Mixture, composition, electroluminescent device and electronic equipment thereof
By using a mixture of hole and electron transport compounds with different structures as the main material for OLED devices, the stability and efficiency problems of blue phosphorescent devices were solved, achieving efficient and stable electroluminescence effects, simplifying the production process and reducing costs.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-08-04
- Publication Date
- 2026-04-03
AI Technical Summary
Existing organic light-emitting devices (OLEDs) suffer from problems such as blue unsaturation, short device lifetime, and high operating voltage in blue phosphorescent devices. Furthermore, the efficiency of phosphorescent OLEDs under hybrid strategies decreases rapidly under high brightness conditions, making it difficult to achieve a combination of light-emitting layer materials with excellent overall performance.
A mixture containing at least three hole-transporting and electron-transporting compounds with different structures is used as a single evaporation source to form an evaporation-stable mixture as the host material for OLED devices, simplifying the manufacturing process and improving performance.
It improves the evaporation stability and overall performance of OLED devices, reduces production costs, and achieves efficient electroluminescence in OLED devices.
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Figure CN121780150A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a mixture or composition comprising three or more compounds, an organic electroluminescent device, and an electronic device comprising the electroluminescent device. In particular, the present invention relates to a mixture or composition comprising three or more compounds, wherein one of the compounds has a structure of Formula 1, an organic electroluminescent device, and an electronic device thereof. Background Technology
[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.
[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as fabrication on flexible substrates.
[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet state emission. The triplet state generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). More recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.
[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.
[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.
[0008] CN115943749A discloses an electronic component, wherein the capping compound of the electronic component is represented by the following general formula. The structure is further restricted to a general formula. The application describes the structure, but does not disclose or teach the mixture formed by premixing such materials with two or more other compounds.
[0009] KR20220009915A discloses a compound having the following general formula. Structure, where R2 is X can be However, it did not disclose or teach the mixtures formed by premixing such compounds with two or more other compounds.
[0010] CN112538060A discloses a compound for use in a capping layer, which has the following general formula. The structure, the specific structure of which is also disclosed Its focus is on placing triarylamine compounds containing benzoxazole structures above the cathode of an electroluminescent device, utilizing their high refractive index optical properties as a capping material to improve the light extraction efficiency of the device. It does not disclose or teach mixtures formed by premixing such compounds with two or more other compounds.
[0011] WO2015163848A1 discloses an electroluminescent device in which the light-emitting layer comprises a premix, the premix comprising a physical mixture of an organometallic phosphorescent dopant and an organic host material having a specific structure. This application focuses on the premix of the two materials, the light-emitting material and the host material, and the application of the mixture in an electroluminescent device, but it does not disclose or teach a mixture comprising a premix of three or more hole and electron transport materials with different structures.
[0012] To obtain devices with better overall performance, one approach is to use multiple raw materials to fabricate the light-emitting layer. In this case, selecting material combinations with better matching properties is particularly important. Therefore, focusing on the combination of different materials and developing new mixtures with better matching properties and high evaporation stability for application in organic electroluminescent devices is a technical problem that urgently needs to be solved by industry professionals. Summary of the Invention
[0013] The present invention aims to provide a novel mixture containing three or more compounds to solve at least some of the aforementioned problems. The novel mixture provided by the present invention comprises at least three hole-transporting compounds and electron-transporting compounds with different structures, wherein the hole-transporting compounds have the structure represented by Formula 1. In particular, the mixture of the present invention exhibits high evaporation stability and can be used as a single evaporation source in the fabrication process of OLED devices, simplifying the production process and reducing production costs. Furthermore, when used as the host material in organic electroluminescent devices, this mixture can yield electroluminescent devices with excellent overall performance.
[0014] According to one embodiment of the present invention, a mixture is disclosed, which comprises at least a first compound, a second compound, and a third compound;
[0015] Wherein, the first compound is a hole-transporting compound; the second compound is an electron-transporting compound; and the third compound is selected from either a hole-transporting compound or an electron-transporting compound.
[0016] The first compound, the second compound, and the third compound have different chemical structures.
[0017] The mixture comprises a premix formed by pre-mixing the first compound, the second compound, and the third compound, wherein at least one of the first compound, the second compound, and the third compound has a mass ratio of C0 in the mixture. When the mixture is deposited under a certain vacuum and at a certain rate, the premix is evaporated on a surface positioned at a certain distance from the evaporated mixture to form n films of a certain thickness, and the at least one compound has a mass ratio of C in the nth film. n n is an integer ≥ 1;
[0018] Among the n films formed by vapor deposition, the mass ratio C of at least one compound in any one of the films is... m The absolute value of the difference between C0 and |C m -C0|≤2%, where m is an integer selected from 1 to n;
[0019] The hole transport compound has the structure represented by Formula 1;
[0020]
[0021] in,
[0022] X is selected from NR n O or S;
[0023] Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0024] If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;
[0025] If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L;
[0026] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0027] Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.
[0028] R w R n R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0029] Adjacent substituent R w They can be arbitrarily connected to form a loop;
[0030] Adjacent substituent R n They can be arbitrarily connected to form a ring.
[0031] According to another embodiment of the present invention, a compound composition is also disclosed, comprising a first compound represented by Formula 1, a second compound represented by Formula 2, and a third compound represented by Formula 1 or Formula 2, wherein the first compound, the second compound, and the third compound have different structures from each other;
[0032]
[0033] in,
[0034] X is selected from NRn O or S;
[0035] Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0036] If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;
[0037] If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L;
[0038] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0039] Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.
[0040]
[0041] in,
[0042] X9 to X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N;
[0043] L'2, L3, and L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.
[0044] Ar 21 Ar 22 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;
[0045] R x R w R n R zEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0046] Adjacent substituent R w They can be arbitrarily connected to form a loop;
[0047] Adjacent substituent R n They can be arbitrarily connected to form a loop;
[0048] Adjacent substituent R x They can be arbitrarily connected to form a ring.
[0049] According to another embodiment of the present invention, an electroluminescent device is also disclosed, comprising: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least the mixture described in the foregoing embodiments.
[0050] According to another embodiment of the present invention, an electronic device comprising the electroluminescent device described in the foregoing embodiments is also disclosed.
[0051] The novel mixture provided by this invention comprises at least three hole-transporting compounds and electron-transporting compounds with different structures, wherein the hole-transporting compounds have the structure represented by Formula 1. In particular, the novel mixture of this invention exhibits high evaporation stability and can be used as a single evaporation source in the fabrication process of OLED devices, simplifying the production process and reducing production costs. Furthermore, this mixture can be used as a host material in organic electroluminescent devices. Attached Figure Description
[0052] Figure 1This is a schematic diagram of an organic light-emitting device that may contain mixtures or compound compositions disclosed herein.
[0053] Figure 2 This is a schematic diagram of another organic light-emitting device that may contain mixtures or compound compositions disclosed herein. Detailed Implementation
[0054] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. Device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.
[0055] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a 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 also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.
[0056] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.
[0057] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.
[0058] OLEDs also require an encapsulation layer, such as Figure 2 An organic light-emitting device 200 is shown schematically and non-limitingly, which is related to... Figure 1 The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.
[0059] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). 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, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.
[0060] The materials and structures described in this article can also be used in other organic electronic devices listed above.
[0061] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.
[0062] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.
[0063] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.
[0064] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
[0065] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplet states, but rather on the transition between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triple gap to facilitate the transition between energy states. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A significant characteristic of TADF is that the delayed component increases with increasing temperature. If the reverse system crossover (RISC) rate is fast enough to minimize the nonradiative decay from the triplet state, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% spin statistics of electrogenerated excitons.
[0066] E-type delayed fluorescence can be observed in excited complex systems or single compounds. Unbound by theory, it is believed that E-type delayed fluorescence requires the luminescent material to have a small singlet-triple bandgap (ΔE). S-T Organic, nonmetallic donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transfer (CT) emission. Spatial separation of the HOMO and LUMO in these donor-acceptor compounds usually produces small ΔE. S-T These states can include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
[0067] Definition of the term "substituent group"
[0068] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.
[0069] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.
[0070] Cycloalkyl – as used herein, comprises cyclic alkyl groups. The cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.
[0071] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can 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, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, heteroalkyl groups may optionally be substituted.
[0072] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can 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, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl. In addition, the alkenyl group can be optionally substituted.
[0073] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may be optionally substituted.
[0074] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can 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 groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4′-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.
[0075] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.
[0076] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.
[0077] Alkoxy groups—as used herein—are represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic groups. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.
[0078] Aryloxy group – 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 can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.
[0079] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.
[0080] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.
[0081] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.
[0082] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.
[0083] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.
[0084] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.
[0085] In this disclosure, unless otherwise defined, the term "substituted alkyl," "substituted cycloalkyl," "substituted heteroalkyl," "substituted heterocyclic," "substituted aralkyl," "substituted alkoxy," "substituted aryloxy," "substituted alkenyl," "substituted alkynyl," "substituted aryl," "substituted heteroaryl," "substituted alkylsilyl," "substituted arylsilyl," "substituted alkylgermanium," "substituted arylgermanium," "substituted amino," "substituted acyl," "substituted carbonyl," and "substituted carboxylic acid" are used interchangeably. Substituted ester group, substituted sulfinyl group, substituted sulfonyl group, substituted phosphinyl group, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester group, sulfinyl, sulfonyl, and phosphinyl. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, and unsubstituted alkyl groups having... Cycloalkyl groups with 3-20 carbon atoms, unsubstituted heteroalkyl groups with 1-20 carbon atoms, unsubstituted heterocyclic groups with 3-20 carbon atoms, unsubstituted aralkyl groups with 7-30 carbon atoms, unsubstituted alkoxy groups with 1-20 carbon atoms, unsubstituted aryloxy groups with 6-30 carbon atoms, unsubstituted alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, and unsubstituted aryl groups with 6-30 carbon atoms. Unsubstituted heteroaryl groups having 3-30 carbon atoms, unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof having 0-20 carbon atoms.
[0086] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.
[0087] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.
[0088] In the compounds mentioned in this disclosure, polysubstituted means including disubstituted, up to the maximum range of available substitutions. When a substituent in a compound mentioned in this disclosure represents polysubstituted (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.
[0089] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, adjacent substituents can 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 and substituents bonded to carbon atoms directly bonded to each other.
[0090] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other via chemical bonds to form a ring, as exemplified by the following formula:
[0091]
[0092] The statement that adjacent substituents can optionally link to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring through chemical bonds, as exemplified by the following formula:
[0093]
[0094] The statement that adjacent substituents can optionally connect to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:
[0095]
[0096] Furthermore, the statement that adjacent substituents can optionally connect to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:
[0097]
[0098] According to one embodiment of the present invention, a mixture is disclosed, which comprises at least a first compound, a second compound, and a third compound;
[0099] Wherein, the first compound is a hole-transporting compound; the second compound is an electron-transporting compound; and the third compound is selected from either a hole-transporting compound or an electron-transporting compound.
