CN113809242A - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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CN113809242A
CN113809242A CN202010538702.0A CN202010538702A CN113809242A CN 113809242 A CN113809242 A CN 113809242A CN 202010538702 A CN202010538702 A CN 202010538702A CN 113809242 A CN113809242 A CN 113809242A
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邝志远
李锋
姚剑飞
蔡维
桑明
王珍
李宏博
王涛
夏传军
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Beijing Summer Sprout Technology Co Ltd
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    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Abstract

Disclosed is an organic electroluminescent device. The organic electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a first metal complex having a ligand structure of formula 1 and a first host compound having a structure of formula 2. The organic electroluminescent device of the invention has obvious improvement on the performance of the device, such as the service life of the device. An electronic device including the organic electroluminescent device is also disclosed.

Description

Organic electroluminescent device
Technical Field
The present invention relates to an organic electroluminescent device. More particularly, it relates to an organic electroluminescent device comprising a metal complex having a ligand structure of formula 1 and a first host compound having a structure of formula 2, and an electronic apparatus comprising the organic electroluminescent device.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
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 manufacturing 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.
US20200127213a1 discloses an organic electroluminescent device comprising a polymer of
Figure BDA0002536583720000011
A first body represented by
Figure BDA0002536583720000021
The second body is shown. In addition, in this applicationSome phosphorescent dopants are also disclosed. However, in the first host compound in this application R2-R4Is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C20 aryl, but specific structures and examples refer to R2-R4Are all hydrogen. This application does not study and focus on R in the first host compound2-R4The introduction of aryl groups will enhance device performance.
WO2019017618A1 discloses an organic optoelectronic device, the light-emitting layer of which comprises
Figure BDA0002536583720000022
A first body represented by
Figure BDA0002536583720000023
A second body formed by bonding
Figure BDA0002536583720000024
The phosphorescent dopant of the formula. In the first host compound of this application R2-R4Is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C20 aryl, but specific structures and examples refer to R2-R4Are all hydrogen. This application does not study and focus on R in the first host compound2-R4The introduction of aryl groups will enhance device performance.
Through intensive research, the inventors of the present invention found that an organic electroluminescent device using a metal complex having a ligand structure of formula 1 and a first host compound having a structure of formula 2 can significantly improve the overall performance of the organic electroluminescent device.
Disclosure of Invention
The present invention is directed to a series of organic electroluminescent devices comprising a metal complex having a ligand structure of formula 1 and a first host compound having a structure of formula 2 to solve at least part of the above problems.
According to an embodiment of the present invention, there is disclosed an organic electroluminescent device including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex and a first host compound;
wherein the first metal complex comprises a metal M and a ligand L coordinated to the metal MaLigand LaHas a structure represented by formula 1:
Figure BDA0002536583720000025
wherein the content of the first and second substances,
the metal M is selected from metals having a relative atomic mass greater than 40;
cy is selected, identically or differently at each occurrence, from substituted or unsubstituted aryl having 5 to 24 ring atoms, substituted or unsubstituted heteroaryl having 5 to 24 ring atoms; the Cy is linked to the metal M through a metal-carbon bond or a metal-nitrogen bond;
z is, identically or differently at each occurrence, selected from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
X1-X8selected, identically or differently at each occurrence, from C, CRxOr N, and X5-X8At least one selected from C, and linked to said Cy;
X5、X6、X7or X8Is linked to the metal M by a metal-carbon or metal-nitrogen bond;
Rxand RzEach 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 heterocyclyl having 7 to 30 carbon atomsSubstituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RzCan optionally be linked to form a ring;
wherein the first host compound has a structure represented by formula 2:
Figure BDA0002536583720000031
wherein the content of the first and second substances,
q is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRq，CRqRqAnd SiRqRqA group of (a); when two R are simultaneously presentqWhen two R are presentqMay be the same or different;
L1and L2Each 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;
ar, identically or differently on each occurrence, 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;
E1-E3selected from CR, identically or differently at each occurrenceeOr N, and E1-E3At least two of which are N;
U1-U8selected from C, identically or differently on each occurrence，CRuOr N, and U5-U8At least one of them is selected from C and is reacted with L1Connecting;
U1-U8at least one of them is selected from CRuAnd said R isuEach occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
W1-W8selected from CR, identically or differently at each occurrencewOr N;
Rq，Re，Ruand RwEach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, mercapto groups, cyano groups, isocyano groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rq，Re，Ru，RwCan optionally be linked to form a ring.
According to another embodiment of the invention, an electronic device is also disclosed, which comprises the organic electroluminescent device described in the previous embodiment.
Disclosed is an organic electroluminescent device comprising a metal complex having a condensed ligand structure of formula 1 and a first host compound having a structure of formula 2. By selecting the special combination of the host compound and the dopant compound, the appropriate energy level matching of the material of the light-emitting layer can be obtained, the concentration of carriers in the light-emitting layer can be effectively regulated and controlled to achieve the expected balance, and compared with the prior art, the performance of the organic electroluminescent device is obviously improved, such as the improvement of the service life of the device and the like.
Drawings
FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. patent No. 5,703, incorporated by reference in its entirety436 and 5,707,745 disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag with 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 injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate a transition from a triplet state back to a singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of the backfill singlet excited state may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-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. In addition, the alkyl group may be optionally substituted. 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, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl are preferable. In addition, the cycloalkyl group may be optionally substituted.
Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron atoms. 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, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. 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 the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 3-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl groups are 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, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
Figure BDA0002536583720000061
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl. 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 and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of 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 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, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, cinnolino, benzoselenophenopyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-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 groups. 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-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable. 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, diphenyltert-butylsilyl group, tri-tert-butylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. In addition, the arylsilyl 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, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which may be substituted with one or more substituents selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an 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, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that 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 BDA0002536583720000081
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 BDA0002536583720000082
further, the expression that adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
Figure BDA0002536583720000083
according to an embodiment of the present invention, there is disclosed an organic electroluminescent device including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first metal complex and a first host compound;
wherein the first metal complex comprises a metal M and a ligand L coordinated to the metal MaLigand LaHas a structure represented by formula 1:
Figure BDA0002536583720000091
wherein the content of the first and second substances,
the metal M is selected from metals having a relative atomic mass greater than 40;
cy is selected, identically or differently at each occurrence, from substituted or unsubstituted aryl having 5 to 24 ring atoms, substituted or unsubstituted heteroaryl having 5 to 24 ring atoms; the Cy is linked to the metal M through a metal-carbon bond or a metal-nitrogen bond;
z is, identically or differently at each occurrence, selected from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
X1-X8selected, identically or differently at each occurrence, from C, CRxOr N, and X5-X8At least one selected from C, and linked to said Cy;
X5、X6、X7or X8Is linked to the metal M by a metal-carbon or metal-nitrogen bond;
Rxand RzEach 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RzCan optionally be linked to form a ring;
wherein the first host compound has a structure represented by formula 2:
Figure BDA0002536583720000092
wherein the content of the first and second substances,
q is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRq，CRqRqAnd SiRqRqA group of (a); when two R are simultaneously presentqWhen two R are presentqMay be the same or different;
L1and L2Each 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;
ar, identically or differently on each occurrence, 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;
E1-E3selected from CR, identically or differently at each occurrenceeOr N, and E1-E3At least two of which are N;
U1-U8selected, identically or differently at each occurrence, from C, CRuOr N, and U5-U8At least one of them is selected from C and is reacted with L1Connecting;
U1-U8at least one of them is selected from CRuAnd said R isuEach occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
W1-W8selected from CR, identically or differently at each occurrencewOr N;
Rq，Re，Ruand RwEach occurrence, identically or differently, 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 unsubstitutedA 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a mercapto group, a cyano group, an isocyano group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphine group, and combinations thereof;
adjacent substituents Rq，Re，Ru，RwCan optionally be linked to form a ring.
