CN117209510A

CN117209510A - Organic electroluminescent material and device thereof

Info

Publication number: CN117209510A
Application number: CN202210586695.0A
Authority: CN
Inventors: 王乐; 王强; 张子岩; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2022-05-30
Filing date: 2022-05-30
Publication date: 2023-12-12

Abstract

An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material has an H-L-Ar structure, and is a novel organic compound formed by connecting indole and pyrrole fused aza-macrocyclic structural fragments with benzo five-membered ring naphthyridine structural fragments through a connecting structure. The compounds can be used as host materials in organic electroluminescent devices, providing better overall performance for the device, such as lower voltage and higher efficiency. Electroluminescent devices and compound compositions comprising the organic electroluminescent material and electronic devices comprising the electroluminescent devices are also disclosed.

Description

Organic electroluminescent material and device thereof

Technical Field

The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. And more particularly, to a compound having an H-L-Ar structure, and an organic electroluminescent device and a compound composition including the same.

Background

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

In 1987, tang and Van Slyke of Isomandah reported a double-layered organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light emitting layer (Applied Physics Letters,1987,51 (12): 913-915). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.

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

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

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

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

The inventors' prior patent application CN113968875A discloses a compound having the structure H-L-E, wherein H hasL is selected from single bond, arylene or heteroarylene, E hasA structure; however, this application does not disclose or teach specific compounds in which indole and pyrrole fused aza-macrocyclic structural fragments are bonded via a linking structure to have benzo-penta-cyclic naphthyridine structural fragments, nor does it teach the use of such compounds in organic electroluminescent devices.

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

Disclosure of Invention

The present application aims to solve at least part of the above problems by providing a series of compounds having the structure H-L-Ar. The compounds are useful as host materials in organic electroluminescent devices. These novel compounds can provide better device performance, such as lower voltage and higher efficiency.

According to an embodiment of the present application, there is disclosed a compound having a structure of H-L-Ar, wherein H has a structure represented by formula 1:

Wherein, in the formula 1,

A ₁ 、A ₂ and A ₃ The ring a, ring B and ring C are selected identically or differently on each occurrence from N or CR, the ring a, ring B and ring C are selected identically or differently on each occurrence from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms;

R _x each occurrence, identically or differently, represents mono-, poly-or unsubstituted;

ar has a structure represented by formula 2:

wherein, in the formula 2,

z is selected from NR _z ，O，S，Se，SiR _z R _z ，CR _z R _z ，BR _z Or PR (PR) _z The method comprises the steps of carrying out a first treatment on the surface of the When two R's are simultaneously present _z When two R _z May be the same or different;

Z ₁ to Z ₁₀ Is selected identically or differently on each occurrence from C, N or CR _z And Z is ₅ And Z ₁₀ At least one of which is N, Z ₁ To Z ₁₀ One of which is selected from C and is linked to L;

l 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;

R，R _z and R is _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Adjacent substituents R, R _z ，R _x Can optionally be linked to form a ring;

". Times" denote the position of attachment of said H to said L.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a compound having an H-L-Ar structure; the specific structure of the compound is shown in the previous examples.

According to another embodiment of the present invention, there is also disclosed a compound composition comprising a compound having the H-L-Ar structure; the specific structure of the compound is shown in the previous examples.

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

The invention discloses a series of novel organic compounds with indole and pyrrole condensed aza-macrocyclic structural fragments bonded benzo five-membered ring naphthyridine structural fragments. The compounds can be used as host materials in organic electroluminescent devices, providing better overall performance for the device, such as lower voltage and higher efficiency.

Drawings

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

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

Detailed Description

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

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

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

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

The OLED also requires an encapsulation layer, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.

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

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

As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.

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

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

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

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

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

Definition of terms for substituents

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

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

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

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

Alkenyl-as used herein, covers straight chain, branched chain, and cyclic alkylene groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. In addition, alkenyl groups may be optionally substituted.

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

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferablyAryl groups of 6 to 20 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms. Examples of the aryl group include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl-4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl. In addition, aryl groups may be optionally substituted.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (including spiro, bridged, fused, etc.), as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

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

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

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

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

according to an embodiment of the present invention, there is disclosed a structure having H-L-Ar, wherein H has a structure represented by formula 1:

wherein, in the formula 1,

Ar has a structure represented by formula 2:

wherein, in the formula 2,

R，R _z and R is _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstitutedAlkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Adjacent substituents R, R _z ，R _x Can optionally be linked to form a ring;

". Times" denote the position of attachment of said H to said L.

