CN106129262B - Ultraviolet organic light-emitting device with double hole injection layers and preparation method thereof - Google Patents
Ultraviolet organic light-emitting device with double hole injection layers and preparation method thereof Download PDFInfo
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- CN106129262B CN106129262B CN201610540845.9A CN201610540845A CN106129262B CN 106129262 B CN106129262 B CN 106129262B CN 201610540845 A CN201610540845 A CN 201610540845A CN 106129262 B CN106129262 B CN 106129262B
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- 238000002347 injection Methods 0.000 title claims abstract description 62
- 239000007924 injection Substances 0.000 title claims abstract description 62
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 7
- 238000004528 spin coating Methods 0.000 claims abstract description 7
- 230000005540 biological transmission Effects 0.000 claims abstract description 6
- 238000002207 thermal evaporation Methods 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 8
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 abstract description 2
- 238000010030 laminating Methods 0.000 abstract 2
- 239000010410 layer Substances 0.000 description 67
- 238000005401 electroluminescence Methods 0.000 description 5
- 229920000144 PEDOT:PSS Polymers 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- FJAOBQORBYMRNO-UHFFFAOYSA-N f16cupc Chemical compound [Cu+2].[N-]1C(N=C2C3=C(F)C(F)=C(F)C(F)=C3C(N=C3C4=C(F)C(F)=C(F)C(F)=C4C(=N4)[N-]3)=N2)=C(C(F)=C(F)C(F)=C2F)C2=C1N=C1C2=C(F)C(F)=C(F)C(F)=C2C4=N1 FJAOBQORBYMRNO-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
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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]
- H10K50/17—Carrier injection layers
-
- 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
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
Abstract
The invention discloses an ultraviolet organic light-emitting device with double hole injection layers and a preparation method thereof, wherein the method comprises the steps of forming the double hole injection layers by laminating a first hole injection layer and a second hole injection layer, the first hole injection layer is made of graphene oxide or PEDOT (graphene oxide: PSS), the second hole injection layer is made of WO3, MoO3 or V2O5, preparing the first hole injection layer on an anode layer by adopting a spin coating process, preparing the second hole injection layer on the first hole injection layer by adopting a vacuum thermal evaporation process, and laminating a hole transmission layer on the second hole injection layer.
Description
The present invention relates to technical field of semiconductor luminescence, and in particular to a kind of to have with the ultraviolet of double hole injection layers
Organic electroluminescence devices and preparation method thereof.
Background technique
Ultraviolet organic electroluminescence device（UV OLED）, because it is in excitation light source, high density data storage, chemical/biological
The application prospect of sensor etc. and be concerned.Since the band gap of ultraviolet luminous organic material is extremely wide, resulting in ultraviolet has
The highest occupied molecular orbital of machine luminescent material（HOMO）Energy level is higher, and hole is difficult to be injected into luminescent layer, in luminescent layer
Hole-electron is seriously uneven, is mainly directed to improve hole injection and transmittability around this way to solve the problem.
Such as buffer layer PEDOT is introduced on ito anode:PSS, CuPc, MoO3, F16CuPc etc. improve Hole injection capacity, but right
For ultraviolet OLED, single layer hole injection layer is obvious insufficient in terms of improving Hole injection capacity, and device performance is undesirable.?
In visible light wave range OLED, also there are many concepts that report proposes double hole injection layers, such as one hundred congruence of Liu to use MeO-TPD/
The bis- hole injection layers of CuPc improve the performance of visible light wave range OLED（With reference to：One hundred congruence of Liu, with novel double hollow cave implanted layer
Organic Light Emitting Diode,《Acta Physica Sinica》2013, volume 62, the 8th phase）.Zhang Jing, fourth are of heap of stone etc. to use the bis- holes HAT-CN/MoO3
The performance of implanted layer raising visible light wave range OLED（With reference to：It opens and waits quietly, the green phosphorescent organic electroluminescence of double holes injections
Part,《Shine journal》2012, the 10th phase；Fourth is of heap of stone etc., novel double hollow cave injection type high efficiency organic electroluminescence diode,《Light
Electronics laser》2011, the 12nd phase）.Hou Jianhua etc. improves top emitting visible light wave range using the bis- hole injection layers of MoO3/C60
The performance of OLED（With reference to：Jian Hua etc. is waited, the performance of top radiation organic EL part is improved using double hole injection layers,《Section
Skill information》2012, the 33rd phase）.However, the hole injection barrier of visible light OLED is lower than ultraviolet organic luminescent device very
More, if existing double hole injection layers are applied directly in ultraviolet OLED, device performance improves less, is hardly obtained reality
Improvement.
Summary of the invention
The present invention provides a kind of preparation method of ultraviolet organic electroluminescence device with double hole injection layers, Yi Jili
The ultraviolet organic luminescent device prepared with this method, can solve the above problem.
The present invention can be effectively facilitated the injection in hole, increase the quantity in hole in luminescent layer, to promote hole-electron
Balance, improve the irradiation level and luminous efficiency of ultraviolet OLED device, while preparation process is simple, practicability is wide.
