CN114678485A - Electroluminescent device - Google Patents

Electroluminescent device Download PDF

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CN114678485A
CN114678485A CN202011546486.0A CN202011546486A CN114678485A CN 114678485 A CN114678485 A CN 114678485A CN 202011546486 A CN202011546486 A CN 202011546486A CN 114678485 A CN114678485 A CN 114678485A
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邝志远
张晗
张奇
王乐
王强
谢梦兰
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Beijing Summer Sprout Technology Co Ltd
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    • HELECTRICITY
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    • H10K50/11OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Abstract

An electroluminescent device is disclosed. The electroluminescent device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a first compound having a structure of formula 1a and a second compound having a ligand structure of formula 2. The novel material combination can enable an electroluminescent device to obtain lower voltage and higher efficiency, and can provide better device performance. Also disclosed is a display module comprising the electroluminescent device, and a combination of compounds of a first compound having a partial structure of formula 1a and a second compound having a ligand structure of formula 2.

Description

Electroluminescent device
Technical Field
The present invention relates to electronic devices, such as electroluminescent devices. More particularly, it relates to a first compound comprising a phenanthrooxazole having a structure represented by formula 1a and the like in an organic layer and a ligand L having a structure represented by formula 2aThe second compound of (a) above.
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 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.
In order to meet the increasing demands of the industry on various aspects of electroluminescent devices, such as color of light emission, color saturation of light emission, driving voltage, light emitting efficiency, device lifetime, etc., researches on phosphorescent devices are still in need. In the research of phosphorescent devices, the matching use of phosphorescent light-emitting materials and host materials is very important, and the matching selection of the phosphorescent light-emitting materials and the host materials is directly related to the light-emitting performance of the devices. The selection and optimization of the combination of phosphorescent light-emitting materials and host materials is therefore an important part of the research relevant in the industry.
Disclosure of Invention
The invention aims to provide an electric field generator with a novel material combinationLight emitting devices address at least some of the above issues. The electroluminescent device uses a first compound having phenanthrooxazole and similar structures and a ligand LaAnd a novel combination of materials consisting of the second compound of (a), which novel combination of materials can be used in the light-emitting layer of an electroluminescent device. The novel material combination can enable an electroluminescent device to obtain lower voltage and higher efficiency, and can provide better device performance.
According to one embodiment of the present invention, there is disclosed an electroluminescent device comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound;
the first compound has a structure represented by formula 1 a:
Figure BDA0002856206100000021
in formula 1a, A1-A10Each independently selected from C, CRAOr N; and A is1-A103 of are C; wherein 2C are adjacent and are connected to the structure represented by formula 1 b; another C is linked to a structure represented by formula 1C:
Figure BDA0002856206100000022
respectively representing the position of the connection of the formula 1b and the formula 1a, and the position of the connection of the formula 1c and the formula 1 a;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
v is selected fromNR2O or S;
RA,R1,R2each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents RA,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex and comprises a ligand L coordinated with the metalaAnd the metal is selected from metals having a relative atomic mass greater than 40; l isaHas a structure represented by formula 2:
Figure BDA0002856206100000031
in formula 2, Z is selected from O, S or Se;
X1-X8selected, identically or differently at each occurrence, from C, CRxOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; said R isy2has-L1-SiRs1Rs2Rs3Is connected withStructuring;
Rx,Ry1,Rs1,Rs2,Rs3each 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 arylsilane groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
L1selected from 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, or a combination thereof;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring.
According to one embodiment of the present invention, a display assembly is disclosed that includes an electroluminescent device as shown in the previous embodiments.
According to another embodiment of the present invention, a combination of compounds is also disclosed, wherein at least the first compound and the second compound are included.
The invention discloses a novel electroluminescent device, which uses a compound consisting of phenanthrooxazole and the likeFirst compound of structure and comprising ligand LaAnd a novel combination of materials consisting of the second compound of (a), which novel combination of materials can be used in the light-emitting layer of an electroluminescent device. The novel material combination enables the novel electroluminescent device to obtain lower voltage and higher efficiency, and can provide better device performance.
Drawings
Fig. 1 is a schematic diagram of an organic light emitting device that may contain electroluminescent devices as disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that may contain electroluminescent devices as disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but 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 50:14-TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson 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. Incorporated by reference in its entiretyUs patent nos. 5,703,436 and 5,707,745, which are incorporated by reference, 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 a schematic, 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 on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or 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, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.
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 (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states 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. 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, 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 BDA0002856206100000051
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-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, and 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, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothiophene bipyridine, benzothiophene, selenophene bipyridine, selenophene bipyridine, 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 the aryl and heteroaryl groups are the same as those 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, and diphenyltert-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, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted by one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, 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, polysubstitution is meant to encompass disubstituted substitutions up to the maximum range of 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 BDA0002856206100000081
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 BDA0002856206100000082
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 BDA0002856206100000083
according to one embodiment of the present invention, there is disclosed an electroluminescent device comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound;
the first compound has a structure represented by formula 1 a:
Figure BDA0002856206100000084
in formula 1a, A1-A10Each independently selected from C, CRAOr N; and A is1-A103 of are C; wherein 2C are adjacent and are connected to the structure represented by formula 1 b; and the other C is linked to a structure represented by formula 1C:
Figure BDA0002856206100000085
represents the position where formula 1b is connected to formula 1a, and the position where formula 1c is connected to formula 1a, respectively;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
v is selected from NR2O or S;
RA,R1,R2each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents RA,R1,R2Can optionally be linked to form a ring;
the second compound is a metal complex and comprises a ligand L coordinated with the metalaAnd the metal is selected from metals having a relative atomic mass greater than 40; l isaHas a structure represented by formula 2:
Figure BDA0002856206100000091
in formula 2, Z is selected from O, S or Se;
X1-X8is selected, identically or differently on each occurrence, from C, CRxOr N;
Y1-Y6is selected, identically or differently on each occurrence, from CRy1、CRy2Or N; the R isy2Having a radical of formula-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
L1selected from 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, or a combination thereof;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring.
In this context, adjacent substituents RA,R1And R2Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents RAOf a substituent RAAnd R2And a substituent R1And R2Any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
In the examples, adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring, is intended to mean for adjacent substituent groups, for example, adjacent substituents RxOf a substituent Rs1And Rs2Of a substituent Rs1And Rs3And a substituent Rs2And Rs3Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these substituent groups may not be connected to form a ring.
According to one embodiment of the present invention, in formula 1a, A1-A10Each independently selected from C, CRAOr N, and A1-A10At least one of which is selected from N.
According to an embodiment of the present invention, wherein the first compound has a structure represented by one of formulas 1a-1 to 1 a-6:
Figure BDA0002856206100000101
in formulae 1a-1 to 1a-6,
A1-A10selected, identically or differently at each occurrence, from C, CRAOr N; and A is1-A10Is C, and is linked to a structure represented by formula 1C:
Figure BDA0002856206100000102
represents the position where formula 1c is linked to formulae 1a-1 to 1 a-6;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
v is selected from NR2O or S;
RA,R1,R2each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents RA,R1And R2Can optionally be linked to form a ring.
In this example, in formulae 1a-1 to 1a-6, A1-A10Selected, identically or differently at each occurrence, from C, CRAOr N; and A is1-A10Is C, and is linked to a structure represented by formula 1C, intended to represent:
in the formulae 1a-1 and 1a-4, A3-A10Selected, identically or differently at each occurrence, from C, CRAOr N; and A is3-A10Is C and is linked to a structure represented by formula 1C;
in the formulae 1a-2 and 1a-5, A1And A4-A10Selected, identically or differently at each occurrence, from C, CRAOr N; and A is1And A4-A10Is C and is linked to a structure represented by formula 1C;
in formulae 1a-3 and 1a-6, A1-A2And A5-A10Selected, identically or differently at each occurrence, from C, CRAOr N; and A is1-A2And A5-A10Is C, and is linked to a structure represented by formula 1C.
