CN110172275A - Electron transfer layer ink and preparation method thereof, electroluminescent device - Google Patents
Electron transfer layer ink and preparation method thereof, electroluminescent device Download PDFInfo
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- CN110172275A CN110172275A CN201910426766.9A CN201910426766A CN110172275A CN 110172275 A CN110172275 A CN 110172275A CN 201910426766 A CN201910426766 A CN 201910426766A CN 110172275 A CN110172275 A CN 110172275A
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- transfer layer
- electron transfer
- layer ink
- surface tension
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- 230000027756 respiratory electron transport chain Effects 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 58
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 239000002019 doping agent Substances 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 21
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 21
- 239000012046 mixed solvent Substances 0.000 claims abstract description 19
- 239000003607 modifier Substances 0.000 claims abstract description 19
- -1 4- tert-butyl-phenyl Chemical group 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- 229960003540 oxyquinoline Drugs 0.000 claims description 7
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- AZQJQRTZFPAGNV-UHFFFAOYSA-N 1-phenylindazole Chemical class C12=CC=CC=C2C=NN1C1=CC=CC=C1 AZQJQRTZFPAGNV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 150000003384 small molecules Chemical class 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 8
- 230000005540 biological transmission Effects 0.000 abstract description 7
- 238000007639 printing Methods 0.000 abstract description 3
- 239000000976 ink Substances 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000006184 cosolvent Substances 0.000 description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960003968 sodium apolate Drugs 0.000 description 2
- 229920002351 sodium apolate Polymers 0.000 description 2
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000003913 materials processing Methods 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229950006451 sorbitan laurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention discloses a kind of electron transfer layer inks and preparation method thereof, electroluminescent device, electron transfer layer ink, and component content percentage by weight includes organic Micromolecule electron transmission material, 0.5wt%-30wt%；Alkali metal complex dopant material, 0.1wt%-5wt%；Surface tension modifier, 0.1wt%-5wt%；Viscosity-controlling agent, 0.1wt%-5wt%；Polarized mixed solvent, 69wt%-99wt%；Secondary solvent, 0.1wt%-30wt%.Electron transfer layer ink of the invention and preparation method thereof, electroluminescent device, preparation-obtained electron transfer layer ink, electron transfer layer ink can be formed in electron transfer layer by printing technology, while can be avoided the solvent damage lower layer luminescent layer in electron transfer layer ink.
Description
Technical field
The present invention relates to fields such as displays, specially a kind of electron transfer layer ink and preparation method thereof, electroluminescent
Device.
Background technique
Self-luminous that organic electroluminescent LED (OLED) has with its own, high comparison, wide colour gamut, big visual angle,
A series of outstanding advantages such as Flexible Displays can be achieved in fast response time, and are considered as most potential next-generation novel flat-plate
Display technology.The OLED product being commercialized at present is mainly to be prepared by high vacuum thermal evaporation deposition, there is and sets
The disadvantages of standby and complex process, energy consumption are high, waste of material is big, at high cost.
Typographical display technology prepares high performance OLED product for low cost and provides an effective approach.Wherein ink-jet
Printing technique greatly improves material by drop by drop instilling the configured ink containing functional material in pixel hole
Expect utilization rate.And high-vacuum equipment is not needed, cost can be effectively reduced, there is pole in terms of preparing large scale oled panel
Big advantage.Meanwhile inkjet printing technology can be used for preparing quantum dot electroluminescent diode (QLED), remove luminescent material
Outside for quanta point material, other materials processing procedure and inkjet printing OLED making technology have very high compatibility.
In inkjet printing OLED device structure common at present, hole injection layer, hole transmission layer and luminescent layer have been realized
Processing procedure is printed, but electron transfer layer and cathode are still vapor deposition processing procedure.This is because most of electron transport layer materials are organic molten
The material of agent dissolution after being configured to ink, is easy the presence of phenomenon of dissolving each other between luminescent layer, leads to the device system of whole soln processing procedure
It is standby to have difficulties.To realize whole soln processing procedure, need to develop the organic electron transport layer ink for not damaging luminescent layer.
Summary of the invention
To solve above-mentioned technical problem: the present invention provides a kind of electron transfer layer ink and preparation method thereof, electroluminescent
Electron transfer layer ink can be formed in electronics by printing technology and passed by device, preparation-obtained electron transfer layer ink
In defeated layer, while it can be avoided the solvent damage lower layer luminescent layer in electron transfer layer ink.
