CN115734641A - Organic electroluminescent device - Google Patents

Abstract

An organic electroluminescent device is disclosed. The organic electroluminescent device includes an anode, a cathode, a light emitting layer disposed between the anode and the cathode, and a first organic layer disposed between the anode and the light emitting layer, the first organic layer including a first compound having a structure of formula 1 and a second compound having a structure of formula 2. The organic electroluminescent device has the excellent characteristics of low voltage and high efficiency, and can provide better device performance. An electronic assembly comprising the organic electroluminescent device is disclosed. Also disclosed is a combination of compounds comprising a first compound having the structure of formula 1 and a second compound having the structure of formula 2.

Description

Organic electroluminescent device

Technical Field

The present invention relates to organic electronic devices, and in particular, to an organic electroluminescent device. And more particularly, to an organic electroluminescent device including a first compound having a structure of formula 1 and a second compound having a structure of formula 2 in a first organic layer, and an electronic assembly including the organic electroluminescent device.

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 photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.

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

OLEDs can be classified into three different types according to their light emitting mechanism. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are capable of generating singlet excitons through reverse intersystem crossing, resulting in high IQE.

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

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

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

Organic electroluminescent devices convert electrical energy into light by applying a voltage across the device. Generally, 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, an electron buffer material, a hole blocking material, an electron transport material, a hole blocking material, and the like according to the function of the material. When a bias is applied to the device, holes are injected from the anode into the light-emitting layer and electrons are injected from the cathode into the light-emitting layer. The holes and electrons meet to form excitons, which recombine to emit light. The hole injection layer is one of important functional layers influencing the performance of the organic electroluminescent device, and the selection and matching of materials of the hole injection layer can have important influence on the performance of the organic electroluminescent device, such as driving voltage, efficiency, service life and the like. Organic electroluminescent devices having characteristics of low driving voltage, high efficiency, long lifetime, etc. are commercially desired, and thus, the development of a novel hole injection layer is a very critical research field.

In most of the early OLED devices, only one layer of organic material is disposed between the anode and the light emitting layer, and the functions of hole injection, hole transport and even electron blocking are considered, for example, in 1987, the first two-layer organic electroluminescent device reported by Tang and Van Slyke in eastman kodak, and the hole injection material used is NPD, TPD, etc. However, these materials do not match the energy levels of the anode material (such as ITO), hole injection is very difficult, and there is a large ohmic loss at the interface, so the device voltage is very high. In order to obtain better interface energy level matching, the hole transport functional material is further divided into a hole injection material and a hole transport material, and the hole injection material at this time is a polyarylamine structure, such as:

the material has a shallow HOMO energy level (the HOMO energy level is about-4.80 eV), and compared with NPD, the material can be better matched with an ITO energy level. In order to obtain a better hole injection effect, the above devices are further improved in the industry, and p-type doping materials are doped into the above materials, and the p-type doping materials are commonly used as follows:

the p-type doping material is a strong electron acceptor, and can generate complete charge transfer (inter charge transfer) with the polyarylamine structure, so that an ohmic contact state is achieved, and the voltage of the device can be greatly reduced. However, it should be noted that although the problem of current limiting by ITO interface injection is solved, the HOMO level of the polyarylate material is shallow, the barrier from the hole injection material to the host material is still large, and the improvement space of the device performance is very small.

For commercial purposes, the industry has chosen to use host materials with deep HOMO levels (around-5.10 eV), such as:

the material is matched with a p-type doping material with deep LUMO to be used as a hole injection material in a device, at the moment, the interface can reach a quasi-ohmic contact or ohmic contact state, the ohmic loss at the interface can be ignored, and the HOMO energy level difference between a host material and a main body material is greatly reduced, so that the material combination enables the device to reach a higher level.

Different p-type doping materials and different host materials can generate different hole injection effects, the energy level matching degree of the two materials is particularly important, and the higher the matching degree is, the better the interface injection effect is. In order to obtain better hole injection effect, it is very important to develop a novel hole injection layer, so that screening a combination of a proper host material and a p-type conductive doping material is crucial to achieving the above purpose, and the device performance can reach a higher level.

U.S. Pat. No. 3,987,311A 1 discloses a compound having the structure of dehydrobenzodioxazole, dehydrobenzodithiazole or dehydrobenzodiselenazole and the like

Organic compounds useful as p-type doping materials with deep LUMO orThe application only focuses on the p-type doped material itself, and does not focus on the effect of the selection of the p-type doped material and the hole transport material on the device performance.

CN112909188A discloses an organic electroluminescent device, mainly focused on a p-type dopant

And a matrix material with triarylamine and carbazole structures

The p-type doping material and other host materials with hole transmission functions are matched to influence the device performance as a hole injection layer, and the effect of the matching of the p-type doping material and other host materials with hole transmission functions on the device performance is not disclosed or paid attention to.

