CN117229309A

CN117229309A - Triarylamine compound and organic electroluminescent device thereof

Info

Publication number: CN117229309A
Application number: CN202311127363.7A
Authority: CN
Inventors: 孙月; 陆影; 杜明珠
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2023-09-01
Filing date: 2023-09-01
Publication date: 2023-12-15

Abstract

The invention provides a triarylamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. Compared with the conventional organic electroluminescent compounds, the compound has asymmetric space configuration and higher glass transition temperature, and the asymmetric triarylamine compound has good thermal stability and film forming property; in addition, the asymmetric triarylamine compound is applied to an organic light-emitting device as a cover layer material, so that the light-emitting efficiency and the driving voltage of the organic light-emitting device can be effectively improved, and the service life of the device can be prolonged. The preparation method of the triarylamine compound is simple, raw materials are easy to obtain, the industrialized demand can be met, the triarylamine compound has good application effect and industrialization prospect, and the triarylamine compound can be widely applied to the fields of panel display, illumination light sources, flexible OLED, organic solar cells and the like.

Description

Triarylamine compound and organic electroluminescent device thereof

Technical Field

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

Background

In recent years, with rapid development of science and technology, demands for display performance have been gradually increased, and in such a situation, organic electroluminescent devices, that is, organic electroluminescent devices (Organic Light Emitting Diode, OLEDs), have been increasingly attracting attention due to their excellent characteristics of low operating voltage, high brightness, high efficiency, high contrast, thin thickness, light weight, wide viewing angle, wide operating temperature range, simple process, and the like.

OLEDs are generally divided into single layer, two layer, three layer, and multi-layer structures. Generally, the organic functional layer is formed between the anode and the cathode or outside one or more of the anode and the cathode. The anode generally adopts ITO (indium tin oxide), the cathode generally adopts a metal material with a smaller work function, and the organic functional layers comprise a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emitting layer (EML), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL) and a cover layer (CPL). Under the drive of an electric field, the device is subjected to electric excitation, and light is emitted through carrier injection, migration, exciton formation by electron-hole, exciton re-radiation recombination.

OLEDs can be classified into bottom-emitting OLEDs and top-emitting OLEDs according to the light-emitting direction. Top emission OLEDs are most common in applications. It is reported that the optical waveguide effect and the surface plasma effect are commonly existing in the device, so that most photons generate non-radiative coupling, and the external quantum efficiency is low. Therefore, how to improve the light extraction efficiency of OLEDs has become a current research hotspot at home and abroad.

In order to improve the light emitting efficiency of the top emission OLEDs, the simplest and most effective method is to form a cover layer as a light extraction functional layer on the transparent electrode. The cladding material can be used to reduce total reflection losses and waveguide losses in OLEDs and to improve light out-coupling efficiency. The cover material should have excellent properties such as high glass transition temperature, high film refractive index in the visible range, corrosion resistance, etc. Therefore, it is important to develop new capping layer materials to improve the luminous efficiency and lifetime of the device.

Disclosure of Invention

In order to overcome the problems in the prior art, the invention aims to provide the triarylamine compound and the organic electroluminescent device thereof based on industrialization targets, the triarylamine compound provided by the invention has asymmetric space configuration, the glass transition temperature of the material is easier to regulate and control, the material has good luminescence property, the asymmetric triarylamine structure compound has good rigidity and better film forming property, and the compound is used for being applied to a covering layer of the device, so that the driving voltage, the luminous efficiency and the service life of the OLED device can be effectively improved.

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

in the above formula I, the formula I is ₁ -Ar ₁ 、*-L ₂ -Ar ₂ 、*-L ₀ -(Ra)n ₀ Are different from each other;

the R is _a Selected from-F, -CF ₃ 、-Si(R ₁ R ₂ R ₃ ) Any one of them; and n is ₀ 1 or more, wherein, when R _a When selected from-F, n ₀ Selected from 5;

the R is ₁ To R ₃ Each independently selected from any one of a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring, and a fused ring group of a C6-C30 aromatic ring;

the Ar is as follows ₁ Selected from the group represented by formula a-1, and a-1 is represented by the following formula a-1 and L ₁ Connecting;

the X is selected from O or S;

each z is independently selected from CH or N;

the R is ₀ Each 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, substituted or unsubstituted C2-C30 heteroaryl;

said n ₁ Selected from 1, 2, 3 or 4; when n is ₁ Above 1, two or more R ₀ Are identical or different from each other, or adjacent twoR is a number of ₀ Are connected with each other to form a substituted or unsubstituted ring;

the Ar is as follows ₂ One or a combination of the following groups:

wherein each E is independently selected from CH or N;

the X is ₁ Selected from O, S, C (R) _e R _f )、N(R _g )、Si(R _k ) ₂ Any one of them;

the R is _e 、R _f Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _e 、R _f Are connected with each other to form a substituted or unsubstituted ring;

the R is _g Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

The R is _k Each independently selected from the group consisting of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ringOne of the bases;

the R is ₄ Each independently selected from one of 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 ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the R is ₅ Each independently selected from one of 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 ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

Said b ₁ Selected from 1, 2, 3, 4 or 5; said b ₂ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b ₃ Selected from 1, 2, 3, 4, 5, 6 or 7; said b ₄ Selected from 1, 2, 3 or 4; said b ₅ Selected from 1, 2 or 3;

the L is ₀ Any one selected from the group consisting of a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 alicyclic ring and a C6 to C30 fused ring group of an aromatic ring, a substituted or unsubstituted C3 to C25 alicyclic ring and a fused ring group of a C2 to C30 heteroaromatic ring;

the L is ₁ Any one selected from a single bond, a substituted or unsubstituted arylene group of C6 to C30, a substituted or unsubstituted heteroarylene group of C2 to C30, a substituted or unsubstituted alicyclic ring of C3 to C30 and a fused ring-back group of an aromatic ring of C6 to C30, a substituted or unsubstituted alicyclic ring of C3 to C25 and a fused ring-back group of a heteroaromatic ring of C2 to C30;

the R is _a Selected from-CF ₃ When the L is ₁ Not selected from single bonds;

the L is ₂ Selected from single bond or one or combination of the following groups:

wherein each Y is independently selected from CH or N;

the X is ₂ 、X ₃ 、X ₄ Each independently selected from O, S, C (R) _p R _q )、N(R _h ) Any one of them;

the R is _p 、R _q Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _p 、R _q Are connected with each other to form a substituted or unsubstituted ring;

the R is _h Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

the R is _b Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _b Are connected with each otherForm a substituted or unsubstituted ring;

the R is ₆ Each independently selected from one of 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 cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

The R is ₇ Each independently selected from one of 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 cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the a ₀ Selected from 1 or 2; the a ₁ Selected from 1, 2, 3 or 4; the a ₂ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the a ₃ Selected from 1, 2, 3, 4, 5 or 6.

The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned between the anode and the cathode or outside one or more than one of the anode and the cathode, and the organic layer contains at least one of the triarylamine compounds.

Advantageous effects

The three-side connected groups of the triarylamine compound shown in the formula I are different from each other, the asymmetric space configuration of the triarylamine compound has easily-controlled glass transition temperature, and can effectively control the crystallinity of materials.

In conclusion, when the asymmetric triarylamine compound provided by the invention is applied to an OLED device, the luminous efficiency of the device can be effectively improved, the driving voltage of the device can be reduced, the service life of the device can be prolonged, and the asymmetric triarylamine compound can be widely applied to commercial production and has good industrialization prospect.

Detailed Description

In the following, a technical solution with embodiments of the present invention will be further clarified and fully elucidated, and it will be apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. Modifications of the invention which are obvious to those skilled in the art are intended to fall within the scope of the invention.

In the present specification, "-" means a moiety attached to another substituent. "-" may be attached at any optional position of the attached group/fragment.

In this specification, when a substituent or linkage site is located across two or more rings, it is meant that it may be attached to any of the two or more rings, in particular to any of the corresponding selectable sites of the rings. For example, the number of the cells to be processed,can indicate-> Can indicate->And so on.

