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 substituents are introduced into the N-ortho positions of both aryl groups of the aromatic amine of the compound, and a (hetero)aryl group is introduced into the N-para position of one of the aryl groups, and a substituent is introduced into the N-meta position of the other aryl group. 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] EP3605635 discloses an organic electroluminescent device, wherein the luminescent material comprises an aromatic amine substituted compound of the general formula: The specific structure is The inventor did not investigate the effect of the structure of the luminescent material on the device performance. The specific structure of the disclosed luminescent material is mainly based on one aryl group having an N-ortho substituent in the aryl amine, which is different from the requirement in the present invention that both aryl groups of the aryl amine have N-ortho substituents. Although this patent application also involves some aryl amines with di-ortho substituents, the present invention also requires that one of the aryl groups is further substituted with an aromatic / heteroaromatic group at the N-para position, in order to increase conjugation and molecular stability, thereby producing efficient and stable deep blue luminescence.

[0007] KR1020140076170A discloses an aromatic amine-substituted pyrene compound, the general formula of which is The specific structure is The application is mainly for aromatic amines containing electron-withdrawing groups, such as phenyl groups substituted with fluorine or cyano. Although the application involves examples of further substituting phenyl groups at the N-ortho and N-para positions of one aromatic group of the amine, the N-ortho substitution of the other aromatic group of the amine is deuterium, which has substantially the same atomic size as hydrogen and does not produce more steric hindrance effects, and does not contain the elements of the present invention that reduce the planarity of each conjugated system, which is different from the two aromatic groups of the aromatic amine in the present invention having N-ortho substituents, and does not disclose and teach that the device performance will be improved when the two aromatic groups of the aromatic amine in the diarylamine-substituted pyrene compound have N-ortho substituents.

[0008] US20100141124A1 discloses a blue fluorescent compound, which is a pyrene compound having an ortho-fluorine-substituted aromatic group, and its general formula is The specific structure is Although some of the disclosed specific compounds have examples of phenyl substituents at both the N-ortho and N-para positions of one aryl group of the aromatic amine, the other aryl group of the aromatic amine is deuterated, and deuterium and hydrogen have substantially the same atomic size, which does not produce more steric hindrance effects, and there is no element that reduces the planarity of each conjugated system of the present invention. Different from the two aryl groups of the aromatic amine in the present invention having N-ortho substituents, there is no disclosure or teaching that the device performance will be improved when both aryl groups of the aromatic amine in the diarylamine-substituted pyrene compound have N-ortho substituents.

[0009] CN106588675A discloses an organic compound having the general formula The disclosed structure is a pyrene compound containing an N-ortho-substituted aromatic amine, and the specific structure is However, the disclosed structure only involves examples in which the N-ortho and N-para positions of the aromatic group in the aromatic amine are substituted with alkyl groups, and does not involve the further introduction of an aromatic group at the N-para position of the aromatic group in the aromatic amine in the present invention to increase the conjugated elements and molecular stability, thereby producing efficient and stable deep blue luminescence.

[0010] These documents disclose some pyrene-based fluorescent materials containing ortho-substituted aromatic amines. Aromatic amine-substituted pyrene plays an important role in the field of blue fluorescence, but fluorescent materials still need to be further developed to obtain higher device performance. Summary of the invention

[0011] 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 longer device life and higher external quantum efficiency.

[0012] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0013]

[0014] Among them, in formula 1,

[0015] Substituent R 1 -R 10 At least one substituent has a structure represented by Formula 2:

[0016]

[0017] And the substituent R 1 -R 10 The remainder of the residues in each occurrence are selected identically or differently from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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;

[0018] Among them, in formula 2,

[0019] * represents the position where the substituent having the structure of Formula 2 is attached to Formula 1;

[0020] 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, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0021] R a Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

[0022] R b , R c and Rd each occurrence is identically or differently selected from the group consisting of: 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 6-30 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 amine having 0-20 carbon atoms, and combinations thereof;

[0023] X 1 To X 6 Each occurrence is the same or different selection from CR X or N;

[0024] R X Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 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 an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0025] 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.

[0026] 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.

[0027] 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. The novel compounds introduce (hetero) aromatic groups into the N-para position of an aromatic group of aromatic amine to increase conjugation and molecular stability, and introduce substituents into the N-ortho position to reduce the planarity of each conjugated system of the molecule, while introducing substituents into the N-ortho position and N-meta position of another aromatic group to increase molecular stability and reduce red shift, thereby generating efficient and stable deep blue luminescence. These novel compounds can provide better device performance, such as longer device life and higher external quantum efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

[0029] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein. DETAILED DESCRIPTION

[0030] 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.

