A fluorene-based compound and an organic electroluminescent device

Abstract

The present invention relates to the field of organic electroluminescent materials, and in particular to a fluorene-based compound and an organic electroluminescent device. The chemical structure of the compound is that the compound of the present invention has good carrier transport properties, a stable chemical structure, and simple molecular synthesis. When different types of aromatic or heteroaromatic groups are connected, the frontier orbital energy level and the triplet energy level can be regulated in a large range, and can be used as a variety of functional materials such as a main material of a light-emitting layer, a hole blocking layer material, and an electron transport layer material. This type of material is applied to OLED devices, and the luminous efficiency and life are improved, while the production cost is reduced.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent materials, in particular to a fluorene-based compound and an organic electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs) are a type of self-luminous electronic components that have the advantages of high contrast, wide viewing angle, and fast response time. In addition, OLEDs are suitable for flexible polymer substrates and can be manufactured into thin, bendable or rollable display products. Therefore, they have been widely used in various consumer electronic products in recent years and are favored by users.

[0003] The working principle of OLED devices is: when the electrodes at both ends are applied with a forward bias, electrons and holes are injected from the cathode and anode respectively, and after physical processes such as migration and recombination, higher energy excitons are formed in the light-emitting layer. As the excitons recover from the excited state to the lower energy and more stable ground state, when the energy is released in the form of photons, the device achieves light emission. In particular, in order to reduce the driving voltage of OLED devices and improve the luminous efficiency, various functional layers and functional layer materials are introduced. For example, a typical OLED device structure is currently: 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.

[0004] In order to meet the market demand for low-power, long-life displays, it is necessary to develop OLED materials with stable chemical structures and excellent performance. Specifically, the materials should have high thermal decomposition temperatures and glass transition temperatures to ensure that the molecules do not decompose during vacuum evaporation and are conducive to the formation of uniform amorphous films; at the same time, they should have good carrier mobility and moderate frontier orbital energy levels. The stability and performance of existing materials need to be further improved. Summary of the invention

[0005] The object of the present invention is to provide a fluorene-based compound and an organic electroluminescent device to solve the problems in the prior art.

[0006] To achieve the above-mentioned object and other related objects, the present invention provides a compound, the chemical structure of which is shown in formula (1):

[0007]

[0008] In formula (1), R 1 ~R 8, which are the same as or different from each other, are independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, nitro, cyano, trifluoromethyl, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, or a substituent represented by formula (2), or R 1 ~R 8 The two adjacent groups in the are linked to each other to form a benzene ring;

[0009]

[0010] In formula (2), L 0 , L 2 are the same as or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene group, or a substituted or unsubstituted C2-C40 heteroarylene group; L 1 is selected from substituted or unsubstituted C10-C40 arylene groups, substituted or unsubstituted C2-C40 heteroarylene groups; Ar is selected from substituted or unsubstituted C6-C40 aryl groups, substituted or unsubstituted C2-C40 heteroaryl groups; n is selected from 0-7 and is an integer; * is a chemical bond connection site;

[0011] The R 9 is selected from substituted or unsubstituted C1-C30 straight chain or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, or a group described in formula (2); wherein, when R 9 When R is selected from aryl or heteroaryl, 9 The substituent may be selected from a plurality of C1-C15 alkyl groups, and adjacent C1-C15 alkyl groups are bonded to form an aliphatic ring;

[0012] For formula (1), the following conditions are met: R 1 ~R 9 At least one of the groups is selected from the group described in formula (2);

[0013] R 10 ~R 18 Selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, and substituted or unsubstituted C6-C18 aryl.

[0014] Another aspect of the present invention provides an organic layer comprising the aforementioned compound.

[0015] Another aspect of the present invention provides use of the aforementioned compound and / or the aforementioned organic layer in an organic electroluminescent device.

[0016] Another aspect of the present invention 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 compound.

[0017] Another aspect of the present invention provides a display or lighting device, comprising the organic electroluminescent device as described above in the present invention.

[0018] Compared with the prior art, the present invention has the following beneficial effects:

[0019] The present invention provides a class of fluorene-based compounds, which have good carrier transport properties, stable chemical structure, simple molecular synthesis, and can achieve regulation of frontier orbital energy levels and triplet energy levels in a wide range when connected to different types of aromatic or heteroaromatic groups, and can be used as a variety of functional materials such as the main material of the light-emitting layer, the hole blocking layer material, and the electron transport layer material. Such materials are applied to OLED devices, and the luminous efficiency and life are improved, while the production cost is reduced. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figure 1 Schematic diagram of a structure of an organic electroluminescent device in an embodiment.

[0021] Figure 2 Schematic diagram of another structure of the organic electroluminescent device in the embodiment.

