EP1578885A2 - Element electroluminescent organique - Google Patents

Element electroluminescent organique

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Publication number
EP1578885A2
EP1578885A2 EP03782338A EP03782338A EP1578885A2 EP 1578885 A2 EP1578885 A2 EP 1578885A2 EP 03782338 A EP03782338 A EP 03782338A EP 03782338 A EP03782338 A EP 03782338A EP 1578885 A2 EP1578885 A2 EP 1578885A2
Authority
EP
European Patent Office
Prior art keywords
emission
spiro
hole conductor
organic electroluminescent
eml
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Withdrawn
Application number
EP03782338A
Other languages
German (de)
English (en)
Inventor
Horst Vestweber
Anja Gerhard
Philipp STÖSSEL
Hubert Spreitzer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Covion Organic Semiconductors GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH, Covion Organic Semiconductors GmbH filed Critical Merck Patent GmbH
Publication of EP1578885A2 publication Critical patent/EP1578885A2/fr
Withdrawn legal-status Critical Current

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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
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    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
    • C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings
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    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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Definitions

  • the present invention describes a novel design principle for organic electroluminescent elements and its use in displays based thereon.
  • Display elements such as in a calculator, mobile phones and other portable applications
  • large-area displays such as traffic signs, posters and other applications
  • OPERATIVE LIFETIME of OLEDs is still very short, so that only simple applications can be realized commercially up to now. From Sanyo were lifetimes for Application-related brightnesses of blue OLEDs in the range of approx. 3000 h are reported. There are similar values for Kodak materials.
  • the aging processes go i. d. Usually accompanied by an increase in voltage. This effect makes voltage driven organic electroluminescent devices, e.g. B. displays or display elements, difficult or impossible. In this case, too, a current-driven control is more complex and expensive. 7.
  • the operating voltage required has been reduced in recent years, but must be further reduced to improve performance efficiency. This is particularly important for portable applications. 8.
  • the operating current required has also been reduced in recent years, but needs to be further reduced to improve performance efficiency. This is especially important for portable applications.
  • organic electroluminescent devices The general structure of organic electroluminescent devices is described, for example, in US 4,539,507 and US 5,151,629.
  • An organic electroluminescent device usually consists of several layers, which are preferably applied to one another by means of vacuum methods. The individual layers are:
  • a carrier plate substrate (usually glass or plastic films).
  • a transparent anode usually indium tin oxide, ITO).
  • a hole injection layer e.g. B. based on copper phthalocyanine (CuPc) or conductive polymers such as polyaniline (PANI) or polythiophene derivatives (such as PEDOT).
  • CuPc copper phthalocyanine
  • PANI polyaniline
  • PEDOT polythiophene derivatives
  • One or more hole transport layers usually based on triarylamine derivatives z.
  • emission Layer EML
  • this layer can partially coincide with layers 4 or 6, but usually consists of fluorescent dyes, e.g. B. N, N'-diphenyl-quinacridone (QA) or
  • Phosphorescent dyes e.g. B. tris (phenylpyridyl) iridium (IrPPy) doped host molecules such as aluminum tris-8-hydroxy-quinolinate (AIQ 3 ).
  • An electron transport layer (ETL): largely based on aluminum tris-8-hydroxy-quinolinate (AIQ 3 ). 7.
  • An electron injection layer (EIL): this layer can partially coincide with layer 6, or a small part of the cathode is specially treated or specially deposited.
  • EIL electron injection layer
  • a thin layer consisting of a material with a high dielectric constant, such as. B. LiF, Li 2 O, BaF 2 , MgO, NaF.
  • a cathode here metals, metal combinations or metal alloys with a low exit function are generally used.
  • This entire device is structured (depending on the application), contacted and finally hermetically sealed, since i. d. R. the lifespan of such
  • the anode consists, for example, of Al / Ni / NiOx or Al / Pt / PtOx or other metal / metal oxide compounds that have a HOMO greater than 5 eV.
  • the cathode consists of the same materials that are described in points 8 and 9 with the
  • the metal such as. B. Ca, Ba, Mg, Al, In, etc.
  • the layer thickness is below 50 nm, better below 30 nm, even better below 10 nm.
  • Another transparent material is applied to this transparent cathode, e.g. B. ITO (indium tin oxide), IZO (indium zinc oxide), etc.
  • EP-A-281381 describes OLEDs in which the EML consists of a HOST (host) material which can transport holes and electrons and a dopant which can emit light. Characteristic of this application is, on the one hand, that the dopant is used in relatively small amounts (usually in the range of approx. 1%), on the other hand, that the HOST material can transport holes as well as electrons (well).
  • EP-A-610514 describes OLEDs which have small amounts ( ⁇ 19%, preferably ⁇ 9%) of hole-transporting compounds in the EML. However, only very special classes of substances are permitted for these compounds. The storage stability of such devices is relatively low.
  • EP-A-1162674 describes OLEDs in which the EML consists of an emitter, doped with a hole-transporting and an electron-transporting substance at the same time. From a technical point of view, the problem here is that three compounds have to be applied in one layer in a very precisely coordinated mixing ratio. This is precisely the prevailing process
  • EP-A-1167488 describes OLEDs which, as EML, have a special combination of anthracene derivatives and aminodistyrylaryl compounds. It is problematic from a technical point of view that the compounds have a very high molecular weight, which leads to the partial decomposition of the molecules in the prevailing process and the sublimation temperatures required for this, and thus to the deterioration of application parameters.
  • the invention therefore relates to an organic electroluminescent device which has at least one emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one emission material capable of emission, characterized in that at least one of the two materials has one or more Contains spiro-9,9'-bifluorene units and the weight ratio of hole conductor material to emission material is 1:99 to 99: 1, preferably 5:95 to 80:20, particularly preferably 5:95 to 25:75.
  • EML emitting layer
  • Capable of emission in the sense of the invention means that the substance shows an emission in the range from 380 to 750 nm as a pure film in an OLED.
  • Electroluminescent device which has at least one emitting layer (EML), said layer being a mixture of at least one hole conductor material and at least one contains emission material capable of emission, the HOMO of the hole conductor material being in the range of 4.8 to 5.8 eV (vs. vacuum) and the compound having at least one substituted or unsubstituted diarylamino group, preferably at least one triarylamino unit or a carbazole group, and the emission material capable of emission contains one or more spiro-9,9'-bifluorene units and the weight ratio of hole conductor material to emission material is 1:99 to 99: 1, preferably 5:95 to 80:20, particularly preferably 5:95 to 25:75.
  • EML emitting layer
  • a further preferred embodiment of the present invention is an organic electroluminescent device which has at least one emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one emission material capable of emission, the HOMO of the hole conductor material being in the range from 4.8 to 5.8 eV (vs.
  • EML emitting layer
  • the compound contains one or more spiro-9,9'-bifluorene units and at least one group selected from substituted or unsubstituted diarylamino, carbazole or thiophene units and the emission material capable of emission is selected from the Group of metal complexes, stilbenamines, stilbenarylenes, condensed aromatic or heteroaromatic systems, but also of phosphorescent heavy metal complexes, rhodamines, coumarins, the substituted or unsubstituted aluminum, zinc, gallium hydroxyquinolinates, bis (p-diarylaminostyryl) aryls ne, DPVBi (4,4'-bis (2,2-diphenylvinyl) biphenyl) and analogous compounds, anthracenes, naphthacenes, pentacenes, pyrenes, perylenes, rubren, quinacridones, benzothiadiazole compounds, DCM (4- (dicyanomethylene) -2
  • a further preferred embodiment of the present invention is an organic electroluminescent device which has at least one emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one emission material capable of emission, the HOMO of the hole conductor material being in the range from 4.8 to 5.8 eV (vs.
  • EML emitting layer
  • the compound contains one or more spiro-9,9'-bifluorene units and at least one group selected from substituted or unsubstituted diarylamino, carbazole or thiophene units and the emission material capable of emission contains at least one spiro Contains 9,9'-bifluorene unit and the weight ratio of hole conductor material to emission material is 1:99 to 99: 1, preferably 5:95 to 80:20, particularly preferably 5:95 to 25:75.
  • the color coordinates are better, i. h - in the blue area in particular - more saturated colors are achieved.
  • Preferred embodiments of the OLED according to the invention are those in which the glass transition temperature T g of the respective hole conductor connection is greater than 90 ° C., preferably greater than 100 ° C., particularly preferably greater than 120 ° C.
  • a likewise preferred embodiment is given when the glass transition temperature T g of the respective emission compound is greater than 100 ° C., preferably greater than 120 ° C., particularly preferably greater than 130 ° C. It is particularly preferred if both the described high glass temperature of the hole conductor and that of the emission material are present at the same time.
  • the preferred embodiments of the devices described here have a further increased operational as well as storage life due to the high glass temperatures.
  • the layer thickness of the EML i. d.
  • the layer thickness of the EML i. d.
  • the range from 5 to 150 nm preferably in the range from 10 to 100 nm, particularly preferably in the range from 15 to 60 nm, very particularly preferably in the range from 20 to 40 nm.
  • Emission layers of 20-40 nm can be selected.
  • the layer thickness must be adjusted accordingly, i. H. increase.
  • the efficiency of corresponding devices is better.
  • the optimal layer thickness ensures a balanced charge balance in the emission layer (emission film) and thus improves efficiency.
  • the power efficiency is thin
  • the OPERATIVE LIFETIME improves several times with an optimal choice of layer thickness, because a lower current is required here with optimal color coordinates and efficiency.
  • Preferred hole conductor compounds are substituted or unsubstituted triarylamine derivatives, such as triphenylamine derivatives, but also corresponding dimeric or oligomeric compounds, i.e. H.
  • Triarylamine derivatives such as triphenylamine derivatives
  • Indolocarbazole derivatives further also thiophene, bisthiophene and oligothiophene derivatives, as well as pyrrole, bispyrrole and oligopyrrole derivatives; in selected In some cases it is also possible for the triarylamino group to be replaced by a hydrazone unit.
  • Particularly preferred hole conductor connections are substituted or unsubstituted connections according to the formulas shown below:
  • Preferred hole conductor connections are spiro-9,9'-bifluorene derivatives, which are 1 to 6
  • Substituents selected from substituted or unsubstituted diarylamino, carbazole, thiophene, bithiophene or oligothiophene groups, but also compounds which contain one or more substituted or unsubstituted spiro-9,9'-bifluorene derivatives as substituents or instead of simple aryl groups. Hole conductor materials which are present as polymers and spiro-9,9'-bifluorene derivatives are preferred
  • Repeat unit contain, or spiro-9,9'-bifluorene derivatives whose M w maximum of 10,000 g / mol Hole conductor materials containing spiro-9.9 ′′ bifluorene derivatives, whose M w is at most 10000 g / mol, are particularly preferred.
