CN113683518A

CN113683518A - Aromatic amine derivative organic electroluminescent material and device thereof

Info

Publication number: CN113683518A
Application number: CN202010418571.2A
Authority: CN
Inventors: 田学超; 毕欣; 张少博; 赵春亮; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2020-05-18
Filing date: 2020-05-18
Publication date: 2021-11-23

Abstract

Disclosed are an aromatic amine derivative organic electroluminescent material and a device thereof. The compound is an aromatic amine substituted pyrene compound, wherein one aryl group of arylamine in the compound has a substituted six-membered (hetero) aromatic ring and saturated ring structure, and the other aryl group is a substituted (hetero) aryl group. The compound can be used as a light-emitting material in an organic electroluminescent device. These novel compounds can provide better device performance such as narrower half-peak width and higher external quantum efficiency. An electroluminescent device and compound formulation are also disclosed.

Description

Aromatic amine derivative organic electroluminescent material and device thereof

Technical Field

The present invention relates to compounds for use in organic electronic devices, such as organic electroluminescent devices. And more particularly, to a pyrene compound substituted with an aromatic amine and an organic electroluminescent device and a compound formulation including 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.

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 OLED phosphorescent materials have been successfully commercialized. The existing phosphorescent blue OLED has the problems of short service life, difficulty in reaching deep blue, blue unsaturation, high working voltage and the like. The fluorescent blue OLED has a longer lifetime than the phosphorescent blue OLED, but has a low efficiency, and thus it is highly desirable to improve the efficiency and other properties of the fluorescent blue electroluminescent device.

WO2010013676A1 discloses diaminopyrene derivatives of the general formula

Wherein, discloses an aminopyrene derivative partially substituted by benzocyclohydrocarbon, and the specific structure is

And the like. However, the patent application does not examine the influence of the introduction of benzocyclohydrocarbon on the device performance, and does not recognize the advantages of the introduction of benzocyclohydrocarbon or the connection of other groups on the benzene ring of benzocyclohydrocarbon, and does not recognize the different effects of the position change of the substituent of the benzoalicyclic ring.

CN109678729A discloses a pyrene compound containing a benzocyclohexane structure, which has a general formula shown in the specification

Wherein Ar is₂Is selected from

The concrete structure is that

And the like. However, only the compounds of benzocyclohexanes with only a few structures are disclosed in the patent application, the influence of the introduction of the benzocyclohexanes on the device performance is not examined, and the device effect obtained by further substitution on the benzene ring of the benzocyclohexanes which is a non-six-membered ring is not disclosed and taught.

CN107556239A discloses a pyrene compound containing an acridine structure, which has a general formula shown in the specification

Wherein Ar is₁And Ar₂Can be heterocyclic radical, and has specific structure

However, the patent application mainly aims at a series of pyrene compounds with acridine substituted aromatic amine, does not pay attention to improvement of device performance caused by benzo-heterocyclic hydrocarbon, and does not disclose and teach that better device effect can be achieved by connecting other groups to the benzene ring of the benzo-heterocyclic hydrocarbon.

These documents disclose fluorescent light-emitting materials having an aromatic amine structure with pyrene as a core. However, the fluorescent light-emitting material still needs to be developed further to obtain higher device performance.

Disclosure of Invention

The present invention aims to solve at least part of the above problems by providing a series of novel pyrene-based compounds having a substituted six-membered (hetero) aromatic ring and an aromatic amine structure of a saturated ring and a substituted (hetero) aryl group.

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

wherein, in the formula 1,

substituent R₁-R₁₀At least one of which has the structure of formula 2:

and the substituent R_l-R_l0The remainder of which are, on each occurrence, identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having from 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

wherein, in the formula 2,

l is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;

X₁-X₅selected, identically or differently at each occurrence, from C, CR_x1，CR_x2Or N; and X₁-X₅At least two of them are adjacent to each other and are connected with the group of formula 2, X₁-X₅At least one of which is CR_x2；

Y₁-Y₅Selected from CR, identically or differently at each occurrence_y1，CR_y2Or N; and Y is₁-Y₅At least one of which is CR_y2；

Z is selected, identically or differently on each occurrence, from C (R)_z)₂，NR_zO, S or Se;

R_x1and R_y1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

R_x2and R_y2Each occurrence, the same or different, is selected from the group consisting of: 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 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 atomsSubstituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

represents the position of the substituent with the structure of formula 2 connected with formula 1;

n is 0, 1,2, 3,4 or 5;

R_zeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;

adjacent substituents R_x1，R_x2，R_y1，R_y2Can optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising the compound having the structure of formula 1. The specific structures of the compounds are described in the preceding examples.

