Aromatic amine derivatives organic electroluminescent materials and devices

Abstract

Disclosed are aromatic amine derivative organic electroluminescent materials and devices thereof. The compound is a pyrene compound substituted with an aromatic amine, wherein a substituent is introduced into the N-ortho position of one aromatic group of the aromatic amine and a (hetero) aromatic group containing an ortho substituent is introduced into the N-para position, and a substituent is introduced into the N-ortho position of another aromatic group, which can increase the conjugation and stability of the molecule while reducing the planarity of each conjugated system of the molecule. The compound can be used as a luminescent material in an organic electroluminescent device. These novel compounds can provide better device performance, such as device life and external quantum efficiency. Also disclosed is an electroluminescent device and a compound formula.

Description

Technical Field

[0001] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a pyrene compound containing aromatic amine substitution, an organic electroluminescent device containing the compound, and a compound formulation. Background Art

[0002] Organic electronic devices include but are not limited to the following categories: 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 photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced 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 the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0004] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet 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 has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, 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). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] The luminescent color of OLED can be achieved by designing the structure of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLED phosphorescent materials have been successfully commercialized. Currently, phosphorescent blue OLEDs have short lifespans, difficulty in achieving deep blue, unsaturated blue, and high operating voltage. Fluorescent blue OLEDs have longer lifespans than phosphorescent blue OLEDs, but have problems such as low efficiency, so there is a great need to improve the efficiency and other performance of fluorescent blue electroluminescent devices.

[0006] KR1020110054192A publicly reported a triarylamine compound with pyrene as the core, the general formula of which is In the application, at least one of R1-R5 is a cyano substituent and at least one is a substituted or unsubstituted aryl group. Most of the specific structures disclosed are aryl amines with a cyano substituent at the N-ortho position of an aryl substituent. The specific structures are The structure of R3 is not further limited, which is different from the requirement in the present application for further introducing an ortho-substituted aromatic group to the N position of the aromatic substituent in the aromatic amine. It is worth noting that the invention does not focus on the impact of the introduction of the ortho-substituted aromatic group on the device performance.

[0007] KR1020140076170A publicly reported the research on triarylamine compounds with pyrene as the core, and its general formula is The compound must contain both an electron-withdrawing group and a deuterated aromatic group, wherein the electron-withdrawing substituent is a halogen, a cyano group, and a trifluoromethyl group. The specific structure is The ortho-substituents of the N-substituted aromatic groups involved in the application are electron-withdrawing fluorine atoms and deuterated aromatic groups, and there is no disclosure or teaching that the device performance will be improved when both aromatic groups of aromatic amine have N-ortho-substituents.

[0008] CN106170474A reports the research on triarylamine compounds with pyrene as the core, and its general formula is The specific structure is Although the application involves a structure in which both aromatic groups of aromatic amine are substituted at the ortho position, it does not further introduce an aromatic group at the N-para position of the aromatic amine as in the present invention to increase the conjugation and stability of the molecule, so as to achieve good luminescence efficiency of the blue light device.

[0009] These documents disclose some fluorescent luminescent materials with aromatic amine structure and pyrene as the core. Diarylamine substituted pyrene compounds play an important role in the field of fluorescent blue light, but fluorescent luminescent materials still need further development to obtain higher device performance. Summary of the invention

[0010] The present invention aims to provide a series of novel pyrene compounds with aromatic amine structures to solve at least part of the above problems. The compounds can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide better device performance, such as external quantum efficiency and device life.

[0011] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0012]

[0013] Among them, in formula 1,

[0014] R1-R 10 At least one substituent has a structure represented by Formula 2:

[0015]

[0016] And the substituent R1-R 10The remaining in each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0017] Among them, in formula 2,

[0018] "*" represents the position where the substituent having the structure of Formula 2 is attached to Formula 1;

[0019] L is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0020] X1 to X4 are selected from CR in the same or different manner at each occurrence. x1 or N;

[0021] Y1 to Y3 are selected from CR y1 or N;

[0022] Z1 to Z4 are selected from CR in the same or different manner at each occurrence. z1 or N;

[0023] R x1The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0024] R y1 and R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, mercapto, phosphino, and combinations thereof;

[0025] R x , R y and R z Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

[0026] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which comprises the compound having the structure of Formula 1. The specific structure of the compound is described in the above embodiments.