  • Particularly preferred hole conductor connections are substituted or unsubstituted connections according to the formulas shown below:
  • Ar 1 , Ar 2 and AR are intended to stand for aromatic or heteroaromatic cycles with 4 to 40 C atoms.
  • preferred emission materials are metal-hydroxy-quinoline complexes, stilbenamines, stilbenarylenes, condensed aromatic or heteroaromatic systems, but also phosphorescent heavy metal complexes, rhodamines, coumarins, for example substituted or unsubstituted aluminum, zinc, gallium-hydroxy-quinolinates, bis (p-diarylaminostyryl) arylene, DPVBi and analogous compounds, anthracenes, naphthacenes, pentacenes, pyrenes, perylenes, rubrene, quinacridones, benzothiadiazole compounds, DCM, DCJTB, iridium, europium or platinum complexes.
  • Particularly preferred emission materials are substituted or unsubstituted compounds according to the formulas shown below:
  • n is the same or different and means 1, 2 or 3,
  • X is the same or different and represents the elements N, O or S,
  • M is the same or different and for the elements Li, Al, Ga, In, Sc, Y, La, Cr, Mo, W,
  • AR stands for aromatic or heteroaromatic cycles with 4 to 40 C atoms; the substituents R are only intended to indicate a preferred position of such groups and are not to be considered as restrictive here.
  • Preferred emission compounds are spiro-9,9'-bifluorene derivatives which have 1 to 6 substituents selected from substituted or unsubstituted arylenes, heteroarylenes, arylvinylenes or diarylvinylenes, but also arylenes, heteroarylenes or arylvinylenes which have one or more substituted or unsubstituted spiro-9 , 9'-bifluorene derivatives have as substituents.
  • emission compounds are substituted or unsubstituted compounds according to the formulas shown below:
  • AR, Ar 1 , Ar 2 and Ar 3 here stand for aromatic or heteroaromatic cycles with 4 to 40 C atoms; n corresponds to 0, 1 or 2; m corresponds to 1 or 2, o corresponds to 1, 2, 3, 4, 5 or 6; the substituents R are only intended to indicate a preferred position of such groups and are not to be considered as restrictive here.
  • the Z radicals in formula (I) can be present more than once on an aromatic ring.
  • the compounds of formula (I) are new.
  • the invention therefore furthermore relates to compounds of the formula (I) in which Z represents one or more groups of the formula
  • AR, Ar 1 , Ar 2 and Ar 3 are, in each occurrence, identical or different aromatic or heteroaromatic cycles with 4 to 40 C atoms, which can be substituted at the free positions with substituents R 1 ; n is the same or different at each occurrence 0, 1 or 2; m is the same or different at each occurrence 1 or 2; o is the same or different at each occurrence 1, 2, 3, 4, 5 or 6; where AR can be bound both to Ar 2 and to Ar 3 and both in the form of a dendrimer; x is the same or different at each occurrence 0, 1, 2, 3 or 4, with the proviso that the sum of all indices x is not equal to zero, R 1 is the same or different at each occurrence is a straight-chain, branched or cyclic alkyl or Alkoxy chain with 1 to 22 C-
  • Atoms in which one or more non-adjacent C atoms are also represented by NR 2 , O, S,
  • -CO-O-, O-CO-O can be replaced, whereby one or more H atoms can also be replaced by fluorine, an aryl or aryloxy group with 5 to 40 C atoms, in which one or more C- Atoms can be replaced by O, S or N, which can also be substituted by one or more non-aromatic radicals R 1 , or Cl, F, CN, N (R 2 ) 2 , B (R 2 ) 2 , whereby also two or more radicals R can form an aliphatic or aromatic, mono- or polycyclic ring system with one another;
  • Each occurrence of R 2 is the same or different H, a straight-chain, branched or cyclic alkyl chain with 1 to 22 C atoms, in which one or more non-adjacent C atoms are also represented by O, S, -CO-O-, O- CO-O can be replaced, where one or more H atoms can also be replaced by fluorine, an aryl group with
  • Electroluminescent devices according to the invention can be represented, for example, as follows:
  • ITO coated substrate The substrate preferred is ITO coated glass with the lowest possible or no ionic impurities, such as. B. flat glass from Merck-Balzers or Akaii. However, other transparent substrates coated with ITO, such as, for. B. flexible plastic films or laminates can be used.
  • the ITO must have the highest possible conductivity with a high
  • ITO layer thicknesses between 50 and 200 nm have proven to be particularly suitable.
  • the ITO coating must be as flat as possible, preferably with a roughness below 2 nm.
  • the substrates are first pre-cleaned with 4% deconex in deionized water.
  • the ITO-coated substrate is then either treated with ozone for at least 10 minutes or with oxygen plasma for a few minutes, or irradiated with an excimer lamp for a short time.
  • HIL Hole Injection Layer
  • PANI polyaniline
  • PEDOT polythiophene
  • the ITO substrate 200 nm, preferably between 40 and 150 nm layer thickness can be applied to the ITO substrate by spin coating, inkjet printing or other coating processes.
  • the ITO substrates coated with PEDOT or PANI are then dried.
  • Several methods are available for drying. Conventionally, the films are in the drying oven for 1 to 10 minutes between 110 and 200 ° C, preferably between 150 and
  • CuPc copper phthalocyanine
  • PEDOT and PANI show a particularly low absorption in the visible range and thus a high level of transparency, which is another necessary property for the HIL.
  • HTL hole transport layers
  • MTDATA 4,4 ', 4 "tris (N-3- methylphenyl) -N-phenyl-amino) -triphenylamine
  • NaphDATA 4,4 ', 4 "-Tris (N-1-naphthyl) -N-phenyl-amino) -triphenylamine) as the first HTL and NPB (N, N '-Di (naphth-1-yl) - N, N'-diphenyl-benzidine) or Spiro-TAD (tetrakis (2,2', 7,7'-diphenylamino) -spiro-9,9'-bifluorene) as second HTL very good results.
  • MTDATA or NaphDATA increase the efficiency in most OLEDs by approx.
  • Spiro-TAD or NPB have a layer thickness between 5 and 150 nm, preferably 10 and 100 nm, particularly preferably between 20 and 60 nm. With increasing layer thickness of NPB and most other triarylamines, higher voltages are required for the same brightness. However, the layer thickness of Spiro-TAD has only a minor influence on the current-voltage-electroluminescence characteristics, ie the voltage required to achieve a certain brightness depends only slightly on the Spiro-TAD layer thickness. All materials are reduced in vacuum sublimation systems at a pressure of less than 10 "5 mbar, preferably less than 10 " 6 mbar, particularly preferably less
  • Emission Layer This layer can be partially with the
  • Layers 3 and / or 5 coincide. It consists e.g. B. from a host material and simultaneous fluorescent dye, such as Spiro-DPVBi (2,2 ', 7,7'-tetrakis (2,2-diphenyl-vinyl) -spiro-9,9'-bifluorene) and a hole transport material, such as z. B. Spiro-TAD. Good results are obtained with a concentration of 5 - 10% Spiro-TAD in Spiro-DPVBi with an EML layer thickness of 15 - 70 nm, preferably 20 - 50 nm.
  • All materials are in vacuum sublimation systems at a pressure of less than 10 "5 mbar , preferably less than 10 "6 mbar, particularly preferably less than 10 " 7 mbar.
  • the evaporation rates can be between 0.01 and 10 nm / s, preferably 0.1 and 1 nm / s.
  • newer processes such as the OPVD or LITI are suitable for the coating of low molecular weight materials
  • a thin layer of 3 - 20 nm, preferably 5 - 10 nm increases the efficiency very effectively. All materials are evaporated in vacuum sublimation systems at a pressure of less than 10 "5 mbar, preferably less than 10 " 6 mbar, particularly preferably less than 10 "7 mbar.
  • the evaporation rates can be between 0.01 and 10 nm / s, preferably 0.1 and 1 nm / s
  • the OPVD is another method of applying these materials to a substrate.
  • Electron Transport Layer Metal hydroxy-quinolates are well suited as ETL materials; aluminum tris-8-hydroxy-quinolate (AIQ 3 ) in particular has proven to be one of the most stable electron conductors. All materials are evaporated in vacuum sublimation systems at a pressure of less than 10 "5 mbar, preferably less than 10 " 6 mbar, particularly preferably less than 10 "7 mbar
  • Evaporation rates can be between 0.01 and 10 nm / s, preferably 0.1 and 1 nm / s.
  • EML Evaporation rates
  • HIL HIL
  • HTL newer processes such as OPVD or LITI are suitable for coating low molecular weight materials.
  • Electron Injection Layer A thin layer with a layer thickness between 0.2 and 8 nm, preferably 0.5 - 5 nm, consisting of one
  • Materials are evaporated in vacuum sublimation systems at a pressure of less than 10 "5 mbar, preferably less than 10 " 6 mbar, particularly preferably less than 10 "7 mbar.
  • the evaporation rates can be between 0.01 and 1 nm / s, preferably 0.1 and 0.5 nm / s ,
  • Cathode Usually metals, metal combinations or metal alloys with a low work function are used here.
  • Encapsulation An effective encapsulation of the organic layers including the EIL and the cathode is essential for organic electroluminescent devices. If the organic display is built on a glass substrate, there are several possibilities. One possibility is to glue the entire structure with a second glass or metal plate, whereby two-component or UV-curing epoxy adhesives have proven to be particularly suitable
  • Electroluminescent device completely or only glued to the edge. If the organic display is only glued on the edge, the durability can be further improved by adding a so-called getter.
  • This getter consists of a very hygroscopic material, especially metal oxides, such as. B. BaO, CaO etc., which binds penetrating water and water vapors. An additional binding of oxygen can be achieved with getter materials such as e.g. B. Ca, Ba, etc.
  • getter materials such as e.g. B. Ca, Ba, etc.
  • Laminates made of alternating thin plastic and inorganic layers e.g. SiO x or SiN x ) have proven particularly useful here. 10.
  • the structure described under points 1 - 9 is suitable for monochrome as well as for full-color passive or actively operated matrix displays for portable devices, such as. B. mobile phones, PDAs, camcorders and other applications.
  • Passive matrix displays require 1000 to several 100,000 cd / m 2 peak brightness depending on the number of pixels; first applications are between 5000 and 20000 cd / m 2 peak brightness.
  • the active matrix control is preferred.
  • the required brightness of the individual pixels is between 50 and 1000 cd / m 2 , preferably between 100 and 300 cd / m 2 .
  • the structure described under points 1 - 9 is also suitable for this.
