DE102020007381A1 - SPIROINDOLENONE - Google Patents

Abstract

The present invention describes spiroindolenones, particularly for use in electronic devices. The invention also relates to a method for producing the spiroindolenones according to the invention and to electronic devices containing them.

Description

The present invention describes spiroindolenones, particularly for use in electronic devices. The invention also relates to a method for producing the compounds according to the invention and to electronic devices containing these compounds.

The structure of organic electroluminescent devices (OLEDs), in which organic semiconductors are used as functional materials, is generally known in the prior art. Organometallic complexes that exhibit phosphorescence are often used as emitting materials. For reasons of quantum mechanics, the use of organometallic compounds as phosphorescence emitters can achieve up to four times the energy and power efficiency. In general, there is still a need for improvement in the case of OLEDs, in particular also in the case of OLEDs that show phosphorescence, for example with regard to efficiency, operating voltage and service life.

The properties of organic electroluminescent devices are not only determined by the emitters used. In particular, the other materials used, such as host and matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials are also of particular importance here. Improvements in these materials can lead to significant improvements in electroluminescent devices.

According to the prior art, aromatic or heteroaromatic compounds, such as, for example, triarylamine or carbazole derivatives, are frequently used as matrix materials for phosphorescent compounds and as hole transport materials. Furthermore, triazine derivatives or pyrimidine derivatives are also used as matrix materials and as electron transport materials.

In general, there is still a need for improvement with these materials, for example for use as matrix materials, in particular with regard to the service life, but also with regard to the efficiency, the operating voltage and the color purity of the device.

The object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which lead to good device properties when used in this device, and to provide the corresponding electronic device .

In particular, it is the object of the present invention to provide connections which lead to a long service life, good efficiency and low operating voltage. The properties of the matrix materials in particular also have a significant influence on the service life and the efficiency of the organic electroluminescent device.

Another object of the present invention can be seen in providing compounds which are suitable for use in a phosphorescent or fluorescent OLED, in particular as a matrix material. In particular, it is an object of the present invention to provide matrix materials which are suitable for red and green phosphorescent OLEDs and optionally also for blue phosphorescent OLEDs.

Furthermore, especially when used as matrix materials, as hole conductor materials or as electron transport materials in organic electroluminescent devices, the compounds should lead to devices which have excellent color purity.

Furthermore, the compounds should be as easy to process as possible, in particular they should exhibit good solubility and film formation. For example, the compounds should exhibit increased oxidation stability and an improved glass transition temperature.

A further object can be seen in providing electronic devices with excellent performance as inexpensively as possible and of constant quality

Furthermore, the electronic devices should be able to be used or adapted for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.

It has surprisingly been found that certain compounds described in more detail below achieve these objectives. The use of the compounds leads to very good properties of organic electronic devices, in particular of organic electroluminescent devices, in particular with regard to service life, color purity, efficiency and operating voltage. Electronic devices, in particular organic electroluminescent devices, which contain compounds of this type, and the corresponding preferred embodiments are therefore the subject matter of the present invention.

wobei für die verwendeten Symbole gilt:

X

ist bei jedem Auftreten gleich oder verschieden N oder CR, vorzugsweise CR;

V

ist eine Gruppe der Formel -C(=O)NR- oder - NRC(=O) -;

Y

ist eine Bindung oder eine Brücke, ausgewählt aus B(R), C(R)₂, Si(R)₂, C=O, C=NR, C=C(R)₂, O, S, Se, S=O, SO₂, N(R), P(R) und P(=O)R;

R

ist bei jedem Auftreten gleich oder verschieden H, D, OH, F, CI, Br, I, CN, NO₂, N(Ar)₂, N(R¹)₂, C(=O)Ar, C(=O)R¹, P(=O)(Ar)², P(Ar)₂, B(Ar)₂, B(OR¹)₂, Si(Ar)₃, Si(R¹)₃, eine geradkettige Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen oder eine verzweigte oder cyclische Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen oder einer Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R² substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch -R¹C=CR¹-, -C=C-, Si(R¹)₂, Ge(R¹)₂, Sn(R¹)₂, C=O, C=S, C=Se, -C(=O)O-, -C(=O)NR¹-, C=NR¹, NR1, P(=O)(R¹), -O-, -S-, -Se-, SO oder SO₂ ersetzt sein können und wobei ein oder mehrere H-Atome durch D, F, Cl, Br, I, CN oder NO₂ ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 60 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste R¹ substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 60 aromatischen Ringatomen, die durch einen oder mehrere Reste R¹ substituiert sein kann, oder einer Aralkyl- oder Heteroaralkylgruppe mit 5 bis 60 aromatischen Ringatomen, die mit einem oder mehreren Resten R¹ substituiert sein kann, oder eine Kombination dieser Systeme; dabei können zwei oder mehrere, vorzugsweise benachbarte Reste R miteinander ein Ringsystem bilden;

