EP1578885A2 - Organic electroluminescent element - Google Patents

Organic electroluminescent element

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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
spiro
hole conductor
material
eml
characterized
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Withdrawn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)
French (fr)
Inventor
Anja Gerhard
Hubert Spreitzer
Philipp STÖSSEL
Horst Vestweber
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
Merck Oled Materials 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 to DE10261545 priority Critical
Priority to DE10261545 priority
Application filed by Merck Patent GmbH, Merck Oled Materials GmbH filed Critical Merck Patent GmbH
Priority to PCT/EP2003/013927 priority patent/WO2004058911A2/en
Publication of EP1578885A2 publication Critical patent/EP1578885A2/en
Application status is Withdrawn legal-status Critical

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    • H01L51/005Macromolecular systems with low molecular weight, e.g. cyanine dyes, coumarine dyes, tetrathiafulvalene
    • H01L51/0059Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H01L51/006Amine 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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    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract

The invention relates to the improvement of organic electroluminescent devices. Said devices are characterised in that the emitting layer (EML) consists of a mixture of two substances, one having hole-conductive characteristics and the other having light-emitting characteristics and that at least one of said substances contains a spiro-9,9'-difluoro unit.

Description

description

The organic electroluminescence

The present invention describes a novel design principle for organic electroluminescent elements, and its use in displays based thereon.

In a number of different applications, which in the broadest sense of the

Electronics industry can be attributed to the use of organic semiconductors as active components (= functional materials) for some time reality or is expected in the near future. So for quite a few years find light-sensitive organic materials (eg. As phthalocyanines) and charge transport materials on an organic basis (usually

Hole transporters based on triarylamine) for use in copying machines. The use of specific semiconducting organic compounds which are capable in some cases also in the emission of light in the visible spectral range is just at the beginning of the launch, for example, in organic electroluminescent devices. Their individual components, the organic light-emitting diodes (OLEDs), have a very broad range of applications as: 1. white or colored backlighting for monochrome or multicolor

Display elements (such. As pocket calculators, mobile phones and other portable applications), the second large-area displays (such. As traffic signs, billboards and other applications)

3. illumination elements in all colors and shapes,

4. monochrome or full-color passive matrix displays for portable applications (such. As mobile phones, PDAs, camcorders and other applications)

5. full-color, large-scale, high-resolution active matrix displays (for various applications such. As mobile phones, PDAs, laptops, Sat television and other

Applications). In these applications, the development is partly already very advanced, but there is still a great need for technical improvements.

Relatively simple OLEDs containing devices, the market has already taken place, as demonstrated by the car radios available in the market with "organic display" from Pioneer.

However, there are still considerable problems which require urgent improvement:

1. To va is the OPERATIONAL LIFE OLEDs, especially very low for BLUE EMISSION, still so far only simple applications can be realized commercially. Sanyo lifetimes for application-relevant brightness blue OLEDs in the range of about 3000 h were reported. Similar values ​​are also to materials of the company. Kodak.

2. This relatively short lifetime gives rise to a further problem: Just for FULL COLOR applications ( "full-color display"), ie displays which have no segmentations, but can represent all colors over the entire surface, it is particularly bad when age here at the colors at different rates, as is currently the case. Typical lifetimes for green and red OLEDs are about 30,000 or 20,000 hours. This causes (which is usually defined by a drop to 50% of initial brightness) before the end of the above life, there is a marked shift in the white point, ie the color fastness of representation is very bad in the display. To avoid this, some display manufacturers define the lifetime than 70% or 90% lifetime (ie, decrease in the initial brightness of 70% and 90% of the initial value). However, this results in the lifetime is even shorter, that is indented for BLUE OLEDs in the range of some 100 hours.

3. To compensate for the decrease in brightness, especially in the blue, the required operating current can be raised. However, such control is much more complicated and expensive.

4. Although the efficiencies of OLEDs, especially in BLUE are quite good, but again, of course - especially for portable applications ( "portable applications") - Improvements still desired.

5. While the color coordinates of OLEDs, especially in BLUE are quite good, but here are of course always room for improvement desired. In particular, the combination of good color coordinates with high efficiency still needs to be improved.

6. The aging processes are usually accompanied by an increase in voltage. This effect makes voltage-driven organic electroluminescent devices, for. As displays or display elements, difficult or impossible. A current-driven addressing is more complex in this case and more expensive. 7. The required operating voltage has been reduced in recent years, but must be further reduced to improve the power efficiency. That's just for portable applications of great importance. 8. The required operating current has likewise been reduced in recent years, but must be further reduced to improve the power efficiency. This is especially important for portable applications.

The reasons mentioned above under 1 to 8, make improvements in the production of OLEDs very desirable.

The general structure of organic electroluminescent devices is described for example in US 4,539,507 and US 5,151, 629th Typically, an organic electroluminescent device consisting of several layers, which are preferably applied to one another by means of vacuum techniques. These layers are specifically:

1. A carrier plate = substrate (typically glass or plastics). 2. A transparent anode (typically indium tin oxide, ITO).

3. A hole injection layer (Hole Injection Layer = HIL): z. B. on the basis of copper phthalocyanine (CuPc), or conductive polymers such as polyaniline (PANI) or polythiophene derivatives (such as PEDOT).

4. One or more hole transport layers (HTL = hole transport layer): usually based on triarylamine derivatives such. B. 4,4 ', 4 "-tris (N-1-naphthyl) -N-phenyl-amino) -triphenylamine (NaphDATA) as the first layer and N, N'-di (naphth-1-yl) - N, N'-diphenyl-benzidine (NPB) as the second hole transport layer.

