CN114163462A

CN114163462A - Polycyclic compounds and devices thereof

Info

Publication number: CN114163462A
Application number: CN202111011389.6A
Authority: CN
Inventors: 赵春亮; 李宏博; 毕欣; 田学超; 王峥; 邝志远
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2020-09-11
Filing date: 2021-09-02
Publication date: 2022-03-11

Abstract

A polycyclic compound and a device thereof are disclosed. The polycyclic compound is a compound having a structure represented by formula 1, and is useful as a light emitting material in an electroluminescent device. These novel compounds can change the molecular orientation with the host in electroluminescent devices, providing better device performance. Also disclosed is a combination of compounds.

Description

Polycyclic compounds and devices thereof

Technical Field

The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a novel polycyclic compound having a structure represented by formula 1, and an organic electroluminescent device and a compound combination comprising the same.

Background

Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.

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

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

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

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

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

KR20200019272A discloses a composition comprising

Electroluminescent devices of compounds of the general structure, to which numerous compound structures are disclosed

Compounds of the structure which have not been converted to thisThe compound is intensively studied, in the structure, because two cyano groups with strong electrons are connected to a benzylic carbon, the benzylic hydrogen has extremely strong acidity, the stability of the structure is seriously influenced, meanwhile, the cyano groups with two strong electrons appear on the same carbon at the same time, the hole bridging capability is also seriously damaged, and finally, the EQE can be reduced. Furthermore, it does not address the different effects that can be brought about when cyano groups are attached to similar backbone structures via other linking groups.

Some compounds having a polycyclic condensed structure with boron, nitrogen, etc. as a central atom are disclosed in the prior art. However, when the material is used as a light-emitting material, the performance of the relevant device is still insufficient, and particularly, the light-emitting wavelength, emission peak width, voltage, efficiency, lifetime and the like of the device still have room for improvement, and further research is still needed.

Disclosure of Invention

The present invention aims to provide a series of novel polycyclic compounds that address at least some of the above problems. The novel polycyclic compound has a structure represented by formula 1 and is useful as a light emitting material in an organic electroluminescent device. These novel compounds can change the molecular orientation with the host in electroluminescent devices, providing better device performance.

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

E-(G)_n

formula 1

Wherein, in the formula 1, n is selected from an integer of 1-10;

e has a structure represented by formula 2:

any n positions in the structure represented by formula 2 are connected with the G;

ring A, ring B, ring C, on each occurrence, are identically or differently selected from an unsaturated carbocyclic ring having 5 to 30 carbon atoms or an unsaturated heterocyclic ring having 3 to 30 carbon atoms;

Y₁selected, identically or differently at each occurrence, from B, P ═ O, P ═ S, As ═ O, As ═ S, SiR 'or GeR';

X₁，X₂selected, identically or differently at each occurrence, from O, NR ", S or Se, said NR" having a structure represented by formula 3:

in formula 3, ring D, identically or differently on each occurrence, is selected from an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;

R_a，R_b，R_c，R_dthe same or different at each occurrence denotes mono-, poly-or unsubstituted;

R’，R_a，R_b，R_c，R_deach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 30 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;

in said formula 1, G, which may be the same or different at each occurrence, has a structure represented by formula 4:

in formula 4, represents the position connecting the E in the structure of the G;

L₁each occurrence, the same or different, is selected from the group consisting of: o, S, Se, (SiRR)_y，PR，(CRR)_yAnd combinations thereof; when a plurality of R are present at the same time, the plurality of R are the same or different;

L₂each occurrence, the same or different, is selected from the group consisting of: o, S, Se, (SiRR)_y，PR，(CRR)_ySubstituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, and combinations thereof; when a plurality of R are present at the same time, the plurality of R are the same or different;

x is, on each occurrence, identically or differently selected from integers from 0 to 10; and when x is 0, L₁Is connected with CN through a single bond;

y is an integer from 1 to 10, the same or different at each occurrence;

r 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;

adjacent substituents R_a，R_b，R_c，R_dAnd R can optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a polycyclic compound having a structure represented by formula 1:

E-(G)_n

formula 1

Wherein, in the formula 1, n is selected from an integer of 1-10;

e has a structure represented by formula 2:

R’，R_a，R_b，R_c，R_deach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkylOr an unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 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;

y is an integer from 1 to 10, the same or different at each occurrence;

According to another embodiment of the present invention, there is also disclosed a compound combination comprising one polycyclic compound which is a polycyclic compound having a structure represented by formula 1.

