WO2016096069A1

WO2016096069A1 - Compounds for electronic devices

Info

Publication number: WO2016096069A1
Application number: PCT/EP2015/002264
Authority: WO
Inventors: Oliver KAUFHOLD; Stefan RIEDMUELLER
Original assignee: Merck Patent Gmbh
Priority date: 2014-12-18
Filing date: 2015-11-11
Publication date: 2016-06-23
Also published as: DE112015005644A5

Abstract

The present application relates to a compound of formula (I), which is suitable for use as a functional material in an electronic device, in particular as an emitter material in an organic electroluminescent device.

Description

Connections for electronic devices

The present invention relates to a compound of a formula (I). The compound is suitable for use as a functional material in an electronic device, in particular in an organic device

Electroluminescent device (OLED). Furthermore, the invention relates to certain embodiments of electronic devices

containing the compound of the formula (I) and also processes for the preparation of the compound of the formula (I). The term electronic device is used according to the

The present invention generally relates to electronic devices containing organic materials. Preferably, these are understood as meaning OLEDs and some other embodiments of electronic devices containing organic materials disclosed in the application later.

The general structure and the functional principle of OLEDs is known to the person skilled in the art and is described inter alia in US Pat. No. 4,539,507, in US Pat. No. 5,151,629, in EP 0676461 and in WO 98/27136.

With regard to the performance data of the electronic devices, further improvements are required, in particular to enable a wide commercial use of the electrical devices, such as in displays or as light sources. In this

The lifecycle, the efficiency and the

Operating voltage of the electronic devices and the realized color values of particular importance.

When using conventional white light sources and monitors is currently the total useful life of the blue-emitting

Limiting component. Therefore, with blue-emitting OLEDs, there is an improvement potential with respect to the life of the electrical devices and the color values of the emitted light. An important starting point for achieving the mentioned improvements is the selection of the emitter connection used in the electronic device.

In the prior art, a plurality of compounds are known as blue-fluorescent emitter compounds, in particular arylamines having one or more fused aryl groups and / or indenofluorene groups. Examples of these are the pyrene-arylamines disclosed in US 5153073. Further examples of arylamine emitters are those in the

WO 2008/006449 disclosed benzoindenofluoreneamines.

Furthermore, US 2012/0161615 describes the use of fluorenamines which have aromatic groups fused to the fluorene system. The compounds described are used as fluorescent emitters, but show mainly green and only a small green-blue emission. In US 2012/0161615 no blue emission is described.

In addition, in EP 1950195 a variety of aromatic

Amine derivatives, including in particular a

5,6,11,12-Tetrahydrochrysene derivative which substituted two

Has diphenylamino groups. The 5,6,11,12-tetrahydrochrysene derivative is used as a fluorescent emitter in an OLED having a blue emission. However, in order to produce a blue emission, the electronic device mentioned in EP 1950195 requires a high level

Operating voltage of 6.5 V. In order to ensure use of the electronic device in displays or light sources, it is advantageous to increase the efficiency of said electronic device. In summary, therefore, the technical task is blue

to provide fluorescent emitters. Furthermore, the object is preferably to provide compounds with which a high

Power efficiency, a long life and a blue emission of the electronic device can be achieved, in which the compounds are introduced. Surprisingly, it has now been found that substituted benzoindenoinden compounds have blue color coordinates and thereby solve the technical problem presented above. Blue color coordinates at

Emitter connections are highly desirable for use in displays and lighting applications and are also highly desirable for matching the color impressions of the different colors in one

Display or in a lighting application.

The invention thus provides a compound of a formula (I)

Formula (I) where: is the same or different CR ¹ or N at each occurrence; is equal to C; is the same or different at each occurrence BR ² , C (R ² ) 2

C (R ² ) ₂ -C (R ² ) ₂₎ -R ² C = CR ² -, -R ² C = N- ₍ Si (R ² ) _2> Si (R ² ) ₂ -Si (R) ₂

O, S, S = O, SO ₂ , NR ² , PR ² or P (= O) R ² ;

R ¹ is the same or different at each occurrence H, N (R ² ) ₂ , D, F, Cl, Br, I, C (= O) R ³ , CN, Si (R ³ ) ₃ , P (= 0) (R ³ ) ₂ , S (= O) R ³ , S (= O) ₂ R ³ , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C Atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 Ring atoms or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

the abovementioned groups may each be substituted by one or more radicals R ³ , where

one or more CH 2 groups in the abovementioned groups by -R ³ C =CR ³ -, -C =C-, Si (R ³ ) ₂₎ C =O, C =NR ³ ,

-C (= O) O-, -C (= O) NR ³ -, NR ³ , P (= O) (R ³ ), -O-, -S-, SO or SO ₂ may be replaced, wherein

one or more H atoms in the above groups may be replaced by D, F, Cl, Br, I or CN, and wherein

two or more radicals R may be linked together and form a ring; is identical or different at each occurrence H, D, F, Cl, Br, I, C (= O) R ³ , CN, Si (R ³ ) _{3 L} N (R ³ ) ₂ , P (= O) (R ³ ) ₂ , S (OO) R ³ , S (OO) ₂ R ³ , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 ring atoms or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

one or more CH 2 groups in the abovementioned groups by -R ³ C =CR ³ -, -CEC-, Si (R ³ ) ₂ , C =O, C =NR ³ ,

-C (= O) O-, -C (= O) NR ³ -, NR ³ , P (= O) (R ³ ), -O-, -S-, SO or SO 2 may be replaced, wherein

two or more radicals R ^{2 may} be linked together and form a ring; is identical or different at each occurrence H, D, F, Cl, Br, I, C (= O) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= O) (R ⁴ ) ₂ , S (= O) R ⁴ , S (= O) ₂ R ⁴ , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 ring atoms or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

the abovementioned groups can each be substituted by one or more radicals R ⁴ , where

one or more Ch groups in the abovementioned groups are represented by -R ⁴ C =CR ⁴ - ₍ -CEC-, Si (R) ₂₎ C =O, C =NR ⁴ ,

-C (= O) O-, -C (= O) NR ⁴ -, NR ⁴ , P (= O) (R ⁴ ), -O-, -S-, SO or SO ₂ may be replaced, wherein

two or more radicals R ^{3 may} be linked together and form a ring;

R ⁴ is the same or different at each occurrence H, D, F, Cl, Br, I, CN, a straight-chain alkyl or alkoxy group having 1 to 20

C atoms, a branched or cyclic alkyl or

Alkoxy group having 3 to 20 carbon atoms, an alkenyl or

Alkynyl group having 2 to 20 carbon atoms, an aromatic or heteroaromatic ring system having 5 to 30 ring atoms or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein two or more radicals R ^{4 may} be linked together and form a ring. The following are general definitions for chemical groups in the context of the present application.

An aryl group for the purposes of this invention contains 6 to 60 aromatic ring atoms. A heteroaryl group in the context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom. The heteroatoms are preferably selected from nitrogen (N), oxygen (O), sulfur (S), silicon (Si) and / or phosphorus (P), and are particularly preferably selected from nitrogen (N), oxygen (O) and / or sulfur (S). This is the basic definition. In the description of the present invention, other preferences will be made indicated, for example, in terms of the number of aromatic

Ring atoms or the number or type of heteroatoms contained, these are valid.

Here, an aryl group or a heteroaryl group is either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or

Thiophene, or a condensed (fused) aromatic or

heteroaromatic polycycle, for example, naphthalene, phenanthrene, quinoline or carbazole understood. A condensed (anneliierter) aromatic or heteroaromatic polycycle consists in the context of the present application of two or more condensed simple aromatic or heteroaromatic cycles.

