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CN109096179A - A kind of aryl amine derivatives, preparation method and application - Google Patents

A kind of aryl amine derivatives, preparation method and application Download PDF

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Publication number
CN109096179A
CN109096179A CN201810813695.3A CN201810813695A CN109096179A CN 109096179 A CN109096179 A CN 109096179A CN 201810813695 A CN201810813695 A CN 201810813695A CN 109096179 A CN109096179 A CN 109096179A
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substituted
unsubstituted
group
aryl
independently selected
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马晓宇
谭野
贺金鑫
王永光
姚明明
王进政
李文军
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Jilin Optical and Electronic Materials Co Ltd
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明提供了一种新型芳胺衍生物。该化合物用于有机电致发光二极管和包含该有机电致发光二极管的显示器装置。该有机电致发光二极管的至少一层，特别是空穴传输层中含有式(Ⅰ)所示的芳胺衍生物，使得有机电致发光二极管具有合适的热稳定性、较低的驱动电压以及较长的寿命和高发光效率。The invention provides a novel arylamine derivative. The compound is used in organic electroluminescent diodes and display devices comprising the organic electroluminescent diodes. At least one layer of the organic electroluminescent diode, especially the hole transport layer contains the arylamine derivative represented by formula (I), so that the organic electroluminescent diode has suitable thermal stability, lower driving voltage and Long life and high luminous efficiency.

Description

A kind of aryl amine derivatives, preparation method and application
Technical field
The present invention relates to organic electroluminescence device technical field more particularly to a kind of aryl amine derivatives, preparation method With application.
Background technique
Organic electroluminescent device is the self-emission device that following principle is utilized: by applying electric field, using by anode Injected holes makes fluorescent substance shine with the recombination energy by cathode injected electrons.The structure of organic electroluminescent device has Body are as follows: anode, cathode and the organic layer to fall between.In order to improve the efficiency and stabilization of organic electroluminescent device Property, organic material layer includes the multilayer with different materials, such as hole injection layer (HIL), hole transmission layer (HTL), shine Layer, electron transfer layer (ETL) and electron injecting layer (EIL).
In this Organic Light Emitting Diode, when applying voltage between the anode and cathode, hole from anode and The exciton that electron injection organic material layer from cathode generates generates the light with specific wavelength when migrating to ground state.
In general, organic electroluminescent device can generate when driving under high temperature environment or taking care of organic electroluminescent device The adverse effects such as the variation of luminescent color, the reduction of luminous efficiency, the raising of driving voltage, the shortening of luminescent lifetime.In order to anti- Only influence, it is necessary to increase the glass transition temperature (Tg) of hole mobile material.Though there is the organic electroluminescent member of long-life The report of part, but the above problem is still fully effective solution.Therefore it provides a kind of organic compound for hole mobile material It is still very necessary.
Summary of the invention
Present invention solves the technical problem that being to provide a kind of aryl amine derivatives, which sends out for organic electroluminescence Optical device has suitable thermal stability, lower driving voltage and longer service life and high-luminous-efficiency.
In view of this, this application provides one kind aryl amine derivatives as shown in formula (I):
Wherein, R1~R8Be independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~ The alkyl of C20, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C2~C30 heteroaryl, replace or not The first of the alkoxy of substituted C1~C20, the aryloxy group of substituted or unsubstituted C6~C20, substituted or unsubstituted C3~C40 Siloxy, the acyl group of substituted or unsubstituted C1~C20, substituted or unsubstituted C2~C20 alkoxy carbonyl, replace or The acyloxy of unsubstituted C2~C20, the amide groups of substituted or unsubstituted C2~C20, substituted or unsubstituted C2~C20 Alkoxycarbonyl amino, the aryloxycarbonylamino of substituted or unsubstituted C7~C20, substituted or unsubstituted C1~C20 Sulfamoylamino group, the sulfonyl of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 alkylthio group, replace or The arylthio of unsubstituted C6~C20, the heterocyclethio of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 Uride base, substituted or unsubstituted C3~C40 silicyl or any two substituent group and place phenyl ring form condensed ring；
Ar1And Ar2It is each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C20 Alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl；
Ar3、Ar4And Ar5It is each independently selected from alkyl, the substituted or unsubstituted C6 of substituted or unsubstituted C1~C20 The heteroaryl of the aryl of~C30 or substituted or unsubstituted C2~C30；
N is 0~5.
