A triarylamine compound and an organic electroluminescent device thereof

Abstract

This invention provides a triarylamine compound and its organic electroluminescent device, relating to the field of organic electroluminescent materials technology. Compared with conventional organic electroluminescent compounds, this compound has an asymmetric spatial configuration and a higher glass transition temperature. Furthermore, the asymmetric triarylamine compound exhibits good thermal stability and film-forming properties. In addition, when used as a capping material in organic light-emitting devices, this asymmetric triarylamine compound can effectively improve the luminous efficiency and driving voltage of the organic electroluminescent device, while also extending the device's lifespan. The preparation method of the triarylamine compound described in this invention is simple, the raw materials are readily available, and it can meet industrialization requirements, demonstrating good application effects and industrialization prospects. It can be widely used in panel displays, lighting sources, flexible OLEDs, organic solar cells, and other fields.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a triarylamine compound and its organic electroluminescent device. Background Technology

[0002] In recent years, with the rapid development of science and technology, people's requirements for display performance have gradually increased. Under this situation, organic light-emitting diodes (OLEDs) have gradually attracted widespread attention due to their excellent characteristics such as low operating voltage, high brightness, high efficiency, high contrast, thinness, light weight, wide viewing angle, wide operating temperature range, and simple process.

[0003] OLED devices are typically classified into single-layer, two-layer, three-layer, and multi-layer structures. They generally consist of organic functional layers located between the anode and cathode, or on the outside of one or more of these electrodes. The anode is typically made of ITO (indium tin oxide), and the cathode is usually made of a metal material with a low work function. The organic functional layers include a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), an electron injection layer (EIL), and a capping layer (CPL). Under an electric field, the device is electrically excited, and through carrier injection, migration, electron-hole formation of excitons, and exciton recombination, light emission occurs.

[0004] Based on the direction of light emission, OLEDs can be divided into bottom-emitting OLEDs and top-emitting OLEDs. Top-emitting OLEDs are the most common in applications. Research reports indicate that current devices generally suffer from optical waveguide effects and surface plasmon effects, which cause most photons to undergo non-radiative coupling, resulting in relatively low external quantum efficiency. Therefore, improving the light extraction efficiency of OLEDs has become a research hotspot both domestically and internationally.

[0005] To improve the luminous efficiency of top-emitting OLEDs, the simplest and most effective method is to form a capping layer on the transparent electrode as a light extraction functional layer. The capping layer material can be used to reduce total internal reflection losses and waveguide losses in OLEDs, thereby improving light coupling output efficiency. The capping layer material should possess excellent properties such as a high glass transition temperature, a high thin-film refractive index in the visible light range, and corrosion resistance. Therefore, developing novel capping layer materials to improve the luminous efficiency and lifespan of devices is crucial. Summary of the Invention

[0006] To overcome the problems existing in the prior art, the purpose of this invention is to provide a triarylamine compound and its organic electroluminescent device based on the prior art and with industrialization as the goal. The triarylamine compound provided by this invention has an asymmetric spatial configuration, which makes it easier to control the glass transition temperature of the material, enabling the material to have good light-emitting performance. Moreover, the asymmetric triarylamine structure compound has good rigidity and good film-forming properties. Using this compound as a capping layer of the device can effectively improve the driving voltage, luminous efficiency and lifespan of the OLED device.

[0007] Specifically, the present invention provides a triarylamine compound, which is represented by the following formula I:

[0008]

[0009] In the above formula I, *-L1-Ar1, *-L2-Ar2, and *-L0-(Ra)n0 are different from each other;

[0010] The R a Selected from any one of -F, -CF3, -Si(R1R2R3); and n0 is greater than or equal to 1, where, when R a When n is selected from -F, n0 is selected from 5;

[0011] R1 to R3 are each independently selected from any one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloalcohol.

[0012] The Ar1 is selected from the group shown in formula a-1, and a-1 is connected to L1 through the * site;

[0013]

[0014] X is selected from O or S;

[0015] Each z is independently selected from CH or N;

[0016] Each of the R0s is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0017] The n1 is selected from 1, 2, 3 or 4; when n1 is greater than 1, two or more R0s are the same or different from each other, or two adjacent R0s are connected to each other to form a substituted or unsubstituted ring;

[0018] The Ar2 is selected from one or a combination of the following groups:

[0019]

[0020] Wherein, each of the E's is independently selected from CH or N;

[0021] X1 is selected from O, S, C(R) e R f ), N(R g ), Si(R) k Any one of 2;

[0022] The R e R f Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R e R f They connect with each other to form substituted or unsubstituted rings;

[0023] The R g It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0024] The R k Each is independently selected from one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0025] Each of the R4s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0026] Each of the R5s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0027] The b1 is selected from 1, 2, 3, 4 or 5; the b2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the b3 is selected from 1, 2, 3, 4, 5, 6 or 7; the b4 is selected from 1, 2, 3 or 4; the b5 is selected from 1, 2 or 3.

[0028] The L0 is selected from any one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings with fused cycloyl groups.

[0029] The L1 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0030] The R a When L1 is selected from -CF3, it is not selected from a single bond;

[0031] The L2 is selected from a single bond or one or a combination of the following groups:

[0032]

[0033] Wherein, each of the Y terms is independently selected from CH or N;

[0034] X2, X3, and X4 are each independently selected from O, S, and C(R). p R q ), N(R h Any one of the following;

[0035] The R p R q Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R p R q They connect with each other to form substituted or unsubstituted rings;

[0036] The R h It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0037] The R b Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R b They connect with each other to form substituted or unsubstituted rings;

[0038] Each of the R6 groups is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0039] Each of the R7s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0040] a0 is selected from 1 or 2; a1 is selected from 1, 2, 3 or 4; a2 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; a3 is selected from 1, 2, 3, 4, 5 or 6.

[0041] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer comprises at least one of the triarylamine compounds described in the present invention.

[0042] Beneficial effects

[0043] The triarylamine compound of Formula I provided by this invention has three groups connected to each other on different sides. Its asymmetric spatial configuration has an easily tunable glass transition temperature, which can effectively control the crystallinity of the material. When this compound is used as a capping material in OLED devices, it has a high glass transition temperature, a high thin film refractive index in the visible light range, and good film-forming properties. This is beneficial for light to be emitted from the front viewing angle of the device, improving the light extraction efficiency of the device and extending the lifespan of the device.

