CN114835718B

CN114835718B - Organic electroluminescent material and device thereof

Info

Publication number: CN114835718B
Application number: CN202110130852.2A
Authority: CN
Inventors: 王乐; 张晗; 王强; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2021-01-30
Filing date: 2021-01-30
Publication date: 2024-10-18
Anticipated expiration: 2041-01-30
Also published as: CN114835718A

Abstract

An organic electroluminescent material and an apparatus thereof are disclosed. The organic electroluminescent material is a novel compound formed by connecting indole and pyrrole condensed aza macrocycles with an aza ring segment bonded with substituted dibenzofuran and the structure similar to the indole and pyrrole condensed aza macrocycles, and can be used as a main body material in an organic electroluminescent device. These novel compounds can reduce the voltage of the device, improve the efficiency of the device, and provide better device performance. In addition, an organic electroluminescent device and a compound combination comprising the compound 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 formed by connecting indole and pyrrole fused azamacrocycles with an azacyclic fragment bonded with a substituted dibenzofuran and its similar structures, and an organic electroluminescent device and a compound combination comprising 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 (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

In 1987, tang and Van Slyke of Isomangan 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 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.

KR1020150077220A discloses an organic electroluminescent compound, an organic optical compound having the following structureThe general formula compound X ₁ disclosed therein may be N (Ar ₁), but does not disclose or teach compounds in which indole and pyrrole fused azamacrocycles are linked to an azacyclic structure to which substituted dibenzofurans and similar structures are bonded.

US20180337340A1 discloses an organic electroluminescent compound and an organic electroluminescent device comprising the same, comprising an organic layer comprising one or more hosts, the first host of which is an organic optical compound having the structure: However, the disclosed compounds must have an azaaromatic ring structural unit of quinoline, quinazoline or quinoxaline and must be bonded at a specific position of quinoline, quinazoline or quinoxaline, and do not disclose or teach compounds in which an indole fused azamacrocycle is linked to an azaheterocyclic structure to which substituted dibenzofurans and similar structures are bonded.

However, there is still room for improvement in many of the currently reported host materials, 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 invention aims to solve at least part of the above problems by providing a compound formed by the attachment of indole and pyrrole fused azamacrocycles to an azacyclic fragment to which is bonded a substituted dibenzofuran and its analogous structures. The compounds are useful as host materials in organic electroluminescent devices. These novel compounds can reduce the voltage of the device, improve the efficiency of the device, and provide better device performance.

According to one embodiment of the present invention, a compound is disclosed having the structure of H-L-E, wherein H has the structure represented by formula 1:

In formula 1, a ₁、A₂ and a ₃ are, identically or differently, selected for each occurrence from N or CR, and ring a, ring B and ring C are, identically or differently, selected from carbocycles having from 5 to 30 carbon atoms, or heterocycles having from 3 to 30 carbon atoms;

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

e has a structure represented by formula 2:

In formula 2, Z is selected from CR _zR_z,SiR_zR_z,NR_z,BR_z,PR_z, O, S or Se; when two R _z are present simultaneously, the two R _z may be the same or different;

Y ₁ to Y ₅ are each independently selected from C, N or CR _Y, and three of Y ₁ to Y ₅ are N;

Y ₆ to Y ₁₃ are each independently selected from C, N, CR _ZY or CR _Y, and at least one of Y ₆ to Y ₁₃ is CR _ZY;

r _ZY is selected identically or differently on each occurrence from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 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 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;

L, L ₁ are, identically or differently, selected from the group consisting of: 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, and combinations thereof;

R, R _z,R_x,R_Y are, identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, 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;

Adjacent substituents R _z,R_Y can optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound of the above embodiment.

According to another embodiment of the present invention, there is also disclosed a combination of compounds comprising the compounds of the above embodiments.

The novel compound formed by connecting indole and pyrrole condensed aza macrocycles with the aza ring fragments bonded with substituted dibenzofuran and the similar structures can be used as a main body material in an organic electroluminescent device. These novel compounds can reduce the voltage of the device, improve the efficiency of the device, and provide better device performance.