In this embodiment, the "adjacent substituents Rx，RzOptionally joined to form a ring "includes any one or more of the following: adjacent substituents RxMay be linked to form a ring, adjacent substituents RzMay be joined to form a ring. In addition, adjacent substituents RxAnd RzMay be joined to form a ring. In another case adjacent substituents Rz，RxAre not connected to form a ring.
In this embodiment, the "adjacent substituents Rq，Re，Ru，RwOptionally joined to form a ring "includes any one or more of the following: adjacent substituents RqMay be linked to form a ring; adjacent substituents RwMay be linked to form a ring; adjacent substituents RuMay be joined to form a ring. Further adjacent substituents RqAnd RuMay be linked to form a ring; adjacent substituents ReAnd RuMay be linked to form a ring; adjacent substituents ReAnd RwMay be joined to form a ring. In another case adjacent substituents Rq，Re，Ru，RwAre not connected to form a ring.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula 2a and formula 2 b:
Figure BDA0002536583720000101
wherein, in formula 2a and formula 2b,
q is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRq，CRqRqAnd SiRqRqA group of (a); when two R are simultaneously presentqWhen two R are presentqMay be the same or different;
L1and L2Each 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;
ar, identically or differently on each occurrence, 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;
in formula 2a, U2-U8Selected, identically or differently at each occurrence, from C, CRuOr N, and U5-U8At least one of them is selected from C and is reacted with L1Connecting;
in formula 2b, U1-U7Selected, identically or differently at each occurrence, from C, CRuOr N, and U5-U7At least one of them is selected from C and is reacted with L1Connecting;
W1-W8selected from CR, identically or differently at each occurrencewOr N;
V1-V5selected from CR, identically or differently at each occurrencev；
Rq，RuAnd RwEach occurrence, identically or differently, 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 unsubstitutedSubstituted 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 unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester groups, mercapto groups, cyano groups, isocyano groups, hydroxy groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Rveach occurrence, identically or differently, is selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
According to one embodiment of the present invention, wherein the first host compound has a structure represented by formula 3a and formula 3 b:
Figure BDA0002536583720000111
wherein, in formula 3a and formula 3b,
q is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRq，CRqRqAnd SiRqRqA group of (a); when two R are simultaneously presentqWhen two R are presentqMay be the same or different;
L1and L2Each 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;
ar, identically or differently on each occurrence, 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;
in formula 3a, U2-U5And U7-U8Selected from CR, identically or differently at each occurrenceuOr N;
in formula 3b, U1-U5And U7Selected from CR, identically or differently at each occurrenceuOr N;
W1-W8selected from CR, identically or differently at each occurrencewOr N;
V1-V5selected from CR, identically or differently at each occurrencev；
Rq，RuAnd RwEach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, mercapto groups, cyano groups, isocyano groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Rveach occurrence, identically or differently, is selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
According to one embodiment of the invention, wherein Q is selected from O or S, the same or different at each occurrence.
According to one embodiment of the invention, wherein Q is O.
According to an embodiment of the present invention, in formula 2, U1-U8Selected, identically or differently, on each occurrence from C or CRu，W1-W8Selected from CR, identically or differently at each occurrencew，V1-V5Selected from CR, identically or differently at each occurrencev。
According to an embodiment of the present invention, in formula 2a, U2-U8Selected, identically or differently, on each occurrence from C or CRu，W1-W8Selected from CR, identically or differently at each occurrencew，V1-V5Selected from CR, identically or differently at each occurrencev。
In formula 2b, U is1-U7Selected, identically or differently, on each occurrence from C or CRu，W1-W8Selected from CR, identically or differently at each occurrencew，V1-V5Selected from CR, identically or differently at each occurrencev。
According to an embodiment of the present invention, in formula 3a, U2-U5And U7-U8Selected from CR, identically or differently at each occurrenceu，W1-W8Selected from CR, identically or differently at each occurrencew，V1-V5Selected from CR, identically or differently at each occurrencev。
In formula 3b, U is1-U5And U7Selected from CR, identically or differently at each occurrenceu，W1-W8Selected from CR, identically or differently at each occurrencew，V1-V5Selected from CR, identically or differently at each occurrencev。
According to one embodiment of the invention, wherein Ru，RwEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atomsSubstituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein Ru，RwEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein RvEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted phenyl groups.
According to one embodiment of the invention, wherein said Ar, on each occurrence, is selected, identically or differently, from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein said Ar, on each occurrence, is selected, identically or differently, 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 invention, wherein said Ar, on each occurrence, is selected, identically or differently, from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or a combination thereof.
According to one embodiment of the invention, Ar is selected, identically or differently at each occurrence, from the group consisting of: phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
According to an embodiment of the present invention, wherein said L1And L2Each occurrence being the same or different and selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted arylene group, a silicon oxide, a silicon nitride, an oxide, a silicon nitride, a glassAn unsubstituted heteroarylene group having 3-24 carbon atoms, or a combination thereof.
According to an embodiment of the present invention, wherein said L1And L2Each 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 present invention, wherein said L1And L2Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof.
According to an embodiment of the present invention, wherein said L1And L2Each occurrence identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
According to an embodiment of the present invention, wherein the first host compound is selected from the group consisting of compound 2-1 to compound 2-50, wherein the specific structures of compound 2-1 to compound 2-50 are shown in claim 8.
According to an embodiment of the present invention, wherein in formula 1, Cy is selected from any one of structures in the group consisting of:
Figure BDA0002536583720000131
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, poly-or unsubstituted;
r is selected, identically or differently on each occurrence, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R can optionally be linked to form a ring;
wherein, '#' represents a position connected to the metal M, and'' represents X in formula 15，X6，X7Or X8The location of the connection.
Herein, "adjacent substituents R can be optionally linked to form a ring" includes any one or more of the following: when at least two substituents R are adjacent in Cy, the adjacent substituents R may be linked to form a ring, so that
Figure BDA0002536583720000132
By way of example, when two adjacent substituents R are present, i.e.
Figure BDA0002536583720000133
Then a plurality of substituents R in the formula may be linked to form a ring
Figure BDA0002536583720000134
Alternatively, adjacent substituents R are not linked to form a ring.