In the present specification, when the position of a substituent or a linking site on a ring is not fixed, it means that it can be linked to Any of the optional sites of the loop. For example, the number of the cells to be processed,can indicate-> Can indicate-> Can represent And so on.

Examples of halogens described herein may include fluorine, chlorine, bromine and iodine.

The alkyl group according to the present invention means a hydrocarbon group having at least one hydrogen atom in an alkane molecule, and may be a straight chain alkyl group or a branched chain alkyl group, preferably having 1 to 30 carbon atoms, preferably having 1 to 25 carbon atoms, preferably having 1 to 20 carbon atoms, 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, dodecyl and the like; the branched alkyl group includes, but is not limited to, isopropyl, isobutyl, sec-butyl, tert-butyl, an isomeric group of 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, but not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

As used herein, "substituted or unsubstituted silyl" refers to-Si (R _n ) ₃ A group wherein each R _n Each 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 ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic ring, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic ring. Preferably, each R _n Each independently selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 10 carbon atoms, particularly preferably 1 to 8 carbon atoms. The cycloalkyl radicals preferably have 3 to 20 carbon atoms, more preferably 3 to 15 carbon atoms, even more preferably 3 to 10 carbon atoms, particularly preferably 3 to 7 carbon atoms. Preferably, each R _n Each 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Examples of the substituted or unsubstituted silyl group may include trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, tri-t-butylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, di-Methyl tertiary butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but is not limited thereto.

The cycloalkyl refers to a hydrocarbon group formed by removing one hydrogen atom in a cycloparaffin molecule, and can be monocyclic cycloalkyl, polycyclic cycloalkyl or bridged cycloalkyl. Preferably 3 to 30 carbon atoms, preferably 3 to 25 carbon atoms, preferably 3 to 20 carbon atoms, preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, particularly preferably 5 to 7 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphene, fenchyl, isobornyl, and the like.

The aryl refers to the generic name of monovalent groups obtained by removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule, and can be monocyclic aryl, polycyclic aryl or condensed ring aryl. Preferably from 6 to 60 carbon atoms, preferably from 6 to 30 carbon atoms, preferably from 6 to 25 carbon atoms, more preferably from 6 to 14 carbon atoms, particularly preferably from 6 to 12 carbon atoms. The monocyclic aryl refers to aryl having only one aromatic ring in the molecule, for example, phenyl, etc., but is not limited thereto; the polycyclic aryl group refers to an aryl group having two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetrabiphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, and the like, but are not limited thereto; the condensed ring aryl group refers to an aryl group having two or more aromatic rings in the molecule and condensed by sharing two adjacent carbon atoms with each other, and specific examples may include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylenyl, fluoranthryl, spirofluorenyl, spirobifluorenyl, and the like.

Heteroaryl according to the present invention refers to the generic term for groups obtained after substitution of one or more aromatic nucleus carbon atoms in the aryl group with heteroatoms, including but not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atoms, preferably having 2 to 60 carbon atoms, preferably having 2 to 30 carbon atoms, more preferably having 2 to 25 carbon atoms, particularly preferably 2 to 20 carbon atoms. The attachment site of the heteroaryl group may be on a ring-forming carbon atom or on a ring-forming heteroatom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group. Specific examples of the monocyclic heteroaryl group may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, and the like; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused ring heteroaryl group may include, but are not limited to, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, dibenzooxazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorene oxaanthracenyl, spirofluorene thianthrenyl, and the like.

The arylene group according to the invention is a generic term for divalent radicals which remain after removal of two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule, and can be a monocyclic arylene group, a polycyclic arylene group or a fused ring arylene group, preferably having 6 to 60 carbon atoms, preferably having 6 to 30 carbon atoms, preferably having 6 to 25 carbon atoms, more preferably having 6 to 20 carbon atoms, particularly preferably having 6 to 18 carbon atoms. The monocyclic arylene group includes phenylene and the like, but is not limited thereto; the polycyclic arylene group includes biphenylene, terphenylene, etc., but is not limited thereto; specific examples may include, but are not limited to, naphthylene, anthrylene, phenanthrylene, pyreylene, triphenylene, fluoranthenylene, and the like.

The heteroarylene group refers to a divalent group in which at least one carbon atom in the arylene group is replaced with a heteroatom including, but not limited to, an oxygen, sulfur, nitrogen, or phosphorus atom. Preferably from 2 to 60, preferably from 2 to 30, more preferably from 2 to 25, particularly preferably from 2 to 20 carbon atoms. The attachment site of the heteroarylene group may be 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. Specific examples of the monocyclic and condensed ring heteroarylene groups may include, but are not limited to, a pyridylene group, a pyrimidinylene group, a triazinylene group, a furanylene group, a thienyl group, a carbazolylene group, a benzofuranylene group, a benzothienyl group, a benzocarbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzocarbazolylene group, and the like; specific examples of the polycyclic heteroarylene group may include bipyridylene group, bipyrimidiylene group, phenylpyridylene group, etc., but are not limited thereto.

The fused ring group of the alicyclic ring and the aromatic ring refers to the general term that after the alicyclic ring and the aromatic ring are fused together, one hydrogen atom is removed, and a monovalent group is left. Preferably having 6 to 60 carbon atoms, preferably having 6 to 30 carbon atoms, preferably having 6 to 25 carbon atoms, preferably having 6 to 18 carbon atoms, still preferably having 6 to 12 carbon atoms, particularly preferably having 6 to 10 carbon atoms, and the fused ring group of the alicyclic and aromatic ring may contain a benzocyclopropane group, a benzocyclobutane group, a benzocyclobutenyl group, a indanyl group, an indenyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a benzocycloheptyl group, a benzocycloheptenyl group, or the like, but is not limited thereto.

The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the sum of monovalent groups obtained by removing one hydrogen atom after the alicyclic ring and the heteroaromatic ring are fused together. Preferably from 5 to 30 carbon atoms, more preferably from 5 to 18 carbon atoms, particularly preferably from 5 to 12 carbon atoms. The fused cyclic group of the alicyclic and heteroaromatic ring may include, but is not limited to, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidbenzocycloheptyl, dibenzofuran-cyclopropyl, dibenzofuran-cyclobutyl, dibenzofuran-cyclopentyl, dibenzofuran-cyclohexyl, dibenzofuran-cycloheptyl, dibenzothiophene-cyclopropyl, dibenzothiophene-cyclobutyl, dibenzothiophene-cyclopentyl, dibenzothiophene-cyclohexyl, dibenzothiophene-cycloheptyl, carbazole-cyclopropyl, carbazole-cyclobutyl, carbazole-cyclopentyl, carbazole-cyclohexyl, carbazole-cycloheptyl, and the like.

The term "fused ring-sub-group" as used herein refers to a generic term for divalent groups obtained by fusing an alicyclic ring to an aromatic ring and then removing two hydrogen atoms. Preferably having 6 to 30 carbon atoms, preferably having 6 to 20 carbon atoms, still preferably having 6 to 18 carbon atoms, and particularly preferably having 6 to 10 carbon atoms, and the fused-back ring group of the alicyclic ring and the aromatic ring may include, but is not limited to, benzocyclopropylene, benzocyclobutylene, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, benzocyclopentylene, benzocyclohexenylene, benzocycloheptylene, naphthocyclopropyl, naphthocyclobutylene, naphthocyclopentyl, naphthocyclohexyl, and the like.

The fused ring group of the alicyclic ring and the heteroaromatic ring refers to the generic term of bivalent groups obtained by fusing the alicyclic ring and the heteroaromatic ring together and removing two hydrogen atoms. Preferably having 3 to 30 carbon atoms, more preferably having 3 to 20 carbon atoms, still more preferably having 3 to 15 carbon atoms, and particularly preferably having 3 to 10 carbon atoms, the fused-back ring group of the alicyclic ring and the heteroaromatic ring may contain a pyrido-cyclopropyl group, a pyrido-cyclobutyl group, a pyrido-cyclopentyl group, a pyrido-cyclohexyl group, a pyrido-benzoheptyl group, a pyrimido-cyclopropyl group, a pyrimido-cyclobutyl group, a pyrimido-cyclopentyl group, a pyrimido-cyclohexyl group, a pyrimido-benzoheptyl group, a dibenzofuran-cyclopropyl group, a dibenzofuran-cyclobutyl group, a dibenzofuran-cyclopentyl group, a dibenzofuran-cyclohexyl group, a dibenzofuran-cycloheptyl group, a dibenzothiophene-cyclopropyl group, a dibenzothiophene-cyclopentyl group, a dibenzothiophene-cyclohexyl group, a dibenzothiophene-cycloheptyl group, a carbazole-cyclopropyl group, a carbazole-benzocarbazolo-cyclopentyl group, a carbazole-carbazolo-cyclohexyl group, a carbazole-carbazolo-cycloheptyl group, and the like, but is not limited thereto.