[0100] The first compound, the second compound, and the third compound have different chemical structures.
[0101] The mixture comprises a premix formed by pre-mixing the first compound, the second compound, and the third compound, wherein at least one of the first compound, the second compound, and the third compound has a mass ratio of C0 in the mixture. When the mixture is deposited under a certain vacuum and at a certain rate, the premix is evaporated on a surface positioned at a certain distance from the evaporated mixture to form n films of a certain thickness, and the at least one compound has a mass ratio of C in the nth film. n n is an integer ≥ 1;
[0102] Among the n films formed by vapor deposition, the mass ratio C of at least one compound in any one of the films is... m The absolute value of the difference between C0 and |C m -C0|≤2%, where m is an integer selected from 1 to n;
[0103] The hole transport compound has the structure represented by Formula 1;
[0104]
[0105] in,
[0106] X is selected from NR n O or S;
[0107] Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0108] If Z1 to Z4 appear the same or different each time, choose C; CR zOr N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;
[0109] If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L;
[0110] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0111] Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.
[0112] R w R n R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0113] Adjacent substituent R w They can be arbitrarily connected to form a loop;
[0114] Adjacent substituent R n They can be arbitrarily connected to form a ring.
[0115] In this paper, "adjacent substituent R" w "Can be optionally linked to form a ring" is intended to indicate that any adjacent substituents R therein wThey can connect to form a ring. It is obvious that any adjacent substituents R... w They can also be left unconnected to form a loop.
[0116] In this paper, "adjacent substituent R" n "Can be optionally linked to form a ring" is intended to indicate that any adjacent substituents R therein n They can connect to form a ring. It is obvious that any adjacent substituents R... n They can also be left unconnected to form a loop.
[0117] In this document, "hole-transporting compounds" refers to compounds whose hole-transporting capability is greater than their electron-transporting capability, which can be used as hole-transporting materials in electroluminescent devices, including but not limited to hole-transporting compounds or bipolar compounds.
[0118] The term "electron transport compound" refers to a compound whose electron transport capability is greater than its hole transport capability, meaning that the compound itself has a greater electron transport capability than its hole transport capability, including but not limited to electron transport compounds or bipolar compounds.
[0119] Hole transport capability and electron transport capability can be determined by those skilled in the art based on the carrier mobility of the material; materials with electron mobility greater than hole mobility have stronger electron transport capability, and vice versa.
[0120] In this article, when the mixture is deposited at a certain vacuum level and a certain evaporation rate, the "certain vacuum level" and "certain evaporation rate" refer to a vacuum level of 10. -6 In cases where Torr is or lower, a certain evaporation rate can be used like Those skilled in the art can make adaptive adjustments according to actual needs to achieve the purpose of vapor deposition.
[0121] According to one embodiment of the present invention, Ar1 and Ar2 are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof; and when the cyclic atoms of Ar1 and Ar2 contain heteroatoms, the heteroatoms are selected from the group consisting of oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms.
[0122] In the embodiments, "the ring atoms of Ar1 and Ar2" refers to atoms in the rings of Ar1 and Ar2. For example, nitrogen atoms in nitrogen heterocyclic groups such as pyridine, carbazole, and quinazoline are ring atoms. Therefore, Ar1 and Ar2 are not selected from any nitrogen heterocyclic groups. For example, nitrogen atoms in amino groups are not ring atoms of Ar1 and Ar2. Therefore, Ar1 and Ar2 can be selected from amino-substituted aryl groups with 6-30 carbon atoms, amino-substituted heteroaryl groups with 3-30 carbon atoms, amino-substituted cycloalkyl groups with 3-20 ring carbon atoms, or combinations thereof.
[0123] According to one embodiment of the present invention, R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenyl groups having 2-20 carbon atoms. substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; and when R zWhen selected from substituted aryl groups having 6-30 carbon atoms or substituted heteroaryl groups having 3-30 carbon atoms, the aryl or heteroaryl group is selected from one or more of deuterium, halogen, unsubstituted alkyl groups having 1-20 carbon atoms, unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 ring atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, and unsubstituted groups having... The group consisting of alkenyl groups with 2-20 carbon atoms, unsubstituted alkynyl groups with 2-20 carbon atoms, unsubstituted aryl groups with 6-30 carbon atoms, unsubstituted heteroaryl groups with 3-30 carbon atoms, unsubstituted alkylsilyl groups with 3-20 carbon atoms, unsubstituted arylsilyl groups with 6-20 carbon atoms, unsubstituted alkylgermanium groups with 3-20 carbon atoms, unsubstituted arylgermanium groups with 6-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphinyl groups, and combinations thereof.
[0124] According to one embodiment of the present invention, wherein at least one of the first, second, and third compounds has a mass ratio of C0 in the mixture, and the mixture is deposited at a certain vacuum degree and a certain rate, the mixture is evaporated on a surface positioned at a certain distance from the evaporated mixture to form n films of a certain thickness, and the at least one compound in the nth film has a mass ratio of C0. n ; n is an integer ≥ 1; wherein, among the n films formed by vapor deposition, the mass ratio C of at least one compound in any one film is... m The absolute value of the difference between C0 and |C m -C0|≤1.5%, where m is an integer selected from 1 to n.
[0125] According to one embodiment of the present invention, when the third compound is selected from hole-transporting compounds, the third compound is heavier than the second compound and the first compound is lighter than the second compound in terms of vapor deposition characteristics.
[0126] According to one embodiment of the present invention, when the third compound is selected from electron transport compounds, the second compound is heavier than the first compound and the third compound is lighter than the first compound in terms of vapor deposition characteristics.
[0127] In this paper, any two compounds are premixed to form a two-component mixture under a certain vacuum degree, such as approximately 10. -6 At Torr or lower, at a certain rate, such as When the two-component mixture is vapor-deposited, it forms n films of a certain thickness on a surface positioned at a certain distance from the mixture being evaporated. As the number of films increases, the mass proportion of one of the compounds generally shows a gradual increasing trend, indicating that the compound is "heavy" in terms of vapor deposition characteristics; conversely, it is "light." As shown in Table 9 below, the proportion of compound A-401 in the films generally shows a gradual increasing trend as the number of films increases (from 22.3% in the first film to 30.1% in the sixth film), indicating that compound A-401 is "heavy" relative to compound B-4.
[0128] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The absolute value of the vapor deposition temperature difference between any two of the first compound, the second compound, and the third compound is less than 30°C.
[0129] In this embodiment, "the vacuum degree is 10" -6 In the case of Torr or lower, the evaporation rate is The vacuum level can be 10. -6 Torr, 10 -7 Torr or 10 -8 Torr; the evaporation rate can be
[0130] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The absolute value of the vapor deposition temperature difference between any two of the first compound, the second compound, and the third compound is less than 20°C.
[0131] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The absolute value of the vapor deposition temperature difference between any two of the first compound, the second compound, and the third compound is less than 10°C.
[0132] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The vapor deposition temperature of the first compound, the second compound, and the third compound is between 120℃ and 390℃.
[0133] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The vapor deposition temperature of the first compound, the second compound, and the third compound is between 140℃ and 370℃.
[0134] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The vapor deposition temperature of the first compound, the second compound, and the third compound is between 160℃ and 360℃.
[0135] According to one embodiment of the present invention, when the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The vapor deposition temperature of the first compound, the second compound, and the third compound is between 200℃ and 350℃.
[0136] According to one embodiment of the present invention, the hole transport compound has a HOMO energy level of -3.5 to -6.0 eV.
[0137] According to one embodiment of the present invention, the hole transport compound has a HOMO energy level of -4.0 to -5.6 eV.
[0138] According to one embodiment of the present invention, the electron transport compound has a LUMO energy level of -1.9 to -3.5 eV.
[0139] According to one embodiment of the present invention, the electron transport compound has a LUMO energy level of -2.0 to -3.0 eV.
[0140] According to one embodiment of the present invention, in the mixture, at least one of the first compound, the second compound, and the third compound has a triplet energy level T1 < 2.65 eV.
[0141] According to one embodiment of the present invention, in the mixture, at least one of the first compound, the second compound, and the third compound has a triplet energy level T1 < 2.60 eV.
[0142] According to one embodiment of the present invention, wherein, in the mixture, the first compound has a structure represented by formula 1-1 or formula 1-2:
[0143]
[0144] in,
[0145] X is selected from NR n O or S;
[0146] Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0147] Z1 to Z4 are selected from CR each time they appear, either identically or differently. z Or N;
[0148] When W1 to W5 appear, they are either identical or different and are selected from C, CR. w Or N, and one of W1 to W5 is selected from C and connected to L;
[0149] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0150] Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.
[0151] R w R n R zEach time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted... Or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0152] Adjacent substituent R w They can be arbitrarily connected to form a loop;
[0153] Adjacent substituent R n They can be arbitrarily connected to form a ring.
[0154] According to one embodiment of the invention, W1 to W5 are selected from C or CR each time they appear, either identically or differently. w And one of W1 to W5 is selected from C and connected to L.
[0155] According to one embodiment of the invention, W1 to W5 are selected from C or R each time they appear, either identically or differently. w And one of W2, W3, and W4 is C and connected to L.
[0156] According to one embodiment of the invention, W1 to W5 are selected from C or R each time they appear, either identically or differently. w And W3 is C and connected to L.
[0157] According to one embodiment of the present invention, X is selected from O or S.
[0158] According to one embodiment of the present invention, X is selected from O.
[0159] According to one embodiment of the present invention, CR is selected the same or different each time Z1 to Z3 occur. z .
[0160] According to one embodiment of the present invention, R w R z R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and combinations thereof.
[0161] According to one embodiment of the present invention, R w R z R n Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, halogen, phenyl, vinyl, naphthyl, biphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiopheneyl. alkyl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.
[0162] According to one embodiment of the present invention, Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, or combinations thereof.
[0163] Ar is selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms.
[0164] According to one embodiment of the invention, Ar1 and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilylfluorenyl, substituted or unsubstituted... alkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or combinations thereof;
[0165] Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilylfluorenyl, substituted or unsubstituted base.
[0166] According to one embodiment of the invention, Ar, Ar1, and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silanyl, substituted or unsubstituted... Base, or a combination thereof.
[0167] According to one embodiment of the invention, Ar, Ar1, and Ar2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted silanyl, substituted or unsubstituted... Base, or a combination thereof.
