WO2006077130A1

WO2006077130A1 - Triarylamine derivatives with space-filling side groups and use thereof

Info

Publication number: WO2006077130A1
Application number: PCT/EP2006/000477
Authority: WO
Inventors: Volker Lischewski; Mirko Tschunarjew; Gerhard Diener; Wolfgang Witt
Original assignee: Sensient Imaging Technologies Gmbh
Priority date: 2005-01-21
Filing date: 2006-01-17
Publication date: 2006-07-27

Abstract

The invention relates to novel triarylamine derivatives, which are provided with at least one special space-filling wing group and to the use thereof as hole transport material in electrophotographic and electroluminescent devices. According to the invention, the organic electroluminescent device is comprised of a layer assembly consisting of a cathode, an electroluminescent layer, which contains an organic compound, and of an anode, the organic compound in the hole transport layer being a novel triarylamine derivative of general formula 1.

Description

Triarylamine derivatives with room-filling side groups and their use

The invention relates to novel triarylamine derivatives which are provided with at least one special space-filling wing group of the general formula 2, and their use as hole transport material in electrophotographic and electroluminescent devices.

Electrophotographic and electroluminescent devices and the use of triarylamine derivatives, including triarylamine di- and tetramers, have long been known. At present, the preferred luminescent material used is tris (-8-hydroxyquinolino) aluminum, the electroluminescence of which has been known since 1965. This metal-chelate complex, optionally doped with coumarin, luminesces green, it also being possible to use beryllium or gallium as metal.

Although initially a relatively high drive voltage of more than 10 volts was required to produce the luminescence effect, the arrangement of an additional hole transport layer between the anode and the luminescent layer reduced the required voltage to less than 10 volts. As hole transport materials, in addition phthalocyanines or biphenylyl-oxadiazole derivatives preferably N, N'-diphenyl-N, N'-bis (m-tolyl) benzidine (TPD) and N ₁ N 'diphenyl-N, N'-di-naphth 1-yl-benzidine (α-NPD) used.

Due to their good charge transport properties, the use of triarylamine derivatives, in particular also of the corresponding dimers, in electro-photographic and electroluminescent applications has already been known for a relatively long time. Specifically, N, N'-bis (-4'-N, N-diphenylaminobiphenylyl)) - N, N'-diphenylbenzidine (EP0650955A1) and N, N'-bis (-4 '(- N-phenyl) N-naphth-1-yl-amino-biphenylyl)) -N, N'-diphenyl-benzidine (JP2000260572) are used alone or in a bilayer association with TPD or α-NPD.

Overall, the life and the efficiency or its time course in the known electroluminescent devices currently do not meet the requirements of the practice and are in need of improvement. Also unsatisfactory are the film-forming properties of the charge transport materials used and their morphological stability within a binder layer. In particular, the inclination of a layer containing said charge transport materials over the service life of an electroluminescent Nescent device or arrangement within the layer to form crystallization centers, depends largely on the glass transition temperature of the materials used. In general, the higher the glass transition temperature, the lower the recrystallization tendency at a given temperature, and the crystallization rate below the glass transition temperature is extremely low. High glass transition temperature compounds therefore allow a high allowable working temperature of the assemblies made therewith.

A high glass transition temperature is strongly favored by the existence of space-filling, sterically demanding groups. WO 03/064373 already discloses triarylamine derivatives which have triarylmethyl or triarylsilyl groups as the wing group and which show elevated glass transition temperatures. However, these compounds contain an aliphatic C or Si atom surrounded by aromatics. Such an aliphatic bond interrupts the conjugated system, which may be expected to negatively impact the redox potential of these compounds; In addition, such aliphatic bonds are chemically relatively unstable and can be expected decomposition phenomena, which can reduce the life of these compounds under the conditions of a functioning OLED device.

The object of the invention is to provide novel compounds which are suitable as charge transport materials and high glass transition temperatures in the range of 100 ⁰ C and show above, preferably in the range greater than 150 ⁰ C, and thus are able to work the area produced with these compounds expand electroluminescent arrangements to temperature ranges from 100 ° C to about 200 ° C while at the same time to enable the lossless application by high vacuum evaporation. In addition, the above-described disadvantages of compounds with aliphatic bonds should be eliminated and decomposition phenomena should be avoided.

According to the invention, the new triarylamine derivatives correspond to the general formula 1

wherein n is an integer of 1-10;

R ¹ , R ² , R ³ and R ^{4 are the} same or different, selected from

Phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, triarylmethyl-aryl, tris-rysilyl-aryl and a biaryl-4'-yl group of the general formula 2,

in the

Ar _{1 is the} same or different and is H and phenyl or phenyl substituted by R ²⁹ to R ³³ ; Ar _{2 is} identical or different and is H and phenyl or phenyl substituted by R ⁹ to R ¹³ ; Ar _{3 is the} same or different and is phenyl or R ¹⁹ to R ²³ -substituted phenyl, where R ⁵ to R ^{33 are} identical or different and are mono- or polysubstituted by H, C ₁ to Ce-alkyl, C ₁ to C ₆ - Alkoxy, dialkylamino (C ₁ to C ₆ ), diarylamino, halogen and / or phenyl, provided that at least one of R ¹ to R ^{4 represents} a biaryl-4'-yl moiety of general formula 2; R ¹ to R ⁴ in the meaning phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl and triarylmethy-aryl by one or a plurality of substituents C ₁ to Cio-alkyl, C ₁ to C ₁₀ alkoxy or halogen may be substituted;

Ar is a structure of formula 3 or 4

3 where n> 1, the structure Ar may be the same or different and wherein Y in formula 3 have the meaning alkenylene or alkynylene (preferably C ₂ -C ₄ ) and x = 0, 1 or 2 and Z in formula 4 is selected from the following structures

wherein R ³⁴ to R ³⁸ , which are the same or different, are H or C- to C ₁₅ alkyl, or R ³⁸ and R ³⁷ or R ³⁶ and R ³⁵ together form a 5- or 6-membered alicyclic or heterocyclic ring and thus together with the five-membered ring to which they are attached form a spiro-ring system, where O, N or S may be the heterocyclic elements; or Ar is a structure of formula 5, 6, 7 or 8 R39

and wherein R ³⁹ to R ^{46 are} identical or different and have the meaning H, phenyl, Ci to C ₅ - alkyl or Ci to C ₃ alkoxy, and the structures of the formulas 3, 4, 5, 6, 7 or 8 with each adjacent nitrogen atoms are connected in any free substitution position.