[0031] 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 one doped with F at a molar ratio of 50:1. 4

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] 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 a metal such as Mg:Ag and 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.

[0032] 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.

[0033] 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.

[0034] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The 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.

[0035] 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.

[0036] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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).

[0041] 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.

[0042] 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).

[0043] Definition of Substituent Terms

[0044] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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 ...

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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:

[0062]

[0063] 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:

[0064]

[0065] Furthermore, the statement that two adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that when one of the two substituents bonded to the carbon atom 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:

[0066]

[0067] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0068]

[0069] Among them, in formula 1,

[0070] Substituent R 1 -R 10 At least one substituent has a structure represented by Formula 2:

[0071]

[0072] And the substituent R 1 -R 10 The remainder of the residues in each occurrence are selected identically or differently from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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;

[0073] Among them, in formula 2,

[0074] * represents the position where the substituent having the structure of Formula 2 is attached to Formula 1;

[0075] 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, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0076] R a Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

[0077] R b , R c and R deach occurrence is identically or differently selected from the group consisting of: 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 6-30 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 amine having 0-20 carbon atoms, and combinations thereof;

[0078] X 1 To X 6 Each occurrence is the same or different selection from CR X or N;

[0079] R X Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 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 an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0080] In this embodiment, the substituent R in Formula 1 1 To R 10 At least one substituent has a structure represented by Formula 2, and R 1 To R 10 The remainder of each occurrence of is selected from the group consisting of the above substituents, either identically or differently. 1 Having the structure represented by Formula 2, then R 1 To R 10 The remainder of 2 To R 10Each occurrence is identical or different and is selected from the group consisting of the above substituents. 1 and R 6 Having the structure represented by Formula 2, then R 1 To R 10 The remainder of 2 To R 5 and R 7 To R 10 Each occurrence is identically or differently selected from the group consisting of the aforementioned substituents.

[0081] According to one embodiment of the present invention, the substituent R 1 To R 10 At least two substituents have a structure represented by Formula 2.

[0082] According to one embodiment of the present invention, the substituent R 1 -R 10 Two of them have the structure represented by Formula 2.

[0083] According to one embodiment of the present invention, the substituent R 1 and R 6 Each independently has a structure represented by Formula 2.

[0084] According to one embodiment of the present invention, the substituent R 2 , R 4 -R 5 , R 7 and R 9 -R 10 is hydrogen, the substituent R 3 and R 8 Each occurrence is identically or differently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms.

[0085] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, the same or different each time it occurs.

[0086] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, the same or different each time it occurs.

[0087] According to one embodiment of the present invention, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof, the same or different each time it occurs;

[0088] According to one embodiment of the present invention, L is selected from a single bond.

[0089] According to one embodiment of the present invention, the substituent R a Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms, or a combination thereof.

[0090] According to one embodiment of the present invention, the substituent R a Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, or a combination thereof.

[0091] According to one embodiment of the present invention, the substituent R a is selected identically or differently on each occurrence from substituted or unsubstituted phenyl.

[0092] According to one embodiment of the present invention, the substituent R b , R c and R d 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof.

[0093] According to one embodiment of the present invention, the substituent R b , R c and R d Each occurrence is identically or differently selected from methyl, ethyl, propyl, isopropyl, cyclopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, trimethylsilyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated cyclopropyl, deuterated tert-butyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, deuterated methylphenyl or a combination thereof.

[0094] According to one embodiment of the present invention, X 1 To X 6 Each occurrence is the same or different selection from CR X , where the substituent R XEach 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 6-30 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, and combinations thereof.

[0095] According to one embodiment of the present invention, the substituent R X Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms.

[0096] According to one embodiment of the present invention, the substituent R X Each occurrence is identically or differently selected from hydrogen, deuterium, methyl, ethyl, propyl, tert-butyl, phenyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated tert-butyl, deuterated phenyl, or a combination thereof.

[0097] According to an embodiment of the present invention, the compound is selected from the group consisting of compound BD1 to compound BD541, and the specific structures of compound BD1 to compound BD541 are shown in claim 9.

[0098] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0099] anode,

[0100] cathode,

[0101] and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of Formula 1:

[0102]

[0103] Among them, in formula 1,

[0104] Substituent R 1 -R 10 At least one substituent has a structure represented by Formula 2:

[0105]

[0106] And the substituent R 1 -R 10The remainder of the residues in each occurrence are selected identically or differently from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted 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;

[0107] Among them, in formula 2,

[0108] * represents the position where the substituent having the structure of Formula 2 is attached to Formula 1;

[0109] 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, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0110] R is selected, at each occurrence, identically or differently, from the group consisting of substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

[0111] R b , R c and R dis selected, at each occurrence, identically or differently, from the group consisting of: 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 6-30 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 amine having 0-20 carbon atoms, and combinations thereof;

[0112] X 1 To X 6 Each occurrence is the same or different selection from CR X or N;

[0113] R X Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 6 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 an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0114] According to one embodiment of the present invention, the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound of Formula 1.

