An arylamine compound and an organic electroluminescence device thereof

Abstract

This invention relates to the field of organic optoelectronic materials technology, specifically to an aromatic amine compound and its organic electroluminescent device. The aromatic amine compound provided by this invention possesses appropriate hole mobility, HOMO, and T1 values. When applied as a hole transport material in OLED devices, it can improve the charge transport efficiency of the device, effectively reduce the driving voltage, and increase luminous efficiency. As an organic functional layer in the hole transport region, it can achieve 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 layer, preventing interface luminescence and avoiding device aging caused by heat generated by interface luminescence. This improves the driving voltage, luminous efficiency, and lifespan. Furthermore, it exhibits excellent thermal and chemical stability, allowing it to be used under extreme temperature conditions and in environments containing water, oxygen, and other corrosive gases, further extending the device's lifespan.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, specifically to an 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. To improve the device's performance in terms of driving voltage, luminous efficiency, color purity, clarity, and lifespan, a hole transport region is typically placed between the anode and the emissive layer, and an electron transport region is placed between the cathode and the emissive layer. The hole transport region primarily functions to inject and transport holes, and can include one or more layers such as a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, and an electron blocking layer. The electron transport region primarily functions to inject and transport electrons, and can also include one or more layers such as an electron injection layer, an electron transport layer, and a hole blocking layer. Furthermore, good energy level matching is required between the organic layers in both charge transport regions and with other functional organic layers (e.g., the light-emitting layer). This prevents excitons from diffusing to the edge of the light-emitting layer, maintaining a high ratio of effective light emission within the light-emitting layer. This not only improves the device's luminous efficiency but also reduces the heat generated by interfacial luminescence, preventing rapid aging of the organic materials and extending the device's lifespan. In addition to placing an organic functional layer between the anode and cathode, a capping layer with high refractive index and high transmittance is also placed on the outer side of the light-emitting electrode (e.g., the outer side of the cathode in a top-emitting device) to further improve the device's luminous efficiency and color purity.

[0004] Currently, hole transport materials that have good energy level matching and appropriate charge transport efficiency with the light-emitting layer materials (guest materials and host materials) used in industry are still very limited and urgently need to be developed by OLED researchers. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides an aromatic amine compound possessing appropriate hole mobility, appropriate highest occupied molecular orbital (HOMO) and triplet energy level (T1) values, as well as excellent thermal and chemical stability. When used as a hole transport material in OLED devices, it can improve the driving voltage, luminous efficiency, and lifespan of OLED devices. It has the structure shown in formula (I):

[0006]

[0007] Wherein, Ar1 is selected from the structure shown in formula (IA), in which X1 to X8 are independently selected from CR4 or nitrogen atoms, and when other groups are attached, they are selected from carbon atoms; R1 to R3 are independently selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted C1 to C12 alkyl group, substituted or unsubstituted C3 to C10 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3 to C7 aliphatic ring and a C6 to C30 aromatic ring, and at least one of R1 to R3 is selected from a substituted or unsubstituted C1 to C12 alkyl group or a substituted or unsubstituted C3 to C10 cycloalkyl group. The L4 is selected from one of the following: a monovalent group formed by the fusion of a C6-C30 aryl group (substituted or unsubstituted), a C2-C30 heteroaryl group (substituted or unsubstituted), and a C6-C30 aromatic ring (substituted or unsubstituted); the L5 is selected from one of the following: a monovalent group formed by the fusion of a C6-C30 aromatic ring (substituted or unsubstituted), a C2-C30 heteroaryl group (substituted or unsubstituted), and a C6-C30 aromatic ring (substituted or unsubstituted);

[0008] Ar2 and Ar3 are independently selected from one of the structures shown in formulas (IB) to (IM):

[0009]

[0010] Wherein, each occurrence of 'a' is selected from 0, 1, 2, 3, 4, or 5; each occurrence of 'b' is selected from 0, 1, 2, 3, or 4; each occurrence of 'c' is selected from 0, 1, 2, or 3; each occurrence of 'd' is selected from 0, 1, or 2; each occurrence of 'e' is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of 'f' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of 'g' is selected from 0 or 1; each occurrence of 'Y1' is selected from oxygen or sulfur atoms; and each occurrence of 'Y2' is selected from oxygen, sulfur, or NR atoms. 10 CR 11 R 12 One of them, the R 10 Each time it appears, it is selected, either identically or differently, from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C7 aliphatic ring fused with a C6-C30 aromatic ring, forming a monovalent group; wherein the R... 11 R 12Each time R5, R6, and R7 appear, they are selected, either identically or differently, from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; R5 and R6 can be linked to form... The C5-C10 carbon ring is substituted or unsubstituted; each time L6 appears, it is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C7 aliphatic ring fused with a C6-C30 aromatic ring; each time Z1-Z8 appears, it is selected from one of the following: a CR4 group or a nitrogen atom, and when other groups are attached, it is selected from one of the following: a carbon atom; each time R8 appears, it is selected from one of the following: a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 arylene ring, a substituted or unsubstituted C6 ... The R8 is selected from one of the following: a C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C8-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; and in formulas (IB) to (IM), at most one R8 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C8-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; and each time the R9 appears, it is the same or different. It is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group; each time R8' appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C8-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring;

[0011] Each time R4 appears, it is selected from the same or different groups of a single bond, hydrogen atom, deuterium atom, halogen atom, cyano, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 heteroaryl, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring. In formula (IA), two adjacent R4s cannot be linked to form a ring, while in formulas (IB) to (IM), two adjacent R4s can be linked to form one of the following: a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyridine ring, or a pyrimidine 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 C8 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 substituents in "substituted or unsubstituted" are independently selected from one of the following: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group, C8-C20 heteroaryl group, and monovalent group formed by fusion of aliphatic ring of C3-C7 and aromatic ring of C6-C20.

