CN102169969A - Anode modification method of organic electroluminescent device - Google Patents
Anode modification method of organic electroluminescent device Download PDFInfo
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- 238000002715 modification method Methods 0.000 title claims abstract description 10
- 239000011521 glass Substances 0.000 claims abstract description 60
- 238000002360 preparation method Methods 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 35
- 238000004070 electrodeposition Methods 0.000 claims abstract description 24
- 239000000758 substrate Substances 0.000 claims abstract description 3
- 238000005401 electroluminescence Methods 0.000 claims description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- 239000008151 electrolyte solution Substances 0.000 claims description 22
- 238000005530 etching Methods 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 239000002019 doping agent Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- NBLHGCDPIWAGAS-UHFFFAOYSA-N 2-ethylthiolane-3,4-dione Chemical compound O=C1C(SCC1=O)CC NBLHGCDPIWAGAS-UHFFFAOYSA-N 0.000 claims description 6
- IOVFHLJNAMPRHI-UHFFFAOYSA-N 2-oxo-2-thiophen-3-ylacetaldehyde Chemical compound O=CC(=O)C=1C=CSC=1 IOVFHLJNAMPRHI-UHFFFAOYSA-N 0.000 claims description 6
- 229940059939 kayexalate Drugs 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 3
- 229940075397 calomel Drugs 0.000 claims description 3
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 3
- 238000003487 electrochemical reaction Methods 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 229920000144 PEDOT:PSS Polymers 0.000 abstract description 38
- 238000012986 modification Methods 0.000 abstract description 16
- 230000004048 modification Effects 0.000 abstract description 16
- 239000000463 material Substances 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 abstract 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 abstract 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 abstract 1
- 229910052594 sapphire Inorganic materials 0.000 abstract 1
- 239000010980 sapphire Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 47
- 239000010408 film Substances 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 15
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000002791 soaking Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 238000004020 luminiscence type Methods 0.000 description 2
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- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- MGQIWUQTCOJGJU-UHFFFAOYSA-N [AlH3].Cl Chemical compound [AlH3].Cl MGQIWUQTCOJGJU-UHFFFAOYSA-N 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
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- 239000011248 coating agent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical class [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 1
- 230000007547 defect Effects 0.000 description 1
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- 230000008021 deposition Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 238000002294 plasma sputter deposition Methods 0.000 description 1
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- 238000005036 potential barrier Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
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- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the field of synthesis and preparation of organic electroluminescent device materials, and particularly relates to an anode modification method of an organic electroluminescent device. The invention adopts an electrochemical deposition method to modify a poly (3, 4-ethylenedioxythiophene)/poly (p-styrenesulfonic acid) (PEDOT: PSS) film on the surface of anode ITO conductive glass, and the modified ITO conductive glass is used as the anode of an organic electroluminescent device. The invention directly finishes the modification of anode ITO conductive glass in an organic electroluminescent device by PEDOT and PSS by using an electrochemical deposition method. The preparation method has simple process and good film forming property. And the introduction of a PEDOT (polymer stabilized ethylene terephthalate) PSS (patterned sapphire substrate) modification layer reduces the starting voltage of the obtained organic electroluminescent device and improves the brightness and quantum efficiency of the device.
Description
Technical field
The invention belongs to the synthetic and preparation field of organic electroluminescence device material, be specifically related to a kind of anode modification method of organic electroluminescence device.
Background technology
1987, the C.W.Tang of U.S. Rochester University and S.A.Vanslyke have reported the double-deck organic film photoelectric device with excellent photoelectric characteristic, and the various countries scientist has launched extensive studies in synthetic, the research of device luminescence mechanism of new material and the aspects such as optimization of device architecture subsequently.Owing to there is bigger injection barrier between the anode of organic electroluminescence device and the luminescent layer, be unfavorable for the injection in hole and the raising of device performance, carry out the performance that suitable modification can improve device by anode to luminescent device.A kind of anode modification method of organic electroluminescence device is disclosed among the TW200820824-A, utilize ammonium sulfide that indium tin oxide (ITO) conductive glass surface is handled, reduce the oxygen defect of ITO conductive glass surface, improve sheet resistance and work function, and then reduced potential barrier between ito thin film and the luminescent layer, and, very big change does not all take place in the roughness of sulfuration back ITO conductive glass surface and transmitance, and this anode modification method can improve the transmitance and the stability of light effectively.