5. An emission layer (EML = Emission Layer): this layer may coincide partly with the layers 4 or 6, but is usually made with fluorescent dyes, z. B. N, N'-diphenyl-quinacridone (QA), or

Matrix materials such. B. tris- (phenylpyridyl) iridium (IrPPy) doped host molecules such as aluminum tris-8-hydroxy-quinolinate (AlQ 3).

6. An electron transport layer (Electron Transport Layer = ETL): mostly based on aluminum tris-8-hydroxy-quinolinate (AlQ 3). 7. An electron injection layer (Electron Injection Layer = EIL): this layer may coincide partly with layer 6, and there will be a small part of the cathode specially treated or specially deposited.

8. A further electron injection layer (Electron Injection Layer = EIL): a thin layer consisting of a material having a high dielectric constant such. B. LiF, Li 2 O, BaF 2, MgO, NaF.

9. A cathode: here, generally metals, metal combinations or metal alloys are used with low work function normally, such. , Ca, Ba, Mg, Al, In, Mg / Ag.

The whole device is appropriately (depending on application) structured to contact, and finally hermetically sealed, as a rule, the life of such

Devices in the presence of water and / or air drastically shortened. The same also applies to inverted structures in which the light is coupled out of the cathode. In inverted OLEDs, the anode, for example, made of Al / Ni / Al or NiOx / Pt / PtOx or other metal / metal oxide compounds which possess a 5 eV HOMO greater there. The cathode consists of the same materials, which are described in Section 8 and 9, with the

Except that the metal such. , Ca, Ba, Mg, Al, In, etc., is very thin and transparent. The layer thickness is below 50 nm, more preferably below 30 nm, more preferably below 10 nm. A further transparent material is also applied to this transparent cathode, z. As ITO (indium tin oxide), IZO (indium zinc oxide), etc ..

The organic electroluminescence devices in which the emissive layer (EML) of more than one substance is, have long been known: • EP-A-281381 describes OLEDs in which the EML of a HOST (host) material, which holes and capable of transporting electrons and can emit a dopant which light is. Flag of this application is on the one hand, that the dopant is used in relatively small amounts (usually in the range of about 1%), on the other hand, that the host material for both holes and electrons can transport (good).

• EP-A-610 514 describes OLEDs which small amounts (<19%, preferably <9%) of hole transporting compounds in the EML have. However, only very specific classes of compounds for these compounds are allowed. The shelf life of such devices is relatively low.

• EP-A-1162674 describes OLEDs in which the EML of an emitter doped with at the same time a hole transporting and an electron transporting substance, there. The problem here is a technical point that three connections have to be applied in one layer in a very precise predetermined mixing ratio here. This is just at the prevailing process

(Vacuum evaporation) is very difficult to achieve technically with sufficient reproducibility.

• EP-A-1167488 describes OLEDs, which have as a special combination of EML and anthracene Aminodistyrylarylverbindungen. The problem here is a technical point that the compounds have a very high molecular weight, resulting in the prevailing process and the required for sublimation to partial decomposition of the molecules and thus to deterioration of application parameters.

It has now surprisingly been found that OLEDs which the novel - listed below - correspond design principle, have significant improvements over the prior art.

The invention is, therefore, an organic electroluminescent device comprising at least an emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one capable of emitting emissive material, characterized in that at least one of the two materials, one or more spiro-9,9'-bifluoreneinheiten and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1, preferably 5: 95 to 80: 20, more preferably 5: 95 to 25: 75 miles.

Emission capable in the sense of the invention means, showing the substance as a pure film in an OLED, an emission in the range 380 to 750 nm.

A preferred embodiment of the present invention is an organic

Electroluminescent device comprising at least an emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one capable of emitting emission material, wherein the HOMO of the hole conductor material in the range of 8.4 to 8.5 eV (vs. vacuum), and a substituted or unsubstituted diarylamino group, preferably at least one Triarylaminoeinheit or Carbazolgruppierung the compound has at least and capable of emitting emission material comprises one or more spiro-9,9'-bifluoreneinheiten and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1, preferably 5: 95 to 80: 20, particularly preferably from 5: 95 to 25: 75 miles.

A further preferred embodiment of the present invention is an organic electroluminescent device comprising at least an emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one capable of emitting emission material, wherein the HOMO of the hole conductor material in the range of 4.8 to 5.8 eV (vs. vacuum), and the compound has one or more spiro-9,9'-bifluoreneinheiten and at least one moiety containing group selected from substituted or unsubstituted diarylamino, carbazole or thiophene units and capable of emitting emission material is selected from the group of the metal complexes, stilbenamines, Stilbenarylene, condensed aromatic or heteroaromatic systems, but also of the phosphorescent heavy metal complexes, rhodamines, coumarins, the substituted or unsubstituted aluminum, zinc, gallium hydroxy-quinolinates, bis (p-diarylaminostyryl) aryls ne, DPVBi (4,4'-bis (2,2-diphenylvinyl) biphenyl) (and analogous compounds, anthracenes, Naphthacene, pentacenes, pyrenes, perylenes, rubrene, quinacridones, benzothiadiazole compounds, DCM (4-dicyanomethylene) -2 -methyl-6- (4-dimethylaminostyryl) -4H-pyran), DCJTB ([2- (1, 1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1, 1, 7 , 7-tetramethyl-1H, 5H-benzo [ij] quinolizine-9-yl) ethenyl] -4H-pyran-4-ylidene] -propandinitril), iridium, europium, or platinum complexes, and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1, preferably 5: 95 to 80: 20, more preferably 5: 95 to 25: 75 miles.

A further preferred embodiment of the present invention is an organic electroluminescent device comprising at least an emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one capable of emitting emission material, wherein the HOMO of the hole conductor material in the range of 4.8 to 5.8 eV (vs. vacuum), and the compound has one or more spiro-9,9'-bifluoreneinheiten and at least one moiety selected from substituted or unsubstituted diarylamino, carbazole or thiophene units and capable of emitting material emitting at least one spiro 9,9' bifluoreneinheit and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1, preferably 5: 95 to 80: 20, more preferably 5: 95 to 25: 75 miles.

