CN101005122A - Method for preparing organic ELD capable of regulating light emitting colors - Google Patents
Method for preparing organic ELD capable of regulating light emitting colors Download PDFInfo
- Publication number
- CN101005122A CN101005122A CNA2006100112271A CN200610011227A CN101005122A CN 101005122 A CN101005122 A CN 101005122A CN A2006100112271 A CNA2006100112271 A CN A2006100112271A CN 200610011227 A CN200610011227 A CN 200610011227A CN 101005122 A CN101005122 A CN 101005122A
- Authority
- CN
- China
- Prior art keywords
- equation
- phenyl
- electron transport
- formula
- transport material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The preparation method includes two types: interface type and mixed type. The interface type includes steps: (1) vacuum depositing or spin coating hole transport material on substrate glass of oxide of stannum indium; (2) vacuum depositing electron transmission material with capability of attracting electrons highly; (3) vacuum depositing cathode layer. The mixed type includes step (1), and then step of vacuum depositing, or spin coating mixing layer of cavity transmission material and electron transmission material. The invention does not need vacuum depositing luminescent material so as to reduce material utilized, and facilitate procedure for preparing device. Using created different activation based compound realizes luminescence in different colors.
Description
Technical field
The present invention relates to a kind of preparation method of Organic Light Emitting Diode, relate in particular to a kind of preparation method who regulates and control the Organic Light Emitting Diode of glow color based on exciplex.
Background technology
After Organic Light Emitting Diode (OLEDs) was in the news from 1987 (C.W.Tang, S.A.VanSlyke, Appl.Phys.Lett.1987,51,913), because its potential application aspect demonstration and illumination has obtained significant progress so far.As everyone knows, be used for showing needing Red Green Blue, for this reason people synthesized various can red-emitting, luminous organic material (C.T.Chen, Chem.Mater.2004,16,4389 of green glow, blue light; A.Kraft, A.C.Grimsdale, A.B.Holmes, Angew.Chem., Int.Ed.1998,37,402; Y.Sato, Semicond.Semimet.2000,64,209.).In preparation during chromatic display, need these red, green, blue luminescent materials all successively spin coating or evaporation to substrate.But often brightness and luminous efficiency are not high with the single layer structure device of these red, green, blue luminescent materials preparation, need to introduce the luminescent properties that hole transmission layer and electron transfer layer improve device.The increase of the fabricate devices material requested and the number of plies can cause drawbacks such as manufacturing process complexity, manufacturing cost increase.We know that the molecule (electron donor) with strong electron donation forms charge-transfer complex or exciplex with the molecule (electron acceptor) with strong electron-withdrawing power easily, the appearance of these new species can cause with respect to electron donor and electron acceptor separately long wavelength's direction of emission peak low-yield emission peak (N.Mataga appears, Y.Murata, J.Am.Chem.Soc.1969,91,3144; D.D.Gebler, Y.Z.Wang, J.W.Blatchford, Appl.Phys.Lett.1997,7O, 1644; R.Aroca, T.D.Cano, J.A.De Saja, Chem.Mater.2003,15,38).The glow color that electron donor by selecting different electron donations and electron-withdrawing power for use and electron acceptor can be regulated and control charge-transfer complex or exciplex.Usually the hole mobile material of usefulness generally all is an electron donor, if select for use suitable electron acceptor as electron transport material, make it realize the luminous of different colours with different hole mobile material formation charge-transfer complex or exciplex, can save this one deck of luminescent material like this, thereby simplify preparation of devices and omit the synthetic of different glow color materials and use.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of Organic Light Emitting Diode of the color tunable control based on exciplex, the Organic Light Emitting Diode of the present invention's preparation comprises two types of interface type and mixed types.
For achieving the above object, the present invention prepares the interface type method of organic light emitting diodes, and its key step is:
A) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form hole transmission layer with speed evaporation or the spin coating hole mobile material on tin indium oxide (ITO) glass substrate of 0.1～2 /s;
B) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form electron transfer layer with speed evaporation electron transport material on hole transmission layer of 0.1～2 /s;
C) evaporation cathode layer on electron transfer layer;
Described hole mobile material is:
N, N '-diphenyl-N, N '-two (3-aminomethyl phenyl)-1,1 '-biphenyl-4,4 '-diamines (TPD), structure as shown in Equation 1:
4,4 '-two-(N-naphthyl-N-phenyl amino) biphenyl (NPB), structure are as shown in Equation 2:
Polyvinylcarbazole (PVK), structure be as shown in Equation 3:
4,4 '-two-(N-carbazyl)-2,2 '-biphenyl (CBP), structure as shown in Equation 4:
Described electron transport material is:
6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (CPQ), structure as shown in Equation 5:
2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines (CPP), structure as shown in Equation 6:
6,7-dimethyl-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (MPQ), structure as shown in Equation 7:
Described cathode layer is lithium, calcium, barium, magnesium, silver, aluminium and their alloy.