Drawings

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

Fig. 2 is a schematic view of another organic light emitting device that may contain the compounds and combinations of compounds 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 various layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2 at 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 m-MTDATA doped with F ₄ -TCNQ at a molar ratio of 50:1, 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 yields 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 include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermyleisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethyl-germylmethyl, triethylgermylmethyl, triethylgermylethyl, tert-butyldimethyl-germanium-based methyl group, triethylgermylmethyl, triethylgermylethyl. In addition, heteroalkyl groups may be optionally substituted.

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

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

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

Heterocyclyl or heterocycle-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxane, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, a thiepinyl group, azetidinyl 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, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy tetrahydrofuranyloxy, tetrahydropyranyloxy methoxy propyloxy, ethoxy ethyloxy, methoxy methyloxy and ethoxy methyloxy. 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, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butyl silicon group, diphenyl isobutyl silicon group, diphenyl tert-butyl silicon group. 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, multiple substitution is meant to encompass double substitution 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:

e has a structure represented by formula 2:

R _ZY is selected identically or differently on each occurrence from the group consisting of: 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 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 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, sulfonyl, phosphino, and combinations thereof;

l, L ₁ are the same or different at each occurrence selected from the group consisting of: 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, and combinations thereof;

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

Adjacent substituents R _z,R_Y can optionally be linked to form a ring.

In this embodiment, adjacent substituents R, R _x can optionally be linked to form a ring, and is intended to mean wherein adjacent groups of substituents, such as between substituents R, between substituents R _x, and between substituents R and R _x, any one or more of which can be linked to form a ring. Obviously, none of these adjacent groups of substituents may be linked to form a ring.

Herein, adjacent substituents R _z,R_Y can optionally be linked to form a ring, intended to mean wherein adjacent groups of substituents, such as between adjacent substituents R _Y in Y ₆-Y₁₃, and between adjacent substituents R _z, any one or more of which groups can be linked to form a ring. Obviously, none of these adjacent groups of substituents may be linked to form a ring.

According to one embodiment of the invention, wherein in formula 1, the rings a, B and C are, identically or differently, selected for each occurrence from a 5-membered carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.

According to one embodiment of the invention, wherein in formula 1, the rings a, B and C are, identically or differently, selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring for each occurrence.

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

Wherein a ₁ to a ₃ are, identically or differently, selected from N or CR for each occurrence, X ₁ to X ₁₀ are, identically or differently, selected from N or CR _x for each occurrence;

R, R _x are, identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, 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.

Herein, adjacent substituents R, R _x can optionally be linked to form a ring, intended to mean that adjacent substituents R can optionally be linked to form a ring, and also intended to mean that adjacent substituents R _x in X ₁ to X ₃ can optionally be linked to form a ring, Also intended to mean that adjacent substituents R _x in X ₄ to X ₆ can optionally be linked to form a ring, and also intended to mean that adjacent substituents R _x in X ₇ to X ₁₀ can optionally be linked to form a ring; And, it is also intended that adjacent substituents R and R _x can optionally be linked to form a ring, for example between A ₁ and X ₃, and/or between A ₃ and X ₁₀, and/or X ₆ and X ₇ may be optionally linked together to form a ring. It will be apparent to those skilled in the art that adjacent substituents R, R _x may not be joined to form a ring, in which case adjacent substituents R are not joined to form a ring, and/or adjacent substituents R _x are not joined to form a ring, and/or adjacent substituents R and R _x are not joined to form a ring.

According to one embodiment of the invention, wherein in formula 1-a, R _x are 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;

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

According to one embodiment of the present invention, wherein at least one of R and R _x in the formula 1-a is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to one embodiment of the present invention, wherein at least one of R and R _x in the formula 1-a is selected from deuterium, phenyl, biphenyl, or pyridyl.

According to one embodiment of the invention, wherein at least one group of adjacent substituents R, R _x in formula 1-a are linked to form a ring.

