EP3888147A1 - Compounds for electronic devices - Google Patents

Abstract

The present invention relates to condensed N-heteroaromatic compounds, to processes for preparing these compounds, and to electronic devices containing said compounds.

Description

Connections for electronic devices

The present application relates to certain N-heteroaromatic

Links. The connections are suitable for use in electronic devices.

Electronic devices in the sense of this application are understood as organic electronic devices, which are organic semiconductor materials

Functional materials included. In particular, this means OLEDs (organic electroluminescent devices). The term OLEDs is understood to mean electronic devices which have one or more layers containing organic compounds and which emit light when electrical voltage is applied. The structure and the general principle of operation of OLEDs are known to the person skilled in the art.

With electronic devices, in particular OLEDs, there is great interest in improving the performance data, in particular

Lifetime, efficiency, operating voltage and color purity. No fully satisfactory solution has yet been found on these points. There is also a need for new, alternative connections for use in electronic devices, particularly in OLEDs.

A big influence on the performance data of electronic

Devices have emissive layers, in particular

phosphorescent emissive layers. New compounds are still being sought for use in these layers, in particular compounds which can serve as matrix material in an emitting layer. For this purpose, in particular, compounds are sought which have a high glass transition temperature TG and a high oxidation and temperature Have stability, in particular high oxidation and temperature stability.

A large number of heteroaromatic are in the prior art

Compounds known for use as matrix material for phosphorescent emitting layers, for example carbazole derivatives and triazine derivatives.

However, there is still a need for alternative connections that are suitable for use in electronic devices, in particular for connections that have one or more of the advantageous properties mentioned above. In particular, there is a need for alternatives to triazine derivatives as matrix materials for phosphorescent emitters.

There is still a need for improvement in the performance data achieved when using the connections in electronic devices, in particular in terms of service life, operating voltage, efficiency and

Color purity of the devices.

It has been found that certain N-heteroaromatic

Connections excellent for use in electronic

Devices are suitable, in particular for use in OLEDs, again particularly for use as matrix materials for

phosphorescent emitters. The connections lead to higher

Lifetime, high efficiency, low operating voltage and high color purity of the devices. Furthermore, the

Compounds have a high glass transition temperature TG and a high oxidation and temperature stability.

The subject of the present application is an electronic one

Device comprising a compound which contains a structural element of a formula (I)

Formula (I), where:

Z ¹ is the same or different at each occurrence C, CR ¹ or N;

Z ² is the same or different at each occurrence C, CR ² or N;

Each occurrence of T ¹ is chosen the same or different from - (C = 0) (NAr ¹ ) -, - (C = S) (NAr ¹ ) -, - (S0 ₂ ) (NAr ¹ ) -, and - (C = 0) 0-;

Ar ¹ is selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with one or more radicals R ³ and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with one or more radicals R ³ ;

Each occurrence of R ¹ is the same or different from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ¹ can be linked and one Can form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ² is the same or different from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ² can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ³ is chosen identically or differently from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ³ can be linked to one another and one Can form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ⁴ is the same or different from H, D, F, CI, Br, I, C (= 0) R ⁵ , CN, Si (R ⁵ ) ₃ , N (R ⁵ ) ₂ , P (= 0) (R ⁵ ) ₂ , OR ⁵ , S (= 0) R ⁵ , S (= 0) ₂ R ⁵ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^{3 may} be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁵ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁵ C = CR ⁵ -, -C ^ C-, Si (R ⁵ ) 2, C = 0, C = NR ⁵ , -C (= 0) 0-, -C (= 0) NR ⁵ -, NR ⁵ , P (= 0) (R ⁵ ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ⁵ is selected identically or differently from H, D, F, CI, Br, I, CN, alkyl or alkoxy groups with 1 to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ⁵ can be linked to one another and form a ring; and wherein said alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems with one or more radicals selected from F and CN can be substituted; k is 0 or 1, where in the case of k = 1 the groups Z ¹ and Z ² which bind to the relevant group T ¹ are C and are connected to one another via the group T ¹ , and where in the case of k = 0 the the relevant group T ^{1 is} not present, and the relevant groups Z ¹ and Z ^{2 are} not connected to one another.

In the context of the present invention, a circle within a six- or five-membered ring means that the ring in question is aromatic or

is heteroaromatic, due to pi-electrons of double bonds or fleteroatoms.

The definition Z ¹ = C means that the structural element of the formula (I) is part of a larger condensed ring system,

for example by placing a benzene ring on it and on one

adjacent Z ^{1 is} condensed. The same applies to Z ² = C.

The divalent group T ¹ can be the same or different in both possible orientations at each occurrence, in the case of - (C = 0) (NAr ¹ ) - for example as - (C = 0) (NAr ¹ ) - or as - (NAr ¹ ) (C = 0) -.

The following definitions apply to the chemical groups used in the present application. They apply if no more specific definitions are given.

An aryl group in the sense of this invention is understood to mean either a single aromatic cycle, that is to say benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene or anthracene. For the purposes of the present application, a condensed aromatic polycycle consists of two or more together condensed individual aromatic cycles. Condensation between cycles means that the cycles share at least one edge with one another. An aryl group in the sense of this invention contains 6 to 40 aromatic ring atoms, none of which is a hetero atom.

For the purposes of this invention, a heteroaryl group means either a single heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a condensed heteroaromatic polycycle, for example quinoline or carbazole. A condensed heteroaromatic polycycle exists in the sense of the present

Registration of two or more individual aromatic or heteroaromatic cycles condensed with one another, at least one of the aromatic and heteroaromatic cycles being a heteroaromatic cycle. Condensation between cycles means that the cycles share at least one edge with one another. A

Heteroaryl group in the sense of this invention contains 5 to 40 aromatic ring atoms, at least one of which represents a hetero atom. The heteroatoms of the heteroaryl group are preferably selected from N, O and S.

Under an aryl or heteroaryl group, each with the above

radicals mentioned can be understood to mean, in particular, groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene,

Fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, acridine, acridine, acridine 6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, benzimidazolo [1,2-ajbenzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole,

Pyrazinimidazole, quinoxaline imidazole, 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.

An aromatic ring system in the sense of this invention is a system which does not necessarily only contain aryl groups, but which can additionally contain one or more non-aromatic rings which are condensed with at least one aryl group. Not this one

aromatic rings contain only carbon atoms as

Ring atoms. Examples of groups included in this definition are tetrahydronaphthalene, fluorene and spirobifluorene. The term aromatic ring system also includes systems which consist of two or more aromatic ring systems which are connected to one another via single bonds, for example biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl and 3,5-diphenyl-1-phenyl. An aromatic ring system in the sense of this invention contains 6 to 40 carbon atoms and no heteroatoms in the ring system. The definition of “aromatic ring system” does not include heteroaryl groups.

A heteroaromatic ring system corresponds to that mentioned above

Definition of an aromatic ring system, with the difference that it must contain at least one heteroatom as a ring atom. As is the case with the aromatic ring system, the heteroaromatic must

Ring system not only contain aryl groups and heteroaryl groups, but one or more can not

contain aromatic rings with at least one aryl or

Heteroaryl group are condensed. The non-aromatic rings can contain only carbon atoms as ring atoms, or they can additionally contain one or more heteroatoms, the

Heteroatoms are preferably selected from N, O and S. An example of such a heteroaromatic ring system is benzopyranyl. Furthermore, the term “heteroaromatic ring system” is understood to mean systems which consist of two or more aromatic or heteroaromatic ring systems which are linked to one another via single bonds

are connected, such as 4,6-diphenyl-2-triazinyl. A

Heteroaromatic ring system in the sense of this invention contains 5 to 40 ring atoms which are selected from carbon and heteroatoms, at least one of the ring atoms being a heteroatom. The heteroatoms of the heteroaromatic ring system are preferably selected from N, O and S.

The terms "heteroaromatic ring system" and "aromatic

Ring system ”as defined in the present application

differ from each other in that an aromatic ring system cannot have a hetero atom as a ring atom, whereas a heteroaromatic ring system must have at least one hetero atom as a ring atom. This heteroatom can be used as a ring atom of a non-aromatic heterocyclic ring or as a ring atom of one

aromatic heterocyclic ring are present.

As defined above, each aryl group is included in the term "aromatic ring system" and each heteroaryl group is included in the term "heteroaromatic ring system".