Preferred compounds are triaryl derivatives of general formula 1, in which at least one of the radicals R ¹ , R ² , R ³ and R ^{4 is} a 2,3,4,5,6-pentaaryl-biaryl-4'yl grouping according to more general Formula 2 is in the form of Formula 2a or a 3,5-diaryl-biaryl-4'-yl grouping according to General Formula 2 in the form of Formula 2b;

2a

2 B

wherein R ⁵ to R ^{33 have} the abovementioned meanings, or R has the meaning of R ⁵ to R ³³ with the above meanings.

Preferred triarylamine derivatives are those of formula 1, wherein n is an integer from 1 to 4, in particular n is 1, 2 or 3, more preferably n is 1 or 3.

Particularly preferred compounds of the formula 1 are those in which at least one radical from R ¹ to R ^{4 is} a 2,3,4,5,6-pentaaryl-4'yl grouping of the formula 2a, where R ⁵ to R ^{33 are} identical or are different and have one or more times the meaning H, alkyl, alkoxy, dialkylamino, diarylamino and halogen, and the radicals R ¹ to R ⁴ in formula 1 are phenyl, biphenylyl, naphthyl, phenanthrenyl, antracenyl, fluorenyl or Triarylmethyl- aryl and may be substituted by one or more substituents C-rC ₆ alkyl, preferably Ci-C ₄ - alkyl, Ci-C ₆ alkoxy, preferably Ci-C ₂ alkoxy, or halogen.

Very particular preference is given to compounds which have at least one radical R ¹ to R ⁴ having a substituted or unsubstituted 2,3,4,5,6-pentaaryl-biaryl-4'-yl grouping of the formula 2a, n = 1 to 4 and R ¹ to R ^{4 are} identical or different and selected from phenyl, biphenylyl, naphthyl or triarylmethyl-aryl, which by one or more substituents, selected from C ₁ -C ₆ -A ^ yI, preferably methyl or tert. Butyl, C ₁ -C ₆ -alkoxy, preferably methoxy, and substituted or unsubstituted 2,3,4,5,6-pentaaryl-biaryl-4'-yl. Particularly preferred compounds of the formula 1 are furthermore those in which at least one radical from R ¹ to R ^{4 is} a 3,5-diaryl-biaryl-4'yl radical of the formula 2b where R ⁵ to R ^{33 are} identical or different and have one or more times the meaning H, alkyl and / or phenyl, and the radicals R ¹ to R ⁴ in formula 1 have the meaning phenyl, Bipheny- IyI, naphthyl, phenanthrenyl, antracenyl, fluorenyl, by one or more substituents Ci-C ₆ alkyl, preferably Ci-C ₄ alkyl, C ₁ -C ₆ -alkoxy, preferably C ₁ -C ₂ - alkoxy, or halogen may be substituted.

Very particular preference is given to compounds of the formula 1 which have, at least with one radical R ¹ to R ^4, a substituted or unsubstituted 3,5-diaryl-biaryl-4'-yl group of the formula 2b, n = 1 to 4 and R ¹ to R ^{4 are} identical or different and are selected from phenyl, biphenylyl, or naphthyl which is substituted by one or more substituents selected from C ₁ -C ₆ -alkyl, preferably methyl or tert. Butyl, C ₁ -C ₆ -alkoxy, preferably methoxy, and substituted or unsubstituted - 3,5-diaryl-biaryl-4'-yl.Z in formula 4 is preferably selected from the following structures

R38 '^ R37 ^ 34

Preferred radicals R ³⁴ to R ³⁸ , which may be identical or different, have the meaning H, C 1 -C ₆ -alkyl or phenyl, in particular methyl or phenyl.

In general formula 3, x is preferably zero or 1. Y in formula 3 is preferably ethene or ethyne.

In a further embodiment of the invention, the radicals R ³⁷ and R ³⁸ together with the carbon atom to which they are attached form a 5- or 6-membered alicyclic or heterocyclic ring and thus form together with the five-membered ring to which they are attached are bonded, a spiro ring system, wherein O, N or S may be the heterocyclic elements. In particular, R ³⁷ and R ^{38 form} a spiroalkane ring.

Preferred radicals R ³⁹ to R ⁴⁶ , which may be identical or different, are hydrogen, methyl or phenyl. The radicals R ⁵ to R ³³ are preferably H, C ₁ -, C ₂ -, C ₃ - or C ₄ -alkyl, in particular methyl or tert. Butyl, Ci-C ₃ alkyloxy, in particular methoxy, dimethylamino, diphenylamino or halogen.

Halogen is preferably fluorine or chlorine.

Further preferred embodiments of the invention are those in which one or two radicals or also all four radicals of R ¹ to R ^{4 represent} a group of formula 2.

Particular preference is given to triarylamine derivatives of the general formula 1 in which n is an integer from 1 to 4, preferably 1, 2 or 3;

R ¹ , R ² , R ³ and R ⁴ , which are the same or different, are

Phenyl, biphenylyl, methylphenyl, naphthyl or triarylmethyl-aryl and substituted or unsubstituted 2,3,4,5,6-pentaaryl-biaryl-4'-yl, where at least one of the radicals R ¹ to R ^{4 is} a 2,3,4 , 5,6-Pentaaryl-biaryl-4'-yl grouping of the general formula 2a, and wherein R ⁵ to R ³³ , which are identical or different, the meaning H, alkyl, alkoxy, dialkylamine, diarylamino or halogen and in which R ¹ to R ^{4 are} each phenyl, biphenylyl, methylphenyl, naphthyl or triarylmethyl-aryl by one or more substituents methyl, tert. Butyl or methoxy may be substituted;

Ar is a structure of formula 3, wherein x is zero or 1 with Y being -CH = CH- or -C≡C-, or of formula 4, wherein, when n> 1, the structure Ar may be the same or different, and wherein Z is selected from the following structures

R38 ' ^N R37 ^ 34

wherein R ³⁴ to R ³⁸ , which are the same or different, are H or C ₁ to C ₆ alkyl, or R ³⁸ and R ³⁷ together form a 5- or 6-membered alicyclic or heterocyclic ring and thus form together with the five-membered ring to which they are attached, a spiro-ring system, wherein O ₁ N or S may be the hetero-cyclic elements.