According to one embodiment of the invention, wherein Cy is selected from
Figure BDA0002536583720000141
Wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, poly-or unsubstituted;
r is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
adjacent substituents R can optionally be linked to form a ring;
wherein, '#' represents a position connected to the metal M, and'' represents a position connected to X in formula 15，X6，X7Or X8The location of the connection.
According to one embodiment of the present invention, wherein X1-X8At least one of which is selected from N.
According to one embodiment of the present invention, wherein X1-X8Selected, identically or differently, on each occurrence from C or CRx。
According to one embodiment of the invention, wherein the ligand LaEach occurrence being the same or different and selected from any one of the group consisting of:
Figure BDA0002536583720000142
Figure BDA0002536583720000151
Figure BDA0002536583720000161
Figure BDA0002536583720000171
Figure BDA0002536583720000181
wherein the content of the first and second substances,
z is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
R，Rxthe same or different at each occurrence represents mono-, poly-, or no substitution;
R，Rxand RzEach 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyanidesA group selected from the group consisting of isocyano, mercapto, hydroxy, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents R, RxAnd RzCan optionally be linked to form a ring.
As used herein, the "adjacent substituents R, RxAnd RzOptionally joined to form a ring "includes any one or more of the following: adjacent substituents R may be linked to form a ring, adjacent substituents RzMay be linked to form a ring, adjacent substituents RxMay be joined to form a ring. In addition, adjacent substituents RzAnd RxMay be linked to form a ring, adjacent substituents R and RxMay be linked to form a ring, adjacent substituents R and RzMay be joined to form a ring. In another case adjacent substituents R, RxAnd RzAre not connected to form a ring.
According to one embodiment of the invention, wherein RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the present invention, wherein the first metal complex has M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein the content of the first and second substances,
the metal M is selected from metals having a relative atomic mass greater than 40;
the ligand La，LbAnd LcOptionally linked to form a multidentate ligand;
m1, 2 or 3, n 0, 1 or 2, q 0, 1 or 2, M + n + q being equal to the oxidation state of the metal M; when m is 2 or more, a plurality of LaMay be the same or different; when n is equal to 2, two LbMay be the same or different; when q is equal to 2, two LcMay be the same or different.
In this example, "the ligand La，LbAnd LcOptionally linked to form a polydentate ligand "includes any one or more of the following: l isa，LbAnd LcAny two of which can be linked to form a tetradentate ligand; l isa，LbAnd LcMay be linked to each other to form a hexadentate ligand. The other is La，LbAnd LcAre not linked and thus do not form multidentate ligands.
According to one embodiment of the invention, wherein the ligand LbAnd LcA structure, which is the same or different at each occurrence, selected from any one of the group consisting of:
Figure BDA0002536583720000191
wherein the content of the first and second substances,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1，CRC1RC2；
Ra，Rb，Rc，RN1，RC1And RC2Each 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 aryl having 3 to 30 carbon atomsA heteroaryl group of carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, a substituted or unsubstituted amino group of 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
ligand LbAnd LcWherein adjacent substituents can optionally be joined to form a ring.
In this example, "ligand LbAnd LcWherein adjacent substituents can optionally be joined to form a ring "includes any one or more of the following: adjacent substituents RaCan be connected to form a ring; adjacent substituents RbCan be connected to form a ring; adjacent substituents RcCan be connected to form a ring; adjacent substituents RaAnd RbCan be connected to form a ring; adjacent substituents RaAnd RcCan be connected to form a ring; adjacent substituents RbAnd RcCan be connected to form a ring; adjacent substituents RC1And RC2Can be connected to form a ring; adjacent substituents RbAnd RC1Can be connected to form a ring; adjacent substituents RaAnd RC1Can be connected to form a ring; adjacent substituents RcAnd RC1Can be connected to form a ring; adjacent substituents RbAnd RC2Can be connected to form a ring; adjacent substituents RaAnd RC2Can be connected to form a ring; adjacent substituents RcAnd RC2Can be connected to form a ring; adjacent substituents RbAnd RN1Can be connected to form a ring; adjacent substituents RaAnd RN1Can be connected to form a ring; adjacent substituents RcAnd RN1May be connected to form a ring. Alternatively, adjacent substitutions are not linked to form a ring.
According to one embodiment of the invention, wherein the ligand LbAnd LcIdentical or different at each occurrenceIs selected from Lb1To Lb195Group of wherein Lb1To Lb195The specific structure of (A) is shown in claim 14.
According to one embodiment of the invention, wherein the metal M is selected, identically or differently at each occurrence, from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.
According to one embodiment of the invention, wherein the metal M is selected from Pt or Ir, identically or differently on each occurrence.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 1 a:
Figure BDA0002536583720000201
wherein the content of the first and second substances,
z is, identically or differently at each occurrence, selected from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
X1-X6selected from CR, identically or differently at each occurrencexOr N;
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
Rxr, on each occurrence, is selected, identically or differently, 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 unsubstitutedSubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R, RxAnd RzCan optionally be linked to form a ring.
According to one embodiment of the invention, wherein the ligand LaEach occurrence being the same or different and is selected from the group consisting of structures represented by any one of the following structures:
Figure BDA0002536583720000211
wherein the content of the first and second substances,
z is selected, identically or differently on each occurrence, from O, S, Se; preferably, Z is O or S; more preferably, Z is O;
R，Rxthe same or different at each occurrence represents mono-, poly-, or no substitution;
R，Rxeach 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groupsA group selected from the group consisting of hydroxy, sulfinyl, sulfonyl, phosphino, and combinations thereof;
preferably, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
adjacent substituents R, RxCan optionally be linked to form a ring.
In this example, the "adjacent substituents R, RxOptionally joined to form a ring "includes any one or more of the following: adjacent substituents R may be linked to form a ring, adjacent substituents RxMay be joined to form a ring. In addition, adjacent substituents R and RxMay be joined to form a ring. In another case adjacent substituents R, RxAre not connected to form a ring.
According to one embodiment of the invention, Z is selected, identically or differently on each occurrence, from O, S.
According to one embodiment of the invention, Z is selected from O, identically or differently on each occurrence.
According to one embodiment of the invention, at least one R isxSelected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.
According to one embodiment of the invention, at least one R isxIs fluorine.
According to one embodiment of the invention, wherein there are at least two RxAnd wherein one R isxIs fluorine, another RxSelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
According to one embodiment of the invention, at least one R isxIs cyano.
According to one embodiment of the invention, wherein there are at least two RxAnd at least one RxIs cyano, another RxSelected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.
According to one embodiment of the invention, wherein there are at least two RxAnd at least one RxIs cyano, another RxSelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
According to one embodiment of the invention, wherein the ligand LaSelected from the following structures:
Figure BDA0002536583720000221
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
As used herein, the "adjacent substituents R, R1-R6Optionally joined to form a ring "includes any one or more of the following: adjacent substituents R may be linked to form a ring, adjacent substituents R1And R2May be linked to form a ring, adjacent substituents R2And R3May be linked to form a ring, adjacent substituents R3And R4May be linked to form a ring, adjacent substituents R4And R5May be linked to form a ring, adjacent substituents R5And R6May be joined to form a ring. In another case adjacent substituents R, R1-R6Are not connected to form a ring.
