CN117659039A

CN117659039A - Organic electroluminescent device

Info

Publication number: CN117659039A
Application number: CN202211050643.8A
Authority: CN
Inventors: 蔡刘欢; 赵春亮; 田学超; 桑明; 邝志远; 夏传军
Original assignee: Beijing Summer Sprout Technology Co Ltd
Current assignee: Beijing Summer Sprout Technology Co Ltd
Priority date: 2022-08-31
Filing date: 2022-08-31
Publication date: 2024-03-08

Abstract

The invention discloses an organic electroluminescent device. The organic electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including at least an organic light emitting layer including a first host material having a structure of formula 1 and a first compound having a structure of formula 3. The electroluminescent device of the present invention exhibits excellent overall device performance, such as higher efficiency and longer lifetime. Also disclosed is an electronic device comprising the organic electroluminescent device, and a compound composition of a first host material having a structure of formula 1 and a first compound having a structure of formula 3.

Description

Organic electroluminescent device

Technical Field

The present invention relates to organic electronic devices, such as organic electroluminescent devices. More particularly, to an organic electroluminescent device comprising a novel material combination of a first host material having a structure of formula 1 and a first compound having a structure of formula 3 in a light emitting layer, and an electronic apparatus comprising the organic electroluminescent device, and a composition of a first host material having a structure of formula 1 and a first compound having a structure of formula 3.

Background

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

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

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

Disclosed in US20180182976A1 are compounds having the general formula:wherein A is tableShown as having at least one substituent comprising one or two fused rings, or unsubstituted benzofuro [3,2-d ] ]Pyrimidine frameworks or substituted or unsubstituted acenothieno [3,2-d ] having at least substituents containing one or two fused rings]A pyrimidine skeleton; ar represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms or a single bond. In this application it is specifically disclosed that the compound +.>Etc. as host materials for use in phosphor devices. The application only researches the application of the compound as a main body material in a phosphorescent device, does not disclose or teach the application of the compound in a TADF device, and does not disclose or teach the application of the compound in the TADF device in combination with the first compound with the structure shown as the formula 3 in the invention.

Disclosed in US2022029105A1 are compounds having the general formula:wherein Q is ¹ Represents O or S, ar ¹ Ar and Ar ² Each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 25 carbon atoms, m and n are each independently 0 or 1, A represents any one of a substituted or unsubstituted benzothiophene carbazole ring, benzofurocarbazole ring, indolocarbazole ring and indenocarbazole ring, ht _uni Represents a skeleton having hole-transporting properties. In this application it is specifically disclosed that the compound +. >Etc. as host materials for use in particular embodiments of phosphor optical devices. The application only researches the application of the compound as a main body material in a phosphorescent device, does not disclose or teach the application of the compound in a TADF device, and does not disclose or teach the application of the compound in the TADF device in combination with the first compound with the structure shown as the formula 3 in the invention.

Disclosed in US2020028091A1A compound having the general formula:wherein Y is ¹ Is O or S; w is identically or differently selected from N or CR ¹ And no more than two of said W are N in one ring; x are identically or differently selected from N or CR ¹ And no more than two of said X's in a ring are N; l (L) ¹ Is a single bond or can be substituted by one or more R ^l A group-substituted aromatic or heteroaromatic ring having 5 to 30 aromatic ring atoms; a is identically or differently selected from N, CAr ^a Or CAr ^b Wherein exactly two A's are bound by at least one CAr ^a Or Car ^b N, the groups of which are separated, and if two N are adjacent to A, then A is CAr ^b ；Ar ^a 、Ar ^b Each independently selected from CN, F or can be substituted with one or more R ^l A group-substituted aromatic or heteroaromatic ring having 5 to 30 aromatic ring atoms. In this application, a specific disclosure is made of Etc. as host materials for use in particular embodiments of phosphorescent devices. The application only researches the application of the compound as a main body material in a phosphorescent device, does not disclose or teach the compound to be used in a TADF device, and does not disclose or teach the application of the compound in combination with the first compound with the structure shown as the formula 3 in the invention in the TADF device.

Some aza-dibenzofive-membered ring compounds are disclosed in the prior art as HOST materials (N-HOST) for use in phosphorescent devices, which can be matched with different types of phosphorescent guest materials, but the prior art does not disclose that the compounds can be used in TADF devices. The inventor has found a new material combination through intensive research, and can provide better device performance in TADF luminescent devices by combining aza-hexa-penta-hexatomic ring compounds with specific structures and different types of compounds with polycyclic condensed structures taking boron, nitrogen and the like as central atoms.

Disclosure of Invention

The present invention aims to provide an organic electroluminescent device with a novel material combination to solve at least part of the above problems. The organic electroluminescent device uses a novel material combination comprising a first host material having the structure of formula 1 and a first compound having the structure of formula 3, which can be used in a light-emitting layer of the organic electroluminescent device. The novel material combinations can exhibit superior overall device performance in devices, such as higher efficiency and longer lifetime.

