CN115734630A - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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CN115734630A
CN115734630A CN202111011386.2A CN202111011386A CN115734630A CN 115734630 A CN115734630 A CN 115734630A CN 202111011386 A CN202111011386 A CN 202111011386A CN 115734630 A CN115734630 A CN 115734630A
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王乐
王强
张晗
邝志远
夏传军
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Beijing Summer Sprout Technology Co Ltd
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Abstract

An organic electroluminescent device is disclosed. The organic electroluminescent device includes a first compound having a structure of H-L-Ar and a second compound having a structure of formula 2 in an organic layer, and the first compound and the second compound may be used as a host material in an electroluminescent device. These new electroluminescent devices have lower voltages and higher efficiencies, providing better device performance. An electronic device and composition are also disclosed.

Description

Organic electroluminescent device
Technical Field
The present invention relates to organic electronic devices, such as organic electroluminescent devices. And more particularly, to an electroluminescent device comprising a first compound having a structure of H-L-Ar and a second compound having a structure of formula 2 in an organic layer.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic Light Emitting Transistors (OLETs), organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, tang and Van Slyke, ismann kodak, reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters,1987,51 (12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as fabrication on flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs of the invention by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED fabrication methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
WO2021132982A1 discloses an organic electroluminescent compound having the following structure:
Figure BDA0003238525660000021
also disclosed is an organic electroluminescent device in which the compound is used as a first host compound, wherein a second host compound may be further included in the organic electroluminescent device. However, the use of this compound as a host material in combination with a second host compound of indole and pyrrole fused azamacrocycle structures is not disclosed.
US20180337340A1 discloses an organic electroluminescent compound, an organic optical compound having the following structure
Figure BDA0003238525660000022
And an organic electroluminescent device using the compound as a host material, wherein the organic electroluminescent device may further compriseA second host material. However, the use of this compound as a host material together with a second host compound having a benzocarbazole structure is not disclosed.
KR20200056589A discloses an organic electroluminescent compound having the following structure:
Figure BDA0003238525660000023
however, the use of this compound as a host material in combination with a second host compound of indole and pyrrole fused azamacrocycle structures is not disclosed.
However, there is still room for improvement in the performance of the multi-host device reported at present, and in order to meet the increasing demand in the industry, especially for the demands of higher device efficiency, longer device lifetime, and lower driving voltage, the new host material combination still needs to be further researched and developed.
Disclosure of Invention
The present invention aims to solve at least part of the above problems by providing a series of electroluminescent devices comprising a first compound having a structure of H-L-Ar and a second compound having a structure of formula 2 in an organic layer. The first compound and the second compound can be used as host materials in an organic electroluminescent device. These new electroluminescent devices have lower voltages and higher efficiencies, providing better device performance.
According to one embodiment of the present invention, there is disclosed an electroluminescent device comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first compound and a second compound;
the first compound has a structure of H-L-Ar, the H having a structure represented by formula 1:
Figure BDA0003238525660000031
in the formula 1, the first and second groups,
A 1 、A 2 and A 3 Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
R x the same or different at each occurrence indicates mono-, poly-or no-substitution;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, -N (R') 2 Or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
r, R' and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a hydroxyl group, a mercapto group, and combinations thereof;
adjacent substituents R, R x Can optionally be linked to form a ring;
the second compound has a structure represented by formula 2:
Figure BDA0003238525660000032
in the formula 2, the first and second groups,
Z 1 to Z 12 Each occurrence, identically or differently, of C, N or CR z And Z is 5 To Z 8 Two of them are C and are each independently of Z 9 ，Z 12 Connecting;
W 1 to W 3 Selected, identically or differently, on each occurrence from N or CR w And W is 1 To W 3 At least one of which is N;
Ar 1 ，Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R z ，R w each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkyl group having 6 to 20 carbon atomsAn arylsilyl group, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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;
adjacent substituents R z 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 electroluminescent device shown in the foregoing embodiment.
According to another embodiment of the present invention, a composition is also disclosed that includes the first compound and the second compound.
The invention discloses a novel electroluminescent device, which comprises a first compound with an H-L-Ar structure and a second compound with a formula 2 structure in an organic layer, wherein the first compound and the second compound can be used as host materials in the electroluminescent device. These new electroluminescent devices have lower voltages and higher efficiencies, providing better device performance.
Drawings
Fig. 1 is a schematic diagram of an organic light emitting device that may contain electroluminescent devices as disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that may contain electroluminescent devices as disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but not by way of limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the various layers and exemplary materials are described in more detail in U.S. Pat. No. 7,279,704B2 at columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50 4 -TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson (Thompson) et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of a protective layer 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 via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent No. 7,968,146b2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. 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. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. 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 state. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε) S-T ). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ E S-T . These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes both straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-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, the cycloalkyl group may be optionally substituted.
Heteroalkyl-as used herein, heteroalkyl comprises one or more carbons in an alkyl chain that are formed by substitution with a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom, and a boron atom. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methylallyl, 1-dimethylallyl, 2-methylallyl, 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 include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be of 6 to 30 carbon atomsPreferably an aryl group of 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
Figure BDA0003238525660000061
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-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 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesitylphenyl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.
Heterocyclyl or heterocyclic-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothiophenepyridine, benzoselenophenepyridine, selenobenzene, cinnoline, dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, and their analogs. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy groups may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include a phenoxy group and a biphenyloxy group. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl substituted alkyl. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-nitrobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenyl-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, the aralkyl group may be optionally substituted.
Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.
Arylsilyl-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl group, phenylbiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, and diphenyltert-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.
Alkylgermyl-as used herein, alkyl-substituted germyl is contemplated. The alkylgermyl group may be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include a trimethylgermyl group, a triethylgermyl group, a methyldiethylgermyl group, an ethyldimethylgermyl group, a tripropylgermyl group, a tributylgermyl group, a triisopropylgermyl group, a methyldiisopropylgermyl group, a dimethylisopropylgermyl group, a tri-tert-butylgermyl group, a triisobutylgermyl group, a dimethyl-tert-butylgermyl group, and a methyl-di-tert-butylgermyl group. In addition, the alkylgermyl group may be optionally substituted.
