EP3887378A1

EP3887378A1 - Electronic device

Info

Publication number: EP3887378A1
Application number: EP19794556.1A
Authority: EP
Inventors: Florian MAIER-FLAIG; Christian EICKHOFF; Frank Voges; Elvira Montenegro; Teresa Mujica-Fernaud; Rémi Manouk ANÉMIAN; Aaron Lackner; Jens ENGELHART
Original assignee: Merck Patent GmbH
Current assignee: Merck Patent GmbH
Priority date: 2018-11-29
Filing date: 2019-10-28
Publication date: 2021-10-06
Also published as: WO2020108899A1; US20230058635A1; CN113227105A; JP2022513170A; KR20210096170A; TW202031865A

Abstract

The invention relates to an electronic device, to the use of same, and to a method for producing same.

Description

Electronic device

The present application relates to an electronic device which contains certain amine compounds in a hole-transporting layer and which contains emissive compounds of a certain structure type in an emitting layer.

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 still great interest in improving the performance data.

A variety of different materials are known as materials for hole-transporting layers in electronic devices, most of which belong to the class of triarylamines, such as

for example N, N '-di (1-naphthyl) - N, N

diphenyl- (1, 1'-biphenyl) -4,4'-diamine (NPD) or tris- (4-carbazolyl-9-ylphenyl) amine (TCTA).

A large number of different connections are also known as emitting connections in electronic devices. in the

Fluorescent compounds, for example pyrenamines, or phosphorescent compounds are essentially used for this use Connections that are usually chosen from

Transition metal complexes with an organometallic bond, in particular iridium complexes such as lr (PPy) 3 (tris [2-phenylpyridinato-C ² , / \ /] iridium (III)). Bridged triarylboron compounds with a certain structure were also used as fluorescent compounds. A high external quantum efficiency was found for these compounds in certain structures when used as emitters in OLEDs.

It is therefore of great interest to appropriately combine these connections with other connections in other layers of the electronic device in order to achieve good properties of the electronic device, in particular with regard to

Lifetime, efficiency, operating voltage, low roll-off and narrow emission band, i.e. an emission band with the smallest possible half-width.

In corresponding studies it has now been found that the

Combination of certain spirobifluorenyl amines or fluorenyl amines in a hole-transporting layer with the above-mentioned triarylboron derivatives in an emitting layer leads to particularly good properties of the electronic device, in particular long life, high efficiency, low operating voltage, low roll-off and

Emission with the smallest possible half-width.

The present invention thus relates to an electronic one

Device, comprising a first electrode, a second electrode, and arranged in between

- An emitting layer E containing a compound of a formula

(E-1), for which applies:

T is B, P, P (= 0) or SiR ^E1 ;

Each occurrence of X is the same or different from O, S, NR ^E2 and C (R ^E2 ) 2, whereby at least one X must be present, which is selected from O, S and NR ^E2 ;

C ¹ , C ² and C ³ are selected identically or differently from ring systems with 5 to 40 ring atoms which are substituted with radicals R ^E3 ;

R ^E1 is selected from H, D, F, CI, Br, I, C (= 0) R ^E4 , CN, Si (R ^E4 ) ₃ , N (R ^E4 ) ₂ , P (= 0) (R ^E4 ) ₂ , OR ^E4 , S (= 0) R ^E4 , S (= 0) ₂ R ^E4 , 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; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ^E4 ; and wherein one or more CH ₂ groups in said alkyl, Alkoxy, alkenyl and alkynyl groups by -R ^E4 C = CR ^E4 -, -C = C-, Si (R ^E4 ) 2, C = 0, C = NR ^E4 , -C (= 0) 0-, -C (= 0) NR ^E4 -, NR ^E4 , P (= 0) (R ^E4 ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ^E2 is the same or different from H, D, F, CI, Br, I, C (= 0) R ^E4 , CN, Si (R ^E4 ) ₃ , N (R ^E4 ) ₂ , P (= 0) (R ^E4 ) ₂ , OR ^E4 , S (= 0) R ^E4 , S (= 0) ₂ R ^E4 , 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 said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic

Ring systems are each substituted with radicals R ^E4 ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ^E4 C = CR ^E4 -, -C = C-, Si (R ^E4 ) ₂ , C = 0,

C = NR ^E4 , -C (= 0) 0-, -C (= 0) NR ^E4 -, NR ^E4 , P (= 0) (R ^E4 ), -O-, -S-, SO or S0 ₂ replaced could be; where two or more radicals R ^E2 can be linked to one another and form a ring, and wherein one or more radicals R ^{E2 can be} linked via their radicals R ^E4 to a ring selected from C ¹ , C ² and C ³ and form a ring can;

With each occurrence, R ^E3 is chosen identically or differently from H, D, F, CI, Br, I, C (= 0) R ^E4 , CN, Si (R ^E4 ) ₃ , N (R ^E4 ) ₂ , P (= 0) (R ^E4 ) ₂ , OR ^E4 , S (= 0) R ^E4 , S (= 0) ₂ R ^E4 , 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 R ^E3 radicals 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 ^E4 ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ^E4 C = CR ^E4 -, -C ^ C-, Si (R ^E4 ) 2, C = 0, C = NR ^E4 , -C (= 0) 0-, -C (= 0) NR ^E4 -, NR ^E4 , P (= 0) (R ^E4 ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ^E4 is chosen the same or different from H, D, F, CI, Br, I, C (= 0) R ^E5 , CN, Si (R ^E5 ) ₃ , N (R ^E5 ) ₂ , P (= 0) (R ^E5 ) ₂ , OR ^E5 , S (= 0) R ^E5 , S (= 0) ₂ R ^E5 , 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 R ^E4 radicals 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 R ^E5 radicals; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ^E5 C = CR ^E5 -, -C ^ C-, Si (R ^E5 ) 2, C = 0, C = NR ^E5 , -C (= 0) 0-, -C (= 0) NR ^E5 -, NR ^E5 , P (= 0) (R ^E5 ), -O-, -S-, SO or SO2 can be replaced;

With each occurrence, R ^E5 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; where two or more R ^E5 radicals 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; o and p are identical or different 0 or 1, where p = 0 and o = 0 means that the group X indicated with p and o, together with their bonds to the rings C ¹ , C ² and C ^3, is omitted;

- A layer H1 between the first electrode and the

emitting layer is arranged, and which contains a compound of a formula (L-1), (L-2) or (L-3)

Formula (L-3) for which the following applies:

Z is C when a group - [Ar ¹ ] _n -N (Ar ² ) 2 is attached to it, and Z is when no group - [Ar ¹ ] _n -N (Ar ² ) 2 is attached to it, with each occurrence the same or different N or CR ¹ ;

Ar ¹ is the same or different at each occurrence an aromatic ring system with 6 to 40 aromatic ring atoms which is substituted by R ³ radicals or a heteroaromatic ring system with 5 to 40 aromatic ring atoms which is substituted by R ³ radicals;

Ar ² is the same or different at each occurrence an aromatic ring system with 6 to 40 aromatic ring atoms which is substituted by R ³ radicals or a heteroaromatic ring system with 5 to 40 aromatic ring atoms which is substituted by R ³ radicals;

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 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 CF 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 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 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 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 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 CF 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 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 ⁴ 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 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; n is the same or different at each occurrence 0, 1, 2, 3 or 4; k is 0 or 1; and

a layer H2 which is arranged between the layer H1 and the emitting layer.

