CN107382908A - A kind of biphenyl compound, organic electroluminescence device and display device - Google Patents
A kind of biphenyl compound, organic electroluminescence device and display device Download PDFInfo
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- CN107382908A CN107382908A CN201710565091.7A CN201710565091A CN107382908A CN 107382908 A CN107382908 A CN 107382908A CN 201710565091 A CN201710565091 A CN 201710565091A CN 107382908 A CN107382908 A CN 107382908A
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- organic electroluminescence
- electroluminescence device
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- anthryl
- fluorenyl
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- BZVKZWJITLAUIG-VFMIJEDLSA-N CC(c(cc1N2CCOCC2)ccc1C(C(CN1CCOCC1)=CC12)=CC1C2C1=C(C=CC=C2)C2=C(c2ccc(cccc3)c3c2)C2=CCCC=C12)c1ccccc1/C(/c1cc(cccc2)c2cc1)=C1/C=CC=CC1 Chemical compound CC(c(cc1N2CCOCC2)ccc1C(C(CN1CCOCC1)=CC12)=CC1C2C1=C(C=CC=C2)C2=C(c2ccc(cccc3)c3c2)C2=CCCC=C12)c1ccccc1/C(/c1cc(cccc2)c2cc1)=C1/C=CC=CC1 BZVKZWJITLAUIG-VFMIJEDLSA-N 0.000 description 1
- GHOOUHFPZAWYDM-UHFFFAOYSA-N CCOCCN(CCOCC)c1cc(-c2c(cccc3)c3c(-c3cc(cccc4)c4cc3)c3c2cccc3)ccc1-c(ccc(-c1c(cccc2)c2c(-c2cc3ccccc3cc2)c2c1cccc2)c1)c1N(CCOCC)CCOCC Chemical compound CCOCCN(CCOCC)c1cc(-c2c(cccc3)c3c(-c3cc(cccc4)c4cc3)c3c2cccc3)ccc1-c(ccc(-c1c(cccc2)c2c(-c2cc3ccccc3cc2)c2c1cccc2)c1)c1N(CCOCC)CCOCC GHOOUHFPZAWYDM-UHFFFAOYSA-N 0.000 description 1
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- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
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Abstract
The present invention relates to display technology field, more particularly to a kind of biphenyl compound, organic electroluminescence device and display device.According to the compound such as formula (1) of the present invention:
Description
Technical field
The present invention relates to display technology field, more particularly to a kind of biphenyl compound, organic electroluminescence device and
Display device.
Background technology
Organic electroluminescence device (Organic Light Emitting Display, abbreviation OLED) is put down as new
Panel display, compared with liquid crystal display (Liquid Crystal Display, abbreviation LCD), there is thin, light, wide viewing angle, master
Move low luminous, glow color continuously adjustabe, cost, fast response time, energy consumption is small, driving voltage is low, operating temperature range is wide, raw
Production. art is simple, luminous efficiency is high and can Flexible Displays the advantages that, obtained the very big concern of industrial circle and scientific circles.
The development of organic electroluminescence device promotes research of the people to electroluminescent organic material.Relative to inorganic hair
Luminescent material, electroluminescent organic material have advantages below:Organic material processing characteristics is good, can pass through evaporation or the side of spin coating
Method film forming on any substrate;The diversity of organic molecular structure allow to by Molecular Design and the method for modification come
Adjust the heat endurance of organic material, mechanical performance, luminous and electric conductivity so that material is significantly improved space.
What the generation of organic electroluminescent was leaned on is the carrier (electronics and hole) transmitted in organic semiconducting materials
Restructuring.It is well known that the electric conductivity of organic material is very poor, there is no the energy band continued in organic semiconductor, the transmission of carrier is normal
Described with jump theory.In order to make organic electroluminescence device reach breakthrough in application aspect, it is necessary to overcome organic material
Electric charge injects and the difficulty of transmittability difference.Scientists pass through the adjustment of device architecture, such as increase device organic material layer
Number, and different organic layers is played the part of different device layers, such as the functional material having can promote electronics from negative electrode
Injection, some functional materials can promote hole to be injected from anode, and some materials can promote the transmission of electric charge, and some materials are then
It can play a part of stopping electronics or hole transport.Certainly in organic electroluminescence device, most important a variety of colors
Luminescent material will also reach the purpose to match with adjacent functional material.Therefore, the organic electroluminescence of excellent in efficiency long lifespan
Part is typically the result of device architecture and the optimization collocation of various organic materials, and this just designs and develops various structures for chemists
Functionalization material provide great opportunities and challenges.
