electroluminescent device, is shown in fig. 1, and includes an anode 110, a hole injection layer 120 (first organic layer), a hole transport layer 130 (third organic layer), an electron blocking layer 140 (second organic layer), a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, a cathode 111, and a capping layer 190, which are sequentially disposed; the preparation method comprises the following steps:

(1) First, a 0.7mm thick glass substrate is used, having a previously patterned thickness of

Indium Tin Oxide (ITO)/silver (Ag)/Indium Tin Oxide (ITO) as an anode, and the ITO surface was treated with oxygen plasma and UV ozone after washing the substrate with deionized water and detergent water. The substrate was then dried in a glove box to remove moisture and loaded onto a rack into a vacuum chamber. The lower isA fixed organic layer under vacuum of about 10 deg.C ^-6 In the case of Torr

The evaporation is carried out on the anode layer in sequence by vacuum thermal evaporation:

(2) A compound HT (hole transport material) and a first organic compound of the present invention, compound 70 (used as a p-type conductive doping material) are simultaneously evaporated on the anode as a hole injection layer (HIL,

) The mass ratio of compound HT to compound 70 is 97;

(3) A compound HT is evaporated on the hole injection layer to serve as a hole transport layer (HTL,

) The hole transport layer is a microcavity adjusting layer, and in order to obtain data under a target color coordinate, the hole transport layer is in a certain range and is not fixed at a certain thickness;

(4) The second organic compound of the present invention, compound II-127, was vapor-deposited on the hole transport layer to serve as an electron blocking layer (EBL,

)；

(5) Compounds GH1, GH2 and GD are simultaneously evaporated on the electron blocking layer as a light emitting layer (EML,

) The mass ratio of the compounds GH1 and GH2 to the compound GD is 47;

(6) A compound HB was vapor-deposited on the light-emitting layer as a hole blocking layer (HBL,

)；

(7) Co-depositing on the hole blocking layer compounds ET and Liq as electron transport layer (ETL,

) The mass ratio of the compound ET to Liq is 40;

(8) Vapor plating on electron transport layer

Metal Yb of thickness as an Electron Injection Layer (EIL);

(9) Metal magnesium and metal silver were co-evaporated on the electron injection layer as cathodes (Cathode,

) The mass ratio of magnesium to silver is 1:9; compound CPL was finally evaporated as a capping layer (CPL,

)；

the device was transferred back to the glove box and encapsulated with a glass cover to complete the device.

Comparative example 1-1

Comparative example 1-1 differs from example 1 only in that compound II-127 in step (4) is replaced with compound GH 1; the other materials and preparation methods were the same as in example 1.

Comparative examples 1 to 2

Comparative examples 1-2 differ from example 1 only in that compound 70 in step (2) is replaced with compound PD-ref; the other materials and preparation methods were the same as in example 1.

Comparative examples 1 to 3

Comparative examples 1-3 differ from example 1 only in that compound 70 in step (2) is replaced with compound PD-ref and compound II-127 in step (4) is replaced with compound GH 1; the other materials and preparation methods were the same as in example 1.

The detailed device hierarchy and thickness are shown in table 4:

TABLE 4 partial device structures of example 1 and comparative examples 1-1 to 1-3

The material structure used in the device is as follows:

device performance testing and analysis

At a current density of 10mA/cm ² Color coordinates (CIEx, CIEy), voltage (V), current Efficiency (CE), and power efficiency (PE, lm/W) of the devices in example 1 and comparative examples 1-1 to 1-3 were tested as follows; the device lifetime (LT 95) is at 80mA/cm ² The luminance decays to 95% of the original luminance under driving. The test data are shown in table 5:

TABLE 5 device Performance of example 1 and comparative examples 1-1 to 1-3

Table 5 shows the results of testing electroluminescent devices comprising different combinations of p-type conductivity dopant materials and electron blocking materials. In embodiment 1, a device structure in which the p-type conductive doping material compound 70 and the electron blocking layer material compound II-127 disclosed in the present invention are combined and matched is used. In comparative example 1-1, a device structure in which a p-type conductive dopant material compound 70 and a conventional electron blocking layer material GH1 were combined and matched was used; compared with comparative example 1-1, the lifetime of example 1 is improved by 61%, while the device current efficiency level 153cd/a and the power efficiency level 119lm/W can be maintained high, and the voltage is improved by 0.3V, but at a lower level. In comparative example 1-2, a device structure in which a conventional p-type conductive dopant material PD-ref was combined with an electron blocking layer material compound II-127 was used; compared with the comparative example 1-2, the voltage of the embodiment 1 is greatly reduced by 1.6V, the service life is improved by 81%, the power efficiency is improved by about 31%, and meanwhile, the higher current efficiency level 153cd/A of the device can be kept; although the current efficiency is improved, the working voltage is high in comparative examples 1 to 2, and there is no advantage in power consumption in comprehensive consideration. In comparative examples 1 to 3, a device structure in which a conventional p-type conductive dopant material PD-ref and a conventional electron blocking layer material GH1 were combined and matched was used; compared with comparative examples 1-3, the voltage of example 1 is greatly reduced by 1.3V, the service life is improved by 163%, the power efficiency is improved by 21%, and meanwhile, the higher device efficiency level 153cd/A can be maintained.

By combining various properties of the device, the device structure formed by combining and matching the p-type conductive doping material compound 70 and the electron blocking layer material compounds II-127 disclosed by the invention shows better device performance than the device structure formed by combining and matching the conventional p-type conductive doping material compound PD-ref and/or the electron blocking layer material compound GH 1.

Example 2

An organic electroluminescent device was distinguished from example 1 only in that compounds HT-1 (hole transport material) and compound 70 (p-type conductivity doping material) were evaporated as a hole injection layer (HIL,

) The mass ratio of the compound HT-1 to 70 is 97; the evaporated compound HT-1 in step (3) is used as a hole transport layer (HTL,

) (ii) a Other materials and preparation methods are the same as those of example 1.

Comparative example 2-1

Comparative example 2-1 differs from example 2 only in that compound II-127 in step (4) is replaced with compound GH 1; other materials and preparation methods were the same as in example 2.

Comparative examples 2 to 2

Comparative example 2-2 differs from example 2 only in that the compound 70 in step (2) is replaced with the compound PD-ref; other materials and preparation methods were the same as in example 2.

Comparative examples 2 to 3

Comparative examples 2-3 differ from example 2 only in that compound 70 in step (2) is replaced with compound PD-ref and compound II-127 in step (4) is replaced with compound GH 1; other materials and preparation methods were the same as in example 2.

The detailed device hierarchy and thickness are shown in table 6:

TABLE 6 partial device structures of example 2 and comparative examples 2-1 to 2-3

The structure of the material used newly in the device is as follows:

device performance testing and analysis

At a current density of 10mA/cm ² Color coordinates (CIEx, CIEy), voltage (V), current Efficiency (CE), and power efficiency (lm/W) of the devices in example 2 and comparative examples 2-1 to 2-3 were tested as follows; the device lifetime (LT 95) is at 80mA/cm ² The luminance decays to 95% of the original luminance under driving. The test data are shown in table 7:

TABLE 7 device Performance of example 2 and comparative examples 2-1 to 2-3

Table 7 shows the results of testing electroluminescent devices comprising different combinations of p-type conductivity dopant materials and electron blocking materials. In embodiment 2, a device structure in which the p-type conductive doping material compound 70 and the electron blocking layer material compound II-127 disclosed in the present invention are combined and matched is used. In comparative example 2-1, a device structure in which a p-type conductive doping material compound 70 and a conventional electron blocking layer material GH1 were combined and matched was used; compared with comparative example 2-1, the lifetime of example 2 was improved by 52%, while maintaining a high device efficiency level of 151cd/A, and the voltage was increased by 0.2V, but at a low level. In comparative example 2-2, a device structure in which a conventional p-type conductive dopant material PD-ref was combined and matched with an electron blocking layer material compound II-127 was used; the voltage and efficiency of example 2 are close to those of comparative example 2-2, and the lifetime is improved by about 20%. In comparative examples 2 to 3, a device structure in which a conventional p-type conductive doping material PD-ref and a conventional electron blocking layer material GH1 were combined and matched was used; compared with comparative examples 2-3, the voltage of example 2 is improved by 0.2V, the service life is improved by 63%, and meanwhile, a higher device efficiency level 151cd/A can be maintained.