According to one embodiment of the invention, wherein the ligand LaEach occurrence being selected identically or differently from La1-1-La1-112Group of wherein La1-1-La1-112The specific structure of (A) is shown in claim 24.
According to one embodiment of the invention, wherein the ligand LaSelected from the following structures:
Figure BDA0002536583720000222
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
R1-R3one of which is cyano;
preferably, R1Is cyano or R2Is cyano;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein the ligand LaSelected from the following structures:
Figure BDA0002536583720000231
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
R1-R3one of which is cyano;
R1-R4one of which is 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
more excellentOptionally, R1Is substituted or unsubstituted phenyl, R2Is cyano; or R1Is cyano, R2Is substituted or unsubstituted phenyl; or R1Is cyano, R2Is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein the ligand LaEach occurrence being selected identically or differently from La2-1-La2-81Group of wherein La2-1-La2-81The specific structure of (A) is shown in claim 24.
According to one embodiment of the invention, wherein the ligand LaSelected from the following structures:
Figure BDA0002536583720000232
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, sulfanyl, sulfinyl, sulfonyl, having from 0 to 20 carbon atomsPhosphino, and combinations thereof;
preferably, the substituent R1-R6At least one of which is fluorine;
more preferably, the substituent R2Is fluorine;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein the ligand LaSelected from the following structures:
Figure BDA0002536583720000241
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, R2Is fluorine, R1Is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
more preferably, R2Is fluorine, R1Is substituted or unsubstituted phenyl;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein the ligand LaEach occurrence being selected identically or differently from La3-1-La3-73Group of wherein La3-1-La3-73The specific structure of (A) is shown in claim 24.
According to one embodiment of the invention, wherein the ligand LaSelected from the following structures:
Figure BDA0002536583720000242
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R2-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof;
adjacent substituents R, R2-R6Can optionally be linked to form a ring.
In this example, the "adjacent substituents R, R2-R6Optionally joined to form a ring "includes any one or more of the following: adjacent substituents R may be linked to form a ring, adjacent substituents R2And R3May be linked to form a ring, adjacent substituents R3And R4May be linked to form a ring, adjacent substituents R4And R5May be linked to form a ring, adjacent substituents R5And R6May be joined to form a ring. In another case adjacent substituents R, R2-R6Are all not connectedLooping.
According to one embodiment of the invention, wherein the ligand LaEach occurrence being selected identically or differently from La4-1-La4-80Group of wherein La4-1-La4-80The specific structure of (A) is shown in claim 24.
According to one embodiment of the present invention, wherein the first metal complex has a structure represented by formula 1 b:
Figure BDA0002536583720000251
wherein the content of the first and second substances,
m is 1,2 or 3;
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6、R9-R16and R is selected, identically or differently on each occurrence, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents can optionally be joined to form a ring.
In this embodiment, "adjacent substituents can optionallyThe linkage to form a ring "includes one or more of the following: adjacent substituents R may be linked to each other to form a ring1And R2May be linked to form a ring, adjacent substituents R2And R3May be linked to form a ring, adjacent substituents R3And R4May be linked to form a ring, adjacent substituents R4And R5May be linked to form a ring, adjacent substituents R5And R6May be linked to form a ring, adjacent substituents R9And R10May be linked to form a ring, adjacent substituents R10And R11May be linked to form a ring, adjacent substituents R11And R12May be linked to form a ring, adjacent substituents R12And R13May be linked to form a ring, adjacent substituents R13And R14May be linked to form a ring, adjacent substituents R14And R15May be linked to form a ring, adjacent substituents R15And R16May be connected to form a ring. In addition, adjacent substituents R and R3-R16May be connected to form a ring. In another case, adjacent substituents are not linked to each other to form a ring.
According to one embodiment of the invention, wherein R1-R6At least one of which is selected from the group consisting of: fluorine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein R9-R16At least one selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted heterocyclyl having 7 to 30 carbon atomsA substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
According to one embodiment of the invention, R9-R16Wherein at least one is selected from the group consisting of: 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 one embodiment of the invention, wherein the substituent R10，R11，R15At least one selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the substituent R10，R11，R15At least one selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the substituent R10，R11，R15At least two of which are selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atomsSubstituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the substituent R10，R11，R15At least 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, and combinations thereof.
According to one embodiment of the invention, wherein the substituent R10，R11，R15Each occurrence, the same or different, is selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the substituent R10，R11，R15Each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.
According to one embodiment of the present invention, wherein the first metal complex is selected from the group consisting of compounds GD1-1 to GD1-87, wherein the specific structures of compounds GD1-1 to GD1-87 are shown in claim 29.
According to one embodiment of the present invention, wherein the first metal complex is selected from the group consisting of compound GD2-1 to compound GD2-80, wherein the specific structures of compound GD2-1 to compound GD2-80 are as set forth in claim 29.
According to one embodiment of the invention, wherein the first metal complex is selected from the group consisting of compound GD3-1 to compound GD3-75, wherein the specific structures of compound GD3-1 to compound GD3-75 are as set forth in claim 29.
According to one embodiment of the present invention, wherein the first metal complex is selected from the group consisting of compound GD4-1 to compound GD4-86, wherein the specific structures of compound GD4-1 to compound GD4-86 are as set forth in claim 29.
According to one embodiment of the present invention, wherein the first metal complex is selected from the group consisting of compound GD5-1 to compound GD5-80, wherein the specific structures of compound GD5-1 to compound GD5-80 are as set forth in claim 29.
According to an embodiment of the present invention, wherein the organic layer is a light emitting layer, the first metal complex is a light emitting material.
According to one embodiment of the present invention, wherein a second host compound comprising at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
According to one embodiment of the invention, the second host material comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolocarbazole, fluorene, silafluorene, and combinations thereof.
According to one embodiment of the invention, wherein the second host compound comprises a compound having a structure represented by formula X:
Figure BDA0002536583720000271
wherein the content of the first and second substances,
LTeach occurrence identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, and combinations thereof;
t is selected, identically or differently on each occurrence, from C, CRtOr N;
Rteach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Ar1each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
adjacent substituents RtCan optionally be joined to form a ring.
As used herein, the "adjacent substituent RtOptionally linked to form a ring "is intended to mean that T is chosen from CR when present in formula XtAdjacent substituent groups, e.g. adjacent substituent groups RtCan be linked to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X-a through formula X-j:
Figure BDA0002536583720000272
Figure BDA0002536583720000281
wherein, in the formulae X-a to X-j,
t is selected, identically or differently on each occurrence, from CRtOr N;
LTeach occurrence identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, and combinations thereof;
Rteach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Ar1each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
adjacent substituents RtCan optionally be joined to form a ring.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X, and T is selected from C or CR, the same or different at each occurrencetWherein R istEach occurrence being the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X, and T is selected from C or CR, the same or different at each occurrencetWherein R istEach occurrence, identically or differently, is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X, and T is selected from C or CR, the same or different at each occurrencetWherein R istEach occurrence, the same or different, is selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
According to an embodiment of the present invention, wherein said Ar1Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof.
