CN107482132A - A kind of organic luminescent device - Google Patents
A kind of organic luminescent device Download PDFInfo
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- CN107482132A CN107482132A CN201710721879.2A CN201710721879A CN107482132A CN 107482132 A CN107482132 A CN 107482132A CN 201710721879 A CN201710721879 A CN 201710721879A CN 107482132 A CN107482132 A CN 107482132A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Abstract
The invention provides a kind of organic luminescent device, is related to organic field of photoelectric technology.Organic luminescent device of the present invention include substrate, anode, negative electrode and one or more layers be placed in organic matter layer between anode and negative electrode and on negative electrode, wherein organic matter layer includes at least one layer being sequentially placed into the coating on the hole injection layer between anode and negative electrode, hole transmission layer, hole auxiliary layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode.Present invention also offers the compound suitable for each organic matter layer, by different compounds different organic layers application, the luminous efficiency and service life of organic luminescent device of the present invention increase significantly, and are a kind of organic electroluminescence devices of excellent performance, can be widely applied to display field.
Description
Technical field
The present invention relates to field of organic electroluminescence, more particularly to a kind of organic luminescent device.
Background technology
The a pair of electrodes of organic electroluminescent (OLED) device by luminescent layer and in luminescent layer both sides is formed.When at two
When applying electric field between electrode, electronics is injected by negative electrode, and hole is injected by anode, and electronics and hole recombine in luminescent layer
Exciton is formed, when exciton is transitted to energy transmitting light caused by stable ground state as excitation state.OLED relies on its self-luminous, regarded
Angular width, all solidstate, true color, reaction speed are fast, high brightness, low driving voltage, thickness of thin, light weight, the advantage such as flexible,
Light and thin type information display device field has obtained increasing application.In recent years, the application field of OLED luminescent devices has been
The information display device of other high quality is extended to from mobile phone.
But traditional OLED display device has the problem of luminous efficiency and service life more, mainly there are following several originals
Cause:On the one hand the luminescent properties of luminous organic material used, and the matching degree between each layer combined material are depended on;On the one hand take
Certainly in exciton utilization rate, because hole is different with the transmission speed of electronics in organic photoelectrical material, conventional device structure holds very much
Easily there is carrier and inject unbalanced problem, cause electronics and hole-recombination efficiency is low and the skew of recombination region, so as to lead
Cause organic electroluminescence device luminous efficiency is low, the life-span is low;On the other hand, the packaged type of organic electroluminescence device is more
For thin-film package, in the process, packaging film may produce tiny passage so that moisture and oxygen contact in environment
To OLED display device.And the negative electrode on upper strata is easily produced often using the higher metal of activity after being contacted with moisture and oxygen
The failure of device.
With the further raising that market is required OLED, higher luminous efficiency, more long-life, more inexpensive turn into
The trend of OLED development, so developing the encapsulating structure and the suitable electroluminescent organic material of matching of a kind of stabilization
Combination, turns into a kind of urgent problem to be solved.
The content of the invention
It is an object of the invention to provide a kind of achievable higher luminous efficiency and the organic electroluminescence of service life
Part.
A kind of organic luminescent device, successively including substrate, anode, negative electrode and one or more layers be placed between anode and negative electrode
And the organic matter layer on negative electrode, described organic matter layer include hole injection layer, the sky being sequentially placed between anode and negative electrode
At least one in coating on cave transport layer, hole auxiliary layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode
Layer;It is at least one layer of in wherein described organic matter layer to contain compound represented by least one Formula I or chemical formula II:
Chemical formula I
Wherein, L1、L2、L3Independently selected from hydrogen, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C1~
C60Alkoxy, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C6~C60It is aryl amine, substituted or unsubstituted
C10~C60Condensed ring radical or substituted or unsubstituted C4~C60Heterocyclic radical,
Chemical formula II
Wherein, L4Selected from singly-bound, substitution or unsubstituted C6~C60Aryl, substituted or unsubstituted C10~C60Condensed ring radical takes
Generation or unsubstituted C4~C60Heterocyclic radical;R1、R2、Ar1、Ar2Independently selected from hydrogen, substituted or unsubstituted C1~C60Alkyl,
Substituted or unsubstituted C1~C60Alkoxy, substituted or non-substituted C6~C60Aryl, substituted or unsubstituted C4~C60Heterocyclic radical
Or substituted or unsubstituted C10~C60;X1~X8Independently selected from nitrogen or carbon.