According to one embodiment of the invention, V in the formulas 1a-1 to 1a-6 is selected from O or S.
According to one embodiment of the present invention, V in the formulas 1a-1 to 1a-6 is O.
According to one embodiment of the invention, wherein R isA,R1And R2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof.
According to one embodiment of the invention, wherein R isA,R1And R2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, phenylpyridinyl, and combinations thereof.
According to an embodiment of the present invention, wherein Ar in formula 1c has a structure represented by one of formulae 1c-1 to 1 c-3:
Figure BDA0002856206100000111
wherein the content of the first and second substances,
in the formula 1c-1, B1-B6Selected from C, CR, the same or different at each occurrenceBOr N;
in the formula 1c-2, B1-B8Selected from C, CR, the same or different at each occurrenceBOr N;
in formula 1c-3, B1-B8Selected from C, CR, the same or different at each occurrenceBOr N; g is selected from CRgRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different;
RB,Rgeach 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 arylsilane groups having 6 to 20 carbon atoms, and combinations thereof;
"means" indicates the position at which the Ar structure is attached to the L in formula 1 c;
adjacent substituents RBAnd RgCan optionally be linked to form a ring.
In this context, adjacent substituents RBAnd RgCan optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents RBIn between, two substituents RgAnd a substituent RBAnd RgAnd any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to an embodiment of the present invention, wherein Ar in formula 1c has a structure represented by one of formulae 1c-11 to 1 c-20:
Figure BDA0002856206100000112
in formulae 1c-11 to 1c-20, B1-BnSelected from CR, identically or differently at each occurrenceBOr N; b is describednCorresponding to the B1-B12The largest of the numbers present in any of formulae 1c-11 to 1c-20, G is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different;
RB,Rgeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 20 carbon atoms, or substituted or unsubstituted aryl having 2 to 20 carbon atomsAlkylsilyl of carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;
"means" indicates the position at which the Ar structure is attached to the L in formula 1 c;
adjacent substituents RBAnd RgCan optionally be linked to form a ring.
Herein, in the formulae 1c-11 to 1c-20, B1-BnSelected from CR, identically or differently at each occurrenceBOr N; b isnCorresponding to said B1-B12The largest of the numbers present in any of formulae 1c-11 to 1c-20, G is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgWhich may be the same or different, are intended to mean:
in the formula 1c-11, B1-B5Selected from CR, identically or differently at each occurrenceBOr N;
in formula 1c-12, B1And B3-B8Selected from CR, identically or differently at each occurrenceBOr N;
in the formula 1c-13, B2-B8Is selected, identically or differently on each occurrence, from CRBOr N;
in formulae 1c-14 and 1c-15, B1And B3-B12Selected from CR, identically or differently at each occurrenceBOr N;
in the formula 1c-16, B1-B4,B7-B12Selected from CR, identically or differently at each occurrenceBOr N;
in the formula 1c-17, B2-B8Is selected, identically or differently on each occurrence, from CRBOr N; g is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different;
in the formula 1c-18, B1,B3-B8Selected from CR, identically or differently at each occurrenceBOr N; g is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different;
in the formulae 1c-19, B1-B2,B4-B8Selected from CR, identically or differently at each occurrenceBOr N; g is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different;
in the formula 1c-20, B1-B3And B5-B8Is selected, identically or differently on each occurrence, from CRBOr N; g is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different.
According to one embodiment of the present invention, in the formula 1c-11, B1、B3、B5At least one of which is N and the others are each independently selected from CRBOr N; b in formulae 1c-12 to 1c-201-BnAt least one of them is N, said BnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-11 to 1c-20, and the others are independently selected from CRBOr N.
In formula 1c-11, B according to one embodiment of the present invention1、B3、B5Two or three of them are N, the others are each independently selected from CRBOr N; b in formulae 1c-12 to 1c-201-BnAt least two of which are N, said BnCorresponding to the B1-B12Present in any one of formula 1c-11 to formula 1c-20The others are independently selected from CRBOr N.
According to one embodiment of the invention, wherein R isBEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof.
According to one embodiment of the invention, wherein R isBEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridinyl, phenylpyridinyl, and combinations thereof.
According to one embodiment of the present invention, wherein B in the formulas 1c-11 to 1c-201-BnAt least one is CRBSaid B isnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-11 to 1c-20, and RBSelected from the group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof.
According to an embodiment of the present invention, wherein B in the formulas 1c-11 to 1c-201-BnAt least one is CRBSaid B isnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-11 to 1c-20, and RBSelected from the group consisting of: deuterium, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothienyl, triphenylene,carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridinyl, phenylpyridinyl, and combinations thereof.
According to an embodiment of the present invention, wherein Ar in formula 1c is selected from the group consisting of Ar-1 to Ar-78, wherein the specific structures of Ar-1 to Ar-78 are shown in claim 9.
According to one embodiment of the present invention, wherein, optionally, the hydrogen energy in the structure of Ar-1 to Ar-78 is partially or completely substituted with deuterium.
According to one embodiment of the invention, wherein L is selected from the group consisting of: a single bond, a substituted or unsubstituted arylene group of 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group of 3 to 18 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene, thienylene, dibenzofuranylene, dibenzothiophenylene, and combinations thereof.
According to one embodiment of the invention, the first compound is selected from the group consisting of E-1 to E-91, wherein the specific structure of E-1 to E-91 is shown in claim 11.
According to one embodiment of the invention, wherein the hydrogen energy in the structure of the compounds E-1 to E-91 is partially or completely substituted by deuterium.
According to an embodiment of the present invention, wherein in said formula 2, Y1-Y6Is selected, identically or differently on each occurrence, from CRy1、CRy2Or N, Y1-Y6At least one of them is selected from CRy2And said R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Rs1,Rs2,Rs3each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atomsSubstituted 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, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
L1selected from 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, or a combination thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring.
In this context, adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring, is intended to mean for the adjacent substituent group, for example, substituent Rs1And Rs2Of a substituent Rs1And Rs3And a substituent Rs2And Rs3And any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring. Any adjacent substituent Ry1Are not connected to form a ring.
According to an embodiment of the present invention, wherein, in formula 2, X1-X4Two of which are adjacent to each other are C, and one of the C is bonded to the metal through a carbon-metal bond, X1-X4The one in ortho position to the carbon-metal bond is selected from CRxAnd R isXSelected from deuterium, halogen, substituted or unsubstituted with 1-20 carbonsAn alkyl group of atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms.
In this embodiment, X1-X4Two of which are adjacent to each other are C, and one of said C is bonded to said metal through a carbon-metal bond, when X is1-X4The one in the ortho position to the carbon-metal bond is selected from CRxAnd said R isxSelected from the group of substituents. For example, when said X is1Is C, X2Is also C and forms a carbon-metal bond with the metal, then L isaHas the advantages of
Figure BDA0002856206100000141
In this case, X1-X4The one in the ortho position to the carbon-metal bond in question is X3,X3Selected from the group consisting of CRxAnd said R isxSelected from the group of substituents. Then, for example, X in said formula 12Is C, X1Is also C and forms a carbon-metal bond with the metal, then said LaHas the advantages of
Figure BDA0002856206100000142
Structure of (1), then X1-X4The ortho position in which the carbon-metal bond is not present may be substituted, which is clearly not the case in the present example.