The key step of preparation mixed type organic light-emitting diodes is:
A) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form hole transmission layer with speed evaporation or the spin coating hole mobile material on tin indium oxide (ITO) glass substrate of 0.1～2 /s;
B) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa, composite material with the speed of 0.1～2 /s evaporation or spin coating hole mobile material and electron transport material on hole transmission layer, to form the mixed layer of hole mobile material and electron transport material, wherein the percentage by weight of electron transport material in mixture is 1%～50%;
C) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form electron transfer layer with speed evaporation electron transport material on hole transmission layer of 0.1～2 /s;
D) evaporation cathode layer on electron transfer layer;
Described hole mobile material is:
N, N '-diphenyl-N, N '-two (3-aminomethyl phenyl)-1,1 '-biphenyl-4,4 '-diamines (TPD), structure as shown in Equation 1:
4,4 '-two-(N-naphthyl-N-phenyl amino) biphenyl (NPB), structure are as shown in Equation 2:
Polyvinylcarbazole (PVK), structure be as shown in Equation 3:
Or
4,4 '-two-(N-carbazyl)-2,2 '-biphenyl (CBP), structure as shown in Equation 4:
Described electron transport material is:
6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (CPQ), structure as shown in Equation 5:
2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines (CPP), structure as shown in Equation 6:
Or
6,7-dimethyl-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline (MPQ), structure as shown in Equation 7:
Described cathode layer is lithium, calcium, barium, magnesium, silver, aluminium and their alloy.
Described Organic Light Emitting Diode, wherein substrate is that one of them is made by glass, pottery, polymer.
Described Organic Light Emitting Diode, wherein hole mobile material is organic small molecule material, macromolecule polymer material or their mixture with electron donation, can adopt vacuum evaporation, gets rid of film, drip film, their film of printing technology preparation.
Described Organic Light Emitting Diode, wherein electron transport material is organic small molecule material, macromolecule polymer material or their mixture with the electronic capability accepted, and can adopt vacuum evaporation, gets rid of film, drip film, their film of printing technology preparation.
Described Organic Light Emitting Diode, wherein hole mobile material and electron transport material easily form charge-transfer complex or exciplex.
Described Organic Light Emitting Diode, wherein the number of plies of organic layer is not limited to 2 or 3 layers, can be more than 1 layer or 3 layers.
The present invention has following feature:
1, for the interface type device: device architecture comprises ito anode, and hole transmission layer has the electron transfer layer of electron-withdrawing power by force, negative electrode.
For hybrid device: device architecture comprises ito anode, hole transmission layer, and hole mobile material and the mixed layer that has the electron transport material of strong electron-withdrawing power to form have the electron transfer layer of strong electron-withdrawing power, negative electrode.
2, for the interface type device: device luminous is derive from exciplex that hole transmission layer and electron transfer layer form at the interface luminous.
For hybrid device: device luminous is derive from the exciplex that forms in hole mobile material and the electron transport material mixed layer luminous.
3, the present invention is by a kind of hole mobile material effect that electron transport material with the different electron donations of strong electron-withdrawing power are arranged, and can produce exciplex luminous of different colours, realizes that glow color regulates and control.
The present invention has the following advantages:
1, the present invention prepares OLEDs and need not the evaporation luminescent material, only need hole mobile material and two kinds of materials of electron transport material just can, reduced the use of material, convenient preparation of devices process.
2, the present invention utilizes the different exciplexs of generation can realize the luminous of different colours.
3, the present invention by hole mobile material selection and with the adjustable glow color of the combination of different acceptor materials.
4, the OLEDs of the present invention's preparation has higher luminosity and efficient.
Description of drawings
Fig. 1 is a device architecture schematic diagram of the present invention: (a) interface type device, (b) hybrid device.
Fig. 2 is used hole mobile material and the fluorescence spectrum of electron transport material under filminess of the present invention.
Fig. 3 for the used electron transport material CPQ of the present invention respectively with the fluorescence spectrum of the mixture of hole mobile material TPD, NPB, PVK, CBP.
Fig. 4 for the used electron transport material CPP of the present invention respectively with the fluorescence spectrum of the mixture of hole mobile material TPD, NPB, PVK, CBP.
Fig. 5 for the used electron transport material MPQ of the present invention respectively with the fluorescence spectrum of the mixture of hole mobile material TPD, NPB, PVK, CBP.