In organic electroluminescence device preparation technology, one kind is referred to as vapour deposition method, i.e., each functional material passes through vacuum
The mode of hot evaporation is plated to film forming on substrate, and this is also the mainstream technology of current industry.But the shortcomings that this technique it is also obvious that
The characteristic of one side organic material determines in itself, hot evaporation is carried out under the high temperature conditions for a long time, to the heat endurance of material
It is it is required that very high;In addition prolonged stability contorting evaporation rate, keep the distribution of thereon material uniformity be also one very
Important requirement;And high vacuum, high temperature deposition, energy consumption are higher;Main, because OLED material production technology itself compares
Complexity, technology content is higher, thus price is costly, and existing process is used by the way that mode is deposited, the utilization of OLED material
Rate is relatively low, typically below 10%.
In the preparation technology of organic electroluminescence device, another is referred to as solwution method, i.e., using solvable OLED materials
Material, is dissolved in solvent, is coated in by modes such as printing, ink-jet, spin coatings on substrate, such a to form some functional layers
Method material is evenly distributed, and saves material, simplifies OLED production technology, reduces OLED production cost.
The content of the invention
Have the invention provides a kind of biphenyl compound, the organic electroluminescence device comprising the compound and with this
The display device of organic electroluminescence devices, the organic electroluminescence device comprising the compound have relatively low driving voltage and compared with
High luminous efficiency.
And biphenyl compound provided by the invention, in organic solvent with preferable dissolubility, and have good
Film forming.In organic electroluminescence device preparation, luminescent layer can be formed by solwution method.
According to an aspect of the present invention, there is provided a kind of biphenyl compound, as shown in formula (1):
Wherein X is selected from the aryl that substituted or unsubstituted carbon number is 6-80;
Wherein A is selected from following structure:
Wherein A1, A2, A3 are independently selected from the aliphatic alkyl, the carbon of alkoxy substitution that carbon number is 1~20
Atomicity is 1~20 aliphatic alkyl.
Further, wherein described substituted or unsubstituted carbon number is 6-80 aryl, it is characterised in that described
Aryl is selected from:Phenyl, xenyl, naphthyl, anthryl, phenanthryl, Sanya phenyl, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentano
Phenanthryl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl;
Wherein described substituent is selected from:Cycloalkyl that alkyl that carbon number is 1-20, carbon number are 3-20, phenyl,
Xenyl, naphthyl, anthryl, phenanthryl, Sanya phenyl, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzene
And fluorenyl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
The biphenyl compound of the present invention preferably is selected from following structure:
According to another aspect of the present invention, there is provided a kind of solution, wherein at least comprising biphenyl class chemical combination of the present invention
Thing and at least one solvent.The solvent is selected from toluene, dimethylbenzene, chlorobenzene, dichloro-benzenes, diphenyl ether, chloroform, ethyl acetate, second
It is more than one or two kinds of in alcohol, isopropanol, n-butanol.
The preparation method of the solution is:In glove box, under nitrogen atmosphere, the compounds of this invention is dissolved in above-mentioned molten
In agent, then obtained by 0.1 micron of membrane filtration.
The fluorescent dye needed for organic electroluminescence device can be added during above-mentioned solution is prepared;Fluorescence
The weight of dyestuff and biphenyl compound of the present invention ratio is 1:100~1:10.
According to another aspect of the present invention, there is provided a kind of organic electroluminescence device, the organic electroluminescence device
Including according to biphenyl compound of the present invention.
Alternatively, the luminescent layer material of main part of the organic electroluminescence device is the biphenyl class chemical combination according to the present invention
Thing.
Optionally, the luminescent layer of described organic electroluminescence device is prepared by solwution method.
According to another aspect of the present invention, there is provided a kind of display device, the display device include having according to the present invention
Organic electroluminescence devices.
Beneficial effects of the present invention are as follows:
Compound provided by the invention is used as to the material of main part of the luminescent layer of organic electroluminescence device, improved organic
The luminous efficiency of electroluminescent device, the driving voltage for reducing organic electroluminescence device.