According to another embodiment of the present invention, there is also disclosed a compound formulation comprising the compound having the structure of formula 1. Specific structures of the compounds are described in the preceding examples.

The invention provides a series of novel pyrene compounds with substituted hexatomic (hetero) aromatic ring, saturated ring and substituted (hetero) aryl aromatic amine structures, which can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide better device performance such as narrower half-peak width and higher external quantum efficiency.

Drawings

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

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

Detailed Description

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

There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:1₄TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The method being incorporated by reference in its entiretyThe principle and use of barrier layers is described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, both of which are incorporated by reference. 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 a transition from a triplet state back to a singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of the backfill singlet excited state 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-comprises both straight and branched chain alkyl groups. 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. In addition, the alkyl group may be optionally substituted. The carbons in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferable.

Cycloalkyl-as used herein, comprises a cyclic alkyl group. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.

Alkenyl-as used herein, encompasses both straight and branched chain olefinic groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include a vinyl group, an allyl 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 1-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group. In addition, alkenyl groups may be optionally substituted.

Alkynyl-as used herein, straight and branched alkynyl groups are contemplated. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chicory, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. 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-triphenyl-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.

Heterocyclyl or heterocyclic-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.

Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated which may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 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, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothienopyridine, thienobipyridine, benzothiophenopyridine, cinnolinopyrimidine, selenobenzodipyridine, selenobenzene, 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-is represented by-O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.

Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.

Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. 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, 1-2-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.

The term "aza" in azafluorene, azaspirobifluorene ring, azadibenzofuran, aza-dibenzothiophene, etc., means that one or more 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 aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, 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, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted with one or more members selected from deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having from 1 to 20 carbon atoms, an unsubstituted aralkyl group having from 7 to 30 carbon atoms, an unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted aryloxy group having from 6 to 30 carbon atoms, an unsubstituted alkenyl group having from 2 to 20 carbon atoms, an unsubstituted aryl group having from 6 to 30 carbon atoms or, preferably, an unsubstituted aryl group having from 6 to 12 carbon atoms, an unsubstituted heteroaryl group having from 3 to 30 carbon atoms or, preferably, an unsubstituted heteroaryl group having from 3 to 12 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, ester, 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, a deuterated substituent, such as deuterated methyl, means that at least one hydrogen atom in said substituent (methyl) is replaced by deuterium.

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 two 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 two 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 two 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 the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:

wherein, in the formula 1,

substituent R₁-R₁₀At least one of which has the structure of formula 2:

and the substituent R₁-R₁₀The remaining of (a) are, identically or differently on each occurrence, 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 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 aryl silicon group having 6 to 20 carbon atoms.An alkyl group, a substituted or unsubstituted amino group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

wherein, in the formula 2,

R_x1and R_y1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine having from 0 to 20 carbon atomsA base, and combinations thereof;

R_x2and R_y2Each occurrence, the same or different, is selected from the group consisting of: 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 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, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

n is 0, 1,2, 3,4 or 5;

adjacent substituents R_x1，R_x2，R_y1，R_y2Can optionally be linked to form a ring;

substituent R_zCan optionally be linked to form a ring.

In this embodiment, the "adjacent substituents R_x1，R_x2，R_y1，R_y2Optionally joined to form a ring "may comprise any one or more of the following: one is the case where there is a connecting ring between adjacent substituents, e.g. adjacent substituents R_x1And R_x1Adjacent and adjacent substituents R_x1And R_x2Adjacent and adjacent substituents R_x2And R_x2Adjacent and adjacent substituents R_y1And R_y1Adjacent and adjacent substituents R_y1And R_y2The substituents R being adjacent and adjacent_y2And R_y2There may be a case where the rings are connected to each other. Alternatively, the adjacent substituents may be not connected to each other to form a ring.