According to an embodiment of the present invention, an organic electroluminescent device is disclosed, which includes:

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, wherein the organic layer comprises at least a light emitting layer;

wherein the light emitting layer comprises at least a first host material and a first compound;

wherein the first host material has a structure represented by formula 1:

in the formula (1) of the present invention,

z is selected from O, S, se, siRR or PR;

X ₁ -X ₈ is selected from CR, identically or differently at each occurrence ₁ ，CR ₂ Or N; and X is ₁ -X ₈ At least two of them are selected from N, X ₁ -X ₈ At least one of them is selected from CR ₁ ；

The R is ₁ Has a structure represented by formula 2:

R _a1 is selected identically or differently on each occurrence from substituted or unsubstituted having from 6 to 30 carbon atomsAryl of a child, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;

l is, identically or differently, selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

* Represents a substituent having the structure of formula 2 attached to the position of formula 1;

R，R ₂ and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl 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 6 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 ₂ Can optionally be linked to form a ring;

wherein the first compound has a structure represented by formula 3:

in formula 3, ring a, ring B, ring C are each independently selected from an aromatic ring having 6-30 carbon atoms, a heteroaromatic ring having 3-30 carbon atoms, or a combination thereof;

wherein Y is selected from B, P = O, P = S, al, ga, as, siR 'or der';

E ₁ ，E ₂ each independently selected from O, N-R _e S or Se, wherein N-R _e Has a structure represented by formula 4;

ring D is, identically or differently, selected for each occurrence from aromatic rings having 6-30 carbon atoms, heteroaromatic rings having 3-30 carbon atoms, or a combination thereof;

R _a ，R _b ，R _c ，R _d each occurrence, identically or differently, is represented as mono-substituted, poly-substituted or unsubstituted;

R’，R _a ，R _b ，R _c ，R _d and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 to 20 carbon atoms, substituted or unsubstituted germanium having 0 to 20 carbon atoms Carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

adjacent substituents R _a ，R _b ，R _c ，R _d Can optionally be linked to form a ring.

According to another embodiment of the present invention, there is also disclosed an electronic device including the organic electroluminescent device as described above.

According to another embodiment of the present invention, a compound composition is also disclosed, comprising at least a first host material and a first compound.

The invention discloses a novel electroluminescent device, which comprises a novel material combination composed of a first main body material with a structure shown in a formula 1 and a first compound with a structure shown in a formula 3, wherein the novel material combination can be used in a light-emitting layer of an organic electroluminescent device, in particular a TADF device. The novel material combinations can exhibit superior overall device performance in devices, such as higher efficiency and longer lifetime.

Drawings

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

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

Detailed Description

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

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

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

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

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

Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, 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 are required to have very small mono-triplet gaps in order for the transition between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.

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

Definition of terms for substituents

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

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

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

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

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

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

Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Aryl groups can beIs 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, wherein at least one ring atom 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 the preferred non-aromatic heterocyclic group is one having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. In addition, the heterocyclic group may be optionally substituted.

Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, wherein at least one heteroatom 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, indenazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza, 1-aza-3-borane, 1-borane, 4-boron, 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, the cycloalkyl group, the heteroalkyl group and the heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group may be optionally substituted.

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

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

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

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

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

Arylgermanium group-as used herein, encompasses at least one aryl or heteroaryl substituted germanium group. The arylgermanium group may be an arylgermanium group having 6-30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of aryl germanium groups include triphenyl germanium group, phenyl biphenyl germanium group, diphenyl biphenyl germanium group, phenyl diethyl germanium group, diphenyl ethyl germanium group, phenyl dimethyl germanium group, diphenyl methyl germanium group, phenyl diisopropyl germanium group, diphenyl isopropyl germanium group, diphenyl butyl germanium group, diphenyl isobutyl germanium group, diphenyl tert-butyl germanium 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, any one or more of which may be selected from the group consisting of deuterium, 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 arylsilane groups having from 6 to 20 carbon atoms, unsubstituted alkylgermanium groups having from 3 to 20 carbon atoms, unsubstituted arylgermanium groups having from 6 to 20 carbon atoms, unsubstituted amino groups having from 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino 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 syntropes in the compound may be preferred because of their enhanced efficiency and stability of the device.

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

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

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

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

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

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

an anode is provided with a cathode,

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

wherein the first host material has a structure represented by formula 1:

in the formula (1) of the present invention,

z is selected from O, S, se, siRR or PR;

The R is ₁ Has a structure represented by formula 2:

R _a1 the same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, or combinations thereof;

R，R ₂ and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substitutedOr unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 6 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, phosphine, and combinations thereof;

Adjacent substituents R, R ₂ Can optionally be linked to form a ring;

wherein the first compound has a structure represented by formula 3:

wherein Y is selected from B, P = O, P = S, al, ga, as, siR 'or der';

R’，R _a ，R _b ，R _c ，R _d and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl 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 6 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;

Herein, adjacent substituents R, R ₂ Can optionally be linked to form a ring, is intended to mean groups of substituents adjacent thereto, e.g. between two substituents R, and two substituents R ₂ Between which any one or more of these adjacent groups of substituents can be linked to form a ring. Obviously, none of these adjacent groups of substituents may be linked to form a ring.