Because biphenyl compound of the present invention is due to the introducing of substituent A so that the configuration distortion of compound becomes big so that
The film forming of material is more preferably;Biphenyl compound contrasts simultaneously and existing for not substituted base A, improves material solubility, makes
Compound provided by the invention is obtained to be more suitable for preparing luminescent layer by solwution method.
Embodiment
Embodiment is only the description of the invention, without forming the limitation to present invention, below in conjunction with
Specific embodiment is further described and described to the present invention.
Have the invention provides a kind of biphenyl compound, the organic electroluminescence device comprising the compound and with this
The display device of organic electroluminescence devices, the organic electroluminescence device comprising the compound have relatively low driving voltage and compared with
High luminous efficiency.
Compound provided by the invention is used as to the material of main part of the organic luminous layer of organic electroluminescence device, improved
The luminous efficiency of organic electroluminescence device, the driving voltage for reducing organic electroluminescence device.
In order to which the compound of the present invention is explained in more detail, the synthetic method pair of above-mentioned particular compound will be enumerated below
The present invention is further described.
The intermediate M-01 of embodiment 1 synthesis:
Compound A-1 synthesis:
In 500 milliliters of there-necked flasks, under nitrogen protection, 220 milliliters of dry toluene, 20.1 grams of (0.05mol) formulas are added
Compound shown in A-0,10.2 grams of (0.12mol) cyclohexylamine, 14.4 grams of (0.15mol) sodium tert-butoxides, 0.58 gram (0.001mol)
Double (dibenzalacetone) palladiums, 2.02 grams of (0.001mol) 10% tri-butyl phosphine toluene solution, be heated to back flow reaction 4
Room temperature is down to after hour, adds watery hydrochloric acid, liquid separation, neutrality is washed with water in organic layer, after being dried with anhydrous magnesium sulfate, crosses silica gel
Post separation, eluent are concentrated to dryness, and with recrystallizing methanol, obtain 17.6 grams of compound shown in formula A-1, yield 85.75%.
To obtained compound A-1, Mass Spectrometer Method, product m/e are carried out:410.
Compound A-2 synthesis:
Compound 16 grams (0.039mol) shown in addition formula A-1 in 1000 milliliters of stainless steel hydrogenation kettles, 300 milliliters of ethanol,
5% palladium carbon 3g, after nitrogen displacement, in 60 DEG C, after control 0.2MPa hydrogen reducings react 6 hours, reaction finishes.Stop anti-
Should, after nitrogen displacement, material is taken out, Filtration of catalyst, 600 milliliters of water will be added in filtrate, separates out solid, filter out
After the solid arrived, with recrystallizing methanol, 10.2 grams of off-white powder shown in formula A-2 are obtained, yield 74.6%,
Mass Spectrometer Method has been carried out to product shown in obtained formula A-2, has obtained the m/e of product:350.
Intermediate M-01 synthesis:
In 1000 milliliters of there-necked flasks, 12.86 grams of (0.2mol) 48% hydrobromic acid aqueous solution is added, stirs lower addition 7.0
Gram compound shown in (0.02mol) formula A-2, it is warming up to backflow and is kept for 5 minutes, be then cooled to 25 DEG C, add 0.5 gram
(0.0035mol) cuprous bromide, then temperature is controlled to be slowly added dropwise 2.76 grams of (0.04mol) NaNO2's between 25~35 DEG C
10 milliliters of aqueous solution, be added dropwise be to slowly warm up to 60~65 DEG C keep 1 hour, then be warming up to 85-90 DEG C keep 2 hours, drop
Temperature, filtering, obtained solid methanol and chloroform mixed solvent crystallization, obtains 4.17 grams of off-white powder shown in formula M-01, receives
Rate 43.62%,
Mass Spectrometer Method has been carried out to product shown in obtained formula M-01, has obtained the m/e of product:478.
Nuclear-magnetism detection is carried out to product shown in obtained formula M-01, obtained nuclear-magnetism parsing data are as follows:
1HNMR (500MHz, CDCl3):δ 7.48 (t, 2H), δ 6.99 (m, 4H), δ 3.06 (t, 8H), δ 1.65 (m, 8H), δ
1.58 (m, 4H).