[0014] 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 opposite to the anode, and the organic layer contains one or more of the aromatic amine compounds described in the present invention.

[0015] Beneficial effects:

[0016] The aromatic amine compounds provided by this invention possess appropriate hole mobility, HOMO, and T1 values. When applied as hole transport materials in OLED devices, they can improve the charge transport efficiency of the devices, effectively reduce the driving voltage, and increase luminous efficiency. As organic functional layers in the hole transport region, they can achieve good energy level matching with other adjacent organic functional layers. When adjacent to the light-emitting layer, they 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. This improves the driving voltage, luminous efficiency, and lifespan. Furthermore, they have excellent thermal and chemical stability, allowing them to be used under extreme temperature conditions and in environments containing water, oxygen, and other corrosive gases, further enhancing the lifespan of the devices. Detailed Implementation

[0017] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. 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.

[0018] 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.

[0019] 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".

[0020] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0021] In this invention, "silyl group" refers to a -SiH3 group, and "substituted or unsubstituted silyl group" means that one or more H atoms on the silyl group are substituted or unsubstituted.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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 group includes furanyl, thiophene, pyrrole, imidazolyl, etc., but is not limited thereto; the polycyclic heteroaryl group includes phenylfuranyl, phenylthiophene, etc., but is not limited thereto; the fused-ring heteroaryl group includes benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiaphene, carbazole, benzocarbazole, acridinel, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but is not limited thereto. The aforementioned heteroaryl groups are preferably thienyl, furanyl, benzothienyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0027] 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.

[0028] 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 the arylene is a divalent group.

[0029] 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.

[0030] 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.

[0031] 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.

[0032] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by 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, substituted or unsubstituted silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3- C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, substituted or unsubstituted silyl, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, 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 cyclopropane Butyl, ethyl-substituted cyclobutyl, deuterated cyclobutyl, 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, tetrahydropyrrole The following groups are used: yl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-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, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophene, trimethylsilyl, triphenylsilyl, where, when substituted by multiple substituents, the multiple substituents may be the same or different from each other.

[0033] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0034] 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 Can represent And so on.

[0035] 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:

[0036]

[0037] 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.

[0038] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0039] This invention provides an aromatic amine compound having the structure shown in formula (I):

[0040]

[0041] Wherein, Ar1 is selected from the structure shown in formula (IA), in which X1 to X8 are independently selected from CR4 or nitrogen atoms, and when other groups are attached, they are selected from carbon atoms; R1 to R3 are independently selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted C1 to C12 alkyl group, substituted or unsubstituted C3 to C10 cycloalkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3 to C7 aliphatic ring and a C6 to C30 aromatic ring, and at least one of R1 to R3 is selected from a substituted or unsubstituted C1 to C12 alkyl group or a substituted or unsubstituted C3 to C10 cycloalkyl group. The L4 is selected from one of the following: a monovalent group formed by the fusion of a C6-C30 aryl group (substituted or unsubstituted), a C2-C30 heteroaryl group (substituted or unsubstituted), and a C6-C30 aromatic ring (substituted or unsubstituted); the L5 is selected from one of the following: a monovalent group formed by the fusion of a C6-C30 aromatic ring (substituted or unsubstituted), a C2-C30 heteroaryl group (substituted or unsubstituted), and a C6-C30 aromatic ring (substituted or unsubstituted);

[0042] Ar2 and Ar3 are independently selected from one of the structures shown in formulas (IB) to (IM):

[0043]

[0044] Wherein, each occurrence of 'a' is selected from 0, 1, 2, 3, 4, or 5; each occurrence of 'b' is selected from 0, 1, 2, 3, or 4; each occurrence of 'c' is selected from 0, 1, 2, or 3; each occurrence of 'd' is selected from 0, 1, or 2; each occurrence of 'e' is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of 'f' is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of 'g' is selected from 0 or 1; each occurrence of 'Y1' is selected from oxygen or sulfur atoms; and each occurrence of 'Y2' is selected from oxygen, sulfur, or NR atoms. 10 CR 11 R 12 One of them, the R 10Each time it appears, it is selected, either identically or differently, from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C7 aliphatic ring fused with a C6-C30 aromatic ring, forming a monovalent group; wherein the R... 11 R 12 Each time R5, R6, and R7 appear, they are selected, either identically or differently, from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; R5 and R6 can be linked to form... The C5-C10 carbon ring is substituted or unsubstituted; each time L6 appears, it is selected from one of the following: a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C7 aliphatic ring fused with a C6-C30 aromatic ring; each time Z1-Z8 appears, it is selected from one of the following: a CR4 group or a nitrogen atom, and when other groups are attached, it is selected from one of the following: a carbon atom; each time R8 appears, it is selected from one of the following: a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 arylene ring, a substituted or unsubstituted C6 ... The R8 is selected from one of the following: a C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C8-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; and in formulas (IB) to (IM), at most one R8 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C8-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring; and each time the R9 appears, it is the same or different. It is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group; each time R8' appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C8-C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring;

[0045] Each time R4 appears, it is selected from the same or different groups of a single bond, hydrogen atom, deuterium atom, halogen atom, cyano, nitro, amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 heteroaryl, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C7 aliphatic ring and a C6-C30 aromatic ring. In formula (IA), two adjacent R4s cannot be linked to form a ring, while in formulas (IB) to (IM), two adjacent R4s can be linked to form one of the following: a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted pyridine ring, or a pyrimidine ring.

[0046] The L1 to L3 are independently selected from one of the following: single bond, substituted or unsubstituted C6 to C30 arylene, substituted or unsubstituted C8 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.

[0047] The substituents in "substituted or unsubstituted" are independently selected from one of the following: deuterium atom, halogen atom, cyano group, C1-C4 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group, C8-C20 heteroaryl group, and monovalent group formed by fusion of aliphatic ring of C3-C7 and aromatic ring of C6-C20.