If the index n is 0, this means that the group -N (Ar ² ) 2 and the spirobifluorenyl or fluorenyl or indenofluorenyl basic structure are linked directly to one another. If the index n is 2, 3, or 4, it means that two, three or four groups Ar ¹ in series

are bound in a row.

The groups “C” in formula (E-1) denote carbon atoms which are part of the ring systems C ¹ , C ² and C ³ . The arc between the C atoms indicates that double bonds exist in such a way that all C atoms each have four bonds and three groups each attached to them.

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

The term “ring system” is understood to mean any rings which can be individual rings, or a system comprising a plurality of individual rings condensed with one another, as occurs, for example, in decalin or fluorene. The rings can be the same or different aliphatic, heteroaliphatic, aromatic or heteroaromatic. The ring atoms can be selected from carbon and fleteroatoms, in particular C, O, S, Si, B, P and N. 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 individual aromatic cycles condensed with one another. 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, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, benzimidazolo [ 1, 2- a] benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole,

Pyrazinimidazole, quinoxaline imidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline, azachazidine, pyrazin 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 with aromatic ring system is the case, the heteroaromatic

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, truxene, indenofluorene , 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 CH2 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-ethylhexylthio, Trifluoromethylthio, pentafluoroethylthio, 2,2,2-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 is preferably equal to B.

X is preferably chosen the same every time it occurs. X is particularly preferably NR ^E2 each time it occurs. At least one of the indices o and p is preferably 1, so that at least two groups X are present in the compound, and at least two groups X in the compound are selected from O, S and NR ^E , particularly preferably NR ^E.

C ¹ , C ² and C ³ are preferably chosen to be the same each time they occur. They are furthermore preferably selected from ring systems in which the ring atoms are selected from C, Si, N, P, O, S, B. The ring systems can be aliphatic, aromatic, heteroaliphatic or heteroaromatic. The individual ring which contains the C atoms shown in formula (E-1) is preferably aromatic or heteroaromatic, particularly preferably aromatic.

C ¹ , C ² and C ^{3 are} preferably aromatic or heteroaromatic, particularly preferably aromatic. C ¹ , C ² and C ³ are preferred for each Appearance the same or different, preferably the same, selected from benzene, naphthalene, fluorene, carbazole, dibenzofuran and dibenzothiophene, each of which is substituted by radicals R ^E3 . C ¹ , C ² and C ³ are particularly preferably equal to benzene, which is in each case substituted by radicals R ^E3 .

R ^E1 is preferably an aromatic or heteroaromatic ring system which is substituted by one or more radicals R ^E4 .

With each occurrence, R ^E2 is preferably selected identically or differently from straight-chain alkyl groups with 1 to 20 C atoms, branched or cyclic alkyl 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 groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ^E4 , where two or more radicals R ^E2 can be linked to one another and form a ring, and one or more radicals R ^E2 via their radicals R ^E4 can be linked with a ring selected from C ¹ , C ² and C ³ and can form a ring. R ^E2 is particularly preferably selected the same or different from aromatic in each occurrence

Ring systems with 6 to 40 aromatic ring atoms, each of which is substituted by radicals R ^E4 , it being possible for two or more radicals R ^{E2 to} be linked to one another and to form a ring, and for one or more radicals R ^{E2 to be selected} via their radicals R ^E4 with a ring can be linked from C ¹ , C ² and C ³ and can form a ring.

According to a preferred embodiment, the residues R ^E2 are chosen the same every time they occur. Furthermore, according to a preferred

Embodiment C ¹ , C ² , C ³ and all residues R ^E2 chosen the same,

in particular identical to phenyl, which can be substituted accordingly, preferably then all phenyl groups in question are equally substituted. With each occurrence, R ^E3 is preferably selected identically or differently from H, D, F, CN, Si (R ^E4 ) 3, N (R ^E4 ) 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 ^E4 ; and wherein in said alkyl or alkoxy groups one or more CFh groups by -C ^ C-, -R ^E4 C = CR ^E4 -, Si (R ^E4 ) 2, C = 0, C = NR ^E4 , -NR ^E4 -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ^E4 - can be replaced.

At least one radical R ^E3 in formula (E-1) is particularly preferably selected from alkyl groups with 1 to 10 C atoms, N (R ^E4 ) 2, aromatic

Ring systems with 6 to 40 aromatic ring atoms, and

heteroaromatic ring systems with 5 to 40 aromatic ring atoms, the alkyl groups mentioned, the aromatic groups mentioned

Ring systems and the heteroaromatic ring systems mentioned are each substituted with radicals R ^E4 . At least one radical R ^E3 in formula (E-1) is very particularly preferably selected from alkyl groups having 1 to 10 C atoms which are substituted by radicals R ^E4 and N (R ^E4 ) 2.

With each occurrence, R ^E4 is preferably selected identically or differently from H, D, F, CN, Si (R ^E5 ) 3, N (R ^E5 ) 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

Alkoxy groups, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ^E5 ; and wherein in said alkyl or alkoxy groups or more CFh groups by -C = C-, -R ^E5 C = CR ^E5 -, Si (R ^E5 ) 2, C = 0, C = NR ^E5 , -NR ^E5 -, -O-, -S-, -C (= 0) 0- or -C (= 0) NR ^E5 - can be replaced.

At least one of the indices o and p is preferably 1. One of the indices o and p is particularly preferably 1 and the other of the indices o and p is 0.

The compound of the formula (E-1) is preferably a mirror-symmetrical compound of a formula (E-1 S)

Formula (E-1 S) where the groups X are selected the same, the groups C ² and C ³ are selected the same, and all groups occurring are selected so that the connection is mirror-symmetrical, with a mirror plane containing the dashed line and is perpendicular to the plane of the paper.

According to a preferred embodiment of the invention, the compound of the formula (E-1) corresponds to the formula (E-1 -1)

Formula (E-1 -1), where the occurring variables are defined as above.