[0044] In summary, the asymmetric triarylamine compounds provided by this invention, when applied to OLED devices, can effectively improve the luminous efficiency of the devices, reduce the driving voltage, and extend the lifespan of the devices. They are widely applicable to commercial production and have good industrialization prospects. Detailed Implementation

[0045] The technical solutions described below, in conjunction with embodiments of the present invention, will further clarify and fully illustrate the invention. Obviously, the described embodiments are merely some, not all, of the embodiments of the present invention. After reading this invention, any modifications of the present invention by those skilled in the art will fall within the scope defined by the present invention.

[0046] In this specification, "-*" refers to the portion connected to another substituent. "-*" can be attached to any optional position of the group / fraction to which it is attached.

[0047] 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 ring. For example, Can represent Can represent And so on.

[0048] 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.

[0049] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0050] 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 30 carbon atoms, more preferably having 1 to 25 carbon atoms, even more preferably having 1 to 20 carbon atoms, and still more preferably having 1 to 15 carbon atoms, particularly preferably having 1 to 10 carbon atoms, and most preferably having 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl groups; the branched-chain alkyl group includes, but is not limited to, isomers of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc., but is not limited thereto.

[0051] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R n )3 groups, wherein each R n Each R is independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each Rn Each group is independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, and substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 8 carbon atoms. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 7 carbon atoms. Preferably, each R... n Each group is independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples of substituted or unsubstituted silyl groups may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc.

[0052] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. It can be a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, or a bridged cycloalkyl group. Preferably, it has 3 to 30 carbon atoms, more preferably 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, even more preferably 5 to 10 carbon atoms, and particularly preferably 5 to 7 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, ferruginyl, and isocamphenyl.

[0053] The aryl group referred to in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl. Preferably, it has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, even more preferably 6 to 14 carbon atoms, and particularly 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, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, 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, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[0054] 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, or phosphorus atoms, and preferably have 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, even more preferably 2 to 25 carbon atoms, and particularly preferably 2 to 20 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0055] The arylene group referred to in this invention refers to the collective term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, even more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 18 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; specific examples may include naphthylene, anthracene, phenanthrene, pyrene, terphenylene, fluoranthracene, etc., but are not limited to.

[0056] The heteroaryl group refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom, including but not limited to oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, even more preferably 2 to 25 carbon atoms, and particularly preferably 2 to 20 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom, and the heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic and fused-ring heteroaryl groups may include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, and dibenzocarbazolyl; specific examples of the polycyclic heteroaryl groups may include, but are not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl.

[0057] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Preferably, they have 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms, even more preferably 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms. The fused alicyclic and aromatic ring groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc.

[0058] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for the monovalent group obtained by removing one hydrogen atom after the alicyclic and heteroaromatic rings are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and particularly preferably 5 to 12 carbon atoms. The fused cycloyl groups of the alicyclic and heterocyclic rings may include, but are not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium-benzocycloheptyl, pyrimidinium-cyclopropyl, pyrimidinium-cyclobutyl, pyrimidinium-cyclopentyl, pyrimidinium-benzohexyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc.

[0059] The fused alicyclic and aromatic ring cycloalgides described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. Preferably, they have 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, even more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 10 carbon atoms. The fused alicyclic and aromatic ring cycloalgides may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0060] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and heteroaromatic rings are fused together. Preferably, they have 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, even more preferably 3 to 15 carbon atoms, and particularly preferably 3 to 10 carbon atoms. The fused alicyclic and heteroaromatic ring groups may include pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinoxopropyl, pyrimidinoxobutyl, pyrimidinoxopentyl, pyrimidinoxocyclohexyl, pyrimidinoxobenzocycloheptyl, etc. Dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, dibenzothiophenocyclohexyl, dibenzothiophenocycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, etc., but not limited to these.

[0061] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, cyano, nitro, amino, halogen atoms, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamine, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamine, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred atom types include deuterium, cyano, nitro, amino, halogen, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, and C1-C12 alkoxy. Specific examples may include: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, and triphenylene. Peryl, pyrene, fluoranyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, carbazoloindolyl, pyrroleyl, furanyl, thiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazoleyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these. Alternatively, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be linked to form a ring.

[0062] The cyclic structure formed by bonding as described in this invention refers to two groups being linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0063]

[0064] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, eight-membered rings, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0065] Specifically, the present invention provides a triarylamine compound, which is represented by the following formula I:

[0066]

[0067] In the above formula I, the *-L1-A r 1. *-L2-Ar2 and *-L0-(Ra)n0 are different from each other;

[0068] The R a Selected from any one of -F, -CF3, -Si(R1R2R3); and n0 is greater than or equal to 1, where, when R a When n is selected from -F, n0 is selected from 5;

[0069] R1 to R3 are each independently selected from any one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloalcohol.

[0070] The Ar1 is selected from the group shown in formula a-1, and a-1 is connected to L1 through the * site;

[0071]

[0072] X is selected from O or S;

[0073] Each z is independently selected from CH or N;

[0074] Each of the R0s is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0075] The n1 is selected from 1, 2, 3 or 4; when n1 is greater than 1, two or more R0s are the same or different from each other, or two adjacent R0s are connected to each other to form a substituted or unsubstituted ring;

[0076] The Ar2 is selected from one or a combination of the following groups:

[0077]

[0078] Wherein, each of the E's is independently selected from CH or N;

[0079] X1 is selected from O, S, C(R) e R f ), N(R g ), Si(R) k Any one of 2;

[0080] The Re R f Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R e R f They connect with each other to form substituted or unsubstituted rings;

[0081] The R g It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0082] The R k Each is independently selected from one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0083] Each of the R4s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0084] Each of the R5s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0085] The b1 is selected from 1, 2, 3, 4 or 5; the b2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the b3 is selected from 1, 2, 3, 4, 5, 6 or 7; the b4 is selected from 1, 2, 3 or 4; the b5 is selected from 1, 2 or 3.

[0086] The L0 is selected from any one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings with fused cycloyl groups.

[0087] The L1 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0088] The R a When L1 is selected from -CF3, it is not selected from a single bond;

[0089] The L2 is selected from a single bond or one or a combination of the following groups:

[0090]

[0091] Wherein, each of the Y terms is independently selected from CH or N;

[0092] X2, X3, and X4 are each independently selected from O, S, and C(R). p R q ), N(R h Any one of the following;

[0093] The R p R qEach is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R p R q They connect with each other to form substituted or unsubstituted rings;

[0094] The R h It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0095] The R b Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R b They connect with each other to form substituted or unsubstituted rings;

[0096] Each of the R6 groups is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0097] Each of the R7s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0098] a0 is selected from 1 or 2; a1 is selected from 1, 2, 3 or 4; a2 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; a3 is selected from 1, 2, 3, 4, 5 or 6.