The devices described above now have the following surprising advantages over the prior art: 1. The operating lifetime increases by a multiple.

2. The efficiency of corresponding devices is compared to systems that do not follow the inventive design, higher.

3. The color coordinates are better d. h will be - achieved more saturated colors - especially in the blue range.

Details on the information given here can be found in the examples described below.

Preferred embodiments of the OLED according to the invention are those where applicable, the glass transition temperature T g of the respective hole conductor compound is greater than 90 ° C, preferably greater than 100 ° C, more preferably greater than 120 ° C.

Another preferred embodiment is given if the glass transition temperature T g of the respective emission compound, more preferably greater than 100 ° C, preferably greater than 120 ° C greater than 130 ° C. It is particularly preferred if both the described high glass transition temperature of the hole conductor, as well as that of the emission material is present simultaneously.

The preferred embodiments of the devices described herein have through the high glass transition temperatures at a further increased operational, as well as bearing life.

In the inventive OLEDs, the layer thickness of the EML usually in the range of 5 to 150 nm, preferably in the range of 10 to 100 nm, more preferably in the range of 15 to 60 nm, very particularly preferably selected in the range of 20 to 40 nm ,

1. The color coordinates are better, with one for each desired color in accordance with the resonance conditions d = λ / 2n, the obtained optimum film thickness. For blue-emitting OLEDs obtained particularly good color coordinates when thin

Emission layers of 20-40 nm are chosen. For green and red OLEDs, the layer thickness must adjusted accordingly, ie increased.

2. The efficiency of corresponding devices is better. The optimal layer thickness ensures a balanced charge balance in the emission layer (emission film), thus improving efficiency. Specifically, the power efficiency is with thin

Emission layers of 20-40 nm greatest.

3. OPERATIONAL LIFE increases by a multiple of at optimum choice of the layer thickness because less current is needed here at optimal color coordinates and efficiency.

Preferred hole conductors compounds are substituted or unsubstituted triarylamine derivatives such as triphenylamine derivatives, but also corresponding dimeric or oligomeric compounds, ie compounds containing two or more Triarylaminuntereinheiten, as a subgroup, corresponding carbazole derivatives, Biscarbazolderivate, or Oligocarbazolderivate also cis- or trans

Indolocarbazole derivatives, furthermore also thiophene, Bisthiophen- and Oligothiophenderivate, as pyrrole, Bispyrrol- and Oligopyrrolderivate; in selected instances, it is also possible that the Triarylaminogruppierung is replaced by a hydrazone unit.

Particularly preferred hole conductors compounds are substituted or unsubstituted compounds according to the shown in the following formulas:

Aryl-A to aryl-C stand for aromatic or heteroaromatic rings, containing from 4 to 40 carbon atoms.

Preferred hole conductors compounds are spiro-9,9'-bifluorenderivate which 1 to 6

Substituents selected from substituted or unsubstituted diarylamino, carbazole, thiophene, bithiophene or Oligothiophengruppierungen wear, but also compounds which as substituents or aryl groups instead of simple one or more substituted or unsubstituted contain spiro-9,9'-bifluorenderivate. Hole conductor materials that are present as polymers and spiro-9,9'-bifluorenderivate are preferred as

Containing repeating unit, or spiro-9,9'-bifluorenderivate whose M w is a maximum of 10000 g / mol, particularly preferably hole conductor materials containing spiro-9,9 '' bifluorenderivate whose M w is a maximum of 10000 g / mol.

Particularly preferred hole conductors compounds are substituted or unsubstituted compounds according to the shown in the following formulas:

Ar 1, Ar 2 and Ar should represent aromatic or heteroaromatic rings, containing from 4 to 40 carbon atoms here.

As already mentioned above, preferred emission materials metal-hydroxy- are chinolinkomplexe, stilbenamines, Stilbenarylene, fused 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) arylenes, DPVBi and analogous compounds, anthracenes, Naphthacene, pentacenes, pyrenes, perylenes, rubrene, quinacridones, benzothiadiazole compounds, DCM, DCJTB, iridium, platinum or europium complexes. Particularly preferred are substituted or unsubstituted emission materials compounds according to the shown in the following formulas:

where n is the same or different and 1, 2 or 3,

X is identical or different and represents the elements N, O or S,

M is identical or different and for the elements Li, Al, Ga, In, Sc, Y, La, Cr, Mo, W,

Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Cu, Au, Zn, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho,

Er, Tm, Yb, or Lu is.

M = Al, Ga

AR stands for aromatic or heteroaromatic rings, containing from 4 to 40 carbon atoms; the substituents R should specify only one preferred position of such groups and are not intended to be limiting here.

Preferred emission compounds are spiro-9,9'-bifluorenderivate which bear 1 to 6 substituents selected from substituted or unsubstituted arylenes, heteroarylenes, Arylvinylenen or Diarylvinylenen, but also arylenes, heteroarylenes Arylvinylene or one or more substituted or unsubstituted spiro-9 , 9'-bifluorenderivate groups as substituents.

Particularly preferred are substituted or unsubstituted emission compounds Compounds according to the shown in the following formulas:

12

Formula (I)

Ar, Ar 1, Ar 2 and Ar 3 stand for aromatic or heteroaromatic rings, containing from 4 to 40 carbon atoms; n equals 0, 1 or 2; m represents 1 or 2, o represents 1, 2, 3, 4, 5 or 6; the substituents R should specify only one preferred position of such groups and are not intended to be limiting here. The radicals Z in formula (I) can be present more than once on an aromatic ring.

