A fluorene-based triarylamine compound and application thereof in an organic electroluminescent device

Abstract

The application relates to the field of organic electroluminescent materials, in particular to a fluorene-based triarylamine compound and application thereof in an organic electroluminescent device. The chemical structure of the triarylamine compound is the fluorene-based triarylamine compound of the application, the synthesis is simple, the molecular structure is stable, the triarylamine compound has excellent hole transport property and electron blocking capacity, can be applied to hole transport layer materials of various color lights by connecting different substituent groups, and can reduce the device cost and improve the light-emitting efficiency and service life of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of organic electroluminescent materials, in particular to a fluorene-based triarylamine compound and its application in organic electroluminescent devices. BACKGROUND

[0002] Organic electroluminescent devices (also known as OLEDs, i.e. organic light-emitting diodes) are a class of self-luminescent electronic devices. Compared with other flat panel display technologies such as liquid crystal display (LCD), plasma display (PDP) and field emission display (FED), organic electroluminescent display has the characteristics of high contrast, wide viewing angle, fast response speed, excellent color performance, etc., and OLED devices can be prepared on flexible substrates to become flexible display products that can be rolled or bent. Therefore, in recent years, OLED displays have been widely used in consumer electronics fields such as mobile phones, tablet computers, wall-mounted televisions, and vehicle display fields.

[0003] OLED devices mainly consist of electrodes, organic light-emitting layers and organic functional layers, forming a sandwich-like structure. When a forward voltage is applied to the electrodes at both ends of the device, electrons and holes are injected from the anode and cathode of the device, respectively, transported through the organic functional layer, and the two types of carriers recombine in the organic light-emitting layer to form tightly bound electron-hole pairs, i.e. excitons. As the energy of the excitons is transferred to the light-emitting material and released in the form of photons, the device emits light. In order to improve the light-emitting efficiency of the device and reduce the driving voltage, suitable functional layer materials such as carrier injection layers, carrier transport layers, etc. are usually introduced. For example, a typical organic electroluminescent device structure includes: anode / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML, light-emitting host material: light-emitting guest material) / electron transport layer (ETL) / electron injection layer (EIL) / cathode. Among them, the hole transport layer material is responsible for transferring holes to the light-emitting layer and plays a very important role.

[0004] In recent years, the proportion of OLED technology-based displays in the consumer electronics field has increased year by year, which requires that its driving power, light-emitting efficiency and service life be no less than those of other conventional displays. Therefore, it is necessary to develop functional layer materials with stable chemical structure and excellent performance. Specifically, the material should have appropriate molecular weight and solubility, so as to be easy to purify and to be thermally deposited in a high vacuum environment; at the same time, it also needs to have good thermal stability and electrochemical stability to ensure the extension of the service life of the device. However, the efficiency and stability of the existing materials need to be further improved. SUMMARY

[0005] In view of the above-mentioned disadvantages of the prior art, the present application aims to provide a fluorene-based triarylamine compound and its application in an organic electroluminescent device, for solving the problems in the prior art.

[0006] To achieve the above-mentioned objects and other related objects, one aspect of the present application provides a fluorene-based triarylamine compound, the chemical structure of the triarylamine compound is shown in formula (1):

[0007]

[0008] In formula (1), R1, R2 are the same or different from each other, and are independently selected from substituted or unsubstituted C1-C12 linear or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R1 and R2 are bonded to form a ring;

[0009] R m 、R n Each occurrence is independently selected from one of deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl, or two R m groups located at adjacent positions are connected to each other to form a substituted or unsubstituted benzene ring; m and n are independently selected from 0, 1, 2, 3, or 4;

[0010] L0, L1, L2 are the same or different from each other, and are each independently selected from a single bond, substituted or unsubstituted C6-C20 arylene, or substituted or unsubstituted C2-C20 heteroarylene;

[0011] Ar1, Ar2 are the same or different from each other, and are each independently selected from substituted or unsubstituted C6-C40 aryl, or substituted or unsubstituted C2-C40 heteroaryl;

[0012] A is selected from substituted or unsubstituted acenyl, or substituted or unsubstituted groups shown in formula (2)-(4):

[0013]

[0014] In formula (2)-(4), Z1-Z 12 are the same or different from each other, and are each independently selected from -N(R d )-, -C(R e )(R f )-, -O- or -S-; wherein, the R d , R e , R f, each independently of one another, hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, or substituted or unsubstituted C2-C18 heteroaryl; * represents a bonding site.

[0015] Another aspect of the present application provides an organic layer comprising the aforementioned fluorene-based triarylamine compound.

[0016] Another aspect of the present application provides the use of the aforementioned fluorene-based triarylamine compound and / or the aforementioned organic layer in an organic electroluminescent device.

[0017] Another aspect of the present application provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer, and the organic layer comprises the aforementioned fluorene-based triarylamine compound.

[0018] Another aspect of the present application provides a display or lighting device comprising the aforementioned organic electroluminescent device.

[0019] Compared with the prior art, the present application has the following advantages:

[0020] The triarylamine compound provided by the present application has good solubility, hole transport properties and chemical stability; in addition, the introduction of cycloalkyl and aryl or heterocycloalkyl and aryl into the molecule is beneficial to obtaining a continuous and uniform amorphous film with excellent thermal stability. The compound provided by the present application is used as a hole transport material in an organic electroluminescent device, which has the advantages of low operating voltage, high luminous efficiency and long service life, and can reduce the production cost of the device. BRIEF DESCRIPTION OF DRAWINGS

[0021] Figure 1 is a schematic structural diagram of an organic electroluminescent device in the embodiment.

[0022] Figure 2 is another schematic structural diagram of an organic electroluminescent device in the embodiment.

[0023] In the drawings:

[0024] 101 substrate

[0025] 102 first electrode

[0026] 103 hole injection layer

[0027] 104 first layer hole transport layer

[0028] 105 second layer hole transport layer

[0029] 106 light-emitting layer

[0030] 107 hole-blocking layer

[0031] 108 electron-transporting layer

[0032] 109 second electrode

[0033] 110 capping layer DETAILED DESCRIPTION

[0034] The specific disclosed fluorene-based compounds and their use in organic electroluminescent devices are described in detail below. Other advantages and benefits of the present application will be apparent from this disclosure. The present application can be implemented or applied in other different specific embodiments, and the details in the present specification can be modified or changed based on different views and applications without departing from the spirit of the present application.

[0035] Before further description of the present application, it should be understood that the scope of the present application is not limited to the particular specific embodiments described below; it should also be understood that the terminology used in the present application is used for the purpose of describing particular specific embodiments only and is not intended to limit the scope of the present application; in the present specification and claims, the singular forms "a", "an" and "the" include the plural forms unless the context clearly indicates otherwise.

[0036] When the embodiments give numerical ranges, it should be understood that, unless the present application indicates otherwise, both endpoints of each numerical range and any number between the two endpoints can be selected. Unless otherwise defined, all technical and scientific terms used in the present application have the same meaning as commonly understood by those skilled in the art. In addition to the specific methods, devices, materials used in the embodiments, any method, device and material of the prior art similar or equivalent to those described in the embodiments of the present application can also be used to implement the present application according to the mastery of the prior art by those skilled in the art and the description of the present application.

