An arylamine compound and an organic electroluminescence device thereof

Abstract

The present application relates to the technical field of organic photoelectric material, in particular to a kind of arylamine compound and organic electroluminescent device thereof.The present application provides a kind of arylamine compound, it has good hole injection transport capacity, also has appropriate energy level, as hole transport material is applied in OLED device, not only can effectively inject and transport hole, also can be well matched with other adjacent organic functional layer, to improve the luminous efficiency of device;It also has good thermal stability and chemical stability, under the working environment of high temperature and corrosive gas, can delay the aging of device, further prolong the service life of device.The arylamine compound provided by the present application can also be applied as cover layer in OLED device, to further improve the luminous efficiency of device.Due to its also has good thermal stability and chemical stability, as cover layer, can also effectively isolate water vapor, oxygen and corrosive gas, further prolong the service life of device.

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, reaching the emissive layer. There, they recombine to generate excitons, releasing energy. Under the influence of an 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 device performance, additional organic functional layers are placed between the anode and the emissive layer, and between the cathode and the emissive layer. Generally, the region between the anode and the emissive layer is the hole transport region, primarily responsible for injecting and transporting holes, including hole injection layers, hole transport layers, luminescent auxiliary layers, and electron blocking layers. The region between the cathode and the emissive layer is the electron transport region, primarily responsible for injecting and transporting electrons, including electron injection layers, electron transport layers, and hole blocking layers.

[0004] Hole transport materials should generally possess good hole injection and transport capabilities, as well as appropriate triplet energy levels (T1), highest occupied orbital levels (HOMO), and lowest unoccupied orbital levels (LUMO). This is beneficial for hole injection and transport, and also allows for good matching with other organic functional layers, thereby improving the luminous efficiency of organic electroluminescent devices, reducing energy consumption, and lowering driving voltage.

[0005] In addition to setting an organic functional layer between the anode and cathode, a capping layer is also set on the outside of the light-emitting electrode (away from the non-light-emitting electrode). Generally, the capping layer has a high refractive index, which can improve the light transmittance of the device, change the light emission direction, and thus improve the luminous efficiency and color purity of the device.

[0006] To further improve the performance of OLED devices, such as driving voltage, luminous efficiency, color purity, and lifespan, it is necessary to develop high-performance hole transport materials and capping layer materials. Summary of the Invention

[0007] To address the aforementioned technical problems, this invention provides an aromatic amine compound possessing appropriate triplet energy levels, HOMO and LUMO, excellent hole injection and transport capabilities, good thermal and chemical stability, and a high refractive index. It can be used as a hole transport material or capping material in OLED devices, thereby effectively improving the luminous efficiency, driving voltage, and lifespan of OLED devices. It has the structure shown in formula (I):

[0008]

[0009] Among them, L1~L3, L 11 ~L 18 Independently 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 9,9-dimethylfluorenylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted triazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinoxalinylene, and substituted or unsubstituted quinoxalinylene, and at least one of L1 to L3 is not selected from single bond;

[0010] The Ar1 to Ar4 are independently selected from one of substituted or unsubstituted C6 to C30 aryl groups and substituted or unsubstituted C2 to C30 heteroaryl groups, and at least one is selected from the structure shown in formula (IA):

[0011]

[0012] In formula (IA), X is selected from oxygen or sulfur atoms each time it appears;

[0013] Each time 'a' appears, it is selected from 0, 1, 2, 3, or 4, either the same or different; each time 'b' appears, it is selected from 0, 1, or 2, either the same or different.

[0014] Each time R1 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 C1-C4 alkyl group, substituted or unsubstituted C5-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R1 groups are connected to form a substituted or unsubstituted C6-C10 aromatic ring.

[0015] Each time R2 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 C1-C4 alkyl group, substituted or unsubstituted C5-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group.

[0016] The substituents in "substituted or unsubstituted" above are selected from deuterium atoms; fluorine atoms; cyano groups; C1-C4 alkyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms and fluorine atoms; C5-C10 cycloalkyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, and C1-C4 alkyl groups; C6-C12 aryl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, C1-C4 alkyl groups, and C5-C10 cycloalkyl groups; and C2-C12 heteroaryl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, C1-C4 alkyl groups, and C5-C10 cycloalkyl groups.

[0017] The condition is that L1~L3, L 11 ~L 18 At least one of Ar1 to Ar4 is substituted by one or more of the following substituents: a deuterium atom, an aryl group of C6 to C12 substituted with one or more deuterium atoms, or a heteroaryl group of C2 to C12 substituted with one or more deuterium atoms.

[0018] 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.

[0019] Beneficial effects:

[0020] The aromatic amine compounds provided by this invention have excellent hole injection and transport capabilities, as well as appropriate triplet energy levels, HOMO, and LUMO. When used as hole transport materials in OLED devices, they can not only effectively inject and transport holes, but also match well with other adjacent organic functional layers, thereby improving the luminous efficiency of the device. They also have excellent thermal and chemical stability, and can delay device aging and further extend the device's lifespan in high-temperature and corrosive gas environments.

[0021] The aromatic amine compounds provided by this invention also have a high refractive index, making them suitable as a capping layer in OLED devices to improve the device's luminous efficiency. Furthermore, due to their excellent thermal and chemical stability, when used as a capping layer, they can effectively isolate moisture, oxygen, and corrosive gases, further extending the device's lifespan. Detailed Implementation

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

[0023] 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.

[0024] 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".

[0025] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0026] 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.

[0027] 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 group is preferably cyclopentane, cyclohexane, cyclopentenyl, 1-adamantane, 2-adamantane, or norbornane.

