A fluorene-containing arylamine compound and an organic electroluminescent device thereof

Abstract

This invention relates to the field of organic optoelectronic materials technology, specifically to a fluorene-containing aromatic amine compound and its organic electroluminescent device. The fluorene-containing aromatic amine compound provided by this invention possesses an appropriate hole mobility, effectively improving the charge transport efficiency of the device, thereby improving the driving voltage and luminous efficiency. It also possesses appropriate HOMO and T1 values, enabling good energy level matching with adjacent organic functional layers. When adjacent to the luminescent layer, it can also block exciton migration to the interface between the luminescent layer and the exciton layer, preventing interfacial luminescence and avoiding device aging caused by heat generated by interfacial luminescence, further improving the device's driving voltage, luminous efficiency, and lifespan. Furthermore, the fluorene-containing aromatic amine compound provided by this invention also exhibits excellent thermal and chemical stability, allowing it to be used over a wide temperature range and in environments containing water, oxygen, and other corrosive gases, thereby delaying device aging and improving device lifespan.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, specifically to a fluorene-containing aromatic amine compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) have the characteristics of being thin and light, having a wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility. They have been widely used in the fields of lighting and display and are considered by the industry to be one of the most promising display and lighting technologies.

[0003] Classic OLED devices have a "sandwich" structure, with an emissive layer sandwiched between two electrodes: a cathode and an anode. This emissive layer contains a luminescent material (guest material). When a specific operating voltage is applied between the two electrodes, holes and electrons are injected from the anode and cathode, respectively, and then reach the emissive layer. There, they recombine to generate excitons, releasing energy. Under the influence of the electric field, the excitons migrate, transferring energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to an excited state. Since the excited state is unstable, the electrons then migrate back to the ground state, releasing energy as light, thus producing the luminescence phenomenon. Generally, the lowest unoccupied molecular orbital (LUMO) of the host material is higher than that of the guest material, while the highest occupied molecular orbital (HOMO) of the host material is lower than that of the guest material. To improve device performance, more organic functional layers are provided between the anode and the light-emitting layer, and between the cathode and the light-emitting layer. Generally, the area between the anode and the light-emitting layer is a hole transport region, which mainly plays the role of injecting and transporting holes, including hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, etc.; the area between the cathode and the light-emitting layer is an electron transport region, which mainly plays the role of injecting and transporting electrons, including electron injection layer, electron transport layer, hole blocking layer, etc.

[0004] In addition to setting an organic functional layer between the anode and cathode, a capping layer is also set on the outside of the light-emitting electrode (away from the non-light-emitting electrode). Generally, the capping layer has a high refractive index, which can improve the light transmittance of the device, change the light emission direction, and thus improve the luminous efficiency and color purity of the device.

[0005] To further improve the performance of OLED devices, such as luminous efficiency, color purity, driving voltage, and lifespan, it is necessary to develop hole transport materials that have high energy level matching with the light-emitting layer and other adjacent organic functional layers, appropriate charge transport performance, and excellent stability. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention provides a fluorene-containing aromatic amine compound that possesses appropriate hole mobility, appropriate HOMO and T1 values, as well as excellent thermal and chemical stability. When used as a hole transport material in OLED devices, it can improve the luminous efficiency and lifespan of OLED devices. It has the structure shown in formula (I):

[0007]

[0008] Wherein, Ar1 is selected from one of the structures shown in formula (IA) or formula (IB):

[0009]

[0010] In formula (IA), R1 and R2 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; or R1 and R2 can be linked to form a substituted or unsubstituted C5-C10 carbide ring. One of X1 to X8 is selected from C linked to L1 in formula (I), and another is selected from C linked to... Connected, the remaining ones are independently selected from CR4 or nitrogen atoms; in formula (IB), Z is selected from one of oxygen atom, sulfur atom, NR5, CR6R7, R5 is selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C7 aliphatic ring fused with C6-C30 aromatic ring monovalent group, R6 and R7 are independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C7 aliphatic ring fused with C6-C30 aromatic ring monovalent group, X1-X 16 One of them is selected from C and connected to L1 in equation (I), and another is selected from C and connected to L1 in equation (IC). The remaining atoms are independently selected from CR4 or nitrogen atoms; in formula (IC), R3 is selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; Y1-Y8 are independently selected from CR4 or nitrogen atoms; R4 is selected from hydrogen atoms, deuterium atoms, halogen atoms, cyano, nitro, and ammonia. One of the following: alkyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring, substituted or unsubstituted silyl, or two adjacent R4s linked together to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthyl ring, a substituted or unsubstituted pyridine ring, or a pyrimidine ring;

[0011] The Ar2 and Ar3 are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring.

[0012] The L1 to L3 are independently selected from one of the following: single bond, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C2 to C30 heteroarylene, and a divalent group formed by the fusion of a substituted or unsubstituted C3 to C7 aliphatic ring and a C6 to C30 aromatic ring.

[0013] The condition is that the molecule contains at least one group of formula (II) as follows:

[0014]

[0015] The Ar mentioned therein 101 Ar is selected from one of the single-bonded, substituted or unsubstituted C6-C30 aryl groups. 102 ~Ar 104 It is independently selected from one of the following: a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.

[0016] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode facing away from the anode, and the organic layer contains one or more of the fluorene-containing aromatic amine compounds described in the present invention.

[0017] Beneficial effects:

[0018] The fluorene-containing aromatic amine compound provided by this invention possesses an appropriate hole mobility, which can effectively improve the charge transport efficiency of the device, thereby improving the driving voltage and luminous efficiency of the device. It also has appropriate HOMO and T1 values, which, when used as a hole transport material, can achieve good energy level matching with adjacent organic functional layers. When adjacent to the light-emitting layer, it can also block exciton migration to the interface between the light-emitting layer and the light-emitting layer, avoiding interfacial luminescence and preventing device aging caused by heat generated by interfacial luminescence, further improving the driving voltage, luminous efficiency and lifespan of the device. The fluorene-containing aromatic amine compound provided by this invention also has good thermal and chemical stability, and can be used in a wide temperature range and in environments with water, oxygen and other corrosive gases, thereby delaying device aging and improving device lifespan. Detailed Implementation

[0019] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0020] In the compounds of this invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and comprises atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0021] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0022] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0023] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0024] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl.

[0025] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0026] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentenyl or cyclohexenyl.

[0027] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0028] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, fused-ring aryl, or a fused group of aryl and aliphatic ring. It preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0029] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0030] The term "group formed by the fusion of aromatic and aliphatic rings" as used in this invention refers to the collective term for a monovalent group formed by the fusion of an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloynyl) and the removal of one hydrogen atom. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. It may include, but is not limited to, benzene, naphthalene, anthracene, phenanthrene, etc. The aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms. It may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of groups formed by the fusion of an aromatic ring and an aliphatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc.

[0031] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0032] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0033] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0034] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0035] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C The 12-membered cycloalkenyl group, C3-C12 heterocycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, and silyl group, when substituted with multiple substituents, have the multiple substituents being the same or different from each other; preferably, this means not being substituted or being substituted with one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated cyclobutane, and cyclopentane. Cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl The substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazoyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl, when substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

[0036] In this specification, when the position of a substituent or linking site on the aromatic ring is not fixed, it means that it can be linked to any of the optional sites on the aromatic ring. For example, Can represent Can represent Can represent And so on.

[0037] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

[0038] The linked ring structure described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 carbon rings) refers to the individual groups being connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0039]

[0040] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0041] In this specification, "at least one" includes, where permitted, one, two, three, four, five or more.

