CN108727281A - A kind of derivative of tri-arylamine group and its organic electroluminescence device - Google Patents
A kind of derivative of tri-arylamine group and its organic electroluminescence device Download PDFInfo
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Abstract
The invention discloses a kind of derivative of tri-arylamine group and its organic electroluminescence devices, are related to organic optoelectronic materials technology.The derivative of tri-arylamine group of the present invention has bipolar structure, has good carrier transmission characteristics, makes electrons and holes can be effective compound in luminescent layer, luminous efficiency is high.In addition derivative of tri-arylamine group of the invention has higher glass transition temperature and thermal stability, is conducive to material filming.The organic electroluminescence device of the present invention includes cathode, anode and one or more organic matter layers, at least one layer in organic matter layer contains the derivative of tri-arylamine group of the present invention, the organic electroluminescence device of the present invention, with lower driving voltage, higher luminous efficiency and luminous brightness, and there is longer service life.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of derivative of tri-arylamine group and its organic electroluminescence
Luminescent device.
Background technology
Organic photoelectrical material is the organic material of the generation with photon and electronics, conversion and transmission characteristic.Currently, organic
Photoelectric material has been applied to organic electroluminescence device (Organic Light-Emitting Diode, OLED).OLED is
Refer to the device that organic photoelectrical material shines under the action of electric current or electric field, electric energy can be converted into luminous energy by it.In recent years
Carry out OLED just to receive more and more attention as FPD of new generation and solid state lighting technology.Compared to liquid crystal display skill
Art, OLED are shone with its low-power consumption, actively, fast response time, high contrast, no angle limit, can make the spies such as Flexible Displays
Point is increasingly used in display and lighting area.
Usual OLED has a multilayered structure, including tin indium oxide (ITO) anode and metallic cathode and be placed in ito anode with
Several organic photovoltaic layers between metallic cathode, such as hole injection layer (HIL), hole transmission layer (HTL), luminescent layer
(EML), electron transfer layer (ETL) and electron injecting layer (EIL) etc..Under certain voltage driving, hole is with electronics respectively by sun
Pole is injected into hole transmission layer and electron transfer layer with cathode, and the two passes through hole transmission layer respectively and electron transfer layer moves to
Luminescent layer forms the compound exciton of hole-electron, the form that exciton passes through luminescence relaxation when the two meets combination in luminescent layer
Ground state is returned to, it is luminous to achieve the purpose that.
For luminescent layer, when using only a kind of material as luminescent layer, produced due to intermolecular interaction
Raw concentration quenching, causes the luminous efficiency of organic electroluminescence device to reduce, therefore in order to improve organic electroluminescence device
Guest materials is usually doped in material of main part and forms luminescent layer by luminous efficiency.
Currently, usually there is the problems such as operation voltage is high, luminous efficiency is low, service life is short in organic electroluminescence device.
Thus, it is that those skilled in the art study all the time to explore the new organic photoelectrical material for organic electroluminescence device
Emphasis direction.For luminescent layer, traditionally material used, can not usually provide the satisfactory characteristics of luminescence, therefore,
There is still a need for design the new better material of main part of performance to improve the performance of organic electroluminescence device.
Invention content
Goal of the invention：In view of the above-mentioned problems, the object of the present invention is to provide a kind of derivative of tri-arylamine group and its Organic Electricities
Electroluminescence device, the derivative of tri-arylamine group are applied as material of main part in organic electroluminescence device, to reduce
The driving voltage of organic electroluminescence devices, improves luminous efficiency and the brightness of organic electroluminescence device, and has extended
The service life of organic electroluminescence devices.
The above-mentioned technical purpose of the present invention is achieved through the following technical solutions：A kind of derivative of tri-arylamine group, this three
Aromatic amino-derivative has the general structure as shown in structural formula I：
Wherein, R1、R2It is independent selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C1~
The alkoxy of C30, the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 heteroaryl in one
Kind；
Ar1、Ar2Independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 it is miscellaneous
One kind in aryl；
L is selected from the miscellaneous sub- virtue of singly-bound, the arlydene of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60
One kind in base.
Preferably, R1、R2The independent alkyl for selecting substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C30
Aryl, substituted or unsubstituted C3~C30 heteroaryl in one kind；
Ar1、Ar2Independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 it is miscellaneous
One kind in aryl；
L is selected from the miscellaneous sub- virtue of singly-bound, the arlydene of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30
One kind in base.
Preferably, R1、R2It is independent selected from methyl, ethyl, propyl, butyl, amyl, cyclopenta, cyclohexyl, substitution or not
Substituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution
Or one kind in unsubstituted quinolines base, substituted or unsubstituted furyl, substituted or unsubstituted thienyl.
