CN104710343B - A kind of electroluminescent organic material and its device of preparation - Google Patents
A kind of electroluminescent organic material and its device of preparation Download PDFInfo
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Abstract
The electroluminescent organic material of the present invention is a kind of new aromatic amine analog derivative, is by ehter bond to link Ar by aminated compounds1And Ar2Upward electronics closeness and the relevant performance of raising, adjust the R of aminated compounds in addition1~R4The advantages of ligand molecular amount and ligand species improve performance and improve function.The use of the organic assembly of amine derivative is that, with high brightness, outstanding heat resistance, long-life, high efficiency, it is synthesized and purification comparison procedure is simple, with low cost, can meet industrialization development demand in the present invention.
Description
Technical field
Organic electroluminescence device the present invention relates to organic electroluminescent compounds and comprising it.Specifically, it is related to
And novel aromatic series aromatic compound is as electroluminescent material, and use them as an organic electroluminescence
Part.
Background technology
Organic electroluminescence device, typically by two opposed electrodes and at least one layer being inserted between two electrodes
Organic luminescent compounds are constituted.Electric charge is injected into the organic layer formed between the anode and cathode, to form electronics and sky
Cave pair, makes the organic compound with fluorescence or phosphorescent characteristics generate light transmitting.
Organic electroluminescence device（OLED）It is a kind of new flat panel display device, with energy-conservation, fast response time, face
Colour-stable, environmental suitability is strong, radiationless, long lifespan, light weight, thickness of thin the features such as.Due to photoelectric communication in recent years and many
Field of media is developed rapidly, and organic optoelectronic material turns into the core of modern society information and electronic industry.
At present, the material of main part in electroluminescent device mainly has small molecule host material and polymer host material two
Class.Using small molecule host material doping phosphorescent complexes many efficient electroluminescent cells have been prepared for as luminescent layer
Part.But preparing small molecule electroluminescent device needs, using complicated technologies such as vacuum evaporations, to substantially increase preparation cost.Together
When, small molecule is easy to the stability that the properties such as crystallization also significantly limit device in itself.In recent years, polymer body material is utilized
The various phosphorescent complexes objects of material doping prepare electroluminescent device as luminescent layer and receive more concern.However, at present
The solubility property and filming performance for the polymer host material reported are relatively poor, so as to influence it as luminescent layer.This hair
Bright technology be the representative species of hole mobile material in the relevant technology of organic electroluminescence device material, current organic electronic such as
Under：
The characteristic of the material currently required that is that material possesses the efficient of heat endurance and quick hole degree of excursion and illuminator
Rate and long-life, the present invention are to provide the material for surmounting performance at this stage.
The content of the invention
The invention provides a kind of good hole mobile material of luminous efficiency, by bisaniline compounds and ether compound
Link together, rise hole degree of excursion, and this new aromatic amine compound is prepared into device, there is good hair
Light efficiency.
Technical scheme is as follows, and the general structure of the new aromatic amine analog derivative is,
[chemical formula 1]
In above-mentioned chemical formula 1, L1Be 0 ~ 2 integer, upper Ar1It is the aryl of carbon number 6 ~ 30（L1>Arlydene when 0, but
Do not include benzopyran compound）、Ar2It is substituted aralkyl, the aralkoxy of carbon number 7 ~ 50, the carbon original of carbon number 7 ~ 50
Aralkyl sulfydryl, the aryl of carbon number 6 ~ 50, the heterocycle of carbon number 5 ~ 50, the substituted or unsubstituted carbon atom of subnumber 7 ~ 50
The aromatic amine of number 6 ~ 30；
R1~R4Represent the same or different hydrogen atom, the aralkyl of substituted or unsubstituted carbon number 7 ~ 50, substitution
Or aralkoxy, aralkyl sulfydryl, the carbon atom of substituted or unsubstituted carbon number 7 ~ 50 of unsubstituted carbon number 7 ~ 50
The aryl of number 6 ~ 50, the heterocycle of substituted or unsubstituted carbon number 5 ~ 50, the virtue of substituted or unsubstituted carbon number 6 ~ 30
Fragrant race's amine.