Arylgermyl-as used herein, encompasses at least one aryl or heteroaryl substituted germyl. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenylbiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, a diphenylt-butylgermanium group. In addition, the arylgermyl group may be optionally substituted.
The term "aza" in azabenzofuran, azabenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo [ f, h ] quinoxaline, dibenzo [ f, h ] quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl groups, substituted cycloalkyl groups, substituted heteroalkyl groups, substituted heterocyclyl groups, substituted aralkyl groups, substituted alkoxy groups, substituted aryloxy groups, substituted alkenyl groups, substituted alkynyl groups, substituted aryl groups, substituted heteroaryl groups, substituted alkylsilyl groups, substituted arylsilyl groups, substituted alkylgermyl groups, substituted arylgermyl groups, substituted amino groups, substituted acyl groups, substituted carbonyl groups, substituted carboxylic acid groups, substituted ester groups, substituted sulfinyl groups, substituted sulfonyl groups, substituted phosphino groups, and refers to alkyl groups, cycloalkyl groups, heteroalkyl groups, heterocyclyl groups, aralkyl groups, alkoxy groups, aryloxy groups, alkenyl groups, alkynyl groups, aryl groups, heteroaryl groups, alkylsilyl groups, arylgermyl groups, amino groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, sulfinyl groups, sulfonyl groups, and phosphino groups, any one or more of which may be substituted with deuterium, halogen, unsubstituted alkyl groups having 1 to 20 carbon atoms, unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted arylalkyl groups having 3 to 20 carbon atoms, unsubstituted arylalkyl groups having 2 to 6 carbon atoms, unsubstituted aryl groups having 2 to 20 carbon atoms, unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, unsubstituted arylgermyl groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, polysubstituted means a range including disubstituted up to the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents may be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (including spiro, bridged, fused, etc.), as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
Figure BDA0003238525660000081
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
Figure BDA0003238525660000091
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to further away carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
Figure BDA0003238525660000092
further, the expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the adjacent two substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
Figure BDA0003238525660000093
according to one embodiment of the present invention, there is disclosed an electroluminescent device comprising:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first compound and a second compound;
the first compound has a structure of H-L-Ar, the H having a structure represented by formula 1:
Figure BDA0003238525660000094
in the formula 1, the first and second groups,
A 1 、A 2 and A 3 Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
R x the same or different at each occurrence indicates mono-, poly-or no-substitution;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, -N (R') 2 Or a combination thereof; when 2R 'are present simultaneously, the 2R's are the same or different;
l is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
r, R' and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atomsAn alkyl group, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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;
"" indicates the position where said H is linked to said L;
adjacent substituents R, R x Can optionally be linked to form a ring;
the second compound has a structure represented by formula 2:
Figure BDA0003238525660000101
in the formula 2, the first and second groups,
Z 1 to Z 12 Selected, identically or differently, at each occurrence from C, N or CR z And Z is 5 To Z 8 Two of them are C and are respectively connected with Z 9 ，Z 12 Are linked to each other and Z 1 To Z 12 One of them is C and is reacted with L 3 Connecting;
W 1 to W 3 Selected, identically or differently, on each occurrence from N or CR w And W is 1 To W 3 At least one of which is N;
Ar 1 ，Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
R z ，R w each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or a pharmaceutically acceptable salt thereofA substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclyl group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl 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;
adjacent substituents R z Can optionally be linked to form a ring.
In this example, the adjacent substituents R, R x Can optionally be linked to form a ring, intended to indicate a group in which adjacent substituents are present, for example between substituents R, substituents R x And the substituents R and R x And any one or more of these substituent groups can be linked to form a ring. Obviously, none of these adjacent substituent groups may be linked to form a ring.
In this context, adjacent substituents R z Can optionally be linked to form a ring, is intended to denote any adjacent substituent R therein z Can be connected to form a ring; obviously, these adjacent substituents R z Or may be both unconnected to form a ring.
According to one embodiment of the present invention, wherein, in formula 1, the ring a, the ring B and the ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.
According to one embodiment of the present invention, wherein, in formula 1, the ring a, the ring B and the ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
According to one embodiment of the invention, wherein H has a structure represented by formula 1A:
Figure BDA0003238525660000111
wherein A is 1 To A 3 Selected, identically or differently, on each occurrence from N or CR, X 1 To X 10 Selected, identically or differently, on each occurrence from N or CR x ；
R and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a hydroxyl group, a mercapto group, and combinations thereof;
adjacent substituents R, R x Can optionally be linked to form a ring.
In this context, the adjacent substituents R, R x Can optionally be linked to form a ring, is intended to mean that the adjacent substituents R can beOptionally joined to form a ring, also intended to denote X 1 To X 3 In (B) an adjacent substituent R x Can optionally be linked to form a ring, is also intended to denote X 4 To X 6 In (B) an adjacent substituent R x Can optionally be linked to form a ring, is also intended to mean X 7 To X 10 In (C) adjacent substituent R x Can optionally be linked to form a ring; and, it is also intended to indicate the adjacent substituents R and R x Can optionally be joined to form a ring, e.g. A 1 And X 3 And/or A 3 And X 10 And/or X 6 And X 7 Can be optionally connected into a ring. It will be apparent to the skilled person that the adjacent substituents R, R x Or may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents R x Nor linked to form a ring, and/or adjacent substituents R and R x Nor are they linked to form a ring.
According to one embodiment of the present invention, wherein R and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof;
adjacent substituents R and R x Can optionally be linked to form a ring.
According to one embodiment of the present invention, wherein R and R x Each occurrence, identically or differently, of hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothienylTriphenylene, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridyl, phenylpyridyl, or a combination thereof;
adjacent substituents R and R x Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein R and R x At least one member selected from deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R and R x Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein R and R x At least one of which is selected from deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridyl, phenylpyridyl, or a combination thereof.
According to one embodiment of the invention, wherein H is selected from the group consisting of H-1 to H-139, and the specific structures of H-1 to H-139 are shown in claim 4.