Fig. 6 is the electroluminescent spectrum of the interface type device of the present invention's preparation: electron transport material is CPQ, and device architecture is respectively:
ITO/TPD/CPQ/Al、ITO/NPB/CPQ/Al、ITO/PVK/CPQ/Al、ITO/NPB/CBP/CPQ/Al。
Fig. 7 is the electroluminescent spectrum of the interface type device of the present invention's preparation: electron transport material is CPP, and device architecture is respectively:
ITO/TPD/CPP/Al、ITO/NPB/CPP/Al、ITO/PVK/CPP/Al、ITO/NPB/CBP/CPP/Al。
Fig. 8 is the electroluminescent spectrum of the hybrid device of the present invention's preparation: electron transport material is CPQ, and device architecture is respectively:
ITO/TPD/TPD：CPQ/CPQ/Al、ITO/NPB/NPB：CPQ/CPQ/Al、
ITO/PVK：CPQ/CPQ/Al、ITO/NPB/CBP/CBP：CPQ/CPQ/Al。
Fig. 9 is the electroluminescent spectrum of the hybrid device of the present invention's preparation: electron transport material is CPP, and device architecture is respectively:
ITO/TPD/TPD：CPP/CPP/Al、ITO/NPB/NPB：CPP/CPP/Al、
ITO/PVK：CPP/CPP/Al，ITO/NPB/CBP/CBP：CPP/CPP/Al。
Figure 10 is the electroluminescent spectrum of the hybrid device of the present invention's preparation: electron transport material is MPQ, and device architecture is respectively:
ITO/TPD/TPD：MPQ/MPQ/Al、ITO/NPB/NPB：MPQ/MPQ/Al、
ITO/PVK：MPQ/MPQ/Al、ITO/NPB/CBP/CBP：MPQ/MPQ/Al。
Embodiment:
The present invention is described in detail below in conjunction with drawings and Examples, and wherein embodiment 1-8 is the interface type preparation of devices, and embodiment 9-20 is the preparation of hybrid device.
The organic semiconducting materials of preparation interface type OLEDs: hole mobile material is TPD, and its structural formula respectively as shown in Equation 1
Electron transport material is CPQ, and its structural formula as shown in Equation 5
The used anode of device is ITO, and negative electrode is aluminium (Al), but negative electrode is not limited to this, also can be metal and their alloys such as lithium, calcium, barium, magnesium, silver.The device architecture that makes up is seen Fig. 1 a.
Implementation step:
The first step: the cleaning of ito glass
Ito glass cleans with washing agent, running water, deionized water, acetone, absolute ethyl alcohol successively, places baking oven to dry then.
Second step: evaporation hole transmission layer
The ito glass sheet of cleaning is placed in the vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, with the deposited at rates hole mobile material TPD of 2 /s.
The 3rd step: evaporation electron transfer layer
In vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, with the deposited at rates electron transport material CPQ of 2 /s.
The gross thickness of organic semiconductor layer is 100nm in the device.
The 4th step: negative electrode preparation
Evaporating Al negative electrode on the ITO substrate of the intact organic layer of evaporation, thickness is 100nm.
The 5th step: the test of device performance
Above-mentioned device is tested under room temperature, atmospheric environment: current-voltage curve is recorded by the HP4140B semi-conductor test instrument; Luminous power is recorded by the NewPort2835C light power meter, can obtain light emission luminance value through conversion; Chromaticity coordinates is recorded by the PR-650 colorimeter.
The device architecture of preparation is ITO/TPD/CPQ/Al.
Embodiment 2
Press the method fabricate devices of embodiment 1, that different is hole mobile material NPB, and structure as shown in Equation 2.
The device architecture of preparation is ITO/NPB/CPQ/Al.
Embodiment 3
The organic semiconducting materials of preparation OLEDs: hole mobile material is PVK, and its structural formula is distinguished as shown in Equation 3:
Electron transport material is CPQ.
The used anode of device is ITO, and negative electrode is aluminium (Al), but negative electrode is not limited to this, also can be metal and their alloys such as lithium, calcium, barium, magnesium, silver.The device architecture that makes up is seen Fig. 1 a.
Implementation step:
The first step: the cleaning of ito glass
Ito glass cleans with washing agent, running water, deionized water, acetone, absolute ethyl alcohol successively, places baking oven to dry then.
Second step: spin coating hole transmission layer
The chloroformic solution (6mg/ml) of spin coating PVK on the ito glass sheet of cleaning.
All the other steps are with embodiment 1.
The device architecture of preparation is ITO/PVK/CPQ/Al.
Embodiment 4
The organic semiconducting materials of preparation OLEDs: hole mobile material is NPB and CBP, and the structural formula of CBP as shown in Equation 4.