Under an aryl or heteroaryl group, which may be substituted in each case with the above-mentioned groups and which can be replaced by any

Aromatic or heteroaromatic positions can be linked, are understood in particular groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, Benzanthracen, Benzphenanthren, tetracene, pentacene, benzopyrene, furan, benzofuran , Isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline,

Benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazine imidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole,

Anthroxazole, phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole,

Benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1, 2,3-triazole, 1, 2,4-triazole, benzotriazole, 1, 2,3-oxadiazole, 1, 2,4-oxadiazole, 1,2,5-oxadiazole, 1, 3,4-oxadiazole, 1, 2,3-thiadiazole, 1, 2,4-thiadiazole, 1, 2,5-thiadiazole, 1, 3,4-thiadiazole, 1, 3,5-triazine,

1, 2,4-triazine, 1, 2,3-triazine, tetrazole, 1, 2,4,5-tetrazine, 1, 2,3,4-tetrazine, 1, 2,3,5-tetrazine, purine, Pteridine, indolizine and benzothiadiazole, or a combination of these groups. Under an aryloxy group according to the definition of the present

The invention will be understood to mean an aryl group as defined above which is attached via an oxygen atom. An analogous definition applies to heteroaryloxy groups.

An aromatic ring system in the sense of this invention contains 5 to 60 carbon atoms in the ring system. A heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, of which at least one ring atom represents a heteroatom. The heteroatoms are preferably selected from nitrogen (N), oxygen (O), sulfur (S), silicon (Si) and / or phosphorus (P), and are particularly preferably selected from nitrogen (N), oxygen (O) and / or sulfur (S). This is the basic definition. If other preferences are given in the description of the present invention, for example with respect to the number of aromatic ring atoms or the number or type of heteroatoms contained, these apply. For the purposes of this invention, an aromatic or heteroaromatic ring system is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which several aryl or heteroaryl groups are also replaced by a nonaromatic moiety (preferably less than 10) % of the atoms other than H), such as. An sp ³ -hybridized C, Si, lower O atom, an sp ² -hybridized C or N atom, or a

sp-hybridized carbon atom, may be connected. For example, systems such as 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl, alkenyl or alkynyl group or linked by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are linked together via single bonds, as aromatic or heteroaromatic ring systems in the sense of this

Understood invention, such as biphenyl, terphenyl or diphenyltriazine. By an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case with radicals as defined above and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, naphthalene .

Anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, Truxen , Isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene,

Benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole,

Isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, Imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyrimididazole,

Pyrazine imidazole, quinoxaline imidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1, 3-thiazole,

Benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine,

Quinoxaline, 1, 5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene,

1, 6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene,

4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1, 2,3-triazole, 1, 2,4-triazole, benzotriazole, 1, 2, 3-oxadiazole, 1, 2,4-oxadiazole, 1, 2,5-oxadiazole, 1, 3,4-oxadiazole, 2,3-thiadiazole, 1, 2,4-thiadiazole, 1, 2,5-thiadiazole , 1, 3,4-thiadiazole, 1, 3,5-triazine, 1, 2,4-triazine,

1, 2,3-triazine, tetrazole, 1, 2,4,5-tetrazine, 1, 2,3,4-tetrazine, 1, 2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole, or a Combination of these groups. In the context of the present invention, a group is a straight-chain alkyl group having 1 to 40 C atoms, or a branched or cyclic alkyl group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms in which also individual H atoms or Ch groups can be substituted by the groups mentioned above in the definition of the radicals. This constitutes the basic Definition. If other preferences are given in the description of the present invention, for example with regard to the number of C atoms, these apply. Preference is given to taking a straight-chain alkyl group having 1 to 40 C atoms, or a branched or cyclic alkyl group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, the groups methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, s -butyl, t -butyl, 2-methylbutyl, n-pentyl, s -pentyl,

Cyclopentyl, neo-pentyl, n-hexyl, cyclohexyl, neo-hexyl, n-heptyl,

Cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl,

Pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl understood. Under an alkoxy or thioalkyl group of 1 to 40

C atoms are preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy , Cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy,

2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio,

2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio,

Cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio

Understood.

In the context of the present application, it is to be understood, inter alia, that the two radicals are linked together by a chemical bond, under the formulation that two or more radicals can form a ring with one another. This is illustrated by the following scheme: ring formation

Furthermore, it should also be understood from the above-mentioned formulation that in the case where one of the two radicals represents hydrogen, the second radical binds to the position to which the hydrogen atom was bonded to form a ring. This will be illustrated by the following scheme: ring formation

the radicals R

In the context of the present application, the formulation that two or more radicals can form a ring with one another means, inter alia, that the two radicals are an aryl group, a heteroaryl group, an aryloxy group, a heteroaryloxy group, an aromatic or heteroaromatic ring system, a cyclic ring Alkyl, alkenyl, or alkynyl group can form in the context of this invention.

It is preferred that the radical Z is CR ¹ .

It is further preferred that the radical X on each occurrence is identically or differently selected from C (R ² ) 2, Si (R ² ) 2, O, S, NR ² , PR ² or P (= O) R ² . More preferably, X is C (R ² ) 2.

It is preferable that compounds of the formula (I) are selected from the formulas (V-1) to (V-36) shown below.

wherein the radical R ^{2 is} as defined above and preferably a straight-chain alkyl group having 1 to 20 C atoms or an aromatic or

heteroaromatic ring system comprising 5 to 30 ring atoms, and more preferably comprises a methyl or phenyl group; wherein the groups of formulas (V-1) to (V-36) may be substituted at free positions with a radical R ¹ ; and wherein the radical R ¹ or R ² may be substituted by one or more of the radicals R ³ .

It is further preferred that the radical R on each occurrence is identically or differently selected from H, N (R ² ) 2, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, or aromatic or heteroaromatic ring systems having 5 to 30 ring atoms, where the abovementioned groups may each be substituted by one or more radicals R ³ . More preferably, R ^{1 is} selected from H or N (R ² ) 2. Furthermore, it is preferred that the radical R ² on each occurrence is identically or differently selected from H, straight-chain alkyl groups having 1 to 0 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms or from aromatic or heteroaromatic ring systems with 5 to 30 ring atoms, where the abovementioned groups can each be substituted by one or more radicals R ³ . R ² is particularly preferably selected from straight-chain alkyl groups having 1 to 6 C atoms or from aromatic or heteroaromatic ring systems having 5 to 25 ring atoms. R ² particularly preferably contains at least one group selected from benzene, naphthalene,

Phenanthrene, fluoranthene, biphenyl, terphenyl, quaterphenyl, fluorene, indenofluorene, spirobifluorene, furan, benzofuran, isobenzofuran,

Dibenzofuran, thiophene, benzothiophene, isobenzothiophene,

Dibenzothiophene, indole, isoindole, carbazole, indolocarbazole,

Indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzimidazole, pyrimidine, pyrazine, benzofluorene, benzindene fluorene,

Benzindenoinden and triazine, where the abovementioned groups may each be substituted by one or more R ³ radicals.

Furthermore, it is preferred that the radical R ³ on each occurrence is identically or differently selected from H, F, Cl, Br, I, N (R) 2, a

straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 30 ring atoms, where the abovementioned groups may each be substituted by one or more radicals R ⁴ , R ³ is particularly preferably selected from H, F, straight-chain alkyl groups having 1 to 6 C atoms or from aromatic ring systems having 5 to 8 ring atoms. It is further preferred that the radical R ¹ is H or N (R ² ) 2, where N (R ² ) 2 is selected from the group consisting of the formulas (R ¹ -1) to (R ¹ -125) , which are shown below.

35

35

35



-26-

where the abovementioned groups can each be substituted by one or more radicals R ³ or R ⁴ .

Furthermore, compounds of the following formula (IA) are preferred:

Formula (IA) wherein one or two of the radicals R ¹ are N (R ² ) 2, and wherein the other occurring radicals are as defined above.