The novel polycyclic compound having the structure represented by formula 1 disclosed in the present invention can be used as a light emitting material in an organic electroluminescent device. These novel compounds can change the molecular orientation with the host in electroluminescent devices, providing better device performance.

Drawings

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

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

Detailed Description

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

Each of these layers has more realFor example. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:1₄TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.

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

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

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

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

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

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

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

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

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

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

The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)_S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ E_S-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).

Definitions for substituent terms

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

E-(G)_n

formula 1

Wherein, in the formula 1, n is selected from an integer of 1-10; for example, n is 1,2, 3,4, 5, 6, 7, 8, 9, or 10;

e has a structure represented by formula 2:

R’，R_a，R_b，R_c，R_deach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atomsA group, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 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;

L₁each occurrence, the same or different, is selected from the group consisting of: o, S, Se, (SiRR)_y，PR，(CRR)_yAnd combinations thereof; when a plurality of R are present at the same time, the plurality of R are the same or different; for example, when L is₁Selected from (SiRR)_yWhen R is the same or different; when L is₁Selected from (CRR)_yWhen R is the same or different;

L₂each occurrence, the same or different, is selected from the group consisting of: o, S, Se, (SiRR)_y，PR，(CRR)_ySubstituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, and combinations thereof; when a plurality of R are present at the same time, the plurality of R are the same or different; for example, when L is₂Selected from (SiRR)_yWhen R is the same or different; when L is₂Selected from (CRR)_yWhen R is the same or different;

x is, on each occurrence, identically or differently selected from integers from 0 to 10; for example, x is 0, 1,2, 3,4, 5, 6, 7, 8, 9, or 10; and when x is 0, L₁Is connected with CN through a single bond;

y is an integer from 1 to 10, the same or different at each occurrence; for example, y is 1,2, 3,4, 5, 6, 7, 8, 9, or 10;

In this embodiment, n arbitrary positions in the structure represented by formula 2 are connected to G, and n positions in formula 2 connected to G structure represented by formula 4 may be on any same or different rings in the structure represented by formula 2. For example, when n is 1, that is, when the structure represented by formula 2 has 1 position to which the G structure represented by formula 4 can be connected, the structure represented by formula 2 is any one of the following 5 structures:

in these structures, "+" indicates the position in the E structure to which the G structure is attached. When n is 2, that is, the structure represented by formula 2 has 2 positions that can be connected to the G structure represented by formula 4, in this case, the two positions that can be connected to the G structure represented by formula 4 may be on the same ring at the same time, for example:

and the like; or on different rings, for example:

and so on. This is also the case when n is 3-10.

In this example, the adjacent substituents R_a，R_b，R_c，R_dR can optionally be linked to form a ring, intended to denote a group in which adjacent substituents are present, for example two substituents R_aIn between, two substituents R_bIn between, two substituents R_cIn between, two substituents R_dOf a substituent R_aAnd R_bOf a substituent R_aAnd R_cOf a substituent R_bAnd R_cOf a substituent R_aAnd R_dOf a substituent R_bAnd R_dOf a substituent R_cAnd R_dAnd between two substituents R, any one or more of these adjacent groups of substituents can be linked to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.

According to one embodiment of the invention, wherein, in formula 2, ring a, ring B, ring C, on each occurrence, are selected, identically or differently, from five-membered unsaturated carbocyclic rings, aromatic rings having 6 to 30 carbon atoms or heteroaromatic rings having 3 to 30 carbon atoms.