  • Active matrix control is suitable for all display applications (such as cell phones, PDAs and other applications), but especially also for large-scale applications such as B. in labtops and televisions. Other applications are white or colored backlighting for monochrome or multicolored display elements (e.g. in the
  • the devices according to the invention can be produced not only by sublimation processes or OPVD processes but also by special printing processes (such as the aforementioned LITI).
  • This has advantages with regard to the scalability of the production as well as with regard to the setting of mixing ratios in the blend layers used.
  • this usually requires appropriate layers (for LITI: transfer
  • These layers then contain (in addition to any auxiliary substances required for the transfer step) the mixture of hole conductor material and emitter material in the desired ratio, as described above. These layers are too
  • the devices according to the invention can also be produced by other printing processes, such as, for example, ink-jet printing.
  • O-SCs organic solar cells
  • O-FETs organic field effect transistors
  • O-lasers organic laser diodes
  • Examples 10 and 11 additionally contained a hole blocking layer (HBL) between EML and ETL.
  • HBL hole blocking layer
  • a 60 nm thick layer PANI from Covion (Pat 010) or a 60 nm thick layer PEDOT from Bayer (Baytron P 4083) was used as the HIL.
  • the PANI layer was produced from a 4% dispersion by spin coating at 4000 rpm. The resulting layer was annealed at 180 ° C for five minutes.
  • the PEDOT layer was produced from a 2% dispersion by spin coating at 3000 rpm. The resulting layer was annealed at 110 ° C for five minutes.
  • the organic materials (HTL-1 / HTL-2 / EML / (HBL) / ETL) were evaporated in succession in a Pfeiffer vacuum evaporation apparatus converted by Covion at a pressure ⁇ 10 "6 mbar.
  • the system was operated with an automatic rate and
  • the unmixed EML layers which were produced as a reference, were evaporated in the Pfeiffer evaporation apparatus, just like HTL-1, HTL-2, ETL and HBL, at a pressure of ⁇ 10 "6 mbar.
  • the mixed EML layers two materials were evaporated at the same time, and the concentrations described in the examples were achieved by adjusting the rates according to the mixing ratios Metals (metal-1 / metal-2) were evaporated in a Balzers evaporation apparatus converted by Covion at a pressure ⁇ 10 "6 mbar.
  • the system was also equipped with an automatic rate and layer thickness control.
  • EML the substances Spiro-DPVBi + Spiro-TAD
  • Spiro-DPVBi + Spiro-TAD the substances Spiro-DPVBi + Spiro-TAD
  • Spiro-TAD the substances Spiro-DPVBi + Spiro-TAD
  • OLEDs were produced as reference without the substance Spiro-TAD in the EML.
  • the service life of the OLED increased by a factor of 3 compared to the reference
  • Example 2 The layer structure corresponded to that described above: Glass / ITO / PEDOT / NaphDATA /
  • Spiro-TAD / EML Spiro-DPVBi (+ Spiro-AA2) / AIQ 3 / Ba / Ag.
  • the two materials of the EML were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (Spiro-DPVBi and Spiro-AA2), with Spiro-AA2 accounting for 10%.
  • OLEDs were produced as reference without the substance Spiro-AA2 in the EML.
  • the service life of the OLED increased by a factor> 8 compared to the reference OLED from approx. 1500 h to> 12000 h.
  • steeper IU-EL characteristics were obtained, ie lower voltages were required to achieve a certain brightness, e.g. B. for a brightness of 100 cd / m 2 instead of 5.5 V only 4.5 V.
  • the two materials of the EML (the substances Spiro-Ant1 and Spiro-TAD) were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (Spiro-Ant1 and
  • the two materials of the EML (the substances Spiro-Ant2 and Spiro-TAD) were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (Spiro-Ant2 and
  • Spiro-TAD Spiro-TAD
  • Spiro-TAD Spiro-TAD
  • OLEDs were produced as reference without the substance Spiro-TAD in the EML.
  • the service life of the OLED increased by a factor> 3 compared to the reference OLED from approx. 300 h to> 900 h.
  • steeper IU-EL characteristics were obtained, ie lower voltages were required to achieve a certain brightness, e.g. B. for a brightness of 100 cd / m 2 instead of 6.5 V only 5.5 V.
  • EML the substances Spiro-Pyren and Spiro-TAD
  • the EML consisted of a mixture of the two substances (Spiro-Pyren and Spiro-TAD), whereby Spiro-TAD had a share of 10%.
  • OLEDs were produced as reference without the substance Spiro-TAD in the EML. In the case of mixing in the EML, the service life of the OLED increased by a factor of 3 compared to the reference
  • the layer structure corresponded to that described above: Glass / ITO / PEDOT / NaphDATA /
  • Spiro-TAD / EML TBPP (+ Spiro-TAD) / AIQ 3 / Ba / Ag.
  • the two materials of the EML (the substances TBPP and Spiro-TAD) were developed and synthesized by Covion. The
  • EML consisted of a mixture of the two substances (TBPP and Spiro-TAD), with Spiro-TAD accounting for 10%. Furthermore, OLEDs were produced as reference without the substance Spiro-TAD in the EML. When mixed in the EML, the service life of the OLED increased by a factor of 10 compared to the reference OLED from approx. 500 h to 5000 h. At the same time, the photometric efficiency (unit cd / A) was up to
  • Example 7 The layer structure corresponded to that described above: Glass / ITO / PEDOT / NaphDATA /
  • Spiro-TAD / EML DTBTD (+ Spiro-TAD) / AIQ 3 / Ba / Ag.
  • the two materials of EML were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (DTBTD and Spiro-TAD), with Spiro-TAD accounting for 10%.
  • OLEDs were produced as reference without the substance Spiro-TAD in the EML. When mixed in the EML, the service life of the OLED increased by a factor of 8 compared to the reference OLED from approx. 500 h to 4000 h.
  • Example 8 The layer structure corresponded to that described above: Glass / ITO / PEDOT / NaphDATA /
  • Spiro-TAD / EML BDPBTD (+ Spiro-TAD) / AIQ 3 / Ba / Ag.
  • the two materials of the EML (the substances BDPBTD and Spiro-TAD) were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (BDPBTD and Spiro-TAD), with Spiro-TAD accounting for 90%.
  • OLEDs were produced as reference without the substance Spiro-TAD in the EML. In the case of mixing in the EML, the service life of the OLED increased by a factor> 10 in comparison to the reference OLED from approx. 1000 h to> 10000 h.
  • the photometric efficiency (unit cd / A) was improved by up to 100%, and the power efficiency was also increased. Furthermore, steeper IU-EL characteristics were obtained, ie lower voltages were required to achieve a certain brightness, e.g. B. for a brightness of 100 cd / m 2 instead of 8 V only 5 V.
  • the substances BDTBTD and Spiro-TAD were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (BDTBTD and Spiro-TAD), with Spiro-TAD accounting for 90%.
  • OLEDs were produced as reference without the substance Spiro-TAD in the EML. In the case of mixing in the EML, the lifespan of the OLED increased by a factor of 10 compared to the reference
  • OLED from approx. 1000 h to> 10000 h.
  • the photometric efficiency (unit cd / A) was improved by up to 400%, and the power efficiency was also increased.
  • steeper IU-EL characteristics were obtained, ie lower voltages were required to achieve a certain brightness, e.g. B. for a brightness of 100 cd / m 2 instead of 9 V only 6 V.
  • OLEDs produced as reference without the substance spiro-carbazole in the EML The photometric efficiency (unit cd / A) has been improved by up to 500% and the power efficiency has also been increased. Furthermore, steeper IU-EL characteristics were obtained, ie lower voltages were required to achieve a certain brightness, e.g. B. for a brightness of 100 cd / m 2 instead of 9 V only 6 V.
  • ITO / PEDOT / NaphDATA / Spiro-TAD / EML IrPPy (+ Spiro-4PP6) / BCP / AIQ 3 / Ba / Ag.
  • IrPPy was synthesized by Covion, and Spiro-4PP6 was developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (IrPPy and Spiro-4PP6), with Spiro-4PP6 accounting for 90%.
  • OLEDs were produced as reference without the substance Spiro-4PP6 in the EML.
  • the photometric efficiency (unit cd / A) was improved by up to 400% and the power efficiency was also increased.
  • steeper IU-EL characteristics were obtained, ie lower voltages were required to achieve a certain brightness, e.g. B. for a brightness of 100 cd / m 2 instead of 9 V only 5.5 V.
  • Example 12 The layer structure corresponded to that described above: Glass / ITO / PEDOT / NaphDATA /
  • Spiro-TAD / EML Spiro-Ant2 (+ CPB) / AIQ 3 / Ba / Ag.
  • the two materials of EML were developed and synthesized by Covion.
  • the EML consisted of a mixture of the two substances (Spiro-Ant2 and CPB), with CPB accounting for 20%.
  • OLEDs were produced as reference without the substance CPB in the EML. In the case of mixing in the EML, the
  • the EML consisted of a mixture of the two substances (Spiro-Pyren and CPB), whereby CPB had a share of 10%.
  • OLEDs were produced as reference without the substance CPB in the EML. When mixed in the EML, the service life of the OLED increased by a factor of 6 compared to the reference OLED from approx. 300 h to> 1800 h.

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Abstract

L'invention concerne des dispositifs électroluminescents organiques améliorés, caractérisés en ce que leur couche émettrice (EML) est constituée d'un mélange de deux substances présentant respectivement des propriétés de conduction par trous et des propriétés d'émission lumineuse, et en ce qu'au moins une de ces substances contient un motif spiro-9,9'-bifluorène.
