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 one of the aromatic groups of the aromatic amine in the compound has a substituted six-membered (hetero) aromatic ring and a saturated ring structure, and the other aromatic group is a substituted (hetero) aromatic 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 a narrower half-peak width and a higher 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 electroluminescent 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] WO2010013676A1 discloses diaminopyrene derivatives, the general formula of which is as follows: Among them, some aminopyrene derivatives with benzocyclic hydrocarbon substitution are disclosed, and the specific structure is However, the patent application did not examine the effect of the introduction of benzocyclic hydrocarbons on device performance, nor did it realize the advantages that the introduction of benzocyclic hydrocarbons or the attachment of other groups to the benzene ring of benzocyclic hydrocarbons can bring, nor did it realize the different effects that can be brought about by changing the position of the substituents of the benzoaliphatic ring.

[0007] CN109678729A discloses a pyrene compound containing a benzocyclohexane structure, the general formula of which is as follows Among them, Ar 2 Selected from The specific structure is However, the patent application only discloses compounds of benzocyclohexane with only a few structures, and does not examine the effect of the introduction of benzocyclohexane on device performance, nor does it disclose or teach the device effect that the cyclic hydrocarbon in the benzocyclohexane is non-six-membered ring and that further substitution on the benzene ring of the benzocyclohexane will achieve.

[0008] CN107556239A discloses a pyrene compound containing an acridine structure, the general formula of which is as follows: Among them, Ar 1 and Ar 2 It can be a heterocyclic group, and the specific structure is However, this patent application mainly targets a series of pyrene compounds with acridine-substituted aromatic amines, and does not pay attention to the improvement of device performance brought by benzoheterocyclic hydrocarbons, nor does it disclose or teach that other groups connected to the benzene ring of benzoheterocyclic hydrocarbons will achieve better device effects.

[0009] These documents disclose some fluorescent luminescent materials with pyrene as the core and aromatic amine structure. However, the fluorescent luminescent materials still need to be further developed to obtain higher device performance. Summary of the invention

[0010] The present invention aims to provide a series of novel pyrene compounds having a substituted six-membered (hetero) aromatic ring and a saturated ring and a substituted (hetero) aromatic aromatic amine structure to solve at least part of the above problems.

[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] Substituent R 1 -R 10 At least one of them has the structure of Formula 2:

[0015]

[0016] And the substituent R l -R l0The 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] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;

[0019] X 1 -X 5 Each occurrence is selected from C, CR, either identically or differently x1 , CR x2 or N; and X 1 -X 5 At least two of them are adjacent to C and connected to ** in formula 2, X 1 -X 5 At least one of them is CR x2 ;

[0020] Y 1 -Y 5 Each occurrence is the same or different selection from CR y1 , CR y2 or N; and Y 1 -Y 5 At least one of them is CR y2 ;

[0021] Z is selected, at each occurrence, identically or differently, from C(R z ) 2 , NR z , O, S or Se;

[0022] R x1 and R y1The 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;

[0023] R x2 and R y2 each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or 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 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;

[0024] * represents the position where the substituent having the structure of Formula 2 is connected to Formula 1;

[0025] n is 0, 1, 2, 3, 4 or 5;

[0026] R zeach occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;

[0027] Adjacent substituent R x1 , R x2 , R y1 , R y2 Can optionally be linked to form a ring.

[0028] 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.

[0029] 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.

[0030] The present invention provides a series of novel pyrene compounds having a substituted six-membered (hetero) aromatic ring and a saturated ring and a substituted (hetero) aromatic aromatic amine structure, which can be used as a luminescent material in an organic electroluminescent device. These novel compounds can provide better device performance, such as a narrower half-peak width and a higher external quantum efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the compounds and compound formulations disclosed herein.

[0032] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the compounds and compound formulations disclosed herein. DETAILED DESCRIPTION

[0033] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1An 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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).

[0044] 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.

[0045] 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).

[0046] Definition of Substituent Terms

[0047] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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 ...