Under an aromatic ring system with 6 to 40 aromatic

Ring atoms or a heteroaromatic ring system with 5 to 40 aromatic ring atoms are understood in particular to be groups which are derived from the groups mentioned above under aryl groups and heteroaryl groups and from biphenyl, terphenyl, quaterphenyl, fluorene, Spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluorene, truxene, isotruxes, spirotruxes, spiroisotruxes,

Indenocarbazole, or combinations of these groups.

In the context of the present invention, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, in which also individual H atoms or Chh groups can be substituted by the groups mentioned above when defining the radicals, preferably the radicals 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 with 1 to 20 C atoms, in which also individual H atoms or CH2 groups by the above in the

Definition of the groups mentioned radicals can be substituted, preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2nd -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-ethylhexylthioethyl, trifluoroethyl, trifluoro , 2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio,

Cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio,

Hexinylthio, heptinylthio or octinylthio understood. In the context of the present application, the wording that two or more radicals can form a ring with one another is to be understood, inter alia, to mean that the two radicals are linked to one another by a chemical bond. Furthermore, the above-mentioned formulation should also be understood to mean that in the event that one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring.

T ¹ is preferably equal to - (C = 0) (NAr ¹ ) -.

Ar ¹ is preferably selected the same or different for each occurrence from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthalene, fluorene, benzofluorene,

Spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran,

Dibenzothiophene, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, benzimidazole, quinazoline, quinoxaline, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, where the monovalent groups can each be substituted by one or more radicals R ³ . Alternatively, Ar ¹ can be selected the same or different for each occurrence from combinations of groups derived from benzene, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene , Benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran,

Dibenzothiophene, carbazole, benzofuran, benzothiophene, indole,

Benzimidazole, quinazoline, quinoxaline, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, where the groups can each be substituted by one or more radicals R ³ .

Ar ¹ is particularly preferably selected the same or different from phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, Naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, triazinyl, pyrimidyl, pyridyl, quinazoline, quinoxaline and quinoline, where the groups mentioned can each be substituted by one or more radicals R ³ .

Preferably no more than one group Z ¹ per formula is N, and the other groups Z ¹ are selected from C and CR ¹ . Z ¹ is preferably selected the same or different from C and CR ¹ for each occurrence.

Preferably no more than one group Z ² per formula is N, and the other groups Z ² are selected from C and CR ² . Z ² is preferably selected the same or different from C and CR ² at each occurrence.

K is preferably 0.

With each occurrence, R ¹ is preferably selected identically or differently from H, D, F, CN, Si (R ⁴ ) 3, N (R ⁴ ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and

Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ ; and wherein in said alkyl or alkoxy groups one or more CFh groups by -C ^ C-, -R ⁴ C = CR ⁴ -, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -NR ⁴ -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ⁴ - can be replaced. With each occurrence, R ¹ is particularly preferably selected identically or differently from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said aromatic

Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ . Each occurrence of R ² is preferably selected identically or differently from H, D, F, CN, Si (R ⁴ ) 3, N (R ⁴ ) 2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and

Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ ; and wherein in said alkyl or alkoxy groups one or more CFh groups by -C ^ C-, -R ⁴ C = CR ⁴ -, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -NR ⁴ -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ⁴ - can be replaced. With each occurrence, R ² is particularly preferably selected identically or differently from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said aromatic

Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ .

With each occurrence, R ³ is preferably selected identically or differently from H, D, F, CN, Si (R ⁴ ) 3, N (R ⁴ ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and

Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ ; and wherein in said alkyl or alkoxy groups one or more CFh groups by -C ^ C-, -R ⁴ C = CR ⁴ -, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -NR ⁴ -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ⁴ - can be replaced. With each occurrence, R ³ is particularly preferably selected identically or differently from H, aromatic ring systems with 6 to 40 aromatic ring systems Ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said aromatic

Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ .

Each occurrence of R ⁴ is preferably selected identically or differently from H, D, F, CN, Si (R ⁵ ) 3, N (R ⁵ ) 2, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and

Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁵ ; and wherein in said alkyl or alkoxy groups one or more CFh groups by -C ^ C-, -R ⁵ C = CR ⁵ -, Si (R ⁵ ) 2, C = 0, C = NR ⁵ , -NR ⁵ -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ⁵ - can be replaced.

R ⁵ is preferably equal to H.

Formula (I) preferably corresponds to one of the following formulas:

where the symbols appearing are as defined above. According to a preferred embodiment, Z ^{1 is the} same or different C or CR ¹ on each occurrence. According to an alternative preferred

The embodiment is exactly one group Z ¹ per formula equal to N, and the remaining groups Z ¹ are the same or different C or CR ¹ each time they occur. According to a further preferred embodiment, Z ^{2 is the} same or different C or CR ² on each occurrence. According to an alternative preferred embodiment, exactly one group Z ² per formula is N, and the remaining groups Z ² are the same or different C or CR ² on each occurrence.

In a preferred embodiment, Z ^{1 is the} same or different C or CR ¹ on each occurrence, and Z ² is the same on each occurrence or different C or CR ² . According to an alternative preferred embodiment, Z ¹ is on each occurrence, identically or differently, C or CR ^1, Z ² and precisely one group per formula is equal to N, and the remaining groups Z ² are on each occurrence, identically or differently, C or CR. ²

It is preferred that the compound containing a structural unit of the formula (I) corresponds to one of the following formulas:

where Ar ^{2 is} selected from aromatic ring systems with 4 to 40 aromatic ring atoms which are substituted with radicals R ^A and heteroaromatic ring systems with 3 to 40 aromatic ring atoms which are substituted with radicals R ^A , and wherein Z ^{1 is the} same or different on each occurrence Is CR ¹ or N and the other symbols are defined as above.

Ar ² is preferably an aromatic ring system with 4 aromatic

Ring atoms which are substituted by radicals R ^A ; that is, condensed benzene, which is substituted with radicals R ^A.

The group Ar ² shown in formulas (I-3) to (1-14) and (1-18) to (I-20) above is fused to the five-ring and six-ring, respectively, just like a benzene group to one in a naphthalene group other benzene group is fused by both benzene groups sharing two carbon atoms and the bond between them.

An example of this is the following falling under formula (I-3)

Embodiment

in which Ar ^{2 is} a unit C4FI4 derived from a benzene ring.

Each occurrence of R ^A is chosen identically or differently from H, D, F, CI Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0 ) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^A can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced.

With each occurrence, R ^A is preferably selected identically or differently from H, D, F, CN, Si (R ⁴ ) 3, N (R ⁴ ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40

aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and

Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁴ .

In the above formulas, Z ¹ is preferably equal to CR ¹ . According to an alternative preferred embodiment, exactly one group Z ¹ per formula is N, and the remaining groups Z ² are CR ¹ .

In formulas (1-1) to (I-20) above there is preferably at least one group R ¹ , R ² , R ³ or R ^A which is selected from

aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R ⁴ (radical A), - Heteroaromatic ring systems with 5 to 40 aromatic

Ring atoms which are substituted by radicals R ⁴ (radical B),

- N (R ⁴ ) ₂ , where groups R ⁴ in groups N (R ⁴ ) 2 are preferred, the same or different for each occurrence, selected from aromatic

Ring systems with 6 to 40 aromatic ring atoms, which are substituted with radicals R ⁵ , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with radicals R ⁵ (radical C).

Corresponding compounds are the subject of the present

Registration.

Residues A are preferably selected the same or different at each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthyl, fluorenyl and spirobifluorenyl, each of which is substituted by radicals R ^A.

At each occurrence, radicals B are preferably selected identically or differently from dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, triazinyl, pyrimidyl, pyridyl, quinazolinyl, quinoxalinyl and quinolinyl, each of which is substituted by radicals R ^A.

Exactly one group R ¹ , R ² , R ³ or R ^A is preferably present in the formulas (1-1) to (I-20) above, which is selected from the above-mentioned radicals A, B or C. Particularly preferred in this case the other existing groups R ¹ , R ² , R ³ and R ^{A are} equal to Fl.

Particularly preferred among the above formulas are formulas (1-1) to (I-4), (1-11), (1-12) and (1-15).

Particularly preferred embodiments of the connection correspond to the following formulas the symbols which occur are as defined above and preferably correspond to their preferred embodiments mentioned above.

In the formulas (1-1-1) to (1-4-1), (1-1 1-1), (1-12-1) and (1-15-1), all groups R ¹ are preferably the same H. All groups R ² are also preferably H. All groups R ³ are H. Also preferred are all groups R ^A are H. All groups R ¹ , R ² , R ³ and R ^A are H .