According to an embodiment of the present invention, wherein, in formula 2, X1-X8And Y1-Y6At least one of them is selected from CRxOr CRy1(ii) a And said R isx,Ry1Each occurrence, the same or different, is selected from the group consisting of: deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having from 0 to 20 carbon atoms.
In this embodiment, X1-X8And Y1-Y6At least one of them is selected from CRxOr CRy1Is referred to as X1-X8At least one of them is selected from CRxOr Y1-Y6At least one of them is selected from CRy1And said R isx,Ry1Each occurrence, identically or differently, is selected from the group of substituents described as being other than hydrogen.
According to an embodiment of the present invention, wherein, in formula 2, X1-X8And Y1-Y6At least two or three of them are selected from CRxAnd/or CRy1(ii) a And said R isx,Ry1Each occurrence, the same or different, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl havingA cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
In this embodiment, X1-X8And Y1-Y6At least two or three of them are selected from CRxAnd/or CRy1Is referred to as X1-X8And Y1-Y6At least comprises any one or more of the following: (1) x1-X8At least two of which are selected from CRx;(2)Y1-Y6At least two of which are selected from CRy1;(3)X1-X8At least two of which are selected from CRxAnd Y is1-Y6At least one of them is selected from CRy1;(4)X1-X8At least one of them is selected from CRxAnd Y is1-Y6At least two of which are selected from CRy1;(5)X1-X8At least three of them are selected from CRx;(6)Y1-Y6At least three of them are selected from CRy1;(7)X1-X8At least one of them is selected from CRxAnd Y is1-Y6At least one of them is selected from CRy1. And in any of the above cases, said Rx,Ry1Each occurrence is selected, identically or differently, from the group of substituents which are not hydrogen.
According to an embodiment of the invention, wherein, theIn the second compound, the LaHas a structure represented by formula 4:
Figure BDA0002856206100000151
wherein the content of the first and second substances,
z is selected from O or S;
X3-X8selected from CR, identically or differently at each occurrencexOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; wherein Y is1-Y6At least one of them is selected from CRy2And said R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
L1selected from the group consisting of single bonds, substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted alkylene groups having 3 to 20 carbon atomsCycloalkylene, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms, and combinations thereof;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring.
According to an embodiment of the invention, wherein the second compound has M (L)a)m(Lb)n(Lc)qThe structure of (1);
wherein, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
La、Lband LcA first ligand, a second ligand and a third ligand, respectively, of the complex; 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 greater than 1, a plurality of LaMay be the same or different; when n is 2, two LbWhich may be the same or different, when q is 2, two LcMay be the same or different;
La、Lband LcOptionally linked to form a multidentate ligand;
Lband LcEach occurrence, the same or different, is selected from the group consisting of:
Figure BDA0002856206100000161
wherein R isa、RbAnd RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1And CRC1RC2
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2
Ra、Rb、Rc、RN1、RN2、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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Ra、Rb、Rc、RN1、RN2、RC1And RC2Can optionally be linked to form a ring.
In this example, the adjacent substituents Ra、Rb、Rc、RN1、RN2、RC1And RC2Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf R is a substituentaAnd RcOf a substituent RbAnd RcOf R is a substituentaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of a substituent RaAnd RC2Of R is a substituentbAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RN2Of a substituent RbAnd RN2And R isC1And RC2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
In this embodiment, La、LbAnd LcCan optionally be linked to form a multidentate ligand, intended to denote La、LbAnd LcOptionally linked to form a tetradentate or hexadentate ligand. Obviously, La、LbAnd LcOr may be both unconnected to form a multidentate ligand.
According to an embodiment of the invention, wherein the second compound has M (L)a)m(Lb)n(Lc)qThe structure of (1);
wherein, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
La、Lband LcA first ligand, a second ligand and a third ligand, respectively, of the complex; 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 greater than 1, a plurality of LaMay be the same or different; when n is 2, two LbWhich may be the same or different, when q is 2, two LcMay be the same or different; l isa、LbAnd LcOptionally linked to form a multidentate ligand;
wherein L isbEach occurrence, identically or differently, is selected from the following structures:
Figure BDA0002856206100000171
Xcand XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2
Ra1、Rb1、Rc1、RN2Each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Ra1、Rb1、Rc1Can optionally be linked to form a ring;
Lceach occurrence, the same or different, is selected from the group consisting of:
Figure BDA0002856206100000172
Ra、Rb、Rcthe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xeeach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN3
Ra、Rb、Rc、RN3Each 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 heterocycle having 3 to 20 ring atomsA group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Ra、Rb、RcCan optionally be linked to form a ring.
In this example, the adjacent substituents Ra1、Rb1、Rc1Can optionally be linked to form a ring, intended to represent a substituent Ra1And Rc1Or a substituent Rb1And Rc1Can be connected to form a ring. It is obvious that the substituent Ra1And Rc1Or a substituent Rb1And Rc1May not be connected to form a ring.
In this example, the adjacent substituents Ra、Rb、RcCan optionally be linked to form a ring, intended to denote when a plurality of substituents R are presentaA plurality of substituents RbA plurality of substituents RcWhen adjacent substituent RaAdjacent and adjacent substituents RbMeta or adjacent substituents RcCan be connected to form a ring. It will be apparent that when a plurality of substituents R are presentbA plurality of substituents RcWhen adjacent substituent RaAdjacent and adjacent substituents RbWith adjacent or adjacent substituents RcMay not be connected to form a ring.
According to an embodiment of the present invention, wherein the second compound has a structure represented by formula 5:
Figure BDA0002856206100000181
wherein the content of the first and second substances,
m is 1 or 2;
z is selected, identically or differently on each occurrence, from O or S; preferably, Z is O;
X3-X8selected from CR, identically or differently at each occurrencexOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; wherein Y is1-Y6At least one of them is selected from CRy2And said R isy2Having a radical of formula-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3,R11,R12,R13,R14,R15,R16,R17each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
L1selected from the group consisting of single bonds,substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene groups having 3 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, and combinations thereof;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring;
adjacent substituents R11,R12,R13,R14,R15,R16,R17Can optionally be linked to form a ring.
In this example, the adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring, intended to denote an adjacent substituent group therein, e.g. two substituents RxOf a substituent Rs1And Rs2Of a substituent Rs1And Rs3And a substituent Rs2And Rs3Any one or more of these substituent groups can be linked to form a ring. Obviously, these substituent groups may not be connected to form a ring.
In this context, adjacent substituents R11,R12,R13,R14,R15,R16,R17Can optionally be linked to form a ring, is intended to mean an adjacent substituent group therein, e.g. substituent R11And R12Of a substituent R11And R13Of a substituent R12And R13Of a substituent R14And R15Of a substituent R15And R16Of a substituent R14And R16Of a substituent R11And R17Of a substituent R12And R17Of a substituent R13And R17Of a substituent R14And R17Of a substituent R15And R17And a substituent R16And R17Of one or more of these substituent groupsAre linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.
According to one embodiment of the invention, wherein R11-R13At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R14-R16At least one 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 heteroalkyl group having 1 to 20 carbon atoms, or combinations thereof;
adjacent substituents R11,R12,R13,R14,R15,R16,R17Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein R11-R13At least two of which are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R14-R16At least two of which are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof;
adjacent substituents R11,R12,R13,R14,R15,R16,R17Can optionally be linked to form a ring.