[0168] According to one embodiment of the present invention, Ar, Ar1, and Ar2 are each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, and silylfluorenyl. Base, or a combination thereof.
[0169] According to one embodiment of the present invention, the first compound is selected from the group consisting of compounds A-1 to A-536; the specific structures of compounds A-1 to A-536 are given in claim 12.
[0170] According to one embodiment of the present invention, the hydrogen in the structure of compounds A-1 to A-536 is partially or completely replaced by deuterium.
[0171] According to one embodiment of the present invention, the first compound is selected from the group consisting of compounds A-1 to A-662; the specific structures of compounds A-1 to A-662 are given in claim 12.
[0172] According to one embodiment of the present invention, the hydrogen in the structure of compounds A-1 to A-662 is partially or completely replaced by deuterium.
[0173] According to one embodiment of the present invention, the electron transport compound comprises at least one chemical group selected from the group consisting of: oxazole, thiazole, benzoxazole, benzothiazole, naphthoxazole, naphthothiazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, azadibenzothiophene, azadibenzofuran, dibenzoselenophene, benzene, pyridine, pyrimidine, carbazole, azacarbazole, indolocarbazole, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, triazine, and combinations thereof.
[0174] In this embodiment, substituted, aza, or fused-ring derivatives of groups such as "oxazole, thiazole, benzoxazole, benzothiazole, naphthoxazole, naphthothiazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, azadibenzothiophene, azadibenzofuran, dibenzoselenophene, benzene, pyridine, pyrimidine, carbazole, azacarbazole, indolocarbazole, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, triazine" are also considered "chemical groups" as described in this embodiment, including but not limited to "substituted oxazole", "substituted naphthoxazole", "azanaphthoxazole", or "phenanthrene oxazole (fused-ring derivative of oxazole)".
[0175] According to one embodiment of the present invention, the electron transport compound comprises a triazine group.
[0176] According to one embodiment of the present invention, the second compound has a structure represented by Formula 2:
[0177]
[0178] in,
[0179] X9 to X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N;
[0180] L'2, L3, L'3 are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0181] R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0182] Ar 21 Ar 22 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0183] Adjacent substituent R x They can be arbitrarily connected to form a ring.
[0184] In this embodiment, "adjacent substituent R" x "Can be optionally linked to form an aromatic ring" is intended to represent two adjacent substituents R x They can be connected by rings. For example, X9 to X 13 Two adjacent substituents R x Between, including but not limited to, such as X9 and X 10 Two adjacent substituents R x Between, X 10 With X 11 Two adjacent substituents R x Between, X 11 With X 12 Two adjacent substituents R x Between, X 12 With X 13 Two adjacent substituents R x Between these substituent groups, one or more of them may optionally be connected to form a ring. Obviously, these substituent groups may also not be connected to form a ring.
[0185] According to one embodiment of the present invention, in formula 2, Ar 21 Ar 22 At least one of the following is selected from dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), silanyl (substituted or unsubstituted), fluorenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), etc. A group, or a combination thereof.
[0186] According to one embodiment of the present invention, the second compound has a structure represented by formula 2-1:
[0187]
[0188] in,
[0189] X1 to X4 are selected from CR each time they appear, either identically or differently. x Or N;
[0190] X5 to X 13 Each time it appears, it is selected from C, CR, either identically or differently. x Or N, and at least one of X5 to X8 is selected from C and connected to L2, X9 to X 13 At least one of them is selected from C and connected to L2;
[0191] L2, L'2, L3, L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.
[0192] Ar 21 Ar 22 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.
[0193] R xEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0194] Adjacent substituent R x They can be arbitrarily connected to form a ring.
[0195] In this embodiment, "adjacent substituent R" x "Can be optionally linked to form a ring" is intended to represent two adjacent substituents R x They can be connected by rings. For example, X1 to X... 13 Any two adjacent substituents R x Between, including but not limited to, two adjacent substituents R in X1 and X2 x Between X2 and X3, two adjacent substituents R x Between X7 and X8, the two adjacent substituents R x Between, X 10 With X 11 Two adjacent substituents R x Between X9 and X 10 Two adjacent substituents R x Between these substituent groups, one or more of them may optionally be connected to form a ring. Obviously, these substituent groups may also not be connected to form a ring.
[0196] According to one embodiment of the present invention, L2, L'2, L3, L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.
[0197] According to one embodiment of the invention, L2, L'2, L3, L'3 are selected, in the same or different ways, from single bonds, or substituted or unsubstituted aryl groups having 6-20 carbon atoms, or combinations thereof.
[0198] According to one embodiment of the present invention, L2, L'2, L3, L'3 are selected, in the same or different ways, from single bonds, or substituted or unsubstituted aryl groups having 6-12 carbon atoms, or combinations thereof.
[0199] According to one embodiment of the present invention, at least one of L2 and L'2 is selected from a single bond.
[0200] According to one embodiment of the present invention, at least one of L3 and L'3 is selected from a single bond.
[0201] According to one embodiment of the present invention, L2 and L'2 are selected from single bonds, and L3 and L'3 are selected from single bonds, or substituted or unsubstituted aryl groups having 6-12 carbon atoms each time they appear.
[0202] According to one embodiment of the present invention, wherein L2, L'2, L3, L'3, each time appearing, are selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted trimethyleneene, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene Base, or a combination thereof.
[0203] According to one embodiment of the present invention, X1 to X4 are selected from CR each time they appear, either identically or differently. x X5 to X 13 Each time it appears, it is selected from C or CR, either the same or different. x And X6 or X7 is selected from C and connected to L2, X 11 Selected from C and connected to L2.
[0204] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 cyclic 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.
[0205] According to one embodiment of the present invention, at least one R x Selected from deuterium.
[0206] According to one embodiment of the present invention, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, phenyl, pyridyl, vinyl, adamantyl, methyl, ethyl, isopropyl, cyclopropane, naphthyl, biphenyl, phenanthrene, triphenylene, tert-butyl, trifluoromethyl, 9,9-dimethylfluorenyl, terphenyl, dibenzothiophene, dibenzofuranyl, benzothiazolyl, benzoxazolyl, phenanthrenexazolyl, phenanthrenethiazolyl Bases and their combinations.
[0207] According to one embodiment of the present invention, Ar 21 Ar 22 Each occurrence has the same or different structure represented by any one of equations Ar-1 to Ar-6:
[0208]
[0209] in,
[0210] Ar Q Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently.
[0211] Q is selected from C and CR each time it appears, either identically or differently. Q Or N, at least one Q is selected from C and connected to L3 or L'3;
[0212] Q1 is selected from O, S, Se, NR Q or CR Q R Q ;
[0213] Q2 is selected from O, S, or Se;
[0214] R QEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0215] Adjacent substituent R Q They can be arbitrarily connected to form a ring.
[0216] In this embodiment, "adjacent substituent R" Q "Can be optionally linked to form a ring" is intended to represent two adjacent substituents R Q They can connect to form a ring. For example, in formulas Ar-1 to Ar-3 and Ar-5 to Ar-6, the two adjacent substituents R on the Q group... Q Between, and in formula Ar-4, the two adjacent substituents R on the Q group. Q Between the Q group and the two adjacent substituents R on the Q1 group Q Between these substituent groups, one or more of them may optionally be connected to form a ring. Obviously, these substituent groups may also not be connected to form a ring.
[0217] According to one embodiment of the present invention, Ar 21 Ar 22 Each occurrence has the same or different structure represented by any one of the formulas Ar-1, Ar-2, and Ar-4.
[0218] According to one embodiment of the invention, L3 and L'3, each time they appear, are selected from single bonds, or from substituted or unsubstituted phenylene groups; Ar 21 Ar 22Each time it appears, it is selected from the same or different structures represented by Ar-1 or Ar-4.
[0219] According to one embodiment of the present invention, -L3-Ar 21 , -L'3-Ar 22 Each occurrence has the same or different structure represented by any one of equations X-1, X-2, X-3, X-4, and X-5:
[0220]
[0221] in,
[0222] Q1 is selected from O, S, Se, NR Q or CR Q R Q ;
[0223] Q is selected from CR each time it appears, either the same or different. Q Or N;
[0224] R Q Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0225] In this embodiment, * indicates the position where formula X-1, formula X-2, formula X-3, formula X-4 or formula X-5 is connected to the triazine group in formula 2 or formula 2-1.
[0226] According to one embodiment of the present invention, Q is selected from C or CR each time it occurs, either identically or differently. Q Q1 is selected from O, S, or CR.Q R Q Q2 is selected from O or S.
[0227] According to one embodiment of the present invention, R Q Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.
[0228] According to one embodiment of the present invention, R Q Each occurrence is selected from the group consisting of the following elements, either identically or differently: hydrogen, deuterium, halogen, phenyl, pyridyl, vinyl, adamantyl, methyl, ethyl, isopropyl, cyclopropane, naphthyl, biphenyl, phenanthrene, triphenylene, tert-butyl, trifluoromethyl, 9,9-dimethylfluorenyl, terphenyl, dibenzothiophene, dibenzofuranyl, benzothiazolyl, benzoxazolyl, phenanthrenexazolyl, phenanthrenethiazolyl Bases and their combinations.
[0229] According to one embodiment of the present invention, Ar Q Selected from phenyl, naphthyl, biphenyl, pyridyl, phenanthrene, 9,9-dimethylfluorenyl, terphenyl, dibenzothiophene, dibenzofuranyl, benzothiazolyl, benzoxazolyl, phenanthiazolyl, phenanthiazolyl. Base, or a combination thereof.
[0230] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds B-1 to B-223, the specific structures of which are given in claim 20.
[0231] According to one embodiment of the present invention, the hydrogen in the structure of compounds B-1 to B-223 can be partially or completely replaced by deuterium.
[0232] According to one embodiment of the present invention, the second compound is selected from the group consisting of compounds B-1 to B-257, the specific structures of which are given in claim 20.
[0233] According to one embodiment of the present invention, the hydrogen in the structure of compounds B-1 to B-257 can be partially or completely replaced by deuterium.
[0234] According to one embodiment of the present invention, the third compound has a structure represented by Formula 1 or Formula 2.
[0235] According to one embodiment of the present invention, the third compound has a structure represented by Formula 1, and the third compound is an isomer or isotope isomer of the first compound; or the third compound has a structure represented by Formula 2, and the third compound is an isomer or isotope isomer of the second compound.
[0236] According to one embodiment of the present invention, the third compound has a structure represented by Formula 1, Formula 1-1 or Formula 1-2, and the third compound is an isomer or isotopic isomer of the first compound.