According to a preferred embodiment, the compound of the formula (E-1 -1) corresponds to a mirror-symmetrical compound of the formula (E-1 - 1 S)

Formula (E-1 -1 S), where the groups X are chosen identically and all occurring groups are selected so that the connection is mirror-symmetrical, with a mirror plane containing the dashed line and perpendicular to

Paper level stands. According to an alternative preferred embodiment, the compound of formula (E-1 -1) is not mirror-symmetrical with respect to the mirror plane shown in formula (E-1 - 1 S).

It is particularly preferred if in formula (E-1 -1)

- T is B, and / or

- X is NR ^E2 , and / or

- one of the indices p and o is 1 and the other of the indices p and o is 0.

- At least one radical R ^{E3 is} selected from alkyl groups with 1 to 10 C atoms, N (R ^E4 ) 2, aromatic ring systems with 6 to 40

aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, wherein the alkyl groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted with radicals R ^E4 .

In formula (E-1-1), R ^E2 is preferably phenyl which is substituted by radicals R ^E4 .

At least one radical R ^E3 in the formula (E-1 -1) is very particularly preferably selected from alkyl groups having 1 to 10 C atoms which are substituted by radicals R ^E4 and N (R ^E4 ) 2.

The formula (E-1-1-1) is particularly preferred where Ar ^E2 is chosen the same or different for each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with radicals R ^E4 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with radicals R ^E4 , particularly preferably phenyl or biphenyl, each of which is substituted by radicals R ^E4 . According to a preferred embodiment, the residues Ar ^E2 are chosen the same every time they occur. According to an alternative preferred embodiment, the residues Ar ^E2 are selected differently each time they occur.

The other variables that occur are defined as above.

In the formula, at least one radical R ^E3 is preferably selected

Alkyl groups with 1 to 10 C atoms, N (R ^E4 ) 2, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic

Ring systems with 5 to 40 aromatic ring atoms, the alkyl groups mentioned, the aromatic ring systems mentioned and the

mentioned heteroaromatic ring systems are each substituted with residues R ^E4 . In the formula, at least one radical R ^E3 is very particularly preferably selected from alkyl groups having 1 to 10 carbon atoms which are substituted by radicals R ^E4 and N (R ^E4 ) 2. According to a preferred embodiment, the compound of the formula (E-1 -1 -1) is mirror-symmetrical with respect to a mirror plane which is perpendicular to the paper plane and contains the bond from boron to the uppermost of the three phenyl groups shown. In this case, preferred in formula (E-1 -1 -1) R ^E2 is phenyl or biphenyl, each of which is substituted by radicals R ^E4 .

According to an alternative preferred embodiment, the compound of the formula (E-1 -1 -1) is not mirror-symmetrical to one

Mirror plane, which is perpendicular to the paper plane and contains the bond from boron to the top of the three phenyl groups shown. In this case, preferred in formula (E-1 -1 -1) R ^{E2 is the} same or different from phenyl and biphenyl, each of which is substituted by radicals R ^E4 .

The formulas (E-1 -1 -1 -1) and (E-1 -1 -1 -2) are very particularly preferred.

where Ar ^E1 is chosen the same or different at each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with radicals R ^E5 and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with radicals R ^E5 , and where Ar ^E2 is chosen the same or different for each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with radicals R ^E4 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted with radicals R ^E4 , particularly preferably phenyl or biphenyl, each of which is substituted by radicals R ^E4 , and where R ^{E3_1 is} selected from alkyl groups having 1 to 10 carbon atoms which are substituted by radicals R ^E4 , preferably methyl, ethyl, n-propyl, i-propyl and tert -Butyl, particularly preferably methyl.

The other variables that occur are defined as above.

Ar ^E1 is preferably selected the same or different for each occurrence from phenyl, biphenyl, terphenyl, fluorenyl, naphthyl, dibenzofuranyl,

Dibenzothiophenyl and carbazolyl, each substituted by R ^E5 , and combinations of two or more of these groups. With each occurrence, Ar ^E1 is particularly preferably selected identically or differently from phenyl, o-biphenyl, m-biphenyl, p-biphenyl, terphenyl, p-tolyl, m-tolyl, o-tolyl, p-tert-butyl-phenyl, m tert-butyl-phenyl, o-tert-butyl-phenyl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl, naphthyl, naphthyl,

Dibenzothiophenyl, dibenzofuranyl, naphthyl phenylene, dibenzofuranyl phenylene, dibenzothiophenyl phenylene, carbazolyl phenylene,

especially N-carbazolyl phenylene.

According to a preferred embodiment, the compound of the formula (E-1 -1 -1 -1) or (E-1 -1 -1 -2) is mirror-symmetrical with respect to one

Mirror plane, which is perpendicular to the paper plane and contains the bond from boron to the top of the three phenyl groups shown. The two groups Ar ^E1 can be chosen the same or different and are preferably chosen the same. According to an alternative preferred embodiment, the compound of the formula (E-1 -1 -1 -1) or (E-1 -1 -1 -2) is not mirror-symmetrical with respect to a mirror plane which is perpendicular to the paper plane and the bond from boron contains the top of the three phenyl groups shown. The two groups Ar ^E1 can be selected the same or different and are preferably selected differently.

Most preferred are the formulas (E-1 -1 -1 -1 -1) and (E-1 -1 -1 -1 -2)

where R ^{E3_1 is} defined as R ^E3 ; and R ^{E3 2 is} selected from alkyl groups with 1 to 10 C atoms which are substituted by radicals R ^E4 , preferably methyl, ethyl, isopropyl and tert-butyl, particularly preferably methyl; and R ^E4_1 is defined as R ^E4 , and the other variables are defined as above.

In formula (E-1 -1 -1 -1 -1) and (E-1 -1 -1 -1 -2), R ^{E3 1} and R ^{E4 1} are preferred in each occurrence, chosen the same or different from H, alkyl groups with 1 to 10 carbon atoms which are substituted with radicals R ^E4 or R ^E5 and are preferably unsubstituted, and aromatic ring systems with 6 to 40 ring atoms which are substituted with radicals R ^E4 or R ^E5 . Exactly exactly one or two R ^E3_1 or R ^{E4 1} radicals per benzene ring are preferably selected from alkyl groups with 1 to 10 C atoms, which are substituted by R ^E4 or R ^E5 radicals and are preferably unsubstituted, and aromatic ring systems with 6 to 40 ring atoms which are substituted by R ^E4 or R ^E5 and the other R ^E3_1 or R ^{E4 1} are equal to H.

