Compounds and uses thereof

Abstract

The application discloses a compound and application thereof, and belongs to the technical field of display. The chemical structural formula of the compound is shown in the following formula: wherein Ar1 and Ar2 are both ; or one of Ar1 and Ar2 is, and the other of Ar1 and Ar2 is a substituted or unsubstituted C6-C12 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group; Ar3 is halogen, a cyano group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C3-C12 heteroaryl group, a substituted or unsubstituted C1-C60 alkyl group or an alkoxy group; A is O, S or Se; L represents a single bond, a substituted or unsubstituted C6-C12 arylene group or a substituted or unsubstituted C3-C12 heteroarylene group; Z1 to Z4 are each independently N or CR5. The OLED device prepared based on the compound has a lower working voltage, higher efficiency and longer cycle life.

Description

Technical Field

[0001] This invention relates to the field of display technology, and in particular to a compound and its applications. Background Technology

[0002] Organic light-emitting devices (OLEDs), also known as organic light-emitting diodes, have advantages such as self-illumination, low power consumption, wide viewing angle, light weight, thinness, fast response, high contrast, low driving voltage, and flexibility, and are widely used in the fields of displays and lighting.

[0003] Typically, an OLED device includes a cathode, an anode, and an electron transport layer, an emissive layer, and a hole transport layer stacked between the cathode and the anode. The hole transport layer is fabricated using a hole injection material.

[0004] Currently, there is still a need to improve the charge transfer capability and thermal stability of hole injection materials in order to further improve the voltage, efficiency and cycle life of OLED devices. Summary of the Invention

[0005] This invention provides a compound and its applications. Devices prepared using this compound exhibit lower operating voltage, higher efficiency, and longer cycle life. The technical solution is as follows: In a first aspect, a compound is provided, the chemical structural formula of which is shown below: ; Among them, Ar1 and Ar2 are both ; Or, one of Ar1 and Ar2 is The other of Ar1 and Ar2 is one of a substituted or unsubstituted C6-C12 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group; Ar3 is one of halogen, cyano, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 heteroaryl, substituted or unsubstituted C1-C60 alkyl, or substituted or unsubstituted C1-C60 alkoxy. A can be O, S, or Se; L represents a single bond, a substituted or unsubstituted C6-C12 arylene, or a substituted or unsubstituted C3-C12 heteroarylene; Z1 to Z4 are each independently either N or CR5; R1 to R5 are each independently one of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, isothiocyanate, isocyanate, sulfonyl pentafluoride, trifluoromethyl, trifluoromethoxy, trifluoromethylsulfonyl, boranyl, sulfinyl, sulfonyl, phosphoxy, and mercapto.

[0006] In some possible implementations, when one of Ar1 and Ar2 is In this case, the other of Ar1 and Ar2 is one of the following: a phenyl group substituted with 1-2 trifluoromethyl groups, a biphenyl group substituted with 1-2 trifluoromethyl groups, a phenyl group substituted with 1-2 fluorine groups, a biphenyl group substituted with 1-2 fluorine groups, a biphenyl group substituted with both fluorine and cyano groups, a biphenyl group substituted with both fluorine and trifluoromethyl groups, a biphenyl group substituted with both cyano and trifluoromethyl groups, or a phenyl group substituted with 1-2 trifluoromethoxy groups.

[0007] In some possible implementations, Ar3 is one of fluorine, cyano, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, phenyl, 1-5 fluorine-substituted phenyl, 1-2 trifluoromethyl-substituted phenyl, 1-2 trifluoromethoxy-substituted phenyl, fluorine and cyano-substituted phenyl, fluorine and trifluoromethyl-substituted phenyl, cyano and trifluoromethyl-substituted phenyl, biphenyl, cyanophenyl, pyridyl, 1-4 fluorine-substituted pyridyl, fluorine and cyano-substituted pyridyl, pyrimidinyl, pentafluoroethylphenyl, and deuterium and trifluoromethyl-substituted phenyl.

[0008] In some possible implementations, Z1 to Z4 are all CR5; Alternatively, one of Z1 to Z4 is N, and the other three are CR5.

[0009] In some possible implementations, R5 is one of hydrogen, deuterium, fluorine, cyano, or trifluoromethyl.

[0010] In some possible implementations, R1 through R4 are all cyano groups.

[0011] In some possible implementations, L is a single key.

[0012] In a second aspect, the invention provides the application of any of the compounds involved in the first aspect of the embodiments in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photosensors.

[0013] Thirdly, a hole injection material is provided, the hole injection material comprising any of the compounds involved in the first aspect of the present invention.

[0014] In some possible implementations, the hole injection material further includes a hole transport compound, wherein the hole transport compound has a mass percentage of 70 wt% to 99.5 wt%. The hole transport compound is selected from at least one of carbazole compounds, triaromatic amine compounds, benzidine diamine compounds, fluorene compounds, phthalocyanine compounds, polythiophene, polyethylene, polybenzene sulfonic acid, quinone compounds, and hexacyanohexatribenzene.

[0015] Fourthly, a charge generation layer material is provided, the charge generation layer material comprising any of the compounds involved in the first aspect of the present invention.

[0016] Fifthly, an organic electroluminescent device is provided, the organic electroluminescent device comprising: a first electrode, a second electrode, and a light-emitting unit disposed between the first electrode and the second electrode; The light-emitting unit includes an electron transport functional layer, a light-emitting layer, and a hole transport functional layer, wherein the hole transport functional layer includes any of the compounds involved in the first aspect of the present invention.

[0017] In some possible implementations, the light-emitting units are configured as multiple units, and a charge generation layer is provided between two adjacent light-emitting units. The charge generation layer includes an N-type charge generation layer and a P-type charge generation layer. The P-type charge-generating layer includes any of the compounds involved in the first aspect of the embodiments of the present invention.

[0018] In some possible implementations, the hole transport functional layer includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole injection layer includes the compound.

[0019] In a sixth aspect, a display device is provided, the display device including the organic electroluminescent device according to the fifth aspect of the present invention.

[0020] This invention provides a compound whose thermal stability is effectively improved by introducing heterocyclic groups. Furthermore, the presence of a conjugated system in the compound is beneficial for enhancing its electrical conductivity. Additionally, the introduction of electron-withdrawing groups helps to regulate the LUMO energy level, improving hole injection and transport capabilities. Therefore, this compound exhibits high electrical conductivity and thermal stability. Consequently, devices fabricated using this compound can effectively reduce operating voltage, improve efficiency, and extend cycle life. Attached Figure Description

[0021] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device provided in an embodiment of the present invention. Detailed Implementation

[0022] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some, not all, of the embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0023] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used in this specification is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0024] In this article, "one or more" refers to any one, two or more of the listed items.

[0025] In this embodiment of the invention, terms such as "first aspect," "second aspect," "third aspect," and "fourth aspect" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or quantity, nor should they be construed as implicitly indicating the importance or quantity of the indicated technical features. Moreover, terms such as "first," "second," "third," and "fourth" serve only as a non-exhaustive enumeration and should be understood not to constitute a closed limitation on the quantity.

[0026] In the embodiments of the present invention, the technical features described in an open-ended manner include both closed technical solutions composed of the listed features and open technical solutions that include the listed features.

[0027] In this embodiment of the invention, numerical ranges are involved. Unless otherwise specified, the numerical ranges are considered continuous and include the minimum and maximum values ​​of the range, as well as every value between the minimum and maximum values. Further, when the range refers to an integer, it includes every integer between the minimum and maximum values ​​of the range. Moreover, when multiple ranges are provided to describe features or characteristics, the ranges can be merged. In other words, unless otherwise specified, all ranges disclosed herein should be understood to include any and all subranges to which they are included.

[0028] Unless otherwise specified, the percentage concentrations mentioned in the embodiments of this invention refer to the final concentration. The final concentration refers to the proportion of the added component in the system after the addition of that component.

[0029] Unless otherwise specified, the temperature parameters in the embodiments of the present invention can be either constant temperature treatment or treatment within a certain temperature range. The constant temperature treatment allows temperature fluctuations within the precision range controlled by the instrument. The room temperature in the embodiments of the present invention generally refers to 4℃~30℃, preferably 20±5℃.

