CN115275030A - Electroluminescent device - Google Patents

Electroluminescent device Download PDF

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CN115275030A
CN115275030A CN202110470664.4A CN202110470664A CN115275030A CN 115275030 A CN115275030 A CN 115275030A CN 202110470664 A CN202110470664 A CN 202110470664A CN 115275030 A CN115275030 A CN 115275030A
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邝志远
张晗
张翠芳
王乐
王强
张奇
谢梦兰
代志洪
路楠楠
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Beijing Summer Sprout Technology Co Ltd
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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 electroluminescent device of the present invention exhibits an excellent combination of device properties such as longer lifetime and higher efficiency. 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 an electroluminescent device comprising a novel material combination of a first compound having a structure of formula 1a and a second compound having a ligand structure of formula 2 in an organic layer and a display module comprising the same, and a compound combination of the first compound having a structure of formula 1a and the second compound having a ligand structure of formula 2.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic Light Emitting Transistors (OLETs), organic 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, by Isman 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 mechanism. The OLEDs of the invention by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi 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 fabricated by solution methods if the materials 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 fluorescent 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 present invention aims to solve at least part of the above problems by providing an electroluminescent device with a novel combination of materials. The electroluminescent device uses a novel material combination consisting of a first compound with a structure shown in a formula 1a and a second compound with a ligand structure shown in a formula 2, and the novel material combination can be used in a light-emitting layer of the electroluminescent device. The novel material combination can show excellent comprehensive device performance in devices, such as longer service life and higher efficiency.
According to one embodiment of the present invention, an electroluminescent device is disclosed, which comprises an anode, 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 BDA0003048871400000021
in the case of the 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 BDA0003048871400000022
* Respectively represent the position of the connection of formula 1b and formula 1a, and the position of the connection of formula 1c and 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, 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,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex comprising a ligand La,LaHas a structure represented by formula 2:
Figure BDA0003048871400000031
in the formula 2, the first and second groups,
ring A and ring B are each independently selected from a five membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
Rd、Rethe same or different at each occurrence represents mono-, poly-, or no substitution;
y is selected from SiRyRy,GeRyRy,NRy,PRyO, S or Se;
when two R are simultaneously presentyWhen two R are presentyMay be the same or different;
X1-X2is selected, identically or differently on each occurrence, from CRxOr N;
R、Rd、Re、Rxand RyEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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 Rd、Rx、RyR and ReCan optionally be linked to form a ring;
the metal is selected from metals having a relative atomic mass greater than 40.
According to another embodiment of the present invention, there is also disclosed a display device comprising the electroluminescent device as described above.
According to another embodiment of the present invention, a combination of compounds is also disclosed, comprising at least a first compound and a second compound.
The invention discloses a novel electroluminescent device, which uses a novel material combination consisting of a first compound with a structure shown in a formula 1a and a second compound with a ligand structure shown in a formula 2, and the novel material combination can be used in a luminous layer of the electroluminescent device. The novel material combination can enable the novel electroluminescent device to obtain longer service life 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 not by way of limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the various layers and exemplary materials are described in more detail in U.S. Pat. No. 7,279,704B2 at columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped at a molar ratio of 50With F4-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. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including a composite cathode having a thin layer of a metal such as Mg: ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of a protective layer can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided via a non-limiting embodiment. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. Pat. No. 7,968,146b2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that a first layer is "in contact with" a second layer, there may be other layers between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "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 that 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 a triplet state and a singlet excited state. 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. Typically, 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).
Definition of terms with respect to substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes both straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.
Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyldimethylsilyl, triethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methylallyl, 1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl is contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
Figure BDA0003048871400000051
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-ylBiphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesitylphenyl and m-quaterphenyl. In addition, the aryl group may be optionally substituted.
Heterocyclyl or heterocyclic-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothienobipyridine, cinnoline, selenobenzene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, azaborizole and analogs thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy groups may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include a phenoxy group and a biphenyloxy group. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-nitrobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenyl-isopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable. In addition, the aralkyl group may be optionally substituted.
Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.
Arylsilyl-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl group, phenylbiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, diphenyltert-butylsilyl group, tri-tert-butylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.
The term "aza" in azabenzofuran, azabenzothiophene, etc., means that one or more of the C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, any of which may be substituted with one or more substituents selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, 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 amino having 2 to 20 carbon atoms, unsubstituted aryl having 2 to 20 carbon atoms, unsubstituted amino having 2 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, 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. Substitutions of other stable isotopes in the compounds may be preferred because they enhance 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 compound cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents may be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, 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 BDA0003048871400000081
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 BDA0003048871400000082
further, the expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which a hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
Figure BDA0003048871400000083
according to one embodiment of the present invention, there is disclosed an electroluminescent device comprising:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, 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 BDA0003048871400000084
in the case of the 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 a structure represented by formula 1 b; and the other C is linked to a structure represented by formula 1C:
Figure BDA0003048871400000085
* Respectively represent the position of the connection of formula 1b and formula 1a, and the position of the connection of formula 1c and 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, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atomsAn arylsilyl group of 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,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex comprising a ligand La,LaHas a structure represented by formula 2:
Figure BDA0003048871400000091
in the formula 2, the first and second groups,
ring a and ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;
Rd、Rethe same or different at each occurrence indicates mono-, poly-, or no substitution;
y is selected from SiRyRy,GeRyRy,NRy,PRyO, S or Se;
when two R are simultaneously presentyWhen two R are presentyMay be the same or different;
X1-X2selected from CR, identically or differently at each occurrencexOr N;
R、Rd、Re、Rxand RyEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or 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 aryloxySubstituted 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 Rd、Rx、RyR and ReCan optionally be linked to form a ring;
the metal is selected from metals having a relative atomic mass greater than 40.
In this context, the 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 R is a substituentAAnd 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 linked to each other to form a ring.