Particularly preferred triarylamine derivatives of the formula 1 are furthermore compounds, in. where n is an integer 1, 2, 3 or 4; R ¹ , R ² , R ³ and R ^{4 are the} same or different selected from phenyl, biphenylyl, naphthyl, phenanthrenyl, substituted or unsubstituted 3, 5, -Diaryl-biaryl-4'-yl of the formula 2b, wherein R is the said Meaning, wherein at least one of the radicals R ¹ to R ^{4 is} a 3, 5-diaryl-biaryl-4'-yl group of the general formula 2b, and wherein R ¹ to R ⁴ in the meaning phenyl, biphenylyl, naphthyl or Phenanthrenyl by one or more substituents C ₁ to C ₆ alkyl, preferably methyl or tert. Butyl, or Ci to C ₆ alkoxy, preferably methoxy, Ar may represent a structure of the formula 4, where n> 1, the structure Ar may be the same or different and wherein Z is selected from the following structures

wherein R ³⁴ to R ³⁸ , which are the same or different, are H or C ₁ to C ₆ alkyl, preferably methyl or phenyl, or R ³⁸ and R ³⁷ together form a 5- or 6-membered alicyclic or heterocyclic ring and thus together with the five-membered ring to which they are attached form a spiro-ring system, where O, N or S represent the heterocyclic elements.

Further preferred triarylamine derivatives of the formula 1 are compounds in which n is an integer 1, 2, 3 or 4;

Ar represents a structure of formula 3, wherein x = zero;

R ¹ , R ² , R ³ and R ^{4 are the} same or different, selected from phenyl, biphenylyl, naphthyl, phenanthrenyl or substituted or unsubstituted 3, 5, -Diaryl-biaryl-4'-yl of the formula 2b, wherein R is the above Meaning, wherein at least one of the radicals R ¹ to R ^{4 is} a 3, 5-diaryl-biaryl-4'-yl group of the general formula 2b, and wherein R ¹ to R ⁴ in the meaning phenyl, biphenylyl, naphthyl or Phenanthrenyl by one or more substituents Ci to C ₆ -alkyl, preferably methyl or tert. Butyl, or C ₁ to C ₆ alkoxy, preferably methoxy, may be substituted.

The invention further relates to an organic electroluminescent device having at least one hole transport layer and a luminescent layer, wherein at least one hole transport layer contains a triarylamine derivative according to formula 1. A further embodiment of the invention consists in that the organic electroluminescent device has a luminescent layer which contains a triarylamine derivative according to formula 1.

The invention also relates to the use of triarylamine derivatives according to formula 1 as hole transport substance or luminescent substance in an organic electroluminescent device and to the use of triarylamine derivatives according to formula 1 as hole transport substance in an electrophotographic arrangement.

An electrophotographic device is typically constructed as follows: Over an electrically conductive metal layer, which can either be applied to a flexible base or consist of an aluminum drum, there is a charge generation layer, which has the task of exposing positive charge carriers into the charge transport layer upon exposure to inject. The assembly is electrostatically charged to several hundred volts prior to imagewise exposure. Under the influence of the high field strength caused thereby - the thickness of the charge generation and transport layer is typically 15-25 μm - the injected positive charge carriers (electron "holes") migrate to the negatively charged charge transport layer and thus lead to the discharge of the surface into the In the subsequent steps of an electrophotographic cycle, the imagewise charged (or discharged) surface is toned, the toner optionally transferred to a material to be printed, fixed there, and finally removed excess toner and residual charge.

An electroluminescent device consists in principle of one or more charge transport layers, which is arranged between two electrodes, at least one of which is transparent, and contains an organic compound. In this case, at an applied voltage from the metal electrode (usually Ca, Mg or Al, often in combination with silver) due to low work function, electrons and holes from the counter electrode are injected into the organic layer, recombine there and form singlet excitons. These go into a short time in the ground state and emit light.

An additional separation of the electron transport layer and the electroluminescent layer leads to an increase in the quantum yield. At the same time, the electroluminescent layer can now be chosen to be very thin. Due to the interchangeability of the fluorescent Irrespective of its electron transport behavior, the emission wavelength can be adjusted in the entire visible spectral range.

Likewise, a splitting of the hole transport layer into two partial layers and with different composition is possible.

According to the invention, the organic electroluminescent device consists of a layer assembly consisting of a cathode, an electroluminescent layer containing an organic compound, and an anode, wherein the organic compound in the hole transport layer is a triarylamine derivative of general formula 1.

A preferred construction consists of the following layers:

Substrate - transparent anode - hole transport layer - electroluminescent layer - electron transport layer - cathode.

A preferred arrangement is characterized in that between the transparent anode and the glass substrate layer, a dielectric spacer layer and a dielectric mirror, consisting of layer pairs, each having a layer thickness of λ / 4, are arranged.

The cathode, which may consist of Al, Mg, In, Ag or alloys of these metals, has a thickness between 100 and 5000 A. The transparent anode may be made of indium tin oxide (ITO) with a thickness of 1000 - 3000 A, an indium-antimony-tin-oxide coating or a semitransparent gold layer, which is located on a glass substrate.

The electroluminescent layer, tris (-8-hydroxyquinolino) -aluminum according to formula

contains as usual luminescent substance, optionally contains other fluorescent substances such. Substituted triphenylbutadienes and / or 1, 3,4-oxadiazole derivatives, distyrylaryl derivatives, quinacridones, salicylidene-Zn complexes, zinc chelate complexes, DCM-doped aluminum chelate complexes, squarine derivatives, 9,10-bissytrylanthracene derivatives or europium complexes. However, it may also contain exclusively luminescent compounds according to the invention or mixtures thereof with known luminescent substances.

The object of the invention could surprisingly be achieved by the compounds of general formula 1, which have at least one space-filling wing group according to formula 2. These wing groups in the form of substituted or unsubstituted polyphenylbenzene units used according to the invention differ from previously known compounds having wing groups with a trityl carbon in that they contain large and branched conjugated electron systems. Due to the different energy levels caused thereby, it was surprising that such compounds nevertheless exhibit good electron conductor properties and moreover have the advantage of high glass transition temperatures.