Preferably, described organic matter layer contains luminescent layer, and luminescent layer is between anode and negative electrode, containing of luminescent layer
At least one of compound shown in formula I or chemical formula II.
Preferably, described organic matter layer contains hole transmission layer, and hole transmission layer is empty between anode and luminescent layer
Contain at least one of compound shown in chemical formula I or chemical formula II in the transport layer of cave.
Preferably, described organic matter layer contains hole auxiliary layer, and hole auxiliary layer is empty between anode and luminescent layer
Cave auxiliary layer and luminescent layer close to, it is middle without other organic matter layers, contain in the auxiliary layer of hole in compound shown in chemical formula II
At least one.
Preferably, described organic matter layer contains electron transfer layer, and electron transfer layer is between luminescent layer and negative electrode, electricity
Sub- transport layer contains compound shown at least one Formula I.
Preferably, described organic matter layer contains coating, and coating is located on negative electrode, the top of device, covering
Layer contains the represented compound of at least one chemical formula II.
Preferably, the L in the chemical type I compound1、L2、L3One kind in group as follows:
Wherein, X, Y, Z are independently selected from hydrogen, cyano group, nitro, C1~C30Alkyl, C1~C30Alkoxy, C1~C30's
Ether alkyl, C6~C30Aryl, C10~C30Condensed ring radical or C4~C30Heterocyclic radical.
Beneficial effects of the present invention:
The present invention provides a kind of organic luminescent device, the organic matter layer of the invention by rationally designing device architecture, improves
Hole and the recombination rate of electronics, the luminous efficiency and service life of device are improved from structural point;One kind provided by the invention has
Machine luminescent device employs specific organic photoelectrical material combination, increases the matching degree between device and material, so that from
Material is in itself and interaction angle improves the luminous efficiency and service life of device.
Brief description of the drawings
Fig. 1 is a kind of organic luminescent device sectional view.
Wherein, the electric transmission of 1/ anode of substrate, 2/ hole injection layer, 3/ hole transmission layer, 4/ hole auxiliary layer, 5/ luminescent layer 6/
The coating 10 of 7/ electron injecting layer of layer, 8/ negative electrode 9/.
Embodiment
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, art technology
The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to protection scope of the present invention.
The invention provides a kind of organic luminescent device, successively including substrate 1, anode 2, negative electrode 9 and one or more layers put
Organic matter layer between anode and negative electrode and on negative electrode.The organic matter layer includes being sequentially placed between anode 2 and negative electrode 9
Hole injection layer 3, hole transmission layer 4, hole auxiliary layer 5, luminescent layer 6, electron transfer layer 7, electron injecting layer 8 and negative electrode 9
On coating 10 at least one layer;It is at least one layer of in organic matter layer to contain at least one Formula I or the institute of chemical formula II
Represent compound:
Chemical formula I
Wherein, L1、L2、L3Independently selected from hydrogen, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C1~
C60Alkoxy, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C6~C60It is aryl amine, substituted or unsubstituted
C10~C60Condensed ring radical or substituted or unsubstituted C4~C60Heterocyclic radical.