Preferably, the R1~R8It is independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted The alkyl of C1~C10, the aryl of substituted or unsubstituted C6~C18, substituted or unsubstituted C2~C15 heteroaryl, take Generation or the alkoxy of unsubstituted C1~C10, the aryloxy group of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~ The siloxy of C20, the acyl group of substituted or unsubstituted C1~C10, substituted or unsubstituted C2~C10 alkoxy carbonyl Base, the acyloxy of substituted or unsubstituted C2~C10, substituted or unsubstituted C2~C10 amide groups, substituted or unsubstituted The aryloxycarbonylamino, substituted or unsubstituted of the alkoxycarbonyl amino of C2~C10, substituted or unsubstituted C7~C14 The sulfamoylamino group of C1~C10, the sulfonyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C1~C10 alkane sulphur Base, the arylthio of substituted or unsubstituted C6~C10, substituted or unsubstituted C1~C10 heterocyclethio, substituted or unsubstituted C1~C10 uride base or substitution, the silicyl of unsubstituted C3~C20 or any two substituent group and place phenyl ring Form condensed ring；
Ar1And Ar2It is each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C10 Alkyl, the aryl of substituted or unsubstituted C6~C18 or the heteroaryl of substituted or unsubstituted C2~C18；
Ar3、Ar4And Ar5It is each independently selected from alkyl, the substituted or unsubstituted C6 of substituted or unsubstituted C1~C5 The heteroaryl of the aryl of~C12 or substituted or unsubstituted C2~C12；
N is 0~3.
Preferably, the Ar3、Ar4And Ar5It is each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted Naphthalene, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, replaces or does not take substituted or unsubstituted anthryl The pyrenyl in generation, substituted or unsubstituted base, substituted or unsubstituted two fluorenyl of 9,9- spiral shell, (9,9- dialkyl group) fluorenyl, substitution Or it is unsubstituted (the substituted or unsubstituted aryl of 9,9- bis-) fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted It is dibenzothiophene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted pyridyl group, substituted or unsubstituted phonetic Piperidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine radical, substituted or unsubstituted benzimidazolyl, substitution Or unsubstituted indyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphthalene Piperidinyl, substituted or unsubstituted benzoxazinyl-, substituted or unsubstituted benzothiazine base, substituted or unsubstituted acridinyl, Substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl or substituted or unsubstituted phenoxazine base.
Preferably, the aryl amine derivatives have as shown in formula (I 1), formula (I 2) or formula (I 3)；
Independent substituted or unsubstituted alkyl, the phenyl selected from hydrogen, C1~C3 of the R1~R8；
Ar3~Ar5It is independent selected from substituted or unsubstituted phenyl, it is substituted or unsubstituted containing heteroatomic phenyl, take Generation or unsubstituted naphthalene substituted or unsubstituted contains heteroatomic naphthalene；
N is 0~2.
Preferably, the structure of the aryl amine derivatives is as follows:
Present invention also provides a kind of preparation methods of aryl amine derivatives, comprising the following steps:
There to be the compound of formula (IV) structure and there is the compound of formula (V) structure in the work of catalyst and alkali metal salt With lower reaction, the aryl amine derivatives with formula (I) structure are obtained；
Wherein, R1~R8Be independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~ The alkyl of C20, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C2~C30 heteroaryl, replace or not The first of the alkoxy of substituted C1~C20, the aryloxy group of substituted or unsubstituted C6~C20, substituted or unsubstituted C3~C40 Siloxy, the acyl group of substituted or unsubstituted C1~C20, substituted or unsubstituted C2~C20 alkoxy carbonyl, replace or The acyloxy of unsubstituted C2~C20, the amide groups of substituted or unsubstituted C2~C20, substituted or unsubstituted C2~C20 Alkoxycarbonyl amino, the aryloxycarbonylamino of substituted or unsubstituted C7~C20, substituted or unsubstituted C1~C20 Sulfamoylamino group, the sulfonyl of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 alkylthio group, replace or The arylthio of unsubstituted C6~C20, the heterocyclethio of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 Uride base, substituted or unsubstituted C3~C40 silicyl or any two substituent group and place phenyl ring form condensed ring；
Ar1And Ar2It is each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C20 Alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl；
Ar3、Ar4And Ar5It is each independently selected from alkyl, the substituted or unsubstituted C6 of substituted or unsubstituted C1~C20 The heteroaryl of the aryl of~C30 or substituted or unsubstituted C2~C30；
M is halogen；
N is 0~5.
Present invention also provides a kind of organic electroluminescent LED, including anode, cathode and the anode and described At least one organic film between cathode, which is characterized in that include described in above scheme at least one described organic film Or above scheme described in aryl amine derivatives prepared by preparation method.
It preferably, include hole transmission layer in the organic film, the material of the hole transmission layer includes the arylamine Derivative.
Present invention also provides a kind of display equipments, including organic electroluminescent LED described in above scheme.
