EP3039730A1 - Emission layers for organic light emitting diodes and methods for their preparation - Google Patents
Emission layers for organic light emitting diodes and methods for their preparationInfo
- Publication number
- EP3039730A1 EP3039730A1 EP14762115.5A EP14762115A EP3039730A1 EP 3039730 A1 EP3039730 A1 EP 3039730A1 EP 14762115 A EP14762115 A EP 14762115A EP 3039730 A1 EP3039730 A1 EP 3039730A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- luminophore
- layer
- light emitting
- organic light
- emitting diode
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 239000003446 ligand Substances 0.000 claims abstract description 31
- 239000010409 thin film Substances 0.000 claims abstract description 30
- 239000004020 conductor Substances 0.000 claims abstract description 29
- 238000000151 deposition Methods 0.000 claims abstract description 29
- 238000010438 heat treatment Methods 0.000 claims abstract description 24
- 230000007935 neutral effect Effects 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 239000002243 precursor Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- -1 poly(9,9-dioctyl fluoren-2,7-diyl) Polymers 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 21
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 11
- 239000011521 glass Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 claims description 7
- 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 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 6
- 239000002985 plastic film Substances 0.000 claims description 5
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 4
- XHYGXHHDNCRYFF-UHFFFAOYSA-K 2-phenoxybenzoate terbium(3+) Chemical compound [Tb+3].[O-]C(=O)c1ccccc1Oc1ccccc1.[O-]C(=O)c1ccccc1Oc1ccccc1.[O-]C(=O)c1ccccc1Oc1ccccc1 XHYGXHHDNCRYFF-UHFFFAOYSA-K 0.000 claims description 3
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 3
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 3
- 229910052693 Europium Inorganic materials 0.000 claims description 3
- 229920000144 PEDOT:PSS Polymers 0.000 claims description 3
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 3
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 claims description 3
- 239000004697 Polyetherimide Substances 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 3
- 229910052771 Terbium Inorganic materials 0.000 claims description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 3
- HKQOBOMRSSHSTC-UHFFFAOYSA-N cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 239000008393 encapsulating agent Substances 0.000 claims description 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 3
- 229920006255 plastic film Polymers 0.000 claims description 3
- 229920001230 polyarylate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229920002530 polyetherether ketone Polymers 0.000 claims description 3
- 229920001601 polyetherimide Polymers 0.000 claims description 3
- 239000011112 polyethylene naphthalate Substances 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 3
- 239000010453 quartz Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 3
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 3
- QISKERKMOGSCJB-UHFFFAOYSA-N 4-iminopentan-2-one Chemical compound CC(=N)CC(C)=O QISKERKMOGSCJB-UHFFFAOYSA-N 0.000 claims description 2
- JCRMFGAOSSVHGK-UHFFFAOYSA-K [Eu+3].[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12 Chemical compound [Eu+3].[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12.[O-]C(=O)c1cccc2ccccc12 JCRMFGAOSSVHGK-UHFFFAOYSA-K 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229920000767 polyaniline Polymers 0.000 claims description 2
- 229920000128 polypyrrole Polymers 0.000 claims description 2
- 229920000123 polythiophene Polymers 0.000 claims description 2
- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 claims 1
- 239000010408 film Substances 0.000 abstract description 17
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 121
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 230000008021 deposition Effects 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004630 atomic force microscopy Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 229920002457 flexible plastic Polymers 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229920000642 polymer Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 239000000725 suspension Substances 0.000 description 3
- 238000007669 thermal treatment Methods 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000001069 Raman spectroscopy Methods 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000004773 frontier orbital Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- GENZLHCFIPDZNJ-UHFFFAOYSA-N [In+3].[O-2].[Mg+2] Chemical compound [In+3].[O-2].[Mg+2] GENZLHCFIPDZNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
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- 230000005284 excitation Effects 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
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- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000000504 luminescence detection Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001314 profilometry Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
-
- 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
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to emission layers for organic light emitting diodes (OLEDs) and, in particular, to methods of preparing them.
- OLEDs organic light emitting diodes
- the invention also relates to OLEDs incorporating emission layers obtained by the methods.
- Luminescent thin films are widely used as emissive layers in such devices as organic thin film transistors, organic solar cells and organic light emitting diodes.
- OLEDs where emissive layers are widely used today, are multilayer heterostructures, consisting at least of an emission layer positioned between a cathode and an anode. When an electric current flows through the structure, electrons and holes are caused to move into the emission layer, resulting in electroluminescence.
- additional layers of p- and/or n-type conductivity and electron- and/or hole-blocking layers are used.