According to one embodiment of the invention, wherein the hydrogen energy in the structure of H-1 to H-139 is partially or completely substituted with deuterium.
According to an embodiment of the present invention, wherein Ar is selected from a structure represented by any one of the group consisting of formula 1-a to formula 1-c:
Figure BDA0003238525660000121
wherein E is selected, identically or differently on each occurrence, from C, N or CR e ；
Q is selected from NR q ，O，S，SiR q R q ，CR q R q ，BR q Or PR q ；
R e And R q Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
adjacent substituents R q ，R e Can optionally be linked to form a ring;
wherein the content of the first and second substances,
Figure BDA0003238525660000122
represents a position in the Ar to which the L is bonded.
According to one embodiment of the invention, wherein Q is selected from NR q O, S or CR q R q 。
According to one embodiment of the present invention, wherein, in formulae 1-a to 1-C, E is selected from C or CR, the same or different at each occurrence e 。
According to an embodiment of the present invention, wherein, in formula 1-a, at least 1 or 2 of said E are N; in formula 1-b, at least 1 or 2 of said E's are N; in formula 1-c, at least 1 or 2 of said E's are N.
According to an embodiment of the invention, wherein R is q And R e Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano groups, and combinations thereof.
According to an embodiment of the invention, wherein R is q And R e Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, phenyl, biphenyl, naphthyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridinyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.
According to an embodiment of the invention, wherein each occurrence of Ar is the same or different and is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted azabicyclofuranyl, substituted or unsubstituted azabicyclthiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted diphenylamino, or a combination thereof.
According to an embodiment of the invention, wherein each occurrence of Ar is the same or different is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, or a combination thereof.
According to one embodiment of the present invention, wherein each occurrence of Ar is selected from the group consisting of Ar-1 to Ar-130, the specific structure of Ar-1 to Ar-130 is as defined in claim 8.
According to one embodiment of the present invention, wherein hydrogen in the structure of Ar-1 to Ar-130 can be partially or completely substituted with deuterium.
According to one embodiment of the invention, wherein L is selected from the group consisting of:
Figure BDA0003238525660000131
wherein ". Sup." denotes a position connected to the H in the structures of the L-1 to L-29,
Figure BDA0003238525660000132
represents the position to which Ar is bonded in the structures of L-1 to L-29.
According to one embodiment of the present invention, wherein hydrogen in the structure of L-1 to L-29 can be partially or completely substituted with deuterium.
According to one embodiment of the invention, the first compound has a structure of H-L-Ar, wherein H is selected from any one of the group consisting of H-1 to H-139, L is selected from any one of the group consisting of L-0 to L-29, and Ar is selected from any one of the group consisting of Ar-1 to Ar-130; optionally, the hydrogen in the first compound can be partially or fully substituted with deuterium.
According to an embodiment of the present invention, wherein the first compound is selected from the group consisting of compound 1 to compound 772; the specific structures of the compounds 1 to 772 are shown in claim 10.
According to an embodiment of the present invention, wherein hydrogen energy in the compounds 1 to 772 is partially or completely substituted by deuterium.
According to an embodiment of the present invention, wherein the second compound has a structure represented by formula 2-1, formula 2-2, or formula 2-3:
Figure BDA0003238525660000141
wherein the content of the first and second substances,
Z 1 to Z 12 Selected, identically or differently, at each occurrence from C, N or CR z And Z is 1 To Z 12 One of them is C and is reacted with L 3 Connecting;
W 1 to W 3 Selected, identically or differently, on each occurrence from N or CR w And W is 1 To W 3 At least two of which are N;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R z and R w Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a hydroxyl group, a mercapto group, and combinations thereof;
Ar 1 、Ar 2 and Ar 3 Each time phase of occurrenceIs selected, identically or differently, from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof;
adjacent substituents R z Can optionally be linked to form a ring.
According to an embodiment of the present invention, wherein the second compound has a structure represented by formula 2-1.
According to an embodiment of the present invention, wherein the second compound has a structure represented by formula 2-1a or formula 2-1 b:
Figure BDA0003238525660000142
Z 1 to Z 4 、Z 7 To Z 12 Selected, identically or differently, on each occurrence from N or CR z ；
W 1 To W 3 Is selected, identically or differently on each occurrence, from N or CR w And W is 1 To W 3 At least two of which are N;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R z and R w Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted 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, or a combination thereofSubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl 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;
Ar 1 、Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R z Can optionally be linked to form a ring.
According to an embodiment of the present invention, wherein said Ar 1 、Ar 2 And Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof.
According to one embodiment of the present invention, wherein Ar 1 、Ar 2 And Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
According to one embodiment of the present invention, wherein Ar 1 、Ar 2 And Ar 3 Each occurrence is the same or different and is selected from the group consisting of Ar1 through Ar 130; the specific structures of Ar1 to Ar130 are as defined in claim 12.
According to an embodiment of the present invention, wherein hydrogen in the structure of Ar1 to Ar130 can be partially or completely substituted by deuterium.
According to the inventionAn embodiment, wherein, in the second compound, W 1 To W 3 Are all N; r is z Each occurrence, the same or different, is selected 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R z Each occurrence, the same or different, is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.
According to an embodiment of the invention, wherein R is z Each occurrence, identically or differently, is selected from hydrogen, deuterium, cyano, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, or a combination thereof.
According to an embodiment of the invention, wherein L 1 、L 2 And L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, or a combination thereof.
According to an embodiment of the invention, wherein L 1 、L 2 And L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.
According to one embodiment of the present invention, wherein the second compound is selected from the group consisting of compound 2-1 to compound 2-205; the specific structures of the compounds 2-1 to 2-205 are shown in claim 15.
According to one embodiment of the present invention, wherein hydrogen energy in the compound 2-1 to the compound 2-205 can be partially or completely substituted by deuterium.
According to an embodiment of the present invention, wherein the organic layer is a light emitting layer, and the first compound and the second compound are host materials.
According to one embodiment of the present invention, wherein the light emitting layer further comprises at least one phosphorescent light emitting material.