In this embodiment, adjacent substituents R, R _z ，R _x Can optionally be linked to form a ring, intended to mean: in said H, adjacent groups of substituents, e.g. between adjacent substituents R, adjacent substituents R _x Between, substituents R and R _x In which any one or more of these substituents can be linked to form a ring, and in which Ar, adjacent groups of substituents, e.g. two, any adjacent substituents R _z Can be connected to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

According to one embodiment of the invention, wherein in formula 1, the ring a, ring B and ring C are, identically or differently, selected from a 5-membered unsaturated carbocycle, a benzene ring, a 5-membered heteroaryl ring, or a 6-membered heteroaryl ring.

According to one embodiment of the present invention, wherein the H has a structure represented by formula 1A:

wherein in formula 1A, A ₁ To A ₃ Is selected identically or differently on each occurrence from N or CR, X ₁ To X ₁₀ At each occurrenceIdentically or differently selected from N or CR _x ；

R and R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Adjacent substituents R, R _x Can optionally be linked to form a ring.

In this embodiment, adjacent substituents R, R _x Can optionally be linked to form a ring, intended to mean that in formula 1A, A ₁ To A ₃ Wherein adjacent substituents R can optionally be linked to form a ring, are also intended to mean X ₁ To X ₃ R is an adjacent substituent _x Can optionally be linked to form a ring, also intended to mean X ₄ To X ₆ R is an adjacent substituent _x Can optionally be linked to form a ring, also intended to mean X ₇ To X ₁₀ R is an adjacent substituent _x Can optionally be linked to form a ring, and is also intended to mean the adjacent substituents R and R _x Can optionally be linked to form a ring, e.g. A ₁ And X ₃ Between, and/or A ₃ And X ₁₀ Between, and/or X ₆ And X ₇ All of which can be optionally connected into a ring; it is obvious to the person skilled in the art that the adjacent substituents R, R _x Or may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents R _x Nor are they linked to form a ring, and/or adjacent substituents R and R _x Nor are they joined to form a ring.

According to one embodiment of the invention, wherein R and R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 amino having 0 to 20 carbon atoms, cyano, isocyano, hydroxy, mercapto, and combinations thereof.

According to one embodiment of the invention, wherein R and R _x At least one of the groups is selected from deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 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, or a combination thereof.

According to one embodiment of the invention, wherein R and R _x At least one of which is selected from deuterium, fluoro, cyano, hydroxy, mercapto, methyl, tridentate methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridinyl, phenylpyridinyl, or a combination thereof.

According to one embodiment of the present invention, wherein R and R in formula 1A _x At least one of which is selected from deuterium, phenyl,biphenyl, or pyridinyl.

According to one embodiment of the present invention, wherein in the formula 1A, A ₁ To A ₃ Adjacent substituents R, X ₁ To X ₃ R is a substituent adjacent to R _x ，X ₄ To X ₆ R is a substituent adjacent to R _x And X ₇ To X ₁₀ R is a substituent adjacent to R _x At least one of the adjacent groups of substituents is linked to form a ring.

In this embodiment, at least one of the adjacent substituent groups is linked to form a ring, which is intended to mean that for the adjacent substituent group present in formula 1A, for example, A ₁ And A ₂ Two adjacent substituents R, A ₂ And A ₃ Two adjacent substituents R, X ₁ And X ₂ Two adjacent substituents R _x ，X ₂ And X ₃ Two adjacent substituents R _x ，X ₄ And X ₅ Two adjacent substituents R _x ，X ₅ And X ₆ Two adjacent substituents R _x ，X ₇ And X ₈ Two adjacent substituents R _x ，X ₈ And X ₉ Two adjacent substituents R _x And X ₉ And X ₁₀ Two adjacent substituents R _x At least one of the groups of substituents is linked to form a ring.

According to one embodiment of the invention, wherein said H is selected from the group consisting of:

/>

wherein ". Times." indicates the position of said H-1 to H-139 to which said L is attached.

According to one embodiment of the invention, wherein the hydrogen in the H-1 to H-139 can be partially or completely replaced by deuterium.