The doped hole injection layer achieves a p-type doping effect through the strong electron capturing capacity of the p-type doping material, and effectively improved hole injection and conductivity can be obtained. In such a doped hole injection layer, on the one hand, it is very important to research and develop more excellent p-type doping materials and/or more excellent hole transport materials; on the other hand, matching of the p-type doped material and the hole transport material is more important, and the mismatch often results in great loss of device performance. Therefore, the selection of a proper combination of p-type doping material and hole transport material is very critical.

Disclosure of Invention

The present invention aims to provide a novel series of organic electroluminescent devices to solve at least some of the above problems. The novel organic electroluminescent device comprises an anode, a cathode, a light-emitting layer arranged between the anode and the cathode, and a first organic layer arranged between the anode and the light-emitting layer, wherein the first organic layer at least comprises a first compound with a structure of a formula 1 and a second compound with a structure of a formula 2. The novel material combination consisting of the first compound and the second compound can be used in a hole injection layer in an organic electroluminescent device, so that the organic electroluminescent device has excellent characteristics of low voltage and high efficiency, and better device performance can be provided.

According to an embodiment of the present invention, there is disclosed an organic electroluminescent device including:

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

a cathode electrode, which is provided with a cathode,

a light emitting layer disposed between an anode and a cathode, and a first organic layer disposed between the anode and the light emitting layer, wherein the first organic layer includes at least a first compound and a second compound, wherein the first compound has a structure represented by formula 1:

in formula 1, X and Y are selected, identically or differently on each occurrence, from NR ', CR "R'", O, S or Se;

Z ₁ and Z ₂ Identically or differently on each occurrence is selected 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 phosphinoxy 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, and combinations thereof;

at least one of R, R 'and R' is a group having at least one electron withdrawing group;

adjacent substituents R, R 'and R' in formula 1 can optionally be linked to form a ring;

the second compound is a monoamine compound and has a structure represented by formula 2:

in formula 2, ar ₃ Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₁ and Ar ₂ Each occurrence, the same or different, is selected from the structures represented by formula 3:

wherein, X ₁ To X ₈ Is selected, identically or differently on each occurrence, from C, CR ₃ Or N; x ₁ To X ₈ One of them is selected from C and is reacted with L ₁ Or L ₂ Connecting; when L is ₁ Or L ₂ When selected from single bonds, X ₁ To X ₈ One of them is selected from C and is connected with N;

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

R ₃ each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and containing oxygen or sulfur atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylcarbonylyl having 6 to 20 carbon atoms, acyl, carbonyl, isothiocarbonyl, sulfonyl, hydroxyl, mercapto, and combinations thereof;

adjacent substituents R in formula 2 ₁ ，R ₂ ，R ₃ Can optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed a compound combination comprising a first compound and a second compound, wherein the first compound has a structure represented by formula 1:

in formula 1, X and Y are, identically or differently on each occurrence, selected from NR ', CR ' R ', O, S or Se;

Z ₁ and Z ₂ Is selected, identically or differently on each occurrence, 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 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 phosphinoxy 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, and combinations thereof;

at least one of R, R 'and R' is a group having at least one electron withdrawing group;

adjacent substituents R, R 'and R' in formula 1 may optionally be linked to form a ring;

the second compound is a monoamine compound and has a structure represented by formula 2:

in formula 2, ar ₃ Selected from substituted orUnsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₁ and Ar ₂ Each occurrence, the same or different, is selected from the structures represented by formula 3:

wherein X ₁ To X ₈ Is selected, identically or differently on each occurrence, from C, CR ₃ Or N; x ₁ To X ₈ One of them is selected from C and is reacted with L ₁ Or L ₂ Connecting; when L is ₁ Or L ₂ When selected from single bonds, X ₁ To X ₈ One of them is selected from C and is connected with N;

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

R ₃ each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and containing oxygen or sulfur atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, carbonyl, cyano, carbonyl, mercapto, and combinations thereof;

adjacent substituents R in formula 2 ₁ ，R ₂ ，R ₃ Can optionally be linked to form a ring.

According to another embodiment of the invention, an electronic assembly is also disclosed, which comprises the organic electroluminescent device described in the above embodiment.

The novel organic electroluminescent device disclosed by the invention comprises a novel material combination consisting of a first compound with a structure of formula 1 and a second compound with a structure of formula 2, which can be used for a hole injection layer, and the effective matching of the two specific materials improves the injection and transmission effects of the device hole; in addition, the material with the structure of formula 2 can be used as a hole injection material, a hole transport material and an electron blocking material, and is directly contacted with the light-emitting layer, and the microcavity effect is adjusted by adjusting the thickness of the material. Compared with the traditional device, the device has the advantages that the number of the electron blocking layers is reduced, the process cost for manufacturing the device is reduced, the complexity of the structure is reduced, the defects possibly existing at the interface are reduced, the hole injection capability is improved, and the device has the excellent characteristics of low voltage and high efficiency.