Described diphenylamine derivative, is any one specific new virtue in following chemical formula 2-1 ~ chemical formula 2-9
Fragrant race's amines：
[chemical formula 2-1] works as R1~R4During for hydrogen,
[chemical formula 2-2] works as R2~R4During for hydrogen,
[chemical formula 2-3] works as R1~R3During for hydrogen,
[chemical formula 2-4] works as R3And R4During for hydrogen,
[chemical formula 2-5] works as R1And R4During for hydrogen,
[chemical formula 2-6] works as R1And R2During for hydrogen,
[chemical formula 2-7] works as R4During for hydrogen,
[chemical formula 2-8] works as R1During for hydrogen,
[chemical formula 2-9] works as R1~R4During for the same or different hydrogen atom,
L1Be 0 ~ 2 integer, in chemical formula 2-1 ~ chemical formula 2-9, Ar1It is the aryl of carbon number 6 ~ 30（L1>Sub- virtue when 0
Base）, Ar2Be the aralkyl, the aralkoxy of carbon number 7 ~ 50, carbon number 7 ~ 50 of carbon number 7 ~ 50 aralkyl sulfydryl,
Aryl, the heterocycle of carbon number 5 ~ 50, the aromatic amine of substituted or unsubstituted carbon number 6 ~ 30 of carbon number 6 ~ 50；
R1~R4Represent aralkyl, the substituted or unsubstituted carbon number 7 ~ 50 of substituted or unsubstituted carbon number 7 ~ 50
Aralkoxy, the aralkyl sulfydryl of substituted or unsubstituted carbon number 7 ~ 50, the aryl of carbon number 6 ~ 50, substitution or do not take
Heterocycle, the aromatic amine of substituted or unsubstituted carbon number 6 ~ 30 of the carbon number 5 ~ 50 in generation.
Wherein any one represents specific new fragrance in the chemical formula 1, including following chemical formula 3-1 ~ chemical formula 3-7
Race's amines：
[chemical formula 3-1]
[chemical formula 3-2]
[chemical formula 3-3]
[chemical formula 3-4]
[chemical formula 3-5]
[chemical formula 3-6]
[chemical formula 3-7]
[chemical formula 3-8]
In above-mentioned chemical formula 3-1 ~ chemical formula 3-8, Ar2It is aralkyl, the virtue of carbon number 7 ~ 50 of carbon number 7 ~ 50
Alkoxy, the aralkyl sulfydryl of carbon number 7 ~ 50, the aryl of carbon number 6 ~ 50, the heterocycle of carbon number 5 ~ 50, substitution or not
The aromatic amine of substituted carbon number 6 ~ 30.
L1Be 0 ~ 2 integer, R1~R4Represent the same or different hydrogen atom, substituted or unsubstituted carbon number 7 ~ 50
Aralkyl, the aralkoxy of substituted or unsubstituted carbon number 7 ~ 50, the virtue of substituted or unsubstituted carbon number 7 ~ 50
Alkane sulfydryl, the aryl of carbon number 6 ~ 50, the heterocycle of substituted or unsubstituted carbon number 5 ~ 50, substituted or unsubstituted carbon are former
The aromatic amine of subnumber 6 ~ 30.
R in above-mentioned chemical formula 1, chemical formula 2-1 ~ 2-9 and chemical formula 3-1 ~ 3-81~R4Wherein appoint in following chemical formula
The specific new aromatic amines compound of one composition of meaning：
The wherein alkoxy of the expression carbon number 1 ~ 30 of X and Y independences, the alkene of substituted or unsubstituted carbon number 2 ~ 30
Base, the aralkyl of substituted or unsubstituted carbon number 7 ~ 30, the aralkoxy of substituted or unsubstituted carbon number 7 ~ 30, take
Generation or the aromatic radical of unsubstituted carbon number 6 ~ 30, the aryloxy group of substituted or unsubstituted carbon number 6 ~ 30, substitution or not
Heterocyclic radical, the aromatic amine of substituted or unsubstituted carbon number 6 ~ 30 of substituted carbon number 5 ~ 30.