US 2006/0049754 A1 discloses a kind of anode layer surface treatment method, and the precursor antianode surface that utilizes plasma sputtering to contain fluorine molecule is modified, and forms the layer of metal fluoride on its surface, has improved the hole injection efficiency of device.US 2007/0170421 A1 discloses the application of hot evaporation coating method aspect the preparation of anode modification layer, and the anode modification layer material is selected (C
xF
y)
nSeries compound, this method not only reduces the difficulty of processing of device, and the overall performance of device is greatly improved simultaneously.A kind of electrochemical deposition preparation and the application of such film in the preparation electroluminescent device of Organic Light-Emitting Display are disclosed among the CN 1822410A, be connected the monomer electrochemical polymerization in the mixed solution of acetonitrile and carrene that forms by chemical bond by electroactive unit and luminescence unit, this device has that technology is simple, device luminous efficiency height, efficient are subjected to electrochemical doping to influence little, easy control area size and the adjustable advantage of glow color.
CuPc class, polyaniline and other conducting polymer materials also are widely used in the hole injection layer material of organic electroluminescence device, modify with antianode, improve the hole injection efficiency.Deposition ten hexafluoro CuPcs formation is haled the electronic molecules layer on the anode ITO electro-conductive glass that CN 1983664A discloses at organic electroluminescence device, form complete dipole layer, by changing organic layer thickness and device architecture, improve the luminous efficiency of organic electroluminescence device, reduced operating voltage.A.J.Heeger (Y.Yang, A.J.Heeger, Applied Physics Letter, 1994,64,1245-1247) reported the hole injection layer of the polyaniline of camphorsulfonic acid doping as organic electroluminescence device, realized the anode modification of conducting polymer first, with not doped polyaniline anode modification layer comparison, the introducing of the polyaniline decorative layer after the doping to luminescent device, improved the hole injection efficiency, the luminosity when voltage is 4.0V has improved two orders of magnitude.US 2006/0240280 A1 discloses four substituting group tetracyano-p-quinodimethane (R with strong oxidizing property
4-TCNQ) series compound is as the anode modification layer of organic electroluminescence device, the result shows, the anode modification layer is by receiving the electric charge from anode material, form contact interface stable, high work function at anode surface, can improve the resistance to overturning of device, simultaneously, this decorative layer also serves as the hole injection layer of device, reduce the cut-in voltage of device, improved the device overall performance.
In recent years, the novel conductive polymer polythiophene has also caused increasing attention in this field.People such as Gross (Markus Gross, David C.M ü ller, Heinz-Georg Nothofer, Ulrich Scherf, Dieter Neher, Christoph Brauchle, Klaus Meerholz, Nature, 2000,405,661-665) reported and use ITO electro-conductive glass that poly-(4,4 '-dimethoxy connects thiophene) (PDBT) modify, in solution, carried out electrochemical doping as anode, use poly-fluorenes class (PF) material to prepare organic electroluminescence device as luminescent layer, the result shows that device performance improves with the raising of doping level.L.Dunsch (F.Zhang, A.Petr, U.Kirbach, L.Dunsch, Journal of Materials Chemistry, 2003,13,265-267) reported poly-the connect electrochemical polymerization of thiophene film (PbT) and the application in organic electroluminescence device thereof, performance test shows, the poly-thiophene that connects makes multilayer device ITO/PbT/NPB/Alq to the modification of ITO electro-conductive glass anode
3The maximum luminous efficiency of/Mg:Ag is increased to 1.7lm/W by 1.1lm/W, and luminosity when voltage is 10V and current density all improve an order of magnitude, and cut-in voltage is reduced to 6.5V by 10V.Heqing Tang (H.Tang, Z.Zhou, Y.Zhong, H.Liao, L.Zhu, Thin Solid Films, 2006,515,2447-2451) reported poly-(3 methyl thiophene)-poly-electrochemistry combined polymerization and application thereof that connects thiophene film, with the work electrode of ITO electro-conductive glass as electrochemical polymerization, directly finished poly-(3 methyl thiophene)-the poly-anode modification that connects thiophene film to organic electroluminescence device, make device ITO/polymer/TPD/Alq
3/ Mg-Ag shows excellent performance, and when voltage was 4V, the luminosity of device reached 100cd/m
2
Summary of the invention
The anode modification method that the purpose of this invention is to provide the simple organic electroluminescence device of a kind of technology, the anode of gained organic electroluminescence device can improve the brightness and the quantum efficiency of device.
