EP1618170A2 - Melanges de semi-conducteurs organiques aptes a l'emission et de matieres matricielles, leur utilisation et composants electroniques contenant ces melanges - Google Patents

Melanges de semi-conducteurs organiques aptes a l'emission et de matieres matricielles, leur utilisation et composants electroniques contenant ces melanges

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Publication number
EP1618170A2
EP1618170A2 EP04726968A EP04726968A EP1618170A2 EP 1618170 A2 EP1618170 A2 EP 1618170A2 EP 04726968 A EP04726968 A EP 04726968A EP 04726968 A EP04726968 A EP 04726968A EP 1618170 A2 EP1618170 A2 EP 1618170A2
Authority
EP
European Patent Office
Prior art keywords
formula
atoms
aromatic
same
occurrence
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Withdrawn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
EP04726968A
Other languages
German (de)
English (en)
Inventor
Anja Gerhard
Horst Vestweber
Philipp STÖSSEL
Susanne Heun
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
Priority claimed from DE10317556.3A external-priority patent/DE10317556B4/de
Priority claimed from DE10355358A external-priority patent/DE10355358A1/de
Application filed by Merck Patent GmbH, Covion Organic Semiconductors GmbH filed Critical Merck Patent GmbH
Priority to EP06014637A priority Critical patent/EP1717291A3/fr
Priority to EP10008254A priority patent/EP2281861A3/fr
Publication of EP1618170A2 publication Critical patent/EP1618170A2/fr
Withdrawn legal-status Critical Current

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    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
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    • C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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Definitions

  • the present invention describes the use of new materials and material mixtures in organic electronic components such as electroluminescent elements and their use in displays based thereon.
  • light-sensitive organic materials e.g. phthalocyanines
  • organic charge transport materials usually triarylamine-based hole transporters
  • OLEDs organic light-emitting diodes
  • Full-color, large-area, high-resolution active matrix displays for a wide variety of applications (such as, for example, mobile telephones, PDAs, laptops, televisions and other applications).
  • the operating voltage required is quite high, especially in the case of efficient phosphorescent OLEDs, and must therefore be reduced in order to improve the power efficiency. This is particularly important for portable applications.
  • organometallic complexes that show phosphorescence instead of fluorescence [M. A. Baldo, S. Lamansky, P.E. Burrows, M.E. Thompson, S.R. Forrest, Appl. Phys. Lett. 1999, 75, 4-6].
  • organometallic compounds For quantum mechanical reasons, up to four times quantum, energy and power efficiency is possible using organometallic compounds.
  • the essential conditions for practical use are, in particular, a long operational lifespan, high stability against thermal stress and a low operating and operating voltage to enable mobile 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, and EP 01202358.
  • An organic electroluminescent device usually consists of several layers which are applied to one another by means of vacuum methods or different printing 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, eg. B. 4,4 ', 4 "tris (N-1-naphthyl-N-phenylamino) triphenylamine (NaphDATA) as the first layer and N, N'-di (naphth-1-yl) - N, N '-diphenyl-benzidine (NPB) as a second hole transport layer.
  • triarylamine derivatives eg. B. 4,4 ', 4 "tris (N-1-naphthyl-N-phenylamino) triphenylamine (NaphDATA) as the first layer and N, N'-di (naphth-1-yl) - N, N '-diphenyl-benzidine (NPB) as a second hole transport layer.
  • emission Layer EML
  • this layer can partially coincide with layers 4 to 8, but usually consists of fluorescent dyes, e.g. B. N, N'-diphenyl-quinacridone (QA), or phosphorescent dyes, e.g. B. Tris (2-phenylpyridyl) iridium (Ir (PPy) s) or Tris (2-benzothiophenyl-pyridyl) iridium (Ir (BTP) 3 ), doped matrix materials such as 4,4'-bis (carbazole-9 -yl) -biphenyl (CBP).
  • the emission layer can also consist of polymers, mixtures of polymers, mixtures of polymers and low-molecular compounds or mixtures of different low-molecular compounds.
  • An electron transport layer mostly based on aluminum tris-8-hydroxyquinolinate (AIQ 3 ).
  • EIL electron injection layer
  • EIL Electron injection layer
  • a cathode here metals, metal combinations or metal alloys with a low work function are generally used.
  • the anode consists, for. B. from AI / Ni / NiOx or Al / Pt / PtOx or other metal / metal oxide combinations that have a HOMO greater than 5 eV.