The above-mentioned preferred embodiments of radicals are also preferred for this embodiment. In particular, X in compounds of the formula (IA) is preferably identically or differently selected on each occurrence from C (R ² ) 2, Si (R ² ) 2, O, S, NR ² , PR ² or P (OO) R ² , More preferably, X is C (R ² ) 2.

It is further preferred that the radical R ¹ on each occurrence is identically or differently selected from H, N (R ² ) 2, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, or aromatic or heteroaromatic ring systems having 5 to 30 ring atoms, where the abovementioned groups may each be substituted by one or more radicals R ³ . More preferably, R ^{1 is} selected from H or N (R ² > 2.

Furthermore, it is preferred that the radical R ² on each occurrence is identically or differently selected from H, straight-chain alkyl groups with 1 to 10 C atoms, branched or cyclic alkyl groups with 3 to 10 C atoms or from aromatic or heteroaromatic ring systems with 5 to 30 ring atoms, where the abovementioned groups can each be substituted by one or more radicals R ³ . R ² is particularly preferably selected from straight-chain alkyl groups having 1 to 6 C atoms or from aromatic or heteroaromatic ring systems having 5 to 25 ring atoms. Furthermore, compounds of the following formula (IB) are preferred:

Formula (Ib) wherein one or two of R ¹ are N (R ² ) 2, and wherein the other occurring groups are as defined above.

The above-mentioned preferred embodiments of radicals are also preferred for this embodiment.

Furthermore, compounds of the following formula (I-C) are preferred:

Formula (lC) wherein the radical R ¹ is N (R ² ) 2, and wherein the other occurring radicals are as defined above.

The same applies to the compounds of the formula (I-C)

Embodiments of radicals as preferred as given above generally for compounds of formula (I). In particular, X is preferably C (R ² ) ₂ .

Very particular preference is given to the above formulas

Formula (IC). The following compounds are examples of compounds of formula (I):

The subject matter of the present application is furthermore a process for the preparation of a compound according to the invention.

Preferably, the present application comprises a method for

Preparation of a compound of the invention, characterized

characterized in that the method at least one

transition metal catalyzed coupling reaction. Preferably, the coupling reaction is selected from Suzuki coupling reactions and Buchwald coupling reactions. In combination with the above preferred embodiment of the method, the method comprises one or more ring closure reactions, more preferably acid-induced ring closure reactions of tertiary alcohols

Methylene bridges.

Particularly preferred embodiments of processes for the preparation of compounds according to the invention are shown below. As a result, the person skilled in possible synthesis methods

proposed, with which he can produce the compounds of the invention. However, the person skilled in the art is not bound by the methods presented. It may, if necessary, modify and adapt it as needed within the framework of its general expertise.

The compounds of the invention can be known with

Synthesis steps of organic chemistry are produced. Preferred reactions are cyclization reactions, Buchwald couplings and Suzuki couplings.

In the following Scheme 1 is a way to make

compounds of the invention shown. The procedure according to

Scheme 1 is particularly useful in the synthesis of compounds of the invention containing a benzoindenoindene group wherein the benzoindenoindene group is substituted with an arylamino group or with multiple arylamino groups.

In Scheme 1, Ar denotes any aryl or

Heteroaryl group, and X denotes any reactive group, preferably a sulfonic acid ester or halogen group, more preferably tosylate, triflate or bromine. All compounds shown may optionally be substituted with one or more organic radicals. In the process according to Scheme 1, an indenyl-naphthyl compound is prepared via a Suzuki coupling on the substituted indene compound with a substituted naphthyl compound. The naphthyl moiety of the indenyl-naphthyl compound contains a

Carboxylic ester group, which serves as precursor of the methylene bridge of

Benzoindenoindens serves. The carboxylic acid ester group of the phenyl-naphthyl compound is converted by the addition of an organometallic compound to a tertiary alcohol, which upon addition of at least one acid undergoes the ring closure reaction to the methylene bridge of Benzoindenoindens. Subsequently, a methylation reaction is carried out to obtain a methyl-substituted benzoindenoindene (4) receive. The further steps are halogenation or a reaction of the methyl-substituted benzoindenoinden (4) with a

Sulfonic acid halide and a subsequent Buchwald coupling. In the Buchwald coupling, a benzoindenoindene derivative is coupled with an arylamine to yield arylamine-substituted benzoindenoindene compounds (5, 6, 7).

The arylamine-substituted benzoindenoindene compounds (5, 6, 7) can be reacted by further halogenations and subsequent Buchwald couplings to obtain benzoindenoindene compounds substituted with two or more arylamine groups.

Thus, the process for preparing a compound of formula (I) comprises the following steps:

Reacting a substituted indene compound with a substituted naphthyl compound to give an indenyl-naphthyl compound;

Reacting the indenyl-naphthyl compound obtained in step (1) with an organometallic compound to obtain a reduced indenyl-naphthyl compound;

Reacting the reduced indenyl naphthyl compound obtained in step (2) with at least one acid to obtain a benzoindenoinden compound;

Reacting the benzoindenoinden compound obtained in step (3) with a methylating reagent to obtain a methyl-substituted benzoindenoinden compound;

Reacting the methyl-substituted benzoindenoinden compound obtained in step (4) with a

Halogenating agent or a sulfonic acid halide;

(6) reacting the compound obtained after step (5) with a substituted amine compound to obtain an amine-substituted benzoindenoindene compound. Scheme 1

The above-mentioned synthesis process according to Scheme 1 may be followed by further functionalization reactions in which the

obtained inventive compounds are further reacted.

The compounds according to the invention described above, in particular compounds which are substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, can be used as monomers for producing corresponding oligomers, dendrimers or polymers. Suitable reactive leaving groups are, for example, sulfonic acid esters, e.g. Tosylate or triflate, bromine, iodine, chlorine, boronic acids, boronic esters, amines, alkenyl or alkynyl groups with terminal CC double bond or CC triple bond, oxiranes, oxetanes, groups which undergo a cycloaddition, for example a 1, 3-dipolar cycloaddition, such as dienes or azides,

Carboxylic acid derivatives, alcohols and silanes. The invention preferably comprises an oligomer, polymer or dendrimer comprising one or more compounds of the formula (I), wherein the bond (s) to the polymer, oligomer or dendrimer are located at any positions substituted in formula (I) by R ¹ or R ² could be.

Depending on the linking of the compound of the formula (I), the compound is part of a side chain or a main chain of the oligomer or polymer. An oligomer in the context of this invention is understood as meaning a compound which is composed of at least three monomer units. A polymer in the context of the invention is understood as meaning a compound which is composed of at least ten monomer units. The polymers, oligomers or

Dendrimers may be conjugated, partially conjugated or non-conjugated. The oligomers or polymers of the invention may be linear, branched or dendritic. In the linearly linked structures, the units of formula (I) may be directly linked together or may be linked together via a divalent group, for example via a substituted or unsubstituted alkylene group, via a heteroatom or via a divalent aromatic or heteroaromatic group. In branched and dendritic structures, for example, three or more units of formula (I) may be linked via a trivalent or higher valent group, for example via a trivalent or more valent aromatic or heteroaromatic group, to a branched or dendritic oligomer or polymer.

The repeat units of the formula (I) in oligomers, dendrimers and polymers have the same preferences as described above for compounds of the formula (I).

To prepare the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with further monomers. Suitable and preferred comonomers are selected from the group consisting of fluorenes (eg EP 842208 or US Pat

WO 2000/22026), spirobifluorenes (eg EP 707020, EP 894107 or WO 2006/061181), paraphenylenes (eg WO 1992/18552), carbazoles (e.g. WO 2004/070772 or WO 2004/113468), thiophenes (eg.