[0048] Preferably, the substituents in "substituted or unsubstituted" are selected from deuterium; fluorine; cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; adamantyl; norbornel; phenyl; naphthyl; anthracene; phenanthrene; triphenylene; 9,9-dimethylfluorenyl; 9,9-diphenylfluorenyl; spirodifluorenyl; dibenzofuranyl; dibenzothiophene; N-phenylcarbazoyl; indanyl; tetrahydronaphthyl; methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, methyl The silylation group is one or more substituted or unsubstituted methyl alkyl groups from the group consisting of alkyl-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, and dibenzothiopheneyl. The silylation group is one or more, and when there are multiple substituted groups, the multiple substituted groups are the same or different. When there are multiple substituted groups, two adjacent substituted groups can be linked to form a substituted or unsubstituted saturated or unsaturated C3 to C6 carbon ring.

[0049] Preferably, the Ar1 is selected from one of the following structures:

[0050]

[0051] Wherein, each time a1 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time b1 appears, it is selected from 0, 1, 2 or 3, either the same or different; each time c1 appears, it is selected from 0, 1 or 2, either the same or different.

[0052] R1 to R3 are independently selected from one of the following: hydrogen atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoleyl. Furthermore, at least one of R1 to R3 is selected from one of the following: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoyl.

[0053] 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 group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted indanyl group, and substituted or unsubstituted tetrahydronaphthyl group.

[0054] The L4 is selected from one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted spirodifluorene, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted indenylene, and substituted or unsubstituted tetrahydronaphthylene.

[0055] The L5 is selected from one of the following: substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, substituted or unsubstituted fluorene, substituted or unsubstituted spirodifluorene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiopheneylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted indenylene, and substituted or unsubstituted tetrahydronaphthylene.

[0056] Preferably, the Ar1 is selected from one of the following structures:

[0057]

[0058]

[0059] Each time a2 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time b2 appears, it is selected from 0, 1, 2 or 3, either the same or different; each time c2 appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different; each time d2 appears, it is selected from 0, 1 or 2, either the same or different.

[0060] R1 to R3 are independently selected from one of the following: hydrogen atom, methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, biphenyl, naphthyl-substituted phenyl, naphthyl, anthracene, phenanthrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, and N-phenylcarbazoyl. Furthermore, at least one of R1 to R3 is selected from methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, biphenyl, naphthyl-substituted phenyl, naphthyl, anthracene, phenanthrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiopheneyl, and N-phenylcarbazoyl.

[0061] The R mentioned 41Each 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, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl, indanyl, and tetrahydronaphthyl.

[0062] The R mentioned 101 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, isopropyl group, tert-butyl group, adamantyl group, norbornel group, phenyl group, deuterated phenyl group, etc. One of them.

[0063] Preferably, the Ar1 is selected from one of the following structures:

[0064]

[0065]

[0066] Wherein, R1 to R3 are as described in this invention.

[0067] Preferably, the aforementioned Choose one of the following structures:

[0068]

[0069] Preferably, the Ar2 and Ar3 are independently selected from one of the following structures:

[0070]

[0071]

[0072] Wherein, each occurrence of a3 is selected from 0, 1, 2, 3, 4, or 5; each occurrence of b3 is selected from 0, 1, 2, 3, or 4; each occurrence of c3 is selected from 0, 1, 2, or 3; each occurrence of d3 is selected from 0, 1, or 2; each occurrence of e3 is selected from 0, 1, 2, 3, 4, 5, or 6; each occurrence of f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; each occurrence of g3 is selected from 0 or 1; each occurrence of h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and each occurrence of i3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0073] The R mentioned 81Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, and at most one R group. 81 Selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted indenyl, or substituted or unsubstituted tetrahydronaphthyl;

[0074] The R mentioned 91 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, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, or substituted or unsubstituted norbornel group.

[0075] The R mentioned 81 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group.

[0076] Preferably, the R 81 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; 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, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornyl, and at most one R 81Selected from deuterated tert-butyl; adamantyl; norbornel; a phenyl group substituted or unsubstituted with one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornel; or a naphthyl group substituted or unsubstituted with one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, and norbornel.

[0077] Preferably, the R 91 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.

[0078] Preferably, the R 81 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; 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, 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, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl.

[0079] Preferably, the Ar2 and Ar3 are independently selected from one of the following structures:

[0080]

[0081]

[0082] Preferably, L1 to L3 are independently selected from a single bond or one of the following structures:

[0083]

[0084] Wherein, each occurrence of a4 is selected from 0, 1, 2, 3, or 4, either the same or different; each occurrence of b4 is selected from 0, 1, 2, or 3, either the same or different; each occurrence of c4 is selected from 0, 1, or 2, either the same or different; each occurrence of d4 is selected from 0, 1, 2, 3, 4, 5, or 6, either the same or different; and each occurrence of e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different.

[0085] The R mentioned 201Each 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, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, substituted or unsubstituted phenyl group, and substituted or unsubstituted naphthyl group.

[0086] The R mentioned 202 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, or substituted or unsubstituted tert-butyl group.

[0087] Preferably, the R 201 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, tert-butyl group, adamantyl group, norbornel group, phenyl group, and deuterated phenyl group.

[0088] Preferably, the R 202 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, and tert-butyl group.

[0089] Preferably, L1 to L3 are independently selected from a single bond or one of the following structures:

[0090]

[0091]

[0092] Preferably, the aromatic amine compound is selected from one of the following compounds:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] The above only lists some specific structural forms of the aromatic amine compounds described in this invention, but 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.

[0106] The aromatic amine compounds of the present invention can be prepared by one of the following synthetic routes:

[0107] Synthesis Route 1:

[0108]

[0109] Synthesis Route 2:

[0110]

[0111] Synthesis Route 3:

[0112]

[0113] In each of the above synthetic routes, X 11 X 12 Each time it appears, it is selected from chlorine, bromine, or iodine atoms, either the same or different;

[0114] Ar1 to Ar3 and L1 to L3 are as described in this invention.