According to an alternative preferred embodiment in the formulas (1-1-1) to (1-4-1), (1-1 1-1), (1-12-1) and (1-15-1) is at least a group selected from groups R ¹ , R ² , R ³ and R ^A selected from the above-mentioned radicals A, B and C. Particularly preferred in this case are the other groups R ¹ , R ² , R ³ and R ^A equal to Fl .

Ar ^{2 is} furthermore preferably a fused-on benzene group which is substituted by radicals R ^A. Accordingly, preferred ones

Embodiments of the formulas (1-3-1), (1-4-1), (1-1 1 -1) and (1-12-1) selected from the following formulas: where the symbols appearing are defined as for formulas (1-1-1) to (I- 4-1), (1-11-1), (1-12-1) and (1-15-1).

Preferred in the formulas (1-3-1 -A), (1-4-1 -A), (1-11-1-A) and (1-12-1 -A) are all groups R ¹ equal to Fl . Furthermore, all groups R ² are preferably Fl. Furthermore, all groups R ³ are preferably Fl. Furthermore, all groups R ^A are preferably equal to Fl. All groups R ¹ , R ² , R ³ and R ^A are particularly preferably equal to Fl. According to an alternative preferred embodiment in the formulas (1-3-1 -A), (1-4-1 -A), (1-1 1 -1 -A) and (1-12-1 -A) is at least a group selected from groups R ¹ , R ² , R ³ and R ^A selected from the above-mentioned radicals A, B and C. Particularly preferred in this case are the other groups R ¹ , R ² , R ³ and R ^A equal to Fl .

Particularly preferred embodiments of the connection correspond to the following formulas:

where the symbols which occur are defined as above, and where R ^{2 is} preferably selected from radicals A, B and C. In the formulas, R ¹ is preferably H.

Particularly preferred embodiments of the connection correspond to the following formulas: where the symbols which occur are defined as above, and where R ^{2 is} preferably selected from radicals A, B and C. In the formulas R ¹ is preferably H and / or R ^A is H, particularly preferably R ¹ and R ^{A are the} same H.

Particularly preferred embodiments of the connection correspond

where the symbols which occur are defined as above, and where R ^{A is} preferably selected from radicals A, B and C. In the formulas R ¹ is preferably H and / or R ² is H, particularly preferably R ¹ and R ^{2 are the} same H.

Particularly preferred embodiments of the connection correspond to the following formulas:

where the symbols which occur are defined as above, and where R ^{1 is} preferably selected from radicals A, B and C. In the formulas R ² is preferably H and / or R ^A is H, particularly preferably R ² and R ^{A are the} same H.

Particularly preferred embodiments of the connection correspond

wherein the symbols that occur are defined as above, and wherein preferably R ¹ is H and / or R ² is H, particularly preferably R ¹ and R ² are H.

Preferred compounds containing a structural unit of the formula (I) are shown below:

For the synthesis of the compounds according to the invention, it is possible to start from commercially available compounds which already contain the pyrrolo-quinazolinone backbone or its modifications according to formula (I). These starting compounds are then halogenated and Ullmann coupling is performed to introduce an aryl or heteroaryl group on the nitrogen atom of the lactam group (Scheme 1). In a subsequent step (Scheme 2) an amino group is introduced in a Buchwald coupling, or an aryl or heteroaryl group is introduced in a Suzuki coupling.

Scheme 1

HetAr = heteroaromatic ring system

T ¹ = - (C = 0) (NAr ¹ ) -

X = reactive group, preferably CI, Br or I.

Scheme 2

HetAr = heteroaromatic ring system

Ar = aromatic or heteroaromatic ring system

T ¹ = - (C = 0) (NAr ¹ ) -

X = reactive group, preferably CI, Br or I.

According to an alternative synthetic method for compounds containing a structural element of formula (I), the procedure shown in Scheme 3 below can be followed.

Scheme 3

X = reactive group, preferably CI, Br or I.

Starting from a 1,3-dicarboxylic acid benzene which bears an amino group in the 2-position or a halogen group in the 2-position, a 1,3-dicarboxylic acid benzene is produced which has an N-pyrrole group in the 2-position wearing. The two carboxylic acid groups are converted into arylamide groups via the corresponding carboxylic acid chlorides. The compound on the pyrrole group is then brominated in positions 2 and 5. Finally, a Buchwald reaction is carried out in which the two nitrogen atoms of the two arylamide groups each form a ring with the pyrrole group.

An alternative process for the preparation of compounds containing a structural element of the formula (I) can be carried out as shown in the following scheme:

Scheme 4

R = organic residue

Starting from a benzimidazole derivative and a 2-fluoro-benzaldehyde derivative, a coupling product is first produced which has a ketone group. This is then converted into an oxime group. The oxime is converted into the two isomeric cyclic lactams in a Beckmann rearrangement. These can be separated from each other by preparative means, for example by chromatography. In a last step, the NH group of the lactam unit is further converted in a Ullmann coupling, so that an aromatic group is bound to the NH group of the lactam unit.

The application thus also relates to a process for the preparation of a compound comprising a structural element of the formula (I), characterized in that starting from a compound of the formula (In-1) or (In-II) wherein HetAr is a heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is substituted with radicals R ² , and Z ¹ in each

Occurrence is the same or different CR ¹ or N,

in a first step a halogen substituent is introduced, preferably CI, Br or I, in a second step in an Ullmann coupling reaction on the nitrogen atom of the lactam group an aromatic or

heteroaromatic ring system is introduced, and in a third step in the position of the halogen substituent, an amino group is introduced via a Buchwald coupling, which carries aromatic or heteroaromatic ring systems as a substituent, or an aromatic or heteroaromatic ring system is introduced via a Suzuki coupling.

An alternative method for producing a compound containing a structural element according to formula (I) is characterized in that starting from a compound of a formula (Int-Ill)

Formula (Int-Ill) where Z ^{1 is the} same or different CR ¹ or N at each occurrence; and HetAr is a heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is substituted with radicals R ² ; and Ar ¹ on each

Appearance the same or different is chosen from aromatic

Ring systems with 6 to 40 aromatic ring atoms, which are substituted by one or more radicals R ³ , and heteroaromatic

Ring systems with 5 to 40 aromatic ring atoms which are substituted by one or more R ³ radicals; characterized in that, in a first step, halogen substituents, preferably Br, are introduced in the two positions vicinal to the N atom of HetAr, and in a second step, the amide groups of the formula (Int-III) in a metal-catalyzed coupling reaction at the positions of the halogen substituents bind to HetAr so that two lactam rings are formed.

An alternative method for producing a compound containing a structural element according to formula (I) is characterized in that a starting compound of a formula (Int-IV)

Formula (Int-IV) where Ar is an aromatic ring system with 6 to 40 aromatic

Is a ring atom which is substituted by radicals R ² and where Z ^{1 is the} same or different at each occurrence CR ¹ or N; in a first step on the corresponding ketone group

Hydroxylamine derivative is implemented, this hydroxylamine derivative is then reacted in a second step in a Beckmann rearrangement, and the lactam derivative obtained is then reacted in a third step on the nitrogen of the lactam unit in a Ullmann coupling.

The Beckmann rearrangement preferably produces two isomeric lactam derivatives, which are separated by chromatography before a further reaction takes place.

Intermediates containing the pyrrolo-quinazolinone backbone or the pyrrolo-quinoxalinone backbone are commercially available in some cases. In the following, known synthetic methods for the preparation of compounds containing the above-mentioned basic structure or variants thereof are shown in the prior art. These show that such starting compounds are accessible to the person skilled in the art within the scope of his general specialist knowledge.

The procedure below (Scheme 5) can be used to produce indolo-quinazolinones:

Scheme 5

The procedures below (Schemes 6 and 7) can be used to produce indolo-quinoxalinones: Scheme 6

The procedures below (Schemes 8 and 9) can be used to produce indolo-quinoxalinones:

Scheme 8

A process for the preparation of benzimidazolo-quinazolinones is shown in the following schemes:

Scheme 10

A process for the preparation of benzimidazolo-quinoxazolinones is shown in the following scheme:

Scheme 12

The compounds containing a structural element of the formula (I), in particular compounds which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, can be used as monomers to produce corresponding oligomers,

Dendrimers or polymers are used. Suitable reactive Leaving groups are, for example, bromine, iodine, chlorine, boronic acids, boronic esters, amines, alkenyl or alkynyl groups with a terminal C - C double bond or CC triple bond, oxiranes, oxetanes, groups which have a cycloaddition, for example a 1,3-dipolar cycloaddition , such as dienes or azides, carboxylic acid derivatives, alcohols and silanes.

