阅读说明：本技术 一种芳胺化合物及其有机电致发光器件 (Arylamine compound and organic electroluminescent device thereof ) 是由 郭建华 刘喜庆 杜明珠 周雯庭 于 2021-07-28 设计创作，主要内容包括：本发明涉及有机光电材料技术领域,具体涉及一种芳胺化合物及其有机电致发光器件。本发明提供的式(I)所述的芳胺化合物具有很好的热稳定性、成膜性和空穴传输能力,具有相对于其他功能层,特别是发光层更适当的HOMO和T1值,能够有效避免在发光层与空穴传输区域之间的界面发光,从而降低有机材料因界面发光而受热老化的速度,进而改善器件的驱动电压、发光效率及使用寿命。(The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic electroluminescent device thereof. The arylamine compound disclosed by the formula (I) has good thermal stability, film forming property and hole transport capability, has more appropriate HOMO and T1 values relative to other functional layers, particularly a light-emitting layer, and can effectively avoid the light emission at the interface between the light-emitting layer and the hole transport region, so that the heat aging speed of an organic material due to the interface light emission is reduced, and the driving voltage, the light-emitting efficiency and the service life of a device are further improved.)

1. An arylamine compound characterized by having a structure represented by formula (I):

wherein, X is selected from oxygen atom or sulfur atom;

said L₁～L₆Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;

ar is₁～Ar₄At least one of the substituents is selected from one of the substituents containing alicyclic rings shown as the following, and the rest is independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30:

wherein e is an integer of 0-2, f is an integer of 0-3, g is an integer of 0-4, h is an integer of 0-6, i is an integer of 0-8, j is an integer of 0-10, and k is an integer of 0-1;

said R₂₁、R₂₂Independently selected from the group consisting of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, isobutyl group, deuterated isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropane group, deuterated cyclopropane group, cyclobutane group, deuterated cyclobutane group, cyclopentane group, deuterated cyclopentyl group, cyclohexane group, deuterated cyclohexane group, cycloheptane group, deuterated cycloheptane group, norbornyl group, deuterated norbornyl group, adamantyl group, deuterated adamantyl group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, anthracenyl group, deuterated anthracenyl group, phenanthrenyl group, deuterated phenanthrenyl group, triphenylenyl group, deuterated triphenylenyl group, pyrenyl group, dibenzofuranyl group, deuterated dibenzofuranyl group, dibenzothiophenyl group, and deuterated phenyl group, Deuterated dibenzothiophene-based, phenylcarbazolyl, deuterated phenylcarbazolyl,One of 9, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl and deuterated spirobifluorenyl, when a plurality of R exist₂₁Or R₂₂When a plurality of R₂₁Same or different, a plurality of R₂₂The same or different;

m is an integer from 0 to 3, and n is an integer from 0 to 4;

said R_a、R_bIndependently selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, when a plurality of R exist_aOr R_bWhen a plurality of R_aSame or different, a plurality of R_bThe same or different;

the above-mentioned "heteroaryl" group contains at least one heteroatom as follows: oxygen atom, sulfur atom, nitrogen atom, silicon atom;

the substituent in the above "substituted or unsubstituted" is independently selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, isobutyl group, deuterated isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropane group, deuterated cyclopropane group, cyclobutane group, deuterated cyclobutane group, cyclopentyl group, deuterated cyclopentyl group, cyclohexane group, deuterated cyclohexane group, cycloheptane group, deuterated cycloheptane group, norbornyl group, deuterated norbornyl group, adamantyl group, deuterated adamantyl group, vinyl group, methoxy group, ethoxy group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, anthracenyl group, deuterated anthracenyl group, phenanthrenyl group, deuterated phenanthrenyl group, triphenylenyl group, deuterated phenyl group, pyrenyl group, deuterated pyrenyl group, and the like, Pyridyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-diphenylfluorenyl, spirobifluorenyl, and deuterated spirobifluorenyl, wherein the number of substituents is one or more, and when a plurality of substituents are present, the plurality of substituents are the same or different.

2. The arylamine compound according to claim 1, wherein L is₁～L₆Independently selected from one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group.

3. The arylamine compound according to claim 1, wherein L is₁～L₆Independently selected from a single bond or one of the following substituents:

wherein a is an integer from 0 to 4, b is an integer from 0 to 2, c is an integer from 0 to 3, and d is an integer from 0 to 1;

said R₁₁Selected from the group consisting of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, isobutyl group, deuterated isobutyl group, tert-butyl group, deuterated tert-butyl group, methoxy group, ethoxy group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, anthryl group, deuterated anthryl group, phenanthryl group, deuterated phenanthryl group, triphenylenyl group, deuterated triphenylenyl group, pyrenyl group, deuterated pyrenyl group, dipyrenyl group, etcBenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl and deuterated spirobifluorenyl, wherein when a plurality of R are present₁₁When a plurality of R₁₁The same or different;

said R₁₂、R₁₃、R₁₈Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl and deuterated naphthyl; when R is₁₂And R₁₃Independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, R is a hydrogen atom, and R is a hydrogen atom, a hydroxyl group₁₂And R₁₃Can be connected to form a substituted or unsubstituted aliphatic ring of C3-C7; when R is₁₂And R₁₃Independently selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, R₁₂And R₁₃May be linked to form a five-membered carbocyclic ring;

said R₁₄One selected from phenyl, deuterated phenyl, naphthyl and deuterated naphthyl;

said R₁₅、R₁₆、R₁₇Independently selected from one of phenylene, deuterated phenyl, naphthylene and deuterated naphthyl;

when R is₁₈R is selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl₁₇And R₁₈May be linked to form a five-membered carbocyclic ring.

4. The arylamine compound according to claim 1, wherein L is₁～L₆Independently selected from single bonds or from the group consisting ofOne of the substituents:

wherein, a is₁Is selected from an integer of 0 to 4, b₁Is selected from an integer of 0 to 6, c₁Is selected from an integer of 0 to 8, d₁An integer selected from 0 to 3.

5. The arylamine compound according to claim 1, wherein Ar is represented by formula₁～Ar₄At least one of which is selected from one of the substituents shown below:

6. the arylamine compound according to claim 1, wherein Ar is not selected from the group consisting of substituents having an alicyclic ring₁～Ar₄The groups are independently selected from one of the following substituents: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl, and substituted or unsubstituted spirofluorenyl.

7. The arylamine compound according to claim 1, wherein Ar is not selected from the group consisting of substituents having an alicyclic ring₁～Ar₄The groups are independently selected from the following groupsOne of the substituents:

wherein l is an integer from 0 to 5, p is an integer from 0 to 3, q is an integer from 0 to 4, and r is an integer from 0 to 2;

said R₃₁Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a cyclobutane group, a cyclopentane group, a deuterated cyclopentane group, a cyclohexane group, a deuterated cyclohexane group, a cycloheptane group, a norbornyl group, a deuterated norbornyl group, an adamantyl group, a deuterated adamantyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a deuterated naphthyl group, an anthracene group, a phenanthryl group, a deuterated phenanthryl group, a triphenylphenyl group, a deuterated triphenylenyl group, a pyrenyl group, a deuterated pyrenyl group, a dibenzofuranyl group, a deuterated n group, a substituted dibenzofuranyl group, a substituted benzene group, Dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl and deuterated spirobifluorenyl when a plurality of R exist₃₁When a plurality of R₃₁The same or different, or any two adjacent groups are connected to form a substituted or unsubstituted aromatic ring of C6-C10;

said R₃₂One selected from phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl and deuterated biphenyl;

said R₃₃、R₃₄、R₃₆Independently selected from the group consisting of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a deuterated methyl group, a deuterated ethyl group, a n-propyl group, a deuterated isopropyl group, a substituted isopropyl group, a,One of sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl and deuterated naphthyl; when R is₃₃And R₃₄Independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, R₃₃And R₃₄Can be connected to form a substituted or unsubstituted aliphatic ring of C3-C7; when R is₃₃And R₃₄Independently selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, R₃₃And R₃₄May be linked to form a five-membered carbocyclic ring;

said R₃₅、R₃₇Independently selected from one of phenylene, deuterated phenyl, biphenylene, deuterated biphenylene, naphthylene and deuterated naphthyl.

