CN117820326A

CN117820326A - Organic electroluminescent material and device thereof

Info

Publication number: CN117820326A
Application number: CN202211180141.7A
Authority: CN
Inventors: 王强; 王乐; 张子岩; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2022-09-27
Filing date: 2022-09-27
Publication date: 2024-04-05

Abstract

An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is an indolocarbazole fused azamacrocyclic compound with the structure shown in the formula 1, and the compound can be used as a main body material in an organic electroluminescent device, provides better comprehensive performance for the device, and can realize low voltage and long service life at the same time. Electroluminescent devices and compound compositions comprising the organic electroluminescent material and electronic devices comprising the electroluminescent devices are also disclosed.

Description

Organic electroluminescent material and device thereof

Technical Field

The present invention relates to a compound for an organic electronic device, such as an organic light emitting device. And more particularly, to a compound having the structure of formula 1, and an organic electroluminescent device and a compound composition including the same.

Background

Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), 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 electroluminescent devices.

In 1987, tang and Van Slyke of Isomandah reported a double-layered 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). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-emitting solid state devices, they offer 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 fabrication on flexible substrates.

OLEDs can be divided into three different types according to their light emission mechanism. The OLED of the Tang and van Slyke invention is a fluorescent OLED. It uses only singlet light emission. The triplet states generated in the device are wasted through non-radiative decay channels. Thus, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation prevents commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters. Thus, both singlet and triplet states can be harvested, achieving a 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by 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 can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.

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

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

The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.

CN114920750A discloses a compound having the following general structureWherein the structure of formula 2 is fused at any two adjacent positions in formula 1, het is selected from 6-18 membered nitrogen containing heteroarylene groups, and Het contains at least 2 nitrogen atoms. This application discloses only the incorporation of fused indolocarbazoles into macrocyclic structuresThe effect on the properties of compounds of electron-deficient electron-transporting groups having at least two nitrogen atoms is entered, but it does not disclose and teach compounds in which an electrically neutral or electron-rich aryl, heteroaryl, amino group is attached by a single bond or arylene group in an indolocarbazole fused azamacrocyclic fragment, nor the use of such compounds as host materials in organic electroluminescent devices.

A compound is disclosed in US20160163998A1, which has the general structureHowever, compounds having indolocarbazole fused azamacrocyclic skeleton structures are not disclosed, nor are the use of such compounds in organic electroluminescent devices taught.

There is still room for further improvement in many of the host materials reported so far, and further research and development of new materials are still needed to meet the increasingly improved demands of the industry, especially for lower driving voltages, higher device efficiency, longer device lifetime, and other performance demands.

Disclosure of Invention

The present invention aims to solve at least part of the above problems by providing a series of novel compounds having the structure of formula 1. The indolocarbazole fused azamacrocyclic compound with the structure shown in the formula 1 can be used as a main body material in an organic electroluminescent device, and can provide better comprehensive performance for the device, for example, can simultaneously obtain low voltage and long service life.

According to one embodiment of the present invention, a compound is disclosed having a structure represented by formula 1:

wherein,

X ₁ to X ₁₇ Is selected from CR, identically or differently at each occurrence _x Or N;

L ₁ selected from single bonds, or substituted or unsubstituted, having 6-30 carbon atomsArylene of the child;

Ar ₁ selected from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, or a combination thereof; wherein the heteroaryl is selected from the group consisting of: dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, carbazolyl, silafluorenyl, and combinations thereof;

when L ₁ Selected from substituted arylene groups, and when Ar ₁ When selected from substituted aryl, substituted heteroaryl or substituted amino, it is meant that any of the arylene, aryl, heteroaryl or amino groups may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl 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 alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium 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, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

R _x And is selected identically or differently on each occurrence 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 atomsA group, a substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Adjacent substituents R _x Can optionally be linked to form an aromatic ring.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a compound having the structure of formula 1, the specific structure of the compound being as shown in the previous embodiment.

According to another embodiment of the present invention, there is also disclosed a compound composition comprising the compound having the structure of formula 1, the specific structure of the compound being as shown in the previous embodiment.

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

The indolocarbazole fused azamacrocyclic compounds having the structure of formula 1 disclosed herein can be used as host materials in organic electroluminescent devices, can provide better overall performance to the device, e.g., can achieve both low voltage and long lifetime, and can be further used in combination with a second compound, e.g., a compound comprising triazine structural units, as a host material in electroluminescent devices.

Drawings

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

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

Detailed Description

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings 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, a light emitting 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 layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent 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 in a 50:1 molar ratio 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. Pat. 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 in a molar ratio of 1:1 as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. 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, including composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically conductive, sputter deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. By way of reference in its entiretyExamples of implant layers are provided in incorporated U.S. patent application publication 2004/0174116. A description of protective layers 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 by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the 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 sublayers. 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, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over 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 an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.

Devices manufactured according to embodiments of the present invention may be incorporated into a variety of 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, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.

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

As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "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 "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.

It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay 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 states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.

Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe _S -T). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally results in a small Δe _S -T. These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

Definition of terms for substituents

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

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

Cycloalkyl-as used herein, includes cyclic alkyl. Cycloalkyl groups may be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably 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, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl are preferred. In addition, cycloalkyl groups may be optionally substituted.

Heteroalkyl-as used herein, a heteroalkyl comprises an alkyl chain in which one or more carbons is replaced by a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl. In addition, heteroalkyl groups may be optionally substituted.