In this embodiment, at least one set of adjacent substituents R, R _x are joined to form a ring, and are intended to represent adjacent groups of substituents, for example, adjacent substituents R _x,X₄ to X ₆ of X ₁ to X ₃, adjacent substituents R _x,A₁ to X ₁₀ of R _x,X₇ to X ₃, adjacent substituents R and R _x of R _x,A₃ and X ₁₀, and adjacent substituents R _x of X ₆ and X ₇, at least one of which are optionally joined to form a ring.

According to one embodiment of the present invention, wherein in formula 1-a, at least one of the adjacent substituents R between a ₁ and a ₃, the adjacent substituents R _x,X₄ to X ₆ between X ₁ and X ₃, the adjacent substituent R _x between X ₇ and X ₁₀, and the adjacent substituents R _x between X ₇ and X ₁₀ are linked to form a ring.

In this embodiment, at least one of the adjacent substituent groups is linked to form a ring, and is intended to mean that for the adjacent substituent groups present in formula 1-a, for example, two adjacent substituents R in A ₁ and A ₂, two adjacent substituents R in A ₂ and A ₃, Two adjacent substituents R _x,X₂ of X ₁ and X ₂ and two adjacent substituents R _x,X₄ of X ₃ and two adjacent substituents R _x,X₅ of X ₅ and two adjacent substituents R _x,X₇ of X ₆ and two adjacent substituents R _x,X₈ of X ₈ and two adjacent substituents R _x of X ₉, And two adjacent substituents R _x in X ₉ and X ₁₀, at least one of which groups is linked to form a ring.

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

Wherein "+" denotes the position of the structure of the H-1 to H-139 to which the 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, in the formula 2, Y ₁,Y₃,Y₅ is N, in which case the E in the compound has a structure represented by formula 2-1:

In the formula 2-1 of the present invention,

Z is selected from CR _zR_z,SiR_zR_z,NR_z,BR_z,PR_z, O, S or Se; when two R _z are present simultaneously, the two R _z may be the same or different;

L ₁ is selected identically or differently on each occurrence from the group consisting of: 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, and combinations thereof;

R _ZY is selected identically or differently on each occurrence from the group consisting of: 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 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 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, cyano, and combinations thereof;

The R _z,R_Y 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 arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof;

Adjacent substituents R _z,R_Y can optionally be linked to form a ring.

According to one embodiment of the invention, wherein, in the formulae 2 and 2-1, L ₁ is selected identically or differently on each occurrence from the group consisting of: single bonds, substituted or unsubstituted arylene groups having 6 to 24 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 24 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein, in the formulae 2 and 2-1, L ₁ is selected identically or differently on each occurrence 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 present invention, wherein, in the formula 2 and the formula 2-1, Z is selected from CR _zR_z,SiR_zR_z,NR_z,BR_z,PR_z, O, S or Se; when two R _z are present simultaneously, the two R _z may be the same or different;

The R _z 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 arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof;

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

Herein, adjacent substituents R _z can optionally be linked to form a ring, which is intended to mean that adjacent substituents R _z in said formula 2 can be linked to form a ring. Obviously, none of these adjacent substituents may be linked to form a ring.

According to one embodiment of the present invention, wherein, in the formula 2 and the formula 2-1, Z is selected from CR _zR_z,NR_z,SiR_zR_z, O, S or Se; when two R _z are present simultaneously, the two R _z may be the same or different;

The R _z is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl groups having 3 to 20 ring atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;

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

According to one embodiment of the present invention, wherein, in the formula 2 and the formula 2-1, Z is selected from O or S.

According to one embodiment of the present invention, wherein, in the formula 2 and the formula 2-1, Y ₆ to Y ₁₃ are each independently selected from C, N, CR _ZY or CR _Y, and at least one of Y ₆ to Y ₁₃ is CR _ZY;

The R _ZY is selected identically or differently on each occurrence from the group consisting of: 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted arylsilane having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, cyano, and combinations thereof;

The R _Y 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 arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, substituted or unsubstituted amino groups having from 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof;

Adjacent substituents R _Y can optionally be linked to form a ring.

Herein, adjacent substituents R _Y can optionally be linked to form a ring, intended to mean that any adjacent substituent R _Y in Y ₆-Y₁₃ can be linked to form a ring. Obviously, none of these adjacent substituents may be linked to form a ring.