Electron transport material is CPQ.
The used anode of device is ITO, and negative electrode is aluminium (Al), but negative electrode is not limited to this, also can be metal and their alloys such as lithium, calcium, barium, magnesium, silver.The device architecture that makes up is seen Fig. 1 a.
Implementation step:
The first step: the cleaning of ito glass
Ito glass cleans with washing agent, running water, deionized water, acetone, absolute ethyl alcohol successively, places baking oven to dry then.
Second step: evaporation hole transmission layer
The ito glass sheet of cleaning is placed in the vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, the deposition one deck hole mobile material NPB of speed elder generation with 2 /s deposits one deck hole mobile material CBP again.The purpose of deposition NPB layer is in order to reduce the energy barrier that the hole is injected into the CBP layer.
All the other steps are with embodiment 1.
The device architecture of preparation is ITO/NPB/CBP/CPQ/Al.
Embodiment 5
Press the method fabricate devices of embodiment 1, that different is electron transport material CPP, and structure as shown in Equation 6.
The device architecture of preparation is ITO/TPD/CPP/Al.
Embodiment 6
Press the method fabricate devices of embodiment 2, that different is electron transport material CPP.
The device architecture of preparation is ITO/NPB/CPP/Al.
Embodiment 7
Press the method fabricate devices of embodiment 3, that different is electron transport material CPP.
The device architecture of preparation is ITO/PVK/CPP/Al.
Embodiment 8
Press the method fabricate devices of embodiment 4, that different is electron transport material CPP.
The device architecture of preparation is ITO/NPB/CBP/CPP/Al.
Embodiment 9
The organic semiconducting materials of preparation mixed type OLEDs: hole mobile material is TPD, and electron transport material is CPQ.The used anode of device is ITO, and negative electrode is aluminium (Al), but negative electrode is not limited to this, also can be metal and their alloys such as lithium, calcium, barium, magnesium, silver.The device architecture that makes up is seen Fig. 1 b.
Implementation step:
The first step: the cleaning of ito glass
Ito glass cleans with washing agent, running water, deionized water, acetone, absolute ethyl alcohol successively, places baking oven to dry then.
Second step: evaporation hole transmission layer
The ito glass sheet of cleaning is placed in the vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, with the deposited at rates hole mobile material TPD of 2 /s.
The 3rd step: the mixed layer of evaporation hole mobile material and electron transport material
In vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, deposit hole mobile material TPD and electron transport material CPQ simultaneously, form TPD: the CPQ mixed layer with the speed of 2 /s.
The 4th step: evaporation electron transfer layer
In vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, with the deposited at rates electron transport material CPQ of 2 /s.
The gross thickness of organic semiconductor layer is 100nm in the device.
The 5th step: negative electrode preparation
Evaporating Al negative electrode on the ITO substrate of the intact organic layer of evaporation, thickness is 100nm.
The 6th step: the test of device performance
Above-mentioned device is tested under room temperature, atmospheric environment: current-voltage curve is recorded by the HP4140B semi-conductor test instrument; Luminous power is recorded by the NewPort2835C light power meter, can obtain light emission luminance value through conversion; Chromaticity coordinates is recorded by the PR-650 colorimeter.
The device architecture of preparation is: ITO/TPD/TPD:CPQ/CPQ/Al.
Embodiment 10
Press the method fabricate devices of embodiment 9, that different is hole mobile material NPB.
The device architecture of preparation is: ITO/NPB/NPB:CPQ/CPQ/Al.
Embodiment 11
The organic semiconducting materials of preparation OLEDs: hole mobile material is PVK, and electron transport material is CPQ.The used anode of device is ITO, and negative electrode is aluminium (Al), but negative electrode is not limited to this, also can be metal and their alloys such as lithium, calcium, barium, magnesium, silver.The device architecture that makes up is seen Fig. 1 b.
Implementation step:
The first step: the cleaning of ito glass
Ito glass cleans with washing agent, running water, deionized water, acetone, absolute ethyl alcohol successively, places baking oven to dry then.
Second step: the mixed layer of spin coating hole mobile material and electron transport material
Hole mobile material PVK and electron transport material CPQ are dissolved in the chloroform jointly, are mixed with solution, wherein the concentration of PVK is 6mg/ml, and CPQ is 5%～30% with respect to the weight ratio of PVK.The above-mentioned solution of spin coating on the ito glass of cleaning forms PVK: the CPQ mixed layer.
The 3rd step: evaporation electron transfer layer
In vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, with the deposited at rates electron transport material CPQ of 2 /s.
The gross thickness of organic semiconductor layer is 100nm in the device.
Negative electrode preparation and device performance test are with embodiment 9.