Alkenyl-as used herein, covers straight chain, branched chain, and cyclic alkylene groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. 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 groups 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 the aryl group 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-condensed 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 '-methylbiphenyl-4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl. In addition, aryl groups may be optionally substituted.

Heterocyclyl or heterocycle-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 nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. 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 nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. 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, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-boron, 1, 3-aza-boron, 1-aza-boron-4-aza, boron-doped compounds, and the like. 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 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 alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group 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 aryloxy groups include phenoxy and biphenoxy. In addition, the aryloxy group may be optionally substituted.

Aralkyl-as used herein, encompasses aryl-substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, cyano, o-cyanobenzyl, o-chlorobenzyl, 1-chlorophenyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, aralkyl groups may be optionally substituted.

Alkyl-as used herein, alkyl-substituted silicon groups are contemplated. The silyl group may be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of the alkyl silicon group include trimethyl silicon group, triethyl silicon group, methyldiethyl silicon group, ethyldimethyl silicon group, tripropyl silicon group, tributyl silicon group, triisopropyl silicon group, methyldiisopropyl silicon group, dimethylisopropyl silicon group, tri-t-butyl silicon group, triisobutyl silicon group, dimethyl-t-butyl silicon group, and methyldi-t-butyl silicon group. In addition, the alkyl silicon group may be optionally substituted.

Arylsilane-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 arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenyl silyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, arylsilane groups may be optionally substituted.

Alkyl germanium group-as used herein, alkyl substituted germanium groups are contemplated. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkyl germanium groups include trimethyl germanium group, triethyl germanium group, methyl diethyl germanium group, ethyl dimethyl germanium group, tripropyl germanium group, tributyl germanium group, triisopropyl germanium group, methyl diisopropyl germanium group, dimethyl isopropyl germanium group, tri-t-butyl germanium group, triisobutyl germanium group, dimethyl-t-butyl germanium group, methyl-di-t-butyl germanium group. In addition, alkyl germanium groups may be optionally substituted.

Arylgermanium group-as used herein, encompasses at least one aryl or heteroaryl substituted germanium group. The arylgermanium group may be an arylgermanium group having 6-30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of aryl germanium groups include triphenylgermanium group, phenylbiphenyl germanium group, diphenylbiphenyl germanium group, phenyldiethyl germanium group, diphenylethyl germanium group, phenyldimethyl germanium group, diphenylmethyl germanium group, phenyldiisopropylgermanium group, diphenylisopropylgermanium group, diphenylbutylgermanium group, diphenylisobutylglycol group, and diphenyltert-butylgermanium group. In addition, the arylgermanium group may be optionally substituted.

The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.

In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, which may be 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 cycloalkyl having 1 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium 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, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof.

It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to 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 equivalent.

In the compounds mentioned in this disclosure, the hydrogen atoms 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 of their enhanced efficiency and stability of the device.

In the compounds mentioned in this disclosure, polysubstituted means inclusive of disubstituted up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.

In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where 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. 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 further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and 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 be taken 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 be taken to mean that the two substituents bound to further distant carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

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

wherein,

L ₁ selected from single bonds, or substituted or unsubstituted arylene groups having 6 to 30 carbon atoms;

When L ₁ Selected from substituted arylene groups, and when Ar ₁ When selected from substituted aryl, substituted heteroaryl or substituted amino, it is meant that any of the arylene, aryl, heteroaryl or amino groups may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted cycloalkyl having 7-30 aralkyl groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, unsubstituted aryl groups having 6-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, unsubstituted amino groups having 0-20 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 _x And is selected identically or differently on each occurrence 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 heteroaryl having 3 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 alkyl 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 alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;

Adjacent substituents R _x Can optionally be linked to form an aromatic ring.

Herein, "adjacent substituent R _x Can optionally be connected toThe formation of an aromatic ring "is intended to mean two adjacent substituents R _x Which may be linked to form an aromatic carbocyclic ring containing no heteroatoms. For example, X ₁ To X ₄ Two adjacent substituents R _x Between X ₅ To X ₈ Two adjacent substituents R _x Between X ₉ To X ₁₁ Two adjacent substituents R _x Between X ₁₂ To X ₁₅ Two adjacent substituents R _x Between, and X ₁₆ And X ₁₇ Two adjacent substituents R _x Between, one or more of these substituent groups may optionally be linked to form an aromatic ring. Obviously, none of these substituent groups may be linked to form a ring.

According to one embodiment of the invention, wherein, when R _x Selected from substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, and, when substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, the adjacent substituents R _x Optionally linked to form an aromatic ring.

According to one embodiment of the invention, wherein adjacent substituents R _x Can be optionally connected to form benzene ring or naphthalene ring.

According to one embodiment of the invention, wherein adjacent substituents R _x And are not connected to form a ring.

According to one embodiment of the invention, wherein Ar ₁ Selected from the structures represented by formula 1-1, formula 1-2, formula 1-3 or formula 1-4;

y is selected identically or differently on each occurrence from C or CR _y And one Y in formula 1-1, formula 1-2 or formula 1-4 is selected from C and is the same as the L ₁ Are connected;

z is selected from CR _z1 R _z2 ，O，S，NR _n Se or SiR _z1 R _z2 ；

R _y ，R _z1 ，R _z2 ，R _n Each time it occurs, the sameOr is selected differently 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 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 0 to 20 carbon atoms, carbonyl, sulfonyl, cyano, sulfonyl, carbonyl, sulfonyl, cyano, sulfonyl, and combinations thereof;

Adjacent substituents R _y ，R _z1 ，R _z2 ，R _n Can optionally be linked to form a ring;

wherein,the L in the formula 1-1 to the formula 1-4 and the formula 1 ₁ The location of the connection.