[0030] There is still a need to improve the charge transfer capability and thermal stability of hole injection layer materials in current related technologies, so as to further improve the driving voltage, luminous efficiency and cycle life of OLED devices.

[0031] The first aspect of this invention provides a compound with the following chemical structural formula: .

[0032] Among them, Ar1 and Ar2 are both ; Or, one of Ar1 and Ar2 is The other of Ar1 and Ar2 is one of a substituted or unsubstituted C6-C12 aryl group or a substituted or unsubstituted C3-C12 heteroaryl group; Ar3 is one of halogen, cyano, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C3-C12 heteroaryl, substituted or unsubstituted C1-C60 alkyl, or substituted or unsubstituted C1-C60 alkoxy. A can be O, S, or Se; L represents a single bond, a substituted or unsubstituted C6-C12 arylene, or a substituted or unsubstituted C3-C12 heteroarylene; Z1 to Z4 are each independently either N or CR5; R1 to R5 are each independently one of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, isothiocyanate, isocyanate, sulfonyl pentafluoride, trifluoromethyl, trifluoromethoxy, trifluoromethylsulfonyl, boranyl, sulfinyl, sulfonyl, phosphoxy, and mercapto.

[0033] It should be noted that the "aryl" used in the embodiments of this invention refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. This can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl. For polycyclic rings, at least one must be an aromatic ring system. For example, "C6~C12 aryl" refers to an aryl group containing 6 to 12 carbon atoms. Each occurrence can be independently C6, C7, C8, C9, C10, C11, or C12 aryl. Suitable examples include, but are not limited to, benzene, biphenyl, and naphthalene.

[0034] In the embodiments of this invention, "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "C3~C12 heteroaryl" refers to a heteroaryl group containing 3 to 12 carbon atoms, and each occurrence can be independently C3 heteroaryl, C4 heteroaryl, C5 heteroaryl, C6 heteroaryl, C7 heteroaryl, C8 heteroaryl, C9 heteroaryl, C10 heteroaryl, C11 heteroaryl, and C12 heteroaryl. Suitable examples include, but are not limited to: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, imidazole, oxazole, thiazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanolopyrrole, furanolofuran, thienofuran, benzoisoxazole, benzoisothiazolium, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-diazonyl, quinoxaline, quinazoline, and quinazolineone. Understandably, "azaaryl" refers to a heteroaryl group whose non-carbon atom is an nitrogen atom.

[0035] Hydrogen includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0036] This invention provides a compound whose thermal stability is effectively improved by introducing heterocyclic groups. Furthermore, the presence of a conjugated system in the compound is beneficial for enhancing its electrical conductivity. Additionally, the introduction of electron-withdrawing groups helps to regulate the LUMO energy level, improving hole injection and transport capabilities. Therefore, this compound exhibits high electrical conductivity and thermal stability. Consequently, devices fabricated using this compound can effectively reduce operating voltage, improve efficiency, and extend cycle life.

[0037] In some examples, when one of Ar1 and Ar2 is In this case, the other of Ar1 and Ar2 is one of the following: a phenyl group substituted with 1-2 trifluoromethyl groups, a biphenyl group substituted with 1-2 trifluoromethyl groups, a phenyl group substituted with 1-2 fluorine groups, a biphenyl group substituted with 1-2 fluorine groups, a biphenyl group substituted with both fluorine and cyano groups, a biphenyl group substituted with both fluorine and trifluoromethyl groups, a biphenyl group substituted with both cyano and trifluoromethyl groups, or a phenyl group substituted with 1-2 trifluoromethoxy groups.

[0038] In this context, a phenyl group with 1-2 trifluoromethyl substituted members refers to a phenyl group that can have one or two trifluoromethyl substituted members. When there are two trifluoromethyl substituted members, they can be located in the ortho, para, or meta positions. Similarly, a phenyl group with 1-2 fluorine substituted members refers to a phenyl group that can have one or two fluorine substituted members. When there are two fluorine substituted members, they can be located in the ortho, para, or meta positions. Similarly, a phenyl group with 1-2 trifluoromethoxy substituted members refers to a phenyl group that can have one or two trifluoromethoxy substituted members. When there are two trifluoromethoxy substituted members, they can be located in the ortho, para, or meta positions.

[0039] A biphenyl with 1-2 trifluoromethyl substitutions means that the biphenyl group can have one or two trifluoromethyl substitutions. When there are two trifluoromethyl substitutions, these two trifluoromethyl groups can be located on the same benzene ring or on different benzene rings of the biphenyl group. For example, a biphenyl group with two trifluoromethyl substitutions can have these two trifluoromethyl groups located on the same benzene ring, and these two trifluoromethyl groups can be in the ortho, para, or meta positions. Similarly, a biphenyl with 1-2 fluorine substitutions means that the biphenyl group can have one or two fluorine substitutions. When there are two fluorine substitutions, these two fluorine groups can be located on the same benzene ring or on different benzene rings of the biphenyl group.

[0040] A biphenyl group with simultaneous fluorine and cyano substitution refers to a biphenyl group having both fluorine and cyano groups substituted on it. The number of fluorine and cyano groups can be set and changed as needed, and there is no specific limitation. For example, the number of fluorine groups can be 1-2, and the number of cyano groups can be 1-2. Furthermore, the fluorine and cyano groups can be located on the same benzene ring or on different benzene rings. For example, a biphenyl group may have one fluorine group and one cyano group, located on two separate benzene rings or on the same benzene ring. Another example is a biphenyl group with two fluorine groups and one cyano group, where the two fluorine groups are located on the same benzene ring, and the cyano group is located on a different benzene ring.

[0041] A biphenyl with simultaneous fluorine and trifluoromethyl substitution refers to a biphenyl group having both fluorine and trifluoromethyl substitutions. The number of fluorine and trifluoromethyl groups can be set and changed as needed, and there is no specific limitation. For example, the number of fluorine groups can be 1-2, and the number of trifluoromethyl groups can be 1-2. Furthermore, the fluorine and trifluoromethyl groups can be located on the same benzene ring or on different benzene rings. For example, a biphenyl group may have one fluorine and one trifluoromethyl group, located on two separate benzene rings or on the same benzene ring. Another example is a biphenyl group with two fluorine groups and one trifluoromethyl group, where the two fluorine groups are located on the same benzene ring, and the trifluoromethyl group is located on another benzene ring.

[0042] A biphenyl group with simultaneous cyano and trifluoromethyl substitution refers to a biphenyl group having both cyano and trifluoromethyl substitutions. The number of cyano and trifluoromethyl groups can be set and changed as needed, and there is no specific limitation. For example, the number of cyano groups can be 1-2, and the number of trifluoromethyl groups can be 1-2. Furthermore, the cyano and trifluoromethyl groups can be located on the same benzene ring or on different benzene rings. For example, a biphenyl group may have one cyano group and one trifluoromethyl group, located on two separate benzene rings or on the same benzene ring.

[0043] The aforementioned groups are electron-withdrawing groups. Introducing electron-withdrawing groups onto bisoxazole groups helps to regulate the LUMO energy level of the compound, enhancing hole injection and transport capabilities. Simultaneously, it can also increase the electron affinity of the compound to some extent, facilitating complete charge transfer between the compound and the hole-transporting compound, thus imparting lower operating voltage, higher current efficiency, and longer lifespan to the device.

[0044] In some examples, Ar3 is one of fluorine, cyano, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, phenyl, 1-5 fluorine-substituted phenyl, 1-2 trifluoromethyl-substituted phenyl, 1-2 trifluoromethoxy-substituted phenyl, fluorine and cyano-substituted phenyl, fluorine and trifluoromethyl-substituted phenyl, cyano and trifluoromethyl-substituted phenyl, biphenyl, cyanophenyl, pyridyl, 1-4 fluorine-substituted pyridyl, fluorine and cyano-substituted pyridyl, pyrimidinyl, pentafluoroethylphenyl, and deuterium and trifluoromethyl-substituted phenyl.