Drawings

Fig. 1 is a schematic view of an organic light emitting device that may contain the organic electroluminescent devices disclosed herein.

Fig. 2 is a schematic view of another organic light emitting device that may contain the organic electroluminescent devices disclosed herein.

Detailed Description

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but not by way of limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the various layers and exemplary materials are described in more detail in U.S. Pat. No. 7,279,704B2, columns 6-10, which are incorporated herein by reference in their entirety.

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50 ₄ m-MTDATA of TCNQ, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1. Examples of cathodes are disclosed in U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, which disclose examples of cathodesIncluding a composite cathode having a thin layer of a metal such as Mg: ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of a protective layer can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.

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

The OLED also requires an encapsulation layer, as shown in fig. 2, which is a schematic, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent No. 7,968,146b2, the entire contents of which are incorporated herein by reference.

Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.

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

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

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

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

It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can 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 mono-triplet gap in order to switch between energy states. Thermal energy can activate a transition from a triplet state back to a 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. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state. 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 singlet-triplet energy gap (Δ Ε) _S-T ). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds typically results in small Δ E _S-T . These states may include CT states. Typically, 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, preferred are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl. 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-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, preferred are cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl. In addition, cycloalkyl groups may be optionally substituted.

Heteroalkyl-as used herein, heteroalkyl comprises one or more carbons in an alkyl chain that are formed by substitution with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom, and a boron atom. 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 the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.

Alkynyl-as used herein, straight chain alkynyl is contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 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 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' -t-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesitylphenyl and m-tetrabiphenyl. In addition, the aryl group may beOptionally 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, benzothiophenepyridine, benzoselenophenepyridine, selenobenzene, cinnoline, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, and their analogs. In addition, heteroaryl groups may be optionally substituted.

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

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

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

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

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

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 tripropyl-germyl group, a tributyl-germyl group, a triisopropylgermyl group, a methyldiisopropylgermyl group, a dimethylisopropyl-germyl 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 diphenyltert-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, azatriphenylene includes dibenzo [ f, h ] quinoxaline, dibenzo [ f, h ] quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-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, polysubstituted means a range including disubstituted 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 be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (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 illustrated by the following equation:

according to an embodiment of the present invention, there is disclosed an organic electroluminescent device including:

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

a cathode electrode, which is provided with a cathode,

a light-emitting layer disposed between an anode and a cathode, and a first organic layer disposed between the anode and the light-emitting layer, wherein the first organic layer contains at least a first compound and a second compound; wherein the first compound has a structure represented by formula 1:

in formula 1, X and Y are selected, identically or differently on each occurrence, from NR ', CR "R'", O, S or Se;

Z ₁ and 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 group, nitro group, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, SCN, OCN, SF ₅ Substituted or unsubstituted with boron alkyl, sulfinyl, sulfonyl, phosphinoAn 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, and combinations thereof;

at least one of R, R 'and R' is a group having at least one electron withdrawing group;

adjacent substituents R, R 'and R' in formula 1 can optionally be linked to form a ring;

the second compound is a monoamine compound and has a structure represented by formula 2:

in formula 2, ar ₃ Selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₁ and Ar ₂ Each occurrence, the same or different, is selected from the structures represented by formula 3:

wherein X ₁ To X ₈ Selected, identically or differently at each occurrence, from C, CR ₃ Or N; x ₁ To X ₈ One of them is selected from C and is reacted with L ₁ Or L ₂ Connecting; when L is ₁ Or L ₂ When selected from single bonds, X ₁ To X ₈ One of them is selected from C and is connected with N;

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

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

adjacent substituents R in formula 2 ₁ ，R ₂ ，R ₃ Can optionally be linked to form a ring.

In the present context, an oxygen or sulfur atom-containing heteroaryl group in formula 2 is intended to mean that the heteroaryl group comprises at least one O or S atom, and that the O or S atom is a ring atom of the heteroaryl group; including but not limited to oxazole, thiazole, oxadiazole, oxatriazole, bisoxazole, thiadiazole, benzoxazole, benzisoxazole, benzothiazole, phenothiazine, phenoxazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine. Obviously, carbazole, indolocarbazole, quinoline, isoquinoline are not within the scope of the oxygen or sulfur atom containing heteroaryl group.

Herein, the second compound is a monoamine compound, and is intended to mean that the second compound has only one amine group structure, and has been shown in formula 2.

In this example, adjacent substituents R, R ', R "and R'" in formula 1 can optionally be linked to form a ring, and is intended to mean that, in formula 1, adjacent substituent groups, such as adjacent substituents R "and R '", adjacent substituents R and R' ", and two adjacent substituents R, any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, none of these adjacent substituent groups may be linked to form a ring.