According to one embodiment of the present invention, wherein Y1-Y6Each independently selected from CRy1Or CRy2
According to one embodiment of the present invention, wherein Y1-Y6At least one of which is selected from N.
According to one embodiment of the invention, wherein Z is O.
According to one embodiment of the present invention, wherein X3-X8At least one of which is selected from N.
According to one embodiment of the present invention, wherein X3-X8One of them is selected from N
According to one embodiment of the present invention, wherein X8Is N.
According to one embodiment of the present invention, wherein X3-X8Each independently selected from CRx
According to one embodiment of the present invention, wherein X3-X8Each independently selected from CRxSaid R isxSelected 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 alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano, or combinations thereof.
According to one embodiment of the present invention, wherein X3-X8Each independently selected from CRxSaid R isxSelected from the group consisting of: hydrogen, deuterium, fluoro, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, and combinations thereof.
According to an embodiment of the invention, wherein X3Selected from the group consisting of CRxAnd said R isxSelected 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 alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano, or combinations thereof.
According to an embodiment of the invention, wherein X3Selected from the group consisting of CRxAnd said R isxSelected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 2Cycloalkyl of 0 ring carbon atoms, cyano, or a combination thereof.
According to an embodiment of the invention, wherein X3Selected from the group consisting of CRxAnd said R isxSelected from methyl or deuterated methyl.
According to an embodiment of the invention, wherein Y1-Y2Selected from CR, identically or differently at each occurrencey1Or N; y is3-Y6Selected from CR, identically or differently at each occurrencey1、CRy2Or N, and Y3-Y6At least one of which is selected from CRy2Said R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Ry1each 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 aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Rs1,Rs2,Rs3each 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 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 aralkyl having 3 to 20 carbon atomsAlkenyl 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, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
L1selected from 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, or a combination thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring.
In this context, adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring, is intended to mean for the adjacent substituent group, for example, substituent Rs1And Rs2Of a substituent Rs1And Rs3And a substituent Rs2And Rs3Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these substituent groups may not be connected to form a ring. Any adjacent substituent Ry1Are not connected to form a ring.
According to an embodiment of the invention, wherein Y1-Y2Is selected, identically or differently on each occurrence, from CRy1Or N; ry1Each 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 aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy having 6 to 30 carbon atomsAn aryloxy group of 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and when said R isy1Selected from the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, 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, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
According to one embodiment of the invention, wherein Rs1,Rs2,Rs3Each 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 cycloalkyl having 1 to 20 carbon atoms, or substituted or unsubstituted heteroalkyl having two or more carbon atomsAn 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 hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring.
According to an embodiment of the invention, wherein Y1-Y2Selected from CR, identically or differently at each occurrencey1Or N; y is3-Y6Selected from CR, identically or differently at each occurrencey1、CRy2Or N, and Y3-Y6At least one of them is selected from CRy2And said R isy2Having the formula-L-SiRs1Rs2Rs3The structure of (1);
Ry1each 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 aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Rs1,Rs2,Rs3each occurrence, the same or different, is selected from the group consisting of: 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 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, and combinations thereof;
l is selected from 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, or a combination thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring.
According to an embodiment of the invention, wherein Y2Selected from the group consisting of CRy1Or CRy2(ii) a The R isy1Selected 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; the R isy2has-L1-SiRs1Rs2Rs3The structure of (1); rs1,Rs2,Rs3Each 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 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 aryloxy having 2 to 20 carbon atomsSubstituted 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, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; l is1Selected from 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, or a combination thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring.
According to one embodiment of the present invention, wherein Y1-Y6Each independently selected from CRy1Or CRy2And Y is1-Y6At least one of which is selected from CRy2Said R isy2has-L1-SiRs1Rs2Rs3In which L is1Selected from single bonds, Rs1、Rs2And Rs3Each independently selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and combinations thereof; and R iss1、Rs2And Rs3At least one or two of which are each independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof.
According to one embodiment of the present invention, wherein Y2And Y4At least one of CR is selected fromy2Said R isy2has-L1-SiRs1Rs2Rs3Structure of (1), wherein L1Selected from single bonds, Rs1、Rs2And Rs3Each independently selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and combinations thereof; and R iss1、Rs2And Rs3At least one or two of which are each independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof.
According to one embodiment of the present invention, wherein Y2Or Y4Selected from the group consisting of CRy2Said R isy2has-L1-SiRs1Rs2Rs3In which L is1Selected from single bonds, Rs1、Rs2And Rs3Each independently selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and combinations thereof; and R iss1、Rs2And Rs3At least one or two of which are each independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof.
According to an embodiment of the invention, wherein Y1-Y6Each independently selected from CRy1Or CRy2And Y is3-Y6At least one of which is selected from CRy2Said R isy2has-L1-SiRs1Rs2Rs3In which L is1Selected from single bonds, Rs1、Rs2And Rs3Each independently selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and combinations thereof; and R iss1、Rs2And Rs3At least one or two of which are each independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms,substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein Rs1、Rs2And Rs3Each independently selected from the group consisting of: methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trifluoromethyl, phenyl, and combinations thereof.
According to an embodiment of the present invention, wherein LaEach occurrence being selected identically or differently from La1To La319The group consisting ofa1To La319See claim 24 for specific structure of (a).
According to an embodiment of the present invention, wherein LbEach occurrence being selected identically or differently from Lb1To Lb322Group of (I), LcEach occurrence being selected identically or differently from Lc1To Lc231A group of (a); said Lb1To Lb322And Lc1To Lc231See claim 25 for specific structure of (a).
According to one embodiment of the invention, wherein the second compound has Ir (L)a)2(Lb) Or Ir (L)a)2(Lc) Or Ir (L)a)(Lc)2The structure of (1); wherein when the second compound has Ir (L)a)2(Lb) In the structure of (1), LaEach occurrence being selected identically or differently from La1To La319Any one or any two of the group consisting of, LbIs selected from the group consisting of Lb1To Lb322Any one of the group consisting of; when the second compound has Ir (L)a)2(Lc) In the structure of (1), LaEach occurrence being selected identically or differently from La1To La319Any one or any two of the group consisting of, LcIs selected from the group consisting of Lc1To Lc231Any one of the group consisting of; when the second compound has Ir (L)a)(Lc)2In the structure of (1), LaIs selected from the group consisting of La1To La319Any one of the group consisting of LcEach occurrence, identically or differently, of a group selected from Lc1To Lc231Any one or any two of the group consisting of.
According to one embodiment of the present invention, wherein the second compound is selected from the group consisting of compound 1 to compound 616, and the specific structures of compound 1 to compound 616 are shown in claim 26.
According to an embodiment of the present invention, wherein the organic layer is a light emitting layer, the first compound is a host material, and the second compound is a light emitting material.
According to one embodiment of the invention, wherein the device emits red or white light.
According to an embodiment of the present invention, wherein the organic layer further includes a third compound having a structure as shown in any one of formulas 3-1 to 3-3:
Figure BDA0002856206100000231
in formulae 3-1 to 3-3, Ar31To Ar35Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
L31to L35Each 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;
x is selected, identically or differently on each occurrence, from CRx1Rx2、NRx3O or S;
R31-R37the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31-R37、Rx1-Rx3each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R31-R37Can optionally be linked to form a ring.
In this example, the adjacent substituents R31-R37Can optionally be linked to form a ring, are intended to mean wherein adjacent groups of substituents, for example, adjacent substituents R31Between, adjacent substituents R32Between, adjacent substituents R33Between, adjacent substituents R31And R32Adjacent substituents R32And R33Adjacent substituents R34Between, adjacent substituents R35Adjacent substituents R36Between, adjacent substituents R37Between, adjacent substituents R34And R35Between, adjacent substituents R35And R36And adjacent substituents R36And R37Any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, none of these adjacent substituent groups may be linked to form a ring.