  • the cathode consists of the same materials that are described in items 9 and 10, with the difference that the metal, such as. B. Ca, Ba, Mg, Al, In, etc., is very thin and therefore transparent.
  • the layer thickness is less than 50 nm, better less than 30 nm, even better less than 10 nm.
  • Another can be applied to this transparent cathode transparent material are applied, e.g. B. ITO (indium tin oxide), IZO (indium zinc oxide), etc.
  • the matrix material of the emission layer plays a special role.
  • the matrix material must enable or improve the charge transport of holes and / or electrons and / or enable or improve the charge carrier recombination and, if appropriate, transfer the energy produced during the recombination to the emitter.
  • this task has hitherto been predominantly carried out by matrix materials which contain carbazole units.
  • the carbazole units such as. B. contain the frequently used 4,4'-bis (N-carbazolyl) -biD_henyl (CBP), but have some disadvantages in practice. These can be seen, among other things, in the often short to very short lifespan of the devices manufactured with them and the often high operating voltages that lead to low power efficiencies. Furthermore, it has been shown that for energetic reasons, CBP is unsuitable for blue-emitting electroluminescent devices, which results in poor efficiency. In addition, the structure of the devices is very complex if CBP is used as the matrix material, since a hole blocking layer and an electron transport layer must also be used. If these additional layers are not used, e.g. B. by Adachi et. al.
  • S, Se or N stands, and which can optionally also form glass-like layers, and at least one emission material B capable of emission, which is a compound which emits light with suitable excitation and at least one element of the
  • the mixtures according to the invention are preferably those which contain at least one matrix material A in which the glass transition temperature T g of the pure substance A is greater than 70 ° C., preferably greater than 100 ° C., particularly preferably greater than 130 ° C.
  • the mixtures described above preferably contain as matrix material A at least one compound of the formula (1), formula (2) and / or formula (3)
  • X is the same or different at each occurrence O, S or Se;
  • Y is N on every occurrence
  • An aromatic or heteroaromatic system in the sense of this invention is to be understood as a system which does not necessarily only contain aromatic or heteroaromatic groups, but also in which several aromatic or heteroaromatic groups by a short non-aromatic unit ( ⁇ 10% of the Atoms, preferably ⁇ 5% of the atoms), such as sp 3 -hybridized C, O, N, etc., can be interrupted.
  • a short non-aromatic unit ⁇ 10% of the Atoms, preferably ⁇ 5% of the atoms
  • systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diphenyl ether, etc. should also be understood as aromatic systems.
  • radical R 1 or R 2 can also be a substituted or unsubstituted vinyl group or a corresponding derivative, ie the compound of the formula (1) is also a can be ⁇ , ⁇ -unsaturated carbonyl compound, or the compound of formula (2) or (3) can also be an ⁇ , ⁇ -unsaturated imine.
  • At least one of the sp 3 -hybridized atoms is a secondary, tertiary or quaternary atom, particularly preferably a tertiary or quaternary atom, very particularly in the case of carbon, silicon or germanium is preferably a quaternary atom.
  • a secondary, tertiary or quaternary atom is understood to mean an atom with two, three or four substituents other than hydrogen.
  • compounds that are dendritic in structure are also preferred.
  • 1,3,5-trisubstituted benzene ketones and corresponding oligoketones which are described, for example, according to N. Nakamura et a /., J. Amer. Chem. Soc. 1992, 114, 1484, or according to K. Matsuda et al., J. Amer. Chem. Soc. 1995, 117, 5550.
  • Mixtures which contain at least one compound of the formula (4) to (9) as matrix material A are likewise preferred,
  • Z is the same or different on each occurrence of CR or N.
  • Organic mixtures which contain at least one of the matrix materials A described above by formulas (1) to (9) are particularly preferred, in which case: X is O or S at each occurrence; Y is N on every occurrence; Z is CR 1 at each occurrence;
  • H atoms can be replaced by F, Cl, Br, I, or an aromatic or heteroaromatic system with 1 to 40 C atoms, where one or more H atoms can be replaced by F, Cl, Br, I and those by one or more, non-aromatic radicals R 1 can be substituted, with several substituents R and / or R 1 , R 2 , both on the same ring and on the two different rings together, in turn, a further mono- or polycyclic, aliphatic or aromatic
  • R 4 , R 5 , R 6 are as described under formulas (1) to (3).
