CN109721598A - Compound, display panel and display device - Google Patents
Compound, display panel and display device Download PDFInfo
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- CN109721598A CN109721598A CN201811634207.9A CN201811634207A CN109721598A CN 109721598 A CN109721598 A CN 109721598A CN 201811634207 A CN201811634207 A CN 201811634207A CN 109721598 A CN109721598 A CN 109721598A
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Abstract
The present invention provides a kind of display panel, the display panel includes organic luminescent device, wherein the organic luminescent device includes anode, hole injection layer, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode, the organic luminescent device further includes the molecular Iy self-assembled layer being arranged between cathode and electron injecting layer, wherein the material of the molecular Iy self-assembled layer is Ar-LmThe compound that-An is indicated, wherein Ar is nitrogenous aromatic heterocycle group, and L is linking group and is selected from aryl or heteroaryl, and m is selected from 0,1 or 2;An is by Ar-LmThe compound that-An is indicated is anchored to the anchoring group of cathode surface.By the way that one layer of molecular Iy self-assembled layer being made of the compound of the present invention is arranged between cathode and electron injecting layer, the interface between cathode and electron injecting layer can be significantly improved, to enhance the binding force between metal electrode (cathode) and electron transfer layer, electron injection degradation phenomenon caused by inhibiting cathode peeling-off, promotes device lifetime.
Description
Technical field
The present invention relates to electroluminescent organic material technical fields, more particularly to a kind of compound of nitrogenous hetero-aromatic ring
And display panel and display device comprising the compound.
Background technique
Organic electroluminescence device (OLED) is as display technology of new generation, and with ultra-thin, self-luminous, visual angle is wide, responds
Fastly, luminous efficiency is high, thermal adaptability is good, simple production process, driving voltage are low, low power consumption and other advantages, is widely used to
The industries such as FPD, Flexible Displays, solid-state lighting and car-mounted display.
In the manufacturing process of existing OLED, it is common practice to one layer of electron transport material or ytterbium doping electricity first be deposited
Sub- transmission material, the connection at metal with organic layer interface is bad, easily causes the stripping of interface organic layer and metal electrode
From causing the difficult of electron injection to increase, so as to cause device lifetime decline.
Summary of the invention
Of the existing technology in order to solve the problems, such as, the present invention provides a kind of compound, and the compound has formula (I) institute
The chemical structure shown:
Wherein, Ar indicates nitrogenous aromatic heterocycle group;
L indicates linking group and is selected from aryl or heteroaryl, and m indicates the number of linking group L and is selected from 0,1 or 2;
An indicates that anchoring group, the anchoring group are used to chemical structure shown in formula (I) being anchored to cathode surface.
The present invention also provides a kind of display panel, the display panel includes organic luminescent device, wherein organic hair
Optical device includes anode, hole injection layer, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode,
It is characterized in that, the organic luminescent device further includes the molecular Iy self-assembled layer being arranged between cathode and electron injecting layer,
Described in molecular Iy self-assembled layer material be compound of the present invention.
In the present invention, by the way that one layer of point being made of the compound of the present invention is arranged between cathode and electron injecting layer
Sub- Iy self-assembled layer can significantly improve the interface between cathode and electron injecting layer, to increase metal electrode (cathode) and electricity
Binding force between sub- transport layer, electron injection degradation phenomenon caused by inhibiting cathode peeling-off, promotes device lifetime.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of existing OLED;
Fig. 2 is the structural schematic diagram of the OLED in one embodiment of the invention;
Fig. 3 is the structural schematic diagram of the OLED in another embodiment of the present invention.
Specific embodiment
Further illustrate that the present invention, these embodiments are only intended to illustrate the present invention below by embodiment and comparative example,
The present invention is not limited to following embodiments.All modifying or equivalently replacing the technical solution of the present invention, without departing from this hair
The range of bright technical solution should all cover within the protection scope of the present invention.