Here, the adjacent substituents R in the formula 2 ₁ ，R ₂ And R ₃ Can optionally be joined to form a ring, intended to represent, in the same formula3 adjacent substituent groups, e.g. adjacent substituents R ₁ And R ₂ Adjacent substituents R ₁ And R ₃ Adjacent substituents R ₂ And R ₃ Two adjacent substituents R ₃ Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.

According to one embodiment of the invention, wherein in formula 1, X and Y are selected, identically or differently at each occurrence, from CR "R '" or NR', wherein R ', R "and R'" are groups having at least one electron-withdrawing group.

According to one embodiment of the invention, wherein, in formula 1, R ', R "and R'" are groups having at least one electron withdrawing group.

According to one embodiment of the invention, wherein, in formula 1, X and Y are selected, identically or differently on each occurrence, from O, S or Se, at least one of R is a group with at least one electron-withdrawing group.

According to one embodiment of the present invention, wherein, in formula 1, each R is a group having at least one electron withdrawing group.

According to an embodiment of the invention, the Hammett constant of the electron-withdrawing group is ≧ 0.05, preferably ≧ 0.3, more preferably ≧ 0.5.

The Hammett substituent constant value of the electron withdrawing group is more than or equal to 0.05, the electron withdrawing capability is strong, the LUMO energy level of the compound can be remarkably reduced, and the effect of improving the charge mobility is achieved.

The hammett substituent constant value includes the para-constant and/or meta-constant of the hammett substituent, and any one of the para-constant and meta-constant satisfies 0.05 or more, which is a preferable optional group in the present invention.

According to an embodiment of the invention, wherein 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 aryl groups substituted with halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ Boryl, sulfinyl, sulfonyl, phosphinoxy, an azaaryl group, substituted with one or more of any of the following: 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, and combinations thereof.

According to an embodiment of the invention, wherein 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.

According to one embodiment of the invention, wherein X and Y, on each occurrence, are selected, identically or differently, from the group consisting of:

O，S，Se，

R ₅ 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 phosphinoxy 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 atomsA group, 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, and combinations thereof;

preferably, R ₅ 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;

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

ar is the same or different at each occurrence and is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl 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 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 borane group, a sulfinyl group, a sulfonyl group, a phosphinoxy 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 aryloxy group having 2 to 20 carbon atomsCarbon atom alkenyl groups, substituted or unsubstituted alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;

a is a group having at least one electron withdrawing group, and for either structure, when R _a ，R _b ，R _c ，R _d ，R _e ，R _f ，R _g ，R _h ，R _v And R _w When one or more 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.

In the present embodiment, ""' indicates a position where the X and Y are linked to a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in the formula 1.

According to one embodiment of the invention, wherein X and Y are selected, identically or differently at each occurrence, from the group consisting of:

O，S，Se，

in the present embodiment, "' indicates the position in said X and Y to which the dehydrobenzodioxazole, dehydrobenzodithiazole, or dehydrobenzodiselenazole ring in said formula 1 is attached.

According to one embodiment of the invention, wherein 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, isocyano, 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 of the following substituted with one or more of boryl, sulfinyl, sulfonyl and phosphinyl: 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.

According to one embodiment of the invention, wherein 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 By one or more of the vinyl groups in (A), 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 Phenyl or biphenyl substituted by one or more of (a), tetrafluoropyridylPyrimidinyl, triazinyl, diphenylboryl, oxaboronyl, and combinations thereof.

According to one embodiment of the invention, wherein X and Y are

According to one embodiment of the invention, wherein R, on each occurrence, is selected, identically or differently, from the group consisting of:

in the present embodiment, it is preferred that,

represents a position where the R group is attached to a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in formula 1.

According to an embodiment of the present invention, wherein two R are the same in one first compound represented by formula 1.

According to an embodiment of the present invention, wherein said first compound is selected from the group consisting of compound 1 to compound 1356; for specific structures of said compounds 1 to 1356 see claim 10.

According to an embodiment of the present invention, wherein the second compound has a structure represented by any one of formulas 2-1 to 2-4:

wherein, X ₁ To X ₈ Is selected, identically or differently on each occurrence, from CR ₃ Or N;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₃ selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

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

R ₃ each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkylAn 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 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing an oxygen atom or a sulfur atom, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

wherein adjacent substituents R ₁ ，R ₂ And R ₃ Can optionally be linked to form a ring.

In this example, the adjacent substituents R ₁ ，R ₂ And R ₃ Can optionally be linked to form a ring, is intended to mean that, in the same structure represented by formula 3, adjacent substituent groups, for example adjacent substituents R ₁ And R ₂ Adjacent substituents R ₁ And R ₃ Adjacent substituents R ₂ And R ₃ Two adjacent substituents R ₃ Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, none of these adjacent substituent groups may be linked to form a ring.

According to one embodiment of the present invention, wherein the second compound has a structure represented by formula 2-1 or formula 2-2.