[0037] The present inventors have made intensive researches and aimed to provide a class of fluorene-based triarylamine compounds. Firstly, fluorene and its derivatives have a special planar biphenyl structure, and the molecular structure is stable, and the thermal stability and chemical stability are good. The introduction of such fragments into the triarylamine system is conducive to obtaining a material with high hole mobility. Secondly, the introduction of aryl fused cycloalkyl or aryl fused heterocycloalkyl fragments can form a certain intermolecular steric hindrance, which can not only improve the solubility of the molecule and reduce the sublimation temperature, but also help to inhibit the intermolecular stacking during film formation, and tend to form a uniform amorphous film with few defects, which is less affected by the joule heat generated during device operation, thereby prolonging the service life of the device. On the other hand, the introduction of a phenylene group between the aryl fused cycloalkyl or aryl fused heterocycloalkyl group and the fluorene group can extend the conjugation, so that the carrier transport properties of the molecule are not sacrificed too much. In addition, by connecting different aromatic groups on the triarylamine, the front-line orbital energy level and singlet and triplet energy levels of the molecule can be easily regulated, thereby meeting the requirements of different color light (for example, red, green and blue light) devices for hole transport layer materials. On this basis, the present application is completed.

[0038] The present application provides a fluorene-based triarylamine compound in the first aspect, and the chemical structure of the fluorene-based triarylamine compound is shown in formula (1):

[0039]

[0040] In formula (1), R1 and R2 are the same or different from each other, and are independently selected from substituted or unsubstituted C1-C12 linear or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R1 and R2 are bonded to form a ring;

[0041] R m , R n Each occurrence is independently selected from one of deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl, or two R m groups located at adjacent positions are connected to each other to form a substituted or unsubstituted benzene ring; m and n are independently selected from 0, 1, 2, 3, or 4;

[0042] L0, L1 and L2 are the same or different from each other, and are independently selected from a single bond, substituted or unsubstituted C6-C20 arylene, or substituted or unsubstituted C2-C20 heteroarylene;

[0043] Ar1, Ar2are the same as or different from each other, and each is independently selected from a substituted or unsubstituted C6-C40 aryl group, or a substituted or unsubstituted C2-C40 heteroaryl group;

[0044] A is selected from a substituted or unsubstituted acenyl group, or a substituted or unsubstituted group represented by formula (2)-(4):

[0045]

[0046] In formula (2)-(4), Z1-Z 12 are the same as or different from each other, and each is independently selected from -N(R d )-, -C(R e )(R f )-, -O- or -S-; wherein, the R d , R e , R f are the same as or different from each other, and each is independently selected from hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C18 aryl group, or a substituted or unsubstituted C2-C18 heteroaryl group; * represents a bonding site.

[0047] In the compound provided by the present application, optionally, the chemical structure of the compound is represented by formula (5)-(16):

[0048]

[0049] In formula (5)-(16), R1-R2, R m -R n , A, L0, L1, L2, Ar1, Ar2, m and n are defined as in formula (1).

[0050] In the compound provided by the present application, in formula (1), R1, R2, R a -R f , L0, L1, L2, A, Z1-Z 12 , Ar1 and Ar2, the "substituted" in "substituted or unsubstituted" is independently selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl; and the substituents of R1-R2, R a -R f , L0, L1, L2, A, Z1-Z 12 , Ar1 and Ar2 are the same as or different from each other.

[0051] In the compounds provided by the present application, the hydrogen on the aromatic ring in formulae (2) to (4) is unsubstituted, or any hydrogen atom on the aromatic ring can be substituted with one of the following groups: deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, -CD3, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylthio, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted C1-C18 keto, substituted or unsubstituted C2-C18 alkoxycarbonyl, substituted or unsubstituted C6-C18 aryloxycarbonyl.

[0052] In the compounds provided by the present application, when R1and R2are the same or different and are independently selected from substituted or unsubstituted C1-C12 straight chain or branched alkyl in formulae (1), (5) to (16), they can be, for example, C1-C10, C1-C8, C1-C6, C1-C5, etc. Alternatively, they can be selected from methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc. The hydrogen on the alkyl group can be further substituted with one or more of the following substituents. The "substituted" in "substituted or unsubstituted" is independently selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituents are selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, biphenylyl, naphthyl, pyridyl, or any combination thereof.

[0053] In the compounds provided herein, in formula (1), (5)-(16), R1, R2, when the same or different, are independently selected from substituted or unsubstituted C3-C12 cycloalkyl. In some embodiments, the cycloalkyl group has 3 to 11 carbon atoms (i.e., C3-C11 cycloalkyl), or 3 to 10 carbon atoms (i.e., C3-C10 cycloalkyl), or 3 to 8 carbon atoms (i.e., C3-C8 cycloalkyl), or 3 to 7 carbon atoms (i.e., C3-C7 cycloalkyl), or 3 to 6 carbon atoms (i.e., C3-C6 cycloalkyl). Optionally, the "cycloalkyl" group includes monocyclic, bicyclic, or tricyclic cycloalkyl groups. Bicyclic and tricyclic cycloalkyl groups include bridged, fused, and spirocyclic cycloalkyl groups. Further optionally, the cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cyclooctyl, decalin, octahydrocyclopenta-2,4-diene, octahydro-lH-indene, spirocyclic groups. The "cycloalkyl" group is optionally unsubstituted or substituted with one or more (e.g., 1-5, 1-4, 1-3, 1-2, or 1) substituents selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituents are selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenylyl, naphthyl, pyridyl, or any combination thereof.

[0054] In the compounds provided herein, when R1, R2are the same or different and are independently selected from substituted or unsubstituted C6-C30 aryl in formula (1), (5)-(16), it refers to a monovalent carbocyclic aromatic group containing 6 to 30 ring atoms and optionally containing one or more fused rings, such as C6-C30, C6-C25, C6-C20, C6-C15 aryl, C6-C12 aryl, and the like. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, the monocyclic aryl group includes, but is not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, and the like. The polycyclic aryl group includes, but is not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group can be substituted, such as 9,9'-dimethylfluorenyl, 9,9'-spirobifluorenyl, and the like. In addition, two of the substituents can be combined to form a spirocyclic structure, such as 9,9'-spirobifluorenyl, and the like. The "aryl" group is optionally substituted aryl. Substituted aryl refers to an aryl group that is substituted one or more times (e.g., 1-4, 1-3, or 1-2 times) with a substituent, such as an aryl group that is mono-, di-, or tri-substituted with a substituent, wherein the substituent is optionally selected, for example, from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituent is selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenyl, naphthyl, pyridyl, or any combination thereof.