[0042] This invention provides a fluorene-containing aromatic amine compound having the structure shown in formula (I):

[0043]

[0044] Wherein, Ar1 is selected from one of the structures shown in formula (IA) or formula (IB):

[0045]

[0046] In formula (IA), R1 and R2 are independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; or R1 and R2 can be linked to form a substituted or unsubstituted C5-C10 carbide ring. One of X1 to X8 is selected from C linked to L1 in formula (I), and another is selected from C linked to... Connected, the remaining ones are independently selected from CR4 or nitrogen atoms; in formula (IB), Z is selected from one of oxygen atom, sulfur atom, NR5, CR6R7, R5 is selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C7 aliphatic ring fused with C6-C30 aromatic ring monovalent group, R6 and R7 are independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C7 aliphatic ring fused with C6-C30 aromatic ring monovalent group, X1-X 16 One of them is selected from C and connected to L1 in equation (I), and another is selected from C and connected to L1 in equation (IC). The remaining atoms are independently selected from CR4 or nitrogen atoms; in formula (IC), R3 is selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; Y1-Y8 are independently selected from CR4 or nitrogen atoms; R4 is selected from hydrogen atoms, deuterium atoms, halogen atoms, cyano, nitro, and ammonia. One of the following: alkyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, a monovalent group formed by the fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring, substituted or unsubstituted silyl, or two adjacent R4s linked together to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthyl ring, a substituted or unsubstituted pyridine ring, or a pyrimidine ring;

[0047] The Ar2 and Ar3 are independently selected from one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and monovalent groups formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring.

[0048] The L1 to L3 are independently selected from one of the following: single bond, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C2 to C30 heteroarylene, and a divalent group formed by the fusion of a substituted or unsubstituted C3 to C7 aliphatic ring and a C6 to C30 aromatic ring.

[0049] The condition is that the molecule contains at least one group of formula (II) as follows:

[0050]

[0051] The Ar mentioned therein 101 Ar is selected from one of the single-bonded, substituted or unsubstituted C6-C30 aryl groups. 102 ~Ar 104 It is independently selected from one of the following: a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.

[0052] Preferably, at least one of Ar1, Ar2, and Ar3 contains at least one group of formula (II).

[0053] Preferably, the substituent in "substituted or unsubstituted" is selected from deuterium atom; halogen atom; cyano; C1-C12 straight-chain or branched alkyl group substituted or unsubstituted by one or more of the following groups: deuterium atom, halogen atom; cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; tert-butyl; phenyl; deuterated phenyl; methyl-substituted phenyl; tert-butyl-substituted phenyl; halogen-substituted phenyl; cyano-substituted phenyl; adamantyl-substituted phenyl; norbornel-substituted phenyl; naphthyl; deuterated naphthyl; anthraceneyl; phenanthrene; biphenyl; pyridyl; pyrimidinyl; dibenzofuranyl; dibenzothiopheneyl; deuterium atom; halogenated or unsubstituted alkyl group ... The following are C3-C12 cycloalkyl groups substituted or unsubstituted with one or more of the following groups: halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; C3-C12 cycloalkenyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; C6-C30 cycloalkenyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl. A aryl group; a C2-C30 heteroaryl group substituted or unsubstituted with one or more of the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; a C6-C30 aromatic ring fused with a substituted or unsubstituted aliphatic ring of C3-C7, substituted or unsubstituted with one or more of the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; a group substituted or unsubstituted with one of the group consisting of deuterium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and benzene. The silylation group is one or more substituted or unsubstituted methyl alkyl groups, consisting of alkyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, halogen-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl, deuterated naphthyl, anthraceneyl, phenanthreneyl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl. The silylation group can be one or more, and when there are multiple substituted groups, the multiple substituted groups may be the same or different. When there are multiple substituted groups, two adjacent substituted groups may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C7 carbon ring.

[0054] Preferably, the substituents in "substituted or unsubstituted" are selected from deuterium atom; fluorine atom; cyano; methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; deuterated methyl; deuterated isopropyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cyclopropenyl; cyclobutenyl; cyclopentenyl; cyclohexenyl; adamantyl alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, and tert-butyl; norbornyl alkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, and tert-butyl; and deuterium atom, methyl, ethyl, isopropyl, n-butyl, and tert-butyl. A phenyl group substituted or unsubstituted with one or more of the following groups: deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; an anthracene group substituted or unsubstituted with one or more of the following groups: deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a phenyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl. The following are substituted or unsubstituted phenanthrene groups from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornel; fluorene groups from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, norbornel, phenyl, naphthyl, and biphenyl; and fluorene groups from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornel. Unsubstituted dibenzofuranyl; dibenzothiophenyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, norbornyl; carbazoyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, norbornyl, phenyl, naphthyl, biphenyl; pyridyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, norbornyl;A pyrimidinyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a pyrazinyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a pyridaz ... of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a pyridazinyl group substituted or unsubstituted by one of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, deuterated isopropyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a pyridazinyl group substituted or unsubstituted by one of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, deuterated isopropyl, deuterated isopropyl Quinolinyl groups substituted or unsubstituted with one or more of the group consisting of butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; isoquinolinyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; quinoxalinyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; A quinazolinyl group substituted or unsubstituted with one or more of the group consisting of isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; an indenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a tetrahydronaphthyl group substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, adamantyl, and norbornyl; a phenyl group substituted with methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, or methyl. The methyl silyl group is selected from the group consisting of phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, pyridyl-substituted phenyl, naphthyl-substituted phenyl, naphthyl, deuterated naphthyl, anthraceneyl, phenanthrene, biphenyl, pyridyl, bipyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, and N-phenylcarbazoyl, and is either substituted or unsubstituted. The methyl silyl group may be one or more substituents. When there are multiple substituents, the multiple substituents may be the same or different. When there are multiple substituents, adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring.

[0055] Preferably, the Ar1 is selected from one of the following structures:

[0056]

[0057]

[0058]

[0059] Wherein, each time a1 appears, it is selected from 1, 2, 3 or 4, either the same or different; each time b1 appears, it is selected from 1, 2 or 3, either the same or different; each time c1 appears, it is selected from 1 or 2, either the same or different; each time d1 appears, it is selected from 1.

[0060] The R mentioned 11 R 21 Independently selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, phenyl substituted with formula (II) group, naphthyl, naphthyl substituted with formula (II) group, anthraceneyl, anthraceneyl substituted with formula (II) group, phenanthrene, phenanthreneyl substituted with formula (II) group, biphenyl, biphenyl substituted with formula (II) group, pyridyl, pyridylyl group substituted with formula (II) group, or when R 11 With R 21 When independently selected from one of phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, phenyl substituted with formula (II) group, naphthyl, naphthyl substituted with formula (II) group, anthraceneyl, anthraceneyl substituted with formula (II) group, phenanthreneyl, phenanthreneyl substituted with formula (II) group, biphenyl, biphenyl substituted with formula (II) group, pyridyl, pyridylyl group substituted with formula (II) group, they can be linked together to form a substituted or unsubstituted five-membered carbon ring;

[0061] The R mentioned 31 It is selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, trifluoromethyl-substituted phenyl, trimethylsilyl-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, and pyridyl.

[0062] The R mentioned 41Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, trifluoromethyl-substituted phenyl. One of the following groups: trimethylsilyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthryl, deuterated phenanthryl, biphenyl, deuterated biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, tert-butyl-substituted biphenyl, adamantyl-substituted biphenyl, norbornene-substituted biphenyl, trifluoromethyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, pyridyl, pyrimidinyl, or a group of formula (II);

[0063] The R mentioned 41a Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, trifluoromethyl-substituted phenyl. One of the following groups: trimethylsilyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthryl, deuterated phenanthryl, biphenyl, deuterated biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, tert-butyl-substituted biphenyl, adamantyl-substituted biphenyl, norbornene-substituted biphenyl, trifluoromethyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, pyridyl, pyrimidinyl, or a group of formula (II).

[0064] Preferred, R 41a One or two of them are selected from the groups of formula (II).

[0065] Preferably, the R 11 R 21 The same is selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, naphthylbiphenyl, pyridyl, or when R 11 With R 21 When all of the following are selected from phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, naphthyl biphenyl, and pyridyl, they can be linked together to form substituted or unsubstituted five-membered carbon rings.