8. The arylamine compound according to claim 1, wherein Ar is not selected from the group consisting of substituents having an alicyclic ring₁～Ar₄The groups are independently selected from one of the following substituents:

9. an arylamine compound characterized by having one of structures represented by formulae (II-A) to (II-F):

wherein, L is₃～L₆、Ar₁～Ar₄And X is the same as in claim 1.

10. An arylamine compound according to claim 1, characterized in that the arylamine compound has one of the structures represented by formulae (III-a) to (III-P):

wherein, L is₃～L₆、Ar₁～Ar₄And X is the same as in claim 1.

11. The arylamine compound according to claim 10, characterized in that the arylamine compound has one of the structures represented by formulae (IV-a) to (IV-F):

wherein, L is₃～L₆、Ar₁～Ar₄And X is the same as in claim 1.

12. An arylamine compound is characterized in that the arylamine compound is selected from one of the following compounds:

13. an organic electroluminescent device comprising an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transport region, a light emitting layer and an electron transport region, and is characterized in that the hole transport region contains one or more arylamine compounds according to any one of claims 1 to 12.

Technical Field

The invention relates to the technical field of organic photoelectric materials, in particular to an arylamine compound and an organic electroluminescent device thereof.

Background

Organic Light-Emitting diodes (OLEDs) have been used to some extent in the field of illumination and display by virtue of their advantages of small thickness, Light weight, wide viewing angle, short response time, wide application temperature range, low energy consumption, high Light-Emitting efficiency, good color purity, good flexibility, etc.

The OLED device is of a sandwich structure and comprises a cathode, an anode and an organic layer arranged between the cathode and the anode, wherein the organic layer is divided into a hole transmission area, an electron transmission area, a light emitting area and the like according to different functions. Under the action of an external electric field, holes and electrons are respectively injected from the anode and the cathode, enter the light emitting region through the hole transmission region and the electron transmission region, are recombined to generate excitons, then release energy, the excitons migrate under the action of the electric field and transfer the energy to the luminescent material in the light emitting region, the electrons in the luminescent material molecules are excited to jump from a ground state to an excited state, and when the electrons return to the ground state from the excited state, the energy is released in the form of light, so that the light emitting phenomenon is generated.

The hole transport region mainly functions to inject and transport holes, and includes a hole injection layer, a hole transport layer, a light emission auxiliary layer, and the like. Hole transport materials should generally possess high hole mobility, good thermal stability, good film formation, a suitable Highest Occupied Molecular Orbital (HOMO) and triplet energy levels (T1). Aromatic amine compounds are one of the most widely used hole transport materials in the field of OLEDs, however, aromatic amine compounds of different structures differ in their properties. For example, different groups directly linked to N may produce different degrees of electronic effects (including inductive and conjugation), resulting in different hole transport capabilities, different HOMO and different T1 values for the compound.

Disclosure of Invention

The invention provides an arylamine compound which has high hole mobility, good thermal stability and excellent film forming property and has HOMO and T1 values matched with a light-emitting layer, and the arylamine compound has a structure shown in a formula (I):

wherein, X is selected from oxygen atom or sulfur atom;

said L₁～L₆Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;

ar is₁～Ar₄At least one of the substituents is selected from one of the substituents containing alicyclic rings shown as the following, and the rest is independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30:

wherein e is an integer of 0-2, f is an integer of 0-3, g is an integer of 0-4, h is an integer of 0-6, i is an integer of 0-8, j is an integer of 0-10, and k is an integer of 0-1;

said R₂₁、R₂₂Independently selected from the group consisting of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, isobutyl group, deuterated isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropyl group, deuterated cyclopropyl group, cyclobutyl group, deuterated cyclobutyl group, cyclopentyl group, deuterated cyclopentyl group, cyclohexyl group, deuterated cyclohexane groupA group selected from the group consisting of a phenyl group, a cycloheptyl group, a deuterated cycloheptyl group, a norbornyl group, a deuterated norbornyl group, an adamantyl group, a deuterated adamantyl group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a deuterated anthracenyl group, a phenanthrenyl group, a deuterated phenanthrenyl group, a triphenylenyl group, a deuterated triphenylenyl group, a pyrenyl group, a deuterated pyrenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a dibenzothienyl group, a phenylcarbazolyl group, a deuterated phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a deuterated 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, a deuterated 9, 9-diphenylfluorenyl group, a spirobifluorenyl group, and a deuterated spirobifluorenyl group, when one or more R is present₂₁Or R₂₂When a plurality of R₂₁Same or different, a plurality of R₂₂The same or different;

m is an integer from 0 to 3, and n is an integer from 0 to 4;

said R_a、R_bIndependently selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, when a plurality of R exist_aOr R_bWhen a plurality of R_aSame or different, a plurality of R_bThe same or different.

The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transmission area, a luminescent layer and an electron transmission area, and the hole transmission area contains one or more than one of the arylamine compounds.

Has the advantages that:

the arylamine compound disclosed by the formula (I) has good hole mobility, has more appropriate HOMO and T1 values relative to other functional layers, particularly a light-emitting layer, is a hole transport material with excellent performance, and can well prevent excitons from migrating to the light-emitting layer and a hole transport region when being used as a light-emitting auxiliary layer, so that light is prevented from emitting at an interface between the light-emitting layer and the hole transport region, and the driving voltage and the light-emitting efficiency of a device can be effectively improved. The arylamine compound has high glass transition temperature (Tg), good thermal stability and good film-forming property, and can effectively avoid the interface luminescence between a luminescent layer and a hole transport region when being used as a luminescence auxiliary layer, thereby reducing the thermal aging speed of organic materials (particularly hole transport materials) due to the interface luminescence and prolonging the service life of devices.

Detailed Description

The following will clearly and completely describe the technical solutions of the specific embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.

In the present specification, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example,can representAnd so on.

The alkyl group in the present invention refers to a hydrocarbon group obtained by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group or a branched-chain alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but is not limited thereto; the branched alkyl group includes, but is not limited to, an isomeric group of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, and the like. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group.

The cycloalkyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from a cycloalkane molecule, and preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms, and examples thereof may include, but are not limited to, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, an adamantyl group, a norbornyl group, and the like. The alkyl group is preferably a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group or a norbornyl group.

The aryl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule, and may be monocyclic aryl group, polycyclic aryl group or condensed ring aryl group, and preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, phenyl group and the like, but is not limited thereto; the polycyclic aromatic group means an aromatic group having two or more independent aromatic rings in the molecule, for example, biphenyl group, terphenyl group and the like, but is not limited thereto; the fused ring aryl group refers to an aryl group in which two or more aromatic rings are contained in a molecule and are fused together by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, and the like. The above aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylene group, or a spirobifluorenyl group.

The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen or phosphorus atom, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl and the like, but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroaryl group includes quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl and the like, but is not limited thereto. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group or a phenoxathiyl group.

The arylene group in the present invention refers to a general term of divalent groups remaining after two hydrogen atoms are removed from the aromatic core carbon of the aromatic compound molecule, and may be monocyclic arylene group, polycyclic arylene group, condensed ring arylene group, or a combination thereof, and preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic arylene group includes phenylene group and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene group, terphenylene group, phenylene-naphthylene group, naphthylene-naphthylene group, phenylene-fluorenylene-phenylene group, phenylene-spirolylene-phenylene group and the like, but is not limited thereto; the condensed ring arylene group includes naphthylene, anthrylene, phenanthrylene, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, benzofluorenylene, and the like, but is not limited thereto. The arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a benzofluorenylene group, or a phenylene-fluorenylene group.