According to one embodiment of the invention, wherein, in formula 2, ring a, ring B, ring C, on each occurrence, are selected, identically or differently, from five-membered unsaturated carbocyclic rings, aromatic rings having 6 to 18 carbon atoms or heteroaromatic rings having 3 to 18 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 2, ring a, ring B, ring C, each occurrence of which is the same or different, is selected from a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzothiole ring, a dibenzothiaole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a silole ring, or a combination thereof.

According to an embodiment of the present invention, wherein, in formula 2, Y₁Selected from B, P ═ O or P ═ S, the same or different at each occurrence.

According to the inventionAn embodiment wherein, in formula 2, Y₁Is B.

According to an embodiment of the present invention, wherein, in formula 2, X₁、X₂Selected from O, NR' or S, the same or different at each occurrence; the NR "has a structure represented by formula 3:

ring D, identically or differently on each occurrence, is selected from aromatic rings having 6 to 30 carbon atoms or heteroaromatic rings having 3 to 30 carbon atoms;

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

R_deach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 30 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_dCan optionally be linked to form a ring.

In this example, the adjacent substituents R_dCan optionally be linked to form a ring, intended to denote any adjacent substituent R_dCan be linked to form a ring. Is obvious and easyIn general, any adjacent substituents R_dOr may be both unconnected to form a ring.

According to an embodiment of the present invention, wherein, in formula 2, X₁、X₂Is selected from NR "identically or differently on each occurrence.

According to an embodiment of the present invention, wherein, in formula 2, X₁、X₂Selected from NR "identically or differently on each occurrence.

According to an embodiment of the present invention, wherein, in formula 2, X₁And/or X₂Selected, identically or differently on each occurrence, from NR' with ring D, identically or differently on each occurrence, being selected from aromatic rings having 6 to 18 carbon atoms or heteroaromatic rings having 3 to 18 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 2, X₁And/or X₂The ring D is selected, identically or differently at each occurrence, from NR ", identically or differently at each occurrence, from a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzothiole ring, a dibenzothiaole ring, a benzothiophene ring, a dibenzoselenophene ring, or a combination thereof.

According to one embodiment of the present invention, wherein E has a structure represented by formula 5:

any n positions in the structure represented by formula 5 are linked to the G represented by formula 4;

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

adjacent substituents R_a，R_b，R_c，R_dCan optionally be linked to form a ring.

In this embodiment, any n positions in the structure represented by formula 5 are connected to the G represented by formula 4, which means that the n positions in the structure represented by formula 5 connected to the G structure represented by formula 4 may be on any of the same or different rings in the structure represented by formula 5. For example, when n is 1, that is, when the structure represented by formula 5 has 1 position to which the G structure represented by formula 4 can be connected, the structure represented by formula 5 is any one of the following 5 structures:

in these structures, "+" indicates the position in the E structure to which the G structure is attached. When n is 2, that is, there are 2 positions in the structure represented by formula 5 that can be connected to the G structure represented by formula 4, in this case, the two positions that can be connected to the G structure represented by formula 4 may be on the same ring at the same time, for example:

and the like; or on different rings, for example:

and so on. This is also the case when n is 3-10.

In this context, adjacent substituents R_a，R_b，R_c，R_dCan optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents R_aIn between, two substituents R_bIn between, two substituents R_cIn between, two substituents R_dOf a substituent R_aAnd R_bOf a substituent R_aAnd R_cOf a substituent R_bAnd R_cOf a substituent R_aAnd R_dOf a substituent R_bAnd R_dAnd a substituent R_cAnd R_dAny one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.