[0027] According to another embodiment of the present invention, a compound formulation is also disclosed, which comprises the compound having the structure of Formula 1. The specific structure of the compound is described in the above embodiment.

[0028] A series of novel pyrene compounds with aromatic amine structures provided by the present invention can be used as luminescent materials in organic electroluminescent devices. These novel compounds introduce an aromatic group containing an ortho-substituent at the N-para position of an aromatic group of the aromatic amine and further have a substituent at the N-ortho position, and contain a substituent at the N-ortho position of another aromatic group of the aromatic amine, so that the conjugation and stability of the molecule can be increased while reducing the planarity of each conjugated system of the molecule. The application of these novel compounds in organic electroluminescent devices can provide better device performance, such as external quantum efficiency and device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

[0030] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein. DETAILED DESCRIPTION

[0031] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0032] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated 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 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 by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0033] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can 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 can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0034] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0035] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an 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 No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0036] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0037] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0038] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0039] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0040] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0041] 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, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0042] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0043] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0044] Definition of Substituent Terms

[0045] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0046] Alkyl - includes straight chain and branched chain alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbon in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferred.

[0047] Cycloalkyl - as used herein includes cyclic alkyl groups. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. In addition, cycloalkyl groups may be optionally substituted. The carbons in the ring may be substituted with other heteroatoms.

[0048] Alkenyl - As used herein, linear and branched olefin groups are encompassed. Preferred alkenyl groups are alkenyl groups containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 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 and 3-phenyl-1-butenyl. In addition, alkenyl groups may be optionally substituted.

[0049] Alkynyl - as used herein, encompasses both straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Additionally, alkynyl groups may be optionally substituted.

[0050] Aryl or aromatic group - As used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, phenanthrene, fluorene, pyrene, letrozole, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quaterphenyl.

[0051] Heterocyclyl or heterocycle - As used herein, both aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclyls are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclyl may also be an aromatic heterocyclyl having at least one heteroatom selected from nitrogen, oxygen, sulfur and selenium atoms.

[0052] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups that may contain from 1 to 5 heteroatoms are contemplated. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 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, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group comprises an oxadiazole, an isocyanine ...

[0053] Alkoxy - is represented by -O-alkyl. Examples and preferred examples of alkyl are the same as those described above. Examples of alkoxy having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. Alkoxy having 3 or more carbon atoms may be linear, cyclic or branched.

[0054] Aryloxy- is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as described above. Examples of aryloxy having 6 to 40 carbon atoms include phenoxy and biphenyloxy.

[0055] Aralkyl - As used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of aralkyl 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, , 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, 1-2-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.

[0056] The term "aza" in azafluorene, azaspirobifluorene ring, azadibenzofuran, aza-dibenzothiophene, etc., refers to one or more CH groups in the corresponding aromatic fragment being replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0057] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be selected from one or more deuterated, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted alkyl having 3 to 20 ring carbon atoms, The present invention may be substituted with an unsubstituted cycloalkyl group having 1 to 20 carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms or preferably an unsubstituted aryl group having 6 to 12 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms or preferably an unsubstituted heteroaryl group having 3 to 12 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group and a combination thereof.

[0058] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (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 a substituent or attaching a fragment are considered equivalent.

[0059] In the compounds mentioned in the present 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. Due to its enhanced efficiency and stability of the device, the replacement of other stable isotopes in the compound may be preferred. In the compounds mentioned in the present disclosure, a deuterated substituent, such as a deuterated methyl, means that at least one hydrogen atom in the substituent (methyl) is replaced by deuterium.