The substituents in the "substituted or unsubstituted" described herein may be independently selected from deuterium, cyano, nitro, amino, halogen atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C1-C12 alkoxy group, substituted or unsubstituted C1-C6 alkylthio group, substituted or unsubstituted C1-C12 alkylamino group, substituted or unsubstituted C6-C30 aryloxy group, substituted or unsubstituted C6-C30 arylamino group, etc., but are not limited thereto, or two adjacent substituents may be linked to form a ring. Deuterium, cyano, nitro, amino, halogen atom, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C12 alkoxy are preferred, and specific examples may include: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, perylenyl, pyrenyl, fluoranthryl, fluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazolyl, 9-phenylcarbazolyl, 9' -spirobifluorenyl, carbazolo indolyl, pyrrolyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, and the like, but is not limited thereto. Or when the substituent is plural, plural substituents are the same or different from each other; or adjacent substituents may be joined to form a ring.

The term "bonded to form a cyclic structure" as used herein means that two groups are attached 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 three-membered ring, four-membered ring, five-membered ring, six-membered ring, seven-membered ring, eight-membered ring, condensed ring or the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole or the like, but is not limited thereto.

in the above formula I, the formula I is ₁ -A _r 1、*-L ₂ -Ar ₂ 、*-L ₀ -(Ra)n ₀ Are different from each other;

the X is selected from O or S;

each z is independently selected from CH or N;

said n ₁ Selected from 1, 2, 3 or 4; when n is ₁ Above 1, two or more R ₀ Are identical or different from each other, or adjacent two R ₀ Are connected with each other to form a substituted or unsubstituted ring;

the Ar is as follows ₂ One or a combination of the following groups:

wherein each E is independently selected from CH or N;

the R is _g Selected from the group consisting of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic ring, and a C6-C30 aromatic ringAny one of a ring-closing group, a substituted or unsubstituted C3-C30 alicyclic ring and a condensed ring group of a C2-C30 heteroaromatic ring;

the R is _k Each independently selected from one of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

the L is ₀ Selected from the group consisting of a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic ring, and a C6-C30 aromatic ring, a substituted or unsubstituted C3-C25 alicyclic ringAny one of a ring and a sub-condensed cyclic group of a C2 to C30 heteroaromatic ring;

wherein each Y is independently selected from CH or N;

the R is _h Selected from the group consisting of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted C3-C30 alicyclic ring and a C2-to-C30 heteroaryl ring Any one of the fused ring groups of the heteroaromatic ring of C30;

the R is _b Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _b Are connected with each other to form a substituted or unsubstituted ring;

Preferably, said R ₁ To R ₃ Each independently selected from the group consisting of 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,A substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropenyl group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, an unsubstituted or unsubstituted quinolinyl group, or a combination thereof.

Preferably, the Ar ₁ Any one selected from the following groups:

the X is selected from O or S;

each z is independently selected from CH or N;

the R is ₈ Each 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, substituted or unsubstituted C2-C30 heteroaryl;

the p is ₁ Selected from 1, 2, 3 or 4; the p is ₂ Selected from 1; the p is ₃ Selected from 1 or 2; the P is ₄ Selected from 1, 2, 3, 4, 5 or 6; the P is ₅ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the p is ₆ Selected from 1, 2 or 3; the P is ₇ Selected from 1, 2, 3, 4, 5, 6 or 7;

preferably, at most two z in each group are selected from N, or at most one z is selected from N.

Preferably, said R ₈ Each independently selected from the group consisting of 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocyclopropane, a substituted or unsubstituted benzocyclobutane, a substituted or unsubstituted indanyl, a substituted or unsubstituted indenyl, a substituted or unsubstituted tetrahydronaphthyl, a substituted or unsubstituted dihydronaphthyl, a substituted or unsubstituted benzocycloheptane, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, or a combination thereof.

Preferably, the Ar ₂ One or a combination of the following groups:

each E is independently selected from CH or N;

the R is ₉ Each independently selected from one of 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 ring groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused ring groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the R is _n Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

the R is _i 、R _j Each independently selected from one of a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C3-C15 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

The m is ₀ Selected from 1, 2, 3 or 4; the m is ₁ Selected from 1, 2, 3, 4 or 5; by a means ofM is as follows ₂ Selected from 1, 2, 3, 4, 5, 6 or 7; the m is ₃ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m is ₄ Selected from 1 or 2; the m is ₅ Selected from 1, 2 or 3; the m is ₆ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the m is ₇ Selected from 1, 2, 3, 4, 5 or 6; the m is ₈ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m is ₉ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the m is ₁₀ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

Preferably, said R ₉ Selected from the group consisting of 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclobutene group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group.

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

Preferably, the L ₀ One selected from the group consisting of:

the X is ₅ 、X ₆ 、X ₇ Each independently selected from O, S, C (R) _o R _s )、N(R _c ) Any one of them;

the R is _o 、R _s Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _o 、R _s Are connected with each other to form a substituted or unsubstituted ring;

the R is _c Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

The R is _w Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _w Are connected with each other to form a substituted or unsubstituted ring;

the R is ₁₂ Each independently selected from one of 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 cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

said e ₀ Selected from 1 or 2; said e ₁ Selected from 1, 2, 3 or 4; said e ₂ Selected from 1, 2, 3, 4, 5 or 6; said e ₃ Selected from 1, 2, 3, 4 or 5; said e ₄ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said e ₅ Selected from 1, 2 or 3; said e ₆ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e ₇ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; when two or more R's are present ₁₂ When two or more R' s ₁₂ Are identical or different from each other, or adjacent two R ₁₂ Are linked to each other to form a substituted or unsubstituted ring.

Still more preferably, the said ₀ -(Ra)n ₀ One selected from the group consisting of:

preferably, when R _a Selected from-CF ₃ 、-Si(R ₁ R ₂ R ₃ ) When n is ₀ Selected from 1, 2 or 3, more preferably 1 or 2.

Preferably, when R _a When selected from-F, n ₀ Selected from 5.

Preferably, said 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 unsubstitutedA substituted trimethylsilyl group, a substituted or unsubstituted triethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropenyl group, a substituted or unsubstituted benzocyclobutanyl group, a substituted or unsubstituted benzocycloanyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphtalenyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group.

Preferably, the L ₁ Selected from a single bond or one of the following groups:

the X is ₈ 、X ₉ 、X ₁₀ Each independently selected from O, S, C (R) _x R _y )、N(R _z ) Any one of them;

the R is _x 、R _y Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substitutedOr any one of an unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring, or R _x 、R _y Are connected with each other to form a substituted or unsubstituted ring;

the R is _z Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

The R is _v Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _v Are connected with each other to form a substituted or unsubstituted ring;

the R is ₁₁ Each independently selected from one of 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 cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the r is ₀ Selected from 1 or 2; the r is ₁ Selected from 1, 2, 3 or 4; the r is ₂ Selected from 1, 2, 3, 4, 5 or 6; the r is ₃ Selected from 1, 2, 3, 4 or 5; the r is ₄ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the r is ₅ Selected from 1, 2 or 3; the r is ₆ Selected from 1, 2, 3, 4, 5, 6 or 7, 8, 9 or 10; the r is ₇ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; when two or more R's are present ₁₁ When two or more R' s ₁₁ Are identical or different from each other, or adjacent two R ₁₁ Are linked to each other to form a substituted or unsubstituted ring.

Preferably, said R ₁₁ Selected from the group consisting of 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclobutene group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group.