[0055] In the compounds provided by the present application, in formula (1), (5)-(16), R1, R2, when the same or different, are independently selected from substituted or unsubstituted C2-C30 heteroaryl groups. For example, C2-C20 heteroaryl groups, C2-C15 heteroaryl groups, C2-C12 heteroaryl groups, C2-C10 heteroaryl groups, etc. Alternatively, for example, selected from pyridyl groups, furanyl groups, thienyl groups, benzofuranyl groups, benzothienyl groups, dibenzofuranyl groups, dibenzothienyl groups, carbazolyl groups, etc. The heteroaryl groups can be unsubstituted or substituted. Substituted heteroaryl groups refer to heteroaryl groups substituted one or more times (for example, 1-4, 1-3, or 1-2 times) by substituents, wherein the substituents are optionally selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl groups, C3-C10 cycloalkyl groups, C1-C10 alkoxy groups, C1-C10 alkylthio groups, C6-C20 aryl groups, C2-C20 heteroaryl groups. Preferably, the substituents are selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy groups, methylthio groups, methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, i-butyl groups, t-butyl groups, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, phenyl groups, tolyl groups, t-butylphenyl groups, biphenyl groups, naphthyl groups, pyridyl groups, or any combination thereof.

[0056] Alternatively, in formula (1), (5)-(16), R1, R2, when the same or different, are independently selected from substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C2-C20 heteroaryl groups.

[0057] In the compounds provided by the present application, in formula (1), (5)-(16), when R1, R2, when the same or different, R1 and R2 are bonded to form a ring, the ring can be formed, for example, in the following manner: R1 and R2 are both selected from C1-C12 straight-chain or branched alkyl groups, and are connected to each other by a single bond to form a substituted or unsubstituted cycloalkyl group. For another example, R1 and R2 are both selected from substituted or unsubstituted C6-C30 aryl groups, and are connected to each other by one of a single bond, -O-, -S-, -N(R a )-, -C(R b )(R c )- to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. R a , R b , R c , when the same or different, are independently selected from substituted or unsubstituted C1-C10 straight-chain or branched alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C2-C20 heteroaryl groups.

[0058] Optionally, R1~R2are simultaneously selected from C1~C12 linear or branched alkyl, and are connected to each other by a single bond to form a substituted or unsubstituted cyclopropane, a substituted or unsubstituted cyclobutane, a substituted or unsubstituted cyclopentane, a substituted or unsubstituted cyclohexane, a substituted or unsubstituted cycloheptane, etc. The substituent group can be, for example, deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenyl, naphthyl, pyridyl, or any combination thereof. The substituted cyclopentane is, for example, The substituted cyclohexane is, for example,

[0059] Optionally, R1~R2are simultaneously selected from substituted or unsubstituted phenyl, and are connected to each other by a single bond, -C(R b )(R c )-, to form a substituted or unsubstituted aromatic ring structure. R1~R2are connected by a single bond to form, for example, etc. Here, the single bond is a bond linker. In other words, are directly connected by a bond linker to form The explanation of the single bond appearing elsewhere is the same as here. No further elaboration is given. For another example, R1~R2are connected by -C(R b )(R c )- to form

[0060] Optionally, R1~R2are simultaneously selected from substituted or unsubstituted phenyl, and are connected to each other by one of -O-, -S-, -N(R a )- to form a substituted or unsubstituted heteroaromatic ring structure. For example, R1~R2are connected by -O- to form etc. For example, R1~R2are connected by -S- to form For another example, R1~R2are connected by -N(R a )- to form etc.

[0061] Further, for the convenience of description, the group formed by the bonding of R1~R2to each other is defined as group E, and group E is selected from any one of the following groups:

[0062]

[0063] In group E, * represents the bonding site, and is bonded to the 9,9'-position of the fluorene group in formula (1) or formula (5)~formula (16) to form a spiro ring structure. For example, when group E is , the compound of formula (1) is

[0064] R a ,R b ,R c are the same or different from each other and are independently selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, t-butylphenyl, naphthyl, or biphenyl. a ,R b ,R c are the same or different from each other and are independently selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, t-butylphenyl, naphthyl, or biphenyl.

[0065] In each of the structures of the group E, a hydrogen atom on any of the benzene rings can be replaced by one of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, ethylphenyl, t-butylphenyl, naphthyl, pyridyl; a hydrogen atom on any of the cycloalkyl groups can be replaced by one of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl.

[0066] Preferably, R1~R2are the same or different from each other and are each independently selected from one of the following groups of substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl; or R1~R2are bonded to each other to form a group E selected from any of the following groups:

[0067]

[0068] wherein R a ,R b ,R c are the same or different from each other and are independently selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, t-butylphenyl, naphthyl, or biphenyl.

[0069] In R1~R2, the "substituted" in "substituted or unsubstituted" is independently selected from one or more of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, wherein the substituents are the same or different from each other. For example, the substituted methyl is -CD3. For another example, the substituted phenyl is benzyl.

[0070] In the compounds provided by the present application, R m ,R neach occurrence is independently selected from one of deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl, or two R m groups attached to each other form a substituted or unsubstituted phenyl ring; m and n are independently selected from 0, 1, 2, 3, 4; m = 0 means that there is no R m group attached to the phenyl ring; n = 0 means that there is no R n group attached to the phenyl ring. m m n n

[0071] In particular embodiments, R m is selected from hydrogen, deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, or biphenyl; or when m > 1, two R m groups attached to adjacent positions form a phenyl ring. When two R a groups attached to adjacent positions form a phenyl ring, the structure is

[0072] In particular embodiments, R n is selected from hydrogen, deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, or biphenyl.

[0073] ​​​​In the compounds provided by this invention, L0, L1, and L2 may be the same as or different from each other, and each is independently selected from single-bonded, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C2-C20 heteroarylene groups. In specific embodiments, L0, L1, and L2 are each independently selected from single-bonded groups, or when not selected from single-bonded groups, they may be the same as or different from each other, and each is independently selected from one of the following substituted or unsubstituted groups: phenylene, naphthylene, pyridinylene, thiopheneylene, selenene, furanylene, pyrroleylene, benzothiopheneylene, benzofuranylene, indoleylene, dibenzothiopheneylene, dibenzofuranylene, fluoreneylene, and carbazoylene. In L0, L1, and L2, the substituents in "substituted or unsubstituted" are independently selected from any one or a combination of the following groups: deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, diphenyl, naphthyl, and pyridyl.

[0074] In the compounds provided by this invention, group A is selected from substituted or unsubstituted acenaphthenic groups, or substituted or unsubstituted groups shown in formulas (2) to (4):

[0075]

[0076] In equations (2) to (4), * represents the bonding site; Z1 to Z 12 Whether they are the same or different, they are each independently selected from -N(R) d )-、-C(R e (R) f -, -O-, or -S-; wherein, the R d R e R f They may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C18 aryl, or substituted or unsubstituted C2-C18 heteroaryl.

[0077] In formulas (2) to (4) of this invention, R d R e R f They may be the same as or different from each other, and each is independently selected from hydrogen.

[0078] In formulas (2) to (4) of this invention, R d R e R f They may be the same as or different from each other, and each is independently selected from deuterium.