[0022] In the figure:

[0023] 101 Base

[0024] 102 first electrode

[0025] 103 Hole injection layer

[0026] 104 First hole transport layer

[0027] 105 Second hole transport layer

[0028] 106 Luminescent Layer

[0029] 107 Hole blocking layer

[0030] 108 Electron transport layer

[0031] 109 second electrode

[0032] 110 Covering DETAILED DESCRIPTION

[0033] The following is a detailed description of the specific disclosed fluorene compounds and the embodiments of their application in organic electroluminescent devices. Those skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and the details in this specification can also be modified or changed in various ways based on different viewpoints and applications without departing from the spirit of the present invention.

[0034] Before further describing the specific embodiments of the present invention, it should be understood that the scope of protection of the present invention is not limited to the specific embodiments described below; it should also be understood that the terms used in the examples of the present invention are for describing the specific embodiments rather than for limiting the scope of protection of the present invention; in the present specification and claims, unless otherwise expressly stated herein, the singular forms "a", "an" and "the" include plural forms.

[0035] When the embodiments give numerical ranges, it should be understood that, unless otherwise specified in the present invention, both endpoints of each numerical range and any numerical value between the two endpoints can be selected. Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those generally understood by those skilled in the art. In addition to the specific methods, equipment, and materials used in the embodiments, according to the grasp of the prior art by those skilled in the art and the record of the present invention, any methods, equipment, and materials of the prior art similar or equivalent to the methods, equipment, and materials described in the embodiments of the present invention can also be used to realize the present invention.

[0036] After a lot of exploration and research, the inventors of the present invention aim to provide a class of compounds based on fluorene. First, fluorene and its derivatives are a class of high-mobility hole transport fragments. When connected to electron-withdrawing aromatic or heteroaryl groups, it is easy to obtain electron transport materials or dual-carrier transport materials with excellent performance, depending on the strength of their electron-withdrawing properties, which can be used as electron transport layers, hole blocking layers or light-emitting layer main materials respectively; secondly, the introduction of a larger volume of acenaphthene groups at the 9-position of fluorene can form a larger steric hindrance, which is beneficial to inhibit intermolecular stacking during the evaporation film formation process, thereby forming a uniform and stable amorphous film and improving the stability of the film; in addition, acenaphthene can be regarded as naphthalene The 1,8-position hydrogen atoms are replaced by cycloalkyl groups, which can play a role in protecting the reactive active sites. The above factors are conducive to increasing the thermal stability and chemical stability of the molecule, thereby improving the efficiency and service life of OLED devices. On this basis, this application is completed.

[0037] The first aspect of the present invention provides a fluorene compound, the chemical structure of the fluorene compound is shown in formula (1): The chemical structure of the fluorene compound is shown in formula (1):

[0038]

[0039] In formula (1), R 1 ~R 8 , which are the same as or different from each other, are independently selected from hydrogen, deuterium, fluorine, chlorine, bromine, nitro, cyano, trifluoromethyl, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, or a substituent represented by formula (2), or R 1 ~R 8 The two adjacent groups in the are linked to each other to form a benzene ring;

[0040]

[0041] In formula (2), L 0 , L 2 are the same as or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene group, or a substituted or unsubstituted C2-C40 heteroarylene group; L 1 is selected from substituted or unsubstituted C10-C40 arylene groups, substituted or unsubstituted C2-C40 heteroarylene groups; Ar is selected from substituted or unsubstituted C6-C40 aryl groups, substituted or unsubstituted C2-C40 heteroaryl groups; n is selected from 0-7 and is an integer; * is a chemical bond connection site. Wherein, L 1 is an arylene group or a heteroarylene group, so, for example, when n=2, it can be regarded as two -L 2 -Ar replaces different positions on the arylene or heteroarylene ring.

[0042] The R 9 is selected from substituted or unsubstituted straight or branched C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 heteroaryl, or a group described in formula (2); wherein, when R 9 When R is selected from aryl or heteroaryl, 9 The substituent may be selected from a plurality of C1-C15 alkyl groups, and adjacent C1-C15 alkyl groups may be bonded to form an aliphatic ring.

[0043] For formula (1), the following conditions are met: R 1 ~R 9 At least one of them is selected from the group described in formula (2).

[0044] R 10 ~R 18 Selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, and substituted or unsubstituted C6-C18 aryl.

[0045] Among the compounds provided by the present invention, the chemical structure of the compound is shown in formula (3), formula (4) or formula (5):

[0046]

[0047] Among them, R 1 ~R 18 The selection is the same as in claim 1. In some embodiments, R 10 ~R 18 are each independently selected from hydrogen or deuterium. 10 ~R 18 Same or different. 1 ~R 9 The selection of is the same as formula (1).

[0048] In the compounds provided by the present invention, in formula (1) to formula (5), the substituted or unsubstituted substituent is selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl, and C2-C30 heteroaryl; and R 1 ~R 9 , R 10 ~R 18 , L 0 , L 1 , L 2 The substituents of Ar and Ar may be the same as or different from each other.

[0049] In the present application, in the description of the number of carbon atoms, for example, C1-C12 means having 1 to 12 carbon atoms. For another example, C3-C30 means having 3 to 30 carbon atoms. The rest is the same as above and will not be described in detail.

