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  • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
  • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
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  • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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  • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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  • H05B33/00—Electroluminescent light sources
  • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
  • H05B33/14—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
  • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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  • C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
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  • Y02E10/549—Organic PV cells

Definitions

• the present invention describes novel compounds and their
• OLEDs organic electroluminescent devices
• the operating voltage is quite high, especially with fluorescent OLEDs, and should therefore be further reduced to improve power efficiency. This is especially important for mobile applications.
• OLEDs according to the prior art show a strong dependence of the operating voltage on the layer thickness of the hole transport layer.
• organic electroluminescent devices which contain certain compounds listed below as blue-emitting dopants in a host material, have significant improvements over the prior art. With these materials it is possible to obtain longer lifetimes with higher efficiency. In addition, unlike prior art materials, these compounds can also be sublimated in significant quantities without appreciable decomposition, and are therefore much easier to handle than prior art materials.
• Ar 1 , Ar 2 , Ar 3 is the same or different at each occurrence and is an aryl or heteroaryl group having 5 to 24 aromatic ring atoms, which may be substituted by one or more R 1 ;
• Ar 4 is the same or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
• R 2 is the same or different at each occurrence, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 carbon atoms;
• X 2 , X 3 is the same or different X 1 at each occurrence and spans a cyclic ring system with Ar 2 and Ar 3 ;
• q is 1, 2 or 3 when Y is bonded through an element of the fifth main group and 2 when Y is oxygen is bound, and is 1 or 2 when Y is linked through another element of the sixth main group;
• r is (3-q) when Y is bonded through an element of the fifth main group, and is (2-q) when Y is bonded through a member of the sixth main group;
• An aryl group or a heteroaryl group in the context of this invention is understood as meaning an aromatic group or heteroaromatic group having a common aromatic electron system, where an aryl group has 6 to 24 C atoms and a heteroaryl group has 2 to 24 C atoms and a total of at least 5 aromatic ring atoms includes.
• the heteroatoms are preferably selected from N, O and / or s.
• this may be a simple homo- or heterocycle, for example benzene, pyridine, thiophene, etc., or it may be a fused aromatic ring system in which at least two aromatic or heteroaromatic rings, for example benzene rings, are fused together ie, having at least one common edge and thereby also a common aromatic system
• This aryl or heteroaryl group may be substituted or unsubstituted, and optionally substituted substituents may form further ring systems Naphthalene, anthracene, phenanthrene, pyrene, etc. as aryl groups and quinoline, acridine, benzothiophene,
• Carbazole, etc. as heteroaryl groups in the context of this invention while for example biphenyl, fluorene, spirobifluorene, etc. represent no aryl groups, since these are separate aromatic electron systems.
• An aromatic ring system in the sense of this invention contains 6 to 40 carbon atoms in the ring system.
• a heteroaromatic ring system in the sense of this invention contains 2 to 40 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of the C atoms and heteroatoms gives at least 5.
• the heteroatoms are preferably selected from N, O and / or S.
• An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups Heteroaryl groups by a short, non-aromatic unit (less than 10% of the atoms other than H, preferably less than 5% of the atoms other than H), such as.
• a short, non-aromatic unit less than 10% of the atoms other than H, preferably less than 5% of the atoms other than H
• an sp 3 -hybridized C, N or O atom may be interrupted.
• systems such as 9,9'-spirobifluorene, 9,9-diaryl fluorene, triarylamine, diaryl ethers, etc. are to be understood as aromatic ring systems in the context of this invention.
• a C 1 - to C 4 -alkyl group in which individual H atoms or CH 2 groups can also be substituted by the abovementioned groups particularly preferably the radicals methyl, ethyl, n-propyl, i Propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s -pentyl, cyclopentyl, n -hexyl, cyclohexyl, n -heptyl, cycloheptyl, n-octyl, cyclooctyl , 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl,
• a C 1 to C 4 o-alkoxy group is more preferably understood as meaning methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
• aryl or heteroaryl group which may be monovalent or bivalent depending on the use, which may be substituted in each case with the abovementioned radicals R 1 and which may be linked via any position on the aromatic or heteroaromatic, are in particular groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzo thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline,
• aromatic and heteroaromatic ring systems are understood to mean, in addition to the abovementioned aryl and heteroaryl groups, for example biphenylene, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, tetrahydropyrene and cis or trans indenofluorene.