According to an embodiment of the present invention, wherein said L ₁ And L ₂ Each occurrence being the same or different and is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted phenanthrenylene group, and a substituted or unsubstituted phenylene groupSubstituted or unsubstituted triphenylene groups, substituted or unsubstituted pyridylene groups, substituted or unsubstituted anthracenylene groups, substituted or unsubstituted pyrenylene groups, or combinations thereof.

According to an embodiment of the present invention, wherein said L ₁ And L ₂ Each occurrence, the same or different, is selected from the group consisting of:

in this embodiment, "+" indicates the position where L-1 to L-13 are bonded to nitrogen in formula 2, and the dotted line indicates that L-1 to L-13 are bonded to Ar in formula 2 ₁ Or Ar ₂ The location of the connection.

According to an embodiment of the present invention, wherein said L ₁ And/or L ₂ Selected from single bonds.

According to an embodiment of the present invention, wherein said Ar ₃ Selected from substituted aryl groups having 6 to 30 carbon atoms, or substituted heteroaryl groups having 3 to 30 carbon atoms, said aryl or heteroaryl groups being substituted with one or more groups selected from the group consisting of: deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 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;

according to an embodiment of the present invention, wherein said Ar ₃ Selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dialkyl fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or combinations thereof.

According to an embodiment of the present invention, wherein said Ar ₃ Selected from the group consisting of:

in this embodiment, the dotted line represents the Ar ₃ The position bonded to nitrogen in formula 2.

According to one embodiment of the invention, wherein R ₁ And R ₂ Each occurrence identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, and substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms. A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein R ₁ And R ₂ Each occurrence, identically or differently, is selected from hydrogen, deuterium, fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, or a combination thereof.

According to one embodiment of the invention, wherein R ₃ Each occurrence, which may be the same or different, is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing an oxygen atom or a sulfur atom, and combinations thereof.

According to one embodiment of the present invention, when R ₃ When selected from the group consisting of substituted alkyl groups having 1 to 20 carbon atoms, substituted aryl groups having 6 to 20 carbon atoms, and substituted heteroaryl groups having 3 to 30 carbon atoms and containing oxygen or sulfur atoms, said alkyl, aryl or heteroaryl groups are substituted with one or more groups selected from the group consisting of: deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclyl groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 20 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms containing oxygen or sulfur atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 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.

According to one embodiment of the invention, wherein R ₃ Each occurrence, identically or differently, is selected from hydrogen, deuterium, fluoro, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, phenanthryl, anthracenyl, pyrenyl, or a combination thereof.

According to an embodiment of the present invention, wherein the second compound is selected from the group consisting of compound C-1 to compound C-116; the specific structures of the compound C-1 to the compound C-116 are shown in claim 16.

According to an embodiment of the invention, wherein the device further comprises a second organic layer, the second organic layer being arranged between the first organic layer and the light emitting layer, the second organic layer comprising at least a second compound.

According to an embodiment of the invention, wherein the first organic layer is in direct contact with the anode.

According to one embodiment of the present invention, wherein the second organic layer is in direct contact with the light emitting layer.

According to one embodiment of the invention, wherein the first organic layer is in direct contact with the second organic layer.

According to another embodiment of the invention, an electronic component is also disclosed, which comprises an organic electroluminescent device, and the specific structure of the organic electroluminescent device is shown in any one of the embodiments.

According to an embodiment of the invention, wherein the electronic component is a display component or a lighting component.

According to another embodiment of the present invention, there is also disclosed a compound combination comprising a first compound and a second compound, wherein the first compound has a structure represented by formula 1:

in formula 1, X and Y are, identically or differently on each occurrence, selected from NR ', CR ' R ', O, S or Se;

Z ₁ and 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, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ Boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstitutedSubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof;

at least one of R, R 'and R' is a group having at least one electron withdrawing group;

adjacent substituents R, R 'and R' in formula 1 can optionally be linked to form a ring;

the second compound is a monoamine compound and has a structure represented by formula 2:

in formula 2, ar ₃ Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₁ and Ar ₂ Each occurrence, the same or different, is selected from the structures represented by formula 3:

wherein, X ₁ To X ₈ Selected from C, identically or differently on each occurrence,CR ₃ or N; x ₁ To X ₈ One of them is selected from C and is reacted with L ₁ Or L ₂ Connecting; when L is ₁ Or L ₂ When selected from single bonds, X ₁ To X ₈ One of them is selected from C and is connected with N;

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

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

adjacent substituents R in formula 2 ₁ ，R ₂ And R ₃ Can optionally be linked to form a ring.

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 US2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that can 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 compound combinations disclosed herein may be used in conjunction with a variety of light emitting dopants, 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, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that can be used in combination.

In the device of the present invention, charge injection, transport layers such as a hole transport layer, an electron transport layer, and an electron injection layer; the luminescent layer at least comprises a luminescent dopant and at least a host compound, and the luminescent dopant can be a fluorescent luminescent dopant and/or a phosphorescent luminescent dopant; a hole blocking layer may also be included.