Herein, adjacent fetchesSubstituent R _a ，R _b ，R _c ，R _d Can optionally be linked to form a ring, intended to mean groups of substituents adjacent thereto, e.g. two substituents R _a Between two substituents R _b Between two substituents R _c Between two substituents R _d Between, substituent R _a And R is _d Between, substituent R _b And R is _d Between and substituent R _c And R is _d Between which any one or more of these adjacent groups of substituents 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 present invention, none of the compounds contained in the light emitting layer is a metal complex.

According to one embodiment of the invention, wherein said X ₁ -X ₈ At least two of them are selected from CR ₁ 。

According to one embodiment of the invention, wherein said X ₁ -X ₈ Of which only two are selected from CR ₁ 。

According to one embodiment of the invention, wherein said X ₁ Selected from CR ₁ ，X ₆ Selected from CR ₁ 。

According to one embodiment of the invention, wherein said X ₃ Selected from CR ₁ ，X ₇ Selected from CR ₁ 。

According to one embodiment of the present invention, wherein the first host material has a structure represented by formula 1-1:

in the case of the formula 1-1,

z is selected from O, S, se, siRR or PR;

X ₁ -X ₈ is selected identically or differently on each occurrence from C, CR ₂ Or N; and X is ₁ -X ₈ At least two of which are selected from N;

R _a1 each time phase occursAnd is selected from the group consisting of substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, or combinations thereof;

Adjacent substituents R, R ₂ Can optionally be linked to form a ring.

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

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

According to one embodiment of the invention, wherein said Z is selected from S.

According to one embodiment of the invention, itThe X is as described in ₁ -X ₈ And only two are selected from N.

According to one embodiment of the invention, wherein said X ₁ -X ₄ And only two are selected from N.

According to one embodiment of the invention, wherein said X ₁ And X ₃ Selected from N.

According to one embodiment of the invention, wherein said X ₂ And X ₄ Selected from N.

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

According to one embodiment of the invention, wherein said L is chosen, identically or differently, for each occurrence, from a single bond.

According to one embodiment of the invention, wherein said R _a1 The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 18 carbon atoms, or combinations thereof.

According to one embodiment of the invention, wherein said R _a1 And is selected, identically or differently, on each occurrence, from the group consisting of: dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, indolocarbazolyl, imidazolyl, pyridyl, triazinyl, benzimidazolyl.

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

According to one embodiment of the invention, wherein said R, R ₂ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuteriumHalogen, cyano, substituted or unsubstituted aryl having from 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 18 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein said R, R ₂ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuropyranyl, dibenzofuranyl, benzothiophenyl, dibenzosilol, benzothiophenyl, dibenzothienyl, dibenzoselenophenyl, triazinyl, and combinations thereof.

According to one embodiment of the invention, wherein the first host material is selected from the group consisting of compound N-1-1 to compound N-1-15, compound N-2-1 to compound N-2-15, compound N-3-1 to compound N-3-15, compound N-4-1 to compound N-4-15, compound N-5-1 to compound N-5-15 and compound N-6-1 to compound N-6-26; the specific structures of the compounds N-1-1 to N-1-15, the compounds N-2-1 to N-2-15, the compounds N-3-1 to N-3-15, the compounds N-4-1 to N-4-15, the compounds N-5-1 to N-5-15 and the compounds N-6-1 to N-6-26 are shown in claim 9.

According to one embodiment of the invention, wherein the hydrogen energy in the structures of compounds N-1-1 to N-1-15, N-2-1 to N-2-15, N-3-1 to N-3-15, N-4-1 to N-4-15, N-5-1 to N-5-15 and N-6-1 to N-6-26 is partially or completely replaced by deuterium.

According to one embodiment of the invention, wherein the E ₁ And E is ₂ At least one of which is selected from N-R _e Wherein N-R _e Has a structure represented by formula 4:

R _d Each occurrence, identically or differently, is represented as mono-substituted, poly-substituted or unsubstituted;

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

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

in the case of the method of claim 5,

ring a, ring B, ring C, and ring D are identically or differently selected at each occurrence from aromatic rings having 6-30 carbon atoms, heteroaromatic rings having 3-30 carbon atoms, or combinations thereof;

y is selected from B, P = O, P = S, al, ga, as, siR 'or der';

Y ₁ to Y ₈ Each independently selected from C, CR' or N;

a. b, c, d are each independently selected from 0 or 1;

L ₁ -L ₄ each occurrence is identically or differently selected from a single bond, O, S, NR' ";

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

Herein, "a, b, c, d" are each independently selected from 0 or 1 "is intended to mean a, b, c, d corresponding Y ₁ And Y is equal to ₂ 、 Y ₃ And Y is equal to ₄ 、Y ₅ And Y is equal to ₆ 、Y ₇ And Y is equal to ₈ Connected or disconnected with each other. For example: when a is 0, Y ₁ And Y is equal to ₂ The break-off is performed; this is also the case when one or more of a, b, c, d are 0. Also for example: when a is 1, b is 0, c is 1, d is 0, and L ₁ 、L ₃ When selected from single bonds, Y ₁ And Y is equal to ₂ Through single bond connection, Y ₃ And Y is equal to ₄ Break off between Y ₅ And Y is equal to ₆ Through single bond connection, Y ₇ And Y is equal to ₈ And disconnected.

