CN105261706B - A kind of organic fluorescence light emitting diode of planar heterojunction sensitization and preparation method thereof - Google Patents
A kind of organic fluorescence light emitting diode of planar heterojunction sensitization and preparation method thereof Download PDFInfo
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- CN105261706B CN105261706B CN201510557886.4A CN201510557886A CN105261706B CN 105261706 B CN105261706 B CN 105261706B CN 201510557886 A CN201510557886 A CN 201510557886A CN 105261706 B CN105261706 B CN 105261706B
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- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
- H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
Abstract
The invention belongs to organic photoelectrical material technical fields, disclose a kind of organic fluorescence light emitting diode of planar heterojunction sensitization and preparation method thereof.The diode includes the substrate, anode, p-type organic semiconductor layer, n-type organic semiconductor layer and the cathode that stack gradually；At least one layer of doping fluorescent material in the p-type organic semiconductor layer and n-type organic semiconductor layer.P-type organic semiconductor layer is made of the organic semiconducting materials for being capable of preferably conduction hole, and n-type organic semiconductor layer is made of the organic semiconducting materials that can preferably conduct electronics.The electroluminescent spectrum of the organic fluorescence light emitting diode of the present invention has relatively low driving voltage and higher luminous efficiency, theoretical internal quantum efficiency can reach 100%, have a good application prospect from adulterated organic fluorescence materials.
Description
Technical field
The invention belongs to organic photoelectrical material technical fields, and in particular to a kind of organic fluorescence hair of planar heterojunction sensitization
Optical diode and preparation method thereof.
Background technology
At present, the research of Organic Light Emitting Diode (OLED) has been introduced into the commercial application stage, and scientific research institutions are high
School, enterprise has all put into a large amount of human and material resources, financial resources carry out relevant study and using work.The research starts from 1987,
Doctor Deng Qingyun of Kodak waits the OLED device developed in patent US4356429 using sandwich device architecture
Light emission luminance reaches 1000cd/m under 10V direct voltage drives2, OLED is made to obtain epoch-making development.However, at such
In the fluorescence OLED device of type, due to the restriction of spin statistics rule, it is merely capable of realizing 25% exciton utilization ratio so that
The maximum external quantum efficiency of device is limited in 5% or so (it is assumed that light extraction efficiency is 20%).1998, the horse what of Jilin University
The research groups such as light professor and professor Forrest of Princeton University obtain great prominent in the development of phosphorescent OLED device
Broken (Synthetic Metals, 1998,94:245-248；Nature,1998,395(6698):151-154) so that phosphorescence
The theoretical maximum internal quantum efficiency of OLED device is promoted to 100%.However, contain rare metal in phosphorescent light-emitting materials, it can pole
Big limitation phosphorescent OLED device cost reduction, at the same it is difficult always the problems such as blue phosphorescent OLED device short life, photochromic purity difference
To solve.Thus, develop the fluorescence luminescent material of low cost, and prepare the full fluorescence OLED that internal quantum efficiency reaches 100%
Device becomes the research hotspot in organic photoelectric field.In recent years, Kyushu University Adachi was taught group and was prolonged using thermal activation
Slow Fluorescence Mechanism realizes a series of efficient fluorescence OLED device, some of which types of devices internal quantum efficiency have reached or
Close to 100%, device efficiency can compare phosphorescent OLED person.However, these utilize thermal activation delayed fluorescence mechanism works
OLED device mostly have wider luminescent spectrum so that the excitation purity that device shines is not high.To solve the problems, such as this, in the industry
Through developing by the use of the material with thermal activation delayed fluorescence characteristic as sensitization main body or co-host, with luminous peak type compared with
Narrow conventional fluorescent material is as doping object, so as to fulfill sensitization object fluorescent emission, obtain high efficiency, high color purity it is glimmering
Light OLED device.Material as sensitized fluorescence main body or auxiliary sensitization main body mainly has these following types：First, have
Compared with small third-line areas' state and the single fluorescent material of singlet splitting energy, usually some typical charge transfer state (CT) molecules
(Nature Communications,2014,5:4016,DOI:10.1038/ncomms5016；Advanced Materials,
2014,26(29):5050-5055)；Second is that material of main part of the two kinds of materials of physical blending collectively as fluorescent guest
(Advanced Materials,2015,27(12):2025-2030).In this device architecture, generally at least there are these
Functional layer：Hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, wherein luminescent layer by two kinds or
Three kinds of person is material doped to be formed.