The anode modification method of organic electroluminescence device of the present invention is to adopt the method for electrochemical deposition, modify poly-(3 at anode ITO conductive glass surface, 4-dioxoethyl thiophene)/gather (p styrene sulfonic acid) (PEDOT:PSS) film, and the ITO electro-conductive glass after will modifying is as the anode of organic electroluminescence device.
The anode modification method of organic electroluminescence device of the present invention may further comprise the steps:
(1) preparation of electrolyte solution
With 3,4-dioxoethyl thiophene (EDOT) and dopant are dissolved in the organic solvent, obtain the required electrolyte solution of electrochemical deposition; The content of EDOT is 1～10wt% in the described electrolyte solution, and the content of dopant is 0.05～5wt%, and surplus is an organic solvent;
Described dopant can be selected from least a in the group that polystyrolsulfon acid (PSSH), kayexalate, polystyrolsulfon acid potassium, ammonium polystyrene sulphonate form;
(2) electrochemical deposition of decorative layer
The electrolyte solution that step (1) is obtained pour into be equipped with Ag/AgCl or calomel electrode as reference electrode, platinized platinum or stainless steel substrates as to electrode, in the electrochemical reaction appts of the ITO of etching electro-conductive glass as work electrode, after configuring applied voltage, open switch; EDOT begins to be deposited as poly-(3 in polymerization on the ITO of etching electro-conductive glass, 4-dioxoethyl thiophene) (PEDOT), polystyrolsulfon acid root (PSS-) mixes in PEDOT simultaneously, gathered (3,4-dioxoethyl thiophene)/gathered (p styrene sulfonic acid) (PEDOT:PSS) film modified ITO electro-conductive glass; Then, the ITO electro-conductive glass that PEDOT:PSS is film modified takes out from electrolyte solution, clean (available acetone cleaning), and the film modified ITO electro-conductive glass of the PEDOT:PSS after will cleaning to place baking oven to carry out drying (can be to carry out drying under 60～120 ℃ in temperature; Can be 0.5～24 hour drying time), obtain having the ITO electro-conductive glass of PEDOT:PSS film as the finishing that the anode of organic electroluminescence device uses.Products obtained therefrom is protected under inert gas (as nitrogen atmosphere) atmosphere and is deposited.
" but dissolving with hydrochloric acid-aluminium displacement-melting-electrolysis process prepares high purity indium (Xu Dongsheng, Liu Jiaxiang, non-ferrous metal, 2008,60,74-76) " method etching ITO electro-conductive glass from useless ITO target to the etching list of references of described ITO electro-conductive glass.In concentration is to soak the indium-tin-oxide of etching ITO conductive glass surface in the hydrochloric acid of 3mol/L.Before soaking etching, the part that at first will need to keep is protected with protective layer stickup covering, and not protected ITO conductive glass surface is fallen by hcl corrosion in soaking etching process, and then obtains the ITO electro-conductive glass of required form.ITO electro-conductive glass after the etching passes through cleaning agent, ethanol, acetone and other organic solvent ultrasonic cleaning successively, and irradiation is standby after 1 hour under ultraviolet light then.
Described organic solvent can be isopropyl alcohol, acetonitrile, chloroform or the mixture of arbitrary proportion between them.
Described applied voltage is 1.0～1.4V, and the time that applies applied voltage is 1～60min.
The thickness of described PEDOT:PSS film is 20～150nm.