According to a preferred embodiment, those in formula (E-1 -1 -1 -1)

Formula (E-1 -1 -1 -1) with units marked with a circle are selected identically, and the units marked with a rectangle are also selected identically. All four marked units are particularly preferably selected identically. The units marked with a circle and a rectangle are preferably the same or different, preferably the same, selected from appropriately substituted benzene, naphthalene, fluorene, dibenzofuran and dibenzothiophene.

Correspondingly substituted benzene is particularly preferred.

The compound of the formula (E-1 -1 -1 -1) can be represented as compound A-B containing the two subunits A and B:

Preferred embodiments of unit A are the following (unit “B” in the formulas correspondingly denotes unit B):

Preferred embodiments of unit B are the following (unit A in the formulas is correspondingly denoted by “A”):

Preferred embodiments of the compounds of the formula (E-1 -1-1 -1) are therefore compounds of the following formulas, in which part A and part B of the formula are selected as follows:

Preferred compounds according to formula (E-1) are shown in the following table:

Layer H1 preferably contains a compound of formula (L-1). A preferred embodiment of the formula (L-1) is the formula (L-1 -1)

Formula (L-1 -1) where Z is CR ¹ on each occurrence and the rest

Variables are defined as above.

The index n is preferably 0, so that the amino group is bonded directly to the spirobifluorenyl group. Furthermore, there is preferably at least one group R ¹ which is selected from alkyl groups with 1 to 10 C atoms and aromatic ring systems with 6 to 40 aromatic rings

Ring atoms, which are each substituted with R ⁴ radicals.

Preferred embodiments of formula (L-1 -1) are formulas (L-1 -1 -1), (L-1 -1 -2) and (L-1 -1 -3)

Formula (L-1 -1 -1)

Formula (L-1 -1 -3) where R ^{1 1 is the} same or different, preferably the same, each time it is selected from alkyl groups with 1 to 10 carbon atoms, preferably methyl and tert-butyl, and aromatic ring systems with 6 to 40 aromatic ring atoms, each of which is substituted by R ⁴ , preferably phenyl which is substituted by R ⁴ , preferably unsubstituted phenyl.

Furthermore, Z is CR ¹ . The other variables are defined as above. In formulas (L-1 -1 -1) and (L-1 -1 -2) Z is preferably CH. The

Spirobifluorenyl backbone in formula (L-1 -1 -3) also carries

Amino group no further substituents.

Particularly preferred as a compound contained in layer H1 is a compound of the formula (L-1 -1 -1), in particular a compound of Formula (L-1 -1 -1) in which n is 0 and R ^{1 1 is} aromatic

Is ring system which is substituted with radicals R ⁴ . It is particularly preferred that n is 0, Z is CH, and R ^{1 1} is phenyl which is substituted by radicals R ⁴ .

Preferred embodiments of formula (L-2) correspond to formula (L- 2-1)

where Z is CR ¹ and the other variables are defined as above. In the formula, index n is preferably equal to 0. Furthermore, it is preferred that at least one group R ¹ as part of a group Z is selected from alkyl groups with 1 to 10 C atoms, preferably methyl and tert-butyl, and aromatic ring systems with 6 up to 40 aromatic ring atoms, each of which is substituted by radicals R ⁴ , preferably phenyl which is substituted by radicals R ⁴ , preferably unsubstituted phenyl.

Preferred embodiments of the formula (L-3) correspond to one of the formulas (L-3-1) and (L-3-2)

where Z is CR ¹ and the other variables are defined as above. In the formulas, index n is preferably 0.

Index n is preferably 0 or 1, particularly preferably 0.

R ¹ is preferably selected the same or different for each occurrence 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.

R ² is preferably selected the same or different for each occurrence from alkyl groups with 1 to 10 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with radicals R ⁴ , and heteroaromatic ring systems which are substituted with radicals R ⁴ . In each occurrence, R ² is particularly preferably selected identically or differently from methyl and phenyl which is substituted by radicals R ⁴ . R ³ is preferably selected the same or different for each occurrence 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

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 are represented 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.

R ⁴ is preferably selected 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

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 are represented 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.

Ar ¹ groups in formulas (L-1), (L-2) and (L-3) and in the preferred embodiments of these formulas are preferably selected identically or differently from divalent groups derived from benzene, biphenyl,

Terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole,

Spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which can be substituted with one or more R ³ radicals. Ar ¹ is very particularly preferably a divalent group derived from benzene, which can in each case be substituted by one or more radicals R ³ . Groups Ar ¹ can be chosen the same or different for each occurrence.

Preferred groups - (Ar ¹ ) _n - correspond to the following formulas:

the dashed lines represent the bonds to the rest of the formula.

Ar ² groups in formulas (L-1), (L-2) and (L-3) and in the preferred ones

Embodiments of these formulas are preferably selected identically or differently from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran , Dibenzothiophene,

Benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine, and triazine, where the monovalent groups can each be substituted with one or more radicals R ³ . As an alternative, the groups Ar ² can be selected the same or different each time they occur from combinations of groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenyl fluorene , Benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyrimidine, pyrazine, pyridazine and triazine, where the groups can each be substituted by one or more radicals R ³ . Particularly preferred groups Ar ² are chosen the same or different for each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, especially 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl , Dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, carbazyl-substituted phenyl, dibenzyl Pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, where the groups mentioned can each be substituted by one or more radicals R ³ .

Preferred groups Ar ² are shown below:

where the groups at all free positions can each be substituted by a radical R ³ , preferably unsubstituted in these positions, and wherein the dashed bond is the bond to the amine nitrogen atom.

Preferred compounds of the formulas (L-1), (L-2) and (L-3) are shown in the following table:

The layer H2 is preferably an electron blocking layer and preferably adjoins the emitting layer directly on the anode side.

Layer H2 preferably contains a triarylamine compound. Layer H2 particularly preferably contains a mono-triarylamine compound. A mono-triarylamine compound is understood to mean a compound which contains one and no more triarylamino groups. It is further preferred that the layer H2 contains a triarylamine compound which has at least one group selected from spirobifluorenyl groups,

Fluorenyl groups, indenofluorenyl groups, dibenzofuranyl groups and Contains dibenzothiophenyl groups. This can be carried out directly or via an aromatic ring system, especially selected from phenylene,

Biphenylene and fluorenylene, as a linker to the nitrogen atom of the amine. The spirobifluorenyl group is particularly preferably bonded in the 1, 3 or 4 position, very particularly preferably in the 1 or 4 position, most preferably in the 4 position. The is particularly preferred

Fluorenyl group bound in 1, 3, or 4-position, very particularly preferably in the 4-position.