Preferred typical examples of triarylamine derivatives of the general formula 1 having at least one wing group according to general formula 2a are in particular compounds having: n = 1 or 3;

Ar = having a structure of formula 3 wherein x = 0 or x = 1 and Y = -CH = CH- or -C = C-; or having a structure of formula 4 wherein R ³⁴ , R ³⁷ and R ^{38 are the} same or different as H or CH ₃ or R ³⁷ and R ³⁸ together form a 6-membered alicyclic ring;

R ¹ to R ⁴ , identical or different, represent a radical selected from among phenyl, biphenyl, methylphenyl, naphthyl, triarylmethyl-aryl and / or a 2,3,4,5,6-pentaaryl-biaryl-4 ' yl moiety of general formula 2a; where one, two or all of the radicals R ¹ to R ^{4 represent} a 2,3,4,5,6-pentaaryl-biaryl-4'-yl grouping of the general formula 2a in which R is the same or different and a or repeatedly has the meaning H and / or CrC ₆ alkyl, preferably H and / or methyl. Particularly preferred are the compounds of the formulas 6 to 20.

10 11

12 13

14 15

16 17

18

19 20

Preferred compounds of the formula I having at least one wing group according to general formula 2b are in particular compounds having: n = 1;

Ar = having a structure of formula 3, where x = 0;

R ¹ to R ⁴ , same or different, are a radical selected from phenyl, biphenylyl, methylphenyl, naphthyl, phenanthrenyl and a 3,5-diaryl-biaryl-4'-yl moiety of the general formula 2b; where one or two of the radicals R ¹ to R ^{4 is} a 3,5-diaryl-biaryl-4'-yl grouping of the general formula 2b, in which R is the same or different and is mono- or polysubstituted H, C ₁ C ₆ -AikyI, and / or phenyl, preferably H and / or methyl.

Particularly preferred compounds of the formula 1 with at least one wing group measure of the general formula 2b are also in particular compounds with: n = 1; Ar = a structure of formula 3, where x = 0; R ¹ and R ^{3 are the} same and are selected from phenyl, biphenylyl, methylphenyl, naphthyl and phenanthrenyl;

R ² and R ^{4 are} each a 3,5-diaryl-biaryl-4'-yl moiety of general formula 2b wherein R is the same or different and is H, C ₁ -C ₆ alkyl or phenyl, preferably H and / or methyl. Preferably, R ² and R ^{4 are} also identical.

Preferred typical examples of triarylamine derivatives according to the general formula 1 having at least one wing group of the general formula 2b are the compounds of the formulas 22 to 27.

22 23

24 25

All compounds were prepared by methods known per se, for. B. the Ullmann synthesis [D. Kagaku: Organic Chemistry, 16, 52 (1959); AH Lewin, T. Cohen: Tetrahedron Letters 1965, 4531] or by noble metal catalytic reactions [SL Buchwald et al., Angew. Chem. Int. Ed. Engl., 34 ( ¹² ) _> 1348 (1995); JF Hartwig et al., Tetrahedron Letters, 36 (21), 3609 (1995)] starting from suitable primary and secondary amines and dihalo-phenylene, dihalobiphenylene, dihalogen-dibenzofurans, dihalodibenzothiophenes, dihalocarbazoles, dihalodibenzosilolen or substituted or unsubstituted or substituted dihalo-hexaphenylbenzenen starting from suitable tertiary halogen biphenyl-4-yl-amines and arylenediamine or optionally hetero-analogous benzidine derivatives or optionally substituted diamino-hexaphenylbenzenen synthesized.

In "Ullmann synthesis" is understood to mean a condensation reaction, halides in the Arylhaloge-, preferably Aryljodide at temperatures of 100-300 ⁰ C under the catalytic use of Cu or Cu-bronze with appropriate substrates to the C- or N-Arylierungsprodukten react, whereby functionally substituted aryl halides can be reacted with appropriate selective protection of sensitive groups.

When two successive hole transport layers are used, at least one layer contains triarylamine derivatives according to formula 1, preferably compounds 6-20 or 22-27.

When using an additional electron transport layer contains these known electron transport materials such. Bis (-aminophenyl) -1, 3,4-oxadiazoles, triazoles or dithionene derivatives.

The use of the preferred hole transport materials according to formulas 6 - 20 and 22 to 27 led to a high dark conductivity of the layers and thus to a low Control voltage of less than 6 volts, resulting in a reduction of the thermal load of the device. At the same time, the hole transport materials used according to the invention have a high glass transition temperature of more than 150 ^° C. and thus also at higher working temperatures have a very low tendency to recrystallise in the layer. Because of this, as well as due to the chemical structure of these relatively large molecules, layers made from these materials with and without binder content are very stable, allowing for the use of the common technique of "spin coating".

Particularly noteworthy is the property of the new compounds to exhibit no molecular changes in the process of layer production by high vacuum evaporation despite complicated molecular structure.

As a further advantage of these new compounds, it can be expected that decomposition phenomena during production, cleaning, during vapor deposition as well as under electrical and thermal stress are significantly minimized

Deposited layers are free from structural defects and have a high transparency in the visible spectral range. The properties mentioned make it possible to produce new organic electroluminescent devices with high luminous efficacy (> 10,000 cd / m.sup.2) with simultaneously significantly improved long-term stability (> 10,000 hours).

The following examples serve to illustrate the present invention, but are not intended to limit it in any way:

Example 1 :

Preparation of N, N'-bis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -N, N'-biphenyl-4-yl-benzidine (Formula 8)

A glass apparatus, consisting of a 500 ml three-necked flask, magnetic stirrer, thermometer and gas inlet tube is provided with a reflux condenser, is 2 hours. Annealed at 120 ⁰ C, remove the bound to the glass walls of water.

The apparatus is purged with nitrogen and charged with 160 ml of Na-dried and N 2 -purged o-xylene while further passing nitrogen through it. With stirring, 6.3 mg of palladium acetate and 5.2 ml of a 1% solution of tri-tert-butylphosphine in dry o-xylene are added to form the catalyst complex. To the resulting clear yellow solution are added 12.9 g of sodium tert-butoxide, 13.1 g of 4,4'-dibromo-biphenyl and 59.0 g of N- (2, 3,4,5, 6-pentaphenyl) biphenyl-4'-yl) -N-biphenyl-4-yl given amine. The entire apparatus is evacuated three times and flooded with nitrogen (securiert).