In this example, the "substituent R" is_zOptionally joined to form a ring "may comprise any one or more of the following: in one case for the substituent R_zIn which there is a connection to form a ring, e.g. when two or more R's are present simultaneously_zWhen R is equal to_zIn which there is a connection to form a ring, e.g. R_zThe two are connected to form a ring to form a spiral ring or bridge ring structure. Another case is for the substituent R_zMay not be connected to form a ring.

In this example, the substituent R in formula 1₁To R₁₀Wherein at least one substituent has the structure of formula 2, and R₁To R₁₀The remainder of (a) are selected, identically or differently on each occurrence, from the group consisting of the substituents mentioned above. For example, when the substituent R₁Having the structure of formula 2, then R₁To R₁₀The remainder of (1), namely R₂To R₁₀Each occurrence is selected, identically or differently, from the group consisting of the substituents mentioned above. When the substituent R is₁And R₆Having the structure of formula 2, then R₁To R₁₀The remainder of (1), namely R₂To R₅And R₇To R₁₀Each occurrence is selected, identically or differently, from the group consisting of the substituents mentioned above.

According to one embodiment of the present invention, wherein the substituent having formula 2 further has a structure of formula 3 or formula 4:

wherein, in formula 3 and formula 4,

in formula 3, X₁-X₃Selected from CR, identically or differently at each occurrence_x1，CR_x2Or N; and at least one is CR_x2；

In formula 4, X₁-X₂And X₅Selected from CR, identically or differently at each occurrence_x1，CR_x2Or N; and at least one is CR_x2；

n is 0, 1,2, 3,4 or 5;

R_x1and R_y1Each 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 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 aralkyl having 2 to 20 carbon atomsAn alkenyl group of carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

R_zeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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 atomsSubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane groups having 6 to 20 carbon atoms, and combinations thereof;

substituent R_zCan optionally be linked to form a ring;

represents the position of the substituent having the structure represented by formula 3 or formula 4 to which formula 1 is attached.

According to one embodiment of the invention, n is 0, 1,2, 3.

According to one embodiment of the invention, wherein n is 1.

According to one embodiment of the invention, wherein the substituent R in formula 1₁And R₆Has a structure represented by formula 2, formula 3 or formula 4, and R₁And R₆Are the same or different; r₂To R₅，R₇To R₁₀The same or different at each occurrence is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms.

According to one embodiment of the invention, wherein the substituent R in formula 1₁And R₆Has a structure represented by formula 2, formula 3 or formula 4, and R₁And R₆Is a phaseThe same or different; r₂，R₄-R₅，R₇And R₉-R₁₀Is hydrogen, R₃And R₈Identically or differently on each occurrence is selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms.

According to one embodiment of the invention, wherein L, identically or differently at each occurrence, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein L, identically or differently at each occurrence, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein L is selected from single bonds.

According to one embodiment of the invention, wherein R_x1And R_y1Each 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 12 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, and combinations thereof.

According to one embodiment of the invention, wherein R_x1And R_y1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof.

According to one embodiment of the invention, wherein R_x1And R_y1Is hydrogen.

According to one embodiment of the present invention, wherein X₁-X₅Selected from C, CR, the same or different at each occurrence_x1Or CR_x2(ii) a And X₁-X₅At least one of them is selected from CR_x2；Y₁-Y₅Selected from CR, identically or differently at each occurrence_y1Or CR_y2(ii) a And Y is₁-Y₅At least one of them is selected from CR_y2。

According to one embodiment of the present invention, wherein X₁-X₅At least one is CR_x2And R is_x2Each occurrence, the same or different, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof.

According to one embodiment of the present invention, wherein X₁-X₅At least one is CR_x2And R is_x2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof.

According to one embodiment of the present invention, wherein X₁-X₅At least one is CR_x2And R is_x2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or a combination thereof.

According to one embodiment of the present invention, wherein X₁-X₅At least one of which, except for the ring-forming atoms, is CR_x2And R is_x2Each occurrence, the same or different, is selected from the group consisting of: phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthryl, anthracenyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiollolyl, dibenzothiapyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

According to one embodiment of the present invention, wherein Y₂To Y₄At least one of which is CR_y2And R is_y2Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.

According to one embodiment of the present invention, wherein Y₂To Y₄At least one of which is CR_y2And R is_y2Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms.