Preferably, Ar1、Ar2It is independent selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or not
Substituted fluorenyl, two fluorenyl of substituted or unsubstituted spiral shell, substituted or unsubstituted carbazyl, substituted or unsubstituted triphenylene
One kind in base, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene.
Preferably, L is independent selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substitution
Or it is unsubstituted sub-pyridyl group, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted fluorenylidene, substituted or unsubstituted
One kind in sub- carbazyl.
Most preferably, the one kind of derivative of tri-arylamine group of the invention in chemical constitution as follows,
Further, the present invention also provides a kind of organic electroluminescence device, which includes sun
Pole, cathode and one or more organic matter layers, organic matter layer is between anode and cathode, at least one layer in organic matter layer
Derivative of tri-arylamine group containing aforementioned present invention.
Preferably, organic matter layer includes luminescent layer, and luminescent layer is mainly made of material of main part and guest materials, material of main part
Include the derivative of tri-arylamine group of the present invention.
Advantageous effect：Compared with prior art, it is an advantage of the invention that since the derivative of tri-arylamine group of the present invention has
Bipolar structure, therefore there are good carrier transmission characteristics, make electrons and holes can be effective compound in luminescent layer, hair
Light efficiency is high.In addition the benzo pyrimidine substituent group with condensed cyclic structure in derivative of tri-arylamine group of the invention, which increases, finishes
The rigidity of structure, and also introduced with large volume of substituent group, such as biphenyl in the derivative of tri-arylamine group of the present invention
Base, fluorenyl, carbazyl etc. effectively raise the glass transition temperature and thermal stability of material, are conducive to material filming.
Organic luminescent device using the derivative of tri-arylamine group of the present invention as organic matter layer has lower driving electricity
Pressure, higher luminous efficiency and luminous brightness, and there is longer service life.
Specific implementation mode
With reference to specific embodiment, the present invention is furture elucidated, it should be understood that these embodiments are merely to illustrate the present invention
Rather than limit the scope of the invention, after having read the present invention, various equivalences of the those skilled in the art to the present invention
The modification of form falls within the application range as defined in the appended claims.
A kind of derivative of tri-arylamine group, the derivative of tri-arylamine group have the general structure as shown in structural formula I：
Wherein, R1、R2It is independent selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C1~
The alkoxy of C30, the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 heteroaryl in one
Kind；
Ar1、Ar2Independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 it is miscellaneous
One kind in aryl；
L is selected from the miscellaneous sub- virtue of singly-bound, the arlydene of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60
One kind in base.
Preferably, R1、R2The independent alkyl for selecting substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C30
Aryl, substituted or unsubstituted C3~C30 heteroaryl in one kind；
Ar1、Ar2Independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 it is miscellaneous
One kind in aryl；
L is selected from the miscellaneous sub- virtue of singly-bound, the arlydene of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30
One kind in base.
Preferably, R1、R2It is independent selected from methyl, ethyl, propyl, butyl, amyl, cyclopenta, cyclohexyl, substitution or not
Substituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution
Or one kind in unsubstituted quinolines base, substituted or unsubstituted furyl, substituted or unsubstituted thienyl.
Preferably, Ar1、Ar2It is independent selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or not
Substituted fluorenyl, two fluorenyl of substituted or unsubstituted spiral shell, substituted or unsubstituted carbazyl, substituted or unsubstituted triphenylene
One kind in base, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene.
Preferably, L is independent selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substitution
Or it is unsubstituted sub-pyridyl group, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted fluorenylidene, substituted or unsubstituted
One kind in sub- carbazyl.
According to the present invention, the substituent group on abovementioned alkyl, alkoxy is independent selected from hydrogen, deuterium, cyano, halogen, fluoroform
The heteroaryl of base, the alkyl of C1~C10, the alkoxy of C1~C10, the aryl of C6~C24 or C3~C24；
Substituent group on above-mentioned aryl, heteroaryl is independent selected from hydrogen, deuterium, cyano, halogen, trifluoromethyl, C1~C10
The heteroaryl of alkyl, the alkoxy of C1~C10, the aryl of C6~C24 or C3~C24.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane
Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth
Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refers to-O- alkyl, wherein the alkyl is as previously defined.
Aryl of the present invention refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total
Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but
It is without being limited thereto.
