CN105176519B - A kind of oled light electric material and its application - Google Patents
A kind of oled light electric material and its application Download PDFInfo
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- CN105176519B CN105176519B CN201510552158.4A CN201510552158A CN105176519B CN 105176519 B CN105176519 B CN 105176519B CN 201510552158 A CN201510552158 A CN 201510552158A CN 105176519 B CN105176519 B CN 105176519B
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- 0 CCC*C(CS1)=NC1=C(C#N)C#N Chemical compound CCC*C(CS1)=NC1=C(C#N)C#N 0.000 description 2
- LAAWIDUXQDGDCR-ARJAWSKDSA-N ClC/C(/Cl)=C(\CCl)/Cl Chemical compound ClC/C(/Cl)=C(\CCl)/Cl LAAWIDUXQDGDCR-ARJAWSKDSA-N 0.000 description 1
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Abstract
The present invention relates to a kind of oled light electric material and its application, the oled light electric material is parent nucleus with 3 axle alkene, by combining containing strong electrophilic thiazole structure, forms a kind of photoelectric material with high thermal stability energy.OLED is manufactured using photoelectric material of the present invention, high brightness is capable of achieving, high efficiency, the effect of low-voltage, the photoelectric material that the present invention is provided can be used as the p-type dopant material of OLED.
Description
Technical field
The present invention relates to a kind of organic electroluminescent LED (OLED) photoelectric material and its application, belong to organic photoelectric material
Material technical field.
Background technology
In recent years, some are increasingly known for the photoelectric material of OLED, it is commonly known that aromatic diamines derive
Thing, as hole mobile material, is obtained enough during using such material in OLED, it is necessary to improve device applied voltage
Luminosity, this results in the shortening of device lifetime, and increased power consumption.To solve these problems, by the electronics that adulterates
Acceptor compound can make hole injection and hole transport in OLED significantly improve (document：He Gufeng,
Appl.Phys.lett.85(2004)3911-3913).Under same luminous efficiency, the addition of its electron acceptor compound can
With reduction OLED operating voltage by a relatively large margin.Strong electron acceptor compound such as four cyano quinone bismethane (TCNQ) or
Tetra- fluoro of 2,3,5,6--four cyano -1,4- benzoquinones bismethanes (F4TCNQ)。
For the method (P doping) for improving hole transport, the physical property of material therefor is in sublimation purification or vacuum evaporation
During there is problem, be directed to the four cyano benzoquinones bismethane (TCNQ or F of vapo(u)rability fluorination extremely rambunctious4TCNQ),
Because its molecular weight is smaller, it is easy to diffuse in sublimation process in equipment, causes contaminated equipment or device, so that this kind of mix
Miscellaneous dose cannot be used for batch production device in.
At present, research and relevant report on p-type dopant material at home, international all few, research in this respect
It is badly in need of further strengthening.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of oled light electric material and its application, the light that the present invention is provided
Electric material is more easy to prepare, can improve OLED luminous efficiency and life-span, reduces the driving voltage and vacuum of OLED
Evaporation controllability is high.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of oled light electric material, the structure such as institute of formula 1
Show：
Wherein, the Ar is the group that following formulas 2 are represented：
The R1-R5 is selected from any one in chlorine, fluorine, nitro, trifluoromethyl, isothiocyanate group or cyano group, and
The R1-R5 is identical or different.
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, the oled light electric material is selected from one of having structure：
The present invention also provides a kind of application of oled light electric material, in organic electroluminescence device, at least one work(
Ergosphere, contains above-mentioned oled light electric material.
The present invention also provides a kind of organic electroluminescence device, including：Luminescent layer between anode layer and cathode layer, and
Hole injection layer between the anode layer and the luminescent layer, wherein, the hole injection layer is by host material and dopant
The mol ratio of composition, the host material and dopant is 1:1-100000：1.
On the basis of above-mentioned technical proposal, the present invention can also do following improvement.