According to one embodiment of the present invention, wherein Y₂To Y₄At least one of which is CR_y2And R is_y2Each occurrence, the same or different, is selected from the group consisting of: phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthryl, anthracenyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiollolyl, dibenzothiapyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

According to one embodiment of the present invention, wherein Y₁And/or Y₅Is CR_y2And R is_y2Each occurrence, identically or differently, is selected from 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, or a combination thereof.

According to one embodiment of the present invention, wherein Y₁And/or Y₅Is CR_y2And R is_y2Each occurrence, the same or different, is selected from the group consisting of: methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, cyclopropyl, deuterated cyclopropyl, n-butyl, deuterated n-butyl, isobutyl, deuterated n-butylIsobutyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl and deuterated cyclohexyl.

According to one embodiment of the invention, wherein Z is C (R)_z)₂And R is_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein Z is CR_zAnd R is_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, halogen, deuterium, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof.

According to one embodiment of the present invention, wherein the compound is selected from the group consisting of compound BD1 through compound BD810, the specific structures of compound BD1 through compound BD810 are shown in claim 12.

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

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

a cathode electrode, which is provided with a cathode,

and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of formula 1:

wherein, in the formula 1,

substituent R₁-R₁₀Wherein at least one substituent has a structure represented by formula 2;

and the substituent R₁-R₁₀The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

wherein, in the formula 2,

R_x1and R_y1Each occurrence is the same or different and is selected fromA 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 heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

represents a position where the substituent having the structure represented by formula 2 is linked to formula 1;

n is 0, 1,2, 3,4 or 5;

R_zat each occurrenceThe same or different is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;

substituent R_zCan optionally be linked to form a ring.

According to one embodiment of the present invention, wherein the organic layer comprises a light emitting layer, wherein the light emitting layer comprises a compound having a structure of formula 1.

According to one embodiment of the present invention, wherein the light emitting layer further comprises a host material.

According to one embodiment of the present invention, wherein the host material comprises a compound having the structure of formula 5:

wherein, in the formula 5,

R_g1to R_g8Each 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, or a pharmaceutically acceptable salt thereofSubstituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

R_g9and R_g10Each independently 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.

According to one embodiment of the invention, a compound formula is also disclosed, which comprises a compound with a structure shown in formula 1, wherein the specific structure of the compound is shown in any embodiment.

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 BD176

First step of

2-bromo-4-iodo-1-methylbenzene (100g,337mmol), phenylboronic acid (49g,404mmol), Pd (PPh)₃)₄(7.8g,6.8mmol)，K₂CO₃(116g,843mmol) was placed in a 1000mL three-necked flask, and 340mL of toluene, THF110mL，H₂O110mL substitution of N₂. Heating to 78 ℃ for reaction. The reaction is carried out until the raw materials completely react, and column chromatography purification is carried out to obtain the intermediate 1(80g,325mmol, 97% yield) of colorless oily liquid.

Second step of

Intermediate 1(81g, 329mmol), NBS (61g,345mmol) was placed in a 2L two-necked flask and 1.3L acetonitrile was added to replace N₂Heating to 80 deg.C, and stirring for reaction. Benzoyl peroxide (BPO, 8g, 33mmol) was added portionwise. The reaction was completed until the starting material reacted completely, and purified by column chromatography to give intermediate 2(82g,253mmol, 77% yield) as a white solid.

The third step

LDA (130mL,260mmol) was placed in a 500mL three-necked flask, stirred under dry ice-ethanol for half an hour, methyl isobutyrate (30mL,260mmol) was added, and stirring was continued for half an hour. Intermediate 2(80g,130mmol) was added. The reaction is carried out until the raw material reaction is completed, and column chromatography purification is carried out to obtain the intermediate 3(50g,145mmol, 98% yield) which is light yellow oily matter.

The fourth step

Intermediate 3(78g,227mmol), KOH (88g,1.57mol) were mixed and H was added₂O230 mL and methanol 23mL, and heating to 100 ℃ for reaction until TLC detection reaction is finished. After cooling and returning the reaction to room temperature, concentrated HCl was added to adjust the pH of the system to acidity, and the intermediate (71g,227mmol) was obtained by filtration.