  • Mixtures which contain at least one compound of the formula (10) to (15) as matrix material A are also preferred.
  • Ar is the same or different in each occurrence an aromatic or heteroaromatic system with 2 to 40 C atoms, preferably with 4 to 30 C atoms, where one or more H atoms can be replaced by F, Cl, Br, I and can be substituted by one or more non-aromatic radicals R 1 , it being possible for a plurality of substituents R 1 , both on the same ring and on different rings, to form a further mono- or polycylic, aliphatic or aromatic ring system; n is the same or different at each occurrence 0 or 1.
  • the present invention also relates to the new compounds of the formulas (10a) to (15),
  • E is the same or different at each occurrence C or N;
  • R 7 is the same or different each time an alkyl, alkoxy or
  • R 7 is an alkyl group without ⁇ -H atoms, the symbols Z, E, A 1 , A 2 and A 3 are to be chosen as desired;
  • R 7 is an aromatic group and at least one Z is N, the symbols E, A 1 , A 2 and A 3 are to be chosen as desired;
  • R 7 is an aromatic group and at least one Z stands for a group CR 1 with R 1 not equal to H, the symbols E, A 1 , A 2 and A 3 are to be chosen as desired;
  • R 7 is an aromatic group and all Z stand for CH and at least one symbol E stands for N, the symbols A 1 , A 2 and A 3 are to be chosen as desired;
  • R 7 is an aromatic group, all Z stand for CH and all E stand for C, at least one of the symbols A 1 , A 2 and / or A 3 for a group R 8 not equal to alkyl stand, while the other two groups can be chosen according to the definition;
  • R 7 is an aromatic group, all Z stand for CH, all E stand for C and the two symbols A 1 and A 2 are chosen according to the definition, whereby at least one of the two symbols stands for a group not equal to H, then the symbol A 3 stands for a group CO-R 7 , where R 7 can be chosen here according to the definition;
  • R 7 is a larger aromatic system, such as, for example, fluorene, spirobifluorene, triarylamine, etc.
  • the symbols Z, E, A ⁇ A 2 and A 3 can be selected as desired.
  • Table 1 Possible combinations of the symbols R 7 , Z, E, A 1 , A 2 and A 3 for compounds according to formula (10a).
  • the matrix materials A - z described above. B. according to Examples 26, 27 and 28 - can, for example, as co-monomers to produce corresponding conjugated, partially conjugated or non-conjugated polymers or as the core of dendrimers - z. B. according to Examples 29, 30 and 31 - find use.
  • the corresponding polymerization is preferably carried out via the halogen functionality. So you can a. in soluble polyfluorenes (e.g. according to EP 842208 or WO 00/22026), poly-spirobifluorenes (e.g. according to EP 707020 or EP 894107), poly-para-phenylenes (e.g. according to WO 92/18552) , Poly-carbazoles or polythiophenes (z. B. according to EP 1028136) are polymerized.
  • conjugated, partially conjugated or non-conjugated polymers or dendrimers described above which contain one or more structural units of the formulas (1) to (15), can be used as matrix material in organic electroluminescent devices.
  • the matrix materials A according to the invention can also be obtained, for example, from the above-mentioned.
  • Reaction types are further functionalized, and so are converted to expanded matrix materials A. Examples include the functionalization with arylboronic acids according to SUZUKI or with amines according to HARTWIG-BUCHWALD.
  • the matrix materials A according to the invention or their mixtures or the polymers or dendrimers containing the matrix materials A, optionally together with the emitters B according to generally known methods known to the person skilled in the art, such as vacuum evaporation, evaporation in a carrier gas stream or from solution applied to a substrate in the form of a film by spin coating or using various printing processes (for example ink-jet printing, off-set printing, LITI printing, etc.).
  • various printing processes for example ink-jet printing, off-set printing, LITI printing, etc.
  • the use of printing processes can have advantages with regard to the scalability of the production and also with regard to the setting of mixing ratios in the blend layers used.
  • the matrix materials described above are used in combination with phosphorescence emitters. These mixtures are characterized in that they contain at least one compound as emitter B, which is characterized in that it emits light with suitable excitation and also at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and contains less than 80.