[0079] In the present application, R d , R e , R f , each independently selected from the group consisting of substituted or unsubstituted C1-C10 alkyl. For example, C1-C10, C1-C8, C1-C6, C1-C5, etc. Alternatively, selected from the group consisting of methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc. The hydrogen on the alkyl group can be further substituted by one or more of the following substituents. The "substituted" in the "substituted or unsubstituted" is independently selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituents are selected from the group consisting of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, biphenylyl, naphthyl, pyridyl, or any combination thereof.

[0080] In the present application, R d , R e , R f, each of which is the same or different, is independently selected from substituted or unsubstituted C3-C10 cycloalkyl. In some embodiments, it has 3 to 8 carbon atoms (i.e., C3-C8 cycloalkyl), or 3 to 7 carbon atoms (i.e., C3-C7 cycloalkyl), or 3 to 6 carbon atoms (i.e., C3-C6 cycloalkyl). Optionally, the "cycloalkyl" includes monocyclic, bicyclic or tricyclic cycloalkyl. Bicyclic and tricyclic cycloalkyl includes bridged, fused and spiro cycloalkyl. Further optionally, the cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cyclooctyl, decalin, octalin, octahydro-lH-indene, spirocyclic. The "cycloalkyl" is optionally unsubstituted or substituted with one or more (e.g., 1-5, 1-4, 1-3, 1-2, or 1) selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituents are selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenyl, naphthyl, pyridyl, or any combination thereof.

[0081] In the present application, R d , R e , R f, each other same or different, independently selected from substituted or unsubstituted C6-C18 aryl. The aryl can be a monocyclic aryl or a polycyclic aryl. In some embodiments, the monocyclic aryl includes, but is not limited to, phenyl, biphenyl, terphenyl, and the like. The polycyclic aryl includes, but is not limited to, naphthyl, anthryl, fluorenyl, and the like. The fluorenyl can be substituted, such as 9,9'-dimethylfluorenyl, 9,9'-spirobifluorenyl, and the like. In addition, two of the substituents can combine with each other to form a spiro structure, such as 9,9'-spirobifluorenyl, and the like. The "aryl" is an optionally substituted aryl. The substituted aryl refers to an aryl substituted one or more times (e.g., 1-4, 1-3, or 1-2 times) with a substituent, such as the aryl is mono-, di-, or tri-substituted with a substituent, wherein the substituent is optionally selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituent is selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenyl, naphthyl, pyridyl, or any combination thereof.

[0082] In the formula (2)-(4) of the present application, the R d , R e , R f , each other same or different, substituted or unsubstituted C2-C18 heteroaryl. For example, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted C2-C12 heteroaryl, or substituted or unsubstituted C2-C10 heteroaryl, and the like. For example, selected from pyridyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like. The heteroaryl group can be unsubstituted or substituted. The substituted heteroaryl refers to a heteroaryl substituted one or more times (e.g., 1-4, 1-3, or 1-2 times) with a substituent, wherein the substituent is optionally selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl. Preferably, the substituent is selected from deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenyl, naphthyl, pyridyl, or any combination thereof.

[0083] In the formula (2) to (4) of the present application, A is selected from substituted or unsubstituted acenaphthenyl, or is selected from a fused ring structure formed by a group G and a benzene ring; the group G is selected from any one of the following structures:

[0084]

[0085]

[0086]

[0087] wherein, * carbon represents a carbon corresponding to the connection of the carbon on the benzene ring; R d The definitions are the same as before. For example forms a The other descriptions are the same as here, and will not be repeated.

[0088] In specific embodiments, the group A includes but is not limited to the following groups:

[0089]

[0090] In the compound provided by the present application, Ar1, Ar2are the same or different from each other, and are each independently selected from substituted or unsubstituted C6-C40 aryl, or substituted or unsubstituted C2-C40 heteroaryl. Alternatively, the Ar1and Ar2are the same or different from each other, and are each independently selected from any one of the following groups:

[0091]

[0092] wherein, X is independently selected from -N-, -CH-, -C(R3)- or -C *a ; R3is independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylthio, substituted or unsubstituted C6-C20 aryl, C2-C20 substituted or unsubstituted heteroaryl; aR3is selected from the group consisting of deuterium, fluorine, chlorine, bromine, cyano, nitro, or one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, pyridyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, and the like. The "substituted" substituents are independently selected from one or more of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, wherein the substituents are the same or different from each other.

[0093] Y is selected from the group consisting of -0-, -S-, -Se-, -N(R4)-, -C(R5)(R6), -Si(R7)(R8)-; R4to R8are each independently selected from the group consisting of substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted C3to C10cycloalkyl, substituted or unsubstituted C6to C20aryl, substituted or unsubstituted C2to C20heteroaryl; or, R5, R6are independently selected from substituted or unsubstituted C1to C6linear or branched alkyl and R5, R6are bonded to each other to form a substituted or unsubstituted C5to C12aliphatic ring; or R7, R8are independently selected from substituted or unsubstituted C6to C12aryl or substituted or unsubstituted C2to C12heteroaryl and R7, R8are connected to each other by one of a single bond, -0-, -S-, -N(R9)-, -C(R 10 )(R 11 )-, to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R9to R 11 are independently selected from the group consisting of deuterium, fluorine, chlorine, bromine, cyano, nitro, substituted or unsubstituted C1to C10alkyl, substituted or unsubstituted C3to C10cycloalkyl, substituted or unsubstituted C1to C10alkoxy, substituted or unsubstituted C1to C10alkylthio, substituted or unsubstituted C6to C20aryl, or C2to C20substituted or unsubstituted heteroaryl.

[0094] Optionally, R4to R8are independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, or one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, pyridyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, and the like. The "substituted" substituents are independently selected from one or more of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, wherein the substituents are the same or different from each other.

[0095] Alternatively, R5and R6are bonded to each other to form a cyclopropane, cyclobutane, cyclopentane, cyclohexane, or cycloheptane, and the like.

[0096] R7and R8are simultaneously selected from substituted or unsubstituted phenyl, and are bonded to each other by one of -C(R 10 )(R 11 )-, to form a substituted or unsubstituted aryl ring group structure. R7and R8are bonded by a single bond, for example, to form and the like. Here, the single bond is a bond linker. In other words, are directly bonded by a bond linker to form The explanation of the single bond elsewhere applies here. No further elaboration. For another example, R7and R8are bonded by -C(R 10 )(R 11 )-, to form

[0097] Alternatively, R7and R8are simultaneously selected from substituted or unsubstituted phenyl, and are bonded to each other by one of -O-, -S-, -N(R9)-, to form a substituted or unsubstituted heteroaryl ring group structure. For example, R7and R8are bonded by -O- to form and the like. For example, R7and R8are bonded by -S- to form For another example, R7and R8are bonded by -N(R9)- to form and the like.

[0098] In X and Y, the "substituted" substituents in "substituted or unsubstituted" are independently selected from any one of the following groups: deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenyl, naphthyl, pyridyl.

