CN108963085A - The electron transport material of solution processable and its preparation and application - Google Patents
The electron transport material of solution processable and its preparation and application Download PDFInfo
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- CN108963085A CN108963085A CN201711015884.8A CN201711015884A CN108963085A CN 108963085 A CN108963085 A CN 108963085A CN 201711015884 A CN201711015884 A CN 201711015884A CN 108963085 A CN108963085 A CN 108963085A
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Abstract
The present invention provides a kind of preparation method of the electron transport material of solution processable, include: that carbon 60 is blended in water containing carboxy derivatives, cationic polyelectrolyte, adsorbs carbon 60 in obtained aqueous solution with cationic polyelectrolyte by electrostatic interaction containing the carboxyl on carboxy derivatives；Water-soluble metal nanoparticle is added into the aqueous solution, is adsorbed in water-soluble metal nanoparticle on the cationic polyelectrolyte by electrostatic interaction.The present invention has the property of higher electron mobility using carbon 60, guarantees that carrier effectively transmits；Based on 60 molecular structure containing carboxy derivatives of carbon, it can be made to form micro-nano structure in film forming procedure, promotion uses it as the light extraction efficiency of the electroluminescent device of electron transfer layer；Decayed using the radiation transistion that the local surface plasma resonance effect of adsorption metal nanoparticle accelerates excitation state exciton, can be improved the fluorescence quantum yield for using its electroluminescent device as electron transfer layer.
Description
Technical field
The present invention relates to electron transport materials, electron transport material and its preparation more particularly to a kind of solution processable
And application.
Background technique
Organic Light Emitting Diode total colouring, backlight and in terms of have broad application prospects and by
To the extensive concern of people.Solution processing type Organic Light Emitting Diode based on inkjet printing technology is due to at low cost, appearance
It easily realizes the advantages such as large-area manufacturing and more has been favored by people, but (such as: operating voltage is high, electric current effect for device performance
The problems such as rate is low, and the service life is poor) there are also a certain distance with vapor deposition type Organic Light Emitting Diode, therefore, solution-type organic light emission two
Pole pipe needs to greatly improve in terms of equilbrium carrier injection and transmission to improve device overall performance.
Currently, method maximally efficient in batch production technique is exactly the doped n-type in electron transport material (as main body)
Dopant.Wherein, LiQ is most widely used as N-type dopant.Due to using the evaporation process of codope, in reality
In production process, the fluctuation of evaporation rate will have a direct impact on the doping ratio of the two, to influence the injection and transmission of electronics, drop
The stability of low device performance, properties of product also cannot be guaranteed.
Summary of the invention
Based on this, for the problem of existing solution processing type electroluminescent device performance difference, it is therefore an objective to provide a kind of solution
The electron transport material of processing prepares the electron transfer layer of electroluminescent device with it, is able to ascend the electricity of electroluminescent device
Flow efficiency, light extraction efficiency, fluorescence quantum yield.
The present invention provides a kind of preparation method of the electron transport material of solution processable, includes the following steps:
Carbon 60 is blended in water containing carboxy derivatives, cationic polyelectrolyte, contains carbon 60 in obtained aqueous solution
Carboxyl on carboxy derivatives is adsorbed with cationic polyelectrolyte by electrostatic interaction；
Water-soluble metal nanoparticle is added into the aqueous solution, water-soluble metal nanoparticle is made to pass through electrostatic interaction
Be adsorbed on the cationic polyelectrolyte to get.
In wherein some embodiments, it is described be blended obtained aqueous solution in cationic polyelectrolyte concentration be 0.5~
1wt%.
In wherein some embodiments, the carbon 60 is not more than 8 containing the carbon atom number of chain derived from carboxy derivatives；
The cationic polyelectrolyte is in polyvinylamine, polyvinyl pyridine, the third alkyl dimethyl ammonium chloride of polydiene or polyethyleneimine
It is one or more.
In wherein some embodiments, the carbon 60 is selected from 60 butyrate of carbon, 60 acetic acid of carbon containing carboxy derivatives
One or both of ester.
In wherein some embodiments, the water-soluble metal nanoparticle is selected from water-soluble gold nanoparticles, water solubility
One of Nano silver grain or water-soluble platinum nanoparticle are a variety of.
In wherein some embodiments, the diameter of the water-soluble metal nanoparticle is 5~10nm.