[0066] Preferably, the Ar1 is selected from one of the following structures:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072] Preferably, the Ar2 and Ar3 are independently selected from one of the following structures:

[0073]

[0074]

[0075] Wherein, the a 101 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the b mentioned above. 101 Each time it appears, it is selected from 1, 2, 3, or 4, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 1, 2, or 3, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 1, 2, 3, 4, 5, or 6, either identically or differently; the e mentioned 101 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 1 or 2, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the h mentioned 101 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, either the same or different.

[0076] The R mentioned 101Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; isopropyl; deuterated isopropyl; tert-butyl; deuterated tert-butyl; adamantyl; methyl-substituted adamantyl; ethyl-substituted adamantyl; deuterated adamantyl; norbornyl; methyl-substituted norbornyl; ethyl-substituted norbornyl; deuterated norbornyl; substituted with deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl A phenyl group substituted with or unsubstituted with one or more of the following: alkyl-substituted norbornyl groups; a phenyl group substituted with or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, or a naphthyl group; a phenyl group substituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, or ethyl-substituted adamantyl. Anthracene group substituted or unsubstituted with one or more of the following: adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl; phenanthryl group substituted or unsubstituted with one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl; phenanthryl group substituted or unsubstituted with one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, and deuterated isopropyl. Triphenylene oxide substituted or unsubstituted with one or more of the following: methyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl; fluorene group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl.Spirodifluorenyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; dibenzofuranyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; A dibenzothiophene group substituted or unsubstituted with one or more of the following: fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; a carbazoyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; one of the groups in formula (II);

[0077] The R mentioned 102The phenyl group is selected from one or more of the following: substituted or unsubstituted phenyl groups, including phenyl groups with deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, naphthyl, and deuterated naphthyl; and phenyl groups substituted with deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, and methyl-substituted norbornyl. Naphthyl groups substituted with or unsubstituted one or more of the following: alkyl, ethyl-substituted norbornyl, deuterated norbornyl, phenyl, and deuterated phenyl; anthracene groups substituted with or unsubstituted one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl; adamantane groups substituted with or unsubstituted one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and methyl. A phenanthrene group substituted with or unsubstituted with one or more of the following: methyl, ethyl-substituted adamanthrene, deuterated adamanthrene, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, or deuterated norbornyl; a phenylene group substituted with or unsubstituted with one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamanthrene, methyl-substituted adamanthrene, ethyl-substituted adamanthrene, deuterated adamanthrene, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, or deuterated norbornyl; a phenylene group substituted with or unsubstituted with one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated... Biphenyl groups substituted or unsubstituted with one or more of the following: isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, and phenyl; fluorenyl groups substituted or unsubstituted with one or more of the following: deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl.Spirodifluorenyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; dibenzofuranyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; A dibenzothiophene group substituted or unsubstituted with one or more of the following: fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; a carbazoyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl; one of the groups in formula (II);

[0078] The R mentioned 103 Each time it appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, and deuterated norbornyl.

[0079] Preferred, R 101 One, two, three or more of the groups selected from formula (II).

[0080] Preferred, R 102 Selected from groups of formula (II).

[0081] Preferably, the Ar2 is selected from one of the following structures:

[0082]

[0083] Wherein, the a 201 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the b mentioned above.201 Each time it appears, it is selected from 1, 2, 3, or 4, either identically or differently; the c mentioned 201 Each time it appears, it is selected from 1, 2, or 3, either identically or differently; the d mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, or 6, either identically or differently; the e mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 201 Each time it appears, it is selected from 1 or 2, either identically or differently; the g mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the h mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, either the same or different.

[0084] The R mentioned 201 Each time it appears, it is selected from the same or different groups of the following: hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; tert-butyl; deuterated tert-butyl; adamantyl; norbornyl; a phenyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl; a naphthyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl; or one of the groups of formula (II).

[0085] The R mentioned 202 Selected from a phenyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, and naphthyl; a naphthyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, and naphthyl; a biphenyl group substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl; or one of the groups in formula (II).

[0086] The R mentioned 203 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group, and tert-butyl group.

[0087] Preferred, R 201 One, two, three or more of the groups selected from formula (II).

[0088] Preferred, R 202Selected from groups of formula (II).

[0089] Preferably, the Ar3 is selected from one of the following structures:

[0090]

[0091] Wherein, the a 301 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the b mentioned above. 301 Each time it appears, it is selected from 1, 2, 3, or 4, either identically or differently; the c mentioned 301 Each time it appears, it is selected from 1, 2, or 3, either identically or differently; the d mentioned 301 Each time it appears, it is selected from 1, 2, 3, 4, 5, or 6, either identically or differently; the e mentioned 301 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 301 Each time it appears, it is either selected from 1 or 2, either the same or different.

[0092] The R mentioned 301 Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; tert-butyl; deuterated tert-butyl; adamantyl; norbornyl; a phenyl group substituted or unsubstituted with one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl; a naphthyl group substituted or unsubstituted with one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl; or one of the groups shown in formula (II).

[0093] The R mentioned 302 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group, and tert-butyl group.

[0094] Preferred, R 301 One, two, three or more of the groups selected from formula (II).

[0095] Preferably, the Ar2 is selected from one of the following structures:

[0096]

[0097]

[0098] Preferably, the Ar3 is selected from one of the following structures:

[0099]

[0100] Preferably, the Ar described in formula (II) 101 Selected from one of single bonds, phenylene, deuterated phenylene, naphthylene, deuterated naphthylene, biphenylene, and deuterated biphenylene, wherein Ar 102 ~Ar 104 It is independently selected from one of methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidinyl-substituted phenyl, naphthyl, deuterated naphthyl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, anthracene, biphenyl, deuterated biphenyl, pyridyl, bipyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, N-phenylcarbazoyl.

[0101] Preferably, the aforementioned Choose one of the following structures:

[0102]

[0103] Preferably, L1 to L3 are independently selected from a single bond or one of the following structures:

[0104]

[0105] Wherein, the a 401 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 401 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 401 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 401 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 401 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0106] The R mentioned 401Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; isopropyl; deuterated isopropyl; tert-butyl; deuterated tert-butyl; adamantyl; norbornyl; a phenyl group substituted or unsubstituted with one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl; a naphthyl group substituted or unsubstituted with one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl;

[0107] The R mentioned 402 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group.

[0108] Preferably, L1 to L3 are independently selected from a single bond or one of the following structures:

[0109]

[0110]

[0111] Preferably, the fluorene-containing aromatic amine compound contains one, two, three, four, or more formula (II) groups. More preferably, the fluorene-containing aromatic amine compound contains one, two, three, or four formula (II) groups.

[0112] Preferably, in the fluorene-containing aromatic amine compound, Ar1 contains one, two, three or more formula (II) groups.

[0113] More preferably, R 41a One or two of them are selected from the groups of formula (II).

[0114] Preferably, in the fluorene-containing aromatic amine compound, Ar2 and Ar3 contain one, two, three or more formula (II) groups.

[0115] More preferably, R 101 One, two, or three of them are selected from groups of formula (II).

[0116] More preferably, R 102 The group is selected from formula (II).

[0117] Preferably, in the fluorene-containing aromatic amine compound, Ar2 contains one, two, three or more formula (II) groups.

[0118] More preferably, R201 One, two, or three of them are selected from groups of formula (II).

[0119] More preferably, R 202 Selected from groups of formula (II).

[0120] Preferably, in the fluorene-containing aromatic amine compound, Ar3 contains one, two, three or more formula (II) groups.

[0121] More preferably, R 301 One, two, or three of them are selected from groups of formula (II).

[0122] More preferably, R 302 Selected from groups of formula (II).

[0123] Preferred, R 41a R 201 R 202 R 301 R 302 One, two, three or four groups are selected from formula (II).

[0124] More preferably, R 201 R 202 R 301 R 302 One, two, three or four groups are selected from formula (II).

[0125] More preferably, R 201 R 202 One or two of them and R 301 R 302 One or two of them are selected from the group of formula (II).