[0099] In particular embodiments, Ar1and Ar2are the same or different from each other and are each independently selected from the group consisting of:

[0100]

[0101] In any of the groups, any one and only one of the carbons on the aromatic ring is a bonding site, or any one of the hydrogens can be replaced with deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl.

[0102] For example Upon substitution of the -D group, for example, the following can be formed

[0103] In the compounds provided herein, m is optionally selected from 0, 1, 2, or 3; further optionally, m is selected from 0, 1, or 2. Further optionally, m is selected from 0, or 1, etc. n is optionally selected from 0, 1, 2, or 3; further optionally, n is selected from 0, 1, or 2. Further optionally, n is selected from 0, or 1, etc.

[0104] In the compounds provided herein, the compound is selected from one or more of the following chemical structures:

[0105]

[0106]

[0107]

[0108]

[0109] In particular, the above structures can be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxyl, carbonyl, ester, imide, phosphine, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroaryl amino, arylamino, arylheteroarylamino, arylphosphine, and heteroaryl.

[0110] A second aspect of the present application provides an organic layer comprising the fluorene-based triarylamine compound of the first aspect of the present application.

[0111] The third aspect of the present application provides a fluorene-based triarylamine compound according to the first aspect of the present application, and / or an organic layer according to the second aspect of the present application for use in an organic electroluminescent device.

[0112] The fourth aspect of the present application provides an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, which is a bottom or top emission device structure, and the organic layer can be a single layer structure or a multi-layer series structure in which two or more organic layers are laminated, and the organic layer includes at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, or an electron transport layer. It can be prepared using common methods and materials for preparing an organic electroluminescent device. The organic layer includes a fluorene-based triarylamine compound according to the first aspect of the present application.

[0113] In the organic electroluminescent device according to the present application, the first electrode serves as an anode layer, and the anode material can be, for example, a material having a large work function so that holes are smoothly injected into the organic layer. It can be, for example, a metal, a metal oxide, a combination of a metal and an oxide, a conductive polymer, or the like. The metal oxide can be, for example, indium tin oxide (ITO), zinc oxide, indium oxide, indium zinc oxide (IZO), or the like.

[0114] In the organic electroluminescent device according to the present application, the second electrode serves as a cathode layer, and the cathode material can be, for example, a material having a small work function so that electrons are smoothly injected into the organic layer. The cathode material can be, for example, a metal or a multi-layer structure material. The metal can be, for example, magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead, or an alloy thereof. The cathode material is preferably selected from magnesium and silver.

[0115] In the organic electroluminescent device according to the present application, the material of the hole injection layer is preferably a material having a highest occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer, which serves as a material that advantageously receives holes from the anode at a low voltage.

[0116] In the organic electroluminescent device according to the present application, the material of the hole transport layer is a material having a high mobility for holes, which is suitable as a material that receives holes from the anode or the hole injection layer and transports the holes to the light-emitting layer. The material of the hole transport layer includes, but is not limited to, an organic material of arylamine, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, or the like.

[0117] In the organic electroluminescent device according to the present application, the material of the light-emitting layer can be generally selected from a material having a good quantum efficiency for fluorescence or phosphorescence as a material that can emit light in the visible region by receiving holes from the hole transport layer and electrons from the electron transport layer and combining the holes and the electrons.

[0118] In the organic electroluminescent device according to the present application, the material of the electron transport layer is a material having high mobility for electrons and is suitable as a material that advantageously receives electrons from the cathode and transports the electrons to the light-emitting layer.

[0119] In the organic electroluminescent device according to the present application, the material of the cover layer generally has a high refractive index, and thus can contribute to improvement in light efficiency of the organic light-emitting device, particularly, improvement in external light-emitting efficiency.

[0120] In the organic electroluminescent device according to the present application, the organic electroluminescent device is an organic photovoltaic device, an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor, or the like.

[0121] Another aspect of the present application provides a display or lighting device comprising the organic electroluminescent device according to the present application.

[0122] Unless otherwise specified, the compounds in the present application for which the synthetic method is not mentioned are commercially available; in the present application, the mass spectrometry is measured by a ZABHS-type mass spectrometer (manufactured by Micromass, UK), and the nuclear magnetic resonance is measured by a Bruker 400MHz-type nuclear magnetic resonance instrument (manufactured by Bruker, Germany).

[0123] Synthetic Examples:

[0124] The compounds involved in the present application can be prepared by the following general synthetic routes, but are not limited thereto. Those skilled in the art can make any modification, equivalent replacement, improvement, etc. on the basis thereof without departing from the principles of the present application, and extend the method to the scope of the technical solutions claimed in the claims of the present application.

[0125]

[0126] wherein, for compounds i, iii and v, X1, X2and X3are independently selected from iodine, bromine or chlorine. Preferably, when X2is selected from bromine, X1is selected from chlorine; preferably, X3is selected from bromine or chlorine.

[0127] For compound iv, when L0is selected from a single bond, X3is hydrogen; when L0is not selected from a single bond, X3is selected from boronic acid group or pinacol boronate group.

[0128] R1~R2、R m ~R n , A, L0, L1, L2, Ar1, Ar2, m and n are as defined in formula (1), formulae (5)~(16).

[0129] The compound provided by the present application can be synthesized by the Suzuki coupling reaction and the Ullmann coupling reaction commonly used in the art, and the preparation operation is mature and simple, and the low-cost large-scale synthesis and production can be realized.

[0130] Synthesis of compound iii:

[0131] Under the nitrogen atmosphere, a three-necked flask was added with compound i (40.0 mmol, 1 eq), compound ii (40.0 mmol, 1 eq) and degassed toluene (200 mL) in sequence, and after being stirred uniformly, tetrakis triphenyl phosphine palladium (924.4 mg, 0.8 mmol, 2% eq), potassium carbonate (13.8 g, 100 mmol, 2.5 eq), degassed ethanol (120 mL) and deionized water (80 mL) were added in sequence. After being stirred sufficiently, the reaction system was heated to reflux under the nitrogen atmosphere, and the analysis by thin layer chromatography showed that the raw material was substantially absent. When the reaction solution was cooled to room temperature, 100 mL of toluene was added to the reaction system, stirred for 5 minutes, and then separated by standing and using a separatory funnel. The organic phase was retained, the aqueous phase was extracted with toluene (3×40 mL), combined with the previously retained organic phase, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography (mobile phase: n-hexane / dichloromethane mixed solvent) to obtain compound iii.