An aspect of of the present present invention provides a kind of compound, and the compound has chemical structure shown in formula (I):
Wherein, Ar indicates nitrogenous aromatic heterocycle group;
L indicates linking group and is selected from aryl or heteroaryl, and m indicates the number of linking group L and is selected from 0,1 or 2;
An indicates anchoring group, improves electron-transport between cathode and electron injecting layer when formula (I) compound is used as
Self-assembled material when, anchoring group is used to chemical structure shown in formula (I) being anchored to cathode surface.
In the present invention, why structure fragment of the nitrogen-containing heterocycle as self assembly is used, is because being adopted in current volume production
Electron transfer layer typically contains the chemical structure of azacyclo-.Have between nitrogenous class heterocycle materials system and adjacent layer more preferable
Level-density parameter.Meanwhile in electron injecting layer, in order to promote electron injection performance and electron transfer efficiency, electron injecting layer
It can be using metal or the material system of 8-hydroxyquinoline lithium and electron transport material doping.Self assembly is carried out using nitrogen-containing heterocycle,
It can make the material system of electron injecting layer and Iy self-assembled layer relatively, compatibility is more preferable, it is not easy to implanted layer and oneself occur
Mutually separation between assembled layers.To not only realize the good combination of Iy self-assembled layer and metallic cathode, while will not be due to
It introduces Iy self-assembled layer and causes to generate between Iy self-assembled layer and electron injecting layer and mutually separate.To which electron injection be better achieved
Energy and electronic transmission performance, and then promote the comprehensive performance of OLED device.
In one embodiment of compound of the present invention, Ar is selected from substituted or unsubstituted azepine aromatic condensed ring base
Group.
In one embodiment of compound of the present invention, Ar is selected from following group:
Wherein, R1Selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, take
Generation or unsubstituted C2-C40 heteroaryl;
# indicates link position.
In an embodiment of compound of the present invention, the anchoring group be selected from sulfydryl, ester group, phosphoryl or
Halogen group elements.
In an embodiment of compound of the present invention, L is selected from phenyl, pyridyl group, naphthalene, anthryl or phenanthryl.
In an embodiment of compound of the present invention, the compound is selected from following compound:
Wherein, R2Selected from hydrogen atom, chlorine atom, fluorine atom, hydroxyl, the alkyl of C1-C20, C1-C20 alkoxy;R3Choosing
From hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-
C40 heteroaryl.
In a specific embodiment of compound of the present invention, the compound is selected from following compound:
Another aspect of the present invention provides a kind of display panel, and the display panel includes organic luminescent device, wherein institute
Stating organic luminescent device includes anode, hole injection layer, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer
And cathode, the organic luminescent device further include the molecular Iy self-assembled layer being arranged between cathode and electron injecting layer, wherein institute
The material for stating molecular Iy self-assembled layer is compound of the present invention.
Electron transport material tool in an embodiment of display panel of the present invention, in the electron transfer layer
Have and is selected from following with the same or similar molecular structure segment of the material of the unimolecule Iy self-assembled layer, the molecular structure segment
Group:
R1Selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, replace or
Unsubstituted C2-C40 heteroaryl;# indicates link position.
One layer is provided in organic luminescent device of the invention, between cathode and electron injecting layer by chemical combination of the invention
The molecular Iy self-assembled layer that object is constituted, since molecular Iy self-assembled layer contains the molecular structure piece similar or identical with electron injecting layer
Section, allows the molecular Iy self-assembled layer to significantly improve the interface between cathode and electron injecting layer, to enhance metal electrode
Binding force between (cathode) and electron transfer layer, electron injection degradation phenomenon caused by inhibiting cathode peeling-off, most
The service life of device is promoted eventually.
In an embodiment of display panel of the present invention, the thickness range of the molecular Iy self-assembled layer is 1-
10nm, preferably 1-5nm.If molecular Iy self-assembled layer is too thick, the effect of generation is simultaneously bad;If too thin, effect is not only resulted in not
It is good, and enforcement difficulty is also increase accordingly.
In an embodiment of display panel of the present invention, the electron transport material in the electron transfer layer is mixed
It is miscellaneous to have thulium or 8-hydroxyquinoline lithium (LiQ).
In an embodiment of display panel of the present invention, the thulium is ytterbium.Metallic ytterbium can
N-type doping is formed with electron transport material, can effectively improve electron mobility.