[0115] In the above synthetic routes, the aromatic amine compound described in this invention can be obtained by reacting compound (Y1) with halides (Y2) and (Y3) via a CN coupling reaction. 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.

[0116] 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.

[0117] 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 opposite to the anode, and the organic layer contains one or more of the aromatic amine compounds described in the present invention.

[0118] 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 aromatic amine compounds described in this invention.

[0119] 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 aromatic amine compounds described in this invention.

[0120] 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.

[0121] 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. Triaromatic amine 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-hexaazabenzenephenanthrene (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 aromatic amine compounds described in this invention, but are not limited thereto.

[0122]

[0123]

[0124] 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 2Substances 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 aromatic amine compounds described in this invention, but not limited thereto.

[0125] 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 [1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-bis([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 aromatic amine compounds described in this invention, but not limited thereto.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134]

[0135] 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 aromatic amine compounds described in this invention.

[0136] 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 aromatic amine compounds described in this invention.

[0137] 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 aromatic amine compounds described in this invention.

[0138] 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 aromatic amine compounds described in this invention.

[0139] 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 aromatic amine compounds described in this invention.

[0140] 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 aromatic amine compounds described in this invention.

[0141] 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 aromatic amine compounds described in this invention.

[0142] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc. There are no special limitations on the thickness of each layer, as long as good device performance is obtained.

[0143] The organic layers mentioned above are preferably prepared using vacuum evaporation, inkjet printing, or spin coating methods.

[0144] 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.

[0145] 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.

[0146] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0147] 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.

[0148] 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.

[0149] Synthesis Example 1: Synthesis of compound DD via CN coupling reaction

[0150] Synthesis of compound DD-27:

[0151]

[0152] Under nitrogen protection, aa-27 (12.10 g, 60.00 mmol), bb-27 (13.75 g, 60.00 mmol), and sodium tert-butoxide (11.53 g, 120.00 mmol) were added to 240 mL of toluene. Pd(dppf)Cl2 (0.44 g, 0.60 mmol) was added with stirring, and the mixture was heated under reflux for 4 h. After the reaction was complete, the reaction solution was cooled to room temperature, washed with distilled water, extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The residue was recrystallized from toluene / methanol (11:3) to give compound DD-27 (16.38 g, 78%). HPLC analysis showed a solid purity ≥99.79%. Mass spectrometry m / z: 349.1069 (theoretical value: 349.1054).

[0153] By substituting the raw materials accordingly and following the synthesis method of compound DD-27, other compounds DD can be obtained, as shown in the table below:

[0154]

[0155]

[0156] Synthesis Example 2: Synthesis of compound DD via C-C coupling reaction

[0157] Synthesis of compound DD-121:

[0158]

[0159] Under nitrogen protection, cc-121 (9.38 g, 60.00 mmol), DD-1 (23.66 g, 60.00 mmol), K2CO3 (16.58 g, 120.00 mmol), Pd(PPh3)4 (0.69 g, 0.60 mmol), 120 mL of ethanol, and 120 mL of water were added to 360 mL of toluene. The mixture was stirred and refluxed for 5.5 h. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The residue was recrystallized from toluene / methanol (8:1 v / v) to give compound DD-121 (17.89 g, 70% yield). HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 425.1379 (theoretical value: 425.1367).

[0160] By substituting the raw materials accordingly and following the synthesis method of compound DD-121, other compounds DD can be obtained, as shown in the table below:

[0161]

[0162] Synthesis Example 3: Synthesis of Compound 1

[0163]

[0164] Under nitrogen protection, CC-1 (8.04 g, 25.00 mmol), DD-1 (9.86 g, 25.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), P(t-Bu)3 (1.20 mL of 0.5 M toluene solution, 0.60 mmol), and sodium tert-butoxide (4.81 g, 50.00 mmol) were added to 140 mL of toluene. The mixture was stirred and refluxed for 7 h. After the reaction was complete, the mixture was cooled to room temperature, washed with distilled water, extracted with dichloromethane, allowed to stand, separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The residue was recrystallized from toluene to give compound 1 (12.54 g, 79%), with a solid purity of ≥99.94% as determined by HPLC. Mass spectrometry m / z: 634.2815 (theoretical value: 634.2804). Theoretical element content (%) C 45 H 38 N₂Si: C, 85.13; H, 6.03; N, 4.41. Measured elemental content (%): C, 85.18; H, 5.99; N, 4.45.

[0165] Synthesis Example 4: Synthesis of Compound 27

[0166]

[0167] Synthesis of compound CC-27:

[0168] Under nitrogen protection, AA-27 (5.73 g, 40.00 mmol), BB-27 (20.30 g, 40.00 mmol), sodium tert-butoxide (7.69 g, 80.00 mmol), and 215 mL of toluene were added to a reaction flask. Pd(OAc)₂ (0.09 g, 0.40 mmol) and P(t-Bu)₃ (1.60 mL of 0.5 M toluene solution, 0.80 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 6 h. After the reaction was complete, the mixture was cooled to room temperature, washed with distilled water, extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The residue was recrystallized from toluene / methanol (7:1 v / v) to give compound CC-27 (17.32 g, 76%). HPLC analysis showed a solid purity ≥ 99.89%. Mass spectrometry m / z: 569.3070 (theoretical value: 569.3083).