- the emission layer and all the other layers of the OLED heterostructure are thin films of typical thickness in the range of 10-500 nm.
- the first reported OLED emission layer to exhibit relatively high electroluminescence efficiency at a low switch-on voltage was reported by C.W. Tang and S.A.Vanslyke in Applied Physics Letters, 51, 1987, 913.
- Their emission layer was composed of tris(8-hydroxyquinolinato)aluminium (Alq 3 ) and they used triarylamine as a hole-conductive layer.
- phosphorescent platinum, iridium, rare earth element compounds, fluorescent compounds of aluminium and zinc, organic small molecules and polymer compounds are used as emission layers.
- PVD physical vapor deposition
- a method of producing thin films is described in published Russian patent number RU 2469124.
- the method comprises forming a thin film coating of a soluble luminophore-containing coordination compound, for example luminophore- containing ternary coordination, deposited from solution onto a substrate, and heat treating the resulting thin film.
- the luminophore-containing ternary complex decomposes to a luminescent coordination compound and a neutral ligand; the neutral ligand is fully removed from the thin film.
- the method allows thin films of non- volatile and insoluble chemical compounds to be obtained.
- J.W. Levell, J.P. Gunning, P.L. Burn, et al, in Org. Electr., ⁇ , (2010), 1561 described obtaining an emission layer by spin-coating of a dichloromethane solution of a mixture of iridium complex (luminophore) and 4,4 -N, N'-dicarbazolebiphenyl (CBP, a conductive material) in a ratio of 1 :5 onto a substrate of glass coated with a layer of indium-tin oxide.
- CBP N'-dicarbazolebiphenyl
- PVK poly-N-vinylcarbazole
- TPD N, N'-bis(3-methylphenyl)-N,N'-bis (phenyl)benzidine
- CBP 4,4 * -N,N'-dicarbazolebiphenyl
- PFO poly(9,9-dioctyl fluoren-2,7-diyl)
- PVB polyvinyl butyral
- the present inventors perceive that there is a need to expand the arsenal of methods for producing the emission layer, in particular based on non-volatile and insoluble luminophores, and to increase its conductivity.
- the present invention provides a process for producing an emissive layer, comprising providing a solution comprising a luminophore-containing compound and a conductive material, depositing a thin film from the resulting solution on a substrate and subsequently heat treating the film at a temperature above 100 °C, and below the temperature at which the emission layer becomes unstable.
- luminophore-containing compound is used to mean both a luminophore per se, a luminophore precursor capable of being converted into a luminophore, and any compound capable of decomposing to form a luminophore.
- the permissible heat treatment temperature range is determined in each case depending on the thermal properties of the selected luminophore-containing compound and conductive material combination.
- the upper limit of the heat treatment temperature range is determined by the temperature stability of the emission layer.
- substrate for the emission layer deposition depends on the device for which the emission layer is obtained.
- a glass plate or polymer film with a deposited anode thin film, and possibly additional conductive layers, may be used as a substrate.
- Deposition of a thin film on a substrate can be carried out by any suitable method.
- a soluble luminophore itself may be used.
- a soluble compound which transforms into a luminophore when heated may be used, in particular, a soluble luminophore- containing ternary coordination compound (mixed-ligand complex (MLC)), which is decomposed by heat treatment into the luminophore and a neutral ligand, the neutral ligand being completely removed from the thin film during the heat treatment decomposition step.
- MLC mixed-ligand complex
- the ligand removal temperature may be equal to the temperature of the MLC decomposition to the luminophore and the neutral ligand, or the ligand removal temperature may be the temperature of evaporation of the neutral ligand. In either case, by "ligand removal temperature” is meant the temperature at which the complete removal occurs of the neutral ligand from the luminophore-containing MLC.
- thermal treatment of the emission layer is carried out at the temperature below the stability of the emission layer, but higher than the ligand removal temperature.
- the neutral ligand and the conductive material are selected so that the neutral ligand, after removal from the MLC, does not interact with the conductive material.
- the conductive material must have, besides all the previously mentioned properties (high electron and hole conductivity, solubility, film forming properties, transparency and corresponding energy of the frontier orbitals), thermal stability at temperatures above 100 °C. Also, if a luminophore-containing MLC is used as the luminophore-containing compound, the conductive material must possess thermal stability to a temperature at least as great as the neutral ligand removal temperature. Furthermore, the conductive material must be soluble in at least one solvent that also dissolves the luminophore-containing compound.