[0060] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0061] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, 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.

[0062] The expression that two adjacent substituents can be optionally linked to form a ring is also intended to be considered to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0063]

[0064] The expression that two adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0065]

[0066] Furthermore, the statement that two adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0067]

[0068] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0069]

[0070] Among them, in formula 1,

[0071] R1-R 10 At least one substituent has a structure represented by Formula 2:

[0072]

[0073] And the substituent R1-R 10 The remaining in each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0074] Among them, in formula 2,

[0075] "*" represents the position where the substituent having the structure of Formula 2 is attached to Formula 1;

[0076] L is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;

[0077] X1 to X4 are selected from CR in the same or different manner at each occurrence. x1 or N;

[0078] Y1 to Y3 are selected from CR y1 or N;

[0079] Z1 to Z4 are selected from CR in the same or different manner at each occurrence. z1 or N;

[0080] R x1The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0081] R y1 and R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, mercapto, phosphino, and combinations thereof;

[0082] R x , R y and R z Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

[0083] In this embodiment, the substituents R1 to R 10 At least one substituent has a structure represented by Formula 2, and R1 to R10 The rest of the substituents in each occurrence are selected from the group consisting of the above substituents in the same or different manner. For example, when the substituent R1 has a structure represented by Formula 2, then R1 to R 10 The remainder of R2 to R 10 Each occurrence is identical or different and is selected from the group consisting of the above substituents. When the substituents R1 and R6 have a structure represented by Formula 2, then R1 to R 10 The rest, namely R2 to R5 and R7 to R 10 Each occurrence is identical or different and is selected from the group consisting of the above substituents. According to one embodiment of the present invention, the substituents R1 to R 10 At least two of them have the structure represented by Formula 2.

[0084] According to one embodiment of the present invention, the substituent R1-R 10 Two of them have the structure represented by Formula 2.

[0085] According to one embodiment of the present invention, the substituents R1 and R6 have a structure represented by Formula 2.

[0086] According to one embodiment of the present invention, R2, R4-R5, R7 and R9-R 10 is hydrogen, and the substituents R3 and R8 are selected, identically or differently, on each occurrence from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms.

[0087] According to one embodiment of the present invention, the substituent R x1 Each occurrence is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 ring carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, or a combination thereof.

[0088] According to one embodiment of the present invention, the substituent R x1 Each occurrence is identically or differently selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or a combination thereof.

[0089] According to one embodiment of the present invention, wherein R x1is selected, at each occurrence, identically or differently, from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, trifluoromethyl, cyano, trimethylsilyl, or a combination thereof.

[0090] According to one embodiment of the present invention, the substituent R y1 Each occurrence is identically or differently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or a combination thereof.

[0091] According to one embodiment of the present invention, the substituent R y1 The same or different at each occurrence is selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or a combination thereof.

[0092] According to one embodiment of the present invention, the substituent R y1 is selected, identically or differently at each occurrence, from hydrogen, deuterium, methyl, ethyl, isopropyl, cyclopropyl, tert-butyl, phenyl, trimethylsilyl, or combinations thereof.

[0093] According to one embodiment of the present invention, Formula 2 is further represented by Formula 3, Formula 4 or Formula 5:

[0094]

[0095] Among them, in formula 3, formula 4 and formula 5,

[0096] "*" represents the position where the structures represented by Formula 3, Formula 4 and Formula 5 are connected to Formula 1;

[0097] L is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0098] R z1each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, mercapto, phosphino, and combinations thereof;

[0099] R x , R y and R z Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

[0100] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms at each occurrence.

[0101] According to one embodiment of the present invention, each occurrence of L is identically or differently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0102] According to one embodiment of the present invention, wherein L is a single bond.

[0103] According to one embodiment of the present invention, the substituent R z1Each occurrence is identically or differently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or a combination thereof.

[0104] According to one embodiment of the present invention, the substituent R z1 Each occurrence is identically or differently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted silane having 3 to 20 carbon atoms, or a combination thereof.