  • Particularly preferred mixtures contain at least one compound of the formula (16) to (19) as emitter B,
  • DCy is the same or different at each occurrence a cyclic group which contains at least one donor atom, preferably nitrogen or phosphorus, via which the cyclic group is bonded to the metal and which in turn can carry one or more substituents R 9 ; the groups DCy and CCy are connected to one another via a covalent bond;
  • CCy is, identically or differently, a cyclic group which contains a carbon atom via which the cyclic group is bonded to the metal and which in turn can carry one or more substituents R 9 ;
  • L is the same or different at each occurrence, a bidentate, chelating ligand, preferably a diketonate ligand,
  • R 4 , R 5 , R 6 are the same or different with each occurrence H or an aliphatic or aromatic hydrocarbon radical with 1 to 20 C atoms.
  • Examples of the emitters described above can be found, for example, in applications WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614, WO 03/099959, WO 03/084972, WO 03/040160, WO 02/081488, WO 02/068435 and DE 10238903.9; these are hereby considered as part of the registration via quotation.
  • the mixture according to the invention contains between 1 to 99% by weight, preferably between 3 and 95% by weight, particularly preferably between 5 and 50% by weight, in particular between 7 and 20% by weight, based on the total mixture of emitter B and matrix material A.
  • the present invention further relates to electronic components, in particular organic electroluminescent devices (OLEDs), organic solar cells (O-SCs), organic field-effect transistors (O-FETs) or organic laser diodes (O-lasers), containing the mixture according to the invention of matrix material A and emission material B.
  • organic electroluminescent devices which have an emitting layer (EML) containing a mixture according to the invention of at least one matrix material A and at least one emission material B capable of emission are particularly preferred.
  • EML emitting layer
  • Organic electroluminescent devices which contain at least one mixture according to the invention in the emitting layer (EML) are particularly preferred, the glass transition temperature T g of the pure substance of the matrix material A being greater than 70 ° C.
  • the organic electroluminescent device can contain further layers, such as, for. B. hole injection layer, hole transport layer, hole blocking layer, electron transport layer and / or electron injection layer.
  • hole injection layer hole transport layer
  • hole blocking layer hole blocking layer
  • electron transport layer electron transport layer
  • / or electron injection layer it should be pointed out that each of these layers does not necessarily have to be present.
  • an OLED that contains neither a separate hole blocking layer nor a separate electron transport layer shows very good results in electroluminescence, in particular a significantly lower voltage and higher power efficiency. This is particularly surprising since a corresponding OLED with a carbazole-containing matrix material without a hole blocking and electron transport layer shows only very low performance efficiencies, in particular with high brightness (cf.
  • Another object of the invention is therefore an organic electroluminescent device containing a mixture according to the invention which directly adjoins the electron transport layer without using a hole blocking layer or which directly adjoins the electron injection layer or the cathode without using a hole blocking layer and an electron transport layer.
  • the organic electroluminescent devices according to the invention show higher efficiency, significantly longer lifespan and, in particular without the use of a hole blocking and electron transport layer, significantly lower operating voltages and higher power efficiencies than OLEDs according to the prior art, which contain CBP as matrix material.
  • Electron transport layers further simplify the structure of the OLED, which represents a considerable technological advantage.
  • the preferred embodiments of the mixtures of matrix material A and emission material B according to the invention are also for the electronic components according to the invention, in particular for the organic electroluminescent devices (OLEDs), organic solar cells (O-SCs), organic field effect transistors (O-FETs) or also organic laser diodes (O Laser). To avoid unnecessary repetitions, we do not list them again here.
  • OLEDs organic electroluminescent devices
  • O-SCs organic solar cells
  • O-FETs organic field effect transistors
  • O-FETs organic field effect transistors
  • O Laser organic laser diodes
  • T g 209 ° C
  • T m 401 ° C.
  • OLEDs were produced using the general process outlined below. In individual cases, of course, this had to be adapted to the respective circumstances (e.g. layer thickness variation in order to achieve optimum efficiency or color).
  • Electroluminescent devices according to the invention can be represented, for example, as follows:
  • ITO-coated substrate The substrate used is preferably ITO-coated glass which contains the lowest possible content or no ionic impurities, such as, for example, 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 combine the highest possible conductivity with high transparency. 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 a 4% deconex solution 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
  • HIL Hole injection layer
  • the polymers polyaniline (PANI) or polythiophene (PEDOT) and their derivatives are particularly suitable. These are usually 1 to 5% aqueous dispersions which are applied in thin layers between 20 and 200 nm, preferably between 40 and 150 nm, 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 dried in the drying oven for 1 to 10 minutes between 110 and 200 ° C, preferably between 150 and 180 ° C. But also newer drying processes, such as.