In an embodiment of display panel of the present invention, the organic luminescent device further includes being arranged in electronics
Hole blocking layer between transport layer and luminescent layer.Layer is stopped by increasing hole, can effectively stop hole to pass through and shine
Layer and reach the interface of electron-transport, electronic barrier layer can effectively stop electronics to pass through luminescent layer and reach hole transport
Interface avoids being quenched for hole resulting from and electronics to a certain extent.
In an embodiment of display panel of the present invention, the organic luminescent device further includes being covered on cathode
On cap.The light extraction efficiency of device not only can be improved in cap, but also cathode can be prevented by gentle by water
The erosion of body, to extend the service life of device.
The present invention also provides a kind of display devices comprising display panel of the present invention.
Embodiment 1
Fig. 2 shows a kind of OLED device structure charts with molecular Iy self-assembled layer of the present invention.The preparation method of the device is such as
It is lower described.
The distilled water of substrate 1, acetone, isopropyl alcohol ultrasonic cleaning of the anode 2 for the ito thin film that film thickness is 100nm will be loaded with
And it is put into oven drying, surface is handled 30 minutes by UV, is then moved in vacuum evaporation chamber.It is 2 × 10 in vacuum degree-6Under Pa
Start that each layer film is deposited, the compound 1 and compound 2 (doping weight ratio is 97:3, similarly hereinafter) that 10nm thickness is deposited form hole
Implanted layer 3 (HIL), the compound 1 that 100nm thickness is then deposited form hole transmission layer 4 (HTL).On the hole transport layer, with change
Dopant material of the object 3 as luminescent layer 5 (EML), material of main part of the compound 4 as luminescent layer 5 are closed, while the doping material is deposited
Material and material of main part form the luminescent layer 5 of 25nm thickness.Then the compound 5 that 10nm thickness is deposited on the light-emitting layer forms electronics and passes
Compound 6 and compound 7 (40:60) is deposited on electron transfer layer 6 then to form the electron injection of 50nm in defeated layer 6 (ETL)
Layer (ETL) 7.One layer of compound 8 is deposited on electron injecting layer 7 (EIL) and forms self-assembled molecule layer 10, in self-assembled molecule layer
The Ag of 100nm thickness is deposited on 10 as cathode 8, the compound 1 that one layer of 70nm thickness is deposited again on 8 surface of cathode forms optics and covers
Cap rock 9 (CPL), so that organic luminescent device be made.The structure of compound used in the device process of this implementation is as follows.
Embodiment 2
Other all preparation steps are all same as Example 1, and different places are, deposit one on electron injecting layer 7
Layer forms self-assembled molecule layer by compound 9.
Comparative example 1
Prepare it is same as Example 1, the difference is that not preparing self-assembled molecule layer.
The test of 1 device performance of table
As it can be seen from table 1 including having for molecular Iy self-assembled layer of the invention relative to the luminescent device in comparative example 1
The service life of machine luminescent device significantly extends.Other performances and comparative example 1 are quite or better than comparative example 1.Its main cause exists
In: in organic luminescent device of the invention, provided with one layer by the compound of the present invention structure between cathode and electron injecting layer
At molecular Iy self-assembled layer, since molecular Iy self-assembled layer contains the molecular structure segment similar or identical with electron injecting layer, make
The interface between cathode and electron injecting layer can be significantly improved by obtaining the molecular Iy self-assembled layer, to enhance metal electrode (cathode)
Binding force between electron transfer layer, electron injection degradation phenomenon caused by inhibiting cathode peeling-off are final to be promoted
The service life of device.
Embodiment 3
Fig. 3 shows another OLED device structure chart with molecular Iy self-assembled layer of the invention.The preparation method of the device
As described below.