By combining various properties of the device, the device structure formed by combining and matching the p-type conductive doped material compound 70 and the electron blocking layer material compound II-127 disclosed by the invention shows better device performance than the device structure formed by combining and matching the conventional p-type conductive doped material compound PD-ref and/or the electron blocking layer material compound GH 1.

Example 3-1

An organic electroluminescent device was distinguished from example 1 only in that compounds HT-2 (hole transport material) and compound 70 (p-type conductivity doping material) were evaporated as a hole injection layer (HIL,

) The mass ratio of the compound HT-2 to 70 is 99; the evaporated compound HT-2 in step (3) serves as a hole transport layer (HTL,

) (ii) a The compound II-127 is vapor-deposited on the hole transport layer in step (4) as an electron blocking layer (EBL,

) (ii) a The other materials and preparation methods were the same as in example 1.

Examples 3 to 2

Example 3-2 differs from example 3-1 only in that compound 70 in step (2) was replaced with compound 1357; other materials and preparation methods were the same as in example 3-1.

Examples 3 to 3

Example 3-3 differs from example 3-1 only in that compound II-127 in step (4) is replaced with compound II-136, and the materials and preparation method are the same as those of example 3-1.

Examples 3 to 4

Example 3-4 differs from example 3-1 only in that the compound II-127 in step (4) is used as an electron blocking layer with the compound II-210 (EBL,

) Other materials and preparation methods were the same as those in example 3-1.

Comparative example 3-1

Comparative example 3-1 differs from example 3-1 only in that compound II-127 in step (4) is replaced with compound GH 1; other materials and preparation methods were the same as in example 3-1.

Comparative example 3-2

Comparative example 3-2 differs from example 3-2 only in that compound II-127 in step (4) is replaced with compound GH 1; other materials and preparation methods were the same as in example 3-2.

Comparative examples 3 to 3

Comparative example 3-3 differs from example 3-1 only in that the compound 70 in step (2) is replaced with the compound PD-ref; the materials and preparation method were the same as in example 3-1.

Comparative examples 3 to 4

Comparative example 3-4 differs from example 3-4 only in that the compound 70 in step (2) is replaced with the compound PD-ref; the materials and preparation methods were the same as in examples 3-4.

Comparative examples 3 to 5

Comparative example 3-5 differs from example 3-1 only in that compound 70 in step (2) is replaced with compound PD-ref and compound II-127 in step (4) is replaced with compound GH 1; other materials and preparation methods were the same as in example 3-1.

The detailed device hierarchy and thickness are shown in table 8:

TABLE 8 partial device structures of examples 3-1 to 3-4 and comparative examples 3-1 to 3-5

The structure of the material used newly in the device is as follows:

device performance testing and analysis

At a current density of 10mA/cm ² The devices of examples 3-1 to 3-4 and comparative examples 3-1 to 3-5 were tested for color coordinates (CIEx, CIEy), voltage (V), current Efficiency (CE), and Power Efficiency (PE) as follows; the device lifetime (LT 95) is at 80mA/cm ² The luminance decays to 95% of the original luminance under driving. The test data are shown in table 9:

TABLE 9 device Performance of examples 3-1 to 3-4 and comparative examples 3-1 to 3-5