• the choice of the Y unit depends on the desired function of the compound according to formula (1). If the compound of the formula (1) is to be used as an emitter in an emission layer or as a hole transport material, for example in a hole transport layer or hole injection layer, then the symbol Y is preferably nitrogen or phosphorus, particularly preferably nitrogen.
• R 1 is H when it is bonded directly to one of the groups Ar 1 to Ar 4 .
• R 1 is particularly preferably when it is bonded to the group X 1 , X 2 , X 3 and / or X 4 , identical or different at each occurrence, methyl, tert-butyl, a phenyl group which by one or more d- to C 4 -alkyl groups may be substituted, or a monovalent heteroaryl group having 5 or 6 aromatic ring atoms, which may be substituted by one or more Ci to C 4 alkyl groups, most preferably methyl or a phenyl group which is replaced by one or more Ci - Can be substituted to C 4 alkyl groups.
• two or more radicals R 1 together form a ring system.
• the index q is preferably equal to 2.
• compounds of formula (1) which are of symmetrical construction and which have a threefold axis of rotation when Y is selected from the fifth main group or have a twofold axis of rotation when Y is selected from the sixth main group, which is not only refers to the aromatic groups Ar 1 to Ar 3 , but also to the bridges X 1 to X 4 and the radicals R 1 and R 2 .
• Examples of preferred compounds according to formula (1) are the structures (1) to (82) depicted below.
• Compounds according to the structures (8), (28) and (53) can be used, for example, as comonomers for the production of corresponding conjugated, partially conjugated or non-conjugated polymers, oligomers or as the core of dendrimers.
• the polymerization is preferably carried out via the halogen functionality.
• polyfluorenes eg according to EP 842208 or WO 00/22026
• poly-spirobifluorenes eg according to EP 707020, EP 894107 or EP 04028865.6
• poly-para-phenylenes e.g.
• polycarbazoles for example according to WO 04/070772 and WO 04/113468
• polyvinylcarbazoles for example according to EP 1028136
• polydihydrophenanthrenes for example US Pat according to WO 05/014689
• polyindenofluorenes for example according to WO 04/041901 and WO 04/113412
• polyketones for example according to WO 05/040302 or else copolymerized in copolymers of several of these units.
• Another object of the invention are thus conjugated, partially conjugated and non-conjugated polymers, oligomers or dendrimers containing one or more compounds of formula (1), wherein one or more bonds of the compound of formula (1) to the polymer or dendrimer are present.
• the compounds of the invention can according to the expert known synthesis steps, such as. As bromination, Suzuki coupling, Hartwig-Buchwald coupling, etc., are shown.
• the indenofluorene precursors can be prepared as depicted in Synthetic Scheme 1: by Suzuki coupling of a benzoic boronic acid and 1,4-dibromo-2,5-bis (methylcarboxylate) benzene followed by ring closure on exposure to a strong acid and reduction the unsubstituted trans-indenofluorene, which can be alkylated with alkylating agents. This can be selectively monobrominated by stoichiometric reaction with a brominating agent or converted into the corresponding amino compound by nitration and reduction.
• Synthesis of tris (indenofluorenyl) amine can be accomplished by Hartwig-Buchwald coupling of the monobromine and amino compounds as shown in Synthetic Scheme 2.
• unsymmetrical bis (indenofluorenyl) aryl amines can be prepared by Hartwig-Buchwald coupling as shown in Synthetic Scheme 3.
• Synthesis of tris (indenofluorenyl) phosphines or phosphine oxides can be accomplished from monobromindofluorene by lithiation and reaction with PCI 3 , as shown in Synthetic Scheme 4. Oxidation then gives the corresponding phosphine oxide.
• other electrophiles can be used here, such as.
• the compounds according to formula (1) can be used in organic electroluminescent devices.
• the compound is preferably used in the emitting layer as a mixture with at least one host material. It is preferred if the compound according to Formula (1) in the mixture is the emitting compound (the dopant).
• Preferred host materials are organic compounds whose emission is shorter than that of the compound of formula (1) or which do not emit at all.
• the invention therefore furthermore relates to mixtures comprising at least one compound of the formula (1) and at least one host material.