According to one embodiment of the invention, wherein, in formula 5, R_a，R_b，R_c，R_dEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 12 carbon atoms, substituted or unsubstituted amino groups having 6 to 30 carbon atoms, and combinations thereof;

According toAn embodiment of the present invention, wherein, in formula 5, R_a，R_b，R_c，R_dEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, naphthyl, phenanthrene, anthracene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiole, dibenzosilole, benzothiophene, dibenzothiophene, dibenzoselenophene, diphenylamino, dibenzofuranylphenylamino, and combinations thereof.

According to an embodiment of the invention, wherein, in formula 1, n is selected from 1,2 or 3.

According to an embodiment of the present invention, wherein, in formula 1, n is 1.

According to one embodiment of the invention, wherein E is selected from any one of the group consisting of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61, and E-10-1 to E-10-24. The specific structures of the E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61 and E-10-1 to E-10-24 are shown in claim 9.

According to one embodiment of the invention, E is selected from any one of the group consisting of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61, E-10-1 to E-10-24, and E-11-1 to E-11-26. The specific structures of the E-1-E-1-45, E-2-1-E-2-28, E-3-1-E-3-39, E-4-1-E-4-104, E-5-1-E-5-79, E-6-1-E-6-88, E-7-1-E-7-56, E-8-1-E-8-179, E-9-1-E-9-61, E-10-1-E-10-24 and E-11-1-E-11-26 are shown in claim 9.

According to one embodiment of the invention, wherein the hydrogen energy in the structures of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61 and E-10-1 to E-10-24 is partially or completely replaced by deuterium.

According to one embodiment of the invention, wherein the hydrogen energy in the structures of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61, E-10-1 to E-10-24, and E-11-1 to E-11-26 is partially or completely substituted by deuterium.

According to an embodiment of the invention, wherein, in formula 4, y is selected from 1,2 or 3.

According to an embodiment of the present invention, wherein, in formula 4, y is 1.

According to an embodiment of the present invention, wherein, in formula 4, L₁Each occurrence of R is selected from the group consisting of CRR, wherein each occurrence of R is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 4, L₁Each occurrence of R is selected from the group consisting of CRR, and each occurrence of R is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;

according to an embodiment of the present invention, wherein, in formula 4, L₁Each occurrence of R is selected from the group consisting of CRR, and each occurrence of R is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, and combinations thereof.

According to an embodiment of the present invention, wherein, in formula 4, when x is not 0, L₁、L₂Each occurrence of the same or different is selected from the group consisting of CRR, wherein each occurrence of the same or different is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted orUnsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 4, when x is not 0, L₁、L₂Each occurrence of the same or different is selected from the group consisting of CRR, wherein each occurrence of the same or different is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 4, when x is not 0, L₁、L₂Each occurrence of the same or different is selected from the group consisting of CRR, wherein each occurrence of the same or different is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, and combinations thereof.

According to an embodiment of the present invention, wherein, in formula 4, L₁Each occurrence of the same or different is selected from the group consisting of CRR, wherein each occurrence of the same or different is selected from the group consisting of: hydrogen, deuterium or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 4, L₁Selected from CRR, identically or differently on each occurrence, wherein at least one of said R is selected from deuterium or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present invention, wherein, in formula 4, L₁Selected from CRR, identically or differently on each occurrence, wherein both R are deuterium, or selected from substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms, identically or differently on each occurrence.

According to an embodiment of the invention, wherein, in formula 4, x is selected from 0, 1,2 or 3.

According to an embodiment of the invention, wherein, in formula 4, x is selected from 0, 1 or 2.

According to an embodiment of the present invention, wherein, in formula 4, x is 1.

According to one embodiment of the invention, wherein G is selected, identically or differently on each occurrence, from any one or more of the group consisting of G-1 to G-55; the specific structures of G-1 to G-55 are shown in claim 15.

According to one embodiment of the present invention, wherein hydrogen in the structure of G-1 to G-55 can be partially or completely substituted with deuterium.