- the present invention allows improvements not only in the characteristics of the emission layer, but also allows emission layers to be produced that are based on insoluble and non-volatile luminophores.
- the invention is able to extend the arsenal of materials for organic light emitting diodes.
- Organic light-emitting diodes may be obtained, in which the emission layer is made by the inventive process.
- the resulting OLED heterostructure is a multilayer structure consisting of a substrate with a transparent anode layer placed thereon, on which an emission layer is deposited by the inventive method, and a cathode.
- additional layers of electron and/or hole-conducting and electron- and/or hole- blocking layers may be used.
- Figure 1 is a cross-sectional side view of a first step in the manufacture of an OLED showing an anode layer deposited on a substrate
- Figure 2 is a cross-sectional side view showing the partially formed OLED structure of Figure 1 after deposition of a hole-transporting layer
- Figure 3 is a cross-sectional side view showing the partially formed OLED structure of Figure 2 after deposition of an emission layer precursor;
- Figure 4 is a cross-sectional side view showing the partially formed OLED structure of Figure 3 after conversion of the emission layer precursor to the final form of the emission layer;
- Figure 5 is a cross-sectional side view showing a partially formed OLED structure of Figure 4 after deposition of a blocking layer and/or cathode layer
- Figure 6 is a cross-sectional side view showing the OLED structure of Figure
- FIGS 1 to 6 illustrate schematically a sequence of steps for manufacturing OLEDs in accordance with the present invention.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2013139931/02A RU2547383C2 (ru) | 2013-08-28 | 2013-08-28 | Способ нанесения эмиссионного слоя |
| PCT/RU2014/000435 WO2015030627A1 (en) | 2013-08-28 | 2014-06-17 | Emission layers for organic light emitting diodes and methods for their preparation |
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| Publication Number | Publication Date |
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| EP3039730A1 true EP3039730A1 (en) | 2016-07-06 |
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| EP14762115.5A Withdrawn EP3039730A1 (en) | 2013-08-28 | 2014-06-17 | Emission layers for organic light emitting diodes and methods for their preparation |
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| EP (1) | EP3039730A1 (ru) |
| RU (1) | RU2547383C2 (ru) |
| WO (1) | WO2015030627A1 (ru) |
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| RU2657497C1 (ru) * | 2017-05-12 | 2018-06-14 | Сиа Эволед | Способ получения эмиссионного слоя на основе соединений редкоземельных элементов и органический светоизлучающий диод |
| CN107022096B (zh) * | 2017-06-01 | 2020-03-27 | 厦门大学 | 具有近紫外激发功能高光透过性复合醋酸纤维素膜的制备 |
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| RU2144236C1 (ru) * | 1997-12-31 | 2000-01-10 | ООО "Научно-производственное предприятие "Кристаллы и Технологии" | Катодолюминесцентный экран |
| JP4754798B2 (ja) * | 2004-09-30 | 2011-08-24 | 株式会社半導体エネルギー研究所 | 表示装置の作製方法 |
| WO2006071328A2 (en) * | 2004-10-08 | 2006-07-06 | The Regents Of The University Of California | High efficiency light-emitting diodes |
| EP2276087A4 (en) * | 2008-04-28 | 2015-04-29 | Dainippon Printing Co Ltd | DEVICE WITH LOCHINJECTION / TRANSPORT COAT, METHOD OF PRODUCTION THEREOF AND INK FOR PRODUCING THE LOCHINJECTION / TRANSPORT COAT |
| DE102008053121A1 (de) * | 2008-10-24 | 2010-04-29 | Merck Patent Gmbh | Doppelkomplex-Salze als Emitter in OLED-Vorrichtungen |
| RU2469124C1 (ru) | 2011-05-23 | 2012-12-10 | Государственное учебно-научное учреждение Факультет наук о материалах Московского государственного университета им. М.В. Ломоносова (ФНМ МГУ) | Способ получения тонких пленок химических соединений |
| RU2475887C1 (ru) * | 2011-08-01 | 2013-02-20 | Закрытое Акционерное Общество "Научно-Производственная Коммерческая Фирма "Элтан Лтд" | Светодиодный источник белого света с удаленным отражательным многослойным фотолюминесцентным конвертером |
| TWI527207B (zh) * | 2011-10-21 | 2016-03-21 | 友達光電股份有限公司 | 可撓式有機發光裝置及其製作方法 |
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| Publication number | Publication date |
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| RU2547383C2 (ru) | 2015-04-10 |
| RU2013139931A (ru) | 2015-03-10 |
| WO2015030627A1 (en) | 2015-03-05 |
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