Ar

ist bei jedem Auftreten gleich oder verschieden ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 30 aromatischen Ringatomen, das mit einem oder mehreren vorzugsweise nicht-aromatischen Resten R¹ substituiert sein kann, dabei können zwei Reste Ar, welche an dasselbe Si-Atom, N-Atom, P-Atom oder B-Atom binden, auch durch eine Einfachbindung oder eine Brücke, ausgewählt aus B(R¹), C(R¹)₂, Si(R¹)₂, C=O, C=NR¹, C=C(R¹)₂, O, S, Se, S=O, SO₂, N(R¹), P(R¹) und P(=O)R¹, miteinander verbrückt sein;

R1

ist bei jedem Auftreten gleich oder verschieden H, D, OH, F, Cl, Br, I, CN, NO₂, N(Ar¹)₂, N(R²)₂, C(=O)Ar¹, C(=O)R², P(=O)(Ar¹)₂, P(Ar¹)₂, B(Ar¹)₂, B(OR²)₂, Si(Ar¹)₃, Si(R²)₃, eine geradkettige Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen oder eine verzweigte oder cyclische Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen oder einer Alkenyl- oder Alkinylgruppe mit 2 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R² substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch -R²C=CR²-, -C≡C-, Si(R²)₂, Ge(R²)₂, Sn(R²)₂, C=O, C=S, C=Se, C=NR², -C(=O)O-, -C(=O)NR²-, NR², P(=O)(R²), -O-, -S-, -Se-, SO oder SO₂ ersetzt sein können und wobei ein oder mehrere H-Atome durch D, F, CI, Br, I, CN oder NO₂ ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 40 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste R² substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 40 aromatischen Ringatomen, die durch einen oder mehrere Reste R² substituiert sein kann, oder einer Aralkyl- oder Heteroaralkylgruppe mit 5 bis 40 aromatischen Ringatomen, die mit einem oder mehreren Resten R² substituiert sein kann, oder eine Kombination dieser Systeme; dabei können zwei oder mehrere, vorzugsweise benachbarte Reste R¹ miteinander ein Ringsystem bilden;

Ar1

ist bei jedem Auftreten gleich oder verschieden ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 30 aromatischen Ringatomen, das mit einem oder mehreren vorzugsweise nichtaromatischen Resten R² substituiert sein kann, dabei können zwei Reste Ar¹, welche an dasselbe Si-Atom, N-Atom, P-Atom oder B-Atom binden, auch durch eine Einfachbindung oder eine Brücke, ausgewählt aus B(R²), C(R²)₂, Si(R²)_2, C=O, C=NR^2, C=C(R²)₂, O, S, Se, S=O, SO₂, N(R²), P(R²) und P(=O)R², miteinander verbrückt sein;

R2

ist bei jedem Auftreten gleich oder verschieden H, D, F, Cl, Br, I, CN, B(OR³)₂, NO₂, C(=O)R³, CR³=C(R³)₂, C(=O)OR³, C(=O)N(R³)₂, Si(R³)₃, P(R³)₂, B(R³)₂, N(R³)₂, NO₂, P(=O)(R³)₂, OSO₂R³, OR³, S(=O)R³, S(=O)₂R³, eine geradkettige Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 1 bis 40 C-Atomen oder eine verzweigte oder cyclische Alkyl-, Alkoxy- oder Thioalkoxygruppe mit 3 bis 40 C-Atomen, die jeweils mit einem oder mehreren Resten R³ substituiert sein kann, wobei eine oder mehrere nicht benachbarte CH₂-Gruppen durch -R³C=CR³-, -C≡C-, Si(R³)₂, Ge(R³)₂, Sn(R³)₂, C=O, C=S, C=NR³, -C(=O)O-, -C(=O)NR³-, NR³, P(=O)(R³), -O-, -S-, -Se-, SO oder SO₂ ersetzt sein können und wobei ein oder mehrere H-Atome durch D, F, Cl, Br, I, CN oder NO₂ ersetzt sein können, oder ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 40 aromatischen Ringatomen, das jeweils durch einen oder mehrere Reste R³ substituiert sein kann, oder eine Aryloxy- oder Heteroaryloxygruppe mit 5 bis 40 aromatischen Ringatomen, die durch einen oder mehrere Reste R³ substituiert sein kann, oder eine Kombination dieser Systeme; dabei können zwei oder mehrere, vorzugsweise benachbarte Substituenten R² auch miteinander ein bilden;

R3

ist bei jedem Auftreten gleich oder verschieden ausgewählt aus der Gruppe bestehend aus H, D, F, CN, einem aliphatischen Kohlenwasserstoffrest mit 1 bis 20 C-Atomen oder einem aromatischen oder heteroaromatischen Ringsystem mit 5 bis 30 aromatischen Ringatomen, in dem ein oder mehrere H-Atome durch D, F, Cl, Br, I oder CN ersetzt sein können und das durch ein oder mehrere Alkylgruppen mit jeweils 1 bis 4 Kohlenstoffatomen substituiert sein kann; dabei können zwei oder mehrere, vorzugsweise benachbarte Substituenten R³ auch miteinander ein bilden.