[0115] According to an embodiment of the present invention, the light-emitting layer further comprises a host material.

[0116] According to one embodiment of the present invention, the host material is a compound having Formula 4:

[0117]

[0118] Among them, in formula 4,

[0119] 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, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof having 0 to 20 carbon atoms;

[0120] 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.

[0121] According to one embodiment of the present invention, a compound formula is also disclosed, which contains a compound having a structure of Formula 1, and the specific structure of the compound is shown in any of the aforementioned embodiments.

[0122] Combination with other materials

[0123] 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.

[0124] 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.

[0125] 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.

[0126] Material synthesis example:

[0127] 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:

[0128] Synthesis Example 1: Synthesis of Compound BD399

[0129] first step

[0130]

[0131] At room temperature, under nitrogen protection, tri(dibenzylideneacetone)dipalladium (6.0 g, 6.6 mmol) and 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (8.0 g, 13.2 mmol) were added to toluene (1000 mL). 2After 20 minutes, intermediate 2 (20.2 g, 100 mmol), intermediate 1 (21.9 g, 120 mmol), and tert-butyl alcohol (19.2 g, 200 mmol) were added successively. 2 After 10 minutes, the system was heated to 110°C and reacted for 4 hours. The reaction solution was filtered and washed with toluene, the solvent was removed under reduced pressure and then column chromatography was performed to obtain a white solid intermediate 3 (25.5 g, 73 mmol, yield: 73%).

[0132] Step 2

[0133]

[0134] At room temperature, under nitrogen protection, palladium acetate (37.0 mg, 0.17 mmol) and tri-tert-butylphosphine tetrafluoroborate (97.0 mg, 0.33 mmol) were added to xylene (40 mL). 2 After 20 minutes, 1,6-dibromopyrene (2.0 g, 5.56 mmol), intermediate 3 (4.85 g, 13.89 mmol), and sodium tert-butoxide (1.7 g, 17.5 mmol) were added successively. 2 After 10 minutes, the system was heated to 90°C until the reaction was complete. The reaction system was filtered through diatomaceous earth and washed with toluene. The yellow-green solid BD399 (1.8 g, 2.0 mmol, yield: 36%) was obtained by multiple recrystallizations in toluene. The product was confirmed to be the target product with a molecular weight of 896.

[0135] Synthesis Example 2: Synthesis of Compound BD459

[0136] first step:

[0137]

[0138] At room temperature and under nitrogen protection, palladium acetate (0.2 g, 1 mmol), intermediate 4 (10 g, 39.5 mmol), intermediate 5 (8.7 g, 47.4 mmol), tri-tert-butylphosphine (4 mL, 2 mmol) and sodium tert-butoxide (8.3 g, 86.9 mmol) were added to toluene (100 mL), and the system was heated to reflux and reacted overnight. The reaction solution was treated with basic alumina and MgSO 4 The mixture was filtered and washed with toluene. The solvent was removed under reduced pressure and column chromatography was performed to obtain white solid intermediate 6 (10.7 g, 30 mmol, yield: 76%).

[0139] Step 2:

[0140]

[0141] At room temperature, under nitrogen protection, palladium acetate (63 mg, 0.28 mmol) and tri-tert-butylphosphine tetrafluoroborate (162 mg, 0.56 mmol) were added to xylene (40 mL). N2 was bubbled into the solution for 20 minutes, and 1,6-dibromopyrene (2 g, 5.56 mmol), intermediate 6 (4.35 g, 12.22 mmol), and sodium tert-butoxide (2.13 g, 22.22 mmol) were added successively. N2 was continued to be bubbled into the solution for 20 minutes. 2 10 minutes, the system was heated to 90 ° C until the reaction was complete. The reaction system was filtered with diatomaceous earth and washed with toluene. The target product was recrystallized from toluene several times to obtain a yellow-green solid BD (1.4 g, 1.51 mmol, yield: 27%). The product was confirmed to be the target product with a molecular weight of 924.