[0028] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentenyl or cyclohexenyl.

[0029] 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.

[0030] 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.

[0031] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

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

[0033] 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.

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

[0035] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted 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 heterocyclic, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3-C12 alkyl, halogen, cycloalkyl ... Cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocyclic, C6-C30 aryl, C3-C30 heteroaryl, silyl, when substituted with multiple substituents, the multiple substituents may be the same or different from each other; preferably, it means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane Alkyl, 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, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazineyl, Ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, methoxy, ethoxy, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazoyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl, where the multiple substituents are the same or different from each other.

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

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

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

[0039]

[0040] This invention provides an aromatic amine compound having the structure shown in formula (I):

[0041]

[0042] Among them, L1~L3, L 11 ~L 18 Independently 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 9,9-dimethylfluorenylene, substituted or unsubstituted pyridinylene, substituted or unsubstituted pyrimidinylene, substituted or unsubstituted pyrazinylene, substituted or unsubstituted pyridazinylene, substituted or unsubstituted triazinylene, substituted or unsubstituted quinolinylene, substituted or unsubstituted isoquinolinylene, substituted or unsubstituted quinoxalinylene, substituted or unsubstituted quinoxalinylene, and substituted or unsubstituted quinoxalinylene, and at least one of L1 to L3 is not selected from single bond;

[0043] The Ar1 to Ar4 are independently selected from one of substituted or unsubstituted C6 to C30 aryl groups and substituted or unsubstituted C2 to C30 heteroaryl groups, and at least one is selected from the structure shown in formula (IA):

[0044]

[0045] In formula (IA), X is selected from oxygen or sulfur atoms each time it appears;

[0046] Each time 'a' appears, it is selected from 0, 1, 2, 3, or 4, either the same or different; each time 'b' appears, it is selected from 0, 1, or 2, either the same or different.

[0047] Each time R1 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 C1-C4 alkyl group, substituted or unsubstituted C5-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R1 groups are connected to form a substituted or unsubstituted C6-C10 aromatic ring.

[0048] Each time R2 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 C1-C4 alkyl group, substituted or unsubstituted C5-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, or substituted or unsubstituted C2-C30 heteroaryl group.

[0049] The substituents in "substituted or unsubstituted" above are selected from deuterium atoms; fluorine atoms; cyano groups; C1-C4 alkyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms and fluorine atoms; C5-C10 cycloalkyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, and C1-C4 alkyl groups; C6-C12 aryl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, C1-C4 alkyl groups, and C5-C10 cycloalkyl groups; and C2-C12 heteroaryl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, fluorine atoms, cyano groups, C1-C4 alkyl groups, and C5-C10 cycloalkyl groups.

[0050] The condition is that L1~L3, L 11 ~L 18 At least one of Ar1 to Ar4 is substituted by one or more of the following substituents: a deuterium atom, an aryl group of C6 to C12 substituted with one or more deuterium atoms, or a heteroaryl group of C2 to C12 substituted with one or more deuterium atoms.

[0051] Preferably, the substituents in "substituted or unsubstituted" are selected from deuterium atom; fluorine atom; cyano; methyl; trifluoromethyl; deuterated methyl; ethyl; deuterated ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; deuterated tert-butyl; cyclopentyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; cyclohexyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; cyclohexyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; cyclohexyl groups substituted or unsubstituted by one of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl. Adamantyl alkyl group substituted or unsubstituted with one or more of the group consisting of methyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; norbornene alkyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; phenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; substituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl. Or unsubstituted naphthyl; furanyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; thiophene group substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; benzofuranyl group substituted or unsubstituted with one or more of the group consisting of deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; Benzothiophene group substituted or unsubstituted with one or more of the group consisting of isopropyl, tert-butyl, and deuterated tert-butyl; dibenzofuran group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; dibenzothiophene group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; pyridyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl.A pyrimidinyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; a triazine group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; a triazine group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; The following are pyrazinyl groups substituted or unsubstituted with one or more of the following groups: methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; pyridazinyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; A quinolinyl group substituted or unsubstituted with one or more of the groups consisting of methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; an isoquinolinyl group substituted or unsubstituted with one or more of the groups consisting of deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, deuterated isopropyl, tert-butyl, and deuterated tert-butyl; A quinoxalinyl group substituted or unsubstituted with one or more of the group consisting of deuterated isopropyl, tert-butyl, and deuterated tert-butyl; or a quinoxalinyl group substituted or unsubstituted with one or more of the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, an isopropyl group, deuterated isopropyl, tert-butyl, and deuterated tert-butyl, wherein the substituents are one or more, and when there are multiple substituents, the multiple substituents may be the same or different.

[0052] Preferably, L1 to L3, L 11 ~L 18 At least one of Ar1 to Ar4 is replaced by more than one deuterium atom.

[0053] Preferably, L1 to L3, L 11 ~L 18 And at least one of the groups in Ar1 to Ar4 that are not of the structure shown in formula (IA) is replaced by one or more deuterium atoms.

[0054] Preferably, L1 to L3, L 11 ~L 18 It is independently selected from a single bond or one of the structures shown below, and at least one of L1 to L3 is not selected from a single bond:

[0055]

[0056] Wherein, the a 11Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either the same or different; d 11 Each time it appears, it is selected from 0 or 1, either the same or different.

[0057] The R mentioned 11 Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, deuterated norbornyl, phenyl, deuterated phenyl, methyl One of the following: substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, deuterated naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, biphenyl, deuterated biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, and cyano-substituted biphenyl.