Preferably, the L ₂ Selected from single bond or one of the groups shown belowOr a combination thereof:

the R is _r Any one selected from a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

the R is _t Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _t Are connected with each other to form a substituted or unsubstituted ring;

the R is _u Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _u Are connected with each other to form a substituted or unsubstituted ring;

the R is ₁₃ Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstitutedSubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring group of substituted or unsubstituted C3-C30 alicyclic ring and C6-C30 aromatic ring, fused ring group of substituted or unsubstituted C3-C30 alicyclic ring and C2-C30 heteroaromatic ring;

the R is ₁₄ Each independently selected from one of 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 cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the k is ₀ Selected from 1 or 2; the k is ₁ Selected from 1, 2, 3 or 4; the k is ₂ Selected from 1, 2, 3, 4, 5 or 6; the k is ₃ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the k is ₄ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the k is ₅ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the k is ₆ Selected from 1, 2, 3, 4 or 5; the k is ₇ Selected from 1, 2 or 3; the k is ₈ Selected from 1, 2, 3, 4, 5, 6 or 7.

Preferably, said 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, and extractionA substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocyclopropenyl group, a substituted or unsubstituted benzocyclobutanyl group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group.

Preferably, said R ₁₄ 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 norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted A pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group.

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

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the triarylamine compounds of formula I of the present invention are shown in the above list of specific structural forms, but the present invention is not limited to these chemical structures, and substituents are included in the compounds of formula I based on the structures of formula I.

In addition, the invention also provides an organic electroluminescent device which comprises at least one of the triarylamine compounds.

Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is positioned 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-containing compounds.

Still preferably, the organic electroluminescent device according to the present invention may include one or more organic layers, the organic layers may include a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, a hole blocking layer, an electron blocking layer, a capping layer, and the like, and specifically, the organic layers between the anode and the cathode may include a light emitting layer, a hole injecting layer, a hole transporting layer, an electron injecting layer, a hole blocking layer, an electron blocking layer, and the like, and the organic layers outside one or more of the anode and the cathode may include a capping layer, and the like. The organic layer may be formed of a single-layer structure or a multilayer structure in which the above organic layers are stacked; meanwhile, each organic layer may further include one or more layers, for example, the hole transport layer includes a first hole transport layer and a second hole transport layer. However, the structure of the organic electroluminescent device is not limited thereto, and may include fewer or more organic layers.

Further preferably, the organic layer is located outside one or more of the anode and the cathode, and the organic layer includes a coating layer including the triarylamine compound according to the present invention.

Most preferably, the organic layer is located outside the cathode, and the organic layer comprises a cover layer, and the cover layer comprises the triarylamine compound of the present invention.

The anode of the present invention is generally preferably a material having a high work function, which may be formed by depositing or sputtering anode material on a substrate. The anode may be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO ₂ ) Zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode may 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 may have a single-layer structure or a multi-layer structure including two or more layers, for example, the anode may have a three-layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.

The hole injection layer is preferably a material having a high work function, and may 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 organic compounds such as phthalocyanine compounds and polycyano-containing conjugated organic materials, but are not limited thereto. 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-hexaazabenzophenanthrene (abbreviated as: HAT-CN), 4',4″ -tris (N, N-diphenylamino) triphenylamine (abbreviated as: TDATA), 4',4″ -tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as: MTDATA), copper (II) phthalocyanine (abbreviated as: cuPc), N' -bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N, N '-diphenyl-biphenyl-4, 4' -diamine (abbreviated as: DNTPD), etc., which may be a single structure composed of a single substance or a single-layer or multi-layer structure formed of different substances.

The hole transport layer may include a first hole transport layer material and a second hole transport layer material, preferably a material having high hole mobility. The hole transport layer material provided by the invention can be selected from any one or more of the following structures: phthalocyanine compounds, anthraquinone compounds, biphenyldiamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, and the like, but are not limited thereto.

The light-emitting layer material of the present invention may use red, green or blue light-emitting materials, and generally comprises a host material (also referred to as a host material) and a doped material (also referred to as a guest material), and the light-emitting layer material may comprise a plurality of host materials and a plurality of doped materials, and the guest material may be a simple fluorescent material or a phosphorescent material, or may be formed by combining fluorescent and phosphorescent materials. The host material of the light-emitting layer is required to have a bipolar charge transport property and an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material, and may include, in addition to the carbazole compound provided by the present invention, anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, and the like, and heterocyclic ring-containing compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, distyrylaryl derivatives, stilbene derivatives, and the like, but are not limited thereto. The guest material may comprise: metal complexes (for example, iridium complex, platinum complex, osmium complex, rhodium complex, terbium complex, europium complex, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., but are not limited thereto.

The electron transport layer may include a first electron transport layer material and a second electron transport layer material. The electron transport material can be selected from any one or more of the following structures: oxadiazole derivatives, anthraquinone dimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinone dimethane and derivatives thereof, fluorenone derivatives, biphenyl-p-benzoquinone derivatives, 8-hydroxyquinoline and metal complexes of derivatives thereof, which may have a single structure formed by a single substance or may have a single-layer structure or a multi-layer structure formed by different substances.

The electron injection layer of the present invention is preferably a material having a low work function, and may 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, and the like, and a mixture material of an electron transporting material and an insulating organic metal salt may also be used, and in particular, the organic metal salt may include a metal acetate, a metal benzoate, or a metal stearate, but is not limited thereto.

The cathode according to the present invention is provided on the electron transport region, and the cathode may be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive 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 including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

The coating layer according to the present invention is provided on the outside of the cathode and 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 according to the present invention. Preferably, the coating material of the present invention is selected from any one or a combination of at least two of the triarylamine compounds described herein.

The method for preparing and forming each of the organic layers, the cathode and the anode is not particularly limited, and any one of vacuum evaporation, ink-jet printing, sputtering, plasma, spin coating, vapor deposition, knife coating, laser thermal transfer, electrospray coating, and slit coating may be used, and each of the organic layers is preferably prepared by vacuum evaporation, ink-jet printing, or spin coating, but is not limited thereto.

The organic light-emitting device can be widely applied to the fields of panel display, illumination light sources, flexible OLED, electronic paper, organic solar cells, digital cameras, organic photoreceptors or organic thin film transistors, vehicle-mounted systems and signal lamps.

Preparation and characterization of the Compounds

Description of the starting materials, reagents and characterization equipment:

the raw materials and reagent sources used in the following examples are not particularly limited, and may be commercially available products or prepared by methods well known to those skilled in the art.

The mass spectrum uses a Wotes G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer in UK, chloroform as a solvent;

the elemental analysis uses a Vario EL cube type organic elemental analyzer of Elementar, germany, and the mass of the sample is 5-10 mg;

the following is one preparation method of the compound represented by the formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compounds of formula I may be prepared by the reaction schemes shown below, using conventional methods well known to those skilled in the art. For example, a carbon-carbon coupling reaction, a carbon-nitrogen coupling reaction, or the like, and the kind and position of substituents or the number of substituents may be changed according to techniques known in the art.

Synthetic route

Preparation of the compound of formula I:

the X is ₁ ～X ₄ Each is independently selected from any one of I, br and Cl; the Ar is as follows ₁ ～Ar ₂ 、R _a 、L ₀ ～L ₂ 、n ₀ The definition of (2) is the same as the definition described above.

Synthesis example 1: preparation of intermediate C-11:

A '-11 (18.52 g,80.00 mmol), b' -11 (13.04 g,80.00 mmol) and K were added in this order to a reaction flask under nitrogen ₂ CO ₃ (16.58 g,120.00 mmol) and 435mL of mixed solvent (toluene: ethanol: water=2:1:1), and after air was replaced with nitrogen three times, pd (PPh) was added ₃ ) ₄ (0.92 g,0.80 mmol) was stirred at reflux temperature for 3 hours, after the reaction was completed, cooled to room temperature, suction filtered to give a cake, and the cake was rinsed with ethanol, and finally the cake was quenched with toluene: ethanol=10: 1 recrystallisation gives intermediate C-11 (17.69 g, 82% yield) with HPLC purity ≡99.83%. Mass spectrum m/z:269.0621 (theory: 269.0607).