According to an embodiment of the present invention, wherein Ar is selected from the structures represented by any one of formulas 2-a to 2-d:

wherein Z is selected from NR _z ，O，S，Se，SiR _z R _z ，CR _z R _z ，BR _z Or PR (PR) _z The method comprises the steps of carrying out a first treatment on the surface of the When two R's are simultaneously present _z When two R _z May be the same or different;

Z ₁ to Z ₁₀ Is selected identically or differently on each occurrence from C or CR _z And Z is ₁ To Z ₁₀ One of which is selected from C and is linked to L;

R _z and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 7 to 30 ring carbon atomsAlkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylate, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

Adjacent substituents R _z Can optionally be linked to form a ring.

In this embodiment, "adjacent substituent R _z Being optionally linked to form a ring "is intended to mean that in said Ar, adjacent groups of substituents, e.g. two adjacent substituents R _z Can optionally be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

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

According to one embodiment of the invention, wherein said R _z And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, phenyl, biphenyl, naphthyl, adamantyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.

According to one embodiment of the invention, wherein Z is selected from NR _z O, S or Se.

According to one embodiment of the invention, wherein Z is selected from O, S or Se.

According to one embodiment of the invention, wherein in Ar, Z ₆ To Z ₉ One of which is selected from C and is linked to said L.

According to one embodiment of the invention, wherein Ar is selected from the group consisting of:

/>

wherein,represents the position of the Ar-1 to Ar-110 linked to the L. />

According to one embodiment of the invention, wherein hydrogen in the Ar-1 to Ar-110 structures can be partially or fully substituted with deuterium.

According to one embodiment of the invention, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein said L is selected from the group consisting of: single bonds, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothienyl, pyridylene, thienyl, and combinations thereof.

According to one embodiment of the invention, wherein said L is selected from the group consisting of:

Wherein ". Times." represents the position of L-1 to L-29 to which the H is attached,represents a position of L-1 to L-29 to which Ar is bonded.

According to one embodiment of the invention, wherein hydrogen in the structures of L-1 to L-29 can be partially or completely replaced by deuterium.

According to one embodiment of the invention, wherein the compound has the structure of H-L-Ar, and wherein H is selected from any one of the group consisting of H-1 to H-139, L is selected from any one of the group consisting of L-0 to L-29, ar is selected from any one of the group consisting of Ar-1 to Ar-110; optionally, the hydrogen in the compound can be partially or fully substituted with deuterium.

According to an embodiment of the present invention, wherein the compound is selected from the group consisting of compound 1 to compound 598, the compound 1 to compound 598 having the structure H-L-Ar, the specific structure of the compound 1 to compound 598 is as defined in claim 11.

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

an anode is provided with a cathode,

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

and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of H-L-Ar, wherein a specific structure of the compound is as shown in any one of the foregoing embodiments.

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

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

According to one embodiment of the invention, the electroluminescent device wherein the luminescent layer further comprises at least one phosphorescent luminescent material.

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

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

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

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

L _a has a structure as shown in formula 3:

wherein,

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

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

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

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

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

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

R _d ，R _e ，R _v and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

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

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

wherein,

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

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

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

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

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

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

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

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

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

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

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

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

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

L _a has a structure as shown in formula 3:

wherein,

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

R _d ，R _e ，R _v and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atomsSubstituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

wherein the ligand L _b The structure is as follows:

wherein R is ₁ To R ₇ Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl Acyl, sulfonyl, phosphino, and combinations thereof.

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

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

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

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

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

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

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

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

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

/>

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

/>

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

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according to another embodiment of the present invention, there is also disclosed a compound composition comprising the compound having an H-L-Ar structure, the specific structure of the compound being as shown in any one of the preceding embodiments.

According to another embodiment of the present invention, an electronic device is also disclosed, which comprises the electroluminescent device according to any of the foregoing embodiments.

Combined with other materials

The materials described herein for specific layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

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

In the examples of material synthesis, all reactions were carried out under nitrogen protection, unless otherwise indicated. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bei Yi g sublimator, etc.), in a manner well known to those skilled in the art.

The method of manufacturing the electroluminescent device is not limited, and the following examples are only examples and should not be construed as limiting. Those skilled in the art will be able to make reasonable modifications to the preparation methods of the following examples in light of the prior art. The proportion of the various materials in the luminescent layer is not particularly limited, and a person skilled in the art can reasonably select the materials within a certain range according to the prior art, for example, the main material can occupy 80% -99% and the luminescent material can occupy 1% -20% based on the total weight of the luminescent layer; or the main material may account for 90% -98% and the luminescent material may account for 2% -10%. In addition, the main body material may be two materials, wherein the proportion of the two main body materials to the main body material may be 99:1 to 1:99, a step of; alternatively, the ratio may be 80:20 to 20:80; alternatively, the ratio may be 60:40 to 40:60. the characteristics of the light emitting device prepared in the examples were tested using equipment conventional in the art, in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.