According to one embodiment of the invention, wherein the compound has the structure of E-G, wherein the E is selected from any one of the group consisting of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, and E-9-1 to E-9-61, and the G is selected from any one of the group consisting of G-1 to G-55; or the compound has E- (G)₂Wherein E is selected from any one of the group consisting of E-10-1 to E-10-24, and G is selected, identically or differently on each occurrence, from any one or any two of the group consisting of G-1 to G-55; optionally, the hydrogen in the structure of the compound can be partially or fully substituted with deuterium.

According to one embodiment of the invention, wherein the compound has the structure of E-G, wherein the E is selected from any one of the group consisting of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61, and E-11-1 to E-11-26, and the G is selected from any one of the group consisting of G-1 to G-55; or the compound has E- (G)₂Wherein E is selected from any one of the group consisting of E-10-1 to E-10-24, and G is selected, identically or differently on each occurrence, from any one or any two of the group consisting of G-1 to G-55; optionally, the hydrogen in the structure of the compound can be partially or fully substituted with deuterium.

According to one embodiment of the present invention, the compound is selected from the group consisting of compound BD1 to compound BD1618, and the specific structures of compound BD1 to compound BD1618 are shown in claim 16.

According to an embodiment of the present invention, wherein hydrogen in the structures of compound BD1 through compound BD1618 can be partially or completely substituted with deuterium.

According to another embodiment of the present invention, a multimeric compound having a structure represented by a multimer of a plurality of structures represented by formula 1 is disclosed:

E-(G)_n

formula 1

Wherein, in the formula 1, n is selected from an integer of 1-10;

e has a structure represented by formula 2:

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

L₁each occurrence, the same or different, is selected from the group consisting of: o, S, Se, (SiR)₂)_y，PR，(CR₂)_yAnd combinations thereof;

L₂each occurrence, the same or different, is selected from the group consisting of: o, S, Se, (SiR)₂)_y，PR，(CR₂)_ySubstituted or unsubstituted arylene groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms, and combinations thereof;

y is an integer from 1 to 10, the same or different at each occurrence;

adjacent substituents R_a，R_b，R_c，R_dR can optionally be linked to form a ring;

the multimeric compound is bonded so that any ring contained in the unit structure represented by the formula 1 is shared by a plurality of structural units, or bonded so that any rings contained in the unit structure represented by the formula 1 are condensed with each other.

According to one embodiment of the present invention, wherein the multimeric compound is a dimer or trimer having 2 or 3 structures represented by formula 1.

According to one embodiment of the invention, wherein the polymeric compound is selected from any one of the group consisting of Oligomer-1 to Oligomer-10:

according to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising a polycyclic or multimeric compound, the polycyclic or multimeric compound having a specific structure as described in any of the preceding embodiments.

According to one embodiment of the present invention, in the device, the organic layer is a light emitting layer, and the polycyclic compound or the multimeric compound is a light emitting material.

According to an embodiment of the present invention, in the device, the organic layer is a light emitting layer, and the polycyclic compound or the multimeric compound is a fluorescent light emitting material or a delayed fluorescent light emitting material.

According to one embodiment of the invention, wherein the device emits blue light.

According to one embodiment of the invention, in the device, the light emitting layer further comprises at least one host material.

According to one embodiment of the present invention, in the device, the at least one host material has a structure represented by formula 6:

wherein, in the formula 6,

R_g1to R_g8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine 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_g9and R_g10Each occurrence being the same or different and is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substitutedOr unsubstituted heteroaryl having 3 to 30 carbon atoms.

According to another embodiment of the present invention, a combination of compounds is also disclosed, which comprises a polycyclic or multimeric compound having a specific structure as described in any of the preceding embodiments.