[0237] According to one embodiment of the present invention, the third compound has a structure represented by Formula 2 or Formula 2-1, and the third compound is an isomer or isotopic isomer of the second compound.
[0238] According to one embodiment of the present invention, the third compound is an isomer or isotopic isomer of the first compound or the second compound.
[0239] In this document, "isotopic isomers" include, but are not limited to, the following two cases: When hydrogen in the structure of compound X is replaced by deuterium, the resulting compound is called compound X'. In this case, compound X', compound X, and compound Z (an isomer of compound X) are all isotopic isomers of each other. For example, compound B-2... With compound B-1 They are isotopic isomers, B-2 With compound B-4 The isomers of compound B-1 are also isotopic isomers of each other.
[0240] According to one embodiment of the present invention, at least one of the first compound, the second compound, and the third compound has a deuteration rate of 5%-100%.
[0241] According to one embodiment of the present invention, at least one of the first compound, the second compound, and the third compound has a deuteration rate of 30%-100%.
[0242] According to one embodiment of the present invention, at least one of the first compound, the second compound, and the third compound has a deuteration rate of 50%-100%.
[0243] According to one embodiment of the present invention, at least one of the first compound, the second compound, and the third compound has a deuteration rate of 60%-100%.
[0244] According to one embodiment of the present invention, at least one of the first compound, the second compound, and the third compound has a deuteration rate of 50%-90%.
[0245] According to one embodiment of the present invention, at least one of the first compound, the second compound, and the third compound has a deuteration rate of 60%-90%.
[0246] In this embodiment, the "deuteration rate of the compound" refers to the percentage of the number of deuterium atoms in the structure of the first compound, the second compound, or the third compound relative to the total number of hydrogen atoms and deuterium atoms in the compound structure.
[0247] In this document, the terms "certain distance" and "certain thickness" used during the film formation process of the evaporated mixture can be adaptively adjusted by those skilled in the art according to actual needs to achieve the purpose of vapor deposition. Exemplarily and non-limitingly, the certain distance can be 10-100 cm, or 30-80 cm, or 35-60 cm. Similarly, exemplarily and non-limitingly, the certain thickness can be 100 cm to... Or 200 to Or 400 to Or 5000 to
[0248] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 0.1-99.9:0.1-99.9:0.1-99.9.
[0249] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 1-99:1-99:1-99.
[0250] According to one embodiment of the present invention, the mass ratio of the first compound, the second compound, and the third compound in the mixture is 10-90:10-90:10-90.
[0251] According to one embodiment of the present invention, when the third compound in the mixture is selected from electron transport compounds, the mass ratio of the first compound, the second compound, and the third compound is 10-40:1-30:50-80.
[0252] According to one embodiment of the present invention, when the third compound in the mixture is selected from electron transport compounds, the mass ratio of the first compound, the second compound, and the third compound is 20-40:1-10:50-80.
[0253] According to one embodiment of the present invention, when the third compound in the mixture is selected from electron transport compounds, the mass ratio of the first compound, the second compound, and the third compound is 25-35:5-10:60-70.
[0254] According to one embodiment of the present invention, when the third compound in the mixture is selected from hole-transporting compounds, the mass ratio of the first compound, the second compound, and the third compound is 10-50:50-80:1-30.
[0255] According to one embodiment of the present invention, when the third compound in the mixture is selected from hole transport compounds, the mass ratio of the first compound, the second compound, and the third compound is 20-50:50-70:1-20.
[0256] According to one embodiment of the present invention, when the third compound in the mixture is selected from hole transport compounds, the mass ratio of the first compound, the second compound, and the third compound is 20-30:50-60:1-10.
[0257] According to one embodiment of the present invention, when the third compound in the mixture is selected from hole transport compounds, the mass ratio of the first compound, the second compound, and the third compound is 30-40:60-70:10-20.
[0258] According to one embodiment of the present invention, the mixture comprises the first compound, the second compound, and the third compound.
[0259] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least the mixture described in any of the foregoing embodiments.
[0260] According to one embodiment of the present invention, in the electroluminescent device, the first electrode is an anode and the second electrode is a cathode.
[0261] According to another embodiment of the present invention, a compound composition is also disclosed, comprising a first compound represented by Formula 1, a second compound represented by Formula 2, and a third compound represented by Formula 1 or Formula 2, wherein the first compound, the second compound, and the third compound have different structures from each other;
[0262]
[0263] in,
[0264] X is selected from NR n O or S;
[0265] Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms;
[0266] If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5;
[0267] If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L;
[0268] L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;
[0269] Ar1 and Ar2 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof.
[0270]
[0271] in,
[0272] X9 to X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N;
[0273] L'2, L3, and L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof.
[0274] Ar 21 Ar 22 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof;
[0275] R x R w R n R zEach time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0276] Adjacent substituent R w They can be arbitrarily connected to form a loop;
[0277] Adjacent substituent R n They can be arbitrarily connected to form a loop;
[0278] Adjacent substituent R x They can be arbitrarily connected to form a ring.
[0279] According to one embodiment of the present invention, the compound composition further comprises at least one phosphorescent material, which is a metal complex.
[0280] According to one embodiment of the present invention, a compound composition is disclosed, comprising the mixture described in any of the above embodiments and at least one phosphorescent material, wherein the phosphorescent material is a metal complex.
[0281] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising: a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least the compound composition described in the foregoing embodiments.
[0282] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the mixture is a host material.
[0283] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the compound composition is a host material.
[0284] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one phosphorescent material.
[0285] According to one embodiment of the present invention, the electroluminescent device emits red light or white light.
[0286] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one phosphorescent material, wherein the maximum emission wavelength of the phosphorescent material is above 580 nm.
[0287] According to one embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one phosphorescent material, wherein the maximum emission wavelength of the phosphorescent material is between 600 nm and 900 nm.
[0288] According to one embodiment of the present invention, the phosphorescent material is a metal complex, the metal complex having M(L) a ) u (L b ) v (L c ) q The general formula;
[0289] M is selected from metals with a relative atomic mass greater than 40;
[0290] L a L b L c These are the first, second, and third ligands that coordinate with M, respectively; L a L b L c They can be selectively linked to form multidentate ligands;
[0291] L a L b L c They can be the same or different; u is 1, 2 or 3; v is 0, 1 or 2; q is 0, 1 or 2; the sum of u, v, and q equals the oxidation state of M; when u is greater than or equal to 2, multiple L a They can be the same or different; when v is 2, the two L's b They can be the same or different; when q is 2, the two Ls c They can be the same or different;
[0292] La It has the structure shown in Equation 3:
[0293]
[0294] in,
[0295] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;
[0296] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;
[0297] Rings D and E via U a and U b Condensation;
[0298] U a and U b Each occurrence is either identical or different and is selected from C or N;
[0299] R d R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0300] V1-V4 are selected from CR each time they appear, either identically or differently. v Or N;
[0301] R d R e R v Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0302] Adjacent substituent R d R e Rv They can be arbitrarily connected to form a loop;
[0303] L b L c Each occurrence may be selected from any of the following structures, either identically or differently:
[0304]
[0305] in,
[0306] R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0307] X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ;
[0308] X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ;
[0309] R a R b R c R N1 R N2 R C1 and R C2Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0310] The ligand L b L c In the structure, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a ring.
[0311] In this paper, adjacent substituents R d R e R v The ability to optionally connect to form a ring is intended to indicate the presence of a substituent R. d Substituent R e Substituent R v When, adjacent substituent groups, such as adjacent substituent R d Substituents R between and adjacent e Substituents R between and adjacent v Substituents R between and adjacent d With R e Substituents R between and adjacent d With R v Between and adjacent substituents R e With R v Between these adjacent substituent groups, any one or more can connect to form a ring. It is obvious that when substituent R is present... d Substituent Re Substituent R v At the same time, these substituent groups may not be connected to form a ring.
[0312] In this paper, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be optionally linked to form a ring, intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, substituent R a and R b Between, substituent R a and R c Between, substituent R b and R c Between, substituent R a and R N1 Between, substituent R b and R N1 Between, substituent R a and R C1 Between, substituent R a and R C2 Between, substituent R b and R C1 Between, substituent R b and R C2 Between, substituent R a and R N2 Between, substituent R b and R N2 Between, and R C1 and R C2 Between these substituent groups, one or more of them can be linked to form a ring. For example, adjacent substituents R a R b It can be optionally connected to form a ring, which can form one or more of the following structures, including but not limited to: Wherein, W is selected from O, S, Se, NR' or CR'R'; wherein R', R a ', R b The definition of ' and the aforementioned R a The same. Obviously, these substituents can also not be connected to form a ring.
[0313] According to one embodiment of the present invention, in Formula 3, two adjacent substituents Re The connection forms a loop.
[0314] According to one embodiment of the present invention, in Formula 3, two adjacent substituents R e They can be linked to form 5-membered unsaturated carbon rings, 5-membered heteroaromatic rings, or benzene rings.
[0315] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a benzene ring or a 6-membered heteroaromatic ring.
[0316] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, and ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbon ring.
[0317] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, ring E is a benzene ring or a 6-membered heteroaromatic ring, and the two adjacent substituents R e They can be linked to form benzene rings or 6-membered heteroaromatic rings.
[0318] According to one embodiment of the present invention, in Formula 3, ring D is a 6-membered heteroaromatic ring, ring E is a 5-membered heteroaromatic ring or a 5-membered unsaturated carbide ring, and the two adjacent substituents R e They can be linked to form benzene rings or 6-membered heteroaromatic rings.
[0319] According to one embodiment of the present invention, in formula 3, R d R e R v At least one or two sets of adjacent substituents are linked to form a ring. For example, two substituents R d The connection forms a ring, or two substituents R e The connection forms a ring, or two substituents R v Linkage to form a ring, or substituent R d With substituent R e The links between them form a ring, or the substituent R d With substituent R v The links between them form a ring, or the substituent R e With substituent R v The two substituents R are connected to form a ring or a ring. d The two substituents R connect to form a ring. e The connection forms a ring, or two substituents R d The two substituents R connect to form a ring. v The connection forms a ring, or two substituents R e The two substituents R connect to form a ring. v Linkage forms a ring, substituent R e With substituent R v The two substituents R are linked to form a ring. vLinkage to form a ring, or substituent R d With substituent R v The two substituents R are linked to form a ring. v The connection forms a loop; R d R e R v A similar situation occurs when more adjacent substituents are linked to form a ring.