The compounds of formula (I) are new. A further subject of the invention are compounds of formula (I) in which Z represents one or more groups of the formula

Formula (I), and is wherein the symbols and indices used:

Ar, Ar 1, Ar 2 and Ar 3 are the same or different at each occurrence aromatic or heteroaromatic rings, containing from 4 to 40 carbon atoms, which may be substituted in the free positions by substituents R 1; n is on each occurrence, identically or differently, 0, 1 or 2; m is on each occurrence, identically or differently, 1 or 2; o is identical or different at each occurrence 1, 2, 3, 4, 5 or 6; wherein Ar can be bonded to both Ar 2 and Ar 3 as well as on to both in the form of a dendrimer; x is on each occurrence, identically or differently, 0, 1, 2, 3 or 4, with the proviso that the sum of all non-zero indices, x, R 1 is on each occurrence, identically or differently, a straight-chain, branched or cyclic alkyl or alkoxy chain having 1 to 22 carbon

Atoms, in which one or more non-adjacent C atoms by NR 2, O, S,

-CO-O-, O-CO-O- and in which one or more H atoms may be replaced by fluorine, an aryl or aryloxy group having 5 to 40 C atoms, in which one or more C atoms may be replaced by O, S or N and which may also be substituted by one or more non-aromatic radicals R 1, or Cl, F, CN, N (R 2) 2, B (R 2) 2, and two or more radicals R together may form an aliphatic or aromatic, mono- or polycyclic ring system; R 2 is on each occurrence, identically or differently, H, a straight-chain, branched or cyclic alkyl chain having 1 to 22 carbon atoms, in which one or more C atoms by non-adjacent O, S, -CO-O-, O- CO-O- and in which one or more H atoms may be replaced by fluorine, an aryl group having 5 to 40 C atoms, in which one or more carbon atoms are replaced by O, S or N may be replaced, which may also be substituted by one or more non-aromatic radicals R. 1

Inventive electroluminescent devices can for example be represented as follows:

1. ITO coated substrate: As a substrate is preferably coated ITO glass with low or no ionic impurities as possible, such. B. flat glass from Merck-Balzers or Akaii used. However, other ITO-coated transparent substrates such. B. flexible plastic films or laminates are used. The ITO has a high conductivity as possible with a high

Connect transparency. ITO layer thicknesses between 50 and 200 nm have been found to be particularly suitable. The ITO coating must as flat as possible, preferably with a roughness of less than 2 nm, its. The substrates are first with 4% Dekonex pre-cleaned in deionized water. Thereafter, the ITO is treated coated substrate either at least 10 minutes with ozone or a few minutes with oxygen plasma or irradiating a short time with an excimer lamp.

2. hole injection layer (Hole Injection Layer = HIL): As HIL is either a polymer or a low molecular weight substance. Particularly suitable are the polymers polyaniline (PANI) or polythiophene (PEDOT) and derivatives thereof. It is usually around 1 to 5% aqueous dispersions, which in thin layers between 20 and

200 nm, preferably between 40 and 150 nm film thickness on the ITO substrate by spin coating, inkjet printing, or other coating methods are applied. Thereafter, the coated PEDOT or PANI ITO substrates are dried. For the drying, several methods are available. Conventionally, the films are in a drying oven 1 to 10 minutes from 110 to 200 ° C, preferably between 150 and

dried 180 ° C. But newer drying methods such. B. irradiation with IR (infrared) light, lead to very good results, the irradiation time lasts only a few seconds. As the low-molecular material preferably thin layers of 5-30 nm copper phthalocyanine (CuPc) may be used. Conventionally, CuPc is in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10" 6 mbar, particularly preferably less than 10 "-7 mbar. However, newer methods such as the OPVD (Organic Physical Vapor Deposition) or LITI (Light Induced thermal Imaging) are suitable for the coating of low molecular weight materials all HIL need not only very well inject holes, but also adhere very well to ITO and glass;. this is both CuPc and for PEDOT and

PANI the case. A particularly low absorption in the visible range and high transparency show PEDOT and PANI, which is another necessary property for the HIL.

3. One or more hole-transport layers (Hole Transport Layer = HTL): Most OLEDs are one or more technical colleges prerequisite for good efficiency and high stability. In this case, one ( '4 "-tris (N-3-methylphenyl) -N-phenyl-amino -triphenylamine), or NaphDATA (4.4 4.4)' achieved with a combination of two layers, for example consisting of triarylamines such as MTDATA, 4 "-tris (N-1-naphthyl) -N-phenyl-amino) triphenylamine) (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 the second HTL very good results. MTDATA or NaphDATA cause an increase in efficiency in most OLEDs by about 20 - 40%; because of the higher glass transition temperature T g is preferred over MTDATA (T g = 100 ° C) NaphDATA (g = 130 ° C T). As a second layer Spiro-TAD (T g = 130 ° C) (T g = 95 ° C) is preferred because of the higher T g relative to NPB. Furthermore, it achieves better efficiencies for blue OLEDs with Spiro-TAD. MTDATA or NaphDATA have a layer thickness between 5 and 100 nm, preferably 10 and 60 nm, more preferably between 15 and 40 nm for thicker layers are required slightly higher voltages 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 10 and 100 nm, more preferably between 20 and 60 nm. With increasing layer thickness of NPB and most other triarylamines are required higher voltages for the same brightness. However, the layer thickness of Spiro-TAD has only a minor influence on the current-voltage electroluminescent characteristics, ie the required voltage to reach a certain brightness depends only slightly from the Spiro-TAD layer thickness. All the materials are in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10" 6 mbar, particularly preferably less