Material synthesis examples:

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

synthesis example 1: synthesis of Compound 99

Step 1: synthesis of intermediate 1

2, 3-dichloro-quinoxaline (6.4 g,32 mmol), 2-chloro-6-hydroxyphenylboronic acid (5 g,29.1 mmol), tetrakis (triphenylphosphine) palladium (1.0 g,0.87 mmol), potassium carbonate (8 g,58.1 mmol), solvent (toluene/ethanol/water=80:20:20 ml) were added to a three-necked flask under nitrogen atmosphere and reacted overnight at 100 ℃. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography using PE/dcm=5:1 to give intermediate 1 (5.9 g, yield: 80%) as a white solid.

Step 2: synthesis of intermediate 3

Intermediate 2 (10 g,30.3 mmol), m-bromofluorobenzene (6.4 g,36.4 mmol), cesium carbonate (19.7 g,60.6 mmol), DMF (150 mL) were added to a three-necked flask under nitrogen and reacted overnight at 140 ℃. After the reaction was completed, cooled to room temperature, distilled water was added to precipitate a solid, and the solid crude product was obtained by filtration and washed with ethanol to obtain intermediate 3 (12.9 g, yield: 88%) as a yellow solid.

Step 3: synthesis of intermediate 4

Intermediate 3 (5 g,10.3 mmol), pinacol biborate (5.2 g,20.6 mmol), potassium acetate (2 g,20.6 mmol), 1' -bis (diphenylphosphino) ferrocene palladium dichloride (376 mg,0.5 mmol), dioxane (60 ml) were added to a three-necked flask under nitrogen and reacted overnight at 110 ℃. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography using PE/dcm=4:1 to give intermediate 4 (4 g, yield: 89%) as a white solid.

Step 4: synthesis of Compound 99

Intermediate 1 (1.8 g,6.9 mmol), intermediate 4 (3.7 g,6.9 mmol), tetrakis (triphenylphosphine) palladium (398.7 mg,0.345 mmol), potassium carbonate (1.9 g,13.8 mmol), solvent (toluene/ethanol/water=60:15:15 ml) were added to a three-necked flask under nitrogen and reacted overnight at 100 ℃. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography using PE/dcm=4:1 to give compound 99 (2.2 g, yield: 51%) as an orange solid. The product was identified as the target product and had a molecular weight of 624.2.

Synthesis example 2: synthesis of Compound 1

Step 1: synthesis of intermediate 5

2, 3-dichloro-quinoxaline (7 g,35 mmol), 2-fluoro-6-hydroxyphenylboronic acid (5 g,32 mmol), tetrakis (triphenylphosphine) palladium (1.1 g,0.96 mmol), potassium carbonate (8.8 g,64 mmol), solvent (toluene/ethanol/water=80:20:20 ml) were added to a three-necked flask under nitrogen atmosphere and reacted overnight at 100 ℃. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography using PE/dcm=4:1 to give intermediate 5 (3 g, yield: 39%) as a white solid.

Step 2: synthesis of Compound 1

Intermediate 5 (2 g,8.4 mmol), intermediate 2 (3 g,9.2 mmol), cesium carbonate (5.5 g,16.8 mmol), DMF (50 mL) were added to a three-necked flask under nitrogen and reacted overnight at 130 ℃. After the reaction was completed, cooled to room temperature, distilled water was added to precipitate a solid, and the solid crude product was obtained by filtration, and recrystallized in toluene to obtain orange solid compound 1 (3.0 g, yield: 65%). The product was identified as the target product and had a molecular weight of 548.2.

Synthesis example 3: synthesis of Compound 104

Step 1: synthesis of Compound 104

Intermediate 6 (0.5 g,2 mmol), intermediate 4 (1.2 g,2.2 mmol), tetrakis (triphenylphosphine) palladium (115 mg,0.1 mmol), potassium carbonate (552 mg,4 mmol), solvent (toluene/ethanol/water=20:4:4 ml) were added to a three-necked flask under nitrogen and reacted overnight at 100 ℃. After the reaction was completed, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, and the solvent was concentrated to remove the solvent, and the crude product was purified by column chromatography using PE/dcm=4:1 to give compound 104 (0.7 g, yield: 56%) as an orange solid. The product was identified as the target product and had a molecular weight of 624.2.