Heteroarylene as used herein refers to the generic term for groups in which one or more of the aromatic core carbons in the arylene group is replaced with a heteroatom, including, but not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms, the linking site of the heteroarylene group may be located on a ring-forming carbon atom or on a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. The monocyclic heteroarylene group includes a pyridylene group, a pyrimidylene group, a triazinylene group, a furanylene group, a thiophenylene group and the like, but is not limited thereto; the polycyclic heteroarylene group includes bipyridyl idene, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroarylene group includes, but is not limited to, a quinolylene group, an isoquinolylene group, an indolyl group, a benzothiophene group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolylene group, a benzothiazolyl group, a dibenzofuranylene group, a dibenzothiophenylene group, a carbazolyl group, a benzocarbazolyl group, an acridinylene group, a 9, 10-dihydroacridine group, a phenoxazinyl group, a phenothiazinylene group, a phenoxathiin group and the like. The heteroaryl group is preferably a pyridylene group, pyrimidylene group, thienylene group, furylene group, benzothienylene group, benzofuranylene group, benzoxazolyl group, benzimidazolylene group, benzothiazolyl group, dibenzofuranylene group, dibenzothiophenylene group, dibenzofuranylene group, carbazolyl group, acridinylene group, phenoxazinyl group, phenothiazinylene group, phenoxathiin group.

Alkoxy in the context of the present invention means-O-alkyl, wherein alkyl is as previously defined.

The alkenyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from an olefin molecule, such as a vinyl group, a styryl group, and the like, but is not limited thereto.

The alkynyl group in the present invention refers to a hydrocarbon group obtained by removing one hydrogen atom from an alkyne molecule, such as an ethynyl group, a phenylethynyl group, and the like, but is not limited thereto.

The alicyclic ring in the present invention refers to cyclic hydrocarbon having aliphatic property, which contains closed carbon ring in the molecule, and can be monocyclic hydrocarbon formed by 3-18, preferably 3-12, more preferably 3-7 carbon atoms, and can be completely unsaturated or partially unsaturated, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but not limited thereto. Multiple monocyclic hydrocarbons can also be linked in a variety of ways: two rings in the molecule can share one carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings may also be interconnected to form a cage-like structure.

The aromatic ring in the present invention means aromatic hydrocarbon, and may be monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon, and examples thereof include benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, and the like, but are not limited thereto.

The "substitution" as referred to herein means that a hydrogen atom in some functional groups is replaced with another atom or functional group (i.e., substituent), and the substituted position is not limited as long as the position is a position at which a hydrogen atom is substituted, and when two or more are substituted, two or more substituents may be the same as or different from each other.

The term "substituted or unsubstituted" as used herein means not substituted or substituted with one or more substituents selected from the group consisting of: deuterium atom, halogen atom, amino group, cyano group, nitro group, substituted or unsubstituted alkyl group of C1 to C30, substituted or unsubstituted cycloalkyl group of C3 to C30, substituted or unsubstituted alkenyl group of C30 to C30, substituted or unsubstituted alkynyl group of C30 to C30, substituted or unsubstituted cycloalkyl group of C30 to C30, substituted or unsubstituted alkoxy group of C30 to C30, substituted or unsubstituted aryl group of C30 to C30, substituted or unsubstituted aryloxy group of C30 to C30, substituted or unsubstituted heteroaryl group of C30 to C30, preferably deuterium atom, halogen atom, cyano group, nitro group, alkyl group of C30 to C30, alkenyl group of C30 to C30, alkynyl group of C30 to C30, alkoxy group of C30 to C30, cycloalkyl group of C30 to C30, aryl group of C30 to C30, heteroaryl group of C30 to C30, and a plurality of substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, chlorine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclopropylalkyl group, cyclobutylalkyl group, cyclopentylalkyl group, cyclohexylalkyl group, cycloheptylalkyl group, adamantyl group, norbornyl group, vinyl group, methoxy group, ethoxy group, phenyl group, pentadeuteroylphenyl group, naphthyl group, anthracenyl group, phenanthryl group, triphenylene group, pyrenyl group, 9-dimethylfluorenyl group, 9-diphenylfluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, quinoxalinyl group, dibenzofuranyl group, dibenzothienyl group, phenylcarbazolyl group, and in the case of being substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other.

The term "integer selected from 0 to M" as used herein means any one of the integers having a value selected from 0 to M, including 0,1, 2 … M-2, M-1, M. For example, the expression "e, b and r are integers selected from 0 to 2" in the present invention means that e, b and r are selected from 0,1 or 2, and the expression "f, m, c and d₁And p is an integer of 0 to 3, and f, m, c, d₁P is selected from 0,1, 2 or 3, the' g, n, a₁And q is an integer of 0 to 4' means g, n, a₁Q is selected from 0,1, 2,3 or 4, the' h, b₁The integer selected from 0 to 6 "means h and b₁Selected from 0,1, 2,3, 4,5 or 6, said "i, c₁The integer selected from 0 to 8 means e and c₁Is selected from 0,1, 2,3, 4,5, 6,7 or 8, the integer of which j is selected from 0 to 10 means that f is selected from 0,1, 2,3, 4,5, 6,7,8, 9 or 10, the integer of which k and d are selected from 0 to 1 means that k and d are selected from 0 or 1, and the integer of which l is selected from 0 to 5 means that l is selected from 0,1, 2,3, 4 or 5; and so on.

The bonding to form a cyclic structure according to the present invention means that the two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:

in the present invention, the ring formed by the connection may be a five-membered ring or a six-membered ring or a fused ring, such as benzene, naphthalene, fluorene, cyclopentene, cyclopentane, cyclohexane acene, quinoline, isoquinoline, dibenzothiophene, phenanthrene or pyrene, but not limited thereto. Wherein, the five-membered ring or six-membered ring can refer to a ring formed by two groups (such as phenyl) and the connected group/segment, and can also refer to a ring formed by two groups (such as ethyl) and the connected group/segment.

The invention provides an arylamine compound, which has a structure shown in a formula (I):

wherein, X is selected from oxygen atom or sulfur atom;

said L₁～L₆Independently selected from a single bond, substituted or unsubstituted arylene of C6-C30, substituted or unsubstituted heteroarylene of C3-C30;

ar is₁～Ar₄At least one of the substituents is selected from one of the substituents containing alicyclic rings shown as the following, and the rest is independently selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30:

wherein e is an integer of 0-2, f is an integer of 0-3, g is an integer of 0-4, h is an integer of 0-6, i is an integer of 0-8, j is an integer of 0-10, and k is an integer of 0-1;

said R₂₁、R₂₂Independently selected from hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated ethyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, and combinations thereofSec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, cyclopropylalkyl, deuterated cyclopropylalkyl, cyclobutylalkyl, deuterated cyclobutylalkyl, cyclopentylalkyl, deuterated cyclopentylalkyl, cyclohexylalkyl, deuterated cyclohexylalkyl, cycloheptyl, deuterated cycloheptyl, norbornyl, deuterated norbornyl, adamantyl, deuterated adamantyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylenyl, deuterated triphenylenyl, pyrenyl, deuterated pyrenyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, and the like, One of spirobifluorenyl group and deuterated spirobifluorenyl group, when a plurality of R exist₂₁Or R₂₂When a plurality of R₂₁Same or different, a plurality of R₂₂The same or different;

m is an integer from 0 to 3, and n is an integer from 0 to 4;

said R_a、R_bIndependently selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl, when a plurality of R exist_aOr R_bWhen a plurality of R_aSame or different, a plurality of R_bThe same or different.