The intermediate (20g, 60mmol) was dissolved in 200mL of dichloromethane, and N was passed through the solution₂Adding one drop of DMF, gradually adding oxalyl chloride (30mL, 60mmol) dropwise until no gas is generated in the systemAfter soaking, the reaction was transferred to an ice-water bath and stirred for half an hour, aluminum trichloride (8g, 60mmol) was added in portions and monitored by TLC until the reaction was complete. Filtered through celite and concentrated. Column chromatography (PE as eluent) gave intermediate 4 as a white solid (6g,18.8mmol, 31% yield).

The fifth step

Intermediate 4(18g,57mmol) was dissolved in 180mL of methanol, stirred in an ice-water bath for half an hour and NaBH was added portionwise₄After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated.

The product was dissolved in dichloromethane and Et was added₃SiH (12.7g,111mmol), was stirred in an ice-water bath for half an hour, gradually added TFA (18g, 155mmol) dropwise until the starting material reacted completely, and purified by column chromatography to give intermediate 5(12g, 39.9mmol, 70% yield) as a colorless oil.

The sixth step

Pd is added at room temperature under the protection of nitrogen₂(dba)₃(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 5(6g,19.9mmol), 4-methyl- [1, 1' -biphenyl]-3-amine (5.5g, 30mmol) and t-BuONa (3.8g,39.8mmol) were added to toluene (100mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 6(6.7g,16.4mmol, yield 82.7%) as a white solid.

Seventh step

Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.38g,6.6mmol), intermediate 6(6.2g, 15.2mmol), Pd (OAc)₂(74mg，0.33mmol)，t-Bu₃P·HBF₄(191mg,0.66mmol) and t-BuONa (1.46g,15.2mmol), xylene (33mL) was added and the system was heated to 95 ℃. After the reaction was completed, the product compound BD176(6g, 5.97mmol, 90% yield) was obtained through column chromatography purification. The product was identified as the target product with a molecular weight of 1004.5.

Synthesis example 2: synthesis of Compound BD109

The first step is as follows:

pd is added at room temperature under the protection of nitrogen₂(dba)₃(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 5(6g,19.9mmol), [1, 1' -biphenylyl]-3-amine (5.5g, 30mmol) and t-BuONa (3.8g,39.8mmol) were added to toluene (100mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 7(6.7g, 16.4mmol, 83% yield) as a colorless oil.

The second step is that:

under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.2g, 6.1mmol), intermediate 7(5.5g, 14mmol), Pd (OAc)₂(68mg，0.3mmol)，tBu₃PH⁺BF₄ ^-(174mg, 0.6mmol) and t-BuONa (1.3g, 14mmol), xylene (30mL) was added and the system was heated to 95 ℃. After the reaction was completed, purification was performed by column chromatography to obtain BD109(5g, 5.1mmol, yield 84%) as a yellow-green solid. The product was identified as the target product with a molecular weight of 976.5.

Synthesis comparative example 1: synthesis of comparative Compound A

The first step is as follows:

pd (OAc)₂(52mg,0.23mmol)，tBu₃PH⁺BF₄ ^-(134mg, 0.46mmol) was charged into a 250mL two-necked flask and xylene (100mL) was added. Introducing N into the solution₂After 20 minutes until the color did not change any more, 1, 6-dibromopyrene (2.77g, 7.68mmol) and the compound bis (4-methyl- [1, 1' -biphenyl) were added successively]-3-yl) amine (5.9g, 16.9mmol), sodium tert-butoxide (3.69g, 38.4 mmol). Continuously introducing N₂For 10 minutes, the system was heated to 90 ℃ until the reaction of the starting materials was complete. After the reaction was completed, purification was performed by column chromatography to obtain the product, comparative compound A (2.4g, 2.68mmol, yield 34.9%). The product was identified as the target product with a molecular weight of 896.4.

Synthesis comparative example 2: synthesis of comparative Compound B

The first step is as follows:

LDA (100mL, 200mmol) was placed in a 250mL three-necked flask, stirred under dry ice-ethanol for half an hour, methyl isobutyrate (23mL, 200mmol) was added, and stirring was continued for half an hour. Benzyl bromide (25g, 100mmol) was added and filtered through celite. After concentration, a crude product intermediate 8 is obtained and directly subjected to the next reaction.