The invention therefore furthermore relates to oligomers, polymers or dendrimers containing one or more compounds containing a structural element of the formula (I), the bond (s) to the polymer, oligomer or dendrimer to any, in formula (I) with R ¹ , R ² or R ³ substituted positions can be localized. Depending on the linkage of the compound, it is part of a side chain of the oligomer or polymer or part of the main chain. For the purposes of this invention, an oligomer is understood to mean a compound which is composed of at least three monomer units. For the purposes of the invention, a polymer is understood to mean a compound which is composed of at least ten monomer units. The polymers, oligomers or dendrimers according to the invention can be conjugated, partially conjugated or non-conjugated. The oligomers or polymers according to the invention can be linear, branched or dendritic. In the linearly linked structures, the units of the formula (I) can be linked directly to one another or they can be linked to one another via a bivalent group, for example via a substituted or unsubstituted alkylene group, via a fletero atom or via a bivalent aromatic or heteroaromatic group. In branched and dendritic structures, for example, three or more units of the formula (I) can be linked via a trivalent or higher-valent group, for example via a trivalent or higher-valent aromatic or heteroaromatic group, to form a branched or dendritic oligomer or polymer. The same preferences apply to the repeat units in oligomers, dendrimers and polymers as described above for compounds containing a structural element of the formula (I).

To freeze the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with other monomers. Suitable and preferred comonomers are selected from fluorenes, spirobifluorenes, paraphenylenes, carbazoles, thiophenes, dihydrophenanthrenes, cis and trans-indofluorenes, ketones,

Phenanthrenes or several of these units. The polymers, oligomers and dendrimers usually contain further units, for example emitting (fluorescent or phosphorescent) units, such as. B. vinyl triarylamines or phosphorescent metal complexes, and / or charge transport units, especially those based on triarylamines.

The polymers, oligomers and dendrimers according to the invention have advantageous properties, in particular long life spans

Efficiencies and good color coordinates.

The polymers and oligomers according to the invention are generally prepared by polymerizing one or more types of monomer, of which at least one monomer in the polymer leads to repeat units of the formula (I). Suitable polymerization reactions are known to the person skilled in the art and are described in the literature. The following are particularly suitable and preferred polymerization reactions which lead to C-C or C-N linkages:

(A) SUZUKI polymerization;

(B) YAMAMOTO polymerization;

(C) STILLE polymerization; and

(D) HARTWIG-BUCHWALD polymerization. How the polymerization can be carried out according to these methods and how the polymers can then be separated from the reaction medium and purified is known to the person skilled in the art and in

Literature described in detail.

Formulations of the compounds according to the invention are required for processing the compounds containing a structural element of the formula (I) from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures of two or more solvents for this.

Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methylbenzoate, mesitylene, tetralin, veratrol, THF, methyl-TFIF, 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, D-terpineol,

Benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone,

Cyclohexylbenzene, decalin, dodecylbenzene, ethylbenzoate, indane,

Methyl benzoate, NMP, p-cymene, phenetol, 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 also relates to a formulation, in particular a solution, dispersion or emulsion

at least one compound containing a structural element according to the formula (I) or at least one polymer, oligomer or dendrimer containing at least one unit of the formula (I) and at least one

Solvent, preferably an organic solvent. A person skilled in the art knows how such solutions can be prepared.

According to a preferred embodiment of the invention, the formulation also contains the compound according to the application

at least one other matrix material and at least one

phosphorescent emitter. The at least one further matrix material and the at least one phosphorescent emitter are each selected from those given below as preferred

Embodiments. After the solvent has been applied and evaporated from the formulation, the mixture of materials remains as

phosphorescent emitting layer with a mixed matrix.

The compounds according to the application 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 the connections according to the application in electronic devices.

The electronic devices are preferably selected from the group consisting of organic integrated circuits (OlCs), 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 organic electroluminescent devices (OLEDs).

Another object of the invention, as already stated above, is an electronic device containing at least one connection as defined above. The electronic device is preferred

selected from the above devices.

It is particularly preferably an organic electroluminescent device (OLED) containing anode, cathode and at least one emitting layer, characterized in that at least one organic layer, which is preferably selected from emitting layers,

Electron transport layers and hole blocking layers, and which is particularly preferably selected from emitting layers, very particularly phosphorescent emitting layers, contains at least one compound as defined above.

In addition to the cathode, anode and at least one emitting layer, the organic electroluminescent device can also contain further layers. These are selected, for example, 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, intermediate layers (interlayers),

Charge generation layers and / or organic or inorganic p / n transitions.

The sequence of the layers of the organic electroluminescent device is preferred:

Anode / hole injection layer / hole transport layer / optionally further hole transport layer (s) / electron blocking layer / emitting layer / hole blocking layer / electron transport layer / optionally further Electron transport layer (s) / electron injection layer / cathode. Additional layers can also be present in the OLED.

It is preferred if at least one hole-transporting layer of the device is p-doped, that is to say contains at least one p-dopant. P-dopants are preferably selected from electron acceptor compounds. Particularly preferred p-dopants are selected from

Quinodimethane compounds, azaindenofluorodione, azaphenalenes, azatriphenylenes, I2, metal halides, are preferred

Transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal of the 3rd

Main group, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one

Oxygen atom as a binding site. Are also preferred

Transition metal oxides as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re2Ü7 _, M0O3, WO3 and Re03. Also preferred are bismuth complexes, in particular Bi (III) complexes, in particular bismuth complexes with benzoic acid derivatives as complex ligands.

The organic electroluminescent device according to the invention can contain several emitting layers. These emission layers particularly preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H. in the emitting layers there are various emissive

Compounds used that can fluoresce or phosphoresce and that emit blue, green, yellow, orange or red light. Three-layer systems, that is to say systems with three emitting layers, are particularly preferred, with one of the three layers showing blue, one of the three layers green and one of the three layers showing orange or red emission. The invention

Compounds are preferred in the emitting layer available. Instead of several color-emitting emitter connections, an individually used emitter connection can also be suitable for generating white light

Wavelength range emitted.

It is preferred according to the invention if the compounds are used in an electronic device which contains one or more phosphorescent emitting compounds in an emitting layer. The compounds are preferred in the

contain emitting layer in combination with the phosphorescent emitting compound, particularly preferably in a mixture with at least one further matrix material. This is preferably selected from hole-conducting matrix materials, electron-conducting matrix materials and matrix materials which have both hole-conducting properties and electron-conducting properties (bipolar matrix materials), particularly preferably from electron-conducting matrix materials and bipolar matrix materials, very particularly preferably from

electron-conducting matrix materials.

The term phosphorescent emitting compounds preferably includes those compounds in which the light is emitted by a spin-prohibited transition, for example a transition from an excited triplet state or a state with a higher spin quantum number, for example a quintet state.

In a preferred embodiment of the present invention, the compound containing a structural element of the formula (I) is used in an emitting layer as a matrix material in combination with one or more phosphorescent emitting compounds. The phosphorescent emitting compound is preferably a red or green phosphorescent emitter. The total proportion of all matrix materials in the phosphorescent emitting layer in this case is between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferably between 85.0 and 97.0% by volume.

Accordingly, the proportion of the phosphorescent emitting compound is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume and particularly preferably for between 3.0 and 15.0% by volume.

According to an alternative embodiment, the phosphorescent emitting layer contains only one matrix compound, preferably one

Compound containing a structural element of formula (I). In this case, the emitting layer is preferably a red phosphorescent emitting layer.

The phosphorescent emissive layer of the organic

Electroluminescent device preferably comprises two or more

Matrix materials (mixed matrix systems). One of them is preferably a compound containing a structural element of the formula (I). The mixed matrix systems preferably comprise two or three different ones

Matrix materials, particularly preferably two different ones

Matrix materials, one of which is preferably a compound containing a structural element of the formula (I).