• host materials are selected from the classes of the oligo- arylenes (eg 2,2 ', 7,7'-tetraphenyl-spirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligo-arylenes containing condensed aromatic groups, the oligo-arylenevinylenes (eg DPVBi or spiro-DPVBi according to EP 676461), the polypodal metal complexes (eg according to WO 04/081017), the hole-conducting compounds (eg according to WO 04/058911), the electron-conducting compounds, in particular Ketones, phosphine oxides, sulfoxides, etc.
• the oligo- arylenes eg 2,2 ', 7,7'-tetraphenyl-spirobifluorene according to EP 676461 or dinaphthylanthracene
• Particularly preferred host materials are selected from the classes of the oligo- arylenes containing naphthalene, anthracene and / or pyrene or atrop isomers of these compounds, the oligo-arylenevinylene, the ketones, the phosphine oxides and the sulfoxides.
• Very particularly preferred host materials are selected from the classes of oligoarylenes containing anthracene and / or pyrene or atropisomers of these compounds, the phosphine oxides and the sulfoxides.
• the proportion of the compound of formula (1) in the mixture of the emitting layer is between 0.1 and 99.0 wt.%, Preferably between 0.5 and 50.0 wt.%, Particularly preferably between 1.0 and 20.0 wt.%, In particular between 1.0 and 10.0 wt. %. Accordingly, the proportion of the host material in the layer is between 1.0 and 99.9% by weight, preferably between 50.0 and 99.5% by weight, especially preferably between 80.0 and 99.0% by weight, in particular between 90.0 and 99.0% by weight.
• the compounds according to formula (1) are used as hole transport material and / or hole injection material, in particular in a hole transport layer and / or in a hole injection layer. This is especially true if the symbol Y stands for N or P. In this case, it may be preferred if the compound is doped with electron acceptor compounds, for example with F 4 -TCNQ or with compounds as described in EP 1476881 or EP 1596445.
• compounds of the formula (1) can be employed either as an emissive unit, as a hole-transporting unit, as an electron-transporting unit or as a matrix for phosphorescent units.
• the compound according to formula (1) is used as hole transport material in a hole transport layer or as hole injection material in a hole injection layer or as electron transport material in an electron transport layer or as hole blocking material in a hole blocking layer, a proportion of 100% may also be preferred
• organic electroluminescent devices characterized in that a plurality of emitting compounds are used in the same layer or in different layers, wherein at least one of these compounds has a structure according to formula (1).
• these compounds have a total of several emission maxima between 380 nm and 750 nm, so that a total of white emission results, ie in addition to the compound of formula (1) at least one further emitting compound is used, which can fluoresce or phosphoresce and the yellow, emitted orange or red light.
• three-layer systems of which at least one of these layers is a
• the organic electroluminescent device may contain further layers. These may be, for example: hole injection layer, hole transport layer, electron transport layer and / or electron injection layer. However, it should be noted at this point that not necessarily each of these layers must be present. Thus, particularly when using compounds according to formula (1) with electron-conducting host materials, very good results continue to be obtained if the organic electroluminescent device does not contain a separate electron transport layer and the emitting layer directly adjoins the electron injection layer or the cathode. Alternatively, the host material may also simultaneously serve as an electron transport material in an electron transport layer.
• the organic electroluminescent device does not contain a separate hole transport layer and the emitting layer directly adjoins the hole injection layer or the anode. Furthermore, it may be preferred if identical or different compounds according to formula (1) are used simultaneously as dopant in the emitting layer and as hole-conducting compound (as pure substance or as mixture) in a hole transport layer and / or as electron-conducting compound in an electron transport layer. Further preferred is an organic electroluminescent device, characterized in that one or more layers are coated with a sublimation process. The materials are vacuum deposited in vacuum sublimation at a pressure of less than 10 '5 mbar, preferably less than 10 "6 mbar, more preferably less than 10 ⁇ 7 mbar.
• an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
• the materials are applied at a pressure between 10 '5 mbar and 1 bar.
• an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
• any printing process such as screen printing, flexographic printing or offset printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (ink jet printing), are produced.
• LITI Light Induced Thermal Imaging, thermal transfer printing
• inkjet printing ink jet printing
• soluble compounds according to formula (1) are necessary. High solubility can be achieved by suitable substitution of the compounds.
• the compounds according to the invention When used in organic electroluminescent devices, the compounds according to the invention have the following surprising advantages over the prior art:
• the stability of corresponding devices is higher compared to systems according to the prior art, which shows above all in a much longer life. 3.