[0050] In some embodiments of the present application, the R 1 ~R 9 Same or different from each other, R 1 ~R 9 Each is selected from substituted or unsubstituted C1-C30 straight chain or branched alkyl, that is, R 1 ~R 9Each of them may be independently selected from substituted or unsubstituted C1-C30 straight-chain alkyl groups, and may also be selected from substituted or unsubstituted C1-C30 branched-chain alkyl groups. Among them, specifically, the alkyl group includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

[0051] In some embodiments of the present application, the R 1 ~R 9 Same or different from each other, R 1 ~R 9 Each is independently selected from substituted or unsubstituted C3 to C30 cycloalkyl groups. Specifically, cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

[0052] In some embodiments of the present application, the R 9 Each is independently selected from substituted or unsubstituted C1 to C30 heteroalkyl groups. Wherein, the heteroalkyl group may be a straight or branched alkyl group containing heteroatoms. Specifically, the heteroalkyl group may include, but is not limited to, alkoxy, alkylthio, alkylsulfonyl, silyl, etc. Alkoxy groups may include, but are not limited to, methoxy, ethoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyl, n-hexyl, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. Examples of alkylthio groups include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3,3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.

[0053] In some embodiments of the present application, the R 1 ~R 9are the same as or different from each other, and are independently selected from substituted or unsubstituted C6-C40 aryl groups, substituted or unsubstituted C2-C40 heteroaryl groups. 1 ~R 9 each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzoselenophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted silylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzonaphthoselenophene, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzospirofluorenyl, or substituted or unsubstituted benzocarbazolyl, etc.

[0054] In the compounds provided by the present invention, the R 1 ~R 8 In the “substituted or unsubstituted”, the “substituted” substituent is selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and fluorenyl, and the substituted substituents may be the same or different from each other.

[0055] In the compounds provided by the present invention, the R 9 The substituents are selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, diphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and fluorenyl, wherein the substituents are the same or different from each other.

[0056] When R 9 When R is selected from aryl or heteroaryl, 9 The substituents of can be selected from a plurality of C1-C12 alkyl groups, and adjacent C1-C12 alkyl groups are bonded to form an aliphatic ring. 9The substituents are selected from a plurality of C1-C8 alkyl groups, and adjacent C1-C8 alkyl groups are bonded to form an aliphatic ring. 9 When selected from aryl or heteroaryl, one or more substitution sites may be substituted by C1-C12 or C1-C8 alkyl. 9 When selected from aryl or heteroaryl, any two adjacent sites may be substituted by an alkyl group having 1 to 12 carbon atoms, or 1 to 8 carbon atoms to form an aliphatic ring. Among them, an aliphatic hydrocarbon ring means a ring formed only by carbon and hydrogen atoms as a non-aromatic ring. Aliphatic hydrocarbon rings include but are not limited to cycloalkylene, and specific examples may include cyclopropylene, cyclobutylene, cyclobutylene, cyclopentylene, cyclopentenylene, cyclohexylene, cyclohexenylene, 1,4-cyclohexadienylene, cycloheptylene, cycloheptenylene, cyclooctylene, cyclooctenylene, etc. For example, when R 9 When selected from phenyl, R 9 When the substituents are two ethyl groups, the two ethyl groups can bond to form a cycloalkyl group, which is connected with the phenyl group to form 1,2,3,4-Tetrahydronaphthalene (THN).

[0057] In some embodiments of the present application, the R 10 ~R 18 Same or different from each other, R 10 ~R 18 Each is selected from substituted or unsubstituted C1-C10 straight chain or branched alkyl groups, that is, R 10 ~R 18 Each of them may be independently selected from substituted or unsubstituted C1-C10 straight-chain alkyl groups, or substituted or unsubstituted C1-C10 branched-chain alkyl groups. Among them, specifically, the alkyl group includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

[0058] In some embodiments of the present application, the R 10 ~R 18 Same or different from each other, R 10 ~R 18Each is selected from substituted or unsubstituted C1-C10 aryl groups, for example, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl and the like.

[0059] In the compounds provided by the present invention, n is selected from 0 to 7 and is an integer. Further, n is selected from 1, 2, 3, 4, 5, 6, 7, etc.

[0060] Among the compounds provided by the present invention, formula (2) In the above, L 0 , L 2 are the same or different; and are each independently selected from a single bond, or the following groups:

[0061]

[0062] Wherein, U is independently selected from N, CH, CR 19 or C* a , and satisfies that there are only two Us that are C* a ; R 19 Independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl, or C2-C30 heteroaryl; * a is the bonding site, or corresponds to * in formula (2).

[0063] In the compounds provided by the present invention, in formula (2), the L 1 Selected from the following groups:

[0064]

[0065] Wherein, V is independently selected from N, CH, CR 20 or C* b , and satisfies that there are only two Vs that are C* b ; W is selected from O, S, NR 21 , or CR 22 R 23 ;

[0066] And satisfying that, among formula (8), formula (9) and formula (11), at least one V is selected from N;

[0067] R 20 independently selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl, or C2-C30 heteroaryl;

[0068] R21 ~R 23 are each independently selected from C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl; or, R 22 , R 23 They are bonded to form a C5-C12 aliphatic ring, or they are bonded to form a C12-C30 aromatic condensed ring.