According to a preferred embodiment, one of the two matrix materials has the function of a hole-transporting material, and the other of the two matrix materials has the function of an electron-transporting material. The compound containing a structural element of the formula (I) is particularly preferred

electron-transporting material, and the further compound which is present in the emitting layer mixed with the compound containing a structural element of the formula (I) is the hole-transporting material. In In this case, the further compound is preferably selected from carbazole compounds, biscarbazole compounds,

Indolocarbazole compounds and indenocarbazole compounds. These preferably have no electron-poor heteroaromatics

Substituents. In this case, the compound containing a structural element of the formula (I) preferably has one or more

electron-poor fleteroaromatics, preferably triazine, as substituents.

According to an alternative preferred embodiment, the compound containing a structural element of the formula (I) is the hole-transporting matrix material, and the further compound which is present in the emitting layer mixed with the compound containing a structural element of the formula (I) is the electron-transporting matrix material. In this case, the further connection is preferably selected

Carbazole compounds and indenocarbazole compounds. These preferably have one or more electron-deficient aromatics, preferably triazine, as substituents. In this case, the compound containing a structural element of the formula (I) preferably has none

electron-poor fleteroaromatics as substituents.

According to a further preferred embodiment of the invention, one of the two materials is a wide-band gap material, and there are one or two further matrix materials in the emitting layer, by means of which an electron-transporting function and / or a hole-transporting function of the mixed matrix are fulfilled . According to a preferred embodiment, this can be done in that, in addition to the wide-bandgap material, a further matrix material is present in the emitting layer, which has electron-transporting properties, and another matrix material is present in the emitting layer, which is hole-transporting

Has properties. Alternatively and particularly preferably, this can be done in that in addition to the wide bandgap material, a single one further matrix material is present in the emitting layer, which is both electron-transporting and hole-transporting

Has properties. Such matrix materials are also referred to as bipolar matrix materials.

According to a further alternative embodiment, in addition to the wide-bandgap matrix material, only a single further matrix material can be present in the emitting layer, which either

predominantly hole-transporting properties or predominantly electron-transporting properties.

In the preferred case that two different matrix materials are present in the emitting layer, these can be in a volume ratio of 1:50 to 1: 1, preferably 1:20 to 1: 1, particularly preferably 1:10 to 1: 1 and very particularly preferably 1: 4 to 1: 1. The compound containing a structural element of the formula (I) is preferably present in the same proportion as the further matrix compound, or it is present in a higher proportion than the further matrix compound.

The absolute proportion of the compound containing a structural element of the formula (I) in the mixture of the emitting layer, when used as matrix material in a phosphorescent emitting layer, is preferably 10% by volume to 85% by volume, more preferably 20% by volume. % to 85% by volume, even more preferably 30% by volume to 80% by volume, most preferably 20% by volume to 60% by volume and most preferably 30% by volume to 50% by volume. -%. The absolute proportion of the second matrix compound in this case is preferably 15% by volume to 90% by volume, more preferably 15% by volume to 80% by volume, even more preferably 20% by volume to 70% by volume. %, very particularly preferably 40% by volume to 80% by volume, and most preferably 50% by volume to 70% by volume. To produce phosphorescent emitting layers of the mixed-matrix type, a solution containing the phosphorescent emitter and the two or more matrix materials can be prepared in accordance with a preferred embodiment of the invention. This can be applied by means of spin coating, printing processes or other processes. In this case, after the solvent has evaporated, the phosphorescent emitting layer of the mixed matrix type remains.

According to an alternative, more preferred embodiment of the invention, the phosphorescent emitting layer of the mixed-matrix type is produced by gas phase deposition. There are two ways in which the layer can be applied. On the one hand, each of the at least two different matrix materials can be presented in one material source, whereupon the two or more different material sources are evaporated simultaneously (“co-evaporation”). On the other hand, the at least two matrix materials can be premixed and the mixture obtained can be placed in a single material source from which it is finally evaporated. The latter

The process is known as the premix process.

The present application therefore also relates to a mixture comprising a compound of the formulas given above and at least one further compound which is selected from

Matrix connections. For this purpose, the preferred embodiments specified in this application with regard to proportions of the

Matrix compounds and their chemical structure are also preferred.

In an alternative preferred embodiment of the invention, the connection is used as an electron-transporting material. This applies in particular if the compound in particular selects at least one group from electron-poor heteroaryl groups, preferably azine groups Contains triazine groups, pyrimidine groups and pyridine groups, and benzimidazole groups.

If the compound is used as an electron transporting material, then it is preferably in a hole blocking layer, one

Electron transport layer or used in an electron injection layer. In a preferred embodiment, the layer containing the compound containing a structural element of the formula (I) is then n-doped, or it is in a mixture with another

electron-transporting compound, preferably lithium quinolinate (LiQ). The compound containing a structural element of the formula (I) can also be present in the layer selected from the hole blocking layer, electron transport layer and electron injection layer, but also as a pure material.

In the present case, an n-dopant is an organic or

understood inorganic compound that is able to donate electrons (electron donor), i.e. a connection that as

Reducing agent works. The compounds used for n-doping can be used as precursors, these precursor compounds releasing n-dopants by activation. N-dopants are preferably selected from electron-rich metal complexes; P = N compounds; N-heterocycles, particularly preferred

Naphthylene carbodiimides, pyridines, acridines and phenazines; Fluorenes and radical compounds.

The following are preferred embodiments for the

different functional materials of the electronic device listed.

Preferred fluorescent emitting compounds are selected from the class of arylamines. Under an arylamine or a

aromatic amine in the sense of this invention is a compound understood that contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bound directly to the nitrogen. At least one of these is preferred aromatic or hetero

aromatic ring systems a condensed ring system, particularly preferably with at least 14 aromatic ring atoms. Preferred examples of this are aromatic anthracenamines, aromatic

Anthracene diamines, aromatic pyrenamines, aromatic pyrendiamines, aromatic chrysenamines or aromatic chrysediamines. An aromatic anthracenamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position. An aromatic anthracene diamine 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, pyrendiamines, chrysenamines and chrysenamines are defined analogously, the diarylamino groups being preferably attached to the pyrene in the 1-position or in the 1,6-position. Further preferred emitting compounds are indenofluorenamines or -diamines, benzoindenofluorenamines or -diamines, and dibenzoindenofluoramines or -diamines, and also indenofluorene derivatives with condensed aryl groups. Pyrene-arylamines are also preferred. Also preferred are benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives which are linked to furan units or to thiophene units.

Preferred matrix materials for fluorescent emitters are selected from the classes of the oligoarylenes (e.g. 2,2 ', 7,7'-tetraphenylspirobifluorene), in particular the oligoarylenes containing condensed aromatic groups, the oligoarylenevinylenes, the polypodal metal complexes, the hole-conducting compounds, the electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides; the atropisomers, the boronic acid derivatives or the

Benzanthracenes. Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, oligoarylenvinylenes, ketones, phosphine oxides and 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. For the purposes of this invention, an oligoarylene is to be understood as a compound in which at least three aryl or arylene groups are bonded to one another.

Particularly suitable phosphorescent emitting compounds (= triplet emitters) are compounds which, when suitably excited, emit light, preferably in the visible range, 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 . Compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used as phosphorescent emitting compounds, in particular compounds which contain iridium, platinum or copper. For the purposes of the present invention, all luminescent iridium, platinum or copper complexes are considered

viewed phosphorescent emissive compounds.

In general, all phosphorescent complexes are suitable, as they are used according to the prior art for phosphorescent OLEDs and as are known to the person skilled in the art in the field of organic electroluminescent devices. Explicit examples of particularly suitable complexes are listed in the following table.

In addition to the compounds according to the application, preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl) or carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, aza-carbazole derivatives, bipolar matrix materials, silanes, azaboroles or boronic esters, triazine derivatives, zinc complexes, diazasilol or tetraazasilol derivatives, carbohydrate derivatives, dibenzazole derivatives, carboxylate derivatives, dibenzazolazole derivatives, dibenzazole derivatives, dicarboxyl derivatives, Derivatives,

Triphenylene derivatives, or lactams. The is particularly preferred

Compound containing a structural element of formula (I) in the

emitting layer in combination with a phosphorescent emitter and a further matrix material, which is preferably selected from the above-mentioned preferred matrix materials and is particularly preferably selected from carbazole compounds,

Biscarbazole compounds, indolocarbazole compounds and

Indenocarbazole compounds.

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

Electron transport layer of the electronic according to the invention

Device can be used, for example, are those in Y.