The present invention therefore relates to a compound comprising at least one structure according to the formula (I), preferably a compound according to the formula (I),

where the following applies to the symbols used:

X

is on each occurrence, identically or differently, N or CR, preferably CR;

V

is a group of the formula -C (= O) NR- or - NRC (= O) -;

Y

is a bond or bridge selected from B (R), C (R) ₂ , Si (R) ₂ , C = O, C = NR, C = C (R) ₂ , O, S, Se, S = O, SO ₂ , N (R), P (R), and P (= O) R;

R.

is on each occurrence, identically or differently, H, D, OH, F, CI, Br, I, CN, NO ₂ , N (Ar) ₂ , N (R ¹ ) ₂ , C (= O) Ar, C (= O ) R ¹ , P (= O) (Ar) ² , P (Ar) ₂ , B (Ar) ₂ , B (OR ¹ ) ₂ , Si (Ar) ₃ , Si (R ¹ ) ₃ , a straight-chain alkyl , Alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms or an alkenyl or Alkynyl group with 2 to 40 carbon atoms, each of which ^{can be substituted by one or more radicals R 2} , where one or more non-adjacent CH ₂ groups are represented by -R ¹ C = CR ¹ -, -C = C-, Si ( R ¹ ) ₂ , Ge (R ¹ ) ₂ , Sn (R ¹ ) ₂ , C = O, C = S, C = Se, -C (= O) O-, -C (= O) NR ¹ -, C = NR ¹ , NR1, P (= O) (R ¹ ), -O-, -S-, -Se-, SO or SO ₂ can be replaced and where one or more H atoms are replaced by D, F, Cl , Br, I, CN or NO ₂ can be replaced, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which ^{can be substituted by one or more radicals R 1} , or an aryloxy or heteroaryloxy group with 5 to 60 aromatic Ring atoms, which can be substituted by one or more radicals R ¹ , or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, which ^{can be substituted by one or more radicals R 1} , or a combination of these systems; two or more, preferably adjacent, radicals R here can form a ring system with one another;

Ar

is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which ^{can be substituted with one or more preferably non-aromatic radicals R 1} , two radicals Ar, which are attached to the same Si atom, N- Bond atom, P atom or B atom, also through a single bond or a bridge, selected from B (R ¹ ), C (R ¹ ) ₂ , Si (R ¹ ) ₂ , C = O, C = NR ¹ , C = C (R ¹ ) ₂ , O, S, Se, S = O, SO ₂ , N (R ¹ ), P (R ¹ ) and P (= O) R ¹ , be bridged to one another;

R1

is on each occurrence, identically or differently, H, D, OH, F, Cl, Br, I, CN, NO ₂ , N (Ar ¹ ) ₂ , N (R ² ) ₂ , C (= O) Ar ¹ , C ( = O) R ² , P (= O) (Ar ¹ ) ₂ , P (Ar ¹ ) ₂ , B (Ar ¹ ) ₂ , B (OR ² ) ₂ , Si (Ar ¹ ) ₃ , Si (R ² ) ₃ , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms or an alkenyl or alkynyl group with 2 to 40 carbon atoms , each of which can be substituted by one or more radicals R ² , one or more non-adjacent CH ₂ groups being replaced by -R ² C = CR ² -, -C≡C-, Si (R ² ) ₂ , Ge (R ² ) ₂ , Sn (R ² ) ₂ , C = O, C = S, C = Se, C = NR ² , -C (= O) O-, -C (= O) NR ² -, NR ² , P (= O) (R ² ), -O-, -S-, -Se-, SO or SO ₂ can be replaced and one or more H atoms by D, F, CI, Br, I, CN or NO ₂ can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which is replaced by one or more radicals R ² subs may be substituted, or an aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms, which can be substituted by one or more radicals R ² , or an aralkyl or heteroaralkyl group with 5 to 40 aromatic ring atoms, which can be substituted with one or more radicals R ² may be substituted, or a combination of these systems; two or more, preferably adjacent, radicals R ^{1 here} can form a ring system with one another;

Ar1

is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which ^{can be substituted with one or more preferably non-aromatic radicals R 2} , two radicals Ar ¹ attached to the same Si atom, N atom , P atom or B atom bond, also through a single bond or a bridge, selected from B (R ² ), C (R ² ) ₂ , Si (R ² ) _2, C = O, C = NR ^2, C = C (R ² ) ₂ , O, S, Se, S = O, SO ₂ , N (R ² ), P (R ² ) and P (= O) R ² , be bridged to one another;