As shown in table 9, in examples 3-1 to 3-4, the device structures of the p-type conductive doping material compound 70 or compound 1357 disclosed in the present invention and the electron blocking material compound II-127, II-136, or II-210 in combination are used respectively. In comparative examples 3-1 and 3-2, device structures were used in which the p-type conductivity dopant compound 70 or compound 1357 was combined with the conventional electron blocking layer material GH1, respectively. Compared with the comparative example 3-1, the voltage, CE and PE of the example 3-1 are basically kept equal, and the service life is improved by 70 percent; the voltage, CE and PE of example 3-2 were substantially equal and the lifetime was improved by 61.5% as compared with comparative example 3-2. In examples 3-3 to 3-4, the voltage, CE and PE were substantially equalized and the lifetime was improved by 38.3% and 53.3% respectively, as compared with comparative example 3-1. Therefore, the device structures using the combination of the p-type conductivity doping material compound 70 or compound 1357 and the electron blocking material compound II-127, II-136 or II-210 disclosed in the present invention, respectively, all show better device performance than the device structures using the combination of the p-type conductivity doping material compound 70 or compound 1357 and the electron blocking material compound GH1 disclosed in the present invention.

In comparative example 3-3, the device structure in which the p-type conductivity dopant compound PD-ref and the electron blocking layer material compound II-127 of the present invention were combined was used, and the voltage of example 3-2 was lower than that of comparative example 3-3, although it was increased by 0.4V, the efficiency was substantially the same, and the lifetime was increased by 52.1%. Therefore, the device structure using the p-type conductive doped material compound 1357 and the electron blocking layer material compound II-127 in combination and matching disclosed by the invention shows better device performance than the device structure using the conventional p-type conductive doped material compound PD-ref and the electron blocking layer material compound II-127 in combination and matching.

In examples 3-1 and 3-4, the device structures of the p-type conductive doped material compound 70 disclosed in the present invention and the electron blocking layer material compounds II-127 and II-210 respectively in combination and matching were used. In comparative examples 3-3 and 3-4, device structures were used in which the p-type conductivity dopant material compound PD-ref was used in combination with the electron blocking layer material compounds II-127 and II-210. Compared with comparative example 3-3, the voltage of example 3-1 was reduced by 0.1V, the efficiency was almost leveled, and the lifetime was improved by 47.8%. Compared with comparative examples 3-4, the voltage of examples 3-4 was reduced by 0.2V, the efficiency was almost the same, and the lifetime was improved by 12.1%. Therefore, the device structures using the p-type conductive doped material compound 70 disclosed by the invention respectively combined and matched with the electron blocking layer material compounds II-127 and II-210 show better device performance than the device structures using the conventional p-type conductive doped material compound PD-ref combined and matched with the electron blocking layer material compounds II-127 and II-210 disclosed by the invention.

In comparative examples 3 to 5, device structures in which a conventional p-type conductivity dopant material compound PD-ref and a conventional electron blocking layer material compound GH1 were used in combination were used. Compared with the comparative examples 3-5, the voltage of the example 3-1 is reduced by 0.2V, the CE is basically leveled, the PE is improved by 8.2 percent, and the service life is improved by 70 percent; the voltage of the embodiment 3-2 is improved by 0.3V, but the voltage is at a lower level, the CE and the PE are basically kept level, and the service life is improved by 75 percent; the voltage of the embodiment 3-3 is reduced by 0.2V, the CE is basically leveled, the PE is improved by 8.2 percent, and the service life is improved by 38.3 percent; the voltage drop of examples 3-4 was 0.2V, CE and PE were substantially leveled, and lifetime was improved by 53.3%. Therefore, the device structure using the p-type conductivity dopant material compound 70 or compound 1357 disclosed in the present invention in combination with the electron blocking layer material compounds II-127, II-136 and II-210 all showed better device performance than the device structure using the conventional p-type conductivity dopant material compound in combination with the conventional electron blocking layer material compound GH 1.

In summary, comparing the examples and the comparative examples, it can be seen that the first organic compound of the present invention is more desirable to be used as a p-type doping material and the second organic compound of the present invention is more desirable to be used as an electron blocking material in combination with each property of the device. The organic electroluminescent device provided by the invention comprises the first organic compound and the second organic compound with specific structures, so that the service life of the device can be greatly prolonged, the device can be kept to have higher efficiency, and the organic electroluminescent device has obvious advantages in industry.

The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent device and its application, but the present invention is not limited to the above process steps, i.e. it does not mean that the present invention must rely on the above process steps to be carried out. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.