[0058] Preferably, the aforementioned Independently selected from one of the following structures:

[0059]

[0060] Wherein, the a 12 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 12 Each time it appears, it is the same or different number 0, 1, 2 or 3; the c mentioned 12 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 12 Each time it appears, it is selected from 0 or 1, either the same or different.

[0061] The R mentioned 12 Each time it appears, it is selected from one of the following groups, either identically or differently: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, deuterated adamantyl, norbornel, deuterated norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl.

[0062] Preferably, the aforementioned Choose one of the following structures:

[0063]

[0064]

[0065]

[0066] Preferably, the aforementioned Selected from those groups mentioned above that contain a deuterium atom.

[0067] Preferably, the aforementioned Independently selected from a single bond or one of the following structures:

[0068]

[0069]

[0070] Wherein, the a 12 b 12 c 12 d 12 R 12 All are as described in this invention.

[0071] Preferably, the aforementioned Independently selected from a single bond or one of the following structures:

[0072]

[0073]

[0074] Preferably, the aforementioned Selected from those groups containing a deuterium atom. Preferably, the... Selected from those groups containing a deuterium atom. Preferably, the... Selected from those groups containing a deuterium atom. Preferably, the... Selected from those groups containing a deuterium atom. Preferably, the formula (IA) is selected from one of the following structures:

[0075]

[0076] Wherein, each time X appears, it is selected from oxygen atoms or sulfur atoms, either the same or different;

[0077] The a mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either the same or different.

[0078] The R mentioned 21Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, deuterated norbornyl, phenyl, deuterated phenyl, methyl One of the following: substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, deuterated naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, biphenyl, deuterated biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, and cyano-substituted biphenyl.

[0079] Preferably, the formula (IA) is selected from one of the following structures:

[0080]

[0081] Wherein, the a 22 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 22 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the c mentioned 22 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 22 Each time it appears, it is selected from 0 or 1, either the same or different.

[0082] The R mentioned 22 Each time it appears, it is selected from the same or different hydrogen atom, deuterium atom, fluorine atom, cyano group, or one of the following structures:

[0083]

[0084] Preferably, the groups in Ar1 to Ar4 that are not of the structure shown in formula (IA) are independently selected from one of the following structures:

[0085]

[0086] Wherein, the a 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 41 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 41Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 41 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the g mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the h mentioned 14 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, either the same or different.

[0087] The R mentioned 41 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, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, methyl-substituted norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl;

[0088] The R mentioned 42 Each time it appears, it is selected from one of the following, either identically or differently: phenyl, deuterated phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, naphthyl-substituted phenyl, naphthyl, deuterated naphthyl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, biphenyl, and deuterated biphenyl.

[0089] Preferably, the groups in Ar1 to Ar4 that are not of the structure shown in formula (IA) are independently selected from one of the following structures:

[0090]

[0091]

[0092] Wherein, the a 42 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 42 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 42 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 42 Each time it appears, it is selected from 0, 1 or 2, either the same or different.

[0093] Preferably, one of Ar1 to Ar4 is selected from the structure shown in formula (IA), and the rest are not the structure shown in formula (IA).

[0094] Preferably, Ar1 is selected from the structure shown in formula (IA), and Ar2 to Ar4 are not the structures shown in formula (IA).

[0095] Preferably, two of Ar1 to Ar4 are selected from the structure shown in formula (IA), and the rest are not the structure shown in formula (IA).

[0096] Preferably, Ar1 and Ar3 are selected from the structure shown in formula (IA), while Ar2 and Ar4 are not the structure shown in formula (IA).

[0097] Preferably, Ar1 and Ar2 are selected from the structure shown in formula (IA), while Ar3 and Ar4 are not the structure shown in formula (IA).

[0098] Preferably, three of Ar1 to Ar4 are selected from the structure shown in formula (IA), and the rest are not the structure shown in formula (IA).

[0099] Preferably, Ar1 to Ar3 are selected from the structures shown in formula (IA), and Ar4 is not the structure shown in formula (IA).

[0100] Preferably, Ar1 to Ar4 are all selected from the structures shown in formula (IA).

[0101] Preferably, at least one of the groups in Ar1 to Ar4 that does not have the structure shown in formula (IA) is selected from those groups containing deuterium atoms. More preferably, when the group in Ar1 to Ar4 that does not have the structure shown in formula (IA) is selected from those groups containing deuterium atoms, the attached... Selected from single keys.

[0102] Preferably, the structure shown in formula (I) satisfies at least one of the following conditions:

[0103] i. The aforementioned Selected from those groups mentioned above that contain a deuterium atom;

[0104] ii. The aforementioned Selected from those groups mentioned above that contain a deuterium atom;

[0105] The above iii Selected from those groups mentioned above that contain a deuterium atom;

[0106] iv. The aforementioned Selected from those groups mentioned above that contain a deuterium atom;

[0107] v. the aforementioned Selected from those groups mentioned above that contain a deuterium atom;

[0108] vi. At least one of the groups in Ar1 to Ar4 that is not of the structure shown in formula (IA) is selected from those groups that contain a deuterium atom.

[0109] Most preferably, the aromatic amine compound is selected from one of the following compounds:

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] The above only lists some specific structural forms of the aromatic amine compounds represented by formula (I), but the present invention is not limited to these chemical structures. Any chemical structure based on formula (I) with substituents as defined in the present invention should be included.