The preparation method of the intermediate C-11 in synthetic example 1 is characterized in that the raw materials are correspondingly replaced, and the intermediate can be prepared, wherein the raw materials are shown in the following table:

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synthesis example 2: preparation of intermediate M-36:

under the protection of nitrogen, m-36 (17.20 g,100.00 mmol), n-36 (29.81 g,100.00 mmol) and K are added into a reaction bottle in sequence ₂ CO ₃ (20.73 g,150.00 mmol) and 540mL of mixed solvent (toluene: ethanol: water=2:1:1), and after three air substitutions with nitrogen, pd (PPh) was added ₃ ) ₄ (1.16 g,1.00 mmol) was stirred at reflux temperature for 4 hours, after the reaction was completed, cooled to room temperature, suction filtered to obtain a cake, and the cake was rinsed with ethanol, and finally the cake was washed with toluene: ethanol=10: 1 recrystallisation gives intermediate M-36 (29.02 g, 84% yield) with HPLC purity ≡99.85%. Mass spectrum m/z:345.1502 (theory: 345.1517).

The preparation method of intermediate M-36 in synthetic example 1 is followed by corresponding replacement of the raw materials, namely the intermediate:

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synthesis example 3: preparation of Compound 11:

preparation of intermediate B-11:

m-11 (9.92 g,60.00 mmol), b-11 (16.76 g,60.00 mmol), sodium tert-butoxide (10.38 g,108.00 mmol) were added to 320ml toluene under nitrogen and Pd (dppf) Cl was added with stirring ₂ (0.48 g,0.65 mmol) and the mixture of the above reactants was heated under reflux for 4 hours. After the reaction is finished, cooling to room temperature, adding distilled water, extracting with dichloromethane, standing for liquid separation, collecting an organic layer, drying with anhydrous magnesium sulfate, filtering, concentrating the filtrate by reduced pressure distillation, cooling for crystallization, filtering, and recrystallizing the obtained solid with ethyl acetate to obtain an intermediateBody B-11 (17.24 g, 79%) showed 99.89% purity of the solid as determined by HPLC. Mass spectrum m/z:363.1825 (theory: 363.1839).

Preparation of Compound 11:

b-11 (14.55 g,40.00 mmol), C-11 (10.79 g,40.00 mmol), pd under nitrogen ₂ (dba) ₃ (0.37g，0.40mmol)、P(t-Bu) ₃ (1.60 mL of a 0.5M toluene solution, 0.80 mmol) and sodium t-butoxide (7.69 g,80.00 mmol) were added to 280mL of toluene, and the mixture was stirred and heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane and distilled water were added to the mixture to extract, the mixture was left to stand for separation, the organic phase was collected and dried over anhydrous magnesium sulfate, the filtrate was concentrated by distillation under reduced pressure, the filtrate was cooled and crystallized, the obtained solid was suction-filtered, and the obtained solid was recrystallized from toluene to obtain compound 11 (17.91 g, 75%), and the purity of the solid was not less than 99.94% as measured by HPLC. Mass spectrum m/z:596.2662 (theory: 596.2679). Theoretical element content (%) C ₃₈ H ₄₀ N ₂ OSi ₂ : c,76.46; h,6.75; n,4.69. Measured element content (%): c,76.51; h,6.72; n,4.73.

Synthesis example 4: preparation of compound 17:

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according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-17, b-11 was replaced with equimolar b-17, and C-11 was replaced with equimolar C-17, to obtain Compound 17 (19.46 g), which was found to have a solid purity of ≡99.97% by HPLC. Mass spectrum m/z:704.3211 (theory: 704.3223). Theoretical element content (%) C ₄₉ H ₄₄ N ₂ OSi: c,83.48; h,6.29; n,3.97. Measured element content (%): c,83.53; h,6.25; n,4.00.

Synthesis example 5: preparation of compound 23:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 was replaced with equimolar b-23, and C-11 was replaced with equimolar C-23, to obtain Compound 23 (18.26 g), which was found to have a solid purity of ≡99.93% by HPLC. Mass spectrum m/z:633.2646 (theory: 633.2632). Theoretical element content (%) C ₄₀ H ₃₉ N ₃ OSi ₂ : c,75.79; h,6.20; n,6.63. Measured element content (%): c,75.84; h,6.16; n,6.67.

Synthesis example 6: preparation of compound 33:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 with equimolar b-33, and C-11 with equimolar C-33, compound 33 (17.29 g) was obtained, and the purity of the solid was ≡ 99.95% by HPLC detection. Mass spectrum m/z:568.2799 (theory: 568.2786). Theoretical element content (%) C ₃₈ H ₂₄ D ₈ N ₂ OSi: c,80.24; h,7.09; n,4.92. Measured element content (%): c,80.19; h,7.12; n,4.88.

Synthesis example 7: preparation of Compound 36:

according to the same manner as that for Compound 11 of Synthesis example 3, except that M-11 was replaced with equimolar M-36, b-11 was replaced with equimolar b-36, and C-11 was replaced with equimolar C-17, compound 36 (19.26 g) was obtained, and the purity of the solid as determined by HPLC was ≡ 99.92%. Mass spectrum m/z:687.2720 (theory: 687.2706). Theoretical element content (%) C ₄₇ H ₃₇ N ₃ OSi: c,82.06; h,5.42; n,6.11. Measured element content (%): c,82.11; h,5.39; n,6.08.

Synthesis example 8: preparation of Compound 68:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-68, b-11 was replaced with equimolar b-68, and C-11 was replaced with equimolar C-17, to obtain Compound 68 (17.37 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:586.2428 (theory: 586.2440). Theoretical element content (%) C ₄₀ H ₃₄ N ₂ OSi: c,81.87; h,5.84; n,4.77. Measured element content (%): c,81.92; h,5.88; n,4.80.

Synthesis example 9: preparation of compound 72:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-72, b-11 was replaced with equimolar b-68, and C-11 was replaced with equimolar C-72, to obtain Compound 72 (18.03 g), and the purity of the solid was ≡ 99.91% by HPLC detection. Mass spectrum m/z:662.2739 (theory: 662.2753). Theoretical element content (%) C ₄₆ H ₃₈ N ₂ OSi: c,83.35; h,5.78; n,4.23. Measured element content (%): c,83.30; h,5.81; n,4.19.

Synthesis example 10: preparation of compound 74:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 with equimolar b-68, and C-11 with equimolar C-17, compound 74 (18.09 g) was obtained, and the purity of the solid was ≡ 99.94% by HPLC detection. Mass spectrum m/z:636.2610 (theory: 636.2597). Theoretical element content (%) C ₄₄ H ₃₆ N ₂ OSi: c,82.98; h,5.70; n,4.40. Measured element content (%): c,83.03; h,5.67; n,4.44.

Synthesis example 11: preparation of Compound 83:

according to the same manner as that for Compound 11 of Synthesis example 3, except that M-11 was replaced with equimolar M-83, b-11 was replaced with equimolar b-83, and C-11 was replaced with equimolar C-17, compound 83 (18.60 g) was obtained, and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:636.2586 (theory: 636.2597). Theoretical element content (%) C ₄₄ H ₃₆ N ₂ OSi: c,82.98; h,5.70; n,4.40. Measured element content (%): c,83.02; h,5.65; n,4.37.

Synthesis example 12: preparation of compound 86:

preparation of intermediate d-86:

according to the same manner as that for intermediate C-11 in Synthesis example 1, a ' -11 was replaced with equimolar a ' -33, b ' -11 with equimolar e-86 to obtain intermediate d-86 (17.59 g), and the purity of the solid was. Mass spectrum m/z:264.1051 (theory: 264.1039).

Preparation of compound 86:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-86, b-11 was replaced with equimolar d-86, and C-11 was replaced with equimolar C-86, to obtain Compound 86 (18.65 g), and the purity of the solid was ≡ 99.93% by HPLC detection. Mass spectrum m/z:665.2815 (theory: 665.2800). Theoretical element content (%) C ₄₅ H ₃₁ D ₄ N ₃ OSi: c,81.17; h,5.90; n,6.31. Measured element content (%): c,81.22; h,5.86; n,6.34.