The technical solution to solve the above problems is: the present invention provides a kind of electron transfer layer ink, and component contains by weight
Measuring percentage includes organic Micromolecule electron transmission material, 0.5wt%-30wt%；Alkali metal complex dopant material,
0.1wt%-5wt%；Surface tension modifier, 0.1wt%-5wt%；Viscosity-controlling agent, 0.1wt%-5wt%；Polarity mixing
Solvent, 69wt%-99wt%；Secondary solvent, 0.1wt%-30wt%.
In an embodiment of the present invention, the electron transfer layer ink, viscosity 1cps-100cps；Its surface
Power is 20dyne/cm-60dyne/cm.
In an embodiment of the present invention, the small organic molecule electron transport material includes 1,3,5- tri- (1- phenyl-benzo
[D] pyrazoles -2- base) benzene, 2,2'- (1,3- phenyl) two [5- (4- tert-butyl-phenyl) -1,3,4- oxadiazoles], three [2,4,6- tri-
Methyl -3- (3- pyridyl group) phenyl] borine, 3,3'- [5'- [3- (3- pyridyl group) base] [1,1':3', 1 "-terphenyl] -3,3 " -
Diyl] two pyridines, at least one of bis- two fluorenes of (two phenenyl phosphinyl) -9,9'- spiral shell of 2,7-.
In an embodiment of the present invention, the alkali metal complex dopant material includes that 8-hydroxyquinoline closes lithium.
In an embodiment of the present invention, the surface tension modifier includes cosolvent, surfactant, adjusts surface
At least one of small molecule compound of power；The small molecule compound for adjusting surface tension includes imidazoles and its derivative
At least one of object, phenol, hydroquinone.
In an embodiment of the present invention, the viscosity-controlling agent includes alcohol, ether, ester, phenol, at least one in aminated compounds
Kind.
In an embodiment of the present invention, the polarized mixed solvent is multicomponent alcoholics compound.
In an embodiment of the present invention, the secondary solvent is alcohols, in ketone, ethers, esters, amides compound
It is a kind of.
The present invention also provides a kind of preparation methods, to prepare the electron transfer layer ink, comprising the following steps:
The each component of the content percentage acquisition electron transfer layer ink by weight；By the small organic molecule electron-transport material
Material, the alkali metal complex dopant material are dissolved in the polarized mixed solvent and are uniformly mixed；The surface tension is added
Regulator and the viscosity-controlling agent, in the case where temperature is 0 DEG C -80 DEG C, stirring -24 hours 0.5 hour until be completely dissolved；Filtering
Obtain electron transfer layer ink.
The present invention also provides a kind of electroluminescent device, the electron transfer layer formed by print process, material therefor
For electron transfer layer ink as described in claim 1.
The beneficial effects of the present invention are: electron transfer layer ink of the invention, uses small organic molecule electron-transport material
Material is used as primary electron transmission material, and alkali metal complex such as 8-hydroxyquinoline closes lithium (Liq) and is used as dopant material, can be effective
Enhancing electron injection and transmittability, polyalcohols solvent can effectively inhibit lower layer as polarized mixed solvent (main solvent)
Luminescent layer is destroyed；Alcohols, ethers, ketone, esters and amides can effectively dissolve organic electronic transmission as secondary solvent
And dopant material can adjust the viscosity and surface tension of electron transfer layer ink by adjusting each solvent composition ratio.This hair
Bright electron transfer layer ink preparation method is simple, only needs at a certain temperature, electron transfer layer ink to be mixed equal
It is even.This ink can be used as the electron transfer layer of electroluminescent device of giving out light, and can avoid the solvent damage in electron transfer layer ink
Lower layer's luminescent layer is advantageously implemented the requirement that device is formed under full stress-strain printing process.
Detailed description of the invention
The present invention is further explained with reference to the accompanying drawings and examples.
Fig. 1 is the structural schematic diagram of the electroluminescent device of giving out light of the embodiment of the present invention.
Appended drawing reference:
1 electroluminescent device of giving out light；
11 anodes；12 hole injection layers；
13 hole transmission layers；14 luminescent layers；
15 electron transfer layers；16 electron injecting layers；
17 cathodes.