While continuing to maintain a nitrogen atmosphere and with stirring, the contents of the flask are heated to 12O ⁰ C in an oil bath. After about 30 minutes, the excretion of NaBr begins. The batch is allowed to react for 3 hours at 12O ⁰ C.

Thereafter, the contents of the flask are diluted with toluene to twice its volume and then poured with stirring into ten times the amount of methanol. The crude product precipitates and can be filtered off. The formed NaBr is soluble in methanol. For purification, the crude product is reprecipitated from xylene with the addition of 10% silica gel and then recrystallized again from N-methylpyrrolidone. Finally, the product is sublimed in maximum vacuum (<10-5 torr). About 30 g of pure N, N'-bis (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -N, N'-biphenyl-4-yl-benzidine are obtained.

Example 2 Preparation of N, N'-bis (N-phenyl-N- (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -aminostilbene (Formula 12)

In the same apparatus as in Example 1 and in an analogous procedure, starting from 160 ml of Na dried over Na and purged with N2 o-xylene, 6.3 mg palladium acetate and 5.2 ml of a 1% solution of tri-tert. Butylphosphine in dry o-xylene, 12.9 g of sodium tert-butoxide, 52.6 g of N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) ~ amine and 14.2 g of 4,4'-Dibromstilben produced in the course of 7 hours at 120 ⁰ C, the crude product. The flask ion content is diluted to twice its volume with hot toluene and then poured with stirring into ten times the amount of methanol. The crude product precipitates and can be filtered off. For purification, the crude product of xylene / dodecane is reprecipitated with addition of 10% silica gel and then recrystallized from DMF again. Finally, the product is sublimed in maximum vacuum (<10-5 torr). About 35 g of pure N, N'-bis (N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -aminostilbene are obtained.

Example 3:

Preparation of 2,7-bis (-N-phenyl-N- (2,3,3,5, β-pentaphenyl-biphenyl---yiyamino),, 9-dimethyl-fluorene (Formula 16)

120 ml of anhydrous o-xylene, 52.6 g of N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -amine and 14.8 g of 2,7-dibromo 9,9-dimethylfluorene is prepared using 12.9 g of sodium tert-butoxide as the dehydrating base, 12.6 mg of palladium acetate and 10.4 ml of a 1% strength Solution of tri-tert-butylphosphine as a catalyst in an apparatus according to Example 1 and according to the procedure given there reacted. Isolation, workup and purification of the reaction product is also carried out analogously to Example 1, wherein the dodecane given there is replaced by a paraffinic branched C 12 hydrocarbon (ISOPAR G ™, Exxon).

About 25 g of purified 2,7-bis (-N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -amino) -9,9-dimethyl-fluorene are obtained ,

Example 4: Preparation of N, N'-bis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -N, N'-diphenyl-benzidine (Formula 6)

4.3 g of 1- (4'-bromophenylyl) -2,3,4,5,6-pentaphenylbenzene, 1.18 g of N, N'-diphenylbenzidine are dissolved in 40 ml of anhydrous o-xylene with 0.81 g of Na tert-butoxide as the base and 1.05 mg of palladium acetate and 0.87 ml of a 1% solution of tri-tert-butylphosphine as a catalyst according to Example 3 were reacted.

Isolation, workup and purification of the reaction product is carried out analogously to Example 1. After sublimation in a maximum vacuum (> 10-5 Torr) gives 2 g of highly pure N, N'-bis (2,3,4,5,6-pentaphenyl-biphenyl -4'-yl) -N, N'-diphenyl-benzidine.

Analogously, compounds 7, 9 to 11, 13 to 15, 17 to 20 were prepared.

The synthesized compounds 6 to 20 have the following glass transition temperatures. This was determined by differential scanning calorimetry:

Example 5:

Electroluminescent arrangement

On a glass substrate, which is coated with an indium tin oxide electrode (ITO), a coating is applied in ultra-high vacuum (10-8 hPa). It consists of a 55 nm thick hole injection layer, consisting of the known starburst compound 21,

21

a 5 nm thick hole transport layer of N, N'-bis (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -N, N'-diphenyl-benzidine, as obtained according to Example 4 , a 30 nm electron transport and emission layer of the chelate complex AIQ3. The layers are deposited at growth rates of about 0.1 nm / s. Subsequently, a 90 nm thick aluminum cathode is applied.

To determine the electroluminescent characteristic, a voltage is applied between the ITO electrode and the aluminum electrode. The power of the emitted light was measured with a large area Si photodiode mounted directly below the glass slide. The following results were achieved: Turn-on Voltage (1 cd / m2) 2.95 Volt max. Luminance (15V) 34100 cd / m2

Photometry Efficiency (100 cd / m2) 2.20 cd / A Lum. Efficiency (100 cd / m2) 1.10 cd / W ext. Quantum Efficiency 0.62%

Example 6:

The electroluminescent device is prepared in the same layer arrangement as in Example 5, but will be in the hole transport layer, the 2,7-bis (N-phenyl-N- (2,3,4,5,6-pentaphenyl-biphenyl-4 ^I - yl) -amino) -9, 9-dimethyl-fluorene used according to Example 3. The following results were achieved:

Turn-on Voltage (1 cd / m2) 3.05 volts max. Luminance (15V) 27800 cd / m2 Photometry Efficiency (100 cd / m2) 2.10 cd / A Lum. Efficiency (100 cd / m2) 1, 18 cd / W ext. Quantum Efficiency 0.33%

Example 7:

Preparation of N, N'-bis (5'φhenyl- [1, 1 '; 3 \ 1''] terphenyl-4-yl) -N, N-diphenyl ^{l-biphenyl-4,4'} ~ diamine (formula 22)

A glass apparatus, consisting of a 500 ml three-necked flask equipped with reflux condenser, magnetic stirrer, thermometer and gas inlet tube, is baked for 2 hours at 120 ° C. to remove the water bound to the glass walls. The apparatus is purged with nitrogen or argon and - with further passing of inert gas - with 160 ml of Na-dried and purged with inert gas o-xylene charged. With stirring, 6.3 mg of palladium acetate and 5.2 ml of a 1% solution of tri-tert-butylphosphine in dry o-xylene are added to form the catalyst complex.