In this context, the adjacent substituents Rd、Rx、RyR and ReCan optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents RdIn between, two substituents ReIn between, two substituents RyIn between, two substituents RxOf a substituent RdAnd RxIn the substituent R and RyAnd a substituent ReAnd R, any one or more of these substituent groups may be bonded to form a ring. Obviously, none of these substituents may be connected to each other 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 BDA0003048871400000101
in formulae 1a-1 to 1a-6,
A1-A10is selected, identically or differently on each occurrence, from C, CRAOr N; and A is1-A10Is C, and is linked to a structure represented by formula 1C:
*-L-Ar
formula 1c;
* Represents the position at which formula 1c is attached 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, 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, 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 arylsilyl group having 2 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having a substituted or unsubstituted aryl groupSubstituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino groups having from 0 to 20 carbon atoms, and combinations thereof;
adjacent substituents RA,R1And R2Can optionally be linked to form a ring.
Herein, in formulae 1a-1 to 1a-6, A1-A10Is selected, identically or differently on 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-A10Is selected, identically or differently on 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, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl havingHeteroaryl of 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-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 BDA0003048871400000111
wherein, the first and the second end of the pipe are connected with each other,
in the formula 1c-1, B1-B6Selected from C, CR, identically or differently at each occurrenceBOr N;
in the formula 1c-2, B1-B8Selected from C, CR, identically or differently at each occurrenceBOr N;
in formula 1c-3, B1-B8Selected from C, CR, identically or differently 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, 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 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, and combinations thereof;
the support "represents the position at which the Ar structure is attached to the L in formula 1c;
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 RgAny 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 BDA0003048871400000112
in formulae 1c-11 to 1c-20, B1-BnSelected from CR, identically or differently at each occurrenceBOr N; b isnCorresponding to the B1-B12The largest of the numbers present in any of formulae 1c-11 to 1c-20, G is selected, identically or differently on each occurrence, 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, substituted or unsubstitutedSubstituted or unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having from 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having from 6 to 20 carbon atoms, and combinations thereof;
"means" indicates the position at which the Ar structure is attached to the L in formula 1c;
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 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 presentgWhich may be the same or different, are intended to mean:
in the formula 1c-11, B1-B5Is selected, identically or differently on each occurrence, from CRBOr 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-B8Is selected, identically or differently on each occurrence, from CRBOr N; g is selected from the group consisting of CR, identically or differently 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-B8Is selected, identically or differently on each occurrence, from CRBOr N; g is selected from the group consisting of CR, identically or differently 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 the group consisting of CR, identically or differently 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 formula 1c-11, B according to one embodiment of the present invention1、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 numbers represented by any one of the formulae 1c-11 to 1c-20, and the others being independently selected from the group consisting of CRBOr N.
According to one embodiment of the present invention, in the formula 1c-11, B1、B3、B5Two or three of which are N, the others being 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-B12The largest number among the numbers represented by any one of the formulae 1c-11 to 1c-20, and the others being independently selected from the group consisting of 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-dimethylfluorenyl, pyridinyl, phenylpyridinyl, 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 numbers represented by any one of the formulae 1c-11 to 1c-20, and RBSelected from the group consisting of: deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkenyl having 6 to 30 carbonsAn aryl group of atoms, a substituted or unsubstituted heteroaryl group 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 being present in 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, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridinyl, phenylpyridinyl, and combinations thereof.
According to an embodiment of the present invention, ar in formula 1c is selected from the group consisting of Ar-1 to Ar-78, wherein 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 structures of Ar-1 to Ar-78 is partially or completely substituted by deuterium.
According to one embodiment of the invention, wherein said 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 said 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 in the structure of said compounds E-1 to E-91 can be partially or completely substituted by deuterium.
According to an embodiment of the invention, wherein in the second compound, ring a and/or ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-18 carbon atoms or a heteroaromatic ring having 3-18 carbon atoms.
According to one embodiment of the invention, wherein in the second compound, ring a and/or ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms or a heteroaromatic ring having 3 to 10 carbon atoms.
According to an embodiment of the present invention, wherein, in the second compound, the LaSelected from the group consisting of structures represented by any one of formulas 2-1 to 2-19:
Figure BDA0003048871400000131
Figure BDA0003048871400000141
wherein the content of the first and second substances,
in the formulae 2-1 to 2-19, X1-X2Selected from CR, identically or differently at each occurrencexOr N; x3-X7Is selected, identically or differently on each occurrence, from CRdOr N; a. Thee1-Ae6Selected from CR, identically or differently at each occurrenceeOr N;
z is selected, identically or differently on each occurrence, from CRfRf,SiRfRf,PRfO, S or NRf(ii) a When two R are simultaneously presentfWhen two R are presentfThe same or different;
y is selected from SiRyRy,NRy,PRyO, S or Se; when two R are simultaneously presentyWhen two R are presentyThe same or different;
R,Rx,Ry,Rd,Reand RfEach 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 alkyl having 3-A cycloalkyl group of 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclyl group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted hydroxyl group having 0 to 20 carbon atoms, an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, Rx,Ry,Rd,ReAnd RfCan optionally be linked to form a ring;
in this context, the adjacent substituents R, Rx,Ry,Rd,ReAnd R can optionally be linked to form a ring, intended to indicate a group of adjacent substituents therein, e.g. two substituents RdIn between, two substituents ReIn between, two substituents RxIn between, two substituents RyIn between, two substituents RfOf R is a substituentdAnd RxOf R is a substituenteAnd RfIn between, the substituents R and RyOf a substituent RyAnd RfAnd the substituents R and RfAnd 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 a preferred embodiment of the present invention, LaSelected from the group consisting of structures represented by formula 2-1, formula 2-5, formula 2-8, formula 2-10, formula 2-11, and formula 2-12.
According to a preferred embodiment of the invention, LaSelected from the group consisting of the structures represented by the formula 2-1.