[0099] Preferably, R1 to R3 are each independently selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted methyl ... One or a combination of the following: unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0100] Preferably, the Ar1 is selected from any one of the following groups:

[0101]

[0102]

[0103] X is selected from O or S;

[0104] Each z is independently selected from CH or N;

[0105] Each of the R8s is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0106] p1 is selected from 1, 2, 3 or 4; p2 is selected from 1; p3 is selected from 1 or 2; p4 is selected from 1, 2, 3, 4, 5 or 6; p5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; p6 is selected from 1, 2 or 3; p7 is selected from 1, 2, 3, 4, 5, 6 or 7.

[0107] Preferably, at most two z groups are selected from N, or at most one z group is selected from N.

[0108] Preferably, each of the R8 groups is independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted silyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted spirodifluorene. The following are included in combination: substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0109] Preferably, the Ar2 is selected from one or a combination of the following groups:

[0110]

[0111]

[0112] Each of the E's is independently selected from CH or N;

[0113] Each of the R9s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring.

[0114] The R n It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0115] The R i R j Each is independently selected from one of the following: substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloyl groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0116] The m0 is selected from 1, 2, 3, or 4; the m1 is selected from 1, 2, 3, 4, or 5; the m2 is selected from 1, 2, 3, 4, 5, 6, or 7; the m3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the m4 is selected from 1 or 2; the m5 is selected from 1, 2, or 3; the m6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the m7 is selected from 1, 2, 3, 4, 5, or 6; the m8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the m9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the m 10 Choose from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0117] Preferably, R9 is selected from hydrogen, deuterium, tritium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted silyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl. One of the following: substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl.

[0118] Preferably, at most two E's in the indicated groups are selected from N, or at most one E's is selected from N.

[0119] Preferably, the L0 is selected from one of the following groups:

[0120]

[0121] X5, X6, and X7 are each independently selected from O, S, and C(R). o R s ), N(R c Any one of the following;

[0122] The R o R s Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R o R sThey connect with each other to form substituted or unsubstituted rings;

[0123] The R c It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0124] The R w Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R w They connect with each other to form substituted or unsubstituted rings;

[0125] The R 12 Each is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0126] The term e0 is selected from 1 or 2; the term e1 is selected from 1, 2, 3 or 4; the term e2 is selected from 1, 2, 3, 4, 5 or 6; the term e3 is selected from 1, 2, 3, 4 or 5; the term e4 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the term e5 is selected from 1, 2 or 3; the term e6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the term e7 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; when there are two or more R... 12 At that time, two or more R 12 The same or different between each other, or two adjacent R 12 They connect with each other to form substituted or unsubstituted rings.

[0127] More preferably, the *-L0-(Ra)n0 is selected from one of the following groups:

[0128]

[0129] Preferably, when R a When n0 is selected from -CF3 or -Si(R1R2R3), n0 is selected from 1, 2 or 3, and more preferably 1 or 2.

[0130] Preferably, when R a When n is selected from -F, n0 is selected from 5.

[0131] Preferably, the R 12 Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted silyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted... Or one of the following: dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0132] Preferably, L1 is selected from a single bond or one of the following groups:

[0133]

[0134] The R a When L1 is selected from -CF3, it is not selected from a single bond;

[0135] The X8, X9, X 10 Each is independently selected from O, S, C(R) x R y ), N(R z Any one of the following;

[0136] The Rx R y Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R x R y They connect with each other to form substituted or unsubstituted rings;

[0137] The R z It is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0138] The R v Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R v They connect with each other to form substituted or unsubstituted rings;

[0139] The R 11 Each is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0140] The r0 is selected from 1 or 2; the r1 is selected from 1, 2, 3 or 4; the r2 is selected from 1, 2, 3, 4, 5 or 6; the r3 is selected from 1, 2, 3, 4 or 5; the r4 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the r5 is selected from 1, 2 or 3; the r6 is selected from 1, 2, 3, 4, 5, 6 or 7, 8, 9 or 10; the r7 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; when there are two or more R... 11 At that time, two or more R 11 The same or different between each other, or two adjacent R 11 They connect with each other to form substituted or unsubstituted rings.

[0141] Preferably, the R 11 Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted silyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted... Or one of the following: dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0142] Preferably, L2 is selected from single bonds or one or a combination of the following groups:

[0143]

[0144]

[0145] The R rIt is selected from any one of substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups;

[0146] The R t Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R t They connect with each other to form substituted or unsubstituted rings;

[0147] The R u Each is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or R u They connect with each other to form substituted or unsubstituted rings;

[0148] The R 13 Each is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0149] The R 14Each is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring;

[0150] k0 is selected from 1 or 2; k1 is selected from 1, 2, 3 or 4; k2 is selected from 1, 2, 3, 4, 5 or 6; k3 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; k4 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; k5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; k6 is selected from 1, 2, 3, 4 or 5; k7 is selected from 1, 2 or 3; k8 is selected from 1, 2, 3, 4, 5, 6 or 7.

[0151] Preferably, the R 13 Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted silyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted... Or one of the following: dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0152] Preferably, the R 14Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted silyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted... Or one of the following: dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0153] Most preferably, the triarylamine compound is selected from any one of the following structures:

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] The above lists some specific structural forms of triarylamine compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0177] In addition, the present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises at least one of the triarylamine compounds described in the present invention.

[0178] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains at least one of the triarylamine compounds described in this invention.

[0179] Preferably, the organic electroluminescent device of the present invention may comprise one or more organic layers. These organic layers may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and a capping layer. Specifically, the organic layer located between the anode and cathode may include a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. The organic layer located outside one or more electrodes of the anode and cathode may include a capping layer. The organic layers may be formed as a single layer or as a multilayer structure with multiple organic layers stacked on top of each other. Furthermore, each organic layer may also include one or more layers; for example, the hole transport layer may include a first hole transport layer and a second hole transport layer. However, the structure of the organic electroluminescent device is not limited to this and may include fewer or more organic layers.

[0180] More preferably, the organic layer is located outside one or more of the electrodes, namely the anode and the cathode, and the organic layer includes a capping layer containing the triarylamine compound described in this invention.

[0181] Most preferably, the organic layer is located outside the cathode, and the organic layer includes a capping layer containing the triarylamine compound described in this invention.

[0182] The anode described in this invention is generally preferably made of a material with a high work function, which can be formed by depositing or sputtering the anode material on a substrate. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. When the anode is a transmission electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmission electrode or a reflection electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure comprising two or more layers; for example, the anode can have a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to this.