Shirota et al., Chem. Rev. 2007, 107 (4), 953-1010

Compounds or other materials as are used in these layers according to the prior art. As materials for the electron transporting layers of the

Device are particularly suitable aluminum complexes, for example Alq3, zirconium complexes, for example Zrq ₄ , 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, diazaphosphole derivatives and phosphine oxide derivatives.

Particularly preferred compounds for use in

Electron transporting layers are shown in the following table:

Preferred materials for hole-transporting layers of OLEDs are indenofluorenamine derivatives, amine derivatives,

Hexaazatriphenylene derivatives, amine derivatives with condensed aromatics, monobenzoindenofluorenamines, dibenzoindenofluorenamines,

Spirobifluorene amines, fluorene amines, spirodibenzopyran amines,

Dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, spiro-bisacridines, xanthene-diarylamines, and 9,10-dihydroanthracene-spiro-amine compounds are used.

Furthermore, the following compounds HT-1 to HT-72 are suitable for use in a layer with a hole-transporting function, in particular in a hole-injection layer, a hole-transport layer and / or an electron blocking layer, or for use in an emitting layer as a matrix material, in particular as a matrix material in one emitting layer containing one or more

phosphorescent emitters:

The compounds HT-1 to HT-72 are generally well suited for the above-mentioned uses in OLEDs of all types and

Composition, not only in OLEDs according to the present

Registration. The connections show good performance data in OLEDs, in particular good service life and good efficiency.

Processes for the preparation of the compounds HT-1 to HT-72 are known in the prior art. For example, processes for the preparation of the compounds HT-16, HT-17 and HT-72 are disclosed in WO2014 / 079527, there on pages 32-33 and in the exemplary embodiments. Manufacturing process of the compound HT-18 are disclosed in WO 2013/120577 and W02017 / 144150 in the description and the exemplary embodiments. Methods for producing the compounds HT-20 to HT-32 are disclosed in WO2012 / 034627, there on p. 39-40 and in the exemplary embodiments.

Metals with a low work function, metal alloys or multilayer structures are made as the cathode of the electronic device

various metals are preferred, such as, for example, alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Alloys made of an alkali or alkaline earth metal and silver, for example an alloy of, are also suitable

Magnesium and silver. In the case of multilayer structures, other metals can also be used in addition to the metals mentioned, which have a relatively high work function, such as, for example, B. Ag or Al, in which case combinations of the metals, such as Ca / Ag, Mg / Ag or Ba / Ag are usually used. It can also be preferred to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. For example, alkali metal or

Alkaline earth metal fluorides, but also the corresponding oxides or

Carbonates in question (e.g. LiF, L12O, BaF2, MgO, NaF, CsF, CS2CO3, etc.). Lithium quinolinate (LiQ) can also be used. The

The layer thickness of this layer is preferably between 0.5 and 5 nm.

Materials with a high work function are preferred as the anode. The anode preferably has a work function greater than 4.5 eV vs. Vacuum on. Metals with a high redox potential are suitable for this, such as Ag, Pt or Au. On the other hand, metal / metal oxide electrodes (eg Al / Ni / NiO _x , Al / PtO _x ) can also be preferred. For some applications, at least one of the electrodes must be transparent or

be partially transparent to either the irradiation of the organic

Materials (organic solar cell) or the extraction of light (OLED, O-LASER). Preferred anode materials here are conductive mixed metal oxides. Indium tin oxide (ITO) or indium zinc oxide (IZO) are particularly preferred. Also preferred are conductive, doped organic materials, in particular conductive doped polymers. Furthermore, the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.

The device is structured (depending on the application), contacted and finally sealed in order to exclude damaging effects of water and air.

In a preferred embodiment, the electronic device is characterized in that one or more layers are coated using a sublimation process. The materials are evaporated in vacuum sublimation systems at an initial pressure of less than 10 ⁵ mbar, preferably less than 10 ⁶ mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10 ⁷ mbar.

An electronic device is also preferred

characterized that one or more layers with the OVPD

(Organic Vapor Phase Deposition) process or with the help of a

Carrier gas sublimation are coated. The materials are applied at a pressure between 10 ⁵ mbar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and structured in this way (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

An electronic device is also preferred

characterized in that one or more layers of solution, such as. B. by spin coating, or by any printing method, such as. B. 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). Soluble connections are necessary for this. High solubility can be achieved by suitable substitution of the compounds.

It is further preferred that one or more layers of solution and one or more layers are applied by a sublimation process to produce an electronic device according to the invention.

Electronic devices containing one or more connections as defined above are preferred in displays as light sources in

Illumination applications and as light sources in medical and / or cosmetic applications (e.g. light therapy).

Examples

A) Synthesis examples

Example a: 7-bromo-6H-indolo [1,2-a] quinazolin-5-one

5.5 g (23.5 mmol) of 6H-indolo [1, 2-a] quinazolin-5-one are placed in 150 ml of CH 2 Cl 2. A solution of 4 g (22.5 mmol) of NBS in 100 ml of acetonitrile is then added dropwise at 0.degree. C., the mixture is allowed to come to room temperature and the mixture is stirred for a further 4 h at this temperature. Then the mixture is mixed with 150 mL water and with CH2CI2 extracted. The organic phase is dried over MgSO4 and the solvents are removed in vacuo. The product is stirred hot with hexane and suction filtered. Yield: 5.5 g (17.6 mmol), 75% of theory. Th., Purity according to ¹ H-NMR about 98%.

The following connections are obtained analogously:

Example b: 7-bromo-6- (3,5-diphenylphenyl) indolo [1,2-a] quinazolin-5-one

31 g (100 mmol) 7-bromo-6H-indolo [1, 2-a] quinazolin-5-one, 106 g (300 mmol) 5'-iodo- [1, 1 '; 3', 1 "] terphenyl , 2.3 g (20 mmol) L-proline and 5.2 g (27mmol, 0.11 eq) copper (l) iodide are stirred in 100 ml at 150 ° C for 30 h

The solution is diluted with water, extracted twice with ethyl acetate, the combined organic phases are dried over Na2SO4 and evaporated. The residue is purified by chromatography (EtOAc / hexane: 2/3). The yield is 30 g (57 mmol) 57% of theory.

The following connections are obtained analogously:

Example c: 6- (3,5-diphenylphenyl) -7-phenyl-indolo [1, 2-a] quinazolin-5-one 13.3 g (110.0 mmol) phenylboronic acid, 59 g (110.0 mmol) 7-bromo-6- (3,5-diphenylphenyl) indolo [1, 2-a] quinazolin-5-one and 44.6 g (210.0 mmol) tripotassium phosphate are dissolved in 500 ml of toluene, 500 ml of dioxane and 500 ml of water are suspended. 913 mg (3.0 mmol) of tri-tolylphosphine and then 112 mg (0.5 mmol) of palladium (II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and then concentrated to dryness. The residue is recrystallized from toluene and from dichloromethane / isopropanol and finally sublimed in a high vacuum. The purity is 99.9%. The yield is 77 g (88 mmol),

corresponding to 80% of theory.

The following connections are obtained analogously:

Example d: Indolo [1,2-a] benzimidazol-11-one oxime 138479 49-9 1

33 g (147 mmol) of indolo [1, 2-a] benzimidazol-11-one are placed in 300 ml of pyridine / 200 methanol, and then 20.5 g of hydroxylammonium chloride are added in portions. The mixture is then heated at 60 ° C for 3.5 hours. After the reaction has ended, the precipitated solid is filtered off with suction and washed with water and 1 M HCl and then with methanol. The yield is 32.4 g (138 mmol), corresponding to 92% of theory.

The following connections can be made analogously:

Example e: Lactam synthesis

A) 5H-Benzimidazolo [1, 2-a] quinoxalin-6-one

B) 6H-Benzimidazolo [1, 2-a] quinazolin-5-one

33 g (140 mmol) of indolo [1, 2-a] benzimidazol-11-one oxime are placed in 300 ml of polyphosphoric acid and finally heated to 170 ° C. for 12 hours. When the reaction has ended, the mixture is poured onto ice, extracted with ethyl acetate, separated and concentrated. The precipitated solid is filtered off and washed with ethanol. The isomers are separated chromatographically.

Yield: 30 g (127 mmol) of the mixture A + B, 94% of theory. Th .; Purity: 98.0% by HPLC. After recrystallization from ethyl acetate / toluene (1: 3), 14 g (42%) (A) and 16 g (48%) (B) are obtained.