A preferred embodiment of the compound of formula (L-1) for use in layer H2 corresponds to a formula (L-1 -2) or (L-1 -3)

where Z is CR ¹ and preferably is CH, and the other variables that occur are defined as above.

A preferred embodiment of the compound of formula (L-2) for use in layer H2 corresponds to a formula (L-2-2)

Formula (L-2-2) where Z is CR ¹ and preferably is CH, and wherein the other variables that occur are defined as above. It is particularly preferred that the layer H2 contains a compound which is selected from compounds of the formulas (L-1), in particular (L-1 -2); (L-2), especially (L-2-2); (L-3), especially (L-3-1) and (L-3-2); (L-4) and (L-5), where formulas (L-4) and (L-5) are defined as follows:

Formula (L-4),

where for the variables that occur:

Y is O, S or NR ³ ;

m is 0, 1, 2 or 3; and

the unsubstituted positions on the benzene rings can each be substituted by a radical R ³ ; and Ar ¹ and Ar ² are defined as above; and

Formula (L-5),

where Z is CR ¹ , preferably CH, and the others

occurring variables are defined as above.

Layer H1 may contain the compound of formula (L-1), (L-2) or (L-3) as a pure material, or it may contain the compound of formula (L-1), (L-2) or (L -3) in combination with one or more others Connections included. If such further compounds are present, they are preferably selected from p-dopants and from hole-transporting compounds. The further hole-transporting compounds are preferably selected from triarylamine compounds, particularly preferably from mono-triarylamine compounds. They are very particularly preferably selected from the preferred specified below

Embodiments of hole transport materials. If the compound of the formula (L-1), (L-2) or (L-3) is present in layer H1 in combination with one or more further hole-transporting compounds, then they and the other hole-transporting compounds are present

Compounds preferably in each case in a proportion of at least 20% in the layer, particularly preferably in each case in a proportion of at least 30%.

The layer H1 can be p-doped or it can be undoped. According to the present invention, preferred p-dopants are those organic electron acceptor compounds which can oxidize one or more of the other compounds in the layer.

Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorendiones, azaphenalenes, azatriphenylenes,

Metal halides, preferably 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 the binding site. Are also preferred

Transition metal oxides as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re2Ü7 _, M0O3, WO3 and Re03. Further preferred are complexes of bismuth in the oxidation state (III), in particular bismuth (III) complexes with

electron deficient ligands, especially carboxylate ligands. The p-dopants are preferably largely uniformly distributed in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole transport material matrix. The p-dopant is preferably present in a proportion of 1 to 10% in the p-doped layer.

In the present application,% in terms of% means volume% when mixtures of compounds which are applied from the gas phase are affected. On the other hand, this means mass% when mixtures of compounds which are applied from solution are affected.

The following compounds are particularly preferred as p-dopants:

In hole-transporting layers of the device, such as

Hole injection layers, hole transport layers and

Electron blocking layers, preferred are indenofluorenamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with condensed aromatics, monobenzoindenofluorenamines,

Dibenzoindenofluorenamines, spirobifluorene amines, fluorene amines, spiro-dibenzopyran amines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine 9-diamine diamine, 9-diamine diamine, 9-diamine diamine, 9-diamine diamine, 9-diamine diamine, 9-diamine diamine diamine, 9-diamine diamine diamine, 9-diamine diamine, di-10-amine, di-8-diamine, diamine-10-diamine, -Dihydroanthracene-spiro compounds with diarylamino groups used. Explicit examples of compounds for use in hole transport layers are shown in the following table:

Furthermore, the following compounds HT-1 to HT-38 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 a emitting layer as matrix material, in particular as matrix material in an emitting layer containing one or more

phosphorescent emitters:

The compounds HT-1 to HT-38 are generally well suited for the uses mentioned above in OLEDs of all types and

Composition, not only in OLEDs according to the present

Registration. Processes for the preparation of these compounds and further relevant disclosure on the use of these compounds are disclosed in the laid-open publications, each of which is listed in parentheses in the table under the respective compounds. The connections show good performance data in OLEDs, in particular good service life and good efficiency.

The electronic device is preferably an organic one

Electroluminescent device. The first electrode of the device is preferably the anode and the second electrode is preferably the cathode. 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 / NiOx, Al / PtOx) 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 coupling 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.

In addition to the anode, cathode, layers H1, H2, and the emitting layer, the device preferably contains further layers, in particular one or more electron-transporting layers. It is further preferred that the device contains a hole injection layer which is directly adjacent to the anode. Layer H1 can assume the function of such a hole injection layer. In this case, it is preferred that the layer H1 is p-doped.

Alternatively, an additional layer can be present in the device, which takes over the function of a hole injection layer. Such a hole injection layer preferably corresponds to one of the following two embodiments: a) it contains a triarylamine and a p-dopant; or b) it contains a single, very electron-poor material

(Electron acceptor). According to a preferred embodiment of embodiment a) the triarylamine is a mono-triarylamine, in particular a triarylamine containing a compound of the formula (L-1), (L-2) or (L-3). According to a preferred embodiment of embodiment b), the electron acceptor is a hexaazatriphenylene derivative, as in

US 2007/0092755.

The device according to the invention preferably contains between anode and cathode:

- A hole injection layer (HIL) directly adjacent to the anode, and

- Layer H1 directly adjacent to the HIL on the cathode side, and

- Layer H2, and. directly adjacent to layer H1 on the cathode side

- The emitting layer directly adjacent to the layer H2 on the cathode side. The device preferably contains one or more electron-transporting layers on the cathode side of the emitting layer.

It preferably contains an electron transport layer and an electron injection layer on the cathode side thereof. There can be an additional one between the emitting layer and the electron transport layer

Hole blocking layer may be arranged.

According to a preferred embodiment of the invention, the device contains two or three, preferably three, identical or different layer sequences stacked one above the other, each of the

Layer sequences each include the following layers:

Hole injection layer, hole transport layer, electron blocking layer, emitting layer, and electron transport layer, and wherein at least one of the layers is sequential

an emitting layer E containing a compound of the formula (E

1 ).

- A layer H1 between the first electrode and the

emitting layer and which contains a compound of the formula (L-1), (L-2) or (L-3), and

- Contains a layer H2, which is arranged between the layer H1 and the emitting layer.

All of the two or three layer sequences preferably contain

an emitting layer E containing a compound of the formula (E

1 ).

- A layer H 1 between the first electrode and the

a layer H2 which is arranged between the layer H1 and the emitting layer. All of the two or three layer sequences preferably emit blue light.

It is further preferred that all of the two or three layer sequences contain an emitting layer E which contains a compound of the formula (E-1).