[0183] The hole injection layer is typically made of a material with a high work function, and can be selected from any one or more of the following structures: metal oxides such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, and titanium oxide; low-molecular-weight organic compounds such as phthalocyanine compounds and conjugated organic materials containing polycyano groups, but not limited to these. Preferably, the hole injection layer of the present invention is selected from 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (abbreviated as: 2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene (abbreviated as: HAT-CN), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviated as: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as: MTDATA), copper phthalocyanine (II) (abbreviated as: CuPc), N,N'-di[4-[di(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-biphenyl-4,4'-diamine (abbreviated as: DNTPD), etc., and can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances.

[0184] The hole transport layer may include a first hole transport layer material and a second hole transport layer material, preferably a material with high hole mobility. The hole transport layer material of this invention may be selected from any one or more of the following structures: phthalocyanine compounds, anthraquinone compounds, biphenyl diamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc., but is not limited thereto.

[0185] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material (also called a matrix material) and a dopant material (also called a guest material). The luminescent layer material can contain multiple host materials and multiple dopant materials. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer needs to possess bipolar charge transport properties and appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. In addition to the carbazole compound provided in this invention, it can also contain anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited to these. The guest material may include, but is not limited to, metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, terbium complexes, europium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, pyrrole derivatives, indole derivatives, carbazole derivatives, etc.

[0186] The electron transport layer may include a first electron transport layer material and a second electron transport layer material. The electron transport material described in this invention may be selected from any one or more of the following structures: metal complexes of oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, bi-benzoquinone derivatives, 8-hydroxyquinoline and its derivatives, which may be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances.

[0187] The electron injection layer of the present invention is preferably made of a material with a low work function, and can be selected from any one or more of the following structures: alkali metal compounds (e.g., lithium oxide, lithium fluoride, cesium carbonate, 8-hydroxyquinoline cesium), metal complexes, etc., and mixtures of electron transport materials and insulating organometallic salts can also be used. In particular, the organometallic salts can include, but are not limited to, metal acetates, metal benzoates or metal stearates.

[0188] The cathode of the present invention is provided in the electron transport region, and the cathode may be selected from a transmission electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmission electrode, the material used to form the cathode may be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode may be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0189] The capping layer of this invention, provided on the outside of the cathode, may be selected from inorganic compounds (e.g., metal oxides, metal nitrides, metal fluorides, etc.), organic compounds (arylamine derivatives, carbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, triazole derivatives, etc.), but is not limited thereto, or any one or a combination of at least two of the triarylamine compounds described in this invention. Preferably, the capping layer material of this invention is selected from any one or a combination of at least two of the triarylamine compounds described in this invention.

[0190] There are no particular limitations on the preparation methods of the above-mentioned organic layers, cathodes, and anodes. Any one of the following methods can be used: vacuum evaporation, inkjet printing, sputtering, plasma, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, and slot coating. The above-mentioned organic layers are preferably prepared by vacuum evaporation, inkjet printing, or spin coating, but are not limited to these methods.

[0191] The organic light-emitting device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, digital cameras, organic photosensitive materials or organic thin-film transistors, automotive systems, and traffic lights.

[0192] Preparation and characterization of compounds

[0193] Description of raw materials, reagents, and characterization equipment:

[0194] The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0195] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0196] 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.

[0197] The following is one method for preparing the compound represented by Chemical Formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of Chemical Formula I can be prepared by the reaction route shown below, using conventional methods well known to those skilled in the art. For example, carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc., and the type and position or number of substituents can be changed according to techniques known in the art.

[0198] Synthetic route

[0199] Preparation of compound I:

[0200]

[0201] X1 to X4 are each independently selected from any one of I, Br, and Cl; Ar1 ​​to Ar2, R a The limitations of L0 to L2 and n0 are the same as those mentioned above.

[0202] Synthesis Example 1: Preparation of Intermediate C-11:

[0203]

[0204] Under nitrogen protection, a'-11 (18.52 g, 80.00 mmol), b'-11 (13.04 g, 80.00 mmol), K2CO3 (16.58 g, 120.00 mmol), and 435 mL of mixed solvent (toluene:ethanol:water = 2:1:1) were added sequentially to the reaction flask. After purging the air three times with nitrogen, Pd(PPh3)4 (0.92 g, 0.80 mmol) was added. The reaction was stirred at reflux temperature for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 10:1 to obtain intermediate C-11 (17.69 g, yield 82%) with HPLC purity ≥ 99.83%. Mass spectrometry m / z: 269.0621 (theoretical value: 269.0607).

[0205] By substituting the raw materials accordingly, the intermediate can be prepared according to the preparation method of intermediate C-11 in Synthesis Example 1. The raw materials are shown in the table below:

[0206]

[0207]

[0208] Synthesis Example 2: Preparation of Intermediate M-36:

[0209]

[0210] Under nitrogen protection, m-36 (17.20 g, 100.00 mmol), n-36 (29.81 g, 100.00 mmol), K2CO3 (20.73 g, 150.00 mmol), and 540 mL of mixed solvent (toluene:ethanol:water = 2:1:1) were added sequentially to the reaction flask. After purging the air three times with nitrogen, Pd(PPh3)4 (1.16 g, 1.00 mmol) was added. The mixture was stirred at reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and washed with ethanol. Finally, the filter cake was recrystallized from toluene:ethanol = 10:1 to obtain intermediate M-36 (29.02 g, yield 84%) with HPLC purity ≥ 99.85%. Mass spectrometry m / z: 345.1502 (theoretical value: 345.1517).

[0211] By substituting the raw materials accordingly, the intermediate can be prepared according to the preparation method of intermediate M-36 in Synthesis Example 1. The raw materials are shown in the table below:

[0212]

[0213]

[0214] Synthesis Example 3: Preparation of Compound 11:

[0215]

[0216] Preparation of intermediate B-11:

[0217] Under nitrogen protection, M-11 (9.92 g, 60.00 mmol), b-11 (16.76 g, 60.00 mmol), and sodium tert-butoxide (10.38 g, 108.00 mmol) were added to 320 mL of toluene. Pd(dppf)Cl2 (0.48 g, 0.65 mmol) was added with stirring. The mixture was heated under reflux for 4 hours. 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 carried out at a lower temperature, filtered, and the resulting solid was recrystallized from ethyl acetate to obtain intermediate B-11 (17.24 g, 79%). HPLC analysis showed the solid purity to be ≥99.89%. Mass spectrometry m / z: 363.1825 (theoretical value: 363.1839).