According to the present invention, the substituted alkyl, substitution alkoxy, substitution aryl, substitution aralkyl, substitution
Aryl amine, substitution condensed ring radical, substitution heterocyclic radical in, the substituent is independently selected from deuterium, C1-C10Alkyl, cyano group, nitre
Base, C6-C24Aryl or C3-C20Heterocyclic radical,
Chemical formula II
Wherein, L4Selected from singly-bound, substitution or unsubstituted C6~C60Aryl, substituted or unsubstituted C10~C60Condensed ring radical takes
Generation or unsubstituted C4~C60Heterocyclic radical;R1、R2、Ar1、Ar2Independently selected from hydrogen, substituted or unsubstituted C1~C60Alkyl,
Substituted or unsubstituted C1~C60Alkoxy, substituted or non-substituted C6~C60Aryl, substituted or unsubstituted C4~C60Heterocyclic radical
Or substituted or unsubstituted C10~C60Condensed ring radical;X1~X8Independently selected from nitrogen or carbon.
According to the present invention, the substituted alkyl, substitution aryl, substitution aralkyl, substitution aryl amine, substitution
In heterocyclic radical, the condensed ring radical substituted, the substituent is independently selected from deuterium, C1-C10Alkyl, C6-C24Aryl or C3-C20Heterocycle
Base.
Preferably, the L in chemical type I compound1、L2、L3One kind in group as follows:
Wherein, X, Y, Z are independently selected from hydrogen, cyano group, nitro, C1~C30Alkyl, C1~C30Alkoxy, C1~C30's
Ether alkyl, C6~C30Aryl, C10~C30Condensed ring radical or C4~C30Heterocyclic radical.
Preferably, a kind of organic luminescent device of the invention contains substrate 1, anode 2, hole injection layer 3, hole transmission layer
4th, luminescent layer 6, electron transfer layer 7, electron injecting layer 8, negative electrode 9, wherein at least one layer containing shown in chemical formula I or chemical formula II
At least one compound.
Preferably, a kind of organic luminescent device of the invention passes containing substrate 1, anode 2, hole injection layer 3, hole successively
Defeated layer 4, hole auxiliary layer 5, luminescent layer 6, electron transfer layer 7, electron injecting layer 8, negative electrode 9, wherein at least one layer contains chemistry
At least one compound shown in formula I or chemical formula II.
Preferably, a kind of organic luminescent device of the invention passes containing substrate 1, anode 2, hole injection layer 3, hole successively
Defeated layer 4, luminescent layer 6, electron transfer layer 7, electron injecting layer 8, negative electrode 9, coating 10, wherein at least one layer contains chemical formula I
Or at least one compound shown in chemical formula II.
Most preferably, a kind of organic luminescent device of the invention passes containing substrate 1, anode 2, hole injection layer 3, hole successively
Defeated layer 4, hole auxiliary layer 5, luminescent layer 6, electron transfer layer 7, electron injecting layer 8, negative electrode 9, coating 10, wherein at least one layer
Contain at least one compound shown in chemical formula I or chemical formula II.
Preferably, described organic matter layer contains luminescent layer 6, and luminescent layer 6 is between anode 2 and negative electrode 9, luminescent layer 6
Contain at least one of compound shown in chemical formula I or chemical formula II.Further preferably, luminescent layer 6 includes fluorescent host and visitor
At least one of body, wherein fluorescent host, object contain at least one of chemical formula I or chemical formula II compound.
Preferably, described organic matter layer contains hole transmission layer 4, hole transmission layer 4 be located at anode 2 and luminescent layer 6 it
Between, at least one of compound shown in chemical formula I or chemical formula II is contained in hole transmission layer 4.
Preferably, described organic matter layer contains hole auxiliary layer 5, hole auxiliary layer 5 be located at anode 2 and luminescent layer 6 it
Between, hole auxiliary layer 5 and luminescent layer 6 close to, it is middle without other organic matter layers, containing shown in chemical formula II in hole auxiliary layer 5
At least one of compound.
Preferably, described organic matter layer contains electron transfer layer 7, electron transfer layer 7 be located at luminescent layer 6 and negative electrode 9 it
Between, electron transfer layer 7 contains compound shown at least one Formula I.
Preferably, described organic matter layer contains coating 10, and coating 10 is located on negative electrode 9, the top of device,
Coating 10 contains the represented compound of at least one chemical formula II.