Specific embodiment
Below in conjunction with Figure of description, the preferred embodiments of the present invention are described in detail, with complete to those of skill in the art
It is whole to introduce technology contents of the invention, prove that the present invention can be implemented with citing, so that technology contents disclosed by the invention are more
It is clear, so that will more readily understand how implement the present invention by those skilled in the art.However the present invention can pass through many differences
The embodiment of form emerges from, and protection scope of the present invention is not limited only to the embodiment mentioned in text, Examples below
The range that is not intended to limit the invention of explanation.
The explanation of following embodiment is to can be used to the particular implementation of implementation to illustrate the present invention with reference to additional schema
Example.Direction term that the present invention is previously mentioned, such as "upper", "lower", "front", "rear", "left", "right", "top", "bottom" etc. are only
With reference to the direction of annexed drawings.Therefore, the direction term used is to illustrate and understand the present invention, rather than to limit this hair
It is bright.
A kind of electron transfer layer ink of the invention, component content percentage by weight include that small organic molecule electronics passes
Defeated material, 0.5wt%-30wt%；Alkali metal complex dopant material, 0.1wt%-5wt%；Surface tension modifier,
0.1wt%-5wt%；Viscosity-controlling agent, 0.1wt%-5wt%；Polarized mixed solvent, 69wt%-99wt%；Secondary solvent,
0.1wt%-30wt%.
The small organic molecule electron transport material includes 1,3,5- tri- (1- phenyl-benzo [D] pyrazoles -2- base) benzene, 2,
2'- (1,3- phenyl) two [5- (4- tert-butyl-phenyl) -1,3,4- oxadiazoles], three [2,4,6- trimethyl -3- (3- pyridyl group) benzene
Base] borine, 3,3'- [5'- [3- (3- pyridyl group) base] [1,1':3', 1 "-terphenyl] -3,3 "-diyl] two pyridines, 2,7- be bis-
At least one of two fluorenes of (two phenenyl phosphinyl) -9,9'- spiral shell.
The alkali metal complex dopant material includes that 8-hydroxyquinoline closes lithium.
The surface tension modifier includes cosolvent, surfactant, adjusts in the small molecule compound of surface tension
At least one；In the present embodiment, the cosolvent can choose hexamethylene, tetrahydrofuran, dimethylformamide；The surface
The mixture of ionic, non-ionic, or both can be selected in activating agent, including fatty acid salt such as stearic acid sodium salt, alkyl
Sulfate, sulfonate such as three sodium apolate of alkylbenzene, sodium alkyl benzene sulfonate, polyoxyethylene propylene glycol stearate, polyoxy
Ethylene shrink sorbitan laurate etc..The small molecule compound for adjusting surface tension includes imidazole and its derivants, benzene
At least one of phenol, hydroquinone.The viscosity-controlling agent includes at least one of alcohol, ether, ester, phenol, aminated compounds.
The polarized mixed solvent is multicomponent alcoholics compound, selects ethylene glycol in the present embodiment.The secondary solvent is alcohols, ketone
One of class, ethers, esters, amides compound.
Embodiment 1
Electron transfer layer ink of the invention, component content percentage by weight include small organic molecule electron-transport material
Material, 30wt%；Alkali metal complex dopant material, 0.1wt%；Surface tension modifier, 0.1wt%；Viscosity-controlling agent,
0.1wt%；Polarized mixed solvent, 69wt%；Secondary solvent, 0.7wt%.
Small organic molecule electron transport material selection 2,2'- (1,3- phenyl) two [5- (4- tert-butyl-phenyl) -1,3,
4- oxadiazoles].The alkali metal complex dopant material is that 8-hydroxyquinoline closes lithium.Two are selected in the surface tension modifier
Methylformamide is small as adjusting surface tension as surfactant, hydroquinone as cosolvent, sodium alkyl benzene sulfonate
Molecular compound；
The viscosity-controlling agent selects aminated compounds.The polarized mixed solvent is multicomponent alcoholics compound, this implementation
Ethylene glycol is selected in example.The secondary solvent selects amides compound.