Preferably, the "heteroaryl" contains at least one heteroatom as follows: oxygen atom, sulfur atom, nitrogen atom, silicon atom.

Preferably, the substituent in the above "substituted or unsubstituted" is independently selected from the group consisting of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, ethyl group, deuterated ethyl group, n-propyl group, deuterated n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, deuterated n-butyl group, sec-butyl group, deuterated sec-butyl group, isobutyl group, deuterated isobutyl group, tert-butyl group, deuterated tert-butyl group, cyclopropyl group, deuterated cyclopropyl group, cyclobutyl group, deuterated cyclobutyl group, cyclopentyl group, deuterated cyclopentyl group, cyclohexyl group, deuterated cyclohexyl group, cycloheptyl group, deuterated cycloheptyl group, norbornyl group, deuterated norbornyl group, adamantyl group, deuterated adamantyl group, vinyl group, methoxy group, ethoxy group, phenyl group, deuterated phenyl group, naphthyl group, deuterated naphthyl group, anthryl group, deuterated anthryl group, phenanthryl group, deuterated phenanthryl group, triphenylene group, deuterated triphenylenyl group, pyrenyl group, phenanthrenyl group, deuterated phenanthrenyl group, and the like, Deuterated pyrenyl, pyridyl, pyrimidyl, triazinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl, deuterated spirobifluorenyl, and deuterated spirobifluorenyl, the number of substituents being one or more, and when a plurality of substituents are present, the plurality of substituents being the same or different.

Preferably, said L₁～L₆Independently selected from one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted carbazolyl group.

Preferably, said L₁～L₆Independently selected from a single bond or one of the following substituents:

wherein a is an integer from 0 to 4, b is an integer from 0 to 2, c is an integer from 0 to 3, and d is an integer from 0 to 1;

said R₁₁Selected from the group consisting of hydrogen atoms, deuterium atoms,One of a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a methoxy group, an ethoxy group, a phenyl group, a deuterated phenyl group, a naphthyl group, a deuterated naphthyl group, an anthracenyl group, a phenanthrenyl group, a deuterated phenanthrenyl group, a triphenylenyl group, a deuterated triphenylenyl group, a pyrenyl group, a deuterated pyrenyl group, a dibenzofuranyl group, a deuterated dibenzofuranyl group, a dibenzothiophenyl group, a phenylcarbazolyl group, a deuterated phenylcarbazolyl group, 9-dimethylfluorenyl group, a deuterated 9, 9-dimethylfluorenyl group, a 9, a deuterated 9-diphenylfluorenyl group, a deuterated 9, a 9-diphenylfluorenyl group, a spirobifluorenyl group, a deuterated spirobifluorenyl group, and a deuterated spirobifluorenyl group, when there are more than one R₁₁When a plurality of R₁₁The same or different;

said R₁₂、R₁₃、R₁₈Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl and deuterated naphthyl; when R is₁₂And R₁₃Independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, R is a hydrogen atom, and R is a hydrogen atom, a hydroxyl group₁₂And R₁₃Can be connected to form a substituted or unsubstituted aliphatic ring of C3-C7; when R is₁₂And R₁₃Independently selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, R₁₂And R₁₃May be linked to form a five-membered carbocyclic ring;

said R₁₄One selected from phenyl, deuterated phenyl, naphthyl and deuterated naphthyl;

said R₁₅、R₁₆、R₁₇Independently selected from phenylene, deuterated phenyl, naphthylene, deuteriumOne of substituted naphthyl;

when R is₁₈R is selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl₁₇And R₁₈May be linked to form a five-membered carbocyclic ring.

Preferably, said L₁～L₆Independently selected from a single bond or one of the following substituents:

wherein, a is₁Is selected from an integer of 0 to 4, b₁Is selected from an integer of 0 to 6, c₁Is selected from an integer of 0 to 8, d₁An integer selected from 0 to 3.

Preferably, said L₁～L₆Independently selected from a single bond or one of the following substituents:

preferably, Ar is₁～Ar₄At least one of which is selected from one of the substituents shown below:

preferably, Ar is not selected from said substituents containing an alicyclic ring₁～Ar₄Independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted phenanthrenylSubstituted or unsubstituted carbazolyl, substituted or unsubstituted fluorenyl and substituted or unsubstituted spirofluorenyl.

Preferably, said Ar not selected from said substituents containing an alicyclic ring₁～Ar₄The groups are independently selected from one of the following substituents:

wherein l is an integer from 0 to 5, p is an integer from 0 to 3, q is an integer from 0 to 4, and r is an integer from 0 to 2;

said R₃₁Selected from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an n-propyl group, a deuterated n-propyl group, an isopropyl group, a deuterated isopropyl group, an n-butyl group, a deuterated n-butyl group, a sec-butyl group, a deuterated sec-butyl group, an isobutyl group, a deuterated isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a deuterated cyclopropane group, a cyclobutane group, a cyclopentane group, a deuterated cyclopentane group, a cyclohexane group, a deuterated cyclohexane group, a cycloheptane group, a norbornyl group, a deuterated norbornyl group, an adamantyl group, a deuterated adamantyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a deuterated naphthyl group, an anthracene group, a phenanthryl group, a deuterated phenanthryl group, a triphenylphenyl group, a deuterated triphenylenyl group, a pyrenyl group, a deuterated pyrenyl group, a dibenzofuranyl group, a deuterated n group, a substituted dibenzofuranyl group, a substituted benzene group, Dibenzothienyl, deuterated dibenzothienyl, phenylcarbazolyl, deuterated phenylcarbazolyl, 9-dimethylfluorenyl, deuterated 9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, deuterated 9, 9-diphenylfluorenyl, spirobifluorenyl and deuterated spirobifluorenyl when a plurality of R exist₃₁When a plurality of R₃₁The same or different, or any two adjacent groups are connected to form a substituted or unsubstituted aromatic ring of C6-C10;

said R₃₂One selected from phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl and deuterated biphenyl;

said R₃₃、R₃₄、R₃₆Independently selected from one of hydrogen atom, deuterium atom, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl, deuterated tert-butyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl and deuterated naphthyl; when R is₃₃And R₃₄Independently selected from one of methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, deuterated n-propyl, isopropyl, deuterated isopropyl, n-butyl, deuterated n-butyl, sec-butyl, deuterated sec-butyl, isobutyl, deuterated isobutyl, tert-butyl and deuterated tert-butyl, R₃₃And R₃₄Can be connected to form a substituted or unsubstituted aliphatic ring of C3-C7; when R is₃₃And R₃₄Independently selected from one of phenyl, deuterated phenyl, naphthyl and deuterated naphthyl, R₃₃And R₃₄May be linked to form a five-membered carbocyclic ring;

said R₃₅、R₃₇Independently selected from one of phenylene, deuterated phenyl, biphenylene, deuterated biphenylene, naphthylene and deuterated naphthyl.

Preferably, said Ar not selected from said substituents containing an alicyclic ring₁～Ar₄The groups are independently selected from one of the following substituents:

preferably, the arylamine compound has one of the structures shown in formulas (II-A) to (II-F):

wherein, L is₃～L₆、Ar₁～Ar₄And X is as defined above.

Preferably, the arylamine compound has one of the structures shown in formulas (III-A) to (III-P):

wherein, L is₃～L₆、Ar₁～Ar₄And X is as defined above.

Preferably, the arylamine compound has one of the structures shown in formulas (IV-A) to (IV-F):

wherein, L is₃～L₆、Ar₁～Ar₄And X is as defined above.