[0218] Preparation of compound 11:

[0219] Under nitrogen protection, B-11 (14.55 g, 40.00 mmol), C-11 (10.79 g, 40.00 mmol), Pd2(dba)3 (0.37 g, 0.40 mmol), P(t-Bu)3 (1.60 mL of 0.5 M toluene solution, 0.80 mmol), and sodium tert-butoxide (7.69 g, 80.00 mmol) were added to 280 mL of toluene. The mixture was stirred and heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, and dichloromethane and distilled water were added for extraction. The mixture was allowed to stand and separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 11 (17.91 g, 75%). The purity of the solid was determined by HPLC to be ≥99.94%. Mass spectrometry m / z: 596.2662 (theoretical value: 596.2679). Theoretical elemental content (%) C 38 H 40 N₂OSi₂: C, 76.46; H, 6.75; N, 4.69. Measured elemental content (%): C, 76.51; H, 6.72; N, 4.73.

[0220] Synthesis Example 4: Preparation of Compound 17:

[0221]

[0222] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-17, b-11 with an equimolar amount of b-17, and C-11 with an equimolar amount of C-17, yielding compound 17 (19.46 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 704.3211 (theoretical value: 704.3223). Theoretical elemental content (%) C 49 H 44 N₂OSi: C, 83.48; H, 6.29; N, 3.97. Measured elemental content (%): C, 83.53; H, 6.25; N, 4.00.

[0223] Synthesis Example 5: Preparation of Compound 23:

[0224]

[0225] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-23, and C-11 with an equimolar amount of C-23, yielding compound 23 (18.26 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 633.2646 (theoretical value: 633.2632). Theoretical elemental content (%) C 40 H 39 N3OSi2: C, 75.79; H, 6.20; N, 6.63. Measured elemental content (%): C, 75.84; H, 6.16; N, 6.67.

[0226] Synthesis Example 6: Preparation of Compound 33:

[0227]

[0228] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-33, and C-11 with an equimolar amount of C-33, yielding compound 33 (17.29 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 568.2799 (theoretical value: 568.2786). Theoretical elemental content (%) C 38 H 24 D8N2OSi: C, 80.24; H, 7.09; N, 4.92. Measured elemental content (%): C, 80.19; H, 7.12; N, 4.88.

[0229] Synthesis Example 7: Preparation of Compound 36:

[0230]

[0231] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-36, b-11 with an equimolar amount of b-36, and C-11 with an equimolar amount of C-17, yielding compound 36 (19.26 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 687.2720 (theoretical value: 687.2706). Theoretical elemental content (%) C 47 H 37 N3OSi: C, 82.06; H, 5.42; N, 6.11. Measured elemental content (%): C, 82.11; H, 5.39; N, 6.08.

[0232] Synthesis Example 8: Preparation of Compound 68:

[0233]

[0234] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-68, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-17, yielding compound 68 (17.37 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 586.2428 (theoretical value: 586.2440). Theoretical elemental content (%) C 40 H 34 N₂OSi: C, 81.87; H, 5.84; N, 4.77. Measured elemental content (%): C, 81.92; H, 5.88; N, 4.80.

[0235] Synthesis Example 9: Preparation of Compound 72:

[0236]

[0237] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-72, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-72, yielding compound 72 (18.03 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 662.2739 (theoretical value: 662.2753). Theoretical elemental content (%) C 46 H 38 N₂OSi: C, 83.35; H, 5.78; N, 4.23. Measured elemental content (%): C, 83.30; H, 5.81; N, 4.19.

[0238] Synthesis Example 10: Preparation of Compound 74:

[0239]

[0240] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-17, yielding compound 74 (18.09 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 636.2610 (theoretical value: 636.2597). Theoretical elemental content (%) C 44 H 36 N₂OSi: C, 82.98; H, 5.70; N, 4.40. Measured elemental content (%): C, 83.03; H, 5.67; N, 4.44.

[0241] Synthesis Example 11: Preparation of Compound 83:

[0242]

[0243] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-83, b-11 with an equimolar amount of b-83, and C-11 with an equimolar amount of C-17, yielding compound 83 (18.60 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 636.2586 (theoretical value: 636.2597). Theoretical elemental content (%) C 44 H 36 N₂OSi: C, 82.98; H, 5.70; N, 4.40. Measured elemental content (%): C, 83.02; H, 5.65; N, 4.37.

[0244] Synthesis Example 12: Preparation of Compound 86:

[0245]

[0246] Preparation of intermediate d-86:

[0247] Following the same preparation method as intermediate C-11 in Synthesis Example 1, a'-11 was replaced with an equimolar amount of a'-33, and b'-11 was replaced with an equimolar amount of e-86, yielding intermediate d-86 (17.59 g). HPLC analysis showed a solid purity ≥ 99.84%. Mass spectrometry m / z: 264.1051 (theoretical value: 264.1039).

[0248] Preparation of compound 86:

[0249] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-86, b-11 with an equimolar amount of d-86, and C-11 with an equimolar amount of C-86, yielding compound 86 (18.65 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 665.2815 (theoretical value: 665.2800). Theoretical elemental content (%) C 45 H 31 D4N3OSi: C, 81.17; H, 5.90; N, 6.31. Measured elemental content (%): C, 81.22; H, 5.86; N, 6.34.

[0250] Synthetic Example 13: Preparation of Compound 96:

[0251]

[0252] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-96, and C-11 with an equimolar amount of C-17, yielding compound 96 (20.08 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 822.3080 (theoretical value: 822.3066). Theoretical elemental content (%) C 59 H 42 N₂OSi: C, 86.10; H, 5.14; N, 3.40. Measured elemental content (%): C, 86.05; H, 5.18; N, 3.37.

[0253] Synthesis Example 14: Preparation of Compound 109:

[0254]

[0255] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-109, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-109, yielding compound 109 (18.19 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 688.2671 (theoretical value: 688.2658). Theoretical elemental content (%) C 46 H 36 N4OSi: C, 80.20; H, 5.27; N, 8.13. Measured elemental content (%): C, 80.15; H, 5.31; N, 8.10.

[0256] Synthetic Example 15: Preparation of Compound 113:

[0257]

[0258] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-113, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-113, yielding compound 113 (19.05 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 743.2839 (theoretical value: 743.2829). Theoretical elemental content (%) C 47 H 37 N7OSi: C, 75.88; H, 5.01; N, 13.18. Measured elemental content (%): C, 75.93; H, 4.98; N, 13.22.

[0259] Synthetic Example 16: Preparation of Compound 115:

[0260]

[0261] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-115, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-115, yielding compound 115 (18.10 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 655.2442 (theoretical value: 655.2455). Theoretical elemental content (%) C 43 H 34 FN3OSi: C, 78.75; H, 5.23; N, 6.41. Measured elemental content (%): C, 78.80; H, 5.19; N, 6.37.