• the compounds can be sublimated well and without significant decomposition, thereby being easier to process and therefore better suited for use in OLEDs than prior art materials.
• the higher thermal stability may be due to the absence of olefinic double bonds.
• the organic electroluminescent devices show no dependence on the layer thickness of the corresponding layer.
• Example 1 T ⁇ s-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1,2b] fluoren-2-yl) amine a) 6,6,12,12 -Tetramethyl-6,12-dihydro-indeno [1 J 2b] fluorene
• the preparation is analogous to the preparation of 9,9-dimethylfluorene from 6,12-dihydro-indeno [1, 2b] fluorene, dimethyl sulfate and sodium hydroxide solution according to JP 08113542. Yield 86.0% d. Th .; Purity 98% n. 1 H-NMR.
• Ethanol is mixed with 4.9 ml (100 mmol) of hydrazine hydrate and then with 300 mg of freshly prepared Raney nickel. After 2 h under reflux, the mixture is allowed to cool, the solvent is removed in vacuo, the residue is taken up in 1000 ml of warm chloroform, the solution is filtered through silica gel, the clear solution is concentrated to 100 ml and 300 ml of ethanol are added. After standing for 12 h, the colorless crystals are filtered off with suction and then recrystallized twice from chloroform / ethanol. Yield: 8.3 g (23.5 mmol), 93.9% of theory. Th .; Purity: 98% n. 1 H-NMR. g) Bis-2- [8-ethyl-6,6,12,12-tetramethyl-6,12-dehydro-indeno [1,2b] fluoren-8-yl] amine
• Example 4 2- (di (4-methylphenyl) amino) -8-ethyl-dispiro [2,7-di-tert-butyl-9,6 ' -indenofluorene [1,2b] fluoren-12 ' , 9 '' - fluoren] a) dispiro [2,7-di-tert-butyl-fluorene-9,6 '-indenofluoren- [1,2-b] - fluorene-12', 9 'fluorene]
• Tris ⁇ -ethyl-e. ⁇ .i ⁇ .IZ-tetramethyl- ⁇ .iZ-dihyclro-cis-indenofluoreno-yl) amine can be synthesized in analogy to Example 1, with cis-indenofluorene starting compound according to WO 04 / 113412 can be synthesized.
• Tris-2- (8-ethyl-1,6,6,12,12-tetramethyl-6,12-dihydro-cis-indenofluoren-2-yl) -phosphine oxide can be synthesized in analogy to Example 3, wherein cis-indenofluorene can be synthesized from starting compound according to WO 04/113412.
• OLEDs takes place according to a general method according to WO 04/058911, which in individual cases is adapted to the respective circumstances (eg layer thickness variation in order to achieve optimum efficiency or color).
• HIL Hole Injection Layer 20 nm PEDOT (spun from water, supplied by H.C.
• HTM-1 evaporated, synthesized according to Example 1
• HTM Hole transport layer 30 nm NPB (N-naphthyl-N-phenyl-4,4 1 -diaminobiphenyl)
• OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (ILJL characteristics) are determined.
• Table 1 shows the results of some OLEDs (Examples 9 to 15) in which the layer thickness of the hole transport layer (HTM) consists of tris-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydroxy) indeno [1, 2b] fluoren-2-yl) amine, summarized.
• HTM hole transport layer
• NaphDATA is used in Comparative Examples.
• the host material H is 9,10-bis (1-naphthyl) anthracene, as dopant D is used. Both are shown below:
• OLEDs containing the hole transport material according to the invention show tris-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1, 2b] fluoren-2-yl) amine a significantly lower operating voltage than with naphDATA according to the prior art as a hole transport material.
• the operating voltage is independent of the Layer thickness of the hole transport layer. This property is of great advantage for the construction of full-color displays since the thickness of the pixels of the primary colors blue, green and red can be made the same by varying the layer thickness of the hole transport layer.
• the hole transport material according to the invention therefore serves here as a thickness compensation layer, without adversely affecting the electrooptical properties of the device.
• this is not the case for a hole transport material (NaphDATA) according to the prior art:
• a significantly higher operating voltage is required.
• Example 16 Preparation of Phosphorescent OLEDs with Bis-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1 J 2b] -fluoren-2-yl) ketone and Tris 2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1,2b] fluorene-2-yl) phosphine oxide
• the preparation of OLEDs is carried out by a general process according to WO 04/093207 which in individual cases is adapted to the respective circumstances (eg layer thickness variation in order to achieve optimum efficiency or color).