Further, the host material is selected from phthalocyanine copper complex (CuPc), 4,4 ', 4 " ,-three (N-3- tolyl-N- benzene
Base-amido) triphenylamine (m-MTDATA), 4,4 ', 4 " ,-three (N- (2- naphthyls)-N- phenyl-amido) triphenylamines (2-TNATA),
N, N, N ', N '-four (4- methoxyl groups-phenyl) benzidine (MeO-TPD), (2,2 ' 7,7 '-four-(N, N- diphenylamines) -9,9- spiral shells two
Fluorenes (spiral shell-TTB), three (terphenyl -4- bases) amine, N, N '-diphenyl-N, N '-(1- naphthyls) -1,1 '-biphenyl -4,4 '-diamines
(NPB) any one or a few in；The dopant is above-mentioned oled light electric material.
Due to a series of oled light electric materials based on 3- axle alkene that the present invention is provided, such material is by 3- axle alkenyls
Strong electrophilic dicyano thiazole is introduced on plinth has the aromatic yl group of strong electron-withdrawing power with other, there is provided can improve
OLED luminous efficiency and life-span, reduce the driving voltage and vacuum evaporation controllability photoelectricity material high of OLED
Material.
Thermogravimetric analysis and the differential thermal analysis test of such material show heat endurance and glass transition temperature higher,
Good amorphous thin film is easily formed, controlling is strong during high-temperature vacuum evaporation.
Thus, electroluminescent device device is manufactured using photoelectric material of the invention, high brightness is capable of achieving, easy film forming is high
Efficiency, the general effect of low-voltage.
Further, relatively low voltage is set in the course of the work and high thermal stability in itself that have and vitrifying turns
Temperature, applies in electroluminescent device, can obtain more stable effect and longer service life.
Also, generally prepare and more facilitate because the compound that the present invention is provided employs simpler synthetic method.Should
For electroluminescent device technical field, it is more easy to obtain as material, cost is lower, and with high brightness, high efficiency, low-voltage
General effect, thus be more suitable for industrial production.
Brief description of the drawings
Fig. 1 is the structural representation of the organic electroluminescence device that device embodiments of the present invention 1 are provided；
In accompanying drawing, the list of parts representated by each label is as follows：
1st, transparent substrate layer, 2, anode layer, 3, hole injection layer, 4, hole transmission layer, 5, luminescent layer, 6, electric transmission
Layer, 7, electron injecting layer, 8, cathode layer.
Specific embodiment
Principle of the invention and feature are described below, example is served only for explaining the present invention, is not intended to limit
Determine the scope of the present invention.
Prepare implementation method
In above-mentioned each molecular structural formula, C is carbon, and N is nitrogen, and Cl is chlorine, and S is sulphur.Thiazolium compounds exists with tetrachloro cyclopropylene
Under nitrogen or inert gas shielding, with lithium hydride, potassium tert-butoxide, sodium tert-butoxide, the hexane solution of butyl lithium, potassium carbonate or carbon
Sour caesium provides alkaline environment, is reacted 5-50 hours under conditions of -70~50 DEG C.
The material of above reaction raw materials material and offer alkaline environment is the art and often uses material or commercially available
Material.
Prepare embodiment
The structure of the specific oled light electric material of present invention synthesis is as follows：
In above-mentioned molecular structural formula, C is carbon, and N is nitrogen, and Cl is chlorine, and S is sulphur.For ease of hereafter quoting, each compound of the above
Structural formula under use numeric suffix, it is and corresponding with compound in embodiment, for example, the compound of the corresponding embodiment 1 of structural formula 1
(i.e. compound 1), the compound (i.e. compound 2) of the correspondence embodiment 2 of structural formula 2, remaining is by that analogy.Molecule in embodiment
Also there is corresponding mark behind formula.