Claims

1. An organic electroluminescent device comprising a cathode and an anode, and an organic layer disposed between the cathode and the anode; the organic layer comprises a first organic layer and a second organic layer; the first organic layer comprises a first organic compound, and the second organic layer comprises a second organic compound;

the first organic compound has a structure as shown in formula I:

r, R ', R ", and R'" are, identically or differently at each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, nitroso group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyloxy group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof;

adjacent substituents in formula I can optionally be linked to form a ring;

the second organic compound has a structure as shown in formula II:

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

2. The organic electroluminescent device of claim 1, wherein the X, Y, identically or differently at each occurrence, is selected from CR "R '" or NR'; r', R "and R" are groups having at least one electron withdrawing group;

preferably, the R, R ', R "and R'" are groups having at least one electron withdrawing group.

3. The organic electroluminescent device according to claim 1, characterized in that X, Y, which are identical or different at each occurrence, are selected from O, S or Se, at least one of R being a group with at least one electron-withdrawing group;

preferably, each of said R is a group having at least one electron withdrawing group.

4. The organic electroluminescent device according to any one of claims 1 to 3, wherein the Hammett constant of the electron-withdrawing group is 0.05 or more, preferably 0.3 or more, more preferably 0.5 or more;

preferably, the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ Boryl, sulfinyl, sulfonyl, phosphinoxy, azaaryl, and substituted with halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ One or at least two of the following groups substituted by boryl, sulfinyl, sulfonyl, phosphinyl and azacyclyl: an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an alkylgermanium group having 3 to 20 carbon atoms, an arylgermanium group having 6 to 20 carbon atoms, and combinations thereof;

more preferably, the electron withdrawing group is selected from the group consisting of: f, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, pyrimidinyl, triazinyl, and combinations thereof.

5. The organic electroluminescent device of claim 1 or 4, wherein the X, Y, identical or different at each occurrence, is selected from the group consisting of:

wherein R is ₂ Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, nitroso group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyloxy group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof;

preferably, said R is ₂ Each occurrence, the same or different, is selected from the group consisting of: f, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazinyl, and combinations thereof;

v, W are selected, identically or differently at each occurrence, from CR _v R _w ，NR _v O, S or Se;

ar, identically or differently on each occurrence, is selected from 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;

A、R _a 、R _b 、R _c 、R _d 、R _e 、R _f 、R _g 、R _h 、R _v and R _w Each time goes outThe nonce is selected, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, nitroso group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinyl group, 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 aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl group having 6 to 20 carbon atoms, and combinations thereof;

a is a group having at least one electron-withdrawing group, and for either of said structures, when R is _a 、R _b 、R _c 、R _d 、R _e 、R _f 、R _g 、R _h 、R _v And R _w When one or at least two of them occur, R _a 、R _b 、R _c 、R _d 、R _e 、R _f 、R _g 、R _h 、R _v And R _w At least one of which is a group having at least one electron-withdrawing group; preferably, the group having at least one electron withdrawing group is selected from the group consisting of: f, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, pentafluorophenyl, 4-cyanotetrafluorophenyl, tetrafluoropyridyl, pyrimidinyl, triazinyl, and combinations thereof;

"-" indicates the position where the X and Y groups are attached to the dehydrobenzodioxazole, dehydrobenzodithiazole or dehydrobenzodiselenazole ring in formula I.

6. The organic electroluminescent device of claim 1 or 4, wherein the X, Y, identical or different at each occurrence, is selected from the group consisting of:

wherein "-" denotes the position at which the X and Y groups are attached to the dehydrobenzodioxazole ring, dehydrobenzodithiazole ring or dehydrobenzodiselenazole ring in formula I.