• OLEDs with an emitter layer consisting of the emitter materials according to the invention bis-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1,2b] fluoren-2-yl) ketone and tris-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1,2b] fluoren-2-yl) phosphine oxide.
• OLEDs are produced with the following structure:
• PEDOT 60 nm spun from water, PEDOT supplied by H. C. Starck; poly- [3,4-ethylenedioxy-2,5-thiophene])
• NaphDATA 20 nm (evaporated, NaphDATA purchased from SynTec;
• Emitter layer CBP (evaporated, CBP obtained from ALDRICH and further purified, finally sublimated twice again, 4,4'-bis (N-carbazolyl) biphenyl) (comparative standard)
• ketone-1 bis (9,9'-spirobifluoren-2-yl) ketone
• BCP 10 nm (evaporated, BCP purchased from ABCR, used as received; 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline); not all examples used AlQ 3 10 nm (evaporated, AlQ 3 supplied by SynTec;
• OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A), the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics), and the lifetime are determined. The lifetime is defined as the time after which the initial brightness of 1000 cd / m 2 has fallen to half.
• the triplet emitters and CBP and ketone-1 used are shown below as comparison materials:
• the OLEDs both the comparative examples and the OLEDs with M1 or M2 as matrix material show red emission with comparable
• the service life achieved by using the matrix materials M1 or M2 according to the invention significantly exceeds that of the comparative examples with the matrix material CBP and also exceeds the comparative examples with the matrix material ketone-1.
• OLEDs are carried out according to a general method according to WO 04/058911, which in each case to the particular circumstances (eg layer thickness variation to achieve optimum efficiency or color) is adjusted.
• HIL Hole Injection Layer 20 nm PEDOT (spun from water, supplied by H.C.
• HTM Hole transport layer 50 nm, tris-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1,2b] fluoren-2-yl) amine (abbreviated as HTM -1, evaporated, synthesized according to Example 1)
• HTM Hole Transport Layer
• NPB N-Naphthyl-N-phenyl-4,4 1 -diaminobiphenyl
• Emission Layer EML 30 nm, doped layer of 9,10-bis (1-naphthylanthracene) as host material
• Table 3 shows the results of some OLEDs (Examples 35-38) in which the electron transport layer (ETM) is prepared from bis-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydroc-indeno [ 1, 2b] fluoren-2-yl) ketone and tris-2- (8- ⁇ ⁇ ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1, 2 b] fluoren-2- yl) phosphine oxide, summarized.
• ETM electron transport layer
• the electron transport material according to the invention is used here for thickness compensation layer, without adversely affecting the electrooptical properties of the device. As can be seen from the comparative examples, this is not the case for an electron transport material AIQ 3 according to the prior art.
• OLEDs takes place according to a general method according to WO 04/058911, which in individual cases is adapted to the respective circumstances (eg layer thickness variation in order to achieve optimum efficiency or color).
• HIL Hole Injection Layer
• PEDOT spin-on from water, supplied by HC Starck, Goslar, Germany; poly (3,4-ethylenedioxy-2,5-thiophene)
• Hole Transport Layer HTM 50 nm tris-2- (8-ethyl-6,6,12,12-tetramethyl-6,12-dihydro-indeno [1,2b] fluoro-2-yl) amine (abbreviated as HTM) 1, evaporated, synthesized according to Example 1)
• HTM Hole transport layer
• NPB N-naphthyl-N-phenyl-4,4 1 -diaminobiphenyl
• EML emission layer
• OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) and the power efficiency (measured in Im / W) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics) are determined.
• Table 4 shows the results of some OLEDs (Examples 40 to 42) in which 2- (di (4-methylphenyl) amino) -8-ethyl-dispiro [2,7-di-tert-butyl-fluorene-9,6 ' -indenofluoren- [1, 2b] fluorene-12', 9 "-fluorene] is used as a deep blue emitter and its degree of doping is varied summarized.
• the host material H is 9,10-bis (1-naphthyl) anthracene, is hereinafter shown:
• OLEDs containing the dopants according to the invention show 2- (di (4-methylphenyl) amino) -8-ethyl-dispiro [2,7-di-tert-butyl-fluorene- 9,6'-indenofluorene [1, 2b] fluoren-12 ' , 9 " -fluorene] efficient deep blue emission.

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