CN1833323A - Light-emitting diode - Google Patents
Light-emitting diode Download PDFInfo
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- CN1833323A CN1833323A CNA2004800224280A CN200480022428A CN1833323A CN 1833323 A CN1833323 A CN 1833323A CN A2004800224280 A CNA2004800224280 A CN A2004800224280A CN 200480022428 A CN200480022428 A CN 200480022428A CN 1833323 A CN1833323 A CN 1833323A
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- 239000000463 material Substances 0.000 claims abstract description 32
- 229920000642 polymer Polymers 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 6
- 150000003112 potassium compounds Chemical class 0.000 claims abstract description 6
- 239000011734 sodium Substances 0.000 claims abstract description 6
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims abstract description 5
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 241000790917 Dioxys <bee> Species 0.000 claims description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000004317 sodium nitrate Substances 0.000 claims description 3
- 235000010344 sodium nitrate Nutrition 0.000 claims description 3
- 229940072033 potash Drugs 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- -1 poly(styrenesulfonate) Polymers 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical class [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 8
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 229920000547 conjugated polymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000010670 acid alkali reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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Classifications
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention pertains to a light-emitting diode (LED) comprising layers of an anode, an acidic hole conducting-injecting material, a light-emitting polymer, and a cathode, characterized in that the hole conducting-injecting material comprises a poly(3,4-ethylenedioxythiophene poly(styrenesulfonate) (PEDOT), which is obtainable by at least partially neutralizing the PEDOT with an anion that is comprised or formed from a sodium or potassium compound, and the light-emitting material comprises a light-emitting p-arylenevinylene polymer (PAV). The invention further relates to a method for increasing the efficiency of said light-emitting diode.
Description
The present invention relates to comprise the light-emitting diode (LED) of anode layer, acid hole-conductive-injection material layer, light-emitting polymer layer and cathode layer.
The poly-LED (based on the LED of polymer) of great majority is made of the two layers of polymers layer that is clipped between two electrode materials: one hole-conductive-injection material and light emitting polymer.This light emitting polymer can be PAV type [poly-(to the arlydene ethenylidene)].For first function, can use poly-(3,4-ethylidene dioxy thiophene, PEDT), the aqueous dispersion form that it can itself and polystyrolsulfon acid (PSS) obtains.This dispersion is called PEDOT and can be commercially available with BAYTRON P VP CH 8000 (high resistance) or Baytron P VP AI 4083 (low resistances) from HC Starck.Because the acidic nature of PSS, the pH value of the PEDOT solution of 2.5% solid content is lower than 2.The effect of PSS is to keep PEDT solubilized and stable in solution.In fact PEDT polymerization under the condition that PSS exists.PEDT moment between polymerization period is doped (oxidation).This obtain can conduction hole electropolymer.Electronegative sulfonate group is served as the equilibrium ion (on three to four unit of PEDT is mixed by positively charged ground usually) of the positively charged PEDT unit that is used for the balance doping.
This LED is known in the art, and for example referring to US 2003/0011306, the document is incorporated herein by reference.
There is the efficient of improving this LED, particularly improves the lasting demand of the brightness of the display that contains these LED.But recommendation improves quantum efficiency by the lithium salts of for example various ether sulfate anion surfactants of organic anion surfactant additive of adding high degree of polarization in US 6284435.
Have now found that, contain PEDOT can be simply as hole-conductive-injection material and PAV type polymer as the usefulness of the LED of light emitting polymer and inexpensive method obtain considerable improvement, and need not to use expensive surfactant or other organic materials.According to the present invention,, can obtain the brightness degree that increases with the pulsed drive pattern at high voltage (10V, preferably 15V at least) at least if used to the PEDOT of small part neutralization and the combination of PAV.Therefore, the invention still further relates to comprise 10V, the preferred LED of the pulse mode driving mechanism of the voltage of 15V at least are provided provide at least.Neutralization can for example by adding for example metal hydroxides of alkali, perhaps can remove the material of deprotonation by other by removing deprotonation and replace realization with metal ion from PEDOT from PEDOT.For example the structure with NaOH neutralization and described polymer provides in Fig. 1.