According to one embodiment of the present invention, wherein the phosphorescent light-emitting material is a metal complex having M (L) a ) m (L b ) n (L c ) q A general formula (II) of (I);
m is selected from metals having a relative atomic mass greater than 40;
L a 、L b 、L c a first ligand, a second ligand and a third ligand coordinated to the M, respectively; l is a 、L b 、L c Optionally linked to form a multidentate ligand;
L a 、L b 、L c may be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of M, n, q is equal to the oxidation state of said M; when m is greater than or equal to 2, a plurality of L a May be the same or different; when n is 2, two L b May be the same or different; when q is 2, two L c May be the same or different;
L a has a structure as shown in formula 3:
Figure BDA0003238525660000161
wherein, the first and the second end of the pipe are connected with each other,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring F is selected from a 5-membered unsaturated carbocyclic ring, a phenyl ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;
ring D and ring F via U a And U b Fusing;
U a and U b Selected, identically or differently on each occurrence, from C orN；
R d ，R f The same or different at each occurrence denotes mono-, poly-or unsubstituted;
V 1 -V 4 selected from CR, identically or differently at each occurrence v Or N;
R d ，R f ，R v each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a hydroxyl group, a mercapto group, and combinations thereof;
adjacent substituents R d ，R f ，R v Can be optionally connected to form a ring;
L b 、L c each occurrence, identically or differently, is selected from any one of the following structures:
Figure BDA0003238525660000162
Figure BDA0003238525660000171
wherein the content of the first and second substances,
R a ，R b and R c The same or different at each occurrence indicates mono-, poly-, or unsubstituted;
X b each occurrence, the same or different, is selected from the group consisting of: o, S, se, NR N1 And CR C1 R C2 ；
X c And X d Each occurrence, the same or different, is selected from the group consisting of: o, S, se and NR N2 ；
R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R C2 Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a hydroxyl group, a mercapto group, and combinations thereof;
the ligand L b 、L c In the structure (1), adjacent substituents R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R C2 Can optionally be linked to form a ring。
In this context, adjacent substituents R d ，R f ，R v Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example adjacent substituents R d Adjacent and adjacent substituents R f Adjacent and adjacent substituents R v Adjacent and adjacent substituents R d And R f Adjacent and adjacent substituents R d And R v Meta and adjacent substituents R f And R v Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these substituent groups may not be connected to form a ring.
In this example, the adjacent substituents R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R C2 Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents R a In between, two substituents R b In between, two substituents R c Of a substituent R a And R b Of a substituent R a And R c Of R is a substituent b And R c Of a substituent R a And R N1 Of a substituent R b And R N1 Of R is a substituent a And R C1 Of a substituent R a And R C2 Of a substituent R b And R C1 Of a substituent R b And R C2 Of R is a substituent a And R N2 Of a substituent R b And R N2 And R is C1 And R C2 And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be linked to each other to form a ring.
According to one embodiment of the present invention, wherein the phosphorescent light-emitting material is a metal complex having M (L) a ) m (L b ) n A general formula (II) of (I);
m is selected from metals having a relative atomic mass greater than 40;
L a 、L b a first ligand and a second ligand coordinated to said M, respectively; l is a radical of an alcohol a 、L b Optionally linked to form a multidentate ligand;
m is 1,2 or 3; n is 0, 1 or 2; the sum of M and n is equal to the oxidation state of M; when m is 2 or more, a plurality of L a May be the same or different; when n is 2, two of L b May be the same or different;
L a has a structure as shown in formula 3:
Figure BDA0003238525660000181
wherein, the first and the second end of the pipe are connected with each other,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring F is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring F via U a And U b (ii) fused;
U a and U b Is selected, identically or differently on each occurrence, from C or N;
R d ，R f the same or different at each occurrence denotes mono-, poly-or unsubstituted;
V 1 -V 4 is selected, identically or differently on each occurrence, from CR v Or N;
R d ，R f ，R v each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted 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 heteroarylSubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents R d ，R f ，R v Can be optionally linked to form a ring;
wherein the ligand L b Has the following structure:
Figure BDA0003238525660000182
wherein R is 1 To R 7 Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a hydroxyl group, a mercapto group, and combinations thereof.
According to one embodiment of the invention, wherein the ligand L b Has the following structure:
Figure BDA0003238525660000191
R 1 -R 3 at least one or two of which are selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R 4 -R 6 At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein the ligand L b Has the following structure:
Figure BDA0003238525660000192
R 1 -R 3 at least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R 4 -R 6 At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
According to an embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is an Ir complex, a Pt complex or an Os complex.
According to one embodiment of the invention, in the device, wherein the phosphorescent light-emitting material isIr complexes of the formula and having Ir (L) a )(L b )(L c )、Ir(L a ) 2 (L b )、Ir(L a ) 2 (L c ) Or Ir (L) a )(L c ) 2 Any of the structures shown.
According to one embodiment of the present invention, wherein the phosphorescent light emitting material is an Ir complex and contains a ligand L in the electroluminescent device a Said L is a Has a structure as shown in formula 3 and comprises at least one structural unit selected from the group consisting of a 6-membered and 6-membered aromatic ring, a 6-membered and 6-membered heteroaromatic ring, a 6-membered and 5-membered aromatic ring and a 6-membered and 5-membered heteroaromatic ring.
According to one embodiment of the invention, wherein, in the electroluminescent device, the phosphorescent light-emitting material is an Ir complex and contains a ligand L a Said L is a Has a structure as shown in formula 3 and comprises at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.
According to one embodiment of the present invention, wherein the phosphorescent light emitting material is an Ir complex and contains a ligand L in the electroluminescent device a Said L is a Any one at each occurrence selected from the group consisting of:
Figure BDA0003238525660000201
according to one embodiment of the invention, wherein, in the electroluminescent device, the phosphorescent light-emitting material is an Ir complex and contains a ligand L b Said L is b Each occurrence, the same or different, is selected from the group consisting of:
Figure BDA0003238525660000211
according to one embodiment of the invention, wherein in the electroluminescent device, the phosphorescent light-emitting material is selected from the group consisting of:
Figure BDA0003238525660000212
Figure BDA0003238525660000221
Figure BDA0003238525660000231
according to another embodiment of the invention, an electronic device is also disclosed, which comprises the electroluminescent device shown in any of the previous embodiments.