[0132] Synthesis of the target compound:

[0133] Under the nitrogen atmosphere, a three-necked flask was added with compound iii (20.0 mmol, 1 eq), compound iv (20.0 mmol, 1 eq) and anhydrous toluene (120 mL) in sequence, and after being stirred sufficiently, sodium tert-butoxide (2.9 g, 30.0 mmol, 1.5 eq), bisbenzaldehyde palladium (113.2 mg, 0.2 mmol, 1% eq) and tri-tert-butyl phosphine (10% n-hexane solution, 1.0 mL, 0.4 mmol, 2% eq) were added in sequence. After being stirred, the above system was mixed sufficiently, heated to reflux under the nitrogen atmosphere, and the analysis by thin layer chromatography showed that the raw material was substantially absent. When the temperature of the reaction system was reduced to room temperature, a mixed solution of 5 mL of concentrated hydrochloric acid (37% aqueous solution) and 100 mL of deionized water was added to the reaction system, and the mixture was separated by standing and using a separatory funnel. The organic phase was retained, the aqueous phase was extracted with toluene (3×30 mL), combined with the previously retained organic phase, and the solvent was removed by distillation under reduced pressure. The crude product was separated by silica gel column chromatography (mobile phase: n-hexane / toluene mixed solvent) and recrystallized from a mixed solvent of toluene / ethanol / n-hexane to obtain the target compound.

[0134] The synthesis of compound ii is achieved by a Suzuki coupling reaction, which can be specifically referred to the preparation method of compound iii, except that the raw material compounds i and ii are replaced by compounds v and vi, respectively, in equal amounts.

[0135] The synthesis of compound iv can be referred to the method provided in the prior art document WO2016064110A1.

[0136] Further, compound i can be synthesized by taking 9,9'-dihydrofluorene derivatives or 9-fluorenone derivatives as starting materials, and the specific synthesis route is as follows.

[0137] a. When R1, R2 are each independently selected from substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl:

[0138]

[0139] Under a nitrogen atmosphere, a reaction bottle is sequentially added with a 9,9'-dihydrofluorene derivative (compound v, 50.0 mmol, 1 eq) and anhydrous tetrahydrofuran (100 mL), and after being stirred uniformly, the solution is cooled to 0°C, and potassium tert-butoxide (5.7 g, 50.0 mmol, 1 eq) is added in batches under a nitrogen atmosphere. After the addition is completed, the reaction system is slowly restored to room temperature, and stirring is continued for 1.5 hours. Then, iodinated alkane R1-I (50.0 mmol, 1 eq) is slowly added, and it is observed that the reaction system becomes a milky white suspension. The suspension is stirred under a nitrogen atmosphere at room temperature for 2 hours, and then filtered, and the filtrate is collected and the solvent is removed under reduced pressure. The obtained intermediate compound is further used as a reaction substrate, and the above experimental procedure is repeated, except that the iodinated alkane is replaced by R2-I in equal amounts, so as to obtain the target compound i.

[0140] b. When R1, R2 are each independently selected from substituted or unsubstituted alkyl, and are connected to each other by a single bond to form a cycloalkyl:

[0141] The synthesis of compound i is carried out by using a method similar to that of case a, except that the iodinated alkane is replaced by diiodinated alkane I-R2-R1-I in equal amounts, so as to obtain the target compound i through one-step reaction.

[0142] c. When R1, R2 are each independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and are connected to each other to form a spiro ring structure:

[0143]

[0144] wherein Z' is selected from a single bond, -O-, -S-, -N(R a )-, -C(R b )(Rc one of the following is connected to form a spiro structure. The R a ,R b ,R c are the same or different from each other, and are independently selected from substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, and substituted or unsubstituted C2-C20 heteroaryl.

[0145] Under a nitrogen atmosphere, a three-necked flask was charged with the bromoaryl compound vi (50.0 mmol, 1 eq) and anhydrous tetrahydrofuran (150 mL), which was stirred uniformly and then cooled to -78°C, and n-butyllithium (22 mL, 2.5 M n-hexane solution, 55.0 mmol, 1.1 eq) was added dropwise. After the dropwise addition was completed, stirring was continued at -78°C for 1 hour, and then anhydrous aluminum chloride (6.7 g, 50.0 mmol, 1 eq) was added in portions, and stirring was continued for 30 minutes. Subsequently, a solution of the fluorenone derivative (compound v, 50.0 mmol, 1 eq) in anhydrous tetrahydrofuran (100 mL) was added dropwise, and after the dropwise addition was completed, the reaction was continued at -78°C for 30 minutes. Subsequently, the reaction system was slowly returned to room temperature, and the reaction was continued at room temperature for 10 hours. Upon analysis by thin layer chromatography, substantially no starting material remained, and 1 M dilute hydrochloric acid (100 mL) was added to quench the reaction. Subsequently, 100 mL of ethyl acetate was added, and after stirring for 3 minutes, the layers were separated by standing, and the organic phase was retained, and the aqueous phase was extracted with ethyl acetate (3 x 40 mL), and the organic phases were combined and dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure, and the crude product was purified by flash column chromatography on silica gel (mobile phase: n-hexane / ethyl acetate mixed solvent) to obtain the target compound i.

[0146] The compounds listed in Table 1 were synthesized by the above-described preparation method, and for each compound Hx, the starting material or intermediate compound i, ii, iv involved in the above-described preparation method is represented by i-x, ii-x, iv-x, respectively. Among them, the main starting materials used, the synthesized intermediates, the yield, and the mass spectrometry characterization data are shown in Table 1.

[0147] Table 1

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] The NMR data of representative compounds involved in the synthesis of examples are shown in Table 2.

[0154] Table 2

[0155]

[0156]

[0157]

[0158] Device examples:

[0159] The compounds of the present application used in the devices are all purified by sublimation, and the purity is all greater than 99.98%.

[0160] The compounds involved in the present application can be used as hole transport materials for blue light, red light, green light and other color light OLED devices. The specific device manufacturing method and test results are given below.

[0161] Preparation of a blue organic electroluminescent device

[0162] Blue device example 1:

[0163] A blue top-emitting organic electroluminescent device is manufactured according to the structure shown in Figure 1 The preparation process is as follows: a transparent ITO film layer (thickness 150 nm) is formed on a glass substrate 101 by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixture of compound 1 and compound H13 of the present application is evaporated on the surface of the anode as a hole injection layer 103, the mixing ratio is 3:97 (mass ratio), and the thickness is 10 nm; then compound H13 of the present application (thickness 100 nm) and compound 1-2 (thickness 20 nm) are evaporated in turn on the surface of the hole injection layer to obtain a first layer of hole transport layer 104 and a second layer of hole transport layer 105, respectively. Next, compound 3 and compound 4 are co-evaporated on the surface of the second hole transport layer 105 at a mass ratio of 95:5 to form an organic light-emitting layer 106 (thickness 30 nm). Then, compound 5 is evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and a mixture of compound 6 and LiQ at a mixing ratio of 4:6 (mass ratio) is evaporated to form an electron transport layer 108 (thickness 30 nm). Then, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at a deposition rate of 1:9 to form a second electrode 109 as a cathode with a thickness of 10 nm. Finally, compound 7 is evaporated as a cover layer with a thickness of 70 nm to complete the manufacture of the organic light-emitting device.

[0164] During the above device preparation process, the vacuum degree is maintained at 2x10 -7Torr to 5 x 10 -6 Torr; the evaporation rate of the organic material was 0.1 A / s to The evaporation rate of the aluminum was 0.1 A / s Thus, the manufacture of the organic light emitting device was completed.