The present invention uses following technical scheme：
A kind of ultraviolet organic luminescent device preparation method with double hole injection layers, including：It is injected using the first hole
Layer and the second hole injection layer splice a group hole injection layer in pairs, the first hole injection layer material using graphene oxide or
PEDOT:PSS, the second hole injection layer material use WO3, MoO3 or V2O5；On the anode layer using spin coating proceeding preparation first
Hole injection layer prepares the second hole injection layer using vacuum thermal evaporation technique on the first hole injection layer, in the second hole
Splice hole transmission layer on implanted layer.
A kind of ultraviolet organic luminescent device with double hole injection layers, including anode layer, hole injection layer, hole transport
Layer, it is characterised in that：The hole injection layer is by graphene oxide or PEDOT:PSS preparation the first hole injection layer with by
Second hole injection layer of WO3, MoO3 or V2O5 preparation splices composition；First hole injection layer splices with anode layer, institute
State the hole transmission layer that splices on the second hole injection layer
Detailed description of the invention
Fig. 1 is one embodiment of the present of invention structural schematic diagram.
Fig. 2 is the structural schematic diagram of the ultraviolet organic luminescent device of traditional single hole injection layer structure.
Fig. 3 is one embodiment of the present of invention（Device one）With the ultraviolet organic luminescent device of traditional structure（Device two）?
The comparison diagram of irradiation level under different voltages.
Fig. 4 is one embodiment of the present of invention（Device one）With the ultraviolet organic luminescent device of traditional structure（Device two）?
The comparison diagram of external quantum efficiency under different current densities.
In Fig. 1, Fig. 2：1. substrate layer；2. anode layer；3. the first hole injection layer；4. the second hole injection layer；5. hole
Transport layer；6. luminescent layer；7. electron transfer layer；8. electron injecting layer；9. reflective metals cathode layer；10. power supply；11. single hole
Implanted layer.
Specific implementation method
Below with embodiment the present invention will be described in detail technical solution and the beneficial effect that can be obtained.
（1）It chooses and is covered with the glass of ITO as substrate and anode material, successively use acetone, cleaning solution, pure water and different
Propyl alcohol is dried after cleaning substrate and anode, is then handled 10-20 minutes through UV-ozone.
（2）The first hole injection layer is prepared using spin coating proceeding on ITO, the first hole injection layer material can be oxidation
Grapheme material or PEDOT:PSS, this example use graphene oxide, concentration 0.5mg/mL.The thickness of first hole injection layer
Degree can be chosen within the scope of 1-60nm, and this example is about 3nm.Process environments：Revolving speed 3000rpm, spin-coating time 30s, heat treatment
120 DEG C of temperature, heat treatment time 20min.
（3）The second hole injection layer is prepared using vacuum thermal evaporation technique under conditions of vacuum degree is better than 5 × 10-4Pa,
Second hole injection layer material can be WO3, MoO3 or V2O5, and this example uses MoO3.The thickness of second hole injection layer can be with
It is chosen within the scope of 1-20nm, this example is about 5nm.Then it is sequentially depositing hole transmission layer CBP again（With a thickness of 50nm）, luminescent layer
TAZ（With a thickness of 35nm）, electron transfer layer BPhen（With a thickness of 50-70nm）, electron injecting layer LiF（With a thickness of 1nm）；Wherein
CBP indicates 4,4 '-bis (carbazol-9-yl) biphenyl；TAZ indicates 3- (4-biphenyl) -4-phenyl-5-tert-
butylphenyl-1,2,4-triazole；Bphen indicates 4,7-diphenyl-1,10-phenanthroline.
（4）Mask plate, deposition of reflective metal cathode layer Al are replaced under conditions of not destroying vacuum（Thickness is not less than
80nm）.
（5）External circuit is constituted from anode layer by the negative connection reflective metals cathode layer of forward direction.
When applying DC voltage, observe that near ultraviolet is emitted isolychn from anode side.It is measured with voltage and current source table
The driving voltage and electric current of device, with the irradiation level and electroluminescent spectrum of spectrum photometer measurement device.External circuit driving electricity
Direct current 3V-20V may be selected in source.
The ultraviolet OLED device of traditional structure for comparison（Device two）, for substrate using glass, anode selects ito film, side
Resistance is about 10 Ω/, and hole injection layer 11 selects MoO3（With a thickness of 5nm）, remaining is same as Example 1.
From the figure 3, it may be seen that the irradiation level of device one is 0.49mW/cm2, and the irradiation level of device two is when voltage is 6V
0.24mW/cm2, the irradiation level of device one are devices 2 more than 2 times.When voltage is 9V, the irradiation level of device one is 3.0mW/
Cm2, than device two（Irradiation level is 2.1mW/cm2）Improve 43%.The maximum irradiation level of device one is 4.7mW/cm2@11V, device
The maximum irradiation level of part two is 3.7mW/cm2@14V, and the maximum irradiance ratio device two of device one improves 27%.Therefore, this hair
The bright irradiation level that can increase substantially ultraviolet OLED.