[0045] In this context, a phenyl group with simultaneous fluorine and cyano substitution refers to a phenyl group having both fluorine and cyano groups substituted on it. The number of fluorine and cyano groups can be set and changed as needed, and is not specifically limited. For example, the number of fluorine groups can be 1-4, and the number of cyano groups can be 1-4. For instance, the number of fluorine groups can be 1, 2, 3, or 4, and the number of cyano groups can be 1, 2, 3, or 4.

[0046] Similarly, a phenyl group simultaneously substituted with fluorine and trifluoromethyl groups refers to a phenyl group having both fluorine and trifluoromethyl groups substituted on it. The number of fluorine and trifluoromethyl groups can be set and changed as needed, and there is no specific limitation. For example, the number of fluorine groups can be 1-4, and the number of trifluoromethyl groups can be 1-4. For instance, the number of fluorine groups can be 1, 2, 3, or 4, and the number of trifluoromethyl groups can be 1, 2, 3, or 4.

[0047] A phenyl group simultaneously substituted with both cyano and trifluoromethyl groups refers to a phenyl group having both cyano and trifluoromethyl groups substituted on it. The number of cyano and trifluoromethyl groups can be set and changed as needed, and is not specifically limited. For example, the number of cyano groups can be 1-4, and the number of trifluoromethyl groups can be 1-4. For instance, the number of cyano groups can be 1, 2, 3, or 4, and the number of trifluoromethyl groups can be 1, 2, 3, or 4.

[0048] A biphenyl with simultaneous fluorine and trifluoromethyl substitution refers to a biphenyl with both fluorine and trifluoromethyl substitution. The amounts of fluorine and trifluoromethyl can be set and changed as needed, and are not specifically limited. For example, the amount of fluorine can be 1-2, and the amount of trifluoromethyl can be 1-2. For instance, the amount of fluorine can be 1 or 2, and the amount of trifluoromethyl can be 1 or 2.

[0049] A pyridyl group with simultaneous fluorine and cyano substitution refers to a pyridyl group that has both fluorine and cyano substitutions. The number of fluorine and cyano groups can be set and changed as needed, and there is no specific limitation. For example, the number of fluorine groups can be 1-2, and the number of cyano groups can be 1-2. For instance, the number of fluorine groups can be 1 or 2, and the number of cyano groups can be 1 or 2.

[0050] A phenyl group simultaneously substituted with both deuterium and trifluoromethyl groups refers to a phenyl group having both deuterium and trifluoromethyl groups substituted on it. The number of deuterium and trifluoromethyl groups can be set and changed as needed, and is not specifically limited. For example, the number of deuterium groups can be 1-4, and the number of trifluoromethyl groups can be 1-4. For instance, the number of deuterium groups can be 1, 2, 3, or 4, and the number of trifluoromethyl groups can be 1, 2, 3, or 4.

[0051] Introducing the aforementioned electron-withdrawing groups onto benzoxazole groups helps to improve the torque of the molecule, effectively suppresses intermolecular interactions in the central conjugated system, enhances doping efficiency, and improves device performance.

[0052] In some examples, Z1 through Z4 are all CR5.

[0053] Alternatively, one of Z1 to Z4 is N, and the other three are CR5.

[0054] When one of Z1 to Z4 is N and the other three are CR5, Z1 can be N and Z2 to Z4 can be CR5; or Z2 can be N and Z1, Z3 and Z4 can be CR5; or Z3 can be N and Z1, Z2 and Z4 can be CR5; or Z4 can be N and Z1 to Z3 can be CR5.

[0055] When Z1 to Z4 are all CR5, the conjugated system can be increased, which helps to improve the conductivity of the compound. When one of Z1 to Z4 is N and the other three are CR5, an electron-withdrawing group is introduced, which helps to regulate the LUMO energy level of the compound and improve the hole injection and transport capabilities.

[0056] In some examples, R5 is one of hydrogen, deuterium, fluorine, cyano, or trifluoromethyl.

[0057] When Z1 to Z4 are all CR5, or when three of Z1 to Z4 are CR5, the R5 values ​​corresponding to different groups can be the same or different. For example, Z1 to Z4 are all CR5, and the R5 values ​​are all hydrogen. Another example is that Z1 to Z4 are all CR5, where the R5 value corresponding to Z1 to Z3 is hydrogen, and the R5 value corresponding to Z4 is trifluoromethyl. Alternatively, the R5 values ​​corresponding to Z1, Z3, and Z4 are hydrogen, and the R5 value corresponding to Z4 is fluorine.

[0058] When R5 is hydrogen or deuterium, it increases the conjugation system, which helps improve the conductivity of the compound. When R5 is fluorine, cyano, or trifluoromethyl, introducing an electron-withdrawing group onto the benzene ring where the benzoxazole and bisoxazole groups are connected (see compounds 30, 55, 138, and 196) helps lower the HOMO level of the benzoxazole group compared to other corresponding compounds without electron-withdrawing groups. This results in both HOMO and LUMO orbitals being distributed on the central bisoxazole conjugated ring, which is beneficial for electron migration. Furthermore, introducing an electron-withdrawing group onto the benzene ring where the benzoxazole and bisoxazole groups are connected also increases the electron affinity of the compound to some extent, facilitating complete charge transfer between the compound and hole-transfer compounds. Additionally, the connection of the benzoxazole group to a substituent-containing benzene ring can increase the twist of the compound, effectively suppressing intermolecular interactions in the central conjugated system, improving the doping efficiency of the compound, and enhancing device performance.

[0059] In some examples, L represents a single bond.

[0060] When L is a single bond, the benzoxazole group is directly connected to the bisoxazole group. The bisoxazole group is not connected to the five-membered oxazole ring end of the benzoxazole group, but to the benzene ring end of the benzoxazole group. Compared with the former, this connection method can maintain the original properties of the bisoxazole ring core skeleton to a greater extent, thereby reducing the changes in molecular properties caused by the introduction of benzoxazole units.

[0061] Regarding the compounds mentioned above, some examples of these compounds are listed below, see compounds 1-320.

[0062]

[0063] Secondly, embodiments of the present invention provide the application of any of the above-mentioned compounds in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, or organic photoreceptors.

[0064] Thirdly, embodiments of the present invention provide a hole injection material, which includes any of the compounds involved in the first aspect described above.

[0065] The hole injection material provided in this embodiment of the invention has all the advantages of the compounds involved in this embodiment of the invention.

[0066] The hole injection material provided in this embodiment of the invention, when applied to organic electroluminescent devices, can be used to prepare the hole injection layer of the organic electroluminescent device, so that the organic electroluminescent device has both high luminous efficiency, low operating voltage and strong thermal stability.

[0067] In some examples, the mass percentage of any compound involved in the first aspect of the present invention in the hole injection material is 0.05wt% to 99.95wt%, which includes, but is not limited to, the range consisting of one or any two of the following values: 0.05%, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 29%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, 50%, 52%, 54%, 56%, 58%, 60%, 62%, 64%, 66%, 68%, 69%, 70%, 72%, 76%, 78%, 80%, 82%, 84%, 86%, 88%, 90%, 92%, 94%, 96%, 98%, 99%, 99.95%, etc. Optionally, the mass percentage of any compound involved in the first aspect of the present invention in the hole injection material is 0.5wt% to 30wt%.

[0068] In other examples, the hole injection material provided in the embodiments of the present invention includes any of the compounds involved in the first aspect and a hole transport compound, wherein the mass percentage of the hole transport compound is 70wt% to 99.5wt%, which includes, but is not limited to, one or any two of the following values ​​in the range: 70%, 72%, 74%, 76%, 78%, 80%, 82%, 84%, 86%, 88%, 90%, 92%, 94%, 96%, 98%, 99%, 99.5%, etc.

[0069] Furthermore, for this type of hole injection material, the mass percentage of any compound involved in the first aspect is 0.5wt% to 30wt%, and the mass percentage of the hole transport compound is 70wt% to 99.5wt%.