The synthesis of the compound 1 of embodiment 1：
To addition 10.40g (33mmol) 2- (4- (perfluor) thiazole -2 (5H)-subunit) malononitrile and 50mL in there-necked flask
Dry THF, under nitrogen protection, slow cooling is added dropwise 44mL (2.5mol/L) butyl lithium hexane solution to -70 DEG C, and 1.0 is small
When drop finish, insulation reaction 3.0hrs.Temperature is less than -70 DEG C in control, and 1.78g (10mmol) tetrachloro cyclopropylene is added dropwise, and drips within 10 minutes
Finish.After drop finishes, -70 DEG C of insulated and stirreds of system 1.0 hours are then to slowly warm up to 20-25 DEG C, stirring reaction 24 hours.Then
Reaction solution is slowly poured into 200g frozen water, add the concentrated hydrochloric acid of mass fraction 36.5% to be acidified to pH=1, and use acetic acid second
Ester is extracted, and ethyl acetate 100mL, coextraction three times are used every time.Ethyl acetate phase is by saturated common salt water washing to pH=7, nothing
Aqueous sodium persulfate is dried, and reduced vacuum desolventizing obtains dark material to without cut, stand-by, without purifying.
Above-mentioned dark material is dissolved in 300g acetic acid, is stirred vigorously down and hydrobromic acid (60mL, quality is progressively added dropwise thereto
Fraction 48%) and concentrated nitric acid (20mL, mass fraction 65%) mixed liquor.20-25 DEG C stir 2.0 hours, filtering, gained filter cake by
Deionized water is washed away, and reduced vacuum is dried, and gradient sublimation purifies to obtain fine work.
The compound, molecular formula C are recognized using DEI-MS39F15N9S3, detected value [M+1]+=975.99, calculated value
975.65。
The synthesis of the compound 2 of embodiment 2
Replace 2- (4- with 2- (4- (2,3,5,6- tetra- fluoro- 4- (trifluoromethyl) phenyl) thiazole -2 (5H)-subunit) malononitrile
(perfluor) thiazole -2 (5H)-subunit) malononitrile, prepared by the synthetic method of compound 1 in embodiment 1.Known using DEI-MS
The not compound, molecular formula C42F21N9S3, detected value [M+1]+=1126.37, calculated value 1125.67.
The synthesis of the compound 3 of embodiment 3
Replace 2- (4- (perfluor) with 2- (4- (4- cyano group -2,3,5,6- tetrafluoros phenyl) thiazole -2 (5H)-subunit) malononitrile
Thiazole -2 (5H)-subunit) malononitrile, prepared by the synthetic method of compound 1 in embodiment 1.The change is recognized using DEI-MS
Compound, molecular formula C42F12N12S3, detected value [M+1]+=997.82, calculated value 996.71.
The synthesis of the compound 4 of embodiment 4
Replace 2- (4- (perfluor) with 2- (4- (the fluoro- 4- nitrobenzophenones of 2,3,5,6- tetra-) thiazole -2 (5H)-subunit) malononitrile
Thiazole -2 (5H)-subunit) malononitrile, prepared by the synthetic method of compound 1 in embodiment 1.The change is recognized using DEI-MS
Compound, molecular formula C39F12N12O6S3, detected value [M+1]+=1057.29, calculated value 1056.67.
The synthesis of the compound 5 of embodiment 5
Replace 2- (4- with 2- (4- (the fluoro- 4- isocyanate phenyls of 2,3,5,6- tetra-) thiazole -2 (5H)-subunit) malononitrile
(perfluor) thiazole -2 (5H)-subunit) malononitrile, prepared by the synthetic method of compound 1 in embodiment 1.Known using DEI-MS
The not compound, molecular formula C42F12N12S6, detected value [M+1]+=1093.47, calculated value 1092.90.
The synthesis of the compound 6 of embodiment 6
Replace 2- (4- (perfluor) thiophenes with 2- (4- (the chloro- 2,3,5,6- tetrafluoros phenyl of 4-) thiazole -2 (5H)-subunit) malononitrile
Azoles -2 (5H)-subunit) malononitrile, prepared by the synthetic method of compound 1 in embodiment 1.The chemical combination is recognized using DEI-MS
Thing, molecular formula C39Cl3F12N9S3, detected value [M+1]+=1026.47, calculated value 1025.01.