[0142] Comparative Synthesis Example 1: Synthesis of Compound A

[0143] first step:

[0144]

[0145] Trisdibenzylideneacetone dipalladium (2.3 g, 2.5 mmol) and 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (3.13 g, 5 mmol) were added to toluene (300 mL) at room temperature under nitrogen protection. 2 After 20 minutes, 4-phenyliodobenzene (14.0 g, 50 mmol), 3-phenylaniline (10.0 g, 60.0 mmol), and sodium tert-butoxide (10.56 g, 110 mmol) were added successively. 2 After 10 minutes, the system was heated to 100°C and reacted for 4 hours. The reaction solution was filtered and washed with tol, the solvent was removed and column chromatography was performed to obtain light yellow oily intermediate 7 (11.24 g, 35 mmol, yield: 75%).

[0146] Step 2:

[0147]

[0148] At room temperature, under nitrogen protection, palladium acetate (112.5 mg, 0.5 mmol) and tri-tert-butylphosphine tetrafluoroborate (289 mg, 1 mmol) were added to xylene (100 mL). N was added to the solution. 2 After 20 minutes, 1,6-dibromopyrene (3.6 g, 10 mmol), intermediate 7 (7.0 g, 22 mmol), and sodium tert-butoxide (2.13 g, 22.22 mmol) were added successively. 210 minutes, the system was heated to 90 ° C until the reaction was complete. The reaction system was filtered with diatomaceous earth and washed with toluene, and the target product compound A (2.4 g, 2.85 mmol, yield: 28.5%) was obtained by multiple recrystallization in toluene. The product was confirmed to be the target product with a molecular weight of 840.

[0149] Comparative Synthesis Example 2: Synthesis of Compound B

[0150] first step:

[0151]

[0152] Tris(dibenzylideneacetone)dipalladium (2.2 g, 2.5 mmol) and 1,1'-binaphthyl-2,2'-bis(diphenylphosphine) (3.0 g, 5.0 mmol) were added to toluene (400 mL) at room temperature under nitrogen protection. 2 After 20 minutes, 4-phenylbromobenzene (10.6 g, 45.53 mmol), intermediate 5 (10.0 g, 54.64 mmol), and sodium tert-butoxide (20.0 g, 205.0 mmol) were added successively. 2 After 10 minutes, the system was heated to 140°C for 18 hours. The reaction solution was filtered through diatomaceous earth and washed with toluene. The solvent was removed and column chromatography was performed to obtain the product as a white solid intermediate 8 (5.0 g, 14.92 mmol, yield: 33%).

[0153] Step 2:

[0154]

[0155] At room temperature, under nitrogen protection, palladium acetate (40.0 mg, 0.17 mmol) and tri-tert-butylphosphine tetrafluoroborate (101.0 mg, 0.35 mmol) were added to xylene (40 mL). 2 After 20 minutes, 1,6-dibromopyrene (2.1.0 g, 5.9 mmol), intermediate 8 (5.0 g, 14.92 mmol), and sodium tert-butoxide (1.6 g, 17.49 mmol) were added successively. 2 10 minutes, the system was heated to 100 ° C until the reaction was complete. The reaction solution was filtered through diatomaceous earth and washed with toluene. The solvent was removed under reduced pressure and column chromatography was performed to obtain a crude product, which was recrystallized from toluene to obtain the target product, yellow-green solid compound B (4.0 g, 46.02 mmol, 78%). The product was confirmed to be the target product with a molecular weight of 868.

[0156] 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.

[0157] Device Embodiment

[0158] Device Example 1

[0159] 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). Then compound BD459 is doped in compound BH and co-evaporated as a light-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.

[0160] Device Example 2

[0161] The implementation of Device Example 2 is the same as that of Device Example 1, except that Compound BD399 is used instead of Compound BD459 in the light emitting layer (EML).

[0162] Device Comparison Example 1

[0163] 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 BD459 in the light emitting layer (EML).

[0164] Device Comparison Example 2

[0165] The implementation of Comparative Device Example 2 is the same as that of Example 1, except that Compound B is used in place of Compound BD459 in the light emitting layer (EML).

[0166] Device Comparison Example 3

[0167] The implementation of Comparative Device Example 3 is the same as that of Example 1, except that Compound C is used in place of Compound BD459 in the light emitting layer (EML).

[0168] 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.

[0169] Table 1 Device structures of device embodiments and comparative examples

[0170]

[0171]

[0172] The material structure used in the device is shown below:

[0173]

[0174]

[0175] The IVL of the device was measured at different current densities and voltages. Table 2 lists the test lifetime LT97, external quantum efficiency (EQE), maximum emission wavelength (λ max ) and full width at half maximum (FWHM) data. LT97 represents the time it takes for the device lifetime to decay to 97% of its initial brightness.