Compound shown in chemical formula I of the present invention, it can be obtained by known conventional synthetic method, for example,
Can by the way that bromination acridine is reacted with the corresponding boric acid of different linking ligands in the presence of palladium catalyst and alkali, so as to
Obtain compound shown in chemical formula I of the present invention.
Preferably, compound shown in chemical formula I may be selected from any one in following chemical formula:
Wherein, the Be- groups in chemical constitution shown in chemical formula I and Pbi- unit structures are as shown below:
Compound shown in chemical formula II of the present invention, it can be obtained by known conventional synthetic method, for example,
Can by the pyridine diindyl that substitutes amino by bromination, coupling, boration, from different linking ligands in palladium catalyst and alkali
In the presence of reacted, so as to obtain compound shown in chemical formula II of the present invention.
Preferably, compound shown in described chemical formula II, may be selected from any one in following chemical formula:
Preferably, the material of main part of luminescent layer 6 of the present invention can be the single layer structure or not that single substance is formed
The single layer structure or sandwich construction that commaterial is formed, when the material of main part of luminescent layer 6 contains described chemical formula I or chemical formula
Shown in II during compound, the material of main part of luminescent layer 6 is selected from the chemical combination A-1~A-36 of chemical formula I, B-1~B-29, C-1~C-60, D-
In 18~D131, E-1~E-191, F-1~F-192, G-1~G-192, and the compound J-1~J-184 of chemical formula II extremely
Few one kind.In addition, the material of main part of luminescent layer 6 is further selected from ADN, 3Ph-anthracene, α-ADN, 4P-NPB, DPVBI
Deng.
Preferably, the object dopant material of luminescent layer 6 of the present invention can be the single layer structure that single substance is formed,
But the single layer structure or sandwich construction that different material is formed, when the object dopant material of luminescent layer 6 contains described chemistry
During compound shown in formula I, the object dopant material of luminescent layer 6 is in chemical type I compound A-1~A-36, B-1~B-29
It is at least one.In addition, the object dopant material of luminescent layer 6 is further selected from DPAP-DPPA, TPPDA, Ir (tpy)3、FIrPic、
DCJTB, DCJT, DCM, DCM2, DMQA, DBQA, TMDBQA, HAT-CN, F4-TCNQ etc..
Preferably, hole transmission layer 4 of the present invention can be the single layer structure or difference that single substance is formed
The single layer structure or sandwich construction that material is formed, when the hole transmission layer 4 is containing shown in chemical formula II of the present invention
During compound, in addition hole transmission layer 4 is selected from least one of the compound I1~I276 of chemical formula II, hole transport
Layer 4 is further selected from α-NPD, TDATA, TPD, TAPC, Spiro-TAD etc..
Preferably, hole auxiliary layer 5 of the present invention can be the single layer structure or difference that single substance is formed
The single layer structure or sandwich construction that material is formed, when the hole auxiliary layer 5 contains the compound shown in described chemical formula II
When, hole auxiliary layer 5 is selected from least one of compound I1~I276 of chemical formula II, and is different from hole transmission layer 5.
Preferably, electron transfer layer 7 of the present invention can be the single layer structure or difference that single substance is formed
The single layer structure or sandwich construction that material is formed, when the electron transfer layer 7 contains the compound shown in described chemical formula II
When, electron transfer layer 7 is selected from least one of compound H-1~H-108 of chemical formula II.In addition, electron transfer layer 7 is gone back
It may be selected from BCP, TPBi, Alq3, Liq, Balq, TAZ and NTAZ etc..
Preferably, coating 10 of the present invention can be the single layer structure or not jljl that single substance is formed
The single layer structure or sandwich construction that matter is formed, when the coating 10 contains the compound shown in described chemical formula II, cover
Cap rock 10 is selected from least one of compound J-1~J-184 of chemical formula II.