According to one embodiment of the present invention, wherein, in the formula 2 and the formula 2-1, Y ₆ to Y ₁₃ are each independently selected from C, CR _ZY or CR _Y;

The R _ZY is selected identically or differently on each occurrence 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 aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof;

the R _Y is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

The R _ZY is selected identically or differently on each occurrence from the group consisting of: methyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, methylphenyl, tert-butylphenyl, tridecylmethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, triphenylenyl, and combinations thereof;

The R _Y is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, methyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, methylphenyl, tert-butylphenyl, trideutero methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, triphenylenyl, and combinations thereof.

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

Wherein, Represents the position of attachment to the L in the structure of the E-1 to E-113.

According to one embodiment of the invention, wherein hydrogen in the structure of E-1 to E-113 can be partially or completely replaced by deuterium.

According to one embodiment of the invention, wherein said L is, identically or differently, selected from the group consisting of: single bonds, substituted or unsubstituted arylene groups having 6 to 24 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 24 carbon atoms, and combinations thereof.

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

wherein ". Times." indicates the position of the structure of L-0 to L-27 to which the H is attached, Represents the position of attachment to the E in the structures of the L-0 to L-27.

According to one embodiment of the invention, wherein hydrogen in the structures of L-1 to L-27 can be partially or completely replaced by deuterium.

According to one embodiment of the present invention, wherein the compound has a structure of H-L-E, and the H is any one selected from the group consisting of H-1 to H-139, the L is any one selected from the group consisting of L-0 to L-27, and the E is any one selected from the group consisting of E-1 to E-113; optionally, hydrogen in the structure of the compound can be partially or fully substituted with deuterium.

According to one embodiment of the present invention, wherein the compound is selected from the group consisting of compound 1 to compound 730, the specific structure of the compound 1 to compound 730 is presented in claim 12.

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 an H-L-E structure, the specific structure of the compound being as described in any of the foregoing embodiments.

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, wherein in the electroluminescent device the organic layer is a light emitting layer, the light emitting layer further comprises at least one host material, the at least one host material being different from the compound, and the at least one host material comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

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 in the electroluminescent device the phosphorescent material is a metal complex having the general formula M (L _a)_m(L_b)_n(L_c)_q;

wherein M is selected from metals having a relative atomic mass greater than 40;

L _a、L_b、L_c is a first ligand, a second ligand and a third ligand coordinated to the M, respectively; l _a、L_b、L_c can optionally be linked to form a multidentate ligand; for example, any two of L _a、L_b and L _c may be linked to form a tetradentate ligand; for another example, L _a、L_b and L _c may be linked to each other to form a hexadentate ligand; or, for another example, none of L _a、L_b、L_c is linked so as not 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 or 1; the sum of M, n, q is equal to the oxidation state of M; when m is 2 or more, the 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 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 are fused via U _a and U _b;

u _a and U _b are, identically or differently, selected from C or N at each occurrence;

R _d,R_e, identically or differently for each occurrence, represents monosubstituted, polysubstituted or unsubstituted;

V ₁-V₄ is selected identically or differently on each occurrence from CR _v or N;

R _d,R_e,R_v 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 is selected identically or differently on each occurrence from any one of the following structures:

Wherein,

R _a,R_b and R _c, which are identical or different at each occurrence, represent monosubstituted, polysubstituted or unsubstituted;

X _b is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR _N1 and CR _C1R_C2;

X _c and X _d are 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 _C2 are 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;

In the structure of the ligand L _b、L_c, adjacent substituents R _a,R_b,R_c,R_N1,R_N2,R_C1 and R _C2 can optionally be linked to form a ring.

Herein, adjacent substituents R _d,R_e,R_v can optionally be linked to form a ring, intended to mean that when substituents R _d, R _e, R _v are present, wherein any one or more of the adjacent groups of substituents, for example, between adjacent substituents R _d, between adjacent substituents R _e, between adjacent substituents R _v, between adjacent substituents R _d and R _e, between adjacent substituents R _d and R _v, and between adjacent substituents R _e and R _v, can be linked to form a ring. Obviously, when substituents R _d, R _e, R _v are present, none of these groups of substituents may be linked to form a ring.