The second step is that:

intermediate 8(27g, 100mmol) and potassium hydroxide (56g,1mol) were mixed, 100mL of water and 10mL of methanol were added, and the mixture was heated to 100 ℃ for reaction until the TLC detection reaction was complete. Cooling, adding concentrated hydrochloric acid to adjust system pH to acidity after reaction returns to room temperature, extracting organic phase with ethyl acetate, combining organic phases, and concentrating.

Dissolve the above product (27g, 100mmol) in 200mL of dichloromethane, N₂Blowing gas, adding one drop of DMF, gradually adding oxalyl chloride (12.8mL, 120mmol) dropwise, after the system does not generate bubbles any more, moving the reaction to an ice water bath, stirring for half an hour, and batchingAluminum trichloride (14.3g,108mmol) was added and monitored by TLC until the reaction was complete. Chromatography by column eluting with PE gave intermediate 9(22g, 91.6mmol, 85% yield) as a white solid.

The third step:

intermediate 9(22g, 99mmol) was dissolved in 300mL of methanol, stirred in an ice-water bath for half an hour and NaBH was added in portions₄After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated.

The product was dissolved in dichloromethane and Et was added₃SiH (22.5g, 198mmol), stirred in an ice-water bath for half an hour, gradually added TFA (34g, 297mmol) dropwise, concentrated, and purified by column chromatography to give intermediate 10(7.7g, 34.4mmol, 35% yield) as a colorless oil.

The fourth step:

pd is added at room temperature under the protection of nitrogen₂(dba₃) (1g, 1.1mmol), intermediate 10(5.1g, 22.7mmol), 4-methyl- [1, 1' -biphenyl]-3-amine (5g, 27.2mmol), BINAP (1.4g, 2.2mmol) and t-BuONa (4.7g, 49.6mmol) were added to xylene (100mL) and the system was heated to 90 ℃ for reaction overnight. Purification by column chromatography after the reaction was complete gave intermediate 11 as a white solid (5.7g, 17.4mmol, 76% yield).

The fifth step:

under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.6g, 7.2mmol) and 2, 2-dimethyl-N- (4-methyl- [1, 1' -biphenyl) are added]-3-yl) -2, 3-dihydro-1H-indan-4-amine (5.7g, 17.4mmol), Pd (OAc)₂(161mg,0.72mmol)，t-Bu₃P·BF₄(406mg,1.4mmol) and t-BuONa (2.7g, 28.2mmol) were added to xylene (20mL) and the system was heated to 100 ℃ until the reaction was complete. And purified by column chromatography to give comparative compound B as a yellow-green solid (1.2g, 1.41mmol, 20% yield). The product was identified as the target product with a molecular weight of 852.4.

Synthesis comparative example 3: synthesis of comparative Compound C

The first step is as follows:

pd is added at room temperature under the protection of nitrogen₂(dba)₃(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 5(6g,19.9mmol), aniline (2.79g,30mmol) and t-BuONa (3.8g,39.8mmol), toluene (100mL) was added and the system was heated to 120 ℃ for 3 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 12(5.3g,16.9mmol, yield 85%) as a colorless oily substance.

The second step is that:

under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.38g,6.6mmol), intermediate 12(4.76g,15.2mmol), Pd (OAc)₂(74mg,0.33mmol)，t-Bu₃P·HBF₄(191mg,0.66mmol) and t-BuONa (1.46g,15.2mmol) were added to xylene (30mL) and the system was heated to 95 ℃. After the reaction was completed, it was purified by column chromatography to obtain comparative compound C (4.68g,5.67mmol, yield 86%) as a yellow-green solid. The product was identified as the target product with a molecular weight of 824.4.

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 of 80nm thickness was cleaned, and then oxygen plasma was usedAnd UV ozone treatment. 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 in a vacuum of about 10 degrees^-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. Compound HI was used as Hole Injection Layer (HIL). The compound HT is used as a Hole Transport Layer (HTL). Compound EB was used as an Electron Blocking Layer (EBL). Then compound BD176 is doped in compound BH and co-evaporated to serve as the light emitting layer (EML). Compound HB was used as a Hole Blocking Layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an Electron Transport Layer (ETL). 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.

Device example 2

The embodiment of device example 2 is the same as device example 1 except that compound BD109 is used instead of compound BD176 in the light emitting layer (EML).