[0126] Preferably, the fluorene-containing aromatic amine compound is selected from one of the following compounds:

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] The above only lists some specific structural forms of the fluorene-containing aromatic amine compounds described in this invention. However, this invention is not limited to these chemical structures. Any structure based on formula (I) with substituents as defined in this invention should be included.

[0154] The fluorene-containing aromatic amine compounds of the present invention can be prepared by one of the following synthetic routes:

[0155] Synthesis Route 1:

[0156]

[0157] Synthesis Route 2:

[0158]

[0159] Synthesis Route 3:

[0160]

[0161] In each of the above synthetic routes, X1 and X2 are selected from chlorine, bromine, or iodine atoms each time they appear;

[0162] Ar1 to Ar3 and L1 to L3 are as described in this invention.

[0163] In the above synthetic routes, compound (Y1) reacts with halides (Y2) and (Y3) via a CN coupling reaction to obtain the fluorene-containing aromatic amine compound described in this invention. The reaction order of compound (Y1) with halides (Y2) and (Y3) is not limited; it can react with (Y2) first and then with (Y3), or vice versa.

[0164] The above reaction route employs reaction types commonly used in organic synthesis, and there are no particular limitations on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation method uses readily available raw materials, has a simple process, and yields excellent results. This invention can also be synthesized using other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0165] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode facing away from the anode, and the organic layer contains one or more of the fluorene-containing aromatic amine compounds described in the present invention.

[0166] Preferably, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0167] Preferably, the organic layer includes a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, wherein the hole transport region contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0168] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light emission assist layer.

[0169] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT-19, compounds p-1 to p-3, and the fluorene-containing aromatic amine compounds described in this invention, but not limited thereto.

[0170]

[0171] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a concentration of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), compounds HT-1 to HT-19 as shown above, and fluorene-containing aromatic amine compounds described in this invention, but not limited thereto.

[0172] The luminescent auxiliary layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1, 1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, compounds HT-1 to HT-19 as shown above, and fluorene-containing aromatic amine compounds of the present invention, but not limited thereto.

[0173] The luminescent layer of the present invention comprises a guest material and a host material, and a dual host material formed by two host materials can be used. The guest material can be a fluorescent compound, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) and other materials can also be used, such as phosphorescent materials, metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridineformyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material. Examples include metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives, benzoxazole derivatives, benzothiazole derivatives or benzimidazole derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, and aromatic amine compounds such as triaromatic amine derivatives or fused polycyclic aromatic amine derivatives. Examples include Alq3, BAlq, TPBI, TPD, 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), and 9,10-bis(2-naphthyl)anthracene (ADN), but are not limited to these.

[0174] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0175] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0176] The electron transport layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can use aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymers, etc. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline) beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but is not limited to these.

[0177] The hole-blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The selected material must have a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the selected material must be lower than that of the main material of the emissive layer to effectively block holes. Further, the electron mobility of the hole-blocking layer material used is 10. -6 cm 2 A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq, but these are not limited to these.

[0178] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0179] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0180] The capping layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, and compound CP-4, but are not limited thereto.

[0181]

[0182] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, wherein the hole injection layer contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0183] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, wherein the hole transport layer contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0184] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, and both the hole injection layer and the hole transport layer contain one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0185] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0186] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole transport layer contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0187] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the light-emitting auxiliary layer contains one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0188] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer and the hole transport layer each contain one or more of the fluorene-containing aromatic amine compounds described in this invention.

[0189] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0190] The thickness of each of the aforementioned organic layers is typically between 5 nm and 100 μm, preferably between 10 nm and 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0191] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0192] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0193] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent.

[0194] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0195] Synthesis Example 1: Synthesis of Compound DD

[0196] Synthesis of compound DD-8:

[0197]

[0198] Under nitrogen protection, bb-8 (9.26 g, 30.0 mmol) and 30 ml of tetrahydrofuran were added to a three-necked flask. After cooling to -78 °C, 5 ml of a mixed solution of n-hexane containing n-butyllithium (1.6 M) was added and stirred for 50 min. Then, 20 ml of a tetrahydrofuran solution containing aa-8 (5.38 g, 27.4 mol) was added dropwise. Stirring was continued at -78 °C for 50 min, and then the mixture was raised to room temperature and stirred for 3 h. After the reaction was complete, 10 ml of saturated ammonium chloride solution was added to the reaction system to separate the organic layer. The organic solvent was then evaporated, and the resulting residue was transferred to a three-necked flask. 65 ml of acetic anhydride and 3 ml of hydrochloric acid were added, and the mixture was stirred at 100 °C for 3 h. The reaction solution was then poured into 30 ml of ice water, where a solid precipitated. The solid was filtered off and recrystallized from n-hexane / ethyl acetate (volume ratio 25:1) to give compound DD-8 (8.16 g, yield 73%). HPLC analysis showed a solid purity ≥99.56%. Mass spectrometry m / z: 407.1449 (theoretical value: 407.1441).

[0199] Following the synthetic method for compound DD-8, compounds aa-8 and bb-8 were replaced with the corresponding compounds (see Table 101 for details) to synthesize the other compounds DD shown in Table 101:

[0200] Table 101

[0201]

[0202]

[0203]

[0204] Synthesis of compound DD-182:

[0205]

[0206] Following the synthetic method of compound DD-8, replacing compound bb-8 with an equimolar amount of compound bb-70 yields compound ee-182 (9.65 g, yield 78%), with a solid purity ≥99.79% as determined by HPLC. Mass spectrometry m / z: 450.0996 (theoretical value: 450.0983).

[0207] Under nitrogen protection, compounds ee-182 (6.77 g, 15 mmol), ff-182 (3.10 g, 15 mmol), potassium carbonate (3.11 g, 22.5 mmol), and Pd2(dba)3 (0.14 g, 0.15 mmol) were added to a three-necked flask, followed by 135 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from toluene to give compound DD-182 (6.32 g, 79% yield). HPLC analysis showed the solid purity to be ≥99.75%. Mass spectrometry m / z: 532.1942 (theoretical value: 532.1958).

[0208] Following the synthetic method for compound DD-182, replace compounds ee-182 and ff-182 with the corresponding compounds (see Table 102 for details) to synthesize the other compounds DD shown in Table 102:

[0209] Table 102

[0210]

[0211] Synthesis Example 2: Synthesis of Compound BB

[0212] Synthesis of compound BB-97:

[0213]

[0214] Under nitrogen protection, compound cc-97 (11.46 g, 50 mmol), compound dd-97 (7.82 g, 50 mmol), potassium carbonate (10.38 g, 75 mmol), and Pd2(dba)3 (0.45 g, 0.5 mmol) were added to a three-necked flask, followed by 450 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 7.5 h. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from toluene to give compound BB-97 (10.69 g, yield 82%). The purity of the solid was ≥99.70% as determined by HPLC. Mass spectrometry m / z: 260.0775 (theoretical value: 260.0788).

[0215] Synthesis of compound BB-679:

[0216]

[0217] Following the synthetic method of compound BB-97, by replacing compound cc-97 with an equimolar amount of BB-191 and dd-97 with an equimolar amount of dd-679, compound BB-679 can be obtained.

[0218] Synthesis of compound BB-596:

[0219]

[0220] Compound BB-191 (11.46 g, 50 mmol), compound dd-596 (10.08 g, 50 mmol), palladium acetate (1.25 g, 5.5 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (4.10 g, 10 mmol), sodium tert-butoxide (7.21 g, 75 mmol), and 250 mL of o-xylene were added to a three-necked flask. The mixture was stirred and refluxed for 3.5 h. After the reaction was complete, the mixture was washed with distilled water and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation. The mixture was then recrystallized from o-xylene to give compound BB-596 (13.12 g, 75% yield). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 349.1044 (theoretical value: 349.1054).