. Evaporated 10 "7 mbar The vapor deposition can be from 0.01 to 10 nm / s preferably from 0.1 to 1 nm / s for the HTL the same as for the HIL applies; newer methods such as the OPVD (Organic Physical Vapor Deposition) or LITI (. Light Induced thermal Imaging) are suitable for the coating of low molecular weight materials 4. emission layer (EML = emission layer). This layer may partially overlap with the

Layers 3 and / or 5 coincide. It consists z. Example, of a host material and simultaneously 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. Is achieved good results in a concentration of 5 - 10% Spiro-TAD in Spiro-DPVBi at a EML layer thickness of 15 - 70 nm preferably 20 -. 50 nm All the materials are in vacuum sublimation at a pressure of less than 10 "5 mbar , preferably less than 10 "6 mbar, particularly preferably 10 smaller" evaporated 7 mbar the vapor deposition can be from 0.01 to 10 nm / s preferably, be 0.1 and 1 nm / s for the EML, the same applies as for the HIL and HTL..; newer methods such as the OPVD or LITI are suitable for the coating of low molecular weight materials. for doped

Layers OPVD has especially great potential because the setting of any mixing ratio is particularly successful. Also, the concentrations of the dopants can be changed continuously. Thus, the requirement for improving the electroluminescence device are optimal in OPVD. 5. An electron-transport and hole blocking layer (Hole Blocking Layer = HBL): As

HBL-material has proven particularly BCP (2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline = bathocuproine) shown to be very effective. A thin layer of 3-20 nm, preferably 5 - 10 nm increases the efficiency very effectively. All the materials are in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10" 6 mbar, particularly preferably less than 10 "evaporated 7 mbar. The vapor deposition can be from 0.01 to 10 nm / s, preferably 0.1 and 1 nm / s respectively. Among other things, the OPVD is another method to apply these materials to a substrate.

6 electron-transporting layer (Electron Transport Layer = ETL): As ETL materials are metal-hydroxy-quino late well suited; especially aluminum tris-8-hydroxy-quinolate (AlQ 3) has been found to be one of the most stable electronic conductor. All the materials are in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10" 6 mbar, particularly preferably less than 10 "7 mbar evaporated. The

can deposition rates of between 0.01 and 10 nm / s, preferably 0.1 and 1 nm / s. For the EML, the same as for the HIL and HTL applies; newer methods such as the OPVD or LITI are suitable for the coating of low molecular weight materials.

7. electron injection layer (Electron Injection Layer = EIL): a thin layer having a layer thickness of between 0.2 and 8 nm, preferably 0.5 - 5 nm consisting of a

Material with a high dielectric constant, in particular inorganic fluorides and oxides such. B. LiF, Li 2 O, BaF2, MgO, NaF and other materials, has proved to be particularly well EIL. Especially in combination with AI this additional layer leads to a significant improvement in the electron injection and thus to improved results with respect to lifetime, quantum and power efficiency. All

Materials in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10" 6 mbar, particularly preferably less than 10 "evaporated 7 mbar. The vapor deposition can be of between 0.01 and 1 nm / s, preferably from 0.1 and 0.5 nm / s ,

8. Cathode: Here are usually used metals, metal combinations or metal alloys having a low work function, such. , Ca, Ba, Cs, K, Na, Mg, Al, In, Mg / Ag.

All the materials are in vacuum sublimation at a pressure of less than 10 "5 mbar, preferably less than 10" 6 mbar, particularly preferably less than 10 "evaporated 7 mbar. The vapor deposition can be of between 0.01 and 1 nm / s, preferably 0.1 and 0.5 nm / s . amounted 9. encapsulation: effective encapsulation of the organic layers including the EIL and the cathode is essential for organic electroluminescence devices, when the organic display is constructed on a glass substrate, there are several ways one way is the bonding of the entire structure with.. a second glass or metal plate. In this case have two-component or UV-curing epoxy adhesive were found to be particularly suitable. Here, the

The electroluminescent device but be completely bonded only at the edge or. When the organic display bonded only at the edge, one can additionally improve the durability by adding a so-called getter. This getter consists of a very hygroscopic material, in particular metal oxides, such. As BaO, CaO, etc., which binds the ingress of water and water vapors. An additional bond of oxygen is achieved with getter materials, such. , Ca, Ba, etc .. In case of flexible substrates is particularly important to ensure a high diffusion barrier. Here, in particular, laminates of alternating plastic and thin inorganic layers have proven (z. B. SiO x or SiN x). 10. Application spectrum: The points 1 - 9 described construction is active-powered for both monochrome as well as full-color passive-matrix displays or for portable devices such. As mobile phones, PDAs, camcorders and other applications suitable. In passive matrix displays are required depending on the number of the pixels 1000 to more than 100,000 cd / m 2 peak brightness; first applications are from 5000 to 20,000 cd / m 2 peak brightness. For full-color large-area high-resolution displays, the active-matrix control preferred. The required brightness of each pixel is between 50 and 1000 cd / m 2, preferably between 100 and 300 cd / m 2. Described construction 9 - Here again, the under 1 is suitable. Active matrix control is for all display applications (such. As mobile phones, PDAs and other applications) suitable, especially for large-scale applications such. As in laptop computers and televisions. Further applications are white or colored backlighting for monochrome or multicolor display elements (such as. For example, in

Calculators, mobile phones and other portable applications), large-area displays (such. As traffic signs, billboards and other applications) or illumination elements in all colors and shapes.

As described above, the manufacture of the devices of the invention can be carried out other than by sublimation or OPVD process by special printing method (such as the called LITI). This has both advantages in terms of scalability of production, and with regard to the setting of mixing ratios in blend layers used. For this purpose, but it is usually necessary, appropriate layers (for LITI: transfer

Layers) to prepare, which is then transmitted only on the actual substrate.

then (in addition to any required excipients which are required for the transfer step), containing the mixture of hole conductor material and the emitter material, as described above in the desired ratio in these layers. These layers are

The present invention, as well as use of these layers to produce devices of the invention.