According to one embodiment of the present invention, wherein, in the formulae 2-1 to 2-19, X1-XnAnd/or Ae1-AemAt least one selected from N, XnCorresponding to the X1-X7The largest sequence number existing in any one of the formulas 2-1 to 2-19, wherein A isemCorresponds to the Ae1-Ae6The largest sequence number among any of the formulae 2-1 to 2-19. For example, for formula 2-1, the XnCorresponding to the X1-X7X having the largest number in the formula 2-15Said A isemCorresponds to the Ae1-Ae6The largest sequence number A in the formula 2-1e4I.e., in the formula 2-1, X1-X5And/or Ae1-Ae4At least one of which is selected from N. As another example, for formulas 2-13, the XnCorresponding to the X1-X7X having the largest number in the formulae 2 to 133Said A isemCorresponds to the Ae1-Ae6The largest A in the formulas 2 to 13e2I.e. X in the formulae 2-131-X3And/or Ae1-Ae2At least one of which is selected from N.
According to one embodiment of the present invention, in formulae 2-1 to 2-19, X1-XnAt least one selected from N, XnCorresponding to the X1-X7The largest sequence number is present in any one of the formulae 2-1 to 2-19.
According to one embodiment of the present invention, in formulae 2-1 to 2-19, X2Is N.
According to one embodiment of the present invention, wherein, in the formulae 2-1 to 2-19, X1-X2Each independently selected from CRx;X3-X7Each independently selected from CRd;Ae1-Ae6Each independently selected from CRe(ii) a Adjacent substituents Rx、Rd、ReCan optionally be linked to form a ring.
In this example, the adjacent substituents Rx、Rd、ReCan optionally be linked to form a ring, intended to denote an adjacent substituent group therein, e.g. two substituents RdIn between, two substituents ReIn between, two substituents RxAnd a substituent RdAnd RxAnd 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 one embodiment of the invention, said Rx、Rd、ReEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, said Rx、Rd、ReAt least two or three of which, on each occurrence, are selected, identically or differently, from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof.
In this embodiment, R isx、Rd、ReAt least two or three of which, on each occurrence, are selected, identically or differently, from the group of substituents mentioned, is intended to mean that the substituents consisting of two R arexSubstituent, all RdSubstituents and all ReAt least two or three substituents of the group of substituents are selected, identically or differently on each occurrence, from the group of substituents mentioned.
According to an embodiment of the present invention, wherein, in formulae 2-1 to 2-11, X4And/or X5Selected from CR in the formulae 2-12 to 2-19, X3Selected from the group consisting of CRd
And said R isdEach occurrence, which is the same or different, is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, said RdEach occurrence, the same or different, is selected 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 present invention, wherein, in formulae 2-1 to 2-19, R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or a combination thereof.
According to one embodiment of the invention, said R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, neopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, trimethylsilyl, or a combination thereof.
According to an embodiment of the present invention, wherein, in formulae 2-1 to 2-19, Y is selected from O or S.
According to an embodiment of the present invention, wherein, in formulae 2-1 to 2-19, Y is O.
According to one embodiment of the present invention, wherein, in the formulae 2-1 to 2-19, X1And X2Each independently selected from CRx
According to one embodiment of the invention, said RxEach occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof.
According to an embodiment of the present invention, wherein, in formulae 2-1 to 2-19, X1Selected from the group consisting of CRx,X2Is N.
According to one embodiment of the invention, said RxSelected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000161
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rx1、Rx2、Rd1、Rd2、Rd3、Re1、Re2、Re3、Re4each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof.
R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000171
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rx1、Rx2、Rd1、Rd2、Rd3and/or Re1、Re2、Re3、Re4At least one or two of which, identically or differently on each occurrence, are selected 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbonsAn atomic heteroaryl group, a substituted or unsubstituted alkylsilyl group of 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6-20 carbon atoms, or a combination thereof;
r is selected from the group consisting of halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000172
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rx1、Rx2、Rd1、Rd2、Rd3and/or Re1、Re2、Re3、Re4At least one or two of which are, identically or differently on each occurrence, selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof;
r is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, 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, or combinations thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000181
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rd2selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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, or a combination thereof;
r is selected from the group consisting of halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof; re1、Re2、Re3、Re4Is selected, identically or differently on each occurrence, 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 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, or a combination thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000182
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rd2selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof;
r is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, 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, or combinations thereof; re1、Re2、Re3、Re4At least one or two of which are, identically or differently on each occurrence, selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000191
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rx1、Rx2、Rd1、Rd2、Rd3、Re1、Re2、Re3、Re4each occurrence of at least one of R, is selected, identically or differently, from the group consisting of: substituted or unsubstituted alkyl groups having 3 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 and combinations thereof.
According to one embodiment of the invention, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure BDA0003048871400000192
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rd1、Rd2、Rd3、Re1、Re2、Re3、Re4each occurrence of at least one of R, is selected, identically or differently, from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.
According to an embodiment of the present invention, wherein said LaIs selected from the group consisting of La1To La168Wherein said L isa1To La168The concrete structure of (3) is shown in claim 19.
According to an embodiment of the present invention, wherein said La1To La168The hydrogen in the structure of (a) can be partially or completely substituted with deuterium.
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 the group consisting of metals having a large relative atomic massA metal at 40; l isa、Lb、LcA first, second and third ligand, respectively, of said complex;
wherein M is 1,2 or 3, n is 0,1 or 2, q is 0,1 or 2,m + n + q equals the oxidation state of metal M; when m is greater than 1, a plurality of LaThe same or different; when n is 2, two LbIdentical or different, when q is 2, two LcThe 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 BDA0003048871400000201
wherein R isa、RbAnd RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, se, 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, 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 atomsA substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a 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;
wherein the adjacent substituents Ra、Rb、Rc、RN1、RN2、RC1And RC2Can optionally be linked to form a ring.