The following connections are made analogously:

Example f) 5- (3-phenylphenyl) benzimidazolo [1, 2-a] quinoxalin-6-one

13.5 g (25 mmol, 1.00 eq.) 5H-benzimidazolo [1, 2-a] quinoxalin-6-one, 21.3 ml (128 mmol, 5.2 eq.) 3-bromobiphenyl and 7.20 g potassium carbonate (52.1 mmol, 2.10 eq.) are placed in 220 ml of dried DMF and rendered inert with argon. Then 0.62 g (2.7 mmol, 0.11 eq) 1, 3-di (2-pyridyl) -1, 3-propanedione and 0.52 g (2.7 mmol, 0.11 eq) copper (I) iodide are added and the mixture for three days heated at 140 ° C. When the reaction has ended, the mixture is carefully concentrated on a rotary evaporator, the precipitated solid is filtered off with suction and washed with water and ethanol. The crude product is purified twice using a fleece extractor (toluene / fleptan 1: 1) and the solid obtained is recrystallized from toluene. After sublimation, 8.2 g (12 mmol, 48%) of the desired target compound are obtained.

The following connections can be made analogously:

Example g) 5-phenyl-3- (9-phenylcarbazol-3-yl) benzimidazolo [1,2-a] quinoxalin-6-one

27.3 (70 mmol) 3-bromo-5-phenyl-benzimidazolo [1, 2-a] quinoxalin-6-one, 20.8 g (75 mmol) phenylcarbazol-3-boronic acid and 14.7 g (139 mmol ) Sodium carbonate are suspended in 200 ml of toluene, 52 ml of ethanol and 100 ml of water. 80 mg (0.69 mmol) of tetrakisphenylphosphine-palladium (O) are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and then concentrated to dryness. The residue is recrystallized from heptane / dichloromethane. The yield is 29 g (54 mmol), corresponding to 77% of theory.

The following connection is obtained analogously:

Example h: 2- (2,5-dibromopyrrol-1-yl) -N1, N3-diphenyl-benzene-1,3-dicarboxamide

[146431-46-1] 4.5 g (12 mmol) of N1, N3-diphenyl-2-pyrrole-1-yl-benzene-1,3-dicarboxamide are placed in 150 ml of CH2Cl2. A solution of 4 g (22.5 mmol) of NBS in 100 ml of acetonitrile is then added dropwise at -5.degree. C., the mixture is allowed to come to room temperature and the mixture is stirred for a further 4 h at this temperature. Then the mixture is mixed with 150 mL water and extracted with CH2CI2. The organic phase is dried over MgSO4 and the solvents are removed in vacuo. The product is stirred hot with hexane and suction filtered. Yield: 3.9 g (17.6 mmol), 70% of theory. Th., Purity according to ¹ H-NMR about 98%.

Example i: Cyclization:

11.8 g (25 mmol) of 2- (2,5-dibromopyrrol-1-yl) -N1, N3-diphenyl-benzene-1,3-dicarboxamide are dissolved in 600 ml of toluene and degassed with argon for 30 minutes. Then 8.1 g (84.8 mmol) of sodium f-butoxide, 476 mg (2.12 mmol) of palladium (II) acetate and 4.2 ml (4.24 mmol) of tri-f-butylphosphine (10M in toluene) are added and stirred under reflux overnight. After the reaction has ended, 200 ml of water are added, the organic phase is separated off and extracted twice with water. The organic phase is dried over sodium sulfate and concentrated to approx. 80 ml on a rotary evaporator. The fancy

Solid is suctioned off and purified by hot extraction in toluene. The product is recrystallized three times with toluene / heptane and

finally sublimated. 6.6 g (17.0 mmol, 71%) of the desired target compound with an HPLC purity> 99.9% are obtained. B) Device examples

The use of the materials according to the invention in OLEDs is presented in the following examples.

Glass plates that are coated with structured ITO (indium tin oxide) with a thickness of 50 nm are first treated with an oxygen plasma, followed by an argon plasma, before the coating. These glass plates, which have been treated with plasma, form the substrates to which the OLEDs are applied.

The OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electrons

blocking layer (EBL) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) and finally a cathode. The cathode is formed by a 100 nm thick aluminum layer. The exact structure of the OLEDs can be found in Tables 1a to 1c. The data of the OLEDs are listed in Tables 2a to 2c. The materials required to manufacture the OLEDs are shown in Table 3.

All materials are thermally evaporated in a vacuum chamber. The emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material or the matrix materials by cover vaporization in a certain volume fraction. An indication like A: B: C (45%: 45%: 10%) means that material A in a volume fraction of 45%, material B in a volume fraction of 45% and material C in a volume fraction of 10 % is present in the shift. Analogously, the electron transport layer or one of the other layers can also consist of a mixture of two materials. The OLEDs are characterized by default. For this purpose, the electroluminescence spectra and the external quantum efficiency (EQE, measured in%) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics, assuming a Lambertian radiation characteristic. The electroluminescence spectra are determined at a luminance of 1000 cd / m ² and the CIE 1931 x and y color coordinates are calculated therefrom. EQE1000 describes the external quantum efficiency that is achieved at 1000cd / m ² .

In Examples E1 to E6, the materials according to the invention are used as matrix material in the emission layer of green phosphorescent OLEDs.

Table 1a: Structure of the OLEDs

Very good results are obtained for all compounds according to the invention

Obtain results for external quantum efficiency.

Table 2a: Data of the OLEDs

Further materials according to the invention are used in Examples E7 to E9 as matrix material in the emission layer of red-phosphorescent OLEDs.

Table 1 b: Structure of the OLEDs

Very good results for the external quantum efficiency are obtained for the two compounds according to the invention.

Table 2b: OLED data

Another material according to the invention is used in Examples E10 and E11 as ETL and HBL of blue fluorescent OLEDs. Use as ETL and HBL in phosphorescent OLEDs is also possible.

Table 1c: Structure of the OLEDs

Very good results for the external quantum efficiency are obtained for the connection according to the invention, with operating voltages U1000 in the range of 4-5 V.