Preferably, the arylamine compound has one of the structures represented by formulae (V-a) to (V-F):

wherein, L is₃～L₆、Ar₁～Ar₄And X is as defined above.

Preferably, Ar is₁～Ar₄Is selected from the group consisting of said alicyclic ring-containing substituents.

Preferably, Ar is₁～Ar₄Two of which are selected from the aliphatic ring-containing substituents.

Preferably, Ar is₁～Ar₄Three of which are selected from the aliphatic ring-containing substituents.

Preferably, Ar is₁～Ar₄Are all selected from the substituents containing an alicyclic ring.

Preferably, Ar not selected from said substituents containing an alicyclic ring is₁～Ar₄In the group, at least one substituent is selected from the following substituents:

most preferably, the arylamine compound is selected from one of the following compounds:

while the above list only shows some specific structural forms of the compounds of formula (I), the present invention is not limited to these listed chemical structures, and all that is based on formula (I) and the substituents are as defined above, should be included.

The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transmission area, a luminescent layer and an electron transmission area, and the hole transmission area contains one or more than one of the arylamine compounds.

The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer comprises a hole transport region, a luminescent layer and an electron transport region, the hole transport region comprises at least one of a hole injection layer, a hole transport layer and a luminescent auxiliary layer, and the hole transport region contains one or more than one of the arylamine compounds.

The hole injection layer of the present invention may have a single-layer structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, allyl compounds, and other substances having high hole injection properties, for example, 4,4',4 ″ -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-Hexaazatriphenylene (HATCN), copper phthalocyanine (CuPC), 2,3,5, 6-tetrafluoro-7, 7',8,8' -tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid) (PEDOT/PSS), and the arylamine compounds described in the present invention can be used, but are not limited thereto. Preferably, the hole injection layer has a single-layer structure composed of a host material and a dopant material, and more preferably, the mass ratio of the host material to the dopant material is 100:1 to 100: 10.

The hole transport layer of the present invention may have a single-layer structure composed of a single substance, or may have a single-layer structure or a multi-layer structure composed of different substances. Triarylamine derivatives having two or more triarylamine structures linked by a single bond or arylene group, and other hole mobilities of 10 can be used^-6cm²Examples of the substance having a/Vs or more include, but are not limited to, N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4, 4' -diamine (TPD), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), 4',4 ″ -tris (N, N-diphenylamino) triphenylamine (TDATA), and the arylamine compound described in the present invention.

The light-emitting auxiliary layer of the present invention may be a single-layer structure formed of a single substance, or a single-layer structure or a multilayer structure formed of different substances, and a triarylamine derivative, a spirofluorene derivative, a dibenzofuran derivative, and other materials having appropriate HOMO and T1 energy levels, in which two or more triarylamine structures are connected by a single bond or an arylene group, may be used, for example, TPD, NPB, N4, N4-bis ([1,1 '-biphenyl ] -4-yl) -N4' -phenyl N4'- [1, 1': 4', 1' -terphenyl ] -4-yl- [1,1' -biphenyl ] -4,4' -diamine, N- ([1,1' -diphenyl ] -4-yl) -N- (9, 9-dimethyl-9H-furan-2-yl) -9,9' -spirobifluorene-2-amine, N-bis ([1,1' -biphenyl ] -4-yl) -3' - (dibenzo [ b, d ] furan-4-yl) - [1,1' -biphenyl ] -4-amine, the arylamine compound described in the present invention, but is not limited thereto.

Preferably, the hole transport region includes a hole injection layer containing one or more of the arylamine compounds of the present invention.

Preferably, the hole transport region comprises a hole transport layer, and the hole transport layer contains one or more of the arylamine compounds described in the present invention.

Preferably, the hole transport region includes a luminescence auxiliary layer, and the luminescence auxiliary layer contains one or more of the arylamine compounds of the present invention.

The invention also provides an organic electroluminescent device which comprises an anode, a cathode, an organic layer between the anode and the cathode and a covering layer arranged on the side of the cathode, which is far away from the anode, wherein the covering layer contains one or more than one of the arylamine compounds.

The covering layer comprises a first covering layer and/or a second covering layer, and when the first covering layer or the second covering layer is included, the covering layer can be a single-layer structure formed by a single substance or a single-layer structure formed by different substances; when the first cover layer and the second cover layer are included, they are a multilayer structure made of a single substance or different substances. The coating material may be organic or inorganic, and preferably, the arylamine compound of the present invention is used.

The arylamine compound shown in the formula (I) can be prepared by the following synthetic route:

wherein, X is₁、X₂Independently selected from a chlorine atom, a bromine atom or an iodine atom, said X, L₁～L₆、R_a、R_b、Ar₁～Ar₄M and n are as defined above.

Compound (Y)₁) And compound (Y)₂) Compound (Y)₃) The arylamine compound shown in the formula (I) can be obtained through one-step or two-step Buchwald reaction. Compound (Y)₁) Can be first reacted with compound (Y)₂) Can also be reacted with the compound (Y) first₃) The reaction, in the case where the compound (Y2) is the same as the compound (Y3), may be carried out in one step, and the reaction conditions such as reaction solvent, catalyst, ligand, base and the like may be any of the conventional methods without particular limitation. The preparation method has the advantages of easily available raw materials, simple preparation process and excellent reaction yield.

The light-emitting layer of the invention may contain only a guest material, or a guest material may be dispersed in a host material. As the guest material, a fluorescent compound such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative and the like can be used, and specific examples thereof include 10- (2-benzothiazolyl) -2,3,6, 7-tetrahydro-1, 1,7, 7-tetramethyl-1H, 5H,11H- [ 1H]Benzopyran [6,7,8-ij]Quinolizin-11-one (C545T), 4' -bis (9-ethyl-3-carbazolenyl) -1,1' -biphenyl (BCzVBi), 4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), and the like; phosphorescent light-emitting materials may also be used, for example, metal complexes such as iridium complex, osmium complex, and platinum complex, and specific examples thereof include bis (4, 6-difluorophenylpyridine-N, C2) picolinatoiridium (FIrpic) and tris (2-phenylpyridine) iridium (Ir (ppy)₃) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)₂(acac)) and the like. The host material is preferably a material having a higher LUMO and a lower HOMO than the guest material, and examples thereof include a metal complex such as an aluminum complex or a zinc complex, a heterocyclic compound such as an oxadiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or an anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and specifically include 8-hydroxyquinoline aluminum (Alq)₃) Bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1,1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (1-phenyl-1H-benzimidazol-2-yl) benzene (TPBI), TPD, 4' -bis (9-Carbazole) Biphenyl (CBP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (2-naphthyl) Anthracene (ADN), and the like.

The electron transport region comprises at least one of an electron injection layer, an electron transport layer and a hole blocking layer.

The electron injection layer can be a single-layer structure formed by a single substance, or a single-layer structure or a multi-layer structure formed by different substances, and one or more of the following substances can be selected: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances having a high electron-injecting property. Specific examples thereof include Li, Ca, Sr, LiF, CsF and CaF₂、BaO、Li₂CO₃、CaCO₃、Li₂C₂O₄、Cs₂C₂O₄、CsAlF₄And LiOx, Yb, Tb, etc.

The electron transport layer of the present invention may have a single-layer structure composed of a single substance, or a single-layer structure or a multilayer structure composed of different substances, and aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, and the like, which have high electron transport properties, for example, Alq₃Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq₂) BAlq, 2- (4-biphenyl) -5-phenyl oxadiazole (PBD), and the like.

The hole-blocking layer of the present invention may have a single-layer structure made of a single substance, or may have a single-layer structure or a multi-layer structure made of different substances. The selected material requires the T1 energy level to be higher than that of the light-emitting layer so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material is lower than that of the host material of the light-emitting layer, so that the hole blocking effect is achieved. Further, the electron mobility of the hole blocking layer material used is 10^-6cm²Above Vs, it is preferable to use triazine derivatives, azabenzene derivatives, etc. because they facilitate electron transport. Most preferred are triazine derivatives.

Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer;

preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer;

preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer and an electron injection layer;

preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

The anode of the present invention may be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or an alloy thereof, or may have a high work function and be a transparent or semi-transparent layer structure, such as Indium Tin Oxide (ITO), indium zinc oxide (ZnO), Aluminum Zinc Oxide (AZO), Indium Gallium Oxide (IGO), indium oxide (In)₂O₃) Or tin oxide (SnO)₂) And (3) forming a layer structure.

The cathode of the invention can be a thin film with low work function made of lithium, calcium, lithium fluoride/aluminum, silver, magnesium-silver alloy and the like, and can be made into a reflecting electrode, a transparent electrode or a semitransparent electrode by adjusting the thickness of the film.

The organic layers, the cathode, the anode and the cover layer can be prepared by any one of vacuum evaporation, ink-jet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing and the like, and the film thickness of each layer is not particularly limited so as to obtain good device performance. The respective organic layers are preferably prepared by a method of vacuum evaporation, inkjet printing, or spin coating.

The thickness of each of the organic layer and the capping layer is usually 5nm to 100um, preferably 10nm to 200 nm. The thickness of the anode and the cathode is adjusted according to the required transparency.

The organic electroluminescent device provided by the invention can be applied to the field of OLED illumination and the field of OLED display, and can be specifically listed as a large-size display such as a smart phone display screen, a tablet computer display screen, an intelligent wearable device display screen, a television and the like, VR (virtual reality) and an automobile tail lamp and the like.

The technical scheme and technical effects of the present invention are further described below by examples and comparative examples.

The mass spectrum of the compound of the invention uses a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer of Watts corporation of England, and chloroform is used as a solvent;

the elemental analysis was carried out by using a Vario EL cube type organic element analyzer of Elementar, Germany, and the sample mass was 5 to 10 mg.

Synthesis example 1: preparation of Compounds m-15, m-16, m-17, m-18, m-19

Under the protection of nitrogen, a three-neck flask is sequentially added with a compound a-1(10.56g, 60mmol), a compound b-1(10.32g, 60mmol) and a compound K₂CO₃(16.58g,120mmol)、Pd(PPh₃)₄(1.38g,1.2mmol), 500mL of a toluene/ethanol/water (3:1:1) mixed solvent was added, the mixture was stirred, and the above reactant system was heated under reflux for 8 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and extracted with deionized water and toluene to obtain an organic layer, and the organic layer was washed with 400mL of deionized water for 3 times, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from toluene to obtain compound m-15(10.45g, yield 78%). Mass spectrum m/z: 223.1376 (theoretical value: 223.1361).

Compounds m-16, m-17, m-18, m-19 were prepared according to the method for the preparation of compound m-15 by substituting equimolar amounts of the starting materials a and b, with yields and mass spectra as shown in Table 1:

TABLE 1

Synthesis example 2: preparation of Compounds Y2, Y3

Toluene (300mL), compound m-1(4.42g, 30mmol), compound n-1(6.21g, 30mmol), palladium acetate (0.10g, 0.45mmol), sodium tert-butoxide (5.77g, 60mmol), and tri-tert-butylphosphine (4mL in toluene) were added to a three-necked flask in this order under nitrogen blanket. And reacted under reflux for 2 hours. After the reaction was stopped, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallized from methanol, filtered with suction and rinsed with methanol to give a recrystallized solid, compound Y2-1(6.81g, 83% yield). Mass spectrum m/z: 273.1536 (theoretical value: 273.1517).

Other Y2 and Y3 compounds were prepared by replacing the equimolar amounts of m and n according to the method for preparing Y2-1, and the yields and mass spectra are shown in Table 2:

TABLE 2

Synthetic example 3: preparation of Compound 15

Toluene (100mL), compound Y1-1(3.73g, 10mmol), compound Y2-1(2.73g, 10mmol), palladium acetate (0.03g, 0.15mmol), sodium tert-butoxide (1.92g, 20mmol), and tri-tert-butylphosphine (1.3mL in toluene) were added to a three-necked flask in this order under nitrogen. And reacted under reflux for 2 hours. After the reaction had ceased, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallised from methanol, filtered and rinsed with methanol to give a recrystallised solid which gave intermediate Z-1(4.04g, 78% yield), mass spectrum m/Z: 517.1060 (theoretical value: 517.1041).

Toluene (50mL), intermediate Z-1(2.59g, 5mmol), compound Y3-1(1.48g, 5mmol), palladium acetate (0.02g, 0.08mmol), sodium tert-butoxide (0.96g, 10mmol), and tri-tert-butylphosphine (0.7mL in toluene) were added to a three-necked flask in this order under nitrogen. And reacted under reflux for 2 hours. After the reaction had ceased, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallised from methanol, filtered with suction and rinsed with methanol to give a recrystallised solid which gave compound 15(2.71g, 74% yield) having a purity of > 99.6% by HPLC. Mass spectrum m/z: 732.3156 (theoretical value: 732.3141). Theoretical element content (%) C₅₄H₄₀N₂O: c, 88.49; h, 5.50; and N, 3.82. Measured elemental content (%): c, 88.46; h, 5.52; n, 3.84.

Synthetic example 4: preparation of Compound 32

Compound 32(2.75g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-2, Y2-2, Y3-2 and Z-2, and the solid purity was ≧ 99.5% by HPLC. Mass spectrum m/z: 722.2739 (theoretical value: 722.2756). Theoretical element content (%) C₅₂H₃₈N₂S: c, 86.39; h, 5.30; and N, 3.87. Measured elemental content (%): c, 86.36; h, 5.36; and N, 3.85.

Synthesis example 5: preparation of Compound 52

Compound 52(3.14g) was obtained by substituting Y2-1, Y3-1 and Z-1 in Synthesis example 3 with equal molar amounts of Y2-3, Y3-3 and Z-3 in that order, and the purity of the solid was ≧ 99.6% by HPLC. Mass spectrum m/z: 814.3026 (theoretical value: 814.3018). Theoretical element content (%) C₅₈H₄₂N₂And OS: c, 85.47; h, 5.19; n, 3.44. Measured elemental content (%): c, 85.49; h, 5.13; and N, 3.45.

Synthetic example 6: preparation of Compound 69

Compound 69(3.30g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-2, Y2-4, Y3-4 and Z-4 in that order, and the solid purity by HPLC ≧ 99.7%. Mass spectrum m/z: 814.3039 (theoretical value: 814.3018). Theoretical element content (%) C₅₈H₄₂N₂And OS: c, 85.47; h, 5.19; n, 3.44. Measured elemental content (%): c, 85.45; h, 5.24; n, 3.41.

Synthetic example 7: preparation of Compound 76

Compound 76(3.19g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-3, Y2-5, Y3-5 and Z-5 in that order, and the solid purity by HPLC ≧ 99.3%. Mass spectrum m/z: 898.4126 (theoretical value: 898.4135). Theoretical element content (%) C₆₅H₃₄D₁₂N₂S: c, 86.82; h, 6.50; and N, 3.12. Measured elemental content (%): c, 86.85; h, 6.43; and N, 3.16.

Synthesis example 8: preparation of Compound 87

Compound 87(3.41g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-4, Y2-6, Y3-6 and Z-6 in this order, and the solid purity by HPLC ≧ 99.5%. Mass spectrum m/z: 873.1136 (theoretical value: 873.1120). Theoretical element content (%) C₆₅H₄₈N₂O: c, 89.42; h, 5.54; and N, 3.21. Measured elemental content (%): c, 89.43; h, 5.59; and N, 3.15.