[0070] Some suitable hole transport compounds are selected from at least one of carbazole compounds, triaromatic amine compounds, benzidine diamine compounds, fluorene compounds, phthalocyanine compounds, polythiophene, polyethylene, polybenzenesulfonic acid, quinone compounds, and hexacyanohexatribenzene.

[0071] For example, the hole transport compound can be any of the following compounds. Furthermore, the materials involved in the hole transport layer and the electron blocking layer can also be any of the following compounds.

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] .

[0078] In some examples, the hole transport compound may also be any of the following compounds.

[0079]

[0080] The aforementioned hole transport compound can form a charge transfer complex with any of the compounds involved in the first aspect of the present invention to generate and transport holes, thereby enhancing the hole injection and transport capabilities of the hole injection material, thereby reducing the operating voltage of the device, improving the luminous efficiency of the device, and extending the lifespan of the device.

[0081] Fourthly, embodiments of the present invention provide a charge generation layer material, which includes any of the compounds involved in the first aspect of the present invention.

[0082] The charge generation layer material provided in this embodiment of the invention possesses all the advantages of the compounds involved in this embodiment. Specifically, it facilitates hole injection into the upper light-emitting unit, achieving charge balance in the stacked device.

[0083] In some examples, the mass percentage of any compound involved in the first aspect of the present invention in the charge generation layer material is 100 wt%.

[0084] In other examples, in addition to any of the compounds involved in the first aspect of the embodiments of the present invention, the charge generation layer material also includes other compounds. The embodiments of the present invention do not specifically limit the compounds, and they can be selected adaptively according to actual needs.

[0085] Fifthly, embodiments of the present invention provide an organic electroluminescent device, which includes: a first electrode, a second electrode, and a light-emitting unit disposed between the first electrode and the second electrode.

[0086] The light-emitting unit includes an electron transport functional layer, a light-emitting layer, and a hole transport functional layer. The hole transport functional layer includes the compound involved in the first aspect of the present invention.

[0087] Specifically, the hole transport functional layer includes the hole injection material involved in the third aspect of the present invention, which includes the compound involved in the first aspect of the present invention and the hole transport compound involved in the third aspect of the present invention.

[0088] The organic electroluminescent device provided in this embodiment of the invention possesses all the advantages of the compounds involved in this embodiment. For example, the organic electroluminescent device combines high luminous efficiency, low operating voltage, and long lifespan.

[0089] In some examples, multiple light-emitting units are provided, and a charge generation layer is provided between two adjacent light-emitting units. The charge generation layer includes an N-type charge generation layer and a P-type charge generation layer; the P-type charge generation layer includes the compound involved in the first aspect of the embodiments of the present invention.

[0090] When there is one light-emitting unit, the organic electroluminescent device is a single-layer device. When there are multiple light-emitting units, the organic electroluminescent device is a multilayer device. Each light-emitting unit includes an electron transport functional layer, a light-emitting layer, and a hole transport functional layer.

[0091] In some examples, the hole transport functional layer includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole injection layer includes the compound involved in the first aspect of the present invention.

[0092] Specifically, the hole injection layer includes a hole injection material, which includes the compound involved in the first aspect of the present invention and the hole transport compound involved in the third aspect of the present invention.

[0093] It should be noted that in OLED devices, p-type doping technology is often used to achieve efficient charge injection and transport. This involves introducing molecular acceptors with high electron affinity into the hole injection layer to promote the transfer of electrons from the hole transport compound to the dopant, thereby forming mobile holes. This significantly improves the material's conductivity and reduces the interface injection barrier. The appropriate use of p-type dopant compounds can greatly improve device performance and extend device lifetime. The compound involved in the first aspect of this invention is used as a p-type dopant compound in the hole injection layer.

[0094] The following example illustrates the concept of a single light-emitting unit and a single-layer organic electroluminescent device.

[0095] As an example, the hole transport functional layer includes a hole injection layer and a hole transport layer, wherein the anode, hole injection layer, hole transport layer, light emission layer, and electron transport functional layer are stacked in sequence.

[0096] As another example, the hole transport functional layer includes a hole transport layer and an electron blocking layer, wherein the anode, hole transport layer, electron blocking layer and light-emitting layer are stacked in sequence.

[0097] As another example, the hole transport functional layer includes a hole transport layer, an electron blocking layer, and a hole injection layer, wherein the anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, and electron transport functional layer are stacked in sequence.

[0098] In some examples, the electron transport functional layer includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0099] The following example uses an organic electroluminescent device as a single-layer device.

[0100] As an example, the electron transport functional layer includes an electron transport layer, wherein the cathode, electron transport layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0101] As another example, the electron transport functional layer includes an electron transport layer and an electron injection layer, wherein the cathode, electron injection layer, electron transport layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0102] As another example, the electron transport functional layer includes an electron transport layer and a hole blocking layer, wherein the cathode, electron transport layer, hole blocking layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0103] As another example, the electron transport functional layer includes an electron transport layer, a hole blocking layer, and an electron injection layer, wherein the cathode, electron injection layer, electron transport layer, hole blocking layer, light-emitting layer, and hole transport functional layer are stacked in sequence.

[0104] When multiple light-emitting units are configured and the organic electroluminescent device is a stacked device, for example, the organic electroluminescent device includes two light-emitting units, and a charge generation layer is provided between the two light-emitting units. The charge generation layer includes an N-type charge generation layer and a P-type charge generation layer. That is, the organic electroluminescent device includes: a first electrode, a first light-emitting unit, an N-type charge generation layer, a P-type charge generation layer, a second light-emitting unit, and a second electrode.

[0105] The first light-emitting unit includes an electron transport functional layer, a light-emitting layer, and a hole transport functional layer. The second light-emitting unit includes an electron transport functional layer, a light-emitting layer, and a hole transport functional layer. The specific details have been introduced earlier and will not be repeated here.

[0106] For any of the organic electroluminescent devices mentioned above, the total thickness of at least one light-emitting unit located between the first electrode and the second electrode can be 1nm-1000nm, including but not limited to any of the following values ​​or a range consisting of any two values: 1nm, 30nm, 50nm, 100nm, 150nm, 200nm, 300nm, 400nm, 500nm, 550nm, 600nm, 700nm, 750nm, 800nm, 850nm, 900nm, 950nm, 1000nm, etc.

[0107] Furthermore, the total thickness of the at least one light-emitting unit can be 50nm-500nm, including but not limited to any of the following values ​​or a range consisting of any two values: 50nm, 100nm, 150nm, 200nm, 250nm, 300nm, 350nm, 400nm, 450nm, and 500nm.

[0108] In some embodiments of the present invention, the preparation method for each functional layer of the light-emitting unit of the organic electroluminescent device includes: vacuum evaporation, molecular beam evaporation, solvent-based dip coating, spin coating, bar coating, or inkjet printing.

[0109] It should be noted that the organic layers in the organic electroluminescent devices involved in the embodiments of the present invention can be prepared by vacuum evaporation, molecular beam evaporation, solvent-based dip coating, spin coating, rod coating, or inkjet printing. Metal electrodes can be prepared by evaporation or sputtering.

[0110] In a sixth aspect, embodiments of the present invention also provide a display device, which includes the organic electroluminescent device provided in the fifth aspect of embodiments of the present invention.

[0111] The display device provided in this embodiment of the invention uses the organic electroluminescent device mentioned above, which helps to reduce power consumption and extend its lifespan.

[0112] For example, the display device may be a mobile phone, tablet, laptop, MP3 player, wearable device, television, electronic screen, vehicle display, special display device, etc.

[0113] The specific embodiments of the present invention will now be described in more detail. While specific embodiments of the present invention are described below, it should be understood that the present invention can be implemented in various forms and should not be limited to the embodiments set forth herein. Where specific techniques or conditions are not specified in the embodiments, they are performed in accordance with the techniques or conditions described in the literature in the art or according to the product instructions. Reagents or instruments whose manufacturers are not specified are all conventional products that can be obtained commercially.

[0114] It should be noted that the serial numbers of the compounds provided in the following embodiments are the same as the compounds with the same serial numbers among the aforementioned compounds 1-320.