In wherein some embodiments, the water-soluble metal nanoparticle is to be added in colloidal form.
The present invention also provides a kind of electron transport materials of solution processable obtained according to above-mentioned preparation method.
The present invention also provides a kind of electron transport materials of above-mentioned solution processable in the electricity for preparing electroluminescent device
Application in sub- transport layer.
The present invention also provides a kind of electroluminescent device, the electron transport material containing above-mentioned solution processable.
Compared with prior art, the beneficial effect of the embodiment of the present invention is:
Carbon 60 is assembled containing carboxy derivatives, cationic polyelectrolyte, metal nanoparticle based on electrostatic adsorption
Together, have the property of higher electron mobility using carbon 60, guarantee effective transmission of carrier；Meanwhile being based on carbon
60 molecular structures containing carboxy derivatives, enable to the electron transport material of solution processable can be with shape in film forming procedure
At micro-nano structure, promotion uses it as the light extraction efficiency of the electroluminescent device of electron transfer layer；Adsorption can also be utilized
Metal nanoparticle local surface plasma resonance effect accelerate excitation state exciton radiation transistion decaying, can be improved use
Its fluorescence quantum yield as the electroluminescent device of electron transfer layer.
Detailed description of the invention
Fig. 1,2 be respectively the embodiment of the present invention C60 butyrate and PDDA are fitted together by Electrostatic Absorption after again with
The schematic diagram that metal nanoparticle is assembled.
Specific embodiment
Make below in conjunction with preparation method of the specific embodiment to the electron transport material of solution processing of the invention further
Detailed description.The embodiment of the present invention provides a kind of preparation method of the electron transport material of solution processable, including walks as follows
It is rapid:
Carbon 60 is blended in water containing carboxy derivatives, cationic polyelectrolyte, makes carbon in obtained aqueous solution by step 1
60 are adsorbed with cationic polyelectrolyte by electrostatic interaction containing the carboxyl on carboxy derivatives.
It should be understood that be maintained at 0.5-1wt% equal for the concentration that cationic polyelectrolyte in obtained aqueous solution is blended
The effect of the application can be achieved.
It should be understood that the carbon 60 is not more than 8 containing the carbon atom number of chain derived from carboxy derivatives, carbon atom mistake
It may mostly influence whether electron mobility and local surface plasma resonance effect；The cationic polyelectrolyte can be polyethylene
Amine, polyvinyl pyridine, the third alkyl dimethyl ammonium chloride of polydiene or polyethyleneimine.Preferably, the cationic polyelectrolyte is
The third alkyl dimethyl ammonium chloride of polydiene or polyethyleneimine.
It should be understood that the carbon 60 can be 60 butyrate of carbon, 60 acetic acid esters of carbon containing carboxy derivatives.
Water-soluble metal nanoparticle is added into the aqueous solution, passes through water-soluble metal nanoparticle for step 2
Electrostatic interaction be adsorbed on the cationic polyelectrolyte to get.
It should be understood that the water-soluble metal nanoparticle can be water-soluble gold nanoparticles, water-soluble silver nanometer
Particle or water-soluble platinum nanoparticle.
It should be understood that the diameter of the water-soluble metal nanoparticle is 5~10nm.The application water-soluble metal nanometer
The diameter of particle is too small to will affect surface plasma resonance effect, excessive, will increase the surface roughness of later period film.
It should be understood that the water-soluble metal nanoparticle is to be added in colloidal form.
The preparation method of colloidal solution described in the embodiment of the present invention is such as:
The colloidal solution synthesis step of water-soluble gold nanoparticles includes:
(1) it is made into the aqueous solution of chloraurate of 0.25mM/L, 100mL is taken to be heated to boiling；
(2) it is vigorously stirred the citric acid three that the lower mass fraction that 1mL is added to the aqueous solution of chloraurate boiled is 5%
Sodium water solution；
(3) continue in the case of being vigorously stirred heating boil 15min, be cooled to room temperature to get.
It can be seen that solution is that flaxen chlorauric acid solution becomes grey after the addition of sodium citrate, then become
Black then gradually stabilizes to the solution of claret, entire color change process about 3min.