The first compound and the second compound used in the present invention can be obtained by referring to the preparation method in the prior art, and are not described herein again. The method of fabricating the electroluminescent device is not limited, and the method of fabricating the following examples is only an example and should not be construed as limiting. The preparation of the following examples can be reasonably modified by those skilled in the art in light of the prior art. For example, the ratio of the materials in each organic layer is not particularly limited, and those skilled in the art can reasonably select the materials within a certain range according to the prior art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by 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-mentioned device usage, testing method, etc., and can obtain the intrinsic data of the sample with certainty and without influence, the above-mentioned relevant contents are not repeated in this patent.

Device embodiment

Example 1: and preparing the fluorescent organic electroluminescent device.

First, a 0.7mm thick glass substrate is used, with a pre-patterned layer thereon

Thick Indium Tin Oxide (ITO) was used as the anode and the ITO surface was treated with oxygen plasma and UV ozone after washing the substrate with deionized water and detergent. The substrate was then dried in a glove box to remove moisture and loaded onto a rack into a vacuum chamber. Organic layers specified below, in a vacuum of about 10 degrees ^-6 In the case of Torr

The evaporation is carried out on the anode layer in sequence by vacuum thermal evaporation:first, compound C-2 and compound 70 were simultaneously evaporated as a hole injection layer (HIL, 97,

) The evaporated compound C-2 was used as a hole transport layer (HTL,

) On which a compound BH and a compound BD are simultaneously evaporated as a light-emitting layer (EML, 98,

) The compound HB was evaporated as a hole blocking layer (HBL,

) Compound ET and Liq were co-deposited as an electron transport layer (ETL, 40,

) Vapor deposition of

Liq in thickness as an Electron Injection Layer (EIL). Finally, metal aluminum is evaporated as a Cathode (Cathode,

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

Example 2: the same preparation method as in example 1 was conducted except that the compound C-12 and the compound 70 were evaporated as a hole injection layer (HIL, 97,

) And the evaporated compound C-12 was used as a hole transport layer (HTL,

)。

comparative example 1: same preparation method as example 1 except for evaporating compound HT-1 and compound 70 asThe hole injection layer (HIL, 97,

) And an evaporated compound HT-1 is used as a hole transport layer (HTL,

)。

comparative example 2: the same preparation method as in example 1 was conducted except that the compound HT-2 and the compound 70 were evaporated as a hole injection layer (HIL, 97,

) And an evaporated compound HT-2 is used as a hole transport layer (HTL,

)。

comparative example 3: the same preparation method as in example 1 was conducted except that the compound C-2 and the compound PD-1 were evaporated as a hole injection layer (HIL, 97,

)。

comparative example 4: the same preparation method as that of example 2 was used except that the compound C-12 and the compound PD-1 were evaporated as a hole injection layer (HIL, 97,

)。

the detailed structures and thicknesses of the hole injection layer and the hole transport layer of the device are shown in the following table. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.

Table 1 shows the partial device structures of examples 1 to 2 and comparative examples 1 to 4:

table 1 partial device structures of examples 1 to 2 and comparative examples 1 to 4

The structure of the materials used in the device is as follows:

table 2 shows device performances of examples 1 to 2 and comparative examples 1 to 4, in which color Coordinates (CIE), voltage (V), power Efficiency (PE) and External Quantum Efficiency (EQE) were measured at a current density of 10mA/cm ² Measured under the conditions.

Table 2 device performance of examples 1 to 2 and comparative examples 1 to 4

Numbering	CIEx	CIEy	V(V)	PE(lm/W)	EQE(％)
						Example 1	0.140	0.094	4.12	5.19	7.91
Example 2	0.139	0.095	4.27	3.90	6.08
						Comparative example 1	0.140	0.103	4.33	3.42	5.05
Comparative example 2	0.138	0.099	4.31	3.63	5.63
						Comparative example 3	0.140	0.094	8.76	1.44	4.70
Comparative example 4	0.139	0.095	10.69	0.66	2.59

Table 2 shows the test results of the electroluminescent device comprising different p-type conductivity dopant materials and hole transport materials used in combination, and it can be seen from the color coordinates that the color coordinates of the illustrated example and the comparative example are substantially the same.

Example 1 and example 2 are compared with comparative example 1 and comparative example 2, respectively, and the examples and comparative examples are different in the host material in HIL, and it is noted that both HT-1 and HT-2 are currently commercially available host materials, and are very excellent hole transport materials. However, the device results show that the voltage of the embodiment is lower than that of the comparative example, the power efficiency and the EQE are also obviously better than that of the comparative example, and the matching degree of the host material and the p-type conductive doping material of the embodiment is higher, and the hole injection effect is better.