EP 1028136), dihydrophenanthrenes (eg WO 2005/014689 or WO 2007/006383), cis- and trans-indenofluorenes (eg WO 2004/041901 or WO 2004/113412), ketones (eg WO 2005/040302), phenanthrenes (eg WO 2005/104264 or WO 2007/017066) or also several of these units. The polymers, oligomers and dendrimers usually also contain further units, for example emitting

(fluorescent or phosphorescent) units, such as. B.

Vinyltriarylamines (for example WO 2007/068325) or phosphorescent metal complexes (for example WO 2006/003000), and / or charge transport units, in particular those based on triarylamines.

The polymers, oligomers and dendrimers according to the invention are generally prepared by polymerization of one or more types of monomer, of which at least one monomer in the polymer

Repeating units of the formula (I) leads. suitable

Polymerization reactions are known in the art and described in the literature. Particularly suitable and preferred

Polymerization reactions leading to C-C or C-N linkages are as follows:

(A) SUZUKI polymerization;

(B) YAMAMOTO polymerization;

(C) SILENT polymerization;

(D) HARTWIG-BUCHWALD polymerization;

(E) NEGISHI polymerization; and

(F) HIYAMA polymerization.

How the polymerization can be carried out by these methods and how the polymers can then be separated off from the reaction medium and purified is known to the person skilled in the art and is described in detail in the literature, for example in WO 2003/048225, WO 2004/037887 and WO 2004/037887 described.

The invention preferably comprises a process for the preparation of the polymers, oligomers and dendrimers according to the invention, which is characterized in that the polymers, oligomers and dendrimers according to the invention are prepared by polymerization according to SUZUKI, polymerization according to YAMAMOTO, polymerization according to SILENCE, polymerization according to HARTWIG-BUCHWALD, polymerization according to NEGISHI or polymerization according to HIYAMA. The

Dendrimers according to the invention can be prepared according to the person skilled in the art

be prepared by known methods or in analogy thereto. Suitable methods are described in the literature, such as. In Frechet, Jean M.J .; Hawker, Craig J., "Hyperbranched polyphenylenes and hyperbranched polyesters: new soluble, three-dimensional, reactive polymers", Reactive & Functional Polymers (1995), 26 (1-3), 127-36; Janssen, H.M .; Meijer, E.

W., "The synthesis and characterization of dendritic molecules", Materials Science and Technology (1999), 20 (Synthesis of Polymers), 403-458; Tomalia, Donald A., "Dendrimer Molecules", Scientific American (1995), 272 (5), 62-6; WO 2002/067343 A1 and WO 2005/026144 A1.

For the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required. These formulations may be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) Fenchone, 1, 2,3,5-tetramethylbenzene, 1, 2,4,5-tetramethylbenzene,

1 - methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol,

2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole,

3,5-dimethylanisole, acetophenone, terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin,

Dodecyl benzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether,

Diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether,

Diethylene glycol dibutyl ether, triethylene glycol dimethyl ether,

Diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether,

Tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, Hexylbenzene, heptylbenzene, octylbenzene, 1, 1-bis (3,4-dimethylphenyl) ethane or mixtures of these solvents.

The invention therefore further provides a formulation, in particular a solution, dispersion or emulsion containing at least one compound of the formula (I) or at least one polymer, oligomer or dendrimer comprising at least one unit of

Formula (I) and at least one solvent, preferably an organic solvent. How such solutions can be prepared is known to the person skilled in the art and is described in WO 2002/072714, for example.

WO 2003/019694 and in the literature cited therein.

The compounds of the formula (I) according to the invention are suitable for use in electronic devices, in particular in organic electroluminescent devices (OLEDs). Depending on the substitution, the compounds are used in different functions and layers.

Another object of the invention is therefore the use of a compound according to formula (I) in an electronic device. In this case, the electronic device is preferably selected from the group consisting of organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs),

organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field quench devices

(OFQDs), organic light-emitting electrochemical cells

(OLECs), organic laser diodes (O-lasers) and particularly preferably from organic electroluminescent devices (OLEDs). Another object of the invention is an electronic device containing at least one compound of formula (I). Preferably, the electronic device is selected from those given above

Devices. Particular preference is given to an organic electroluminescent device comprising anode, cathode and at least one emitting layer, characterized in that at least one Organic layer of the organic electroluminescent device contains at least one compound according to formula (I).

In addition to the cathode, anode and the emitting layer, the organic electroluminescent device may contain further layers. These are, for example, selected from one or more

Hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers,

Electron blocking layers, exciton blocking layers,

Interlayers, Charge Generation Layers (IDMC 2003, Taiwan, Session 21 OLED (5), T.E.

Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and / or organic or inorganic p / n transitions. It should be noted, however, that not necessarily each of these layers

must be present and the choice of layers always depends on the compounds used and in particular on the fact that it is a fluorescent or phosphorescent electroluminescent device. The sequence of layers of the organic electroluminescent device is preferably the following: anode hole injection layer hole transport layer emitting layer electron transport layer electron injection layer cathode.

It should again be noted that not all of the layers mentioned must be present, and / or that additional layers may be present.

The subject matter of the invention preferably comprises an electronic device comprising an anode, a hole injection layer, a hole transport layer, an emitting layer, a

An electron transport layer, an electron injection layer and a cathode, wherein a compound of the formula (I) is preferably in the

is contained in the emitting layer. The subject matter of the invention preferably comprises an electronic device comprising an emitting layer comprising the compound H1 and a compound of the formula I-3, and comprising an electron transport layer comprising the compound ETM1:

Connection ETM1

The organic electroluminescent device according to the invention may comprise an emitting layer which has an emission maximum in the blue color range in a wavelength range between 420 nm and 490 nm. The organic electroluminescent device according to the invention may contain a plurality of emitting layers. Particularly preferably, these emission layers have a total of several in this case

Emission maxima between 380 nm and 750 nm, so that overall white emission results, d. H. In the emitting layers, various emitting compounds are used which can fluoresce or phosphoresce and which emit blue or green or yellow or orange or red light. Particularly preferred are three-layer systems, ie systems with three emitting layers, wherein preferably at least one of these layers contains at least one compound according to formula (I) and wherein the three layers show blue, green and orange or red emission (for the basic structure see eg WO 2005/011013). It should be noted that for the production of white light instead of multiple colored emitting

Emitter compounds may also be a single emitter used, which emits in a wide wavelength range.

Alternatively and / or additionally, the inventive

Compounds may also be present in the hole transport layer or in another layer.

It is preferred if the compound according to formula (I) is used in an emitting layer. In particular, the

A compound according to formula (I) for use as emissive material (emitter compound).

The compound of the invention is particularly suitable for use as a blue emitting emitter compound. In this case, the electronic device in question may contain a single emitting layer containing the compound of the invention, or it may contain two or more emitting layers. The further emitting layers may contain one or more compounds according to the invention or alternatively other compounds. When the compound of the present invention is used as an emissive material in an emitting layer, it is preferably used in U.S.P.

Combination with one or more matrix materials used.

The proportion of the compound according to the invention in the mixture of the emitting layer in this case is preferably between 0.1 and 50.0% by volume, more preferably between 0.5 and 20.0% by volume, even more preferably between 1.0 and 10.0% by volume, and completely more preferably between 1.0 and 5.0% by volume. Accordingly, the proportion of the matrix material or the matrix materials is preferably between 50.0 and 99.9% by volume, more preferably between 80.0 and 99.5% by volume, even more preferably between 90.0 and 99.0% by volume, and very particularly preferably between 95.0 and 99.0% by volume.