R2

is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, B (OR ³ ) ₂ , NO ₂ , C (= O) R ³ , CR ³ = C (R ³ ) ₂ , C (= O) OR ³ , C (= O) N (R ³ ) ₂ , Si (R ³ ) ₃ , P (R ³ ) ₂ , B (R ³ ) ₂ , N (R ³ ) ₂ , NO ₂ , P (= O) (R ³ ) ₂ , OSO ₂ R ³ , OR ³ , S (= O) R ³ , S (= O) ₂ R ³ , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 C. Atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, each of which ^{can be substituted by one or more radicals R 3} , one or more non-adjacent CH ₂ groups being replaced by -R ³ C = CR ³ -, -C≡C-, Si (R ³ ) ₂ , Ge (R ³ ) ₂ , Sn (R ³ ) ₂ , C = O, C = S, C = NR ³ , -C (= O ) O-, -C (= O) NR ³ -, NR ³ , P (= O) (R ³ ), -O-, -S-, -Se-, SO or SO ₂ can be replaced and where one or several H atoms can be replaced by D, F, Cl, Br, I, CN or NO ₂ , or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which can be substituted ^{by one or more radicals R 3} ann, or an aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms, which ^{can be substituted by one or more radicals R 3} , or a combination of these systems; two or more, preferably adjacent, substituents R ^{2 can} also form one with one another;

R3

is on each occurrence, identically or differently, selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms in which one or more H Atoms can be replaced by D, F, Cl, Br, I or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; two or more, preferably adjacent, substituents R ^{3 can} also form one with one another.

Adjacent carbon atoms in the context of the present invention are carbon atoms that are directly linked to one another. Furthermore, “adjacent radicals” in the definition of the radicals means that these radicals are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply accordingly, inter alia, to the terms “neighboring groups” and “neighboring substituents”.

The formulation that two or more radicals can form a ring with one another is to be understood in the context of the present description, inter alia, to mean that the two radicals are linked to one another by a chemical bond with formal elimination of two hydrogen atoms. This is illustrated by the following scheme.

Furthermore, the abovementioned formulation should also be understood to mean that, in the event that one of the two radicals represents hydrogen, the second radical binds to the position to which the hydrogen atom was bound to form a ring. This should be made clear by the following scheme:

A condensed aryl group, a condensed aromatic ring system or a condensed heteroaromatic ring system for the purposes of the present invention is a group in which two or more aromatic groups condense to one another via a common edge, i.e. H. fused, so that, for example, two carbon atoms belong to the at least two aromatic or heteroaromatic rings, such as in naphthalene, for example. In contrast, fluorene, for example, is not a condensed aryl group for the purposes of the present invention, since the two aromatic groups in fluorene do not have a common edge. Corresponding definitions apply to heteroaryl groups and to fused ring systems, which can, but do not have to, contain heteroatoms.

For the purposes of this invention, an aryl group contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms; For the purposes of this invention, a heteroaryl group contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. Here, under an aryl group or heteroaryl group, either a simple aromatic cycle, that is benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.

For the purposes of this invention, an aromatic ring system contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, in the ring system. A heteroaromatic ring system for the purposes of this invention contains 1 to 60 carbon atoms, preferably 1 to 40 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5. The heteroatoms are preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups also exist a non-aromatic unit (preferably less than 10% of the atoms other than H), such as e.g. B. a C, N or O atom or a carbonyl group, can be interrupted. For example, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and likewise systems in which two or more aryl groups are, for example, replaced by one linear or cyclic alkyl group or are interrupted by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are bonded directly to one another, such as. B. biphenyl, terphenyl, quaterphenyl or bipyridine, can also be understood as an aromatic or heteroaromatic ring system.

A cyclic alkyl, alkoxy or thioalkoxy group in the context of this invention is understood to mean a monocyclic, a bicyclic or a polycyclic group.

In the context of the present invention, a C ₁ - to C ₂₀ -alkyl group in which individual H atoms or CH ₂ groups can also be substituted by the groups mentioned above, for example the radicals methyl, ethyl, n-propyl, i -Propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n -Hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-heptyl, cycloheptyl , 1-methylcyclohexyl, n-octyl, 2-ethylhexyl, cyclooctyl, 1-bicyclo [2.2.2] octyl, 2-bicyclo [2.2.2] octyl, 2- (2,6-dimethyl) octyl , 3- (3,7-dimethyl) octyl, adamantyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, 1,1-dimethyl-n-hex-1-yl-, 1,1-dimethyl-n-hept -1-yl-, 1,1-dimethyl-n-oct-1-yl-, 1,1-dimethyl-n-dec-1 -yl-, 1,1-dimethyl-n-dodec-1-yl- , 1,1-dimethyl-n-tetradec-1-yl-, 1,1-dimethyl-n-hexadec-1-yl-, 1,1-dimethyl-n-octadec-1-yl-, 1,1- Diethy In-hex-1-yl-, 1,1-diethyl-n-hept-1-yl-, 1,1-diethyl-n-oct-1-yl-, 1,1-diethyl-n-dec-1 -yl-, 1,1-diethyl-n-dodec-1-yl-, 1,1-diethyl-n-tetradec-1-yl-, 1,1-diethyln-n-hexadec-1-yl-, 1 , 1-diethyl-n-octadec-1-yl-, 1- (n-propyl) -cyclohex-1-yl-, 1- (n-butyl) -cyclohex-1-yl-, 1- (n-hexyl ) -cyclohex-1-yl-, 1- (n-octyl) -cyclohex-1-yl- and 1- (n-decyl) -cyclohex-1-yl- understood. An alkenyl group is understood to mean, for example, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl. An alkynyl group is understood to mean, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. A C ₁ - to C ₄₀ -alkoxy group includes, for example Methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy understood.

An aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, preferably 5 - 40 aromatic ring atoms, which can also be substituted by the above-mentioned radicals and which can be linked via any positions on the aromatic or heteroaromatic, are understood as meaning, for example, groups, which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthene, dihydrophylene cis- or trans-indenofluorene, cis- or trans-monobenzoindenofluoren, cis- or trans-dibenzoindenofluoren, truxen, isotruxen, spirotruxen, spiroisotruxen, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene , Carbazole, indolocarbazole, indenocarbazole, pyridine, Quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, Pyrazinimidazole, quinoxaline imidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline, 1,5-diazaant 2,7 Diazapyren, 2,3-diazapyren, 1,6-diazapyren, 1,8-diazapyren, 4,5-diazapyren, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubine, 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.

wobei die verwendeten Symbole V und X die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweisen.In a preferred embodiment, the compounds according to the invention can contain at least one structure according to the formula (II), where the compounds can preferably be represented by structures of the formula (II),

where the symbols V and X used have the meaning given above, in particular for formula (I).

In a preferred embodiment it can be provided that the radical R bonded to the N atom in group V comprises an aromatic or heteroaromatic radical, preferably the N atom bonds to an aromatic or heteroaromatic radical, particularly preferably to an aryl or heteroaryl group.

wobei die verwendeten Symbole X und R die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweisen. Hierbei sind Strukturen gemäß Formel (IIIa) bevorzugt.The compounds according to the invention can preferably comprise structures according to the formulas (IIa) and / or (IIIb), the compounds preferably being able to be represented by structures of the formulas (IIa) and / or (IIIb),

where the symbols X and R used have the meaning given above, in particular for formula (I). Structures according to formula (IIIa) are preferred here.

wobei die verwendeten Symbole X und R die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweisen und m 0, 1, 2, 3, oder 4, vorzugsweise 0, 1, 2 oder 3, besonders bevorzugt 0, 1 oder 2 ist. Hierbei sind Strukturen gemäß Formel (IVa) bevorzugt.Furthermore, it can be provided that the compounds according to the invention comprise structures according to the formulas (IVa) and / or (IVb), wherein the compounds can preferably be represented by structures of the formulas (IVa) and / or (IVb),

where the symbols X and R used have the meaning given above, in particular for formula (I), and m is 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2. Structures according to formula (IVa) are preferred here.

wobei die verwendeten Symbole X und R die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweisen und m bei jedem Auftreten gleich oder verschieden 0, 1, 2, 3, oder 4, vorzugsweise 0, 1, 2 oder 3, besonders bevorzugt 0, 1 oder 2 ist. Hierbei sind Strukturen gemäß Formel (Va) bevorzugt.Furthermore, it can be provided that the compounds according to the invention comprise structures according to the formulas (Va) and / or (Vb), wherein the compounds can preferably be represented by structures of the formulas (Va) and / or (Vb),

where the symbols X and R used have the meaning given above, in particular for formula (I), and m on each occurrence, identically or differently, 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, particularly preferably 0 , Is 1 or 2. Structures according to formula (Va) are preferred here.

It can preferably be provided that in formulas (I), (II), (Illa), (IIIb), (IVa), (IVb), (Va) or (Vb) at most two groups X per ring represent N, preferably at least one, particularly preferably at least two, of the groups X per ring are selected from CH and CD.

In formulas (I), (II), (lilac), (IIIb), (IVa), (IVb), (Va) or (Vb), no more than four, preferably no more than two, groups X are preferably N , particularly preferably all groups X stand for CR, where preferably at most 4, particularly preferably at most 3 and especially preferably at most 2 of the groups CR for which X stands are not the same as the group CH.

wobei R die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweist und m bei jedem Auftreten gleich oder verschieden 0, 1, 2, 3, oder 4, vorzugsweise 0, 1, 2 oder 3, besonders bevorzugt 0, 1 oder 2 ist. Hierbei sind Strukturen gemäß Formel (VIa) bevorzugt.Furthermore, it can be provided that the compounds according to the invention comprise structures according to the formulas (VIa) and / or (VIb), wherein the compounds can preferably be represented by structures of the formulas (Via) and / or (VIb),

where R has the meaning given above, in particular for formula (I), and m is on each occurrence, identically or differently, 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2 . Structures according to formula (VIa) are preferred here.

The sum of the indices m in structures of the formulas (IVa), (IVb), (Va), (Vb), (Vla), or (Vlb) is preferably at most 6, preferably at most 4 and particularly preferably at most 2.