In this embodiment, the adjacent substituents Ra,Rb,Rc,RN1,RC1And RC2Can optionally be linked to form a ring, intended to denote an adjacent group of substituents, e.g. two substituents RaIn between, two substituents RbIn between, two substituents RcAnd a substituent RaAnd RbOf a substituent RaAnd RcOf R is a substituentbAnd RcOf a substituent RC1And RC2Of a substituent RbAnd RC1Of a substituent RaAnd RC1Of a substituent RcAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RC2Of R is a substituentcAnd RC2Of a substituent RbAnd RN1Of R is a substituentaAnd RN1Of a substituent RcAnd RN1Any one or more of these substituent groups may be linked to form a ring. Obviously, these adjacent substituents may not be connected to form a ring.
According to one embodiment of the invention, wherein the metal M is selected from Ir, rh, re, os, pt, au or Cu; preferably, M is selected from Ir or Pt; more preferably, M is Ir.
According to an embodiment of the invention, wherein LbEach occurrence of the same orVariously selected from the following structures:
Figure BDA0003048871400000202
wherein R is11–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 arylalkyl 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 amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
According to an embodiment of the invention, wherein LbEach occurrence, identically or differently, is selected from the following structures:
Figure BDA0003048871400000211
wherein R is11-R13At least one is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, 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, orAnd (4) combining.
According to one embodiment of the present invention, wherein LbEach occurrence, identically or differently, is selected from the following structures:
Figure BDA0003048871400000212
wherein R is11-R13At least 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.
According to an embodiment of the invention, wherein LbEach occurrence, identically or differently, is selected from the following structures:
Figure BDA0003048871400000213
wherein R is11-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.
According to an embodiment of the present invention, wherein said LbIs selected from the group consisting of Lb1To Lb322The group consisting ofcIs selected from the group consisting of Lc1To Lc231Wherein L isb1To Lb322And Lc1To Lc231The specific structure of (A) is shown in claim 22.
According to one embodiment of the present invention, the device wherein the second compound is an Ir complex having a structure such as Ir (L)a)(Lb)(Lc)、Ir(La)2(Lb)、Ir(La)2(Lc) And Ir (L)a)(Lc)2Any one of the structures shown in; when the second compound has Ir (L)a)(Lb)(Lc) In the structure of (1), the LaIs selected from the group consisting of La1To La168Any one of the group consisting of LbIs selected from the group consisting of Lb1To Lb322Any one of the group consisting ofcIs selected from the group consisting of Lc1To Lc231Any one of the group consisting of; when the second compound has Ir (L)a)2(Lb) In the structure (1), the LaIs selected from the group consisting of La1To La168Any one or any two of the group consisting of, the 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), the LaIs selected from the group consisting of La1To La168Any one or any two of the group consisting of, the 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), the LaIs selected from the group consisting of La1To La168Any one of the group consisting of LcIs selected from the group consisting of Lc1To Lc231Any one or any two of the group consisting of.
According to an embodiment of the invention, wherein the second compound is selected from the group consisting of C1To C145Group consisting of wherein said C1To C145The concrete structure of (3) is shown in claim 23.
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 an embodiment of the present invention, wherein the organic layer further includes a third compound having a structure represented by one of formulas 3-1 to 3-3:
Figure BDA0003048871400000221
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; and when Ar is31To Ar35When it is heteroaryl, at least one atom is selected from N, O or S;
L31to L35Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
x is selected from CRx3Rx4、NRx5O or S;
R31-R37the same or different at each occurrence is indicative of mono-, poly-or unsubstituted;
R31-R37each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 6 to 20 carbon atomsSubstituted 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;
Rx3-Rx5each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R31-R37Can optionally be linked to form a ring.
In this context, adjacent substituents R31-R37Can optionally be linked to form a ring, intended to denote an adjacent substituent group therein, e.g. two substituents R31In between, two substituents R32In between, two substituents R33In between, two substituents R34In between, two substituents R35In between, two substituents R36In between, two substituents R37Of R is a substituent31And R32Of R is a substituent32And R33Of a substituent R34And R35Of a substituent R35And R36And a substituent R36And R37And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be linked to each other to form a ring.
According to one embodiment of the present invention, the organic layer is a light emitting layer, and the third compound is a host material.
According to one embodiment of the present invention, wherein in the formula 3-1, adjacent substituents R31、R32、R33At least one group is connected into a ring.
In this context, the adjacent substituents R31、R32、R33At least one group being linked to form a ring, intended to indicate an adjacent group of substituents therein, e.g. two substituents R31In between, two substituents R32In between, two substituents R33Of R is a substituent31And R32And a substituent R32And R33At least one of these substituent groups is linked to form a ring.
According to an embodiment of the present invention, wherein in said formula 3-1, adjacent substituents R31、R32、R33At least one group is connected to form a ring, and the formed ring at least comprises 1 six-membered ring.
According to one embodiment of the present invention, the third compound is selected from a structure represented by one of formulas 3-11 to 3-21:
Figure BDA0003048871400000231
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; and when Ar is31To Ar35When it is heteroaryl, at least one atom is selected from N, O or S;
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 from CRx3Rx4、NRx5O or S;
R31-R33and R38The same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31-R33and R38The 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 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 alkoxySubstituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Rx3-Rx5each occurrence, the same or different, is selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R31-R33And R38Can optionally be linked to form a ring.
In this context, adjacent substituents R31-R33And R38Can optionally be linked to form a ring, is intended to mean a group in which adjacent substituents are present, for example two substituents R31In between, two substituents R32In between, two substituents R33In between, two substituents R38Of a substituent R31And R38Of a substituent R32And R38Of R is a substituent33And R38Of R is a substituent31And R32And a substituent R32And R33And 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 one embodiment of the invention, said R31-R38Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, cyano, hydroxy, mercapto, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl havingHeteroaryl of 3 to 30 carbon atoms, and combinations thereof; said L is31To 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 Ar35Each 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 one embodiment of the invention, said R31-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-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 Ar35Each occurrence, the same or different, is selected from the group consisting of: phenyl, deuterated phenyl, methylphenyl, fluorophenyl, t-butylphenyl, trideuteromethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.