Device architecture of the present invention is most preferably as shown in Figure 1:The hole of 1/ anode of substrate, 2/ hole-injecting material 3/
The coating 10 of 8/ negative electrode of transmission material 4/ hole auxiliary layer, 5/ luminescent layer, 6/ electron transfer layer, 7/ electron injecting layer 9/.Wherein, base
Plate 1 is transparent glass, plastics or quartz;Anode 2 is transparent tin indium oxide ITO or indium zinc oxide IZO;Hole auxiliary layer 5
Using the material with unipolarity hole transporting properties, the transmission of assist holes, beneficial to hole and electronics in the effective of luminescent layer
Compound, its film thickness monitoring existsIn the range of;Luminescent layer 6 includes luminescent layer material of main part and object dopant material;Negative electrode
9 use Ag or Ag alloy;It is the shortcomings that coating 10 is used to weaken metallic cathode translucency difference, former in optics for reducing luminous energy
The reflection on part surface, increase the luminous flux of device transmitted light, so as to improve the output rating of light, its film thickness monitoring exists
In the range of.
Compound shown in chemical formula I or chemical formula II of the present invention can be used separately as hole according to the difference of property
Transport layer 4, hole auxiliary layer 5, the main body of luminescent layer 6, luminescent layer 6 adulterate object, electron transfer layer 7, coating 10, institute of the present invention
A kind of organic luminescent device stated can be selected and combined according to the characteristic of device parameter requirements and material.To manufactured with
The organic electroluminescence device of lower same configuration:Compound/this hair shown in ITO/2-TNATA/ α-NPD or of the present invention chemical formulas II
Compound shown in bright described chemical formula of the present invention II/ ADN, 3Ph-anthracene or of the present invention chemical formulas
I or chemical formula II shown in compound:DPAP-DPPA、TPPDA、Ir(tpy)3Or compound/TPBi shown in chemical formula I of the present invention
Or compound shown in the chemical formulas II of the present invention of compound/LiF/Al/ shown in chemical formula I of the present inventionAccording to reality
Border needs can clipped organic layer.
Organic electroluminescence device of the present invention can be widely applied to Display panel, illumination OLED, flexible OLED, electronics
The fields such as paper, Organophotoreceptor or OTFT.
Comparing embodiment 1
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes, 2 are cleaned repeatedly with distilled water
It is secondary, ultrasonic washing 10 minutes, distilled water cleaning terminate after, isopropanol, acetone, methanol equal solvent in order ultrasonic washing with
After dry, be transferred in plasma washing machine, by aforesaid substrate wash 5 minutes, be sent in evaporator.
Hole injection layer 2-TNATA is deposited successively on the ito transparent electrode being already prepared toHole is deposited
Transport layerLuminescent layer main body A DN (9,10-Di (2-naphthyl) anthracene) is deposited:Object adulterates
DPAP-DPPA (6- (4- (diphenylamino) phenyl)-N, N-diphenyl pyren-1-amine) 5%So
After electron transfer layer is depositedNegative electrodeSaid process organic matter vaporization plating speed is to maintainLiF isAl is
[embodiment 1-3]
ADN in comparing embodiment 1 is changed into compound B-1, B-13, B-20 shown in the chemical formula I in embodiment 1-3.
Table 1 is the moieties of chemical formula I or II of the present invention and compares the characteristics of luminescence of the luminescent device of material preparation
Test result.
The characteristics of luminescence of [table 1] luminescent device is surveyed
As can be seen from Table 1, organic luminescent device of the embodiment of the present invention uses chemical compounds I compound as luminescent layer
Main body, the luminous efficiency and service life of device are significantly improved.
Comparing embodiment 2.:
Hole injection layer 2-TNATA is deposited on the ito transparent electrode being already prepared toHole transport is deposited
Layer a-NPDADN (9,10-Di (2-naphthyl) anthracene) and dopant DPAP-DPPA (6- (4-
(diphenylamino) phenyl)-N, N-diphenyl pyren-1-amine) 5% evaporationThen evaporation electricity
Sub- transport layerNegative electrodeSaid process organic matter vaporization plating speed is to maintainLiF isAl is
[embodiment 4-5]
DPAP-DPPA in comparing embodiment 2 is changed into compound A-6, A-10 shown in the chemical formula I in embodiment 4-5.