[0262] Synthesis Example 17: Preparation of Compound 123:

[0263]

[0264] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-123, b-11 with an equimolar amount of b-123, and C-11 with an equimolar amount of C-17, yielding compound 123 (17.75 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 607.2659 (theoretical value: 607.2672). Theoretical elemental content (%) C 40 H 25 D7N2O2Si: C, 79.04; H, 6.47; N, 4.61. Measured elemental content (%): C, 78.99; H, 6.51; N, 4.58.

[0265] Synthetic Example 18: Preparation of Compound 146:

[0266]

[0267] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-146, yielding compound 146 (18.28 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 736.2898 (theoretical value: 736.2910). Theoretical elemental content (%) C 52 H 40 N₂OSi: C, 84.75; H, 5.47; N, 3.80. Measured elemental content (%): C, 84.80; H, 5.50; N, 3.76.

[0268] Synthesis Example 19: Preparation of Compound 163:

[0269]

[0270] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-163, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-163, yielding compound 163 (18.82 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 662.2346 (theoretical value: 662.2357). Theoretical elemental content (%) C 41 H 31 F5N2O: C, 74.31; H, 4.72; N, 4.23. Measured elemental content (%): C, 74.26; H, 4.68; N, 4.26.

[0271] Synthesis Example 20: Preparation of Compound 171:

[0272]

[0273] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-171, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-171, yielding compound 171 (19.34 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 690.2621 (theoretical value: 690.2608). Theoretical elemental content (%) C 43 H 27 D4F5N2O: C, 74.77; H, 5.11; N, 4.06. Measured elemental content (%): C, 74.82; H, 5.07; N, 4.10.

[0274] Synthesis Example 21: Preparation of Compound 176:

[0275]

[0276] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-17, yielding compound 176 (19.64 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 654.1719 (theoretical value: 654.1731). Theoretical elemental content (%) C 41 H 23 F5N2O: C, 75.22; H, 3.54; N, 4.28. Measured elemental content (%): C, 75.17; H, 3.50; N, 4.31.

[0277] Synthesis Example 22: Preparation of Compound 187:

[0278]

[0279] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-187, and C-11 with an equimolar amount of C-187, yielding compound 187 (19.33 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 710.2370 (theoretical value: 710.2357). Theoretical elemental content (%) C 45 H 31 F5N2O: C, 76.05; H, 4.40; N, 3.94. Measured elemental content (%): C, 76.10; H, 4.36; N, 3.97.

[0280] Synthetic Example 23: Preparation of Compound 193:

[0281]

[0282] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-193, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-193, yielding compound 193 (20.78 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 711.2321 (theoretical value: 711.2309). Theoretical elemental content (%) C 44 H 30F5N3O: C, 74.25; H, 4.25; N, 5.90. Measured elemental content (%): C, 74.30; H, 4.29; N, 5.87.

[0283] Synthesis Example 24: Preparation of Compound 201:

[0284]

[0285] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-201, b-11 with an equimolar amount of b-201, and C-11 with an equimolar amount of C-17, yielding compound 201 (19.21 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 716.1499 (theoretical value: 716.1510). Theoretical elemental content (%) C 40 H 21 F9N2O: C, 67.04; H, 2.95; N, 3.91. Measured elemental content (%): C, 66.99; H, 2.91; N, 3.88.

[0286] Synthesis Example 25: Preparation of Compound 208:

[0287]

[0288] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-208, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-208 to obtain compound 208 (19.48 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 705.1856 (theoretical value: 705.1840). Theoretical elemental content (%) C 44 H 24 F5N3O: C, 74.89; H, 3.43; N, 5.95. Measured elemental content (%): C, 74.94; H, 3.39; N, 5.98.

[0289] Synthesis Example 26: Preparation of Compound 213:

[0290]

[0291] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-213, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-213 to obtain compound 213 (18.37 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 706.1779 (theoretical value: 706.1792). Theoretical elemental content (%) C43 H 23 F5N4O: C, 73.08; H, 3.28; N, 7.93. Measured elemental content (%): C, 73.13; H, 3.32; N, 7.89.

[0292] Synthesis Example 27: Preparation of Compound 216:

[0293]

[0294] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-115, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-216 to obtain compound 216 (19.50 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 727.1292 (theoretical value: 727.1306). Theoretical elemental content (%) C 40 H 18 F9N3O: C, 66.03; H, 2.49; N, 5.78. Measured elemental content (%): C, 65.98; H, 2.52; N, 5.82.

[0295] Synthesis Example 28: Preparation of Compound 269:

[0296]

[0297] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-269, b-11 with an equimolar amount of b-269, and C-11 with an equimolar amount of C-269, yielding compound 269 (18.12 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 580.2151 (theoretical value: 580.2138). Theoretical elemental content (%) C 36 H 28 F4N2O: C, 74.47; H, 4.86; N, 4.82. Measured elemental content (%): C, 74.52; H, 4.90; N, 4.79.

[0298] Synthesis Example 29: Preparation of Compound 288:

[0299]

[0300] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-288, b-11 with an equimolar amount of b-269, and C-11 with an equimolar amount of C-288, yielding compound 288 (19.69 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 683.2173 (theoretical value: 683.2184). Theoretical elemental content (%) C 45 H 28 F3N3O: C, 79.05; H, 4.13; N, 6.15. Measured elemental content (%): C, 79.10; H, 4.09; N, 6.18.

[0301] Synthesis Example 30: Preparation of Compound 292:

[0302]

[0303] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-292, b-11 with an equimolar amount of b-269, and C-11 with an equimolar amount of C-292, yielding compound 292 (18.47 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 584.1839 (theoretical value: 584.1824). Theoretical elemental content (%) C 36 H 23 F3N4O: C, 73.96; H, 3.97; N, 9.58. Measured elemental content (%): C, 74.00; H, 4.02; N, 9.61.

[0304] Synthesis Example 31: Preparation of Compound 314:

[0305]

[0306] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-314, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-314, yielding compound 314 (19.28 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 642.2579 (theoretical value: 642.2593). Theoretical elemental content (%) C 41 H 17 D9F3N3O: C, 76.62; H, 5.49; N, 6.54. Measured elemental content (%): C, 76.57; H, 5.51; N, 6.50.

[0307] Synthesis Example 32: Preparation of Compound 323:

[0308]

[0309] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-17, yielding compound 323 (18.47 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 632.2090 (theoretical value: 632.2075). Theoretical elemental content (%) C 42 H 27 F3N2O: C, 79.73; H, 4.30; N, 4.43. Measured elemental content (%): C, 79.68; H, 4.26; N, 4.39.