Example 1 and example 2 are compared with comparative example 3 and comparative example 4 respectively, the difference between the examples and the comparative examples is that p-type conductive doping materials are different, the device result shows that the voltage of the examples is only about 4.2V, while the voltage of the comparative examples is as high as 8.76V and 10.69V, and the examples and the comparative examples have the advantage of rolling property; furthermore, the embodiments are also absolutely advantageous, both in terms of power efficiency and EQE, again demonstrating the higher degree of matching of the hole injection material combinations of the embodiments.

It can be seen from the above results that the p-type conductive doped material and the host material in examples 1 and 2 are more matched, the hole injection capability is higher, and the device performance is more excellent, so that it is proved that when the combination of the first compound and the second compound selected by the invention is used as a hole injection layer material, the organic electroluminescent device can have excellent performance and unique advantages of low voltage and high efficiency, and the wide prospect in commercial application is indicated.

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

Claims (21)

1. An organic electroluminescent device, comprising:

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

a cathode electrode, which is provided with a cathode,

a light-emitting layer disposed between an anode and a cathode, and a first organic layer disposed between the anode and the light-emitting layer, wherein the first organic layer contains at least a first compound and a second compound; wherein the first compound has a structure represented by formula 1:

in formula 1, X and Y are, identically or differently on each occurrence, selected from NR ', CR ' R ', O, S or Se;

Z ₁ and Z ₂ Identically or differently on each occurrence is selected 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, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF ₅ A boryl group, a sulfinyl group, a sulfonyl group, a phosphinoxy 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, and combinations thereof;

at least one of R, R 'and R' is a group having at least one electron withdrawing group;

adjacent substituents R, R 'and R' in formula 1 may optionally be linked to form a ring;

the second compound is a monoamine compound and has a structure represented by formula 2:

in formula 2, ar ₃ Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms, or a combination thereof;

Ar ₁ and Ar ₂ Each occurrence, the same or different, is selected from the structures represented by formula 3:

wherein X ₁ To X ₈ Selected, identically or differently at each occurrence, from C, CR ₃ Or N; x ₁ To X ₈ One of them is selected from C and is reacted with L ₁ Or L ₂ Connecting;

R ₁ and R ₂ Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atomsA silicon group, a substituted or unsubstituted arylsilane group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

R ₃ each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms and containing oxygen or sulfur atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylcarbonylyl having 6 to 20 carbon atoms, acyl, carbonyl, isothiocarbonyl, sulfonyl, hydroxyl, mercapto, and combinations thereof;

adjacent substituents R in formula 2 ₁ ，R ₂ ，R ₃ Can optionally be linked to form a ring.

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

3. The organic electroluminescent device of claim 1, wherein in formula 1, X and Y are selected, identically or differently on each occurrence, from O, S or Se, at least one of R being a group having at least one electron-withdrawing group; preferably, each R is a group having at least one electron withdrawing group.

4. An organic electroluminescent device as claimed in 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.

5. The organic electroluminescent device of any one of claims 1 to 4, wherein 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 Boryl, sulfinyl, sulfonyl, phosphinoxy, an azaaryl group, substituted with one or more of any of the following: 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, and combinations thereof;

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.

6. The organic electroluminescent device of any one of claims 1,4 or 5, wherein X and Y, the same or different at each occurrence, are selected from the group consisting of:

O，S，Se，

R ₅ each occurrence, the same or different, 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 phosphinoxy 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, and combinations thereof;

preferably, R ₅ 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 and W are selected, identically or differently on each occurrence, from CR _v R _w ，NR _v O, S or Se;

ar is the same or different at each occurrence and is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl 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 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 phosphinoxy 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, and combinations thereof;

a is a group having at least one electron withdrawing group, and for either structure, when R _a ，R _b ，R _c ，R _d ，R _e ，R _f ，R _g ，R _h ，R _v And R _w In the presence of one or more of (a), R _a ，R _b ，R _c ，R _d ，R _e ，R _f ，R _g ，R _h ，R _v And R _w 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;

preferably, wherein X and Y are, identically or differently on each occurrence, selected from the group consisting of:

O，S，Se，

"" denotes a position in said X and Y to which a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in said formula 1 is bonded.

7. The organic electroluminescent device of any one of claims 1 to 6, wherein R, identically or differently 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 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 of the following substituted with one or more of boryl, sulfinyl, sulfonyl and phosphinyl: 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, R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, methylIsopropyl group, 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 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, by F, CN or CF ₃ One or more substituted phenyl or biphenyl groups of (a), tetrafluoropyridyl, pyrimidinyl, triazinyl, diphenylboryl, oxaboroanthracenyl, and combinations thereof.

8. The organic electroluminescent device as claimed in claim 7, wherein X and Y are

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

preferably, two R are the same in one first compound represented by formula 1;

represents a position where the R group is linked to a dehydrobenzodioxazole ring, a dehydrobenzodithiazole ring or a dehydrobenzodiselenazole ring in formula 1.