For this purpose, the present invention relates to above-mentioned LED, wherein hole-conductive-injection material comprises poly-(3,4-ethylidene dioxy thiophene poly-(styrene sulfonate) (PEDOT), this PEDOT can be by making PEDOT with comprising or result from the anionicsite in sodium or the potassium compound and obtain, and luminescent material comprises that it is luminous to arlydene ethenylidene polymer (PAV).
Described sodium or potassium compound be NaOH or potassium hydroxide, sodium nitrate or potassium nitrate, sodium carbonate or potash or sodium acid carbonate or saleratus preferably, and more preferably NaOH.When being at least 3, pH value that PEDOT is neutralized obtained best effect.Preferably, the pH value is 3-7, more preferably 5.5-6.5.The neutralization of PEDOT can be obtained by the conventional acid alkali reaction, for example use NaOH, perhaps original position is by catching proton from PEDOT under the condition of aqueous solvent and obtain being used to remove, for example also can be under the situation of sodium nitrate, form nitrate anion under these conditions, nitrate anion is caught proton from PEDOT, leave solution with gaseous state nitric acid form.
The invention still further relates to the method that is used to increase light-emitting diode (LED) efficient, this diode comprises anode layer, acid hole-conductive-injection material layer, light-emitting polymer layer and cathode layer, wherein hole-conductive-injection material comprises poly-(3,4-ethylidene dioxy thiophene poly-(styrene sulfonate) (PEDOT), luminescent material comprises luminous poly-(to the arlydene ethenylidene) (PAV), it is characterized in that described acid hole-conductive-injection material is at least in part with the anion neutralization that comprises or result from sodium or potassium compound.
In the accompanying drawings:
Fig. 1 has schematically shown the embodiment according to LED of the present invention in profile.
In Fig. 1, provided the schematic diagram of LED. This LED that illustrates have glass normally base material 1, can be ITO anode 2, comprise PEDOT layer 3, comprise layer 4 and the negative electrode 5 of PPV.
Mention especially patent application WO 96/08047, wherein disclose various raw materials and preparation method thereof, the disclosure content is by being incorporated herein by reference. The material that is used for conductibility transparent polymer (CTP) layer is the mixture of poly-3,4-ethylidene dioxy thiophene and polystyrolsulfon acid (PEDOT).
Active layer is between two electrode layers of conductive material. At least the described electrode layer of one deck must be to be transparent or semitransparent for the utilizing emitted light in the active layer. One of electrode layer serves as for (just) electrode that the hole is injected active layer. The material of this electrode layer has high work function and usually is made of indium oxide layer or indium tin oxide (ITO) layer. In addition, this layer is transparent for utilizing emitted light in active layer. Because gratifying electrical conductivity and the high grade of transparency of ITO, ITO is particularly suitable. Another electrode layer serves as for (bearing) electrode with the electronic injection active layer.
The material that is used for this layer has lower work function and usually is made of for example indium, calcium, barium or magnesium layer.
The electrode layer of ITO is provided by vacuum evaporation, sputter or CVD method. This electrode layer and usually also have positive electrode layer (for example being made of calcium) to cover to construct with mask by traditional photoetching method or by part during vacuum-deposition method according to pattern, this pattern is corresponding to the required pattern of display. In a representative instance of display, the electrode of the first electrode layer and the second electrode lay has line structure, but it also forms the rectangle LED matrix of drive mutually thus with right angle intersection.
This rectangle LED constitutes the pixel or the pictorial element of display.If the electrode of first electrode layer and the second electrode lay is connected with power supply, then form light emitting pixel in the crosspoint of electrode.Simply mode forms display by this way.The pixel structure is not limited to specific shape.Basically all primitive shapes all may produce the sector display that for example is used for display icon or simple picture and text.It should be noted that according to the present invention, except that passive-matrix structure, also use active matrix structure.
The term light emitting polymer comprises homopolymers, terpolymer, copolymer, block copolymer, oligomer (comprising low molecular weight compound) etc., it can be any poly-(to the arlydene ethenylidene) (PAV) electroluminescent material of type, for example poly-(to phenylene vinylidene), wherein phenylene can be substituted, as is disclosed in WO 98/27136.Gather (to phenylene vinylidene) (PPV), more especially the PPV of phenyl replacement is the preferred polymer type that uses.PAV type polymer comprises at least two identical or different arlydene ethenylidene parts.Thus, also can comprise other luminous components, for example fluorenes or spiral shell fluorenes part according to copolymer of the present invention etc.