[0129] The aromatic amine compound represented by formula (I) of this invention can be prepared by the following synthetic route:

[0130]

[0131] Wherein, Y1 and Y2 are independently selected from chlorine atoms, bromine atoms, or iodine atoms;

[0132] The L1~L3, L 11 ~L 18 Ar1 to Ar4 are as described in this invention.

[0133] In the above synthetic route, the target compound (I) is obtained by reacting halide (A) with aromatic amine compounds (B) and (C) via a Buchwald-Hartwig coupling reaction. The reaction order of halide (A) with aromatic amine compounds (B) and (C) is not limited; it can react with (B) first and then with (C), or with (C) first and then with (B), or with both (B) and (C) simultaneously.

[0134] All the above reaction routes employ commonly used reaction types in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation methods use readily available raw materials, have simple processes, and yield excellent results. The compound represented by formula (I) provided by 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.

[0135] 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.

[0136] Preferably, the organic layer includes a hole transport region between the anode and the cathode, and the hole transport region contains one or more of the aromatic amine compounds described in this invention.

[0137] Preferably, the organic layer includes a light-emitting layer between the anode and the cathode, and the light-emitting layer contains one or more of the aromatic amine compounds described in this invention.

[0138] Preferably, the organic layer includes a cover layer on the side of the cathode opposite to the anode, and the cover layer contains one or more of the aromatic amine compounds described in this invention.

[0139] Preferably, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region between the anode and the cathode, wherein at least one of the hole transport region and the light-emitting layer contains one or more of the aromatic amine compounds described in this invention; more preferably, the hole transport region contains one or more of the aromatic amine compounds described in this invention.

[0140] Preferably, the organic layer includes a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode facing away from the anode, wherein at least one of the hole transport region, the light-emitting layer, and the capping layer contains one or more of the aromatic amine compounds described in this invention; more preferably, the hole transport region or the capping layer contains one or more of the aromatic amine compounds described in this invention.

[0141] 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.

[0142] Preferably, the hole transport region includes at least two of the following: a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer; more preferably, the hole transport region includes a hole injection layer and a hole transport layer.

[0143] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0144] 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.

[0145]

[0146] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances containing / Vs or more, 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. Preferably, the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] Preferably, the electron transport region includes at least two of the following: an electron injection layer, an electron transport layer, and a hole blocking layer; more preferably, the electron transport region includes an electron injection layer and an electron transport layer.

[0151] Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] The capping 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. 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, compound CP-4, and the aromatic amine compounds described in this invention, but are not limited thereto.

[0158]

[0159] The aforementioned organic layers, cathode, anode, and capping layer can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0160] The thickness of each of the aforementioned organic layers and capping 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.

[0161] 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.

[0162] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0163] 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.

[0164] 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.

[0165] Synthesis Example 1: Synthesis of intermediate CC / EE

[0166]

[0167] Under nitrogen protection, AA-35 (11.82 g, 60.00 mmol), BB-35 (9.62 g, 60.00 mmol), potassium carbonate (10.37 g, 75.00 mmol), and Pd(PPh3)4 (0.83 g, 0.72 mmol) were added to a reaction flask, along with 400 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give intermediate EE-35 (11.59 g, yield 83%); HPLC purity ≥ 99.74%. Mass spectrometry m / z: 232.0582 (theoretical value: 232.0593).

[0168] Following the above synthesis method, other intermediates EE / CC required for this invention were synthesized, and the relevant raw materials are shown in Table 101:

[0169] Table 101:

[0170]

[0171] Synthesis Example 2: Synthesis of intermediate bb / dd

[0172]

[0173] Under nitrogen protection, intermediates CC-25 (13.66 g, 50.00 mmol), DD-25 (7.16 g, 50.00 mmol), and sodium tert-butoxide (7.51 g, 78.13 mmol) were added to 400 mL of toluene. Pd2(dba)3 (1.69 g, 1.85 mmol) and P(t-Bu)3 (0.80 mL of 0.5 M toluene solution, 0.11 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 4 h. After the reaction was complete, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was then carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene / methanol (10:3) to obtain intermediate bb-25 (12.75 g, yield 76%) with an HPLC purity ≥ 99.48%. Mass spectrometry m / z: 335.1325 (theoretical value: 335.1310).

[0174] Following the above synthesis method, the intermediate bb / dd required for this invention was synthesized, and the relevant raw materials are shown in Table 102:

[0175] Table 102:

[0176]

[0177]

[0178]

[0179]

[0180] Synthesis Example 3: Synthesis of Compound 25

[0181]

[0182] Synthesis of intermediate cc-25:

[0183] Under nitrogen protection, aa-25 (8.61 g, 40.00 mmol), bb-25 (10.61 g, 30.00 mmol), and sodium tert-butoxide (5.19 g, 54.00 mmol) were added to 260 mL of toluene. Pd(OAc)₂ (0.08 g, 0.36 mmol) and P(t-Bu)₃ (3.00 mL of 0.5 M toluene solution, 1.50 mmol) were added with stirring. The mixture of the above reactants was heated under reflux 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. After standing and separation, the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The obtained solid was recrystallized from toluene / methanol (10:3) to obtain intermediate cc-25 (12.30 g, 80%). HPLC analysis showed that the solid purity was ≥99.81%. Mass spectrometry m / z: 511.1829 (theoretical value: 511.1813).