In this embodiment, any one group selected from the group consisting of a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted silyl group, a substituted arylsilyl group, a substituted alkylgermanium group, a substituted arylgermanium group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxylic acid group, a substituted ester group, a substituted sulfinyl group, a substituted sulfonyl group, a substituted phosphino group, and an alkyl group, a cycloalkyl group, a heteroalkyl group, a heterocyclic group, an aralkyl group, an alkoxy group, an aryloxy group, an alkenyl group, an alkynyl group, an aryl group, an alkylsilyl group, an alkylgermanium group, an arylgermanium group, an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a sulfinyl group, a sulfonyl group, and a phosphino group, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted alkylgermanium group having 3 to 20 carbon atoms, unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

Herein, "adjacent substituent R _y ，R _z1 ，R _z2 ，R _n Can optionally be linked to form a ring "is intended to mean that in formulae 1-1 to 1-4, adjacent substituents R _y Between adjacent substituents R _z1 And R is _z2 Between adjacent substituents R _y And R is _z1 Between adjacent substituents R _y And R is _z2 Between, and adjacent substituents R _y And R is _n Between which one or more of these substituent groups may optionally be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

According to one embodiment of the invention, wherein Ar ₁ Selected from the structures represented by formulas 1-1 or 1-4.

According to one embodiment of the invention, wherein R _y ，R _z1 ，R _z2 And is selected identically or differently on each occurrence from the group consisting ofThe group: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, cyano groups, and combinations thereof; adjacent substituents R _y ，R _z1 ，R _z2 Can optionally be linked to form a ring.

According to one embodiment of the invention, wherein R _y ，R _z1 ，R _z2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, t-butyl, adamantyl, norbornyl, cyclopentyl, cyclohexyl, vinyl, phenyl, naphthyl, biphenyl, phenanthryl, triphenylene, 9-dimethylfluorenyl, cyano, and combinations thereof.

According to one embodiment of the invention, wherein Z is selected from O, S or NR _n 。

According to one embodiment of the invention, wherein R _n And is selected identically or differently on each occurrence from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms.

According to one embodiment of the invention, wherein R _n And is selected, identically or differently, for each occurrence from: phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene,a group or a 9, 9-dimethylfluorenyl group.

According to one embodiment of the invention, wherein Ar ₁ The groups are selected, identically or differently, for each occurrence, from substituted or unsubstituted aryl groups having from 6 to 24 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted silafluorenyl groups, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, or combinations thereof.

According to one embodiment of the invention, wherein Ar ₁ And is selected identically or differently on each occurrence from the group consisting of: phenyl, naphthaleneGroup, biphenyl group, phenanthryl group, terphenyl group, triphenylene group,a group, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenylcarbazolyl, diphenylamino, or a combination thereof.

According to one embodiment of the invention, wherein X ₁ To X ₁₇ Is selected from CR, identically or differently at each occurrence _x 。

According to one embodiment of the invention, wherein R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof.

According to one embodiment of the invention, wherein R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, adamantyl, norbornyl, cyclopentyl, cyclohexyl, vinyl, phenyl, naphthyl, biphenyl, phenanthryl, triphenylene, 9-dimethylfluorenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenylcarbazolyl, cyano, and combinations thereof.

According to one embodiment of the invention, wherein L ₁ Selected from single bonds, or substituted or unsubstituted arylene groups having 6 to 24 carbon atoms.

According to one embodiment of the invention, wherein L ₁ Selected from single bond, phenylene, naphthylene, biphenylene or phenanthrylene.

According to an embodiment of the invention, wherein the compound is selected from the group consisting of compounds a-1 to a-187, the specific structure of a-1 to a-187 is seen in claim 8.

According to one embodiment of the invention, the hydrogen energy in the structures of compounds a-1 to a-187 is partially or completely replaced by deuterium.

According to an embodiment of the present invention, there is also disclosed an electroluminescent device including a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer including a compound having a structure of formula 1, the specific structure of the compound being as shown in any one of the previous embodiments.

According to one embodiment of the invention, wherein in the electroluminescent device, the organic layer is a light emitting layer.

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

According to an embodiment of the present invention, in the electroluminescent device, wherein the organic layer is a light emitting layer, and includes a second compound selected from structures represented by formula 2:

In the formula (2) of the present invention,

Q ₁ to Q ₃ Is selected from CR, identically or differently at each occurrence _Q Or N, and Q ₁ To Q ₃ At least two of which are selected from N;

R’ ₁ ，R’ ₂ ，R’ ₃ ，R _Q and is selected identically or differently on each occurrence 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 atomsSubstituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Adjacent substituents R' ₁ ，R’ ₂ ，R’ ₃ ，R _Q Can optionally be linked to form a ring.

In this embodiment, "adjacent substituent R' ₁ ，R’ ₂ ，R’ ₃ ，R _Q Being able to be optionally linked to form a ring "is intended to mean that in formula 2, adjacent substituents R' ₁ And R is _Q Between adjacent substituents R' ₂ And R is _Q Between adjacent substituents R' ₃ And R is _Q In between, any one or more of these substituent groups may be linked to form a ring. Obviously, none of these adjacent groups of substituents may be linked to form a ring.

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

According to one embodiment of the present invention, wherein, in formula 2, R' ₁ ，R’ ₂ ，R’ ₃ ，R _Q The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, or combinations thereof.