Described chemical formula 1 can be expressed as any one in following chemical formula 4-1 ~ chemical formula 4-8 and represent the new of feature
Aromatic amines compound.
[chemical formula 4-1] works as R1~R4During for hydrogen,
[chemical formula 4-2] works as R3、R4For hydrogen, R1、R2During for phenyl,
[chemical formula 4-3] works as R1、R4For hydrogen, R2、R3During for phenyl,
[chemical formula 4-4] works as R1、R2For hydrogen, R3、R4During for phenyl,
[chemical formula 4-5] works as R1、R2、R3For phenyl, R4During for hydrogen,
[chemical formula 4-6] works as R2、R3、R4For phenyl, R1During for hydrogen,
[chemical formula 4-7] works as R1~R4During for phenyl,
[chemical formula 4-8] works as R1~R4During for pyridine radicals,
In above-mentioned chemical formula 4-1 ~ chemical formula 4-8, L1Be 0 ~ 2 integer.Ar1It is the aryl of carbon number 6 ~ 30（L1>When 0
Arlydene, but do not include benzo class compound）, Ar2It is aralkyl, the aralkyl oxygen of carbon number 7 ~ 50 of carbon number 7 ~ 50
Base, the aralkyl sulfydryl of carbon number 7 ~ 50, the aryl of carbon number 6 ~ 50, the heterocycle of carbon number 5 ~ 50, substitution or unsubstituted
Carbon number 6 ~ 30 aromatic amine.
In order to more specifically describe heretofore described diphenylamine derivative, its specific manifestation form is at least, whenIt is respectively selected from compound E ~ L compounds in following radicals, i.e. specification embodiment.
With it is a kind of in 184 kinds of noval chemical compounds of above-mentioned chemical formula 4-1 ~ 4-8 composition, i.e., compound E in specification embodiment ~
L.Compound E ~ L is exactly the specific structure type of the compound, but this series compound does not limit to and these listed changes
Learn structure.It is every based on chemical formula 1, the R in above-mentioned protection domain1~R4、A1、A2、L1Any combination should all be included in
It is interior.
Still further aspect of the present invention be to provide the new aromatic amine analog derivative including chemical formula 1 above be made have
Organic electroluminescence devices.
Additional aspects of the present invention are a kind of organic luminescent devices, including first electrode, second electrode and are placed in described two
One or more organic compound layers between electrode, it is characterised in that at least one organic compound layer includes at least one
New aromatic amines compound of the present invention.
Above-mentioned new aromatic amine derivative is single form or included with other material mixing forms in above-mentioned organic layer.
Above-mentioned organic matter layer wherein at least includes hole injection layer, hole transmission layer, had both possessed hole injection but also with sky
Cave transmission technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both possesses electronics biography
Any one layer in the defeated layer but also with electron injection technical ability.
Above-mentioned hole injection layer, above-mentioned hole transmission layer, above-mentioned both possessed hole injection but also with hole transport technical ability layer
In at least one be conventional hole injecting material, hole transporting material and both possess hole injection but also with hole transport technical ability
Material, it is also possible to be the material of electron-transporting material generation.
" organic matter layer " refers to the whole disposed between organic electronic device first electrode and second electrode in this patent
The term of layer.