The device architecture of preparation is ITO/PVK:CPQ/CPQ/Al.
Embodiment 12
The organic semiconducting materials of preparation OLEDs: hole mobile material is NPB and CBP, and electron transport material is CPQ.The used anode of device is ITO, and negative electrode is aluminium (Al), but negative electrode is not limited to this, also can be metal and their alloys such as lithium, calcium, barium, magnesium, silver.The device architecture that makes up is seen Fig. 1 b.
Implementation step:
The first step: the cleaning of ito glass
Ito glass cleans with washing agent, running water, deionized water, acetone, absolute ethyl alcohol successively, places baking oven to dry then.
Second step: evaporation hole transmission layer
The ito glass sheet of cleaning is placed in the vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, the deposition one deck hole mobile material NPB of speed elder generation with 2 /s deposits one deck hole mobile material CBP again.The purpose of deposition NPB layer is to reduce the energy barrier that the hole is injected into the CBP layer.
The 3rd step: the mixed layer of evaporation hole mobile material and electron transport material
In vacuum chamber, 4 * 10
-4Under the vacuum degree of Pa, deposit hole mobile material CBP and electron transport material CPQ simultaneously, form CBP: the CPQ mixed layer with the speed of 2 /s.
All the other steps are with embodiment 9.
The device architecture of preparation is ITO/NPB/CBP/CBP:CPQ/CPQ/Al.
Embodiment 13
Press the method fabricate devices of embodiment 9, that different is electron transport material CPP.
The device architecture of preparation is ITO/TPD/TPD:CPP/CPP/Al.
Embodiment 14
Press the method fabricate devices of embodiment 10, that different is electron transport material CPP.
The device architecture of preparation is ITO/NPB/NPB:CPP/CPP/Al.
Embodiment 15
Press the method fabricate devices of embodiment 11, that different is electron transport material CPP.
The device architecture of preparation is ITO/PVK:CPP/CPP/Al.
Embodiment 16
Press the method fabricate devices of embodiment 12, that different is electron transport material CPP.
The device architecture of preparation is ITO/NPB/CBP/CBP:CPP/CPP/Al.
Embodiment 17
Press the method fabricate devices of embodiment 9, that different is electron transport material MPQ, and structure as shown in Equation 7.
The device architecture of preparation is ITO/TPD/TPD:MPQ/MPQ/Al.
Embodiment 18
Press the method fabricate devices of embodiment 10, that different is electron transport material MPQ.
The device architecture of preparation is ITO/NPB/NPB:MPQ/MPQ/Al.
Embodiment 19
Press the method fabricate devices of embodiment 11, that different is electron transport material MPQ.
The device architecture of preparation is ITO/PVK:MPQ/MPQ/Al.
Embodiment 20
Press the method fabricate devices of embodiment 12, that different is electron transport material MPQ.
The device architecture of preparation is ITO/NPB/CBP/CBP:MPQ/MPQ/Al.
Hole mobile material and the fluorescence spectrum of electron transport material under filminess that the present invention is used have been showed among Fig. 2, the fluorescent emission that can find out hole mobile material is all in royal purple light or purple light zone, in blue region, the fluorescent emission of MPQ is in the purple light zone in the fluorescent emission of blue green light zone, CPP for electron transport material CPQ fluorescent emission.
Fig. 3,4 and 5 is the fluorescence spectrum of electron transport material when mixing mutually with the hole mobile material of different electron donations.A new emission peak can occur in the long wavelength's direction with respect to its one pack system emission peak as can be seen, this is that electron transport material and hole mobile material form the luminous result of exciplex.
Fig. 6 and 7 electroluminescent spectrums for the interface type device of the present invention preparation can be found out similarly with 4 fluorescence spectrum with Fig. 3 respectively, the emission of exciplex occurred and occupy an leading position.
Fig. 8,9 and 10 electroluminescent spectrums for the hybrid device of the present invention preparation are respectively to Fig. 3,4 similar with 5 fluorescence spectrum.
Provided the electroluminescence characters of the device of the present invention's preparation in the table 1.The device that forms exciplex with CPP and hole mobile material has preferable performance, and high-high brightness can reach 3140cd/m
2(device CBP: CPP).