According to an embodiment of the present invention, wherein said Ar1Each occurrence, the same or different, is selected from the group consisting of: phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, dibenzofuranyl, biphenylBenzothienyl, and combinations thereof.
According to an embodiment of the present invention, wherein said LTThe same or different at each occurrence is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.
According to an embodiment of the present invention, wherein said LTEach occurrence identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group.
According to an embodiment of the present invention, wherein said LTIs a single bond, phenyl or biphenyl.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula X-h.
According to an embodiment of the present invention, wherein the second host compound is selected from the group consisting of compounds X-1 to X-126, wherein the specific structures of compounds X-1 to X-126 are shown in claim 37.
According to one embodiment of the present invention, wherein the organic layer is a light-emitting layer comprising a first metal complex, a first host compound and a second host compound, the total weight of the first metal complex is 1% to 30% by weight of the light-emitting layer.
According to one embodiment of the present invention, the total weight of the first metal complex is 3% to 13% by weight of the light emitting layer.
According to an embodiment of the invention, an electronic device is also disclosed, which comprises the organic electroluminescent device of any one of the foregoing embodiments.
In combination with other materials
The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
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 materials in the light-emitting layer is not particularly limited, and those skilled in the art can reasonably select the materials within a certain range according to the prior art, for example, the first host compound accounts for 10% to 90%, the second host compound accounts for 10% to 90%, and the dopant compound accounts for 1% to 60% of the total weight of the light-emitting layer material; or preferably, the dopant compound comprises 3% to 30%. More preferably, the first host compound is 20% to 65%, the second host compound is 20% to 65%, and the dopant compound is 3% to 30%. The characteristics of the light emitting devices prepared in the examples were tested using equipment conventional in the art, in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent. The compounds such as the first metal complex, the first host compound and the second host compound used in the present invention are easily available to those skilled in the art, and may be obtained, for example, by commercially available methods, or by referring to a preparation method in the prior art, or by referring to a preparation method in chinese application No. CN2019100770790, and are not described herein again.
Example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of torr, the evaporation was performed by thermal vacuum evaporation at a rate of 0.2 to 2 angstroms/second in turn on an ITO anode. Compound HI was used as Hole Injection Layer (HIL). The compound HT is used as a Hole Transport Layer (HTL). The compound X-4 was used as an Electron Blocking Layer (EBL). Then the compound GD2-2 is doped in the first body 2-1 and the second bodyIn host X-4, co-evaporation was used as the light-emitting layer (8:46:46, EML). H2 was used as a Hole Blocking Layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.
Comparative example 1a
Comparative example 1a was prepared the same as example 1 except that compound H2 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 1b
Comparative example 1b was prepared the same as example 1 except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Example 2
Example 2 was prepared in the same manner as in example 1, except that the compound GD2-12 was used in place of the compound GD2-2 in the light-emitting layer (EML).
Comparative example 2a
Comparative example 2a was prepared the same as example 2 except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Example 3
Example 3 was prepared as in example 1, except that the compound GD2-43 was used in place of the compound GD2-2 in the light emitting layer (EML).
Comparative example 3a
Comparative example 3a was prepared the same as example 3 except that compound H2 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 3b
Comparative example 3b was prepared as in example 3, except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Example 4
Example 4 was prepared in the same manner as in example 1, except that the compound GD2-59 was used in place of the compound GD2-2 in the light-emitting layer (EML).
Comparative example 4a
Comparative example 4a was prepared the same as example 4 except that compound H1 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 4b
Comparative example 4b was prepared the same as example 4 except that compound H2 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 4c
Comparative example 4c was prepared the same as example 4 except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Example 5
Example 5 was prepared in the same manner as in example 1 except that the compound GD4-1 was used in place of the compound GD2-2 in the light-emitting layer (EML).
Comparative example 5a
Comparative example 5a was prepared the same as example 5 except that compound H1 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 5b
Comparative example 5b was prepared the same as example 5 except that compound H2 was used instead of compound 2-1 in the light emitting layer (EML).
Example 6
Example 6 was prepared in the same manner as in example 1, except that the compound GD4-58 was used in place of the compound GD2-2 in the light-emitting layer (EML).
Comparative example 6a
Comparative example 6a was prepared the same as example 6 except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Example 7
Example 7 was prepared in the same manner as in example 1 except that the compound GD4-59 was used in place of the compound GD2-2 in the light-emitting layer (EML).
Comparative example 7a
Comparative example 7a was prepared the same as example 7 except that compound H2 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 7b
Comparative example 7b was prepared the same as example 7 except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Example 8
Example 8 was prepared as in example 1, except that the compound GD1-87 was used in place of the compound GD2-2 in the light-emitting layer (EML).
Comparative example 8a
Comparative example 8a was prepared the same as example 8 except that compound H2 was used instead of compound 2-1 in the light emitting layer (EML).
Example 9
Example 9 was prepared in the same manner as in example 1 except that compound GD5-77 was used in place of compound GD2-2 in the light-emitting layer (EML).
Comparative example 9a
Comparative example 9a was prepared the same as example 9 except that compound H3 was used instead of compound 2-1 in the light emitting layer (EML).
Comparative example 10
Comparative example 10 was prepared as in example 1, except that the compound Ir (ppy) was used in the light emitting layer (EML)3Instead of compound GD 2-2.
The detailed device portion layer structures and thicknesses are shown in the following table. Wherein more than one of the materials used is obtained by doping different compounds in the recited weight ratios.
Table 1 device structures of examples and comparative examples
Figure BDA0002536583720000321
Figure BDA0002536583720000331
Figure BDA0002536583720000341
The material structure used in the device is as follows:
Figure BDA0002536583720000342
Figure BDA0002536583720000351
table 2 shows the results at 15 mA/cm2CIE data, Current Efficiency (CE) measured at constant current, and measured at 10000 cd/m2Measured lifetime of the device at luminance (LT 95).
TABLE 2 device data
Figure BDA0002536583720000352
Figure BDA0002536583720000361
Discussion:
in example 1, comparative examples 1a and 1b, for using GD2-2, which is an Ir complex-based phosphorescent dopant containing a dibenzofuranylpyridine ligand of the present invention, as a light emitting material, a compound 2-1 of the present invention, a reference compound H2 and a reference compound H3 were used as a first host compound, respectively. Example 1 compared to comparative example 1a, the current efficiency was the same as comparative example, but the device lifetime was improved by 42.9%. Example 1 has improved current efficiency compared to comparative example 1b, while device lifetime is improved by about 48.6%.
In example 2 and comparative example 2a, for using the Ir complex-based phosphorescent dopant GD2-12 containing the dibenzofuranylpyridine ligand of the invention as a light emitting material, when the compound 2-1 of the invention was used as the first host compound, the current efficiency of the device was improved and the lifetime of the device was improved by 57% compared to when the reference compound H3 was used as the first host compound.