These are by the use of the material with thermal activation delayed fluorescence characteristic as the sensitization type for being sensitized main body or co-host
Fluorescence OLED device has the following disadvantages：(1) multilayer organic layer so that device preparation flow is cumbersome, is unfavorable for time cost
Reduction；(2) material of multilayer multiple types causes device preparation that the cost of material is needed also to increase significantly；(3) different organic phases
Between easily exist mutually stablize the problem of, so as to influence device lifetime；(4) easy Presence of an interface pressure between different organic layers
Drop so that the more difficult reduction of driving voltage of device increases power consumption during device work.
Based on considerations above, develop a kind of simple plane PN hetero-junctions formed using transmission material of novel structure and make
For sensitivity speck, high efficiency, the fluorescence OLED device of high color purity by the use of conventional fluorescent organic material as dopant are realized
Just it is particularly important.
Invention content
In order to solve the disadvantage that the more than prior art and shortcoming, primary and foremost purpose of the invention is to provide a kind of plane
The organic fluorescence light emitting diode of hetero-junctions sensitization.
Another object of the present invention is to provide a kind of organic fluorescence light emitting diode of above-mentioned planar heterojunction sensitization
Preparation method.
The object of the invention is achieved through the following technical solutions：
A kind of organic fluorescence light emitting diode of planar heterojunction sensitization, substrate, anode, p-type including stacking gradually have
Machine semiconductor layer, n-type organic semiconductor layer and cathode, stratose structure diagram are as shown in Figure 1；The p-type is organic partly to be led
Fluorescent material is mixed in body layer and n-type organic semiconductor layer at least one layer.
The material for preparing of the p-type organic semiconductor layer includes but not limited to following material：
The material for preparing of the n-type organic semiconductor layer includes but not limited to following material：
The fluorescence dopant material includes but not limited to following material：
The p-type organic semiconductor layer and n-type organic semiconductor layer can be single-layer or multi-layers；P-type organic semiconductor
Layer prepares blending of the material for one-component material or multi-component material with n-type organic semiconductor layer.
One layer of anode buffer layer can be also added between the anode and p-type organic semiconductor layer；Cathode and N-type organic half
One layer of cathode buffer layer can be also added between conductor layer.
The substrate is rigid substrate such as glass, quartz, sapphire etc. and flexible substrate such as polyimides, poly- pair
Ethylene terephthalate, mylar's fat, polyethylene naphthalate or other polyester materials and metal,
Alloy or stainless steel film etc..
The anode and cathode are metal or metal oxide；The preferred tin indium oxide of the metal oxide
(ITO), the group of one or more of fluorine-doped tin dioxide (FTO), zinc oxide (ZnO) and indium gallium zinc oxide (IGZO)
It closes.
The luminescent spectrum of the organic fluorescence light emitting diode of the planar heterojunction sensitization derives from the fluorescent material mixed.
The preparation method of the organic fluorescence light emitting diode of above-mentioned planar heterojunction sensitization, includes the following steps：
The substrate material with anode layer is taken, it is organic to be then sequentially prepared p-type organic semiconductor layer, N-type on the anode layer
Semiconductor layer and cathode layer obtain the organic fluorescence light emitting diode of planar heterojunction sensitization.