This application provides a kind of aryl amine derivatives, which is not easy to crystallize, and therefore, arylamine provided by the present application spreads out Biology has film uniformity, in situation without being bound by theory, the film uniformity make in OLED emitter and material of main part it Between mutually separation reduce；Further, aryl amine derivatives can improve its effectiveness parameters, such as emission spectra for organic electroluminescence device Wire shaped, efficiency and service life.In addition, aryl amine derivatives are soluble in organic solvent, such as toluene, dimethylbenzene and 3- phenoxy group first Benzene, and solution processing is stood, it can effectively reduce cost, thus derivative provided by the present application is used for organic electroluminescence device With suitable thermal stability, lower driving voltage, longer service life and high-luminous-efficiency.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
The embodiment of the invention discloses one kind aryl amine derivatives as shown in formula (I):
Wherein, R1~R8Be independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~ The alkyl of C20, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C2~C30 heteroaryl, replace or not The first of the alkoxy of substituted C1~C20, the aryloxy group of substituted or unsubstituted C6~C20, substituted or unsubstituted C3~C40 Siloxy, the acyl group of substituted or unsubstituted C1~C20, substituted or unsubstituted C2~C20 alkoxy carbonyl, replace or The acyloxy of unsubstituted C2~C20, the amide groups of substituted or unsubstituted C2~C20, substituted or unsubstituted C2~C20 Alkoxycarbonyl amino, the aryloxycarbonylamino of substituted or unsubstituted C7~C20, substituted or unsubstituted C1~C20 Sulfamoylamino group, the sulfonyl of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 alkylthio group, replace or The arylthio of unsubstituted C6~C20, the heterocyclethio of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 Uride base, substituted or unsubstituted C3~C40 silicyl or any two substituent group and place phenyl ring form condensed ring；
Ar1And Ar2It is each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C20 Alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl；
Ar3、Ar4And Ar5It is each independently selected from alkyl, the substituted or unsubstituted C6 of substituted or unsubstituted C1~C20 The heteroaryl of the aryl of~C30 or substituted or unsubstituted C2~C30；
N is 0~5.
In the aryl amine derivatives of the application, R1、R2、R3、R4、R5、R6、R7And R8It may be the same or different, herein Without particularly limiting；It is independent selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C20 Alkyl, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C2~C30 heteroaryl, substituted or unsubstituted The monosilane of the aryloxy group of the alkoxy of C1~C20 or substituted or unsubstituted C6~C20, substituted or unsubstituted C3~C40 Oxygroup, the acyl group of substituted or unsubstituted C1~C20, the alkoxy carbonyl of substituted or unsubstituted C2~C20, substitution do not take The acyloxy of the C2~C20 in generation, the amide groups of substituted or unsubstituted C2~C20, substituted or unsubstituted C2~C20 alcoxyl Base carbonylamino, the aryloxycarbonylamino of substituted or unsubstituted C7~C20, substituted or unsubstituted C1~C20 ammonia sulphur Acylamino-, the sulfonyl of substituted or unsubstituted C1~C20, the alkylthio group of substituted or unsubstituted C1~C20, substitution do not take The arylthio of the C6~C20 in generation, the heterocyclethio of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 acyl Urea groups or substitution, the silicyl of unsubstituted C3~C40 or any two substituent group and place phenyl ring form condensed ring；Specifically , the R1~R8It is independently selected from the alkane of hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C10 Base, the aryl of substituted or unsubstituted C6~C18, the heteroaryl of substituted or unsubstituted C2~C15, substituted or unsubstituted C1 The alkoxy of~C10, the aryloxy group of substituted or unsubstituted C6~C18, substituted or unsubstituted C3~C20 monosilane oxygen Base, the acyl group of substituted or unsubstituted C1~C10, substituted or unsubstituted C2~C10 alkoxy carbonyl, substituted or unsubstituted The acyloxy of C2~C10, the amide groups of substituted or unsubstituted C2~C10, substituted or unsubstituted C2~C10 alkoxy Carbonylamino, the aryloxycarbonylamino of substituted or unsubstituted C7~C14, substituted or unsubstituted C1~C10 sulfonamides Amino, the sulfonyl of substituted or unsubstituted C1~C10, substituted or unsubstituted C1~C10 alkylthio group, substituted or unsubstituted The arylthio of C6~C10, the heterocyclethio of substituted or unsubstituted C1~C10, substituted or unsubstituted C1~C10 uride Base or substitution, the silicyl of unsubstituted C3~C20 or any two substituent group and place phenyl ring form condensed ring；More specifically , the R1~R8Be independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, methyl, ethyl, propyl, butyl, amyl, Hexyl, phenyl, phenyl or alkoxy containing pyridyl, containing fluorophenyl, cyano-containing.
In aryl amine derivatives, Ar1And Ar2It can be the same or different, be each independently selected from hydrogen, deuterium, halogen, cyanogen Base, hydroxyl, nitro, the alkyl of substituted or unsubstituted C1~C20, substituted or unsubstituted C6~C30 aryl or substitution or not Substituted C2~C30 heteroaryl；More specifically, Ar1And Ar2Be each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, The alkyl of substituted or unsubstituted C1~C10, the aryl of substituted or unsubstituted C6~C18 or substituted or unsubstituted C2~ The heteroaryl of C18；More specifically, Ar1And Ar2It is independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, methyl, second Base, propyl, butyl, amyl, hexyl, phenyl, the phenyl containing pyridyl, containing fluorophenyl, cyano-containing.