A double layer of adjacent n-CGL and p-CGL is preferably arranged between the layer sequences, the n-CGL being arranged on the anode side and the p-CGL correspondingly on the cathode side. CGL stands for charge generation layer

Charge generation layer. Materials for use in such layers are known to those skilled in the art. A p-doped amine is preferably used in the p-CGL, particularly preferably a material which is selected from the preferred structural classes of

Hole transport materials.

Suitable materials, such as those in the electron injection layer, in the electron transport layer and / or the hole blocking layer of the

In addition to the compounds according to the invention, the device according to the invention can be used, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107 (4), 953-1010 or other materials of the type known from the prior art Layers are used. In particular, all materials which are known according to the prior art for use in these layers can be used as materials for these layers.

Aluminum complexes, for example Alq3, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, are particularly suitable.

Oxadiazole derivatives, aromatic ketones, lactams, boranes,

Diazaphosphole derivatives and phosphine oxide derivatives. Explicit examples of suitable compounds are shown in the following table.

In addition to the compound of the formula (E-1), the emitting layer of the device preferably contains one or more further compounds, preferably exactly one further compound. The compound of the formula (E-1) represents the emitting compound and the further compound represents the matrix compound. The compound of the formula (E-1) is preferably present in the layer in a proportion of 0.5% to 15%, preferably 0.5% to 10%, particularly preferably 3% -6%. The further compound is preferably present in the layer in a proportion of 85% to 99.5%, preferably in a proportion of 90% -99.5% and particularly preferably in a proportion of 94% -97%.

The further compound is preferably selected from compounds which are known in the prior art as matrix materials for fluorescent emitters, in particular compounds selected from the classes of the oligoarylenes (e.g. 2,2 ', 7,7'-tetraphenylspirobifluorene), in particular the Oligoarylenes containing condensed aromatic groups, the

Oligoarylenvinylenes, the polypodal metal complexes, the hole-conducting compounds, the electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides; of atropisomers, boronic acid derivatives and benzanthracenes. Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, oligoarylene vinylenes, 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. Most preferred are materials selected from the classes of anthracenes and benzanthracenes. Under a

For the purposes of this invention, oligoarylene is understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.

The compound of formula (E-1) is preferably a fluorescent one

Connection. It preferably emits blue light. The compound can also emit light, also preferably blue light, by the thermally activated delayed fluorescence (TADF) mechanism. In this case it is preferred that

for LUMO (E), i.e. the LUMO energy level of the emitting compound of the formula (E-1), and HOMO (matrix), i.e. the HOMO energy level of the matrix material, the following applies:

LUMO (E) - HOMO (matrix)> Si (E) - 0.4 eV;

particularly preferred:

LUMO (E) - HOMO (matrix)> Si (E) - 0.3 eV;

and very particularly preferred:

LUMO (E) - HOMO (matrix)> Si (E) - 0.2 eV.

Si (E) is the energy of the first excited singlet state of the compound of formula (E-1).

It is further preferred that the energy of the Ti state of the

Matrix material of the emitting layer, hereinafter referred to as Ti (matrix), is at most 0.1 eV lower than the energy of the Ti state of the compound of the formula (E-1), hereinafter referred to as Ti (E).

Ti (matrix)> Ti (E) is particularly preferred. The following applies very particularly preferably: Ti (matrix) - Ti (E)> 0.1 eV, most preferably Ti (matrix) - Ti (E)> 0.2 eV.

Examples of suitable matrix materials in the emitting layer in the case of emission of the compound of formula (E-1) according to the TADF mechanism are ketones, phosphine oxides, sulfoxides and sulfones, triarylamines, carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl), or m-CBP, indolocarbazole derivatives, indenocarbazole derivatives, azacarbazoles, bipolar matrix materials, silanes, azaboroles or boronic esters, diazasilole derivatives, diazaphosphole derivatives, triazine derivatives, zinc complexes, or bridged carbazole derivatives. Electron-transporting organic compounds are also preferred for this use. Are particularly preferred

Electron-transporting organic compounds which have a LUMO energy level of at most -2.50 eV, particularly preferably at most -2.60 eV, very particularly preferably at most -2.65 eV, and most preferably at most -2.70 eV.

Particularly preferred matrix materials in the emitting layer in the case of emission of the compound of the formula (E-1) according to the TADF mechanism are selected from the classes of the triazines

Pyrimidines, the lactams, the metal complexes, in particular the Be, Zn or Al complexes, the aromatic ketones, the aromatic

Phosphine oxides, the azaphospholes, the azaboroles, which are substituted with at least one electron-conducting substituent, the quinoxalines, the quinolines and the isoquinolines.

The emitting layer of the device preferably emits blue light.

According to a preferred embodiment of the invention, the device emits light through the anode and the substrate layer (bottom emission).

According to an alternative, likewise preferred embodiment of the invention, the device emits light through the cathode (top emission). In this embodiment, the cathode is designed to be partially transparent and partially reflective. For example, an alloy of Ag and Mg can be used as the cathode. The anode is in this

Embodiment highly reflective. Furthermore, in this case the device preferably contains a coupling-out layer which is applied to the cathode and which preferably contains an amine compound. The layer thicknesses in this embodiment are based on those used

Adapt materials, in particular to the refractive index of the Layers and the location of the recombination zone in the emitting layer in order to achieve an optimal resonance effect.

In the embodiment with top emission, an excellent efficiency of the OLED, combined with a narrow emission band, can be achieved.

After the layers have been applied, the device can be structured, contacted and finally sealed in order to exclude damaging effects of water and air.

In a preferred embodiment, the device is characterized in that one or more layers with one

Sublimation processes are coated. 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.

It is further preferred that one or more layers of the device are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation. The materials are applied at a pressure between 10 ⁵ mbar and 1 bar. 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).

It is further preferred that one or more layers of the device from solution, such as. B. by spin coating, or with any

Printing processes such as B. screen printing, flexo printing, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing.

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

A method for producing the device initially comprises

Provision of a substrate with an anode, in a later step the application of the layer H 1, in a later step the application of the layer H2, in a later step the

Application of the emitting layer, and in a later step the application of the anode. The layers H1 and H2 and the emitting layer are preferably applied from the gas phase. All layers between the anode and cathode are particularly preferred

Device applied from the gas phase.

The devices according to the invention are preferably used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications.

Examples

A) General manufacturing process for the OLEDs and characterization of the OLEDs

Glass platelets coated with structured ITO (indium tin oxide) with a thickness of 50 nm form the substrates to which the OLEDs are applied.

The OLEDs have the following layer structure: substrate / hole

injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) /

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 the following tables. The materials present in the individual layers of the OLED are shown in the following table.