By flexible, transparency is high, polyimides (PI) substrate distilled water resistant to high temperature, acetone, isopropyl alcohol ultrasonic cleaning
And it is put into oven drying, surface is handled 30 minutes by UV, is then moved in vacuum evaporation chamber.It is 2 × 10 in vacuum degree-6Under Pa
Start that each layer film is deposited.On the PI substrate 1 of smooth flexible high-temperature resistant, the compound 1 that one layer of 70nm thickness is deposited forms light
It learns coating 9 (CPL), the Ag of 100nm thickness is deposited in optical coatings 9 as cathode 8, stratification conjunction is deposited on cathode 8
Object 10 forms self-assembled molecule layer 10, and evaporation metal ytterbium and compound 11 (3:97) are in self-assembled molecule layer to form 50nm's
Electron injecting layer 7 (EIL), the compound 12 that 10nm thickness is then deposited on electron injecting layer 7 form electron transfer layer 6 (ETL),
On electron transfer layer 6, use compound 13 as the dopant material of luminescent layer, material of main part of the compound 4 as luminescent layer, together
When be deposited the dopant material and material of main part, form the luminescent layer 5 of 25nm thickness, then on luminescent layer 5 vapor deposition 100nm thickness change
It closes object 1 and forms hole transmission layer 4 (HTL), the compound 1 and (the doping weight of compound 2 of 10nm thickness are deposited on hole transmission layer 4
Amount is than being 97:3) hole injection layer 3 is formed, one layer of ITO of sputter is as anode 2 on hole injection layer 3.It is deposited on anode 2
One layer of Ag is completed as reflecting layer (not shown), device preparation.
Embodiment 4
Other all preparation steps are all same as Example 3, and different places are, one layer is deposited on cathode 8 by changing
It closes object 15 and forms self-assembled molecule layer.
Comparative example 2
Preparing for the device of comparative example 2 is same as Example 3, the difference is that not preparing self-assembled molecule layer.
The test of 2 device performance of table
From table 2 it can be seen that including having for molecular Iy self-assembled layer of the invention relative to the luminescent device in comparative example 1
The service life of machine luminescent device significantly extends.
It is not for limiting claim, any this field skill although the application is disclosed as above with preferred embodiment
Art personnel without departing from the concept of this application, can make several possible variations and modification, therefore the application
Protection scope should be subject to the range that the claim of this application is defined.
Claims (16)
1. a kind of compound, which is characterized in that the compound has chemical structure shown in formula (I):
Wherein, Ar indicates nitrogenous aromatic heterocycle group;
L indicates linking group and is selected from aryl or heteroaryl, and m indicates the number of linking group L and is selected from 0,1 or 2;
An indicates anchoring group.
2. compound according to claim 1, which is characterized in that Ar is selected from substituted or unsubstituted azepine aromatic condensed ring base
Group.
3. compound according to claim 1, which is characterized in that Ar is selected from following group:
Wherein, R1Selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, replace or
Unsubstituted C2-C40 heteroaryl;
# indicates link position.
4. according to claim 1 have compound, which is characterized in that the anchoring group is selected from sulfydryl, ester group, phosphinylidyne
Base or halogen-containing group.
5. according to claim 1 have compound, which is characterized in that L is selected from phenyl, pyridyl group, naphthalene, anthryl or phenanthrene
Base.
6. compound according to any one of claims 1 to 5, which is characterized in that the compound is selected from following compound:
Wherein, R2Selected from hydrogen atom, chlorine atom, fluorine atom, hydroxyl, the alkyl of C1-C20, C1-C20 alkoxy;R3Selected from hydrogen
Atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C2-C40 are miscellaneous
Aryl.
7. compound according to any one of claims 1 to 5, which is characterized in that the compound is selected from following compound:
8. a kind of display panel, the display panel includes organic luminescent device, wherein the organic luminescent device include anode,
Hole injection layer, hole transmission layer, organic luminous layer, electron transfer layer, electron injecting layer and cathode, which is characterized in that described
Organic luminescent device further includes the molecular Iy self-assembled layer being arranged between cathode and electron injecting layer, wherein the molecular self-assembling
The material of layer is compound described in any one of claims 1 to 7.