Such as, above-mentioned organic layer includes luminescent layer, and above-mentioned organic layer includes phosphorescence host, fluorescent host, phosphorescence doping
And more than one in fluorescence doping, including above-mentioned new aromatic amine derivative in above-mentioned luminescent layer, i) above-mentioned fluorescent host
Can be above-mentioned new aromatic amine derivative ii) doping of above-mentioned fluorescence can be above-mentioned aromatic amine derivative iii）Above-mentioned fluorescence
It can be above-mentioned new aromatic amine derivative that main body and fluorescence, which adulterate,.
Above-mentioned luminescent layer is can also red, yellow or cyan luminescent layer.Such as, above-mentioned new virtue during above-mentioned luminescent layer cyan
Fragrant race's amine derivative uses in cyan main body or cyan doping purposes that there is provided high efficiency, high brightness, high-resolution and long-life
Organic luminescent device.
And above-mentioned organic layer includes electron transfer layer, above-mentioned electron transfer layer includes above-mentioned new aromatic amine and derived
Thing.Wherein above-mentioned electron transfer layer is to include the compound containing metal beyond above-mentioned new aromatic amine derivative again.
Above-mentioned organic layer all includes luminescent layer and electron transfer layer, and above-mentioned luminescent layer and electron transfer layer each include above-mentioned
Aromatic amine derivative（Above-mentioned luminescent layer and electron transfer layer include above-mentioned new amine derivant can also it is identical can not also
Together）.
Described new aromatic amine derivative and conventional material and preparation of the above-mentioned organic electronic device using chemical formula 1
It is prepared by the method for organic electronic device.
Another aspect of the present invention is that above-mentioned device can be used in organic luminescent device（OLED）, organic photovoltaic cell
（OSC）, Electronic Paper（e-Paper）, Organophotoreceptor（OPC）Or OTFT（OTFT）.Organic luminescent device is profit
With evaporation metal and conductive oxide on the method substrate such as film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) and
Their alloy formation anode, layer, luminescent layer, hole blocking layer and electron transfer layer are passed in its above-mentioned hole injection layer, hole
It is prepared by the method for its later above-mentioned evaporation cathode.Cathode substance starts organic matter layer, anode material on substrate beyond above method
Evaporation makes organic luminescent device in order.
Above-mentioned organic matter layer is can also to include hole injection layer, hole to pass on layer, luminescent layer, hole blocking layer and electronics
The sandwich construction of transport layer, and above-mentioned organic matter layer is to substitute evaporation coating method using various high polymer material solvent engineering,
Such as, spin-coating（spin-coating）, strip
Shaping（tape-casting）, scraping blade method（doctor-blading）, silk-screen printing（Screen-Printing）、
The method such as ink jet printing or thermal imaging (Therma8Imaging) reduces number of plies manufacture.
Being according to the organic assembly of the present invention can also above luminous, back side illuminated or lighting at two sides by the material used.
The compound of the present invention is organic photovoltaic cell, illumination OLED, flexibility OLED, Organophotoreceptor, organic crystal
Organic luminescent device can also be applicable in the organic assemblies such as pipe and is applicable similar principle.
Another aspect of the present invention is to provide the preparation method of above-mentioned new aromatic amine derivative, including Zhi Change react, also
Original reaction, C-C coupled reactions and aminating reaction.
The preparation method of above-mentioned new aromatic amine analog derivative is as follows：
The stage of C-C couplings or aminating reaction is carried out according to reaction equation (1-1), (1-2) and (1-3)；
According to reaction equation（1-4）, reaction equation（1-5）Carry out the stage that aminating reaction synthesizes Q-3；
According to reaction equation（1-6）Q-3 is generated to Q-4 stage by hydrolysis；
According to reaction equation（1-7）, by reaction equation（1-1）Obtained intermediate and Q-4 synthesizes new fragrance through reduction reaction
Race's amines stage.
Ar in above-mentioned chemical formula1And Ar2And L1And R1~ R4Definition it is identical with aforementioned Chemistry Figure 1.