According to one embodiment of the present invention, wherein, in formula 2, R' ₁ ，R’ ₂ ，R’ ₃ ，R _Q And is selected identically or differently on each occurrence from the group consisting of: phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene, diphenylAnd a furan group, dibenzothiophene group, carbazole group, 9-dimethylfluorene group, A group, a benzoxazolyl group, a phenanthrooxazole group, a benzothiazolyl group, and combinations thereof.

According to one embodiment of the present invention, wherein in formula 2, Q ₁ To Q ₃ Selected from N.

According to an embodiment of the present invention, wherein the second compound is selected from the group consisting of compounds B-1 to B-67, the specific structure of compounds B-1 to B-67 is shown in claim 14.

According to one embodiment of the invention, wherein the hydrogen energy in the structures of compounds B-1 to B-67 is partially or completely replaced by deuterium.

According to one embodiment of the invention, wherein in the organic electroluminescent device, the organic layer is a light emitting layer comprising at least one phosphorescent light emitting material.

According to one embodiment of the invention, wherein the phosphorescent material is a metal complex having M (L _a ) _m (L _b ) _n (L _c ) _q Is of the general formula (I);

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

L _a 、L _b 、L _c a first ligand, a second ligand and a third ligand coordinated to the M; l (L) _a 、L _b 、L _c Can optionally be linked to form a multidentate ligand;

L _a 、L _b 、L _c may be the same or different; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of M, n, q is equal to the oxidation state of M; when m is greater than or equal to 2, a plurality of L _a May be the same or different; when n is 2, two L _b May be the same or different; when q is 2, two L _c May be the same or different;

L _a has a structure as shown in formula 3:

wherein,

ring D is selected from a 5 membered heteroaryl ring or a 6 membered heteroaryl ring;

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

ring D and ring E via U _a And U _b Condensing;

U _a and U _b Selected identically or differently on each occurrence from C or N;

R _d ，R _e each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;

V ₁ -V ₄ is selected from CR, identically or differently at each occurrence _v Or N;

R _d ，R _e ，R _v and is selected, identically or differently, on each occurrence, 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 aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Adjacent substituents R _d ，R _e ，R _v Can optionally be linked to form a ring;

L _b 、L _c each occurrence is identically or differently selected from any one of the following structures:

/>

wherein,

R _a ，R _b and R is _c Each occurrence, identically or differently, represents mono-substituted, poly-substituted, or unsubstituted;

X _b and is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR _N1 And CR (CR) _C1 R _C2 ；

X _c And X _d And is selected identically or differently on each occurrence from the group consisting of: o, S, se and NR _N2 ；

R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 And is selected identically or differently on each occurrence 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 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 alkylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 0 to 20 carbon atoms Amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

the ligand L _b 、L _c In the structure of (a), adjacent substituent R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 Can optionally be linked to form a ring.

Herein, adjacent substituents R _d ，R _e ，R _v Can optionally be linked to form a ring, intended to mean that when a substituent R is present _d R is substituent R _e R is substituent R _v In which adjacent substituents, e.g. adjacent substituents R _d Between and adjacent substituents R _e Between and adjacent substituents R _v Between and adjacent substituents R _d And R is R _e Between and adjacent substituents R _d And R is R _v Between and adjacent substituents R _e And R is R _v Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, when substituents R are present _d R is substituent R _e R is substituent R _v In this case, none of the substituents may be bonded to form a ring.

Herein, adjacent substituents R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 Can optionally be linked to form a ring, intended to mean groups of substituents adjacent thereto, e.g. two substituents R _a Between two substituents R _b Between two substituents R _c Between, substituent R _a And R is _b Between, substituent R _a And R is _c Between, substituent R _b And R is _c Between, substituent R _a And R is _N1 Between, substituent R _b And R is _N1 Between, substituent R _a And R is _C1 Between, substituent R _a And R is _C2 Between, substituent R _b And R is _C1 Between, substituent R _b And R is _C2 Between, substituent R _a And R is _N2 In between the two,substituent R _b And R is _N2 Between, and R _C1 And R is _C2 In between, any one or more of these substituent groups may be linked to form a ring. For example, the number of the cells to be processed,r is an adjacent substituent _a ，R _b Can optionally be linked to form a ring, which can form a ring comprising, but not limited to, one or more of the following structures: />/>

Wherein W is selected from O, S, se, NR ' or CR ' R '; wherein said R', R _a ’，R _b ' definition and R _a The same applies. Obviously, these substituents may not all be linked to form a ring.

According to one embodiment of the present invention, wherein, in formula 3, R _d 、R _e 、R _v At least one or two groups of adjacent substituents are linked to form a ring. For example, two substituents R _d Joined to form a ring, or two substituents R _e Joined to form a ring, or two substituents R _v Joined to form a ring, or substituent R _d And substituent R _e Forms a ring, or substituent R _d And substituent R _v Forms a ring, or substituent R _e And substituent R _v Is connected with each other to form a ring, or two substituents R _d Two substituents R simultaneously linked to form a ring _e Joined to form a ring, or two substituents R _d Two substituents R simultaneously linked to form a ring _v Joined to form a ring, or two substituents R _e Two substituents R simultaneously linked to form a ring _v Are linked to form a ring, substituent R _e And substituent R _v Simultaneously 2 substituents R linked to form a ring _v Joined to form a ring, or substituent R _d And substituent R _v Simultaneously 2 rings are connected to form a ringSubstituent R _v The connection forms a ring; r is R _d 、R _e 、R _v Similar situation is true when more groups of adjacent substituents are joined to form a ring.