The preparation of the devices of the invention can be carried out by other printing processes such as ink-jet printing (ink jet printing process).

The present application text and in the following in the examples below are only to organic light emitting diodes and the corresponding displays. Despite this restriction of the description is for the specialist without further inventive step

Intervention possible to make respective layers according to the invention and to apply such. To call for example for organic solar cells (O-SCs), organic field effect transistors (O-FETs), or organic laser diodes (O-laser), only a few more applications.

The present invention is further illustrated by the following examples without wishing to restrict it. The skilled artisan can prepare further inventive devices from the description and the examples mentioned without inventive step.

Examples: The examples listed below have the following layer structure:

Glass / ITO (80 nm) / HIL (60 nm) / HTL-1 (20 nm) / HTL-2 (20 nm) / EML (20 - 40 nm) / ETL (10 - 20 nm) / metal-1 ( 5 nm) / metal 2 (150 nm). Examples 10 and 11 additionally contained between EML and ETL a blocking layer for holes (HBL). Hence this gave the following layer structure: Glass / ITO (80 nm) / HIL (60 nm) / HTL-1 (20 nm) / HTL-2 (20 nm) / EML (20 - 40 nm) / HBL (5 - 10 nm) / ETL (10 - 20 nm) / metal-1 (5 - 10 nm) /

Metal 2 (150 nm).

• with 80 nm ITO coated glass was purchased from Merck-Balzers.

• As HIL a 60 nm thick layer of PANI was Covion (Pat 010) or a 60 nm thick layer of PEDOT by the company Bayer (Baytron P 4083) was used. The PANI layer was prepared from a 4% dispersion by spin coating at 4000 rpm. The resulting film was annealed for five minutes at 180 ° C. The PEDOT film was prepared from a 2% dispersion by spin coating at 3000 rpm. The resulting film was annealed for five minutes at 110 ° C.

• As HTL 1 NaphDATA was used by the company Syntec. This material was purified by sublimation prior to use in OLEDs.

• The HTL-2 Spiro-TAD was used by Covion.

• The EML is described in detail in Examples 1-13.

• As HBL BCP was used by the company ABCR. This material was purified by sublimation prior to use in OLEDs. • The ETL was AIQ 3 is used by the company Covion.

• The metal-1 Ba was used by the company Aldrich.

• As metal-2 Ag was used by the company Aldrich.

The organic materials (HTL-1 / HTL-2 / EML / (HBL) / ETL) were evaporated in a converted from Covion vapor deposition apparatus of Pfeiffer vacuum at a pressure of <10 "6 mbar in succession. The system was equipped with an automatic installment and

Film thickness control facilities. The unmixed EML layers were prepared as reference were the same as HTL-1, HTL-2, ETL and HBL evaporated in the Pfeiffer vapor deposition apparatus at a pressure <10 "6 mbar. In the mixed EML layers (mixtures of two different materials) were evaporated two materials at the same time. the concentrations described in the examples were achieved by the rate corresponding to the mixing ratios were adjusted. the metals (metal 1 / metal 2) were in a converted from Covion vapor deposition apparatus of Balzers at a pressure <10 "6 mbar vapor-deposited. The plant was also equipped with an automatic rate and film thickness control.

The substances listed in the examples of the mixtures are the following

Examples shown again.

Example 1 :

The layer structure was as described above: glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = Spiro-DPVBi (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of

EML (the substances spiro-DPVBi + Spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (Spiro-DPVBi + Spiro-TAD), said spiro-TAD had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of 3 compared with the reference

OLED of about 1500 h to 4500 h. At the same time, the photometric efficiency (unit cd / A) was improved by about 10% and the power efficiency was also increased. Presented a mixture of spiro-TAD and spiro-DPVBi at a concentration of 15% spiro DPVBi ago, so the service life increased by a factor of four from 1500 hours to 6000 hours. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. As for a brightness of 100 cd / m 2 instead of 5.5 V only 4.5 V.

Example 2: The layer structure was as described above: glass / ITO / PEDOT / NaphDATA /

Spiro-TAD / EML = Spiro-DPVBi (+ spiro-AA2) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances spiro-DPVBi, and spiro-AA2) developed by Covion and synthesized. The EML consisted of a mixture of the two substances (Spiro-DPVBi, and spiro-AA2), said spiro-AA2 had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance spiro-AA2 in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of> 8 in comparison to the reference OLED h of about 1,500 to> 12,000 h. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 5.5 V, only 4.5 V.

Example 3:

The layer structure was as described above: glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = Spiro-Ant1 (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances spiro Ant 1 and spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (spiro Ant 1 and

Spiro-TAD), said spiro-TAD had a proportion of 50%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor> 100 in comparison to the reference OLED from about 100 hours to> 10,000 h. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. As for a brightness of 100 cd / m 2 instead of 6 V only 4.5 V.

Example 4:

The layer structure was as described above: glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = Spiro-Ant2 (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances spiro Ant 2 and spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (spiro Ant 2 and

Spiro-TAD), said spiro-TAD had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor> 3 in comparison to the reference OLED h of about 300 to> 900 h. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 6.5 V, only 5.5 V.

Example 5:

The layer structure was as described above: glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = Spiro-pyrene (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of

EML (the substances spiro-pyrene and spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (spiro-pyrene and spiro-TAD), said spiro-TAD had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of 3 compared with the reference

OLED of about 1500 h to 4500 h. At the same time, the photometric efficiency (unit cd / A) has been improved by up to 20%, and the power efficiency was also increased. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 5.5 V, only 4.5 V.