[0310] Synthesis Example 33: Preparation of Compound 353:

[0311]

[0312] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-353, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-353, yielding compound 353 (19.00 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 678.2754 (theoretical value: 678.2765). Theoretical elemental content (%) C 45 H 25 D6F3N2O: C, 79.63; H, 5.49; N, 4.13. Measured elemental content (%): C, 79.58; H, 5.53; N, 4.09.

[0313] Synthesis Example 34: Preparation of Compound 364:

[0314]

[0315] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-364, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-364, yielding compound 364 (18.80 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 701.1913 (theoretical value: 701.1902). Theoretical elemental content (%) C 42 H 25 F6N3O: C, 71.89; H, 3.59; N, 5.99. Measured elemental content (%): C, 71.94; H, 3.63; N, 5.96.

[0316] Synthesis Example 35: Preparation of Compound 370:

[0317]

[0318] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-370, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-370, yielding compound 370 (18.81 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 734.2280 (theoretical value: 734.2293). Theoretical elemental content (%) C 48 H 29 F3N4O: C, 78.46; H, 3.98; N, 7.63. Measured elemental content (%): C, 78.51; H, 4.02; N, 7.59.

[0319] Synthesis Example 36: Preparation of Compound 390:

[0320]

[0321] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-23, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-390, yielding compound 390 (18.47 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 732.2400 (theoretical value: 732.2388). Theoretical elemental content (%) C 50 H 31 F3N2O: C, 81.95; H, 4.26; N, 3.82. Measured elemental content (%): C, 82.00; H, 4.30; N, 3.79.

[0322] Synthesis Example 37: Preparation of Compound 414:

[0323]

[0324] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-414, b-11 with an equimolar amount of b-414, and C-11 with an equimolar amount of C-414, yielding compound 414 (17.60 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 578.1973 (theoretical value: 578.1960). Theoretical elemental content (%) C 36 H 30 N4SSi: C, 74.70; H, 5.22; N, 9.68. Measured elemental content (%): C, 74.65; H, 5.18; N, 9.71.

[0325] Synthesis Example 38: Preparation of Compound 514:

[0326]

[0327] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-514, b-11 with an equimolar amount of b-68, and C-11 with an equimolar amount of C-514, yielding compound 514 (18.23 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 632.1790 (theoretical value: 632.1776). Theoretical elemental content (%) C 40 H 32 N₂S₂Si: C, 75.91; H, 5.10; N, 4.43. Measured elemental content (%): C, 75.86; H, 5.06; N, 4.47.

[0328] Synthesis Example 39: Preparation of Compound 636:

[0329]

[0330] Following the same preparation method as compound 11 in Synthesis Example 3, M-11 was replaced with an equimolar amount of M-636, b-11 with an equimolar amount of b-163, and C-11 with an equimolar amount of C-636, yielding compound 636 (20.39 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 738.1890 (theoretical value: 738.1877). Theoretical elemental content (%) C 44 H 27 F5N4S: C, 71.53; H, 3.68; N, 7.58. Measured elemental content (%): C, 71.48; H, 3.71; N, 7.62.

[0331] Synthesis Example 40: Preparation of Compound 702:

[0332]

[0333] Following the same preparation method as compound 11 in Example 3, M-11 was replaced with an equimolar amount of M-702, b-11 with an equimolar amount of b-314, and C-11 with an equimolar amount of C-702, yielding compound 702 (18.74 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 624.1582 (theoretical value: 624.1596). Theoretical elemental content (%) C 38 H 23F3N4S: C, 73.06; H, 3.71; N, 8.97. Measured elemental content (%): C, 73.11; H, 3.67; N, 9.00.

[0334] [Device Example 1]

[0335] First, an ITO / Ag / ITO glass substrate was cut into 50mm × 50mm × 0.7mm pieces to serve as the anode. The substrate was washed twice with distilled water, then ultrasonically cleaned for 30 minutes. Next, it was ultrasonically cleaned for 15 minutes each with solvents such as acetone, isopropanol, and methanol, followed by UV ozone cleaning for 30 minutes. The substrate was then placed in an evaporation deposition machine. A 35nm thick layer of compound HI-1 was deposited on the prepared ITO transparent electrode on the glass substrate as a hole injection layer. A 40nm thick layer of HT-1 was then vacuum-deposited on the hole injection layer as a hole transport layer. Under the same vacuum deposition conditions, a 35nm thick layer of host material and dopant (5wt%) was deposited on the hole transport layer as a light-emitting layer. The host material was GH, and the dopant was GD, mixed and deposited at a mass ratio of 98:2. A 10 nm layer of HB-1 was sequentially deposited on the upper surface of the light-emitting layer as a hole-blocking layer. On the hole-blocking layer, an ET-1 layer (30 nm) was sequentially deposited as an electron transport layer by vacuum evaporation, followed by an electron injection layer of LiF (1 nm) and a cathode of Mg:Ag (10 nm). Subsequently, compound 11 prepared in Example 1 was deposited on the cathode as a capping layer (65 nm) to prepare an organic electroluminescent device.

[0336]

[0337] [Device Examples 2-38]

[0338] Compounds 17, 23, 33, 36, 68, 72, 74, 83, 86, 96, 109, 113, 115, 123, 146, 163, 171, 176, 187, 193, 201, 208, 213, 216, 269, 288, 292, 314, 323, 353, 364, 370, 390, 414, 514, 636, and 702 of the present invention were used to replace compound 11 in device example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0339] [Comparative Device Examples 1-7]

[0340] Comparative Examples 1-7: Fabrication of Comparative Organic Electroluminescent Devices 1-7

[0341] By replacing compound 11 in the capping layer of Example 1 with Ref-1 to Ref-7 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 7 were obtained.

[0342] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0343] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-38 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-7 are shown in Table 1 below.

[0344] Table 1:

[0345]

[0346]

[0347] As shown in Table 1, the triarylamine compounds of this invention have excellent asymmetric spatial configurations and easily tunable glass transition temperatures, resulting in good rigidity. When used as capping materials for organic electroluminescent devices, the driving voltage, luminous efficiency, and lifespan of the devices are significantly improved, indicating that the triarylamine compounds of this invention are a class of high-performance OLED capping materials.