  • Irradiation with IR (infrared) light lead to very good results, the irradiation time generally taking less than a few seconds.
  • Thin layers, between 5 and 30 nm, of copper phthalocyanine (CuPc) are preferably used as the low molecular weight material.
  • CuPc copper phthalocyanine
  • All HIL not only have to inject holes very well, they also have to adhere very well to ITO and glass; this is the case for CuPc as well as for PEDOT and PANI.
  • 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-phenylamino) -triphenylamine) or 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 4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenylamino) -triphenylamine)
  • NaphDATA 4,4', 4 "-Tris (N-1-naphthyl-N-
  • MTDATA or NaphDATA have a layer thickness between 5 and 100 nm, preferably between 10 and 60 nm, particularly preferably between 15 and 40 nm. For thicker layers, somewhat higher voltages are required in order to achieve the same brightness; at the same time, the number of defects is reduced.
  • Spiro-TAD or NPB have a layer thickness between 5 and 150 nm, preferably between 10 and 100 nm, particularly preferably between 20 and 60 nm.
  • 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.
  • high molecular weight triarylamines can also be used.
  • Emission layer This layer can partially coincide with layers 3 and / or 5. It consists e.g. B. from a low molecular weight matrix material and a low molecular weight guest material, the phosphorescent dopant, such as CBP or one of the matrix materials A described above as the matrix material and lr (PPy) 3 as the dopant. Good results are achieved at a concentration of 5-30% lr (PPy) 3 in CBP or in one of the matrix materials A described above with an EML layer thickness between 10 and 100 nm, preferably between 10 and 50 nm.
  • High-molecular light-emitting compounds (polymers) can also be used, it being possible for one or both components of the host-guest system to be high-molecular.
  • HBL electron transport and hole blocking layer
  • BAIq have proven to be particularly effective as HBL material.
  • low molecular weight HBLs can also use high molecular weight HBLs.
  • OLEDs which contain mixtures according to the invention continue to show very good results even without such a hole blocking layer. Therefore, a hole blocking layer was not used in all of the examples described below.
  • Electron Transport Layer Metal hydroxyquinolates are well suited as ETL materials; aluminum tris-8-hydroxy-quinolate (Alq 3 ) in particular has proven to be one of the most stable electron conductors. Instead of low-molecular ETLs, high-molecular ETLs can also be used. However, it has been shown that OLEDs which contain mixtures according to the invention continue to show very good results, in particular very low voltages and high power efficiencies, even without such an electron transport layer. Therefore, an electron transport layer was not used in all of the examples described below.
  • Electron Injection Layer A thin layer with a layer thickness between 0.2 and 8 nm, preferably between 0.5 and 5 nm, consisting of a material with a high dielectric constant, in particular inorganic fluorides and oxides, such as, for. B. LiF, Li 2 0, BaF 2 , MgO, NaF, and other materials, has proven to be particularly good as EIL. Especially in combination with AI, this additional layer leads to a significant improvement in electron injection and thus to improved results in terms of service life, quantum and power efficiency.
  • EIL Electron Injection Layer
  • Cathode Usually metals, metal combinations or metal alloys with a low work function are used here.
  • All low molecular weight materials of HIL, HTL, EML, HBL, ETL, EIL and cathode are, preferably smaller, in vacuum sublimation systems at a pressure of less than 10 ⁇ 5 mbar
  • the evaporation rates can be between 0.01 and 10 nm / s, preferably 0.1 and 1 nm / s.
  • Newer processes such as OPVD (Organic Physical Vapor Deposition) or LITI (Light Induced Thermal Imaging) are also suitable for the coating of low molecular weight materials, as are other printing techniques.
  • the OPVD has great potential for doped layers, because the setting of any mixing ratio is particularly successful.
  • the concentrations of the dopants can also be changed continuously. Thus, the prerequisites for the improvement of the electroluminescent device are optimal with the OPVD.
  • the devices according to the invention can also be produced by special printing processes (such as the LITI mentioned).
  • 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. For this, however, it is generally necessary to prepare appropriate layers (for LITI: transfer layers), which are then only transferred to the actual substrate.