[0069] * b is the bonding site, or corresponds to * in formula (2).

[0070] In the compounds provided by the present invention, in formula (2), the L 0 , L 2 are the same or different; and are each independently selected from a single bond, or the following groups:

[0071]

[0072] In any of the groups, any two and only two carbon atoms on the aromatic rings are bonding sites; or any hydrogen atom can be replaced by one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, and quinoxalinyl.

[0073] In the compounds provided by the present invention, in formula (2), the L 1 Selected from the following groups:

[0074]

[0075] In any of the groups, any two and only two carbon atoms on the aromatic rings are bonding sites; or any hydrogen atom can be replaced by one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, methylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, and quinoxalinyl.

[0076] In the compounds provided by the present invention, in formula (2), Ar is selected from the following groups, and when the number of Ar is more than 1, different Ars are the same or different from each other:

[0077]

[0078] Wherein, X is selected from N, CH, CR 24 or C*c , and satisfies that there is only one X that is C* c ; R 24 Selected from deuterium, fluorine, chlorine, bromine, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, C6-C30 aryl, or C2-C30 heteroaryl; * c For L 2 bonding site.

[0079] Y is selected from O, S, NR 25 , CR 26 R 27 、SiR 28 R 29 ; R 25 ~R 29 are each independently selected from C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl; or, R 26 , R 27 They are bonded to form a C5-C12 aliphatic ring, or they are bonded to form a C12-C30 aromatic condensed ring.

[0080] In the compounds provided by the present invention, Ar is selected from the following groups, and when the number of Ar is more than 1, different Ars are the same or different from each other:

[0081]

[0082]

[0083]

[0084] In any of the above groups, any and only one carbon on the aromatic ring is a bonding site, or any hydrogen atom can be replaced by deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, or quinoxalinyl.

[0085] Among the compounds provided by the present invention, the chemical structures of the compounds are shown in Formula (12) to Formula (15):

[0086]

[0087] R 1 ~R 9 At least one of the following groups:

[0088] The above groups can be regarded as specific selections of compounds of formula (2). 1 ~R 9 Except for the above-mentioned groups, the other options are the same as those in formula (1) and the further limitations on the compounds of formula (1). For example, when R 1 When selected from the above groups, R 2 ~R 9 is selected from the same compounds as those in formula (1) and the further limitations on the compounds of formula (1).

[0089] Among the compounds provided by the present invention, the compound is selected from any one of the following chemical structures:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] Specifically, the above structure may be unsubstituted or substituted with one or more substituents selected from the following. For example, it may be deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylheteroarylamine group, an arylphosphino group, and a heteroaryl group.

[0099] The second aspect of the present invention provides an organic layer, comprising the compound described in the first aspect of the present invention.

[0100] The third aspect of the present invention provides use of the compound according to the first aspect of the present invention and / or the organic layer according to the second aspect of the present invention in an organic electroluminescent device.

[0101] The fourth aspect of the present invention 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 light-emitting device structure, wherein the organic layer may be a single-layer structure, or a multilayer tandem structure having two or more organic layers laminated thereon, wherein the organic layer may include 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. The organic layer may be prepared using common methods and materials for preparing organic electroluminescent devices. The organic layer includes the compound described in the first aspect of the present invention.

[0102] In the organic electroluminescent device provided by the present invention, the first electrode serves as an anode layer, and the anode material may be, for example, a material having a large work function, so that holes are smoothly injected into the organic layer. For example, it may be a metal, a metal oxide, a combination of a metal and an oxide, a conductive polymer, etc. The metal oxide may be, for example, indium tin oxide (ITO), zinc oxide, indium oxide, and indium zinc oxide (IZO).

[0103] In the organic electroluminescent device provided by the present invention, the second electrode serves as a cathode layer, and the cathode material may be, for example, a material having a small work function, so that electrons are smoothly injected into the organic layer. The cathode material may be, for example, a metal or a multilayer structure material. The metal may 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.

[0104] In the organic electroluminescent device provided by the present invention, the material of the hole injection layer is preferably a material whose highest occupied molecular orbital (HOMO) is between the work function of the anode material and the HOMO of the surrounding organic layer as a material that is advantageous for receiving holes from the anode at low voltage.

[0105] In the organic electroluminescent device provided by the present invention, the material of the hole transport layer is a material having high mobility for holes and is suitable as a material for receiving holes from the anode or the hole injection layer and transporting 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 part and a non-conjugated part, and the like.

[0106] In the organic electroluminescent device provided by the present invention, the material of the light-emitting layer can generally be selected from materials with good quantum efficiency for fluorescence or phosphorescence as materials that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and from the electron transport layer respectively and combining the holes with the electrons. The compound of the present invention can be used as the main material of the light-emitting layer.