[0221] Synthesis Example 3: Synthesis of Compound 8

[0222]

[0223] Under nitrogen protection, compounds AA-8 (4.96 g, 30 mmol), BB-8 (9.22 g, 30 mmol), Pd(OAc)2 (0.08 g, 0.35 mmol), P(t-Bu)3 (0.07 g, 0.35 mmol), sodium tert-butoxide (4.81 g, 50 mmol), and 150 mL of toluene were added to a three-necked flask. The mixture was stirred and refluxed for 4 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic phase was dried over anhydrous magnesium sulfate, and the organic solvent was removed by rotary evaporation. The mixture was then recrystallized from toluene / methanol (10:3) to give compound CC-8 (9.99 g, yield 85%). The purity of the solid was ≥99.78% as determined by HPLC. Mass spectrometry m / z: 391.1745 (theoretical value: 391.1756).

[0224] Under nitrogen protection, compound CC-8 (3.92 g, 10 mmol), compound DD-8 (4.08 g, 10 mmol), Pd2(dba)3 (0.12 g, 0.13 mmol), BINAP (0.17 g, 0.27 mmol), sodium tert-butoxide (1.61 g, 16.7 mmol), and 50 mL of toluene were added to a three-necked flask. The mixture was stirred and refluxed for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing, the liquid was separated, and the organic phase was dried over anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation, and the mixture was recrystallized from toluene / methanol (10:1) to give compound 8 (5.72 g, 75%). The purity of the solid was ≥99.93% as determined by HPLC. Mass spectrometry m / z: 762.3451 (theoretical value: 762.3430). Theoretical elemental content (%) C 55 H 46 N₂Si: C, 86.57; H, 6.08; N, 3.67. Measured elemental content (%): C, 86.53; H, 6.09; N, 3.69.

[0225] Synthesis Example 4: Synthesis of Compound 31

[0226]

[0227] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-31, compound BB-8 was replaced with an equimolar amount of compound BB-31, compound CC-8 was replaced with an equimolar amount of compound CC-31, and compound DD-8 was replaced with an equimolar amount of compound DD-31 to obtain compound 31 (5.96 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 815.3683 (theoretical value: 815.3696). Theoretical elemental content (%) C 58 H 49 N3Si: C, 85.36; H, 6.05; N, 5.15. Measured elemental content (%): C, 85.35; H, 6.03; N, 5.19.

[0228] Synthesis Example 5: Synthesis of Compound 70

[0229]

[0230] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-70, compound CC-8 was replaced with an equimolar amount of compound CC-70, and compound DD-8 was replaced with an equimolar amount of compound DD-70 to obtain compound 70 (6.14 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 807.4275 (theoretical value: 807.4260). Theoretical elemental content (%) C 59 H 57 NSi: C, 87.68; H, 7.11; N, 1.73. Measured elemental content (%): C, 87.70; H, 7.13; N, 1.69.

[0231] Synthesis Example 6: Synthesis of Compound 79

[0232]

[0233] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-79, compound BB-8 was replaced with an equimolar amount of compound BB-79, compound CC-8 was replaced with an equimolar amount of compound CC-79, and compound DD-8 was replaced with an equimolar amount of compound DD-70, thus obtaining compound 79 (6.37 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 805.4120 (theoretical value: 805.4104). Theoretical elemental content (%) C 59 H 55 NSi: C, 87.90; H, 6.88; N, 1.74. Measured elemental content (%): C, 87.95; H, 6.85; N, 1.72.

[0234] Synthesis Example 7: Synthesis of Compound 97

[0235]

[0236] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-97, compound BB-8 was replaced with an equimolar amount of compound BB-97, compound CC-8 was replaced with an equimolar amount of compound CC-97, and compound DD-8 was replaced with an equimolar amount of compound DD-97, thus obtaining compound 97 (6.47 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 850.3731 (theoretical value: 850.3743). Theoretical elemental content (%) C 62 H 50N₂Si: C, 87.49; H, 5.92; N, 3.29. Measured elemental content (%): C, 87.48; H, 5.90; N, 3.33.

[0237] Synthesis Example 8: Synthesis of Compound 119

[0238]

[0239] Under nitrogen protection, compound CC-119 (2.69 g, 10 mmol), compound DD-119 (7.34 g, 10 mmol), Pd2(dba)3 (0.12 g, 0.13 mmol), BINAP (0.17 g, 0.27 mmol), sodium tert-butoxide (1.61 g, 16.7 mmol), and 50 mL of toluene were added to a three-necked flask. The mixture was stirred and refluxed for 6 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing, the liquid was separated, and the organic phase was dried over anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation, and the mixture was recrystallized from toluene / methanol (10:1) to give compound 119 (6.46 g, 70%). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrometry m / z: 921.4173 (theoretical value: 921.4186). Theoretical elemental content (%) C 66 H 59 NSi2: C, 85.94; H, 6.45; N, 1.52. Measured elemental content (%): C, 85.90; H, 6.46; N, 1.55.

[0240] Synthesis Example 9: Synthesis of Compound 122

[0241]

[0242] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-122, compound CC-8 was replaced with an equimolar amount of compound CC-122, and compound DD-8 was replaced with an equimolar amount of compound DD-122 to obtain compound 122 (6.48 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 875.3959 (theoretical value: 875.3947). Theoretical elemental content (%) C 65 H 53 NSi: C, 89.10; H, 6.10; N, 1.60. Measured elemental content (%): C, 89.14; H, 6.11; N, 1.57.

[0243] Synthesis Example 10: Synthesis of Compound 182

[0244]

[0245] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-182, compound BB-8 was replaced with an equimolar amount of compound BB-79, compound CC-8 was replaced with an equimolar amount of compound CC-182, and compound DD-8 was replaced with an equimolar amount of compound DD-182 to obtain compound 182 (6.23 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 818.4119 (theoretical value: 818.4105). Theoretical elemental content (%) C 60 H 46 D5NSi: C, 87.97; H, 6.89; N, 1.71. Measured elemental content (%): C, 87.96; H, 6.86; N, 1.75.

[0246] Synthesis Example 11: Synthesis of Compound 191

[0247]

[0248] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-191, compound CC-8 was replaced with an equimolar amount of compound CC-191, and compound DD-8 was replaced with an equimolar amount of compound DD-191 to obtain compound 191 (6.56 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 897.4173 (theoretical value: 897.4186). Theoretical elemental content (%) C 64 H 59 NSi2: C, 85.57; H, 6.62; N, 1.56. Measured elemental content (%): C, 85.55; H, 6.64; N, 1.57.

[0249] Synthesis Example 12: Synthesis of Compound 214

[0250]

[0251] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-214, compound CC-8 was replaced with an equimolar amount of compound CC-214, and compound DD-8 was replaced with an equimolar amount of compound DD-70 to obtain compound 214 (6.27 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 813.3413 (theoretical value: 813.3427). Theoretical elemental content (%) C 59 H 47NOSi: C, 87.05; H, 5.82; N, 1.72. Measured elemental content (%): C, 87.08; H, 5.83; N, 1.68.

[0252] Synthesis Example 13: Synthesis of Compound 275

[0253]

[0254] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-275, compound CC-8 was replaced with an equimolar amount of compound CC-275, and compound DD-8 was replaced with an equimolar amount of compound ee-182 to obtain compound 275 (6.40 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 852.3918 (theoretical value: 852.3900). Theoretical elemental content (%) C 62 H 52 N₂Si: C, 87.28; H, 6.14; N, 3.28. Measured elemental content (%): C, 87.26; H, 6.11; N, 3.30.

[0255] Synthesis Example 14: Synthesis of Compound 337

[0256]

[0257] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-337, compound CC-8 was replaced with an equimolar amount of compound CC-337, and compound DD-8 was replaced with an equimolar amount of compound DD-70 to obtain compound 337 (7.22 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 913.4116 (theoretical value: 913.4104). Theoretical elemental content (%) C 68 H 55 NSi: C, 89.33; H, 6.06; N, 1.53. Measured elemental content (%): C, 89.36; H, 6.04; N, 1.50.