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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:

[0065]

[0066] 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:

[0067]

[0068] 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:

[0069]

[0070] According to one embodiment of the present invention, a compound having a structure of Formula 1 is disclosed:

[0071]

[0072] Among them, in formula 1,

[0073] Substituent R 1 -R 10 At least one of them has the structure of Formula 2:

[0074]

[0075] And the substituent R 1 -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;

[0076] Among them, in formula 2,

[0077] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;

[0078] X 1 -X 5 Each occurrence is selected from C, CR, either identically or differently x1 , CR x2 or N; and X 1 -X 5 At least two of them are adjacent to C and connected to ** in formula 2, X 1 -X 5 At least one of them is CR x2 ;

[0079] Y 1 -Y 5 Each occurrence is the same or different selection from CR y1 , CR y2 or N; and Y 1 -Y 5 At least one of them is CRy2 ;

[0080] Z is selected, at each occurrence, identically or differently, from C(R z ) 2 , NR z , O, S or Se;

[0081] R x1 and R y1 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;

[0082] R x2 and R y2 each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or 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 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;

[0083] * represents the position where the substituent having the structure of Formula 2 is connected to Formula 1;

[0084] n is 0, 1, 2, 3, 4 or 5;

[0085] Rz each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;

[0086] Adjacent substituent R x1 , R x2 , R y1 , R y2 can optionally be linked to form a ring;

[0087] Substituent R z Can optionally be linked to form a ring.

[0088] In this embodiment, "the adjacent substituent R x1 , R x2 , R y1 , R y2 "Can be optionally connected to form a ring" may include any one or more of the following situations: one situation is that there are adjacent substituents connected to form a ring, for example, adjacent substituents R x1 and R x1 Between and adjacent substituents R x1 and R x2 Between and adjacent substituents R x2 and R x2 Between and adjacent substituents R y1 and R y1 Between and adjacent substituents R y1 and R y2 Between and adjacent substituents R y2 and R y2 Any one or more of the substituents may be connected to form a ring. Another situation is that the adjacent substituents may not be connected to form a ring.

[0089] In this embodiment, the substituent R z "can be optionally connected to form a ring" may include any one or more of the following situations: one situation is for the substituent R z There are cases where there is a connection to form a ring, for example, when there are two or more Rz When these R z There are cases where there is a connection to form a ring, such as R z After being connected to form a ring, a spiro ring or a bridged ring structure is formed. Another case is that for the substituent R z They can also not be connected to form a ring.

[0090] In this embodiment, the substituent R in Formula 1 1 To R 10 At least one substituent has a structure of 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 With the structure of formula 2, R 1 To R 10 The remainder of 2 To R 10 Each occurrence is identical or different and is selected from the group consisting of the above substituents. 1 and R 6 With the structure of formula 2, 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.

[0091] According to one embodiment of the present invention, the substituent represented by Formula 2 further has a structure of Formula 3 or Formula 4:

[0092]

[0093] Among them, in formula 3 and formula 4,

[0094] In formula 3, X 1 -X 3 Each occurrence is the same or different selection from CR x1 , CR x2 or N; and at least one is CR x2 ;

[0095] In formula 4, X 1 -X 2 and X 5 Each occurrence is the same or different selection from CR x1 , CR x2 or N; and at least one is CR x2 ;

[0096] Y 1 -Y 5Each occurrence is the same or different selection from CR y1 , CR y2 or N; and Y 1 -Y 5 At least one of them is CR y2 ;

[0097] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;

[0098] Z is selected, at each occurrence, identically or differently, from C(R z ) 2 , NR z , O, S or Se;

[0099] n is 0, 1, 2, 3, 4 or 5;

[0100] R x1 and R y1 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;

[0101] R x2 and R y2each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or 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 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;

[0102] R z each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;

[0103] Adjacent substituent R x1 , R x2 , R y1 , R y2 can optionally be linked to form a ring;

[0104] Substituent R z can optionally be linked to form a ring;

[0105] * represents the position where the substituent having the structure represented by Formula 3 or Formula 4 is connected to Formula 1.

[0106] According to one embodiment of the present invention, n is 0, 1, 2, or 3.

[0107] According to one embodiment of the present invention, n is 1.

[0108] According to one embodiment of the present invention, the substituent R in Formula 11 and R 6 has a structure represented by Formula 2, Formula 3 or Formula 4, and R 1 and R 6 are the same or different; R 2 To R 5 , R 7 To 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, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof.

[0109] According to one embodiment of the present invention, the substituent R in Formula 1 1 and R 6 has a structure represented by Formula 2, Formula 3 or Formula 4, and R 1 and R 6 are the same or different; R 2 , R 4 -R 5 , R 7 and R 9 -R 10 is hydrogen, R 3 and R 8 and is selected, identically or differently on each occurrence, from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms.