Synthesis example 13: preparation of compound 96:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 with equimolar b-96, and C-11 with equimolar C-17, compound 96 (20.08 g) was obtained, and the purity of the solid was ≡ 99.98% by HPLC detection. Mass spectrum m/z:822.3080 (theory: 822.3066). Theoretical element content (%) C ₅₉ H ₄₂ N ₂ OSi: c,86.10; h,5.14; n,3.40. Measured element content (%): c,86.05; h,5.18; n,3.37.

Synthesis example 14: preparation of compound 109:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-109, b-11 was replaced with equimolar b-68, and C-11 was replaced with equimolar C-109, to obtain Compound 109 (18.19 g), and the purity of the solid was ≡ 99.92% by HPLC detection. Mass spectrum m/z:688.2671 (theory: 688.2658). Theoretical element content (%) C ₄₆ H ₃₆ N ₄ OSi: c,80.20; h,5.27; n,8.13. Measured element content (%): c,80.15; h,5.31; n,8.10.

Synthesis example 15: preparation of Compound 113:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-113, b-11 was replaced with equimolar b-68, and C-11 was replaced with equimolar C-113, to obtain Compound 113 (19.05 g), which was found to have a solid purity of ≡99.97% by HPLC. Mass spectrum m/z:743.2839 (theory: 743.2829). Theoretical element content (%) C ₄₇ H ₃₇ N ₇ OSi: c,75.88; h,5.01; n,13.18. Measured element content (%): c,75.93; h,4.98; n,13.22.

Synthesis example 16: preparation of compound 115:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-115, b-11 with equimolar b-68, and C-11 with equimolar C-115, compound 115 (18.10 g) was obtained, and the purity of the solid was ≡ 99.93% by HPLC detection. Mass spectrum m/z:655.2442 (theory: 655.2455). Theoretical element content (%) C ₄₃ H ₃₄ FN ₃ OSi: c,78.75; h,5.23; n,6.41. Measured element content (%): c,78.80; h,5.19; n,6.37.

Synthesis example 17: preparation of compound 123:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-123, b-11 was replaced with equimolar b-123, and C-11 was replaced with equimolar C-17, to obtain Compound 123 (17.75 g), which was found to have a solid purity of ≡99.94% by HPLC. Mass spectrum m/z:607.2659 (theory: 607.2672). Theoretical element content (%) C ₄₀ H ₂₅ D ₇ N ₂ O ₂ Si: c,79.04; h,6.47; n,4.61. Measured element content (%): c,78.99; h,6.51; n,4.58.

Synthesis example 18: preparation of compound 146:

according to the same manner as that for Compound 11 of Synthesis example 3, except that M-11 was replaced with equimolar M-23, b-11 was replaced with equimolar b-68, and C-11 was replaced with equimolar C-146, compound 146 (18.28 g) was obtained, and the purity of the solid as determined by HPLC was ≡ 99.98%. Mass spectrum m/z:736.2898 (theory: 736.2910). Theoretical element content (%) C ₅₂ H ₄₀ N ₂ OSi：C,84.75；H,5.47；N,3.80。Measured element content (%): c,84.80; h,5.50; n,3.76.

Synthesis example 19: preparation of compound 163:

according to the same manner as that for preparing compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-163, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-163, to obtain compound 163 (18.82 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:662.2346 (theory: 662.2357). Theoretical element content (%) C ₄₁ H ₃₁ F ₅ N ₂ O: c,74.31; h,4.72; n,4.23. Measured element content (%): c,74.26; h,4.68; n,4.26.

Synthesis example 20: preparation of compound 171:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-171, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-171, to obtain Compound 171 (19.34 g), which was found to have a solid purity of ≡99.93% by HPLC. Mass spectrum m/z:690.2621 (theory: 690.2608). Theoretical element content (%) C ₄₃ H ₂₇ D ₄ F ₅ N ₂ O: c,74.77; h,5.11; n,4.06. Measured element content (%): c,74.82; h,5.07; n,4.10.

Synthesis example 21: preparation of compound 176:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 with equimolar b-163, and C-11 with equimolar C-17, compound 176 (19.64 g) was obtained, and HPLC detection was performedThe purity of the solid is not less than 99.95 percent. Mass spectrum m/z:654.1719 (theory: 654.1731). Theoretical element content (%) C ₄₁ H ₂₃ F ₅ N ₂ O: c,75.22; h,3.54; n,4.28. Measured element content (%): c,75.17; h,3.50; n,4.31.

Synthesis example 22: preparation of Compound 187:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 was replaced with equimolar b-187, and C-11 was replaced with equimolar C-187, to obtain Compound 187 (19.33 g), and the purity of the solid was ≡ 99.91% by HPLC detection. Mass spectrum m/z:710.2370 (theory: 710.2357). Theoretical element content (%) C ₄₅ H ₃₁ F ₅ N ₂ O: c,76.05; h,4.40; n,3.94. Measured element content (%): c,76.10; h,4.36; n,3.97.

Synthesis example 23: preparation of compound 193:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-193, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-193, to give Compound 193 (20.78 g), which was found to have a solid purity of ≡ 99.97% by HPLC. Mass spectrum m/z:711.2321 (theory: 711.2309). Theoretical element content (%) C ₄₄ H ₃₀ F ₅ N ₃ O: c,74.25; h,4.25; n,5.90. Measured element content (%): c,74.30; h,4.29; n,5.87.

Synthesis example 24: preparation of compound 201:

the compound according to synthesis example 311, M-11 was replaced with equimolar M-201, b-11 with equimolar b-201, and C-11 with equimolar C-17 to give compound 201 (19.21 g), which was found to have a solid purity of ≡ 99.92% by HPLC. Mass spectrum m/z:716.1499 (theory: 716.1510). Theoretical element content (%) C ₄₀ H ₂₁ F ₉ N ₂ O: c,67.04; h,2.95; n,3.91. Measured element content (%): c,66.99; h,2.91; n,3.88.

Synthesis example 25: preparation of compound 208:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-208, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-208, to obtain Compound 208 (19.48 g), which was found to have a solid purity of ≡ 99.95% by HPLC. Mass spectrum m/z:705.1856 (theory: 705.1840). Theoretical element content (%) C ₄₄ H ₂₄ F ₅ N ₃ O: c,74.89; h,3.43; n,5.95. Measured element content (%): c,74.94; h,3.39; n,5.98.

Synthesis example 26: preparation of compound 213:

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according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-213, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-213, to obtain Compound 213 (18.37 g), and the purity of the solid was ≡ 99.94% by HPLC detection. Mass spectrum m/z:706.1779 (theory: 706.1792). Theoretical element content (%) C ₄₃ H ₂₃ F ₅ N ₄ O: c,73.08; h,3.28; n,7.93. Measured element content (%): c,73.13; h,3.32; n,7.89.

Synthesis example 27: preparation of compound 216:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-115, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-216, to obtain Compound 216 (19.50 g), which was found to have a solid purity of ≡99.96% by HPLC. Mass spectrum m/z:727.1292 (theory: 727.1306). Theoretical element content (%) C ₄₀ H ₁₈ F ₉ N ₃ O: c,66.03; h,2.49; n,5.78. Measured element content (%): c,65.98; h,2.52; n,5.82.

Synthesis example 28: preparation of Compound 269:

according to the same manner as that of Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-269, b-11 was replaced with equimolar b-269, and C-11 was replaced with equimolar C-269, whereby Compound 269 (18.12 g) was obtained, and the purity of the solid was ≡ 99.91% by HPLC detection. Mass spectrum m/z:580.2151 (theory: 580.2138). Theoretical element content (%) C ₃₆ H ₂₈ F ₄ N ₂ O: c,74.47; h,4.86; n,4.82. Measured element content (%): c,74.52; h,4.90; n,4.79.

Synthesis example 29: preparation of compound 288:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-288, b-11 was replaced with equimolar b-269, and C-11 was replaced with equimolar C-288, to obtain Compound 288 (19.69 g), which was found to have a solid purity of ≡ 99.98% by HPLC. Mass spectrum m/z:683.2173 (theory: 683.2184). Theoretical element content (%) C ₄₅ H ₂₈ F ₃ N ₃ O: c,79.05; h,4.13; n,6.15. Measured element content (%): c,79.10; h,4.09; n,6.18.