[0320] According to one embodiment of the present invention, in the electroluminescent device, the phosphorescent material is a metal complex, and the metal complex has M(L) a ) u (L b ) v The general formula;
[0321] M is selected from metals with a relative atomic mass greater than 40;
[0322] L a L b The first and second ligands, respectively, coordinate with M; L a L b They can be selectively linked to form multidentate ligands;
[0323] u is 1, 2, or 3; v is 0, 1, or 2; the sum of u and v equals the oxidation state of M; when u is greater than or equal to 2, multiple L a They can be the same or different; when v is 2, the two L's b They can be the same or different;
[0324] L a It has the structure shown in Equation 3:
[0325]
[0326] in,
[0327] Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring;
[0328] Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring;
[0329] Rings D and E via U a and U b Condensation;
[0330] U a and U b Each occurrence is either identical or different and is selected from C or N;
[0331] R d R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution;
[0332] V1-V4 are selected from CR each time they appear, either identically or differently. v Or N;
[0333] R d R e R v Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;
[0334] Adjacent substituent R d R e R v They can be arbitrarily connected to form a loop;
[0335] The ligand L b It has the following structure:
[0336]
[0337] R1 to R7 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted groups having 2-20 carbon atoms. Alkenyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.
[0338] According to an embodiment of the present invention, in the electroluminescent device, wherein the ligand L b It has the following structure:
[0339]
[0340] Wherein, at least one of R1-R3 is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least one of R4-R6 is selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.
[0341] According to an embodiment of the present invention, in the electroluminescent device, wherein the ligand L b It has the following structure:
[0342]
[0343] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or combinations thereof.
[0344] According to an embodiment of the present invention, in the electroluminescent device, wherein the ligand L b It has the following structure:
[0345]
[0346] Wherein, at least two of R1-R3 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof; and / or at least two of R4-R6 are selected, in the same or different manner each time they appear, from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or combinations thereof.
[0347] According to one embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex, a Pt complex, or an Os complex.
[0348] According to an embodiment of the present invention, in the electroluminescent device, the phosphorescent material is an Ir complex and has Ir(L) ? a (L) b (L) c ), Ir(L a )2(L b ), Ir(L a (L) b )2、Ir(L a )2(L c ) or Ir(L a (L) c Any of the structures shown in )2.
[0349] According to one embodiment of the present invention, wherein L a It has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of a 6-membered 6-membered aromatic ring, a 6-membered 6-membered heteroaromatic ring, a 6-membered 5-membered aromatic ring and a 6-membered 5-membered heteroaromatic ring.
[0350] According to an embodiment of the present invention, in the electroluminescent device, wherein L a It has the structure shown in Formula 3 and contains at least one structural unit selected from the group consisting of naphthalene, phenanthrene, quinoline, isoquinoline and azaphenanthrene.
[0351] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. a The L a Each time it appears, choose either the same or different one from any of the following groups of structures:
[0352]
[0353]
[0354]
[0355]
[0356]
[0357]
[0358]
[0359]
[0360] In the structure described, TMS represents trimethylsilyl.
[0361] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is an Ir complex and contains ligand L. b The L b Each time it appears, choose either the same or different one from any of the following groups of structures:
[0362]
[0363] According to one embodiment of the present invention, in the organic electroluminescent device, the phosphorescent material is selected from metal complexes, and the specific structure of the metal complexes is described in claim 26.
[0364] The specific structures of the phosphorescent materials listed above are merely exemplary and not limiting. Of course, the phosphorescent materials mentioned above are not limited to the mixtures described in this invention; they can also be used in combination with other main materials in the prior art.
[0365] According to one embodiment of the present invention, in the fabrication of the organic electroluminescent device of the present invention, when three or more host materials and a luminescent material are co-deposited to form a luminescent layer, the luminescent layer can be formed by co-depositing the three or more host materials and the luminescent material in different evaporation sources, or by placing a pre-mixed mixture of the three or more host materials in the same evaporation source and then co-depositing it with the luminescent material placed in another evaporation source. This pre-mixing method can further save evaporation sources. Taking the present invention as an example, the luminescent layer can be formed by co-depositing the first compound having the structure of Formula 1, the second compound having the structure of Formula 2, and the third compound having the structure of Formula 1 or Formula 2, along with the luminescent material, in different evaporation sources, or by placing a pre-mixed mixture of the first compound, the second compound, and the third compound in one evaporation source and then co-depositing it with the luminescent material placed in another evaporation source.
[0366] According to an embodiment of the present invention, a method for fabricating an electroluminescent device is also disclosed, the electroluminescent device comprising any of the mixtures described above, the steps of which include:
[0367] Step 1: Provide a substrate and deposit a first electrode on it;
[0368] Step 2: An organic layer is formed by vapor deposition of the mixture as described in any of the preceding embodiments on the first electrode;
[0369] Step 3: Deposit a second electrode on the organic layer.
[0370] The device fabricated using the method described herein may also include other organic layers, which may be disposed between the organic layer formed in step 2 and the two electrode layers. The organic layer formed in step 2 is preferably a light-emitting layer, which may further contain other compounds, preferably phosphorescent compounds.
[0371] According to another embodiment of the present invention, an electronic device is also disclosed, which includes the electroluminescent device described in any of the foregoing embodiments.
[0372] Combination with other materials
[0373] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0374] Materials described herein for use in specific layers of organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the mixtures and compound compositions disclosed herein can be used in combination with a variety of light-emitting dopants, substrates, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.
[0375] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Bruker's nuclear magnetic resonance spectrometer, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometry, gas chromatography-mass spectrometry, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Kesite's electrochemical workstation, Anhui Beiyike's sublimation apparatus, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using equipment conventional in the art (including but not limited to evaporation machines manufactured by Angstrom Engineering, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Beijing Liangtuo, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.
[0376] Material synthesis example:
[0377] The preparation methods of the first, second, and third compounds selected in this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:
[0378] Synthesis Example 1: Synthesis of Compound A-401
[0379] Step 1: Synthesis of Intermediate 2
[0380]
[0381] Under nitrogen protection, intermediate 1 (50.00 g, 265.92 mmol), benzaldehyde (31.04 g, 292.52 mmol), and ethanol (500 mL) were added to a three-necked flask and reacted at 80 °C for 16 h. After the reaction was complete, the solvent was removed by concentration, the solid was washed three times with petroleum ether and dissolved in dichloromethane (500 mL). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 90.55 g, 398.89 mmol) was added and the mixture was reacted at room temperature for 12 h. After the reaction was complete, the reaction solution was extracted with dichloromethane, the organic phase was washed with water, and the solvent was removed. The crude product was purified by column chromatography using PE / DCM = 1 / 1 to give a white solid intermediate 2 (50 g, yield: 69%).
[0382] Step 2: Synthesis of Intermediate 4
[0383]
[0384] Under nitrogen protection, intermediate 2 (40.00 g, 145.92 mmol), intermediate 3 (25.10 g, 160.51 mmol), tetrakis(triphenylphosphine)palladium (1.69 g, 1.46 mmol), potassium carbonate (40.33 g, 291.80 mmol), toluene (200 mL), ethanol (50 mL), and water (50 mL) were added to a three-necked flask, and the mixture was reacted at 100 °C for 16 h. After the reaction was complete, the mixture was extracted with ethyl acetate, washed with water, concentrated to remove the solvent, and the crude product was purified by column chromatography using PE / DCM = 1 / 1 to give a white solid intermediate 4 (35 g, yield: 78%).
[0385] Step 3: Synthesis of compound A-401
[0386]
[0387] Under nitrogen protection, intermediates 4 (3.00 g, 9.81 mmol), 5 (3.64 g, 9.81 mmol), bis(benzylacetone)palladium (111.25 mg, 0.20 mmol), 2-biscyclohexylphosphine-2′,6′-dimethoxybiphenyl (161.12 mg, 0.39 mmol), sodium tert-butoxide (1.89 g, 19.62 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was complete, the liquid was filtered off, and the crude product was purified by column chromatography using PE / DCM = 1 / 1 to give a pale yellow solid compound A-401 (4.8 g, yield: 76%). The product was identified as the target product with a molecular weight of 640.25.
[0388] Synthesis Example 2: Synthesis of Compound A-402
[0389]
[0390] Under nitrogen protection, intermediates 4 (3.00 g, 9.81 mmol), 6 (3.64 g, 9.81 mmol), bis(benzylacetone)palladium (111.25 mg, 0.20 mmol), 2-biscyclohexylphosphine-2′,6′-dimethoxybiphenyl (161.12 mg, 0.39 mmol), sodium tert-butoxide (1.89 g, 19.62 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was complete, the liquid was filtered off, and the crude product was purified by column chromatography using PE / DCM = 1 / 1 to give a pale yellow solid compound A-402 (4.4 g, yield: 70%). The product was identified as the target product with a molecular weight of 640.25.
[0391] Synthesis Example 3: Synthesis of Compound A-405
[0392]
[0393] Under nitrogen protection, intermediates 4 (3.20 g, 10.47 mmol), 7 (3.89 g, 10.47 mmol), tris(dibenzylacetone)dipalladium (479.19 mg, 0.52 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxybiphenyl (429.66 mg, 1.05 mmol), sodium tert-butoxide (2.01 g, 20.93 mmol), and xylene (100 mL) were added to a three-necked flask and reacted at 140 °C for 2 h. After the reaction was complete, the liquid was filtered off, and the crude product was purified by column chromatography using PE / DCM = 1 / 1 to give a pale yellow solid compound A-405 (5.6 g, yield: 84%). The product was identified as the target product with a molecular weight of 640.25.
[0394] Synthesis Example 4: Synthesis of Compound B-1
[0395]
[0396] Under nitrogen protection, intermediate 1-1 (8.2 g, 20.8 mmol), intermediate 2-1 (6 g, 20.8 mmol), tetrakis(triphenylphosphine)palladium (721 mg, 0.6 mmol), potassium carbonate (5.7 g, 41.6 mmol), and solvent (toluene / ethanol / water 80 / 20 / 20 mL) were added to a three-necked flask, and the mixture was reacted overnight at 90 °C. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added to precipitate a white solid. The solid was filtered, and recrystallized from toluene to give compound B-1 (9.3 g, yield: 74%). This product was identified as the target product with a molecular weight of 601.22.
[0397] Synthesis Example 5: Synthesis of Compound B-4
[0398]
[0399] Under nitrogen protection, intermediate 1-1 (6.9 g, 17.4 mmol), intermediate 2-2 (5 g, 17.4 mmol), tetrakis(triphenylphosphine)palladium (603 mg, 0.5 mmol), potassium carbonate (4.8 g, 34.8 mmol), and solvent (toluene / ethanol / water 80 / 20 / 20 mL) were added to a three-necked flask, and the mixture was reacted overnight at 90 °C. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added to precipitate a white solid. The solid was filtered, and recrystallized from toluene to give compound B-4 (8.2 g, yield: 78%). This product was identified as the target product with a molecular weight of 601.22.