Ar3、Ar4And Ar5It may be the same or different, this application is not particularly limited, each independently The aryl or substituted or unsubstituted C2 of alkyl, substituted or unsubstituted C6~C30 selected from substituted or unsubstituted C1~C20 The heteroaryl of~C30；More specifically, Ar3、Ar4And Ar5It is each independently selected from the alkyl of substituted or unsubstituted C1~C5, takes The heteroaryl of the aryl or substituted or unsubstituted C2~C12 of generation or unsubstituted C6~C12；More specifically, Ar3、Ar4And Ar5 Be each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, substitution or Unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted base, takes substituted or unsubstituted benzo phenanthryl Generation or unsubstituted two fluorenyl of 9,9- spiral shell, (9,9- dialkyl group) fluorenyl, substituted or unsubstituted (9,9- bis- is substituted or unsubstituted Aryl) fluorenyl, substituted or unsubstituted carbazyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted hexichol And furyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted pyrazinyl, substitution Or it is unsubstituted triazine radical, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indyl, substituted or unsubstituted Quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphthyridines base, substituted or unsubstituted benzoxazinyl-, Substituted or unsubstituted benzothiazine base, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substitution do not take The phenothiazinyl in generation or substituted or unsubstituted phenoxazine base.
Aryl amine derivatives provided by the present application specifically can be as shown in formula (I 1), formula (I 2) or formula (I 3)；
Independent substituted or unsubstituted alkyl, the phenyl selected from hydrogen, C1~C3 of the R1~R8；
Ar3~Ar5It is independent selected from substituted or unsubstituted phenyl, it is substituted or unsubstituted containing heteroatomic phenyl, take Generation or unsubstituted naphthalene substituted or unsubstituted contains heteroatomic naphthalene；
N is 0~2.
In this application, the substituent group in the alkyl of for example above-mentioned substituted C1~C20 of the substituted group is halogen The naphthenic base of element, nitro, cyano, alkoxy, methyl, ethyl, propyl, butyl or C3~C6, for other bases in the application Group is also the same in this way, herein without repeating.
In this application, the structural formula of specific aryl amine derivatives is additionally provided, as follows:
Present invention also provides the preparation method of the aryl amine derivatives, specifically:
There to be the compound of formula (IV) structure and there is the compound of formula (V) structure in the work of catalyst and alkali metal salt With lower reaction, the aryl amine derivatives with formula (I) structure are obtained；
Wherein, R1~R8Be independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~ The alkyl of C20, the aryl of substituted or unsubstituted C6~C30, substituted or unsubstituted C2~C30 heteroaryl, replace or not The first of the alkoxy of substituted C1~C20, the aryloxy group of substituted or unsubstituted C6~C20, substituted or unsubstituted C3~C40 Siloxy, the acyl group of substituted or unsubstituted C1~C20, substituted or unsubstituted C2~C20 alkoxy carbonyl, replace or The acyloxy of unsubstituted C2~C20, the amide groups of substituted or unsubstituted C2~C20, substituted or unsubstituted C2~C20 Alkoxycarbonyl amino, the aryloxycarbonylamino of substituted or unsubstituted C7~C20, substituted or unsubstituted C1~C20 Sulfamoylamino group, the sulfonyl of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 alkylthio group, replace or The arylthio of unsubstituted C6~C20, the heterocyclethio of substituted or unsubstituted C1~C20, substituted or unsubstituted C1~C20 Uride base, substituted or unsubstituted C3~C40 silicyl or any two substituent group and place phenyl ring form condensed ring；
Ar1And Ar2It is each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1~C20 Alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl；
Ar3、Ar4And Ar5It is each independently selected from alkyl, the substituted or unsubstituted C6 of substituted or unsubstituted C1~C20 The heteroaryl of the aryl of~C30 or substituted or unsubstituted C2~C30；
M is halogen；
N is 0~5.
Above-mentioned catalyst can be catalyst well known to those skilled in the art, exemplary tetrakis triphenylphosphine palladium；The alkali Exemplary metal salt is sodium carbonate or potassium carbonate.
In above-mentioned preparation process, the compound with formula (IV) structure is prepared in the following manner:
By raw material M-0, Pd2(dba)3, connection boric acid frequency alcohol ester and potassium acetate be dissolved in dry Isosorbide-5-Nitrae-dioxane, In nitrogen atmosphere, reactant is flowed back and is stirred 12 hours, then extracted 3 times with methylene chloride and distilled water, it is dry with magnesium sulfite Extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product, intermediate M-1 by silica gel column chromatography；
In nitrogen atmosphere, intermediate M-1, three (4- bromophenyl) amine and tetrakis triphenylphosphine palladium are put into flask and dissolved In the in the mixed solvent (volume ratio 3:1:1) of toluene, second alcohol and water；Then, above-mentioned reactant is added in the aqueous solution of potassium carbonate In, it is then refluxed for and stirs 12 hours；After reaction, reactant is extracted with ethyl acetate, simultaneously with the dry extraction product of magnesium sulfite Filtering, then, is concentrated under reduced pressure filtration product, purifies enriched product using silica gel column chromatography, obtains intermediate M-2；
By raw material M-2, Pd2(dba)3, connection pinacol borate and potassium acetate be dissolved in dry Isosorbide-5-Nitrae-dioxane, In nitrogen atmosphere, reactant is flowed back and is stirred 12 hours, then extracted 3 times with methylene chloride and distilled water, it is dry with magnesium sulfite Dry extraction product simultaneously filters, and is then concentrated under reduced pressure filtration product, purifies enriched product, intermediate M- by silica gel column chromatography 3 i.e. with the compound of formula (IV) structure.