Synthetic example 9: preparation of Compound 88

In the same manner as in synthesis example 3, Y1-1, Y3-1 and Z-1 were replaced with equimolar amounts of Y1-5, Y3-7 and Z-7 in that order to obtain compound 88(3.45g), and the solid purity by HPLC ≧ 99.2%. Mass spectrum m/z: 920.3754 (theoretical value: 920.3767). Theoretical element content (%) C₆₉H₄₈N₂O: c, 89.97; h, 5.25; and N, 3.04. Measured elemental content (%): c, 89.96; h, 5.29; and N, 3.02.

Synthetic example 10: preparation of Compound 102

Compound 102(3.06g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were sequentially substituted with equimolar amounts of Y1-6, Y2-4, Y3-4 and Z-24, and the solid purity by HPLC ≧ 99.5%. Mass spectrum m/z: 814.3027 (theoretical value: 814.3018). Theoretical element content (%) C₅₈H₄₂N₂And OS: c, 85.47; h, 5.19; n, 3.44. Measured elemental content (%): c, 85.49; h, 5.13; and N, 3.47.

Synthetic example 11: preparation of Compound 154

Compound 154(3.46g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-6, Y2-4, Y3-8 and Z-8 in that order, and the solid purity by HPLC ≧ 99.4%. Mass spectrum m/z: 864.3189 (theoretical value: 864.3174). Theoretical element content (%) C₆₂H₄₄N₂And OS: c, 86.08; h, 5.13; and N, 3.24. Measured elemental content (%): c, 86.04; h, 5.15; and N, 3.27.

Synthetic example 12: preparation of Compound 200

Compound 200(2.96g) was obtained by replacing Y1-1, Y2-1 and Z-1 in Synthesis example 3 with equal molar amounts of Y1-7, Y2-7 and Z-9 in that order, and the purity of the solid was ≧ 99.1% by HPLC. Mass spectrum m/z: 822.3259 (theoretical value: 822.3246). Theoretical element content (%) C₆₀H₄₂N₂O₂: c, 87.56; h, 5.14; and N, 3.40. Measured elemental content (%): c, 87.51; h, 5.17; and N, 3.42.

Synthetic example 13: preparation of Compound 228

Compound 228(3.35g) was obtained by the same procedure except that Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y2-8, Y3-9 and Z-10 in that order, and the solid purity was ≧ 99.6% by HPLC. Mass spectrum m/z: 892.4376 (theoretical value: 892.4393). Theoretical element content (%) C₆₆H₅₆N₂O: c, 88.75; h, 6.32; and N, 3.14. Measured elemental content (%): c, 88.71; h, 6.38; n, 3.11.

Synthesis example 14: preparation of compound 279

Compound 279(3.17g) was obtained by the same procedure except for replacing Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 with equimolar amounts of Y1-8, Y2-9, Y3-10 and Z-11 in that order, and the solid purity by HPLC ≧ 99.1%. Mass spectrum m/z: 866.3680 (theoretical value: 866.3695). Theoretical element content (%) C₆₃H₅₀N₂S: c, 87.26; h, 5.81; and N, 3.23. Measured elemental content (%): c, 87.28; h, 5.88; and N, 3.16.

Synthetic example 15: preparation of Compound 286

Compound 286(2.72g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-9, Y2-10, Y3-11 and Z-12, and the solid purity was ≧ 99.3% by HPLC. Mass spectrum m/z: 810.3627 (theoretical value: 810.3610). Theoretical element content (%) C₆₀H₄₆N₂O: c, 88.86; h, 5.72; and N, 3.45. Measured elemental content (%): c, 88.83; h, 5.78; n, 3.41.

Synthetic example 16: preparation of Compound 315

Compound 315(3.06g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-5, Y2-9, Y3-12 and Z-13 in this order, and the solid purity by HPLC ≧ 99.7%. Mass spectrum m/z: 860.3419 (theoretical value: 860.3403). Theoretical element content (%) C₆₃H₄₄N₂O₂: c, 87.88; h, 5.15; and N, 3.25. Measured elemental content (%): c, 87.87; h, 5.20; and N, 3.23.

Synthetic example 17: synthesis of Compound 381

Compound 381(3.46g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-2, Y2-20, Y3-18 and Z-22 in this order, and the solid purity by HPLC ≧ 99.2%. Mass spectrum m/z: 946.5275 (theoretical value: 946.5260). Theoretical element content (%) C₆₈H₇₀N₂S: c, 86.21; h, 7.45; and N, 2.96. Measured elemental content (%): c, 86.24; h, 7.40; and N, 2.97.

Synthetic example 18: synthesis of Compound 398

Compound 398(2.83g) was obtained by the same procedure except for replacing Y2-1, Y3-1 and Z-1 in Synthesis example 3 with equimolar amounts of Y2-21, Y3-19 and Z-23 in that order, and the solid purity by HPLC ≧ 99.0%. Mass spectrum m/z: 807.3317 (theoretical value: 807.3332). Theoretical element content (%) C₅₇H₃₇D₅N₂And OS: c, 84.72; h, 5.86; and N, 3.47. Measured elemental content (%): c, 84.70; h, 5.91; and N, 3.45.

Synthetic example 19: preparation of Compound 408

Compound 408(3.03g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-4, Y2-11, Y3-3 and Z-14 in this order, and the solid purity by HPLC ≧ 99.8%. Mass spectrum m/z: 840.3183 (theoretical value: 840.3174). Theoretical element content (%) C₆₀H₄₄N₂And OS: c, 85.68; h, 5.27; n, 3.33. Measured elemental content (%): c, 85.63; h, 5.30; and N, 3.35.

Synthesis example 20: preparation of Compound 427

Compound 427(2.96g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-10, Y2-12, Y3-3 and Z-15 in that order, and the solid purity by HPLC ≧ 99.5%. Mass spectrum m/z: 870.3657 (theoretical value: 870.3644). Theoretical element content (%) C₆₂H₅₀N₂And OS: c, 85.48; h, 5.79; and N, 3.22. Measured elemental content (%): c, 85.49; h, 5.73; and N, 3.26.

Synthetic example 21: preparation of Compound 439

Toluene (50mL), compound Y1-11(1.63g, 5mmol), compound Y2-4(2.99g, 10mmol), palladium acetate (0.04g, 0.16mmol), sodium tert-butoxide (1.92g, 20mmol), and tri-tert-butylphosphine (1.4mL in toluene) were added to a three-necked flask in this order under nitrogen. And reacted under reflux for 2 hours. After the reaction had ceased, the mixture was cooled to room temperature, filtered through celite, the filtrate was concentrated, recrystallised from methanol, filtered with suction and rinsed with methanol to give the recrystallised solid, compound 439(3.13g, 82% yield) having a solid purity ≧ 99.8% by HPLC. Mass spectrum m/z: 762.3602 (theoretical value: 762.3610). Theoretical element content (%) C₅₆H₄₆N₂O: c, 88.15; h, 6.08; n, 3.67. Measured elemental content (%): c, 88.11; h, 6.06; and N, 3.70.

Synthetic example 22: preparation of Compound 464

The same procedures were repeated except for replacing Y1-11 and Y2-4 in Synthesis example 21 with equimolar amounts of Y1-12 and Y2-13, respectively, to give compound 464(3.25g)And the purity of the solid is not less than 99.4 percent by HPLC (high performance liquid chromatography). Mass spectrum m/z: 822.2719 (theoretical value: 822.2739). Theoretical element content (%) C₅₆H₄₂N₂OS₂: c, 81.72; h, 5.14; and N, 3.40. Measured elemental content (%): c, 81.70; h, 5.18; and N, 3.39.