According to another embodiment of the present invention, a composition is also disclosed that includes the first compound and the second compound. The specific structures of the first compound and the second compound are shown in any one of the preceding embodiments.
In combination with other materials
The materials described herein for a particular layer in an organic light emitting device can 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 US2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of light emitting dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application US2015/0349273A1, paragraphs 0080-0101, which is incorporated herein by reference in its entirety. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Example of material Synthesis:
in the materials synthesis examples, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai prism technique fluorescence spectrophotometer, electrochemical workstation of wuhan kospace, sublimator of bulgar, etc.) in a manner well known to those skilled in the art.
Synthesis example 1: synthesis of Compounds 2 to 6
Step 1: synthesis of intermediate 2
Figure BDA0003238525660000241
Intermediate 1 (30g, 93.5 mmol), o-bromobenzoic acid (22.5g, 112.2mmol), tetrakistriphenylphosphine palladium (3.2g, 2.8 mmol), potassium carbonate (25.8 g, 187mmol), solvent (toluene/ethanol/water =280/70/70 mL) were added to a three-necked flask under nitrogen and reacted overnight at 80 ℃. After the completion of the reaction, it was cooled to room temperature, distilled water was added, the mixture was extracted with methylene chloride, the organic phase was washed with water, concentrated to remove the solvent, and the crude product was purified by column chromatography to give intermediate 2 as a yellow solid (2.8 g, yield: 72%).
Step 2: synthesis of intermediate 3
Figure BDA0003238525660000242
Under nitrogen protection, intermediate 2 (22g, 93.5 mmol), triphenylphosphine (52.7g, 201.3mmol) and o-dichlorobenzene (150 mL) were added to a three-necked flask and reacted at 200 ℃ overnight. After completion of the reaction, it was cooled to room temperature, and the crude product was purified by column chromatography (eluent: PE/DCM = 2.
And 3, step 3: synthesis of intermediate 4
Figure BDA0003238525660000243
Under the protection of nitrogen, adding the intermediate 3 (7g, 23.6mmol), iodobenzene (5.8g, 28.3mmol), cuprous chloride (237.6mg, 2.4mmol), potassium carbonate (9.8g, 70.8mmol), 18-crown-6 (633.6mg, 2.4mmol), 1, 10-phenanthroline (432mg, 2.4mmol) and N-methylpyrrolidone (80 mL) into a three-necked bottle, and reacting at 180 ℃ overnight. Cooled to room temperature, then distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and purified by column chromatography (eluent: PE/EA = 20) to give intermediate 4 as an off-white solid (6 g, yield: 68%).
And 4, step 4: synthesis of intermediate 5
Figure BDA0003238525660000251
Intermediate 4 (5.8g, 15.5 mmol) was dissolved in dry tetrahydrofuran (50 mL) under nitrogen, followed by dropwise addition of n-butyllithium (7.4mL, 18.6 mmol) slowly at-78 ℃ and reaction at this temperature for 1 hour. Triisopropyl borate (5.7 g,30.1 mmol) was then added dropwise slowly at-78 ℃ and after completion of the addition, the reaction was allowed to warm to room temperature slowly overnight. After completion of the reaction, water was slowly added dropwise to quench, the mixture was extracted with dichloromethane, the organic phase was washed with water, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and purified by column chromatography (eluent: PE/EA = 10) to give intermediate 5 as a gray solid (5.5 g, yield: 85%).
And 5: synthesis of Compounds 2 to 6
Figure BDA0003238525660000252
Intermediate 5 (3 g,7.1 mmol), 2-chloro-4- (dibenzofuran-1-yl) -6-phenyl- [1,3,5] triazine (2.8g, 7.8mmol), tetrakistriphenylphosphine palladium (410mg, 0.36mmol), potassium carbonate (2.0g, 14.2mmol), and a solvent (toluene/ethanol/water =40/10/10 mL) were charged into a three-necked flask under nitrogen atmosphere, and reacted at 100 ℃ overnight. After completion of the reaction, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the solvent was removed by concentration, and after the crude product was purified by column chromatography (eluent: PE/DCM = 4) compound 2-6 was obtained as a yellow solid (2.7 g, yield: 63%). The product was identified as the target product, molecular weight 614.2.
Synthesis example 2: synthesis of Compounds 2-7
Figure BDA0003238525660000253
Intermediate 5 (3g, 7.1 mmol), intermediate 6 (3.4g, 7.8mmol), tetratriphenylphosphine palladium (410mg, 0.36mmol), potassium carbonate (2.0g, 14.2mmol), and a solvent (toluene/ethanol/water =40/10/10 mL) were charged into a three-necked flask under nitrogen protection, and reacted at 100 ℃ overnight. After completion of the reaction, cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the solvent was removed by concentration, and after the crude product was purified by column chromatography (eluent: PE/DCM =4: 1), compound 2-7 was obtained as a yellow solid (2.4 g, yield: 63%). The product was identified as the target product, with a molecular weight of 690.2.
Synthesis example 3: synthesis of Compounds 2-111
Figure BDA0003238525660000261
Intermediate 7 (2.4 g,5.7 mmol), 2-chloro-4- (dibenzofuran-1-yl) -6-phenyl- [1,3,5] triazine (2.2g, 6.27mmol), palladium tetratriphenylphosphine (329mg, 0.3mmol), potassium carbonate (1.6g, 11.4 mmol), and a solvent (toluene/ethanol/water =40/10/10 mL) were added to a three-necked flask under nitrogen atmosphere and reacted overnight at 100 ℃. After completion of the reaction, it was cooled to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the solvent was removed by concentration, and the crude product was purified by column chromatography (eluent: PE/DCM = 5/1) to obtain compounds 2-111 as off-white solids (2.1 g, yield: 60%). The product was identified as the target product, molecular weight 614.2.