[0115] The following examples involve the synthesis of compounds, including intermediate compounds (hereinafter referred to as intermediates). These compounds and intermediates were separated by column chromatography and characterized by elemental analysis and high-resolution mass spectrometry (1HRMS).

[0116] Example 1 Example 1 provides compound 2, and the synthetic route and method are shown below:

[0117] Step 1: Synthesis of intermediate 2-1 Intermediate 2,3-dibromoaniline (25.00 g, 100 mmol) and triethylamine (22.26 g, 220 mmol) were dissolved in 150 mL of dichloromethane and added to a three-necked flask. Then, 2-trifluoromethylbenzoyl chloride (25.03 g, 120 mmol) was dissolved in 50 mL of dichloromethane and slowly added dropwise to the flask at room temperature. After the addition was complete, the mixture was stirred and reacted at room temperature for 3 h. After the reaction was complete, the reaction mixture was washed with water, followed by extraction and washing with dichloromethane and saturated sodium chloride aqueous solution. The organic phase was then dried over sodium sulfate. The mixture was filtered, the solvent was concentrated to dryness, and the crude product was purified by column chromatography (dichloromethane to n-hexane volume ratio = 1:1) to obtain the target compound 2-1 (33.84 g, yield 80.0%).

[0118] Step 2: Synthesis of intermediate 2-2 Intermediate 2-1 (30.00 g, 71.28 mmol) and cesium carbonate (46.45 g, 142.56 mmol) were dissolved in 150 mL of dimethyl sulfoxide and added to a single-necked flask. The mixture was heated to 140 °C and stirred overnight. After the reaction was complete, the reaction solution was cooled to room temperature and extracted and washed with ethyl acetate and saturated sodium chloride aqueous solution. The organic phase was then dried over sodium sulfate. The mixture was filtered, and the solvent was concentrated to dryness. The crude product was purified by column chromatography (ethyl acetate to n-hexane, volume ratio = 1:15) to obtain the target compound 2-2 (20.00 g, yield 82.0%).

[0119] Step 3: Synthesis of intermediates 2-3 Intermediate 2-2 (20.00 g, 58.45 mmol), pinacol diborate (19.30 g, 76.00 mmol), and dried potassium acetate (11.47 g, 116.9 mmol) were dissolved in 150 mL of dried toluene and added to a three-necked flask. Then, under N2 protection, 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (0.85 g, 1.169 mmol) was added to the reaction mixture, and the mixture was heated to reflux and stirred for 4 h. After the reaction was complete, the mixture was cooled to room temperature. The mixture was extracted and washed with dichloromethane and a saturated sodium chloride aqueous solution, and then the organic phase was dried over sodium sulfate. The mixture was filtered, the solvent was concentrated to dryness, and the crude product was purified by column chromatography (ethyl acetate to n-hexane, volume ratio = 1:5) to obtain the target compound 2-3 (15.69 g, yield 69.0%).

[0120] Step 4: Synthesis of intermediates 2-4 4,8-Dibromobenzo[1,2-D:4,5-D']bis(oxazole) (5.34 g, 16.80 mmol), 2-3 (15.69 g, 40.32 mmol), and potassium carbonate (9.29 g, 67.20 mmol) were dissolved in a dioxane:water mixture of 80 mL:16 mL and added to a three-necked flask. Under N2 protection, tridibenzylacetone dipalladium (Pd2(dba)3, 0.61 g, 0.67 mmol) and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (Xphos, 0.64 g, 1.34 mmol) were added to the reaction mixture, and the mixture was heated to reflux and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature. The mixture was then extracted and washed with dichloromethane and a saturated sodium chloride aqueous solution, and the organic phase was dried over sodium sulfate. The solvent was concentrated to dryness by filtration, and the crude product was purified by column chromatography (dichloromethane and n-hexane volume ratio = 1:8) to obtain the target compound 2-4 (6.42 g, yield 56.0%).

[0121] Step 5: Synthesis of intermediates 2-5 Intermediate 2-4 (6.42 g, 9.40 mmol) was dissolved in 40 mL of ultra-dry tetrahydrofuran under nitrogen protection and added to a three-necked flask. The reaction solution was cooled to -20 °C, and 20 mL of bis(trimethylsilyl)aminolithium (1.0 M, dissolved in tetrahydrofuran solution) was added dropwise. The reaction was continued at this temperature for 2 h, and then elemental iodine (4.77 g, 18.8 mmol) was added. The temperature was raised to room temperature and the reaction was continued for 0.5 h. After the reaction was completed, the solution was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography (ethyl acetate to n-hexane volume ratio = 1:8) to obtain intermediate 2-5 (7.16 g, yield 81.5%).

[0122] Step 6: Synthesis of intermediates 2-6 Intermediate 2-5 (7.00 g, 7.49 mmol), malononitrile (1.98 g, 29.96 mmol), and potassium carbonate (6.21 g, 44.94 mmol) were dissolved in 50 mL of N,N-dimethylformamide and added to a three-necked flask. Tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.35 g, 0.30 mmol) was then added to the reaction mixture under N2 protection, and the mixture was heated to 80 °C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature. Dilute hydrochloric acid was slowly added dropwise in an ice-water bath, resulting in the precipitation of a large amount of solid. The crude product was filtered and further purified by recrystallization to obtain the target compound 2-6 (3.34 g, yield 55.1%).

[0123] Step 7: Synthesis of Compound 2 Intermediate 2-6 (3.24 g, 4.0 mmol) was dissolved in 15 mL of dichloromethane solution. Then, under N2 protection, bis(trifluoroacetoxy)iodobenzene (PIFA, 3.44 g, 8.0 mmol) was added in portions, and the reaction was carried out overnight at room temperature. After the reaction was completed, the solution was concentrated until a suitable amount of solvent remained and a large amount of solid precipitated. The solid was filtered to obtain target product 2 (2.51 g, yield 77.53%).

[0124] Example 2 Example 2 provides compound 14, and the synthetic route and method are shown below:

[0125] Step 1: Synthesis of Intermediate 14-1 The synthesis method of intermediate 14-1 is the same as that of intermediate 2-1, with a yield of 85.50%.

[0126] Step 2: Synthesis of intermediate 14-2 The synthesis method of intermediate 14-2 is the same as that of intermediate 2-2, with a yield of 80.24%.

[0127] Step 3: Synthesis of intermediate 14-3 The synthesis method of intermediate 14-3 is the same as that of intermediate 2-3, with a yield of 68.50%.

[0128] Step 4: Synthesis of intermediate 14-4 The synthesis method of intermediate 14-4 is the same as that of intermediate 2-4, with a yield of 55.35%.

[0129] Step 5: Synthesis of intermediate 14-5 The synthesis method of intermediate 14-5 is the same as that of intermediate 2-5, with a yield of 85.11%.

[0130] Step 6: Synthesis of intermediate 14-6 The synthesis method of intermediate 14-6 is the same as that of intermediate 2-6, with a yield of 52.83%.

[0131] Step 7: Synthesis of Compound 14 The synthesis method of compound 14 is the same as that of compound 2, with a yield of 75.54%.

[0132] Example 3 Example 3 provides compound 30, and the synthetic route and method are shown below:

[0133] Step 1: Synthesis of intermediate 30-1 The synthesis method of intermediate 30-1 is the same as that of intermediate 2-1, with a yield of 87.10%.

[0134] Step 2: Synthesis of intermediate 30-2 The synthesis method of intermediate 30-2 is the same as that of intermediate 2-2, with a yield of 81.20%.

[0135] Step 3: Synthesis of intermediate 30-3 The synthesis method of intermediate 30-3 is the same as that of intermediate 2-3, with a yield of 65.20%.

[0136] Step 4: Synthesis of intermediate 30-4 The synthesis method of intermediate 30-4 is the same as that of intermediate 2-4, with a yield of 52.65%.

[0137] Step 5: Synthesis of intermediate 30-5 The synthesis method of intermediate 30-5 is the same as that of intermediate 2-5, with a yield of 82.01%.

[0138] Step 6: Synthesis of intermediate 30-6 The synthesis method of intermediate 30-6 is the same as that of intermediate 2-6, with a yield of 55.63%.