The structure of described organic electroluminescence device comprises ITO electro-conductive glass anode, organic layer and the negative electrode that above-mentioned electrochemical deposition method is modified.Organic layer can be (1) N, N '-diphenyl-N, N ' (2-naphthyl)-(1,1 '-phenyl)-4,4 '-diamines (NPB)/oxine aluminium (Alq
3); (2) gather [2-methoxyl group-5-(2 '-the ethylhexyl ether)-1, the 4-styryl] (MEH-PPV); (3) Polyvinyl carbazole (PVK): three (2-phenylpyridine) iridium (Ir (ppy)
3)/2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP)/Alq
3(4) PVK:Ir (ppy)
3: DCJTB/BCP/Alq
3Negative electrode can be Mg, Ag and Al or be mixed with the alloy that obtains between them according to a certain percentage.
The present invention utilizes the method for electrochemical deposition directly to finish the modification of PEDOT:PSS to anode ITO electro-conductive glass in the organic electroluminescence device.Preparation method's technology of the present invention is simple, good film-forming property.The introducing of PEDOT:PSS decorative layer has reduced the cut-in voltage of gained organic electroluminescence device, has improved the brightness and the quantum efficiency of device.
Description of drawings
Fig. 1 is the structural representation of organic electroluminescence device among the present invention.Wherein:
(a) device architecture is ITO/NPB/Alq
3/ LiF/Al;
(b) device architecture is ITO/PEDOT:PSS/NPB/Alq
3/ LiF/Al;
(c) device architecture is ITO/MEH-PPV/Al;
(d) device architecture is ITO/PEDOT:PSS/MEH-PPV/Al;
(e) device architecture is ITO/PEDOT:PSS/NPB/Alq
3/ Mg:Ag;
(f) device architecture is ITO/PEDOT:PSS/PVK:Ir (ppy)
3/ BCP/Alq
3/ LiF/Al;
(g) device architecture is ITO/PEDOT:PSS/PVK:Ir (ppy)
3: DCJTB/BCP/Alq
3/ LiF/Al.
Embodiment
Among Comparative Examples and the embodiment, the etching of ITO electro-conductive glass is identical with cleaning operation.
In concentration is to soak the indium-tin-oxide of etching ITO conductive glass surface in the hydrochloric acid of 3mol/L.Before soaking etching, the part that at first will need to keep is protected with protective layer stickup covering, and not protected ITO conductive glass surface is fallen by hcl corrosion in soaking etching process, and then obtains the ITO electro-conductive glass of required form.ITO electro-conductive glass after the etching passes through cleaning agent, ethanol, acetone and other organic solvent ultrasonic cleaning successively, and irradiation is standby after 1 hour under ultraviolet light then.
Among Comparative Examples and the embodiment, the device performance method of testing is identical.
The device performance test is at room temperature to carry out in the air, adopts the Keithley2410 source measuring unit record current-voltage curve of U.S. Keithley company.Utilize the brightness-voltage curve of the PR650 spectral measurement unit record comparative device of U.S. Photo Research.The device performance test result sees Table 1.
Comparative Examples 1
With the anode of commercially available not modified ITO electro-conductive glass as organic electroluminescence device, list of references " a kind of organic electroluminescence device " (Zhang Zhiqiang, Hao Yuying etc., spectroscopy and spectrum analysis with mutual interspersed interfacial structure, 2009,29,3232-3235) with " utilizing the organic electroluminescence device of LiF/Al " (Li Chuannan etc., photon journal as electrode, 30,2001, the 86-89) method in is carried out the preparation of organic electroluminescence device.3 * 10
-4Under the Pa condition successively at the hole transmission layer (NPB) of anode surface evaporation one deck 20nm thickness, the luminescent layer (Alq of one deck 50nm thickness
3) and cathode layer (LiF/Al), finish comparative device (ITO/NPB/Alq
3/ LiF/Al) preparation, its structure is shown in Fig. 1 (a).
Comparative Examples 2
(1) spin-coating method of anode modification layer preparation:
With KW-4 type sol evenning machine (manufacturing of research department of Microelectronics Institute of the Chinese Academy of Sciences) with commercially available PEDOT:PSS colloidal solution (model is Baytron P), the method that adopts spin coating obtains the film modified ITO electro-conductive glass of the thick PEDOT:PSS of 30nm in commercially available ITO conductive glass surface coating by the size of adjusting rotating speed.