Device prepares implementation method
Described with reference to Fig. 1.Organic electroluminescence device include transparent substrate layer 1, anode layer 2, hole injection layer 3,
Hole transmission layer 4, luminescent layer 5, electron transfer layer 6, electron injecting layer 7 and cathode layer 8.
In organic electroluminescence device, each layer of the above is from bottom to up according to transparent substrate layer 1, anode layer 2, hole injection layer
3rd, the structural order arrangement of hole transmission layer 4, luminescent layer 5, electron transfer layer 6, electron injecting layer 7 and cathode layer 8.
Make the material work that such electro-luminescence display device can be used all known or futures to be expected to develop
It is the material of each layer, material is made film by each layer by vapour deposition method, spin-coating method or casting method.Thickness is not particularly limited, and leads to
It is often 2nm~5000nm.Furthermore, the method for luminescent material thin-film is readily available uniform film layer and is difficult to generate pin hole
Experience for, preferred vapour deposition method.Evaporation condition is generally preferably in boat, 50 DEG C~400 DEG C of heating-up temperature, vacuum 10-6Pa
~10-3Pa, evaporation rate 0.01nm/s~50nm/s, -150 DEG C of substrate temperature~300 DEG C, thickness 5nm~5um.
Anode layer 2 has the function of injecting holes into hole transmission layer 4, and anode layer 2 is generally constituted by the following substances：Such as
The metals such as aluminium, gold, silver, nickel, palladium or platinum；Such as indium oxide, tin oxide, zinc oxide, indium tin composite oxides, indium zinc composite oxide
Deng metal oxide；Such as cupric iodide metal halide；Carbon black；Or partially electronically conductive macromolecule etc..
Hole injection layer 3 is used to promote hole to be injected into luminescent layer 5 by anode layer 2, and device architecture of the invention is empty
Cave implanted layer 3 can be used the oled light electric material provided by host material and the present invention to be formed.Wherein, host material is selected from phthalocyanine
Copper complex (CuPc), 4,4’, 4 " ,-three (N-3- tolyls-N- phenyl-amido) triphenylamines (m-MTDATA), 4,4 ', 4 " ,-
Three (N- (2- naphthyls)-N- phenyl-amido) triphenylamines (2-TNATA), N, N, N ', N '-four (4- methoxyl groups-phenyl) benzidine
(MeO-TPD), (2,2 ' 7,7 '-four-(N, N- diphenylamines) -9,9- spiral shells two fluorenes (spiral shell-TTB), three (terphenyl -4- bases) amine, N,
One kind in N '-diphenyl-N, N '-(1- naphthyls) -1,1 '-biphenyl -4,4 '-diamines (NPB).
Hole transmission layer 4 is the high efficiency from the injection of anode layer 2 hole and can effectively transmit injected holes material
Material.Accordingly, it would be desirable to the ionization potential of the material is low, high to the permeability of visible ray, hole mobility is high, stable in properties, in addition it is also necessary to
The light being not likely to produce when preparing or using turns into the impurity of trap (trap).It is in contact, it is necessary to hole additionally, due to luminescent layer 5
Transport layer 4 does not make to carry out the light delustring of light emitting layer 5, and forms exciplex not between luminescent layer 5 and reduce efficiency, common
Hole mobile material can enumerate with N, N '-diphenyl-N, N '-(1- naphthyls) -1,1 '-biphenyl -4,4 '-diamines (NPB) is
The aromatic diamine containing more than two tertiary amines of representative, triphen amine have the aromatic amine chemical combination of star radial configuration
Thing, carbazole analog derivative etc..
Luminescent layer 5 is formed by luminescent substance, wherein, between the electrode for being applied with electric field, this luminescent substance is because of hole
With electronics in conjunction with and excite, it is strong luminous so as to show.Usual luminescent layer 5 contains the doping type material as luminescent substance
And host material.In order to obtain high efficiency electroluminescent device, a kind of adoptable dopant material of its luminescent layer 5, or using many
Plant dopant material.Dopant material can be simple fluorescence or phosphor material, or be formed by different fluorescence and phosphorescence matched combined,
Luminescent layer 5 can be single emitting layer material, or the recombination luminescence layer material being superimposed.