[0107] In the organic electroluminescent device provided by the present invention, the material of the electron transport layer is a material with high electron mobility, which is suitable as a material that advantageously receives electrons from the cathode and transports the electrons to the light-emitting layer. The compound of the present invention can be used as an electron transport material or a hole blocking material.

[0108] In the organic electroluminescent device provided by the present invention, the material of the cover layer generally has a high refractive index, and thus can help improve the light efficiency of the organic light-emitting device, especially help improve the external light-emitting efficiency.

[0109] The organic electroluminescent device provided by the present invention is an organic photovoltaic device, an organic light-emitting device, an organic solar cell, an electronic paper, an organic photoreceptor, an organic thin film transistor, etc.

[0110] Another aspect of the present invention provides a display or lighting device, comprising the organic electroluminescent device of the present invention.

[0111] The specific preparation method of the above-mentioned new compound of the present invention will be described in detail below by taking multiple synthesis examples as examples, but the preparation method of the present invention is not limited to these multiple synthesis examples. Those skilled in the art can make any modifications, equivalent substitutions, improvements, etc. on this basis without departing from the principles of the present invention, and expand the method to the scope of the technical solution claimed for protection by the claims of the present invention.

[0112] Unless otherwise specified, the compounds not mentioned in the present invention are all commercially available products; the mass spectrum in the present invention is measured by a ZABHS mass spectrometer (manufactured by Micromass, UK), and the nuclear magnetic resonance is measured by a Bruker 400 MHz nuclear magnetic resonance instrument (manufactured by Bruker, Germany).

[0113] The following compounds are specifically synthesized in the examples of the present invention. Other compounds involved in the present invention can be synthesized by similar methods with reference to the synthetic routes given in the following examples.

[0114]

[0115] Synthesis Example:

[0116] Synthesis of compound E2:

[0117]

[0118] 1. Synthesis of compound iii-E2

[0119] Under nitrogen atmosphere, 3-boronic acid-9-fluorenone (compound i-E2, 9.0g, 40.0mmol, 1eq), compound ii-E2 (13.8g, 40.0mmol, 1eq) and degassed toluene (200mL) were added to a dry three-necked flask in sequence, and after stirring evenly, tetrakistriphenylphosphine palladium (924.4mg, 0.8mmol, 2%eq), potassium carbonate (13.8g, 100mmol, 2.5eq) and degassed ethanol (80mL) and deionized water (80mL) were added in sequence. After sufficient stirring, the reaction system was heated to reflux under nitrogen atmosphere. After reacting for 9 hours, there was basically no raw material remaining by thin layer chromatography analysis, and heating was stopped. When the reaction solution was cooled to room temperature, 100 mL of toluene was added to the reaction system, stirred for 3 minutes, and then allowed to stand for stratification. The liquid was separated with a separatory funnel, and the organic phase was retained. The aqueous phase was extracted with toluene (3×40 mL), combined with the above-retained organic phase, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by flash silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / dichloromethane) to obtain compound iii-E2 (15.6 g, yield 80.0%). Mass spectrum (m / z) = 488.17 [M+H] + .

[0120] 2. Synthesis of compound v-E2

[0121] Under nitrogen atmosphere, compound iii-E2 (7.3 g, 15.0 mmol, 1 eq), p-toluenesulfonyl hydrazide (4.2 g, 22.5 mmol, 1.5 eq) and anhydrous toluene (150 mL) were added to a dry three-necked flask in sequence, and after mixing evenly, the reaction system was heated to 80° C. and stirred for 2 hours under nitrogen atmosphere. Subsequently, potassium carbonate (4.1 g, 30.0 mmol, 2 eq) and acenaphthene-5-boric acid (compound iv-E2, 4.5 g, 22.5 mmol, 1.5 eq) were added to the reaction mixture in sequence, and the reaction was continued at 110° C. for 6 hours. The reaction system was cooled to room temperature, and a saturated sodium bicarbonate aqueous solution (120 mL) was slowly added. After standing for stratification, the organic phase was collected using a separatory funnel. The aqueous phase was extracted with toluene (3×40 mL) and combined with the aforementioned organic phase. The obtained organic phase was washed with saturated brine in turn, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by rapid silica gel column chromatography (the mobile phase was a mixed solvent of n-hexane / toluene) to obtain compound iv-6 (7.4 g, yield 78.8%). Mass spectrum (m / z) = 626.25 [M+H] + .