Furthermore, compounds with structures according to the formulas (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), or (VIb) are preferred, which are characterized in that at least one of the radicals R is independently a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms, preferably with 1 to 10 carbon atoms, a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, preferably with 1 to 10 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, especially preferably with 5 to 18 aromatic ring atoms, which is through a or more radicals R or R ¹ can be substituted, preferably an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, especially preferably with 5 to 18 aromatic ring atoms, which is replaced by one or more R este radicals R or R ¹ can be substituted, particularly preferably an aryl group or a heteroaryl group with 5 to 40 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, especially preferably with 5 to 18 aromatic ring atoms, which are represented by one or more radicals R or R ¹ , wherein aryl groups with 6 to 40 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, especially preferably with 5 to 18 aromatic ring atoms, are very particularly preferred.

It can also be provided that the substituents R of the heteroaromatic ring system according to the formulas (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa) , or (VIb) with the ring atoms of the heteroaromatic ring system do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system. This includes the formation of a condensed ring system with possible substituents R ^1, R ² , R ³ , which can be bonded to the R radicals. It can preferably be provided that the substituents R according to the formulas (I), (II), (Illa), (Illb), (IVa), (IVb), (Va), (Vb), (Vla), or ( Vlb) do not form a ring system with the ring atoms of the heteroaromatic ring system. This includes the formation of a ring system with possible substituents R ^1, R ² , R ³ , which can be bonded to the R radicals.

If two radicals, which can in particular be selected from R, R ¹ , R ² , R and / or R ³ , form a ring system with one another, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic. The radicals which form a ring system with one another can be adjacent, ie these radicals are bonded to the same carbon atom or to carbon atoms that are directly bonded to one another, or they can be further apart.

According to a preferred embodiment, compounds according to the invention are represented by structures of the formula (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), or (VIb ) representable. Accordingly, compounds according to a structure of the formula (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), or (VIb) are preferred. Compounds comprising structures according to formula (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), or (VIb) preferably have one Molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol and very particularly preferably less than or equal to 1200 g / mol .

Furthermore, preferred compounds according to the invention are distinguished by the fact that they can be sublimed. These compounds generally have a molar mass of less than approx. 1200 g / mol.

In a further preferred embodiment it can be provided that the group R in the structures set out above is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1 -, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl and / or triphenylenyl, each of which can be substituted by one or more radicals R or R ¹ , with the exception of fluorenyl and carbazolyl, but are preferably unsubstituted, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylene groups being particularly preferred are.

If X stands for CR or if the aromatic and / or heteroaromatic groups are substituted by substituents R, then these substituents R are preferably selected from the group consisting of H, D, F, CN, N (Ar) ₂ , C (= O) Ar, P (= O) (Ar) ₂ , a straight-chain alkyl or alkoxy group with 1 to 10 carbon atoms or a branched or cyclic alkyl or alkoxy group with 3 to 10 carbon atoms or an alkenyl group with 2 to 10 C atoms, each of which ^{can be substituted by one or more radicals R 1} , one or more nonadjacent CH ₂ groups can be replaced by O and one or more H atoms can be replaced by D or F, an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which ^{can be substituted in each case with one or more radicals R 1} , but is preferably unsubstituted, or an aralkyl or heteroaralkyl group with 5 to 25 aromatic ring atoms, which is substituted with one or more radicals R ¹ can be uated; two substituents R, which are bonded to the same carbon atom or to adjacent carbon atoms, can optionally form a monocyclic or polycyclic, aliphatic, aromatic or heteroaromatic ring system which can be substituted ^{by one or more radicals R 1;} where Ar, identically or differently on each occurrence, is an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, which in each case ^{can be substituted with one or more radicals R 1} , an aryloxy group with 5 to 40 aromatic ring atoms, which with one or more radicals R ¹ may be substituted, or an aralkyl group with 5 to 40 aromatic ring atoms, each of which ^{may be substituted with one or more radicals R 1} , where optionally two or more, preferably adjacent substituents R ^{1 is} a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system can preferably form a mono- or polycyclic, aliphatic ring system which can be ^{substituted by one or more radicals R 2} , where the symbol R ^{2 can have} the meaning given above, in particular for formula (I). Preferably, Ar, identically or differently on each occurrence, represents an aryl or heteroaryl group with 5 to 24, preferably 5 to 12 aromatic ring atoms, each of which ^{can be substituted by one or more radicals R 1} , but is preferably unsubstituted.

Examples of suitable groups Ar are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, especially branched terphenyl, quaterphenyl, especially branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1 -, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl and 1-, 2-, 3- or 4-carbazolyl, each of which ^{can be substituted by one or more radicals R 1} , but are preferably unsubstituted.

These substituents R are particularly preferably selected from the group consisting of H, D, F, CN, N (Ar) ₂ , a straight-chain alkyl group with 1 to 8 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 8 carbon atoms, preferably with 3 or 4 carbon atoms, or an alkenyl group with 2 to 8 carbon atoms, preferably with 2, 3 or 4 carbon atoms, each with one or several radicals R ¹ can be substituted, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each with one or more not -aromatic radicals R ¹ can be substituted, but is preferably unsubstituted; optionally two substituents R, which are bonded to the same carbon atom or to adjacent carbon atoms, can form a monocyclic or polycyclic, aliphatic ring system which ^{can be substituted with one or more radicals R 1} , but is preferably unsubstituted, where Ar is as defined above may have.