[0139] Step 7: Synthesis of Compound 30 The synthesis method of compound 30 is the same as that of compound 2, with a yield of 78.14%.

[0140] Example 4 Example 4 provides compound 55, and the synthetic route and method are shown below:

[0141] Step 1: Synthesis of intermediate 55-1 The synthesis method of intermediate 55-1 is the same as that of intermediate 2-1, with a yield of 83.40%.

[0142] Step 2: Synthesis of intermediate 55-2 The synthesis method of intermediate 55-2 is the same as that of intermediate 2-2, with a yield of 79.30%.

[0143] Step 3: Synthesis of intermediate 55-3 The synthesis method of intermediate 55-3 is the same as that of intermediate 2-3, with a yield of 66.50%.

[0144] Step 4: Synthesis of intermediate 55-4 The synthesis method of intermediate 55-4 is the same as that of intermediate 2-4, with a yield of 54.35%.

[0145] Step 5: Synthesis of intermediate 55-5 The synthesis method of intermediate 55-5 is the same as that of intermediate 2-5, with a yield of 80.50%.

[0146] Step 6: Synthesis of intermediate 55-6 The synthesis method of intermediate 55-6 is the same as that of intermediate 2-6, with a yield of 57.30%.

[0147] Step 7: Synthesis of Compound 55 The synthesis method of compound 55 is the same as that of compound 2, with a yield of 79.64%.

[0148] Example 5 Example 5 provides compound 63, and the synthetic route and method are shown below:

[0149] Step 1: Synthesis of intermediate 63-1 The synthesis method of intermediate 63-1 is the same as that of intermediate 2-1, with a yield of 87.20%.

[0150] Step 2: Synthesis of intermediate 63-2 The synthesis method of intermediate 63-2 is the same as that of intermediate 2-2, with a yield of 76.50%.

[0151] Step 3: Synthesis of intermediate 63-3 The synthesis method of intermediate 63-3 is the same as that of intermediate 2-3, with a yield of 64.70%.

[0152] Step 4: Synthesis of intermediate 63-4 The synthesis method of intermediate 63-4 is the same as that of intermediate 2-4, with a yield of 52.80%.

[0153] Step 5: Synthesis of intermediate 63-5 The synthesis method of intermediate 63-5 is the same as that of intermediate 2-5, with a yield of 81.05%.

[0154] Step 6: Synthesis of intermediate 63-6 The synthesis method of intermediate 63-6 is the same as that of intermediate 2-6, with a yield of 55.60%.

[0155] Step 7: Synthesis of Compound 63 The synthesis method of compound 63 is the same as that of compound 2, with a yield of 83.04%.

[0156] Example 6 Example 6 provides compound 105, and the synthetic route and method are shown below:

[0157] Step 1: Synthesis of intermediate 105-1 The synthesis method of intermediate 105-1 is the same as that of intermediate 2-1, with a yield of 87.20%.

[0158] Step 2: Synthesis of intermediate 105-2 The synthesis method of intermediate 105-2 is the same as that of intermediate 2-2, with a yield of 83.50%.

[0159] Step 3: Synthesis of intermediate 105-3 The synthesis method of intermediate 105-3 is the same as that of intermediate 2-3, with a yield of 72.50%.

[0160] Step 4: Synthesis of intermediate 105-4 The synthesis method of intermediate 105-4 is the same as that of intermediate 2-4, with a yield of 73.56%.

[0161] Step 5: Synthesis of intermediate 105-5 The synthesis method of intermediate 105-5 is the same as that of intermediate 2-5, with a yield of 78.53%.

[0162] Step 6: Synthesis of intermediate 105-6 The synthesis method of intermediate 105-6 is the same as that of intermediate 2-6, with a yield of 63.30%.

[0163] Step 7: Synthesis of Compound 105 The synthesis method of compound 105 is the same as that of compound 2, with a yield of 80.64%.

[0164] Example 7 Example 7 provides compound 111, and the synthetic route and method are shown below:

[0165] Step 1: Synthesis of intermediate 111-1 The synthesis method of intermediate 111-1 is the same as that of intermediate 2-1, with a yield of 85.20%.

[0166] Step 2: Synthesis of intermediate 111-2 The synthesis method of intermediate 111-2 is the same as that of intermediate 2-2, with a yield of 82.50%.

[0167] Step 3: Synthesis of intermediate 111-3 The synthesis method of intermediate 111-3 is the same as that of intermediate 2-3, with a yield of 71.50%.

[0168] Step 4: Synthesis of intermediate 111-4 The synthesis method of intermediate 111-4 is the same as that of intermediate 2-4, with a yield of 68.36%.

[0169] Step 5: Synthesis of intermediate 111-5 The synthesis method of intermediate 111-5 is the same as that of intermediate 2-5, with a yield of 73.83%.

[0170] Step 6: Synthesis of intermediate 111-6 The synthesis method of intermediate 111-6 is the same as that of intermediate 2-6, with a yield of 60.30%.

[0171] Step 7: Synthesis of Compound 111 The synthesis method of compound 111 is the same as that of compound 2, with a yield of 78.64%.

[0172] Example 8 Example 8 provides compound 121, and the synthetic route and method are shown below:

[0173] Step 1: Synthesis of intermediate 121-1 The synthesis method of intermediate 121-1 is the same as that of intermediate 2-1, with a yield of 84.50%.

[0174] Step 2: Synthesis of intermediate 121-2 The synthesis method of intermediate 121-2 is the same as that of intermediate 2-2, with a yield of 75.50%.

[0175] Step 3: Synthesis of intermediate 121-3 The synthesis method of intermediate 121-3 is the same as that of intermediate 2-3, with a yield of 65.70%.

[0176] Step 4: Synthesis of intermediate 121-4 The synthesis method of intermediate 121-4 is the same as that of intermediate 2-4, with a yield of 70.26%.

[0177] Step 5: Synthesis of intermediate 121-5 The synthesis method of intermediate 121-5 is the same as that of intermediate 2-5, with a yield of 72.63%.

[0178] Step 6: Synthesis of intermediate 121-6 The synthesis method of intermediate 121-6 is the same as that of intermediate 2-6, with a yield of 65.20%.

[0179] Step 7: Synthesis of Compound 121 The synthesis method of compound 121 is the same as that of compound 2, with a yield of 77.14%.

[0180] Example 9 Example 9 provides compound 138, and the synthetic route and method are shown below:

[0181] Step 1: Synthesis of intermediate 138-1 The synthesis method of intermediate 138-1 is the same as that of intermediate 2-1, with a yield of 85.20%.

[0182] Step 2: Synthesis of intermediate 138-2 The synthesis method of intermediate 138-2 is the same as that of intermediate 2-2, with a yield of 76.60%.

[0183] Step 3: Synthesis of intermediate 138-3 The synthesis method of intermediate 138-3 is the same as that of intermediate 2-3, with a yield of 68.40%.

[0184] Step 4: Synthesis of intermediate 138-4 The synthesis method of intermediate 138-4 is the same as that of intermediate 2-4, with a yield of 62.06%.

[0185] Step 5: Synthesis of intermediate 138-5 The synthesis method of intermediate 138-5 is the same as that of intermediate 2-5, with a yield of 70.50%.

[0186] Step 6: Synthesis of intermediate 138-6 The synthesis method of intermediate 138-6 is the same as that of intermediate 2-6, with a yield of 60.10%.

[0187] Step 7: Synthesis of Compound 138 The synthesis method of compound 138 is the same as that of compound 2, with a yield of 81.24%.

[0188] Example 10 Example 10 provides compound 187, and the synthetic route and method are shown below:

[0189] Step 1: Synthesis of intermediate 187-1 (2',4'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)boronic acid (16.70 g, 50.00 mmol), 4,8-dibromobenzo[1,2-D:4,5-D']bis(oxazole) (20.66 g, 65.00 mmol), and potassium carbonate (13.82 g, 100.00 mmol) were dissolved in a toluene:ethanol:water mixture of 160 mL:10 mL:10 mL and added to a three-necked flask. Tetra(triphenylphosphine)palladium (Pd(PPh3)4, 0.61 g, 0.67 mmol) was added to the reaction mixture under N2 protection, and the mixture was heated to reflux and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature. The organic phase was then dried over sodium sulfate after extraction and washing with dichloromethane and a saturated aqueous sodium chloride solution. The solvent was concentrated to dryness by filtration, and the crude product was purified by column chromatography (dichloromethane and n-hexane = 1:15) to obtain the target compound 187-1 (13.71 g, yield 52.0%).