  • Encapsulation An effective encapsulation of the organic layers including the EIL and the cathode is indispensable for organic electroluminescence devices. If the organic display is built on a glass substrate, there are several options. One option is to glue the entire structure to a second glass or metal plate. Two-component or UV-curing epoxy adhesives have proven to be particularly suitable. The electroluminescent device can be glued completely or only at 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.
  • the first example describes a comparison standard according to the prior art, in which the emitter layer consists of the host material CBP and the guest material lr (PPy) 3 (synthesized according to WO 02/060910). Furthermore, an OLED with an emitter layer consisting of the host material bis (9,9 ' -spiro-bifluoren-2-yl) ketone and the guest material lr (PPy) 3 is described.
  • the second example describes a further comparison between CBP and bis (9,9 '-spiro-bifluorene-2-yl) ketone (s. Example 1) with the red emitter Ir (BTP) 3 (synthesized according to WO 02/060910).
  • the third example describes two OLEDs, one with a deep red emitter lr (piq) 3 with bis (9,9 ' -spiro-bifluoren-2-yl) ketone and the other one with a red emitter lr (FMepiq) 3 with bis ( 9,9'-spiro-bifluorene-2-yl ketone).
  • piq deep red emitter lr
  • FMepiq red emitter lr
  • Emitter layer CBP 20 nm (evaporated; CBP obtained from ALDRICH and further purified, finally sublimed twice; 4,4'-bis (N-carbazolyl) biphenyl) (comparison standard)
  • Bathocuproin (BCP) 10 nm (evaporated; BCP purchased from ABCR, used as received;
  • OLEDs which have not yet been optimized, were characterized as standard; For this purpose, the electroluminescence spectra, the efficiency (measured in Cd / A) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics), and the service life were determined.
  • Matrix material M3 Matrix material 4
  • the OLEDs both the comparison standard OLED with CBP, and the OLED with bis (9,9 ' spiro-bifluoren-2-yI) ketone as host material show a green emission, resulting from the dopant lr (PPy) 3 .
  • OLEDs produced with the host material CBP a maximum efficiency of about 25 cd / A is typically obtained and 4.8 V are required for the reference luminance of 100 cd / m 2 .
  • OLEDs produced with the host material bis (9,9 '-spiro- bifluoren-2-yl) ketone a maximum efficiency of about 30 cd / A, where the required voltage for the reference luminance of 100 cd / m 2 even on 4.6 V drops. Efficiency is particularly high if neither a hole blocking layer (HBL) nor one Electron transport layer (ETL) is used and the doped emission layer (EML) extends to the cathode.
  • HBL hole blocking layer
  • ETL Electron transport layer
  • a maximum efficiency of over 35 cd / A is achieved, and the voltage required for the reference luminance of 100 cd / m 2 even drops below 3 V.
  • the power efficiency increases with use of bis (9,9 '-spiro-bifluorene-2-yl) ketone as the host material (A) against CBP ( ⁇ ) as the host material by 20% to 100% (Fig. 1).
  • Very high power efficiencies up to 50 Im / W (o) are obtained if neither a hole blocking layer (HBL) nor an electron transport layer (ETL) is used and the doping of the emission layer (EML) extends to the cathode.
  • HBL hole blocking layer
  • ETL electron transport layer
  • the two life curves (Fig. 2) with CBP and with bis (9,9 ' -spiro-bifluoren-2-yl) ketone as host materials (both used here with hole blocking and electron transport layers) were shown in the same figure for better comparability.
  • the figure shows the course of the luminance, measured in cd / m 2 , over time.
  • the lifespan is usually the time after which only 50% of the initial luminance is reached.
  • a lifespan of approximately 150 hours is obtained with an initial brightness of 1400 cd / m 2 , which corresponds to an accelerated measurement, since the initial brightness is significantly higher than the brightness required for typical active matrix-controlled display applications required (250 cd / m 2 ).
  • a lifespan of approximately 2000 hours is obtained with the same initial brightness, which corresponds to a lifespan increase of approximately 1300%; this also applies if neither a hole blocking layer (HBL) nor an electron transport layer (ETL) is used.
  • HBL hole blocking layer
  • ETL electron transport layer
  • lifetimes can now be calculated for an initial brightness of 250 cd / m 2 .
  • the service life is only 4700 hours, which is significantly less than the 10,000 hours required for display applications.
  • bis (9,9 ' - spiro-bifluoren-2-yl) ketone gives a lifespan of over 60,000 hours, which clearly exceeds the minimum requirements.