To the resulting clear yellow solution are added 12.9 g of sodium tert-butoxide, 18.84 g of N.NT-diphenylbenzidine and 44.24 g of 1- (4-bromophenyl) -3,5-diphenyl-benzene. The entire charged apparatus is evacuated three times and flooded with inert gas (securiert). While continuing to maintain a protective gas atmosphere and stirring, the contents of the flask are heated to 120 ^° C. in an oil bath. After about 30 minutes, the excretion of NaBr begins. The batch is allowed to react for 3 hours at 12O ⁰ C. Thereafter, the contents of the flask are diluted with toluene to twice its volume and then poured with stirring into ten times the amount of methanol. The crude product precipitates and can be filtered off. The formed NaBr is soluble in methanol. For purification, the crude product is reprecipitated from xylene with the addition of 10% silica gel and then recrystallized again from N-methylpyrrolidone. Finally, the product is sublimed in maximum vacuum (<10-5 torr). About 30 g of pure N, N'-bis- (5'-phenyl- [1,1 ', 3', 1 "] terphenyl-4-yl) -N, N'-diphenyl-biphenyl-4 are obtained, 4'-diamine The glass transition temperature T ₉ is 164 ° C.

Example 8

Preparation of N, N'-bis- (5'-phenyl- [1,1 ', 3', 1 "] terphenyl-4-yl) -N, N'-di-p-tolylbiphenyl-4,4 '- diamine (formula 23)

In the same apparatus as in Example 7 and in an analogous procedure, starting from 160 ml of Na dried over Na and purged with N2 o-xylene, 6.3 mg palladium acetate and 5.2 ml of a 1% solution of tri-tert. butylphosphine in dry o-xylene, 12.9 g of sodium tert-butoxide, 20.41 g of N, N'-di-p-tolylbenzidine and 44.24 g of 1- (4-bromophenyl) -3,5- diphenyl-benzene in the course of 4 hours at 120 ⁰ C, the crude product prepared.

The flask ion content is diluted to twice its volume with hot toluene and then poured with stirring into ten times the amount of methanol. The crude product precipitates and can be filtered off. For purification, the crude product is reprecipitated from xylene with the addition of 10% silica gel and then recrystallized once again from DMF / NMP mixture 1: 1. Finally, the product is sublimed in maximum vacuum (<10-5 torr). About 35 g of pure N, N'-bis- (5'-phenyl- [1,1 ', 3', 1 "] terphenyl-4-yl) -N, N'-di-p-tolyl- biphenyl-4,4-diamine ^l having a glass transition temperature T ₉ of 162 ⁰ C.

Example 9:

Preparation of N, N'-bis- (5'-phenyl- [1,1 ', 3', 1 "] terphenyl-4-yl) -N ₁ N'-di-phenanthren-9-ylbiphenyl-4 '4'-diamine (formula 27)

160 ml of anhydrous o-xylene, 55.7 g of (5'-phenyl- [1, 1 ', 3', 1 "] terphenyl-4" -yl) -phenanthren-9-yl-amine and 17.5 g of 4 , 4'-Dibromobiphenyl are prepared using 12.9 g of sodium tert-butoxide as the dehydrating base, 12.6 mg of palladium acetate and 10.4 ml of 1% strength Solution of tri-tert-butylphosphine as a catalyst in an apparatus according to Example 7 and according to the procedure given there reacted. Isolation, work-up and purification of the reaction product are likewise carried out analogously to Example 1, wherein the XyIoI indicated there is replaced by mesitylene. About 25 g of purified N, N'-bis- (5'-phenyl- [1 J ', 3] -terphenyl-4-yl) -N, N'-di-phenanthren-9-yl-biphenyl-4 are obtained, 4'-diamine whose glass transition temperature T _{9 has} a value of 187 ° C.

Analogously, compounds 24 to 26 were prepared. The synthesized compounds 22 to 27 have the following glass transition temperatures. This was determined by differential scanning calorimetry:

Example 10:

Electroluminescent arrangement

21

a 5 nm thick hole transport layer of N, N'-bis (5'-phenyl- [1, 1 '; 3 ^I, 1 "] terphenyl-4-yl) - N, N'-di-phenanthrene-9-yl -biphenyl-4,4'-diamine, as obtained according to example 9, of a 30 nm thick electron transport and emission layer of the chelate complex AIQ 3. The layers are deposited at growth rates of about 0.1 nm / s Thick aluminum cathode applied.

To determine the electroluminescent characteristic, a voltage is applied between the ITO electrode and the aluminum electrode. The power of the emitted light was measured with a large area Si photodiode mounted directly below the glass slide.

The following results were achieved:

Turn-on Voltage (1 cd / m ² ) 2.85 volts max. Luminance (13V) 51100 cd / m ²

Photometry Efficiency (100 cd / m ² ) 2.40 cd / A

Lum. Efficiency (100 cd / m ² ) 1.40 cd / W ext. Quantum Efficiency 0.71%

Claims

claims

1. Triarylamine derivatives of the general formula 1

wherein n is an integer of 1-10;

R ¹ , R ² , R ³ and R ^{4 are the} same or different, selected from

Phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, triarylmethylaryl, triarylsilyl-aryl and a biaryl-4'-yl grouping of the general formula 2,

in the

Ar-i, identical or different, is H and phenyl or phenyl which is substituted by R ²⁹ to R ³³ ; Ar _{2 is} identical or different and is H and phenyl or phenyl substituted by R ⁹ to R ¹³ ; Ar _{3 is,} identically or differently, H and phenyl or phenyl which is substituted by R ¹⁹ to R ²³ , R ⁵ to R ^{33 being} identical or different and having one or more times the meaning H, C ₁ -C ₆ -alkyl, C ₁ - C ₆ alkoxy, dialkylamino (C ₁ -C ₆ ), diarylamino, halogen and / or phenyl; with the proviso that at least one of R ¹ to R ^{4 is} a biaryl-4'-yl moiety of general formula 2;

and wherein R ¹ to R ⁴ in the meaning phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, triarylmethyl-aryl be substituted by one or more substituents C ₁ to C ₁₀ alkyl, C ₁ to C ₁₀ -alkoxy or halogen can;