7. The organic electroluminescent device according to any one of claims 1 to 6, wherein R is selected, identically or differently at each occurrence, from the group consisting of: hydrogen, deuterium, halogen, nitroso group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ Boryl, sulfinyl, sulfonyl, phosphinoxy, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, and substituted with halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ Any one of the following groups substituted with one or at least two of boryl, sulfinyl, sulfonyl and phosphinyl groups: an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, and combinations thereof;

preferably, said R, equal or different at each occurrence, is selected from the group consisting of: hydrogen, deuterium, methyl, isopropyl, NO ₂ ，SO ₂ CH ₃ ，SCF ₃ ，C ₂ F ₅ ，OC ₂ F ₅ ，OCH ₃ Diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, mesityl oxide, or CF ₃ One or at least two substituted vinyl groups of (A) by CN or CF ₃ Substituted ethynyl, dimethylphosphinoxy, diphenylphosphinoxy, F, CF ₃ ，OCF ₃ ，SF ₅ ，SO ₂ CF ₃ Cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis (trifluoromethyl) phenyl, bis (trifluoromethoxy) phenyl, 4-cyanotetrafluorophenyl, substituted by F, CN or CF ₃ Or at least two substituted phenyl or biphenyl groups, a tetrafluoropyridyl group, a pyrimidinyl group, a triazinyl group, a diphenylboryl group, a oxaboro-anthracenyl group, and combinations thereof.

8. The organic electroluminescent device as claimed in claim 7, wherein the X, Y is

9. The organic electroluminescent device according to any one of claims 1 to 8, wherein R is selected from the group consisting of the following structures, the same or different at each occurrence:

wherein the content of the first and second substances,

represents said RA position at which a group is attached to a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in formula I;

preferably, both R in one compound of formula I are the same.

10. The organic electroluminescent device according to claim 9, wherein the first organic compound has a structure represented by formula III:

in the formula III, two Zs are the same, two R structures are the same or different, and Z, X, Y, R is respectively selected from atoms or groups shown in the following table;

the compound having the structure of formula III is selected from the group consisting of:

11. the organic electroluminescent device according to claim 1, wherein the second organic compound has a structure represented by any one of formulas II-1 to II-3:

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

12. The organic electroluminescent device of claim 1, wherein the second organic compound has a structure according to formula II-4 or formula II-5:

adjacent substituents R ₃ Can optionally be linked to form a ring;

adjacent substituents R ₄ Can optionally be linked to form a ring.

13. The organic electroluminescent device according to any one of claims 1 to 12, wherein the ring B and the ring C are selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dimethylfluorenyl group, the occurrence of each of which is the same or different.

14. The organic electroluminescent device according to claim 1, wherein the second organic compound is selected from the group consisting of:

15. the organic electroluminescent device according to claim 1, characterized in that the LUMO level of the first organic compound is greater than 5.05eV and/or the HOMO level of the second organic compound is less than 5.45eV.

16. The organic electroluminescent device according to any one of claims 1 to 15, wherein the first organic layer further comprises a third organic compound having a HOMO level of 5.09eV or more;

preferably, the third organic compound comprises any one or at least two chemical building blocks selected from the group consisting of: triarylamines, carbazoles, fluorenes, spirobifluorenes, thiophenes, furans, phenyls, oligophenylenes, oligofluorenes, and combinations thereof.

17. The organic electroluminescent device according to any one of claims 1 to 16, wherein a third organic layer is further provided between the first organic layer and the second organic layer, the third organic layer containing a fourth organic compound;

the fourth organic compound comprises any one or at least two chemical building blocks selected from the group consisting of: triarylamines, carbazoles, fluorenes, spirobifluorenes, thiophenes, furans, phenyls, oligophenylenes, oligofluorenes, and combinations thereof;

the fourth compound is the same or different from the third compound;

preferably, the fourth organic compound and the third organic compound are the same.

18. The organic electroluminescent device according to any one of claims 1 to 17, wherein the first organic layer and the anode are in contact with each other; the thickness of the first organic layer is 0.1-40 nm;

preferably, the organic electroluminescent device comprises a light-emitting layer, and the second organic layer is arranged between the anode and the light-emitting layer and is in contact with the light-emitting layer; the thickness of the second organic layer is 1 to 100nm.

19. A display module comprising an organic electroluminescent device as claimed in any one of claims 1 to 18.

20. Use of the organic electroluminescent device as claimed in any one of claims 1 to 18 in an electronic device, an electronic element module, a display device or a lighting device.