(2) preparation of organic electroluminescence device:
ITO electro-conductive glass after modifying in the step (1) is carried out organic electroluminescence device (ITO/PEDOT:PSS/NPB/Alq as anode
3/ LiF/Al) preparation, the device preparation process is with Comparative Examples 1, and its device architecture is shown in Fig. 1 (b).
Comparative Examples 3
The preparation of organic electroluminescence device: will be without the ITO electro-conductive glass of any modification anode as organic electroluminescence device, list of references " research of the orange red smooth OLED of polymer MEH-PPV " (lock vanadium etc., 2007, photoelectric device, 28, method 324-353) is carried out the preparation of organic electroluminescence device (ITO/MEH-PPV/Al).Is the MEH-PPV luminescent layer of 80nm at anode surface spin coating one layer thickness earlier, 120 ℃ of following vacuumize 20 minutes is subsequently 3 * 10
-4Evaporation one layer thickness is about the Al cathode layer of 100nm under the Pa condition, finishes device, and its device architecture is shown in Fig. 1 (c).Comparative Examples 4
(1) spin-coating method of anode modification layer preparation: with Comparative Examples 2.
(2) preparation of organic electroluminescence device: the ITO electro-conductive glass after modifying in the step (1) is carried out the preparation of organic electroluminescence device (ITO/PEDOT:PSS/MEH-PPV/Al) as anode, the device preparation process is with Comparative Examples 3, and its device architecture is shown in Fig. 1 (d).
Embodiment 1
(1) electrolyte solution preparation: EDOT and polystyrolsulfon acid are dissolved in the isopropyl alcohol, obtain the required electrolyte solution of electrochemical deposition; The content of EDOT is 6.6wt% in the described electrolyte solution, and the content of polystyrolsulfon acid is 0.095wt%, and surplus is an isopropyl alcohol.
(2) electrochemical deposition of decorative layer: with the electrolyte solution for preparing in the step (1) pour into be equipped with Ag/AgCl as reference electrode, platinized platinum as being in the electrochemical reaction appts of work electrode to electrode, through the ITO of etching electro-conductive glass; After configuring applied voltage, open switch; EDOT begins to be deposited as PEDOT in polymerization on the ITO of etching work electrode, and polystyrolsulfon acid root (PSS-) mixes in PEDOT simultaneously, obtains the film modified ITO electro-conductive glass of PEDOT:PSS; Then; the ITO electro-conductive glass that PEDOT:PSS is film modified takes out from electrochemical solution; clean with acetone; and be placed in the baking oven and carried out drying under 80 ℃ 6 hours; obtain having the ITO electro-conductive glass of PEDOT:PSS film, under the nitrogen atmosphere protection, deposit standby as the finishing that the anode of organic electroluminescence device uses.Described applied voltage is 1.0V, and the time that applies applied voltage is 7min, obtains thickness and be the ITO electro-conductive glass of modification of the PEDOT:PSS film of 30nm.
(3) preparation of organic electroluminescence device: the ITO electro-conductive glass that PEDOT:PSS in the step (2) is modified is as the anode of organic electroluminescence device, and the device preparation process is with Comparative Examples 1, and its device architecture is shown in Fig. 1 (b).
Embodiment 2
(1) electrolyte solution preparation: compound method is with embodiment 1, but the content of EDOT is 5.7wt%, and the content of polystyrolsulfon acid is 0.95wt%, and surplus is an acetonitrile.
(2) electrochemical deposition of decorative layer: electrochemical deposition method is with embodiment 1, but applied voltage is 1.2V, and the time that applies applied voltage is 4min, and obtaining thickness is the film modified ITO electro-conductive glass of PEDOT:PSS of 50nm, baking temperature is 120 ℃, and be 0.5 hour drying time.
(3) preparation of organic electroluminescence device: the ITO electro-conductive glass that PEDOT:PSS in the step (2) is modified is as the anode of organic electroluminescence device, and the device preparation process is with Comparative Examples 1, and its device architecture is shown in Fig. 1 (b).
Embodiment 3
(1) electrolyte solution preparation: compound method is with embodiment 1, but the content of EDOT is 2.5wt%, the content of kayexalate is 1.20wt%, and the content of ammonium polystyrene sulphonate is 1.60wt%, and surplus is that volume ratio is 50: 50 the acetonitrile and the mixture of chloroform.