Table 3: Structural formulas of the materials for the OLEDs

Claims

Expectations 1 . Electronic device containing a compound containing a structural element of a formula (I) Formula (I) where: Z ¹ is the same or different at each occurrence C, CR ¹ or N; Z ² is the same or different at each occurrence C, CR ² or N; Each occurrence of T ¹ is chosen the same or different from - (C = 0) (NAr ¹ ) -, - (C = S) (NAr ¹ ) -, - (S0 ₂ ) (NAr ¹ ) -, and - (C = 0) 0-; Ar ¹ is selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with one or more radicals R ³ and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with one or more radicals R ³ ; Each occurrence of R ¹ is the same or different from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C- Atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ¹ can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced; Each occurrence of R ² is the same or different from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ² can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced; Each occurrence of R ³ is chosen identically or differently from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C- Atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^{3 may} be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced; Each occurrence of R ⁴ is the same or different from H, D, F, CI, Br, I, C (= 0) R ⁵ , CN, Si (R ⁵ ) ₃ , N (R ⁵ ) ₂ , P (= 0) (R ⁵ ) ₂ , OR ⁵ , S (= 0) R ⁵ , S (= 0) ₂ R ⁵ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^{3 may} be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁵ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁵ C = CR ⁵ -, -C ^ C-, Si (R ⁵ ) 2, C = 0, C = NR ⁵ , -C (= 0) 0-, -C (= 0) NR ⁵ -, NR ⁵ , P (= 0) (R ⁵ ), -O-, -S-, SO or SO2 can be replaced; Each occurrence of R ⁵ is selected identically or differently from H, D, F, CI, Br, I, CN, alkyl or alkoxy groups with 1 to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ⁵ can be linked to one another and form a ring; and wherein said alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted with one or more radicals selected from F and CN; k is 0 or 1, where in the case of k = 1 the groups Z ¹ and Z ² which bind to the relevant group T ¹ are C and are connected to one another via the group T ¹ , and where in the case of k = 0 the the relevant group T ^{1 is} not present, and the relevant groups Z ¹ and Z ^{2 are} not connected to one another. 2. Electronic device according to claim 1, characterized in that T ^{1 is} equal to - (C = 0) (NAr ¹ ) -. 3. Electronic device according to claim 1 or 2, characterized characterized in that Ar ^{1 is selected the} same or different for each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, triazinyl, pyrimidyl, pyridyl, quinazoline, quinoxaline, quinoxaline where the groups mentioned can each be substituted by one or more radicals R ³ . 4. Electronic device according to one or more of claims 1 to 3, characterized in that Z ¹ is chosen the same or different from C and CR ¹ with each occurrence. 5. Electronic device according to one or more of claims 1 to 4, characterized in that k is 0. 6. Electronic device according to one or more of claims 1 to 5, characterized in that R ¹ is chosen the same or different for each occurrence from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R ⁴ ; and R ² is chosen the same or different for each occurrence from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R ⁴ ; and R ³ is chosen the same or different for each occurrence from H, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R ⁴ ; and - R ⁴ is chosen the same or different for each occurrence from H, D, F, CN, Si (R ⁵ ) 3, N (R ⁵ ) ₂ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic Alkyl or alkoxy groups with 3 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; said alkyl and Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ⁵ ; and wherein in the said alkyl or alkoxy groups one or more CFh groups by -C ^ C-, -R ⁵ C = CR ⁵ -, Si (R ⁵ ) 2, C = 0, C = NR ⁵ , -NR ⁵ -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ⁵ - can be replaced; and - R ^{5 is} equal to Fl. 7. Electronic device according to one or more of claims 1 to 6, characterized in that the compound containing a structural unit according to formula (I) corresponds to one of the following formulas: in which Ar ^{2 is} selected from aromatic ring systems with 4 to 40 aromatic ring atoms which are substituted with radicals R ^A and heteroaromatic ring systems with 3 to 40 aromatic ring atoms which are substituted with radicals R ^A , where R ^A is chosen the same or different for each occurrence from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^A can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CH ₂ groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) ₂ , C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or S0 ₂ can; and where Z ^{1 is the} same or different at each occurrence CR ¹ or N; and wherein the other symbols are defined as in one or more of claims 1 to 6. 8. Electronic device according to claim 7, characterized in that Ar ^{2 is} fused benzene that is substituted with one or more radicals R ^A. 9. Electronic device according to claim 7 or 8, characterized characterized in that R ^{A is the} same or different in each occurrence is selected from H, D, F, CN, Si (R ⁴ ) 3, N (R ⁴ ) 2, straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 C- Atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic Ring systems with 5 to 40 aromatic ring atoms; wherein said alkyl and alkoxy groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with R ⁴ groups. 10. Electronic device according to claim 9, characterized in that it is an organic electroluminescent device and contains anode, cathode and at least one emitting layer, and that the compound containing a structural element of the formula (I) in an emitting layer together with at least one phosphorescent emitter is contained, or that the compound containing a structural element of formula (I) selected in a layer selected from hole blocking layers, electron transport layers and Electron injection layers are included. 11. Organic electroluminescent device according to claim 10, characterized in that the compound containing a structural element of the formula (I) is contained in an emitting layer of the device together with at least one phosphorescent emitter and at least one further compound, the further compound being a matrix material. 12. Organic electroluminescent device according to claim 11, characterized in that the further connection is selected from hole transporting matrix materials, preferably carbazole compounds, Biscarbazole compounds, indolocarbazole compounds and indenocarbazole compounds. in which Ar ^{2 is} selected from aromatic ring systems with 4 to 40 aromatic ring atoms which are substituted with radicals R ^A and heteroaromatic ring systems with 3 to 40 aromatic ring atoms which are substituted with radicals R ^A , where R ^A is chosen the same or different for each occurrence from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^A can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CH ₂ groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) ₂ , C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or S0 ₂ can; and where Z ^{1 is the} same or different at each occurrence CR ¹ or N; Ar ^{1 is} selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with one or more radicals R ³ and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with one or more radicals R ³ ; R ^{1 is selected the} same or different for each occurrence from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ¹ can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced; R ^{2 is selected the} same or different for each occurrence from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein two or more radicals R ² can be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced; R ^{3 is selected the} same or different for each occurrence from H, D, F, CI, Br, I, C (= 0) R ⁴ , CN, Si (R ⁴ ) ₃ , N (R ⁴ ) ₂ , P (= 0) (R ⁴ ) ₂ , OR ⁴ , S (= 0) R ⁴ , S (= 0) ₂ R ⁴ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^{3 may} be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁴ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁴ C = CR ⁴ -, -C ^ C-, Si (R ⁴ ) 2, C = 0, C = NR ⁴ , -C (= 0) 0-, -C (= 0) NR ⁴ -, NR ⁴ , P (= 0) (R ⁴ ), -O-, -S-, SO or SO2 can be replaced; R ⁴ is chosen the same or different for each occurrence from H, D, F, CI, Br, I, C (= 0) R ⁵ , CN, Si (R ⁵ ) ₃ , N (R ⁵ ) ₂ , P (= 0) (R ⁵ ) ₂ , OR ⁵ , S (= 0) R ⁵ , S (= 0) ₂ R ⁵ , straight-chain alkyl or alkoxy groups with 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups with 3 up to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ^{3 may} be linked to one another and form a ring; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ⁵ ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ⁵ C = CR ⁵ -, -C ^ C-, Si (R ⁵ ) 2, C = 0, C = NR ⁵ , -C (= 0) 0-, -C (= 0) NR ⁵ -, NR ⁵ , P (= 0) (R ⁵ ), -O-, -S-, SO or SO2 can be replaced; R ^{5 is selected the} same or different for each occurrence from H, D, F, CI, Br, I, CN, alkyl or alkoxy groups with 1 to 20 C atoms, alkenyl or alkynyl groups with 2 to 20 C atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R ⁵ can be linked together and form a ring; and wherein said alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted with one or more radicals selected from F and CN; wherein at least one group R ¹ , R ² , R ³ or R ^{A is} present, which is selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R ⁴ (radical A), - Heteroaromatic ring systems with 5 to 40 aromatic Ring atoms which are substituted by radicals R ⁴ (radical B), - N (R ⁴ ) ₂ (residue C). 14. oligomer, polymer or dendrimer containing one or more compounds according to claim 13, wherein the bond (s) to the polymer, oligomer or dendrimer are located at any position in formula (I) substituted by R ¹ , R ² or R ³ can. 15. Formulation containing at least one compound according to claim 13 or at least one polymer, oligomer or dendrimer according to claim 14, and at least one solvent. 16. Use of a compound according to claim 13 in one electronic device. 17. A method for freezing a connection according to claim 13, characterized in that either a) starting from a compound of formula (lnt-1) or (lnt-ll) wherein HetAr is a heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is substituted with radicals R ² , and Z ¹ in each Occurrence is the same or different CR ¹ or N, in a first step a halogen substituent is introduced, preferably CI, Br or I, in a second step in an Ullmann coupling reaction on the nitrogen atom of the lactam group an aromatic or heteroaromatic ring system is introduced, and in a third step in the position of the halogen substituent an amino group is introduced via a Buchwald coupling which carries aromatic or heteroaromatic ring systems as a substituent, or an aromatic or heteroaromatic ring system is introduced via a Suzuki coupling; or b) starting from a compound of a formula (Int-Ill) Formula (Int-Ill) where Z ^{1 is the} same or different CR ¹ or N at each occurrence; and HetAr is a heteroaromatic ring system with 5 to 40 aromatic ring atoms, which is substituted with radicals R ² ; and Ar ^{1 is selected the} same or different at each occurrence from aromatic Ring systems with 6 to 40 aromatic ring atoms, which are substituted by one or more radicals R ³ , and heteroaromatic Ring systems with 5 to 40 aromatic ring atoms which are substituted by one or more R ³ radicals; in a first step, halogen substituents, preferably Br, are introduced in the two positions vicinal to the N atom of HetAr, and in a second step the amide groups of the formula (Int-III) in a metal-catalyzed coupling reaction at the positions of Bind halogen substituents to HetAr to form two lactam rings; or c) a starting compound of a formula (Int-IV) Formula (Int-IV), where Ar is an aromatic ring system with 6 to 40 aromatic Is a ring atom which is substituted by radicals R ² and where Z ^{1 is the} same or different at each occurrence CR ¹ or N; in a first step on the corresponding ketone group Hydroxylamine derivative is implemented, this hydroxylamine derivative then in in a second step in a Beckmann rearrangement, and the lactam derivative obtained is then reacted in a third step on the nitrogen of the lactam unit in a Ullmann coupling. 18. Mixture containing at least one compound according to claim 13 and at least one further compound which is selected from Matrix materials for phosphorescent emitters.