According to one embodiment of the invention, the electroluminescent device wherein the phosphorescent material is a metal complex having M (L _a ) _m (L _b ) _n Is of the general formula (I);

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

L _a 、L _b a first ligand and a second ligand coordinated to the M, respectively; l (L) _a 、L _b Can optionally be linked to form a multidentate ligand;

m is 1, 2 or 3; n is 0, 1 or 2; the sum of M and n is equal to the oxidation state of M; when m is greater than or equal to 2, a plurality of L _a May be the same or different; when n is 2, two L _b May be the same or different;

L _a has a structure as shown in formula 3:

wherein,

ring D and ring E via U _a And U _b Condensing;

R _d ，R _e ，R _v and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedSubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 ring carbon atoms, substituted or unsubstituted heterocyclyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl 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, substituted or unsubstituted arylgermyl groups having 0 to 20 carbon atoms, substituted or unsubstituted aminoxy groups having 6 to 20 carbon atoms, carbonyl groups, sulfonyl groups, cyano groups, sulfonyl groups, and combinations thereof;

wherein the ligand L _b The structure is as follows:

wherein R is ₁ To R ₇ Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 aryl having 6 to 30 carbon atomsA substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl silicon group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl silicon group having 6 to 20 carbon atoms, a substituted or unsubstituted alkyl germanium group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl germanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphine group, and combinations thereof.

According to one embodiment of the invention, the electroluminescent device wherein the ligand L _b The structure is as follows:

wherein R is ₁ -R ₃ At least one selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R ₄ -R ₆ At least one of which is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.

wherein R is ₁ -R ₃ At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 1 to 20 carbon atoms, or combinations thereof; and/or R ₄ -R ₆ At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 1 to 20 carbon atoms, or combinations thereof.

wherein R is ₁ -R ₃ At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof; and/or R ₄ -R ₆ At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof.

According to one embodiment of the invention, the electroluminescent device wherein the phosphorescent material is an Ir complex, a Pt complex or an Os complex.

According to one embodiment of the invention, the electroluminescent device wherein the phosphorescent material is an Ir complex and has Ir (L _a )(L _b )(L _c )、Ir(L _a ) ₂ (L _b )、Ir(L _a )(L _b ) ₂ 、Ir(L _a ) ₂ (L _c ) Or Ir (L) _a )(L _c ) ₂ Any of the structures shown.

According to one embodiment of the invention, wherein L _a Having a structure as shown in formula 3 and comprising at least one member selected from the group consisting of a 6-membered and 6-membered aromatic ring, a 6-membered and 6-membered heteroaromatic ring, a 6-membered and 5-membered aromatic ring and a 6-membered and 5-membered heteroaromatic ring Is a structural unit of the group.

According to one embodiment of the invention, the electroluminescent device, wherein L _a Has a structure as shown in formula 3 and comprises at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

According to one embodiment of the invention, the phosphorescent material is an Ir complex and comprises a ligand L in the electroluminescent device _a The L is _a And is selected from any one of the group consisting of the following structures, identically or differently, at each occurrence:

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according to one embodiment of the invention, wherein in the electroluminescent device the phosphorescent material is an Ir complex and comprises a ligand L _b The L is _b And is selected from any one of the group consisting of the following structures, identically or differently, at each occurrence:

according to one embodiment of the invention, wherein in the electroluminescent device, the phosphorescent light-emitting material is selected from the group consisting of:

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according to another embodiment of the present invention, there is also disclosed a compound composition comprising a compound having a structure represented by formula 1, the specific structure of the compound being as shown in any one of the preceding embodiments.

According to another embodiment of the present invention, wherein the compound composition further comprises a second compound selected from the group consisting of structures represented by formula 2:

Wherein,

R’ ₁ ，R’ ₂ ，R’ ₃ ，R _Q and is selected identically or differently on each occurrence 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 atomsA substituted or unsubstituted aryloxy group having from 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

According to another embodiment of the present invention, an electronic device is also disclosed, which includes an electroluminescent device, and the specific structure of the electroluminescent device is as shown in any one of the foregoing embodiments.

According to another embodiment of the present invention, in the preparation of the electroluminescent device of the present invention, when two or more host materials and a light emitting material are used to form a light emitting layer by co-evaporation, the two or more host materials and the light emitting material are respectively placed in different evaporation sources, or a mixture of the two or more host materials pre-mixed is placed in the same evaporation source and then co-evaporated with the light emitting material placed in another evaporation source to form a light emitting layer, and this pre-mixing manner can further save the evaporation source. Taking the present invention as an example, the compound having the structure of formula 1, the second compound, and the light-emitting material of the present invention may be co-evaporated in different evaporation sources to form the light-emitting layer, or the mixture having the structure of formula 1 and the second compound may be pre-mixed in the same evaporation source and co-evaporated with the light-emitting material placed in another evaporation source to form the light-emitting layer.

Combined with other materials

The materials described herein for specific 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 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

Materials described herein as useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

In the examples of material synthesis, all reactions were carried out under nitrogen protection, unless otherwise indicated. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bei Yi g sublimator, etc.), in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.

Material synthesis examples:

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

synthesis example 1: synthesis of Compound A-1

Step 1: synthesis of intermediate 3

Intermediate 1 (25.0 g,89.3 mmol), intermediate 2 (16.8 g,98 mmol), palladium acetate (0.89 g,4.45 mmol), tris (o-methylphenyl) phosphine (4.7 g,17.8 mmol), cesium carbonate (58.2 g,178.6 mmol), DMF (200 mL) were added to a three-necked flask under nitrogen atmosphere and reacted at 140℃for 32h. After the reaction was completed, cooled to room temperature, filtered, the filtrate was extracted with ethyl acetate, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography (PE/dcm=2:1) to give intermediate 3 (13 g, yield: 60%) as a white solid.