Ar represents a structure of formulas 3 or 4,

or

3 4

where n> 1, the structure Ar may be the same or different and wherein Y has the meaning alkenylene or alkynylene and x = 0, 1 or 2 may be and wherein Z is selected from the following structures

R38 'v _R 37 R36 / ^ R35 ^ ₃₄

wherein R ³⁴ to R ³⁸ , which are the same or different, are H or C ₁ to C ₁₅ alkyl, or R ³⁸ and R ³⁷ or R ³⁶ and R ³⁵ together form a 5- or 6-membered alicyclic or heterocyclic Ring and thus together with the ring to which they are attached form a spiro-ring system, where O, N or S may be the heterocyclic elements; or Ar is a structure of formula 5, 6, 7 or 8 is R39

and wherein R ³⁹ to R ⁴⁶ which are identical or different, is H, phenyl, Ci to C _δ -alkyl or C ₁ to C have ₃ alkoxy, and the structures 3, 4, 5, 6, 7 or 8 are connected to the respective adjacent nitrogen atoms in any free substitution position.

Triarylamine derivatives of the formula 1 according to claim 1, characterized in that at least one of the radicals R ¹ to R ^{4 is} a 2,3,4,5,6-pentaaryl-biaryl-4'-yl grouping according to general formula 2 in the form from formula 2a

2a is where R ⁵ to R ^{33 have} the abovementioned meanings.

3. triarylamine derivatives of the formula 1 according to claim 1 or 2, characterized in that at least one of the radicals R ¹ to R ^{4 is} a 2,3,4,5,6-pentaaryl-biaryl-4'-yl grouping according to formula 2a and R ⁵ to R ^{33 denote,} identically or differently, the meaning H, alkyl,

Alkoxy, dialkylamino, diarylamino or halogen, and R ¹ to R ⁴ in formula 1 in the meaning phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, triarylmethyl-aryl by one or more substituents C ₁ to C ₆ alkyl , preferably C ₁ to C ₄ alkyl; C ₁ to C ₆ alkoxy, preferably C ₁ to C ₂ alkoxy, or halogen may be substituted.

4. triarylamine derivatives of the formula 1 according to any one of claims 2 or 3, characterized in that n is an integer from 1 to 4; R ¹ , R ² , R ³ and R ^{4 are the} same or different selected

Phenyl, biphenylyl, naphthyl, triarylmethyl-aryl or substituted or unsubstituted 2,3,4,5,6-pentaaryl-biaryl-4'-yl, where at least one of the radicals R ¹ to R ^{4 is} a 2,3, 4,5,6-Pentaaryl-biaryl-4'-yl

Grouping the general formula 2a, wherein R ⁵ to R ^33, identically or differently, have the meaning H, alkyl, alkoxy, dialkylamino, diarylamino or halogen, and in which R ¹ to R ^{4 are} each phenyl, biphenylyl or naphthyl or triarylmethyl-aryl by one or more substituents C ₁ to C ₆ alkyl, preferably methyl or tert. Butyl, or Ci to C ₆ alkoxy, preferably methoxy, may be substituted;

Ar is a structure of formula 3 wherein x is zero, or of formula 4, where n> 1, the structure Ar may be the same or different and Z is selected from the following structures

R38 '-R37 | J, 34

wherein R ³⁴ to R ^{38 are the} same or different from H or C ₁ to C ₆ alkyl, or R ³⁸ and R ³⁷ together form a 5- or 6-membered alicyclic or heterocyclic ring and thus form together with the five-membered ring they are bonded, a spiro ring system, wherein O, N or S may be the heterocyclic elements.

5. triarylamine derivatives of the formula 1 according to one of claims 1 to 4, characterized in that n = 1 or 3, preferably 1.

6. triarylamine derivatives according to one of claims 1 to 5, characterized in that the radicals R ⁵ to R ^{33 is} H, methyl, methoxy, dimethylamino, diphenylamino or halogen, preferably H or methyl.

7. triarylamine derivatives according to one of claims 1 to 6, characterized in that halogen has the meaning fluorine or chlorine.

8. triarylamine derivatives according to claim 1, characterized in that R ³⁴ to R ^{38 have} the meaning of methyl or phenyl.

9. triarylamine derivatives of the formula 1 according to claim 1, characterized in that at least one of the radicals R ¹ to R ^{4 is} a 3,5-diaryl-biaryl-4'-yl grouping of the general formula 2 in the form of formula 2b represents

2 B

wherein R is the meaning of R to R with the o.g. Has meanings.

10. triarylamine derivatives of the formula 1 according to claim 9, characterized in that at least one of the radicals R ¹ to R ^{4 is} a 3,5-diaryl-biaryl-4'-yl grouping of the general formula 2b and R is the same or is different and has one or more times the meaning H, C ₁ -C ₆ -AlkVl and / or phenyl, and wherein R ¹ to R ⁴ in formula 1 in the meaning phenyl, biphenylyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl by one or more substituents C ₁ to C ₆ alkyl, preferably C ₁ to C ₄ alkyl; C ₁ to C ₆ alkoxy, preferably C ₁ to C ₂ alkoxy, or halogen may be substituted.

11. triarylamine derivatives of formula 1 according to any one of claims 9 or 10, characterized in that n is an integer from 1 to 4; R ¹ , R ² , R ³ and R ^{4 are the} same or different, selected from phenyl, biphenylyl,

Naphthyl, phenanthrenyl, substituted or unsubstituted 3, 5, -diaryl-biaryl-4'-yl of the formula 2b, wherein R is as defined in claim 10 g. Meaning, wherein at least one of the radicals R ¹ to R ^{4 is} a 3, 5-diaryl-biaryl-4'-yl group of the general formula 2b, and wherein R ¹ to R ⁴ in the meaning phenyl, biphenylyl, naphthyl or Phenanthrenyl by one or more substituents Ci to C ₆ -alkyl, preferably methyl or part. Butyl, or Ci to C ₆ alkoxy, preferably methoxy, may be substituted,

Ar represents a structure of formula 4, where n> 1, the structure Ar may be the same or different and Z is selected from the following structures