[0105] According to one embodiment of the present invention, the substituent R z1 is selected at each occurrence from methyl, ethyl, isopropyl, butyl, cyclopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, deuterated methylphenyl, or a combination thereof.

[0106] According to one embodiment of the present invention, the substituent R x , R y , R z Each occurrence is identically or differently selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or a combination thereof.

[0107] According to one embodiment of the present invention, the substituent R x , R y , R z and is selected, at each occurrence, identically or differently, from methyl, ethyl, isopropyl, butyl, isobutyl, tert-butyl, neopentyl, cyclopropyl, cyclopentyl, cyclohexyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl and deuterated phenyl.

[0108] According to an embodiment of the present invention, the compound is selected from the group consisting of compound BD1 to compound BD622, and the specific structures of compound BD1 to compound BD622 are shown in claim 11.

[0109] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0110] anode,

[0111] cathode,

[0112] and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of Formula 1:

[0113]

[0114] Among them, in formula 1,

[0115] R1-R 10 The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0116] And, R1-R 10 At least one substituent has a structure represented by Formula 2;

[0117]

[0118] Among them, in formula 2,

[0119] "*" represents the position where the substituent having Formula 2 is attached to Formula 1;

[0120] L is selected, at each occurrence, identically or differently, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0121] X1 to X4 are selected from CR in the same or different manner at each occurrence. x1 or N;

[0122] Y1 to Y3 are selected from CR y1 or N;

[0123] Z1 to Z4 are selected from CR in the same or different manner at each occurrence. z1 or N;

[0124] R x1 The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0125] R y1 and R z1 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, mercapto, phosphino, and combinations thereof;

[0126] R x , R y and R zThe same or different at each occurrence is selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

[0127] According to an embodiment of the present invention, the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound of Formula 1.

[0128] According to an embodiment of the present invention, the light-emitting layer further comprises a host material.

[0129] According to one embodiment of the present invention, the light-emitting layer further comprises a compound having Formula 6:

[0130]

[0131] Among them, in formula 6,

[0132] R g1 To R g8 The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0133] R g9 and R g10 is selected, identically or differently on each occurrence, from substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 6 to 30 carbon atoms.

[0134] According to one embodiment of the present invention, a compound formulation is also disclosed, which comprises a compound having a structure of Formula 1, and the specific structure of the compound is shown in any of the aforementioned embodiments.

[0135] Combination with other materials

[0136] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is 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 therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0137] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is 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 therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0138] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0139] Material synthesis example:

[0140] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0141] Synthesis Example 1: Synthesis of Compound BD9

[0142] first step

[0143]

[0144] At room temperature, under a nitrogen atmosphere, 4-bromo-2-methylaniline (500 g, 2687 mmol), o-methylphenylboric acid (40.0 g, 295.6 mmol), tetrakis(triphenylphosphine)palladium (9.3 g, 8.1 mmol), and potassium carbonate (93.0 g, 671.8 mmol) were added to tetrahydrofuran / water (3 / 1, 1300.0 mL) in sequence, and then the temperature was raised to 80°C to react overnight. After the reaction was complete, the diatomaceous earth was filtered while hot, the filtrate was concentrated, and the mixture was purified by column chromatography to obtain a transparent oily intermediate 1 (26.0 g, 131.8 mmol, yield 49%).

[0145] Step 2

[0146]

[0147] At room temperature and under nitrogen protection, tri(dibenzylideneacetone)dipalladium (6.0 g, 6.6 mmol) and 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (8.0 g, 13.2 mmol) were added to toluene (1000 mL). N2 was introduced into the solution for 20 minutes, and intermediate 2 (41.0 g, 158.2 mmol), intermediate 1 (26.0 g, 131.8 mmol), and sodium tert-butoxide (31.0 g, 330.0 mmol) were added successively. N2 was introduced for 10 minutes, and the system was heated to 110°C for 4 hours. The reaction solution was filtered and washed with toluene, the solvent was removed by rotation, and column chromatography was performed to obtain white solid intermediate 3 (35.0 g, 92.7 mmol, yield 70%).