The material of main part of luminescent layer 5 not only needs to have ambipolar charge transport quality, while appropriate energy rank is needed,
Excitation energy is efficiently transferred to guest emitting material, the material of this class can enumerate diphenylethyllene aryl derivatives,
Stibene derivative, carbazole derivates, triarylamine derivatives, anthracene derivant, pyrene derivatives, coronene derivative
Deng.
Relative to material of main part, the incorporation weight of guest materials is preferably 0.01%-20%.The material of this class can be lifted
Go out the metal complexs such as iridium, nail, platinum, rhenium, palladium.
The material of the electron transfer layer 6 of above-mentioned electroluminescent device is constituted, can be by the electroluminescent hair that possesses electronic transport property
Selection is arbitrarily used in luminescent material, such material can enumerate such as 1,3,5- tri- (1- naphthyl -1H- benzimidazolyl-2 radicals -
Base) benzimidazoles derivative, three (8-hydroxyquinoline) aluminium (Alq such as benzene (TPBI)3) etc. metal complex, 2- (4 ' -2-methyl-2-phenylpropanes
Base) -5- (4 '-xenyl) -1,3,4- oxadiazoles (PBD) Deng oxadiazole derivatives, 4,7- diphenyl -1,10- ferrosins
(BPhen) the phenanthroline derivative such as, triazole derivative, quinoline, quinoxaline derivant etc..
The usable material of cathode layer 8 of above-mentioned electroluminescent device can select metal of the work function less than 4eV, alloy, lead
Conductive compounds and their mixture.Its concrete example is aluminium, calcium, magnesium, lithium, magnesium alloy, aluminium alloy etc..In order to efficiently obtain
Electroluminescence is taken, the transmitance of at least one of electrode is preferably set to more than 10%.Cathode layer 8 can be by dry
Method such as vacuum evaporation, vapour deposition or sputtering are formed.
Device embodiments and device comparative example
It is material to describe compound provided by the present invention in detail by device embodiments 1-6 and comparative example 1 and 2, is prepared
Electroluminescent device and its effect that the present invention is provided.Wherein, the compound that device embodiments 1-6 is provided using the present invention is used as sky
Cave implanted layer p-type dopant material, and its advantage is proved with comparative example 1 and 2.
Further, since the method provided according to device embodiments 1, is hole injection from the compound that the present invention is provided
The p-type dopant material of layer, you can prepare, so summary.
Device embodiments 1
With reference to the preparation method and Figure of description of device, and the compound provided from the present invention is used as hole injection layer
Dopant material, prominent its application and effect in organic electroluminescence device hole injection layer.
A) anode layer 2 on cleaning transparent substrate layer 1：Each 15 points are cleaned with deionized water, acetone, EtOH Sonicate respectively
Clock, is then processed 2 minutes in plasma cleaner；
B) the co-evaporation hole injection layer 3 on anode layer 2, NPB as host material, prepared by the embodiment of the present invention 1
, used as dopant material, doping is than being 5% (weight of compound 1 accounts for the 5% of compound 1 and NPB gross weights), thickness for compound 1
It is 30nm；
C) on hole injection layer 3, TCTA is deposited with by vacuum evaporation mode, its thickness is 10nm, this layer of organic material
Material is used as hole transmission layer 4.
D) the co-evaporation luminescent layer 5 on hole transmission layer 4, CBP is used as material of main part, Ir (ppy)3Mixed as phosphorescence
Miscellaneous material, phosphor material doping ratio is 5% (quality of phosphor material accounts for the 5% of phosphor material and material of main part gross weight),
Thickness is 30nm；
E) on the compound of doping type luminescent layer 5, compound-material Alq is deposited with by vacuum evaporation mode3, thickness is
30nm, this layer of organic material is used as electron transfer layer 6；
F) on electron transfer layer 6, vacuum evaporation electron injecting layer LiF, thickness is 0.5nm, and the layer is electron injection
Layer 7；
G) on electron injecting layer 7, Al layers of vacuum evaporation negative electrode, thickness is 100nm, and the layer is cathode layer 8.