[0258] Synthesis Example 15: Synthesis of Compound 378

[0259]

[0260] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-378, compound CC-8 was replaced with an equimolar amount of compound CC-379, and compound DD-8 was replaced with an equimolar amount of compound DD-70 to obtain compound 378 (6.71 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 881.4404 (theoretical value: 881.4417). Theoretical elemental content (%) C 65 H 59 NSi: C, 88.49; H, 6.74; N, 1.59. Measured elemental content (%): C, 88.46; H, 6.75; N, 1.57.

[0261] Synthesis Example 16: Synthesis of Compound 414

[0262]

[0263] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-97, compound BB-8 with an equimolar amount of compound BB-79, compound CC-8 with an equimolar amount of compound CC-414, and compound DD-8 with an equimolar amount of compound DD-414, to obtain compound 414 (7.11 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 887.3959 (theoretical value: 887.3947). Theoretical elemental content (%) C 66 H 53 NSi: C, 89.25; H, 6.01; N, 1.58. Measured elemental content (%): C, 89.28; H, 6.03; N, 1.55.

[0264] Synthesis Example 17: Synthesis of Compound 421

[0265]

[0266] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-97, compound BB-8 was replaced with an equimolar amount of compound BB-191, compound CC-8 was replaced with an equimolar amount of compound CC-421, and compound DD-8 was replaced with an equimolar amount of compound DD-421 to obtain compound 421 (6.36 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 825.3780 (theoretical value: 825.3791). Theoretical elemental content (%) C 61 H 51NSi: C, 88.68; H, 6.22; N, 1.70. Measured elemental content (%): C, 88.70; H, 6.19; N, 1.74.

[0267] Synthesis Example 18: Synthesis of Compound 445

[0268]

[0269] According to the synthesis method in Example 8, compound CC-119 was replaced with an equimolar amount of compound CC-421, and compound DD-119 was replaced with an equimolar amount of compound DD-445 to obtain compound 445 (7.26 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 873.3779 (theoretical value: 873.3791). Theoretical elemental content (%) C 65 H 51 NSi: C, 89.30; H, 5.88; N, 1.60. Measured elemental content (%): C, 89.34; H, 5.87; N, 1.58.

[0270] Synthesis Example 19: Synthesis of Compound 467

[0271]

[0272] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-79, compound CC-8 was replaced with an equimolar amount of compound CC-467, and compound DD-8 was replaced with an equimolar amount of compound DD-414 to obtain compound 467 (6.99 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 883.4038 (theoretical value: 883.4030). Theoretical elemental content (%) C 63 H 57 NSi2: C, 85.57; H, 6.50; N, 1.58. Measured elemental content (%): C, 85.52; H, 6.53; N, 1.60.

[0273] Synthesis Example 20: Synthesis of Compound 491

[0274]

[0275] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-491, compound CC-8 was replaced with an equimolar amount of compound CC-491, and compound DD-8 was replaced with an equimolar amount of compound DD-445 to obtain compound 491 (7.19 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 887.3595 (theoretical value: 887.3583). Theoretical elemental content (%) C 65 H 49 NOSi: C, 87.90; H, 5.56; N, 1.58. Measured elemental content (%): C, 87.94; H, 5.54; N, 1.56.

[0276] Synthesis Example 21: Synthesis of Compound 533

[0277]

[0278] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-533, compound CC-8 was replaced with an equimolar amount of compound CC-533, and compound DD-8 was replaced with an equimolar amount of compound DD-533, thus obtaining compound 533 (6.93 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 814.3779 (theoretical value: 814.3792). Theoretical elemental content (%) C 60 H 42 D5NSi: C, 88.41; H, 6.43; N, 1.72. Measured elemental content (%): C, 88.42; H, 6.45; N, 1.70.

[0279] Synthesis Example 22: Synthesis of Compound 585

[0280]

[0281] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-585, compound BB-8 was replaced with an equimolar amount of compound BB-585, compound CC-8 was replaced with an equimolar amount of compound CC-585, and compound DD-8 was replaced with an equimolar amount of compound DD-585, thus obtaining compound 421 (6.65 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 885.3440 (theoretical value: 885.3427). Theoretical elemental content (%) C 65 H 47 NOSi: C, 88.10; H, 5.35; N, 1.58. Measured elemental content (%): C, 88.16; H, 5.33; N, 1.55.

[0282] Synthesis Example 23: Synthesis of Compound 596

[0283]

[0284] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-596, compound BB-8 was replaced with an equimolar amount of compound BB-596, compound CC-8 was replaced with an equimolar amount of compound CC-596, and compound DD-8 was replaced with an equimolar amount of compound DD-533, thus obtaining compound 596 (7.19 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 898.3732 (theoretical value: 898.3743). Theoretical elemental content (%) C 66 H 50 N₂Si: C, 88.16; H, 5.60; N, 3.12. Measured elemental content (%): C, 88.15; H, 5.58; N, 3.16.

[0285] Synthesis Example 24: Synthesis of Compound 601

[0286]

[0287] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-601, compound CC-8 was replaced with an equimolar amount of compound CC-601, and compound DD-8 was replaced with an equimolar amount of compound DD-601 to obtain compound 601 (7.85 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 911.3958 (theoretical value: 911.3947). Theoretical elemental content (%) C 68 H 53 NSi: C, 89.53; H, 5.86; N, 1.54. Measured elemental content (%): C, 89.58; H, 5.84; N, 1.52.

[0288] Synthesis Example 25: Synthesis of Compound 628

[0289]

[0290] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-182, compound BB-8 was replaced with an equimolar amount of compound BB-628, compound CC-8 was replaced with an equimolar amount of compound CC-628, and compound DD-8 was replaced with an equimolar amount of compound DD-628 to obtain compound 628 (6.34 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 856.4250 (theoretical value: 856.4261). Theoretical elemental content (%) C 63 H 48 D5NSi: C, 88.27; H, 6.82; N, 1.63. Measured elemental content (%): C, 88.28; H, 6.80; N, 1.66.

[0291] Synthesis Example 26: Synthesis of Compound 630

[0292]

[0293] According to the synthesis method in Example 8, compound CC-119 was replaced with an equimolar amount of compound CC-421, and compound DD-119 was replaced with an equimolar amount of compound DD-630 to obtain compound 630 (6.69 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 891.4276 (theoretical value: 891.4260). Theoretical elemental content (%) C 66 H 57 NSi: C, 88.84; H, 6.44; N, 1.57. Measured elemental content (%): C, 88.87; H, 6.46; N, 1.55.

[0294] Synthesis Example 27: Synthesis of Compound 652

[0295]

[0296] According to the synthesis method in Example 3, compound BB-8 was replaced with an equimolar amount of compound BB-652, compound CC-8 was replaced with an equimolar amount of compound CC-652, and compound DD-8 was replaced with an equimolar amount of compound DD-652 to obtain compound 652 (6.42 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 867.3878 (theoretical value: 867.3896). Theoretical elemental content (%) C 63 H 53 NOSi: C, 87.16; H, 6.15; N, 1.61. Measured elemental content (%): C, 87.14; H, 6.17; N, 1.63.

[0297] Synthesis Example 28: Synthesis of Compound 679

[0298]

[0299] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-97, compound BB-8 was replaced with an equimolar amount of compound BB-679, compound CC-8 was replaced with an equimolar amount of compound CC-679, and compound DD-8 was replaced with an equimolar amount of compound DD-679, thus obtaining compound 679 (6.03 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 825.3781 (theoretical value: 825.3791). Theoretical elemental content (%) C 61 H 51 NSi: C, 88.68; H, 6.22; N, 1.70. Measured elemental content (%): C, 88.67; H, 6.21; N, 1.74.

[0300] Synthesis Example 29: Synthesis of Compound 684

[0301]

[0302] According to the synthesis method in Example 8, compound CC-119 was replaced with an equimolar amount of compound CC-421, and compound DD-119 was replaced with an equimolar amount of compound DD-684 to obtain compound 684 (5.83 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 809.3489 (theoretical value: 809.3478). Theoretical elemental content (%) C 60 H 47 NSi: C, 88.96; H, 5.85; N, 1.73. Measured elemental content (%): C, 88.97; H, 5.83; N, 1.71.