[0148] Step 3

[0149]

[0150] At room temperature and under nitrogen protection, palladium acetate (37.0 mg, 0.17 mmol) and tri(tert-butyl)phosphine tetrafluoroborate (97.0 mg, 0.33 mmol) were added to xylene (40 mL). N2 was passed into the solution for 20 minutes, and 1,6-dibromopyrene (2.0 g, 5.56 mmol), intermediate 3 (5.2 g, 13.89 mmol), and sodium tert-butoxide (1.7 g, 17.5 mmol) were added successively. N2 was continued to be passed for 10 minutes, and the system was heated to 90°C until the reaction was complete. The reaction solution was filtered and washed with toluene, and the target product BD9 was recrystallized from toluene several times as a yellow-green solid (1.6 g, 1.68 mmol, yield 30%). The product was confirmed to be the target product with a molecular weight of 952.

[0151] Synthesis Example 2: Synthesis of Compound BD549

[0152]

[0153] At room temperature, under nitrogen protection, intermediate 3 (10.7 g, 28.36 mmol) and potassium tert-butoxide (5.7 g, 51 mmol) were dissolved in deuterated dimethyl sulfoxide (25 g), and stirred at room temperature for 10 min. The temperature was slowly raised to 70 ° C, and then lowered to room temperature after 4 h. The mixture was extracted with DCM / H2O system and concentrated. Column chromatography was performed with PE / TOL (10:1) as eluent to obtain intermediate 4 (yielded 90%).

[0154]

[0155] At room temperature and under nitrogen protection, palladium acetate (37.0 mg, 0.17 mmol) and tri(tert-butyl)phosphine tetrafluoroborate (97.0 mg, 0.33 mmol) were added to xylene (40 mL). N2 was passed into the solution for 20 minutes, and 1,6-dibromopyrene (2.0 g, 5.56 mmol), intermediate 4 (5.3 g, 13.89 mmol), and sodium tert-butoxide (1.7 g, 17.5 mmol) were added successively. N2 was continued to be passed for 10 minutes, and the system was heated to 90°C until the reaction was complete. The reaction solution was filtered and washed with toluene, and the target product BD549 was obtained by multiple recrystallizations in toluene as a yellow-green solid (1.1 g, 1.05 mmol, yield 19%). The product was confirmed to be the target product with a molecular weight of 976.

[0156] Comparative Synthesis Example 1: Synthesis of Comparative Compound B

[0157] first step:

[0158]

[0159] At room temperature and under nitrogen protection, tri(dibenzylideneacetone)dipalladium (6.0 g, 6.6 mmol) and 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (8.0 g, 13.2 mmol) were added to toluene (1000 mL). N2 was introduced into the solution for 20 minutes, and 2-methyl-4-phenylbromobenzene (36.9 g, 150 mmol), 2-methyl-4-phenylaniline (32.9 g, 180 mmol), and sodium tert-butoxide (31.6 g, 330.0 mmol) were added successively. N2 was introduced for 10 minutes, and the system was heated to 110°C for 4 hours. The reaction solution was filtered and washed with toluene, the solvent was removed, and column chromatography was performed to obtain a white solid intermediate 5 (35.2 g, 101 mmol, yield 67%).

[0160] Step 2:

[0161]

[0162] At room temperature and under nitrogen protection, palladium acetate (71.1 mg, 0.33 mmol) and tri-tert-butylphosphine tetrafluoroborate (194.0 mg, 0.66 mmol) were added to xylene (40 mL). N2 was introduced into the solution for 20 minutes, and 1,6-dibromopyrene (2.4 g, 6.76 mmol), intermediate 5 (5.2 g, 14.89 mmol), and sodium tert-butoxide (1.7 g, 17.5 mmol) were added successively. N2 was continued to be introduced for 10 minutes, and the system was heated to 90°C until the reaction was complete. The reaction solution was filtered and washed with toluene, and the target product compound B was obtained by multiple recrystallizations in toluene as a yellow-green solid (3.55 g, 3.68 mmol, yield 54.4%). The product was confirmed to be the target product with a molecular weight of 896.