A kind of preparation method is additionally provided in the present embodiment, preparing the electron transfer layer ink, including it is following
Step: content percentage obtains small organic molecule electron transport material, 30wt% by weight；Alkali metal complex dopant material,
0.1wt%；Surface tension modifier, 0.1wt%；Viscosity-controlling agent, 0.1wt%；Polarized mixed solvent, 69wt%；It assists molten
Agent, 0.7wt%.Small organic molecule electron transport material, alkali metal complex dopant material are dissolved in polarized mixed solvent
It is uniformly mixed；Surface tension modifier and viscosity-controlling agent is added, in the case where temperature is 0 DEG C -80 DEG C, stirs -24 hours 0.5 hour
Until being completely dissolved；Filtering obtains electron transfer layer ink.
Embodiment 2
Electron transfer layer ink of the invention, component content percentage by weight include small organic molecule electron-transport material
Material, 10wt%；Alkali metal complex dopant material, 2wt%；Surface tension modifier, 2wt%；Viscosity-controlling agent, 2wt%；Pole
Property mixed solvent, 80wt%；Secondary solvent, 4wt%.
The small organic molecule electron transport material selects 1,3,5- tri- (1- phenyl-benzo [D] pyrazoles -2- base) benzene.Institute
Stating alkali metal complex dopant material is that 8-hydroxyquinoline closes lithium.
Select hexamethylene as cosolvent, three sodium apolate of alkylbenzene as surface in the surface tension modifier
Activating agent, imidazole and its derivants are the small molecule compound for adjusting surface tension.
The viscosity-controlling agent selects ether compound.The polarized mixed solvent is multicomponent alcoholics compound, this implementation
Ethylene glycol is selected in example.The secondary solvent selects ether compound.
A kind of preparation method is additionally provided in the present embodiment, preparing the electron transfer layer ink, including it is following
Step: content percentage obtains small organic molecule electron transport material, 10wt% by weight；Alkali metal complex dopant material,
2wt%；Surface tension modifier, 2wt%；Viscosity-controlling agent, 2wt%；Polarized mixed solvent, 80wt%；Secondary solvent,
4wt%.Small organic molecule electron transport material, alkali metal complex dopant material are dissolved in polarized mixed solvent and mixed
It is even；Surface tension modifier and viscosity-controlling agent is added, in the case where temperature is 0 DEG C -80 DEG C, stirring -24 hours 0.5 hour until complete
Fully dissolved；Filtering obtains electron transfer layer ink.
Embodiment 3
Electron transfer layer ink of the invention, component content percentage by weight include small organic molecule electron-transport material
Material, 5wt%；Alkali metal complex dopant material, 5wt%；Surface tension modifier, 5wt%；Viscosity-controlling agent, 5wt%；Pole
Property mixed solvent, 69wt%；Secondary solvent, 11wt%.
Small organic molecule electron transport material selection 2,2'- (1,3- phenyl) two [5- (4- tert-butyl-phenyl) -1,3,
4- oxadiazoles].The alkali metal complex dopant material is that 8-hydroxyquinoline closes lithium.Two are selected in the surface tension modifier
Methylformamide is small as adjusting surface tension as surfactant, hydroquinone as cosolvent, sodium alkyl benzene sulfonate
Molecular compound；
The viscosity-controlling agent selects aminated compounds.The polarized mixed solvent is multicomponent alcoholics compound, this implementation
Ethylene glycol is selected in example.The secondary solvent selects amides compound.
After testing, the electron transfer layer ink that the embodiment of the present invention 1 to embodiment 3 is prepared,
Viscosity is 1cps-100cps；Its surface tension is 20dyne/cm-60dyne/cm.
A kind of preparation method is additionally provided in the present embodiment, preparing the electron transfer layer ink, including it is following
Step: content percentage obtains small organic molecule electron transport material, 5wt% by weight；Alkali metal complex dopant material,
5wt%；Surface tension modifier, 5wt%；Viscosity-controlling agent, 5wt%；Polarized mixed solvent, 69wt%；Secondary solvent,
11wt%.Small organic molecule electron transport material, alkali metal complex dopant material are dissolved in polarized mixed solvent and are mixed
Uniformly；Surface tension modifier and viscosity-controlling agent is added, in the case where temperature is 0 DEG C -80 DEG C, stirring -24 hours 0.5 hour until
It is completely dissolved；Filtering obtains electron transfer layer ink.
As shown in Figure 1, successively level is provided with anode 11, hole the present invention also provides a kind of electroluminescent device 1
Implanted layer 12, hole transmission layer 13, luminescent layer 14, electron transfer layer 15, electron injecting layer 16, cathode 17.Wherein, the electronics
Transport layer 15 is formed by print process, i.e., is printed the electron transfer layer ink of the invention to the hair by print process
The electron transfer layer 15 is formed on photosphere.