The structural formula of above-mentioned reaction specifically:
Present invention also provides a kind of organic electroluminescent LEDs comprising anode, cathode and the anode and yin At least one organic film between pole includes aryl amine derivatives described in above scheme at least one described organic film.
In a particular embodiment, hole injection layer, hole transmission layer, luminescent layer, hole are provided between anode and cathode Barrier layer, electron transfer layer and electron injecting layer, the material of the hole transmission layer include above-mentioned aryl amine derivatives.
Present invention also provides a kind of display equipments comprising above-mentioned organic electroluminescent LED.
For a further understanding of the present invention, below with reference to embodiment to aryl amine derivatives provided by the invention, its preparation side Method is described in detail with application, and protection scope of the present invention is not limited by the following examples.
Embodiment 1
It is in nitrogen atmosphere, the 2- of intermediate M-3-1-1,3.82g (15.88mmol) of 10.0g (11.7mmol) is chloro- The tetrakis triphenylphosphine palladium of 4- phenylquinazoline and 0.15g (0.13mmol) are put into flask and are dissolved in the toluene of 250ml, ethyl alcohol With the in the mixed solvent (volume ratio 3:1:1) of water；Then, the aqueous solution of the potassium carbonate of 7.3g (52.92mmol) is added above-mentioned In reactant, it is then refluxed for and stirs 12 hours；After reaction, reactant is extracted with ethyl acetate, is extracted with magnesium sulfite is dry Product simultaneously filters；Then, it is concentrated under reduced pressure filtration product, uses silica gel column chromatography (solvent ratio: petroleum ether/dichloromethane Alkane=3:1) purification enriched product, obtain the compound 14 (yield=82%) of 9.05g, mass spectrum: theoretical value 833.38；It surveys Magnitude is 833.40；Above-mentioned reaction process is specific as follows:
Embodiment 2
Identical as 1 preparation method of embodiment, difference is: the chloro- 4- phenylquinazoline of 2- being replaced with 4- bromo biphenyl, finally The compound 21 (yield=87%) of 90g, mass spectrum: theoretical value 781.37 are obtained；Measured value is 781.39.Reaction process Shown in specific as follows:
Embodiment 3
Identical as 1 preparation method of embodiment, difference is: M-3-1-1 is replaced with the chloro- 4- phenyl quinazoline azoles of M-3-1-2,2- Quinoline replaces with 4- bromo biphenyl, finally obtains the compound 61 (yield: yield=84%) of 8.65g, mass spectrum: theoretical value is 905.40；Measured value is 805.38.Shown in reaction process is specific as follows:
Embodiment 4
Identical as 1 preparation method of embodiment, difference is: M-3-1-1 is replaced with the chloro- 4- phenyl quinazoline azoles of M-3-2-1,2- Quinoline replaces with chloro- 4, the 6- diphenyl -1,3,5-triazines of 2-, finally obtains the compound 58 (yield: yield=82%) of 9.18g, Mass spectrum: theoretical value 984.42, measured value 984.40.Shown in reaction process is specific as follows:
Embodiment 5
Identical as 1 preparation method of embodiment, difference is: M-3-1-1 is replaced with the chloro- 4- phenyl quinazoline azoles of M-3-3-1,2- Quinoline replaces with 4- bromo biphenyl, finally obtains the compound 113 (yield: yield=88%) of 9.02g, mass spectrum: theoretical value is 1029.43 measured value 1029.40.Shown in reaction process is specific as follows:
Embodiment 6
It is by coating layer thicknessIto glass substrate be placed in distilled water and clean 2 times, ultrasonic washing 30 minutes, use Distilled water cleans 2 times repeatedly, and ultrasonic washing 10 minutes, after distilled water cleans, isopropanol, acetone, methanol equal solvent were pressed It is dry after sequence ultrasonic washing, it is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, evaporator is sent to In；4,4', 4 "-three [the 2- naphthylphenyl amino] triphens for being 50nm by evaporation thickness on the ito transparent electrode having had been prepared for Base amine (2-TNATA) is used as hole injection layer；Then the compound prepared by embodiment 1 is true on the hole injection layer of formation Empty evaporation thickness is the hole transmission layer of 30nm；Then the blue main body material that evaporation thickness is 30nm on above-mentioned hole transmission layer Expect 9,10- bis- (2- naphthalene) anthracene (AND) and dopant material N1, N1, N6, N6- tetraphenyl pyrene -1,6- diamines (TPPDA), main body material The weight ratio of material and dopant material is 95:5；Then on above-mentioned luminescent layer vacuum evaporation with a thickness of 10nm bis- (2- methyl -8- Oxyquinoline-N1,08)-(1,1 '-biphenyl -4- hydroxyl) aluminium (BAlq) is used as hole blocking layer；It is true on above-mentioned hole blocking layer Empty evaporation thickness is the Alq3 of 40nm as electron transfer layer；Vacuum evaporation is on above-mentioned electron transfer layer with a thickness of 0.5nm fluorine Change lithium (LiF), as electron injecting layer；The aluminium that last evaporation thickness is 150nm completes organic electroluminescence hair as cathode, with this The preparation of optical device.