[0176] Table 2 Device data

[0177] Part Number <![CDATA[λ max (nm)]]> FWHM(nm) EQE(%) LT97 / (h) Example 1 460 33.0 9.36 663 Example 2 463 33.4 8.83 804 Comparative Example 1 470 35.0 7.92 300 Comparative Example 2 469 34.1 8.46 66 Comparative Example 3 456 32.2 8.88 269

[0178] discuss:

[0179] Compared with Comparative Example 1, the EQE of Example 2 is improved by 11.5%, the LT97 is improved by about 1.7 times, the half-peak width is narrowed by 1.6nm, and the maximum emission wavelength is blue-shifted by 7nm; compared with Comparative Example 2, the EQE of Example 2 is improved by 4.4%, the LT97 is improved by about 11.2 times, the half-peak width is narrowed by 0.7nm, and the maximum emission wavelength is blue-shifted by 6nm.

[0180] Compared with Comparative Examples 1 and 2, the EQE of Example 1 is improved by at least 10.6%, and the LT97 is improved by at least about 1.2 times.

[0181] The above results show that in the same device structure, the use of pyrene containing two N-ortho-substituted aromatic amines as fluorescent materials has higher EQE and device life in the device results, compared with pyrene containing unsubstituted or singly substituted aromatic amines at the N-ortho-position as fluorescent materials, and effectively increases the blue light-emitting performance.

[0182] Compared with Comparative Example 3, Example 2 has a similar EQE. Although the maximum emission wavelength is red-shifted by 7 nm, the LT97 is increased by nearly 2 times.

[0183] The above results show that in the same device structure, the use of pyrene containing an N-para-aryl substituted aromatic amine as a fluorescent material is compared to the use of pyrene containing an N-meta-aryl substituted aromatic amine as a fluorescent material. The N-para-aryl substituted aromatic amine increases the stability of the conjugated pair. Although the emission is red-shifted, it has a much longer lifetime, effectively increasing the blue luminescence performance.

[0184] Compared with Comparative Example 3, the EQE of Example 1 is improved by 5.4%, the lifetime is improved by 146%, and the maximum emission wavelength is 4nm different, which is 3nm narrower than the 7nm difference between Example 2 and Comparative Example 3.

[0185] The above results show that in the same device structure, the introduction of ortho-alkyl substitution using para-aryl groups can further improve EQE and effectively increase blue light-emitting performance.

[0186] In summary, the inventors of the present application have obtained substituted pyrene compounds having the structure of formula 2 through the design of the compound structure, that is, in the pyrene compounds substituted with aromatic amines, both aromatic groups in the aromatic amines are substituted at the N-ortho position and further one of the aromatic groups is substituted at the N-para position with a (hetero) aromatic group, and the other aromatic group is substituted at the N-meta position. When such compounds are applied to organic electroluminescent devices, the device life and external quantum efficiency are greatly improved, and ultimately a very good device effect is achieved.

[0187] 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, The substituents R1 and R6 have a structure of Formula 2: And the substituents R2-R5, R7-R 10 Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium, halogen; wherein, in Formula 2, * represents the position where the substituent having the structure of Formula 2 is attached to Formula 1; L is selected from a single bond; R a , R d is selected, identically or differently at each occurrence, from substituted or unsubstituted phenyl; R b , R c is selected, identically or differently on each occurrence, from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; X1 to X6 are selected from CH; Wherein, the substituted phenyl group means that the ortho position of the phenyl connection position can be substituted by one or more selected from deuterium, unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof; the substituted alkyl group means that the alkyl group can be substituted by one or more selected from deuterium, unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof.

2. The compound according to claim 1, wherein the substituents R1 and R6 have a structure of Formula 2, and the substituents R2-R5, R7-R 10 Each occurrence is identically or differently selected from the group consisting of: hydrogen, deuterium.

3. The compound as claimed in claim 1, wherein the substituents R2-R5, R7-R 10 For hydrogen.

4. The compound according to claim 1, wherein the substituent R b and R c On each occurrence it is identically or differently selected from substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.

5. The compound according to claim 1, wherein the substituent R b and R c Each occurrence is identically or differently selected from methyl, ethyl, propyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated tert-butyl, or a combination thereof.

6. The compound of claim 1, wherein the compound is selected from the group consisting of:

7. An electroluminescent device comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound according to any one of claims 1 to 6. 8 . The organic electroluminescent device as claimed in claim 7 , wherein the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises the compound of Formula 1.

9. The organic electroluminescent device as claimed in claim 8, wherein the light-emitting layer further comprises a host material.

10. The organic electroluminescent device according to claim 9, wherein the host material is a compound having Formula 4: in, In formula 4, 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, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof having 0 to 20 carbon atoms; 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 composition comprising the compound according to any one of claims 1 to 6.

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