[0165] The chemical structures of the compounds 1, 1-2, 1-3, 1-4, 5, 6, 7 and LiQ are shown in Table 3

[0166] Table 3

[0167]

[0168]

[0169] Blue light device examples 2 to 10

[0170] An organic electroluminescent device was produced in the same manner as in blue light device example 1, except that the compound H13 was replaced by the compounds (H20, H46, H78, H108, H113, H132, H157, H214, H283) in the formation of the hole injection layer and the hole transport layer, respectively, in Table 4.

[0171] Comparative examples 1 to 4

[0172] An organic electroluminescent device was produced in the same manner as in blue light device example 1, except that the compound H13 was replaced by the compounds HTA, HTB, HTC and HTD in the formation of the hole injection layer and the hole transport layer, respectively.

[0173] The chemical structures of the compounds HTA, HTB, HTC and HTD are shown below:

[0174]

[0175] The operating voltage and efficiency of the organic electroluminescent device produced as above were calculated by a computer-controlled Keithley 2400 test system. The device lifetime in the dark condition was obtained using a Polaronix (McScience Co.) lifetime measurement system equipped with a power source and a photodiode as a detection unit, and LT95 indicates the time required for the device luminance to decay to 95% of the initial luminance. The test results are shown in Table 4.

[0176] Table 4

[0177]

[0178] Preparation of a red organic electroluminescent device

[0179] Red light device example 1:

[0180] According to such Figure 2 The structure shown illustrates the fabrication of a red bottom-emitting organic electroluminescent device. The fabrication process is as follows: A transparent ITO film (150 nm thick) is formed on a glass substrate 101 using magnetron sputtering, resulting in a first electrode 102 serving as the anode. A mixture of compound 1 and compound 2 is deposited on the anode surface as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm. Subsequently, compound 2 (100 nm thick) and compound H10 (20 nm thick) of this invention are sequentially deposited on the hole injection layer surface, yielding a first hole transport layer 104 and a second hole transport layer 105, respectively. Next, compounds 2-3 and 2-4 are co-deposited on the surface of the second hole transport layer 105 at a mass ratio of 95:5 to form an organic light-emitting layer 106 (40 nm thick). Subsequently, compound 5 is sequentially deposited on the surface of the organic light-emitting layer to form a hole-blocking layer 107 (10 nm thick), and compound 6 and LiQ in a 4:6 mass ratio are deposited to form an electron transport layer 108 (30 nm thick). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at a 1:9 evaporation rate to form a second electrode 109 with a thickness of 10 nm as a cathode, thus completing the fabrication of the organic light-emitting device.

[0181] During the fabrication of the aforementioned device, the vacuum level was maintained at 2 × 10⁻⁶ throughout the entire process. -7 Torr up to 5×10 -6 Torr; the evaporation rate of organic matter is between; to Between these points, the evaporation rate of aluminum is This completes the fabrication of organic light-emitting devices.

[0182] The chemical structures of compounds 1, 5, 6, 7 and LiQ are as described above, and the chemical structures of compounds 2, 2-3, 2-4 are shown in Table 5.

[0183] Table 5

[0184]

[0185] Red light device examples 2-10

[0186] Except that, when forming the light-emitting layer, compound H10 was replaced with compounds listed in Table 6 (H21, H60, H89, H111, H142, H165, H180, H245, H325), the organic electroluminescent device was fabricated using the same method as in Example 1 of the red light device.

[0187] Comparative Examples 5-7

[0188] Except that compounds HTE, HTF, and HTG were used to replace compound H10 during the formation of the light-emitting layer, the organic electroluminescent device was fabricated using the same method as in Example 1 of the red light device. The chemical structures of compounds HTE, HTF, and HTG are shown below:

[0189]

[0190] The operating voltage and efficiency of the organic electroluminescent device prepared above were calculated using a computer-controlled Keithley 2400 testing system. The device lifetime under dark conditions was obtained using a Polaronix (McScience Co.) lifetime measurement system equipped with a power supply and photodiodes as detection units. LT95 represents the time required for the device brightness to decay to 95% of its initial brightness. The test results are shown in Table 6.

[0191] Table 6

[0192]

[0193] Fabrication of green organic light-emitting devices

[0194] Example 1 of green light device:

[0195] According to such Figure 2 The structure shown is used to fabricate a green bottom-emitting organic electroluminescent device. The fabrication process is as follows: A transparent ITO film (150 nm thick) is formed on a glass substrate 101 by magnetron sputtering to obtain a first electrode 102 as the anode. A mixture of compound 1 and compound 2 is deposited on the anode surface as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm. Subsequently, compound 2 (100 nm thick) and compound H17 (40 nm thick) of the present invention are sequentially deposited on the surface of the hole injection layer to obtain a first hole transport layer 104 and a second hole transport layer 105, respectively. Next, on the surface of the second hole transport layer 105, compounds 3-3A, 3-3B, and 3-4 are co-deposited in a mass ratio of 45:45:10 to form an organic light-emitting layer 106 (40 nm thick). Subsequently, compound 5 is sequentially deposited on the surface of the organic light-emitting layer to form a hole-blocking layer 107 (10 nm thick), and compound 6 and LiQ in a 4:6 mass ratio are deposited to form an electron transport layer 108 (30 nm thick). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at a 1:9 evaporation rate to form a second electrode 109 with a thickness of 10 nm as a cathode, thus completing the fabrication of the organic light-emitting device.

[0196] During the fabrication of the aforementioned device, the vacuum level was maintained at 2 × 10⁻⁶ throughout the entire process. -7Torr to 5 x 10 -6 Torr; the evaporation rate of the organic material was 0.1 A / sec to The evaporation rate of aluminum was 0.1 A / sec Thus, the manufacture of the organic light emitting device was completed.

[0197] The chemical structures of compounds 1, 2, 5, 6, 7 and LiQ are as previously described, and the chemical structures of compounds 3-3A, 3-3B, 3-4 are shown in Table 7.

[0198] Table 7

[0199]

[0200] Green light device examples 2 to 10

[0201] An organic electroluminescent device was produced in the same manner as in green light device example 1, except that in the formation of the light emitting layer, compound H17 was replaced by the following compounds (H17, H53, H102, H138, H192, H212, H255, H281, H311, H341) in Table 8, respectively.

[0202] Comparative examples 8 to 10

[0203] An organic electroluminescent device was produced in the same manner as in green light device example 1, except that in the formation of the light emitting layer, compound H17 was replaced by compounds HTH, HTI and HTJ. The chemical structures of compounds HTH, HTI and HTJ are shown below.

[0204]

[0205] The operating voltage and efficiency of the organic electroluminescent device produced as above were calculated by a computer controlled Keithley 2400 test system. The device lifetime in the dark was obtained using a Polaronix (McScience Co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit, and LT95 indicates the time required for the device luminance to decay to 95% of the initial luminance. The test results are shown in Table 8.