According to one embodiment of the invention, the third compound is selected from the group consisting of H-1 to H-136, wherein the specific structure of H-1 to H-136 is shown in claim 28.
According to one embodiment of the invention, wherein, optionally, the hydrogen energy in the structure of H-1 to H-136 is partially or completely substituted with deuterium.
According to an embodiment of the invention, wherein the electroluminescent device emits red light.
According to one embodiment of the invention, wherein the electroluminescent device emits white light.
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 one embodiment of the invention, a combination of compounds is disclosed comprising at least a first compound and a second compound;
wherein the content of the first and second substances,
the first compound has a structure represented by formula 1 a:
Figure BDA0003048871400000241
in the case of the 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 BDA0003048871400000251
* Represents the position of formula 1b connected with formula 1a and the position of formula 1c connected with 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 having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene 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, 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,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex comprising a ligand La,LaHas a structure represented by formula 2:
Figure BDA0003048871400000252
in the case of the formula 2, the reaction mixture,
ring a and ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;
Rd、Rethe same or different at each occurrence represents mono-, poly-, or no substitution;
y is selected from SiRyRy,GeRyRy,NRy,PRyO, S or Se;
when two R are simultaneously presentyWhen two R are presentyMay be the same or different;
X1-X2is selected, identically or differently on each occurrence, from CRxOr N;
R、Rd、Re、Rxand RyEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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 Rd、Rx、RyR and ReCan optionally be linked to form a ring.
According to one embodiment of the present invention, wherein the combination of compounds further comprises a third compound having a structure represented by one of formulas 3-1 to 3-3:
Figure BDA0003048871400000261
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; and when Ar is31To Ar35When heteroaryl, at least one atom is selected from N, O or S;
L31to L35Each occurrence, the same or different, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
x is selected from CRx3Rx4、NRx5O or S;
R31-R37the same or different at each occurrence is indicative of mono-, poly-or unsubstituted;
R31-R37each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted 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;
Rx3-Rx5each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R31-R37Can optionally be linked to form a ring.
According to an embodiment of the present invention, wherein the first compound, the second compound and the third compound may be further selected from the group described in any of the previous embodiments.
In combination with other materials
The materials described herein for a particular layer in an organic light emitting device can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161, paragraphs 2016/0359122A1, which is hereby incorporated by reference in its entirety. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application US2015/0349273A1, paragraphs 0080-0101, 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 and the second compound are not limited, and the preparation method can be prepared by conventional synthesis methods by those skilled in the art, and the details are not repeated herein. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the person skilled in the art knows the relevant contents of the above-mentioned device usage, testing method, etc., and can obtain the intrinsic data of the sample with certainty and without influence, the above-mentioned relevant contents are not repeated in this patent.
Those skilled in the art will be able to obtain or make a variety of compounds within the present application, including but not limited to the first compound, the second compound, the third compound. Or can be made by referring to Chinese application with application numbers CN202011219604.7 and CN202110348602.6, which are not described in detail herein.
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 one 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% -98%, and the luminescent material can account for 2% -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.
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. Organic layers specified below, in a vacuum of about 10 degrees-8In the case of Torr, the amount of the catalyst is 0.01 to 5
Figure BDA0003048871400000271
The rate of (a) was successively evaporated on the ITO anode by thermal vacuum. Compound HI is used as Hole Injection Layer (HIL) with a thickness of
Figure BDA0003048871400000272
The compound HT is used as Hole Transport Layer (HTL) with a thickness of
Figure BDA0003048871400000273
For Compound EBAs Electron Blocking Layer (EBL) with a thickness of
Figure BDA0003048871400000274
Then the compound E-9 as the first host, the compound H-35 as the second host and the compound C as the dopant are added8Co-evaporation as the light emitting layer (EML) with a thickness of
Figure BDA0003048871400000275
The compound HB was used as a hole-blocking layer (HBL) with a thickness of
Figure BDA0003048871400000276
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 BDA0003048871400000277
Finally, evaporation
Figure BDA0003048871400000278
8-hydroxyquinoline-lithium (Liq) as an Electron Injection Layer (EIL) in thickness and evaporation deposited
Figure BDA0003048871400000279
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 compound C was used in the light emitting layer (EML)27In place of the compound C8As a dopant.
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 in place of the compound E-9 and the compound H-35 as the host in the light-emitting layer (EML) and the compound RD-A was used in place of the compound C8As a dopant.
Device comparative example 2
Device comparative example 2 was conducted in the same manner as device example 1 except thatReplacement of Compound C with Compound RD-A in the light-emitting layer (EML)8As a dopant.
Device comparative example 3
Device comparative example 3 was implemented in the same manner as 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).
Device comparative example 4
Device comparative example 4 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).
TABLE 1 device structures of device examples and comparative examples
Figure BDA00030488714000002710
Figure BDA0003048871400000281
The material structure used in the device is as follows:
Figure BDA0003048871400000282
Figure BDA0003048871400000291
table 2 shows the results at 15mA/cm2External Quantum Efficiency (EQE) data measured at Current Density and at 5000cd/m2Life (LT 97) data measured at brightness.
TABLE 2 device data
Device numbering EQE(%) LT97(h)
Example 1 24.04 1362.09
Example 2 25.00 1501.60
Comparative example 1 21.3 245.8
Comparative example 2 20.52 122.2
Comparative example 3 22.45 1188.64
Comparative example 4 22.59 1157.30
As can be seen from the comparison of the data between examples 1 and 2 and comparative examples 3 and 4, respectively, the EQE of the second compound of the present invention was increased from 22.45% and 22.59% which had already reached very high levels in comparative examples 3 and 4 to 24.04% and 25.00%, respectively, and from 7.1% and 10.7%, respectively, in the first compound of the present invention compared to the commercial host material compound RH-a, and the increase was very significant; more importantly, the device lifetime is prolonged from 1157 hours and 1188 hours which reach a very high level in comparative examples 3 and 4 to 1362 hours and 1501 hours respectively, the lifting amplitudes are 14.6 percent and 29.7 percent respectively, and the lifting amplitudes are very large. Therefore, the combination of the first compound and the second compound is greatly improved in external quantum efficiency and device service life, excellent device performance is obtained and far exceeds the device effect when a commercial host material is adopted, and the results fully prove the superiority of the combination of the first compound and the second compound.