(2) electrochemical deposition of decorative layer: electrochemical deposition method is with embodiment 1, but applied voltage is initially 1.0V, voltage raises gradually then, when being the 60min end to the time that applies applied voltage, applied voltage rises to 1.4V, obtaining thickness is the film modified ITO electro-conductive glass of PEDOT:PSS of 80nm, and baking temperature is 60 ℃, and be 24 hours drying time.
(3) preparation of organic electroluminescence device: the ITO electro-conductive glass that PEDOT:PSS in the step (2) is modified is as the anode of organic electroluminescence device, and the device preparation process is with Comparative Examples 1, and its device architecture is shown in Fig. 1 (b).
Embodiment 4
(1) electrolyte solution preparation: compound method is with embodiment 1, but the content of EDOT is 6.5wt%, and dopant is a kayexalate, and content is 0.19wt%, and surplus is the mixture (acetonitrile: the volume ratio of chloroform is 80: 20) of acetonitrile and chloroform.
(2) electrochemical deposition of decorative layer: electrochemical deposition method is with embodiment 1, but reference electrode is selected calomel electrode for use, and applied voltage is 1.2V, and the time that applies applied voltage is 10min, and obtaining thickness is the film modified ITO electro-conductive glass of PEDOT:PSS of 50nm.
(3) preparation of organic electroluminescence device: list of references " Improved hole injection and performance of multilayer OLED devices via electrochemically prepared-polybithiphene layers " (F.Zhang, A.Petr, U.Kirbach, L.Dunsch, Journal of Materials Chemistry, 2003,13, preparation of devices method 265-267), preparation organic electroluminescence device (ITO/PEDOT:PSS/NPB/Alq
3/ Mg:Ag), its device architecture is shown in Fig. 1 (e).
Embodiment 5
(1) electrolyte solution preparation: compound method is with embodiment 1, but the content of EDOT is 1.0wt%, and dopant is a kayexalate, and content is 5.0wt%, and surplus is the mixture (acetonitrile: the volume ratio of isopropyl alcohol is 20: 80) of acetonitrile and isopropyl alcohol.
(2) electrochemical deposition of decorative layer: electrochemical deposition method is with embodiment 1, but applied voltage is 1.2V, and the time that applies applied voltage is 1min, and obtaining thickness is the film modified ITO electro-conductive glass of PEDOT:PSS of 20nm.
(3) preparation of organic electroluminescence device: the ITO electro-conductive glass that PEDOT:PSS in the step (2) is modified is as the anode of organic electroluminescence device, and the device preparation process is with embodiment 4, and its device architecture is shown in Fig. 1 (e).
Embodiment 6
(1) electrolyte solution preparation: compound method is with embodiment 1, but the content of EDOT is 10.0wt%, and dopant is a kayexalate, and content is 0.05wt%, and surplus is the mixture (isopropyl alcohol: the volume ratio of chloroform is 50: 50) of isopropyl alcohol and chloroform.
(2) electrochemical deposition of decorative layer: electrochemical deposition method is with embodiment 1, but applied voltage is 1.3V, and the time that applies applied voltage is 60min, and obtaining thickness is the film modified ITO electro-conductive glass of PEDOT:PSS of 150nm.
(3) preparation of organic electroluminescence device: the ITO electro-conductive glass that PEDOT:PSS in the step (2) is modified is as the anode of organic electroluminescence device, and the device preparation process is with embodiment 4, and its device architecture is shown in Fig. 1 (e).
Embodiment 7
(1) electrolyte solution preparation: with embodiment 2.
(2) electrochemical deposition of decorative layer: with embodiment 2.
(3) organic electroluminescence device preparation: the ITO electro-conductive glass that PEDOT:PSS in the step (2) is modified is as the anode of organic electroluminescence device, and the device preparation process is with Comparative Examples 3, and its device architecture is shown in Fig. 1 (d).
Embodiment 8
(1) electrolyte solution preparation: with embodiment 2.
(2) electrochemical deposition of decorative layer: with embodiment 2.