Preferred matrix materials for use in combination with the compounds according to the invention as emitter are selected from the classes of the oligoarylenes (for example 2,2 ', 7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the oligoarylenes containing condensed aromatic groups, the oligoarylenevinylenes (eg DPVBi or spiro-DPVBi according to EP 676461), the polypodal metal complexes (eg according to WO 2004/081017), the hole-conducting

Compounds (for example according to WO 2004/058911), the electron-conducting

Compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (for example according to WO 2005/084081 and WO 2005/084082), the atropisomers (for example according to WO 2006/048268), the boronic acid derivatives (for example according to US Pat

WO 2006/117052) or the benzanthracenes (for example according to US Pat

WO 2008/145239). Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylenevinylenes, the ketones, the phosphine oxides and the sulfoxides. Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzphenanthrene and / or pyrene or atropisomers of these compounds. In the context of this invention, an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another. Preferred matrix materials for use in combination with the compound of formula (I) in the emissive layer are shown in the following table.

The compounds according to the invention can also be used in other layers, for example as hole transport materials in a hole injection or hole transport layer or electron blocking layer.

If the compound according to formula (I) as hole transport material in a hole transport layer, a hole injection layer or a

Used electron blocking layer, so the compound as

Pure material, ie in a proportion of 100%, be used in the hole transport layer, or it can be used in combination with one or more other compounds. According to a preferred embodiment, the organic layer comprising the compound of the formula (I) then additionally contains one or more p-dopants. As p-dopants according to the present invention are preferably those used organic electron acceptor compounds which can oxidize one or more of the other compounds of the mixture.

Particularly preferred embodiments of p-dopants are those described in WO 2011/073149, EP 1968131, EP 2276085, EP 2213662, EP 1722602, EP 2045848, DE 102007031220, US 8044390, US 8057712, WO

2009/003455, WO 2010/094378, WO 2011/120709, US 2010/0096600 and WO 2012/095143 disclosed compounds.

In the following, generally preferred classes of materials are listed for use as corresponding functional materials in the organic electroluminescent devices according to the invention.

Particularly suitable as phosphorescent emitters are compounds which emit light, preferably in the visible range, with suitable excitation and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80. Preference is given as phosphorescent emitter compounds which copper, molybdenum, tungsten, rhenium,

Ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper.

In this case, for the purposes of the present invention, all luminescent iridium, platinum or copper complexes as phosphorescent

Viewed connections.

Examples of the phosphorescent emitters described above can be found in applications WO 2000/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO

2005/033244, WO 2005/019373 and US 2005/0258742 are taken. In general, all the phosphorescent complexes used in the prior art for phosphorescent OLEDs and as known to those skilled in the art of organic electroluminescent devices are suitable for use in the devices according to the invention. Also, the expert can without inventive step further phosphorescent complexes in

Use combination with the compounds of the invention in OLEDs.

Preferred fluorescent emitters are in addition to the compounds of the invention selected from the class of arylamines. An arylamine or an aromatic amine in the context of this invention is understood as meaning a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a fused ring system, more preferably at least 14 aromatic ring atoms.

Preferred examples of these are aromatic anthracene amines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic

Chrysenediamines. By an aromatic anthracene amine is meant a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position. An aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position. Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, the diarylamino groups being attached to the pyrene preferably in the 1-position or in the 1,6-position. Preferred matrix materials for use with fluorescent emitter compounds are listed above.

Preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, z. B. CBP (Ν, Ν-biscarbazolylbiphenyl) or in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 2008/086851 disclosed carbazole derivatives, indolocarbazole derivatives, for. B. according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, for. B. according to WO 2010/136109, WO 2011/000455 or WO 2013/041176,

Azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for. B. according to

WO 2007/137725, Silanes, z. B. according to WO 2005/111172, azaborole or boronic esters, z. B. according to WO 2006/117052, triazine derivatives, z. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746,

Zinc complexes, e.g. B. according to EP 652273 or WO 2009/062578, diazasilol or tetraazasilol derivatives, z. B. according to WO 2010/054729,

Diazaphosphole derivatives, e.g. B. according to WO 2010/054730, bridged carbazole derivatives, z. According to US 2009/0136779, WO 2010/050778, WO 2011/042107, WO 2011/088877 or WO 2012/143080,

Triphenylene derivatives, eg. B. according to WO 2012/048781, or lactams, z. B. according to WO 2011/116865 or WO 2011/137951.

Suitable charge transport materials, as used in the hole injection or hole transport layer or in the electron blocking layer or in the

Electron transport layer of the inventive electronic

Device can be used in addition to the

Compounds according to the invention include, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107 (4), 953-1010 or other materials used in these layers according to the prior art.

As materials for the electron transport layer, it is possible to use all materials as used in the prior art as electron transport materials in the electron transport layer. In particular, aluminum complexes, for example Alq3, are suitable.

Zirconium complexes, for example Zrq4, lithium complexes, for example Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives,

Pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes,

Diazaphospholderivate and Phosphinoxidderivate. Further suitable materials are derivatives of the abovementioned compounds, as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300. Preferred as hole transport materials which can be used in a hole transport, hole injection or electron blocking layer in the electroluminescent device according to the invention,

Indenofluorenamine derivatives (for example according to WO 06/122630 or US Pat

WO 06/100896), the amine derivatives disclosed in EP 1661888,

Hexaazatriphenylene derivatives (for example according to WO 01/049806), amine derivatives with condensed aromatics (for example in accordance with US Pat. No. 5,061,569), which are described in US Pat

WO 95/09147 disclosed amine derivatives, monobenzoindenofluoreneamines (for example according to WO 08/006449), dibenzoindenofluoreneamines (for example according to WO 07/140847), spirobifluorene amines (for example according to WO 2012/034627 or WO 2013 / 120577), fluorene amines (eg according to WO 2014/015937, WO 2014/015938 and WO 2014/015935), spiro-dibenzopyran amines (eg according to WO 2013/083216) and dihydroacridine derivatives (e.g. B. according to WO 2012/150001). The compounds according to the invention can also be used as hole transport materials.

As the cathode of the organic electroluminescent device, low work function metals, metal alloys or multilayer structures of various metals are preferable, such as

Alkaline earth metals, alkali metals, main group metals or lanthanides (eg Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys of an alkali or alkaline earth metal and silver, for example an alloy of magnesium and silver. In multilayer structures, it is also possible, in addition to the metals mentioned, to use further metals which have a relatively high work function, such as, for example, As Ag or Al, which then usually combinations of metals, such as Ca / Ag, Mg / Ag or Ba / Ag are used. The cathode can preferably have a layer thickness between 50 and 150 nm. Particularly preferably, the layer thickness of the cathode is 100 nm. It may also be preferred between a metallic cathode and the

organic semiconductors to introduce a thin intermediate layer of a material with a high dielectric constant. Suitable examples of these are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (eg LiF, L 12 O, BaF 2, MgO, NaF, CsF, CS 2 CO 3, etc.). Furthermore, lithium-quinolinate can be used for this purpose (LiQ) can be used. The layer thickness of this layer is preferably between 0.5 and 5 nm.

As the anode of the organic electroluminescent device, high work function materials are preferred. Preferably, the anode has a

Work function greater than 4.5 eV vs. Vacuum up. For this purpose, on the one hand

Metals with high redox potential suitable, such as Ag, Pt or Au. On the other hand, metal / metal oxide electrodes (eg.

Al / Ni / NiOx, Al / PtOx) may be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent to either irradiate the organic material (organic

Solar cell) or the extraction of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Particularly preferred are indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is furthermore given to conductive, doped organic materials, in particular conductive doped polymers.

The device is structured accordingly (depending on the application), contacted and finally sealed, since the life of the devices according to the invention can be shortened in the presence of water and / or air.

In a preferred embodiment, the inventive

Organic electroluminescent device characterized in that one or more layers are coated by a sublimation process. The materials are in vacuum sublimation at an initial pressure less than 10 ^"5 mbar, preferably less than

10 " ⁶ mbar, but it is also possible that the

Initial pressure is even lower, for example, less than 10 ^{~ 7} mbar. Also preferred is 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 at a pressure between 10 ^"5 mbar and 1 bar are applied. A special case of this method is the OVJP (organic vapor jet printing) method, in which the materials are applied directly through a nozzle and thus structured (for example, BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).