Embodiment 7
Identical as the preparation method of embodiment 6, difference is: the chemical combination of embodiment 1 is replaced with the compound of embodiment 2 Object is prepared for organic electroluminescence device.
Embodiment 8
Identical as the preparation method of embodiment 6, difference is: the chemical combination of embodiment 1 is replaced with the compound of embodiment 3 Object is prepared for organic electroluminescence device.
Embodiment 9
Identical as the preparation method of embodiment 6, difference is: the chemical combination of embodiment 1 is replaced with the compound of embodiment 4 Object is prepared for organic electroluminescence device.
Embodiment 10
Identical as the preparation method of embodiment 6, difference is: the chemical combination of embodiment 1 is replaced with the compound of embodiment 5 Object is prepared for organic electroluminescence device.
Comparative example
Identical as the preparation method of embodiment 6, difference is: with following structural formula, compound replaces embodiment as a comparison 1 compound is prepared for organic electroluminescence device.
With the thermal decomposition temperature for the compound that thermogravimetry measurement embodiment 1,2,3,4,5 synthesizes.Using differential scanning The glass transition temperature Tg of calorimetry measurement above compound.The results are shown in Table 1；
The thermal decomposition temperature and Tg tables of data of the compound of 1 Examples 1 to 5 of table preparation
Organic electroluminescence device is prepared and to device using the part particular compound and above-mentioned control compounds of the application Part applies with forward dc bias voltage, measures Organic Electricity using the PR-650 photometric device of Photo Research company Photoluminescence Properties, and in 5000cd/m2Benchmark gray scale under using the biometrics device of McScience company determine T95 Service life.The results are shown in Table 2；
The performance data table of 2 embodiment of table and the organic electroluminescence device of comparative example preparation
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should be pointed out that pair For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out Some improvements and modifications, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
The foregoing description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, as defined herein General Principle can be realized in other embodiments without departing from the spirit or scope of the present invention.Therefore, of the invention It is not intended to be limited to the embodiments shown herein, and is to fit to and the principles and novel features disclosed herein phase one The widest scope of cause.

Claims (9)

1.一种如式(Ⅰ)所示的芳胺衍生物：1. A arylamine derivative as shown in formula (I): 其中，R1～R8各自独立的选自氢、氘、卤素、氰基、羟基、硝基、取代或未取代的C1～C20的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C2～C30的杂芳基、取代或未取代的C1～C20的烷氧基、取代或未取代的C6～C20的芳氧基、取代或未取代的C3～C40的甲硅烷氧基、取代或未取代的C1～C20的酰基、取代或未取代的C2～C20的烷氧基羰基、取代或未取代的C2～C20的酰氧基、取代或未取代的C2～C20的酰胺基、取代或未取代的C2～C20的烷氧基羰基氨基、取代或未取代的C7～C20的芳氧基羰基氨基、取代或未取代的C1～C20的氨磺酰氨基、取代或未取代的C1～C20的磺酰基、取代或未取代的C1～C20的烷硫基、取代或未取代的C6～C20的芳硫基、取代或未取代的C1～C20的杂环硫基、取代或未取代的C1～C20的酰脲基、取代或未取代的C3～C40的甲硅烷基或任意两个取代基与所在苯环形成稠环；Wherein, R 1 to R 8 are each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, Substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C3-C40 silane Oxygen, substituted or unsubstituted C1-C20 acyl, substituted or unsubstituted C2-C20 alkoxycarbonyl, substituted or unsubstituted C2-C20 acyloxy, substituted or unsubstituted C2-C20 Amide, substituted or unsubstituted C2-C20 alkoxycarbonylamino, substituted or unsubstituted C7-C20 aryloxycarbonylamino, substituted or unsubstituted C1-C20 sulfamoylamino, substituted or unsubstituted Substituted C1-C20 