Example 6:

The layer structure corresponded to that described above: glass / ITO / PEDOT / NaphDATA /

Spiro-TAD / EML = TBPP (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances TBPP and spiro-TAD) were developed by Covion and synthesized. The

EML consisted of a mixture of the two substances (TBPP and Spiro-TAD), said spiro-TAD had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of 10 compared to the reference OLED from 500 h to 5000 h. At the same time, the photometric efficiency (unit cd / A) was up to

100% improved, and the power efficiency was also increased. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 7 V only 6 V.

Example 7: The layered construction was as described above: glass / ITO / PEDOT / NaphDATA /

Spiro-TAD / EML = DTBTD (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances DTBTD and spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (DTBTD and Spiro-TAD), said spiro-TAD had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of 8 in comparison to the reference OLED from 500 h to 4000 h.

EXAMPLE 8 The layer structure was as described above: glass / ITO / PEDOT / NaphDATA /

Spiro-TAD / EML = BDPBTD (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances BDPBTD and spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (BDPBTD and Spiro-TAD), said spiro-TAD had a proportion of 90%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of> 10 in comparison to the reference OLED from about 1000 h> 10,000 h. At the same time, the photometric efficiency (unit cd / A) has been improved by up to 100%, and the power efficiency was also increased. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 8 V only 5 V.

Example 9:

The layer structure was as described above: glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = BDTBTD (+ Spiro-TAD) / AlQ 3 / Ba / Ag. The two materials of the EML

(The substances BDTBTD and spiro-TAD) were developed by Covion and synthesized. The EML consisted of a mixture of the two substances (BDTBTD and Spiro-TAD), said spiro-TAD had a proportion of 90%. Furthermore, OLEDs were produced as a reference without the substance spiro-TAD in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of 10 compared with the reference

OLED of about 1000 h to> 10000 h. At the same time, the photometric efficiency (unit cd / A) has been improved by up to 400%, and the power efficiency was also increased. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 9 V only 6 V.

EXAMPLE 10 The layer structure corresponded to that described above, including the HBL: Glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = IrPPy (+ spiro-carbazole) / BCP / Alq3 / Ba / Ag. IrPPy was synthesized by Covion, and spiro-carbazole was developed by Covion and synthesized. The EML consisted of a mixture of the two substances (IrPPy and spiro-carbazole), said spiro-carbazole had a proportion of 90%. Furthermore, were

OLEDs produced as a reference without the substance spiro-carbazole in the EML. The photometric efficiency (unit cd / A) was improved by up to 500%, and the power efficiency was also increased. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 9 V only 6 V.

Example 11:

The layer structure was as described above, including the HBL: Glass /

ITO / PEDOT / NaphDATA / Spiro-TAD / EML = IrPPy (+ spiro 4PP6) / BCP / Alq3 / Ba / Ag. IrPPy was synthesized by Covion, and spiro-4PP6 developed by Covion and synthesized. The EML consisted of a mixture of the two substances (IrPPy and spiro-4PP6), said spiro-4PP6 had a proportion of 90%. Furthermore, OLEDs were produced as a 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. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 9 V, only 5.5 V.

EXAMPLE 12 The layer structure was as described above: glass / ITO / PEDOT / NaphDATA /

Spiro-TAD / EML = Spiro-Ant2 (+ CPB) / AlQ 3 / Ba / Ag. The two materials of the EML (the substances spiro Ant 2 and CPB) developed by Covion and synthesized. The EML consisted of a mixture of the two substances (spiro Ant2 and CPB), wherein CPB had a proportion of 20%. Furthermore, OLEDs were produced as a reference without the substance CPB in the EML. In the case of the mixture in the EML increased the

Lifetime of the OLED by a factor of 6 compared to the reference OLED from about 300 hours to> 1800 hours. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 7 V only 6 V. In addition, the improved color coordinates: In the reference OLED CIE values of x = 0.15 to y = 12:15 achieved, with a proportion of 20% CPB were achieved x = y = 0:15 and 0:12.

Example 13:

The layer structure was as described above: glass / ITO / PEDOT / NaphDATA / Spiro-TAD / EML = Spiro-pyrene (+ CPB) / AlQ 3 / Ba / Ag. CPB was synthesized by Covion, and spiro-pyrene was developed by Covion and synthesized. The EML consisted of a mixture of the two substances (spiro-pyrene and CPB), wherein CPB had a proportion of 10%. Furthermore, OLEDs were produced as a reference without the substance CPB in the EML. In the case of the mixture in the EML, the lifetime of the OLED increased by a factor of 6 compared to the reference OLED from about 300 hours to> 1800 hours. Furthermore steeper IU EL were obtained characteristics, that is, to achieve a particular brightness, lower voltages were needed, z. B. for a brightness of 100 cd / m 2 instead of 7 V only 6 V. In addition, the improved color coordinates: In the reference OLED CIE values of x = 0.15 to y = 12:20 achieved, with a proportion of 10% CPB were achieved x = y = 0:15 and 0:17.