According to an embodiment of the present invention, wherein the organic layer is a light emitting layer, and the third compound is a host material.
According to an embodiment of the present invention, wherein, in formula 3-1, adjacent substituents R31、R32、R33At least one group of the groups is connected to form a ring.
According to an embodiment of the present invention, wherein, in formula 3-1, adjacent substituents R31、R32、R33At least one group of the two groups is connected to form a ring, and the formed ring at least comprises 1 six-membered ring.
According to an embodiment of the present invention, wherein the third compound has a structure represented by one of formulas 3-11 to 3-21:
Figure BDA0002856206100000232
Figure BDA0002856206100000241
wherein, in formulae 3-11 to 3-21,
Ar31each occurrence, identically or differently, is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
L31each 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;
x is selected, identically or differently on each occurrence, from CRx1Rx2、NRx3O or S;
R31、R32、R33、R38the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31、R32、R33、R38、Rx1-Rx3the occurrences being the same or different selected from the group consisting of: hydrogen, deuterium, halogen, substituted or notA substituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
adjacent substituents R31、R32、R33、R38Can optionally be linked to form a ring.
In this example, the adjacent substituents R31、R32、R33、R38Can optionally be linked to form a ring is intended to mean where adjacent groups of substituents, e.g. adjacent substituents R31Between, adjacent substituents R32Adjacent substituents R33Adjacent substituents R31And R32Adjacent substituents R32And R33Between, adjacent substituents R31And R38Adjacent substituents R32And R38And adjacent substituents R33And R38And any one or more of these adjacent substituent groups can be linked to form a ring. Obviously, these adjacent substituent groups may not be connected to form a ring.
According to an embodiment of the present invention, wherein, in formulae 3-11 to 3-21, R is31-R38Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy,a mercapto group, a substituted or unsubstituted alkyl group having 1 to 20 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, and combinations thereof;
said L31Each occurrence, the same or different, is selected from the group consisting of: a single bond, substituted or unsubstituted arylene of 6 to 18 carbon atoms, substituted or unsubstituted heteroarylene of 3 to 18 carbon atoms, and combinations thereof;
ar is31、Rx1-Rx3Each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-11 to 3-21, R is31-R38Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, phenylpyridinyl, and combinations thereof;
said L is31Selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene, thienylene, dibenzofuranylene, dibenzothiophenylene, and combinations thereof;
ar is31、Rx1-Rx3Each occurrence, the same or different, is selected from the group consisting of: phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, trideuteromethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.
According to one embodiment of the inventionWherein, in formulae 3-1 to 3-3, the R31-R37Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof;
said L31To L35Each occurrence, the same or different, is selected from the group consisting of: a single bond, substituted or unsubstituted arylene of 6 to 18 carbon atoms, substituted or unsubstituted heteroarylene of 3 to 18 carbon atoms, and combinations thereof;
ar is31To Ar35、Rx1-Rx3Each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 3-1 to 3-3, R is31-R37Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, phenylpyridinyl, and combinations thereof;
said L31To L35Selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene, thienylene, dibenzofuranylene, dibenzothiophenylene, and combinations thereof;
ar is31To Ar35、Rx1-Rx3Each occurrence, the same or different, is selected from the group consisting of: phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, trideuteromethylphenyl, biphenyl, naphthyl, deuteratedNaphthyl, dibenzofuranyl, dibenzothienyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.
According to one embodiment of the present invention, wherein the third compound is selected from the group consisting of compound H-1 to compound H-136, and the specific structures of the compound H-1 to compound H-136 are shown in claim 31.
According to one embodiment of the present invention, wherein the hydrogen energy in the structures of said compound H-1 to compound H-136 is partially or completely substituted by deuterium.
According to one embodiment of the present invention, a display assembly is disclosed that includes an electroluminescent device having a specific structure as shown in any of the foregoing embodiments.
According to an embodiment of the invention, a combination of compounds is also disclosed, wherein at least the first compound and the second compound are included.
In this embodiment, the first compound and the second compound may be further selected from the structures described in any of the preceding embodiments.
According to an embodiment of the invention, wherein the combination of compounds further comprises a third compound having a structure as shown in any one of the preceding.
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. 0161 (paragraph 0132-0161) of US2016/0359122A1, 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 useful for particular layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. For example, the compound combinations disclosed herein may be used in conjunction with a variety of light emitting dopants, hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application 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.
The preparation methods of the first compound, the second compound and the third compound are not limited, and can be obtained commercially by those skilled in the art, or can be obtained easily by referring to the preparation methods in the prior art, or can be obtained by referring to patent applications with application numbers of US16481644, US15770215 and CN2020114924937, and are not described herein again.
The method of fabricating the electroluminescent device is not limited, and the method of fabricating the following examples is only an example and should not be construed as limiting. 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 each material in the light-emitting layer is not particularly limited, and those skilled in the art can reasonably select the material within a certain range according to the prior art, for example, the host material may account for 80% to 99% and the light-emitting material may account for 1% to 20% based on the total weight of the light-emitting layer material; or the main material can account for 90% -99%, and the luminescent material can account for 1% -10%. In addition, the host material may be one or two materials, wherein the proportion of the two host materials in the host material may be 100: 0 to 1: 99; alternatively, the ratio may be 80: 20 to 20: 80; alternatively, the ratio may be 60: 40 to 40: 60. in an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, 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.
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 120nm thick, was cleaned and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was dried in a glove box filled with nitrogen gas to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of Torr
Figure BDA0002856206100000261
Figure BDA0002856206100000262
The rate of (a) was successively evaporated on the ITO anode by thermal vacuum. Compound HI was used as a Hole Injection Layer (HIL) with a thickness of
Figure BDA0002856206100000263
The compound HT is used as Hole Transport Layer (HTL) with a thickness of
Figure BDA0002856206100000264
Compound EB was used as an Electron Blocking Layer (EBL) with a thickness of
Figure BDA0002856206100000265
Then, the compound E-9 as a first host, the compound H-35 as a second host, and the compound 250 as a dopant were co-evaporated to be used as an emission layer (EML) with a thickness of
Figure BDA0002856206100000266
The compound HB was used as a hole-blocking layer (HBL) with a thickness of
Figure BDA0002856206100000267
On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron-transporting layer (ETL) with a thickness of
Figure BDA0002856206100000268
Finally, evaporation
Figure BDA0002856206100000269
8-hydroxyquinoline-lithium (Liq) as an Electron Injection Layer (EIL) in thickness and evaporation deposited
Figure BDA00028562061000002610
As a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
Device example 2
Device example 2 was implemented in the same manner as device example 1 except that the compound 182 was used as a dopant instead of the compound 250 in the light emitting layer (EML).
Device example 3
Device example 2 was implemented in the same manner as device example 1, except that the compound 323 was used as a dopant instead of the compound 250 in the light emitting layer (EML).
Device example 4
Device example 2 was implemented in the same manner as device example 1, except that the compound 360 was used as a dopant instead of the compound 250 in the light emitting layer (EML).
Device example 5
Device example 5 was implemented in the same manner as device example 1, except that compound 484 was used as a dopant in place of compound 250 in the light emitting layer (EML).