[0122] 3. Synthesis of Compound E2

[0123] Under a nitrogen atmosphere, compound iv-6 (6.3 g, 10.0 mmol, 1 eq), bis(dibenzylideneacetone)palladium (283.5 mg, 0.5 mmol, 5% eq), triphenylphosphine (262.3 mg, 1.0 mmol, 10% eq), potassium tert-butoxide (1.3 g, 12.0 mmol, 1.2 eq), 5-bromoacenaphthene (compound vi-E2, 2.8 g, 12.0 mmol, 1.2 eq) and anhydrous toluene (100 mL) were added in sequence to a dry three-necked flask. After sufficient stirring, the temperature was raised to 100°C under a nitrogen atmosphere and the reaction was allowed to react for 12 hours. The reaction system was cooled to room temperature, deionized water (60 mL) was added to quench the reaction, and the organic phase was collected by a separatory funnel after standing for stratification. The aqueous phase was extracted with toluene (3×40 mL) and combined with the above organic phase. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The crude product was purified by rapid silica gel column chromatography (mobile phase was a mixed solvent of n-hexane / toluene) and recrystallization to obtain compound E2 (5.8 g, yield 74.6%). The total yield of the three-step reaction was 47.0%. Mass spectrum (m / z) = 778.31 [M+H] + .

[0124] The compounds listed in Table 1 were synthesized by referring to the preparation method of compound E2, except that raw material compounds ix, ii-x and vi-x were used to replace compounds i-E2, ii-E2 and vi-E2 in equivalent amounts, respectively. The main raw materials used, the synthesized intermediates, the yields and the mass spectrometry characterization data are shown in Table 1.

[0125] Table 1

[0126]

[0127]

[0128]

[0129] Synthesis of compound E106

[0130]

[0131] 1. Synthesis of compound vi-E106

[0132]

[0133] Referring to the preparation method of compound iii-E2, compound vi-E106 was synthesized, except that 1-bromo-3-iodobenzene (compound vii-E106) and compound viii-E106 were used to replace 3-bromo-9-fluorenone (compound i-E2) and compound ii-E2 in equivalent amounts, respectively. Yield 82.8%, mass spectrum (m / z) = 568.13 [M+H] + .

[0134] Referring to the preparation method of compound E2, compound E106 was synthesized by two-step reaction, except that compounds i-E106 (7H-benzo[c]fluorene-7-one) and vi-E106 were used to replace compounds iii-E2 and v-E2 in equivalent amounts. The total yield of the three-step reaction was 44.5%. Mass spectrum (m / z) = 856.36 [M+H] + .

[0135] The compounds listed in Table 2 were synthesized by referring to the preparation method of compound E106, except that the raw material compounds 9-fluorenone, vii-x and viii-x were used in equivalent amounts to replace the compounds 7H-benzo[c]fluoren-7-one, vii-E106 and viii-E106, respectively. The main raw materials used, the synthesized intermediates, the yields and the mass spectrometry characterization data are shown in Table 2.

[0136] Table 2

[0137]

[0138]

[0139] The NMR data of the representative compounds involved in the synthesis examples are shown in Table 3.

[0140] Table 3

[0141]

[0142]

[0143] Device Example:

[0144] The compounds used in the device are all purified by sublimation, and the purity is greater than 99.98%.

[0145] The compounds involved in the present invention, some embodiments of which can be used as the main material of the light-emitting layer of a blue light fluorescent OLED device; some embodiments of which can be used as the main material of the light-emitting layer of a green light phosphorescent OLED device; some embodiments of which can be used as the main material of the light-emitting layer of a red light phosphorescent OLED device; and other embodiments of which can be used as the electron transport material of an OLED device.

[0146] Preparation of blue organic electroluminescent devices (as the main material of the light-emitting layer)

[0147] Blue light device embodiment 1: according to Figure 1 The structure shown is used to make a blue top-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. On the surface of the anode, a mixed material of compound 1 and compound 1-1 is evaporated as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound 1-1 (thickness 100nm) and compound 1-2 (thickness 20nm) are sequentially evaporated 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, the compound E157 of the present invention and compound 1-4 (thickness 30nm, mass ratio 95:5) are co-evaporated on the surface of the second hole transport layer 105 to form a blue light emitting layer 106. Subsequently, compound 5 (thickness 10nm) is sequentially evaporated to form a hole blocking layer 107, and compound 6 and LiQ with a mixing ratio of 4:6 (mass ratio) are formed to form an electron transport layer 108 (thickness 30nm). After that, ytterbium (Yb) with a thickness of 3nm, magnesium (Mg) with a thickness of 10nm, and silver (Ag) are sequentially deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to obtain a second electrode 109 as a cathode. Finally, compound 7 (thickness 70nm) is evaporated as a covering layer material to complete the manufacture of the organic light-emitting device.

[0148] The chemical structures of compounds 1, 1-1, 1-2, 1-3, 1-4, 5, 6, 7 and LiQ are shown in Table 4.

[0149] Table 4

[0150]

[0151] Blue light device embodiments 2 to 8

[0152] The organic electroluminescent device was prepared by the same method as in Example 1 of the blue light device, except that compound E163, E167, E171, E185, E200, E210 and E222 in Table 5 were used to replace compound E157 when forming the light-emitting layer.

[0153] Comparative Example 1

[0154] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound 1-3 (chemical structure shown in Table 4) was used instead of compound E157 when forming the light-emitting layer.