[0190] Step 2: Synthesis of intermediate 187-2 The synthesis method of intermediate 187-2 is the same as that of intermediate 2-4, with a yield of 56.80%.

[0191] Step 3: Synthesis of intermediate 187-3 The synthesis method of intermediate 187-3 is the same as that of intermediate 2-5, with a yield of 69.50%.

[0192] Step 4: Synthesis of intermediate 187-4 The synthesis method of intermediate 187-4 is the same as that of intermediate 2-6, with a yield of 62.40%.

[0193] Step 5: Synthesis of Compound 187 The synthesis method of compound 187 is the same as that of compound 2, with a yield of 80.75%.

[0194] Example 11 Example 11 provides compound 196, and the synthetic route and method are shown below:

[0195] Step 1: Synthesis of intermediate 196-1 The synthesis method of intermediate 196-1 is the same as that of intermediate 187-1, with a yield of 50.40%.

[0196] Step 2: Synthesis of intermediate 196-2 The synthesis method of intermediate 196-2 is the same as that of intermediate 2-4, with a yield of 59.30%.

[0197] Step 3: Synthesis of intermediate 196-3 The synthesis method of intermediate 196-3 is the same as that of intermediate 2-5, with a yield of 71.20%.

[0198] Step 4: Synthesis of intermediate 196-4 The synthesis method of intermediate 196-4 is the same as that of intermediate 2-6, with a yield of 64.04%.

[0199] Step 5: Synthesis of Compound 196 The synthesis method of compound 196 is the same as that of compound 2, with a yield of 81.05%.

[0200] Example 12 Example 12 provides compound 278, and the synthetic route and method are shown below:

[0201]

[0202] Step 1: Synthesis of intermediate 278-1 The synthesis method of intermediate 278-1 is the same as that of intermediate 187-1, with a yield of 56.08%.

[0203] Step 2: Synthesis of intermediate 278-2 The synthesis method of intermediate 278-2 is the same as that of intermediate 2-1, with a yield of 85.60%.

[0204] Step 3: Synthesis of intermediate 278-3 Intermediate 278-2 (17.20 g, 50 mmol) and Lawson's reagent (12.13 g, 30 mmol) were dissolved in 80 mL of dry toluene. The mixture was heated under reflux and stirred for 2 h under nitrogen protection. After the reaction was complete, the reaction solution was cooled, and the toluene was removed by concentration. The crude product was purified by column chromatography (dichloromethane and n-hexane, volume ratio = 1:1) and further purified by recrystallization from n-hexane / ethyl acetate to obtain the target compound 278-3 (14.95 g, yield 83.0%).

[0205] Step 4: Synthesis of intermediate 278-4 Intermediate 278-3 (14.95 g, 41.50 mmol) and tetramethylpiperidine oxide (TEMPO, 12.97 g, 83.0 mmol) were mixed and dissolved in 120 mL of dry chloroform to remove oxygen. The reaction mixture was stirred under argon protection and irradiated with a 45 W compact fluorescent lamp (CFL) for 12 h. After the reaction was complete, the mixture was extracted and washed with dichloromethane and saturated sodium chloride aqueous solution, and then the organic phase was dried with sodium sulfate. The mixture was filtered, the solvent was concentrated to dryness, and the crude product was purified by column chromatography using silica gel column chromatography (hexane:dichloromethane volume ratio = 1:15) to obtain the target compound 278-4 (12.93 g, yield 87.0%).

[0206] Step 5: Synthesis of intermediate 278-5 The synthesis method of intermediate 278-5 is the same as that of intermediate 2-3, with a yield of 68.50%.

[0207] Step 6: Synthesis of intermediate 278-6 The synthesis method of intermediate 278-6 is the same as that of intermediate 2-4, with a yield of 58.40%.

[0208] Step 7: Synthesis of intermediate 278-7 The synthesis method of intermediate 278-7 is the same as that of intermediate 2-5, with a yield of 71.20%.

[0209] Step 8: Synthesis of intermediate 278-8 The synthesis method of intermediate 278-8 is the same as that of intermediate 2-6, with a yield of 59.80%.

[0210] Step 9: Synthesis of Compound 278 The synthesis method of compound 278 is the same as that of compound 2, with a yield of 82.20%.

[0211] The calculated and measured MS-FAB values ​​of the compounds provided in Examples 1-12 and the intermediates in the synthesis process are shown in Table 1.

[0212]

[0213] The calculated and measured values ​​of the elemental analysis of the compounds provided in Examples 1-12 are shown in Table 2.

[0214]

[0215] Application Examples The following examples, Application Examples 1-12 and Comparative Examples 1-5, further illustrate the application effects of the compounds provided in the above examples in OLED devices. The OLED devices involved in Application Examples 1-12 and Comparative Examples 1-5 are manufactured using the same process, employing the same substrate material and electrode material, and maintaining the same electrode film thickness. The difference lies in the hole injection layer of the different OLED devices.

[0216] See Figure 1 The OLED device comprises a glass substrate 110, an anode 120, a hole injection layer 130, a hole transport layer 140, an electron blocking layer 150, a light-emitting layer 160, a hole blocking layer 170, an electron transport layer 180, an electron injection layer 190, a cathode 200, and a light extraction layer 210, arranged in sequence. The specific structure is: glass / anode (ITO) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / light-emitting layer (EML, main material: blue luminescent material) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) / cathode / light extraction layer (CPL).

[0217] The fabrication method of the OLED device corresponding to Application Example 1 is as follows: The transparent conductive ITO glass substrate (with an anode) (China Southern Glass Group Co., Ltd.) was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and then sequentially washed with ethanol, acetone, and deionized water. It was then baked in a clean environment until all moisture was removed, cleaned with ultraviolet photosynthetic ozone, and treated with oxygen plasma for 30 seconds. The anode-bearing glass substrate was then placed in a vacuum chamber and evacuated.

[0218] Hole injection layer: Compound HT: Compound 2 (mass ratio of 97:3, thickness of 10nm) was deposited on ITO as a hole injection layer at a deposition rate of 0.1nm / s.

[0219] Hole transport layer: Compound HT is deposited on the hole injection layer to form a 120 nm thick hole transport layer at a deposition rate of 0.1 nm / s.

[0220] Electron blocking layer: Compound EB is deposited on the surface of the hole transport layer to form a 10 nm thick electron blocking layer at a deposition rate of 0.1 nm / s.

[0221] Emitting layer: A 20nm thick emitting layer is deposited on the electron blocking layer. The emitting layer includes compound BH and guest material BD. BH is the host emitting material and BD is the phosphorescent dopant guest material with a doping mass percentage of 2% and a deposition rate of 0.1nm / s.

[0222] Hole blocking layer: Compound HB is deposited on the surface of the light-emitting layer to form a 5nm thick hole blocking layer at a deposition rate of 0.1nm / s.

[0223] Electron transport layer: A 30 nm thick layer of compounds ET and LiQ (weight ratio 5:5) was deposited on the surface of the hole blocking layer as an electron transport layer. LiQ is lithium 8-hydroxyquinoline, and the deposition rate was 0.1 nm / s.

[0224] Electron injection layer: A 1 nm thick LiQ layer is deposited on the surface of the electron transport layer as the electron injection layer.

[0225] Cathode: A cathode with a thickness of 15 nm was fabricated on the surface of the electron injection layer. The cathode was made of Mg and Ag with a mass ratio of 1:9.

[0226] Optical extraction layer: An 80nm thick CPL is deposited on the cathode surface as an optical extraction layer.