Device comparative example 1
Device comparative example 1 was conducted in the same manner as in device example 1 except that the compound RH-a was used as a host instead of the compound E-9 and the compound H-35 in the light-emitting layer (EML) and the compound 484 was used as a dopant instead of the compound 250 (the weight ratio of the compound RH-a to the compound 484 was 98: 2).
Device comparative example 2
Device comparative example 2 was conducted in the same manner as in device example 1 except that the compound RH-a was used as a host in place of the compound E-9 and the compound H-35 in the light-emitting layer (EML) (the weight ratio of the compound RH-a to the compound 250 was 98: 2).
Device comparative example 3
Device comparative example 3 was implemented in the same manner as device example 2 except that the compound RH-a was used instead of the compound E-9 and the compound H-35 as a host in the light-emitting layer (EML) (the weight ratio of the compound RH-a to the compound 182 was 98: 2).
Device comparative example 4
Device comparative example 4 was conducted in the same manner as in device example 3 except that the compound RH-a was used as a host in place of the compound E-9 and the compound H-35 in the light-emitting layer (EML) (the weight ratio of the compound RH-a to the compound 323 was 98: 2).
Device comparative example 5
Device comparative example 5 was implemented in the same manner as in device example 4 except that the compound RH-a was used as a host in place of the compound E-9 and the compound H-35 in the light emitting layer (EML) (the weight ratio of the compound RH-a to the compound 360 was 98: 2).
The device layer structures and thicknesses are shown in the table below. Wherein more than one of the materials used is obtained by doping different compounds in the recited weight ratios.
TABLE 1 device structures of device examples and comparative examples
Figure BDA0002856206100000271
Figure BDA0002856206100000281
The material structure used in the device is as follows:
Figure BDA0002856206100000282
Figure BDA0002856206100000291
the IVL characteristics of the device were measured. Table 2 shows the results at 15mA/cm2Voltage (V) and External Quantum Efficiency (EQE) data measured at current density.
TABLE 2 device data
Device numbering Voltage(V) EQE(%)
Example 1 3.45 26.19
Example 2 3.97 24.50
Example 3 3.63 23.94
Example 4 3.56 26.68
Example 5 3.50 22.86
Comparative example 1 3.94 19.65
Comparative example 2 4.11 22.81
Comparative example 3 3.81 20.14
Comparative example 4 4.01 20.85
Comparative example 5 4.34 25.14
In table 2, the comparison of the data of examples 1 to 4 and comparative examples 2 to 5 shows that the high EQE level of the examples is greatly improved to a very high level, which fully shows the excellent characteristics of the combination of the host compound and the light emitting dopant compound selected in the present invention, such that the EQE can be significantly improved. In addition, the comparison of the voltage data of examples 1 to 4 and comparative examples 2 to 5 also fully demonstrates the low voltage advantage of the combination of the first and second compounds of the present invention. In addition, as can be seen from the comparison of example 5 and comparative example 1, the EQE increase amplitude of example 5 is also as high as 16.2%, and example 5 also has a lower voltage than comparative example 1. This result again confirms the unique advantage of the combination of the first and second compounds selected in the present invention that can bring about the significant increase and decrease in voltage of the EQE. These results show that the combination of the first compound and the second compound of the present invention can achieve a large improvement in device performance, demonstrating the superiority of the combination of the first compound and the second compound of the present invention.
In summary, the combination of the first compound and the second compound disclosed by the invention can show excellent comprehensive device performance in the device, such as lower driving voltage, higher efficiency and good commercial development potential, because the two compounds can be well matched with each other in terms of energy.
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 (33)

1. An electroluminescent device, comprising:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound;
the first compound has a structure represented by formula 1 a:
Figure FDA0002856206090000011
in the case of the formula 1a,
A1-A10each independently selected from C, CRAOr N; and A is1-A103 of (a) is C; wherein 2C are adjacent and are connected to the structure represented by formula 1 b; another C is linked to a structure represented by formula 1C:
Figure FDA0002856206090000012
respectively representing the position of the connection of the formula 1b and the formula 1a, and the position of the connection of the formula 1c and the formula 1 a;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
v is selected from NR2O or S;
RA,R1,R2each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents RA,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex and comprises a ligand L coordinated with the metalaAnd the metal is selected from metals having a relative atomic mass greater than 40; l is a radical of an alcoholaHas a structure represented by formula 2:
Figure FDA0002856206090000013
in formula 2, Z is selected from O, S or Se;
X1-X8selected, identically or differently at each occurrence, from C, CRxOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; the R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
L1selected from 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, or a combination thereof;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring.
2. The electroluminescent device of claim 1, wherein the first compound has a structure represented by one of formulas 1a-1 to 1 a-6:
Figure FDA0002856206090000021
in formulae 1a-1 to 1a-6,
A1-A10selected, identically or differently at each occurrence, from C, CRAOr N; and A is1-A10Is C and is linked to a structure represented by formula 1C, formula 1C being as described in claim 1;
v is selected from NR2O or S;
RA,R1,R2each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents RA,R1And R2Can optionally be linked to form a ring.
3. An electroluminescent device as claimed in claim 2 wherein V in formulae 1a-1 to 1a-6 is selected from O or S;
preferably, V in the formulas 1a-1 to 1a-6 is O.
4. An electroluminescent device as claimed in any one of claims 1 to 3 wherein R isA,R1And R2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof;
preferably, wherein R isA,R1And R2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, hydroxyl, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, phenylpyridinyl, and combinations thereof.
5. The electroluminescent device of any one of claims 1-4, wherein Ar in formula 1c has a structure represented by one of formulae 1c-1 to 1 c-3:
Figure FDA0002856206090000031
wherein the content of the first and second substances,
in the formula 1c-1, B1-B6Selected from C, CR, the same or different at each occurrenceBOr N;
in the formula 1c-2, B1-B8Each occurrence of the same or different is selected from C, CRBOr N;
in formula 1c-3, B1-B8Selected from C, CR, the same or different at each occurrenceBOr N; g is selected from CRgRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two R are simultaneously presentgWhen two R are presentgMay be the same or different;
RB,Rgeach 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 arylsilane groups having 6 to 20 carbon atoms, and combinations thereof;
"means" indicates the position at which the Ar structure is attached to the L in formula 1 c;
adjacent substituents RBAnd RgCan optionally be linked to form a ring.
6. The electroluminescent device of claim 5, wherein Ar in formula 1c has a structure represented by one of formulae 1c-11 to 1 c-20:
Figure FDA0002856206090000032
in formulae 1c-11 to 1c-20, B1-BnSelected from CR, identically or differently at each occurrenceBOr N; b isnCorresponding to said B1-B12The largest of the numbers present in any of formulae 1c-11 to 1c-20, G is selected from CR, the same or different at each occurrencegRg,SiRgRg,NRg,BRg,PRgO, S or Se; when two exist at the same timeR isgWhen two R are presentgMay be the same or different;
RB,Rgeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane groups having 6 to 20 carbon atoms, and combinations thereof;
"means" indicates the position at which the Ar structure is attached to the L in formula 1 c;
adjacent substituents RBAnd RgCan optionally be linked to form a ring;
preferably, in formula 1c-11, B1、B3、B5At least one of which is N and the others are each independently selected from CRBOr N; b in formulae 1c-12 to 1c-201-BnAt least one of them is N, said BnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-12 to 1c-20, and the others are independently selected from CRBOr N;
more preferably, in formula 1c-11, B1、B3、B5Two or three of them are N, the others are each independently selected from CRB(ii) a B in formulae 1c-12 to 1c-201-BnAt least two of which are N, said BnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-12 to 1c-20, and the others are independently selected from CRB
7. The electroluminescent device of claim 6, wherein RBEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof;
preferably, wherein R isBEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridinyl, phenylpyridinyl, and combinations thereof.