In combination with other materials

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

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

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

Materials synthesis example:

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

synthesis example 1: synthesis of Compound BD20

The first step is as follows: synthesis of intermediate 1

Under the protection of nitrogen, palladium acetate (Pd (OAc)₂580mg,2.6mmol), tri-tert-butylphosphine tetrafluoroborate (t-Bu)₃PBF₄1.5g,52mmol), 1-bromo-2, 3-dichlorobenzene (24g,107mmol), bis (4-tert-butylphenyl) amine (60g,214mmol) and sodium tert-butoxide (t-BuONa,20g,214mmol) were mixed and xylene (500mL) was added. The system was heated to 140 ℃ and reacted overnight. After completion of the reaction, the reaction solution was filtered through magnesium sulfate and a silica gel layer, and washed with toluene to remove most of the solvent, and the precipitated solid was filtered. Recrystallization from PE/Tol-5/1 gave intermediate 1(30g,44.7 mmol).

The second step is that: synthesis of intermediate 2

Under the protection of nitrogen, adding the intermediate 1(20g,30mmol) into tert-butyl benzene (t-butylbenzene,150mL), then cooling to-30 ℃, dropwise adding tert-butyl lithium (t-BuLi,1.3M,40mL), removing the cooling bath after dropwise adding, returning to room temperature, heating to 60 ℃, reacting for 1h, cooling to-30 ℃, and dropwise adding boron tribromide (BBr)₃5mL,60mmol), returning to room temperature, stirring for 30 minutes, cooling to 0 ℃, dropwise adding N, N-diisopropylethylamine (DIPEA,10mL,60mmol), removing the ice bath, reacting until the system does not release heat, and heating the reaction to 120 ℃ for reaction overnight. Adding ammonium chloride solution in ice bath to quench reaction, adding ethyl acetate for extraction, concentrating the organic phase, dissolving the filtered solid in toluene, and recrystallizing to obtain intermediate 2(9.66g,15 mmol).

The third step: synthesis of intermediate 3

Under the protection of nitrogen, intermediate 2(9.66g,15mmol) was added to tetrahydrofuran (150mL), the reaction system was cooled to 0 ℃, NBS (2.67g,15mmol) was added in portions, and the reaction was slowly warmed to room temperature for overnight reaction. After the reaction was completed, intermediate 3(6.5g,10mmol) was isolated by column chromatography.

The fourth step: synthesis of intermediate 4

Under nitrogen protection, intermediate 3(6.5g,10mmol), palladium acetate (112mg,0.5mmol), and 2-dicyclohexylphosphine-2 ', 6' -dimethoxybiphenyl (SPhos,0.41g,1mmol) were added to tetrahydrofuran, and a solution of (2- (1, 3-dioxolan-2-yl) ethyl) zinc chloride (0.5M,30mmol) was slowly added thereto at room temperature, followed by reaction at room temperature overnight. After the reaction was completed, intermediate 4(0.967g,1.3mmol) was isolated by column chromatography.

The fifth step: synthesis of BD20

Under nitrogen protection, intermediate 4(0.967g,1.3mmol) was dissolved in tetrahydrofuran, diluted hydrochloric acid (1M,1mL) was added, the mixture was stirred at room temperature for 1 hour, the tetrahydrofuran was dried by spinning, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, and the organic phases were dried by spinning. Then, ethanol/water 3:1(4mL) was added thereto, hydroxylamine hydrochloride (0.28g,4mmol) was added thereto, the reaction was carried out for 2 hours after heating to 70 ℃, the organic phase was dried by spinning after the reaction solution was cooled to room temperature, the aqueous phase was extracted with dichloromethane, the organic phases were combined and dried by spinning, acetic anhydride (3mL) was added thereto, the reaction was heated to 120 ℃ and reacted for 1 hour. After the reaction, water was added, and an organic phase was obtained by extraction with dichloromethane, and finally, compound BD20(0.2g, 0.28mmol) was isolated by column chromatography. The product was identified as the target product with a molecular weight of 679.5.