For clarity, the examples listed in the above-mentioned are

Substances listed again below:

spiro PP6

DTBTD

TBPP

Claims

claims
1. The organic electroluminescence device comprising at least an emitting layer (EML), which contains a mixture of at least one hole conductor material and at least one capable of emitting emissive material, characterized in that at least one of the two materials, one or more spiro 9, 9'-bifluoreneinheiten and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1.
2. The organic electroluminescence device according to claim 1, characterized in that the emitting layer (EML) includes a mixture of at least one hole conductor material and at least one capable of emitting emission material, wherein the HOMO of the hole conductor material in the range of 8.4 to 8.5 eV (vs. vacuum), and the compound at least one substituted or unsubstituted diarylamino group, a Triarylaminoeinheit or
having Carbazolgruppierung and capable of emitting emission material comprises one or more spiro-9,9'-bifluoreneinheiten and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1.
3. The organic electroluminescence device according to claim 1, characterized in that the emitting layer (EML) includes a mixture of at least one hole conductor material and at least one capable of emitting emission material, wherein the HOMO of the hole conductor material in the range of
4.8 to
5.8 eV (vs. vacuum), and the compound has one or more spiro-9,9' bifluoreneinheiten and at least one moiety selected from substituted or unsubstituted diarylamino, Triarylamino-, carbazole or thiophene units and capable of emitting emission material is selected from the group of metal complexes stilbenamines, Stilbenarylene, condensed aromatic or heteroaromatic systems, but also of the phosphorescent heavy metal complexes, rhodamines, coumarins, substituted or unsubstituted
, Gallium-hydroxy-quinolinates aluminum, zinc, bis (p-diarylaminostyryl) arylenes, DPVBi (4,4'-bis (2,2-diphenylvinyl) biphenyl) and analogous compounds, anthracenes, Naphthacene, pentacenes, pyrenes, perylenes, rubrene, quinacridones, benzothiadiazole compounds, DCM (4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran), DCJTB ([2- (1, 1-dimethylethyl) -6- [2- (2,3,6,7-tetrahydro-1, 1, 7,7-tetramethyl-
1H, 5H-benzo [ij] quinolizine-9-yl) ethenyl] -4H-pyran-4-ylidene] -propandinitril), iridium, europium or platinum complexes, and the weight ratio of hole conductor material to emission material 1: 99-99 : 1. 4. The organic electroluminescence device according to claim 1, characterized in that the emitting layer (EML) includes a mixture of at least one hole conductor material and at least one capable of emitting emission material, wherein the HOMO of the hole conductor material in the range of 8.4 to 8.5 eV (vs. vacuum), and the compound has one or more spiro-9,9' bifluoreneinheiten and at least one moiety selected from substituted or unsubstituted diarylamino, Triarylamino-, carbazole or thiophene units and capable of emitting material emitting at least one spiro-9,9 '- bifluoreneinheit and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1.
The organic electroluminescent device according to one or more of claims 1 to 4, characterized in that the weight ratio of hole conductor material to emission material 5: 95 to 80: 20th
6. The organic electroluminescent device according to one or more of claims 1 to 4, characterized in that the weight ratio of hole conductor material to emission material 5: 95 to 25: 75 miles.
7. The organic electroluminescence device according to one or more of claims 1 to 6, characterized in that the glass transition temperature Tg of the hole conductor materials is greater than 90 ° C.
8. The organic electroluminescence device according to one or more of
Claims 1 to 7, characterized in that the glass transition temperature is greater than 100 ° C T g of the emissive materials.
9. Compounds of formula (I),
wherein Z is one or more groups of the formula
is and wherein applies to the symbols and indices: Ar, Ar 1, Ar 2 and Ar 3 are on each occurrence, the same or different aromatic or heteroaromatic compounds having 4 to 40 carbon atoms which be substituted in the free positions by substituents R 1 can; n is on each occurrence, identically or differently, 0, 1 or 2; m is on each occurrence, identically or differently, 1 or 2; o is identical or different at each occurrence 1, 2, 3, 4, 5 or 6; wherein Ar can be bonded to both Ar 2 and Ar 3 as well as on to both in the form of a dendrimer; x is on each occurrence, identically or differently, 0, 1, 2, 3 or 4, with the proviso that the sum of all indices x is non-zero,
R 1 is on each occurrence, identically or differently, a straight-chain, branched or cyclic alkyl or AI koxy chain having 1 to 22 carbon atoms, in which one or more non-adjacent C atoms by NR 2, O, S, -CO -O-, O-CO-O- and in which one or more H atoms may be replaced by fluorine, an aryl or aryloxy group having 5 to 40 C atoms, in which one or more carbon atoms by O, S or N may be replaced, which can also be substituted by one or more non-aromatic radicals R, or Cl, F, CN, N (R 2) 2, B (R 2) 2, wherein two or more R 1 together can form an aliphatic or aromatic, mono- or polycyclic ring system; R 2 is on each occurrence, identically or differently, H, a straight-chain, branched or cyclic alkyl chain having 1 to 22 carbon atoms, in which one or more C atoms by non-adjacent O, S, -CO-O-, O- CO-O- and in which one or more H atoms may be replaced by fluorine, an aryl group having 5 to 40 C atoms, in which one or more carbon atoms are replaced by O, S or N may be replaced, which können.steht also be substituted by one or more non-aromatic radicals R. 1
10. Use of the compounds according to claim 9 for the preparation of organic electroluminescent devices.
11. The organic electroluminescent device according to one or more of claims 1 to 10, characterized in that one or more layers are produced by a sublimation.
12. The organic electroluminescent device according to one or more of Claims
1 to 10, characterized in that one or more layers with the OPVD (Organic Physical Vapor Deposition) method can be applied.
13. The organic electroluminescent device according to one or more of claims 1 to 10, characterized in that one or more layers are applied by printing techniques.
14. The organic electroluminescent device according to claim 13, characterized in that it is in the printing art to the ink jet method.
15. The organic electroluminescent device according to claim 13, characterized in that it is in the printing art to the LITI method (Light Induced Thermal Imaging).
16. Organic layers for producing organic electroluminescence devices using the LITI method according to claim 15, comprising at least one hole conductor material and at least one emissive material capable of emission, characterized in that at least one of the two materials bifluoreneinheiten spiro-9,9'-one or more and the weight ratio of hole conductor material to emission material from 1: 99 to 99: 1.
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KR20050085239A (en) 2005-08-29
CN100489056C (en) 2009-05-20
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WO2004058911A2 (en) 2004-07-15
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