[0169] Synthesis of compound 27:

[0170] Under nitrogen protection, CC-27 (14.24 g, 25.00 mmol), DD-27 (8.75 g, 25.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), P(t-Bu)3 (1.20 mL of 0.5 M toluene solution, 0.60 mmol), and sodium tert-butoxide (4.81 g, 50.00 mmol) were added to 140 mL of toluene. The mixture was stirred and refluxed for 7.5 h. After the reaction was complete, the mixture was cooled to room temperature, washed with distilled water, extracted with dichloromethane, allowed to stand, and separated. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The residue was recrystallized from toluene to give compound 27 (16.12 g, 73%), with a solid purity of ≥99.96% as determined by HPLC. Mass spectrometry m / z: 882.4355 (theoretical value: 882.4369). Theoretical elemental content (%) C 64 H 58 N₂Si: C, 87.03; H, 6.62; N, 3.17. Measured elemental content (%): C, 86.98; H, 6.59; N, 3.21.

[0171] Synthesis Example 5: Synthesis of Compound 34

[0172]

[0173] Following the same preparation method as compound 27 in Example 4, AA-27 was replaced with an equimolar amount of AA-34, BB-27 with an equimolar amount of BB-34, and DD-27 with an equimolar amount of DD-1, yielding compound 34 (13.52 g, yield 72%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 750.3054 (theoretical value: 750.3066). Theoretical elemental content (%) C 53 H 42 N₂OSi: C, 84.76; H, 5.64; N, 3.73. Measured elemental content (%): C, 84.81; H, 5.59; N, 3.76.

[0174] Synthesis Example 6: Synthesis of Compound 51

[0175]

[0176] Following the same preparation method as compound 27 in Example 4, AA-27 was replaced with an equimolar amount of AA-51, BB-27 with an equimolar amount of BB-51, and DD-27 with an equimolar amount of DD-51, yielding compound 51 (13.52 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 730.2485 (theoretical value: 730.2474). Theoretical elemental content (%) C 49 H 38 N2OSSi: C, 80.51; H, 5.24; N, 3.83. Measured elemental content (%): C, 80.46; H, 5.28; N, 3.79.

[0177] Synthesis Example 7: Synthesis of Compound 59

[0178]

[0179] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-59 to obtain compound 59 (13.69 g, yield 77%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 710.3104 (theoretical value: 710.3117). Theoretical elemental content (%) C 51 H 42 N₂Si: C, 86.16; H, 5.95; N, 3.94. Measured elemental content (%): C, 86.21; H, 5.99; N, 3.91.

[0180] Synthesis Example 8: Synthesis of Compound 60

[0181]

[0182] Following the same preparation method as compound 27 in Synthesis Example 4, AA-27 was replaced with an equimolar amount of AA-34, BB-27 with an equimolar amount of BB-60, and DD-27 with an equimolar amount of DD-60, yielding compound 60 (13.93 g, yield 75%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 742.3754 (theoretical value: 742.3743). Theoretical elemental content (%) C 53 H 50 N₂Si: C, 85.67; H, 6.78; N, 3.77. Measured elemental content (%): C, 85.72; H, 6.81; N, 3.80.

[0183] Synthesis Example 9: Synthesis of Compound 67

[0184]

[0185] Following the same preparation method as compound 27 in Synthesis Example 4, AA-27 was replaced with an equimolar amount of AA-34, BB-27 with an equimolar amount of BB-67, and DD-27 with an equimolar amount of DD-67, yielding compound 67 (14.40 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 777.4479 (theoretical value: 777.4465). Theoretical elemental content (%) C 55 H 43 D9N2Si: C, 84.89; H, 7.90; N, 3.60. Measured elemental content (%): C, 84.94; H, 7.86; N, 3.63.

[0186] Synthesis Example 10: Synthesis of Compound 68

[0187]

[0188] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-68, and DD-1 was replaced with an equimolar amount of DD-68, yielding compound 68 (14.44 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 790.2852 (theoretical value: 790.2838). Theoretical elemental content (%) C 55 H 42 N₂SSi: C, 83.50; H, 5.35; N, 3.54. Measured elemental content (%): C, 83.45; H, 5.39; N, 3.50.

[0189] Synthesis Example 11: Synthesis of Compound 103

[0190]

[0191] Following the same preparation method as compound 27 in Synthesis Example 4, AA-27 was replaced with an equimolar amount of AA-103, BB-27 with an equimolar amount of BB-103, and DD-27 with an equimolar amount of DD-103, yielding compound 103 (13.22 g, yield 71%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 744.3349 (theoretical value: 744.3336). Theoretical elemental content (%) C 52 H 45 FN2Si: C, 83.83; H, 6.09; N, 3.76. Measured elemental content (%): C, 83.80; H, 6.11; N, 3.79.

[0192] Synthesis Example 12: Synthesis of Compound 113

[0193]

[0194] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-113 to obtain compound 113 (13.79 g, yield 78%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 706.3189 (theoretical value: 706.3200). Theoretical elemental content (%) C 48 H 46 N2Si2: C, 81.54; H, 6.56; N, 3.96. Measured elemental content (%): C, 81.49; H, 6.60; N, 3.93.

[0195] Synthesis Example 13: Synthesis of Compound 115

[0196]

[0197] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-115, and DD-1 was replaced with an equimolar amount of DD-113, yielding compound 115 (15.68 g, yield 72%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 870.3812 (theoretical value: 870.3826). Theoretical elemental content (%) C 61 H 54 N₂Si₂: C, 84.09; H, 6.25; N, 3.22. Measured elemental content (%): C, 84.14; H, 6.21; N, 3.26.

[0198] Synthesis Example 14: Synthesis of Compound 121

[0199]

[0200] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-121 to obtain compound 121 (13.51 g, yield 76%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 710.3131 (theoretical value: 710.3117). Theoretical elemental content (%) C 51 H 42 N₂Si: C, 86.16; H, 5.95; N, 3.94. Measured elemental content (%): C, 86.21; H, 5.99; N, 3.91.

[0201] Synthesis Example 15: Synthesis of Compound 141

[0202]

[0203] Following the same preparation method as Compound 1 in Synthesis Example 3, CC-1 was replaced with an equimolar amount of CC-141, and DD-1 was replaced with an equimolar amount of DD-121, yielding Compound 141 (15.32 g, yield 70%). HPLC analysis showed a solid purity ≥ 99.93%. 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, 87.78; H, 5.81; N, 3.17.