All materials are thermally evaporated in a vacuum chamber. The emission layer consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter) that passes through the matrix material or the matrix materials

Cover vaporization is added in a certain volume fraction. An indication like H: SEB (95%: 5%) means that the material H in a volume fraction of 95% and the material SEB in one

Volume share of 5% is present in the layer.

Similarly, there is the electron transport layer and the

Hole injection layer made of a mixture of two materials.

The OLEDs are characterized by default. For this purpose, the operating voltage and the external quantum efficiency (EQE, measured in%) as a function of the luminance, calculated from current-voltage-luminance characteristics, assuming a Lambertian

Beam characteristics determined. The specification EQE @ 10mA / cm ² denotes the external quantum efficiency that is achieved at 10mA / cm ² . The specification U @ 10 mA / cm ² denotes the operating voltage at 10 mA / cm ² .

B) Production and characterization of OLEDs according to the invention with a bottom emission structure

OLEDs with the following structure are manufactured:

In the OLEDs E1 to E4, the connection used in the HIL and HTL varies. The compounds HTM-1 to HTM-4 are used, which are spirobifluorenyl amines or fluorenyl amines. In the EBL the spirobifluorenyl amine EBM-1 is used in all cases.

The comparison OLED V1 is constructed identically to the OLED E1, with the only difference that the connection SdT is present as the emitter instead of the connection SEB in the emitting layer.

The following device data can be achieved with the OLEDs:

In all OLEDs E1 to E4 according to the invention, a good one

Operating voltage and high efficiency achieved. The half width of the emission is in all cases around 26 nm. The comparison OLED V1 shows a significantly poorer efficiency and an increased operating voltage than the corresponding OLED E1 according to the invention.

OLEDs are also manufactured with the following structures:

The connection HTM-3 is always used in the HIL and the HTL in the OLEDs E5 to E10. The compound HTM-3 is a 2-spirobifluorenyl amine which carries a phenyl group as a substituent on the spiro. In the OLEDs E5 to E10, the connection used in the EBL varies. It will be the

Connections EBM-2 to EBM-7 used the different

Have structures. The compounds EBM-2 to EBM-7 are selected from spirobifluorenyl amines, indenofluorenyl amines, fluorenyl amines and amines with phenylene dibenzofuran groups on the amine.

The following device data can be achieved with the OLEDs:

Good operating voltage and high efficiency are achieved in all cases. The full width at half maximum of the emission is approx.

28 nm.

C) Production and characterization of OLEDs according to the invention with a top emission structure

OLEDs with the following structure are manufactured:

Substrate / HIL / HTL / EBL / EML / ETL / EIL / cathode /

Decoupling layer.

The substrate is in each case a glass plate which is coated with structured ITO (indium tin oxide) with a thickness of 50 nm. The cathode consists of a 15 nm thick layer made of a mixture of 91% Ag and 9% Mg. The coupling-out layer consists of a 70 nm thick layer made of the compound HTM-1. The structure of the layers HIL, HTL, EBL, EML, ETL and EIL is shown in the following table:

The OLED E11 has color coordinates CIE x, y = 0.14, 0.05. It achieves a very high EQE at 10 mA / cm ² of 16% -19%. The emission band of the OLEDs is very narrow and has a half width between 17 and 18 nm.

Furthermore, the following OLEDs with top emission structure can be produced, in which HTM-1 is replaced by HTM-2, HTM-3 or HTM-4, or EBM-1 by one of the materials EBM- compared to the OLED E11. 2 until the EBM-7 is replaced:

OLEDs can be obtained which have color coordinates CIE x, y = 0.14, 0.05. After adjusting the layer thicknesses to the material combination used to optimize the resonance effect, very high values for the EQE at 10 mA / cm ² of 16% -19% can be achieved with these OLEDs, and very small half-value widths of the emission band from 17 to 18 nm.

30th

Claims

Expectations

1. Electronic device, comprising a first electrode, a second electrode, and arranged in between

- An emitting layer E containing a compound of a formula

for which applies:

T is B, P, P (= 0) or SiR ^E1 ;

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; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R ^E4 ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ^E4 C = CR ^E4 -, -C ^ C-, Si (R ^E4 ) 2, C = 0, C = NR ^E4 , -C (= 0) 0-, -C (= 0) NR ^E4 -, NR ^E4 , P (= 0) (R ^E4 ), -O-, -S-, SO or SO2 can be replaced;

Each occurrence of R ^E3 is the same or different from H, D, F, CI, Br, I, C (= 0) R ^E4 , CN, Si (R ^E4 ) ₃ , N (R ^E4 ) ₂ , P (= 0) (R ^E4 ) ₂ , OR ^E4 , S (= 0) R ^E4 , S (= 0) ₂ R ^E4 , 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 R ^E3 radicals 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 ^E4 ; and wherein one or more CFh groups in said alkyl, alkoxy, alkenyl and alkynyl groups are represented by -R ^E4 C = CR ^E4 -, -C ^ C-, Si (R ^E4 ) 2, C = 0, C = NR ^E4 , -C (= 0) 0-, -C (= 0) NR ^E4 -, NR ^E4 , P (= 0) (R ^E4 ), -O-, -S-, SO or SO2 can be replaced;

With each occurrence, R ^E5 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; where two or more radicals R ^E5 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; o and p are identical or different 0 or 1, where p = 0 and o = 0 means that the group X indicated with p and o, together with their bonds to the rings C ¹ , C ² and C ^3, is omitted;

- A layer H1 between the first electrode and the

Formula (L-2) for which applies:

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 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 ¹ are linked to one another can and 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 Ch 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 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 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 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 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;

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 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 are linked to one another can and 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 Chh groups in said alkyl, alkoxy, alkenyl and alkynyl groups 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 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 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 ⁴ 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 ⁵ ; and wherein one or more CH ₂ 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 S0 ₂ can;

Alkynyl groups, aromatic ring systems and heteroaromatic Ring systems with one or more radicals selected from F and CN can be substituted; n is the same or different at each occurrence 0, 1, 2, 3 or 4; k is 0 or 1; and

a layer H2 which is arranged between the layer H1 and the emitting layer.

2. Electronic device according to claim 1, characterized in that the group T is equal to B.

3. Electronic device according to claim 1 or 2, characterized

characterized that the group X is equal to NR ^E2 at each occurrence.

4. Electronic device according to one or more of claims 1 to 3, characterized in that R ^E2 is chosen the same or different for each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms, each of which is substituted with radicals R ^E4 , two or more R ^E2 radicals can be linked to one another and can form a ring, and one or more R ^E2 radicals can be linked via their R ^E4 radicals to a ring selected from C ¹ , C ² and C ³ and can form a ring.