The substituents R are very particularly preferably selected from the group consisting of H or an aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, preferably with 6 to 13 aromatic ring atoms, which can each be substituted ^{with one or more non-aromatic radicals R 1} , but is preferably unsubstituted.

In a preferred embodiment it can be provided that the radical R bonded to the N atom in structures of the formulas (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), or (VIb) comprises an aromatic or heteroaromatic radical, preferably the N atom bonds to an aromatic or heteroaromatic radical, particularly preferably to an aryl or heteroaryl group.

Preferably, it can be provided, characterized in that the compound comprises a hole transport group, wherein a group R preferably comprises a hole transport group, preferably represents.

According to a further embodiment, one of the radicals R is a group selected from arylamino groups, preferably di- or triarylamino groups, heteroarylamino groups, preferably di- or triheteroarylamino groups, carbazole groups, carbazole groups being preferred. These groups can also be viewed as a hole-transporting group.

It can preferably be provided that the compound comprises an electron transport group, one group R preferably comprising, preferably representing, an electron transport group. Electron transport groups are well known in the art and promote the ability of compounds to transport and / or conduct electrons.

Furthermore, compounds comprising at least one structure according to formula (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), or (VIb) or their preferred embodiments, surprising advantages in which the group R comprises at least one structure selected from the group consisting of pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinazolines, quinoxalines, quinolines, isoquinolines, imidazoles and / or benzimidazoles, with pyrimidines, Triazines and quinazolines are particularly preferred.

bedeuten, worin W bei jedem Auftreten gleich oder verschieden ein aromatisches oder heteroaromatisches Ringsystem mit 5 bis 30 aromatischen Ringatomen, welches durch einen oder mehrere Reste R¹ substituiert sein kann, ein Stickstoffatom, ein Boratom, ein Phosphoratom oder eine Phosphanoxidgruppe darstellt, die gestrichelte Bindung die Anbindungsposition markiert und die Symbole Ar und R¹ die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweisen.In a preferred embodiment it can be provided that at least one group R in the formulas (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa ), or (VIb) represents a group which can be represented by the formula L ¹ -Z, in which L ^{1 represents} a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30, aromatic ring atoms, which is represented by one or several radicals R ¹ can be substituted, represents ZR ¹ , Ar or a group of the formula Z ^a or Z ^b , in which the symbols Ar and R ^{1 have} the meaning given above, in particular for formula (I), and Z ^a or Z ^b

mean, in which W on each occurrence, identically or differently, represents an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which ^{can be substituted by one or more radicals R 1} , a nitrogen atom, a boron atom, a phosphorus atom or a phosphine oxide group, the dashed bond the attachment position is marked and the symbols Ar and R ^{1 have} the meaning given above, in particular for formula (I).

It can also be provided that at least one group R, preferably all of the groups R in the formulas (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb) , (VIa), or (VIb) represent a group which can be represented by the radicals of the formula R ¹ , as set out above and below.

wobei das Symbol X N, CR oder C darstellt, falls an X die Gruppe -L¹-Z gebunden ist, und die verwendeten Symbole R, L¹ und Z die zuvor, insbesondere für Formeln (I) und/oder (L¹-Z) genannte Bedeutung aufweisen. Hierbei sind Strukturen gemäß Formeln (Vlla), (Vllc) und/oder (VIIe) bevorzugt. In einer bevorzugten Ausführungsform kann vorgesehen sein, dass das Symbol X für N oder CR¹ steht, wobei R¹ die zuvor, insbesondere für Formeln (I) genannte Bedeutung aufweist.It can preferably be provided that the compounds according to the invention comprise structures according to the formulas (VIIa), (VIIb), (VIIc), (VIId), (VIIe) or (VIIf), the compounds preferably being represented by structures of the formulas (VIIa), (VIIb), (VIIc), (VIId), (VIIe) or (VIIf) can be displayed,

where the symbol X representsN, CR or C, if the group -L ¹ -Z is bonded to X, and the symbols R, L ¹ and Z used above, in particular for formulas (I) and / or (L ¹ -Z ) have the meaning mentioned. Structures according to formulas (VIIa), (VIIc) and / or (VIIe) are preferred here. In a preferred embodiment it can be provided that the symbol X stands for N or CR ¹ , where R ^{1 has} the meaning given above, in particular for formulas (I).

It can further be provided that in structures according to formulas (VIIa), (VIIb), (VIIc), (VIId), (VIIe) or (VIIf), at most two groups X per ring represent N, preferably at least one, particularly preferably at least two of the groups X per ring are selected from CH and CD.