According to one embodiment of the invention, wherein the rings a, B, C and D are, identically or differently, selected at each occurrence from aromatic rings having 6-18 carbon atoms, heteroaromatic rings having 3-18 carbon atoms, or a combination thereof.

According to one embodiment of the invention, wherein the ring a, ring B, ring C and ring D are, identically or differently, selected for each occurrence from the group consisting of benzene rings, pyridine rings, carbazole rings, N-phenylcarbazole rings, dibenzofuran rings, dibenzothiophene rings.

According to one embodiment of the invention, wherein the rings a, B, C and D are selected identically or differently on each occurrence from benzene rings.

According to one embodiment of the invention, wherein Y is selected from B, P =o or p=s.

According to one embodiment of the invention, wherein Y is B.

According to one embodiment of the invention, wherein said Y ₁ To Y ₈ Each independently selected from C or CR).

According to an embodiment of the present invention, wherein the first compound has a structure represented by formula 5-1:

wherein,

a. b, c, d are each independently selected from 0 or 1;

R _a ，R _b ，R _c ，R _d each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;

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

According to one embodiment of the invention, wherein a is 0, b is 0, c is 0 and d is 0.

According to one embodiment of the present invention, the a+b+c+d is 1 or more.

According to one embodiment of the invention, wherein said a+b+c+d is equal to 2.

According to one embodiment of the invention, wherein a is 1, b is 0, c is 1 and d is 0.

According to one embodiment of the invention, wherein a is 1, b is 0, c is 0 and d is 1.

According to one embodiment of the invention, wherein a is 1, b is 0, c is 1, d is 0, and L ₁ 、L ₃ Selected from single bonds.

According to one embodiment of the invention, wherein a is 1, b is 0, c is 0, d is 1, and L ₁ 、L ₄ Selected from single bonds.

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

According to one embodiment of the invention, wherein said R _a ，R _b ，R _c ，R _d And is selected, identically or differently, on each occurrence, from the group consisting of: hydrogen, deuterium, fluorine, methyl, deuteromethyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzosilol, benzothiophenyl, dibenzothienyl, dibenzoselenophenyl, and combinations thereof.

According to one embodiment of the invention, wherein the first compound is selected from the group consisting of compound BD1 to compound BD 62; the specific structures of the compounds BD1 to BD62 are shown in claim 17.

According to one embodiment of the present invention, hydrogen in the structures of the compounds BD1 to BD62 can be partially or completely substituted with deuterium.

According to one embodiment of the present invention, the light emitting layer includes a second host material having a triplet energy level of 2.69eV or more.

According to one embodiment of the invention, wherein the second host material has a structure represented by formula 6:

In the case of the method of 6,

L ₁₁ selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

ar is selected from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted amino group having from 0 to 30 carbon atoms, or a combination thereof;

R ₃ each occurrence, identically or differently, represents mono-substituted, poly-substituted or unsubstituted;

R ₃ and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted 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;

adjacent substituents R ₃ Can optionally be linked to form a ring.

Herein, adjacent substituents R ₃ Can optionally be linked to form a ring, intended to mean two substituents R ₃ Can be connected to form a ring. Obviously, two substituents R ₃ Or may not be connected to form a ring.

According to one embodiment of the present invention, wherein the second host material has a structure represented by formula 6-1 or formula 6-2:

L ₁₁ each occurrence is identically or differently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted amino group having from 0 to 30 carbon atoms, or a combination thereof;

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

adjacent substituents R ₃ Can optionally be linked to form a ring.

According to one embodiment of the present invention, wherein the second host material has a structure represented by formula 6-3 or formula 6-4:

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

Adjacent substituents R ₃ Can optionally be linked to form a ring.

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

According to one embodiment of the invention, wherein said R ₃ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, and combinations thereof.

According to one embodiment of the invention, wherein said R ₃ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, tetraphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzosilol, benzothiophenyl, dibenzothiophenyl, dibenzoselenophenyl, and combinations thereof.

According to an embodiment of the invention, wherein the second host material is selected from the group consisting of compounds P-1 to P-24, the specific structure of compounds P-1 to P-24 is given in claim 19.

According to one embodiment of the invention, the hydrogen energy in the structures of compounds P-1 to P-24 is partially or completely replaced by deuterium.

According to one embodiment of the invention, wherein the first compound is a delayed fluorescence light emitting material, the first host material is an n-type host material, and the second host material is a p-type host material.