The intermediate M-02 of embodiment 2~intermediate M-13 synthesis
With reference to intermediate M-01 synthetic method, the first step is simply synthesized to the cyclohexylamine used in the process of compound A-1
Change corresponding amine into.Specific reaction amine used and mass spectrum and nuclear magnetic data are listed as follows:
The compound P-1 of embodiment 3 synthesis
The synthesis of intermediate B -01
In 1000 milliliters of there-necked flasks, 400 milliliters of tetrahydrofurans, chemical combination shown in 23.9 grams of (0.05mol) formula M-01 are added
Thing, -78 DEG C are cooled under nitrogen protection, the hexane solution of 75 milliliters of (0.12mol) 1.6M n-BuLi is slowly added dropwise, adds
Bi Yu -70~-78 DEG C are incubated 30 minutes, add the trimethylborate that 13.5 grams (0.13mol) steam again, are then to slowly warm up to
25 DEG C are reacted 2 hours, add watery hydrochloric acid hydrolysis, add ethyl acetate extraction, and organic layer is concentrated to dryness, with ethyl alcohol recrystallization,
Obtain 11.7 grams of product shown in formula B-01, HPLC 97.9%, yield 57.35%.
Compound P-1 synthesis:
In 1000 milliliters of there-necked flasks, 300 milliliters of toluene of addition, 300 milliliters of ethanol, 100 milliliters of water, 20.4 grams
Compound shown in (0.05mol) formula B-01,36.6 grams of bromo- 10- phenylanthracenes of (0.011mol) 9-, 27.6 grams of (0.2mol) carbonic acid
Potassium, nitrogen protection is lower to add 1.16 grams of (0.001mol) tetra-triphenylphosphine palladiums, is to slowly warm up to 70 DEG C and reacts 8 hours, cools, point
Liquid, cross silicagel column after organic layer washing and decolourize, eluent is concentrated to dryness, silica gel column chromatography separation, ethyl acetate:Petroleum ether=1:
5 elutions, obtain 28.7 grams of product shown in formula P-1, yield 69.66%.
Mass Spectrometer Method has been carried out to product shown in obtained formula P-1, has obtained the m/e of product:824
Nuclear-magnetism detection is carried out to product shown in obtained formula P-1, obtained nuclear-magnetism parsing data are as follows:
1HNMR (500MHz, CDCl3):δ 8.21 (m, 8H), δ 7.78 (d, 2H), δ 7.66 (m, 4H), δ 7.55 (m, 4H), δ
7.42 (m, 10H), δ 7.00 (d, 2H), δ 6.58 (m, 2H), δ 3.06 (m, 8H), δ 1.70~1.56 (m, 12H).
Embodiment 4 compound P-2, P-7, P-10, P-11, P-17, P-20, P-21, P-23, P-27, P-30, P-31, P-
38 synthesis
Reference compound P-1 synthetic method, it is different according to the concrete structure of compound, M-01 therein is changed into accordingly
M-02~M-13 in one kind;Change the bromo- 10- phenylanthracenes of 9- used in the process of synthesis compound P-1 into corresponding bromo
Thing.The species and mass spectrum and nuclear magnetic data of particular compound are listed as follows:
According to another aspect of the present invention, there is provided a kind of organic electroluminescence device, the organic electroluminescence device
Include the biphenyl compound according to the present invention.
The typical structure of organic electroluminescence device is:Substrate/anode/hole injection layer/hole transmission layer (HTL)/has
Machine luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer/negative electrode.Organic electroluminescence device structure can be single-shot light
Layer can also be multi-luminescent layer.
Wherein, substrate can use the substrate in conventional organic electroluminescence device, such as:Glass or plastics.Anode can be with
Using transparent high conductivity material, such as:Indium tin oxygen (ITO), indium zinc oxygen (IZO), tin ash (SnO2), zinc oxide (ZnO).
The hole-injecting material (Hole Injection Material, abbreviation HIM) of hole injection layer, it is desirable to which there is height
Heat endurance (high Tg), have less potential barrier with anode or hole-injecting material, vapour deposition method prepares organic electroluminescent
During device, it is desirable to which the vacuum evaporation of material energy forms pin-hole free films.Conventional HIM is aromatic multi-amine class compound, mainly
Derivative of tri-arylamine group.When preparing organic electroluminescence device for solwution method, it is desirable to which material has suitable solubility, by solution
After being coated on substrate, after solution evaporation, fine and close, uniform unformed film can be formed on substrate.Conventional HIM material masters
There is PEDOT:PSS.
The hole mobile material (Hole Transport Material, abbreviation HTM) of hole transmission layer, it is desirable to which there is height
Heat endurance (high Tg), higher cavity transmission ability, can vacuum evaporation formed pin-hole free films.Conventional HTM is
Aromatic multi-amine class compound, mainly derivative of tri-arylamine group.