In this embodiment, adjacent substituents R _a,R_b,R_c,R_N1,R_N2,R_C1 and R _C2 can optionally be joined to form a ring, which is intended to mean groups of substituents wherein adjacent substituents, for example, between two substituents R _a, between two substituents R _b, Between the two substituents R _c, between the substituents R _a and R _b, between the substituents R _a and R _c, Between substituents R _b and R _c, between substituents R _a and R _N1, between substituents R _b and R _N1, Between substituents R _a and R _C1, between substituents R _a and R _C2, between substituents R _b and R _C1, Between substituents R _b and R _C2, between substituents R _a and R _N2, between substituents R _b and R _N2, And between R _C1 and R _C2, any one or more of these substituent groups may be linked to form a ring. obviously, these substituents may not all be linked to form a ring.

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

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

L _a、L_b is a first ligand and a second ligand, respectively, that coordinate to the M; 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; q is 0 or 1; the sum of M, n, q is equal to the oxidation state of M; when m is 2 or more, the 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 are fused via U _a and U _b;

adjacent substituents R _d,R_e,R_v can optionally be linked to form a ring;

Wherein the ligand L _b has the following structure:

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

According to one embodiment of the invention, in the electroluminescent device, the ligand L _b has the following structure:

Wherein at least one of R ₁-R₃ is selected from the group consisting of substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and/or at least one of R ₄-R₆ is selected from the group consisting of substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.

wherein at least two of R ₁-R₃ are, identically or differently, 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 at least two of R ₄-R₆ 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 at least two of R ₁-R₃ 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 at least two of R ₄-R₆ 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, wherein in the electroluminescent device the phosphorescent material is an Ir complex, a Pt complex or an Os complex.

According to one embodiment of the invention, wherein in the electroluminescent device, the phosphorescent light emitting material is an Ir complex and has a structure shown in either Ir(L_a)(L_b)(L_c)、Ir(L_a)₂(L_b)、Ir(L_a)₂(L_c) or Ir (L _a)(L_c)₂).

According to one embodiment of the invention, wherein in the electroluminescent device the phosphorescent light emitting material is an Ir complex and comprises a ligand L _a, the L _a having the structure as shown in formula 4 and comprising 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, wherein in the electroluminescent device the phosphorescent light-emitting material is an Ir complex and comprises a ligand L _a, the L _a having a structure as shown in formula 4 and comprising at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.

According to one embodiment of the invention, wherein in the electroluminescent device the phosphorescent material is an Ir complex and comprises a ligand L _a, the L _a at each occurrence being any one selected from the group consisting of:

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 _b at each occurrence being any one selected from the group consisting of:

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

according to another embodiment of the present invention, there is also disclosed a compound combination comprising the compound having an H-L-E structure, the specific structure of the compound being as shown in any one of the preceding 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. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, the evaporator manufactured by Angstrom Engineering, the optical test system manufactured by Frieda, st. O. F. And the lifetime test system, 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 180

Step 1: synthesis of intermediate 2

Intermediate 1 (4 g,9.2 mmol), o-fluorobenzeneboronic acid (1.5 g,11.1 mmol), tetrakis triphenylphosphine palladium (531.5 mg,0.46 mmol), potassium carbonate (2.5 g,18.4 mmol), dioxane (80 mL), water (16 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 (PE/dcm=10/1) to give intermediate 2 (4 g, yield: 89%) as a white solid.

Step 2: synthesis of Compound 180

Intermediate 2 (3 g,6.1 mmol), intermediate 3 (2 g,6.1 mmol), cesium carbonate (4 g,12.2 mmol), DMAC (N, N-dimethylacetamide, 80 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, 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 (PE/dcm=30/1) to give compound 180 (3 g, yield: 61%) as a yellow solid. The product was identified as the target product, molecular weight 803.3.