[0204] Synthesis Example 16: Synthesis of Compound 167

[0205]

[0206] Following the same preparation method as Compound 1 in Synthesis Example 3, CC-1 was replaced with an equimolar amount of CC-167, and DD-1 was replaced with an equimolar amount of DD-167, yielding Compound 167 (14.63 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 790.3004 (theoretical value: 790.3016). Theoretical elemental content (%) C 55 H 42 N2O2Si: C, 83.51; H, 5.35; N, 3.54. Measured elemental content (%): C, 83.46; H, 5.39; N, 3.57.

[0207] Synthesis Example 17: Synthesis of Compound 176

[0208]

[0209] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-176, and DD-1 was replaced with an equimolar amount of DD-176, yielding compound 176 (14.68 g, yield 75%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 782.3527 (theoretical value: 782.3513). Theoretical elemental content (%) C 54 H 50 N₂Si₂: C, 82.82; H, 6.44; N, 3.58. Measured elemental content (%): C, 82.77; H, 6.39; N, 3.62.

[0210] Synthesis Example 18: Synthesis of Compound 185

[0211]

[0212] Following the same preparation method as Compound 1 in Synthesis Example 3, CC-1 was replaced with an equimolar amount of CC-176, and DD-1 was replaced with an equimolar amount of DD-185, yielding Compound 185 (14.65 g, yield 77%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 760.3285 (theoretical value: 760.3274). Theoretical elemental content (%) C 55 H 44 N₂Si: C, 86.80; H, 5.83; N, 3.68. Measured elemental content (%): C, 86.75; H, 5.79; N, 3.71.

[0213] Synthesis Example 19: Synthesis of Compound 205

[0214]

[0215] Following the same preparation method as compound 27 in Example 4, AA-27 was replaced with an equimolar amount of AA-34, BB-27 with an equimolar amount of BB-205, and DD-27 with an equimolar amount of DD-205, yielding compound 205 (15.17 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 830.3643 (theoretical value: 830.3630). Theoretical elemental content (%) C 59 H 42 D4N2OSi: C, 85.26; H, 6.06; N, 3.37. Measured elemental content (%): C, 85.31; H, 6.10; N, 3.40.

[0216] Synthesis Example 20: Synthesis of Compound 218

[0217]

[0218] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-218 to obtain compound 218 (14.57 g, yield 71%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 820.3261 (theoretical value: 820.3274). Theoretical elemental content (%) C 60 H 44 N₂Si: C, 87.77; H, 5.40; N, 3.41. Measured elemental content (%): C, 87.82; H, 5.36; N, 3.38.

[0219] Synthesis Example 21: Synthesis of Compound 223

[0220]

[0221] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-223, and DD-1 was replaced with an equimolar amount of DD-223 to obtain compound 223 (14.84 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 801.3571 (theoretical value: 801.3557). Theoretical elemental content (%) C 58 H 35 D7N2Si: C, 86.85; H, 6.16; N, 3.49. Measured elemental content (%): C, 86.90; H, 6.20; N, 3.52.

[0222] Synthesis Example 22: Synthesis of Compound 227

[0223]

[0224] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-227, and DD-1 was replaced with an equimolar amount of DD-227 to obtain compound 227 (15.77 g, yield 70%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 900.2981 (theoretical value: 900.2994). Theoretical elemental content (%) C 64 H 44 N₂SSi: C, 85.30; H, 4.92; N, 3.11. Measured elemental content (%): C, 85.25; H, 4.88; N, 3.07.

[0225] Synthesis Example 23: Synthesis of Compound 229

[0226]

[0227] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-229, and DD-1 was replaced with an equimolar amount of DD-218, yielding compound 229 (15.50 g, yield 72%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 860.3600 (theoretical value: 860.3587). Theoretical elemental content (%) C 63 H 48 N₂Si: C, 87.87; H, 5.62; N, 3.25. Measured elemental content (%): C, 87.92; H, 5.58; N, 3.29.

[0228] Synthesis Example 24: Synthesis of Compound 231

[0229]

[0230] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-231, and DD-1 was replaced with an equimolar amount of DD-218, yielding compound 231 (15.65 g, yield 69%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 906.3417 (theoretical value: 906.3430). Theoretical elemental content (%) C 67 H 46 N₂Si: C, 88.71; H, 5.11; N, 3.09. Measured elemental content (%): C, 88.66; H, 5.07; N, 3.12.

[0231] Synthesis Example 25: Synthesis of Compound 233

[0232]

[0233] Following the same preparation method as compound 27 in Synthesis Example 4, AA-27 was replaced with an equimolar amount of AA-34, BB-27 with an equimolar amount of BB-233, and DD-27 with an equimolar amount of DD-218, yielding compound 233 (15.29 g, yield 71%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 860.3211 (theoretical value: 860.3223). Theoretical elemental content (%) C 62 H 44 N₂OSi: C, 86.48; H, 5.15; N, 3.25. Measured elemental content (%): C, 86.53; H, 5.19; N, 3.22.

[0234] Synthesis Example 26: Synthesis of Compound 244

[0235]

[0236] Following the same preparation method as compound 27 in Synthesis Example 4, AA-27 was replaced with an equimolar amount of AA-244, BB-27 with an equimolar amount of BB-244, and DD-27 with an equimolar amount of DD-244, yielding compound 244 (15.32 g, yield 68%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 900.3161 (theoretical value: 900.3172). Theoretical elemental content (%) C 64 H 44 N2O2Si: C, 85.30; H, 4.92; N, 3.11. Measured elemental content (%): C, 85.25; H, 4.88; N, 3.07.