[0155] For the organic electroluminescent device prepared as above, its operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions was obtained using a Polaronix (McScience Co.) life measurement system equipped with a power supply and a photodiode as a detection unit. Each group of blue light device embodiments was produced and tested in the same batch as the device of comparative example 1. The operating voltage, efficiency and life of the device of comparative example 1 were recorded as 1, and the ratios of the corresponding indicators of the blue light device embodiments 1 to 8 and the device of comparative example 1 were calculated, as shown in Table 5.

[0156] Table 5

[0157] Light-emitting layer host material Relative working voltage Relative efficiency Relative lifespan Comparative Example 1 Compound 1-3 1 1 1 Blue light device embodiment 1 E157 0.940 1.059 1.427 Blue light device embodiment 2 E163 0.963 1.115 1.990 Blue light device embodiment 3 E167 0.931 1.107 1.743 Blue light device embodiment 4 E171 0.960 1.094 1.889 Blue light device embodiment 5 E185 0.956 1.075 1.356 Blue light device embodiment 6 E200 0.935 1.082 1.800 Blue light device embodiment 7 E210 0.946 1.103 1.468 Blue light device embodiment 8 E222 0.952 1.063 1.384

[0158] Preparation of red organic electroluminescent devices (as the main material of the light-emitting layer)

[0159] Red light device embodiment 1:

[0160] According to Figure 2 The structure shown is used to make a red bottom-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound 1 and compound 1-1 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound 1-1 (thickness 100nm) and compound 2-2 (thickness 20nm) are sequentially evaporated 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, the compound E16 of the present invention and compound 2-4 are co-evaporated at a mass ratio of 95:5 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound 5 is sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound 6 and LiQ with a mixing ratio of 4:6 (mass ratio) are formed into an electron transport layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, completing the manufacture of the organic light-emitting device.

[0161] The chemical structures of compounds 1, 5, 6, 7 and LiQ are described above, and the chemical structures of compounds 2-2, 2-3 and 2-4 are shown in Table 6.

[0162] Red light device embodiments 2 to 4

[0163] The organic electroluminescent device was prepared by the same method as in Example 1 of the red light device, except that compound E16, E58, E88 and E90 in Table 7 were used to replace compound E16 when forming the light-emitting layer.

[0164] Comparative Example 2

[0165] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound 2-3 (chemical structure shown in Table 6) was used instead of compound E16 when forming the light-emitting layer.

[0166] Table 6

[0167]

[0168] For the organic electroluminescent device prepared as above, its operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions was obtained using a Polaronix (McScience Co.) life measurement system equipped with a power supply and a photodiode as a detection unit. Each group of red light device embodiments was produced and tested in the same batch as the device of comparative example 2. The operating voltage, efficiency and life of the device of comparative example 2 were recorded as 1, and the ratios of the corresponding indicators of the red light device embodiments 1 to 4 and the device of comparative example 2 were calculated, as shown in Table 7.

[0169] Table 7

[0170] Light-emitting layer host material Relative working voltage Relative efficiency Relative lifespan Comparative Example 2 Compound 2-3 1 1 1 Red light device embodiment 1 E16 0.963 1.157 1.352 Red light device embodiment 2 E58 0.958 1.210 1.264 Red light device embodiment 3 E88 0.936 1.173 1.280 Red light device embodiment 4 E90 0.941 1.188 1.300

[0171] Preparation of green organic electroluminescent devices (as the main material of the light-emitting layer)

[0172] Green light device embodiment 1:

[0173] According to Figure 2The structure shown is used to make a red bottom-emitting organic electroluminescent device, and the preparation process is as follows: on a glass substrate 101, a transparent ITO film layer (thickness 150nm) is formed by a magnetron sputtering process to obtain a first electrode 102 as an anode. A mixed material of compound 1 and compound 1-1 is evaporated on the surface of the anode as a hole injection layer 103, with a mixing ratio of 3:97 (mass ratio) and a thickness of 10nm; then compound 1-1 (thickness 100nm) and compound 3-2 (thickness 40nm) are sequentially evaporated 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, the compound E59, compound 3-3A and compound 3-4 of the present invention are co-evaporated at a mass ratio of 45:45:10 to form an organic light-emitting layer 106 (thickness 40nm). Subsequently, compound 5 is sequentially evaporated on the surface of the organic light-emitting layer to form a hole blocking layer 107 (thickness 10 nm), and compound 6 and LiQ with a mixing ratio of 4:6 (mass ratio) are formed into an electron transport layer 108 (thickness 30 nm). Finally, magnesium (Mg) and silver (Ag) are mixed and deposited on the surface of the electron transport layer 108 at an evaporation rate of 1:9 to form a second electrode 109 with a thickness of 10 nm as a cathode, completing the manufacture of the organic light-emitting device.

[0174] The chemical structures of compounds 1, 5, 6, 7 and LiQ are described above, and the chemical structures of compounds 3-2, 3-3A, 3-3B and 3-4 are shown in Table 8.