The preferred soluble conjugated polymer that uses is because they are easy to for example apply with spin coating proceeding or by ink-jet.The preferred dissolution degree improves by replacing conjugation PPV derivative with alkyl and/or alkoxyl or phenyl.This luminescent material can also be the low molecular material that mixes, for example with the dyestuff oxine aluminium that mixes of quinoline a word used for translation ketone for example, deposit in vacuum technology.
Depend on the preparation of described conjugated polymer, described polymer can contain the non-conjugated units of 5-10%.Have now found that this non-conjugated units has increased electroluminescent efficient, electroluminescent efficient defines by the proton number of each injection electronics in the active layer.
Above-mentioned conjugation PAV derivative can be dissolved in the conventional organic solvent, for example halogenated hydrocarbons such as chloroform and the aromatic hydrocarbon that optionally is substituted for example toluene, dimethylbenzene, methyl phenyl ethers anisole, chlorobenzene and.Methyl benzoate and oxolane also can be used as solvent.
The degree of polymerization of described conjugated polymer is 10-100000.
The bed thickness of described conjugated polymer luminescent layer is usually between 10-250nm, particularly between the 50-130nm.
Described LED structure can be arranged on the base material, and this base material is for example made by glass, quartz glass, pottery or synthetic resin material.Transistor or other electronic installations may reside in and form so-called active matrix base material between base material and the transparency electrode.Translucent or the transparent base of preferred use.Rou Xing electroluminescent device if desired then uses the transparent membrane of synthetic resin.Suitable transparent flexible resin is for example polyamide, polyethylene terephthalate, Merlon, polyethylene and polyvinyl chloride.
The present invention sets forth by the following example.
The usefulness of described equipment under given brightness, the cd/A of unit
BAYTRON P VP CH 8000 usefulness cesium hydroxides (comparative example) or NaOH neutralization.Find that CsOH does not have advantageous effect for the usefulness of LED.In pH 1-7 scope, can not obtain to surpass the brightness of 100000cd/m2.
In contrast, NaOH has the effect favourable to this usefulness.Have been found that pH is high more, usefulness is high more.Use NaOH also to make and to obtain the LCD that brightness surpasses 100000cd/m2 as alkali.At pH 4, even may reach more high brightness above 200000cd/m2.
The equipment that is used for acquisition table data has the standard device structure of ITO, 200nm PEDOT, 80nm SY-LEP and Ba/Al negative electrode.This equipment promptly drives at 200Hz with under 1% pulse duty cycle of the voltage that illustrates in the form bracket by pulse mode.
SY-LEP is commercially available from German Covion, and it is the copolymer that has the construction unit of following structure at least.
| Compound | pH | Eff. (cd/A) is when 20000cd/m2 | Eff. (cd/A) is when 60000cd/m2 | Eff. (cd/A) is when 200000cd/m2 |
| Ref. | 1 | 10(8.3) | 9(12.0) | - |
| CsOH | 2 | 9(9.0) | 8.5(13.0) | - |
| CsOH | 3 | 7(11，5) | 6.5(16.0) | - |
| CsOH | 4 | 2.5-3.5(16.0) | - | - |
| CsOH | 5 | 2.5-3.5(16.0) | - | - |
| CsOH | 6 | 2.5-3.5(16.5) | - | - |
| NaOH | 2 | 9.5-11(10.0) | 8-9(13.5) | - |
| NaOH | 3 | 11-13(10.3) | 13-15(14.0) | - |
| NaOH | 4 | 9-10(12.5) | 15-17(14.5) | 17-23(17.5) |
| NaOH | 5 | 7.5-10(11.5) | 11-16(13.0) | 15-20(16.2) |
| NaOH | 6 | 16-17(10.5) | 20-25(12.0) | 28-40(15.0) |
Ref: in adding and compound
Eff.=usefulness
Voltage during brightness degree shown in obtaining illustrates between bracket.