[0237] Synthesis Example 27: Synthesis of Compound 245

[0238]

[0239] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-176, and DD-1 was replaced with an equimolar amount of DD-245 to obtain compound 245 (15.95 g, yield 70%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 910.3391 (theoretical value: 910.3379). Theoretical elemental content (%) C 66 H 46 N₂OSi: C, 87.00; H, 5.09; N, 3.07. Measured elemental content (%): C, 86.95; H, 5.13; N, 3.11.

[0240] Synthesis Example 28: Synthesis of Compound 246

[0241]

[0242] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-246, and DD-1 was replaced with an equimolar amount of DD-246 to obtain compound 246 (15.27 g, yield 69%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 884.3575 (theoretical value: 884.3587). Theoretical elemental content (%) C 65 H 48 N₂Si: C, 88.20; H, 5.47; N, 3.16. Measured elemental content (%): C, 88.15; H, 5.51; N, 3.20.

[0243] Synthesis Example 29: Synthesis of Compound 247

[0244]

[0245] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-247, and DD-1 was replaced with an equimolar amount of DD-247 to obtain compound 247 (15.58 g, yield 74%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 841.3864 (theoretical value: 841.3852). Theoretical elemental content (%) C 60 H 51 N3Si: C, 85.57; H, 6.10; N, 4.99. Measured elemental content (%): C, 85.62; H, 6.06; N, 5.02.

[0246] Synthesis Example 30: Synthesis of Compound 252

[0247]

[0248] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-252 to obtain compound 252 (15.77 g, yield 76%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 829.3852 (theoretical value: 829.3839). Theoretical elemental content (%) C 60 H 35 D9N2Si: C, 86.81; H, 6.43; N, 3.37. Measured elemental content (%): C, 86.76; H, 6.39; N, 3.40.

[0249] Synthesis Example 31: Synthesis of Compound 260

[0250]

[0251] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-260, and DD-1 was replaced with an equimolar amount of DD-260, yielding compound 260 (15.41 g, yield 75%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 821.3237 (theoretical value: 821.3226). Theoretical elemental content (%) C 59 H 43 N3Si: C, 86.20; H, 5.27; N, 5.11. Measured elemental content (%): C, 86.16; H, 5.32; N, 5.08.

[0252] Synthesis Example 32: Synthesis of Compound 276

[0253]

[0254] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-276 to obtain compound 276 (15.93 g, yield 71%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 896.3576 (theoretical value: 896.3587). Theoretical elemental content (%) C 66 H 48 N₂Si: C, 88.35; H, 5.39; N, 3.12. Measured elemental content (%): C, 88.40; H, 5.42; N, 3.08.

[0255] Synthesis Example 33: Synthesis of Compound 278

[0256]

[0257] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-278, and DD-1 was replaced with an equimolar amount of DD-278 to obtain compound 278 (15.35 g, yield 70%). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 876.3914 (theoretical value: 876.3900). Theoretical elemental content (%) C 64 H 52 N₂Si: C, 87.63; H, 5.98; N, 3.19. Measured elemental content (%): C, 87.58; H, 6.02; N, 3.22.

[0258] Synthesis Example 34: Synthesis of Compound 288

[0259]

[0260] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-231, and DD-1 was replaced with an equimolar amount of DD-288, yielding compound 288 (15.46 g, yield 72%). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 858.3441 (theoretical value: 858.3430). Theoretical elemental content (%) C 63 H 46 N₂Si: C, 88.07; H, 5.40; N, 3.26. Measured elemental content (%): C, 88.12; H, 5.36; N, 3.30.

[0261] Synthesis Example 35: Synthesis of Compound 299

[0262]

[0263] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-299, and DD-1 was replaced with an equimolar amount of DD-299, yielding compound 299 (15.90 g, yield 73%). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 870.4225 (theoretical value: 870.4214). Theoretical elemental content (%) C 63 H 38 D 10 N₂Si: C, 86.85; H, 6.71; N, 3.22. Measured elemental content (%): C, 86.90; H, 6.66; N, 3.19.

[0264] Synthesis Example 36: Synthesis of Compound 312

[0265]

[0266] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-312, and DD-1 was replaced with an equimolar amount of DD-312, yielding compound 312 (15.66 g, yield 75%). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 834.3419 (theoretical value: 834.3430). Theoretical elemental content (%) C 61 H 46 N₂Si: C, 87.73; H, 5.55; N, 3.35. Measured elemental content (%): C, 87.68; H, 5.59; N, 3.38.

[0267] Synthesis Example 37: Synthesis of Compound 321

[0268]

[0269] Following the same preparation method as compound 1 in Example 3, DD-1 was replaced with an equimolar amount of DD-321 to obtain compound 321 (15.55 g, yield 69%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 900.3851 (theoretical value: 900.3838). Theoretical elemental content (%) C 66 H 44 D4N2Si: C, 87.96; H, 5.82; N, 3.11. Measured elemental content (%): C, 88.01; H, 5.78; N, 3.09.

[0270] Synthesis Example 38: Synthesis of Compound 328

[0271]

[0272] Following the same preparation method as compound 1 in Example 3, CC-1 was replaced with an equimolar amount of CC-227, and DD-1 was replaced with an equimolar amount of DD-328, yielding compound 328 (15.49 g, yield 70%). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 884.3598 (theoretical value: 884.3587). Theoretical elemental content (%) C 65 H 48 N₂Si: C, 88.20; H, 5.47; N, 3.16. Measured elemental content (%): C, 88.16; H, 5.52; N, 3.20.

[0273] The following are compounds other than the aromatic amine compounds described in this invention used in the device fabrication examples:

[0274]

[0275] 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.

[0276] Comparative device fabrication example 1: Comparative device 1

[0277] 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.