Synthetic example 23: preparation of Compound 525

Compound 525(3.01g) was obtained by replacing Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 with equimolar amounts of Y1-8, Y2-14, Y3-13 and Z-16 in that order, and the remaining steps were repeated in the same manner, and the solid purity by HPLC ≧ 99.3%. Mass spectrum m/z: 792.2825 (theoretical value: 792.2810). Theoretical element content (%) C₅₅H₄₀N₂O₂S: c, 83.30; h, 5.08; and N, 3.53. Measured elemental content (%): c, 83.36; h, 5.03; n, 3.51.

Synthetic example 24: preparation of Compound 530

Compound 530(3.46g) was obtained by substituting Y1-11 and Y2-4 in Synthesis example 21 with equimolar amounts of Y1-13 and Y2-15 in that order, and the purity of the solid was ≧ 99.5% by HPLC. Mass spectrum m/z: 886.4337 (theoretical value: 886.4321). Theoretical element content (%) C₆₄H₅₈N₂S: c, 86.64; h, 6.59; and N, 3.16. Measured elemental content (%): c, 86.62; h, 6.64; and N, 3.13.

Synthetic example 25: preparation of compound 537

Y2-1, Y3-1 and Z-1 in synthetic example 3 were sequentially substituted with equimolar amounts of Y2-16, Y3-3 and Z-17, and the other steps were the same to obtainPurity ≧ 99.8% by HPLC was determined for compound 537(3.58 g). Mass spectrum m/z: 894.3599 (theoretical value: 894.3582). Theoretical element content (%) C₆₄H₄₂D₄N₂And OS: c, 85.87; h, 5.63; and N, 3.13. Measured elemental content (%): c, 85.84; h, 5.69; and N, 3.10.

Synthetic example 26: preparation of Compound 544

Compound 544(3.26g) was obtained by the same procedures except for replacing Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 with equimolar amounts of Y1-14, Y2-17, Y3-14 and Z-18 in that order, and the solid purity was ≧ 99.4% by HPLC. Mass spectrum m/z: 869.3475 (theoretical value: 869.3488). Theoretical element content (%) C₆₂H₃₉D₅N₂And OS: c, 85.58; h, 5.68; and N, 3.22. Measured elemental content (%): c, 85.59; h, 5.72; and N, 3.20.

Synthetic example 27: preparation of Compound 546

Compound 546(3.07g) was obtained by the same procedure except for replacing Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 with equimolar amounts of Y1-6, Y2-18, Y3-15 and Z-19 in that order, and had a solid purity of 99.1% by HPLC. Mass spectrum m/z: 864.3185 (theoretical value: 864.3174). Theoretical element content (%) C₆₂H₄₄N₂And OS: c, 86.08; h, 5.13; and N, 3.24. Measured elemental content (%): c, 86.02; h, 5.18; and N, 3.27.

Synthetic example 28: synthesis of Compound 563

The substituents Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were sequentially replaced withThe same procedures were repeated except for the molar amounts of Y1-6, Y2-19, Y3-16 and Z-20 to give compound 563(3.16g) having a solid purity of 99.2% by HPLC. Mass spectrum m/z: 878.3350 (theoretical value: 878.3331). Theoretical element content (%) C₆₃H₄₆N₂And OS: c, 86.07; h, 5.27; n, 3.19. Measured elemental content (%): c, 86.09; h, 5.22; and N, 3.22.

Synthetic example 29: synthesis of Compound 599

Compound 599(3.33g) was obtained by the same procedures except for replacing Y1-1, Y3-1 and Z-1 in Synthesis example 3 with equimolar amounts of Y1-15, Y3-17 and Z-21 in that order, and the purity of the solid was 99.7% by HPLC. Mass spectrum m/z: 864.3156 (theoretical value: 864.3174). Theoretical element content (%) C₆₂H₄₄N₂And OS: c, 86.08; h, 5.13; and N, 3.24. Measured elemental content (%): c, 86.05; h, 5.19; and N, 3.20.

Synthetic example 30: synthesis of Compound 610

Compound 610(3.12g) was obtained by the same procedure except that Y1-1, Y2-1, Y3-1 and Z-1 in Synthesis example 3 were replaced with equimolar amounts of Y1-6, Y2-22, Y3-10 and Z-25 in this order, and the solid purity by HPLC ≧ 99.6%. Mass spectrum m/z: 878.3680 (theoretical value: 878.3695). Theoretical element content (%) C₆₄H₅₀N₂S: c, 87.43; h, 5.73; n, 3.19. Measured elemental content (%): c, 87.46; h, 5.77; n, 3.11.

Synthetic example 31: synthesis of Compound 611

Y1-1, Y2-1, Y3-1, Y in Synthesis example 3,The compound 611(2.92g) was obtained by replacing Z-1 with equimolar amounts of Y1-4, Y2-23, Y3-17 and Z-26 in that order, and the purity of the solid was ≧ 99.1% by HPLC. Mass spectrum m/z: 798.2722 (theoretical value: 798.2705). Theoretical element content (%) C₅₇H₃₈N₂And OS: c, 85.69; h, 4.79; n, 3.51. Measured elemental content (%): c, 85.65; h, 4.85; and N, 3.49.

The organic materials in the preparation examples are purified by sublimation, and the purity is over 99.99 percent. The ITO/Ag/ITO glass substrate used in the preparation examples was purchased from Shenzhen Nangu display device science and technology Limited.

The following are other compounds used in the preparation examples in addition to the arylamine compound of the present invention:

a combined IVL test system is formed by test software, a computer, a K2400 digital source meter of Keithley company in the United states and a PR788 spectral scanning luminance meter of Photo Research company in the United states, and the device prepared by the invention is tested at the current density of 15mA/cm at the atmospheric pressure and the room temperature²Luminous efficiency and driving voltage at the time of the formation of the electrodes. The lifetime (luminance decay to 95% of the initial luminance) of the devices prepared according to the invention was tested at atmospheric pressure and room temperature using the McScience M6000 OLED lifetime test system. The test results are shown in table 3.

Comparative device preparation example 1: comparison device 1

Firstly, the ITO glass substrate is ultrasonically cleaned for 20 minutes by deionized water for 2 times, then is ultrasonically cleaned for 20 minutes by isopropanol, acetone and methanol in sequence, is exposed in ultraviolet rays and ozone for 30 minutes, and is finally placed in vacuum evaporation equipment for standby.

Evaporating each organic material layer and the cathode layer by layer on the ITO glass substrate, and specifically comprises the following steps: a. 2-TNATA is taken as a hole injection layer and has the thickness of 60 nm; b. NPB is used as a hole transport layer and has the thickness of 60 nm; c. the compound D-1 is used as a luminescence auxiliary layer and has the thickness of 20 nm; d. (piq)₂Ir (acac) and CBP (mass ratio of 5: 95) as a light-emitting layer, and the thickness is 30 nm; e. BAlq is used as a hole blocking layer and has the thickness of 10 nm; f. alq₃As an electron transport layer, the thickness is 50 nm; g. LiF is used as an electron injection layer and has the thickness of 0.2 nm; h. al as a cathode and having a thickness of 150 nm.

Comparative device preparation examples 2 to 3: comparison device 2-3

And replacing the compound D-1 with compounds D-2 and D-3 respectively, and obtaining the comparative devices 2-3 by the same steps as the comparative device preparation example 1.

Device preparation examples 1 to 29: light emitting device 1 to 29

The compound D-1 was replaced with the arylamine compound of the present invention in synthesis examples 3 to 31, respectively, and the remaining steps were the same as in comparative device preparation example 1, whereby light-emitting devices 1 to 29 were obtained.

TABLE 3

The device data of table 3 show that when the arylamine compound of formula (I) is used as a light emission auxiliary layer in an OLED device, the driving voltage, the light emission efficiency, and the lifetime of the device are significantly improved.

It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.