[0110] 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 arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof.

[0111] 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 arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof.

[0112] According to one embodiment of the present invention, wherein L is selected from a single bond.

[0113] According to one embodiment of the present invention, wherein R x1 and R y1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-6 carbon atoms, substituted or unsubstituted cycloalkyl having 3-6 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-6 carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, substituted or unsubstituted heteroaryl having 3-12 carbon atoms, substituted or unsubstituted alkylsilyl having 3-6 carbon atoms, substituted or unsubstituted arylsilyl having 6-12 carbon atoms, and combinations thereof.

[0114] According to one embodiment of the present invention, wherein R x1 and R y1 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof.

[0115] According to one embodiment of the present invention, wherein R x1 and R y1 For hydrogen.

[0116] According to one embodiment of the present invention, wherein X 1 -X 5 Each time it appears, it is selected from C, CR x1 or CR x2 ; and X 1 -X 5 At least one of the following is selected from CR x2 ; Y 1 -Y 5 Each occurrence is the same or different selection from CR y1 or CR y2 ; and Y 1 -Y 5 At least one of the following is selected from CR y2 .

[0117] According to one embodiment of the present invention, wherein X 1 -X 5 At least one CR x2 , and R x2 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof.

[0118] According to one embodiment of the present invention, wherein X 1 -X 5 At least one CR x2 , and R x2 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.

[0119] According to one embodiment of the present invention, wherein X 1 -X 5 At least one CR x2 , and R x2 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.

[0120] According to one embodiment of the present invention, wherein X 1 -X 5 At least one of the atoms except the ring atoms is CR x2 , and R x2 Each occurrence is identically or differently selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthryl, anthracenyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, and combinations thereof.

[0121] According to one embodiment of the present invention, wherein Y 2 To Y 4 At least one of them is CR y2 , and R y2 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.

[0122] According to one embodiment of the present invention, wherein Y 2 To Y 4 At least one of them is CR y2 , and R y2 Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 18 carbon atoms and substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms.

[0123] According to one embodiment of the present invention, wherein Y 2 To Y 4 At least one of them is CR y2 , and R y2Each occurrence is identically or differently selected from substituted or unsubstituted aryl having 6 to 18 carbon atoms and substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms.

[0124] According to one embodiment of the present invention, wherein Y 2 To Y 4 At least one of them is CR y2 , and R y2 Each occurrence is identically or differently selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthryl, anthracenyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothiolaryl, dibenzothiolaryl, benzothiophenyl, dibenzothiophenyl, dibenzoselenophene, and combinations thereof.

[0125] According to one embodiment of the present invention, wherein Y 1 and / or Y 5 CR y2 , and R y2 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, or a combination thereof.

[0126] According to one embodiment of the present invention, wherein Y 1 and / or Y 5 CR y2 , and R y2 Each occurrence is identically or differently selected from the group consisting of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, cyclopropyl, deuterated cyclopropyl, n-butyl, deuterated n-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl and deuterated cyclohexyl.

[0127] According to one embodiment of the present invention, wherein Z is C(R z ) 2 , and R z 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof.

[0128] According to one embodiment of the present invention, Z is CR z , and R zEach occurrence is identically or differently selected from the group consisting of hydrogen, halogen, deuterium, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, and combinations thereof.

[0129] According to an embodiment of the present invention, the compound is selected from the group consisting of compound BD1 to compound BD810, and the specific structures of compound BD1 to compound BD810 are shown in claim 12.

[0130] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0131] anode,

[0132] cathode,

[0133] and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of Formula 1:

[0134]

[0135] Among them, in formula 1,

[0136] Substituent R 1 -R 10 At least one substituent has a structure represented by Formula 2;

[0137]

[0138] And the substituent R 1 -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;

[0139] Among them, in formula 2,

[0140] L is identically or differently selected at each occurrence from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;

[0141] X 1 -X 5 Each occurrence is selected from C, CR, either identically or differently x1 , CR x2 or N; and X 1 -X 5 At least two of them are adjacent to C and connected to ** in formula 2, X 1 -X 5 At least one of them is CR x2 ;

[0142] Y 1 -Y 5 Each occurrence is the same or different selection from CR y1 , CR y2 or N; and Y 1 -Y 5 At least one of them is CR y2 ;

[0143] Z is selected, at each occurrence, identically or differently, from C(R z ) 2 , NR z , O, S or Se;

[0144] R x1 and R y1 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 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;

[0145] R x2 and R y2each occurrence is identically or differently selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or 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 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;

[0146] * represents the position where the substituent having the structure represented by Formula 2 is connected to Formula 1;

[0147] n is 0, 1, 2, 3, 4 or 5;

[0148] R z each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, 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, and combinations thereof;

[0149] Adjacent substituent R x1 , R x2 , R y1 , R y2 can optionally be linked to form a ring;

[0150] Substituent R z Can optionally be linked to form a ring.