After completing organic electroluminescence device, the driving voltage of measurement device, quantum efficiency, current efficiency, power efficiency
And brightness, its result is in table 1.
Device embodiments 2
The present embodiment is with the difference of device embodiments 1：Hole injection layer mixes in organic electroluminescence device
Miscellaneous material is changed into the compound 2 of the preparation of the embodiment of the present invention 2, as a result in table 1.
Device embodiments 3
The present embodiment is with the difference of device embodiments 1：Hole injection layer mixes in organic electroluminescence device
Miscellaneous material is changed into the compound 3 of the preparation of the embodiment of the present invention 3, is as a result displayed in table 1.
Device embodiments 4
The present embodiment is with the difference of device embodiments 1：Hole injection layer mixes in organic electroluminescence device
Miscellaneous material is changed into the compound 4 of the preparation of the embodiment of the present invention 4, as a result in table 1.
Device embodiments 5
The present embodiment is with the difference of device embodiments 1：Hole injection layer mixes in organic electroluminescence device
Miscellaneous material is changed into the compound 5 of the preparation of the embodiment of the present invention 5, as a result in table 1.
Device embodiments 6
The present embodiment is with the difference of device embodiments 1：Hole injection layer mixes in organic electroluminescence device
The compound 6 that miscellaneous material is changed into the preparation of the embodiment of the present invention 6 is material, as a result in table 1.
Device comparative example 1
Unlike device comparative example 1 and device embodiments 1：The hole injection layer 3 of organic electroluminescence device only has NPB
Used as hole-injecting material, any dopant that undopes makes hole injection layer.
Device comparative example 2
Unlike device comparative example 1 and device embodiments 1：The hole injection layer 3 of organic electroluminescence device is made with NPB
It is host material, the F of doping 5%4TCNQ, hole injection layer is made instead of the compounds of this invention.
The result of the organic electroluminescence device made by device comparative example 1 and 2 is in table 1.
Table 1
From the point of view of result by table 1, photoelectric material of the present invention is applied to electroluminescent device making, obtains good table
Existing, material of the present invention is used as the hole injection layer p-type dopant material of electroluminescent device, either efficiency, brightness
It is obviously improved than known electroluminescent materials with driving voltage, the driving voltage of particularly device is greatly reduced.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all it is of the invention spirit and
Within principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.
Claims (4)
1. a kind of oled light electric material, it is characterised in that structure is selected from one of having structure：
2. a kind of application of oled light electric material, it is characterised in that in organic electroluminescence device, at least one function
Layer, contains the oled light electric material described in claim 1.
3. a kind of organic electroluminescence device, it is characterised in that including：Luminescent layer between anode layer and cathode layer, Yi Jisuo
The hole injection layer between anode layer and the luminescent layer is stated, wherein, the hole injection layer is by host material and dopant group
It is the oled light electric material described in claim 1 into, the dopant, the mol ratio of the host material and dopant is 1:1-
100000：1.
4. organic electroluminescence device according to claim 3, it is characterised in that the host material is selected from CuPc network
Compound, 4,4 ', 4 " ,-three (N-3- tolyls-N- phenyl-amido) triphenylamines, 4,4 ', 4 " ,-three (N- (2- naphthyls)-N- phenyl-
Amido) triphenylamine, N, N, N ', N '-four (4- methoxyl groups-phenyl) benzidine, (2,2 ' 7,7 '-four-(N, N- diphenylamines) -9,9-
The fluorenes of spiral shell two, three (terphenyl -4- bases) amine, N, appointing in N '-diphenyl-N, N '-(1- naphthyls) -1,1 '-biphenyl -4,4 '-diamines
Anticipate one or more；The dopant is the oled light electric material described in claim 1.
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