Heteroaryl of the present invention refers to the group that one or more of aryl aromatic core carbon is substituted by hetero atom
General name, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, and the heteroaryl can be bicyclic heteroaryl or condensed ring heteroaryl
Base, example may include pyridyl group, pyrrole radicals, pyridyl group, thienyl, furyl, indyl, quinolyl, isoquinolyl, benzo thiophene
Pheno base, benzofuranyl, dibenzofuran group, dibenzothiophene, carbazyl etc., but not limited to this.
Arlydene of the present invention refer to aromatic hydrocarbon molecule aromatic core carbon on remove two hydrogen atoms after, be left univalent perssad
General name, can be monocycle arlydene or condensed ring arlydene, example may include phenylene, biphenylene, naphthylene, anthrylene,
Phenanthrylene or sub- pyrenyl etc., but not limited to this.
Heteroarylidene of the present invention refers to the base that one or more of arlydene aromatic core carbon is substituted by hetero atom
The general name of group, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, the heteroarylidene can be monocycle heteroarylidene or
Condensed ring heteroarylidene, example may include sub-pyridyl group, sub- pyrrole radicals, sub-pyridyl group, sub- thienyl, furylidene, sub- indyl,
Sub- quinolyl, sub- isoquinolyl, sub- benzothienyl, sub- benzofuranyl, sub- dibenzofuran group, sub- dibenzothiophene,
Sub- carbazyl etc., but not limited to this.
Chain-like alkyl of the carbon atom numbers such as propyl of the present invention, butyl, amyl more than two includes their isomers, such as
Isopropyl, isobutyl group, sec-butyl, tertiary butyl, isopentyl, neopentyl, tertiary pentyl etc., but not limited to this.
The alkyl of substituted or unsubstituted C1~C30 of the present invention, the alkoxy of substituted or unsubstituted C1~C30,
The aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 heteroaryl refer to substitution before alkyl, alcoxyl
Base, aryl, the total number of carbon atoms on heteroaryl are respectively 1~30,1~30,6~60,3~60, and so on.
As an example, it is not particularly limited, derivative of tri-arylamine group of the invention is in chemical constitution as follows
One kind,
The synthetic route of the derivative of tri-arylamine group of the present invention is as follows：
Wherein, R is independent selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C1~C30
Alkoxy, the aryl of substituted or unsubstituted C6~C60 or the heteroaryl of substituted or unsubstituted C3~C60；
Ar1、Ar2The independent aryl selected from substituted or unsubstituted C6~C60 or substituted or unsubstituted C3~C60
Heteroaryl；
L is selected from the heteroaryl of singly-bound, the aryl of substituted or unsubstituted C6~C60 or substituted or unsubstituted C3~C60
Base.
(1) 3- nitrobenzene boronic acids, ethyl alcohol, adjacent Iodoaniline, K are sequentially added into reaction bulb3PO4、Pd(PPh3)4, react mixed
It closes object to be heated to reflux under protection of argon gas 6 hours, ethyl alcohol is then removed under reduced pressure.Residue with Ethyl acetate dissolve, successively use water,
Saturated salt solution respectively washed once, and solvent is removed under reduced pressure in anhydrous sodium sulfate drying, filtering.Obtained residue silica gel column layer
Analysis purifying, obtains compound E.
Compound E, tetrahydrofuran are added into reaction bulb, hydrochloric acid is added into above-mentioned solution in stirring and dissolving.Ice-water bath
Under, the aqueous solution of sodium nitrite is added dropwise into reaction solution.After twenty minutes, the aqueous solution of potassium iodide is added dropwise in stirring under ice-water bath.It stirs
It mixes after ten minutes, solution is slowly increased to room temperature, is stirred for 1 hour.Finally, the sodium thiosulfate solution of 1M is added dropwise, until anti-
Answer liquid color constant.Liquid separation is extracted with ethyl acetate, organic phase washed with water and saturated common salt water washing, anhydrous slufuric acid
Sodium is dried, and solvent is removed under reduced pressure in filtering.Residue is purified with silica gel column chromatography, obtains compound F.
Compound F, 2- (2- bromophenyls) -2- propyl alcohol, Pd (dba) are sequentially added into reaction bulb2、PPh3、Cs2CO3, first
Benzene, stirs 24 hours under conditions of reflux, after reaction.It is cooled to room temperature, hydrochloric acid is added into reaction solution, with acetic acid second
Ester is extracted, organic phase saturated common salt water washing, and solvent, crude product silicagel column is removed under reduced pressure in anhydrous sodium sulfate drying
Chromatographic purifying obtains compound G.
