CN105261706A - Planar heterojunction sensitized organic fluorescence light-emitting diode and preparation method therefor - Google Patents
Planar heterojunction sensitized organic fluorescence light-emitting diode and preparation method therefor Download PDFInfo
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- CN105261706A CN105261706A CN201510557886.4A CN201510557886A CN105261706A CN 105261706 A CN105261706 A CN 105261706A CN 201510557886 A CN201510557886 A CN 201510557886A CN 105261706 A CN105261706 A CN 105261706A
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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 the technical field of organic photoelectric materials, and discloses a planar heterojunction sensitized organic fluorescence light-emitting diode and a preparation method therefor. The diode comprises a substrate, a positive electrode, a P type organic semiconductor layer, an N type organic semiconductor layer and a negative electrode that are laminated in sequence; at least one layer of the P type organic semiconductor layer and the N type organic semiconductor layer is doped with a fluorescent material; the P type organic semiconductor layer is made from an organic conductor material capable of well conducting holes, and the N type organic semiconductor layer is made from an organic conductor material capable of well conducting electronics. The electroluminescence spectrum of the organic fluorescence light-emitting diode comes from the doped organic fluorescent material, so that the organic fluorescence light-emitting diode is lower in driving voltage and higher in luminous efficiency, the internal quantum efficiency can reach 100% theoretically, and the organic fluorescence light-emitting diode is wide in application prospects.
Description
Technical field
The invention belongs to organic photoelectrical material technical field, be specifically related to organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization and preparation method thereof.
Background technology
At present, the research of Organic Light Emitting Diode (OLED) has entered into the commercial application stage, scientific research institutions, colleges and universities, and enterprise has all dropped into a large amount of human and material resources, financial resources carry out relevant investigation and application work.This research starts from 1987, and OLED luminosity under 10V direct voltage drive that doctor Deng Qingyun etc. of Kodak adopts sandwich device architecture to develop in patent US4356429 reaches 1000cd/m
2, make OLED obtain epoch-making development.But, in the fluorescence OLED of the type, due to the restriction of spin statistics rule, only can realize the exciton utilization ratio of 25%, make the maximum external quantum efficiency of device be limited in about 5% (assuming that light extraction efficiency is 20%).1998, the research groups such as the Ma Yuguang professor of Jilin University and professor Forrest of Princeton University obtained important breakthrough (SyntheticMetals, 1998,94:245-248 in the development of phosphorescent OLED device; Nature, 1998,395 (6698): 151-154), make the maximum internal quantum efficiency of the theory of phosphorescent OLED device rise to 100%.But containing rare metal in phosphorescent light-emitting materials, can greatly reduce by restriction phosphorescent OLED device cost, the problem such as blue phosphorescent OLED life-span short, photochromic purity difference is difficult to solve simultaneously always.Thus, the fluorescence luminescent material of development low cost, and the study hotspot preparing that full fluorescence OLED that internal quantum efficiency reaches 100% becomes organic photoelectric field.In recent years, Kyushu University Adachi teaches group and utilizes thermal activation delayed fluorescence mechanism to achieve a series of efficient fluorescence OLED, wherein some types of devices internal quantum efficiency has reached or close to 100%, and device efficiency can have been compared phosphorescent OLED.But these utilize the OLED of thermal activation delayed fluorescence mechanism works mostly to have wider luminescent spectrum, make the colorimetric purity of device luminescence not high.For head it off, develop in the industry and utilized the material with thermal activation delayed fluorescence characteristic as sensitization main body or co-host, using the narrower conventional fluorescent material of glow peak type as doping object, thus realize sensitization object fluorescent emission, obtain the fluorescence OLED of high efficiency, high color purity.Material as sensitized fluorescence main body or auxiliary sensitization main body mainly contains these kinds following: one is the single fluorescent material had compared with small third-line areas' state and singlet splitting energy, generally some typical charge transfer state (CT) molecules (NatureCommunications, 2014,5:4016, DOI:10.1038/ncomms5016; AdvancedMaterials, 2014,26 (29): 5050-5055); Two is that the bi-material of physical blending is jointly as the material of main part (AdvancedMaterials, 2015,27 (12): 2025-2030) of fluorescent guest.In this device architecture, generally at least there are these functional layers: hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer, wherein luminescent layer material dopedly to be formed by two kinds or three kinds.
These utilize the material with thermal activation delayed fluorescence characteristic to have the following disadvantages as the sensitization type fluorescence OLED of sensitization main body or co-host: (1) multilayer organic layer makes device preparation flow loaded down with trivial details, is unfavorable for the reduction of time cost; (2) material of multilayer multiple types makes device prepare needs the cost of material also greatly to raise; (3) easily there is mutually stable problem between different organic phase, thus may device lifetime be affected; (4) easy Presence of an interface pressure drop between different organic layer, makes the more difficult reduction of the driving voltage of device, adds power consumption during devices function.