[0151] According to an embodiment of the present invention, the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound having a structure of Formula 1.

[0152] According to an embodiment of the present invention, the light-emitting layer further comprises a host material.

[0153] According to one embodiment of the present invention, the host material comprises a compound having a structural formula 5:

[0154]

[0155] Among them, in formula 5,

[0156] R g1 To R g8 Each of the following is independently 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 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 amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0157] R g9 and R g10 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0158] 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.

[0159] Combination with other materials

[0160] 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.

[0161] 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.

[0162] 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.

[0163] Material synthesis example:

[0164] 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:

[0165] Synthesis Example 1: Synthesis of Compound BD176

[0166] first step

[0167]

[0168] 2-Bromo-4-iodo-1-methylbenzene (100 g, 337 mmol), phenylboronic acid (49 g, 404 mmol), Pd(PPh 3 ) 4 (7.8 g, 6.8 mmol), K 2 CO3 (116 g, 843 mmol) was placed in a 1000 mL three-necked flask, and 340 mL of toluene, 110 mL of THF, and H 2 O110mL, replace N 2 The reaction was heated to 78°C and the reaction was continued until the reaction of the raw materials was complete. The intermediate 1 (80 g, 325 mmol, yield 97%) was obtained by column chromatography.

[0169] Step 2

[0170]

[0171] Intermediate 1 (81 g, 329 mmol) and NBS (61 g, 345 mmol) were placed in a 2 L two-necked bottle, and 1.3 L of acetonitrile was added to replace N 2 , heated to 80°C, stirred for reaction. Benzoyl peroxide (BPO, 8 g, 33 mmol) was added in batches. The reaction was continued until the reaction of the raw materials was complete, and column chromatography was used for purification to obtain a white solid intermediate 2 (82 g, 253 mmol, yield 77%).

[0172] Step 3

[0173]

[0174] Place LDA (130 mL, 260 mmol) in a 500 mL three-necked flask, stir under dry ice-ethanol for half an hour, add methyl isobutyrate (30 mL, 260 mmol), and continue stirring for half an hour. Add intermediate 2 (80 g, 130 mmol). React until the raw materials react completely, and purify by column chromatography to obtain light yellow oil intermediate 3 (50 g, 145 mmol, yield 98%).

[0175] Step 4

[0176]

[0177] Intermediate 3 (78 g, 227 mmol) and KOH (88 g, 1.57 mol) were mixed and H 2 O 230mL, methanol 23mL, heated to 100℃ for reaction, until TLC detected that the reaction was complete. Cooled, the reaction returned to room temperature, concentrated HCl was added to adjust the pH of the system to acidic, and filtered to obtain the intermediate (71g, 227mmol).

[0178] The above intermediate (20 g, 60 mmol) was dissolved in 200 mL of dichloromethane and N 2, add a drop of DMF, gradually add oxalyl chloride (30mL, 60mmol), after the system no longer produces bubbles, move the reaction to an ice-water bath and stir for half an hour, add aluminum chloride (8g, 60mmol) in batches, and monitor by TLC until the reaction is complete. Filter through diatomaceous earth and concentrate. Column chromatography (PE as eluent) to obtain white solid intermediate 4 (6g, 18.8mmol, yield 31%).

[0179] Step 5

[0180]

[0181] Intermediate 4 (18 g, 57 mmol) was dissolved in 180 mL of methanol, stirred in an ice-water bath for half an hour, and NaBH 4 After the reaction is complete, the mixture is filtered through celite and the filtrate is concentrated.

[0182] The above product was dissolved in dichloromethane and Et 3 SiH (12.7 g, 111 mmol) was placed in an ice-water bath and stirred for half an hour, TFA (18 g, 155 mmol) was gradually added dropwise, and the reaction was continued until the reaction of the raw materials was complete. Column chromatography was used for purification to obtain a colorless oil intermediate 5 (12 g, 39.9 mmol, yield 70%).