EP03782338A 2002-12-23 2003-12-09 Element electroluminescent organique Withdrawn EP1578885A2 (fr)

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Families Citing this family (422)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004339136A (ja) * 2003-05-15 2004-12-02 Idemitsu Kosan Co Ltd スピロ結合含有化合物、発光性塗膜形成用材料及びそれを用いた有機エレクトロルミネッセンス素子
KR101175808B1 (ko) * 2003-07-21 2012-08-24 메르크 파텐트 게엠베하 유기 전자발광 부품
DE10350722A1 (de) 2003-10-30 2005-05-25 Covion Organic Semiconductors Gmbh Metallkomplexe
JP4351935B2 (ja) * 2004-03-10 2009-10-28 富士フイルム株式会社 有機電界発光素子
DE102004021989A1 (de) 2004-05-04 2005-12-15 Covion Organic Semiconductors Gmbh Organische elektronische Vorrichtungen
DE102004031000A1 (de) * 2004-06-26 2006-01-12 Covion Organic Semiconductors Gmbh Organische Elektrolumineszenzvorrichtungen
KR100688030B1 (ko) * 2004-09-14 2007-02-28 김환규 아릴 에테르형 덴드론을 함유한 새로운 발광 이리듐(ⅲ)착화합물과 그의 제조 방법
US8344410B2 (en) 2004-10-14 2013-01-01 Daktronics, Inc. Flexible pixel element and signal distribution means
US7893948B1 (en) 2004-10-14 2011-02-22 Daktronics, Inc. Flexible pixel hardware and method
US7868903B2 (en) * 2004-10-14 2011-01-11 Daktronics, Inc. Flexible pixel element fabrication and sealing method
KR101224708B1 (ko) * 2004-10-19 2013-01-21 삼성전자주식회사 (올리고티오펜-아릴렌) 유도체 및 이를 이용한유기박막트랜지스터
JP2006156267A (ja) * 2004-12-01 2006-06-15 Sony Corp 表示装置の製造方法および表示装置
JP4801429B2 (ja) * 2004-12-06 2011-10-26 株式会社半導体エネルギー研究所 発光素子、及び該発光素子を有する発光装置
CN101894917B (zh) * 2004-12-06 2012-08-29 株式会社半导体能源研究所 发光元件和使用该元件的发光装置
US20060214567A1 (en) * 2005-03-25 2006-09-28 Yongchun Luo Organic electroluminescent element
EP1871856A1 (fr) * 2005-04-12 2008-01-02 Merck Patent GmbH Dispositifs electroluminescents organiques
DE102005040411A1 (de) 2005-08-26 2007-03-01 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102005043163A1 (de) 2005-09-12 2007-03-15 Merck Patent Gmbh Verbindungen für organische elektronische Vorrichtungen
TWI268952B (en) 2005-09-21 2006-12-21 Au Optronics Corp Spiro silane compound and organic electroluminescent device using the same
DE102005058543A1 (de) * 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
DE102005058557A1 (de) 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102005058558A1 (de) * 2005-12-08 2007-06-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
JP5093879B2 (ja) * 2006-03-20 2012-12-12 国立大学法人京都大学 ピレン系有機化合物、トランジスタ材料及び発光トランジスタ素子
JP4823730B2 (ja) * 2006-03-20 2011-11-24 新日鐵化学株式会社 発光層化合物及び有機電界発光素子
DE102006013802A1 (de) * 2006-03-24 2007-09-27 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102006031990A1 (de) 2006-07-11 2008-01-17 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
WO2008105349A1 (fr) * 2007-02-28 2008-09-04 Semiconductor Energy Laboratory Co., Ltd. Elément émettant de la lumière utilisant un dérivé de spirofluorène et appareil électronique
KR100892021B1 (ko) * 2007-03-26 2009-04-07 고려대학교 산학협력단 광굴절 덴드론 화합물, 광굴절 덴드리머 화합물 및 그의 제조방법, 상기 화합물을 이용한 광굴절 소자 및 상기 소자의 제조방법
DE102007024850A1 (de) 2007-05-29 2008-12-04 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
WO2009066600A1 (fr) * 2007-11-19 2009-05-28 Idemitsu Kosan Co., Ltd. Dérivé de monobenzochrysène, matière de dispositif électroluminescent organique contenant celui-ci et dispositif électroluminescent organique utilisant la matière de dispositif électroluminescent organique
DE102008008953B4 (de) * 2008-02-13 2019-05-09 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102008018670A1 (de) 2008-04-14 2009-10-15 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102008024182A1 (de) 2008-05-19 2009-11-26 Merck Patent Gmbh Verbindungen für organische elektronische Vorrichtung
US8324800B2 (en) * 2008-06-12 2012-12-04 Global Oled Technology Llc Phosphorescent OLED device with mixed hosts
US9604245B2 (en) 2008-06-13 2017-03-28 Kateeva, Inc. Gas enclosure systems and methods utilizing an auxiliary enclosure
JP5312861B2 (ja) * 2008-07-15 2013-10-09 日本放送協会 有機ｅｌ素子および有機ｅｌディスプレイ
DE102008035413A1 (de) 2008-07-29 2010-02-04 Merck Patent Gmbh Verbindungen für organische elektronische Vorrichtungen
DE102008054141A1 (de) 2008-10-31 2010-05-06 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
DE102009022858A1 (de) 2009-05-27 2011-12-15 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
DE102008063490B4 (de) 2008-12-17 2023-06-15 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung
DE102008064200A1 (de) 2008-12-22 2010-07-01 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102009005289B4 (de) 2009-01-20 2023-06-22 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung und elektronische Vorrichtungen, enthaltend diese
DE102009005290A1 (de) * 2009-01-20 2010-07-22 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
DE102009005288A1 (de) 2009-01-20 2010-07-22 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009005746A1 (de) 2009-01-23 2010-07-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009007038A1 (de) 2009-02-02 2010-08-05 Merck Patent Gmbh Metallkomplexe
DE102009009277B4 (de) 2009-02-17 2023-12-07 Merck Patent Gmbh Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen
DE102009012346B4 (de) 2009-03-09 2024-02-15 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung und Verfahren zu deren Herstellung
DE102009017064A1 (de) 2009-04-09 2010-10-14 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
CN120623053A (zh) * 2009-05-29 2025-09-12 株式会社半导体能源研究所 芴衍生物、发光元件、发光器件、电子器件和照明器件
DE102009023155A1 (de) 2009-05-29 2010-12-02 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
CN102421858A (zh) 2009-06-22 2012-04-18 默克专利有限公司 导电制剂
DE102009031021A1 (de) 2009-06-30 2011-01-05 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009032922B4 (de) 2009-07-14 2024-04-25 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung, deren Verwendung sowie elektronische Vorrichtung
DE102009033371A1 (de) 2009-07-16 2011-05-12 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009034625A1 (de) 2009-07-27 2011-02-03 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
WO2011015265A2 (fr) 2009-08-04 2011-02-10 Merck Patent Gmbh Dispositifs électroniques comprenant des hydrocarbures polycycliques
DE102009041289A1 (de) 2009-09-16 2011-03-17 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102009053645A1 (de) * 2009-11-17 2011-05-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtung
US9666806B2 (en) 2009-09-16 2017-05-30 Merck Patent Gmbh Formulations for the production of electronic devices
DE102009042693A1 (de) 2009-09-23 2011-03-24 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009048791A1 (de) 2009-10-08 2011-04-14 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102009051172A1 (de) 2009-10-29 2011-05-05 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009053191A1 (de) 2009-11-06 2011-05-12 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009052428A1 (de) 2009-11-10 2011-05-12 Merck Patent Gmbh Verbindung für elektronische Vorrichtungen
DE102009053382A1 (de) 2009-11-14 2011-05-19 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102009053836A1 (de) 2009-11-18 2011-05-26 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
EP2517537B1 (fr) 2009-12-22 2019-04-03 Merck Patent GmbH Surfactants fonctionnels électroluminescents
WO2011076323A1 (fr) 2009-12-22 2011-06-30 Merck Patent Gmbh Formulations comprenant des matériaux fonctionnels à phases séparées
WO2011076314A1 (fr) 2009-12-22 2011-06-30 Merck Patent Gmbh Formulations électroluminescentes
KR20120123361A (ko) 2009-12-23 2012-11-08 메르크 파텐트 게엠베하 유기 반도성 화합물을 포함하는 조성물
CN102668152A (zh) 2009-12-23 2012-09-12 默克专利有限公司 包括聚合粘结剂的组合物
DE102010005697A1 (de) 2010-01-25 2011-07-28 Merck Patent GmbH, 64293 Verbindungen für elektronische Vorrichtungen
DE102010006121B4 (de) 2010-01-29 2022-08-11 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010009193B4 (de) 2010-02-24 2022-05-19 MERCK Patent Gesellschaft mit beschränkter Haftung Zusammensetzung enthaltend Fluor-Fluor Assoziate, Verfahren zu deren Herstellung, deren Verwendung sowie organische elektronische Vorrichtung diese enthaltend
DE102010009903A1 (de) 2010-03-02 2011-09-08 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
DE102010010481A1 (de) 2010-03-06 2011-09-08 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE102010010631A1 (de) 2010-03-09 2011-09-15 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