In example 3, comparative examples 3a and 3b, for using the Ir complex-based phosphorescent dopant GD2-43 containing the dibenzofuranylpyridine ligand of the invention as a light emitting material, the compound 2-1 of the invention, the reference compound H2 and the reference compound H3 were used as the first host compound, respectively. Example 3 compared to comparative example 3a, the current efficiency was improved, while the device lifetime was improved by 68.7%. Compared with comparative example 3b, the current efficiency is improved, and the service life of the device is improved by 19.8%.
In example 4, comparative examples 4a, 4b and 4c, for using the Ir complex-based phosphorescent dopant GD2-59 containing the dibenzofuranylpyridine ligand of the present invention as a light emitting material, the compound 2-1 of the present invention, the reference compound H1, the reference compound H2 and the reference compound H3 were used as the first host compound, respectively. Compared with comparative example 4a, the current efficiency is improved, and the service life of the device is improved by 89.7%; compared with comparative example 4b, the current efficiency is improved, and the service life of the device is improved by about 76.9%; compared with comparative example 4c, the current efficiency is substantially equivalent to that of the comparative example, but the device lifetime is improved by about 22.7%.
In example 5, comparative examples 5a and 5b, for using GD4-1, which is an Ir complex-based phosphorescent dopant containing a dibenzofuranylpyridine ligand of the present invention, as a light emitting material, a compound 2-1 of the present invention, a reference compound H1 and a reference compound H2 were used as a first host compound, respectively. Example 5 compared to comparative example 5a, the current efficiency was the same as comparative example, but the device lifetime was improved by about 99.4%; compared with comparative example 5b, the current efficiency is equivalent to that of comparative example, but the device lifetime is improved by 94.2%.
In example 6 and comparative example 6a, for using the Ir complex-based phosphorescent dopant GD4-58 containing the dibenzofuranylpyridine ligand of the invention as a light emitting material, when the material 2-1 of the invention was used as the first host, the current efficiency of the device was improved and the lifetime of the device was improved by about 26.7% compared to when the reference compound H3 was used as the first host.
In example 7, comparative examples 7a and 7b, for using the Ir complex-based phosphorescent dopant GD4-59 containing the dibenzofuranylpyridine ligand of the invention as a light emitting material, the compound 2-1 of the invention, the reference compound H2 and the reference compound H3 were used as the first host compound, respectively. Compared with the comparative example 7a, the current efficiency is improved, and the service life of the device is improved by about 63.9 percent; compared to comparative example 7b, the current efficiency was the same as comparative example, but the device lifetime was improved by about 8.2%.
In example 8 and comparative example 8a, when GD1-87, which is an Ir complex-based phosphorescent dopant containing a dibenzofuranylpyridine ligand of the present invention, was used as a light-emitting material, the current efficiency of the device was comparable to that of the comparative example, but the device lifetime was improved by 19.6%, when the material 2-1 of the present invention was used as the first host, compared to the reference compound H2.
In example 9 and comparative example 9a, when GD5-77, which is an Ir complex-based phosphorescent dopant containing a dibenzofuranylpyridine ligand of the present invention, was used as a light-emitting material, the current efficiency of the device was comparable to that of the comparative example, but the device lifetime was improved by 7.6%, when the material 2-1 of the present invention was used as the first host, compared to the reference compound H3.
Examples 1 to 9 using an Ir complex-based phosphorescent dopant containing a dibenzofuranylpyridine ligand of the present invention as a light-emitting material, and Ir (ppy) phosphorescent dopants not of the present invention3The current efficiency is improved considerably or slightly, and the device lifetime is improved considerably, especially up to 150% in example 5 (1606.3hrs vs.638.8hrs) in comparison with comparative example 10, which is a luminescent material. Therefore, the Ir complex phosphorescent dopant containing the dibenzofuranylpyridine ligand and the first host compound are matched, and the Ir complex phosphorescent dopant containing the dibenzofuranylpyridine ligand and the first host compound have particularly excellent effects on improving the current efficiency and prolonging the service life of a device.
In summary, compared with other devices, when the metal complex-based dopant having the ligand of formula 1 and the first host compound having the structure of formula 2 of the present invention are used in the organic layer, the current efficiency of the device is equivalent to or improved compared with the comparative example, but it is important that the lifetime of the device is significantly improved, and most of the devices are significantly improved. This provides the industry with a superior combination of materials for the light emitting layer.
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 (39)

1. An organic 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 metal complex and a first host compound;
wherein the first metal complex comprises a metal M and a ligand L coordinated to the metal MaLigand LaHas a structure represented by formula 1:
Figure FDA0002536583710000011
wherein the content of the first and second substances,
the metal M is selected from metals having a relative atomic mass greater than 40;
cy is selected, identically or differently at each occurrence, from substituted or unsubstituted aryl having 5 to 24 ring atoms, substituted or unsubstituted heteroaryl having 5 to 24 ring atoms; the Cy is linked to the metal M through a metal-carbon bond or a metal-nitrogen bond;
z is, identically or differently at each occurrence, selected from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
X1-X8selected, identically or differently at each occurrence, from C, CRxOr N, and X5-X8At least one selected from C, and linked to said Cy;
X5、X6、X7or X8Is linked to the metal M by a metal-carbon or metal-nitrogen bond;
Rxand RzEach 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RzCan optionally be linked to form a ring;
wherein the first host compound has a structure represented by formula 2:
Figure FDA0002536583710000012
wherein the content of the first and second substances,
q is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRq，CRqRqAnd SiRqRqA group of (a); when two R are simultaneously presentqWhen two R are presentqMay be the same or different;
L1and L2Each 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;
ar, identically or differently on each occurrence, 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;
E1-E3selected from CR, identically or differently at each occurrenceeOr N, and E1-E3At least two of which are selected from N;
U1-U8selected, identically or differently at each occurrence, from C, CRuOr N, and U5-U8At least one of them is selected from C and is reacted with L1Connecting;
U1-U8at least one of them is selected from CRuAnd said R isuEach occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms;
W1-W8selected from CR, identically or differently at each occurrencewOr N;
Rq，Re，Ruand RwEach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, mercapto groups, cyano groups, isocyano groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rq，Re，Ru，RwCan optionally be linked to form a ring.
2. The organic electroluminescent device as claimed in claim 1, wherein the first host compound has a structure represented by formula 2a or formula 2 b:
Figure FDA0002536583710000021
wherein, in formula 2a and formula 2b,
Ar、L1、L2、Q、W1-W8has the same definition as in claim 1;
U1-U8selected, identically or differently at each occurrence, from C, CRuOr N, and U5-U8At least one of them is selected from C and is reacted with L1Connecting;
V1-V5selected from CR, identically or differently at each occurrencev；
RuEach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, mercapto groups, cyano groups, isocyano groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Rveach occurrence, identically or differently, is selected from the group consisting of: the presence of hydrogen in the presence of hydrogen,substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
3. The organic electroluminescent device as claimed in claim 2, wherein the first host compound has a structure represented by formula 3a or formula 3 b:
Figure FDA0002536583710000031
wherein, in formula 3a and formula 3b,
Ar、L1、L2、、Q、V1-V5、W1-W8has the same definition as in claim 2;
U1-U5、U7-U8selected from CR, identically or differently at each occurrenceuOr N;
Rueach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, mercapto groups, cyano groups, isocyano groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
4. An organic electroluminescent device as claimed in any one of claims 1 to 3, wherein Q is the same or different at each occurrence and is selected from O or S; preferably, Q is O.