[0184] Synthesis of compound 25:

[0185] Under nitrogen protection, intermediates cc-25 (5.13 g, 10.00 mmol), dd-25 (3.35 g, 10.00 mmol), and sodium tert-butoxide (1.15 g, 12.00 mmol) were added to 180 mL of toluene. Pd2(dba)3 (0.12 g, 0.13 mmol) and X-Phos (0.12 g, 0.26 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and the layers were separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was precipitated by cooling and filtered again. The resulting solid was recrystallized from toluene to give compound 25 (5.60 g, 73%). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 766.3866 (theoretical value: 766.3861). Theoretical element content (%) C 56 H 42 D4N2O: C, 87.69; H, 6.57; N, 3.65. Measured elemental content (%): C, 83.62; H, 6.54; N, 3.69.

[0186] Synthesis Example 4: Synthesis of Compound 35

[0187]

[0188] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-35, bb-35, and dd-35, respectively, to obtain compound 35 (5.49 g, yield 71%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 772.3379 (theoretical value: 772.3392). Theoretical elemental content (%) C 57 H 36 D4N2O: C, 88.57; H, 5.74; N, 3.62. Measured elemental content (%): C, 88.59; H, 5.71; N, 3.66.

[0189] Synthesis Example 5: Synthesis of Compound 40

[0190]

[0191] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-40, bb-40, and dd-40, respectively, to obtain compound 40 (5.42 g, yield 69%), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 784.3652 (theoretical value: 784.3634). Theoretical elemental content (%) C 56 H 24 D 14 N2S: C, 85.67; H, 6.67; N, 3.57. Measured elemental content (%): C, 85.62; H, 6.64; N, 3.59.

[0192] Synthesis Example 6: Synthesis of Compound 80

[0193]

[0194] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-40, bb-80, and dd-80, respectively, to obtain compound 80 (5.19 g, yield 70%), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 740.3183 (theoretical value: 740.3169). Theoretical elemental content (%) C 52 H 28 D7N3O2: C, 84.30; H, 5.71; N, 5.67. Measured elemental content (%): C, 84.34; H, 5.69; N, 5.68.

[0195] Synthesis Example 7: Synthesis of Compound 90

[0196]

[0197] Under nitrogen protection, aa-40 (2.36 g, 10.00 mmol), bb-90 (8.11 g, 20.00 mmol), and sodium tert-butoxide (2.5 g, 26.00 mmol) were added to 200 mL of toluene. Pd2(dba)3 (0.22 g, 0.24 mmol) and X-Phos (0.22 g, 0.48 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 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. Crystallization was then carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 90 (5.93 g, 67%). HPLC analysis showed the solid purity to be ≥99.92%. Mass spectrometry m / z: 884.4202 (theoretical value: 884.4218). Theoretical element content (%) C 64 H 40 D8N2O2: C, 86.84; H, 6.38; N, 3.16. Measured elemental content (%): C, 86.88; H, 6.36; N, 3.13.

[0198] Synthesis Example 8: Synthesis of Compound 91

[0199]

[0200] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-40, bb-91, and dd-91, respectively, to obtain compound 91 (6.39 g, yield 72%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 887.3573 (theoretical value: 887.3560). Theoretical elemental content (%) C 65 H 37 D5N2O2: C, 87.91; H, 5.33; N, 3.15. Measured elemental content (%): C, 87.94; H, 5.30; N, 3.12.

[0201] Synthesis Example 9: Synthesis of Compound 92

[0202]

[0203] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-40, bb-92, and dd-92, respectively, to obtain compound 92 (5.97 g, yield 73%), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 817.3332 (theoretical value: 817.3322). Theoretical elemental content (%) C 58 H 31D7N2O3: C, 85.16; H, 5.54; N, 3.42. Measured elemental content (%): C, 85.13; H, 5.51; N, 3.46.

[0204] Synthesis Example 10: Synthesis of Compound 124

[0205]

[0206] Following the preparation method of Synthesis Example 7, bb-90 was replaced with an equimolar amount of bb-124 to obtain compound 124 (6.11 g, yield 69%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 884.3049 (theoretical value: 884.3031). Theoretical elemental content (%) C 58 H 32 D4N6O4: C, 78.72; H, 4.56; N, 9.50. Measured elemental content (%): C, 78.70; H, 4.57; N, 9.55.

[0207] Synthesis Example 11: Synthesis of Compound 140

[0208]

[0209] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-140, bb-140, and dd-140, respectively, to obtain compound 140 (4.78 g, yield 68%), with HPLC purity ≥ 99.90%. Mass spectrometry m / z: 702.2932 (theoretical value: 702.2945). Theoretical elemental content (%) C 50 H 26 D8N2S: C, 85.43; H, 6.02; N, 3.99. Measured elemental content (%): C, 85.41; H, 6.08; N, 3.96.

[0210] Synthesis Example 12: Synthesis of Compound 148

[0211]

[0212] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-148, bb-148, and dd-148, respectively, to obtain compound 148 (6.25 g, yield 70%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 891.4158 (theoretical value: 891.4175). Theoretical elemental content (%) C 66 H 37D9N2O: C, 88.85; H, 6.21; N, 3.14. Measured elemental content (%): C, 88.81; H, 6.23; N, 3.18.

[0213] Synthesis Example 13: Synthesis of Compound 160

[0214]

[0215] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-160, bb-160, and dd-160, respectively, to obtain compound 160 (5.37 g, yield 69%), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 777.3475 (theoretical value: 777.3485). Theoretical elemental content (%) C 55 H 31 D7N4O: C, 84.91; H, 5.83; N, 7.20. Measured elemental content (%): C, 84.96; H, 5.80; N, 7.18.