Device comparative example 1

Device comparative example 1 was the same as device example 1 except that compound a was used in place of compound BD176 in the light emitting layer (EML).

Device comparative example 2

Device comparative example 2 was the same as device example 1 except that compound C was used in place of compound BD176 in the light emitting layer (EML).

Device comparative example 3

Device comparative example 3 was the same as device example 1 except that compound B was used in place of compound BD176 in the light emitting layer (EML).

The detailed structure and thickness of the device layer portions are shown in table 1. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.

TABLE 1 device structures of device examples and comparative examples

The material structure used in the device is as follows:

IVL was measured for all the examples and comparative devices at different current densities and voltages. At a constant current of 1000cd/m²External Quantum Efficiency (EQE), maximum emission wavelength (. lamda.) was measured_max) Full width at half maximum (FWHM) and CIE data.

Table 2 device data for example 1, comparative example 1 and comparative example 3

Device numbering	CIE(x,y)	λmax(nm)	FWHM(nm)	EQE(％)
					Example 1	0.135,0.118	461	29.70	9.12
Comparative example 1	0.140,0.098	456	32.20	8.88
					Comparative example 3	0.135,0.118	461	30.10	9.05

Discussion:

table 2 shows the device data of example 1, comparative example 1 and comparative example 3, from which it can be seen that the device example 1 has an External Quantum Efficiency (EQE) of 9.12%, a maximum emission wavelength of 461nm, a CIE of (0.135,0.118) and a half-peak width of 29.7 nm; comparative example 1 the External Quantum Efficiency (EQE) was 8.88%, the maximum emission wavelength was 456nm, the CIE was (0.140,0.098), and the half-peak width was 32.2 nm. Example 1 showed an increase in EQE of 2.7% and a narrowing of the half-width by 3.5nm compared to comparative example 1. From the results of example 1 compared with comparative example 1, due to the introduction of a specific benzo-saturated ring substituent into one aryl group in the arylamine, higher EQE and narrower half-peak width are obtained in the device results, and the blue luminescence performance is effectively increased.

Comparative example 3 the External Quantum Efficiency (EQE) was 9.05%, the maximum emission wavelength was 461nm, the CIE was (0.135,0.118), and the half-peak width was 30.1 nm. Compared with the result of comparative example 3, the EQE is improved by 0.77 percent due to the further introduction of the aryl group on the benzo saturated ring, and the half-peak width is narrowed by 0.4nm, so that the blue luminescence property is effectively improved.

Table 3 device data for example 2 and comparative example 2

Discussion:

table 3 shows the device data of example 2 and comparative example 2, from which it can be seen that example 2 has an External Quantum Efficiency (EQE) of 9.02%, a maximum emission wavelength of 463nm, a CIE of (0.133,0.129), and a half-peak width of 30.5 nm; comparative example 2 the External Quantum Efficiency (EQE) was 8.65%, the maximum emission wavelength was 463nm, CIE was (0.133 ), and the half-peak width was 30.5 nm. Compared with comparative example 2, the EQE of example 2 is improved by 4.27%, and the half-peak width and the maximum emission wavelength are kept unchanged. Example 2 it can be seen that an increase in EQE can be achieved by introducing a phenyl substituent in the other aryl group of the arylamine compared to comparative example 2.

In conclusion, the novel compound obtained by introducing the substituted hexabasic (hetero) aromatic ring and the saturated ring structure into one aryl group of the aromatic amine substituted pyrene compound and introducing the substituted (hetero) aryl group into the other aryl group is applied to the organic electroluminescent device, so that the blue emission wavelength, the EQE and the half-peak width are higher, and the comprehensive performance of the device is improved.

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

Claims

1. A compound having the structure of formula 1:

wherein, in the formula 1,

substituent R₁-R₁₀At least one of which has the structure of formula 2:

wherein, in the formula 2,

R_x2and R_y2Each occurrence, the same or different, is selected from the group consisting of: 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 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 having 0 to 20 carbon atomsA group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

n is 0, 1,2, 3,4 or 5;

substituent R_zCan optionally be linked to form a ring.