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

Device example 1

First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was at a vacuum of about 10-⁸In the case of torr, the evaporation was performed by thermal vacuum evaporation at a rate of 0.2 to 2 angstroms/second in turn on an ITO anode. The evaporated compound HI is used as a hole injection layer (HIL,

). The evaporated compound HT is used as a hole transport layer (HTL,

). The evaporated compound EB is used as an electron blocking layer (EBL,

). Then, compound BH and compound BD20 were simultaneously evaporated to serve as a light emitting layer (EML, weight ratio 98:2,

). The evaporation compound HB was used as a hole blocking layer (HBL,

). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were simultaneously evaporated as an electron transport layer (ETL, weight ratio 40:60,

). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.

The material structure used in the device is as follows:

at a constant current of 10mA/cm²Next, the External Quantum Efficiency (EQE) of example 1 was measured to be 7.81%, the maximum emission wavelength (λ)_max) At 464nm, with CIE coordinates (0.129,0.096) and a full width at half maximum (FWHM) of 28.9nm, indicating that compounds of formula 1 containing a characteristic cyano substitution are capable of providing high efficiency light emission in a device.

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

Claims

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

E-(G)_n

formula 1

Wherein, in the formula 1, n is selected from an integer of 1-10;

e has a structure represented by formula 2:

R’，R_a，R_b，R_c，R_deach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atomsA heterocyclic group of 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 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;

y is an integer from 1 to 10, the same or different at each occurrence;

2. The compound of claim 1, wherein in formula 2, ring a, ring B, ring C, identically or differently at each occurrence, are selected from five-membered unsaturated carbocyclic rings, aromatic rings having 6 to 30 carbon atoms or heteroaromatic rings having 3 to 30 carbon atoms;

preferably, ring a, ring B, ring C, identically or differently on each occurrence, are selected from five-membered unsaturated carbocyclic rings, aromatic rings having 6 to 18 carbon atoms or heteroaromatic rings having 3 to 18 carbon atoms;

more preferably, ring a, ring B, ring C, each occurrence, is selected, identically or differently, from a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzothiole ring, a dibenzothiaole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, a cyclopentadiene ring, a furan ring, a thiophene ring, a thiaole ring, or a combination thereof.

3. The compound according to claim 1 or 2, wherein, in formula 2, Y is₁Selected, identically or differently at each occurrence, from B, P ═ O or P ═ S;

preferably, Y₁Is B.

4. A compound according to any one of claims 1 to 3, wherein, in formula 2, X₁、X₂Selected from O, NR' or S, the same or different at each occurrence;

preferably, X₁、X₂Is selected from NR "identically or differently on each occurrence of at least one of;

more preferably, X₁And X₂Selected from NR "identically or differently on each occurrence.

5. The compound of any one of claims 1 to 4, wherein, in formula 2, X₁And/or X₂Identically or differently on each occurrence from NR' with identically or differently on each occurrence from an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms;

preferably, ring D, identically or differently at each occurrence, is selected from a benzene ring, a pyridine ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzothiole ring, a dibenzothiaole ring, a benzothiophene ring, a dibenzothiophene ring, a dibenzoselenophene ring, or a combination thereof.

6. The compound of any one of claims 1-5, wherein E has a structure represented by formula 5:

R_a，R_b，R_c，R_deach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atomsAn alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 30 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;

7. The compound of any one of claims 1-6, wherein, in formula 5, R_a，R_b，R_c，R_dEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 12 carbon atoms, substituted or unsubstituted amino groups having 6 to 20 carbon atoms, and combinations thereof;

adjacent substituents R_a，R_b，R_c，R_dCan optionally be linked to form a ring;

preferably, said R is_a，R_b，R_c，R_dEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, naphthylPhenanthrene, anthracene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiole, dibenzothiaole, benzothiophene, dibenzothiophene, dibenzoselenophene, diphenylamino, dibenzofuranylphenylamino, and combinations thereof.

8. The compound of any one of claims 1-7, wherein in formula 1, n is selected from 1,2 or 3;

preferably, n is 1.