Table 2 is tested for the characteristics of luminescence of the moieties of chemical formula I of the invention and the luminescent device for comparing material preparation
As a result.
The characteristics of luminescence of [table 2] luminescent device is surveyed
As can be seen from Table 2, organic luminescent device of the embodiment of the present invention uses chemical compounds I compound as luminescent layer
Object adulterates, and the luminous efficiency and service life of device are significantly improved.
Comparing embodiment 3:
Hole injection layer 2-TNATA will be deposited on the ito transparent electrode being already prepared toHole transmission layer a-
NPD (N, N'- bis- (1- naphthyls)-N, N'- diphenyl-(1,1'- biphenyl) -4,4'- diamines)3Ph-anthracene
((2,9,10- triphenyls anthracene)) and doping Ir (tpy)3 Electron transfer layerNegative electrodeSaid process organic matter vaporization plating speed is to maintainLiF isAl is
[embodiment 6-14]
3Ph-anthracene in comparing embodiment 3 is changed into compound E- shown in the chemical formula I in embodiment 6-14
33、E-42、E-60、E-89、E-137、E-155、E-173、E-170、E-175。
Table 3 is the moieties of chemical formula I or II of the present invention and compares the characteristics of luminescence of the luminescent device of material preparation
Test result.
The characteristics of luminescence test result of [table 3] luminescent device
As can be seen from Table 3, organic luminescent device of the embodiment of the present invention uses chemical compounds I compound as luminescent layer
Main body, the luminous efficiency and service life of device are significantly improved.
Comparing embodiment 4:
Hole injection layer 2-TNATA will be deposited on the ito transparent electrode being already prepared toHole transport is deposited
Layer a-NPDADN (9,10- bis- (2- naphthyls) anthracene) and dopant material TPPDA (N1, N1, N6, N6- is deposited
Tetraphenylpyrene-1,6-diamine) 5% mixingElectron transfer layer is depositedNegative electrodeSaid process organic matter vaporization plating speed is to maintainLiF isAl is
[embodiment 15-23]
TPBi in comparing embodiment 4 is changed into compound H-1, H-6, H- shown in the chemical formula I in embodiment 15-23
14、H-8、H-7、H-42、H-43、H-44、H-45。
Table 4 is tested for the characteristics of luminescence of the moieties of chemical formula I of the invention and the luminescent device for comparing material preparation
As a result
The characteristics of luminescence of [table 4] luminescent device
As can be seen from Table 4, organic luminescent device of the embodiment of the present invention is passed using chemical compounds I compound as electronics
Defeated layer, the luminous efficiency and service life of device are significantly improved.
Comparing embodiment 5:
Hole injection layer 2-TNATA will be deposited on the ito transparent electrode being already prepared toHole transport is deposited
Layer a-NPDMain body A DN (9,10-Di (2-naph thyl) anthracene) and dopant material TPPDA
The mixing evaporations of (N1, N1, N6, N6-tetraphenylpyren-1,6-di amine) 5%Then electronics is deposited to pass
Defeated layerNegative electrodeSaid process organic matter vaporization plating speed is to maintainLiF isAl is
[embodiment 24-26]
A-NPD in comparing embodiment 5 is changed into compound I-37, I-91, I- shown in the chemical formula II in embodiment 1-3
193。
Table 5 is tested for the characteristics of luminescence of the moieties of chemical formula II of the invention and the luminescent device for comparing material preparation
As a result.
【Table 5】The characteristics of luminescence of luminescent device
As can be seen from Table 5, organic luminescent device of the embodiment of the present invention uses compound ii compound as hole
Transport layer, the luminous efficiency and service life of device are significantly improved.
Embodiment 27-29
On the basis of embodiment 23, hole auxiliary layer embodiment 27- is deposited respectively between hole transmission layer and luminescent layer
29
The characteristics of luminescence test for the luminescent device that table 6 is prepared for the moieties of chemical formula II and embodiment 23 of the present invention
As a result.