[0216] Synthesis Example 14: Synthesis of Compound 166

[0217]

[0218] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-160, bb-166, and dd-166, respectively, to obtain compound 166 (6.07 g, yield 71%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 855.1208 (theoretical value: 855.1190). Theoretical elemental content (%) C 63 H 34 D 10 N₂O: C, 88.49; H, 6.36; N, 3.28. Measured elemental content (%): C, 88.43; H, 6.38; N, 3.31.

[0219] Synthesis Example 15: Synthesis of Compound 189

[0220]

[0221] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-160, bb-189, and dd-189, respectively, to obtain compound 189 (6.20 g, yield 74%), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 837.3756 (theoretical value: 837.3767). Theoretical elemental content (%) C 62 H39 D5N2O: C, 88.86; H, 5.89; N, 3.34. Measured elemental content (%): C, 88.88; H, 5.91; N, 3.31.

[0222] Synthesis Example 16: Synthesis of Compound 202

[0223]

[0224] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-202, bb-202, and dd-202, respectively, to obtain compound 202 (5.27 g, yield 68%), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 774.4289 (theoretical value: 774.4270). Theoretical elemental content (%) C 56 H 22 D 18 N₂O: C, 86.78; H, 7.54; N, 3.61. Measured elemental content (%): C, 86.77; H, 7.51; N, 3.67.

[0225] Synthesis Example 17: Synthesis of Compound 207

[0226]

[0227] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-160, bb-207, and dd-207, respectively, to obtain compound 207 (5.93 g, yield 72%), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 823.3119 (theoretical value: 823.3109). Theoretical elemental content (%) C 60 H 38 DFN2O: C, 87.46; H, 4.89; N, N, 3.40. Measured elemental content (%): C, 87.48; H, 4.92; N, 3.45.

[0228] Synthesis Example 18: Synthesis of Compound 212

[0229]

[0230] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-212, bb-212, and dd-212, respectively, to obtain compound 212 (6.00 g, yield 75%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 800.3689 (theoretical value: 800.3705). Theoretical elemental content (%) C59 H 40 D4N2O: C, 88.47; H, 6.04; N, 3.50. Measured elemental content (%): C, 88.44; H, 6.02; N, 3.55.

[0231] Synthesis Example 19: Synthesis of Compound 257

[0232]

[0233] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-257 and bb-257, respectively, to obtain compound 257 (5.65 g, yield 74%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 762.2935 (theoretical value: 762.2948). Theoretical elemental content (%) C 52 H 26 D 10 N2S2: C, 81.85; H, 6.07; N, 3.67. Measured elemental content (%): C, 81.88; H, 6.03; N, 3.72.

[0234] Synthesis Example 20: Synthesis of Compound 261

[0235]

[0236] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-261 and bb-261, respectively, to obtain compound 261 (6.94 g, yield 76%), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 912.3441 (theoretical value: 912.3448). Theoretical elemental content (%) C 64 H 36 D8N2S2: C, 84.17; H, 5.74; N, 3.07. Measured elemental content (%): C, 84.19; H, 5.70; N, 3.08.

[0237] Synthesis Example 21: Synthesis of Compound 264

[0238]

[0239] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-257 and bb-264, respectively, to obtain compound 264 (6.45 g, yield 73%), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 882.4012 (theoretical value: 882.4030). Theoretical elemental content (%) C 64 H 34 D10 N2O2: C, 87.04; H, 6.16; N, 3.17. Measured elemental content (%): C, 87.06; H, 6.13; N, 3.19.

[0240] Synthesis Example 22: Synthesis of Compound 278

[0241]

[0242] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-257 and bb-278, respectively, to obtain compound 278 (6.36 g, yield 72%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 882.4047 (theoretical value: 882.4030). Theoretical elemental content (%) C 64 H 34 D 10 N2O2: C, 87.04; H, 6.16; N, 3.17. Measured elemental content (%): C, 87.01; H, 6.19; N, 3.12.

[0243] Synthesis Example 23: Synthesis of Compound 287

[0244]

[0245] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-287 and bb-287, respectively, to obtain compound 287 (5.87 g, yield 68%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 862.4270 (theoretical value: 862.4282). Theoretical elemental content (%) C 62 H 30 D 14 N2O2: C, 86.28; H, 6.77; N, 3.25. Measured elemental content (%): C, 86.32; H, 6.72; N, 3.28.

[0246] Synthesis Example 24: Synthesis of Compound 327

[0247]

[0248] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-327, bb-327, and dd-327, respectively, to obtain compound 327 (5.41 g, yield 73%), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 740.3627 (theoretical value: 740.3612). Theoretical elemental content (%) C 54 H28 D 10 N₂O: C, 87.53; H, 6.53; N, 3.78. Measured elemental content (%): C, 87.51; H, 6.59; N, 3.74.

[0249] Synthesis Example 25: Synthesis of Compound 348

[0250]

[0251] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-348 and bb-257, respectively, to obtain compound 348 (5.62 g, yield 67%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 838.3258 (theoretical value: 838.3261). Theoretical elemental content (%) C 58 H 30 D 10 N2S2: C, 83.02; H, 6.00; N, 3.34. Measured elemental content (%): C, 83.05; H, 6.03; N, 3.31.

[0252] Synthesis Example 26: Synthesis of Compound 364

[0253]

[0254] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-364, bb-364, and dd-364, respectively, to obtain compound 364 (6.52 g, yield 72%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 904.4253 (theoretical value: 904.4269). Theoretical elemental content (%) C 67 H 40 D8N2O: C, 88.90; H, 6.23; N, 3.09. Measured elemental content (%): C, 88.93; H, 6.21; N, 3.03.