Further preferred is an organic electroluminescent device, characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such. As screen printing, flexographic printing, Nozzle Printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (ink jet printing), are produced. For this purpose, soluble compounds according to formula (I) are necessary. High solubility can be achieved by suitable substitution of the compounds.

It is furthermore preferred for one or more layers of solution and one or more layers to be used for producing an organic electroluminescent device according to the invention

Sublimation method are applied.

According to the invention, the electronic devices comprising one or more compounds according to the invention can be used in displays, as light sources in illumination applications and as light sources in medical and / or cosmetic applications (eg light therapy).

Exemplary embodiments A) Synthesis examples

General reaction scheme:

5, 6, 7

v)

A-1) Synthesis of building blocks (i) to (v)

2- (1H-inden-2-yl) -4,4,5,5-tetramethyl-1,2,2-dioxaborolane (i)

2-Bromo-1 - / - indene (10.0 g, 51 mmol), bispinacolato-diborane (13.5 g, 53 mmol) and potassium acetate (14.9 g, 151 mmol) are dissolved in 150 mL

Dissolved 1,4-dioxane and added tricyclohexylphosphine (564 mg, 2.0 mmol, 4 mol%) and palladium (II) acetate (228 mg, 1.0 mmol, 2 mol%). The reaction mixture is heated for 18 hours at 110 ° C, then cooled to room temperature and expanded with distilled water. After phase separation, the aqueous phase is extracted with dichloromethane. The combined organic phases are washed several times washed with distilled water, dried over magnesium sulfate and filtered through alumina. Subsequently, the organic phase is concentrated under reduced pressure. The residue obtained is under

Cold action crystallized and finally the solvent removed in vacuo. 11.8 g of product are isolated as a dark brown solid (97% of theory).

Ethyl 1- (1H-inden-2-yl) -2-naphthoate (ii)

(i) (18.1 g, 75 mmol) and potassium phosphate (32.0 g, 150 mmol) are dissolved in a mixture of 130 mL toluene and 100 mL distilled water and treated with 1-bromonaphthalene-2-carboxylic acid ethyl ester (22.1 g, 78 mmol),

Tri (o-tolyl) phosphine (703 mg, 2.3 mmol, 3 mol%) and palladium (II) acetate (85 mg, 0.4 mmol, 0.5 mol%). The reaction mixture is heated at 95 ° C for 19 hours, then cooled to room temperature, and expanded with distilled water. After

Phase separation, the aqueous phase is extracted several times with toluene. The combined organic phases are washed with distilled water, dried over magnesium sulfate and filtered through alumina. The organic phase is concentrated under reduced pressure. The crude residue obtained is passed through silica gel

(Cyclohexane / ethyl acetate, 100: 1) filtered, concentrated and the

Solvent removed in vacuo. 20.5 g of a brown oil are obtained (88% of theory).

2- (1- (1H-inden-2-yl) -naphthalen-2-yl) -propan-2-ol (iii)

(U) (18.9 g, 60 mmol) is dissolved in 210 mL of tetrahydrofuran and treated at 0 ° C with 54.5 mL of a methyl magnesium chloride solution (140 mmol, 20% solution in tetrahydrofuran). The reaction mixture is warmed to room temperature overnight, hydrolyzed with saturated ammonium chloride solution and neutralized with 4% hydrochloric acid. The mixture is expanded with distilled water and extracted with toluene. The combined organic phases are distilled several times

Water and washed once with sodium bicarbonate solution and then dried over magnesium sulfate. The organic phase is removed under reduced pressure to give the crude product, which is treated several times with heptane, the heptane then in Vacuum is removed. The crude product is then filtered. 13.9 g of a brownish solid (73% of theory) are obtained.

7,7-dimethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene (iv)

(iii) (12.6 g, 42 mmol) is dissolved in 130 mL of dichloromethane and at -10 ° C with a mixture of methanesulfonic acid (6.9 mL, 105 mmol) and

Polyphosphoric acid (10.9 g, 94 mmol). The reaction mixture is warmed to room temperature overnight and then admixed with 50 ml of ethanol. After phase separation, the reaction mixture is dilated with distilled water and the aqueous phase is washed with

Extracted dichloromethane. The organic phase is washed with distilled water until all acid residues have been removed and then the solvent is removed under reduced pressure. The solid obtained is recrystallized in heptane, then treated with methanol and filtered, with the solid subsequently with

Methanol is washed and finally over silica gel

(Cyclohexane / dichloromethane 100: 1, 50: 1) is filtered. 5.7 g of a light red solid (48% of theory) are obtained.

5-Bromo-7,7,12,12-tetramethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-ajnaphthalene (v)

7,7,12,12-Tetramethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene (4) (250 mg, 0.8 mmol) is dissolved in 15 mL tetrahydrofuran and then at 0 ° C with 1 equivalent / V-bromosuccinimide (145 mg, 0.81 mmol). The reaction mixture is warmed to room temperature and stirred overnight. After addition of aqueous

Sodium sulfite solution, the phases are separated. The organic phase is extracted with dichloromethane, washed with aqueous sodium sulfite solution and with distilled water, dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. 308 mg of a yellow solid (98% of theory) are obtained. Synthesis of the target compound (4)

iv 4,7,7,12,12-tetramethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene (4)

7,7,12,12-tetramethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene (4) was synthesized in analogy to the following literature procedure:

J. Med. Chem., 2001, Vol. 44, 2601-2611.

(iv) (5.6 g, 19.7 mmol) was mixed with 77.7 mL of

Potassium bis (trimethylsilyl) amide (51 mmol, 15% solution in toluene) and methyl iodide (3.2 mL, 51 mmol) were added. 4.95 g of a brownish solid (81% of theory) are obtained.

A-3) Synthesis of the target compounds (5) to (7)

7,7,12,12-Tetramethyl-W, W-diphenyl, 1-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene-5-amine (5)

(v) (100 mg, 0.26 mmol), palladium (II) acetate (1.2 mg, 5 pmol, 2 mol%), tri-fer-butyl-phosphine (10.3 μL, 10 pmol, 4 mol%, 1.0 M in toluene). . 1.3 equivalents of sodium ferf-butoxide (32.8 mg, 0.33 mmol) and

1 .1 equivalents of diphenylamine (48.3 mg, 0.28 mmol) are added

Inertatmosphäre placed in a reaction vessel and the reaction vessel then sealed. 5 ml of dried toluene are added and the reaction solution is then heated for 24 hours with stirring at 90 ° C. to 110 ° C. After cooling the

Reaction mixture to room temperature, the reaction mixture with distilled water and the phases are separated. After phase separation, the aqueous phase is extracted several times with toluene. The organic phase is then washed with distilled water, dried over magnesium sulfate, the solvent is removed and the crude residue obtained is filtered through silica gel (heptane / dichloromethane, 5: 1). 49 mg of a yellow solid (40% of theory) are obtained. / V, A / bis (2,4-dimethylphenyl) -7,7,12,12-tetramethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene-5-amine (6 )

(v) (100 mg, 0.26 mmol), palladium (II) acetate (1 .2 mg, 5 pmol, 2 mol%), 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (4.2 mg, 10 pmol, 4 mol%) and 1 .1 equivalents of bis (2,4-dimethyl) phenylamine (63.8 mg, 0.28 mmol) are added under inert atmosphere in a reaction vessel and the reaction vessel is then sealed. 5 ml of dried toluene are added and then n-hexyllithium (135 [iL, 334 pmol, 2.47 M in hexane) is added carefully with stirring at room temperature. The reaction mixture is then heated for three hours with stirring at 90 ° C to 1 0 ° C. After this