[0183] Step 6

[0184]

[0185] At room temperature and under nitrogen protection, Pd 2 (dba) 3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 5 (6 g, 19.9 mmol), 4-methyl-[1,1′-biphenyl]-3-amine (5.5 g, 30 mmol) and t-BuONa (3.8 g, 39.8 mmol) were added to toluene (100 mL), and the system was heated to 120° C. for 2 h. After the reaction was completed, white solid intermediate 6 (6.7 g, 16.4 mmol, yield 82.7%) was obtained by column chromatography purification.

[0186] Step 7

[0187]

[0188] At room temperature, under nitrogen protection, 1,6-dibromopyrene (2.38 g, 6.6 mmol), intermediate 6 (6.2 g, 15.2 mmol), Pd(OAc) 2 (74 mg, 0.33 mmol), t-Bu 3 P·HBF4 (191 mg, 0.66 mmol) and t-BuONa (1.46 g, 15.2 mmol), xylene (33 mL) was added, and the system was heated to 95°C. After the reaction was completed, the product compound BD176 (6 g, 5.97 mmol, yield 90%) was obtained by column chromatography purification. The product was identified as the target product with a molecular weight of 1004.5.

[0189] Synthesis Example 2: Synthesis of Compound BD109

[0190] first step:

[0191]

[0192] At room temperature and under nitrogen protection, Pd 2 (dba) 3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 5 (6 g, 19.9 mmol), [1,1′-biphenyl]-3-amine (5.5 g, 30 mmol) and t-BuONa (3.8 g, 39.8 mmol) were added to toluene (100 mL), and the system was heated to 120° C. for 2 h. After the reaction was completed, it was purified by column chromatography to obtain a colorless oil intermediate 7 (6.7 g, 16.4 mmol, yield 83%).

[0193] Step 2:

[0194]

[0195] At room temperature, under nitrogen protection, 1,6-dibromopyrene (2.2 g, 6.1 mmol), intermediate 7 (5.5 g, 14 mmol), Pd(OAc) 2 (68 mg, 0.3 mmol), tBu 3 PH + BF 4 - (174 mg, 0.6 mmol) and t-BuONa (1.3 g, 14 mmol), xylene (30 mL) was added, and the system was heated to 95°C. After the reaction was completed, it was purified by column chromatography to obtain a yellow-green solid BD109 (5 g, 5.1 mmol, yield 84%). The product was identified as the target product with a molecular weight of 976.5.

[0196] Comparative Synthesis Example 1: Synthesis of Comparative Compound A

[0197] first step:

[0198]

[0199] Pd(OAc) 2 (52 mg, 0.23 mmol), tBu 3 PH + BF 4 - (134 mg, 0.46 mmol) was placed in a 250 mL two-necked bottle and xylene (100 mL) was added. N 2 After 20 minutes, until the color stopped changing, 1,6-dibromopyrene (2.77 g, 7.68 mmol), bis(4-methyl-[1,1′-biphenyl]-3-yl)amine (5.9 g, 16.9 mmol), and sodium tert-butoxide (3.69 g, 38.4 mmol) were added successively. 2 After 10 minutes, the system was heated to 90°C until the raw materials reacted completely. After the reaction was completed, the product was purified by column chromatography to obtain the comparative compound A (2.4 g, 2.68 mmol, yield 34.9%). The product was identified as the target product with a molecular weight of 896.4.

[0200] Comparative Synthesis Example 2: Synthesis of Comparative Compound B

[0201] first step:

[0202]

[0203] LDA (100 mL, 200 mmol) was placed in a 250 mL three-necked flask, stirred under dry ice-ethanol for half an hour, methyl isobutyrate (23 mL, 200 mmol) was added, and stirring was continued for half an hour. Benzyl bromide (25 g, 100 mmol) was added thereto, and filtered through diatomaceous earth. After concentration, the crude product intermediate 8 was obtained, which was directly subjected to the next step of reaction.

[0204] Step 2:

[0205]

[0206] Mix intermediate 8 (27 g, 100 mmol) and potassium hydroxide (56 g, 1 mol), add 100 mL of water and 10 mL of methanol, and heat to 100°C to react until the reaction is complete as detected by TLC. Cool and wait for the reaction to return to room temperature, add concentrated hydrochloric acid to adjust the pH of the system to acidic, extract the organic phase with ethyl acetate, combine the organic phases, and concentrate.