The method of the preparation includes hot evaporation, spin coating, brushing, spraying, dip-coating, roller coating, printing or inkjet printing.
The present invention preparation method and obtained product has the following advantages that and advantageous effect：
(1) device architecture according to the present invention is simple, and preparation flow is few, while can realize low driving voltage and height
External quantum efficiency；
(2) device organic layer according to the present invention does not contain precious metal element, conducive to the material cost of device is reduced；
(3) the involved device of invention does not need to especially increase sensitization main body or auxiliary sensitization material of main part, it is only necessary to
The plane PN hetero-junctions formed by the use of charge transport materials is reduced device and prepares required material kind as sensitivity speck
Class；
(4) device according to the present invention can carry out radioluminescence using singlet and triplet excitons simultaneously, theoretical
Internal quantum efficiency reaches 100%, can realize high excitation purity and and high luminous efficiency simultaneously.
Description of the drawings
Fig. 1 is the stratose structure diagram of the organic fluorescence light emitting diode of the planar heterojunction sensitization of the present invention；
Current density-brightness of the organic fluorescence light emitting diode of planar heterojunction sensitization that Fig. 2 is obtained for embodiment 1-
Voltage characteristic curve；
Fig. 3 is current efficiency-outer quantum of the organic fluorescence light emitting diode of planar heterojunction sensitization that embodiment 1 obtains
Efficiency-current density characteristics curve graph；
Fig. 4 be the DMQA doping concentrations that embodiment 1 obtains be 0.1% (a), 0.2% (b), 0.4% (c) and 0.6% (d)
Planar heterojunction sensitization electroluminescent light spectrogram of the organic fluorescence light emitting diode under different current densities；
Fig. 5 is the organic fluorescence LED device 1 of planar heterojunction sensitization and the electricity of device 2 that embodiment 2 obtains
Current density-brightness-voltage characteristic curve graph；
Fig. 6 is the organic fluorescence LED device 1 of planar heterojunction sensitization and the electricity of device 2 that embodiment 2 obtains
Flow efficiency-external quantum efficiency-current density characteristics curve graph；
Fig. 7 is the organic fluorescence LED device 1 (a) and device 2 of planar heterojunction sensitization that embodiment 2 obtains
(b) the electroluminescent light spectrogram under different current densities.
Specific embodiment
With reference to embodiment and attached drawing, the present invention is described in further detail, but embodiments of the present invention are unlimited
In this.
Embodiment 1
Take same lot number ITO Conducting Glass several, specification is 30 millimeters × 30 millimeters, and ITO thickness is about 90 nanometers,
Square resistance is about 20 ohms/squares.Successively with acetone, micron level semiconductor special purpose detergent, deionized water, isopropanol ultrasound
Cleaning 15 minutes, to remove the dirt of substrate surface.It is for use to be subsequently placed into 80 degrees Celsius of drying in insulating box.ITO after drying
Substrate is handled 4 minutes with plasma glow start equipment, further removes the organic pollution of surface attachment.Then ITO substrates
It is transferred to anhydrous and oxygen-free, the glove box full of high pure nitrogen.In this glove box, device is fitted into Vacuum Deposition chamber.Unlatching machine
Tool pumps and molecular pump, when plating intracavitary reaches 4 × 10-4High vacuum after start hot evaporation film.Using specific mask plate, successively
The N-type organic semiconducting materials that vapor deposition anode buffer layer material TAPC, p-type organic semiconducting materials TCTA, DMQA mix
TmPyTZ (doping concentration 0.1%, 0.2%, 0.4%, 0.6%, molar ratio), cathode cushioning layer material lithium fluoride, cathode
Material metal aluminium.The thickness of vapor deposition layer is monitored in real time by quartz crystal oscillator film thickness detector, controls anode buffer layer material respectively
The thickness of TAPC is 25 nanometers, the thickness of TCTA layers of p-type organic semiconducting materials is 10 nanometers, the N-type of DMQA doping organic half
The thickness that TmPyTZ layers of conductor material is 60 nanometers.Obtain the organic fluorescence light emitting diode of planar heterojunction sensitization：Ito glass
Substrate/TAPC (25 nanometers)/TCTA (10 nanometers)/DMQA adulterates TmPyTZ (60 nanometers)/lithium fluoride (1 nanometer)/aluminium.