Cooling of the reaction mixture to room temperature is the

Reaction mixture with distilled water and the phases are separated. After phase separation, the aqueous phase is extracted several times with toluene. The organic phase is then washed with distilled water, dried over magnesium sulfate and the solvent removed. The tube residue obtained is about

Silica gel (heptane / dichloromethane, 5: 1) filtered. 51 mg of a yellow solid (37% of theory) are obtained. / V- (2,4-difluorophenyl) - / V- (2,4-dimethylphenyl) -7,7,12,12-tetramethyl-7,12-dihydrobenzo [4,5] pentaleno [1,2-a] naphthalene-5-amine (7)

(v) (110 mg, 0.27 mmol), palladium (II) acetate (1.2 mg, 6 μητιοΙ, 2 mol%) and 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (4.6 mg, 10 pmol, 4 mol%). ) are added under inert atmosphere in a reaction vessel and the reaction vessel is then sealed. There are 5 mL of dried toluene and then 1.1 equivalents

A / - (2,4-Difluorophenyl) -2,4-dimethylaniline (70.1 mg, 0.3 mmol). Next, at room temperature, n-hexyllithium (144 pL, 355 pmol, 2.47 M in hexane) is added to the reaction mixture with stirring. The reaction mixture is then heated for three hours with stirring at 90 ° C to 110 ° C. After cooling to room temperature, distilled water is added to the reaction mixture and the phases are separated. After phase separation, the aqueous phase is extracted several times with toluene. The organic phase is then washed with distilled water, dried over magnesium sulfate, freed from solvent and filtered through silica gel (heptane / dichloromethane 10: 1, 8: 1, 6: 1). 61 mg of a yellow solid (41% of theory) are obtained.

B) Emission data

The indicated amount of the corresponding compound of the formula (I) is weighed into a 100 ml measuring cylinder and made up to 100 ml with toluene. It is then checked by optical visual inspection that the solid is completely dissolved. A lot of the solution

corresponding compound of formula (I) is placed in a first cuvette and then absorption spectra and / or

Photolumineszenzspektren the corresponding compound of formula (I) recorded. The reference solution is toluene, which is added to a second cuvette.

Absorption spectra were recorded on the device Lambda 9, UV / VIS / NIR

Spectrometer, the company Perkin Elmer measured. Photoluminescence spectra were measured on the F-4500, Fluorescence Spectrophotometer, Hitachi.

B-1) Emission Data of Comparative Compounds (1) to (3)

Connection (1)

Compound (2)

Compound (3)

B-2) Emission data of the target compounds (4) to (7)

Connection (4)

Connection (5)

Connection (6)

Connection (7)

¹ : absorption measurement

2: emission measurement

³ : Excitation wavelength of the emission measurement in nm

4: concentration of the compound in toluene in 10 ^"5 mol / L

5: Color value according to the CIE standard system

6: maxima of the absorption, or emission peaks in nm, the

Main maximum in nm is underlined

7: edge of the absorption, emission peaks

8: half width of the emission peak in nm and in electron volts (eV)

Upon excitation, comparative compounds (1) to (3) based on an indenoinden parent emitted ultraviolet and violet light having wavelengths of 366 nm (compound 1), 406 nm (compound 2), and 426 nm (compound 3).

Surprisingly, it has now been found that the inventive

Compounds of formula (I) based on a benzoindenoindene base have emissions that are significantly shifted to longer wavelengths. The target compounds (5, 6, 7) have, in particular, emissions which lie in the wavelength range of the blue visible light. This is how connection 5 appears Emission maximum at 458 nm, compound 6 an emission maximum at 459 nm and compound 7 an emission maximum at 458 nm.

Thus, the target compounds (5, 6, 7) comprise compounds that exhibit blue emission upon excitation and, accordingly, are for use as blue singlet emitters in electronic

Devices are suitable.

C) Chemical properties of the target compounds

For the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required in which the compounds according to the invention have a sufficient

Concentrate.

The target compounds (5, 6, 7) are in nonpolar solvents, such as e.g. Heptane or toluene, a high solubility, and are therefore suitable for processing from the liquid phase.

For example, the target compound 6 has a solubility of 36 g / L in toluene at room temperature and a solubility of 12 g / L in heptane. For example, the target compound 6 at 98 ° C in heptane a

Solubility of 100 g / L and the target compound 6 can be advantageously recrystallized from heptane.

When manufacturing electronic devices with the

Compounds of the invention can be applied to the OVPD (Organic Vapor Phase Deposition) method or carrier gas sublimation. In this case, the compounds according to the invention are added under reduced pressure from the gas phase to a solid surface in order to apply one or more layers of the compounds according to the invention to the solid surface. In order to achieve a particularly effective addition of the compounds according to the invention from the gas phase, a low sublimation temperature of the compounds according to the invention is advantageous. The target compounds (4, 5, 6, 7) have a low

Sublimation temperature, and are therefore suitable for processing from the gaseous phase. For example, points

Target compound 6 has a sublimation temperature between 140 ° C and 160 ° C.

D) Device examples: Production of OLEDs

The preparation of inventive OLEDs and OLEDs according to the prior art is carried out according to a general method according to WO 04/058911, based on the conditions described here

(Layer thickness variation, materials) is adjusted.

In the following examples (see Tables 1 to 3) the data of different OLEDs are presented. The substrates used are glass plates coated with structured ITO (indium tin oxide) of thickness 50 nm. The OLEDs have in principle the following layer structure: substrate / buffer (20 nm) / hole injection layer (HIL, comprising

Materials HIL1 (major component) and HIL2 (dopant, 3 vol%), 20 nm) / hole transport layer (HTL, 20 nm) / emission layer (EML, 20 nm) / electron transport layer (ETL, 30 nm) / electron injection layer (LiQ 1 nm ) and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. As a buffer, a 20 nm thick layer of Pedot P057 (purchased from HC-Starck Baytron) is applied by spin coating. All remaining materials are thermally evaporated in a vacuum chamber. The structure of the EML and the ETL of the OLEDs and the materials used in this layer are shown in Table 1. The structures of the materials used in the OLED are shown in Table 3, where HIL1 is a first material of the hole injection layer and HIL2 is a second material of the hole injection layer, HTL being the material of the hole transport layer, where ETM1 and LiQ are the materials of the electron transport layer, and wherein LiQ the material of

Electron injection layer is.

The emission layer (EML) always consists of at least one

Matrix material (host, H) and an emitting dopant (dopant, D), the matrix material by cover evaporation in a certain

Volume fraction is added. An indication such as H1: D1 (95%: 5%) here means that the matrix material H1 is present in a volume fraction of 95% and the emitting compound D1 in a proportion of 5% in the layer. Similarly, the electron transport layer may consist of a mixture of two materials.

The OLEDs are characterized by default. For this purpose, the electroluminescence spectra are recorded, the external quantum efficiency (EQE, measured in percent) as a function of luminance, assuming a Lambertian radiation characteristic of current-voltage-luminance characteristics (lUL characteristics) calculated and finally determines the life of the components. The

Electroluminescence spectra are recorded at a luminance of 1000 cd / m ² and used to calculate the CIE 1931 x and y color coordinates. The specification EQE @ 1000 cd / m ² designates the external one

Quantum efficiency at an operating luminance of 1000 cd / m ² . The lifetime LD50 @ 50mA / cm ² is the time that elapses until the

Starting brightness (cd / m ² ) at a current density of 50mA / cm ^{2 has} fallen to half. The data obtained for the various OLEDs are summarized in Table 2.