R38 ' ^N R37 ^ 34

12. triarylamine derivatives of the formula 1 according to claim 9, characterized in that n is an integer from 1-4 is;

Ar represents a structure of formula 3, wherein x = zero;

R ¹ , R ² , R ³ and R ^{4 are the} same or different, selected from phenyl, biphenylyl, naphthyl, phenanthrenyl or substituted or unsubstituiert.es 3, 5, -Diaryl-biaryl-4'-yl of the formula 2b, wherein R has the abovementioned meaning, where at least one of the radicals R ¹ to R ^{4 is} a 3, 5-diaryl-biaryl-4'-yl grouping of the general formula 2b, and in which R ¹ to R ^{4 are} phenyl, biphenylyl, Naphthyl or phenanthrenyl by one or more substituents C ₁ to C ₆ alkyl, preferably methyl or tert. Butyl, or Ci to C ₆ alkoxy, preferably methoxy, may be substituted.

13. triarylamine derivatives according to any one of claims 9 to 12, characterized in that n is 1 or 3, preferably 1, has.

14. triarylamine derivatives according to one of Ansprüchw 9 to 13, characterized in that

Halogen has the meaning fluorine or chlorine.

15. triarylamine derivatives according to any one of claims 9 to 14, characterized in that n = 1;

Ar = represents a structure of formula 3 with x = 0;

R ¹ to R ^{4 are} identical or different and selected from phenyl, biphenylyl,

Methylphenyl, naphthyl, phenanthrenyl and a 3,5-diaryl-biaryl-4'-yl group of the general formula 2b, wherein one or two of the radicals R ¹ to R ^{4 is} a 3,5-diaryl-biaryl-4'-yl Represent grouping of the general formula 2b, in which R is the same or 4'-yl grouping of the general formula 2b, in which R is the same or different and has the meaning H, C ₁ -C ₆ -Alkyl and / or phenyl, preferably H and / or methyl.

16. triarylamine derivatives according to claim 15, characterized in that

R ¹ and R ^{3 are} identical and selected from phenyl, biphenylyl, methylphenyl,

Naphthyl and phenanthrenyl; and

R ² and R ^{4 are} identical and each represents a 3,5-diaryl-biaryl-4'-yl moiety of the general formula 2b.

17. Compounds according to one of claims 1 to 16

N, N'-bis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -N, N'-diphenyl-benzidine;

N, N'-bis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -N, N'-dinaphth-1-yl-benzidine;

N, N'-bis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -N, N'-biphenyl-4-yl-benzidine; N, N'-bis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -N, N'-di- (4-methylphenyl) -benzidine;

N, N'-bis (2, 3, 5, 6-tetraphenyl-4- (4-methylphenyl) -biphenyl-4'-yl) -N, N'-diphenylbenzidine;

N, N'-bis- (3,5-diphenyl-2,6-di (-4-methoxyphenyl) -4- (4-methylphenyl) -biphenyl-4'-yl) -

N, N'-diphenylbenzidine;

4,4'-bis - ((N-phenyl-N- (2,3,3,5,6-pentaphenyl-biphenyl-4'-yl)) -amino) -diphenylethylene; 4,4'-bis - ((N-phenyl-N- (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl)) -amino) -diphenylacetylene;

N- (2,3,4,5,6-pentaphenyl-biphenyl-4'-yl) -N- (4-methylphenyl) -N'-phenyl-N'-naphth-1-yl-benzidine;

N- (2, 3, 4, 5, 6-penta- (4-methylphenyl) -biphenyl-4'-yl) -N-phenyl-N'-diphenylbenzidine; 2, 7-bis (-N-phenyl-N- (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -amino) -9,9-dimethyl-fluorene;

N, N, N ', N'-tetrakis (2, 3, 4, 5, 6-pentaphenyl-biphenyl-4'-yl) -benzidines; fyQ-dimethyl-N ^ '- bis-ft'-tß'.S' ^ '^' ß'-pentaphenyl-biphenyl ^ -y-O-phenyl-amino] - biphenyl-4-yl} -N, N'-diphenyl -9H-fluorenene-2, 7-diamine; 1,1-Bis- (4- (N- (4-methyl-phenyl) -N- (2 ', 3', 4 ', 5', 6'-pentaphenyl-biphenyl-4-yl) -amino) -phenyl ) cyclohexanes;

N, N'-bis (2, 3, 4, 5, 6-pentaphenylbiphenyl-4'-yl) -N, N'-di- (4- (t- (4-methylphenyl) -methyl) - phenyl) -benzidine;

N ^ '- bis-f''-phenyl-fH''r''-terphenyl-y-O-N'-diphenyl-biphenyl-A'-diamine; N, N'-bis- (5'-phenyl- [1,1 ', 3 \ 1 "] terphenyl-4-yl) -N, N'-di-p-tolyl-biphenyl-4,4'-diamine ; N, N'-Bi9- (5 '- (4-methylphenyl) -4 "-methyl-1,1', 3 ', 1"] -terphenyl-4-yl) -N, N'-diphenyl-biphenyl-4 , 4'-diamine;

N, N'-B! S- (5'-phenyl- [1,1 ', 3 \ 1 "] terphenyl-4-yl) -N, N'-di- (biphenyl-4-yl) -biphenyl- 4,4'-diamines; N, N'-bis (5'-phenyl- [1,1 ', 3'-imidophenyl-4-yl) -N, N'-di- (naphth-1-yl) -biphenyl -4,4'-diamine;

N, N'-bis- (5'-phenyl- [1,1 ', 3', 1ψψ-phenyl-4-yl) -N, N'-di-phenanthren-9-yl-biphenyl-4,4'- diamine.

18. An organic electroluminescent device having at least one hole transport layer and a luminescent layer, characterized in that at least one hole transport layer contains at least one triarylamine derivative according to one of claims 1 to 17.

19. An organic electroluminescent device according to claim 18, characterized in that the luminescent layer contains at least one triarylamine derivative according to one of claims 1 to 17.

20. Use of triarylamine derivatives according to one of claims 1 to 17 as a hole transport substance or luminescent substance in an organic electroluminescent device.

21. Use of triarylamine derivatives according to one of claims 1 to 17 as Lochtransportsubstanz in an electrophotographic arrangement.