Beneficial effect：
The new aromatic amine analog derivative of the present invention is ether, Ar will to be linked in bisaniline compounds1And Ar2Upward electronics
Closeness and the relevant performance of raising, adjust the R of diphenylamines in addition1And R4Ligand molecular amount and ligand species improve performance and improvement
The advantages of function.In the present invention using the organic assembly of amine derivative be with high brightness, outstanding heat resistance, the long-life,
High efficiency.
Embodiment：
Another aspect of the present invention is to provide the preparation method of above-mentioned new aromatic amine derivative, including displacement is reacted, also
Former reaction, coupling reaction, aminating reaction etc..
The preparation method of above-mentioned new aromatic amine analog derivative is as follows：
The stage of C-C couplings or aminating reaction is carried out according to reaction equation (1-1), (1-2) and (1-3)；
According to reaction equation（1-4）, reaction equation（1-5）Carry out the stage that aminating reaction synthesizes Q-3；
According to reaction equation（1-6）Q-3 is generated to Q-4 stage by hydrolysis；
According to reaction equation（1-7）, by reaction equation（1-1）Obtained intermediate and Q-4 synthesizes new fragrance through reduction reaction
Race's amines stage.
Ar in above-mentioned chemical formula1And Ar2And L1And R1~ R4Definition it is identical with aforementioned Chemistry Figure 1.
The following is the implementation example of the present invention, example below is to aid in what the present invention understood and provided, is not
Present disclosure is limited to this scope.And the specific preparation side for not enumerating compound in various embodiments of the present invention
Method is the method described in embodiment about industry commonly used method, when preparing other compounds, can also be referred to.
The preparation of intermediate：
Intermediate 4- bromo- N, N- diphenyl-naphthalidines（A-1）Synthesis：
The bromo- 4- iodine naphthalenes of 1-（10mmol, 3.3g）, diphenylamine（20mmol, 3.38g）Add
Cuprous iodide is added under 100mL there-necked flasks, nitrogen（2mmol, 0.4g）, potassium carbonate（20mmol, 1.4g）, adjacent Féraud
Quinoline（2mmol, 0.4g）, DMF50mL, 155 DEG C of reaction 3d.Post processing：Extraction, organic phase boiled after being evaporated with ethanol, after use acetic acid
Ethyl ester and petroleum ether recrystallize to obtain product A-1（1.53g, y=50%）.
The synthesis of intermediate A -2：
The compound of following [table 1] is obtained with the ratio of same molar according to above-mentioned A-1 preparation method.
【Table 1】
Intermediate 9,9'-（The chloro- 1,3- phenylenes of 5-）It is double（9H- carbazoles）（A-3）Synthesis：
1,3,5- tribromo-benzenes（10mmol, 3.2g）, carbazole（40mmol, 6.7g）Add 100mL
Cuprous iodide is added under there-necked flask, nitrogen（4mmol, 0.8g）, potassium carbonate（40mmol, 2.8g）, Phen
（4mmol, 0.8g）, DMF50mL, 155 DEG C of reaction 3d.Post processing：Extraction, organic phase is boiled after being evaporated with ethanol, uses acetic acid second afterwards
Ester and petroleum ether recrystallize to obtain product 9,9'-（The chloro- 1,3- phenylenes of 5-）It is double（9H- carbazoles）(A-3)（3.4g, y=70%）.
The synthesis of intermediate A -4：
The compound of following [table 2] is obtained with the ratio of same molar according to above-mentioned A-3 preparation method.
【Table 2】
Intermediate 4,4'-（The chloro- 1,3- phenylenes of 5-）The synthesis of two pyridines (A-5)：
By the bromo- 5- chlorobenzenes of 1,3- bis-（10mmol, 2.70g）, 4- pyridine boronic acids（20mmol, 2.46g）, toluene（30mL）、
Wet chemical（2N, 16mL）It is put into there-necked flask, nitrogen displacement, nitrogen protection is lower to add four triphenyl phosphorus palladiums
（0.2mmol, 0.21g）90 DEG C of reactions are stayed overnight, and A-5 (1.73g, 65%) is obtained after reaction treatment.