The preparation methods of the first compound and the second compound selected in the present invention are not limited, and those skilled in the art can prepare the compound by using a conventional synthesis method, or can easily prepare the compound by referring to the synthesis methods of the above compounds 2-6, compounds 2-7, and compounds 2-111, or can prepare the compound by referring to the preparation methods in patent applications such as US20180337340A1, US20210167297A1, and CN202011399426.0, and the preparation methods thereof are not described herein again. The method of fabricating the organic electroluminescent device is not limited, and the method of fabricating the following examples is only an example and should not be construed as a limitation. The preparation of the following examples can be reasonably modified by those skilled in the art in light of the prior art. For example, the ratio of the first compound and the second compound is not particularly limited, and can be reasonably selected by a person skilled in the art within a certain range according to the prior art, for example, the total weight of the first compound and the second compound accounts for 99.5% to 80.0% of the total weight of the light emitting layer, based on the total weight of the light emitting layer material, and the weight ratio of the first compound and the second compound is between 1; alternatively, the weight ratio of the first compound to the second compound may be between 20; alternatively, the weight ratio of the first compound to the second compound may be between 50 and 90. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the person skilled in the art knows the relevant contents of the above device usage, testing method, etc., and can obtain the inherent data of the sample with certainty and without influence, the above related contents are not further described herein.
Device example 1
First, a glass substrate, having an 80nm thick Indium Tin Oxide (ITO) anode, was cleaned and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was dried in a glove box filled with nitrogen gas to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. Organic layers specified below, in a vacuum of about 10 degrees -8 In the case of Torr
Figure BDA0003238525660000262
Are sequentially evaporated on the ITO anode by thermal vacuum. Compound HI was used as a Hole Injection Layer (HIL) with a thickness of
Figure BDA0003238525660000263
The compound HT is used as Hole Transport Layer (HTL) with a thickness of
Figure BDA0003238525660000264
Compound EB was used as an Electron Blocking Layer (EBL) with a thickness of
Figure BDA0003238525660000265
Then, the compound 117 as a first host, the compound 2 to 6 as a second host, and the compound RD as a dopant were co-evaporated to be used as a light-emitting layer (EML, compound 117: compound 2 to 6: compound RD =49, weight ratio) to have a thickness of
Figure BDA0003238525660000266
The compound HB was used as a hole-blocking layer (HBL) with a thickness of
Figure BDA0003238525660000267
On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron-transporting layer (ETL) with a thickness of
Figure BDA0003238525660000268
Finally, vapor deposition
Figure BDA0003238525660000269
8-hydroxyquinoline-lithium (Liq) as an Electron Injection Layer (EIL) in thickness and evaporation deposited
Figure BDA00032385256600002610
As a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
Device example 2
Device example 2 is the same as device example 1 except that compounds 2-7 are used as the second host in place of compounds 2-6 in the light emitting layer (EML).
Device example 3
Device example 3 is the same as device example 1 except that compounds 2-111 are used as the second host in place of compounds 2-6 in the light emitting layer (EML).
Device comparative example 1
Device comparative example 1 was the same as device example 1 except that compounds 2-6 were used instead of compounds 2-6 and compound 117 as hosts in the light emitting layer (EML).
Device comparative example 2
Device comparative example 2 was the same as device example 1 except that compounds 2 to 7 were used as hosts in the light emitting layer (EML) instead of compounds 2 to 6 and compound 117.
Device comparative example 3
Device comparative example 3 was the same as device example 1 except that compounds 2 to 111 were used as hosts in the light emitting layer (EML) instead of compounds 2 to 6 and compound 117.
Device comparative example 4
Device comparative example 4 was the same as device example 1 except that compound 117 was used instead of compounds 2 to 6 and compound 117 as a host in the light emitting layer (EML).
The detailed device layer structure and thickness are shown in the table below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
TABLE 1 partial device structures of device examples and comparative examples
Figure BDA0003238525660000271
Figure BDA0003238525660000281
The material structure used in the device is as follows:
Figure BDA0003238525660000282
table 2 shows the results at a constant current of 15mA/cm 2 Under the conditions, the maximum emission wavelength (. Lamda.) of the device examples and the device comparative examples was measured max ) Voltage (Voltage) and Power Efficiency (PE).
TABLE 2 device data
Device ID λ max (nm) Voltage[V] PE[lm/W]
Example 1 624 4.26 14.94
Example 2 624 4.37 14.38
Example 3 624 4.43 13.53
Comparative example 1 623 4.95 12.24
Comparative example 2 623 5.22 10.46
Comparative example 3 624 4.93 11.42
Comparative example 4 623 4.97 7.7
Discussion:
as can be seen from the data in Table 2, the maximum emission wavelengths of the examples and comparative examples remained substantially the same. In terms of voltage, example 1 is 0.69V lower than comparative example 1 by 14.0%; example 2 is 0.85V lower than comparative example 2, which is a 16.3% reduction; example 3 was 0.5V lower than comparative example 3 by 10.1%. In the aspect of power efficiency, compared with comparative example 1, the power efficiency of example 1 is improved by 2.7lm/W, and the amplification is 22.1%; compared with comparative example 2, the improvement of example 2 by 3.92lm/W is realized, and the amplification is 37.5%; example 3 is improved by 2.11lm/W compared with comparative example 3, and the amplification is 18.5%. Compared with comparative example 4, examples 1 to 3 all have obvious reduction in voltage compared with comparative example 4, and more importantly, examples 1 to 3 all have great improvement in power efficiency compared with comparative example 4, and the improvement range is over 75.7%. As can be seen from the above data, the electroluminescent device of the present invention, which includes the first compound and the second compound in the organic layer, has a lower voltage and higher efficiency, with significantly improved device performance. The combined use of the first compound and the second compound can better balance the migration of holes and electrons, thereby improving the efficiency of the device. The unique advantages of the combination of the first compound and the second compound selected for use in the present invention are demonstrated.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.