5. Electronic device according to one or more of claims 1 to 4, characterized in that R ^{E3 is selected the} same or different for each occurrence from H, D, F, CN, Si (R ^E4 ) 3, N (R ^E4 ) 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 the heteroaromatic mentioned

Ring systems are each substituted with radicals R ^E4 ; and wherein in said alkyl or alkoxy groups one or more CFh groups by -C = C-, -R ^E4 C = CR ^E4 -, Si (R ^E4 ) ₂ , C = 0, C = NR ^E4 , -NR ^E4 -, -O-, -S-, - C (= 0) 0- or -C (= 0) NR ^E4 - can be replaced.

6. Electronic device according to one or more of claims 1 to 5, characterized in that at least one radical R ^E3 in formula (E- 1) is selected from alkyl groups having 1 to 10 C atoms which are substituted by radicals R ^E4 , and N (R ^E4 ) ₂ .

7. Electronic device according to one or more of claims 1 to 6, characterized in that R ^{E4 is selected the} same or different for each occurrence from H, D, F, CN, Si (R ^E5 ) 3, N (R ^E5 ) 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

aromatic ring systems and the heteroaromatic mentioned

Ring systems are each substituted with radicals R ^E5 ; and wherein in said alkyl or alkoxy groups one or more CFI ₂ groups by -C = C-, -R ^E5 C = CR ^E5 -, Si (R ^E5 ) ₂ , C = 0, C = NR ^E5 , -NR ^E5 -, -O-, -S-, - C (= 0 ) 0- or -C (= 0) NR ^E5 - can be replaced.

8. Electronic device according to one or more of claims 1 to 7, characterized in that one of the indices o and p is 1 and the other of the indices o and p is 0.

9. Electronic device according to one or more of claims 1 to 8, characterized in that the compound of formula (E-1) one

where R ^{E3_1 is} defined as R ^E3 ; and R ^{E3 2 is} selected from alkyl groups with 1 to 10 C atoms which are substituted by radicals R ^E4 , preferably methyl, ethyl, isopropyl and tert-butyl, particularly preferably methyl; and R ^{E4_1 is} defined as R ^E4 , and wherein the other variables are defined as in one or more of claims 1 to 8, preferably as in claim 1.

10. Electronic device according to one or more of claims 1 to 9, characterized in that the layer H contains a compound of formula (L-1).

1 1. Electronic device according to one or more of claims 1 to 10, characterized in that the compound of formula (L-1) corresponds to a formula selected from formulas (L-1 -1 -1) to (L-1 -1 -3)

Formula (L-1 -1 -1)

Formula (L-1 -1 -3) where R ^{1 1} is chosen the same or different for each occurrence from alkyl groups with 1 to 10 C atoms, and aromatic ring systems with 6 to 40 aromatic ring atoms, each of which is substituted by radicals R ⁴ , and where Z is CR ¹ , and where Z is CFI, and wherein the other variables are defined as in one or more of the

Claims 1 to 10, preferably as in claim 1.

12. Electronic device according to one or more of claims 1 to 1 1, characterized in that

R ¹ and R ³ are chosen the same or different for each occurrence 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 up 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 radicals R ⁴ ; and wherein in said alkyl or alkoxy groups one or more CH ₂ 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; and further characterized in that

R ^{2 is selected the} same or different for each occurrence

Alkyl groups with 1 to 10 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted with radicals R ⁴ , and heteroaromatic ring systems, which are substituted with radicals R ⁴ ; and further characterized in that

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

heteroaromatic ring systems are each substituted with radicals R ⁵ ; and wherein one or more CH ₂ groups in said alkyl or alkoxy groups

S-, -C (= 0) 0- or -C (= 0) NR ⁵ - can be replaced.

13. Electronic device according to one or more of claims 1 to 12, characterized in that groups Ar ^{1 are selected} identically or differently from divalent groups derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, Spirobifluorene, dibenzofuran, dibenzothiophene, and carbazole, each of which can be substituted with one or more R ³ radicals.

14. Electronic device according to one or more of claims 1 to 13, characterized in that Ar ² is chosen the same or different for each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9'-dimethylfluorenyl and 9 , 9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl,

Benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, phenyl-substituted-pyrylylyl-pyrylylyl-pyrylylyl-substituted-pyryl and triazinyl-substituted phenyl, where the groups mentioned can each be substituted by one or more radicals R ³ .

15. Electronic device according to one or more of claims 1 to 14, characterized in that the layer H2 directly adjoins the emitting layer on the anode side.

16. Electronic device according to one or more of claims 1 to 15, characterized in that the layer H2 contains a compound which has a formula selected from formulas (L-1 -2), (L-2-2), (L- 3-1), (L-3- 2), (L-4) and (L-5) where Z is CR ¹ and Y is O, S or NR ³ ; and m is 0, 1, 2 or 3; and the unsubstituted positions on the benzene rings in formula (L-4) can each be substituted by a radical R ³ , and the other variables are defined as in one or more of claims 1 to 15, preferably as in claim 1.

17. Electronic device according to one or more of claims 1 to 16, characterized in that between the anode and cathode:

- contains a hole injection layer (HIL) directly adjacent to the anode, and

contains the layer H1 directly on the cathode side adjacent to the HIL, and

contains layer H2 directly adjacent to layer H1 on the cathode side,

contains the emitting layer directly on the cathode side adjacent to the layer H2, and

- Contains one or more electron-transporting layers on the cathode side of the emitting layer.

18. Electronic device according to one or more of claims 1 to 17, characterized in that the emitting layer contains, in addition to the compound of the formula (E-1), a matrix compound which is an anthracene compound.

19. Electronic device according to one or more of claims 1 to 18, characterized in that it is an organic

Electroluminescent device is.

20. Electronic device according to one or more of claims 1 to 19, characterized in that it emits blue light.

21. Electronic device according to one or more of claims 1 to 20, characterized in that it is an organic

Electroluminescent device that emits light through the cathode.

22. Electronic device according to one or more of claims 1 to 21, characterized in that it comprises two or three identical or different layer sequences stacked one above the other, each of the layer sequences comprising the following layers:

an emitting layer E containing a compound of the formula (E

1 ). - A layer H1 between the first electrode and the

23. A method for producing a device according to one or more of claims 1 to 22, comprising first the provision of a substrate with an anode, in a later step the application of layer H1, in a later step the application of layer H2, in one the emitting layer is applied later, and the anode is applied in a later step.

24. Use of an electronic device according to one or more of claims 1 to 22 in displays, as a light source in

Lighting applications, or as a light source in medical and / or cosmetic applications.