[0207] The above product (27 g, 100 mmol) was dissolved in 200 mL of dichloromethane. 2After blowing air, add a drop of DMF, gradually add oxalyl chloride (12.8 mL, 120 mmol), and after the system no longer produces bubbles, move the reaction to an ice-water bath and stir for half an hour, add aluminum chloride (14.3 g, 108 mmol) in batches, and monitor by TLC until the reaction is complete. Through column chromatography, eluting with PE, a white solid intermediate 9 (22 g, 91.6 mmol, yield 85%) was obtained.

[0208] Step 3:

[0209]

[0210] Intermediate 9 (22 g, 99 mmol) was dissolved in 300 mL of methanol, stirred in an ice-water bath for half an hour, and NaBH was added in batches. 4 After the reaction is complete, the mixture is filtered through celite and the filtrate is concentrated.

[0211] The above product was dissolved in dichloromethane and Et 3 SiH (22.5 g, 198 mmol) was placed in an ice-water bath and stirred for half an hour, TFA (34 g, 297 mmol) was gradually added dropwise, concentrated, and purified by column chromatography to obtain a colorless oil intermediate 10 (7.7 g, 34.4 mmol, yield 35%).

[0212] Step 4:

[0213]

[0214] At room temperature and under nitrogen protection, Pd 2 (dba 3 )(1g, 1.1mmol), intermediate 10 (5.1g, 22.7mmol), 4-methyl-[1,1′-biphenyl]-3-amine (5g, 27.2mmol), BINAP (1.4g, 2.2mmol) and t-BuONa (4.7g, 49.6mmol) were added to xylene (100mL), and the system was heated to 90°C for overnight reaction. After the reaction was completed, it was purified by column chromatography to obtain a white solid intermediate 11 (5.7g, 17.4mmol, yield 76%).

[0215] Step 5:

[0216]

[0217] At room temperature, under nitrogen protection, 1,6-dibromopyrene (2.6 g, 7.2 mmol), 2,2-dimethyl-N-(4-methyl-[1,1′-biphenyl]-3-yl)-2,3-dihydro-1H-indan-4-amine (5.7 g, 17.4 mmol), Pd(OAc) 2(161 mg, 0.72 mmol), t-Bu 3 P.BF 4 (406 mg, 1.4 mmol) and t-BuONa (2.7 g, 28.2 mmol) were added to xylene (20 mL), and the system was heated to 100°C until the reaction was complete. After purification by column chromatography, a yellow-green solid comparative compound B (1.2 g, 1.41 mmol, yield 20%) was obtained. The product was identified as the target product with a molecular weight of 852.4.

[0218] Comparative Synthesis Example 3: Synthesis of Comparative Compound C

[0219] first step:

[0220]

[0221] At room temperature and under nitrogen protection, Pd 2 (dba) 3 (910 mg, 0.99 mmol), BINAP (1.18 g, 1.99 mmol), intermediate 5 (6 g, 19.9 mmol), aniline (2.79 g, 30 mmol) and t-BuONa (3.8 g, 39.8 mmol), toluene (100 mL) were added, and the system was heated to 120 ° C for 3 h. After the reaction was completed, it was purified by column chromatography to obtain a colorless oil intermediate 12 (5.3 g, 16.9 mmol, yield 85%).

[0222] Step 2:

[0223]

[0224] At room temperature, under nitrogen protection, 1,6-dibromopyrene (2.38 g, 6.6 mmol), intermediate 12 (4.76 g, 15.2 mmol), Pd(OAc) 2 (74 mg, 0.33 mmol), t-Bu 3 P·HBF 4 (191 mg, 0.66 mmol) and t-BuONa (1.46 g, 15.2 mmol) were added to xylene (30 mL), and the system was heated to 95°C. After the reaction was completed, the yellow-green solid comparative compound C (4.68 g, 5.67 mmol, yield 86%) was obtained by column chromatography separation and purification. The product was identified as the target product with a molecular weight of 824.4.

[0225] 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.

[0226] Device Example 1

[0227] 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 BD176 is 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.

[0228] Device Example 2

[0229] The implementation of Device Example 2 is the same as that of Device Example 1, except that Compound BD109 is used instead of Compound BD176 in the light emitting layer (EML).

[0230] Device Comparison Example 1

[0231] 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 BD176 in the emission layer (EML).