Based on above consideration, develop plane P N heterojunction that a kind of novel structure simply utilizes transferring material to form as sensitivity speck, realize utilizing conventional fluorescent organic material just to seem particularly important as the high efficiency of dopant, the fluorescence OLED of high color purity.
Summary of the invention
In order to solve the shortcoming and defect part of above prior art, primary and foremost purpose of the present invention is the organic fluorescence light-emitting diode providing a kind of planar heterojunction sensitization.
Another object of the present invention is to the preparation method of the organic fluorescence light-emitting diode that a kind of above-mentioned planar heterojunction sensitization is provided.
The object of the invention is achieved through the following technical solutions:
An organic fluorescence light-emitting diode for planar heterojunction sensitization, comprises the substrate, anode, p-type organic semiconductor layer, n-type organic semiconductor layer and the negative electrode that stack gradually, and its stratose structural representation as shown in Figure 1; One deck is had at least to mix fluorescent material in described p-type organic semiconductor layer and n-type organic semiconductor layer.
The material of preparing of described p-type organic semiconductor layer includes but not limited to following material:
The material of preparing of described n-type organic semiconductor layer includes but not limited to following material:
Described fluorescence dopant material includes but not limited to following material:
Described p-type organic semiconductor layer and n-type organic semiconductor layer can be single or multiple lifts; The material of preparing of p-type organic semiconductor layer and n-type organic semiconductor layer is the blended of one-component material or multi-component material.
Also one deck anode buffer layer can be added between described anode and p-type organic semiconductor layer; Also one deck cathode buffer layer can be added between negative electrode and n-type organic semiconductor layer.
Described substrate be rigid substrate as glass, quartz, sapphire etc., and flexible substrate is as polyimides, PETG, mylar's fat, PEN or other polyester material and metal, alloy or stainless steel film etc.
Described anode and negative electrode are metal or metal oxide; One or more combination in described metal oxide preferential oxidation indium tin (ITO), fluorine-doped tin dioxide (FTO), zinc oxide (ZnO) and indium gallium zinc oxide (IGZO).
The luminescent spectrum of the organic fluorescence light-emitting diode of described 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, comprises the following steps:
Get the backing material with anode layer, then prepare p-type organic semiconductor layer, n-type organic semiconductor layer and cathode layer successively on the anode layer, obtain the organic fluorescence light-emitting diode of planar heterojunction sensitization.
The method of described preparation comprises hot evaporation, spin coating, brushing, spraying, dip-coating, roller coat, printing or inkjet printing.
Preparation method of the present invention and the product tool obtained have the following advantages and beneficial effect:
(1) device architecture involved in the present invention is simple, and preparation flow is few, can realize low driving voltage and high external quantum efficiency simultaneously;
(2) device organic layer involved in the present invention, not containing precious metal element, is beneficial to the material cost reducing device;
(3) device involved by invention does not need to increase sensitization main body or auxiliary sensitization material of main part especially, only needs the plane P N heterojunction utilizing charge transport materials to form as sensitivity speck, decreases the material category required for device preparation;
(4) device involved in the present invention can utilize singlet and triplet excitons to carry out radioluminescence simultaneously, and theoretical internal quantum efficiency reaches 100%, can realize high colorimetric purity and and high luminous efficiency simultaneously.
Accompanying drawing explanation
Fig. 1 is the stratose structural representation of the organic fluorescence light-emitting diode of planar heterojunction sensitization of the present invention;
Fig. 2 is the current density-brightness-voltage characteristic curve chart of the organic fluorescence light-emitting diode of the planar heterojunction sensitization that embodiment 1 obtains;
Fig. 3 is the current efficiency-external quantum efficiency-current density characteristics curve chart of the organic fluorescence light-emitting diode of the planar heterojunction sensitization that embodiment 1 obtains;
The electroluminescent spectrum figure of organic fluorescence light-emitting diode under different current density of the planar heterojunction sensitization of Fig. 4 to be DMQA doping content that embodiment 1 obtains be 0.1% (a), 0.2% (b), 0.4% (c) and 0.6% (d);
Fig. 5 is the organic fluorescence LED device 1 of the planar heterojunction sensitization that embodiment 2 obtains and the current density-brightness-voltage characteristic curve chart of device 2;
Fig. 6 is the organic fluorescence LED device 1 of the planar heterojunction sensitization that embodiment 2 obtains and the current efficiency-external quantum efficiency-current density characteristics curve chart of device 2;
Fig. 7 is the organic fluorescence LED device 1 (a) of the planar heterojunction sensitization that embodiment 2 obtains and the electroluminescent spectrum figure under different current density of device 2 (b).