Compound G, malonic methyl ester nitrile, potassium cyanide, potassium hydroxide, dimethylformamide are sequentially added into reaction bulb,
It is stirred overnight under conditions of 60 DEG C.Solvent is boiled off under reduced pressure, is then added to sodium hydrate aqueous solution.Mixture is set to return
Stream about 1 hour.It is extracted with ethyl acetate, is detached by column chromatography, and recrystallized in methane and heptane,
Obtain compound H.
Compound H and dimethylformamide are added into reaction bulb makes the two mix, and is cooled to 0 DEG C.Into mixed liquor
N- bromo-succinimides are added dropwise.So that gained mixture is warming up to room temperature, then stirs 4 hours.Distilled water is added dropwise,
Filter cake is recovered by filtration, is purified by column chromatography, obtains compound K.
(2) compound K, tetrahydrofuran are added into flask, and the diethyl ether solution containing compound M is added dropwise, it will be anti-
It answers mixture to be stirred 3 hours under conditions of reflux, after being cooled to 0 DEG C, it is molten that the tetrahydrofuran containing compound D is added dropwise
Liquid (150ml) is cooled to 0 DEG C after stirring reaction mixture 2 hours under conditions of reflux, and the ammonium chloride water of saturation is added
Solution is extracted with ethyl acetate, and organic phase is purified by column chromatography, obtains intermediate A.
Intermediate A, intermediate B, Pd (PPh are sequentially added into flask under protection of argon gas3)4, toluene, sodium carbonate it is water-soluble
Liquid, return stirring 8 hours.It after above-mentioned reaction solution is cooled to room temperature, is extracted with toluene, merges organic phase, by organic phase
With saturated common salt water washing, organic phase carries out column chromatography after drying, concentration, by stationary phase of silica gel, obtains shown in structural formula I
Product.
The synthetic route of the derivative of tri-arylamine group of the present invention is not particularly limited, those skilled in the art may be used
Known popular response.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device include anode, cathode with
And one or more organic matter layers, between anode and cathode, at least one layer in organic matter layer contains above-mentioned organic matter layer
The derivative of tri-arylamine group of the present invention.
The organic matter layer of the organic electroluminescence device of the present invention can have single layer structure, or with two layers or more
Multilayered structure.The organic matter layer of the organic electroluminescence device of the present invention can include hole injection layer, hole transmission layer, shine
Any one layer in layer, electron transfer layer, electron injecting layer or arbitrary multilayer.Derivative of tri-arylamine group containing the present invention
The thickness of organic matter layer is not higher than 6 μm, preferably not higher than 0.3 μm, and more preferably 0.002~0.3 μm.If desired, containing
Having the organic matter layer of the derivative of tri-arylamine group of the present invention can further include as known in the art can carry out hole injection, sky
Cave transmission shines, the other materials of electron-transport and electron injection.
The derivative of tri-arylamine group of the present invention specifically can be as the master in the luminescent layer for preparing organic electroluminescence device
Body material.The organic electroluminescence device of use is preferably：ITO on transparent glass is attached to as anode, hole injection layer,
Hole transmission layer, luminescent layer (material of main part：Guest materials), electron transfer layer, electron injecting layer, metallic cathode.
The organic electroluminescence device of the present invention can be prepared by known methods using known materials, however, Organic Electricity
The structure of electroluminescence device is without being limited thereto.
The organic electroluminescence device of the present invention can be widely applied to FPD, solid state lighting, Organophotoreceptor or have
The fields such as machine thin film transistor (TFT).
The present invention is not particularly limited the raw material employed in following embodiment, can be for commercial product or using this
Preparation method known to field technology personnel is prepared.
Embodiment 1：The preparation of compound H：
3- nitrobenzene boronic acids (1.0g, 5.99mmol), ethyl alcohol (15ml), adjacent Iodoaniline are sequentially added in reaction bulb
(1.57g,7.19mmol)、K3PO4(3.18g,14.98mmol)、Pd(PPh3)4(346mg, 0.3mmol), reaction mixture exists
It is heated to reflux 6 hours under argon gas protection, ethyl alcohol is then removed under reduced pressure.Residue with Ethyl acetate dissolves, and uses water, saturation food successively
Brine respectively washed once, and solvent is removed under reduced pressure in anhydrous sodium sulfate drying, filtering.Obtained residue is purified with silica gel column chromatography,
Obtain compound E (1.19g, 93%).