The comparison of data between examples 1 and 2 and comparative example 2 shows that the device performance of the examples has obvious advantages: compared with the comparative example 2, the EQE of the examples 1 and 2 is respectively improved by 14.6 percent and 17.9 percent, and meanwhile, the service life is also improved by dozens of times compared with the comparative example 2, which reaches over 1300 hours, thereby realizing the great improvement. These results again demonstrate the superiority of the first and second compound combinations of the present invention.
As can be seen from a comparison of comparative examples 1 and 2, when the same dopant compound RD-a is used, the EQE is reduced, the lifetime is greatly shortened, and the device performance is deteriorated when the first compound of the present invention is used as a host material, as compared with when the compound RH-a is used as a host material. However, as can be seen from the comparison between examples 1 and 2 and comparative examples 3 and 4, when the same second compound of the present invention is used as a dopant, the EQE and lifetime are greatly improved and the device performance is improved when the first compound of the present invention is used as a host material, compared with when the compound RH-a is used as a host material. From the above comparison, it can be seen that although the compound RD-a has structural similarity with the second compound of the present invention, when the first compound and the second compound of the present invention are used in combination, an unexpected great improvement is brought about in device performance. The unexpected advantages of the first and second compound combinations of the present invention are further reflected by the distinct device performance variations exhibited by such similar compound structures when combined with different compounds.
In summary, the combination of the first compound and the second compound disclosed in the present invention can show excellent overall device performance in devices, such as longer lifetime, higher external quantum 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 (31)

1. 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 FDA0003048871390000011
in the case of the 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 FDA0003048871390000012
* Represents the position of formula 1b connected with formula 1a and the position of formula 1c connected with 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 having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene 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, 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,R1And R2Can optionally be linked to form a ring;
the second compound is a metal complex comprising a ligand La,LaHas a structure represented by formula 2:
Figure FDA0003048871390000013
in the formula 2, the first and second groups,
ring A and ring B are each independently selected from a five membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms;
Rd、Rethe same or different at each occurrence represents mono-, poly-, or no substitution;
y is selected from SiRyRy,GeRyRy,NRy,PRyO, S or Se;
when two R are simultaneously presentyWhen two R are presentyMay be the same or different;
X1-X2selected from CR, identically or differently at each occurrencexOr N;
R、Rd、Re、Rxand RyEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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 Rd、Rx、RyR and ReCan optionally be linked to form a ring;
the metal is selected from metals having a relative atomic mass greater than 40.
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 FDA0003048871390000021
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, 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,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 RA,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, dibenzothienyl, triphenylenyl, carbazolyl, 9-phenylcarbazolyl, 9-dimethylfluorenyl, pyridyl, phenylpyridyl, 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 FDA0003048871390000031
wherein the content of the first and second substances,
in the formula 1c-1, B1-B6Is selected from C, CR, identically or differently at each occurrenceBOr N;
in the formula 1c-2, B1-B8Selected from C, CR, identically or differently at each occurrenceBOr N;
in formula 1c-3, B1-B8Is selected from C, CR, identically or differently at each occurrenceBOr N; g is selected from CRgRg,SiRgRg,NRg,BRg,PRg,O,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, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, and combinations thereof;
the support "represents the position at which the Ar structure is attached to the L in formula 1c;
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 FDA0003048871390000032
in formulae 1c-11 to 1c-20, B1-BnIs selected, identically or differently on each occurrence, from CRBOr 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, identically or differently on each occurrence, 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, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl groups having 3 to 20 ring atoms, substituted or unsubstituted 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, and combinations thereof;
"means" indicates the position at which the Ar structure is attached to the L in formula 1c;
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 which 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 which are N, the others being independently selected from CRB(ii) a B in formulae 1c-12 to 1c-201-BnAt least two of which are N, said BnCorresponding to said 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. Such asThe 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-dimethylfluorenyl, pyridinyl, phenylpyridinyl, and combinations thereof.
8. An 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 being present in 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 formulae 1c-11 to 1c-201-BnAt least one is CRBSaid B isnCorresponding to the B1-B12The largest number being present in 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-dimethylfluorenyl, pyridyl, phenylpyridyl, and the likeAnd (4) combining.
9. The electroluminescent device of any one of claims 1-8, wherein Ar in the formula 1c is selected from the group consisting of the following structures:
Figure FDA0003048871390000051
Figure FDA0003048871390000061
Figure FDA0003048871390000071
wherein, optionally, the hydrogen energy in the structures of Ar-1 through Ar-78 is partially or fully substituted with deuterium;
the support means indicates the position where the Ar structure is attached to the L in formula 1 c.
10. The electroluminescent device of any one of claims 1-9, wherein said 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 one of claims 1-10, wherein the first compound is selected from the group consisting of the following structures:
Figure FDA0003048871390000072
Figure FDA0003048871390000081
Figure FDA0003048871390000091
Figure FDA0003048871390000101
Figure FDA0003048871390000111
Figure FDA0003048871390000121
wherein, optionally, the hydrogen energy in the structures of said compounds E-1 to E-91 can be partially or completely substituted by deuterium.
12. An electroluminescent device as claimed in any one of claims 1 to 11 wherein in the second compound, ring a and/or ring B are each independently selected from a five membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms or a heteroaromatic ring having 3 to 18 carbon atoms;
preferably, ring a and/or ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms.