KR101757016B1 (ko) 2010-03-11 2017-07-11 메르크 파텐트 게엠베하 방사성 섬유
EP2544765A1 (fr) 2010-03-11 2013-01-16 Merck Patent GmbH Fibres en thérapie et cosmétique
DE102010012738A1 (de) 2010-03-25 2011-09-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010013068A1 (de) 2010-03-26 2011-09-29 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
DE102010013806B4 (de) 2010-04-03 2021-06-10 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
WO2011128034A1 (fr) 2010-04-12 2011-10-20 Merck Patent Gmbh Composition ayant des performances améliorées
CN102844902B (zh) 2010-04-12 2016-06-08 默克专利有限公司 用于制备有机电子器件的组合物和方法
DE102010014933A1 (de) * 2010-04-14 2011-10-20 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
WO2011137922A1 (fr) 2010-05-03 2011-11-10 Merck Patent Gmbh Formulations et dispositifs électroniques
DE102010019306B4 (de) 2010-05-04 2021-05-20 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtungen
WO2011138889A1 (fr) * 2010-05-07 2011-11-10 住友化学株式会社 Élément organique de conversion photoélectrique
DE102010020044A1 (de) 2010-05-11 2011-11-17 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
WO2011147523A1 (fr) 2010-05-27 2011-12-01 Merck Patent Gmbh Formulation et procédé pour la préparation de dispositifs électroniques organiques
US10190043B2 (en) 2010-05-27 2019-01-29 Merck Patent Gmbh Compositions comprising quantum dots
JP6054290B2 (ja) 2010-06-15 2016-12-27 メルク パテント ゲーエムベーハー 金属錯体
DE102010024335A1 (de) 2010-06-18 2011-12-22 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
DE102010024542A1 (de) 2010-06-22 2011-12-22 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102010024897A1 (de) 2010-06-24 2011-12-29 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010027317A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
WO2012010238A1 (fr) 2010-07-17 2012-01-26 Merck Patent Gmbh Amélioration de la pénétration et de l'action
JP2013539584A (ja) 2010-07-26 2013-10-24 メルク パテント ゲーエムベーハー 量子ドットおよびホスト
CN103026525B (zh) 2010-07-26 2016-11-09 默克专利有限公司 在器件中的纳米晶体
JP5968885B2 (ja) 2010-07-30 2016-08-10 メルク パテント ゲーエムベーハー 有機エレクトロルミネセンスデバイス
DE102010033548A1 (de) 2010-08-05 2012-02-09 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102010045405A1 (de) 2010-09-15 2012-03-15 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010048074A1 (de) 2010-10-09 2012-04-12 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
DE102010048608A1 (de) 2010-10-15 2012-04-19 Merck Patent Gmbh Materialien für organische Elektrolumineszenzvorrichtungen
DE102010048607A1 (de) 2010-10-15 2012-04-19 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
CN103228647B (zh) 2010-11-24 2017-02-15 默克专利有限公司 用于有机电致发光器件的材料
DE102010054316A1 (de) 2010-12-13 2012-06-14 Merck Patent Gmbh Substituierte Tetraarylbenzole
DE102011106849A1 (de) 2010-12-15 2012-06-21 Merck Patent Gmbh Verfahren zur Synthese N-N verknüpfter und um die N-N Bindung rotationsgehinderter bis-N-heterocyclische Carbene und deren Einsatz als Liganden für Metallkomplexe
DE102010055902A1 (de) 2010-12-23 2012-06-28 Merck Patent Gmbh Organische Elektrolumineszenzvorrichtung
DE112011104715A5 (de) 2011-01-13 2014-02-06 Merck Patent Gmbh Verbindungen für organische Elektrolumineszenzvorrichtungen
US8751777B2 (en) 2011-01-28 2014-06-10 Honeywell International Inc. Methods and reconfigurable systems to optimize the performance of a condition based health maintenance system
DE102011010841A1 (de) 2011-02-10 2012-08-16 Merck Patent Gmbh (1,3)-Dioxan-5-on-Verbindungen
DE102011011104A1 (de) 2011-02-12 2012-08-16 Merck Patent Gmbh Substituierte Dibenzonaphtacene
WO2012110178A1 (fr) 2011-02-14 2012-08-23 Merck Patent Gmbh Dispositif et procédé de traitement de cellules et de tissu cellulaire
DE102011011539A1 (de) 2011-02-17 2012-08-23 Merck Patent Gmbh Verbindungen für elektronische Vorrichtungen
US9923152B2 (en) 2011-03-24 2018-03-20 Merck Patent Gmbh Organic ionic functional materials
CN103459403B (zh) 2011-04-04 2016-08-17 默克专利有限公司 金属络合物
EP2695213B1 (fr) 2011-04-05 2019-11-13 Merck Patent GmbH Dispositif électroluminescent organique
CN106025099B (zh) 2011-04-12 2018-09-07 精工爱普生株式会社 发光元件、发光装置、认证装置以及电子设备
JP6271417B2 (ja) 2011-04-13 2018-01-31 メルク パテント ゲーエムベーハー 電子素子のための材料
EP2697226B1 (fr) 2011-04-13 2017-01-18 Merck Patent GmbH Composés pour dispositifs électroniques
JP6022541B2 (ja) 2011-04-18 2016-11-09 メルク パテント ゲーエムベーハー 電子デバイスのための化合物
EP2699571B1 (fr) 2011-04-18 2018-09-05 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
JP5765034B2 (ja) 2011-04-18 2015-08-19 セイコーエプソン株式会社 チアジアゾール系化合物、発光素子用化合物、発光素子、発光装置、認証装置および電子機器
WO2012149992A1 (fr) 2011-05-04 2012-11-08 Merck Patent Gmbh Dispositif de conservation de produits frais
KR101970940B1 (ko) 2011-05-05 2019-04-22 메르크 파텐트 게엠베하 전자 소자용 화합물
JP6195823B2 (ja) 2011-05-05 2017-09-13 メルク パテント ゲーエムベーハー 電子素子のための化合物
JP6223961B2 (ja) 2011-05-12 2017-11-01 メルク パテント ゲーエムベーハー 有機イオン性機能材料、組成物および電子素子
KR101934135B1 (ko) 2011-06-03 2019-04-05 메르크 파텐트 게엠베하 유기 전계발광 디바이스
KR101972184B1 (ko) 2011-06-03 2019-04-24 메르크 파텐트 게엠베하 금속 착물
CN102842686A (zh) * 2011-06-21 2012-12-26 卡帝瓦公司 用于控制有机发光器件的性质的材料和方法
KR101747059B1 (ko) 2011-06-21 2017-07-11 카티바, 인크. Oled 마이크로 공동 및 버퍼 층을 위한 물질과 그 생산 방법
US9012892B2 (en) 2011-06-21 2015-04-21 Kateeva, Inc. Materials and methods for controlling properties of organic light-emitting device
KR101943676B1 (ko) 2011-06-28 2019-01-29 메르크 파텐트 게엠베하 금속 착물
KR102088637B1 (ko) 2011-07-29 2020-03-13 메르크 파텐트 게엠베하 전자 소자용 화합물
KR101983019B1 (ko) 2011-08-03 2019-05-28 메르크 파텐트 게엠베하 전자 소자용 물질
ITMI20111520A1 (it) * 2011-08-08 2013-02-09 Eni Spa Concentratore solare luminescente comprendente composti benzotiadiazolici disostituiti
KR20130018547A (ko) 2011-08-09 2013-02-25 세이코 엡슨 가부시키가이샤 티아디아졸계 화합물, 발광 소자, 발광 장치, 인증 장치, 전자 기기
JP5790279B2 (ja) 2011-08-09 2015-10-07 セイコーエプソン株式会社 発光素子、発光装置および電子機器
KR101967014B1 (ko) 2011-08-10 2019-04-08 메르크 파텐트 게엠베하 금속 착물
DE102012016192A1 (de) 2011-08-19 2013-02-21 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
KR101914951B1 (ko) 2011-08-22 2018-11-05 메르크 파텐트 게엠베하 유기 전계발광 디바이스
JP6174030B2 (ja) 2011-09-21 2017-08-02 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイス用のカルバゾール誘導体
EP2764558B1 (fr) 2011-10-06 2019-02-27 Merck Patent GmbH Dispositif électroluminescents organiques
DE102011116165A1 (de) 2011-10-14 2013-04-18 Merck Patent Gmbh Benzodioxepin-3-on-Verbindungen
KR101903216B1 (ko) 2011-10-20 2018-10-01 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR102045197B1 (ko) 2011-10-27 2019-11-18 메르크 파텐트 게엠베하 전자 소자용 물질
DE102011117422A1 (de) 2011-10-28 2013-05-02 Merck Patent Gmbh Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen
DE102011117364A1 (de) 2011-10-29 2013-05-02 Merck Patent Gmbh Hautaufheller in der Phototherapie
EP2773721B1 (fr) 2011-11-01 2015-11-25 Merck Patent GmbH Dispositif électroluminescent organique
KR101885244B1 (ko) * 2011-11-07 2018-08-06 삼성전자주식회사 유기 광전 소자 및 이미지 센서
US10305040B2 (en) 2011-11-17 2019-05-28 Merck Patent Gmbh Spiro dihydroacridine derivatives and the use thereof as materials for organic electroluminescence devices
KR20180126629A (ko) 2011-12-12 2018-11-27 메르크 파텐트 게엠베하 전자 소자용 화합물
DE102012022880B4 (de) 2011-12-22 2024-12-24 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend organische Schichten
CN103172554B (zh) * 2011-12-26 2016-08-17 昆山维信诺显示技术有限公司 一类有机化合物及其应用
JP5970811B2 (ja) 2011-12-28 2016-08-17 セイコーエプソン株式会社 発光素子、発光装置および電子機器
CN102617466B (zh) * 2011-12-31 2014-04-23 上海师范大学 一类“上-下”不对称型叔丁基螺二芴化合物
US9385337B2 (en) 2012-01-30 2016-07-05 Merck Patent Gmbh Nanocrystals on fibers
KR102015765B1 (ko) 2012-02-14 2019-10-21 메르크 파텐트 게엠베하 유기 전계발광 소자용 스피로비플루오렌 화합물
US9324952B2 (en) 2012-02-28 2016-04-26 Seiko Epson Corporation Thiadiazole, compound for light-emitting elements, light-emitting element, light-emitting apparatus, authentication apparatus, and electronic device
KR102268696B1 (ko) 2012-03-15 2021-06-23 메르크 파텐트 게엠베하 전자 소자
JP6105040B2 (ja) 2012-03-23 2017-03-29 メルク パテント ゲーエムベーハー エレクトロルミネッセンス素子のための９，９’−スピロビキサンテン誘導体
KR102198635B1 (ko) 2012-04-20 2021-01-05 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치
JP6324948B2 (ja) 2012-05-24 2018-05-16 メルク パテント ゲーエムベーハー 縮合複素環式芳香族環を含む金属錯体
DE102012011335A1 (de) 2012-06-06 2013-12-12 Merck Patent Gmbh Verbindungen für Organische Elekronische Vorrichtungen