[0255] Synthesis Example 27: Synthesis of Compound 386

[0256]

[0257] Following the preparation method of Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-364, bb-148, and dd-386, respectively, to obtain compound 386 (5.34 g, yield 72%), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 741.3220 (theoretical value: 741.3226). Theoretical elemental content (%) C53 H 35 D5N2S: C, 85.79; H, 6.11; N, 3.78. Measured elemental content (%): C, 85.75; H, 6.16; N, 3.76.

[0258] Synthesis Example 28: Synthesis of Compound 395

[0259]

[0260] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-395 and bb-395, respectively, to obtain compound 395 (6.17 g, yield 70%), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 880.4855 (theoretical value: 880.4844). Theoretical elemental content (%) C 63 H 48 D8N2O2: C, 85.87; H, 7.32; N, 3.18. Measured elemental content (%): C, 85.89; H, 7.36; N, 3.14.

[0261] Synthesis Example 29: Synthesis of Compound 415

[0262]

[0263] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-415 and bb-415, respectively, to obtain compound 415 (6.05 g, yield 68%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 888.3407 (theoretical value: 888.3417). Theoretical elemental content (%) C 58 H 31 D7N2O3: C, 83.75; H, 5.89; N, 3.15. Measured elemental content (%): C, 83.71; H, 5.84; N, 3.18.

[0264] Synthesis Example 30: Synthesis of Compound 420

[0265]

[0266] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-420 and bb-420, respectively, to obtain compound 420 (6.09 g, yield 71%), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 856.3888 (theoretical value: 856.3874). Theoretical elemental content (%) C 62 H 32 D 10N2O2: C, 86.88; H, 6.11; N, 3.27. Measured elemental content (%): C, 86.83; H, 6.15; N, 3.25.

[0267] Synthesis Example 31: Synthesis of Compound 424

[0268]

[0269] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-415, bb-424, and dd-424, respectively, to obtain compound 424 (5.70 g, yield 73%), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 780.3578 (theoretical value: 780.3561). Theoretical elemental content (%) C 56 H 28 D 10 N2O2: C, 86.12; H, 6.19; N, 3.59. Measured elemental content (%): C, 86.15; H, 6.14; N, 3.62.

[0270] Synthesis Example 32: Synthesis of Compound 446

[0271]

[0272] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-446 and bb-446, respectively, to obtain compound 446 (5.13 g, yield 68%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 754.3387 (theoretical value: 754.3404). Theoretical elemental content (%) C 54 H 26 D 10 N2O2: C, 85.91; H, 6.14; N, 3.71. Measured elemental content (%): C, 85.95; H, 6.11; N, 3.74.

[0273] Synthesis Example 33: Synthesis of Compound 492

[0274]

[0275] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-492, bb-257, and dd-424, respectively, to obtain compound 492 (5.74 g, yield 72%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 796.3345 (theoretical value: 796.3333). Theoretical elemental content (%) C 56 H28D10 N₂O: C, 88.30; H, 5.59; N, 3.89. Measured elemental content (%): C, 88.34; H, 5.56; N, 3.83.

[0276] Synthesis Example 34: Synthesis of Compound 506

[0277]

[0278] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-506, bb-506, and dd-506, respectively, to obtain compound 506 (5.85 g, yield 70%), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 835.3601 (theoretical value: 835.3611). Theoretical elemental content (%) C 62 H 37 D5N2O: C, C, 89.07; H, 5.67; N, 3.35. Measured elemental content (%): C, 89.02; H, 5.69; N, 3.32.

[0279] Synthesis Example 35: Synthesis of Compound 516

[0280]

[0281] Following the preparation method in Synthesis Example 3, aa-25, bb-25, and dd-25 were replaced with equimolar amounts of aa-516, dd-424, and dd-516, respectively, to obtain compound 516 (5.82 g, yield 69%), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 842.3319 (theoretical value: 842.3305). Theoretical elemental content (%) C 59 H 34 D5N3O3: C, 84.06; H, 5.26; N, 4.98. Measured elemental content (%): C, 84.09; H, 5.28; N, 4.93.

[0282] Synthesis Example 36: Synthesis of Compound 537

[0283]

[0284] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-537 and dd-537, respectively, to obtain compound 537 (5.49 g, yield 68%), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 807.3655 (theoretical value: 807.3670). Theoretical elemental content (%) C 57 H 29 D10 N3O2: C, 84.73; H, 6.11; N, 5.20. Measured elemental content (%): C, 84.71; H, 6.17; N, 5.24.

[0285] Synthesis Example 37: Synthesis of Compound 547

[0286]

[0287] Following the preparation method of Synthesis Example 7, aa-40 and bb-90 were replaced with equimolar amounts of aa-547 and bb-547, respectively, to obtain compound 547 (6.17 g, yield %), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 880.3191 (theoretical value: 880.3208). Theoretical elemental content (%) C 62 H 32 D6N2O4: C, 84.56; H, 5.01; N, 3.22. Measured elemental content (%): C, 84.52; H, 5.03; N, 3.18.

[0288] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0289] The following are compounds other than the aromatic amine compounds described in this invention used in the device fabrication examples:

[0290]

[0291] 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 lifespan (brightness decaying 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.

[0292] Comparative device fabrication example 1: Comparative device 1

[0293] 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.

[0294] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HATCN as a hole injection layer with a thickness of 5 nm; b) HT-20 as a hole transport layer with a thickness of 40 nm; c) BH and BD (mass ratio 97:3) as a light-emitting layer with a thickness of 35 nm; d) NBphen and Liq (mass ratio 5:1) as an electron transport layer with a thickness of 35 nm; e) LiF as an electron injection layer with a thickness of 0.2 nm; f) Mg and Ag (mass ratio 6:1) as a cathode with a thickness of 10 nm; g) CP-4 as a capping layer with a thickness of 100 nm.