Compound E (1.19g, 5.6mmol), tetrahydrofuran (15ml), stirring and dissolving, to above-mentioned molten are added into reaction bulb
The hydrochloric acid (14ml) of 4M is added in liquid.Under ice-water bath, the water of sodium nitrite (463.79mg, 6.72mmol) is added dropwise into reaction solution
Solution (5ml).After twenty minutes, the aqueous solution (5ml) of potassium iodide (2.32g, 14mmol) is added dropwise in stirring under ice-water bath.10 points of stirring
Zhong Hou, solution are slowly increased to room temperature, are stirred for 1 hour.Finally, the sodium thiosulfate solution of 1M is added dropwise, until reaction solution face
Color is constant.Liquid separation is extracted with ethyl acetate, organic phase washed with water and saturated common salt water washing, anhydrous sodium sulfate drying,
Filtering, is removed under reduced pressure solvent.Residue is purified with silica gel column chromatography, obtains compound F (1.31g, 72%).
Sequentially added into reaction bulb compound F (195mg, 0.6mmol), 2- (2- bromophenyls) -2- propyl alcohol (107.5mg,
0.5mmol)、Pd(dba)2(9.6mg,0.025mmol)、PPh3(34mg,0.05mmol)、Cs2CO3(390mg,1.2mmol)、
Toluene (2ml), stirs 24 hours under conditions of reflux, after reaction.It is cooled to room temperature, the salt of 1M is added into reaction solution
Sour (6ml), is extracted, organic phase saturated common salt water washing with ethyl acetate, and anhydrous sodium sulfate drying is removed under reduced pressure molten
Agent, crude product are purified with silica gel column chromatography, obtain compound G (109.3mg, 80%).
Sequentially added into reaction bulb compound G (153g, 0.56mol), malonic methyl ester nitrile (166.5g, 1.68mol),
Potassium cyanide (40.1g, 0.62mol), potassium hydroxide (62.9g, 1.12mol), dimethylformamide (1L), under conditions of 60 DEG C
It is stirred overnight.Solvent is boiled off under reduced pressure, is then added to 10% sodium hydrate aqueous solution of 500ml.Mixture is set to return
Stream about 1 hour.It is extracted with ethyl acetate, is detached by column chromatography, and recrystallized in methane and heptane,
Obtain compound H (81g, 54%).
The dimethylformamide of compound H (79.7g, 297mmol) and 500ml is added into reaction bulb makes the two mix,
And it is cooled to 0 DEG C.N- bromo-succinimides (312mmol) are added dropwise into mixed liquor.Gained mixture is set to be warming up to room
Then temperature stirs 4 hours.Distilled water is added dropwise, filter cake is recovered by filtration, is purified by column chromatography, obtains compound K
(95.9g, 93%).
The preparation of compound TM1
Compound K (14.2g, 41mmol), tetrahydrofuran (200ml) are added into flask, and is added dropwise containing chemical combination
Reaction mixture is stirred 3 hours under conditions of reflux, is being cooled to 0 by the diethyl ether solution (27.6ml) of object M1 (82mmol)
After DEG C, the tetrahydrofuran solution (150ml) containing compound D1 (6.9g, 49.2mmol) is added dropwise, reaction mixture is existed
After being stirred 2 hours under conditions of reflux, it is cooled to 0 DEG C, the aqueous ammonium chloride solution of saturation is added, is extracted with ethyl acetate, it is organic
It is mutually purified by column chromatography, obtains intermediate A 1.
Sequentially added under protection of argon gas into flask intermediate A 1 (53.7g, 105mmol), intermediate B 1 (29.0g,
100mmol)、Pd(PPh3)4(2.31g, 2mmol), toluene (300ml), aqueous sodium carbonate (2M, 150ml), return stirring 8 are small
When.It after above-mentioned reaction solution is cooled to room temperature, is extracted with toluene, merges organic phase, organic phase is washed with saturated common salt
It washs, organic phase carries out column chromatography after drying, concentration, by stationary phase of silica gel, obtains compound TM1 (58.1g, 86%).Matter
Compose m/z：Theoretical value：675.84；Measured value：677.51.Theoretical elemental content (%) C50H33N3：C,88.86；H,4.92；N,
6.22；Survey constituent content (%)：C,88.82；H,4.98；N,6.20.The above results confirm that it is target product to obtain product.
Embodiment 2：The preparation of compound TM13
Change the compound M1 in embodiment 1 into equimolar compound M2, other steps with the synthesis phase of embodiment 1
Together, compound TM13 (62.4g, 83%) is obtained.Mass spectrum m/z：Theoretical value：751.93；Measured value：753.52.Theoretical elemental contains
Measure (%) C56H37N3：C,89.45；H,4.96；N,5.59；Survey constituent content (%)：C,89.41；H,5.03；N,5.56.On
Stating result confirms that it is target product to obtain product.