Herein, a p-type host material is an organic compound comprising carbazole groups or a triarylamine organic compound, typically having a HOMO value greater than-5.8 eV; the n-type host material is an organic compound containing chemical groups such as pyridine, pyrimidine, triazine, azadibenzofuran, azadibenzothiophene, azacarbazole and the like, and the LUMO value of the n-type host material is generally smaller than-2.3 eV.

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

According to one embodiment of the invention, the organic electroluminescent device emits white light.

According to another embodiment of the present invention, an electronic device is also disclosed, which comprises an organic electroluminescent device as described in any of the previous embodiments.

According to another embodiment of the present invention, there is also disclosed a compound composition comprising at least a first host material and a first compound, the first host material and the first compound being as described in any of the preceding embodiments.

According to another embodiment of the present invention, there is also disclosed a compound composition comprising at least a first host material, a second host material, and a first compound, the first host material, the second host material, and the first compound being as described in any 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 luminescent dopants disclosed herein may be used in combination with a variety of hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.

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

Material synthesis examples:

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

synthesis example 1: synthesis of Compound N-1-6

The first step:

5-bromo-2-fluorobenzonitrile (34 g,170 mmol), ethyl thioglycolate (20.4 g,170 mmol) and diisopropylethylamine (21.9 g,170 mmol) were dissolved in 100mL of N, N-dimethylformamide, and after stirring at room temperature for 30min, potassium carbonate (23.5 g,170 mmol) was added to the system, which was heated to 80℃for overnight reaction. TLC showed complete reaction, the system was cooled to room temperature, ice water was added to the reaction system, precipitate formed, and intermediate 1 (38.0 g,127mmol, 75%) was obtained by water washing.

And a second step of:

intermediate 1 (38.0 g,127 mmol) and methyl acetate (39.6 g,381 mmol) were dissolved in 127mL of ethylene glycol methyl ether, the reaction system was evacuated to replace nitrogen, heated to 150 ℃ and refluxed overnight for reaction, after TLC detection to complete the reaction, the system was cooled to room temperature, the product precipitated, filtered, the product was washed with ethanol until the filtrate was colorless, and the solid was collected and dried to give product as off-white granular solid intermediate 2 (32 g,114.3mmol, 90%).

And a third step of:

Intermediate 2 (32 g,114.3 mmol) was dissolved in 115mL phosphorus oxychloride, two drops of N, N-dimethylformamide were added as catalyst, heated to 110℃and refluxed to completion of the reaction for about 5 hours (TLC monitoring). The system was cooled to room temperature, slowly poured into ice water, neutralized to pH 8-9 with sodium hydroxide, then the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, dried, spun-dried, and intermediate 3 (33.6 g,112mmol, 98%) was obtained by column chromatography.

Fourth step:

intermediate 3 (3.36 g,11.2 mmol), carbazole (5.6.g, 33.6 mmol), pd ₂ (dba) ₃ (1.0 g,1.2 mmol), sphos (0.9 g,2.24 mmol), sodium t-butoxide (4.3 g,44.8 mmol) were dissolved in 112mL of xylene and heated to 140℃and reacted overnight. After the reaction was completed, the mixture was filtered and concentrated to give compound N-1-6 (2.3 g,4.5mmol, 40%) by column chromatography. The product was identified as the target product and had a molecular weight of 516.1.

Synthetic comparative example 1: synthesis of Compound HB

The first step:

2-chloro-4-aminopyridine (128 g,1 mol) and N-iodosuccinimide (224 g, 1M) were mixed, acetic acid (500 mL) was added, and the mixture was heated to 90℃to react. After the reaction was completed, it was purified by column chromatography to give intermediate 4 (79 g,311 mmol, 31%).

And a second step of:

intermediate 4 (79 g,311 mmol), p-bromophenylthiophenol (58 g,307 mmol), cuprous iodide (3 g,15 mmol), ethylene glycol (35 mL,614 mmol), and potassium carbonate (85 g,614 mmol) were added to a 2L two-necked flask under nitrogen atmosphere, and isopropanol 1L was added. Heated to 90 ℃. After the reaction was completed, purification by column chromatography gave intermediate 5 (70 g, 222mmol, 71%).

And a third step of:

intermediate 5 (49.5 g,157 mmol) was dissolved in acetic acid (600 mL), nitroso isoamyl ester (20 mL, 157 mmol) was added, and after stirring at room temperature for 1 hour, the reaction was continued with additional nitroso isoamyl ester (7 mL) for 1 hour. After the reaction was completed, it was purified by column chromatography to give intermediate 6 (36.8 g,123mmol, 78%).

Fourth step:

intermediate 6 (14.5 g,50 mmol), carbazole (25 g,150 mmol), pd under nitrogen ₂ (dba) ₃ (4.5 g,5 mmol), sphos (8 g,20 mmol), t-BuOK (28.8 g,300 mmol) were mixed, xylene (1.25. 1.25L) was added and heated to 140℃for reaction. After the completion of the reaction, the compound HB (9 g,17.5mmol, 35%) was obtained by column chromatography purification. The product was identified as the target product and had a molecular weight of 515.1.

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 obtain other compound structures of the present invention by modifying it.