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

Device example 1

First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was baked in a glove box filled with nitrogen gas to remove moisture, and then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 ^-8 In the case of Torr Is evaporated on the ITO anode in sequence by thermal vacuum. Co-evaporation of Compound HT and Compound HI was used as hole injection layer (HIL, weight ratio 97:3, ">). The compound HT is used as hole transport layer (HTL, -/-A)>). Compound EB is used as electron blocking layer (EBL, -/-for)>). Then co-evaporation of compound 99 as host and compound RD as dopant was used as light emitting layer (EML, weight ratio 98:2, +.>). Use of Compound HB as hole blocking layer (HBL, -/->). On the hole blocking layer, a compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL, weight ratio 40:60,). Finally, vapor deposition->8-hydroxyquinoline-lithium (Liq) as Electron Injection Layer (EIL) in thickness, and vapor depositionIs used as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.

Device example 2

The embodiment of device example 2 is the same as device example 1 except that compound 104 is used as a host in place of compound 99 in the light-emitting layer (EML).

Device comparative example 1

The embodiment of device comparative example 1 is the same as device example 1 except that compound a is used as a host in place of compound 99 in the light-emitting layer (EML).

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

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

The material structure used in the device is as follows:

table 2 shows the constant current of 15mA/cm ² Voltage (voltage), power Efficiency (PE), current Efficiency (CE), and External Quantum Efficiency (EQE) data for the device examples and device comparative examples were measured under the conditions.

Table 2 device data for device examples 1-2 and comparative example 1

Device ID	Voltage[V]	PE(lm/W)	CE[cd/A]	EQE[％]
					Example 1	4.05	18.12	23.4	24.8
Example 2	3.66	17.4	20.3	21.7
					Comparative example 1	4.24	12.27	16.6	15.5

Discussion:

as can be seen from the data of table 2, using the compound of the present invention in the light emitting layer can obtain more excellent device performance than comparative example, specifically, examples 1 and 2 are reduced by 0.19V, 0.58V, respectively, in terms of voltage, and example 1 is improved by 47.7%,41%,60% respectively, in terms of power efficiency, current efficiency, and external quantum efficiency, compared to comparative example 1; example 2 was improved by 41.8%,22.3% and 40% compared to comparative example 1, respectively.

The data show that the specific benzofurazoles and the substituents with similar structures are introduced on the indole pyrrole fused aza macrocyclic structural fragments through the connecting structures, so that the comprehensive performance of the device using the compound as a main body material is obviously improved, and the high efficiency is obtained under the condition of low driving voltage, thereby indicating the unique advantages of the compound, and having wide commercial development prospect and application value.

In addition, example 2 using the compound 104 of the present invention as a host material achieved a great improvement in device efficiency over comparative example 1, reaching an industry excellent level, and further achieved a significant 11% reduction in voltage based on the low voltage of example 1. This shows that when used as a host material, the compounds of the present invention wherein the indole and pyrrole fused azamacrocycles are specifically attached to the naphthalene ring of benzofurazanaphthalene via a linking structure can achieve further improvement in device voltage while ensuring excellent device efficiency, with unique advantages in terms of reduced energy consumption, over other compounds of the attachment site.

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

Claims

1. A compound having a structure of H-L-Ar, wherein H has a structure represented by formula 1:

wherein, in the formula 1,

ar has a structure represented by formula 2:

wherein, in the formula 2,

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

adjacent substituents R, R _z ，R _x Can optionally be linked to form a ring;

". Times" denote the position of attachment of said H to said L.

2. The compound of claim 1, wherein the ring a, ring B, and ring C are, identically or differently, selected from a 5-membered unsaturated carbocycle, a benzene ring, a 5-membered heteroaryl ring, or a 6-membered heteroaryl ring at each occurrence.

3. The compound of claim 1 or 2, wherein the H has a structure represented by formula 1A:

wherein in formula 1A, A ₁ To A ₃ Is selected identically or differently on each occurrence from N or CR, X ₁ To X ₁₀ Is selected identically or differently on each occurrence from N or CR _x ；

R and R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms Substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

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

preferably, R and R _x And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 amino having 0 to 20 carbon atoms, cyano, isocyano, hydroxy, mercapto, and combinations thereof.