[0303] Synthesis Example 30: Synthesis of Compound 690

[0304]

[0305] Following the synthesis method of Example 8, compound CC-119 was replaced with an equimolar amount of compound CC-421, and compound DD-119 was replaced with an equimolar amount of compound DD-690 to obtain compound 690 (5.70 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 825.3414 (theoretical value: 825.3427). Theoretical elemental content (%) C 60 H 47NOSi: C, 87.23; H, 5.73; N, 1.70. Measured elemental content (%): C, 87.25; H, 5.74; N, 1.65.

[0306] Synthesis Example 31: Synthesis of Compound 715

[0307]

[0308] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-97, compound BB-8 was replaced with an equimolar amount of compound BB-715, compound CC-8 was replaced with an equimolar amount of compound CC-715, and compound DD-8 was replaced with an equimolar amount of compound ee-182, thus obtaining compound 715 (6.64 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 873.3778 (theoretical value: 873.3791). Theoretical elemental content (%) C 65 H 51 NSi: C, 89.30; H, 5.88; N, 1.60. Measured elemental content (%): C, 89.28; H, 5.86; N, 1.63.

[0309] Synthesis Example 32: Synthesis of Compound 725

[0310]

[0311] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-725, compound BB-8 was replaced with an equimolar amount of compound BB-725, compound CC-8 was replaced with an equimolar amount of compound CC-725, and compound DD-8 was replaced with an equimolar amount of compound ee-182, thus obtaining compound 725 (6.92 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 897.3781 (theoretical value: 897.3791). Theoretical elemental content (%) C 67 H 51 NSi: C, 89.59; H, 5.72; N, 1.56. Measured elemental content (%): C, 89.56; H, 5.75; N, 1.58.

[0312] Synthesis Example 33: Synthesis of Compound 734

[0313]

[0314] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-97, compound BB-8 was replaced with an equimolar amount of compound BB-734, compound CC-8 was replaced with an equimolar amount of compound CC-734, and compound DD-8 was replaced with an equimolar amount of compound ee-182 to obtain compound 734 (6.21 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 874.3755 (theoretical value: 874.3743). Theoretical elemental content (%) C 64 H 50 N₂Si: C, 87.83; H, 5.76; N, 3.20. Measured elemental content (%): C, 87.80; H, 5.74; N, 3.24.

[0315] Synthesis Example 34: Synthesis of Compound 783

[0316]

[0317] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-182, compound BB-8 was replaced with an equimolar amount of compound BB-783, compound CC-8 was replaced with an equimolar amount of compound CC-783, and compound DD-8 was replaced with an equimolar amount of compound DD-783, thus obtaining compound 783 (7.34 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 940.4247 (theoretical value: 940.4261). Theoretical elemental content (%) C 70 H 48 D5NSi: C, 89.32; H, 6.21; N, 1.49. Measured elemental content (%): C, 89.35; H, 6.25; N, 1.44.

[0318] Synthesis Example 35: Synthesis of Compound 800

[0319]

[0320] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-800, compound BB-8 was replaced with an equimolar amount of compound BB-715, compound CC-8 was replaced with an equimolar amount of compound CC-800, and compound DD-8 was replaced with an equimolar amount of compound DD-70 to obtain compound 800 (8.02 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 965.3529 (theoretical value: 965.3511). Theoretical elemental content (%) C 70 H 51NSSi: C, 87.01; H, 5.32; N, 1.45. Measured elemental content (%): C, 87.06; H, 5.30; N, 1.41.

[0321] Synthesis Example 36: Synthesis of Compound 813

[0322]

[0323] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-813, compound BB-8 was replaced with an equimolar amount of compound BB-715, compound CC-8 was replaced with an equimolar amount of compound CC-813, and compound DD-8 was replaced with an equimolar amount of compound DD-70 to obtain compound 813 (7.62 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 975.4269 (theoretical value: 975.4260). Theoretical elemental content (%) C 73 H 57 NSi: C, 89.80; H, 5.88; N, 1.43. Measured elemental content (%): C, 89.82; H, 5.85; N, 1.46.

[0324] Synthesis Example 37: Synthesis of Compound 826

[0325]

[0326] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-596, compound BB-8 was replaced with an equimolar amount of compound BB-826, compound CC-8 was replaced with an equimolar amount of compound CC-826, and compound DD-8 was replaced with an equimolar amount of compound ee-182, thus obtaining compound 826 (6.57 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 887.3595 (theoretical value: 887.3583). Theoretical elemental content (%) C 65 H 49 NOSi: C, 87.90; H, 5.56; N, 1.58. Measured elemental content (%): C, 87.94; H, 5.57; N, 1.55.

[0327] Synthesis Example 38: Synthesis of Compound 835

[0328]

[0329] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-725, compound BB-8 was replaced with an equimolar amount of compound BB-835, compound CC-8 was replaced with an equimolar amount of compound CC-835, and compound DD-8 was replaced with an equimolar amount of compound ee-182 to obtain compound 835 (7.23 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 963.4280 (theoretical value: 963.4260). Theoretical elemental content (%) C 72 H 57 NSi: C, 89.68; H, 5.96; N, 1.45. Measured elemental content (%): C, 89.62; H, 5.99; N, 1.44.

[0330] Synthesis Example 39: Synthesis of Compound 839

[0331]

[0332] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-596, compound BB-8 with an equimolar amount of compound BB-715, compound CC-8 with an equimolar amount of compound CC-839, and compound DD-8 with an equimolar amount of compound DD-414 to obtain compound 839 (8.02 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 921.3776 (theoretical value: 921.3791). Theoretical elemental content (%) C 69 H 51 NSi: C, 89.86; H, 5.57; N, 1.52. Measured elemental content (%): C, 89.88; H, 5.56; N, 1.55.

[0333] Synthesis Example 40: Synthesis of Compound 876

[0334]

[0335] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-596, compound BB-8 was replaced with an equimolar amount of compound BB-876, compound CC-8 was replaced with an equimolar amount of compound CC-879, and compound DD-8 was replaced with an equimolar amount of compound ee-182, thus obtaining compound 876 (6.49 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 913.4123 (theoretical value: 913.4104). Theoretical elemental content (%) C 68 H 55NSi: C, 89.33; H, 6.06; N, 1.53. Measured elemental content (%): C, 89.38; H, 6.04; N, 1.51.

[0336] Synthesis Example 41: Synthesis of Compound 885

[0337]

[0338] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-596, compound BB-8 was replaced with an equimolar amount of compound BB-885, compound CC-8 was replaced with an equimolar amount of compound CC-885, and compound DD-8 was replaced with an equimolar amount of compound DD-70, thus obtaining compound 885 (7.19 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 909.3779 (theoretical value: 909.3791). Theoretical elemental content (%) C 68 H 51 NSi: C, 89.73; H, 5.65; N, 1.54. Measured elemental content (%): C, 89.75; H, 5.68; N, 1.49.

[0339] Synthesis Example 42: Synthesis of Compound 901

[0340]

[0341] According to the synthesis method in Example 3, compound AA-8 was replaced with an equimolar amount of compound AA-901, compound BB-8 was replaced with an equimolar amount of compound BB-901, compound CC-8 was replaced with an equimolar amount of compound CC-901, and compound DD-8 was replaced with an equimolar amount of compound DD-414 to obtain compound 901 (6.38 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 873.3799 (theoretical value: 873.3791). Theoretical elemental content (%) C 65 H 51 NSi: C, 89.30; H, 5.88; N, 1.60. Measured elemental content (%): C, 89.35; H, 5.86; N, 1.61.

[0342] The following are other compounds besides the fluorene-containing aromatic amine compounds described in this invention used in the device fabrication examples:

[0343]

[0344] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 15 mA / cm². 2 The luminous efficiency and driving voltage were measured. The lifetime (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Tables 1 and 2.