Embodiment 3：The preparation of compound TM49
Change the intermediate B 1 in embodiment 1 into equimolar intermediate B 3, other steps with the synthesis phase of embodiment 1
Together, compound TM49 (62.6g, 79%) is obtained.Mass spectrum m/z：Theoretical value：792.00；Measured value：794.62.Theoretical elemental contains
Measure (%) C59H41N3：C,89.48；H,5.22；N,5.31；Survey constituent content (%)：C,89.45；H,5.27；N,5.28.On
Stating result confirms that it is target product to obtain product.
Embodiment 4：The preparation of compound TM62
Change the intermediate B 1 in embodiment 1 into equimolar intermediate B 4, other steps with the synthesis phase of embodiment 1
Together, compound TM49 (61.2g, 78%) is obtained.Mass spectrum m/z：Theoretical value：792.99；Measured value：794.62.Theoretical elemental contains
Measure (%) C58H40N4：C,87.85；H,5.08；N,7.07；Survey constituent content (%)：C,87.83；H,5.13；N,7.04.On
Stating result confirms that it is target product to obtain product.
Embodiment 5：The preparation of compound TM94
Change the compound D1 in embodiment 1 into equimolar compound D5, intermediate B 1 changes equimolar intermediate into
B5, other steps are identical as the synthesis of embodiment 1, obtain compound TM49 (64.9g, 81%).Mass spectrum m/z：Theoretical value：
801.99；Measured value：802.52.Theoretical elemental content (%) C60H39N3：C,89.86；H,4.90；N,5.24；Actual measurement element contains
It measures (%)：C,89.82；H,4.96；N,5.22.The above results confirm that it is target product to obtain product.
Embodiment 6：The preparation of compound TM105
Change the intermediate B 1 in embodiment 1 into equimolar intermediate B 6, other steps with the synthesis phase of embodiment 1
Together, compound TM49 (61.0g, 77%) is obtained.Mass spectrum m/z：Theoretical value：792.00；Measured value：794.73.Theoretical elemental contains
Measure (%) C59H41N3：C,89.48；H,5.22；N,5.31；Survey constituent content (%)：C,89.44；H,5.29；N,5.27.On
Stating result confirms that it is target product to obtain product.
Embodiment 7：The preparation of compound TM113
Compound K (14.2g, 41mmol), tetrahydrofuran (200ml) are added into flask, and is added dropwise containing chemical combination
Reaction mixture is stirred 3 hours under conditions of reflux, is being cooled to 0 by the diethyl ether solution (27.6ml) of object M1 (82mmol)
After DEG C, the tetrahydrofuran solution (150ml) containing compound D1 (6.9g, 49.2mmol) is added dropwise, reaction mixture is existed
After being stirred 2 hours under conditions of reflux, it is cooled to 0 DEG C, the aqueous ammonium chloride solution of saturation is added, is extracted with ethyl acetate, it is organic
It is mutually purified by column chromatography, obtains intermediate A 1.
Sequentially added into round-bottomed flask intermediate A 1 (19.2g, 37.5mmol), intermediate B 7 (6.4g, 37.5mmol),
t-BuONa(5.4g,56.25mmol)、Pd2(dba)3(0.686g, 0.75mmol) and the toluene (200mL) of ultrasonic deoxygenation, with
Addition is dissolved in the P (t-Bu) in toluene (3mL) afterwards3(0.36g, 1.8mmol), is refluxed overnight under nitrogen protection, will react
The organic layer MgSO for after liquid is cooled to room temperature, being handled, and being obtained with ethyl acetate and water4Dry, decompression boils off molten
Agent, using silica gel as stationary phase, dichloromethane/hexane is eluant, eluent, and crude product is carried out column chromatography, obtains compound TM113
(16.9g, 75%).Mass spectrum m/z：Theoretical value：599.74；Measured value：601.52.Theoretical elemental content (%) C44H29N3：C,
88.12；H,4.87；N,7.01；Survey constituent content (%)：C,88.09；H,4.91；N,7.00.The above results confirmation is produced
Object is target product.
Embodiment 8：The preparation of compound TM127
Changing the compound M1 in embodiment 7 into equimolar M2, intermediate B 1 changes equimolar intermediate B 8 into, other
Step is identical as the synthesis of embodiment 1, obtains compound TM127 (20.6g, 73%).Mass spectrum m/z：Theoretical value：751.93；
Measured value：753.73.Theoretical elemental content (%) C56H37N3：C,89.45；H,4.96；N,5.59；Survey constituent content (%)：
C,89.42；H,5.01；N,5.57.The above results confirm that it is target product to obtain product.