4. A compound according to any one of claims 1 to 3, wherein R and R _x At least one of the group consisting of deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 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, or a combination thereof;

Preferably, R and R _x At least one of which is selected from deuterium, fluoro, cyano, hydroxy, mercapto, methyl, tridentate methyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridinyl, phenylpyridinyl, or a combination thereof.

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

wherein "+" denotes the position of said H-1 to H-139 attached to said L;

optionally, hydrogen in the H-1 to H-139 structures can be partially or fully substituted with deuterium.

6. The compound of claim 1, wherein Ar is selected from the structures represented by any one of formulas 2-a to 2-d:

R _z and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

Adjacent substituents R _z Can optionally be linked to form a ring;

preferably, wherein said R _z And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 3 carbon atomsHeteroaryl groups of 0 carbon atoms and combinations thereof;

more preferably, R _z And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, phenyl, biphenyl, naphthyl, adamantyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.

7. The compound of claim 1 or 6, wherein Z is selected from NR _z O, S or Se; preferably, Z is selected from O, S or Se.

8. The compound of claim 1 or 6, wherein said Z ₆ To Z ₉ One of which is selected from C and is linked to said L.

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

/>

wherein,represents a position of the Ar-1 to Ar-110 to which the L is attached;

optionally, hydrogen in the Ar-1 to Ar-110 structures can be partially or fully substituted with deuterium.

10. The compound of any one of claims 1-9, wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof;

preferably, said L is selected from the group consisting of: single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothienyl, pyridylene, thienyl, and combinations thereof;

more preferably, the L is selected from the group consisting of:

wherein ". Times." represents the position of L-1 to L-29 to which the H is attached,represents a position of L-1 to L-29 to which Ar is bonded;

optionally, hydrogen in the L-1 to L-29 structures can be partially or fully substituted with deuterium.

11. The compound of claim 10, wherein the compound has the structure of H-L-Ar, and wherein H is selected from any one of the group consisting of H-1 to H-139, L is selected from any one of the group consisting of L-0 to L-29, and Ar is selected from any one of the group consisting of Ar-1 to Ar-110; optionally, hydrogen in the compound can be partially or fully substituted with deuterium;

Preferably, the compound is selected from the group consisting of compound 1 to compound 598; wherein the compounds 1 to 598 have the structure H-L-Ar, H, L and Ar respectively correspond to the structures selected from the following tables:

/>

wherein, optionally, hydrogen in the structures of compounds 1-598 can be partially or fully substituted with deuterium.

12. An electroluminescent device, comprising:

an anode is provided with a cathode,

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

and an organic layer disposed between the anode and cathode, the organic layer comprising the compound of any one of claims 1 to 11.

13. The electroluminescent device of claim 12 wherein the organic layer is a light emitting layer; preferably, the compound is a host material.

14. The electroluminescent device of claim 13 wherein the light emitting layer further comprises at least one phosphorescent light emitting material.

15. The electroluminescent device of claim 14 wherein the phosphorescent material is a metal complex having M (L _a ) _m (L _b ) _n (L _c ) _q Is of the general formula (I);

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

L _a has a structure as shown in formula 3:

wherein,

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

wherein,

X _b and is selected identically or differently on each occurrence from the group consisting ofAnd (3) a group consisting of: o, S, se, NR _N1 And CR (CR) _C1 R _C2 ；

16. The electroluminescent device of claim 14 wherein the phosphorescent material is a metal complex having M (L _a ) _m (L _b ) _n Is of the general formula (I);

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

L _a has a structure as shown in formula 3:

wherein,

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

R _d ，R _e ，R _v and is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted Substituted 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 alkylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium 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, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

wherein the ligand L _b The structure is as follows:

wherein R is ₁ To R ₇ Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl Sulfonyl, phosphino, and combinations thereof;

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

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

17. The electroluminescent device of claim 15 or 16, wherein the phosphorescent light emitting material is an Ir complex, a Pt complex or an Os complex;

preferably, the phosphorescent material is an Ir complex and has Ir (L _a )(L _b )(L _c )、Ir(L _a ) ₂ (L _b )、Ir(L _a )(L _b ) ₂ 、Ir(L _a ) ₂ (L _c ) Or Ir (L) _a )(L _c ) ₂ Any of the structures shown.

18. A compound composition comprising a compound according to any one of claims 1-11.

19. An electronic device comprising the electroluminescent device of any one of claims 12 to 17.