The invention discloses an organic electroluminescent device, wherein a novel material combination composed of a first main body material with a structure of formula 1 and a first compound with a structure of formula 3 is used in a light-emitting layer of the organic electroluminescent device. In addition, the light-emitting layer of the organic electroluminescent device can further comprise a second host material, and the triplet energy level of the second host material is required to be greater than or equal to 2.69eV so as to be better applied to the TADF electroluminescent device.

Determination of triplet energy level:

triplet energy level (T) ₁ ) Is measured in an ultralow temperature state by utilizing the characteristics of triplet excitons having a long lifetime. Specifically, 10 was produced by dissolving a compound in a 2-methyltetrahydrofuran solvent ^-5 M concentration solution, the solution was placed in a quartz sample tube, then placed in a Dewar flask, cooled to 77K, and a 350nm light source was irradiated to a sample for phosphorescence measurement to measure phosphorescence spectrum. The spectrum was measured by using a spectrophotometer model F98 manufactured by Shanghai optical technologies Co., ltd.

The vertical axis of the phosphorescence spectrum is the phosphorescence intensity, and the horizontal axis is the wavelength. Taking a minimum value lambda with respect to the peak on the short wavelength side of the phosphorescence spectrum ₁ After (nm), the wavelength value is brought into the following conversion formula F ₁ Thereby calculating the triplet energy level.

Conversion F ₁ ：T ₁ (eV)＝1240/λ ₁

The triplet energy level of compound P-3 was measured by the above method to be 2.71eV, more than 2.69eV.

The method of manufacturing the electroluminescent device is not limited, and the following examples are only examples and should not be construed as limiting. Those skilled in the art will be able to make reasonable modifications to the preparation methods of the following examples in light of the prior art. The proportion of the various materials in the luminescent layer is not particularly limited, and a person skilled in the art can reasonably select the materials within a certain range according to the prior art, for example, the main material can occupy 80% -99% and the luminescent material can occupy 1% -20% based on the total weight of the luminescent layer; or the main material can account for 90% -99%, and the luminescent material can account for 1% -10%; or the main material may occupy 95% -99% and the luminescent material may occupy 1% -5%. In addition, the main body material may be one or two materials, wherein the proportion of the two main body materials to the main body material may be 100:0 to 1:99, a step of; alternatively, the ratio may be 80:20 to 20:80; alternatively, the ratio may be 60:40 to 40:60. in an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Frieda, st. John's, an ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art.

Device example 1

First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was baked in a glove box to remove moisture. The substrate is then mounted on a substrate support and loaded into a vacuum chamber. The organic layer specified below was at a vacuum level of about 10 ^-8 The deposition was performed sequentially on the ITO anode by thermal vacuum deposition at a rate of 0.2-2 a/s in the case of a tray. Co-evaporation of Compound HI and Compound HT as Hole Injection Layer (HIL) with thickness ofThe compound HT is used as a Hole Transport Layer (HTL) with a thickness of +.>Compound P-3 is used as Electron Blocking Layer (EBL) with thickness +.>Then co-evaporation of the compound N-1-6 as the first host, the compound P-3 as the second host, and the first compound BD17 as the dopant was used as the light emitting layer (EML) with a thickness +.>And the weight ratio of the compound P-3 to the compound N-1-6 to the compound BD17 is 49:49:2. Using Compound HB as Hole Blocking Layer (HBL) with a thickness of +.>On the hole blocking layer, co-evaporating compound ET and 8-hydroxyquinoline-lithium (Liq) as Electron Transport Layer (ETL) with thickness of +.>Finally, vapor deposition->8-hydroxyquinoline-lithium (Liq) of thickness as electron injection layer and vapor deposition +. >Is used as a cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

Device example 2

The embodiment of device example 2 was the same as device example 1, except that compound BD3 was used in place of compound BD17 in the light-emitting layer (EML), and the weight ratio of compound P-3 to compound N-1-6 to compound BD3 was 88.3:9.7:2.

Device example 3

The embodiment of device example 3 is the same as device example 1 except that compound BD37 is substituted for compound BD17 in the light emitting layer (EML).

Device comparative example 1

The embodiment of device comparative example 1 was the same as device example 1 except that compound HB was used in place of compound N-1-6 in the light-emitting layer (EML).

Device comparative example 2

The embodiment of device comparative example 2 was the same as device example 2, except that compound HB was used in place of compound N-1-6 in the light-emitting layer (EML).

Device comparative example 3

The embodiment of device comparative example 3 was the same as device example 3, except that compound HB was used in place of compound N-1-6 in the light-emitting layer (EML).

Table 1 partial device structures of device examples and comparative examples

The material structure used in the device is as follows:

at 10mA/cm ² The CIE values of example 1 and comparative example 1, the maximum emission wavelength (lambda _max ) Half width of peak (FWHM), external Quantum Efficiency (EQE), and device lifetime (LT 97). In order to more intuitively show the comparison of the data, the external quantum efficiency and lifetime of comparative example 1 were set to 1.00, and the external quantum efficiency and lifetime of example 1 were each converted from the corresponding data of comparative example 1, and the relevant data and conversion results are shown in table 2.