Table 1
| Give body and acceptor | Electroluminescence peak position (nm) | The CIE coordinate | Glow color | High-high brightness (cd/m 2) | Maximum luminous efficiency (cd/A) |
| TPD/CPQ | 656 | (0.64，0.33) | Red | 148 | 0.1 |
| NPB/CPQ | 645 | (0.60，0.33) | Red | 135 | 0.1 |
| PVK/CPQ | 593 | (0.49，0.46) | Yellow | 867 | 1.4 |
| CBP/CPQ | 539 | (0.37，0.53) | Yellowish green | 1759 | 1.7 |
| TPD/CPP | 629 | (0.62，0.35) | Red | 275 | 0.2 |
| NPB/CPP | 621 | (0.63，0.35) | Red | 214 | 0.2 |
| PVK/CPP | 585 | (0.44，0.44) | Yellow | 1526 | 2.9 |
| CBP/CPP | 525 | (0.32，0.48) | Yellowish green | 2148 | 1.8 |
| TPD∶CPQ | 651 | (0.65，0.33) | Red | 79 | 0.06 |
| NPB∶CPQ | 643 | (0.60，0.33) | Red | 60 | 0.04 |
| PVK∶CPQ | 591 | (0.46，0.47) | Yellow | 1106 | 2.2 |
| CBP∶CPQ | 542 | (0.37，0.53) | Yellowish green | 983 | 1.0 |
| TPD∶CPP | 631 | (0.62，0.35) | Red | 272 | 0.2 |
| NPB∶CPP | 624 | (0.62，0.36) | Red | 261 | 0.2 |
| PVK∶CPP | 577 | (0.44，0.44) | Yellow | 1760 | 3.3 |
| CBP∶CPP | 527 | (0.31，0.48) | Yellowish green | 3140 | 1.9 |
| TPD∶MPQ | 490 | (0.20，0.34) | Bluish-green | 328 | 0.4 |
| TPB∶MPQ | 488 | (0.19，0.33) | Bluish-green | 378 | 0.6 |
| PVK∶MPQ | 419 | (0.11，0.19) | Royal purple | 4 | 0.04 |
| CBP∶MPQ | 428 | (0.16，0.09) | Royal purple | 101 | 0.3 |
Claims (7)
1. the preparation method of the regulatable Organic Light Emitting Diode of glow color, the key step that wherein prepares the interface type Organic Light Emitting Diode is:
A) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form the film of hole transmission layer with speed evaporation or the spin coating hole mobile material on tin indium oxide (ITO) glass substrate of 0.1～2 /s;
B) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form the film of electron transfer layer with speed evaporation electron transport material on hole transmission layer of 0.1～2 /s;
C) evaporation cathode layer on electron transfer layer;
Described hole mobile material is:
N, N '-diphenyl-N, N '-two (3-aminomethyl phenyl)-1,1 '-biphenyl-4,4 '-diamines, structure as shown in Equation 1:
Formula 1,
4,4 '-two-(N-naphthyl-N-phenyl amino) biphenyl, structure are as shown in Equation 2:
Formula 2,
Polyvinylcarbazole, structure be as shown in Equation 3:
Formula 3 or
4,4 '-two-(N-carbazyl)-2,2 '-biphenyl, structure as shown in Equation 4:
Formula 4;
Described electron transport material is:
6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline, structure as shown in Equation 5:
2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines, structure as shown in Equation 6:
6,7-dimethyl-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline, structure as shown in Equation 7:
Described cathode layer is lithium, calcium, barium, magnesium, silver, aluminium and their alloy.
2. the preparation method of the regulatable Organic Light Emitting Diode of glow color, the key step that wherein prepares the mixed type organic light-emitting diodes is:
A) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form the film of hole transmission layer with speed evaporation or the spin coating hole mobile material on tin indium oxide (ITO) glass substrate of 0.1～2 /s;
B) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa, composite material with the speed of 0.1～2 /s evaporation or spin coating hole mobile material and electron transport material on hole transmission layer, with the film of the mixed layer that forms hole mobile material and electron transport material, wherein the percentage by weight of electron transport material in mixture is 1%～50%;
C) in 2 * 10
-5～8 * 10
-4Under the vacuum degree of Pa,, form the film of electron transfer layer with speed evaporation electron transport material on hole transmission layer of 0.1～2 /s;
D) evaporation cathode layer on electron transfer layer;
Described hole mobile material is:
N, N '-diphenyl-N, N '-two (3-aminomethyl phenyl)-1,1 '-biphenyl-4,4 '-diamines, structure as shown in Equation 1:
Formula 1,
4,4 '-two-(N-naphthyl-N-phenyl amino) biphenyl, structure are as shown in Equation 2:
Formula 2,
Polyvinylcarbazole, structure be as shown in Equation 3:
Formula 3 or
4,4 '-two-(N-carbazyl)-2,2 '-biphenyl, structure as shown in Equation 4:
Formula 4;
Described electron transport material is:
6,7-dicyano-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline, structure as shown in Equation 5:
2,3-dicyano-5,6-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl pyrazines, structure as shown in Equation 6:
6,7-dimethyl-2,3-two-[4-(2,3,4, the 5-tetraphenyl) phenyl]-phenyl quinoxaline, structure as shown in Equation 7:
Described cathode layer is lithium, calcium, barium, magnesium, silver, aluminium and their alloy.