WO2013185871A1 (fr) 2012-06-12 2013-12-19 Merck Patent Gmbh Composés pour dispositifs électroniques
KR102161955B1 (ko) 2012-07-10 2020-10-06 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
EP2872590B1 (fr) 2012-07-13 2018-11-14 Merck Patent GmbH Complexes metalliques
KR101807925B1 (ko) 2012-07-23 2017-12-11 메르크 파텐트 게엠베하 화합물 및 유기 전계 발광 디바이스
EP2875019B1 (fr) 2012-07-23 2017-03-29 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
CN104488359B (zh) 2012-07-23 2018-01-23 默克专利有限公司 2‑二芳基氨基芴的衍生物和含有所述2‑二芳基氨基芴衍生物的有机电子复合体
EP3424907B1 (fr) 2012-07-23 2025-03-12 Merck Patent GmbH Raccordements et dispositifs électro-organiques
EP2882763B1 (fr) 2012-08-07 2018-08-22 Merck Patent GmbH Complexes métalliques
JP6271550B2 (ja) 2012-08-10 2018-01-31 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセント素子のための材料
KR101374218B1 (ko) 2012-08-21 2014-03-12 충남대학교산학협력단 색상 튜닝이 가능한 벤조싸이아다이아졸계 발광 초분지 공액화 고분자 및 이를 사용한 전기발광소자
EP2898042B1 (fr) 2012-09-18 2016-07-06 Merck Patent GmbH Matériaux pour dispositifs électroniques
DE112013004610A5 (de) 2012-09-20 2015-06-03 Merck Patent Gmbh Metallkomplexe
DE102012020167A1 (de) 2012-10-13 2014-04-17 Eberhard Karls Universität Tübingen Metallkomplexe
CN107011365A (zh) 2012-10-18 2017-08-04 精工爱普生株式会社 噻二唑系化合物、发光元件用化合物、发光元件、发光装置、认证装置以及电子设备
KR101963104B1 (ko) 2012-10-31 2019-03-28 메르크 파텐트 게엠베하 전자 디바이스
JP5724987B2 (ja) * 2012-10-31 2015-05-27 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
US9748492B2 (en) 2012-11-02 2017-08-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
DE102012021650A1 (de) 2012-11-03 2014-05-08 Eberhard Karls Universität Tübingen Metallkomplexe
KR101716069B1 (ko) 2012-11-12 2017-03-13 메르크 파텐트 게엠베하 전자 소자용 재료
WO2014082705A1 (fr) 2012-11-30 2014-06-05 Merck Patent Gmbh Dispositif électronique
WO2014106524A2 (fr) 2013-01-03 2014-07-10 Merck Patent Gmbh Matériaux pour dispositifs électroniques
CN104884572B (zh) 2013-01-03 2017-09-19 默克专利有限公司 用于电子器件的材料
CN104045816B (zh) * 2013-03-13 2016-08-24 海洋王照明科技股份有限公司 一种含丙二腈-咔唑-苯并二噻吩共聚物及其制备方法与应用
DE102013008189A1 (de) 2013-05-14 2014-12-04 Eberhard Karls Universität Tübingen Metallkomplexe
WO2015014427A1 (fr) 2013-07-29 2015-02-05 Merck Patent Gmbh Dispositif électro-optique et son utilisation
KR20220025211A (ko) 2013-07-30 2022-03-03 메르크 파텐트 게엠베하 전자 소자용 물질
CN105408448B (zh) 2013-07-30 2018-11-02 默克专利有限公司 用于电子器件的材料
CN104465827B (zh) * 2013-09-18 2017-07-25 常州亚玛顿股份有限公司 高效率太阳能电池模组结构
KR102310370B1 (ko) 2013-10-02 2021-10-07 메르크 파텐트 게엠베하 Oled 에서의 사용을 위한 붕소 함유 화합물
JP6716457B2 (ja) 2013-12-06 2020-07-01 メルク パテント ゲーエムベーハー アクリル酸エステルおよび／またはメタクリル酸エステル単位を含むポリマーバインダーを含む組成物
JP6585048B2 (ja) 2013-12-06 2019-10-02 メルク パテント ゲーエムベーハー 置換オキセピン
JP6896422B2 (ja) 2013-12-06 2021-06-30 メルク パテント ゲーエムベーハー 化合物および有機電子素子
WO2015086108A1 (fr) 2013-12-12 2015-06-18 Merck Patent Gmbh Matériaux pour dispositifs électroniques
JP2015187942A (ja) * 2014-03-26 2015-10-29 日本放送協会 発光素子、発光素子の製造方法および表示装置
WO2015165563A1 (fr) 2014-04-30 2015-11-05 Merck Patent Gmbh Matériaux pour dispositifs électroniques
DE102014008722B4 (de) 2014-06-18 2024-08-22 Merck Patent Gmbh Zusammensetzungen für elektronische Vorrichtungen, Formulierung diese enthaltend, Verwendung der Zusammensetzung, Verwendung der Formulierung sowie organische elektronische Vorrichtung enthaltend die Zusammensetzung
CN116655603A (zh) 2014-07-21 2023-08-29 默克专利有限公司 用于电子器件的材料
EP3189551B1 (fr) 2014-09-05 2021-01-27 Merck Patent GmbH Formulations et procédé de fabrication d'un dispositif électroluminescent organique
KR102409803B1 (ko) 2014-10-10 2022-06-17 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 표시 장치, 전자 기기, 및 조명 장치
KR102384649B1 (ko) 2014-11-10 2022-04-11 삼성디스플레이 주식회사 유기 발광 소자
KR102385230B1 (ko) 2014-11-19 2022-04-12 삼성디스플레이 주식회사 유기 발광 소자
US10683453B2 (en) 2014-12-12 2020-06-16 Merck Patent Gmbh Organic compounds with soluble groups
KR102363260B1 (ko) * 2014-12-19 2022-02-16 삼성디스플레이 주식회사 유기 발광 소자
WO2016107663A1 (fr) 2014-12-30 2016-07-07 Merck Patent Gmbh Formulations et dispositifs électroniques
JP7030519B2 (ja) 2015-01-30 2022-03-07 メルク パテント ゲーエムベーハー 低粒子含有量をもつ調合物
US20180006237A1 (en) 2015-01-30 2018-01-04 Merck Patent Gmbh Materials for electronic devices
KR102343572B1 (ko) * 2015-03-06 2021-12-28 삼성디스플레이 주식회사 유기 발광 소자
JP6800879B2 (ja) 2015-03-30 2020-12-16 メルク パテント ゲーエムベーハー シロキサン溶媒を含む有機機能性材料の調合物
EP3297978B1 (fr) 2015-05-18 2020-04-01 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
JP6692126B2 (ja) * 2015-06-03 2020-05-13 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
CN111477766B (zh) 2015-06-12 2023-04-07 默克专利有限公司 作为用于oled制剂的溶剂的含有非芳族环的酯
CN106328816B (zh) * 2015-06-16 2018-11-13 昆山国显光电有限公司 一种有机电致发光器件及其制备方法
US20180212166A1 (en) 2015-07-15 2018-07-26 Merck Patent Gmbh Composition comprising organic semiconducting compounds
KR102660538B1 (ko) 2015-07-22 2024-04-24 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
JP6983754B2 (ja) 2015-07-29 2021-12-17 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
KR102599157B1 (ko) 2015-08-14 2023-11-06 메르크 파텐트 게엠베하 유기 전계발광 소자용 페녹사진 유도체
WO2017036573A1 (fr) 2015-08-28 2017-03-09 Merck Patent Gmbh Composés pour dispositifs électroniques
WO2017036572A1 (fr) 2015-08-28 2017-03-09 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique comprenant un solvant contenant un groupe époxy
KR101991050B1 (ko) * 2015-10-06 2019-06-20 주식회사 엘지화학 스피로형 화합물 및 이를 포함하는 유기 발광 소자
US11005042B2 (en) 2015-12-10 2021-05-11 Merck Patent Gmbh Formulations containing ketones comprising non-aromatic cycles
EP4084109A1 (fr) 2015-12-15 2022-11-02 Merck Patent GmbH Esters contenant des groupes aromatiques comme solvants pour formulations électroniques organiques
JP7438661B2 (ja) 2015-12-16 2024-02-27 メルク パテント ゲーエムベーハー 固体溶媒を含む調合物
KR20180095028A (ko) 2015-12-16 2018-08-24 메르크 파텐트 게엠베하 둘 이상의 상이한 용매의 혼합물을 함유하는 제형
JP7051691B2 (ja) 2016-02-05 2022-04-11 メルク パテント ゲーエムベーハー 電子素子のための材料
KR102776731B1 (ko) 2016-02-17 2025-03-05 메르크 파텐트 게엠베하 유기 기능성 재료의 제형
DE102016003104A1 (de) 2016-03-15 2017-09-21 Merck Patent Gmbh Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter
EP3455326B1 (fr) 2016-05-11 2021-02-24 Merck Patent GmbH Compositions pour cellules électrochimiques
EP3464244B1 (fr) 2016-06-03 2021-11-17 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
JP2019523997A (ja) 2016-06-16 2019-08-29 メルク パテント ゲーエムベーハー 有機機能材料の調合物
CN109312183A (zh) 2016-06-17 2019-02-05 默克专利有限公司 有机功能材料的制剂
TW201815998A (zh) 2016-06-28 2018-05-01 德商麥克專利有限公司 有機功能材料之調配物
EP3478698B1 (fr) 2016-06-30 2021-01-13 Merck Patent GmbH Procédé pour séparer des mélanges d'énantiomères de complexes métalliques
TWI745395B (zh) 2016-07-08 2021-11-11 德商麥克專利有限公司 有機電致發光裝置用之材料
TWI749026B (zh) 2016-07-14 2021-12-11 德商麥克專利有限公司 金屬錯合物
WO2018019688A1 (fr) 2016-07-25 2018-02-01 Merck Patent Gmbh Complexes métalliques trouvant application comme émetteurs dans des dispositifs électroluminescents organiques
WO2018024719A1 (fr) 2016-08-04 2018-02-08 Merck Patent Gmbh Formulation d'une matière fonctionnelle organique
WO2018054798A1 (fr) 2016-09-21 2018-03-29 Merck Patent Gmbh Complexes métalliques trouvant application comme émetteurs dans des dispositifs électroluminescents organiques
TWI764942B (zh) 2016-10-10 2022-05-21 德商麥克專利有限公司 電子裝置
US11430962B2 (en) 2016-10-12 2022-08-30 Merck Patent Gmbh Binuclear metal complexes and electronic devices, in particular organic electroluminescent devices containing said metal complexes
CN109937207A (zh) 2016-10-12 2019-06-25 默克专利有限公司 金属络合物
CN109790192A (zh) 2016-10-13 2019-05-21 默克专利有限公司 金属络合物
DE102017008794A1 (de) 2016-10-17 2018-04-19 Merck Patent Gmbh Materialien zur Verwendung in elektronischen Vorrichtungen
KR102451842B1 (ko) 2016-10-31 2022-10-07 메르크 파텐트 게엠베하 유기 기능성 재료의 제형
WO2018077662A1 (fr) 2016-10-31 2018-05-03 Merck Patent Gmbh Formulation d'une matière organique fonctionnelle
KR102683884B1 (ko) 2016-11-02 2024-07-11 메르크 파텐트 게엠베하 전자 소자용 재료
JP7073388B2 (ja) 2016-11-08 2022-05-23 メルク パテント ゲーエムベーハー 電子デバイスのための化合物
TWI756292B (zh) 2016-11-14 2022-03-01 德商麥克專利有限公司 具有受體基團與供體基團之化合物
TW201833118A (zh) 2016-11-22 2018-09-16 德商麥克專利有限公司 用於電子裝置之材料
US11584753B2 (en) 2016-11-25 2023-02-21 Merck Patent Gmbh Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)
US11453680B2 (en) 2016-11-25 2022-09-27 Merck Patent Gmbh Bisbenzofuran-fused indeno[1,2-B]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED)