[0278] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HTL-1 and p-1 (mass ratio 100:3) as hole injection layer with a thickness of 10 nm; b) HTL-1 as hole transport layer with a thickness of 30 nm; c) MADN and BD (mass ratio 95:5) as light-emitting layer with a thickness of 35 nm; d) TPBi as hole blocking layer with a thickness of 20 nm; e) HNBphen and Liq (mass ratio 6:4) as electron transport layer with a thickness of 20 nm; f) LiF as electron injection layer with a thickness of 0.1 nm; g) Mg and Ag (mass ratio 7:3) as cathode with a thickness of 10 nm; h) CP-4 as capping layer with a thickness of 100 nm.

[0279] Comparative device fabrication examples 2-3: Comparative devices 2-3

[0280] By replacing HTL-1 in the hole injection layer and hole transport layer with HTL-2 and HTL-3 respectively, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 and 3 can be obtained.

[0281] Device fabrication examples 1-36: Light-emitting devices 1-36

[0282] By replacing HTL-1 in the hole injection layer and hole transport layer with the aromatic amine compounds of the present invention synthesized in Synthesis Examples 3 to 38, and with the other steps being the same as in Comparative Device Preparation Example 1, light-emitting devices 1 to 36 can be obtained.

[0283] Table 1

[0284]

[0285]

[0286] Comparative device fabrication example 4: Comparative device 4

[0287] 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.

[0288] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-8 and p-1 (mass ratio 100:3) as hole injection layer, with a thickness of 30 nm; b) HT-8 as hole transport layer, with a thickness of 35 nm; c) HTL-1 as light-emitting auxiliary layer, with a thickness of 25 nm; d) RH-1, RH-2 and Ir(dpm)PQ2 (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 20 nm; f) HNBphen and Liq (mass ratio 7:3) as electron transport layer, with a thickness of 20 nm; g) LiF as electron injection layer, with a thickness of 0.1 nm; h) Mg and Ag (mass ratio 3:7) as cathode, with a thickness of 10 nm; i) CP-4 as capping layer, with a thickness of 120 nm.

[0289] Comparative device fabrication examples 5-6: Comparative devices 5-6

[0290] By replacing HTL-1 in the light-emitting auxiliary layer with HTL-2 and HTL-3 respectively, and following the same steps as in Comparative Device Preparation Example 4, Comparative Devices 5 and 6 can be obtained.

[0291] Device fabrication examples 37-72: Light-emitting devices 37-72

[0292] By replacing HTL-1 in the light-emitting auxiliary layer with the aromatic amine compounds of the present invention synthesized in Examples 3 to 38, and with all other steps being the same as in Comparative Device Preparation Example 4, light-emitting devices 37 to 72 can be obtained.

[0293] Table 2

[0294]

[0295]

[0296]

[0297] The device data in Tables 1 and 2 show that the 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 aromatic amine compounds provided by this invention are a class of high-performance OLED materials with promising application prospects.

[0298] 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. An aromatic amine compound, characterized in that, It has the structure shown in equation (I): Wherein, Ar1 is selected from one of the following structures: Each time a2 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time b2 appears, it is selected from 0, 1, 2 or 3, either the same or different; each time d2 appears, it is selected from 0, 1 or 2, either the same or different. R1 to R3 are independently selected from one of methyl, deuterated methyl, ethyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, pyridyl, pyrimidinyl, dibenzofuranyl, and dibenzothiopheneyl. 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 group, methyl group, deuterated methyl group, trifluoromethyl group, isopropyl group, and tert-butyl group. The R mentioned 101 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, fluorine, cyano, methyl, deuterated methyl, isopropyl, tert-butyl, and one of the following structures: ； The Ar2 and Ar3 mentioned are independently selected from one of the following structures: Wherein, each occurrence of a3 is selected from 0, 1, 2, 3, 4 or 5, either the same or different; each occurrence of b3 is selected from 0, 1, 2, 3 or 4, either the same or different; each occurrence of c3 is selected from 0, 1, 2 or 3, either the same or different; each occurrence of d3 is selected from 0, 1 or 2, either the same or different; and each occurrence of g3 is selected from 0 or 1, either the same or different. The R mentioned 81 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, substituted or unsubstituted phenyl group, and at most one R group. 81 Selected from substituted or unsubstituted phenyl groups; The R mentioned 81 Each time it appears, it is selected from hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted phenyl group, either the same or different. The L1 is selected from a single bond or one of the following structures: The L2 to L3 are independently selected from a single bond or one of the following structures: Wherein, each occurrence of a4 is selected from 0, 1, 2, 3 or 4, either the same or different; each occurrence of b4 is selected from 0, 1, 2 or 3, either the same or different. The R mentioned 201 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, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, or substituted or unsubstituted tert-butyl group. The substituents in "substituted or unsubstituted" are independently selected from one of deuterium atom, halogen atom, cyano group, and C1-C4 alkyl group.

2. The aromatic amine compound according to claim 1, characterized in that, The Ar1 mentioned is selected from one of the following structures: R1 to R3 are independently selected from one of methyl, deuterated methyl, ethyl, isopropyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, biphenyl, naphthyl, pyridyl, and pyrimidinyl. 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 group, methyl group, deuterated methyl group, and trifluoromethyl group; The R mentioned 101 Each time it appears, it is selected from hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, isomethyl group, or other similar groups, either identically or differently. One of propyl and tert-butyl.

3. The aromatic amine compound according to claim 1, characterized in that, The aforementioned Selected from the structure shown below A sort of: 。 4. The aromatic amine compound according to claim 1, characterized in that, The Ar2 and Ar3 mentioned are independently selected from one of the following structures: The R mentioned 81 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, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, and substituted or unsubstituted adamantyl group; The R mentioned 81 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted tert-butyl group, or substituted or unsubstituted phenyl group.

5. The 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: The R mentioned 201 Each time it appears, it is selected from either hydrogen or deuterium atoms, either the same or different.

6. An aromatic amine compound, characterized in that, The 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, characterized in that, The hole transport region contains one or more of the aromatic amine compounds described in any one of claims 1 to 6.

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