8. The electroluminescent device as claimed in claim 6 or 7, wherein B in the formulae 1c-11 to 1c-201-BnAt least one is CRBSaid B isnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-11 to 1c-20, and RBSelected from the group consisting of: deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof;
preferably, wherein B in said formula 1c-11 to formula 1c-201-BnAt least one is CRBSaid B isnCorresponding to the B1-B12The largest number among the groups represented by any one of the formulae 1c-11 to 1c-20, and RBSelected from the group consisting of: deuterium, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridylPhenylpyridyl, and combinations thereof.
9. The electroluminescent device of any one of claims 1-8, wherein said Ar is selected from the group consisting of the following structures:
Figure FDA0002856206090000041
Figure FDA0002856206090000051
Figure FDA0002856206090000061
Figure FDA0002856206090000071
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
10. The electroluminescent device of any one of claims 1-9, wherein L is selected from the group consisting of: a single bond, substituted or unsubstituted arylene of 6 to 18 carbon atoms, substituted or unsubstituted heteroarylene of 3 to 18 carbon atoms, and combinations thereof;
preferably, wherein said L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene, thienylene, dibenzofuranylene, dibenzothiophenylene, and combinations thereof.
11. The electroluminescent device of any of claims 1-10, wherein the first compound is selected from the group consisting of:
Figure FDA0002856206090000072
Figure FDA0002856206090000081
Figure FDA0002856206090000091
Figure FDA0002856206090000101
Figure FDA0002856206090000111
Figure FDA0002856206090000121
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
12. The electroluminescent device of claim 1, wherein in said formula 2, Y1-Y6Selected from CR, identically or differently at each occurrencey1、CRy2Or N, Y1-Y6At least one of them is selected from CRy2And said R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Rs1,Rs2,Rs3each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 ring carbon atomsA heteroalkyl group of carbon atoms, a substituted or unsubstituted 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 hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L1selected 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, or a combination thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring.
13. The electroluminescent device of claim 1, wherein in formula 2, X1-X4Two of which are adjacent to each other are C, and one of the C is bonded to the metal through a carbon-metal bond, X1-X4The one in the ortho position to the carbon-metal bond is selected from CRxAnd R isXSelected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylUnsubstituted 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, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof.
14. The electroluminescent device of claim 1, wherein in formula 2, X1-X8And Y1-Y6At least one of them is selected from CRxOr CRy1(ii) a And said R isx,Ry1Each occurrence, the same or different, is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
preferably, X1-X8And Y1-Y6At least two or three of them are selected from CRxAnd/or CRy1(ii) a And said R isx,Ry1Each occurrence, the same or different, is 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 unsubstitutedA substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
15. The electroluminescent device of any one of claims 1-14, wherein in the second compound, the LaHas a structure represented by formula 4:
Figure FDA0002856206090000141
wherein the content of the first and second substances,
z is selected from O or S;
X3-X8is selected, identically or differently on each occurrence, from CRxOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; wherein Y is1-Y6At least one of them is selected from CRy2And said R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3each 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, substitutedOr a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L1selected 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;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring.
16. The electroluminescent device of any one of claims 1-15, wherein the second compound has M (L)a)m(Lb)n(Lc)qThe structure of (1);
wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
La、Lband LcA first ligand, a second ligand and a third ligand, respectively, of the complex; 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 greater than 1, a plurality of LaMay be the same or different; when n is 2, two LbWhich may be the same or different, when q is 2, two LcMay be the same or different;
La、Lband LcOptionally linked to form a multidentate ligand;
Lband LcEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0002856206090000142
Figure FDA0002856206090000151
wherein R isa、RbAnd RcThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1And CRC1RC2
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2
Ra、Rb、Rc、RN1、RN2、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, substitutedOr unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
adjacent substituents Ra、Rb、Rc、RN1、RN2、RC1And RC2Can optionally be linked to form a ring.
17. The electroluminescent device of any one of claims 1-15, wherein the second compound has M (L)a)m(Lb)n(Lc)qThe structure of (1);
wherein, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
La、Lband LcA first ligand, a second ligand and a third ligand, respectively, of the complex; 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 greater than 1, a plurality of LaMay be the same or different; when n is 2, two LbWhich may be the same or different, when q is 2, two LcMay be the same or different; l isa、LbAnd LcOptionally linked to form a multidentate ligand;
wherein L isbEach occurrence, identically or differently, is selected from the following structures:
Figure FDA0002856206090000152
Xcand XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2
Ra1、Rb1、Rc1、RN2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 ring carbon atomsA heteroalkyl group of carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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;
adjacent substituents Ra1、Rb1、Rc1Can optionally be linked to form a ring;
Lceach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0002856206090000161
Ra、Rb、Rcthe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Xeeach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN3
Ra、Rb、Rc、RN3Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy having 6 to 30 carbon atomsSubstituted 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, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Ra、Rb、RcCan optionally be linked to form a ring.
18. The electroluminescent device of any one of claims 1-17, wherein the second compound has a structure represented by formula 5:
Figure FDA0002856206090000171
wherein the content of the first and second substances,
m is 1 or 2;
z is selected, identically or differently on each occurrence, from O or S; preferably, Z is O;
X3-X8selected from CR, identically or differently at each occurrencexOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; wherein Y is1-Y6At least one of them is selected from CRy2And said R isy2has-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3,R11,R12,R13,R14,R15,R16,R17each 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 unsubstitutedA substituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
L1selected 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;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring;
adjacent substituents R11,R12,R13,R14,R15,R16,R17Can optionally be linked to form a ring;
preferably, wherein R11-R13At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R14-R16At least one 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 heteroalkyl group having 1 to 20 carbon atoms, or combinations thereof;
more preferably, wherein R11-R13At least two of which are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R14-R16At least two of which are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
19. An electroluminescent device as claimed in any one of claims 14 to 18 in which Y is1-Y6Each independently selected from CRy1Or CRy2
20. An electroluminescent device as claimed in any one of claims 14 to 19 wherein Z is O.
21. An electroluminescent device as claimed in any one of claims 1 to 20 in which Y is1-Y2Selected from CR, identically or differently at each occurrencey1Or N; y is3-Y6Selected from CR, identically or differently at each occurrencey1、CRy2Or N, and Y3-Y6At least one of which is selected from CRy2Said R isy2Having a radical of formula-L1-SiRs1Rs2Rs3The structure of (1);
Ry1each 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 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 atomsOr unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Rs1,Rs2,Rs3each 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 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, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
L1selected 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, or a combination thereof;
adjacent substituents Rs1,Rs2,Rs3Can optionally be linked to form a ring;
preferably, Rs1,Rs2,Rs3Each occurrence, the same or different, is selected from the group consisting of: 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 aryl having 7 to 30 carbon atomsAn alkyl group, 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, and combinations thereof.
22. An electroluminescent device as claimed in any one of claims 1 to 20 in which Y is1-Y6Each independently selected from CRy1Or CRy2And Y is1-Y6At least one of which is selected from CRy2Said R isy2has-L1-SiRs1Rs2Rs3In which L is1Selected from single bonds, Rs1、Rs2And Rs3Each independently selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and combinations thereof; and R iss1、Rs2And Rs3At least one or two of which are each independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, or combinations thereof;
preferably, Y2And Y4At least one of CR is selected fromy2
More preferably, Y2Or Y4Selected from the group consisting of CRy2
23. An electroluminescent device as claimed in claim 21 or 22 in which Rs1、Rs2And Rs3Each independently selected from the group consisting of: methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trifluoromethyl, phenyl, and combinations thereof.