[0232] Device Comparison Example 2

[0233] The implementation of Comparative Device Example 2 is the same as that of Example 1, except that Compound C is used instead of Compound BD176 in the light emitting layer (EML).

[0234] Device Comparison Example 3

[0235] The implementation of Comparative Device Example 3 is the same as that of Example 1, except that Compound B is used in place of Compound BD176 in the emission layer (EML).

[0236] 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.

[0237] Table 1 Device structures of device embodiments and comparative examples

[0238]

[0239] The material structure used in the device is shown below:

[0240]

[0241]

[0242] The IVL of all the devices of the embodiments and comparative examples was measured at different current densities and voltages. 2 The external quantum efficiency (EQE) and the maximum emission wavelength (λ max ), half maximum width (FWHM) and CIE data.

[0243] Table 2 Device data of Example 1, Comparative Example 1 and Comparative Example 3

[0244] Part Number CIE(x,y) λmax(nm) FWHM(nm) EQE(%) Example 1 0.135,0.118 461 29.70 9.12 Comparative Example 1 0.140,0.098 456 32.20 8.88 Comparative Example 3 0.135,0.118 461 30.10 9.05

[0245] discuss:

[0246] Table 2 shows the device data of Example 1, Comparative Example 1 and Comparative Example 3. It can be seen from the table that the external quantum efficiency (EQE) of device Example 1 is 9.12%, the maximum emission wavelength is 461nm, CIE is (0.135, 0.118), and the half-peak width is 29.7nm; the external quantum efficiency (EQE) of Comparative Example 1 is 8.88%, the maximum emission wavelength is 456nm, CIE is (0.140, 0.098), and the half-peak width is 32.2nm. Compared with Comparative Example 1, the EQE of Example 1 is increased by 2.7%, and the half-peak width is narrowed by 3.5nm. From the results of Example 1 compared with Comparative Example 1, due to the introduction of a specific benzo saturated ring substituent in an aromatic group in the aromatic amine, the device results have a higher EQE and a narrower half-peak width, which effectively increases the blue luminescence performance.

[0247] The external quantum efficiency (EQE) of Comparative Example 3 is 9.05%, the maximum emission wavelength is 461nm, the CIE is (0.135, 0.118), and the half-peak width is 30.1nm. Compared with the results of Comparative Example 3, due to the further introduction of aromatic groups on the benzo saturated ring, the EQE of Example 1 is increased by 0.77%, and the half-peak width is narrowed by 0.4nm, which effectively increases the blue luminescence performance.

[0248] Table 3 Device data of Example 2 and Comparative Example 2

[0249]

[0250]

[0251] discuss:

[0252] Table 3 shows the device data of Example 2 and Comparative Example 2. It can be seen from the table that the external quantum efficiency (EQE) of Example 2 is 9.02%, the maximum emission wavelength is 463nm, the CIE is (0.133, 0.129), and the half-peak width is 30.5nm; the external quantum efficiency (EQE) of Comparative Example 2 is 8.65%, the maximum emission wavelength is 463nm, the CIE is (0.133, 0.133), and the half-peak width is 30.5nm. Compared with Comparative Example 2, the EQE of Example 2 is improved by 4.27%, and the half-peak width and the maximum emission wavelength remain unchanged. Compared with Comparative Example 2, it can be seen that by introducing a phenyl substituent in another aromatic group of the aromatic amine, the EQE can be improved.

[0253] In summary, the novel compound obtained by introducing a substituted six-membered (hetero) aromatic ring and a saturated ring structure into one of the aromatic groups of the aromatic amine-substituted pyrene compound and introducing a substituted (hetero) aromatic group into the other aromatic group is applied to an organic electroluminescent device, and finally a bluer emission wavelength, a higher EQE, and a narrower half-width are achieved in the device, thereby improving the overall performance of the device.

[0254] 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, wherein the compound is selected from the following structures: BD176:

2. An electroluminescent device, comprising: anode, cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 1.

3. The electroluminescent device of claim 2, wherein the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises the compound of claim 1. The electroluminescent device according to claim 3 , wherein the light-emitting layer further comprises a host material.

5. The electroluminescent device according to claim 4, wherein the host material comprises a compound having a structure of Formula 5: in, In formula 5, Rg1 to Rg8 are selected, at each occurrence, 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 alkyl having 2 to 20 carbon atoms, alkenyl, 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, nitrile, isonitrile, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; Rg9 and Rg 10 Each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. A composition comprising the compound of claim 1.

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