sulfonyl, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C6-C20 arylthio, substituted or unsubstituted C1-C20 heterocyclic thio, substituted Or an unsubstituted C1-C20 ureide group, a substituted or unsubstituted C3-C40 silyl group, or any two substituents form a condensed ring with the benzene ring; Ar1和Ar2各自独立地选自氢、氘、卤素、氰基、羟基、硝基、取代或未取代的C1～C20的烷基、取代或未取代的C6～C30芳基、取代或未取代的C2～C30杂芳基；Ar 1 and Ar 2 are each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1～C20 alkyl, substituted or unsubstituted C6～C30 aryl, substituted or unsubstituted Substituted C2～C30 heteroaryl; Ar3、Ar4和Ar5各自独立地选自取代或未取代的C1～C20的烷基、取代或未取代的C6～C30的芳基或取代或未取代的C2～C30的杂芳基；Ar 3 , Ar 4 and Ar 5 are each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heteroaryl; n为0～5。n is 0-5. 2.根据权利要求1所述的芳胺衍生物，其特征在于，所述R1～R8各自独立的选自氢、氘、卤素、氰基、羟基、硝基、取代或未取代的C1～C10的烷基、取代或未取代的C6～C18的芳基、取代或未取代的C2～C15的杂芳基、取代或未取代的C1～C10的烷氧基、取代或未取代的C6～C18的芳氧基、取代或未取代的C3～C20的甲硅烷氧基、取代或未取代的C1～C10的酰基、取代或未取代的C2～C10的烷氧基羰基、取代或未取代的C2～C10的酰氧基、取代或未取代的C2～C10的酰胺基、取代或未取代的C2～C10的烷氧基羰基氨基、取代或未取代的C7～C14的芳氧基羰基氨基、取代或未取代的C1～C10的氨磺酰氨基、取代或未取代的C1～C10的磺酰基、取代或未取代的C1～C10的烷硫基、取代或未取代的C6～C10的芳硫基、取代或未取代的C1～C10的杂环硫基、取代或未取代的C1～C10的酰脲基或取代、未取代的C3～C20的甲硅烷基或任意两个取代基与所在的苯环形成稠环；2. The arylamine derivative according to claim 1, wherein the R 1 to R 8 are each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1 ~C10 alkyl group, substituted or unsubstituted C6~C18 aryl group, substituted or unsubstituted C2~C15 heteroaryl group, substituted or unsubstituted C1~C10 alkoxy group, substituted or unsubstituted C6 ~C18 aryloxy group, substituted or unsubstituted C3~C20 silyloxy group, substituted or unsubstituted C1~C10 acyl group, substituted or unsubstituted C2~C10 alkoxycarbonyl group, substituted or unsubstituted C2-C10 acyloxy, substituted or unsubstituted C2-C10 amido, substituted or unsubstituted C2-C10 alkoxycarbonylamino, substituted or unsubstituted C7-C14 aryloxycarbonylamino , substituted or unsubstituted C1-C10 sulfamoylamino, substituted or unsubstituted C1-C10 sulfonyl, substituted or unsubstituted C1-C10 alkylthio, substituted or unsubstituted C6-C10 aryl Thio group, substituted or unsubstituted C1～C10 heterocyclic thio group, substituted or unsubstituted C1～C10 ureido group or substituted or unsubstituted C3～C20 silyl group or any two substituents with the The benzene ring forms a condensed ring; Ar1和Ar2各自独立地选自氢、氘、卤素、氰基、羟基、硝基、取代或未取代的C1～C10的烷基、取代或未取代的C6～C18的芳基或取代或未取代的C2～C18的杂芳基；Ar 1 and Ar 2 are each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1～C10 alkyl, substituted or unsubstituted C6～C18 aryl or substituted or Unsubstituted C2-C18 heteroaryl; Ar3、Ar4和Ar5各自独立地选自取代或未取代的C1～C5的烷基、取代或未取代的C6～C12的芳基或取代或未取代的C2～C12的杂芳基；Ar 3 , Ar 4 and Ar 5 are each independently selected from substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C12 aryl or substituted or unsubstituted C2-C12 heteroaryl; n为0～3。n is 0-3. 3.根据权利要求1所述的芳胺衍生物，其特征在于，所述Ar3、Ar4和Ar5各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的芘基、取代或未取代的苝基、取代或未取代的9,9-螺二芴基、(9,9-二烷基)芴基、取代或未取代的(9,9-二取代或未取代的芳基)芴基、取代或未取代的咔唑基、取代或未取代的二苯并噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的吡嗪基、取代或未取代的三嗪基、取代或未取代的苯并咪唑基、取代或未取代的吲哚基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的萘啶基、取代或未取代的苯并噁嗪基、取代或未取代的苯并噻嗪基、取代或未取代的吖啶基、取代或未取代的吩嗪基、取代或未取代的吩噻嗪基或者取代或未取代的吩噁嗪基。3. The arylamine derivative according to claim 1, wherein the Ar 3 , Ar 4 and Ar 5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted 9,9- Spirobifluorenyl, (9,9-dialkyl)fluorenyl, substituted or unsubstituted (9,9-disubstituted or unsubstituted aryl)fluorenyl, substituted or unsubstituted carbazolyl, substituted or Unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted Triazinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphthyridinyl , substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl or substituted or unsubstituted phenoxazinyl. 4.