The light emitting diode for the different DMQA dopant concentrations that the present embodiment obtains carries out photoelectric properties test：It is prepared by device
Cheng Hou takes out device from vapor deposition cavity, using glass cover-plate, by the packaging plastic of epoxy resin in glove box into
Row simplified package.It then takes out in air and is tested, CS200 brightness of the test equipment for Konica-Minolta company generation
Meter, device current information of voltage are measured by the 2400 source tables that Keithley company generates.It can by information such as brightness, electric current, voltages
Current efficiency, the power efficiency of device are extrapolated respectively.Under the supposed premise of lambertian distribution, according to brightness, current density, electricity
The external quantum efficiency of photoluminescence spectrum calculating device.The electroluminescent spectrum of device is produced by PhotoResearch companies
PR705 equipment is tested and is obtained.
The organic fluorescence light emitting diode of planar heterojunction sensitization that this implementation obtains：(25 receive ito glass substrate/TAPC
Rice)/TCTA (10 nanometers)/DMQA doping TmPyTZ (60 nanometers)/lithium fluoride (1 nanometer)/aluminium current density-luminance-voltage
Performance diagram, current efficiency-external quantum efficiency-current density characteristics curve graph and the electroluminescent under different current densities
Spectrogram difference is as shown in Figure 2, Figure 3 and Figure 4.DMQA in (a), (b), (c) and (d) corresponding device in wherein Fig. 4
Doping concentration be 0.1%, 0.2%, 0.4% and 0.6%.
Understand that device is from fluorescein it is found that the doping concentration with fluorescein DMQA increases by 2~4 result
Luminous component is gradually presented, and spectral signature shows as shining for fluorescein.Under 0.6% doping concentration, spectrum is presented as glimmering
The luminescence feature of light element, the external quantum efficiency for realizing device maximum at this time is 9.57%, has been more than outside conventional fluorescent device 5%
The limitation of quantum efficiency.The device is the type of device that unilateral N-type organic material side is doped using fluorescein DMQA.
Embodiment 2
For preparation process such as embodiment 1 but without anode buffer layer, p-type organic semiconducting materials are respectively selected as DMQA doping
TAPC (doping concentration 0.7%, molar ratio) and DMQA doping TCTA (doping concentration 1.1%, molar ratio), N
Type organic semiconducting materials are the TmPyTZ (doping concentration 0.7%, molar ratio) of DMQA doping.P-type is organic partly leads for control
The thickness of body material layer is 25 nanometers and the thickness of N-type organic semiconductor material is 60 nanometers, respectively obtains planar heterojunction
The organic fluorescence light emitting diode of sensitization：Ito glass substrate/(60 receive DMQA doping TAPC (25 nanometers)/DMQA doping TmPyTZ
Rice)/lithium fluoride (1 nanometer)/aluminium (device 1) and ito glass substrate/DMQA doping TCTA (25 nanometers)/DMQA adulterates TmPyTZ
(60 nanometers)/lithium fluoride (1 nanometer)/aluminium (device 2).The device is bilateral p-type semiconductor material and N-type organic semiconducting materials
The type of device being doped simultaneously using fluorescein DMQA.