9. The compound of any one of claims 1-8, wherein E is selected from the group consisting of:

in the above structure, TMS represents trimethylsilyl;

optionally, the hydrogen in the structures of E-1-1 through E-1-45, E-2-1 through E-2-28, E-3-1 through E-3-39, E-4-1 through E-4-104, E-5-1 through E-5-79, E-6-1 through E-6-88, E-7-1 through E-7-56, E-8-1 through E-8-179, E-9-1 through E-9-61, E-10-1 through E-10-24, and E-11-1 through E-11-26 can be partially or fully substituted with deuterium.

10. The compound of any one of claims 1-9, wherein y is selected from 1,2, or 3;

preferably, y is 1.

11. The compound of any one of claims 1-10, wherein in formula 4, L₁Each occurrence of the same or different is selected from the group consisting of CRR, wherein each occurrence of the same or different is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 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;

preferably, wherein said R, identically or differently at each occurrence, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;

more preferably, wherein said R, identically or differently at each occurrence, is selected from the group consisting of: hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, and combinations thereof.

12. The compound of any one of claims 1-11, wherein in formula 4, L is when x is not 0₁、L₂Each occurrence of the same or different is selected from the group consisting of CRR, wherein each occurrence of the same or different is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 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;

13. The compound of any one of claims 1-12, wherein in formula 4, L₁Selected from the group consisting of CRR, identically or differently on each occurrence, wherein said R is identical or differently on each occurrenceVariously selected from the group consisting of: hydrogen, deuterium or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

preferably, at least one of said R is selected from deuterium or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms;

more preferably, both of said two R are deuterium, or said two R, on each occurrence, are selected, identically or differently, from substituted or unsubstituted alkyl groups having from 1 to 20 carbon atoms.

14. The compound of any one of claims 1-13, wherein x is selected from 0, 1,2, or 3;

preferably, x is selected from 0, 1 or 2;

more preferably, x is 1.

15. The compound of any one of claims 1-14, wherein G, on each occurrence, is selected, identically or differently, from any one or more of the group consisting of:

optionally, the hydrogen in the structures of G-1 through G-55 can be partially or fully substituted with deuterium.

16. The compound of any one of claims 1-15, wherein the compound has the structure of E-G, wherein the E is selected from any one of the group consisting of E-1-1 to E-1-45, E-2-1 to E-2-28, E-3-1 to E-3-39, E-4-1 to E-4-104, E-5-1 to E-5-79, E-6-1 to E-6-88, E-7-1 to E-7-56, E-8-1 to E-8-179, E-9-1 to E-9-61, and E-11-1 to E-11-26, the G is selected from any one of the group consisting of G-1 to G-55; or the compound has E- (G)₂Wherein E is selected from any one of the group consisting of E-10-1 to E-10-24, and G is selected, identically or differently on each occurrence, from any one or any two of the group consisting of G-1 to G-55; optionally, the hydrogen in the structure of the compound can be partially or fully substituted with deuterium;

preferably, the compound is selected from the group consisting of compound BD 1-compound BD 1618; wherein compound BD 1-compound BD1570 have structures E-G, wherein E and G correspond to structures selected from those listed in the following table:

wherein the compound BD 1571-compound BD1618 has an E- (G)₂Wherein two G's are the same, said E and said G's each correspond to a structure selected from the structures listed in the following table:

optionally, the hydrogen in the structures of compounds BD1 through BD1618 can be partially or fully substituted with deuterium.

17. An electroluminescent device, comprising:

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

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and cathode, the organic layer comprising a compound of any one of claims 1-16.

18. The device of claim 17, wherein the organic layer is an emissive layer and the compound is an emissive material;

preferably, the device emits blue light.

19. The device of claim 18, wherein the light emitting layer further comprises at least one host material;

preferably, the at least one host material has a structure represented by formula 6:

wherein, in the formula 6,

R_g1to R_g8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted heterocyclyl having 7-an aralkyl group of 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

R_g9and R_g10Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

20. A combination of compounds comprising a compound of any one of claims 1-16.