[0295] Comparative device fabrication example 2: Comparative device 2

[0296] By replacing HT-20 with HT-21 in the hole transport layer, and following the same steps as in Comparative Device Preparation Example 1, Comparative Device 2 can be obtained.

[0297] Device fabrication examples 1-35: Light-emitting devices 1-35

[0298] By replacing HT-20 in the hole transport layer with the aromatic amine compounds of the present invention in Synthesis Examples 3-37, and with all other steps being the same as in Comparative Device Preparation Example 1, light-emitting devices 1-35 can be obtained.

[0299] Table 1

[0300]

[0301]

[0302] Comparative device fabrication example 3: Comparative device 3

[0303] 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.

[0304] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-5 and p-1 (mass ratio 100:3) as hole injection layer with a thickness of 15nm; b) HT-5 as hole transport layer with a thickness of 35nm; c) GH-1, GH-2 and Ir(ppy)2(m-bppy) (mass ratio 48:48:4) as light-emitting layer with a thickness of 35nm; d) BAlq as hole blocking layer with a thickness of 25nm; e) NBphen and Liq (mass ratio 5:1) as electron transport layer with a thickness of 25nm; f) LiF as electron injection layer with a thickness of 0.3nm; g) Mg and Ag (mass ratio 1:1) as cathode with a thickness of 10nm; h) CP-5 as capping layer with a thickness of 100nm.

[0305] Device fabrication examples 36-70: Light-emitting devices 36-70

[0306] By replacing CP-5 in the hole transport layer with the aromatic amine compounds of the present invention in Synthetic Examples 3 to 37, and with all other steps being the same as in Comparative Device Preparation Example 3, light-emitting devices 36 to 70 can be obtained.

[0307] Table 2

[0308]

[0309]

[0310] The device data in Tables 1 and 2 show that the aromatic amine compounds described in this invention, when used as hole transport materials or capping layer materials in OLED devices, can achieve excellent device performance: as shown in Table 1, when used as a hole transport layer, they can effectively reduce the driving voltage of the device, improve the luminous efficiency of the device, and extend the device's lifespan; as shown in Table 2, when used as a capping layer, they can effectively improve the luminous efficiency and lifespan of the device. In summary, the compounds provided by this invention are a class of high-performance OLED materials with excellent application prospects.

[0311] 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): in, The aforementioned Independently selected from one of the following structures: The aforementioned , , , Independently selected from a single bond or one of the following structures: Wherein, the a 12 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 12 Each time it appears, it is the same or different number 0, 1, 2 or 3; the c mentioned 12 Each time it appears, it is selected from 0, 1, or 2, either the same or different. The R mentioned 12 Each time it appears, it is selected from one of the following atoms: hydrogen atom, deuterium atom, methyl, isopropyl, tert-butyl, and phenyl, either the same or different. At least one of Ar1 to Ar4 is selected from the structure shown in formula (IA), which is selected from one of the following structures: Wherein, each time X appears, it is selected from oxygen atoms or sulfur atoms, either the same or different; The a mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either the same or different. The R mentioned 21 Each time it appears, it is selected from one of the hydrogen atom and the phenyl group, either the same or different. The groups in Ar1 to Ar4 that are not of the structure shown in formula (IA) are independently selected from one of the following structures: Wherein, the a 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 41 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 41 Each time it appears, it is selected from 0, 1, or 2, either the same or different. The R mentioned in 41 Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, adamantyl group, methyl-substituted adamantyl group, ethyl-substituted adamantyl group, phenyl group, deuterated phenyl group; the remaining R 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, isopropyl group, tert-butyl group, phenyl group, and deuterated phenyl group. The R mentioned 42 Each time it appears, it is selected from one of phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, naphthyl, deuterated naphthyl, and biphenyl, either the same or different. The condition is that the structure shown in equation (I) satisfies at least one of the following conditions: i. The aforementioned Selected from those groups mentioned above that contain a deuterium atom; ii. The aforementioned Selected from those groups mentioned above that contain a deuterium atom; iii. The aforementioned Selected from those groups mentioned above that contain a deuterium atom; iv. The aforementioned Selected from those groups mentioned above that contain a deuterium atom; v. the aforementioned Selected from those groups mentioned above that contain a deuterium atom; vi. At least one of the groups in Ar1 to Ar4 that is not of the structure shown in formula (IA) is selected from those groups that contain a deuterium atom.

2. The aromatic amine compound according to claim 1, characterized in that, The formula (IA) is selected from one of the following structures: 。 3. The aromatic amine compound according to claim 1, characterized in that, The groups in Ar1 to Ar4 that are not of the structure shown in formula (IA) are independently selected from one of the following structures: 。 4. An aromatic amine compound, characterized in that, The aromatic amine compound is selected from one of the following structures:

5. 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 organic layer contains one or more of the aromatic amine compounds according to any one of claims 1 to 4.

6. The organic electroluminescent device according to claim 5, wherein the organic layer includes a hole transport region between the anode and the cathode, characterized in that, The hole transport region contains one or more of the aromatic amine compounds according to any one of claims 1 to 4.

7. The organic electroluminescent device according to claim 5, wherein the organic layer includes a capping layer on the side of the cathode opposite to the anode, characterized in that, The coating layer contains one or more of the aromatic amine compounds according to any one of claims 1 to 4.

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