10. The organic electroluminescent device according to claim 9, wherein the first compound is selected from the group consisting of compound 1 to compound 1356; the compounds 1 to 1356 have the structures represented by formula 1-1:

wherein, two Z are the same, and Z, X, Y and R respectively correspond to atoms or groups selected from the following table:

11. the organic electroluminescent device according to claim 1, wherein the second compound has a structure represented by any one of formulae 2-1 to 2-4:

wherein X ₁ To X ₈ Selected from CR, identically or differently at each occurrence ₃ Or N;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₃ selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

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

R ₃ each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 3 to 20 ring atomsA cyclic group, 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 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing an oxygen atom or a sulfur atom, 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, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R ₁ ，R ₂ And R ₃ Can optionally be linked to form a ring;

preferably, the second compound has a structure represented by formula 2-1 or formula 2-2.

12. The organic electroluminescent device as claimed in any one of claims 1 to 11, wherein L ₁ And L ₂ Each occurrence identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzoselenophenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted pyrenylene group, or a combination thereof;

preferably, L ₁ And/or L ₂ Selected from single bonds.

13. The organic electroluminescent device as claimed in any one of claims 1 to 12, wherein Ar is Ar ₃ Is selected from substitution has 6-(ii) aryl of 30 carbon atoms, or substituted heteroaryl of 3 to 30 carbon atoms, said aryl or heteroaryl being substituted with one or more groups selected from the group consisting of: deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted heterocyclic groups having 3 to 20 ring atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted alkynyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanyl groups having 3 to 20 carbon atoms, unsubstituted arylgermanyl groups having 6 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;

preferably, ar ₃ Selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dialkyl fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, or combinations thereof.

14. The organic electroluminescent device as claimed in any one of claims 1 to 13, wherein R is ₁ And R ₂ Each occurrence identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, and substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms. SubstitutionOr unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or combinations thereof;

preferably, R ₁ And R ₂ Each occurrence, identically or differently, is selected from hydrogen, deuterium, fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, or a combination thereof.

15. The organic electroluminescent device as claimed in any one of claims 1 to 14, wherein R is ₃ Each occurrence, identically or differently, is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing an oxygen atom or a sulfur atom, and combinations thereof;

preferably, when R is ₃ When selected from the group consisting of substituted alkyl groups having 1 to 20 carbon atoms, substituted aryl groups having 6 to 20 carbon atoms, and substituted heteroaryl groups having 3 to 30 carbon atoms and containing oxygen or sulfur atoms, said alkyl, aryl or heteroaryl groups are substituted with one or more groups selected from the group consisting of: deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 20 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms containing oxygen or sulfur atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 carbon atoms, unsubstituted cycloalkyl having 2 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 carbon atoms, and the likeAlkylgermyl groups of carbon atoms, unsubstituted arylgermyl groups having 6 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;

more preferably, R ₃ Selected from hydrogen, deuterium, fluoro, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, triphenylene, phenanthryl, anthracenyl, pyrenyl, or combinations thereof.

16. The organic electroluminescent device as claimed in claim 1, wherein the second compound is selected from the group consisting of:

17. the organic electroluminescent device of claim 1, wherein the device further comprises a second organic layer disposed between the first organic layer and the light-emitting layer, the second organic layer comprising at least the second compound.

18. The organic electroluminescent device of any one of claims 1 to 17, wherein the first organic layer is in direct contact with the anode.

19. The organic electroluminescent device of claim 17, wherein the second organic layer is in direct contact with the light-emitting layer.

20. A combination of compounds comprising a first compound and a second compound; the first compound has a structure represented by formula 1:

in formula 1, X and Y are selected, identically or differently on each occurrence, from NR ', CR "R'", O, S or Se;

Z ₁ and Z ₂ Is selected, identically or differently on each occurrence, 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 phosphinoxy 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, and combinations thereof;

at least one of R, R 'and R' is a group having at least one electron withdrawing group;

adjacent substituents R, R 'and R' in formula 1 can optionally be linked to form a ring;

the second compound is a monoamine compound and has a structure represented by formula 2:

in formula 2, ar ₃ Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstitutedUnsubstituted heteroaryl having 3 to 30 carbon atoms;

L ₁ and L ₂ Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;

Ar ₁ and Ar ₂ Each occurrence, the same or different, is selected from the structures represented by formula 3:

wherein, X ₁ To X ₈ Is selected, identically or differently on each occurrence, from C, CR ₃ Or N; x ₁ To X ₈ One of them is selected from C and is reacted with L ₁ Or L ₂ Connecting;

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

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

adjacent substituents R in formula 2 ₁ ，R ₂ And R ₃ Can optionally be linked to form a ring.

21. An electronic assembly comprising the organic electroluminescent device of any one of claims 1 to 19.

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