9. display panel according to claim 8, which is characterized in that the electron transport material tool in the electron transfer layer
There is following group:
Wherein, R1Selected from hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, substituted or unsubstituted C6-C40 aryl, replace or
Unsubstituted C2-C40 heteroaryl;
# indicates link position.
10. display panel according to claim 8, which is characterized in that the thickness range of the molecular Iy self-assembled layer is 1-
10nm。
11. display panel according to claim 10, which is characterized in that the thickness range of the molecular Iy self-assembled layer is 1-
5nm。
12. compound according to claim 8, which is characterized in that the electron transport material in the electron transfer layer is mixed
It is miscellaneous to have thulium or 8-hydroxyquinoline lithium.
13. compound according to claim 12, which is characterized in that the thulium is ytterbium.
14. display panel according to claim 8, which is characterized in that the organic luminescent device further includes being arranged in electricity
Hole blocking layer between sub- transport layer and luminescent layer.
15. display panel according to claim 8, which is characterized in that the organic luminescent device further includes being covered on yin
Cap on extremely.
16. a kind of display device, including the described in any item display panels of claim 8 to 15.
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Cited By (8)
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CN110128403A (en) * | 2019-05-31 | 2019-08-16 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
CN110156686A (en) * | 2019-05-27 | 2019-08-23 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
CN110379936A (en) * | 2019-07-23 | 2019-10-25 | 云谷(固安)科技有限公司 | Organic elctroluminescent device and display device |
CN111072578A (en) * | 2019-11-25 | 2020-04-28 | 武汉华星光电半导体显示技术有限公司 | P-type dopant and organic light emitting diode |
CN111116488A (en) * | 2019-12-27 | 2020-05-08 | 武汉天马微电子有限公司 | Organic compound, display panel and display device |
CN113130804A (en) * | 2021-04-02 | 2021-07-16 | 昆山国显光电有限公司 | Display panel |
CN114341144A (en) * | 2019-09-06 | 2022-04-12 | 日本放送协会 | Organic thin film, method for producing organic thin film, organic electroluminescent element, display device, lighting device, organic thin film solar cell, thin film transistor, photoelectric conversion element, coating composition, and material for organic electroluminescent element |
WO2023167234A1 (en) * | 2022-03-02 | 2023-09-07 | 三菱瓦斯化学株式会社 | Compound, organic thin film, photoelectric conversion element, imaging element, photosensor and solid-state imaging device |
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CN110128403A (en) * | 2019-05-31 | 2019-08-16 | 上海天马有机发光显示技术有限公司 | Compound, display panel and display device |
CN110128403B (en) * | 2019-05-31 | 2022-01-11 | 武汉天马微电子有限公司 | Compound, display panel and display device |
CN110379936A (en) * | 2019-07-23 | 2019-10-25 | 云谷(固安)科技有限公司 | Organic elctroluminescent device and display device |
CN110379936B (en) * | 2019-07-23 | 2021-12-14 | 云谷(固安)科技有限公司 | Organic electroluminescent display device and display apparatus |
CN114341144A (en) * | 2019-09-06 | 2022-04-12 | 日本放送协会 | Organic thin film, method for producing organic thin film, organic electroluminescent element, display device, lighting device, organic thin film solar cell, thin film transistor, photoelectric conversion element, coating composition, and material for organic electroluminescent element |
EP4026836A4 (en) * | 2019-09-06 | 2023-08-30 | Nippon Hoso Kyokai | Organic thin film, method for producing organic thin film, organic electroluminescent element, display device, lighting device, organic thin film solar cell, thin film transistor, photoelectric conversion element, coating composition and material for organic electroluminescent elements |
CN111072578A (en) * | 2019-11-25 | 2020-04-28 | 武汉华星光电半导体显示技术有限公司 | P-type dopant and organic light emitting diode |
CN111116488A (en) * | 2019-12-27 | 2020-05-08 | 武汉天马微电子有限公司 | Organic compound, display panel and display device |
CN113130804A (en) * | 2021-04-02 | 2021-07-16 | 昆山国显光电有限公司 | Display panel |
CN113130804B (en) * | 2021-04-02 | 2022-09-20 | 昆山国显光电有限公司 | Display panel |
WO2023167234A1 (en) * | 2022-03-02 | 2023-09-07 | 三菱瓦斯化学株式会社 | Compound, organic thin film, photoelectric conversion element, imaging element, photosensor and solid-state imaging device |
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Application publication date: 20190507 |