The synthesis of the colloidal solution of above-mentioned water-soluble gold nanoparticles may be implemented in following range: reducing agent is not limited to
White phosphorus, ascorbic acid, tannic acid etc. also can be used in trisodium citrate；The concentration of aqueous solution of chloraurate is 0.2~0.3mM/L；It is described
The mass fraction of reducing agent is 4.5~5.5%；The volume ratio of aqueous solution of chloraurate and reducing agent solution be 100:(0.5~
1.5)。
The colloidal solution synthesis step of water-soluble Ag nanoparticle includes:
(1) 10mg silver nitrate is added in 100mL deionized water, is vigorously stirred 60min；
(2) 30mg trisodium citrate is added into silver nitrate solution obtained by step (1), is vigorously stirred 30min；
(3) mixed solution obtained by step (2) is placed and is irradiated 3 hours in the UV lamp, is vigorously stirred, solution colour has most
It is first it is colourless become faint yellow, finally switch to it is red to get.
The colloidal solution synthesis step of above-mentioned water solubility Ag nanoparticle can be achieved in the following range: every 100mL is gone
The weight that silver nitrate is added in ionized water is 5~15mg；Reducing agent is not limited to trisodium citrate, and white phosphorus, Vitamin C also can be used
Acid, tannic acid etc.；The corresponding quality that reducing agent is added of every 10mg silver nitrate is 25~35mg.
The preparation of the embodiment of the present invention is carried out based on physical absorption, i.e., only passes through electrostatic adsorption spreading out carbon 60
Biology, cationic polyelectrolyte and metal nano ion fit together the compound material of acquisition.
The embodiment of the present invention also provides a kind of electron-transport material of solution processable obtained according to above-mentioned preparation method
Material.
When the electron transport material light of solution processable provided in an embodiment of the present invention is used as electron transfer layer, enable to
The electroluminescent device for having the electron transfer layer has high-fluorescence quantum yield.It is analyzed as follows:
Ability (0.01~0.1cm that carbon 60 efficiently transmits electronics is utilized2/ v.s), also use the spy of carbon 60
Different molecular structure, can be a kind of micro- using being formed in film forming procedure in the later period compared to planar molecule since carbon 60 is in ball-type
Micro-nano structure either has the scattering layer of many microballoons similar to lenticule, and the surface roughness of film forming also will increase, thus
The total reflection of emergent light may be implemented, raising uses it as the light extraction efficiency of the electroluminescent device of electron transfer layer.
Because Electrostatic Absorption metal nanoparticle can generate local surface plasma resonance effect, excitation state can be accelerated
The radiation transistion of exciton is decayed, and fluorescence quantum yield is improved.The mechanism that specific resonance effects occurs are as follows: the table of metal nanoparticle
Face phasmon is collective oscillation of the local in the charge density of metal surface, specifically, when the metal nanoparticle of very little
When by light radiation, the electromagnetic field of oscillation causes the valence electron of metal that resonance oscillations, the electron cloud relative atom of valence electron occurs
Core shifts, and the Coulomb force (being equivalent to restoring force) between atomic nucleus and valence electron forces electronics relative atom core to make oscillation fortune
It is dynamic.In this way, the electron density of superficial layer (about several angstroms) generates phugoid oscillation, and the electron density of internal layer remains unchanged.Gold
The coupling of the oscillation eelctric dipole of the luminescent material radiation transistion of the electromagnetic field and luminescent layer of metal surface phasmon, can accelerate electricity
Excitation state exciton radiation transistion rate in electroluminescence device (such as diode), so that enhancing uses it as the electricity of electron transfer layer
The fluorescence quantum yield of electroluminescence device.
The electron transport material that the embodiment of the present invention also provides a kind of above-mentioned solution processable is preparing electroluminescent cell
Application in the electron transfer layer of part.
The embodiment of the present invention also provides a kind of electroluminescent device, the electron transport material containing above-mentioned solution processable.
Based on the analysis of the electron transport material feature above to solution processable, it is prepared into the electron-transport of electroluminescent device
When layer, based on institute carbon containing 60 efficiently transmitting electronic capability, 60 pairs of the ball-type carbon influences at membrane structure to improve electricity
The light extraction efficiency of electroluminescence device, the resonance effects also generated based on electron transport layer materials and luminescent material, makes electroluminescent
The fluorescence quantum yield of device (such as electroluminescent diode) is promoted.