Step 2: synthesis of intermediate 5

Intermediate 3 (8.5 g,35.1 mmol), intermediate 4 (12.1 g,38.4 mmol), palladium acetate (0.35 g,1.75 mmol), 4, 5-bis-diphenylphosphine-9, 9-dimethylxanthene (Xantphos, 2.0g,3.5 mmol), sodium t-butoxide (6.7 g,70 mmol), toluene (160 mL) were added to a three-necked flask under nitrogen atmosphere and reacted at 90℃for 16h. After the reaction was completed, cooled to room temperature, extracted with ethyl acetate, the organic phase was washed with water, the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography (PE/dcm=4:1) to give intermediate 5 (13 g, yield: 86%) as a white solid.

Step 3: synthesis of intermediate 6

Intermediate 5 (13 g,30.2 mmol), palladium acetate (304 mg,1.5 mmol), tri-tert-butylphosphine (870 mg,3 mmol), potassium carbonate (8.2 g,60.3 mmol), N-dimethylacetamide (120 mL) were added to a three-necked flask under nitrogen atmosphere and reacted at 110℃for 16h. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography (PE/dcm=6:1) to give intermediate 6 (10 g, yield: 95%) as a white solid.

Step 4: synthesis of intermediate 7

Intermediate 6 (10.0 g,28.5 mmol), pinacol biborate (10.85 g,42.7 mmol), palladium acetate (283 mg,1.4 mmol), tricyclohexylphosphine (784 mg,2.8 mmol), potassium acetate (5.6 g,57 mmol), xylene (200 mL) were added to a three-necked flask under nitrogen atmosphere and reacted at 130℃for 16h. After the reaction was completed, cooled to room temperature, filtered, the filtrate was extracted with ethyl acetate, the organic phase was washed with water, and the solvent was removed by concentration, and the crude product was purified by column chromatography (PE/ea=10:1) to give intermediate 7 (9 g, yield: 71%) as a white solid.

Step 5: synthesis of intermediate 9

Intermediate 7 (9.0 g,20.4 mmol), intermediate 8 (4.5 g,22.4 mmol), tetrakis (triphenylphosphine) palladium (1.0 g,1.02 mmol), potassium carbonate (5.6 g,40.4 mmol), toluene (160 mL), ethanol (40 mL), water (40 mL) were added under nitrogen to a three-necked flask and reacted at 100℃for 16h. After the reaction was completed, cooled to room temperature, extracted with ethyl acetate, the organic phase was washed with water, the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography (PE/dcm=4:1) to give intermediate 9 (5 g, yield: 56%) as a yellow solid.

Step 6: synthesis of intermediate 10

Intermediate 9 (3.0 g,6.8 mmol), triphenylphosphine (4.5 g,17.2 mmol) and o-dichlorobenzene (30 mL) were charged to a three-necked flask under nitrogen and reacted at 190℃for 16h. After the reaction was completed, cooled to room temperature, and the crude product was purified by column chromatography (PE/dcm=4:1) to give intermediate 10 (2.4 g, yield: 89%) as a white solid.

Step 7: synthesis of Compound A-4

Intermediate 10 (1.5 g,3.7 mmol), intermediate 11 (0.94 g,4.1 mmol), tris (dibenzylideneacetone) dipalladium (0.21 g,1.75 mmol), 2-dicyclohexylphosphine-2, 6 dimethoxy-1, 1-biphenyl (Sphos, 0.15g,0.37 mmol), sodium t-butoxide (710 mg,7.4 mmol), xylene (100 mL) were added to a three-necked flask under nitrogen atmosphere and reacted at 130℃for 16h. After the reaction was completed, cooled to room temperature, extracted with ethyl acetate, the organic phase was washed with water, the solvent was removed by concentration, and the crude product was purified by column chromatography (PE/dcm=4:1) to give compound a-4 (1 g, yield: 48.5%) as a pale yellow solid. The product was identified as the target product and had a molecular weight of 558.2.

Synthesis example 2: synthesis of Compound A-2

Intermediate 10 (1.4 g,3.4 mmol), intermediate 12 (0.84 g,4.1 mmol), tris (dibenzylideneacetone) dipalladium (0.31 g,0.34 mmol), 2-dicyclohexylphosphine-2, 6 dimethoxy-1, 1-biphenyl (Sphos, 0.28g,0.68 mmol), sodium t-butoxide (653 mg,6.8 mmol), xylene (100 mL) were added to a three-necked flask under nitrogen atmosphere and reacted at 130 ℃ for 16h. After the reaction was completed, cooled to room temperature, extracted with ethyl acetate, the organic phase was washed with water, the solvent was removed by concentration, and the crude product was purified by column chromatography (PE/dcm=4:1) to give compound a-2 (1.3 g, yield: 72%) as a pale yellow solid. The product was identified as the target product and had a molecular weight of 532.2.

Those skilled in the art will recognize that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other compound structures of the present invention.