[0400] Synthesis Example 6: Synthesis of Compound B-225
[0401]
[0402] Under nitrogen protection, intermediates 1-2 (1.9 g, 5.31 mmol), intermediates 2-3 (2.23 g, 5.31 mmol), tetrakis(triphenylphosphine)palladium (306.82 mg, 0.27 mmol), potassium carbonate (1.47 g, 10.62 mmol), and solvent (toluene / ethanol / water 80 / 20 / 20 mL) were added to a three-necked flask, and the mixture was reacted overnight at 90 °C. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added to precipitate a white solid. The solid was filtered, and recrystallized from toluene to give compound B-225 (1.6 g, yield: 49%). This product was identified as the target product with a molecular weight of 615.19.
[0403] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can improve it to obtain other compound structures selected in this invention.
[0404] Determination of the triplet energy level (T1) of the compound: In this paper, the triplet energy level (T1) of the compound was determined at ultra-low temperatures using the characteristics of long-lived triplet excitons. Specifically, the compound to be tested was dissolved in 2-methyltetrahydrofuran solvent to prepare 10 -5 A solution of concentration M was prepared, placed in a quartz tube, then placed in a Dewar flask and cooled to 77K. The solution of the test compound was irradiated with a 350nm light source, and the phosphorescence spectrum was measured. The spectrum was measured using a spectrophotometer (model F98) manufactured by Shanghai Lingguang Technology Co., Ltd. The vertical axis of the phosphorescence spectrum represents phosphorescence intensity, and the horizontal axis represents wavelength. The minimum value λ1 (nm) of the peak on the shorter wavelength side of the phosphorescence spectrum was taken, and this wavelength value was substituted into the following conversion formula F1 to calculate the triplet energy of the test compound. Conversion formula F1: T1 (eV) = 1240 / λ1. The triplet energy levels of some compounds in this paper, measured using the above method, are recorded in Table 1.
[0405] Table 1. Triplet energy levels (T1) of some compounds.
[0406]
[0407]
[0408] The structure of the compound used is as follows:
[0409]
[0410] In this invention, the HOMO (highest occupied orbital) and LUMO (lowest unoccupied orbital) values of all compounds were obtained by cyclic voltammetry (CV). The tests were conducted using a CorrTest CS120 electrochemical workstation manufactured by Wuhan CorrTest Instruments Co., Ltd., employing a three-electrode system: a platinum disk electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. The test temperature was 25℃, using 0.1 mol / L tetrabutylammonium hexafluorophosphate as the supporting electrolyte and anhydrous DCM as the solvent to prepare 10... -3 A mol / L solution was used, and nitrogen gas was bubbled into the solution for 10 min to remove oxygen before the test. Instrument parameters were set as follows: scan rate 100 mV / s, potential interval 0.5 mV, and test window 1 V to -0.5 V. In this paper, all "HOMO level" and "LUMO level" energy levels are represented by negative values; the smaller the value (i.e., the larger the absolute value), the deeper the energy level. " / " indicates that it was not detected.
[0411] Table 2 shows the HOMO and LUMO energy levels of some compounds.
[0412] compound HOMO[eV] LUMO[eV] Compound A-401 -5.283 -2.347 Compound A-402 -5.300 -2.353 Compound A-405 -5.313 -2.346 Compound B-1 / -2.829 Compound B-4 / -2.811 Compound B-225 / -2.853
[0413] The method for testing the vapor deposition temperature of the compound in this invention is to vapor deposit the compound under test using a vapor deposition machine manufactured by Angstrom Engineering Incorporated: the compound under test is loaded into the evaporation source, and the vapor deposition temperature is determined under a vacuum of approximately 10 °C. -6 In the case of Torr, The required temperature (evaporation temperature) for vapor deposition of the compounds at the specified rate is listed in Table 3. Table 3 lists the required vapor deposition temperatures for compounds A-401, A-402, A-405, B-1, B-4, and B-225 of the present invention when vapor deposited using the above method.
[0414] Table 3 shows the evaporation temperatures of some compounds.
[0415]
[0416] Using multiple (usually three or more) raw materials to prepare the light-emitting layer is beneficial for obtaining light-emitting devices with better overall performance. However, if the conventional preparation method is used, where each component is used as a separate evaporation source, the preparation process and cost will be significantly increased. The desired approach is to premix the multi-component materials to form a premix with high evaporation stability, and then use it as a single evaporation source to reduce the complexity of the vacuum deposition process.
[0417] However, the stability of the composition in the film formed by the evaporation of the mixture has a significant impact on device performance. Therefore, for a premix to be used as a single evaporation source, its co-evaporation must be stable; that is, the smaller the deviation in the deposition ratio of the film formed by the mixture during the vacuum deposition process, the better. However, when two compounds are mixed together, it is difficult to achieve a stable co-evaporation mixture because the possible interactions between them can affect the stability of the evaporated film.
[0418] Through research, the inventors have provided a novel mixture comprising at least three hole-transporting compounds and electron-transporting compounds with distinct structures, wherein the hole-transporting compounds are represented by Formula 1. The mixture of this invention enables stable single-source co-evaporation. In particular, the stability of the film deposited from the mixture can be improved by selecting hole-transporting compounds and electron-transporting compounds with specific "heavy" and "light" evaporation characteristics, as provided in this invention. The stability of this mixture can be demonstrated by compositional analysis of films manufactured from a single co-evaporation source containing this three-component premix. Specifically:
[0419] Mixture examples
[0420] Mixture Example 1: Compounds A-401, A-402, and B-1 were pre-melted and mixed in a weight ratio of A-401:A-402:B-1 = 2.5:0.5:7 to form mixture MX1 of the present invention. The pre-mixed mixture MX1 was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the evaporation was carried out under a vacuum of approximately 10... -6 In the case of Torr, The mixture MX1 evaporates at a rate that is then deposited onto a glass substrate. During the deposition process... The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are shown in Table 4.
[0421] Table 4 records and displays the composition (%) of the membranes sequentially deposited from the premixed MX1 as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column, eluent: methanol / isopropanol (6 / 4), detection wavelength: 229 nm.
[0422] Table 4. Component proportions of MX1 mixture in the membrane.
[0423]
[0424]
[0425] Mixture Example 2: Compounds A-401, A-402, and B-1 were pre-melted and mixed in a weight ratio of A-401:A-402:B-1 = 3.5:0.5:6 to form mixture MX2 of the present invention. The pre-mixed mixture MX2 was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the evaporation was carried out under a vacuum of approximately 10... -6 In the case of Torr, The MX2 mixture evaporates at a rate that is then deposited onto a glass substrate. During the deposition process... The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are shown in Table 5.
[0426] Table 5 records and displays the composition (%) of the membranes sequentially deposited from the premixed MX2 as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column, eluent: methanol / isopropanol (6 / 4), detection wavelength: 229 nm.
[0427] Table 5. Component proportions of the MX2 mixture in the membrane.
[0428]
[0429] Mixture Example 3: Compounds A-401, B-1, and B-4 were pre-melted and mixed in a weight ratio of A-401:B-1:B-4 = 3:6:1 to form mixture MX3 of the present invention. Mixture MX3 was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the evaporation was carried out under a vacuum of approximately 10... -6 In the case of Torr, The MX3 mixture was evaporated at a rate of [percentage missing] and deposited onto a glass substrate. The deposition formed a thickness of [missing information]. The film is then continuously replaced with a substrate without stopping deposition and cooling of the evaporation source to form multiple films with a thickness of [thickness value missing]. The membrane was analyzed by HPLC, and the results are shown in Table 6.
[0430] Table 6 records and displays the composition (%) of the membranes sequentially deposited from the premixed MX3 as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column, eluent: methanol / isopropanol (6 / 4), detection wavelength: 229 nm.
[0431] Table 6. Component proportions of MX3 mixture in the membrane.
[0432] membrane A-401(%) B-1 + B-4 (%) Membrane 1 30.0 70.0 Membrane 2 29.4 70.6 Membrane 3 29.7 70.3 Membrane 4 29.9 70.1 Membrane 5 29.8 70.2 Membrane 6 30.1 69.9
[0433] Mixture Example 4: Compounds A-401, A-405, and B-225 were pre-melted and mixed in a weight ratio of A-401:A-405:B-225 = 3.5:0.5:6 to form mixture MX4 of the present invention. The pre-mixed mixture MX4 was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the evaporation was carried out under a vacuum of approximately 10... -6In the case of Torr, The MX4 mixture evaporates at a rate that is then deposited onto a glass substrate. During the deposition process... The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are presented in Table 7.
[0434] Table 7 records and displays the composition (%) of the membranes sequentially deposited from the premixed MX4 as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column, eluent: methanol / isopropanol (6 / 4), detection wavelength: 229 nm.
[0435] Table 7. Component proportions of MX4 mixture in the membrane.
[0436]
[0437] Comparative Example 1: Compounds A-401 and B-1 were pre-melted and mixed in a weight ratio of A-401:B-1 = 3:7 to form comparative mixture C-MX1. The pre-mixed mixture was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the vacuum degree was approximately 10. -6 In the case of Torr, The rate of deposition allows the C-MX1 mixture to co-evaporate and deposit onto the glass substrate. The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are collected in Table 8.
[0438] Table 8 records and displays the composition (%) of the membranes sequentially deposited from the two-component premixture C-MX1, as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column; eluent: methanol / isopropanol (6 / 4); detection wavelength: 229 nm.
[0439] Table 8 shows the component proportions of the comparative mixture C-MX1 in the membrane.
[0440]
[0441] Comparative Example 2: Compounds A-402 and B-1 were pre-melted and mixed in a weight ratio of A-402:B-1 = 3:7 to form comparative mixture C-MX2. The pre-mixed mixture was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the vacuum degree was approximately 10. -6 In the case of Torr, The rate allows the C-MX2 mixture to co-evaporate and deposit onto the glass substrate. During deposition... The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are presented in Table 9.
[0442] Table 9 records and displays the composition (%) of the membranes sequentially deposited from the two-component premixture C-MX2, as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column; eluent: methanol / isopropanol (6 / 4); detection wavelength: 229 nm.
[0443] Table 9 Comparative composition ratios of C-MX2 mixtures in the membrane
[0444]
[0445]
[0446] Comparative Example 3: Compounds A-401 and B-4 were pre-melted and mixed in a weight ratio of A-401:B-4 = 3:7 to form comparative mixture C-MX3. The pre-mixed mixture was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the vacuum degree was approximately 10. -6 In the case of Torr, The rate of deposition allows the C-MX3 mixture to co-evaporate and deposit onto the glass substrate. The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are presented in Table 10.