Organic luminous layer includes material of main part (host) and guest materials, and wherein guest materials is luminescent material, such as is contaminated
Material.In some cases, material of main part can be directly used as organic luminous layer without using guest materials.Material of main part needs
Possess following characteristics:Reversible electrochemical redox current potential, match with adjacent hole transmission layer and electron transfer layer
HOMO energy levels and lumo energy, good and the hole to match and electron transport ability, good high heat endurance and into
Film, and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer, also with corresponding fluorescent dye
Or good energy transfer between phosphorescent coloring.The luminescent material of organic luminous layer, it is necessary to possess following spy by taking dyestuff as an example
Point:With high fluorescence or phosphorescence quantum efficiency;The absorption spectrum of dyestuff had with the emission spectrum of main body it is overlapping, i.e., it is main
Body is adapted to dyestuff energy, can effectively energy transmission from main body to dyestuff;The emission peak of red, green, blue is as narrow as possible, to obtain
Good excitation;Stability is good, can be deposited etc..When preparing organic luminous layer with solwution method, also require that material has
Suitable solubility, by solution coating after on substrate, after solution evaporation, it can be formed on substrate fine and close, uniform unformed
Film.
The electron transport material (Electron transport Material, abbreviation ETM) of electron transfer layer requires ETM
There are reversible and sufficiently high electrochemical reduction current potential, suitable HOMO energy levels and LUMO (Lowest Unoccupied
Molecular Orbital, lowest unoccupied molecular orbital) energy level value enables electronics preferably to inject, and is preferably provided with
Hole blocking ability;Higher electron transport ability, the film forming having had and heat endurance.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.When vapour deposition method prepares organic electroluminescence device, electron transfer layer typically uses Alq3
(8-hydroxyquinoline aluminium) either TAZ (3- phenyl -4- (1 '-naphthyl) -5- benzene -1,2,4- triazoles) or the TPBi ((N- of 1,3,5- tri-
Phenyl -2- benzimidazoles) benzene) or it is derived from any two kinds of collocation of these three materials.
According to another aspect of the present invention, there is provided a kind of display device, the display device include having according to the present invention
Organic electroluminescence devices.
, can be by all functional layers therein using evaporation legal system in the preparation process of organic electroluminescence device
It is standby, one layer therein or multilayer can also be prepared using vapour deposition method, other functional layers are prepared using solwution method, can also be incited somebody to action
All functional layers therein are prepared using solwution method.
It is as can be seen here, more according to the optional factor of the compound of the present invention, organic electroluminescence device and display device,
Different embodiments can be combined into according to the claim of the present invention.Embodiments of the invention are only as to the specific of the present invention
Description, is not intended as limitation of the present invention.Make below in conjunction with the organic electroluminescence device of the compound containing the present invention
For embodiment, the present invention is described further.
The concrete structure of material therefor is seen below in embodiment:
Embodiment 5
From the main body material of compound of the invention as the organic luminous layer in blue-fluorescence organic electroluminescence device
Material;Comparative example selects material of main parts of the ADN as the organic luminous layer in blue-fluorescence organic electroluminescence device.
Organic electroluminescence device structure is:ITO/NPB (40nm)/Blue-light emitting host material (30nm):DPAVBi [5%]/
Alq3(20nm)/LiF(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, the ultrasonic oil removing in acetone and alcohol mixed solvent, is toasted under clean environment
Moisture is removed to complete, with being cleaned under the conditions of ultraviolet light and ozone, and with low energy cation beam bombarded surface.
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation NPB is 40nm as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness on anode tunic.
The vacuum evaporation Blue-light emitting host material on hole transmission layer:DPAVBi [5%] is used as organic electroluminescence device
Luminescent layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm;Wherein " DPAVBi [5%] " refers to mixing for blue light dyestuff
The weight part ratio of miscellaneous ratio, i.e. Blue-light emitting host material and DPAVBi is 100:5.
Electron transfer layers of the vacuum evaporation Alq3 as organic electroluminescence device on luminescent layer, its evaporation rate are
0.1nm/s, evaporation total film thickness are 20nm;
Vacuum evaporation 0.5nm LiF on the electron transport layer, 150nm Al are as electron injecting layer and negative electrode.