The synthesis of intermediate A -6 and A-7：
The compound of following [table 3] is obtained with same molar ratio according to above-described embodiment A-5 preparation method.
【Table 3】
Intermediate 9-（4- chlorphenyls）Luxuriant and rich with fragrance (B-1) synthesis：
Luxuriant and rich with fragrance (10mmol, 1.93g), 4- chlorophenylboronic acids (10mmol, 1.56g), four triphenyl phosphorus palladiums by 9- bromines
(0.01mmol, 0.1g), aqueous sodium carbonate（2N,30mL）It is fitted into 100ml three-necked flasks, is taken out after addition 30ml toluene
Vacuum-logical nitrogen three times, is warming up to 70 DEG C, reaction is stayed overnight.Reaction solution is cooled to room temperature, and point liquid takes toluene phase, crosses silica gel funnel
Rinse to without product, be spin-dried for, ethyl acetate dissolving petroleum ether separates out B-1（3.6g, y=50%）.
Intermediate B -2 ~ B-7 synthesis：
The compound of following [table 4] is obtained with the ratio of same molar according to the preparation method of above-mentioned intermediate B -1.
【Table 4】
Intermediate 3- chloro-5-methoxyls-N, N- diphenylamine（C-1）Synthesis：
The bromo- 3- chloro-5-methoxyls benzene of 1-（10mmol, 2.2 g）, carbazole（20mmol, 3.38g）100mL there-necked flasks are added,
Cuprous iodide is added under nitrogen（2mmol, 0.4g）, potassium carbonate（20mmol, 1.4g）, Phen（2mmol,
0.4g）, DMF50mL, 155 DEG C of reaction 3d.Post processing：Extraction, organic phase is boiled after being evaporated with ethanol, rear to use ethyl acetate and oil
Ether recrystallizes to obtain product C-1（1.24g, y=40%）.
Intermediate C-2 ~ C-4 synthesis：
Preparation method according to above-mentioned intermediate C-1 obtains the compound of following [table 5] with identical mol ratio.
【Table 5】
The synthesis of intermediate 3- (9H- carbazole -9- bases) -5- methoxyl groups-N, N- diphenylamine (D-1)：
By intermediate C-1（10mmol, 3.09g）, carbazole（30mmol, 7.29g）Add under 100mL there-necked flasks, nitrogen and add
Enter cuprous iodide（3mmol, 0.6g）, potassium carbonate（30mmol, 4.15g）, Phen（3mmol, 0.6g）, DMF50mL, 180
DEG C reaction 3d.Post processing：Extraction, organic phase is boiled after being evaporated with ethanol, recrystallizes to obtain product D-1 with ethyl acetate and petroleum ether afterwards
（1.98g, y=45%）.
Intermediate D-2 ~ D-8 synthesis：
Above-described embodiment D-1 preparation method obtains the compound of following [table 6] with identical mol ratio.
【Table 6】
The synthesis of intermediate 3- (9H- carbazole -9- bases) -5- (diphenyl amino) phenol (E-1)：
Add D-1 (20 mmol, 8.81g), HBr (11mL), the tri-n-octyl methyl ammonium chloride of 47% concentration in reaction bulb
（2g）105 DEG C of heating, by terminating reaction after TLC thirty.Pillar was extracted with ethyl acetate and water to obtain（E-1）（7.25g, y=
85%）.
Intermediate E -2 ~ E-8 synthesis：
Preparation method according to above-described embodiment E-1 obtains the compound of following [table 4] with identical mol ratio.