Claims (19)

1. An electroluminescent device, comprising:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first compound and a second compound;
the first compound has a structure of H-L-Ar, the H having a structure represented by formula 1:
Figure FDA0003238525650000011
in the formula 1, the first and second groups,
A 1 、A 2 and A 3 Each occurrence of which is identical or different, is selected from N or CR, and each occurrence of ring A, ring B and ring C is identical or different, is selected from the group consisting of compounds having from 5 to 18 carbon atomsOr a heterocycle having 3 to 18 carbon atoms;
R x the same or different at each occurrence denotes mono-, poly-or no-substitution;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, -N (R') 2 Or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
r, R' and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
adjacent substituents R, R x Can optionally be linked to form a ring;
the second compound has a structure represented by formula 2:
Figure FDA0003238525650000012
in the formula 2, the first and second groups,
Z 1 to Z 12 Each occurrence, identically or differently, of C, N or CR z And Z is 5 To Z 8 Two of them are C and are respectively connected with Z 9 ，Z 12 Connecting;
W 1 to W 3 Selected, identically or differently, on each occurrence from N or CR w And W is 1 To W 3 At least one of which is N;
Ar 1 ，Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R z ，R w each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl groupAcid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R z Can optionally be linked to form a ring.
2. The electroluminescent device of claim 1, wherein said ring a, ring B, and ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms;
preferably, said ring a, ring B and ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring.
3. The electroluminescent device of claim 1 or 2, wherein H has a structure represented by formula 1A:
Figure FDA0003238525650000021
wherein A is 1 To A 3 Selected, identically or differently, on each occurrence from N or CR, X 1 To X 10 Selected, identically or differently, on each occurrence from N or CR x ；
R and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstitutedSubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl 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, R x Can optionally be linked to form a ring;
preferably, R and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, and combinations thereof;
more preferably, R and R x Each occurrence, identically or differently, is selected from hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridyl, phenylpyridyl, or a combination thereof.
4. The electroluminescent device of claim 1 or 3, wherein H is selected from the group consisting of the following structures:
Figure FDA0003238525650000031
Figure FDA0003238525650000041
Figure FDA0003238525650000051
Figure FDA0003238525650000061
Figure FDA0003238525650000071
Figure FDA0003238525650000081
wherein ". X" represents the position of the structure of H-1 to H-139 to which L is attached;
optionally, the hydrogen in the structures of H-1 through H-139 can be partially or fully substituted with deuterium.
5. The electroluminescent device of claim 1, wherein Ar is selected from a structure represented by any one of the group consisting of formula 1-a to formula 1-c:
Figure FDA0003238525650000082
wherein E is selected, identically or differently on each occurrence, from C, N or CR e ；
Q is selected from NR q ，O，S，SiR q R q ，CR q R q ，BR q Or PR q ；
R e And R q Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstitutedAn alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclyl group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl 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 sulfenyl group, a sulfonyl group, a phosphino group, a combination thereof;
adjacent substituents R q ，R e Can optionally be linked to form a ring;
wherein the content of the first and second substances,
Figure FDA0003238525650000083
represents the position in said Ar to which said L is attached;
preferably, Q is selected from NR q O, S or CR q R q 。
6. The electroluminescent device of claim 5, wherein in formulas 1-a to 1-C, E is selected from C or CR, the same or different at each occurrence e 。
7. An electroluminescent device as claimed in claim 5 or 6 wherein R is q And R e Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkane having 3 to 20 ring carbon atomsA substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a cyano group, and combinations thereof;
preferably, said R is q And R e Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, phenyl, biphenyl, naphthyl, 9-phenylcarbazolyl, naphthylphenyl, phenylpyridyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, triphenylene, terphenyl, and combinations thereof.
8. The electroluminescent device of any one of claims 1-7, wherein the Ar, either the same or different at each occurrence, is selected from the group consisting of:
Figure FDA0003238525650000091
Figure FDA0003238525650000101
Figure FDA0003238525650000111
Figure FDA0003238525650000121
wherein the content of the first and second substances,
Figure FDA0003238525650000122
represents a position to which the L is bonded in the structure of Ar-1 to Ar-130;
optionally, the hydrogen energy in the structures of Ar-1 through Ar-130 can be partially or fully substituted with deuterium.
9. The electroluminescent device of claim 8, wherein L is selected from the group consisting of:
Figure FDA0003238525650000123
Figure FDA0003238525650000131
wherein "+" indicates a position connected to the H in the structure of the L-1 to L-29,
Figure FDA0003238525650000132
represents a position to which Ar is bonded in the structures of L-1 to L-29;
optionally, the hydrogen in the structures of L-1 to L-29 can be partially or fully substituted with deuterium.
10. The electroluminescent device according to claim 9, wherein the first compound has a structure of H-L-Ar, wherein H is selected from any one of the group consisting of H-1 to H-139, L is selected from any one of the group consisting of L-0 to L-29, and Ar is selected from any one of the group consisting of Ar-1 to Ar-130; optionally, the hydrogen in the first compound can be partially or fully substituted with deuterium;
preferably, the first compound is selected from the group consisting of compound 1 to compound 772; the compounds 1 through 772 have the structure of H-L-Ar, wherein H, L, and Ar each correspond to a structure selected from the following table:
Figure FDA0003238525650000133
Figure FDA0003238525650000141
Figure FDA0003238525650000151
Figure FDA0003238525650000161
Figure FDA0003238525650000171
Figure FDA0003238525650000181
Figure FDA0003238525650000191
Figure FDA0003238525650000201
wherein, optionally, the hydrogen energy in said compounds 1 to 772 is partially or completely substituted by deuterium.
11. The electroluminescent device of claim 1, wherein the second compound has a structure represented by formula 2-1, formula 2-2, or formula 2-3:
Figure FDA0003238525650000202
wherein the content of the first and second substances,
Z 1 to Z 12 Selected, identically or differently, at each occurrence from C, N or CR z And Z is 1 To Z 12 One of them is C and is reacted with L 3 Connecting;
W 1 to W 3 Selected, identically or differently, on each occurrence from N or CR w And W is 1 To W 3 At least two of which are N;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R z and R w Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
Ar 1 、Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R z Can optionally be linked to form a ring;
preferably, the second compound has a structure represented by formula 2-1;
more preferably, the second compound has a structure represented by formula 2-1a or formula 2-1 b:
Figure FDA0003238525650000211
Z 1 to Z 4 、Z 7 To Z 12 Selected, identically or differently, on each occurrence from N or CR z ；
W 1 To W 3 Is selected, identically or differently on each occurrence, from N or CR w And W is 1 To W 3 At least two of which are N;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R z and R w Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, isocyanic acid group, cyano group, isocyanic acid group, hydroxyl group, and the likeMercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Ar 1 、Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R z Can optionally be linked to form a ring.