Synthesis example 30: preparation of compound 292:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-292, b-11 was replaced with equimolar b-269, and C-11 was replaced with equimolar C-292, to obtain Compound 292 (18.47 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:584.1839 (theory: 584.1824). Theoretical element content (%) C ₃₆ H ₂₃ F ₃ N ₄ O: c,73.96; h,3.97; n,9.58. Measured element content (%): c,74.00; h,4.02; n,9.61.

Synthesis example 31: preparation of compound 314:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-314, b-11 was replaced with equimolar b-314, and C-11 was replaced with equimolar C-314, to obtain Compound 314 (19.28 g), which was found to have a solid purity of ≡ 99.95% by HPLC. Mass spectrum m/z:642.2579 (theory: 642.2593). Theoretical element content (%) C ₄₁ H ₁₇ D ₉ F ₃ N ₃ O: c,76.62; h,5.49; n,6.54. Measured element content (%): c,76.57; h,5.51; n,6.50.

Synthesis example 32: preparation of compound 323:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 with equimolar b-314, and C-11 with equimolar C-17, compound 323 (18.47 g) was obtained, and the purity of the solid was ≡ 99.91% by HPLC detection. Mass spectrum m/z:632.2090 (theoretical value) : 632.2075). Theoretical element content (%) C ₄₂ H ₂₇ F ₃ N ₂ O: c,79.73; h,4.30; n,4.43. Measured element content (%): c,79.68; h,4.26; n,4.39.

Synthesis example 33: preparation of Compound 353:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-353, b-11 was replaced with equimolar b-314, and C-11 was replaced with equimolar C-353, whereby Compound 353 (19.00 g) was obtained, and the purity of the solid was ≡ 99.93% by HPLC detection. Mass spectrum m/z:678.2754 (theory: 678.2765). Theoretical element content (%) C ₄₅ H ₂₅ D ₆ F ₃ N ₂ O: c,79.63; h,5.49; n,4.13. Measured element content (%): c,79.58; h,5.53; n,4.09.

Synthesis example 34: preparation of compound 364:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-364, b-11 was replaced with equimolar b-314, and C-11 was replaced with equimolar C-364, to obtain Compound 364 (18.80 g), and the purity of the solid was ≡ 99.98% by HPLC detection. Mass spectrum m/z:701.1913 (theory: 701.1902). Theoretical element content (%) C ₄₂ H ₂₅ F ₆ N ₃ O: c,71.89; h,3.59; n,5.99. Measured element content (%): c,71.94; h,3.63; n,5.96.

Synthesis example 35: preparation of compound 370:

following the same procedure as for the preparation of Compound 11, synthesis example 3, M-11 was replaced with Equimolar M-370, b-11 replaced with equimolar b-314 and C-11 replaced with equimolar C-370, giving compound 370 (18.81 g) with a solid purity of > 99.96% as measured by HPLC. Mass spectrum m/z:734.2280 (theory: 734.2293). Theoretical element content (%) C ₄₈ H ₂₉ F ₃ N ₄ O: c,78.46; h,3.98; n,7.63. Measured element content (%): c,78.51; h,4.02; n,7.59.

Synthesis example 36: preparation of compound 390:

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according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-23, b-11 was replaced with equimolar b-314, and C-11 was replaced with equimolar C-390, to obtain Compound 390 (18.47 g), and the purity of the solid was ≡ 99.94% by HPLC detection. Mass spectrum m/z:732.2400 (theory: 732.2388). Theoretical element content (%) C ₅₀ H ₃₁ F ₃ N ₂ O: c,81.95; h,4.26; n,3.82. Measured element content (%): c,82.00; h,4.30; n,3.79.

Synthesis example 37: preparation of compound 414:

according to the same manner as that for Compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-414, b-11 was replaced with equimolar b-414, and C-11 was replaced with equimolar C-414, to obtain Compound 414 (17.60 g), which was found to have a solid purity of ≡ 99.97% by HPLC. Mass spectrum m/z:578.1973 (theory: 578.1960). Theoretical element content (%) C ₃₆ H ₃₀ N ₄ SSi: c,74.70; h,5.22; n,9.68. Measured element content (%): c,74.65; h,5.18; n,9.71.

Synthesis example 38: preparation of compound 514:

according to the same manner as that for Compound 11 of Synthesis example 3, except that M-11 was replaced with equimolar M-514, b-11 was replaced with equimolar b-68, and C-11 was replaced with equimolar C-514, compound 514 (18.23 g) was obtained, and the purity of the solid was ≡ 99.92% by HPLC detection. Mass spectrum m/z:632.1790 (theory: 632.1776). Theoretical element content (%) C ₄₀ H ₃₂ N ₂ S ₂ Si: c,75.91; h,5.10; n,4.43. Measured element content (%): c,75.86; h,5.06; n,4.47.

Synthesis example 39: preparation of compound 636:

according to the same manner as that for Compound 11 in Synthesis example 3, M-11 was replaced with equimolar M-636, b-11 was replaced with equimolar b-163, and C-11 was replaced with equimolar C-636, to obtain Compound 636 (20.39 g), which was found to have a solid purity of ≡ 99.96% by HPLC. Mass spectrum m/z:738.1890 (theory: 738.1877). Theoretical element content (%) C ₄₄ H ₂₇ F ₅ N ₄ S: c,71.53; h,3.68; n,7.58. Measured element content (%): c,71.48; h,3.71; n,7.62.

Synthesis example 40: preparation of compound 702:

according to the same manner as that for preparing compound 11 of Synthesis example 3, M-11 was replaced with equimolar M-702, b-11 was replaced with equimolar b-314, and C-11 was replaced with equimolar C-702, to obtain compound 702 (18.74 g), and the purity of the solid was ≡ 99.96% by HPLC detection. Mass spectrum m/z:624.1582 (theory: 624.1596). Theoretical element content (%) C ₃₈ H ₂₃ F ₃ N ₄ S: c,73.06; h,3.71; n,8.97. Measured element content (%): c,73.11; h,3.67; n,9.00.

Device example 1

Firstly, an ITO/Ag/ITO glass substrate was cut into a size of 50 mm. Times.50 mm. Times.0.7 mm as an anode, the glass substrate was washed with distilled water 2 times, then with ultrasonic waves for 30 minutes, then with solvents such as acetone, isopropyl alcohol and methanol in this order, and with ultrasonic waves for 15 minutes, and with UV ozone for 30 minutes, and then sent to a vapor deposition machine. A compound HI-1 having a thickness of 35nm was vapor-deposited on the prepared ITO transparent electrode as a hole injection layer on a glass substrate. HT-1 of 40nm was vacuum deposited as a hole transport layer on the hole injection layer. Host material and dopant (5 wt%) having a thickness of 35nm were evaporated as light emitting layers on the hole transport layer under the same vacuum deposition conditions. Wherein, the host material is GH, GD is taken as a doping agent, and the following steps are 98:2 mass ratio and mixing evaporation. On the upper surface of the light-emitting layer, HB-1 with the thickness of 10nm is sequentially evaporated to serve as a hole blocking layer, ET-1 (30 nm) is sequentially evaporated to serve as an electron transport layer by a vacuum evaporation mode, an electron injection layer LiF (1 nm) is evaporated, and a cathode Mg is evaporated: ag (10 nm). Subsequently, the compound 11 prepared in example 1 above was evaporated as a coating layer (65 nm) on a cathode to prepare an organic electroluminescent device.

Device examples 2 to 38

An organic electroluminescent device was produced by the same production method as in device example 1, except that compound 11 in device example 1 was replaced with compound 17, compound 23, compound 33, compound 36, compound 68, compound 72, compound 74, compound 83, compound 86, compound 96, compound 109, compound 113, compound 115, compound 123, compound 146, compound 163, compound 171, compound 176, compound 187, compound 193, compound 201, compound 208, compound 213, compound 216, compound 269, compound 288, compound 292, compound 314, compound 323, compound 353, compound 364, compound 370, compound 390, compound 414, compound 514, compound 636 and compound 702 according to the invention.