  • the OLEDs both the reference standard OLED with CBP and the OLED with bis (9,9 ' - spiro-bifluoren-2-yl) ketone as the host material, show a red emission resulting from the dopant lr (BTP) 3 .
  • the two spectra are shown in Fig. 3.
  • a maximum efficiency of about 8 cd / A is typically obtained for OLEDs produced with the host material CBP and 6.2 V are required for the reference luminance of 100 cd / m 2 .
  • OLEDs made with the host material bis (9,9 ' -spiro- bifluoren-2-yl) ketone a maximum efficiency of over 1 1 cd / A, whereby the voltage required for the reference luminance of 100 cd / m 2 even drops to 5.2 V (Fig. 4).
  • the two life curves (Fig. 5) were shown in the same figure for better comparability.
  • the figure shows the course of the luminance, measured in cd / m 2 , over time.
  • lifetimes can now be calculated for an initial brightness of 250 cd / m 2 .
  • the lifespan is only 1600 hours, which is significantly less than the 10,000 hours required for display applications.
  • bis (9,9'-spiro-bifluoren-2-yl) ketone gives a lifespan of over 8,200 hours, which is close to the minimum requirement.
  • the OLEDs show a deep red emission and a red emission, resulting from the dopants lr (piq) 3 (A) and lr (FMepiq) 3 ( ⁇ ).
  • the two spectra are shown in FIG. 6.
  • Ir (piq) 3 in bis (9,9 '-spiro-bifluorene-2-yl) ketone (A)
  • FIG. 8 shows the lifespan of Jr (piq) 3 with bis (9,9 ' -spiro-bifluoren-2-yl) ketone at a constant current of 10 mA / cm 2 with an initial brightness of approx. 800 cd / m 2 and 5 mA cm 2 with an initial brightness of approx. 400 cd / m 2 .
  • An extrapolation gives a lifespan of approx.

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Abstract

La présente invention concerne de nouveaux mélanges d'au moins deux substances, l'une servant de matière matricielle et l'autre étant une matière apte à l'émission qui contient au moins un élément d'ordre de grandeur supérieur à 20. L'invention a également pour objet l'utilisation de ces mélanges dans des composants électroniques organiques, des éléments électroluminescents et des affichages.
EP04726968A 2003-04-15 2004-04-13 Melanges de semi-conducteurs organiques aptes a l'emission et de matieres matricielles, leur utilisation et composants electroniques contenant ces melanges Withdrawn EP1618170A2 (fr)

Priority Applications (2)

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EP06014637A EP1717291A3 (fr) 2003-04-15 2004-04-13 Mélanges de semi-conducteurs organiques aptes à l'émission et de matières matricielles, leur utilisation et composants électroniques contenant ces mélanges
EP10008254A EP2281861A3 (fr) 2003-04-15 2004-04-13 Mélanges de semi-conducteurs organiques destinés à l'émission et matériaux de matrice, leur utilisation et composants électroniques pourvus de ces mélanges

Applications Claiming Priority (3)

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DE10317556.3A DE10317556B4 (de) 2003-04-15 2003-04-15 Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend diese
DE10355358A DE10355358A1 (de) 2003-11-25 2003-11-25 Mischungen von organischen zur Emission befähigten Halbleiter und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend dieses
PCT/EP2004/003861 WO2004093207A2 (fr) 2003-04-15 2004-04-13 Melanges de semi-conducteurs organiques aptes a l'emission et de matieres matricielles, leur utilisation et composants electroniques contenant ces melanges

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EP10008254A Withdrawn EP2281861A3 (fr) 2003-04-15 2004-04-13 Mélanges de semi-conducteurs organiques destinés à l'émission et matériaux de matrice, leur utilisation et composants électroniques pourvus de ces mélanges
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EP1717291A3 (fr) 2007-03-21
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EP1717291A2 (fr) 2006-11-02
JP5318347B2 (ja) 2013-10-16
KR101162933B1 (ko) 2012-07-05
EP2281861A2 (fr) 2011-02-09
WO2004093207A3 (fr) 2005-06-09
WO2004093207A2 (fr) 2004-10-28
JP5362759B2 (ja) 2013-12-11
JP2011201878A (ja) 2011-10-13
JP2006523740A (ja) 2006-10-19
US20060208221A1 (en) 2006-09-21

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