3. Organic Light Emitting Diode as claimed in claim 1 or 2 is characterized in that, described substrate is that one of them is made by glass, pottery, polymer.
4. Organic Light Emitting Diode as claimed in claim 1 or 2, it is characterized in that, described hole mobile material is organic small molecule material, macromolecule polymer material or their mixture with electron donation, can adopt vacuum evaporation, gets rid of film, drip film, their film of printing technology preparation.
5. Organic Light Emitting Diode as claimed in claim 1 or 2, it is characterized in that, described electron transport material is organic small molecule material, macromolecule polymer material or their mixture with the electronic capability accepted, and can adopt vacuum evaporation, gets rid of film, drip film, their film of printing technology preparation.
6. Organic Light Emitting Diode as claimed in claim 1 or 2 is characterized in that described hole mobile material and electron transport material easily form charge-transfer complex or exciplex.
7, Organic Light Emitting Diode as claimed in claim 1 or 2 is characterized in that, the number of plies of described organic layer is not limited to 2 or 3 layers, can be more than 1 layer or 3 layers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100112271A CN100466332C (en) | 2006-01-18 | 2006-01-18 | Method for preparing organic ELD capable of regulating light emitting colors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006100112271A CN100466332C (en) | 2006-01-18 | 2006-01-18 | Method for preparing organic ELD capable of regulating light emitting colors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101005122A true CN101005122A (en) | 2007-07-25 |
| CN100466332C CN100466332C (en) | 2009-03-04 |
Family
ID=38704119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100112271A Expired - Fee Related CN100466332C (en) | 2006-01-18 | 2006-01-18 | Method for preparing organic ELD capable of regulating light emitting colors |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100466332C (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100457739C (en) * | 2006-01-18 | 2009-02-04 | 中国科学院化学研究所 | Dentritic pattern compound, preparation method and application |
| CN102414858A (en) * | 2009-05-05 | 2012-04-11 | 皇家飞利浦电子股份有限公司 | Electroluminescent device |
| CN101562232B (en) * | 2009-05-25 | 2012-05-23 | 中国科学院长春应用化学研究所 | Color-adjustable organic electroluminescent device and preparation method thereof |
| CN103078051A (en) * | 2011-10-26 | 2013-05-01 | 富士迈半导体精密工业（上海）有限公司 | LED (Light-Emitting Diode) crystal grain |
| WO2016086567A1 (en) * | 2014-12-01 | 2016-06-09 | 京东方科技集团股份有限公司 | Light-emitting device and manufacturing method therefor, display apparatus, and optical detection apparatus |
| CN105957979A (en) * | 2011-02-16 | 2016-09-21 | 株式会社半导体能源研究所 | Light-emitting element |
| CN107408636A (en) * | 2015-01-08 | 2017-11-28 | 保土谷化学工业株式会社 | Organic electroluminescence device |
| WO2018219200A1 (en) * | 2017-05-27 | 2018-12-06 | 京东方科技集团股份有限公司 | Organic electroluminescent device, oled substrate and display device |
| CN109494308A (en) * | 2018-11-21 | 2019-03-19 | 上海天马有机发光显示技术有限公司 | A kind of display panel and display device |
| CN113314678A (en) * | 2021-05-28 | 2021-08-27 | 北京京东方技术开发有限公司 | Quantum dot light-emitting device, manufacturing method thereof and display device |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102569677A (en) * | 2012-01-17 | 2012-07-11 | 苏州大学 | Methods for manufacturing dielectric layer and organic electroluminescent device |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2307035A1 (en) * | 1997-03-12 | 1998-09-17 | Yunzhang Wang | Bilayer polymer electroluminescent device featuring interface electroluminescence |
| CN1156198C (en) * | 2001-04-29 | 2004-06-30 | 清华大学 | Flexible organic electroluminescent device |
| JP3848646B2 (en) * | 2003-10-22 | 2006-11-22 | 松下電器産業株式会社 | Organic light emitting device |
-
2006
- 2006-01-18 CN CNB2006100112271A patent/CN100466332C/en not_active Expired - Fee Related
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100457739C (en) * | 2006-01-18 | 2009-02-04 | 中国科学院化学研究所 | Dentritic pattern compound, preparation method and application |
| CN102414858B (en) * | 2009-05-05 | 2014-11-05 | 皇家飞利浦电子股份有限公司 | Electroluminescent device |
| CN102414858A (en) * | 2009-05-05 | 2012-04-11 | 皇家飞利浦电子股份有限公司 | Electroluminescent device |
| CN101562232B (en) * | 2009-05-25 | 2012-05-23 | 中国科学院长春应用化学研究所 | Color-adjustable organic electroluminescent device and preparation method thereof |