The current density for the light emitting diode that the present embodiment obtains-brightness-voltage characteristic curve graph, current efficiency-outer amount
Electroluminescent light spectrogram under sub- efficiency-current density characteristics curve graph and different current densities is respectively such as Fig. 5, Fig. 6 and Fig. 7 institute
Show, wherein the electroluminescent light spectrogram of Fig. 7 (a) devices 1；Fig. 7 (b) is the electroluminescent light spectrogram of device 2.Result can from figure
To find out：Using the planar heterojunction that p-type organic semiconducting materials TAPC and N-type organic semiconducting materials TmPyTZ are formed into
During row doping, the electroluminescent spectrum of device has showed the feature of fluorescein DMQA transmittings, and device realizes 8.0%
Maximum external quantum efficiency, while the cut-in voltage of device is down to 2.16V.Have using p-type organic semiconducting materials TCTA and N-type
Machine semi-conducting material TmPyTZ form planar heterojunction carry out bilateral doping fluorescent element DMQA when, it can be seen that device it is electroluminescent
Luminescent spectrum shows as the transmitting of purer fluorescein, and shining for of TCTA/TmPyTZ planar heterojunctions itself is quenched significantly
, illustrate effectively to be sensitized shining for object fluorescein by this planar heterojunction structure.The outer quantum of maximum of device
Efficiency still reaches 8%, has been more than the theoretical limitation of maximum 5% external quantum efficiency of conventional fluorescent OLED device.This illustrates to lead to
Plane PN hetero-junctions is crossed as sensitivity speck, can realize shining, while realize triplet excitons for sensitization object fluorescent molecular
Radiation with singlet exciton utilizes.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (7)
1. a kind of organic fluorescence light emitting diode of planar heterojunction sensitization, it is characterised in that：Including substrate, the sun stacked gradually
Pole, p-type organic semiconductor layer, n-type organic semiconductor layer and cathode；The p-type organic semiconductor layer and N-type organic semiconductor
At least one layer of doping fluorescent material in layer；
The p-type organic semiconductor layer prepares blending of the material for one or both of TAPC and TCTA：
The n-type organic semiconductor layer prepares material as TmPyTZ：
The fluorescence dopant material is being total to one or more of following (a)~(i) molecular structural formula materials
It is mixed：
2. a kind of organic fluorescence light emitting diode of planar heterojunction sensitization according to claim 1, it is characterised in that：Institute
The p-type organic semiconductor layer and n-type organic semiconductor layer stated are single-layer or multi-layer.
3. a kind of organic fluorescence light emitting diode of planar heterojunction sensitization according to claim 1, it is characterised in that：Institute
One layer is individually or simultaneously added between the anode and p-type organic semiconductor layer stated, between cathode and N-type organic semiconducting materials to delay
Rush layer.
4. a kind of organic fluorescence light emitting diode of planar heterojunction sensitization according to claim 1, it is characterised in that：Institute
The substrate stated is glass, quartz, sapphire, polyimides, polyethylene terephthalate, mylar's fat, is gathered
(ethylene naphthalate), metal, alloy or stainless steel film.
5. a kind of organic fluorescence light emitting diode of planar heterojunction sensitization according to claim 1, it is characterised in that：Institute
The anode and cathode stated are metal or metal oxide；The metal oxide refer to tin indium oxide, fluorine-doped tin dioxide,
The combination of one or more of zinc oxide and indium gallium zinc oxide.
6. a kind of organic fluorescence light emitting diode of planar heterojunction sensitization according to claim 1, it is characterised in that：Institute
The luminescent spectrum for stating the organic fluorescence light emitting diode of planar heterojunction sensitization derives from the fluorescent material mixed.
7. a kind of preparation side of the organic fluorescence light emitting diode of planar heterojunction sensitization of claim 1~6 any one of them
Method, it is characterised in that include the following steps：
The substrate material with anode layer is taken, is then sequentially prepared that p-type organic semiconductor layer, N-type are organic partly to be led on the anode layer
Body layer and cathode layer obtain the organic fluorescence light emitting diode of planar heterojunction sensitization；The method of the preparation include hot evaporation,
Spin coating, brushing, spraying, dip-coating, roller coating, printing or inkjet printing.
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