Comparative device examples 1 to 7

Comparative examples 1 to 7: preparation of comparative organic electroluminescent devices 1 to 7

The compound 11 in the cover layer of example 1 was changed to Ref-1 to Ref-7, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 1 to 7.

Test software, a computer, a K2400 digital source list manufactured by Keithley company, U.S. and a PR788 spectral scanning luminance meter manufactured by Photo Research, U.S. are combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. Life testing an M6000 OLED life test system from McScience was used.

The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emitting characteristics of the devices 1 to 38, and the organic electroluminescent devices obtained in comparative examples 1 to 7 in the examples of the device according to the present invention are shown in table 1 below.

Table 1:

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as shown by the results in Table 1, the triarylamine compound has excellent asymmetric space configuration and easy-to-control glass transition temperature, so that the compound has better rigidity, and when the triarylamine compound is used as a coating material of an organic electroluminescent device, the driving voltage, the luminous efficiency and the service life of the device are obviously improved, and the triarylamine compound is an OLED coating material with excellent performance.

Device example 39

Firstly, an ITO/Ag/ITO glass substrate was cut into a size of 50 mm. Times.50 mm. Times.0.7 mm as an anode, the glass substrate was washed with distilled water 2 times, then with ultrasonic waves for 30 minutes, then with solvents such as acetone, isopropyl alcohol and methanol in this order, and with ultrasonic waves for 15 minutes, and with UV ozone for 30 minutes, and then sent to a vapor deposition machine. A hole injection layer was formed on the glass substrate by vapor deposition of a compound HI-2 having a thickness of 35nm on the prepared ITO transparent electrode. HT-2 of 40nm was vacuum deposited as a hole transport layer on the hole injection layer. Host material and dopant (8 wt%) were evaporated as a light emitting layer on the hole transport layer to a thickness of 35nm under the same vacuum deposition conditions. Wherein, the host material is RH, RD is taken as a doping agent, and the following steps are 98:2 mass ratio and mixing evaporation. On the upper surface of the light-emitting layer, HB-2 with the thickness of 10nm is sequentially evaporated to serve as a hole blocking layer, ET-2 (30 nm) is sequentially evaporated to serve as an electron transport layer by a vacuum evaporation mode, an electron injection layer LiF (1 nm) is evaporated, and a cathode Mg is evaporated: ag (12 nm). Subsequently, the compound 11 prepared in the above example 39 was evaporated on a cathode as a coating layer (65 nm) to prepare an organic electroluminescent device.

Device examples 40 to 76

An organic electroluminescent device was produced by the same production method as in device example 39, except that compound 11 in device example 39 was replaced with compound 17, compound 23, compound 33, compound 36, compound 68, compound 72, compound 74, compound 83, compound 86, compound 96, compound 109, compound 113, compound 115, compound 123, compound 146, compound 163, compound 171, compound 176, compound 187, compound 193, compound 201, compound 208, compound 213, compound 216, compound 269, compound 288, compound 292, compound 314, compound 323, compound 353, compound 364, compound 370, compound 390, compound 414, compound 514, compound 636 and compound 702 according to the invention.

Comparative device examples 8 to 14

Comparative examples 8 to 14: preparation of comparative organic electroluminescent devices 8 to 14

The compound 11 in the cover layer of example 39 was changed to Ref-1 to Ref-7, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 8 to 14.

The environment tested was atmospheric and the temperature was room temperature. The results of testing the light emission characteristics of devices 39 to 76, and organic electroluminescent devices obtained in comparative examples 8 to 14 in examples of the device according to the present invention are shown in Table 2 below.

Table 2:

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as shown by the results in Table 2, the triarylamine compound has excellent asymmetric space configuration and easy-to-control glass transition temperature, so that the compound has better rigidity, and when the triarylamine compound is used as a coating material of an organic electroluminescent device, the driving voltage, the luminous efficiency and the service life of the device are obviously improved, and the triarylamine compound is an OLED coating material with excellent performance.

It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims

1. A triarylamine compound, wherein the triarylamine compound has a structure represented by formula I:

the X is selected from O or S;

each z is independently selected from CH or N;

the Ar is as follows ₂ One or a combination of the following groups:

Wherein each E is independently selected from CH or N;

The R is ₄ Each independently selected from hydrogen, deuterium, tritium,Cyano, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C15 alkyl, substituted or unsubstituted C3 to C15 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, one of a fused ring group of a substituted or unsubstituted C3 to C30 alicyclic ring and a C6 to C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3 to C30 alicyclic ring and a C2 to C30 heteroaromatic ring;

wherein each Y is independently selected from CH or N;

the R is ₆ Each independently selected from 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, one of a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

2. The triarylamine compound of claim 1 wherein Ar ₁ Any one selected from the following groups:

the X is selected from O or S;

each z is independently selected from CH or N;

The p is ₁ Selected from the group consisting of1. 2, 3 or 4; the p is ₂ Selected from 1; the p is ₃ Selected from 1 or 2; the P is ₄ Selected from 1, 2, 3, 4, 5 or 6; the P is ₅ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the p is ₆ Selected from 1, 2 or 3; the P is ₇ Selected from 1, 2, 3, 4, 5, 6 or 7.

3. The triarylamine compound of claim 1 wherein Ar ₂ One or a combination of the following groups:

each E is independently selected from CH or N;

The R is _i 、R _j Each independently selected from substituted or unsubstituted silyl, substituted or unsubstitutedC1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the m is ₀ Selected from 1, 2, 3 or 4; the m is ₁ Selected from 1, 2, 3, 4 or 5; the m is ₂ Selected from 1, 2, 3, 4, 5, 6 or 7; the m is ₃ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m is ₄ Selected from 1 or 2; the m is ₅ Selected from 1, 2 or 3; the m is ₆ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the m is ₇ Selected from 1, 2, 3, 4, 5 or 6; the m is ₈ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; the m is ₉ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the m is ₁₀ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

4. The triarylamine compound of claim 1 wherein L ₀ One selected from the group consisting of:

said e ₀ Selected from 1 or 2; said e ₁ Selected from 1, 2, 3 or 4; said e ₂ Selected from 1, 2, 3, 4, 5 or 6; said e ₃ Selected from 1, 2, 3, 4 or 5; said e ₄ Selected from 1, 2, 3, 4, 5, 6, 7 or 8; said e ₅ Selected from 1, 2 or 3; said e ₆ Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said e ₇ Selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; when two or more R's are present ₁₂ When two or more R' s ₁₂ Are identical or different from each other, or adjacent two R ₁₂ Are connected with each other to form a substituted or unsubstitutedA ring.

5. The triarylamine compound of claim 1 wherein L ₁ Selected from a single bond or one of the following groups:

the R is _x 、R _y Each 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, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, or R _x 、R _y Are connected with each other to form a substituted or unsubstituted ring;

The R is _v Each independently selected from 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, substituted or unsubstituted C3-C30 lipidAny one of a condensed ring group of a ring and a C6-C30 aromatic ring, a condensed ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring, or R _v Are connected with each other to form a substituted or unsubstituted ring;

6. The triarylamine compound of claim 1 wherein L ₂ Selected from single bond or one or combination of the following groups:

the R is _r Selected from substituted or unsubstituted monosilanesAny one of a group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroaromatic ring;

the R is ₁₃ Each independently selected from one of 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 cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cyclic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic rings;

the R is ₁₄ Each independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1% to One of C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C6-C30 aromatic rings, and fused ring groups of substituted or unsubstituted C3-C30 alicyclic rings and C2-C30 heteroaromatic rings;

7. The triarylamine compound of claim 1 wherein said triarylamine compound is selected from any one of the following chemical structures:

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8. an organic electroluminescent device comprising an anode, a cathode, and an organic layer located between the anode and the cathode or outside one or more of the anode and the cathode, characterized in that the organic layer comprises any one of the triarylamine compounds described in any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, wherein the organic layer comprises a capping layer comprising any one of the triarylamine compounds of claims 1 to 7.