[0447] Table 10 records and displays the composition (%) of the membranes sequentially deposited from the two-component premixture C-MX3, as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column; eluent: methanol / isopropanol (6 / 4); detection wavelength: 229 nm.
[0448] Table 10 shows the component proportions of the C-MX3 mixture in the membrane.
[0449]
[0450] Comparative Example 4: Compounds A-405 and B-225 were pre-melted and mixed in a weight ratio of A-405:B-225 = 4:6 to form comparative mixture C-MX4. The pre-mixed mixture was then ground into powder and loaded into an evaporation source. The distance between the evaporation source and the glass substrate was set to 35-60 cm, and the vacuum degree was approximately 10. -6 In the case of Torr, The rate allows the C-MX4 mixture to co-evaporate and deposit onto the glass substrate. During deposition... The substrate is continuously replaced after the film is deposited without stopping the deposition and cooling of the source to form multiple layers with... The membrane was analyzed by HPLC, and the results are presented in Table 11.
[0451] Table 11 records and displays the composition (%) of the membranes sequentially deposited from the two-component premixture C-MX4, as analyzed by HPLC. HPLC analysis conditions used: Analytical column: ODS column; eluent: methanol / isopropanol (6 / 4); detection wavelength: 229 nm.
[0452] Table 11 shows the component proportions of the C-MX4 mixture in the membrane.
[0453]
[0454] Discussion: As can be seen from the data in Tables 4 to 11 above, the mixture of three or more hole-transporting compounds and electron-transporting compounds with different structures in this invention can achieve the desired stable single-source co-evaporation by specifically selecting a hole-transporting compound with the structure of Formula 1 and combining it with two or more other compounds.
[0455] Based on the data in Tables 4 to 11 above, calculate the stability of a certain component mass ratio in the membrane, where C m The mass proportion of the compound in the m-th membrane is C. m C0 indicates that its mass proportion in the premixture is C0, |C m -C0| represents the mass proportion C of the compound in any one of the n membranes. m The absolute value of the difference between C0 and m, where m is an integer from 1 to n; |C m -C0| max C represents the mass proportion of the compound in any one of the n membranes. m The maximum absolute value of the difference from C0. Tables 4-9 use A-401 as an example, Tables 5-8 use B-1 as an example, and Tables 7-11 use B-225 as an example. The data is shown in Table 12 below:
[0456] Table 12 Stability data of the membrane
[0457] Mixture Number <![CDATA[|C m -C0| max ]]> Mixture Number <![CDATA[|C m -C0| max ]]> MX1 1.2% C-MX1 3.4% MX2 1.2% C-MX2 4.7% MX3 0.6% C-MX3 7.7% MX4 1.1% C-MX4 9.3%
[0458] The calculation of the above data, taking MX3 as an example: According to mixture example 3, the C0 of compound A-401 is 30%, n = 6; m is selected from 1, 2, 3, 4, 5, 6; |C1-C0| = 0%, |C2-C0| = 0.6%; |C3-C0| = 0.3%; |C4-C0| = 0.1%; |C5-C0| = 0.2%; |C6-C0| = 0.1%; Based on the above data, it can be determined that |C m -C0| max =0.6%.
[0459] As can be seen from the data in Table 12, the proportions of each component in the film formed by the mixtures MX1-MX4 show only slight fluctuations. This data demonstrates that the mixtures of the present invention exhibit higher stability when evaporated as a single evaporation source, and their application in OLED devices can simplify the production process and reduce production costs.
[0460] In particular, the inventors were pleasantly surprised to discover that by selecting hole-transporting compounds and electron-transporting compounds with specific "heavy" and "light" evaporation characteristics to form the mixture of the present invention, its evaporation stability can be further improved. Specifically, as shown in Table 8, the weight ratio of hole-transporting compound A-401 in films 1-6 gradually decreases overall, meaning A-401 is lighter than B-1; similarly, as shown in Table 9, the weight ratio of hole-transporting compound A-402 in films 1-6 gradually increases overall, meaning A-402 is heavier than B-1. As shown in Table 11, the weight ratio of hole transport compound A-405 in membranes 1-6 gradually decreases, meaning A-405 is lighter than B-225. Mixed Examples 1-2 are mixtures MX1 and MX2 formed by premixing electron transport compound B-1, hole transport compound A-402 (which is heavier than B-1), and hole transport compound A-401 (which is lighter than B-1) in different proportions. Mixed Example 4 is mixture MX4 formed by premixing electron transport compound B-225, hole transport compound A-405 (which is lighter than B-225), and hole transport compound A-401 (which is heavier than B-225) in different proportions. As shown in Table 12, the proportions of each component in the membranes prepared from MX1, MX2, and MX4 fluctuate only slightly, indicating good stability. Hybrid Example 3, which employs hole-transporting compound A-401, electron-transporting compound B-1 (which is "heavier" than A-401), and electron-transporting compound B-4 (which is "lighter" than A-401), achieves further improvements compared to MX1 and MX2, which already have high evaporation stability.
[0461] Furthermore, using the mixture of the present invention to prepare devices not only simplifies the process but also achieves excellent overall device performance. To support the above viewpoint, a set of examples of OLED devices prepared by the premix of the present invention are provided.
[0462] Device Example 1
[0463] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -6 In the case of Torr, The deposition rate was achieved sequentially on the ITO anode via thermal vacuum. Compounds HT and HI were co-deposited as a hole injection layer (HIL, weight ratio 97:3), with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, the mixture MX4 of the present invention, which serves as the main material (the weight ratio of compounds A-401, A-405, and B-225 in the mixture MX4 is 35:5:60), is placed in the same evaporation source and co-deposited with compound RD, which serves as a dopant in another evaporation source, to form an emissive layer (EML, the weight ratio of mixture MX4 to compound RD is 97:3), with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL, weight ratio 40:60), with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.
[0464] The detailed device layer structure and thickness are shown in the table below. The layers use more than one material; they are obtained by doping different compounds in the stated weight ratios.
[0465] Table 13 Device structure of Device Example 1
[0466]
[0467]
[0468] The structure of the new material used in the device is shown below:
[0469]
[0470] Table 14 lists the constant current of 10 mA / cm². 2 Under the given conditions, the measured maximum emission wavelength (λ) of the device max The full width at half maximum (FWHM), voltage (V), current efficiency (CE), power efficiency (PE), and external quantum efficiency (EQE) data are available, as well as at 80 mA / cm². 2 The device lifetime (LT97) was tested under constant current. Device lifetime (LT97) refers to the time required for the device brightness to decay to 97% of its initial brightness.
[0471] Table 14 Device data for Device Example 1
[0472]
[0473] The data in Table 14 show that Device Example 1 exhibits excellent overall device performance, such as high device efficiency and long device lifetime. Therefore, the mixture of the present invention can not only be used as a single evaporation source in the fabrication process of OLED devices, simplifying the production process and reducing production costs; but also, as a host material, it can still achieve excellent device performance.
[0474] In summary, the novel mixture disclosed in this invention exhibits high evaporation stability and provides excellent device performance, thus possessing broad application prospects.
[0475] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.
Claims
1. A mixture comprising at least a first compound, a second compound, and a third compound; in, The first compound is a hole-transporting compound; The second compound is an electron transport compound; The third compound is selected from hole-transporting compounds or electron-transporting compounds; The first compound, the second compound, and the third compound have different chemical structures. The mixture comprises a premix formed by pre-mixing the first compound, the second compound, and the third compound, wherein at least one of the first compound, the second compound, and the third compound has a mass ratio of C0 in the mixture. When the mixture is deposited under a certain vacuum and at a certain rate, the premix is evaporated on a surface positioned at a certain distance from the evaporated mixture to form n films of a certain thickness, and the at least one compound has a mass ratio of C in the nth film. n n is an integer ≥ 1; Among the n films formed by vapor deposition, the mass ratio C of at least one compound in any one of the films is... m The absolute value of the difference between C0 and |C m -C0|≤2%, where m is an integer selected from 1 to n; The hole transport compound has the structure represented by Formula 1; in, X is selected from NR n O or S; Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5; If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L; L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar1 and Ar2 are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof. R w R n R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R w They can be arbitrarily connected to form a loop; Adjacent substituent R n They can be arbitrarily connected to form a ring.
2. The mixture of claim 1, wherein, At least one of the first, second, and third compounds has a mass ratio of C0 in the mixture. When the mixture is deposited at a certain vacuum level and a certain rate, n films of a certain thickness are formed by evaporating the mixture on a surface positioned at a certain distance from the mixture being evaporated, and the mass ratio of the at least one compound in the nth film is C0. n ; n is an integer ≥ 1; wherein, among the n films formed by vapor deposition, the mass ratio C of at least one compound in any one film is... m The absolute value of the difference between C0 and |C m -C0|≤1.5%.
3. The mixture of claim 1, wherein, When the third compound is selected from hole-transporting compounds, the third compound is heavier than the second compound in terms of vapor deposition characteristics, and the first compound is lighter than the second compound. When the third compound is selected from electron transport compounds, the second compound is heavier than the first compound and the third compound is lighter than the first compound in terms of vapor deposition characteristics.
4. The mixture as described in claim 1 or 3, wherein, When the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, the vacuum degree is 10. -6 In the case of Torr or lower, the evaporation rate is The absolute value of the temperature difference between any two vapor deposition processes is less than 30℃; Preferably, the absolute value of the vapor deposition temperature difference between any two of the first compound, the second compound, and the third compound is less than 20°C; More preferably, the absolute value of the temperature difference between any two vapor deposition processes is less than 10°C.
5. The mixture as described in claim 1 or 3, wherein, When the first compound, the second compound, and the third compound are deposited at the same rate under the same vacuum degree, wherein the vacuum degree is 10... -6 In the case of Torr or lower, the evaporation rate is The vapor deposition temperature of the first compound, the second compound, and the third compound is between 120℃ and 390℃; Preferably, the vapor deposition temperature of the first compound, the second compound, and the third compound is between 140°C and 370°C; More preferably, the vapor deposition temperature of the first compound, the second compound, and the third compound is between 160°C and 360°C; most preferably, the vapor deposition temperature of the first compound, the second compound, and the third compound is between 200°C and 350°C.
6. The mixture as claimed in claim 1 or 3, wherein, At least one of the first compound, the second compound, and the third compound has a triplet energy level T1 < 2.65 eV; preferably, T1 < 2.60 eV.