Embodiment 9：The preparation of compound TM147
Changing the compound M1 in embodiment 7 into equimolar M9, intermediate B 1 changes equimolar intermediate B 9 into, other
Step is identical as the synthesis of embodiment 1, obtains compound TM147 (19.1g, 70%).Mass spectrum m/z：Theoretical value：725.90；
Measured value：726.52.Theoretical elemental content (%) C54H35N3：C,89.35；H,4.86；N,5.79；Survey constituent content (%)：
C,89.31；H,4.93；N,5.77.The above results confirm that it is target product to obtain product.
Embodiment 10：The preparation of compound TM158
Changing the compound M1 in embodiment 7 into equimolar M10, intermediate B 1 changes equimolar intermediate B 10 into,
His step is identical as the synthesis of embodiment 1, obtains compound TM158 (23.0g, 74%).Mass spectrum m/z：Theoretical value：
828.03；Measured value：829.74.Theoretical elemental content (%) C62H41N3：C,89.93；H,4.99；N,5.07；Actual measurement element contains
It measures (%)：C,89.91；H,5.03；N,5.05.The above results confirm that it is target product to obtain product.
Embodiment 11：The preparation of compound TM162
Change the intermediate B 1 in embodiment 7 into equimolar intermediate B 11, synthesis of other steps with embodiment 1
It is identical, obtain compound TM162 (21.1g, 71%).Mass spectrum m/z：Theoretical value：792.00；Measured value：794.24.Theoretical elemental
Content (%) C59H41N3：C,89.48；H,5.22；N,5.31；Survey constituent content (%)：C,89.44；H,5.28；N,5.29.
The above results confirm that it is target product to obtain product.
Embodiment 12：The preparation of compound TM175
Change the intermediate B 1 in embodiment 7 into equimolar intermediate B 12, synthesis of other steps with embodiment 1
It is identical, obtain compound TM175 (21.0g, 70%).Mass spectrum m/z：Theoretical value：764.93；Measured value：766.47.Theoretical elemental
Content (%) C56H36N4：C,87.93；H,4.74；N,7.32；Survey constituent content (%)：C,87.91；H,4.78；N,7.30.
The above results confirm that it is target product to obtain product.
Other target products are synthesized with reference to the synthetic method of above-described embodiment 1-12.
Application Example 1：The preparation of luminescent device 1
Selection ito glass is anode, is dried as in vacuum chamber after ultrasonic cleaning, is evacuated to 5 × 10-5Pa, above-mentioned
Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer
NPB is as hole transmission layer, evaporation thickness 30nm.Vacuum evaporation the compound of the present invention TM1 conducts on the hole transport layer
Shine layer main body, 10% Ir (ppy)3As doping, evaporation thickness 30nm.Vacuum evaporation Alq on the light-emitting layer3As electricity
Sub- transport layer, evaporation thickness 35nm.Vacuum evaporation LiF is as electron injecting layer, evaporation thickness on the electron transport layer
0.5nm.Vacuum evaporation Al is as cathode, evaporation thickness 100nm on electron injecting layer.
Application Example 2：The preparation of luminescent device 2
Change the compound TM1 in Application Example 1 into compound TM13, other steps are identical as Application Example 1.
Application Example 3：The preparation of luminescent device 3
Change the compound TM1 in Application Example 1 into compound TM49, other steps are identical as Application Example 1.
Application Example 4：The preparation of luminescent device 4
Change the compound TM1 in Application Example 1 into compound TM62, other steps are identical as Application Example 1.
Application Example 5：The preparation of luminescent device 5
Change the compound TM1 in Application Example 1 into compound TM94, other steps are identical as Application Example 1.
Application Example 6：The preparation of luminescent device 6
Change the compound TM1 in Application Example 1 into compound TM105, other steps are identical as Application Example 1.
Application Example 7：The preparation of luminescent device 7
Change the compound TM1 in Application Example 1 into compound TM113, other steps are identical as Application Example 1.
Application Example 8：The preparation of luminescent device 8
Change the compound TM1 in Application Example 1 into compound TM127, other steps are identical as Application Example 1.
Application Example 9：The preparation of luminescent device 9
Change the compound TM1 in Application Example 1 into compound TM147, other steps are identical as Application Example 1.
Application Example 10：The preparation of luminescent device 10
Change the compound TM1 in Application Example 1 into compound TM158, other steps are identical as Application Example 1.
Application Example 11：The preparation of luminescent device 11
Change the compound TM1 in Application Example 1 into compound TM162, other steps are identical as Application Example 1.