13. The electroluminescent device of any one of claims 1-12, wherein said LaA structure selected from the group consisting of structures represented by any one of formulas 2-1 to 2-19:
Figure FDA0003048871390000131
wherein, the first and the second end of the pipe are connected with each other,
in formulae 2-1 to 2-19, X1-X2Is selected, identically or differently on each occurrence, from CRxOr N; x3-X7Selected from CR, identically or differently at each occurrencedOr N; a. Thee1-Ae6Is selected, identically or differently on each occurrence, from CReOr N;
z is selected, identically or differently on each occurrence, from CRfRf,SiRfRf,PRfO, S or NRf(ii) a When two R are simultaneously presentfWhen two R are presentfThe same or different;
y is selected from SiRyRy,NRy,PRyO, S or Se; when two R are simultaneously presentyWhen two R are presentyThe same or different;
R,Rx,Ry,Rd,Reand RfEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted hydroxyl group having 0 to 20 carbon atoms, an amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R, Rx,Ry,Rd,ReAnd RfCan optionally selectThe ground is connected to form a ring;
preferably, LaSelected from the group consisting of structures represented by formula 2-1, formula 2-5, formula 2-8, formula 2-10, formula 2-11, and formula 2-12;
more preferably, LaSelected from the group consisting of the structures represented by the formula 2-1.
14. The electroluminescent device of claim 13, wherein X is represented by formula 2-1 to formula 2-191-XnAnd/or Ae1-AemAt least one of them is selected from N, XnCorresponding to the X1-X7The largest number among the above-mentioned groups represented by any of the formulas 2-1 to 2-19, wherein A isemCorresponds to the Ae1-Ae6The largest sequence number among any of the formulae 2-1 to 2-19;
preferably, in formulae 2-1 to 2-19, X1-XnAt least one selected from N, XnCorresponding to the X1-X7The largest sequence number among any one of the formulae 2-1 to 2-19;
more preferably, X2Is N.
15. The electroluminescent device of claim 13, wherein in formulae 2-1 to 2-19, X1-X2Each independently selected from CRx;X3-X7Each independently selected from CRd;Ae1-Ae6Each independently selected from CRe(ii) a Adjacent substituents Rx、Rd、ReCan optionally be linked to form a ring;
preferably, said R isx、Rd、ReEach 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 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 alkyl having 6 to 20 carbon atomsArylsilyl groups of (a), cyano, and combinations thereof;
more preferably, said Rx、Rd、ReAt least two or three of which, on each occurrence, are selected, identically or differently, from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof.
16. The electroluminescent device of any of claims 1-11, wherein the ligand LaHas a structure represented by formula 2-20 or formula 2-21:
Figure FDA0003048871390000141
wherein, in formulae 2-20 and formulae 2-21,
y is selected from O or S;
Rx1、Rx2、Rd1、Rd2、Rd3、Re1、Re2、Re3、Re4each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof;
r is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, and combinations thereof;
preferably, Rx1、Rx2、Rd1、Rd2、Rd3Neutralization/or Re1、Re2、Re3、Re4Is selected, identically or differently on each occurrence, 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 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, or a combination thereof; r is selected from the group consisting of halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof;
more preferably, Rx1、Rx2、Rd1、Rd2、Rd3Neutralization/or Re1、Re2、Re3、Re4At least one or two of which are, identically or differently on each occurrence, selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; r is selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstitutedA substituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.
17. The electroluminescent device of claim 16, wherein Rd2Selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted 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, or a combination thereof; r is selected from the group consisting of halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof; re1、Re2、Re3、Re4At least one or two of which, on each occurrence, are the same or different, are selected from deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, or combinations thereof;
preferably, Rd2Selected 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl havingA heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof; r is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, 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, or combinations thereof; r ise1、Re2、Re3、Re4Is selected, identically or differently on each occurrence, from a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, or a combination thereof.
18. The electroluminescent device as claimed in claim 16 or 17, wherein in formulae 2 to 20 and 2 to 21, Rx1、Rx2、Rd1、Rd2、Rd3、Re1、Re2、Re3、Re4Each occurrence of at least one of R, is selected, identically or differently, from the group consisting of: substituted or unsubstituted alkyl groups having 3 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, and combinations thereof;
preferably, Rd1、Rd2、Rd3、Re1、Re2、Re3、Re4And at least one of R, which is the same or different at each occurrence, is selected from the group consisting of: substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.
19. The electroluminescent device of any one of claims 1-18, wherein LaEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0003048871390000161
Figure FDA0003048871390000171
Figure FDA0003048871390000181
Figure FDA0003048871390000191
Figure FDA0003048871390000201
Figure FDA0003048871390000211
in the above structure, TMS represents trimethylsilyl;
optionally, said La1To La168The hydrogen in the structure of (a) can be partially or completely substituted with deuterium.
20. The electroluminescent device of any of claims 1-19, wherein the second compound has M (L)a)m(Lb)n(Lc)qThe structure of (1);
wherein the metal M is selected from metals having a relative atomic mass greater than 40; l isa、Lb、LcA first, second and third ligand, respectively, of said complex;
wherein M is 1,2 or 3, n is 0,1 or 2, q is 0,1 or 2,m + n + q is equal to the oxidation state of metal M; when m is greater than 1, a plurality of LaThe same or different; when n is 2, two LbIdentical or different, when q is 2, two of LcThe 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 FDA0003048871390000212
Figure FDA0003048871390000221
wherein R isa、RbAnd RcThe same or different at each occurrence indicates mono-, poly-, or no substitution;
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, 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,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;
wherein the adjacent substituents Ra、Rb、Rc、RN1、RN2、RC1And RC2Can optionally be linked to form a ring.
21. An electroluminescent device as claimed in claim 20 wherein the metal M is selected from Ir, rh, re, os, pt, au or Cu; preferably, M is selected from Ir or Pt; more preferably, M is Ir.