Device example 1

First, a glass substrate having a 120nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was baked in a glove box filled with nitrogen gas to remove moisture, and then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 ^-8 In the case of Torr Is evaporated on the ITO anode in sequence by thermal vacuum. Co-evaporation of Compound HT and Compound HI was used as hole injection layer (HIL, weight ratio 97:3, ">). The compound HT is used as hole transport layer (HTL, -/-A)>). Compound EB is used as electron blocking layer (EBL, -/-for)>). Then the compound A-2 of the present invention as a first host and the compound B-14 as a second host and acts asCompound RD, which is a dopant, is co-evaporated for use as a light emitting layer (EML, weight ratio 58:40:2, ">). Use of Compound HB as hole blocking layer (HBL, -/->). On the hole blocking layer, a compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL, weight ratio 40:60, < > >). Finally, vapor deposition->8-hydroxyquinoline-lithium (Liq) with a thickness as an Electron Injection Layer (EIL) and vapor-deposited +.>Is used as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.

Device example 2

The embodiment of device example 2 is the same as device example 1 except that the compound a-4 of the present invention is used in place of the compound a-2 of the present invention in the light emitting layer (EML) as a host.

Device comparative example 1

The embodiment of device comparative example 1 is the same as device example 1 except that compound C is used in place of the compound a-2 of the present invention in the light emitting layer (EML) as a main body.

Device comparative example 2

Embodiment of device comparative example 2 is the same as device example 1 except that compound D is used in place of the inventive compound A-2 as a host in the light-emitting layer (EML)

The detailed device layer structure and thickness are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.

TABLE 1 device structures for device examples 1-2 and comparative examples 1-2

The material structure used in the device is as follows:

table 2 shows the constant current of 15mA/cm ² Maximum emission wavelength (lambda) of device measured under the condition _max ) And voltage (V) data, and at a constant current of 80mA/cm ² Device lifetime (LT 97) measured under the condition, device lifetime (LT 97) refers to the time required for the device luminance to decay to 97% of its original luminance.

TABLE 2 device data for device examples 1-2 and comparative examples 1-2

Device ID	λ _max (nm)	Voltage[V]	LT97[h]
				Example 1	620	3.62	59
Example 2	620	3.48	88
				Comparative example 1	621	4.00	0.5
Comparative example 2	620	4.13	46.3

As can be seen from the data in table 2, the maximum emission wavelengths of the examples and comparative examples are substantially identical. The voltages of example 1 and example 2 were reduced by 0.38V and 0.52V, respectively, as compared to comparative example 1; more importantly, in terms of device lifetime, the lifetime of examples 1 and 2 was significantly improved by 117-fold and 175-fold, respectively, compared to comparative example 1. Compared with the compound C, the novel compound with the structure shown in the formula 1 formed by fusing the seven-membered ring on the N atom of the indolocarbazole structural fragment has stronger rigidity and better stability, and can simultaneously achieve the reduction of the voltage of the device and the remarkable improvement of the service life of the device when being used as a main material in the device, so that the device performance is more excellent.

Example 1 and example 2 also exhibited more excellent overall properties than comparative example 2: in terms of device voltage, the voltages of example 1 and example 2 were reduced by 0.51V, 0.65V, respectively; in terms of device lifetime, the lifetimes of example 1 and example 2 were each improved by a large margin of 27%, 90%. This shows that compared with compound D with triazinyl bonded to indolocarbazole fused azamacrocyclic fragment, the compound with the structure of formula 1 of the present invention has made a breakthrough in both device voltage reduction and device lifetime extension when used as host material.

From the above results, it can be seen that the compound disclosed by the invention can prolong the service life of the device while reducing the operating voltage of the device, so that the compound has wide commercial development prospect and application value.

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

Claims

1. A compound having a structure represented by formula 1:

wherein,

When L ₁ Selected from substituted arylene groups, and when Ar ₁ Selected from the group consisting of substituted aryl, substituted heteroaryl and substituted amino, meaning that the arylene, aryl, heteroaryl or ammoniaAny one of the groups may be substituted with one or more groups selected from 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 alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, carbonyl groups, cyano groups, isocyanate groups, sulfonyl groups, and combinations thereof;

R _x And is selected identically or differently on each occurrence 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 heteroaryl having 3 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 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 alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 0 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, Isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

adjacent substituents R _x Can optionally be linked to form an aromatic ring.

2. The compound of claim 1, wherein Ar ₁ Selected from the structures represented by formula 1-1, formula 1-2, formula 1-3, or formula 1-4:

z is selected from CR _z1 R _z2 ，O，S，NR _n Se or SiR _z1 R _z2 ；

R _y ，R _z1 ，R _z2 ，R _n And is selected identically or differently on each occurrence 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 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl A group, sulfonyl group, phosphino group, and combinations thereof;

wherein,the L in the formula 1-1 to the formula 1-4 and the formula 1 ₁ The position of the connection;

preferably, the Ar ₁ Selected from the structures represented by formulas 1-1 or 1-4.

3. The compound of claim 2, wherein R _y ，R _z1 ，R _z2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, cyano groups, and combinations thereof;

adjacent substituents R _y ，R _z1 ，R _z2 Can optionally be linked to form a ring;

preferably, R _y ，R _z1 ，R _z2 And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, t-butyl, adamantyl, norbornyl, cyclopentyl, cyclohexyl, vinyl, phenyl, naphthyl, biphenyl, phenanthryl, triphenylene, 9-dimethylfluorenyl, cyano, and combinations thereof.

4. The compound of claim 2, wherein Z is selected from O, S or NR _n ；

Preferably, R _n The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;

more preferably, R _n Selected identically or differently on each occurrence from phenyl, naphthyl, biphenyl, phenanthryl,a terphenyl group, a triphenylene group,a group or a 9, 9-dimethylfluorenyl group.