【Table 4】
Synthetic example：
Embodiment 3- (9H- carbazole -9- bases) -5- (1- naphthyls epoxide)-N, N- diphenylamines（F-1）：
D-1 is added into 100mL there-necked flasks（4.26g, 10mmol）It is dissolved in 50ml acetonitriles, cesium carbonate is added afterwards
（20mmol, 6.5g）, copper（0.2mmol, 12mg）, a bromonaphthalene（11mmol, 2.27g）The lower 80 DEG C of reactions 4h of nitrogen protection, reaction
Extracted after end, be evaporated organic phase column chromatography and obtain product F-1（3.86g, y=70%）, MS/FAB (M+)：552.24.
Embodiment F-2 ~ F-22：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 8] with identical mol ratio.
【Table 8】
Embodiment G-1 ~ G-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 9] with identical mol ratio.
【Table 9】
Embodiment H-1 ~ H-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 11] with identical mol ratio.
【Table 11】
Embodiment I-1 ~ I-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 12] with identical mol ratio.
【Table 12】
Embodiment J-1 ~ J-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 13] with identical mol ratio.
【Table 13】
Embodiment K-1 ~ K-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 14] with identical mol ratio.
【Table 14】
Embodiment L-1 ~ L-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 15] with identical mol ratio.
【Table 15】
Embodiment M-1 ~ M-22 synthesis：
Preparation method according to above-described embodiment F-1 obtains the compound of following [table 16] with identical mol ratio.
【Table 16】
Device prepares embodiment：
Fisher Co., Ltd's coating layer thickness is placed on cleaning 2 times in distilled water for 1500 ito glass substrate, ultrasonic wave is washed
Wash 30 minutes, wash 30 minutes, cleaned repeatedly with distilled water 2 times in order by isopropanol, acetone, methanol, ultrasonic washing 10
Minute, dry, be transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, is sent in evaporator.It will have been prepared for
Evaporation hole injection layer 2-TNATA evaporations 500, hole transmission layer a-NPD or embodiment F ~ implementation on good ito transparent electrode
Example M materials evaporation 300, hole blocking layer and hole transmission layer TPBi400, negative electrode LiF5, Al2000；Said process
It is 0.2/sec that organic matter vaporization plating speed, which is to maintain 1/sec, LiF, and Al is 3 ~ 7/sec.
The electron luminescence characteristic of the organic luminescent device of above method manufacture is represented in table 17.
[table 17]
From the above-mentioned result of table 17, it is seen that the middle luminous efficiency and life characteristic of new aromatic amine derivative of the invention
Increase significantly.It should be appreciated that the application of the present invention is not limited to above-mentioned citing, those of ordinary skill in the art are come
Say, can according to the above description be improved or converted, all these modifications and variations should all belong to right appended by the present invention will
The protection domain asked.
The present invention is can to obtain luminous efficiency and the life-span is good using the organic luminescent device of new aromatic amine derivative
Good result, so the present invention is useful in the high OLED industries of practicality.The organic luminescent device of the present invention is plane face
Plate is shown, planar illuminant, illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or
Light source, display board, the mark of dosing machine class etc. are suitable to be used.
Claims (3)
1. a kind of aromatic amine compound, it is characterised in that the aromatic amine compound molecule formula is：
[chemical formula 1]
Wherein, L1For 0 or 1；Ar1For phenyl, naphthyl, phenanthryl, pyrenyl, the fluorenyl of 9,9'- spiral shells two, carbazyl；Ar2For phenyl,、；R1~R4For hydrogen, phenyl or pyridine radicals；And work as L1For 1 when, Ar1Group is subunit.
2. a kind of aromatic amine compound, it is characterised in that the aromatic amine compound is shown in following chemical formula
Compound：
F-1,F-2,
F-4,F-6,
F-8,F-9,
F-10,G-2,
G-8,H-2,
H-8,I-8,
J-8,K-8,
L-8,M-8。
3. a kind of organic luminescent device, including first electrode, second electrode and it is placed in one or more between two electrode
Organic compound layer, it is characterised in that at least one organic compound layer is comprising at least one such as claim 1 or claim
Aromatic amine compound described in 2.
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