As shown in Figure 4, the maximum external quantum efficiency of device one is 1.36%@3.75mA/cm2, the outer quantum of maximum of device two
Efficiency is 1.14%@6.87mA/cm2, and the maximum external quantum efficiency of device one improves 19% than device two.Therefore, the present invention
The external quantum efficiency of ultraviolet OLED can be increased substantially.
The present invention has also been carried out using PEDOT:PSS prepares the first hole injection layer, WO3 and V2O5 is respectively adopted
The ultraviolet organic luminescent device for preparing double hole injection layer structures of the second hole injection layer is infused with traditional single hole
The contrast test for entering the ultraviolet organic luminescent device of layer structure obtains approximate as a result, details are not described herein with Fig. 3, Fig. 4.
Claims (1)
1. a kind of ultraviolet organic luminescent device preparation method with double hole injection layers, it is characterised in that this method is as follows：
（1）, choose and be covered with the glass of ITO as substrate and anode, successively acetone, cleaning solution, pure water and isopropanol is used to wash
It dries after net substrate and anode, is then handled 10-20 minutes through UV-ozone；
（2）, on ITO using spin coating proceeding prepare the first hole injection layer, the first hole injection layer material is graphene oxide,
The concentration of graphene oxide be 0.5mg/mL, the first hole injection layer with a thickness of 3nm, spin coating proceeding environment：Revolving speed
3000rpm, spin-coating time 30s, 120 DEG C of heat treatment temperature, heat treatment time 20min；
（3）, vacuum degree be better than 5 × 10-4Under conditions of Pa using vacuum thermal evaporation technique prepare the second hole injection layer, second
Hole injection layer material is MoO3, the second hole injection layer with a thickness of 5nm, be then sequentially depositing again hole transmission layer CBP, hair
Photosphere TAZ, electron transfer layer BPhen, electron injecting layer LiF；
Wherein,
CBP indicates 4,4 '-bis (carbazol-9-yl) biphenyl；
TAZ indicates 3- (4-biphenyl) -4-phenyl-5-tert-butylphenyl-1,2,4-triazole；
Bphen indicates 4,7-diphenyl-1,10-phenanthroline；
Hole transmission layer CBP with a thickness of 50nm, luminescent layer TAZ with a thickness of 35nm, electron transfer layer BPhen with a thickness of
50-70nm, electron injecting layer LiF with a thickness of 1nm；
（4）, mask plate, deposition of reflective metal cathode layer Al, reflective metals cathode layer Al are replaced under conditions of not destroying vacuum
Thickness be not less than 80nm；
（5）, from anode layer by the negative connection reflective metals cathode layer of forward direction constitute external circuit.
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106784202A (en) * | 2017-02-28 | 2017-05-31 | Tcl集团股份有限公司 | QLED devices and preparation method thereof |
| CN107068884B (en) * | 2017-04-05 | 2019-07-05 | 桂林电子科技大学 | A kind of ultraviolet organic electroluminescence device of high efficiency and preparation method thereof |
| CN109935669B (en) * | 2017-12-15 | 2021-05-28 | Tcl科技集团股份有限公司 | Preparation method of reduced graphene oxide, hole injection material and preparation method thereof |
| CN109449313B (en) * | 2018-10-24 | 2021-06-08 | 桂林电子科技大学 | Method for preparing hole injection layer in organic light-emitting diode based on sol-gel method and constructed organic light-emitting diode |
| CN110048004B (en) * | 2019-03-26 | 2021-11-23 | 武汉华星光电半导体显示技术有限公司 | Organic electroluminescent device and preparation method thereof |
| CN109980113A (en) * | 2019-04-04 | 2019-07-05 | 上海大学 | A kind of Organic Light Emitting Diode and preparation method thereof |
| CN110165064B (en) * | 2019-05-29 | 2021-06-08 | 桂林电子科技大学 | Hole-controlled organic electroluminescent device with gradient energy level and preparation method thereof |
| CN111081904A (en) * | 2019-12-02 | 2020-04-28 | 武汉华星光电半导体显示技术有限公司 | Preparation method of graphene oxide film, OLED device and preparation method |
| CN113130835B (en) * | 2019-12-31 | 2022-06-21 | Tcl科技集团股份有限公司 | Quantum dot light-emitting diode and preparation method thereof |
| CN111883693A (en) * | 2020-07-27 | 2020-11-03 | 湖北工业大学 | Perovskite light-emitting diode based on oxide hole injection layer and preparation method thereof |
| CN112133840A (en) * | 2020-09-28 | 2020-12-25 | 电子科技大学中山学院 | Graphene OLED device and preparation method thereof |
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| CN204464323U (en) * | 2015-02-09 | 2015-07-08 | 桂林电子科技大学 | A kind of ultraviolet organic electroluminescence device injecting transmission based on gradient-structure hole |
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