7. The mixture according to any one of claims 1-6, wherein, The first compound has a structure represented by formula 1-1 or formula 1-2: in, X is selected from NR n O or S; Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; Z1 to Z4 are selected from CR each time they appear, either identically or differently. z Or N; When W1 to W5 appear, they are either identically or differently selected from C, CR. w Or N, and one of W1 to W5 is selected from C and connected to L; L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar1 and Ar2 are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof. R w R n R z Each time it appears, it is selected from the group consisting of the same or different elements: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted... Or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R w They can be arbitrarily connected to form a loop; Adjacent substituent R n They can be arbitrarily connected to form a ring.
8. The mixture as claimed in claim 1 or 7, wherein, When W1 to W5 appear, they are either the same or different and are selected from C or CR. w And one of W1 to W5 is selected from C and connected to L; Preferably, one of W2, W3 and W4 is C and connected to L.
9. The mixture of claim 1 or 7, wherein X is selected from O or S; Preferably, X is selected from O.
10. The mixture of claim 1 or 7, wherein R w R z R n Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and combinations thereof; Preferably, R w R z R n Each time it appears, it is selected from the group consisting of the following, either the same or different: hydrogen, deuterium, halogen, phenyl, vinyl, naphthyl, biphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiopheneyl. alkyl, methyl, ethyl, tert-butyl, adamantyl, cyclohexyl, cyclopentyl, and combinations thereof.
11. The mixture of claim 1 or 7, wherein Ar1 and Ar2 are selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms, substituted or unsubstituted cycloalkyl groups having 4-10 cyclic carbon atoms, or combinations thereof. Ar is selected from substituted or unsubstituted aryl groups having 6-25 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-24 carbon atoms; Preferably, Ar1 and Ar2, each time appearing, are selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilylfluorenyl, substituted or unsubstituted... alkyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclohexyl, or combinations thereof; Ar is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted spirosilylfluorenyl, substituted or unsubstituted base; More preferably, Ar, Ar1, and Ar2, each time appearing, are selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, and silylfluorenyl. Base, or a combination thereof.
12. The mixture of claim 1, wherein, The first compound is selected from the group consisting of the following compounds: Optionally, the hydrogen in the structure of compounds A-1 to A-662 may be partially or completely replaced by deuterium.
13. The mixture according to claim 1 or 3, wherein, The electron transport compound comprises at least one chemical group selected from the group consisting of: oxazole, thiazole, benzoxazole, benzothiazole, naphthoxazole, naphthothiazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, azadibenzothiophene, azadibenzofuran, dibenzoselenophene, benzene, pyridine, pyrimidine, carbazole, azacarbazole, indolocarbazole, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, triazine, and combinations thereof; Preferably, the electron transport compound contains a triazine group.
14. The mixture according to any one of claims 1-13, wherein, The second compound has a structure represented by Formula 2: in, X9 to X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N; L'2, L3, L'3 are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Ar 21 Ar 22 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Adjacent substituent R x They can be arbitrarily connected to form a loop; Preferably, Ar 21 Ar 22 At least one of the following is selected from dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), silanyl (substituted or unsubstituted), fluorenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), etc. A group, or a combination thereof; Adjacent substituent R x They can be arbitrarily connected to form a ring.
15. The mixture as claimed in claim 1 or 14, wherein, The second compound has a structure represented by Formula 2-1: in, X1 to X4 are selected from CR each time they appear, either identically or differently. x Or N; X5 to X 13 Each time it appears, it is selected from C, CR, either identically or differently. x Or N, and at least one of X5 to X8 is selected from C and connected to L2, X9 to X 13 At least one of them is selected from C and connected to L2; L2, L'2, L3, L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof. Ar 21 Ar 22 Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently. R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R x They can be arbitrarily connected to form a ring.
16. The mixture of claim 15, wherein, L2, L'2, L3, L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof. Preferably, L2, L'2, L3, and L'3 are selected, either identically or differently, from single bonds, or from substituted or unsubstituted aryl groups having 6-20 carbon atoms, or combinations thereof; More preferably, L2, L'2, L3, and L'3, each time appearing, are selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted trimethyleneene, substituted or unsubstituted 9,9-dimethylfluorene, substituted or unsubstituted terphenylene, substituted or unsubstituted phenylene... Base, or a combination thereof.
17. The mixture of claim 15, wherein, X1 to X4 are selected from CR each time they appear, either identically or differently. x X5 to X 13 Each time it appears, it is selected from C or CR, either the same or different. x And X6 or X7 is selected from C and connected to L2, X 11 Selected from C and connected to L2; Preferably, R x Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; More preferably, R x Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, phenyl, pyridyl, vinyl, adamantyl, methyl, ethyl, isopropyl, cyclopropane, naphthyl, biphenyl, phenanthrene, triphenylene, tert-butyl, trifluoromethyl, 9,9-dimethylfluorenyl, terphenyl, dibenzothiophene, dibenzofuranyl, benzothiazolyl, benzoxazolyl, phenanthrenexazolyl, phenanthrenethiazolyl Bases and their combinations.
18. The mixture of claim 14 or 15, wherein, Ar 21 Ar 22 Each occurrence has the same or different structure represented by any one of equations Ar-1 to Ar-6: in, Ar Q Each time it appears, it is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof, either identically or differently. Q is selected from C and CR each time it appears, either identically or differently. Q Or N, at least one Q is selected from C and connected to L3 or L'3; Q1 is selected from O, S, Se, NR Q or CR Q R Q ; Q2 is selected from O, S, or Se; R Q Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R Q They can be arbitrarily connected to form a loop; Preferably, Ar 21 Ar 22 Each time it appears, it has the same or different structure represented by any one of the formulas Ar-1, Ar-2 and Ar-4.
19. The mixture of claim 18, wherein, In formulas Ar-1 to Ar-6, Q is selected from C or CR each time it appears, either the same or different. Q Q1 is selected from O, S, or CR. Q R Q Q2 is selected from O or S; Preferably, R Q Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; More preferably, R Q Each occurrence is selected from the group consisting of the following elements, either identically or differently: hydrogen, deuterium, halogen, phenyl, pyridyl, vinyl, adamantyl, methyl, ethyl, isopropyl, cyclopropane, naphthyl, biphenyl, phenanthrene, triphenylene, tert-butyl, trifluoromethyl, 9,9-dimethylfluorenyl, terphenyl, dibenzothiophene, dibenzofuranyl, benzothiazolyl, benzoxazolyl, phenanthrenexazolyl, phenanthrenethiazolyl Bases and their combinations.
20. The mixture of claim 1, wherein the second compound is selected from the group consisting of: Optionally, the hydrogen in the structure of compounds B-1 to B-257 may be partially or completely replaced by deuterium.
21. The mixture of claim 14, wherein, The third compound has a structure represented by Formula 1 or Formula 2; Preferably, the third compound has a structure represented by Formula 1, and the third compound is an isomer or isotope isomer of the first compound; or the third compound has a structure represented by Formula 2, and the third compound is an isomer or isotope isomer of the second compound.
22. The mixture of claim 1, wherein, The deuteration rate of at least one of the first compound, the second compound, and the third compound is 5%-100%; Preferably, the deuteration rate is 30%-100%; More preferably, the deuteration rate is 50%-100%.
23. An electroluminescent device, comprising: A first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises at least a mixture as described in any one of claims 1-22.
24. The electroluminescent device as claimed in claim 23, wherein, The organic layer is a light-emitting layer, and the mixture is the main material.
25. The electroluminescent device as claimed in claim 24, wherein, The organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one phosphorescent material; preferably, the maximum emission wavelength of the phosphorescent material is above 580 nm.
26. The electroluminescent device as claimed in claim 25, wherein, The phosphorescent material is a metal complex, and the metal complex has M(L) a ) u (L b ) v (L c ) q The general formula; M is selected from metals with a relative atomic mass greater than 40; L a L b L c These are the first, second, and third ligands that coordinate with M, respectively; L a L b L c They can be selectively linked to form multidentate ligands; L a L b L c They can be the same or different; u is 1, 2 or 3; v is 0, 1 or 2; q is 0, 1 or 2; the sum of u, v, and q equals the oxidation state of M; when u is greater than or equal to 2, multiple L a They can be the same or different; when v is 2, the two L's b They can be the same or different; when q is 2, the two Ls c They can be the same or different; L a It has the structure shown in Equation 3: in, Ring D is selected from a 5-membered heteroaryl ring or a 6-membered heteroaryl ring; Ring E is selected from a 5-membered unsaturated carbon ring, a benzene ring, a 5-membered heteroaromatic ring, or a 6-membered heteroaromatic ring; Rings D and E via U a and U b Condensation; U a and U b Each occurrence is either identical or different and is selected from C or N; R d R e Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; V1-V4 are selected from CR each time they appear, either identically or differently. v Or N; R d R e R v Each time it appears, it is selected from the group consisting of, either identically or differently, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R d R e R v They can be arbitrarily connected to form a loop; L b L c Each occurrence may be selected from any of the following structures, either identically or differently: in, R a R b and R c Each occurrence, whether identical or different, indicates monosubstitution, polysubstitution, or no substitution; X b Each time it appears, choose from the following groups, either the same or different: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each time it appears, choose from the following groups, either the same or different: O, S, Se, and NR. N2 ; R a R b R c R N1 R N2 R C1 and R C2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, and substituted or unsubstituted alkenes having 2-20 carbon atoms. alkyl, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; The ligand L b L c In the structure, adjacent substituents R a R b R c R N1 R N2 R C1 and R C2 They can be arbitrarily connected to form a loop; Preferably, the phosphorescent material is selected from the group consisting of the following metal complexes: In the structure described, TMS represents trimethylsilyl.
27. An electronic device comprising the electroluminescent device according to any one of claims 23-26.
28. A compound composition comprising a first compound represented by Formula 1, a second compound represented by Formula 2, and a third compound represented by Formula 1 or Formula 2, wherein the first compound, the second compound, and the third compound have different structures from each other; in, X is selected from NR n O or S; Ar is selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; If Z1 to Z4 appear the same or different each time, choose C; CR z Or N, and one of Z1 to Z4 is selected from C and connected to a six-membered ring containing W1 to W5; If W1 to W5 appear the same or different each time, choose C; CR w Or N, and one of W1 to W5 is selected from C and connected to L; L is selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof; Ar1 and Ar2 are selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, or combinations thereof. in, X9 to X 13 Each time it appears, it is selected from CR in the same or different ways. x Or N; L'2, L3, and L'3, each time appearing, are selected from single bonds, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof. Ar 21 Ar 22 Selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; R x R w R n R z Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, and substituted or unsubstituted alkyl groups having 1-20 carbon atoms. Alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; Adjacent substituent R w They can be arbitrarily connected to form a loop; Adjacent substituent R n They can be arbitrarily connected to form a loop; Adjacent substituent R x They can be arbitrarily connected to form a ring.
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