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
Get same lot number ITO Conducting Glass some, specification is 30 millimeters × 30 millimeters, and ITO thickness is about 90 nanometers, and its square resistance is about 20 ohms/square.Use acetone, micron order semiconductor special purpose detergent, deionized water, the ultrasonic cleaning of isopropyl alcohol 15 minutes successively, to remove the dirt of substrate surface.Put into insulating box 80 degrees Celsius oven dry subsequently stand-by.ITO substrate after oven dry plasma glow start device processes 4 minutes, the further organic pollution of removing surface attachment.Subsequently ITO substrate-transfer to anhydrous and oxygen-free, the glove box being full of high pure nitrogen.In this glove box, device is loaded in Vacuum Deposition chamber.Open mechanical pump and molecular pump, when reaching 4 × 10 in plating chamber
-4high vacuum after start hot evaporated film.Utilize specific mask plate, (doping content is 0.1% to the N-type organic semiconducting materials TmPyTZ that mixes of evaporation anode buffer layer material TAPC, P type organic semiconducting materials TCTA, DMQA successively, 0.2%, 0.4%, 0.6%, molar ratio), cathode cushioning layer material lithium fluoride, cathodic metal aluminium.The thickness of evaporation layer is monitored in real time by quartz crystal oscillator film thickness detector, and the thickness controlling anode buffer layer material TAPC is respectively 25 nanometers, the thickness of P type organic semiconducting materials TCTA layer is 10 nanometers, the thickness of the N-type organic semiconducting materials TmPyTZ layer of DMQA doping is 60 nanometers.Obtain the organic fluorescence light-emitting diode of planar heterojunction sensitization: ito glass substrate/TAPC (25 nanometer)/TCTA (10 nanometer)/DMQA adulterates TmPyTZ (60 nanometer)/lithium fluoride (1 nanometer)/aluminium.
The light-emitting diode of the different DMQA dopant concentration that the present embodiment obtains carries out photoelectric properties test: after prepared by device, device is taken out from evaporation cavity, utilizes glass cover-plate, carry out simplified package by the packaging plastic of epoxy resin in glove box.Then take out in air and test, testing equipment is the CS200 luminance meter that Konica-Minolta company generates, and 2400 sources that device current information of voltage is generated by Keithley company are shown to measure.Current efficiency, the power efficiency of device can be extrapolated respectively by information such as brightness, electric current, voltages.Under the supposed premise of lambertian distribution, according to the external quantum efficiency of brightness, current density, electroluminescent spectrum calculating device.The PR705 testing of equipment that the electroluminescent spectrum of device is produced by PhotoResearch company and obtaining.
The organic fluorescence light-emitting diode of the planar heterojunction sensitization that this enforcement obtains: ito glass substrate/TAPC (25 nanometer)/TCTA (10 nanometer)/DMQA adulterates the current density-brightness-voltage characteristic curve chart of TmPyTZ (60 nanometer)/lithium fluoride (1 nanometer)/aluminium, current efficiency-external quantum efficiency-current density characteristics curve chart and the electroluminescent spectrum figure under different current density respectively as shown in Figure 2, Figure 3 and Figure 4.In the device that (a), (b), (c) and (d) wherein in Fig. 4 is corresponding respectively, the doping content of DMQA is 0.1%, 0.2%, 0.4% and 0.6%.
Result by 2 ~ 4 is known, and along with the doping content of fluorescein DMQA increases, the luminous component that device derives from fluorescein presents gradually, and spectral signature shows as the luminescence of fluorescein.Under the doping content of 0.6%, spectrum is presented as the luminescence feature of fluorescein, and now achieving the maximum external quantum efficiency of device is 9.57%, has exceeded the restriction of conventional fluorescent device 5% external quantum efficiency.This device is that monolateral N-type organic material side utilizes fluorescein DMQA to carry out the type of device of adulterating.