[0345] Comparative device fabrication example 1: Comparative device 1

[0346] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0347] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HTL-1 and p-1 (mass ratio 100:7) as hole injection layer with a thickness of 35 nm; b) HTL-1 as hole transport layer with a thickness of 35 nm; c) GH-1, GH-2 and Ir(ppy)2(m-bppy) (mass ratio 32:64:4) as light-emitting layer with a thickness of 40 nm; d) TPBi as hole blocking layer with a thickness of 25 nm; e) NBphen and Liq (mass ratio 7:3) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 0.1 nm; g) Mg and Ag (mass ratio 9:1) as cathode with a thickness of 10 nm; h) CP-4 as capping layer with a thickness of 100 nm.

[0348] Comparative device fabrication example 2: Comparative device 2

[0349] By replacing HTL-1 in the hole injection layer and hole transport layer with HTL-2, and following the same steps as in Comparative Device Preparation Example 1, Comparative Device 2 can be obtained.

[0350] Device fabrication examples 1-40: Light-emitting devices 1-40

[0351] By replacing HTL-1 in the hole injection layer and hole transport layer with the fluorene-containing aromatic amine compounds of the present invention synthesized in Synthesis Examples 3 to 42, and with all other steps being the same as in Comparative Device Preparation Example 1, light-emitting devices 1 to 40 can be obtained.

[0352] Table 1

[0353]

[0354]

[0355] Comparative device fabrication example 3: Comparative device 3

[0356] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0357] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-1 and p-1 (mass ratio 100:5) as hole injection layer with a thickness of 20 nm; b) HT-1 as hole transport layer with a thickness of 35 nm; c) HTL-1 as light-emitting auxiliary layer with a thickness of 35 nm; d) RH-1, RH-2 and Ir(dpm)(piq)2 (mass ratio 47:47:6) as light-emitting layer with a thickness of 35 nm; e) TPBi as hole blocking layer with a thickness of 25 nm; f) NBphen and Liq (mass ratio 7:3) as electron transport layer with a thickness of 25 nm; g) LiF as electron injection layer with a thickness of 0.1 nm; h) Mg and Ag (mass ratio 7:3) as cathode with a thickness of 10 nm; i) CP-4 as capping layer with a thickness of 100 nm.

[0358] Comparative device fabrication example 4: Comparative device 4

[0359] By replacing HTL-1 in the light-emitting auxiliary layer with HTL-2, and following the same steps as in Comparative Device Preparation Example 4, Comparative Device 4 can be obtained.

[0360] Device fabrication examples 41-80: Light-emitting devices 41-80

[0361] By replacing HTL-1 in the light-emitting auxiliary layer with the fluorene-containing aromatic amine compounds of the present invention synthesized in Examples 3 to 42, and with all other steps being the same as in Comparative Device Preparation Example 3, light-emitting devices 41 to 80 can be obtained.

[0362] Table 2

[0363]

[0364]

[0365]

[0366] The device data in Tables 1 and 2 show that the fluorene-containing aromatic amine compounds described in this invention, when used as hole transport materials in OLED devices, significantly improve luminous efficiency, lifespan, and driving voltage. In summary, the fluorene-containing aromatic amine compounds provided by this invention are a class of high-performance OLED materials with excellent application prospects.

[0367] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A fluorene-containing aromatic amine compound, characterized in that, It has the structure shown in equation (I): Ar1 is selected from one of the following structures: Wherein, each time a1 appears, it is selected from 1, 2, 3 or 4, either the same or different; each time b1 appears, it is selected from 1, 2 or 3, either the same or different; each time c1 appears, it is selected from 1 or 2, either the same or different; each time d1 appears, it is selected from 1. The R mentioned 11 R 21 It is independently selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, naphthyl, anthracene, phenanthryl, biphenyl, and pyridyl; The R mentioned 31 It is selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, trifluoromethyl-substituted phenyl, trimethylsilyl-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, and pyridyl. The R mentioned 41 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, trifluoromethyl-substituted phenyl, trimethylsilyl-substituted phenyl, pyridyl, and pyrimidinyl. The R mentioned 41a Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, trifluoromethyl-substituted phenyl, trimethylsilyl-substituted phenyl, pyridyl, pyrimidinyl, and group of formula (II); The Ar2 is selected from substituted or unsubstituted pyridinyl groups or one of the following structures: Wherein, the a 201 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the b mentioned above. 201 Each time it appears, it is selected from 1, 2, 3, or 4, either identically or differently; the c mentioned 201 Each time it appears, it is selected from 1, 2, or 3, either identically or differently; the d mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, or 6, either identically or differently; the e mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 201 Each time it appears, it is selected from 1 or 2, either identically or differently; the g mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the h mentioned 201 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, either the same or different. The R mentioned 201 Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; tert-butyl; deuterated tert-butyl; adamantyl; norbornel; a phenyl group substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornel; or one of the groups of formula (II). The R mentioned 202 Selected from phenyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, and naphthyl; naphthyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, and naphthyl; biphenyl groups substituted or unsubstituted with one or more of the following: deuterium atom, fluorine atom, cyano, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl; and one of the groups in formula (II). The R mentioned 203 Each time it appears, it is selected from one of the following groups: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group, and tert-butyl group, either the same or different. The Ar3 is selected from one of the following structures: Wherein, the a 301 Each time it appears, it is selected from 1, 2, 3, 4, or 5, either identically or differently; the b mentioned above. 301 Each time it appears, it is selected from 1, 2, 3, or 4, either identically or differently; the c mentioned 301 Each time it appears, it is selected from 1, 2, or 3, either identically or differently; the d mentioned 301 Each time it appears, it is selected from 1, 2, 3, 4, 5, or 6, either identically or differently; the e mentioned 301 Each time it appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 301 Each time it appears, it is either selected from 1 or 2, either the same or different. The R mentioned 301 Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; tert-butyl; deuterated tert-butyl; adamantyl; norbornel; a phenyl group substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornel; or one of the groups shown in formula (II). The R mentioned 302 Each time it appears, it is selected from one of the following groups: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group, and tert-butyl group, either the same or different. The L1 to L3 are independently selected from a single bond or one of the following structures: Wherein, the a 401 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 401 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 401 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 401 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 401 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different. The R mentioned 401 Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; cyano group; methyl group; deuterated methyl group; trifluoromethyl group; isopropyl group; deuterated isopropyl group; tert-butyl group; deuterated tert-butyl group. The R mentioned 402 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, and deuterated tert-butyl group. The condition is that at least one of Ar1, Ar2, and Ar3 contains at least one group of formula (II) as follows: The Ar mentioned therein 101 Ar is selected from one of single-bonded, substituted or unsubstituted phenylene groups. 102 ~Ar 104 It is independently selected from one of substituted or unsubstituted C1-C6 alkyl groups and substituted or unsubstituted C6-C14 aryl groups; In Ar2, "substituted or unsubstituted pyridyl" refers to "substituted or unsubstituted" and Ar 101 ~Ar 104 The term "substituted or unsubstituted" as used herein refers to something that is not substituted or is substituted by one or more substituents selected from the group consisting of: deuterium atom, halogen atom, cyano group, and C1-C12 alkyl group.

2. The fluorene-containing aromatic amine compound according to claim 1, characterized in that, The Ar1 mentioned is selected from one of the following structures: 。 3. The fluorene-containing aromatic amine compound according to claim 1, characterized in that, The Ar2 is selected from one of the following structures: 。 4. The fluorene-containing aromatic amine compound according to claim 1, characterized in that, The Ar3 is selected from one of the following structures: 。 5. The fluorene-containing aromatic amine compound according to claim 1, characterized in that, The L1 to L3 are independently selected from a single bond or one of the following structures: 。 6. A fluorene-containing aromatic amine compound, characterized in that, The fluorene-containing aromatic amine compound is selected from one of the following compounds: 。 7. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode facing away from the anode, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The hole transport region contains one or more of the fluorene-containing aromatic amine compounds as described in any one of claims 1 to 6.

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