[0163] Comparative Synthesis Example 2: Synthesis of Comparative Compound C

[0164] first step:

[0165]

[0166] At room temperature and under nitrogen protection, palladium acetate (112.5 mg, 0.5 mmol) and tri(tert-butyl)phosphine tetrafluoroborate (289 mg, 1 mmol) were added to xylene (100 mL). N2 was introduced into the solution for 20 minutes, and 1,6-dibromopyrene (3.6 g, 10 mmol), di(4-biphenyl)amine (7.0 g, 22 mmol), and sodium tert-butoxide (2.13 g, 22.22 mmol) were added successively. N2 was introduced for 10 minutes, and the system was heated to 90°C until the reaction was complete. The reaction solution was filtered and washed with toluene, and the target product compound C (2.4 g, 2.85 mmol, yield 28.5%) was obtained by multiple recrystallizations in toluene. The product was confirmed to be the target product with a molecular weight of 840.

[0167] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0168] Device Embodiment

[0169] Device Example 1

[0170] First, the glass substrate with an 80nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 In the case of 1000 Å / s, the ITO anode is deposited by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI is used as a hole injection layer (HIL). Compound HT is used as a hole transport layer (HTL). Compound EB is used as an electron blocking layer (EBL). Compound BD9 is then doped in compound BH and co-evaporated as an emitting layer (EML). Compound HB is used as a hole blocking layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) are co-evaporated as an electron transport layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1 nm is evaporated as an electron injection layer, and 120 nm of aluminum is evaporated as a cathode. The device is then transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0171] Device Example 2

[0172] The implementation of Comparative Device Example 2 is the same as that of Example 1, except that BD549 is used in place of compound BD9 in the light emitting layer (EML).

[0173] Device Comparison Example 1

[0174] The implementation of Comparative Device Example 1 is the same as that of Example 1, except that Compound A is used in place of Compound BD9 in the emission layer (EML).

[0175] Device Comparison Example 2

[0176] The implementation of Comparative Device Example 2 is the same as that of Example 1, except that Compound B is used instead of Compound BD9 in the emission layer (EML).

[0177] Device Comparison Example 3

[0178] The implementation of Comparative Device Example 3 is the same as that of Example 1, except that Compound C is used instead of Compound BD9 in the emission layer (EML).

[0179] The detailed structure and thickness of the device layer are shown in Table 1. For the layers using more than one material, different compounds are doped in the weight ratios recorded.

[0180] Table 1 Device structures of device embodiments and comparative examples

[0181]

[0182] The material structure used in the device is shown below:

[0183]

[0184]

[0185] The lifetime LT97 and external quantum efficiency (EQE) data tested at 1000 nits are shown in Table 2. LT97 represents the time when the device lifetime decays to 97% of the initial brightness.

[0186] Table 2 Device data

[0187] Part Number EQE(%) LT97(hrs) Example 1 9.46 616 Example 2 9.56 827 Comparative Example 1 8.88 269 Comparative Example 2 8.83 571 Comparative Example 3 7.90 256

[0188] discuss:

[0189] Comparison between Example 1 and Comparative Example 3 shows that the lifetime is increased by 140% and the EQE is increased by nearly 20%. Comparison between Example 2 and Comparative Example 3 shows that the lifetime is increased by 223% and the EQE is increased by 21%. It can be seen that in the same device structure, the fluorescent luminescent material introduces an ortho-substituted aryl group into the N-para position of the aryl group in the aromatic amine and substitutes at the N-ortho position. Compared with the fluorescent luminescent material without any ortho-substituent to produce steric hindrance effect, the device lifetime and EQE are improved more.