Claims (9)
1. a light-emitting diode (LED), this diode comprises anode layer, acid hole-conductive-injection material layer, light-emitting polymer layer and cathode layer, it is characterized in that described hole-conductive-injection material comprises poly-(3,4-ethylidene dioxy thiophene poly-(styrene sulfonate) (PEDOT), it can be by making PEDOT with comprising or forms anion from sodium or potassium compound to small part and acquisition, and that luminescent material comprises is luminous to arlydene ethenylidene polymer (PAV).
2. the LED of claim 1, wherein said compound is NaOH or potassium hydroxide, sodium nitrate or sells sour potassium, sodium carbonate or potash or sodium acid carbonate or saleratus.
3. the LED of claim 2, wherein said compound is a NaOH.
4. each LED among the claim 1-3, wherein pH is greater than 3.
5. each LED among the claim 1-4, wherein pH is 3-7, preferred 5.5-6.5.
6. each described LED among the claim 1-5, wherein said PAV is poly-(to phenylene vinylidene).
7. each LED among the claim 1-6 comprises being applicable to 10V, the preferred pulse mode driving mechanism of the voltage of 15V at least at least being provided.
8. the method for the driving LED of claim 8, wherein said LED drives with pulse mode under the voltage of 10V, preferred 15V at least at least.
9. be used to improve the method for light-emitting diode (LED) efficient, this light-emitting diode comprises anode layer, acid hole-conductive-injection material layer, light-emitting polymer layer and cathode layer, wherein said hole-conductive-injection material comprises poly-(3,4-ethylidene dioxy thiophene poly-(styrene sulfonate) (PEDOT), luminescent material comprises poly-(to the arlydene ethenylidene) (PAV), it is characterized in that acid hole-conductive-injection material is at least in part with the anion neutralization that comprises or result from sodium or potassium compound.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03102446.6 | 2003-08-06 | ||
| EP03102446 | 2003-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1833323A true CN1833323A (en) | 2006-09-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2004800224280A Pending CN1833323A (en) | 2003-08-06 | 2004-07-29 | Light-emitting diode |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1656707A1 (en) |
| JP (1) | JP2007501514A (en) |
| KR (1) | KR20060061810A (en) |
| CN (1) | CN1833323A (en) |
| TW (1) | TW200510511A (en) |
| WO (1) | WO2005015654A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4381080B2 (en) * | 2003-09-29 | 2009-12-09 | 大日本印刷株式会社 | Organic electroluminescence device and method for producing the same |
| US20070077451A1 (en) * | 2005-09-30 | 2007-04-05 | Pierre-Marc Allemand | Neutralized anode buffer layers to improve processing and performances of organic electronic devices |
| JP4301260B2 (en) | 2006-07-06 | 2009-07-22 | セイコーエプソン株式会社 | Method for manufacturing organic EL device and electronic device |
| JP5037104B2 (en) * | 2006-12-11 | 2012-09-26 | 信越ポリマー株式会社 | Conductive laminate and method for producing the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19652261A1 (en) * | 1996-12-16 | 1998-06-18 | Hoechst Ag | Aryl-substituted poly (p-arylenevinylenes), process for their preparation and their use in electroluminescent devices |
| WO2002084759A1 (en) * | 2001-04-17 | 2002-10-24 | Koninklijke Philips Electronics N.V. | Led comprising a conductive transparent polymer layer with low sulfate and high metal ion content |
| DE10123115B4 (en) * | 2001-05-07 | 2006-05-24 | Samsung SDI Co., Ltd., Suwon | Hole injection layer of an organic light-emitting diode and method for its production |
-
2004
- 2004-07-29 CN CNA2004800224280A patent/CN1833323A/en active Pending
- 2004-07-29 EP EP04744677A patent/EP1656707A1/en not_active Withdrawn
- 2004-07-29 KR KR1020067002239A patent/KR20060061810A/en not_active Application Discontinuation
- 2004-07-29 WO PCT/IB2004/051324 patent/WO2005015654A1/en not_active Application Discontinuation
- 2004-07-29 JP JP2006522466A patent/JP2007501514A/en active Pending
- 2004-08-03 TW TW093123158A patent/TW200510511A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200510511A (en) | 2005-03-16 |
| JP2007501514A (en) | 2007-01-25 |
| EP1656707A1 (en) | 2006-05-17 |
| KR20060061810A (en) | 2006-06-08 |
| WO2005015654A1 (en) | 2005-02-17 |
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