In wherein some embodiments, the electronics of above-mentioned solution processable contained by the electron transfer layer of electroluminescent device is passed
The concentration of defeated material is 15~25mg/mL；Adjust solvent that the concentration uses can for one of water, methanol, DMF or
It is the mixture dilution of three.
In wherein some embodiments, electron transfer layer with a thickness of 30~40nm.
In order to enable above-described embodiment content is clearer, specific, it is exemplified below:
Embodiment 1
The present embodiment provides a kind of by 60 butyrate of carbon, cationic polyelectrolyte (PDDA) and water-soluble gold nanoparticles
The technical solution of the electron transport material of solution processable is prepared by Electrostatic Absorption.
One, the electron transport material of solution processable and its preparation
(1) the colloidal solution synthesis step of water-soluble gold nanoparticles includes:
The aqueous solution of chloraurate for preparing 0.25mM/L, takes 100mL to be heated to boiling；
It is vigorously stirred the trisodium citrate that the lower mass fraction that 1mL is added to the aqueous solution of chloraurate boiled is 5%
Aqueous solution；
Continue in the case of being vigorously stirred heating boil 15min, be cooled to room temperature to get.
(2) under normal temperature and pressure, C60 butyrate and cationic polyelectrolyte (PDDA) are blended in aqueous solution (PDDA concentration
For 30min in 0.5wt%), inhale the carboxyl of the upper surface of C60 butyrate by electrostatic interaction with cationic polyelectrolyte
It is attached, see Fig. 1；
(3) under normal temperature and pressure, the colloidal solution of dissolubility gold nanoparticle obtained by step (1) is added in step (2), altogether
It mixes to get Fig. 2 is seen.
Two, inversion type electroluminescent device is prepared
(1) base-plate cleaning: deionized water, acetone, washing lotion, deionized water will be passed through with the glass substrate of 150nm ITO
It is cleaned by ultrasonic with five step of isopropanol, every each 10~15min of step, is placed in vacuum drying oven and is dried for standby after cleaning up；
(2) prepared by electron transfer layer:
By the electron transport material H of solution processable2O dilution passes the electronics of solution processable in gained dilution
The concentration of defeated material is 20mg/mL；
By above-mentioned dilution drop on the ITO cleaned up, spin coating forms the film of one layer of about 35nm thickness, adds in nitrogen
100 DEG C of 20min of heat form electron transfer layer；
(3) prepared by luminescent layer: the ITO that spin coating has electron transfer layer being transferred in the glove box full of nitrogen, in its (electricity
Sub- transport layer) (solvent is paraxylene, concentration 15mg/mL by the luminescent layer P-PPV of one layer of 80nm thickness of spin coating above；Solvent
It can be toluene, chlorobenzene)；100 DEG C of 20min are heated in nitrogen；
(4) prepared by hole transmission layer: the hole mobile material CBP of one layer of 30nm thickness, evaporation rate being deposited on the light-emitting layer
ForVacuum degree is 2X10-4Pa forms hole transmission layer；
(5) prepared by hole injection layer: the hole-injecting material MoO of one layer of 10nm thickness being deposited on the hole transport layer3, vapor deposition
Rate isVacuum degree is 2X10-4Pa forms hole injection layer；
(6) prepared by electrode: the Al (can also use Ag, Au) that one layer of 120nm thickness is finally deposited is used as electrode, wherein evaporation rate
Control isVacuum degree is 2X10-4Pa。
Embodiment 2
60 acetic acid esters of carbon, polyethyleneimine and water-soluble silver nanoparticle are inhaled by electrostatic the present embodiment provides a kind of
The technical solution of the electron transport material of attached preparation solution processable.
One, the electron transport material of solution processable and its preparation
(1) the colloidal solution synthesis step of water-soluble silver nanoparticle includes:
10mg silver nitrate is added in 100mL deionized water, 60min is vigorously stirred；
30mg trisodium citrate is added in step gained silver nitrate solution upwards, is vigorously stirred 30min；
Mixed solution obtained by upper step is placed and is irradiated 3 hours in the UV lamp, is vigorously stirred, solution colour has initial nothing
Discoloration be it is faint yellow, finally switch to it is red to get.