12. The electroluminescent device of claim 1 or 11, wherein Ar is Ar 1 、Ar 2 And Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof;
preferably, ar 1 、Ar 2 And Ar 3 Each occurrence identically or differently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a combination thereof;
more preferably, ar 1 、Ar 2 And Ar 3 Each occurrence, the same or different, is selected from the group consisting of:
Figure FDA0003238525650000212
Figure FDA0003238525650000221
Figure FDA0003238525650000231
Figure FDA0003238525650000241
wherein the content of the first and second substances,
Figure FDA0003238525650000251
the structures of Ar1 to Ar130 are represented by the formula 2 1 、L 2 Or the position to which the N atom is attached;
optionally, the hydrogen energy in the structures of Ar1 through Ar130 is partially or fully substituted with deuterium.
13. An electroluminescent device as claimed in claim 1 or 11, wherein in the second compound, W 1 To W 3 Are all N; r z Each occurrence, the same or different, is selected 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof;
preferably, said R is z Each occurrence, identically or differently, is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
more preferably, R z Each occurrence, the same or different, is selected from hydrogen, deuterium, cyano, phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, or a combination thereof.
14. An electroluminescent device as claimed in claim 1 or 11 wherein L 1 、L 2 And L 3 Each timeWhen present, the same or different, are selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, or a combination thereof;
preferably, L 1 、L 2 And L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a combination thereof.
15. The electroluminescent device of claim 1, wherein the second compound is selected from the group consisting of the following structures:
Figure FDA0003238525650000252
Figure FDA0003238525650000261
Figure FDA0003238525650000271
Figure FDA0003238525650000281
Figure FDA0003238525650000291
Figure FDA0003238525650000301
Figure FDA0003238525650000311
Figure FDA0003238525650000321
Figure FDA0003238525650000331
Figure FDA0003238525650000341
Figure FDA0003238525650000351
Figure FDA0003238525650000361
Figure FDA0003238525650000371
Figure FDA0003238525650000381
Figure FDA0003238525650000391
wherein, optionally, the hydrogen in said compounds 2-1 to 2-205 can be partially or fully substituted with deuterium.
16. The electroluminescent device of claim 1, wherein the organic layer is a light emitting layer and the first and second compounds are host materials.
17. The electroluminescent device of claim 16 wherein said light-emitting layer further comprises at least one phosphorescent light-emitting material;
preferably, the phosphorescent light-emitting material is a metal complex having M (L) a ) m (L b ) n (L c ) q A general formula (I);
m is selected from metals having a relative atomic mass greater than 40;
L a 、L b 、L c a first ligand, a second ligand and a third ligand coordinated to the M, respectively; l is a radical of an alcohol a 、L b 、L c Optionally linked to form a multidentate ligand;
L a 、L b 、L c may be the same or different; m is 1,2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of M, n, q is equal to the oxidation state of said M; when m is 2 or more, a plurality of L a May be the same or different; when n is 2, two L b May be the same or different; when q is 2, two L c May be the same or different;
L a has a structure as shown in formula 3:
Figure FDA0003238525650000401
wherein the content of the first and second substances,
ring D is selected from a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring F is selected from a 5-membered unsaturated carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring or a 6-membered heteroaromatic ring;
ring D and ring F via U a And U b (ii) fused;
U a and U b Is selected, identically or differently on each occurrence, from C or N;
R d ，R f the same or different at each occurrence denotes mono-, poly-or unsubstituted;
V 1 -V 4 each time goes outThe occurrences being the same or different and selected from CR v Or N;
R d ，R f ，R v each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
adjacent substituents R d ，R f ，R v Can be optionally connected to form a ring;
L b 、L c each occurrence, which may be the same or different, is selected from any one of the following structures:
Figure FDA0003238525650000402
Figure FDA0003238525650000411
wherein the content of the first and second substances,
R a ，R b and R c The same or different surface at each occurrenceMono-, poly-, or unsubstituted;
X b each occurrence, the same or different, is selected from the group consisting of: o, S, se, NR N1 And CR C1 R C2 ；
X c And X d Each occurrence, the same or different, is selected from the group consisting of: o, S, se and NR N2 ；
R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R C2 Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
the ligand L b 、L c In the structure (1), adjacent substituents R a ，R b ，R c ，R N1 ，R N2 ，R C1 And R C2 Can optionally be linked to form a ring.
18. An electronic device comprising the electroluminescent device of any one of claims 1-17.
19. A composition comprising a first compound and a second compound,
the first compound has a structure of H-L-Ar, the H having a structure represented by formula 1:
Figure FDA0003238525650000412
in the case of the formula 1, the compound,
A 1 、A 2 and A 3 Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
R x the same or different at each occurrence denotes mono-, poly-or no-substitution;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted arylamino having 3 to 30 carbon atoms, or combinations thereof;
l is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
r and R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 1 to 20 carbon atoms, or substituted or unsubstituted aryl having 2 to 20 carbon atomsAn alkylsilyl group of atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanyl 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;
adjacent substituents R, R x Can optionally be linked to form a ring;
the second compound has a structure represented by formula 2:
Figure FDA0003238525650000421
in the formula 2, the first and second groups,
Z 1 to Z 12 Each occurrence, identically or differently, of C, N or CR z And Z is 5 To Z 8 Two of them are C and are respectively connected with Z 9 ，Z 12 Connecting;
W 1 to W 3 Selected, identically or differently, on each occurrence from N or CR w And W is 1 To W 3 At least one of which is N;
Ar 1 ，Ar 2 and Ar 3 Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
L 1 ，L 2 and L 3 Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
R z ，R w each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 ring carbon atomsA heteroalkyl group of carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl 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;
adjacent substituents R z Can optionally be linked to form a ring.
CN202111011386.2A 2021-08-31 2021-08-31 Organic electroluminescent device Pending CN115734630A (en)

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