5. The organic electroluminescent device as claimed in any one of claims 1 to 2, wherein U is1-U8Selected, identically or differently, on each occurrence from C or CRu，W1-W8Selected from CR, identically or differently at each occurrencew，V1-V5Selected from CR, identically or differently at each occurrencev；
Preferably, wherein Ru，RwEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, 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, and combinations thereof.
6. The organic electroluminescent device of any one of claims 1 to 5, wherein the Ar, identically or differently at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof;
preferably, Ar is selected, identically or differently at each occurrence, from the group consisting of: phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
7. The organic electroluminescent device as claimed in any one of claims 1 to 6, wherein L is1And L2Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 24 carbon atoms, or a combination thereof;
preferably, wherein said L1And L2Each occurrence being the same or different and selected from the group consisting of a single bond, substituted or unsubstituted phenyl, substituted or unsubstitutedBiphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl.
8. The organic electroluminescent device of claim 1, wherein the first host compound is selected from the group consisting of:
Figure FDA0002536583710000041
Figure FDA0002536583710000051
Figure FDA0002536583710000061
Figure FDA0002536583710000071
Figure FDA0002536583710000081
9. the organic electroluminescent device according to any one of claims 1 to 8, wherein in formula 1, Cy is identically or differently at each occurrence selected from any one of the structures consisting of:
Figure FDA0002536583710000082
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, poly-or unsubstituted;
r is selected, identically or differently on each occurrence, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, Cy is selected, identically or differently on each occurrence, from
Figure FDA0002536583710000083
Adjacent substituents R can optionally be linked to form a ring;
wherein, '#' represents a position connected to the metal M, and'' represents X in formula 15，X6，X7Or X8The location of the connection.
10. The organic electroluminescent device as claimed in any one of claims 1 to 9, wherein X1-X8At least one of which is selected from N.
11. The organic electroluminescent device as claimed in any one of claims 1 to 9, wherein X1-X8Selected, identically or differently, on each occurrence from C or CRx。
12. An organic electroluminescent device as claimed in any one of claims 1 to 9Wherein the ligand LaEach occurrence being the same or different and selected from any one of the group consisting of:
Figure FDA0002536583710000091
Figure FDA0002536583710000101
Figure FDA0002536583710000111
Figure FDA0002536583710000121
Figure FDA0002536583710000131
wherein the content of the first and second substances,
z is selected, identically or differently on each occurrence, from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
R，Rxthe same or different at each occurrence represents mono-, poly-, or no substitution;
R，Rxand RzEach 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 atomsAn alkoxy group of 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, RxAnd RzCan optionally be linked to form a ring;
preferably, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
13. The organic electroluminescent device as claimed in any one of claims 1 to 12, wherein the first metal complex has M (L)a)m(Lb)n(Lc)qA general formula (II) of (I);
wherein the content of the first and second substances,
the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, the metal M being the same or different at each occurrence; preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;
the ligand La，LbAnd LcOptionally linked to form a multidentate ligand;
m is selected from 1,2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, M + n + q is equal to the oxidation state of the metal M; when m is 2 or more, a plurality of LaMay be the same or different; when n is equal to 2, two LbMay be the same or different; when q is equal to 2Two of LcMay be the same or different;
preferably, wherein the ligand LbAnd LcA structure, which is the same or different at each occurrence, selected from any one of the group consisting of:
Figure FDA0002536583710000132
Figure FDA0002536583710000141
wherein the content of the first and second substances,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1，CRC1RC2；
Ra，Rb，Rc，RN1，RC1And RC2Each 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups,mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
ligand LbAnd LcWherein adjacent substituents can optionally be joined to form a ring.
14. The organic electroluminescent device as claimed in claim 13, wherein the ligand LbAnd LcEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0002536583710000142
Figure FDA0002536583710000151
Figure FDA0002536583710000161
Figure FDA0002536583710000171
Figure FDA0002536583710000181
Figure FDA0002536583710000191
Figure FDA0002536583710000201
15. the organic electroluminescence according to any one of claims 1 to 9 and 13Device wherein the ligand LaHas a structure represented by formula 1 a:
Figure FDA0002536583710000202
wherein the content of the first and second substances,
z is, identically or differently at each occurrence, selected from the group consisting of O, S, Se, NRz，CRzRzAnd SiRzRzA group of (a); when two R are simultaneously presentzWhen two R are presentzMay be the same or different;
X1-X6selected from CR, identically or differently at each occurrencexOr N;
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
Rxr and RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3 to 20 ring atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, hydroxyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
adjacent substituents R, RxAnd RzCan optionally be linked to form a ring.
16. As in claimThe organic electroluminescent device as claimed in any one of claims 1 to 9 and 13, wherein the ligand LaEach occurrence being the same or different and is selected from the group consisting of structures represented by any one of the following structures:
Figure FDA0002536583710000211
wherein the content of the first and second substances,
z is selected, identically or differently on each occurrence, from O, S, Se; preferably, Z is O or S; more preferably, Z is O;
R，Rxthe same or different at each occurrence represents mono-, poly-, or no substitution;
R，Rxeach 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atomsHeteroaryl of a group, substituted or unsubstituted alkylsilyl of 3-20 carbon atoms, cyano, and combinations thereof;
adjacent substituents R, RxCan optionally be linked to form a ring.
17. The organic electroluminescent device as claimed in any one of claims 1 to 16, wherein at least one R isxSelected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.
18. The organic electroluminescent device as claimed in any one of claims 1 to 17, wherein at least one R isxIs fluorine or cyano.
19. The organic electroluminescent device as claimed in any one of claims 1 to 16, wherein at least two R's are presentxAnd wherein one R isxIs fluorine or cyano, the other RxSelected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
20. The organic electroluminescent device as claimed in any one of claims 1 to 9 and 13, wherein the ligand LaSelected from the following structures:
Figure FDA0002536583710000221
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substitutedOr 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, and combinations thereof;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
21. The organic electroluminescent device as claimed in any one of claims 1 to 9, 13 and 19, wherein the ligand LaSelected from the following structures:
Figure FDA0002536583710000222
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
R1-R3one of which is cyano;
preferably, R1Is cyanoOr R2Is cyano;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
22. The organic electroluminescent device as claimed in any one of claims 1 to 9 and 13, wherein the ligand LaSelected from the following structures:
Figure FDA0002536583710000231
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6and R is selected, identically or differently on each occurrence, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
preferably, the substituent R1-R6At least one of which is fluorine;
more preferably, R2Is fluorine, R1Is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
adjacent substituents R, R1-R6Can optionally be linked to form a ring.