E) Use of compounds according to the invention as dopants in fluorescent OLEDs

In particular, compounds according to the invention are suitable as blue-fluorescent dopants. As an example according to the invention, the dopant D1 is measured here. As the examples E1 to E3 show, were for the inventive

Dotand D1 as a fluorescent dopant achieves favorable values for external quantum efficiency, with blue emission and good lifetime (LD50). Table 1: Structure of the OLEDs

Example EMI ETL

Thickness / nm thickness / nm

E1 H1 (95%): D1 (5%) 20 nm ETM1 (50%): LiQ (50%) 30 nm

E2 H1 (97%): D1 (3%) 20 nm ETM1 (50%): LiQ (50%) 30 nm

E3 H1 (99%): D1 (1%) 20 nm ETM1 (50%): LiQ (50%) 30 nm

Table 3: Structures of the materials used

NDP-9

HIL2 (p-dopant, commercial

HIL1 available from Novaled GmbH,

Dresden)

HTL

D1 ETM1

LiQ

Claims

claims

Compound of a formula (I)

Formula (I) where:

Z is the same or different CR ¹ or N at each occurrence; Y is equal to C;

X is the same or different at each occurrence, BR ² , C (R ² ) 2,

C (R ² ) 2-C (R ² ) ₂₎ -R ² C = CR ² -, -R ² C = N-, Si (R ² ) ₂ , Si (R ² ) ₂ -Si (R ² ) ₂ , C = O, O, S, S = O, SO _2> NR ² , PR ² or P (= O) R ² ; is identical or different at each occurrence H, N (R ² ) ₂ , D, F, Cl, Br, I, C (= O) R ³ , CN, Si (R ³ ) ₃ , P (= 0) (R ³ ) ₂ , S (= O) R ³ , S (= O) ₂ R ³ , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms , an alkenyl or alkynyl group having 2 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

one or more CH ₂ groups in the abovementioned groups by -R ³ C =CR ³ -, -C =C-, Si (R ³ ) ₂ , C =O, C =NR ³ , -C (= O) O-, -C (= O) NR ³ -, NR ³ , P (= O) (R ³ ), -O-, -S-, SO or SO 2 may be replaced, wherein

two or more radicals R ^{1 may} be linked together and form a ring; is identical or different at each occurrence H, D, F, Cl, Br, I, C (= O) R ³ , CN, Si (R ³ ) ₃ , N (R ³ ) ₂ , P (= O) (R ³ ) ₂ , S (= O) R ³ , S (= O) ₂ R ³ , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms , an alkenyl or alkynyl group having 2 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

one or more CH 2 groups in the abovementioned groups by -R ³ C = CR ³ -, -C = C-, Si (R ³ ) ₂ , C = O, C = NR ³ , -C (= O) O -, -C (= O) NR ³ -, NR ³ , P (= O) (R ³ ), -O-, -S-, SO or SO 2 may be replaced, wherein

two or more radicals R ^{2 may} be linked together and form a ring; is identical or different at each occurrence H, D, F, Cl, Br, I, C (= O) R ⁴ , CN, Si (R ⁴ ) ₃₎ N (R ⁴ ) _2> P (= O) (R ) ₂ , S (= O) R ⁴ , S (= O) ₂ R ⁴ , a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aromatic or heteroaromatic ring system having 5 to 30 ring atoms or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

one or more Chb groups in the above groups by -R ⁴ C = CR ⁴ -, -C = C-, Si (R ⁴ ) ₂ , C = O, C = NR ⁴ , -C (= O) O -, -C (= O) NR ⁴ -, NR ⁴ , P (= O) (R ⁴ ), -O-, -S-, SO or SO 2 may be replaced, wherein

two or more radicals R ^{3 may} be linked together and form a ring;

R ⁴ is the same or different H, D, F, Cl at each occurrence

Br, I, CN, a straight-chain alkyl or alkoxy group having 1 to 20 C atoms, a branched or cyclic alkyl or alkoxy group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms aromatic or heteroaromatic ring system having 5 to 30 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 30 ring atoms, wherein

two or more radicals R ^{4 may} be linked together and form a ring.

Compound according to claim 1, characterized in that the radical Z is CR ¹ .

Compound according to Claim 1 or 2, characterized in that the radical X on each occurrence is identically or differently selected from C (R ² ) ₂ , Si (R ² ) ₂ , O, S, NR ² , PR ² or P (= O) R ² , and preferably equal to C (R ² ) 2.

4. A compound according to one or more of claims 1 to 3,

characterized in that the radical R ¹ on each occurrence is identically or differently selected from H, N (R ² ) 2, straight-chain Alkyl groups having 1 to 10 carbon atoms, branched or cyclic alkyl groups having 3 to 10 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 ring atoms, where the abovementioned groups may each be substituted by one or more radicals R ³ .

Compound according to one or more of Claims 1 to 4, characterized in that the radical R ² on each occurrence is identically or differently selected from H, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C Atoms, or from aromatic or heteroaromatic ring systems having 5 to 30 ring atoms, where the abovementioned groups may each be substituted by one or more radicals R ³ . 6. A compound according to one or more of claims 1 to 5,

characterized in that the radical R ³ in each occurrence is identically or differently selected from H, F, Cl, Br, I, N (R ⁴ ) 2, straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 ring atoms, where the abovementioned groups may each be substituted by one or more radicals R ⁴ .

7. A compound according to one or more of claims 1 to 6,

characterized in that the radical R is H or N (R ² ) 2, where N (R ² ) 2 is selected from the group consisting of the formulas (R ¹ -1) to (R-125):

(R ¹ -D (R ¹ -2)

35



ĨR -125) where the abovementioned groups can each be substituted by one or more radicals R ³ or R ⁴ .

8. A compound according to one or more of claims 1 to 7,

characterized in that it corresponds to the following formula (I-A)

Formula (IA) wherein one or two of R ¹ are N (R ² ) 2, and wherein the other occurring groups are as defined in one or more of claims 1 to 7.

9. A compound according to one or more of claims 1 to 8,

characterized in that it corresponds to the following formula (I-B)

Formula (Ib) wherein one or two of R ¹ are N (R ² ) 2, and wherein the other occurring groups are as defined in one or more of claims 1 to 7.

An oligomer, polymer or dendrimer comprising one or more compounds according to one or more of claims 1 to 9, wherein the bond (s) to the polymer, oligomer or dendrimer can be located in any position substituted in formula (I) with R ¹ or R ² .

A formulation comprising at least one compound according to one or more of claims 1 to 9 or at least one polymer, oligomer or dendrimer according to claim 10 and at least one solvent.

Process for the preparation of a compound according to one or more of claims 1 to 9, comprising the following steps:

(1) reacting a substituted indene compound with a substituted naphthyl compound to give an indenyl-naphthyl compound;

(2) reacting the indenyl-naphthyl compound obtained in step (1) with an organometallic compound to obtain a reduced indenyl-naphthyl compound;

(3) reacting the reduced indenyl naphthyl compound obtained in step (2) with at least one acid to obtain a benzoindenoinden compound;

(4) reacting the benzoindenoindene compound obtained in step (3) with a methylating reagent to obtain a methyl-substituted benzoindenoinden compound;

(5) reacting the methyl-substituted benzoindenoindene compound obtained in step (4) with a

Halogenating agent or a sulfonic acid halide;

(6) reacting the compound obtained after step (5) with a substituted amine compound to obtain an amine-substituted benzoindenoindene compound.

Electronic device selected from the group consisting of organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs), organic solar cells (OSCs), organic optical detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices (OLEDs) containing at least one compound according to one or more of claims 1 to 9.

Electronic device according to claim 13, selected from organic electroluminescent devices, characterized

characterized in that the compound according to one or more of claims 1 to 9 in at least one organic layer selected from hole transport layer, hole injection layer,

Electron blocking layer and emitting layer is contained, and that the compound according to one or more of claims 1 to 9 is preferably contained in the emitting layer.

Use of a compound according to one or more of claims 1 to 9 in an electronic device.