(3) organic light-emitting device preparation: list of references " based on the white color organic electroluminescence device of dopant dye DCJTB in polymer " (Zhang Yanfei etc., spectroscopy and spectrum analysis, 2008,28, method 760-762) prepares organic electroluminescence device ITO/PEDOT:PSS/PVK:Ir (ppy)
3/ BCP/Alq
3/ LiF/Al.The ITO electro-conductive glass that PEDOT:PSS is modified is as the anode of organic electroluminescence device, and ito anode surface spin coating one layer thickness of modifying at PEDOT:PSS is the PVK:Ir (ppy) of 50nm
3Luminescent layer, 80 ℃ of following vacuum treatments 30 minutes.Subsequently 3 * 10
-4Under the Pa condition successively the evaporation one layer thickness BCP (hole blocking layer) and the thickness that are about 10nm be the Alq of 20nm
3(electron transfer layer) is at last 3 * 10
-4The Al cathode layer that evaporation one layer thickness is about 100nm under the Pa condition is finished the preparation of organic electroluminescence device, and device architecture is shown in Fig. 1 (f).The mass percent of the composition in the device between each material of luminescent layer is 100: 5.
Embodiment 9
(1) electrolyte solution preparation: with embodiment 2.
(2) electrochemical deposition of decorative layer: with embodiment 2.
(3) organic light-emitting device preparation: the luminescent layer material is PVK:Ir (ppy)
3: DCJTB, PVK, Ir (ppy)
3With the mass percent of DCJTB be 100: 5: 2, the device preparation process is with embodiment 6, its device architecture is shown in Fig. 1 (g).
Table 1 organic electroluminescence device The performance test results tables of data
Claims (6)
1. the anode modification method of an organic electroluminescence device is characterized in that, this method may further comprise the steps:
(1) preparation of electrolyte solution
With 3,4-dioxoethyl thiophene and dopant are dissolved in the organic solvent, obtain electrolyte solution; In the described electrolyte solution 3, the content of 4-dioxoethyl thiophene is 1～10wt%, and the content of dopant is 0.05～5wt%, and surplus is an organic solvent;
Described dopant is selected from least a in the group that polystyrolsulfon acid, kayexalate, polystyrolsulfon acid potassium, ammonium polystyrene sulphonate form;
(2) electrochemical deposition of decorative layer
The electrolyte solution that step (1) is obtained pour into be equipped with Ag/AgCl or calomel electrode as reference electrode, platinized platinum or stainless steel substrates as to electrode, in the electrochemical reaction appts of the ITO of etching electro-conductive glass as work electrode, after configuring applied voltage, open switch; 3,4-dioxoethyl thiophene begins to be deposited as poly-(3 in polymerization on the ITO of etching electro-conductive glass, 4-dioxoethyl thiophene), the polystyrolsulfon acid root is poly-(3 simultaneously, 4-dioxoethyl thiophene) mixes in, gathered (3,4-dioxoethyl thiophene)/gathered (p styrene sulfonic acid) film modified ITO electro-conductive glass; Then, to gather (3,4-dioxoethyl thiophene)/gather (p styrene sulfonic acid) film modified ITO electro-conductive glass from electrolyte solution, to take out, clean, and poly-(3 after will cleaning, 4-dioxoethyl thiophene)/poly-(p styrene sulfonic acid) film modified ITO electro-conductive glass places baking oven to carry out drying, obtains the ITO electro-conductive glass that finishing that the anode as organic electroluminescence device uses has poly-(3,4-dioxoethyl thiophene)/poly-(p styrene sulfonic acid) film.
2. method according to claim 1 is characterized in that: the temperature of described drying is 60～120 ℃.
3. method according to claim 1 and 2 is characterized in that: the time of described drying is 0.5～24 hour.
4. method according to claim 1 is characterized in that: described organic solvent is isopropyl alcohol, acetonitrile, chloroform or the mixture of arbitrary proportion between them.
5. method according to claim 1 is characterized in that: described applied voltage is 1.0～1.4V, and the time that applies applied voltage is 1～60min.
6. method according to claim 1 is characterized in that: the thickness of described poly-(3,4-dioxoethyl thiophene)/poly-(p styrene sulfonic acid) film is 20～150nm.
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