22. An electroluminescent device as claimed in claim 20 or 21 wherein LbEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0003048871390000222
Figure FDA0003048871390000231
Figure FDA0003048871390000241
Figure FDA0003048871390000251
Figure FDA0003048871390000261
Figure FDA0003048871390000271
Figure FDA0003048871390000281
Figure FDA0003048871390000291
wherein L iscEach occurrence, the same or different, is selected from the group consisting of:
Figure FDA0003048871390000292
Figure FDA0003048871390000301
Figure FDA0003048871390000311
Figure FDA0003048871390000321
Figure FDA0003048871390000331
Figure FDA0003048871390000341
23. an electroluminescent device as claimed in any one of claims 1 to 22 wherein the second compound is an Ir complex and has a composition such as Ir (L) sa)(Lb)(Lc)、Ir(La)2(Lb)、Ir(La)2(Lc) And Ir (L)a)(Lc)2Any one of the structures shown in; when the second compound has Ir (L)a)(Lb)(Lc) In the structure of (1), the LaIs selected from the group consisting of La1To La168Any one of the group consisting of LbIs selected from the group consisting of Lb1To Lb322Any one 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)2(Lb) In the structure (1), the LaIs selected from the group consisting of La1To La168Any 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), the LaIs selected from the group consisting of La1To La168Any 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 (1), the LaIs selected from the group consisting of La1To La168Any one of the group consisting of LcIs selected from the group consisting of Lc1To Lc231Any one or any two of the group
Preferably, the second compound is selected from the group consisting of the following structures:
Figure FDA0003048871390000351
Figure FDA0003048871390000361
Figure FDA0003048871390000371
Figure FDA0003048871390000381
Figure FDA0003048871390000391
Figure FDA0003048871390000401
Figure FDA0003048871390000411
Figure FDA0003048871390000421
Figure FDA0003048871390000431
24. the electroluminescent device of any one of claims 1-23, 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.
25. The electroluminescent device of any one of claims 1-24, wherein the organic layer further comprises a third compound having a structure represented by one of formulae 3-1 to 3-3:
Figure FDA0003048871390000441
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; and when Ar is31To Ar35When it is heteroaryl, at least one atom is selected from N, O or S;
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 from CRx3Rx4、NRx5O or S;
R31-R37the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31-R37each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group,isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Rx3-Rx5each occurrence, the same or different, is selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents 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.
26. The electroluminescent device of claim 25, wherein in said formula 3-1, adjacent substituents R31、R32、R33At least one group of the groups is connected to form a ring;
preferably, in said 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 is selected from the group consisting of structures represented by one of formulas 3-11 to 3-21:
Figure FDA0003048871390000442
Figure FDA0003048871390000451
wherein, in formulae 3-11 to 3-21,
X,Ar31,L31and R31-R33Has the same definition as in claim 25;
R38the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R38the occurrences are, identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkane having 1 to 20 carbon atomsA group, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclyl group having 3 to 20 ring atoms, a substituted or unsubstituted arylalkyl 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 R31-R33And R38Can optionally be linked to form a ring.
27. An electroluminescent device as claimed in claim 25 or 26, wherein R31-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 Ar35Each 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 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, dibenzothienyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 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 Ar35Each occurrence, the same or different, is selected from the group consisting of: phenyl, deuterated phenyl, methylphenyl, fluorophenyl, t-butylphenyl, trideuteromethylphenyl, biphenyl, naphthyl, deuterated naphthyl, dibenzofuranyl, dibenzothienyl, 9-dimethylfluorenyl, carbazolyl, pyridyl, pyrimidinyl, 4-cyanophenyl, 3-cyanophenyl, triphenylene, and combinations thereof.
28. The electroluminescent device of claim 25, wherein the third compound is selected from the group consisting of the following structures:
Figure FDA0003048871390000461
Figure FDA0003048871390000471
Figure FDA0003048871390000481
Figure FDA0003048871390000491
Figure FDA0003048871390000501
Figure FDA0003048871390000511
Figure FDA0003048871390000521
Figure FDA0003048871390000531
wherein, optionally, the hydrogen energy in the structure of said H-1 to H-136 is partially or fully substituted with deuterium.
29. The electroluminescent device of any one of claims 1-28, which emits red or white light.
30. A display assembly comprising an electroluminescent device as claimed in any one of claims 1 to 29.
31. A combination of compounds comprising at least a first compound and a second compound;
wherein the content of the first and second substances,
the first compound has a structure represented by formula 1 a:
Figure FDA0003048871390000541
in the case of the 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 a structure represented by formula 1 b; another C is linked to a structure represented by formula 1C:
Figure FDA0003048871390000542
* Respectively represent the position of the connection of formula 1b and formula 1a, and the position of the connection of formula 1c and 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, 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,R1And R2Can be optionally connected toForming a ring by grafting;
the second compound is a metal complex comprising a ligand La,LaHas a structure represented by formula 2:
Figure FDA0003048871390000543
in the formula 2, the first and second groups,
ring a and ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;
Rd、Rethe same or different at each occurrence represents mono-, poly-, or no substitution;
y is selected from SiRyRy,GeRyRy,NRy,PRyO, S or Se;
when two R are simultaneously presentyWhen two R are presentyMay be the same or different;
X1-X2selected from CR, identically or differently at each occurrencexOr N;
R、Rd、Re、Rxand RyEach occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, 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,carbonyl, carboxylic acid groups, ester groups, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents Rd、Rx、RyR and ReCan optionally be linked to form a ring;
preferably, the combination of compounds further comprises a third compound having a structure represented by one of formulas 3-1 to 3-3:
Figure FDA0003048871390000551
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; and when Ar is31To Ar35When heteroaryl, at least one atom is selected from N, O or S;
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 from CRx3Rx4、NRx5O or S;
R31-R37the same or different at each occurrence denotes mono-, poly-or unsubstituted;
R31-R37each 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 aryloxy having 2 to 20 carbon atomsAn alkenyl group of 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;
Rx3-Rx5each occurrence, the same or different, is selected from the group consisting of: substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R31-R37Can optionally be linked to form a ring.
CN202110470664.4A 2021-04-30 2021-04-30 Electroluminescent device Pending CN115275030A (en)

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