24. An electroluminescent device as claimed in claim 1 in which LaEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0002856206090000191
Figure FDA0002856206090000201
Figure FDA0002856206090000211
Figure FDA0002856206090000221
Figure FDA0002856206090000231
Figure FDA0002856206090000241
Figure FDA0002856206090000251
Figure FDA0002856206090000261
Figure FDA0002856206090000271
Figure FDA0002856206090000281
Figure FDA0002856206090000291
Figure FDA0002856206090000301
Figure FDA0002856206090000311
25. an electroluminescent device as claimed in any one of claims 16 to 24 wherein LbEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0002856206090000312
Figure FDA0002856206090000321
Figure FDA0002856206090000331
Figure FDA0002856206090000341
Figure FDA0002856206090000351
Figure FDA0002856206090000361
Figure FDA0002856206090000371
Figure FDA0002856206090000381
wherein L iscEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0002856206090000382
Figure FDA0002856206090000391
Figure FDA0002856206090000401
Figure FDA0002856206090000411
Figure FDA0002856206090000421
Figure FDA0002856206090000431
26. the electroluminescent device of any of claims 16-25, wherein the second compound has Ir (L)a)2(Lb) Or Ir (L)a)2(Lc) Or Ir (L)a)(Lc)2The structure of (1);
wherein when the second compound has Ir (L)a)2(Lb) In the structure of (1), LaEach occurrence being selected identically or differently from La1To La319Any one or any two of the group consisting of, LbIs selected from the group consisting of Lb1To Lb322Any one of the group consisting of; when the second compound has Ir (L)a)2(Lc) In the structure of (1), LaEach occurrence being selected identically or differently from La1To La319Any one or any two of the group consisting of, LcIs selected from the group consisting of Lc1To Lc231Any one of the group consisting of; when the second compound has Ir (L)a)(Lc)2In the structure of (1), LaIs selected from the group consisting of La1To La319Any one of the group consisting of LcEach occurrence, identically or differently, of a group selected from Lc1To Lc231Any one or any two of the group consisting of;
preferably wherein said second compound is selected from the group consisting of compound 1 to compound 616;
wherein said compound 1 to compound 496 have Ir (L)a)2(Lb) Wherein two L areaSame, LaAnd LbEach corresponding to a structure selected from those listed in the following table:
Figure FDA0002856206090000441
Figure FDA0002856206090000451
Figure FDA0002856206090000461
Figure FDA0002856206090000471
Figure FDA0002856206090000481
wherein compounds 497 to 616 have Ir (L)a)2(Lb) Wherein two L areaDifferent, LaAnd LbRespectively corresponding to the structures listed in the following table:
Figure FDA0002856206090000482
Figure FDA0002856206090000491
27. the electroluminescent device of any of claims 1-26, wherein the organic layer is a light emitting layer, the first compound is a host material, and the second compound is a light emitting material;
preferably, the device emits red or white light.
28. The electroluminescent device of any one of claims 1-27, wherein the organic layer further comprises a third compound having a structure as shown in any one of formulas 3-1 to 3-3:
Figure FDA0002856206090000492
in formulae 3-1 to 3-3, Ar31To Ar35Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
L31to L35Each 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;
x is selected, identically or differently on each occurrence, from CRx1Rx2、NRx3O or S;
R31-R37the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31-R37、Rx1-Rx3each 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 groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents R31-R37Can optionally be linked to form a ring;
preferably, the organic layer is a light emitting layer and the third compound is a host material.
29. The electroluminescent device of claim 28, wherein in formula 3-1, adjacent substituents R31、R32、R33At least one group of the groups is connected to form a ring;
preferably, in formula 3-1, adjacent substituents R31、R32、R33At least one group of the two groups is connected to form a ring, and the formed ring at least comprises 1 six-membered ring;
more preferably, the third compound has a structure represented by one of formulas 3-11 to 3-21:
Figure FDA0002856206090000501
wherein, in formulae 3-11 to 3-21,
Ar31each occurrence, identically or differently, is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
L31each 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;
x is selected, identically or differently on each occurrence, from CRx1Rx2、NRx3O or S;
R31、R32、R33、R38the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31、R32、R33、R38、Rx1-Rx3the occurrences being the same or different 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 heteroaryl groupsOr 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, carbonyl, carboxylic acid group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
adjacent substituents R31、R32、R33、R38Can optionally be linked to form a ring.
30. The electroluminescent device of claim 28 or 29, wherein R is31-R38Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxyl, mercapto, substituted or unsubstituted alkyl groups having 1 to 20 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, and combinations thereof;
said L31To L35Each occurrence, the same or different, is selected from the group consisting of: a single bond, substituted or unsubstituted arylene of 6 to 18 carbon atoms, substituted or unsubstituted heteroarylene of 3 to 18 carbon atoms, and combinations thereof;
ar is31To Ar35、Rx1-Rx3Each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted aryl groups having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 18 carbon atoms, and combinations thereof;
preferably, wherein said R31-R38Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorineCyano, hydroxy, mercapto, methyl, trideuteromethyl, vinyl, phenyl, biphenyl, naphthyl, 4-cyanophenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, pyridyl, phenylpyridyl, and combinations thereof;
said L is31To L35Selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, pyridylene, thienylene, dibenzofuranylene, dibenzothiophenylene, and combinations thereof;
ar is31To Ar35、Rx1-Rx3Each occurrence, the same or different, is selected from the group consisting of: phenyl, deuterated phenyl, methylphenyl, fluorophenyl, tert-butylphenyl, trideuteromethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridinyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.
31. The electroluminescent device of any one of claims 28 to 30, wherein the third compound is selected from the group consisting of:
Figure FDA0002856206090000511
Figure FDA0002856206090000521
Figure FDA0002856206090000531
Figure FDA0002856206090000541
Figure FDA0002856206090000551
Figure FDA0002856206090000561
Figure FDA0002856206090000571
Figure FDA0002856206090000581
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
32. A display assembly comprising an electroluminescent device as claimed in any one of claims 1 to 31.
33. A combination of compounds comprising at least a first compound and a second compound;
the first compound has a structure as represented by formula 1 a:
Figure FDA0002856206090000591
in formula 1a, A1-A10Each independently selected from C, CRAOr N; and A is1-A103 of (a) is C; wherein 2C are adjacent and are connected to the structure represented by formula 1 b; another C is linked to a structure represented by formula 1C:
Figure FDA0002856206090000592
respectively representing the position of the connection of the formula 1b and the formula 1a, and the position of the connection of the formula 1c and the formula 1 a;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
v is selected from NR2O or S;
RA,R1,R2each 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 arylsilane groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents RA,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex and comprises a ligand L coordinated with the metalaAnd the metal is selected from metals having a relative atomic mass greater than 40; l isaHas a structure represented by formula 2:
Figure FDA0002856206090000593
in formula 2, Z is selected from O, S or Se;
X1-X8selected, identically or differently at each occurrence, from C, CRxOr N;
Y1-Y6selected from CR, identically or differently at each occurrencey1、CRy2Or N; the R isy2Having a radical of formula-L1-SiRs1Rs2Rs3The structure of (1);
Rx,Ry1,Rs1,Rs2,Rs3each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
L1selected 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, or a combination thereof;
adjacent substituents Rx,Rs1,Rs2,Rs3Can optionally be linked to form a ring.
CN202011546486.0A 2020-12-24 2020-12-24 Electroluminescent device Pending CN114678485A (en)

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