[0348] [Device Example 39]

[0349] First, an ITO / Ag / ITO glass substrate was cut into 50mm × 50mm × 0.7mm pieces to serve as the anode. The substrate was washed twice with distilled water, then ultrasonically cleaned for 30 minutes. Next, it was ultrasonically cleaned for 15 minutes each with solvents such as acetone, isopropanol, and methanol, followed by UV ozone cleaning for 30 minutes. The substrate was then placed in an evaporation deposition machine. A 35nm thick layer of compound HI-2 was deposited on the prepared ITO transparent electrode on the glass substrate as a hole injection layer. A 40nm thick layer of HT-2 was then vacuum-deposited on the hole injection layer as a hole transport layer. Under the same vacuum deposition conditions, a 35nm thick layer of host material and dopant (8wt%) was deposited on the hole transport layer as a light-emitting layer. The host material was RH, and the dopants were mixed and deposited at a mass ratio of 98:2. A 10 nm layer of HB-2 was sequentially deposited on the upper surface of the light-emitting layer as a hole-blocking layer. On the hole-blocking layer, an ET-2 layer (30 nm) was sequentially deposited as an electron transport layer by vacuum evaporation, followed by an electron injection layer of LiF (1 nm) and a cathode of Mg:Ag (12 nm). Subsequently, compound 11 prepared in Example 39 was deposited on the cathode as a capping layer (65 nm) to prepare an organic electroluminescent device.

[0350]

[0351] [Device Examples 40–76]

[0352] Compounds 17, 23, 33, 36, 68, 72, 74, 83, 86, 96, 109, 113, 115, 123, 146, 163, 171, 176, 187, 193, 201, 208, 213, 216, 269, 288, 292, 314, 323, 353, 364, 370, 390, 414, 514, 636, and 702 of the present invention were used to replace compound 11 in device example 39 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 39.

[0353] [Comparative Device Examples 8-14]

[0354] Comparative Examples 8-14: Fabrication of Comparative Organic Electroluminescent Devices 8-14

[0355] By replacing compound 11 in the capping layer of Example 39 with Ref-1 to Ref-7 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 8 to 14 were obtained.

[0356] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0357] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 39-76 in the device embodiments of this invention, and those of comparative embodiments 8-14, are shown in Table 2 below.

[0358] Table 2:

[0359]

[0360]

[0361] As shown in Table 2, the triarylamine compounds of this invention have excellent asymmetric spatial configurations and easily tunable glass transition temperatures, resulting in good rigidity. When used as capping materials for organic electroluminescent devices, the driving voltage, luminous efficiency, and lifespan of the devices are significantly improved, indicating that the triarylamine compounds of this invention are a class of high-performance OLED capping materials.

[0362] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A triarylamine compound, characterized in that, The triarylamine compounds have the structure shown in Formula I: In the above formula I, the , , They are different from each other; The Ar1 is selected from any one of the following groups, and the group is connected to L1 via a * site: X is selected from O or S; Each z in the group is independently selected from CH or N, and at most two z are selected from N; the z in the remaining groups are selected from CH. Each of the R8 groups is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl. p1 is selected from 1, 2, 3, or 4; p2 is selected from 1; p3 is selected from 1 or 2; p4 is selected from 1, 2, 3, 4, 5, or 6; p5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; p6 is selected from 1, 2, or 3. The Ar2 is selected from one or a combination of the following groups: Each of the E's is independently selected from CH; Each of the R9s mentioned herein is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted dihydroindyl, and substituted or unsubstituted tetrahydronaphthyl. The remaining R9 are each independently selected from one of hydrogen, deuterium, tritium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, and substituted or unsubstituted phenyl. The R i R j Each is independently selected from one of the substituted or unsubstituted C1 to C6 alkyl groups; The m0 is selected from 1, 2, 3, or 4; the m1 is selected from 1, 2, 3, 4, or 5; the m2 is selected from 1, 2, 3, 4, 5, 6, or 7; the m3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the m4 is selected from 1 or 2; the m5 is selected from 1, 2, or 3; the m6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the m7 is selected from 1, 2, 3, 4, 5, or 6. The Selected from one of the following groups: R a Selected from -CF3, -Si(R1R2R3), n0 is selected as 1 or 2; or R a Selected from -F, n0 is selected from 5; each of R1 to R3 is independently selected from any one of substituted or unsubstituted C1 to C6 alkyl groups and substituted or unsubstituted C6 to C12 aryl groups; The R 12 It is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, and substituted or unsubstituted phenyl; The term e0 is selected from 1 or 2; the term e1 is selected from 1, 2, 3 or 4; the term e5 is selected from 1, 2 or 3; when there are two or more R... 12 At that time, two or more R 12 They are the same as or different from each other; The L1 is selected from a single bond or one of the following groups: The R a When L1 is selected from -CF3, it is not selected from a single bond; The R 11 Each is independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl; The r0 is selected from 1 or 2; the r1 is selected from 1, 2, 3 or 4; the r2 is selected from 1, 2, 3, 4, 5 or 6; the r3 is selected from 1, 2, 3, 4 or 5; the r4 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the r5 is selected from 1, 2 or 3; the r6 is selected from 1, 2, 3, 4, 5, 6 or 7, 8, 9 or 10; The L2 is selected from a single bond or one or a combination of the following groups: The R 13 Each is independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl; k0 is selected from 1 or 2; k1 is selected from 1, 2, 3 or 4; k2 is selected from 1, 2, 3, 4, 5 or 6; k3 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; k5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; k7 is selected from 1, 2 or 3; The substituents in "substituted or unsubstituted" in R9 are independently selected from: deuterium, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The substituents mentioned in the remaining "substituted or unsubstituted" are independently selected from: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl; The condition is that the triarylamine compound is not: .

2. The triarylamine compound according to claim 1, characterized in that, The Ar1 is selected from any one of the following groups: Each of the R8 groups is independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, C1-C6 alkyl, and phenyl.

3. The triarylamine compound according to claim 1, characterized in that, The Ar2 is selected from one or a combination of the following groups: Each of the R9s is independently selected from one of the following: hydrogen, deuterium, tritium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, and substituted or unsubstituted phenyl.

4. The triarylamine compound according to claim 1, characterized in that, The Selected from one of the following groups: R a Selected from -CF3, -Si(R1R2R3), n0 is selected as 1 or 2; or R a Selected from -F, n0 is selected from 5; each of R1 to R3 is independently selected from any one of substituted or unsubstituted C1 to C6 alkyl groups, substituted or unsubstituted phenyl groups; The R 12 It is selected from one of hydrogen, deuterium, and tritium.

5. The triarylamine compound according to claim 1, characterized in that, The L1 is selected from a single bond or one of the following groups: The R 11 Each is independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1 to C6 alkyl groups.

6. The triarylamine compound according to claim 1, characterized in that, The L2 is selected from a single bond or one or a combination of the following groups: The R 13 Each is independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1 to C6 alkyl groups.

7. A triarylamine compound, characterized in that, The triarylamine compounds are selected from any of the following chemical structures:

8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, characterized in that, The organic layer includes a capping layer, which contains any one of the triarylamine compounds according to any one of claims 1 to 7.

Images