2. The compound of claim 1, wherein the substituent having formula 2 further has the structure of formula 3 or formula 4:

wherein, in formula 3 and formula 4,

X₁-X₃and X₅Selected from CR, identically or differently at each occurrence_x1，CR_x2Or N; and X₁-X₃And X₅At least one of which is CR_x2；

Y₁-Y₅、L、Z、n、R_x1And R_x2Has the same definition as in claim 1;

represents a position where the substituent having a structure represented by formula 3 or formula 4 is attached to formula 1.

3. The compound of any one of claims 1-2, wherein n is 0, 1,2, 3; preferably, n is 1.

4. The compound of claim 2, wherein substituent R₁And R₆Has a structure represented by formula 3 or formula 4, and R₁And R₆Are the same or different; r₂To R₅，R₇To R₁₀The same or different at each occurrence is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

preferably, the substituent R₁And R₆Has a structure represented by formula 2, formula 3 or formula 4, and R₁And R₆Are the same or different; r₂，R₄-R₅，R₇And R₉-R₁₀Is hydrogen, R₃And R₈Is selected, identically or differently on each occurrence, from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted alkyl havingCycloalkyl groups having 3 to 20 ring carbon atoms.

5. The compound of any one of claims 1-4, wherein L, identically or differently at each occurrence, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;

preferably, L is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof;

more preferably, L is selected from single bonds.

6. The compound of any one of claims 2-5, wherein X₁-X₃And X₅Selected from CR, identically or differently at each occurrence_x1Or CR_x2And X₁-X₃And X₅At least one of them is selected from CR_x2；Y₁-Y₅Selected from CR, identically or differently at each occurrence_y1Or CR_y2And Y is₁-Y₅At least one of them is selected from CR_y2。

7. The compound of any one of claims 1-6, wherein R_x1And R_y1Each 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 12 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, and combinations thereof;

preferably, wherein R_x1And R_y1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, methyl, ethyl, n-propylIsopropyl, cyclopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof.

More preferably, R_x1And R_y1Is hydrogen.

8. The compound of any one of claims 1-7, wherein X₁-X₅At least one is CR_x2And R is_x2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;

preferably, R_x2Each occurrence, the same or different, is selected from the group consisting of: phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthryl, anthracenyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiollolyl, dibenzothiapyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

9. The compound of any one of claims 1-8, wherein Y is₂-Y₄At least one is CR_y2And R is_y2Selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof;

preferably, R_y2Each occurrence, the same or different, is selected from the group consisting of: phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthryl, anthracenyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiollolyl, dibenzothiapyrrolyl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

10. The compound of claim 9, wherein Y₁And/or Y₅Is CR_y2And R is_y2Identical or different at each occurrenceSelected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof;

preferably, R_y2Each occurrence, the same or different, is selected from the group consisting of: methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, cyclopropyl, deuterated cyclopropyl, n-butyl, deuterated n-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, and deuterated cyclohexyl.

11. The compound of any one of claims 1-10, wherein Z is C (R)_z)₂And R is_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof;

preferably, R_zEach occurrence, the same or different, is selected from the group consisting of: hydrogen, halogen, deuterium, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof;

substituent R_zCan optionally be linked to form a ring.

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

13. an electroluminescent device, comprising:

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

a cathode electrode, which is provided with a cathode,

wherein, in the formula 1,

substituent R₁-R₁₀At least one of them has a structure represented by formula 2;

and the substituent R₁-R₁₀The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

wherein, in the formula 2,

X₁-X₅selected, identically or differently at each occurrence, from C, CR_x1，CR_x2Or N; and X₁-X₅At least two of which are adjacent to each other are C,and is linked to X in formula 2₁-X₅At least one of which is CR_x2；

R_x1and R_y1Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

R_x2and R_y2Each occurrence, the same or different, is selected from the group consisting of: 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 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 atomsA group, 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 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 mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

n is 0, 1,2, 3,4 or 5;

substituent R_zCan optionally be linked to form a ring.

14. The organic electroluminescent device as claimed in claim 13, wherein the organic layer comprises a light emitting layer, wherein the light emitting layer comprises a compound having the structure of formula 1.

15. The organic electroluminescent device according to claim 14, wherein the light-emitting layer further comprises a host material;

preferably, the host material comprises a compound having the structure of formula 5:

wherein, in the formula 5,

R_g1to R_g8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 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 arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, isonitrile group, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;

16. A compound formulation comprising a compound as defined by any one of claims 1 to 12.