Table 2 device data

From the data in table 2, it can be seen that example 1 has excellent device performance relative to comparative example 1. In example 1, a combination of the first host material having the specific structure of the present invention and the first compound BD17 was used, which exhibited a narrowing of the half-width by 0.9nm, an enhancement of the eqe by 7%, and particularly an enhancement of the device lifetime by 122% compared to comparative example 1, which used a combination of the host material having no specific structure of the present invention and the first compound BD17, and a dramatic enhancement was achieved, demonstrating the advantages of the specific combination of the first host material having the specific structure of the present invention and the first compound.

At 10mA/cm ² The CIE values of example 2 and comparative example 2, the maximum emission wavelength (lambda _max ) External Quantum Efficiency (EQE) and device lifetime (LT 97). To more intuitively show the comparison of the data, the external quantum efficiency and lifetime of comparative example 2 were set to 1.00, and the external quantum efficiency and lifetime of example 2 were each converted from the corresponding data of comparative example 2, and the relevant data and conversion results are shown in table 3.

Table 3 device data

From the data in table 3, it can be seen that example 2 has excellent device performance relative to comparative example 2. In example 2, a combination of the first host material having the specific structure of the present invention and the first compound BD3 was used, which improved the external quantum efficiency by 22% and the device lifetime by 71% compared to comparative example 2, which used a combination of the host material having no specific structure of the present invention and the first compound BD3, and a significant improvement was achieved, demonstrating the advantages of the specific combination of the first host material having the specific structure of the present invention and the first compound.

At 10mA/cm ² The CIE values of example 3 and comparative example 3, the maximum emission wavelength (lambda _max ) External Quantum Efficiency (EQE) and device lifetime (LT 97). To more intuitively show the comparison of the data, the external quantum efficiency and lifetime of comparative example 3 were set to 1.00, and the external quantum efficiency and lifetime of example 3 were each converted from the corresponding data of comparative example 3, and the relevant data and conversion results are shown in table 4.

Table 4 device data

From the data in table 4, it can be seen that example 3 has excellent device performance relative to comparative example 3. In example 3, a combination of the first host material having the specific structure of the present invention and the first compound BD37 was used, which showed 5% improvement in EQE, particularly 80% improvement in device lifetime, compared to comparative example 3, which used a combination of the host material not having the specific structure of the present invention and the first compound BD37, and significant improvement was achieved, demonstrating the advantages of the specific combination of the first host material having the specific structure of the present invention and the first compound.

The comparison of the results shows that the specific combination of the first main body material with the specific structure and the first compound can be used for the blue light TADF electroluminescent device to obtain more excellent comprehensive device performance, such as higher efficiency, and particularly can greatly prolong the service life of the device. Meanwhile, according to the above embodiments, it can be seen that the first host material of the present invention can be combined with different types of first compounds of a polycyclic condensation structure with boron, nitrogen, etc. as central atoms, so that the range of the compounds of the polycyclic condensation structure with boron, nitrogen, etc. as central atoms that can be used in TADF devices is greatly widened.

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. An organic electroluminescent device, comprising:

an anode is provided with a cathode,

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

wherein the first host material has a structure represented by formula 1:

in the formula (1) of the present invention,

z is selected from O, S, se, siRR or PR;

X ₁ -X ₈ is selected from CR, identically or differently at each occurrence ₁ ，CR ₂ Or N; and X is ₁ -X ₈ At least two of them are selected from N, X ₁ -X ₈ At least one ofSelected from CR ₁ ；

The R is ₁ Has a structure represented by formula 2:

R，R ₂ and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;

Adjacent substituents R, R ₂ Can optionally be linked to form a ring;

wherein the first compound has a structure represented by formula 3:

wherein Y is selected from B, P = O, P = S, al, ga, as, siR 'or der';

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

2. The organic electroluminescent device of claim 1, wherein the X ₁ -X ₈ At least two of them are selected from CR ₁ The method comprises the steps of carrying out a first treatment on the surface of the Preferably X ₁ -X ₈ Of which only two are selected from CR ₁ 。

3. The organic electroluminescent device according to claim 1 or 2, wherein the first host material has a structure represented by formula 1-1:

in the case of the formula 1-1,

z is selected from O, S, se, siRR or PR;

Adjacent substituents R, R ₂ Can optionally be linked to form a ring.

4. The organic electroluminescent device of any one of claims 1-3, wherein the Z is selected from O, S, or Se; preferably, Z is selected from O or S; more preferably, Z is selected from S.

5. The organic electroluminescent device as claimed in any one of claims 1 to 4, wherein the X ₁ -X ₈ Wherein only two are selected from N; preferably, wherein said X ₁ -X ₄ And only two are selected from N.

6. The organic electroluminescent device of any one of claims 1-5, wherein the L is, identically or differently, selected from a single bond, a substituted or unsubstituted arylene group having 6-12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-12 carbon atoms, or a combination thereof;

preferably, L is selected, identically or differently, for each occurrence, from a single bond.