5. A compound according to claim 1 or 2, wherein Ar ₁ The groups are selected, identically or differently, on each occurrence, from substituted or unsubstituted aryl groups having from 6 to 24 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted silafluorenyl groups, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, or combinations thereof;

preferably Ar ₁ And is selected, identically or differently, for each occurrence from: phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene,a group, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenylcarbazolyl, diphenylamino, or a combination thereof.

6. The compound of any one of claims 1-5, wherein X ₁ To X ₁₇ Is selected from CR, identically or differently at each occurrence _x ，R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof;

Preferably, R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, adamantyl, norbornyl, cyclopentyl, cyclohexyl, vinyl, phenyl, naphthyl, biphenyl, phenanthrylTriphenylene, 9-dimethylfluorenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenylcarbazolyl, cyano, and combinations thereof.

7. The compound of any one of claims 1-6, wherein L ₁ Selected from single bonds, or substituted or unsubstituted arylene groups having 6 to 24 carbon atoms;

preferably L ₁ Selected from single bond, phenylene, naphthylene, biphenylene or phenanthrylene.

8. The compound of claim 1, wherein the compound is selected from the group consisting of:

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optionally, the hydrogen in the structures of compounds a-1 to a-187 can be partially or fully substituted with deuterium.

9. An electroluminescent device, comprising:

a cathode electrode, which is arranged on the surface of the cathode,

an anode is provided with a cathode,

and an organic layer disposed between the cathode and anode, the organic layer comprising the compound of any one of claims 1 to 8.

10. The electroluminescent device of claim 9 wherein the organic layer is a light emitting layer;

Preferably, the organic layer is a light emitting layer, and the compound is a host material.

11. The electroluminescent device of claim 10, wherein the organic layer is a light emitting layer and comprises a second compound selected from the group consisting of structures represented by formula 2:

in the formula (2) of the present invention,

R’ ₁ ，R’ ₂ ，R’ ₃ ，R _Q and is selected identically or differently on each occurrence 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 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms Alkylsilyl, substituted or unsubstituted arylsilyl having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having from 6 to 20 carbon atoms, substituted or unsubstituted amino having from 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

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

preferably, the second compound is a host material.

12. The electroluminescent device of claim 11, wherein in formula 2, R' ₁ ，R’ ₂ ，R’ ₃ ，R _Q The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, or combinations thereof;

preferably, R' ₁ ，R’ ₂ ，R’ ₃ ，R _Q And is selected identically or differently on each occurrence from the group consisting of: phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, triphenylene, 9-dimethylfluorenyl,a group, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzoxazolyl, phenanthroxazole, benzothiazolyl, and combinations thereof.

13. An electroluminescent device as claimed in claim 11 or 12 wherein in formula 2Q ₁ To Q ₃ Selected from N.

14. The electroluminescent device of claim 11 wherein the second compound is selected from the group consisting of:

/>

wherein, optionally, hydrogen in the structures of the compounds B-1 to B-67 can be partially or completely substituted by deuterium.

15. The electroluminescent device of any one of claims 9-14, wherein the organic layer is a light emitting layer comprising at least one phosphorescent light emitting material.

16. The electroluminescent device of claim 15 wherein the phosphorescent material is a metal complex having M (L _a ) _m (L _b ) _n (L _c ) _q Is of the general formula (I);

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

L _a 、L _b 、L _c a first ligand and a second ligand which are coordinated with the M respectivelyAnd a third ligand; l (L) _a 、L _b 、L _c Can optionally be linked to form a multidentate ligand;

L _a has a structure as shown in formula 3:

wherein,

ring D and ring E via U _a And U _b Condensing;

R _d ，R _e ，R _v and is selected, identically or differently, on each occurrence, 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 aryl having 2 to 20 carbon atomsAlkenyl of atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl of 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl of 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl of 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl of 6 to 20 carbon atoms, substituted or unsubstituted amino of 0 to 20 carbon atoms, acyl, carbonyl, carboxylate, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein,

R _a ，R _b ，R _c ，R _N1 ，R _N2 ，R _C1 And R is _C2 And is selected identically or differently on each occurrence 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 cycloalkyl having 3 to 20 ring carbon atomsAn aralkyl group of 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group of 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group of 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group of 6 to 20 carbon atoms, a substituted or unsubstituted amino group of 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

17. The electroluminescent device of claim 15 wherein the phosphorescent material is a metal complex having M (L _a ) _m (L _b ) _n Is of the general formula (I);

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

L _a has a structure as shown in formula 3:

wherein,

ring D and ring E via U _a And U _b Condensing;

wherein the ligand L _b The structure is as follows:

wherein R is ₁ To R ₇ Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Preferably, wherein R ₁ -R ₃ At least one or two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 1 to 20 carbon atoms, or combinations thereof; and/or R ₄ -R ₆ At least one or two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 1 to 20 carbon atoms, or combinations thereof;

more preferably, wherein R ₁ -R ₃ At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof; and/or R ₄ -R ₆ At least two of which are, identically or differently, selected from the group consisting of substituted or unsubstituted alkyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having from 2 to 20 carbon atoms, or combinations thereof.

18. A compound composition comprising a compound of any one of claims 1 to 8.

19. The compound composition of claim 18, comprising a second compound selected from the group consisting of structures represented by formula 2:

wherein,

R’ ₁ ，R’ ₂ ，R’ ₃ ，R _Q and is selected identically or differently on each occurrence 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 atomsAlkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

20. An electronic device comprising the electroluminescent device of any one of claims 9 to 17.