The above is merely preferred embodiments of the present invention, it should be appreciated that illustrative embodiments as described herein should only by
It is considered descriptive, is used to help understand method and its core concept of the invention, and is not intended to restrict the invention.Every
The class suitable for other exemplary embodiments should be usually considered to the description of features or aspect in a illustrative embodiments
Like features or aspect.Although reference example embodiment describes the present invention, it can suggest those skilled in the art's progress
Various change and change.The invention is intended to cover these variations and change in the scope of the appended claims.
Claims (10)
1. a kind of electron transfer layer ink, which is characterized in that its component content percentage by weight includes
2. electron transfer layer ink according to claim 1, which is characterized in that the viscosity of the electron transfer layer ink is
1cps-100cps；The surface tension of the electron transfer layer ink is 20dyne/cm-60dyne/cm.
3. according to right want 1 described in electron transfer layer ink, which is characterized in that the small organic molecule electron transport material packet
Include 1,3,5- tri- (1- phenyl-benzo [D] pyrazoles -2- base) benzene, 2,2'- (1,3- phenyl) two [5- (4- tert-butyl-phenyl) -1,3,
4- oxadiazoles], three [2,4,6- trimethyl -3- (3- pyridyl group) phenyl] borines, 3,3'- [5'- [3- (3- pyridyl group) phenyl]
[1,1':3', 1 "-terphenyl] -3,3 "-diyl] two pyridines, in bis- two fluorenes of (two phenenyl phosphinyl) -9,9'- spiral shell of 2,7- at least
It is a kind of.
4. electron transfer layer ink according to claim 1, which is characterized in that the alkali metal complex dopant material packet
It includes 8-hydroxyquinoline and closes lithium.
5. electron transfer layer ink according to claim 1, which is characterized in that the surface tension modifier includes molten altogether
At least one of agent, surfactant, the small molecule compound for adjusting surface tension；The small molecule for adjusting surface tension
Compound includes at least one of imidazole and its derivants, phenol, hydroquinone.
6. electron transfer layer ink according to claim 1, which is characterized in that the viscosity-controlling agent include alcohol, ether,
At least one of ester, phenol, aminated compounds.
7. electron transfer layer ink according to claim 1, which is characterized in that the polarized mixed solvent is polyalcohols
Compound.
8. electron transfer layer ink according to claim 1, which is characterized in that the secondary solvent is alcohols, ketone, ether
One of class, esters, amides compound.
9. a kind of preparation method, to prepare electron transfer layer ink as described in claim 1, which is characterized in that including with
Lower step:
The content percentage each component that obtains electron transfer layer ink as described in claim 1 by weight；
It is molten that the small organic molecule electron transport material, the alkali metal complex dopant material are dissolved in the polarity mixing
It is uniformly mixed in agent；
The surface tension modifier and the viscosity-controlling agent is added, in the case where temperature is 0 DEG C -80 DEG C, stirs 0.5 hour -24
Hour is until be completely dissolved；
Filtering obtains the electron transfer layer ink.
10. a kind of electroluminescent device, which is characterized in that including the electron transfer layer formed by print process, material therefor
For electron transfer layer ink as described in claim 1.