Application Example 12：The preparation of luminescent device 12
Change the compound TM1 in Application Example 1 into compound TM175, other steps are identical as Application Example 1.
Comparative example 1
Selection ito glass is anode, is dried as in vacuum chamber after ultrasonic cleaning, is evacuated to 5 × 10-5Pa, above-mentioned
Vacuum evaporation 2T-NATA is as hole injection layer, evaporation thickness 10nm in anode grid substrate.The vacuum evaporation on hole injection layer
NPB is as hole transmission layer, evaporation thickness 30nm.The luminous layer main body of vacuum evaporation CBP conducts on the hole transport layer, 10%
Ir (ppy)3As doping, evaporation thickness 30nm.Vacuum evaporation Alq on the light-emitting layer3As electron transfer layer, vapor deposition is thick
Degree is 35nm.Vacuum evaporation LiF is as electron injecting layer, evaporation thickness 0.5nm on the electron transport layer.In electron injecting layer
Upper vacuum evaporation Al is as cathode, evaporation thickness 100nm.
The characteristics of luminescence of organic electroluminescence device prepared by Application Example 1-12 of the present invention and comparative example 1
Test result is as shown in table 1.
Table 1
From table 1 it follows that the derivative of tri-arylamine group of the present invention is applied to organic electroluminescent as material of main part
In device, which shows lower driving voltage, higher luminous efficiency and longer service life,
And there is preferable durability and reliability.
Claims (8)
1. a kind of derivative of tri-arylamine group, which is characterized in that the derivative of tri-arylamine group has the structure as shown in structural formula I
General formula：
Wherein, the R1、R2It is independent selected from hydrogen, the alkyl of substituted or unsubstituted C1~C30, substituted or unsubstituted C1~
The alkoxy of C30, the aryl of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 heteroaryl in one
Kind；
The Ar1、Ar2Independent aryl selected from substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60 it is miscellaneous
One kind in aryl；
The L is selected from the miscellaneous sub- virtue of singly-bound, the arlydene of substituted or unsubstituted C6~C60, substituted or unsubstituted C3~C60
One kind in base.
2. a kind of derivative of tri-arylamine group according to claim 1, which is characterized in that
The R1、R2The independent alkyl for selecting substituted or unsubstituted C1~C10, substituted or unsubstituted C6~C30 aryl,
One kind in the heteroaryl of substituted or unsubstituted C3~C30；
The Ar1、Ar2Independent aryl selected from substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30 it is miscellaneous
One kind in aryl；
The L is selected from the miscellaneous sub- virtue of singly-bound, the arlydene of substituted or unsubstituted C6~C30, substituted or unsubstituted C3~C30
One kind in base.
3. a kind of derivative of tri-arylamine group according to claim 1, which is characterized in that
The R1、R2It is independent to be selected from methyl, ethyl, propyl, butyl, amyl, cyclopenta, cyclohexyl, substituted or unsubstituted benzene
Base, substituted or unsubstituted naphthalene, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidine radicals, substitution or unsubstituted
Quinolyl, substituted or unsubstituted furyl, one kind in substituted or unsubstituted thienyl.
4. a kind of derivative of tri-arylamine group according to claim 1, which is characterized in that
The Ar1、Ar2It is independent to be selected from the substituted or unsubstituted naphthalene of substituted or unsubstituted phenyl, substituted or unsubstituted fluorenes
Base, two fluorenyl of substituted or unsubstituted spiral shell, substituted or unsubstituted carbazyl, substituted or unsubstituted triphenylene, substitution or
One kind in unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene.
5. a kind of derivative of tri-arylamine group according to claim 1, which is characterized in that
The L is independent to be selected from singly-bound, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substitution or does not take
The sub-pyridyl group in generation, substituted or unsubstituted sub- quinolyl, substituted or unsubstituted fluorenylidene, substituted or unsubstituted sub- carbazole
One kind in base.
6. a kind of derivative of tri-arylamine group according to claim 1, which is characterized in that the derivative of tri-arylamine group is selected from
One kind in chemical constitution as follows,
7. a kind of organic electroluminescence device, which is characterized in that the organic electroluminescence device includes anode, cathode and one
A or multiple organic matter layers, between anode and cathode, at least one layer in the organic matter layer contains the organic matter layer
Derivative of tri-arylamine group described in claim 1-6 any one.
8. a kind of organic electroluminescence device according to claim 7, which is characterized in that the organic matter layer includes shining
Layer, the luminescent layer are mainly made of material of main part and guest materials, and the material of main part includes claim 1-6 any one
The derivative of tri-arylamine group.
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