[0175] Green light device embodiments 2 to 6

[0176] An organic electroluminescent device was prepared by the same method as in Example 1 of the green light device, except that compound E70, E106, E117, E130 and E141 in Table 9 were used to replace compound E59 respectively when forming light emission.

[0177] Comparative Example 3

[0178] An organic electroluminescent device was prepared in the same manner as in Example 1, except that compound 3-3B (chemical structure shown in Table 8) was used instead of compound E59 when forming the light-emitting layer.

[0179] The structures of the main materials used in the above embodiments and comparative examples are shown in Table 8 below:

[0180] Table 8

[0181]

[0182] For the organic electroluminescent device prepared as above, its operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions was obtained using a Polaronix (McScience Co.) life measurement system equipped with a power supply and a photodiode as a detection unit. Each group of embodiment devices was produced and tested in the same batch as the device of comparative example 3. The operating voltage, efficiency and life of the device of comparative example 3 were recorded as 1, and the ratios of the corresponding indicators of the green light device embodiments 1 to 6 and the device of comparative example 3 were calculated, as shown in Table 9.

[0183] Table 9

[0184]

[0185] Preparation of blue organic electroluminescent devices (as electron transport layer material)

[0186] Blue light device embodiments 9 to 14

[0187] An organic electroluminescent device was prepared by the same method as that of the blue light device comparative example 1, except that when forming the electron transport layer, compound E2, E12, E27, E44, E51, and E136 in the following Table 10 were used to replace compound 6.

[0188] Blue light device comparative example 4

[0189] The organic electroluminescent device was prepared by the same method as that of the blue light device comparative example 1, except that compound E-Com (chemical structure as follows) was used instead of compound 6 when forming the electron transport layer.

[0190]

[0191] For the organic electroluminescent device prepared as above, its operating voltage and efficiency were calculated by a computer-controlled Keithley 2400 test system. The device life under dark conditions was obtained using a Polaronix (McScience Co.) life measurement system equipped with a power supply and a photodiode as a detection unit. Each group of blue light device embodiments was produced and tested in the same batch as the device of comparative example 4. The operating voltage, efficiency and life of the device of comparative example 4 were recorded as 1, and the ratios of the corresponding indicators of the blue light device embodiments 9 to 14 and the device of comparative example 4 were calculated, as shown in Table 10.

[0192] Table 10

[0193] Electron transport materials Relative working voltage Relative efficiency Relative lifespan Comparative Example 1 E-Com 1 1 1 Blue light device embodiment 9 E2 0.925 1.110 1.210 Blue light device embodiment 10 E12 0.908 1.053 1.195 Blue light device embodiment 11 E27 0.914 1.090 1.275 Blue light device embodiment 12 E44 0.900 1.088 1.160 Blue light device embodiment 13 E51 0.929 1.100 1.236 Blue light device embodiment 14 E136 0.946 1.077 1.263

[0194] The above description is only a preferred specific implementation manner of the present invention, but the protection scope of the present invention is not limited thereto. Any technician familiar with the technical field can make equivalent replacements or changes according to the technical scheme and inventive concept of the present invention within the technical scope disclosed by the present invention, which should be covered by the protection scope of the present invention.

Claims

1. A compound, the chemical structure of which is shown in formula (1): In formula (1), R1 to R8 are the same as or different from each other and are independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, a substituent shown in formula (2), or two adjacent groups among R1 to R8 are linked to form a benzene ring; In the R1 to R8, the "substituted or unsubstituted" substituent is selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and fluorenyl, wherein the "substituted" substituents are the same or different from each other; In formula (2), L0 and L2 are the same or different and are independently selected from a single bond, In any group, any two and only two carbon atoms on the aromatic ring are bonding sites; or any hydrogen atom can be replaced by one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, and quinoxalinyl; L1 is selected from In any group, any two and only two carbon atoms on the aromatic ring are bonding sites; or any hydrogen atom can be replaced by one of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, and quinoxalinyl; Ar is selected from In any of the above groups, any one and only one carbon on the aromatic ring is a bonding site, or any hydrogen atom can be substituted by deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, or quinoxalinyl; n is 1 and is an integer; * is the chemical bond connection site; The R9 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, or the group described in formula (2); the substituent of R9 is selected from one or more of deuterium, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and fluorenyl, wherein the substituents are the same or different from each other; For formula (1), the following conditions are met: at least one of R1 to R9 is selected from the group described in formula (2); R 10 ~R 18 Selected from hydrogen, deuterium, C1-C10 alkyl, and C6-C18 aryl.

2. A compound, characterized in that The compound is selected from any one of the following chemical structures:

3. An organic layer comprising the compound according to claims 1 to 2, wherein the organic layer is a light-emitting layer or an electron transporting layer.

4. Use of the compound according to any one of claims 1 to 2 or the organic layer according to claim 3 in an organic electroluminescent device.

5. 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 light-emitting layer and the electron transport layer comprise the compound as described in any one of claims 1 to 2.

6. A display or lighting device, characterized in that: It comprises the organic electroluminescent device as claimed in claim 5.

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