23. The organic electroluminescent device as claimed in any one of claims 1 to 9 and 13, wherein the ligand LaSelected from the following structures:
Figure FDA0002536583710000232
wherein the content of the first and second substances,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R2-R6and R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, and combinations thereof;
adjacent substituents R, R2-R6Can optionally be linked to form a ring.
24. The organic electroluminescent device as claimed in any one of claims 1 to 9 and 13, wherein the ligand LaEach occurrence being the same or different and selected from any one of the group consisting of:
Figure FDA0002536583710000241
Figure FDA0002536583710000251
Figure FDA0002536583710000261
Figure FDA0002536583710000271
Figure FDA0002536583710000281
Figure FDA0002536583710000291
Figure FDA0002536583710000301
Figure FDA0002536583710000311
Figure FDA0002536583710000321
Figure FDA0002536583710000331
Figure FDA0002536583710000341
Figure FDA0002536583710000351
Figure FDA0002536583710000361
Figure FDA0002536583710000371
Figure FDA0002536583710000381
Figure FDA0002536583710000391
Figure FDA0002536583710000401
Figure FDA0002536583710000411
Figure FDA0002536583710000421
25. the organic electroluminescent device as claimed in any one of claims 1, 13 to 23, wherein the first metal complex has a structure represented by formula 1 b:
Figure FDA0002536583710000422
wherein the content of the first and second substances,
m is 1,2 or 3;
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted;
R1-R6、R9-R16and R is selected, identically or differently on each occurrence, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents can optionally be joined to form a ring.
26. The organic electroluminescent device as claimed in claim 25, wherein R1-R6At least one of which is selected from the group consisting of: fluorine, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 15 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 15 carbon atoms, cyano groups, and combinations thereof.
27. An electroluminescent device as claimed in claim 25 or 26 in which R9-R16At least one selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted heteroarylAn 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a hydroxyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
preferably, R9-R16Wherein at least one is selected from the group consisting of: 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.
28. An electroluminescent device as claimed in claim 25 or 26 in which R10，R11，R15One or two or three of which, on each occurrence, are selected, identically or differently, from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
preferably, R10，R11，R15One or two or three of which, on each occurrence, are selected, identically or differently, 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, and combinations thereof.
29. An electroluminescent device as claimed in any one of claims 1 to 9 and 13 wherein the first metal complex is selected from the group consisting of:
Figure FDA0002536583710000431
Figure FDA0002536583710000441
Figure FDA0002536583710000451
Figure FDA0002536583710000461
Figure FDA0002536583710000471
Figure FDA0002536583710000481
Figure FDA0002536583710000491
Figure FDA0002536583710000501
Figure FDA0002536583710000511
Figure FDA0002536583710000521
Figure FDA0002536583710000531
Figure FDA0002536583710000541
Figure FDA0002536583710000551
Figure FDA0002536583710000561
Figure FDA0002536583710000571
Figure FDA0002536583710000581
Figure FDA0002536583710000591
Figure FDA0002536583710000601
Figure FDA0002536583710000611
Figure FDA0002536583710000621
Figure FDA0002536583710000631
Figure FDA0002536583710000641
Figure FDA0002536583710000651
Figure FDA0002536583710000661
Figure FDA0002536583710000671
Figure FDA0002536583710000681
Figure FDA0002536583710000691
Figure FDA0002536583710000701
Figure FDA0002536583710000711
Figure FDA0002536583710000721
Figure FDA0002536583710000731
Figure FDA0002536583710000741
Figure FDA0002536583710000751
Figure FDA0002536583710000761
Figure FDA0002536583710000771
Figure FDA0002536583710000781
Figure FDA0002536583710000791
Figure FDA0002536583710000801
Figure FDA0002536583710000811
Figure FDA0002536583710000821
Figure FDA0002536583710000831
30. an electroluminescent device as claimed in any one of claims 1 to 29 wherein the organic layer is a light-emitting layer and the first metal complex is a light-emitting material.
31. The electroluminescent device of claim 30 wherein said light-emitting layer further comprises a second host compound comprising at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof;
preferably, the second host material comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolocarbazole, fluorene, silafluorene, and combinations thereof.
32. The electroluminescent device of claim 31, wherein the second host compound comprises a compound having a structure represented by formula X:
Figure FDA0002536583710000832
wherein the content of the first and second substances,
LTeach occurrence being the same or different and being selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylene groupUnsubstituted cycloalkylene having 3-20 carbon atoms, substituted or unsubstituted arylene having 6-20 carbon atoms, substituted or unsubstituted heteroarylene having 3-20 carbon atoms, and combinations thereof;
t is selected, identically or differently on each occurrence, from C, CRtOr N;
Rteach occurrence, identically or differently, 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, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, hydroxyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Ar1each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
adjacent substituents RtCan optionally be joined to form a ring.
33. The electroluminescent device of claim 32, wherein the second host compound has a structure represented by one of formulae X-a to X-j:
Figure FDA0002536583710000841
Figure FDA0002536583710000851
wherein, in the formulae X-a to X-j,
T、LT、Ar1has the same definition as in claim 32.
34. The electroluminescent device of claim 32 or 33, wherein the second host compound has a structure represented by formula X, and T is selected from C or CR, the same or different at each occurrencetWherein R istEach occurrence identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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;
preferably, wherein RtEach occurrence, identically or differently, is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms;
more preferably, wherein RtEach occurrence, the same or different, is selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
35. The organic electroluminescent device as claimed in any one of claims 32 to 34, wherein the Ar is1Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof;
preferably, wherein said Ar is1Each time goes outThe nonce is selected, identically or differently, from the group consisting of: phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, terphenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
36. The organic electroluminescent device as claimed in any one of claims 32 to 35, wherein the LTEach occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
preferably, wherein said LTEach occurrence identically or differently selected from the group consisting of a single bond, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group;
more preferably, wherein said LTIs a single bond, phenyl or biphenyl.
37. The electroluminescent device of any one of claims 31-33, wherein the second host compound is selected from the group consisting of:
Figure FDA0002536583710000861
Figure FDA0002536583710000871
Figure FDA0002536583710000881
Figure FDA0002536583710000891
Figure FDA0002536583710000901
Figure FDA0002536583710000911
Figure FDA0002536583710000921
Figure FDA0002536583710000931
Figure FDA0002536583710000941
Figure FDA0002536583710000951
Figure FDA0002536583710000961
Figure FDA0002536583710000971
38. an electroluminescent device as claimed in any one of claims 31 to 37 wherein the organic layer is a light-emitting layer comprising a first metal complex, a first host compound and a second host compound, preferably the total weight of the first metal complex is from 1% to 30% by weight of the light-emitting layer;
more preferably, the total weight of the first metal complex is 3% to 13% of the weight of the light-emitting layer.
39. An electronic device comprising the organic electroluminescent device according to any one of claims 1 to 38.
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