| CN105957979B (en) * | 2011-02-16 | 2018-02-23 | 株式会社半导体能源研究所 | Light-emitting component |
| US10573829B2 (en) | 2011-02-16 | 2020-02-25 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| CN105957979A (en) * | 2011-02-16 | 2016-09-21 | 株式会社半导体能源研究所 | Light-emitting element |
| US10593895B2 (en) | 2011-02-16 | 2020-03-17 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| US10586934B2 (en) | 2011-02-16 | 2020-03-10 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting element |
| CN103078051A (en) * | 2011-10-26 | 2013-05-01 | 富士迈半导体精密工业（上海）有限公司 | LED (Light-Emitting Diode) crystal grain |
| WO2016086567A1 (en) * | 2014-12-01 | 2016-06-09 | 京东方科技集团股份有限公司 | Light-emitting device and manufacturing method therefor, display apparatus, and optical detection apparatus |
| CN107408636B (en) * | 2015-01-08 | 2019-07-26 | 保土谷化学工业株式会社 | Organic electroluminescence device |
| US10505119B2 (en) | 2015-01-08 | 2019-12-10 | Hodogaya Chemical Co., Ltd. | Organic electroluminescence device |
| CN107408636A (en) * | 2015-01-08 | 2017-11-28 | 保土谷化学工业株式会社 | Organic electroluminescence device |
| WO2018219200A1 (en) * | 2017-05-27 | 2018-12-06 | 京东方科技集团股份有限公司 | Organic electroluminescent device, oled substrate and display device |
| US10720592B2 (en) | 2017-05-27 | 2020-07-21 | Hefei Xinsheng Optoelectronics Technology Co., Ltd. | Organic light emitting diode, OLED display substrate and display device |
| CN109494308A (en) * | 2018-11-21 | 2019-03-19 | 上海天马有机发光显示技术有限公司 | A kind of display panel and display device |
| CN113314678A (en) * | 2021-05-28 | 2021-08-27 | 北京京东方技术开发有限公司 | Quantum dot light-emitting device, manufacturing method thereof and display device |
| CN113314678B (en) * | 2021-05-28 | 2024-04-09 | 北京京东方技术开发有限公司 | Quantum dot light emitting device, manufacturing method thereof and display device |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100466332C (en) | 2009-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100466332C (en) | Method for preparing organic ELD capable of regulating light emitting colors | |
| CN1302565C (en) | High efficiency multi-color electro-phosphorescent OLEDs | |
| CN102292839B (en) | By the OLED stability that the hole transmission layer of doping improves | |
| CN101217187B (en) | Preparation method if organic electroluminescence device with super-thin layer structure | |
| CN102136550B (en) | White light organic electroluminescent device and preparation method thereof | |
| CN101170853A (en) | A white light organic EL part consisting of RGB and its making method | |
| CN102031104B (en) | Bipolar phosphorescent main material containing anthracene derivatives of tetraphenyl silicane and carbazole and organic electroluminescent device | |
| CN102097598B (en) | Organic light-emitting device and production method thereof | |
| CN102903854A (en) | White-light organic electroluminescent device and production method thereof | |
| CN109802047A (en) | A kind of organic luminescent device and preparation method thereof based on infrared band | |
| CN109256473A (en) | White organic LED and preparation method | |
| CN101118953A (en) | Organic electroluminescent device and method for producing the same | |
| CN100495761C (en) | Organic electro-white light device and producing method thereof | |
| CN1921171A (en) | White light organic electroluminescent device | |
| CN100386903C (en) | Preparation method of white organic electroluminescent device | |
| CN101123298A (en) | A structure-optimized white light organic EL part | |
| CN102208552A (en) | White-light organic electroluminescent device and preparation method thereof | |
| CN107086271A (en) | A kind of fluorescent/phosphorescent mixed white light OLED | |
| CN102130301B (en) | White organic electroluminescence device based on color conversion and manufacturing method thereof | |
| TWI740209B (en) | Quantum dot light-emitting diode and manufacturing method thereof | |
| CN101022155A (en) | Organic electroluminescent device and producing method thereof | |
| CN108682748A (en) | A kind of series connection white light organic electroluminescent device | |
| CN100454608C (en) | Method for making white-light organic light-emitting-diode | |
| CN101170852A (en) | An organic EL part with ultra-thin layer structure | |
| CN109841759A (en) | A kind of OLED device and preparation method thereof based on platinum complex |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090304 Termination date: 20120118 |