[0227] The partial composition of the OLED devices prepared in Application Examples 2-12 and Comparative Examples 1-5 can be found in Table 3 below.

[0228]

[0229] The raw material compounds involved in the fabrication of the aforementioned OLED devices are shown below:

[0230]

[0231]

[0232]

[0233] .

[0234] The performance of each OLED device listed in Table 3 was tested. During the testing process, a known driving circuit was used to connect the anode and cathode. The test items are shown below: Using a Photo Research PR655 spectrometer, at 1000 cd / cm 2 Under certain brightness conditions, the driving voltage, turn-on voltage @1 nit, current efficiency, and color coordinates (CIEy) of each device were tested.

[0235] The room temperature and high temperature lifetimes of each device were tested using a Jinghe D3000-96CH lifetime meter under the following conditions: 20 mA / cm².2 The time (LT95) for the brightness to return to 95% of its initial brightness under current density in both ambient (27°C) and high (85°C) environments is the unit of device lifetime, expressed in Hr.

[0236] Obtain the efficiency degradation coefficient φ of the device, where, , This is expressed as the device's maximum current efficiency. This indicates a drive current of 50mA / cm. 2 The current efficiency of the device is measured by φ. A larger φ value indicates a more severe efficiency roll-off, while a smaller φ value indicates that the rapid efficiency degradation at high current densities has been controlled.

[0237] The relevant test data are shown in Table 4.

[0238]

[0239] As shown in Table 4, when the hole injection layer was prepared using the compounds provided in the embodiments of the present invention, the driving voltage of the OLED device was controlled between 3.24V and 3.63V, all lower than the upper limit of 3.63V. In contrast, the driving voltage of Comparative Examples 1-5 was as high as 3.80V to 4.60V, which was significantly higher.

[0240] When the hole injection layer was prepared using the compounds provided in the embodiments of the present invention, the turn-on voltage of the OLED devices was generally between 2.58V and 2.97V, while the turn-on voltage of Comparative Examples 1-5 was between 3.00V and 3.45V. This result indicates that the compounds used in the present invention can effectively reduce the turn-on voltage and driving voltage of the devices, thereby significantly improving the energy efficiency of the devices and reducing power consumption.

[0241] Furthermore, when the hole injection layer was prepared using the compounds provided in the embodiments of the present invention, the current efficiency of the OLED devices was consistently in the range of 220 cd / A to 247 cd / A, significantly higher than the current efficiencies of 178 cd / A to 203 cd / A in Comparative Examples 1-5. This result demonstrates that the compounds used in this invention can significantly improve the luminous efficiency of the device, making the energy conversion process more efficient and suitable for display and lighting applications requiring high brightness and low power consumption.

[0242] Furthermore, when the hole injection layer was prepared using the compounds provided in the embodiments of the present invention, the room temperature lifetime (LT95) of the OLED devices was greater than or equal to 220 hours, with most exceeding 240 hours and reaching a maximum of 260 hours. In contrast, the room temperature lifetime of Comparative Examples 1-5 was only 182 to 203 hours.

[0243] When the hole injection layer was prepared using the compounds provided in the embodiments of this invention at a high temperature of 85°C, the high-temperature lifetime of the OLED devices was greater than or equal to 160 hours, with most devices having a lifetime between 170 and 200 hours. In contrast, the lifetimes of Comparative Examples 1-5 were only 127 to 151 hours, showing a significant difference. These results demonstrate that the compounds used in this invention significantly improve the thermal stability and long-term operational reliability of the devices, especially under high-temperature operating conditions, where their advantages are even more pronounced.

[0244] Furthermore, when the hole injection layer was prepared using the compound provided in the embodiments of the present invention, the efficiency decay coefficient φ of the OLED device ranged from 0.201 to 0.226, with an average value of 0.214. In contrast, the efficiency decay coefficient φ of Comparative Examples 1-5 was as high as 0.294.

[0245] The results show that the device prepared using the compound provided in the embodiments of the present invention can still maintain a high luminous efficiency under high brightness operating conditions, effectively alleviating the efficiency roll-off problem, and enabling it to meet the application requirements of high brightness display scenarios (such as automotive displays, outdoor large screens, etc.).

[0246] In summary, the compounds used in the embodiments of this invention improve the device voltage, device efficiency, and device lifetime of organic electroluminescent devices when preparing hole injection layers. These performance improvements are attributed to the compounds possessing suitable LUMO energy levels and high electron mobility, as well as the effective doping and molecular structure distortion that suppresses film crystallinity.

[0247] The above description is merely for the purpose of enabling those skilled in the art to understand the technical solutions of the present invention, and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A compound, characterized in that, The chemical structural formula of the compound is shown below: ； Among them, Ar1 and Ar2 are both ; Or, one of Ar1 and Ar2 is The other one of Ar1 and Ar2 is one of the following: a phenyl group substituted with 1-2 trifluoromethyl groups, a biphenyl group substituted with 1-2 trifluoromethyl groups, a phenyl group substituted with 1-2 fluorine groups, a biphenyl group substituted with 1-2 fluorine groups, a biphenyl group substituted with both fluorine and cyano groups, a biphenyl group substituted with both fluorine and trifluoromethyl groups, a biphenyl group substituted with both cyano and trifluoromethyl groups, or a phenyl group substituted with 1-2 trifluoromethoxy groups. Ar3 is one of the following: halogen, cyano, trifluoromethyl, pentafluoroethyl, trifluoromethoxy, phenyl, phenyl with 1-5 fluorine-substituted, phenyl with 1-2 trifluoromethyl-substituted, phenyl with 1-2 trifluoromethoxy-substituted, phenyl with both fluorine and cyano substituted, phenyl with both fluorine and trifluoromethyl substituted, phenyl with both cyano and trifluoromethyl substituted, biphenyl with both fluorine and trifluoromethyl substituted, cyanophenyl, pyridyl, pyridyl with 1-4 fluorine-substituted, pyridyl with both fluorine and cyano substituted, pyrimidinyl, pentafluoroethylphenyl, and phenyl with both deuterium and trifluoromethyl substituted. A can be O, S, or Se; L indicates a single bond; Z1 to Z4 are each independently either N or CR5; R1 to R4 are all cyano groups, and R5 is one of hydrogen, deuterium, halogen, cyano, or trifluoromethyl.

2. The compound according to claim 1, characterized in that, Z1 to Z4 are all CR5; Alternatively, one of Z1 to Z4 is N, and the other three are CR5.

3. The use of the compound according to any one of claims 1-2 in organic electroluminescent devices, organic solar cells, organic thin-film transistors, organic photodetectors, organic field-effect transistors, organic integrated circuits, and organic photoreceptors.

4. A hole injection material, characterized in that, The hole injection material includes the compound according to any one of claims 1-2.

5. The hole injection material according to claim 4, characterized in that, The hole injection material further includes a hole transport compound, wherein the hole transport compound has a mass percentage of 70 wt% to 99.5 wt%. The hole transport compound is selected from at least one of carbazole compounds, triaromatic amine compounds, benzidine diamine compounds, fluorene compounds, phthalocyanine compounds, polythiophene, polyethylene, polybenzene sulfonic acid, quinone compounds, and hexacyanohexatribenzene.

6. A charge-generating layer material, characterized in that, The charge-generating layer material includes the compound according to any one of claims 1-2.

7. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes: a first electrode, a second electrode, and a light-emitting unit disposed between the first electrode and the second electrode; The light-emitting unit includes an electron transport functional layer, a light-emitting layer, and a hole transport functional layer, wherein the hole transport functional layer includes the compound according to any one of claims 1-2.

8. The organic electroluminescent device according to claim 7, characterized in that, The light-emitting unit is configured as a plurality of units, and a charge generation layer is provided between two adjacent light-emitting units. The charge generation layer includes an N-type charge generation layer and a P-type charge generation layer. The P-type charge-generating layer comprises the compound according to any one of claims 1-2.

9. The organic electroluminescent device according to claim 8, characterized in that, The hole transport functional layer includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole injection layer includes the compound.

10. A display device, characterized in that, The display device includes the organic electroluminescent device according to any one of claims 7-9.

Images