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| CN201910426766.9A CN110172275A (en) | 2019-05-22 | 2019-05-22 | Electron transfer layer ink and preparation method thereof, electroluminescent device |
| PCT/CN2019/090613 WO2020232769A1 (en) | 2019-05-22 | 2019-06-11 | Electron transport layer ink, manufacturing method therefor, and electroluminescent component |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111876022A (en) * | 2019-09-24 | 2020-11-03 | 广东聚华印刷显示技术有限公司 | Composite ink, preparation method thereof and electroluminescent device |
| CN112300631A (en) * | 2020-11-06 | 2021-02-02 | 广东聚华印刷显示技术有限公司 | Ink for ink-jet printing, preparation method thereof and light-emitting device |
| CN112420937A (en) * | 2020-11-26 | 2021-02-26 | 合肥福纳科技有限公司 | Use of organic molecules for preparing solid films with improved thermal stability |
| CN114058206A (en) * | 2020-11-04 | 2022-02-18 | 广东聚华印刷显示技术有限公司 | Electron transport layer ink and light emitting device |
| CN116355460A (en) * | 2021-12-27 | 2023-06-30 | 广东聚华印刷显示技术有限公司 | Composite solution, preparation method thereof and electroluminescent device |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116376360B (en) * | 2023-05-24 | 2023-08-11 | 南京邮电大学 | A kind of electronic transmission material ink and application thereof for inkjet printing |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101331625A (en) * | 2005-10-28 | 2008-12-24 | 日产化学工业株式会社 | Charge-transporting varnish for spray or inkjet application |
| CN106575717A (en) * | 2014-05-30 | 2017-04-19 | 欧司朗Oled股份有限公司 | Organic optoelectronic component and method for producing same |
| CN107210364A (en) * | 2015-01-19 | 2017-09-26 | 西门子公司 | Amino phosphazene base is used as the n-type dopant in organic electronic product |
| CN107706318A (en) * | 2017-10-16 | 2018-02-16 | 深圳市华星光电半导体显示技术有限公司 | Electron transfer layer ink-jet printing ink and preparation method thereof |
| CN108003196A (en) * | 2012-07-19 | 2018-05-08 | Udc 爱尔兰有限责任公司 | Dual-nuclei structure model containing carbene ligands and its purposes in OLED |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103346259B (en) * | 2013-07-01 | 2016-01-20 | 苏州大学 | A kind of organic solar batteries |
| CN107623076B (en) * | 2017-09-29 | 2019-12-06 | 深圳市华星光电半导体显示技术有限公司 | All-solution OLED device and its manufacturing method |
| CN108963087A (en) * | 2017-11-29 | 2018-12-07 | 广东聚华印刷显示技术有限公司 | Quanta point electroluminescent device and display |
| CN109326743B (en) * | 2018-09-20 | 2020-09-01 | 苏州大学 | A kind of preparation method of light-emitting diode based on nano-tungsten bronze |
| CN109599508B (en) * | 2018-12-17 | 2021-03-30 | 嘉兴纳鼎光电科技有限公司 | Electroluminescent device and preparation method thereof |
| CN109825129A (en) * | 2019-02-25 | 2019-05-31 | 深圳市华星光电半导体显示技术有限公司 | Electron transfer layer ink and its preparation method |
-
2019
- 2019-05-22 CN CN201910426766.9A patent/CN110172275A/en active Pending
- 2019-06-11 WO PCT/CN2019/090613 patent/WO2020232769A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101331625A (en) * | 2005-10-28 | 2008-12-24 | 日产化学工业株式会社 | Charge-transporting varnish for spray or inkjet application |
| CN108003196A (en) * | 2012-07-19 | 2018-05-08 | Udc 爱尔兰有限责任公司 | Dual-nuclei structure model containing carbene ligands and its purposes in OLED |
| CN106575717A (en) * | 2014-05-30 | 2017-04-19 | 欧司朗Oled股份有限公司 | Organic optoelectronic component and method for producing same |
| CN107210364A (en) * | 2015-01-19 | 2017-09-26 | 西门子公司 | Amino phosphazene base is used as the n-type dopant in organic electronic product |
| CN107706318A (en) * | 2017-10-16 | 2018-02-16 | 深圳市华星光电半导体显示技术有限公司 | Electron transfer layer ink-jet printing ink and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 侯建华: "《顶发射有机电致发光器件》", 31 December 2017 * |
| 陶友田等: "《高效有机电致磷光双极主体材料的合成与性能》", 31 May 2015 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111876022A (en) * | 2019-09-24 | 2020-11-03 | 广东聚华印刷显示技术有限公司 | Composite ink, preparation method thereof and electroluminescent device |
| CN114058206A (en) * | 2020-11-04 | 2022-02-18 | 广东聚华印刷显示技术有限公司 | Electron transport layer ink and light emitting device |
| CN112300631A (en) * | 2020-11-06 | 2021-02-02 | 广东聚华印刷显示技术有限公司 | Ink for ink-jet printing, preparation method thereof and light-emitting device |
| CN112420937A (en) * | 2020-11-26 | 2021-02-26 | 合肥福纳科技有限公司 | Use of organic molecules for preparing solid films with improved thermal stability |
| CN116355460A (en) * | 2021-12-27 | 2023-06-30 | 广东聚华印刷显示技术有限公司 | Composite solution, preparation method thereof and electroluminescent device |
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