Embodiment 2
Preparation process is as embodiment 1 but without anode buffer layer, P type organic semiconducting materials be chosen as respectively DMQA doping TAPC (doping content is 0.7%, molar ratio) and DMQA doping TCTA (doping content is 1.1%, molar ratio), N-type organic semiconducting materials be DMQA doping TmPyTZ (doping content is 0.7%, molar ratio).The thickness of control P type organic semiconductor material is the thickness of 25 nanometers and N-type organic semiconductor material is 60 nanometers, obtains the organic fluorescence light-emitting diode of planar heterojunction sensitization respectively: ito glass substrate/DMQA adulterate TmPyTZ (60 nanometer)/lithium fluoride (1 nanometer)/aluminium (device 1) and ito glass substrate/DMQA of TAPC (25 nanometer)/DMQA that adulterate adulterates TCTA (25 nanometer)/DMQA doping TmPyTZ (60 nanometer)/lithium fluoride (1 nanometer)/aluminium (device 2).This device is that bilateral P type semiconductor material and N-type organic semiconducting materials utilize fluorescein DMQA to carry out the type of device of adulterating simultaneously.
Electroluminescent spectrum figure under the current density-brightness-voltage characteristic curve chart of the light-emitting diode that the present embodiment obtains, current efficiency-external quantum efficiency-current density characteristics curve chart and different current density respectively as shown in Fig. 5, Fig. 6 and Fig. 7, the wherein electroluminescent spectrum figure of Fig. 7 (a) device 1; The electroluminescent spectrum figure that Fig. 7 (b) is device 2.Result as can be seen from figure: when the planar heterojunction utilizing P type organic semiconducting materials TAPC and N-type organic semiconducting materials TmPyTZ to form is adulterated, the electroluminescent spectrum of device has showed the feature of fluorescein DMQA transmitting, device achieves the maximum external quantum efficiency of 8.0%, and the cut-in voltage of device is low to moderate 2.16V simultaneously.When the planar heterojunction utilizing P type organic semiconducting materials TCTA and N-type organic semiconducting materials TmPyTZ to form carries out bilateral doping fluorescent element DMQA, can see that the electroluminescent spectrum of device shows as the transmitting of purer fluorescein, the luminescence of of TCTA/TmPyTZ planar heterojunction itself, by cancellation greatly, describes by the sensitization luminescence of object fluorescein effectively of this planar heterojunction structure.The maximum external quantum efficiency of device still reaches 8%, has exceeded the theory restriction of maximum 5% external quantum efficiency of conventional fluorescent OLED.Which illustrate by plane P N heterojunction as sensitivity speck, can realize the luminescence of sensitization object fluorescence molecule, the radiation simultaneously realizing triplet excitons and singlet exciton utilizes.
Above-described embodiment is the present invention's preferably execution mode; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from Spirit Essence of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (10)
1. an organic fluorescence light-emitting diode for planar heterojunction sensitization, is characterized in that: comprise the substrate, anode, p-type organic semiconductor layer, n-type organic semiconductor layer and the negative electrode that stack gradually; One deck doping fluorescent material is had at least in described p-type organic semiconductor layer and n-type organic semiconductor layer.
2. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to claim 1, is characterized in that: described p-type organic semiconductor layer prepare material for having one or more blended in the material of following (1) ~ (48) molecular structural formula:
3. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to claim 1, is characterized in that: the material of preparing of described n-type organic semiconductor layer is one or more blended had in the molecular structural formula material of following ETM-1 ~ 55:
4. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to claim 1, is characterized in that: described fluorescence dopant material is for having one or more blended in following (a) ~ (i) molecular structural formula material:
5. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to any one of Claims 1 to 4, is characterized in that: described p-type organic semiconductor layer and n-type organic semiconductor layer are single or multiple lift.
6. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to any one of Claims 1 to 4, is characterized in that: add one deck resilient coating individually or simultaneously between described anode and p-type organic semiconductor layer, between negative electrode and N-type organic semiconducting materials.
7. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to any one of Claims 1 to 4, is characterized in that: described substrate is glass, quartz, sapphire, polyimides, PETG, mylar's fat, PEN, metal, alloy or stainless steel film.
8. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to any one of Claims 1 to 4, is characterized in that: described anode and negative electrode are metal or metal oxide; Described metal oxide refers to one or more the combination in tin indium oxide, fluorine-doped tin dioxide, zinc oxide and indium gallium zinc oxide.
9. the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization according to any one of Claims 1 to 4, is characterized in that: the luminescent spectrum of the organic fluorescence light-emitting diode of described planar heterojunction sensitization derives from the fluorescent material mixed.
10. the preparation method of the organic fluorescence light-emitting diode of a kind of planar heterojunction sensitization described in any one of claim 1 ~ 9, is characterized in that comprising the following steps:
Get the backing material with anode layer, then prepare p-type organic semiconductor layer, n-type organic semiconductor layer and cathode layer successively on the anode layer, obtain the organic fluorescence light-emitting diode of planar heterojunction sensitization; The method of described preparation comprises hot evaporation, spin coating, brushing, spraying, dip-coating, roller coat, printing or inkjet printing.
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