(2) under normal temperature and pressure, 60 acetic acid esters of carbon, polyethyleneimine are blended in aqueous solution, and (polyethyleneimine amine concentration is
30min in 1wt%) makees the carboxyl of the upper surface of 60 acetic acid esters of carbon and cationic polyelectrolyte polyethyleneimine by electrostatic
With being adsorbed；
(3) under normal temperature and pressure, the colloidal solution of dissolubility Nano silver grain obtained by step (1) is added in step (2), altogether
It is mixed to get.
Two, inversion type electroluminescent device is prepared
(1) base-plate cleaning: deionized water, acetone, washing lotion, deionized water will be passed through with the glass substrate of 150nm ITO
It is cleaned by ultrasonic with five step of isopropanol, every each 10~15min of step, is placed in vacuum drying oven and is dried for standby after cleaning up；
(2) prepared by electron transfer layer:
By the electron transport material methanol dilution of solution processable, pass the electronics of solution processable in gained dilution
The concentration of defeated material is 25mg/mL；
By above-mentioned dilution drop on the ITO cleaned up, spin coating forms the film of one layer of about 35nm thickness, adds in nitrogen
100 DEG C of 20min of heat form electron transfer layer；
(3) prepared by luminescent layer: the ITO that spin coating has electron transfer layer being transferred in the glove box full of nitrogen, in its (electricity
Sub- transport layer) (solvent is paraxylene, concentration 15mg/mL by the luminescent layer P-PPV of one layer of 80nm thickness of spin coating above；Solvent
It can be toluene, chlorobenzene)；100 DEG C of 20min are heated in nitrogen；
(4) prepared by hole transmission layer: the hole mobile material CBP of one layer of 30nm thickness, evaporation rate being deposited on the light-emitting layer
ForVacuum degree is 2X10-4Pa forms hole transmission layer；
(5) prepared by hole injection layer: the hole-injecting material MoO of one layer of 10nm thickness being deposited on the hole transport layer3, vapor deposition
Rate isVacuum degree is 2X10-4Pa forms hole injection layer；
(6) prepared by electrode: the Ag (can also use Al, Au) that one layer of 120nm thickness is finally deposited is used as electrode, wherein evaporation rate
Control isVacuum degree is 2X10-4Pa。
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
1. a kind of preparation method of the electron transport material of solution processable, which comprises the steps of:
Carbon 60 is blended in water containing carboxy derivatives, cationic polyelectrolyte, carbon 60 in obtained aqueous solution is made to contain carboxyl
Carboxyl on derivative is adsorbed with cationic polyelectrolyte by electrostatic interaction；
Water-soluble metal nanoparticle is added into the aqueous solution, adsorbs water-soluble metal nanoparticle by electrostatic interaction
In on the cationic polyelectrolyte to get.
2. the preparation method of the electron transport material of solution processable according to claim 1, which is characterized in that described total
The concentration of cationic polyelectrolyte is 0.5~1wt% in mixed obtained aqueous solution.
3. the preparation method of the electron transport material of solution processable according to claim 1, which is characterized in that the carbon
60 carbon atom numbers containing chain derived from carboxy derivatives are not more than 8；The cationic polyelectrolyte is selected from polyvinylamine, gathers
One of vinylpyridine, the third alkyl dimethyl ammonium chloride of polydiene or polyethyleneimine are a variety of.
4. the preparation method of the electron transport material of solution processable according to claim 3, which is characterized in that the carbon
60 are selected from one or both of 60 acetic acid esters of 60 butyrate of carbon or carbon containing carboxy derivatives.
5. the preparation method of the electron transport material of solution processable according to claim 1, which is characterized in that the water
Solube metallic nanoparticle in water-soluble gold nanoparticles, water-soluble silver nanoparticle, water-soluble platinum nanoparticle one
Kind is a variety of.
6. the preparation method of the electron transport material of solution processable according to claim 1, which is characterized in that the water
The diameter of solube metallic nanoparticle is 5~10nm.
7. the preparation method of the electron transport material of solution processable according to claim 1, which is characterized in that described
Water-soluble metal nanoparticle is to be added in colloidal form.
8. the electron transport material for the solution processable that the described in any item preparation methods of claim 1 to 7 obtain.
9. the electron transport material of solution processable according to any one of claims 8 is in the electron transfer layer for preparing electroluminescent device
Application.
10. a kind of electroluminescent device, which is characterized in that its electron-transport material for containing solution processable described in claim 8
Material.
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