根据权利要求1所述的芳胺衍生物，其特征在于，所述芳胺衍生物具有如式(Ⅰ1)、式(Ⅰ2)或式(Ⅰ3)所示；4. The arylamine derivative according to claim 1, characterized in that, the arylamine derivative is as shown in formula (I1), formula (I2) or formula (I3); 所述R1～R8独立的选自氢、C1～C3的取代或未取代的烷基、苯基；The R1-R8 are independently selected from hydrogen, C1-C3 substituted or unsubstituted alkyl, phenyl; Ar3～Ar5独立的选自取代或未取代的苯基、取代或未取代的含有杂原子的苯基、取代的或未取代的萘基或取代或未取代的含有杂原子的萘基；Ar 3 to Ar 5 are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted phenyl containing heteroatoms, substituted or unsubstituted naphthyl or substituted or unsubstituted naphthyl containing heteroatoms; n为0～2。n is 0-2. 5.根据权利要求1所述的芳胺衍生物，其特征在于，所述芳胺衍生物的结构如下所示：5. arylamine derivatives according to claim 1, is characterized in that, the structure of described arylamine derivatives is as follows: 6.一种芳胺衍生物的制备方法，包括以下步骤：6. A preparation method of arylamine derivatives, comprising the following steps: 将具有式(Ⅳ)结构的化合物与具有式(V)结构的化合物在催化剂与碱金属盐的作用下反应，得到具有式(Ⅰ)结构的芳胺衍生物；reacting the compound having the structure of formula (IV) with the compound having the structure of formula (V) under the action of a catalyst and an alkali metal salt to obtain an arylamine derivative having the structure of formula (I); 其中，R1～R8各自独立的选自氢、氘、卤素、氰基、羟基、硝基、取代或未取代的C1～C20的烷基、取代或未取代的C6～C30的芳基、取代或未取代的C2～C30的杂芳基、取代或未取代的C1～C20的烷氧基、取代或未取代的C6～C20的芳氧基、取代或未取代的C3～C40的甲硅烷氧基、取代或未取代的C1～C20的酰基、取代或未取代的C2～C20的烷氧基羰基、取代或未取代的C2～C20的酰氧基、取代或未取代的C2～C20的酰胺基、取代或未取代的C2～C20的烷氧基羰基氨基、取代或未取代的C7～C20的芳氧基羰基氨基、取代或未取代的C1～C20的氨磺酰氨基、取代或未取代的C1～C20的磺酰基、取代或未取代的C1～C20的烷硫基、取代或未取代的C6～C20的芳硫基、取代或未取代的C1～C20的杂环硫基、取代或未取代的C1～C20的酰脲基、取代或未取代的C3～C40的甲硅烷基或任意两个取代基与所在苯环形成稠环；Wherein, R 1 to R 8 are each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, Substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C3-C40 silane Oxygen, substituted or unsubstituted C1-C20 acyl, substituted or unsubstituted C2-C20 alkoxycarbonyl, substituted or unsubstituted C2-C20 acyloxy, substituted or unsubstituted C2-C20 Amide, substituted or unsubstituted C2-C20 alkoxycarbonylamino, substituted or unsubstituted C7-C20 aryloxycarbonylamino, substituted or unsubstituted C1-C20 sulfamoylamino, substituted or unsubstituted Substituted C1-C20 sulfonyl, substituted or unsubstituted C1-C20 alkylthio, substituted or unsubstituted C6-C20 arylthio, substituted or unsubstituted C1-C20 heterocyclic thio, substituted Or an unsubstituted C1-C20 ureide group, a substituted or unsubstituted C3-C40 silyl group, or any two substituents form a condensed ring with the benzene ring; Ar1和Ar2各自独立地选自氢、氘、卤素、氰基、羟基、硝基、取代或未取代的C1～C20的烷基、取代或未取代的C6～C30芳基、取代或未取代的C2～C30杂芳基；Ar 1 and Ar 2 are each independently selected from hydrogen, deuterium, halogen, cyano, hydroxyl, nitro, substituted or unsubstituted C1～C20 alkyl, substituted or unsubstituted C6～C30 aryl, substituted or unsubstituted Substituted C2～C30 heteroaryl; Ar3、Ar4和Ar5各自独立地选自取代或未取代的C1～C20的烷基、取代或未取代的C6～C30的芳基或取代或未取代的C2～C30的杂芳基；Ar 3 , Ar 4 and Ar 5 are each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heteroaryl; M为卤素；M is halogen; n为0～5。n is 0-5. 7.一种有机电致发光二极管，包括阳极、阴极以及所述阳极和所述阴极之间的至少一个有机薄膜，其特征在于，所述至少一个有机薄膜中包括如权利要求1～5任一项所述的或权利要求6所述的制备方法所制备的芳胺衍生物。7. An organic electroluminescent diode, comprising an anode, a cathode, and at least one organic thin film between the anode and the cathode, characterized in that, the at least one organic thin film includes any one of claims 1 to 5 The arylamine derivative prepared by the preparation method described in item or claim 6. 8.根据权利要求7所述的有机电致发光二极管，其特征在于，所述有机薄膜中包括空穴传输层，所述空穴传输层的材料包括所述芳胺衍生物。8 . The organic electroluminescence diode according to claim 7 , wherein the organic thin film includes a hole transport layer, and the material of the hole transport layer includes the aromatic amine derivative. 9.一种显示器装置，包括权利要求7～8任一项所述的有机电致发光二极管。9. A display device comprising the organic electroluminescent diode according to any one of claims 7-8.
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