[0190] In Example 1 and Comparative Example 1, the lifetime was increased by 129% and the EQE was increased by 6%. In Example 2 and Comparative Example 1, the lifetime was increased by 207% and the EQE was increased by 7.6%. It can be seen that in the same device structure, when the pyrene compound containing ortho-substituted aromatic groups is introduced into the N-para position of aromatic amine as the fluorescent luminescent material, the molecular conjugation and stability can be effectively increased compared to the pyrene compound with aromatic substituents introduced into the N-meta position. At the same time, due to the steric effect of the ortho-substituent, the planarity of the molecular conjugated system can be reduced, and finally the device lifetime and efficiency are improved.

[0191] Comparison between Example 1 and Comparative Example 2 shows that the lifetime is increased by about 8% and the EQE is increased by 7%. Comparison between Example 2 and Comparative Example 2 shows that the lifetime is increased by about 44.8% and the EQE is increased by 8.2%. It can be seen that in the same device structure, the pyrene compound with an ortho-substituent further introduced into the N-para aromatic group of aromatic amine as a fluorescent luminescent material can reduce the planarity of the molecular conjugated system compared to the pyrene compound without an ortho-aromatic substituent at the N-para position, and can obtain a longer device lifetime and a higher EQE.

[0192] In summary, in the present invention, in the aromatic amine-substituted pyrene compound, a (hetero) aromatic group containing an ortho substituent is introduced into the N-para position of one aromatic group of the aromatic amine and substitution is performed at the N-ortho position; a substituent is introduced into the N-ortho position of another aromatic group, and further contains substituents at other positions. The obtained compound is applied to fluorescent luminescent materials to obtain better device efficiency, such as longer device lifetime and EQE.

[0193] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present 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 may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. A compound having a structure of Formula 1: in, In formula 1, Substituent R1-R 10 There are two structures represented by formula 4: And the substituent R1-R 10 The remaining in each occurrence are identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano; Wherein, in Formula 4, "*" represents the position where the substituent having the structure of Formula 4 is connected to Formula 1; L is selected from a single bond; R z1 is selected, identically or differently at each occurrence, from substituted phenyl; R x , R y and R z Each occurrence is identically or differently selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms; The substituted alkyl, substituted alkylsilyl, and substituted phenyl refer to any one of the alkyl, alkylsilyl, and phenyl groups which may be substituted by one or more deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, cyano, and combinations thereof; Among them, the R z1 Each occurrence of being identically or differently selected from substituted phenyl means that the substituted phenyl is ortho-substituted.

2. The compound as claimed in claim 1, wherein the substituents R1 and R6 have a structure represented by Formula 4.

3. The compound as claimed in claim 1, wherein R2, R4-R5, R7 and R9-R 10 is hydrogen, and the substituents R3 and R8 are the same or different on each occurrence and are selected from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms.

4. The compound as claimed in claim 1, wherein the substituent R z1 is selected, at each occurrence, identically or differently, from methylphenyl, deuterated phenyl, deuterated methylphenyl.

5. The compound according to any one of claims 1 to 3, wherein the substituent R x , R y , R z Each occurrence is identically or differently selected from substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.

6. The compound according to any one of claims 1 to 3, wherein the substituent R x , R y , R z and is selected, at each occurrence, identically or differently, from methyl, ethyl, isopropyl, butyl, isobutyl, tert-butyl, neopentyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated butyl.

7. The compound of claim 1, wherein the compound is selected from the group consisting of: in, TMS stands for trimethylsilyl.

8. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound having the structure of Formula 1 as claimed in any one of claims 1 to 7. 9 . The electroluminescent device of claim 8 , wherein the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound having Formula 1.

10. The electroluminescent device of claim 9, wherein the light-emitting layer further comprises a compound having Formula 6: in, In formula 6, R g1 To R g8 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino; R g9 and R g10 is selected, identically or differently on each occurrence, from substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl having 6 to 30 carbon atoms.

11. A compound composition comprising the compound according to any one of claims 1 to 7.

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