The characteristics of luminescence of [table 6] luminescent device
As can be seen from Table 6, organic luminescent device of the embodiment of the present invention using chemical compounds I as electron transfer layer,
The compound of chemical formula II is significantly improved as hole auxiliary layer, the luminous efficiency and service life of device.
Embodiment 30-32
On the basis of embodiment 29, coating is deposited on negative electrode respectively
The characteristics of luminescence test for the luminescent device that table 7 is prepared for the moieties of chemical formula II and embodiment 29 of the present invention
As a result.
The characteristics of luminescence of [table 7] luminescent device
As can be seen from Table 7, organic luminescent device of the embodiment of the present invention is passed using chemical type I compound as electronics
Defeated layer, the different compounds of chemical formula II have respectively as hole auxiliary layer, coating, the luminous efficiency and service life of device
It is obvious to improve.
A kind of organic luminescent device of the present invention using chemical formula I and chemical formula II different compounds respectively as
Hole transmission layer, hole auxiliary layer, luminous layer main body, the doping of luminescent layer object, electron transfer layer, coating, the hair of its device
Light efficiency and luminescent lifetime, which are obtained for, to be significantly improved.A kind of organic luminescent device of the present invention is a kind of excellent performance
Organic electroluminescence device, Display panel is can be widely applied to, illuminate OLED, flexible OLED, Electronic Paper, Organophotoreceptor or have
The fields such as machine thin film transistor (TFT).
Claims (7)
1. a kind of organic luminescent device, successively including substrate, anode, negative electrode and one or more layers be placed between anode and negative electrode and
Organic matter layer on negative electrode, it is characterised in that the organic matter layer includes the hole note being sequentially placed between anode and negative electrode
Enter in the coating on layer, hole transmission layer, hole auxiliary layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode
At least one layer;It is at least one layer of in organic matter layer to contain compound represented by least one Formula I or chemical formula II:
Chemical formula I
Wherein, L1、L2、L3Independently selected from hydrogen, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C1~C60Alkane
Epoxide, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C6~C60Aryl amine, substituted or unsubstituted C10~
C60Condensed ring radical or substituted or unsubstituted C4~C60Heterocyclic radical,
Chemical formula II
Wherein, L4Selected from singly-bound, substitution or unsubstituted C6~C60Aryl, substituted or unsubstituted C10~C60Condensed ring radical or substitution or
Unsubstituted C4~C60Heterocyclic radical;R1、R2、Ar1、Ar2Independently selected from hydrogen, substituted or unsubstituted C1~C60Alkyl, substitution
Or unsubstituted C1~C60Alkoxy, substituted or non-substituted C6~C60Aryl, substituted or unsubstituted C4~C60Heterocyclic radical takes
Generation or unsubstituted C10~C60Condensed ring radical;X1~X8Independently selected from nitrogen or carbon.
2. a kind of organic luminescent device according to claim 1, it is characterised in that containing luminous in described organic matter layer
Layer, for luminescent layer between anode and negative electrode, luminescent layer contains at least one in compound shown in chemical formula I or chemical formula II
Kind.
3. a kind of organic luminescent device according to claim 1, it is characterised in that contain hole in described organic matter layer
Transport layer, hole transmission layer contain chemical formula I or shownization of chemical formula II between anode and luminescent layer in hole transmission layer
At least one of compound.
4. a kind of organic luminescent device according to claim 1, it is characterised in that contain hole in described organic matter layer
Auxiliary layer, hole auxiliary layer is between anode and luminescent layer, and hole auxiliary layer and luminescent layer are close to centre is without other organic matters
Layer, contain at least one of compound shown in chemical formula II in the auxiliary layer of hole.
5. a kind of organic luminescent device according to claim 1, it is characterised in that contain electronics in described organic matter layer
Transport layer, for electron transfer layer between luminescent layer and negative electrode, electron transfer layer contains chemical combination shown at least one Formula I
Thing.