7. The organic electroluminescent device according to any one of claims 1 to 6, wherein the R _a1 The same or different at each occurrence is selected from substituted or unsubstituted aryl groups having from 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 18 carbon atoms, or combinations thereof;

preferably, R _a1 And is selected, identically or differently, on each occurrence, from the group consisting of: dibenzothienyl, dibenzofuranyl, dibenzoselenophenyl, carbazolyl, indolocarbazolyl, imidazolyl, pyridyl, triazinyl, benzimidazolyl.

8. The organic electroluminescent device according to any one of claims 1 to 7, wherein the R, R ₂ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

preferably, said R, R ₂ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, and combinations thereof;

more preferably, said R, R ₂ And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, cyano, phenyl, biphenyl, triphenylene, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiophenylDibenzosilol, benzothienyl, dibenzothienyl, dibenzoselenophenyl, triazinyl, and combinations thereof.

9. The organic electroluminescent device of claim 1, wherein the first host material is selected from the group consisting of:

/>

wherein, optionally, hydrogen in the above structure can be partially or completely substituted with deuterium.

10. The organic electroluminescent device of claim 1, wherein the E ₁ And E is ₂ At least one of which is selected from N-R _e Wherein N-R _e Has a structure represented by formula 4:

R _d and is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted alkenyl having 6 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, substituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted carbon atoms.

11. The organic electroluminescent device of claim 10, wherein the first compound has a structure represented by formula 5:

in the case of the method of claim 5,

y is selected from B, P = O, P = S, al, ga, as, siR 'or der';

Y ₁ to Y ₈ Each independently selected from C, CR' or N;

a. b, c, d are each independently selected from 0 or 1;

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

12. The organic electroluminescent device of claim 11, wherein the ring a, ring B, ring C, and ring D are, identically or differently, selected from an aromatic ring having 6-18 carbon atoms, a heteroaromatic ring having 3-18 carbon atoms, or a combination thereof;

preferably, ring a, ring B, ring C and ring D are, identically or differently, selected for each occurrence from the group consisting of benzene rings, pyridine rings, carbazole rings, N-phenylcarbazole rings, dibenzofuran rings, dibenzothiophene rings;

more preferably, ring a, ring B, ring C and ring D are selected identically or differently for each occurrence from benzene rings.

13. The organic electroluminescent device of claim 11 or 12, wherein Y is selected from B, P =o or p=s; preferably, wherein said Y is B.

14. The organic electroluminescent device of any one of claims 11-13, wherein a is 0, b is 0, c is 0, and d is 0.

15. The organic electroluminescent device according to any one of claims 11 to 13, wherein a+b+c+d is 1 or more;

preferably, a+b+c+d is equal to 2;

more preferably, a is 1, b is 0, c is 1, d is 0, or a is 1, b is 0, c is 0, d is 1;

most preferably, a is 1, b is 0, c is 1, d is 0, and L ₁ 、L ₃ Selected from single bonds, or a is 1, b is 0, c is 0, d is 1, andL ₁ 、L ₄ selected from single bonds.

16. The organic electroluminescent device of any one of claims 11-15, wherein the R _a ，R _b ，R _c ，R _d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted silyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having 6 to 20 carbon atoms, and combinations thereof;

preferably, wherein said R _a ，R _b ，R _c ，R _d And is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, carbazolyl, indolyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzosilol, benzothiophenyl, dibenzothienyl, dibenzoselenophenyl, and combinations thereof.

17. The organic electroluminescent device of claim 1, wherein the first compound is selected from the group consisting of:

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18. The organic electroluminescent device according to claim 1, wherein the light-emitting layer comprises a second host material having a triplet energy level of 2.69eV or more;

preferably, the second host material has a structure represented by formula 6:

in the case of the method of 6,

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

adjacent substituents R ₃ Can optionally be linked to form a ring.

19. The organic electroluminescent device of claim 18, wherein the second host material is selected from the group consisting of:

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20. The organic electroluminescent device of claim 18, wherein the first compound is a delayed fluorescence light emitting material, the first host material is an n-type host material, and the second host material is a p-type host material.

21. The organic electroluminescent device of any one of claims 1-20, wherein the organic electroluminescent device emits blue or white light.

22. An electronic device comprising the organic electroluminescent device of any one of claims 1-21.

23. A compound composition comprising at least a first host material and a first compound; wherein the first host material has a structure represented by formula 1:

in formula 1, Z is selected from O, S, se, siRR or PR;

r is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;

X ₁ -X ₈ Identical or different at each occurrenceIs selected from the group consisting of CR ₁ ，CR ₂ Or N; and X is ₁ -X ₈ At least two of them are selected from N, X ₁ -X ₈ At least one of them is selected from CR ₁ ；

R ₁ Has a structure represented by formula 2:

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

adjacent substituents R, R ₂ Can optionally be linked to form a ring;

wherein the first compound has a structure represented by formula 3:

wherein Y is selected from B, P = O, P = S, al, ga, as, siR 'or der';

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