[0206] Table 8

[0207]

[0208]

[0209] As can be seen from Table 4, Table 6 and Table 8, the compound of the present application used in the hole transport layer of the blue light, red light and green light organic electroluminescent device can effectively reduce the driving voltage, improve the device efficiency and prolong the service life. Specifically, in Comparative Examples 1-4, the amine group and the biphenyl group are located at different positions of the fluorene, and the device performance exhibited in driving voltage, device efficiency and service life is different; in Comparative Examples 8-10 and Comparative Examples 5-7, as the aryl group connected on the fluorene changes from none to biphenyl, the driving voltage of the device is reduced and the efficiency and the service life are improved, which may be due to the increase of effective conjugation contact between molecules caused by the extension of conjugation, which is more conducive to the carrier hopping between molecules. In the blue light device embodiment, compared with Comparative Examples 1-4, the driving voltage of the device is reduced by at least 4.0%, the device efficiency is improved by at least 3.8%, and the LT95 service life is improved by at least 16.7%; in the red light device embodiment, compared with Comparative Examples 5-7, the driving voltage of the device is reduced by at least 5.7%, the device efficiency is improved by at least 11.1%, and the LT95 service life is improved by at least 15.5%; in the green light device embodiment, compared with Comparative Examples 8-10, the driving voltage of the device is reduced by at least 5.7%, the device efficiency is improved by at least 11.1%, and the LT95 service life is improved by at least 15.5%. The reason is that the introduction of the non-planar structure aryl and cycloalkyl promotes the formation of isotropic amorphous stacking of molecules, so that the film morphology is more stable during device operation; at the same time, the conjugated backbone based on fluorene can ensure that the molecule has good hole transport properties. Therefore, the compound of the present application used as the hole transport layer of the organic electroluminescent device shows excellent characteristics in driving voltage, device efficiency and stability.

[0210] The above description is only the preferred embodiment of the present application, but the protection scope of the present application is not limited thereto, and any person skilled in the art can make equivalent replacements or changes to the technical solution and the inventive concept of the present application within the technical range disclosed by the present application, which should be covered within the protection scope of the present application.

Claims

1. A fluorene-based triarylamine compound, the chemical structure of the compound being represented by formula (6), (8), (13), (15): ###0001### (6) (8) (13) (15) wherein R1, R2 are the same as or different from each other, and are independently selected from the group consisting of substituted or unsubstituted C1-C12 linear or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R1 and R2 are bonded to form a group E selected from any one of the following groups: ###0002### wherein L0, L1, L2 are the same as or different from each other, and are each independently selected from the group consisting of a single bond, substituted or unsubstituted C6-C20 arylene, or substituted or unsubstituted C2-C20 heteroarylene; and Ar1, Ar2 are the same as or different from each other, and are each independently selected from the group consisting of: ###0003### wherein in any of the groups, the carbon on any one and only one of the aromatic rings is a bonding site, or any one of the hydrogen atoms can be replaced by one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl; and A is selected from the group consisting of substituted or unsubstituted groups represented by formula (2)-(4): ###0004### (2) (3) (4) wherein R1, R2 are the same as or different from each other, and are independently selected from the group consisting of substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl; and / or, in formula (2)-(4), the hydrogen on the aromatic ring is unsubstituted, or any one of the hydrogen atoms on the aromatic ring can be replaced by one of deuterium, fluorine, chlorine, cyano, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C18 aryl, C2-C18 heteroaryl. R1, R2 are the same as or different from each other, and are each independently selected from the group consisting of substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl; In the group E, * indicates the bonding site to the 9,9'-position of the fluorene group in formula (6), (8), (13), (15) to form a spiro structure; said R a , R b , R c are the same as or different from each other and are independently selected from a substituted or unsubstituted C1-C10 linear or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 heteroaryl group; in each of the structures of the group E, a hydrogen atom on any one of the benzene rings can be replaced by one of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, ethylphenyl, t-butylphenyl, naphthyl, pyridyl; a hydrogen atom on any one of the cycloalkyl groups can be replaced by one of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl; R m , R n each occurrence is independently selected from one of deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio; m and n are each independently selected from 0, 1, 2, 3, or 4; In R1-R2, the "substituted" in "substituted or unsubstituted" is independently selected from one or more of deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, wherein the substituents are the same as or different from each other. ​ ​ ​ In equations (2) to (4), Z1 to Z 12 Whether the two are the same or different, they are each independently selected from -C(R) e (R) f )-;in, R e , R f , each independently of one another, are selected from the group consisting of hydrogen, deuterium, C1-C10-alkyl; * denotes the bonding site; R1, R2, R a ~R c , L0, L1, L2, A, the "substituted" in the "substituted or unsubstituted" is independently selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, -CD3, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C20 aryl, C2-C20 heteroaryl; and, R1-R2, R a ~R c , L0, L1, L2, A are the same or different from each other.

2. The fluorene-based triarylamine-based compound according to claim 1, wherein ​ ​ 3. The fluorene-based triarylamine compound according to any one of claims 1 to 2, wherein ​ R a , R b , R c are the same or different from each other and are independently selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, t-butylphenyl, naphthyl, or biphenyl; ​ 4. The fluorene-based triarylamine compound according to any one of claims 1 to 2, wherein R m selected from deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl; and / or, R n selected from deuterium, tritium, fluorine, chlorine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclobutyl, cyclopentyl, cyclohexyl.

5. The fluorene-based triarylamine compound according to any one of claims 1 to 2, wherein L0, L1, L2are each independently selected from a single bond, or when not a single bond, are each independently selected from one of the following groups, substituted or unsubstituted: phenylene, naphthylene, pyridylene, thienylene, selenophenylene, furanylene, pyrrolylene, benzothienylene, benzofuranylene, indolyiene, dibenzothienylene, dibenzofuranylene, fluorenylene, carbazolyiene; In L0, L1, L2, the substituents of "substituted" in "substituted or unsubstituted" are independently selected from any one or combination of the following groups: deuterium, fluorine, chlorine, cyano, nitro, trifluoromethyl, -CD3, methoxy, methylthio, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, t-butylphenyl, biphenylyl, naphthyl, pyridyl.

6. A fluorene-based triarylamine-based compound characterized in that, The fluorene-based triarylamine compound is selected from any one of the following chemical structures:

7. An organic layer comprising the fluorene-based triarylamine compound according to any one of claims 1 to 6.

8. Use of the fluorene-based triarylamine compound according to any one of claims 1 to 6 or the organic layer according to claim 7 for the production of an organic electroluminescent device.

9. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer or an electron transport layer, and the organic layer comprises the fluorene-based triarylamine compound according to any one of claims 1 to 6.

10. The organic electroluminescent device according to claim 9, wherein The organic electroluminescent device is selected from an organic photovoltaic device, electronic paper, an organic photoreceptor or an organic thin film transistor.

11. A display or illumination device, characterized in that It comprises the organic electroluminescent device according to any one of claims 9 to 10. The organic electroluminescent device is selected from an organic photovoltaic device, electronic paper, an organic photoreceptor or an organic thin film transistor. It comprises the organic electroluminescent device according to any one of claims 9 to 10.

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