WO2018104202A1 (fr) 2016-12-06 2018-06-14 Merck Patent Gmbh Procédé de préparation d'un dispositif électronique
WO2018108760A1 (fr) 2016-12-13 2018-06-21 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique
KR102504432B1 (ko) 2016-12-22 2023-02-27 메르크 파텐트 게엠베하 적어도 2종의 유기-기능성 화합물을 포함하는 혼합물
US11261291B2 (en) 2016-12-22 2022-03-01 Merck Patent Gmbh Materials for electronic devices
CN106848077B (zh) * 2017-01-11 2018-08-28 山东师范大学 一种有机电致发光器件及其制备方法、显示屏
TWI791481B (zh) 2017-01-30 2023-02-11 德商麥克專利有限公司 形成有機電致發光（ｅｌ）元件之方法
TWI763772B (zh) 2017-01-30 2022-05-11 德商麥克專利有限公司 電子裝置之有機元件的形成方法
WO2018141706A1 (fr) 2017-02-02 2018-08-09 Merck Patent Gmbh Matériaux pour dispositifs électroniques
CN117440703A (zh) 2017-03-01 2024-01-23 默克专利有限公司 有机电致发光器件
CN110325524A (zh) 2017-03-02 2019-10-11 默克专利有限公司 用于有机电子器件的材料
US10186668B2 (en) * 2017-03-04 2019-01-22 Feng-wen Yen Organic electroluminescent material and use thereof
WO2018165101A1 (fr) * 2017-03-06 2018-09-13 Qatar Foundation For Education, Science And Community Development Dérivés de dispiro-oxépine pour semi-conducteurs optoélectroniques
CN110446611B (zh) 2017-03-31 2021-05-25 默克专利有限公司 用于有机发光二极管(oled)的印刷方法
KR102632027B1 (ko) 2017-04-10 2024-01-31 메르크 파텐트 게엠베하 유기 기능성 재료의 제형
EP3609977B1 (fr) 2017-04-13 2024-05-29 Merck Patent GmbH Composition pour dispositifs électroniques organiques
EP3615542B1 (fr) 2017-04-25 2023-08-23 Merck Patent GmbH Composés pour dispositifs électroniques
JP7330898B2 (ja) 2017-05-03 2023-08-22 メルク パテント ゲーエムベーハー 有機機能材料の調合物
TW201920343A (zh) 2017-06-21 2019-06-01 德商麥克專利有限公司 電子裝置用材料
US11767299B2 (en) 2017-06-23 2023-09-26 Merck Patent Gmbh Materials for organic electroluminescent devices
CN110770363A (zh) 2017-06-26 2020-02-07 默克专利有限公司 均质混合物
WO2019002190A1 (fr) 2017-06-28 2019-01-03 Merck Patent Gmbh Matériaux pour dispositifs électroniques
TWI786143B (zh) 2017-07-03 2022-12-11 德商麥克專利有限公司 有機電致發光裝置及其產製方法
TWI813576B (zh) 2017-07-03 2023-09-01 德商麥克專利有限公司 具有低含量苯酚類雜質的調配物
KR102616338B1 (ko) 2017-07-05 2023-12-20 메르크 파텐트 게엠베하 유기 전자 디바이스용 조성물
JP7247121B2 (ja) 2017-07-05 2023-03-28 メルク パテント ゲーエムベーハー 有機電子デバイスのための組成物
WO2019016184A1 (fr) 2017-07-18 2019-01-24 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique
TWI776926B (zh) 2017-07-25 2022-09-11 德商麥克專利有限公司 金屬錯合物
US20200212301A1 (en) 2017-07-28 2020-07-02 Merck Patent Gmbh Spirobifluorene derivatives for use in electronic devices
CN107394051B (zh) * 2017-08-14 2019-12-27 上海天马有机发光显示技术有限公司 一种发光器件及显示装置
EP3679024B1 (fr) 2017-09-08 2022-11-02 Merck Patent GmbH Matériaux pour dispositifs électroniques
CN108675975A (zh) 2017-10-17 2018-10-19 默克专利有限公司 用于有机电致发光器件的材料
EP3698417A1 (fr) * 2017-10-19 2020-08-26 Cynora Gmbh Dispositif d'éclairage pour véhicules à moteur et températures de fonctionnement augmentées
TWI785142B (zh) 2017-11-14 2022-12-01 德商麥克專利有限公司 用於有機電子裝置之組成物
KR20250035612A (ko) 2017-11-23 2025-03-12 메르크 파텐트 게엠베하 전자 디바이스용 재료
TWI838352B (zh) 2017-11-24 2024-04-11 德商麥克專利有限公司 用於有機電致發光裝置的材料
TWI820057B (zh) 2017-11-24 2023-11-01 德商麥克專利有限公司 用於有機電致發光裝置的材料
TWI791701B (zh) 2017-12-13 2023-02-11 德商麥克專利有限公司 金屬錯合物
KR20250086794A (ko) 2017-12-15 2025-06-13 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 치환된 방향족 아민
CN111418081B (zh) 2017-12-15 2024-09-13 默克专利有限公司 有机功能材料的制剂
JP7402800B2 (ja) 2017-12-20 2023-12-21 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング ヘテロ芳香族化合物
KR102710151B1 (ko) 2018-02-26 2024-09-25 메르크 파텐트 게엠베하 유기 기능성 재료의 포뮬레이션
TW201938761A (zh) 2018-03-06 2019-10-01 德商麥克專利有限公司 用於有機電致發光裝置的材料
TWI802656B (zh) 2018-03-06 2023-05-21 德商麥克專利有限公司 用於有機電致發光裝置之材料
EP3765444B1 (fr) 2018-03-16 2026-01-14 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
TWI828664B (zh) 2018-03-19 2024-01-11 愛爾蘭商Ｕｄｃ愛爾蘭責任有限公司 金屬錯合物
CN112166112A (zh) 2018-05-30 2021-01-01 默克专利有限公司 用于有机电子器件的组合物
WO2019238782A1 (fr) 2018-06-15 2019-12-19 Merck Patent Gmbh Formulation d'un matériau fonctionnel organique
TWI837167B (zh) 2018-08-28 2024-04-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
TWI823993B (zh) 2018-08-28 2023-12-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
WO2020043646A1 (fr) 2018-08-28 2020-03-05 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
KR102769406B1 (ko) 2018-09-12 2025-02-17 메르크 파텐트 게엠베하 유기 전계발광 디바이스용 재료
JP2022502829A (ja) 2018-09-24 2022-01-11 メルク パテント ゲーエムベーハー 粒状材料を製造するための方法
CN112771024A (zh) 2018-09-27 2021-05-07 默克专利有限公司 用于制备空间位阻型含氮杂芳族化合物的方法
CN120025253A (zh) 2018-09-27 2025-05-23 默克专利有限公司 可用作有机电子器件中的活性化合物的化合物
CN112930343A (zh) 2018-10-31 2021-06-08 默克专利有限公司 用于有机电致发光器件的材料
EP3878022A1 (fr) 2018-11-06 2021-09-15 Merck Patent GmbH Procédé de formation d'un élément organique d'un dispositif électronique
TW202035345A (zh) 2019-01-17 2020-10-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
TWI850329B (zh) 2019-02-11 2024-08-01 愛爾蘭商Ｕｄｃ愛爾蘭責任有限公司 金屬錯合物
WO2020169241A1 (fr) 2019-02-18 2020-08-27 Merck Patent Gmbh Composition pour dispositifs électroniques organiques
US20220127286A1 (en) 2019-03-04 2022-04-28 Merck Patent Gmbh Ligands for nano-sized materials
JP7598873B2 (ja) 2019-04-11 2024-12-12 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機エレクトロルミネッセンス素子のための材料
JP7608358B2 (ja) 2019-04-15 2025-01-06 ユー・ディー・シー アイルランド リミテッド 金属錯体
JP7693654B2 (ja) 2019-09-19 2025-06-17 メルク パテント ゲーエムベーハー ２種のホスト材料の混合物、およびこれを含む有機エレクトロルミネッセントデバイス
KR20220090539A (ko) 2019-10-25 2022-06-29 메르크 파텐트 게엠베하 유기 전자 디바이스에서 사용될 수 있는 화합물
US12593607B2 (en) 2019-11-04 2026-03-31 Udc Ireland Limited Materials for organic electroluminescent devices
TW202134252A (zh) 2019-11-12 2021-09-16 德商麥克專利有限公司 有機電致發光裝置用材料
KR102377685B1 (ko) 2019-11-29 2022-03-23 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2021110720A1 (fr) 2019-12-04 2021-06-10 Merck Patent Gmbh Complexes métalliques
TW202136471A (zh) 2019-12-17 2021-10-01 德商麥克專利有限公司 有機電致發光裝置用的材料
JP7620631B2 (ja) 2019-12-18 2025-01-23 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機エレクトロルミネッセンス素子のための芳香族化合物
CN114867729A (zh) 2019-12-19 2022-08-05 默克专利有限公司 用于有机电致发光器件的多环化合物
US20230139809A1 (en) 2020-01-29 2023-05-04 Merck Patent Gmbh Benzimidazole derivatives
CN115135741A (zh) 2020-02-25 2022-09-30 默克专利有限公司 杂环化合物在有机电子器件中的用途
WO2021175706A1 (fr) 2020-03-02 2021-09-10 Merck Patent Gmbh Utilisation de composés sulfone dans un dispositif électronique organique
TW202200529A (zh) 2020-03-13 2022-01-01 德商麥克專利有限公司 有機電致發光裝置
CN115298187A (zh) 2020-03-17 2022-11-04 默克专利有限公司 用于有机电致发光器件的杂芳族化合物
EP4122028B1 (fr) 2020-03-17 2024-10-16 Merck Patent GmbH Composés hétérocycliques pour dispositifs électroluminescents organiques
KR20220157456A (ko) 2020-03-23 2022-11-29 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 재료
EP4126880A1 (fr) 2020-03-26 2023-02-08 Merck Patent GmbH Composés cycliques pour dispositifs électroluminescents organiques
EP4132939B1 (fr) 2020-04-06 2024-01-31 Merck Patent GmbH Composés polycycliques pour dispositifs électroluminescents organiques
WO2021213917A1 (fr) 2020-04-21 2021-10-28 Merck Patent Gmbh Émulsions comprenant des matériaux fonctionnels organiques
TW202214791A (zh) 2020-04-21 2022-04-16 德商麥克專利有限公司 有機功能性材料之調配物
CN111423450B (zh) * 2020-04-29 2021-10-26 上海天马有机发光显示技术有限公司 化合物、显示面板以及显示装置
EP4168397B1 (fr) 2020-06-18 2025-08-20 Merck Patent GmbH Indénoazanaphtalènes
CN115867426A (zh) 2020-06-23 2023-03-28 默克专利有限公司 生产混合物的方法
JP2023531470A (ja) 2020-06-29 2023-07-24 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機エレクトロルミネッセンス素子のためのヘテロ芳香族化合物
WO2022002771A1 (fr) 2020-06-29 2022-01-06 Merck Patent Gmbh Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2022017998A1 (fr) 2020-07-22 2022-01-27 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
CN115776981A (zh) 2020-07-22 2023-03-10 默克专利有限公司 用于有机电致发光器件的材料
CN116134113B (zh) 2020-08-13 2025-12-26 Udc爱尔兰有限公司 金属络合物
EP4222155B1 (fr) 2020-09-29 2025-06-11 UDC Ireland Limited Complexes d'iridium hexadentés tripodes mononucléaires destinés à être utilisés dans des delo
WO2022079067A1 (fr) 2020-10-16 2022-04-21 Merck Patent Gmbh Composés comprenant des hétéroatomes pour dispositifs électroluminescents organiques
EP4229064A1 (fr) 2020-10-16 2023-08-23 Merck Patent GmbH Composés hétérocycliques pour dispositifs électroluminescents organiques
KR20230114756A (ko) 2020-12-08 2023-08-01 메르크 파텐트 게엠베하 잉크 시스템 및 잉크젯 인쇄를 위한 방법