Synthesis example 2: synthesis of Compound 177

Step 1: synthesis of intermediate 5

Intermediate 4 (4 g,9.2 mmol), o-fluorobenzeneboronic acid (1.5 g,11.1 mmol), tetrakis triphenylphosphine palladium (531.5 mg,0.46 mmol), potassium carbonate (2.5 g,18.4 mmol), dioxane (80 mL), water (16 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 (PE/dcm=4/1) to give intermediate 5 (3.3 g, yield: 73%) as a white solid.

Step 2: synthesis of Compound 177

Intermediate 5 (3 g,6.1 mmol), intermediate 3 (2 g,6.1 mmol), cesium carbonate (4 g,12.2 mmol), DMAC (80 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, 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 (PE/dcm=30/1) to give compound 177 (1 g, yield: 20%) as a yellow solid. The product was identified as the target product, molecular weight 803.3.

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

Device example 1

First, a glass substrate having a 120nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was baked in a glove box filled with nitrogen gas to remove moisture, and then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was prepared under a vacuum of about 10 ^-8 Torr Is evaporated on the ITO anode in sequence by thermal vacuum. The compound HI was used as a Hole Injection Layer (HIL) with a thickness ofThe compound HT is used as a Hole Transport Layer (HTL) with a thickness ofCompound EB is used as Electron Blocking Layer (EBL) with thickness ofThen co-evaporating the compound 180 of the present invention as a host and the compound RD as a dopant to be used as an emitting layer (EML) with a thickness ofUsing compound HB as a Hole Blocking Layer (HBL) with a thickness ofOn the hole blocking layer, the compound ET and 8-hydroxyquinoline-lithium (Liq) are co-evaporated to form an Electron Transport Layer (ETL) with the thickness ofFinally, vapor deposition8-Hydroxyquinoline-lithium (Liq) as Electron Injection Layer (EIL) in thickness, and vapor deposition Is used as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.

Device comparative example 1

The embodiment of device comparative example 1 is the same as device example 1 except that compound a is used in place of compound 180 of the present invention as a host in the light emitting layer (EML).

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

Table 1 device structures of device examples and comparative examples

The material structure used in the device is as follows:

The maximum emission wavelength (λ _max), drive Voltage (Voltage) and Power Efficiency (PE) of the device examples and device comparative examples measured at a constant current of 15mA/cm ² are shown in Table 2.

Table 2 device data

Device ID	λ_max(nm)	Voltage[V]	PE[lm/W]
				Example 1	625	3.38	19.25
Comparative example 1	626	3.72	17.95

Discussion:

as can be seen from the data in table 2, the maximum emission wavelengths of example 1 and comparative example 1 remain substantially the same; in terms of driving voltage, the voltage of the embodiment 1 is reduced by 0.34V by 3.38V compared with 3.72V of the comparative embodiment 1, and the amplitude is reduced by 9.1%; the power efficiency of example 1 was increased by 1.3lm/W compared to 17.95lm/W of comparative example 1 by 19.25lm/W, and the amplification was 7.2%. From the above data, it can be seen that the compounds of the present invention can provide devices with lower voltages and higher efficiencies, demonstrating the more excellent properties of the compounds of the present invention.

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-E, wherein H has a structure represented by formula 1-a:

In formula 1-a, a ₁、A₂ and a ₃ are selected identically or differently for each occurrence from CR, X ₁ to X ₁₀ are selected identically or differently for each occurrence from CR _x;

e has a structure represented by formula 2:

in formula 2, Z is selected from O;

y ₁ to Y ₅ are each independently selected from C, N or CR _Y, and Y ₁,Y₃,Y₅ is N;

Y ₆ to Y ₁₃ are each independently selected from C, CR _ZY or CR _Y, and at least one of Y ₆ to Y ₁₃ is CR _ZY;

r _ZY is selected identically or differently on each occurrence from the group consisting of: halogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxazole, substituted or unsubstituted benzothiazole;

L is selected from the group consisting of, identically or differently, for each occurrence: a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;

L ₁, the same or different at each occurrence, is selected from: a single bond;

R, R _x,R_Y are, identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 12 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxazole, substituted or unsubstituted benzothiazole;