The performance for the organic electroluminescence device being prepared is tested, and test result is as shown in table 1.
Table 1
As can be seen from Table 1, using the blue-fluorescence organic electroluminescence device of the compounds of this invention relative to using industry
The ADN inside generally used blue-fluorescence organic electroluminescence device, obtain higher current efficiency and relatively low driving electricity
Pressure.
Embodiment 6
Using the compound of the present invention as emitting layer material, organic electroluminescence device is prepared by solwution method.Contrast
Example, as emitting layer material, organic electroluminescence device is prepared by solwution method from ADN.
Organic electroluminescence device structure is:ITO/NPB (40nm)/emitting layer material (30nm)/Alq3 (20nm)/LiF
(0.5nm)/Al(150nm)。
Organic electroluminescence device preparation process is as follows:The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, the ultrasonic oil removing in acetone and alcohol mixed solvent, is toasted under clean environment
Moisture is removed to complete, with being cleaned under the conditions of ultraviolet light and ozone, and with low energy cation beam bombarded surface.
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Vacuum evaporation NPB is 40nm as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness on anode tunic.
The above-mentioned glass substrate that hole transmission layer has been deposited is placed in glove box, under nitrogen atmosphere, by chemical combination of the present invention
Solution (0.5% chlorobenzene solution) (comparative example uses AND) spin coater of thing is uniformly spin-coated on 4000r/min speed
On glass substrate, vacuum drying removes solvent, the painting prepared in 60 minutes at a temperature of glass substrate then is placed in into 150 degree
The glass substrate of luminescent layer is covered.
The above-mentioned glass substrate for being coated with luminescent layer is transferred in vacuum chamber, vacuum evaporation Alq3 makees on luminescent layer
For the electron transfer layer of organic electroluminescence device, its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm;
Vacuum evaporation 0.5nm LiF on the electron transport layer, 150nm Al are as electron injecting layer and negative electrode.
The performance for the organic electroluminescence device being prepared is tested, and test result is as shown in table 2.
Table 2
As can be seen from Table 2, using the compounds of this invention organic electroluminescence device relative to the organic electroluminescence using ADN
Luminescent device, obtain higher current efficiency and relatively low driving voltage.
Obviously, those skilled in the art can carry out the essence of various changes and modification without departing from the present invention to the present invention
God and scope.So, if these modifications and variations of the present invention belong to the scope of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to comprising including these changes and modification.
Claims (8)
1. a kind of biphenyl compound, it is characterised in that shown in the compound such as formula (1):
Wherein X is selected from the aryl that substituted or unsubstituted carbon number is 6-80;
Wherein A is selected from following structure:
Wherein A1, A2, A3 are independently selected from the aliphatic alkyl, the carbon atom of alkoxy substitution that carbon number is 1~20
Number is 1~20 aliphatic alkyl.
2. biphenyl compound according to claim 1:
Wherein described substituted or unsubstituted carbon number is 6-80 aryl, it is characterised in that the carbon number is 6-
80 aryl is selected from:Phenyl, xenyl, naphthyl, anthryl, phenanthryl, Sanya phenyl, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, ring
Penta and phenanthryl, Spirofluorene-based, benzo fluorenyl, indeno anthryl, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl;
Wherein described substituent is selected from:Cycloalkyl that alkyl that carbon number is 1-20, carbon number are 3-20, phenyl, biphenyl
Base, naphthyl, anthryl, phenanthryl, Sanya phenyl, pyrenyl, fluorenyl, fluoranthene base, indeno fluorenyl, cyclopentaphenanthreneyl, Spirofluorene-based, benzfluorene
Base, dibenzo fluorenyl, naphtho- anthryl, benzo anthryl.
3. biphenyl compound according to claim 1, it is characterised in that the compound is selected from:
A kind of a kind of 4. solution, wherein at least comprising biphenyl compound and at least one solvent described in claim 1-3.
5. a kind of organic electroluminescence device, it is characterised in that it is any that the organic electroluminescence device includes claim 1-3
Described biphenyl compound.
6. organic electroluminescence device as claimed in claim 5, it is characterised in that the organic electroluminescence device lights
Layer main body material is any described biphenyl compounds of claim 1-3.
7. organic electroluminescence device as claimed in claim 5, it is characterised in that the organic electroluminescence device lights
Layer is prepared by solwution method.
8. a kind of display device, it is characterised in that including organic electroluminescence device as claimed in claim 5.
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