US20240101560A1 (en) 2020-12-18 2024-03-28 Merck Patent Gmbh Nitrogenous heteroaromatic compounds for organic electroluminescent devices
TW202241905A (zh) 2020-12-18 2022-11-01 德商麥克專利有限公司 用於有機電致發光裝置的氮化合物
CN117084000A (zh) 2021-04-09 2023-11-17 默克专利有限公司 用于有机电致发光器件的材料
TW202309243A (zh) 2021-04-09 2023-03-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
TW202309242A (zh) 2021-04-09 2023-03-01 德商麥克專利有限公司 用於有機電致發光裝置之材料
EP4079742B1 (fr) 2021-04-14 2026-04-01 UDC Ireland Limited Complexes métalliques
EP4326826A1 (fr) 2021-04-23 2024-02-28 Merck Patent GmbH Formulation d'un matériau fonctionnel organique
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WO2022200638A1 (fr) 2021-07-06 2022-09-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
JP2024528219A (ja) 2021-08-02 2024-07-26 メルク パテント ゲーエムベーハー インクを組み合わせることによる印刷方法
EP4402141A1 (fr) 2021-09-13 2024-07-24 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
KR20240064697A (ko) 2021-09-14 2024-05-13 메르크 파텐트 게엠베하 유기 전계 발광 디바이스용 붕소 복소환 화합물
CN118056486A (zh) 2021-09-28 2024-05-17 默克专利有限公司 用于电子器件的材料
WO2023052272A1 (fr) 2021-09-28 2023-04-06 Merck Patent Gmbh Matériaux pour dispositifs électroniques
EP4410071A1 (fr) 2021-09-28 2024-08-07 Merck Patent GmbH Matériaux pour dispositifs électroniques
EP4410074B1 (fr) 2021-09-28 2025-05-21 Merck Patent GmbH Matériaux pour dispositifs électroniques
TW202349760A (zh) 2021-10-05 2023-12-16 德商麥克專利有限公司 電子裝置之有機元件的形成方法
KR20230049946A (ko) * 2021-10-07 2023-04-14 엘지디스플레이 주식회사 유기발광다이오드 및 이를 포함하는 유기발광장치
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EP4437814A1 (fr) 2021-11-25 2024-10-02 Merck Patent GmbH Matériaux pour dispositifs électroniques
KR20240128020A (ko) 2021-12-21 2024-08-23 메르크 파텐트 게엠베하 중수소화 유기 화합물의 제조 방법
EP4479385A1 (fr) 2022-02-14 2024-12-25 Merck Patent GmbH Matériaux pour dispositifs électroniques
WO2023161167A1 (fr) 2022-02-23 2023-08-31 Merck Patent Gmbh Hétérocycles azotés pour dispositifs électroluminescents organiques
WO2023161168A1 (fr) 2022-02-23 2023-08-31 Merck Patent Gmbh Hétérocycles aromatiques pour dispositifs électroluminescents organiques
WO2023213837A1 (fr) 2022-05-06 2023-11-09 Merck Patent Gmbh Composés cycliques pour dispositifs électroluminescents organiques
CN119156361A (zh) 2022-05-18 2024-12-17 默克专利有限公司 用于氘化的有机化合物的制备方法
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CN119452060A (zh) 2022-07-11 2025-02-14 默克专利有限公司 用于电子器件的材料
EP4311849B1 (fr) 2022-07-27 2025-01-29 UDC Ireland Limited Complexes metalliques
EP4568964A1 (fr) 2022-08-09 2025-06-18 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
EP4590653A1 (fr) 2022-09-22 2025-07-30 Merck Patent GmbH Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques
CN119894856A (zh) 2022-09-22 2025-04-25 默克专利有限公司 用于有机电致发光器件的含氮化合物
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EP4619484A1 (fr) 2022-11-17 2025-09-24 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
TW202440819A (zh) 2022-12-16 2024-10-16 德商麥克專利有限公司 有機功能性材料之調配物
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EP4640022A1 (fr) 2022-12-19 2025-10-29 Merck Patent GmbH Matériaux pour dispositifs électroniques
CN120379953A (zh) 2022-12-20 2025-07-25 默克专利有限公司 用于制备氘化芳族化合物的方法
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EP4652169A1 (fr) 2023-01-17 2025-11-26 Merck Patent GmbH Hétérocycles pour dispositifs électroluminescents organiques
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EP4683925A1 (fr) 2023-03-20 2026-01-28 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
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EP4720070A1 (fr) 2023-05-25 2026-04-08 Merck Patent GmbH Dérivés de tris[1,2,4]triazolo[1,5-a:1',5'-c:1'',5''-e][1,3,5]triazine destinés à être utilisés dans des dispositifs électroluminescents organiques
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EP4486099B1 (fr) 2023-06-30 2026-04-29 UDC Ireland Limited Composés pour dispositifs électroluminescents organiques
CN121487940A (zh) 2023-07-12 2026-02-06 默克专利有限公司 用于电子器件的材料
KR20260044229A (ko) 2023-07-27 2026-04-01 메르크 파텐트 게엠베하 유기 발광 디바이스 및 유기 센서를 위한 재료
WO2025032039A1 (fr) 2023-08-07 2025-02-13 Merck Patent Gmbh Procédé de préparation d'un dispositif électronique
WO2025045816A1 (fr) 2023-08-29 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
CN121753521A (zh) 2023-08-30 2026-03-27 默克专利有限公司 用于有机发光器件的材料
WO2025045842A1 (fr) 2023-08-30 2025-03-06 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
CN121773745A (zh) 2023-08-30 2026-03-31 默克专利有限公司 用于有机发光器件的材料
WO2025045935A1 (fr) 2023-08-31 2025-03-06 Merck Patent Gmbh Composés aromatiques contenant des groupes cyano pour dispositifs électroluminescents organiques
CN121969629A (zh) 2023-10-04 2026-05-01 默克专利有限公司 用于有机电致发光器件的材料
WO2025109056A1 (fr) 2023-11-24 2025-05-30 Merck Patent Gmbh Hétérocycles contenant de l'oxygène pour dispositifs électroluminescents organiques
WO2025119821A1 (fr) 2023-12-05 2025-06-12 Merck Patent Gmbh Composition de matériau pour dispositifs électroluminescents organiques
WO2025132194A1 (fr) 2023-12-20 2025-06-26 Merck Patent Gmbh Nouveaux matériaux pour dispositifs électroluminescents organiques
WO2025132547A1 (fr) 2023-12-21 2025-06-26 Merck Patent Gmbh Procédé mécanochimique de deutération de composés organiques
WO2025132551A1 (fr) 2023-12-22 2025-06-26 Merck Patent Gmbh Matériaux pour dispositifs électroniques
WO2025181097A1 (fr) 2024-02-29 2025-09-04 Merck Patent Gmbh Hétérocycles contenant de l'azote pour dispositifs électroluminescents organiques
WO2025181044A1 (fr) 2024-02-29 2025-09-04 Merck Patent Gmbh Composés contenant de l'azote pour dispositifs électroluminescents organiques
WO2025181124A1 (fr) 2024-03-01 2025-09-04 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025195961A1 (fr) 2024-03-19 2025-09-25 Merck Patent Gmbh Dispositifs électroluminescents organiques
WO2025196145A1 (fr) 2024-03-22 2025-09-25 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2025210013A1 (fr) 2024-04-04 2025-10-09 Merck Patent Gmbh Composés pour dispositifs électroniques, en particulier composés pour oled
WO2026008710A1 (fr) 2024-07-05 2026-01-08 Merck Patent Gmbh Composés de silicium cyclique pour dispositifs électroluminescents organiques
WO2026022016A1 (fr) 2024-07-22 2026-01-29 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
WO2026041632A1 (fr) 2024-08-21 2026-02-26 Merck Patent Gmbh Matériaux hétérocycliques pour dispositifs électroluminescents organiques
WO2026073855A1 (fr) 2024-10-01 2026-04-09 Merck Patent Gmbh Composés de silicium pour dispositifs électroluminescents organiques

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) * 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
US5151629A (en) * 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
EP0676461B1 (fr) * 1994-04-07 2002-08-14 Covion Organic Semiconductors GmbH Composés spiro et leur application comme matières électroluminescentes
FR2773158B1 (fr) * 1997-12-30 2000-02-04 Atochem Elf Sa Procede de polymerisation radicalaire controlee faisant intervenir une faible quantite de radical libre stable
US6392339B1 (en) * 1999-07-20 2002-05-21 Xerox Corporation Organic light emitting devices including mixed region
US7027682B2 (en) * 1999-09-23 2006-04-11 Arizona State University Optical MEMS switching array with embedded beam-confining channels and method of operating same
JP4554047B2 (ja) * 2000-08-29 2010-09-29 株式会社半導体エネルギー研究所 発光装置
KR100832766B1 (ko) * 2000-12-22 2008-05-27 메르크 파텐트 게엠베하 붕소 또는 알루미늄계 스피로 화합물 및 전자 산업에서의이들의 용도
TW545080B (en) * 2000-12-28 2003-08-01 Semiconductor Energy Lab Light emitting device and method of manufacturing the same
WO2002077060A1 (fr) * 2001-03-24 2002-10-03 Covion Organic Semiconductors Gmbh Polymeres conjugues contenant des unites spirobifluorene et des unites fluorene et leur utilisation
ATE529494T1 (de) * 2002-07-19 2011-11-15 Idemitsu Kosan Co Organische elektrolumineszente vorrichtungen und organisches lichtemittierendes medium

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2004058911A2 *

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JP2006511939A (ja) 2006-04-06
US20060063027A1 (en) 2006-03-23
WO2004058911A3 (fr) 2005-12-08
WO2004058911A2 (fr) 2004-07-15
CN1756824A (zh) 2006-04-05
KR101030158B1 (ko) 2011-04-18
KR20050085239A (ko) 2005-08-29

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