The substituted alkyl group, substituted aryl group, substituted pyridyl group, substituted pyrimidyl group, substituted dibenzothienyl group, substituted dibenzofuranyl group, substituted carbazolyl group, substituted benzoxazol group, substituted benzothiazole group refers to any one of alkyl group, aryl group, pyridyl group, pyrimidyl group, dibenzothienyl group, dibenzofuranyl group, carbazolyl group, benzoxazole group, benzothiazole group may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl group having 1 to 12 carbon atoms, unsubstituted aryl group having 6 to 20 carbon atoms, pyridyl group, pyrimidyl group, dibenzothienyl group, dibenzofuranyl group, carbazolyl group, benzoxazole group, benzothiazole group, cyano group.

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

Wherein a ₁ to a ₃ are selected identically or differently for each occurrence from CR, X ₁ to X ₁₀ are selected identically or differently for each occurrence from CR _x;

Wherein R, R _x are selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms.

3. The compound as recited in claim 1, wherein in formula 1-a, at least one of R and R _x is selected from deuterium, substituted or unsubstituted aryl groups having 6-20 carbon atoms.

4. The compound of claim 1, wherein at least one of R and R _x is selected from deuterium, phenyl, biphenyl.

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

wherein optionally, hydrogen energy in the H-1, H-102 to H-110, H-121, H-123 to H-139 is partially or fully substituted with deuterium.

6. The compound of claim 1, wherein Y ₆ to Y ₁₃ are each independently selected from C, CR _ZY or CR _Y;

The R _ZY is selected identically or differently on each occurrence from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms;

The R _Y is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 12 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

7. The compound of claim 1, wherein R _ZY is selected identically or differently on each occurrence from the group consisting of: methyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, methylphenyl, tert-butylphenyl, tridecylmethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, triphenylenyl;

The R _Y is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, methyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, methylphenyl, tert-butylphenyl, trideutero methylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, triphenylenyl.

8. The compound of claim 5, wherein E is selected from the group consisting of:

wherein, optionally, hydrogen energy in the structures E-1 to E-55, E-68, E-73, E-75, E-82 to E-96, E-99 to E-103 is partially or fully substituted with deuterium.

9. The compound of claim 1, wherein L is, identically or differently, selected from the group consisting of: substituted or unsubstituted arylene groups having 6 to 12 carbon atoms.

10. The compound of claim 1, wherein L is, identically or differently, selected from the group consisting of: phenylene, naphthylene, biphenylene, terphenylene, triphenylene.

11. The compound of claim 8, wherein L is, identically or differently, selected from the group consisting of:

wherein ". Times." indicates the position of the structure of said L-1 to L-14, L-17 to L-19, L-21 to L-27 to which said H is attached, Represents the position of attachment to E in the structures of L-1 to L-14, L-17 to L-19, L-21 to L-27;

Wherein, optionally, hydrogen in the structures of L-1 to L-14, L-17 to L-19, L-21 to L-27 can be partially or completely substituted with deuterium.

12. The compound of claim 11, wherein the compound has the structure of H-L-E, and the H is any one selected from the group consisting of H-1, H-102 to H-110, H-121, H-123 to H-139, the L is any one selected from the group consisting of L-1 to L-14, L-17 to L-19, L-21 to L-27, and the E is any one selected from the group consisting of E-1 to E-55, E-68, E-73, E-75, E-82 to E-96, E-99 to E-103. Optionally, hydrogen in the structure of the compound can be partially or fully substituted with deuterium.

13. The compound of claim 11, wherein the compound is selected from the group consisting of compounds having the structure H-L-E, wherein H, L and E each correspond to a structure selected from the following tables:

14. 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 1-13.

15. The electroluminescent device of claim 14 wherein the organic layer is a light emitting layer and the compound is a host material.

16. The electroluminescent device of claim 15 wherein the light-emitting layer further comprises at least one phosphorescent light-emitting material.

17. The electroluminescent device of claim 16 wherein the phosphorescent material is a metal complex.

18. The electroluminescent device of claim 16 wherein the phosphorescent material is an Ir complex, pt complex or Os complex.

19. A combination of compounds comprising a compound according to any one of claims 1 to 13.