6. a kind of organic luminescent device according to claim 1, it is characterised in that contain covering in described organic matter layer
Layer, coating are located on negative electrode, and the top of device, coating contains the represented compound of at least one chemical formula II.
7. a kind of organic luminescent device according to claim 1, it is characterised in that in described chemical type I compound
L1、L2、L3One kind in group as follows:
Wherein, X, Y, Z are independently selected from hydrogen, cyano group, nitro, C1~C30Alkyl, C1~C30Alkoxy, C1~C30Ether alkane
Base, C6~C30Aryl, C10~C30Condensed ring radical or C4~C30Heterocyclic radical.
Priority Applications (1)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110964002A (en) * | 2019-12-13 | 2020-04-07 | 长春海谱润斯科技有限公司 | Arylamine derivative and organic light-emitting device thereof |
CN113972331A (en) * | 2021-10-25 | 2022-01-25 | 京东方科技集团股份有限公司 | Light-emitting device, display panel and display device |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1751024A (en) * | 2003-01-10 | 2006-03-22 | 出光兴产株式会社 | Nitrogen-containing heterocyclic derivative and organic electroluminescent element using same |
CN102924431A (en) * | 2012-10-31 | 2013-02-13 | 吉林大学 | Organic luminescent compound containing acridine core and application thereof in electroluminescent device |
CN103420910A (en) * | 2012-07-26 | 2013-12-04 | 烟台万润精细化工股份有限公司 | Electron-transport blue luminescent material and use thereof |
CN103619821A (en) * | 2011-04-27 | 2014-03-05 | 保土谷化学工业株式会社 | Compound with acridan ring structure, and organic electroluminescent element |
CN104650032A (en) * | 2015-01-23 | 2015-05-27 | 北京鼎材科技有限公司 | Acridine derivatives, and preparation method and application thereof |
CN106279148A (en) * | 2015-05-22 | 2017-01-04 | 上海和辉光电有限公司 | Promote OLED high temperature, the material of high current density performance and application thereof |
CN106749215A (en) * | 2016-12-09 | 2017-05-31 | 中节能万润股份有限公司 | A kind of compound, preparation method and applications based on monosubstituted base acridine |
CN106816537A (en) * | 2015-11-30 | 2017-06-09 | 乐金显示有限公司 | Organic light-emitting display device and forming method thereof |
-
2017
- 2017-08-22 CN CN201710721879.2A patent/CN107482132A/en active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1751024A (en) * | 2003-01-10 | 2006-03-22 | 出光兴产株式会社 | Nitrogen-containing heterocyclic derivative and organic electroluminescent element using same |
CN103619821A (en) * | 2011-04-27 | 2014-03-05 | 保土谷化学工业株式会社 | Compound with acridan ring structure, and organic electroluminescent element |
CN103420910A (en) * | 2012-07-26 | 2013-12-04 | 烟台万润精细化工股份有限公司 | Electron-transport blue luminescent material and use thereof |
CN102924431A (en) * | 2012-10-31 | 2013-02-13 | 吉林大学 | Organic luminescent compound containing acridine core and application thereof in electroluminescent device |
CN104650032A (en) * | 2015-01-23 | 2015-05-27 | 北京鼎材科技有限公司 | Acridine derivatives, and preparation method and application thereof |
CN106279148A (en) * | 2015-05-22 | 2017-01-04 | 上海和辉光电有限公司 | Promote OLED high temperature, the material of high current density performance and application thereof |
CN106816537A (en) * | 2015-11-30 | 2017-06-09 | 乐金显示有限公司 | Organic light-emitting display device and forming method thereof |
CN106749215A (en) * | 2016-12-09 | 2017-05-31 | 中节能万润股份有限公司 | A kind of compound, preparation method and applications based on monosubstituted base acridine |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110964002A (en) * | 2019-12-13 | 2020-04-07 | 长春海谱润斯科技有限公司 | Arylamine derivative and organic light-emitting device thereof |
CN113972331A (en) * | 2021-10-25 | 2022-01-25 | 京东方科技集团股份有限公司 | Light-emitting device, display panel and display device |
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