In structures according to the formulas (VIIa), (VIIb), (VIIc), (VIId), (VIIe) or (VIIf), no more than four, preferably no more than two groups X represent N, particularly preferably all groups X are CR, where preferably at most 4, particularly preferably at most 3 and especially preferably at most 2 of the groups CR for which X is not the same as the group CH.

wobei die Symbole Ar und R¹ die zuvor, insbesondere für Formeln (I) genannte Bedeutung aufweisen und die Gruppe -L¹-Z die zuvor für Formel (L¹-Z) genannte Bedeutung aufweist, m bei jedem Auftreten unabhängig 0, 1, 2, 3, oder 4, vorzugsweise 0, 1, 2 oder 3, besonders bevorzugt 0,1 oder 2 ist und n bei jedem Auftreten unabhängig 0, 1, 2, oder 3, vorzugsweise 0, 1 oder 2, besonders bevorzugt 0 oder 1 ist. Hierbei sind Verbindungen mit Gruppen der Formeln (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf) oder (VIIIm) bevorzugt.It can preferably be provided that the compounds according to the invention have structures according to the formulas (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf), (VIIIg), (VIIIh), (VIIIi), ( VIIIj), (VIIIk), (VIIIl), (VIIIm) or (VIIIn), the compounds preferably being represented by structures of the formulas (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf ), (VIIIg), (VIIIh), (VIIIi), (VIIIj), (VIIIk), (VIIIl), (VIIIm) or (VIIIn) can be displayed,

where the symbols Ar and R ^{1 have} the meaning given above, in particular for formulas (I), and the group -L ¹ -Z has the meaning given above for formula (L ¹ -Z), m at each occurrence independently 0, 1, 2, 3, or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2 and n is independently 0, 1, 2, or 3, preferably 0, 1 or 2, particularly preferably 0 or, on each occurrence 1 is. In this connection, compounds with groups of the formulas (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf) or (VIIIm) are preferred.

wobei die Symbole Ar und R¹ die zuvor, insbesondere für Formeln (I) genannte Bedeutung aufweisen und die Gruppe -L¹-Z die zuvor für Formel (L¹-Z) genannte Bedeutung aufweist, m bei jedem Auftreten unabhängig 0, 1, 2, 3, oder 4, vorzugsweise 0, 1, 2 oder 3, besonders bevorzugt 0,1 oder 2 ist und n 0, 1, 2, oder 3, vorzugsweise 0, 1 oder 2, besonders bevorzugt 0 oder 1 ist. Hierbei sind Verbindungen mit Gruppen der Formeln (IXa), (IXb), (IXc), (IXd), (IXe), (IXg), (IXh), (IXi), (IXk), (IXm), (IXo), (IXp), (IXq) oder (IXr) bevorzugt, wobei Verbindungen mit Gruppen der Formeln (IXa), (IXc), (IXe), (IXg), (IXi), (IXk), (IXm), (IXo) oder (IXq) besonders bevorzugt und Verbindungen mit Gruppen der Formeln (IXa), (IXc), (IXg), (IXo) oder (IXq) ganz besonders bevorzugt sind.It can preferably be provided that the compounds according to the invention have structures according to the formulas (IXa), (IXb), (IXc), (IXd), (IXe), (IXf), (IXg), (IXh), (IXi), (IXj), (IXk), (IXI), (IXm), (IXn), (IXo ), (IXp), (IXq) or (IXr), the compounds preferably being represented by structures of the formulas (IXa), (IXb), (IXc), (IXd), (IXe), (IXf), (IXg) , (IXh), (IXi), (IXj), (IXk), (IXI), (IXm), (IXn), (IXo), (IXp), (IXq) or (IXr) can be displayed,

where the symbols Ar and R ^{1 have} the meaning given above, in particular for formulas (I), and the group -L ¹ -Z has the meaning given above for formula (L ¹ -Z), m at each occurrence independently 0, 1, 2, 3, or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2 and n is 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1. Here are compounds with groups of the formulas (IXa), (IXb), (IXc), (IXd), (IXe), (IXg), (IXh), (IXi), (IXk), (IXm), (IXo) , (IXp), (IXq) or (IXr) preferred, whereby compounds with groups of the formulas (IXa), (IXc), (IXe), (IXg), (IXi), (IXk), (IXm), (IXo ) or (IXq) are particularly preferred and compounds with groups of the formulas (IXa), (IXc), (IXg), (IXo) or (IXq) are very particularly preferred.

Furthermore, it can be provided that in structures according to the formulas (VIIIa) to (VIIIn) or (IXa) to (IXr) the sum of the indices m and n is at most 5, preferably at most 3 and particularly preferably at most 1.

In a preferred embodiment it can be provided that the radical R or Ar bonded to the N atom in structures of the above formulas, inter alia in (VIIa) to (VIIf), (VIIIa) to (VIIIn) or (IXa) to ( IXr) comprises an aromatic or heteroaromatic radical, preferably the N atom binds to an aromatic or heteroaromatic radical, particularly preferably to an aryl or heteroaryl group. Here, in particular, a bond is formed between an N atom and a C atom which is part of an aromatic or heteroaromatic ring.

Furthermore, it can be provided that the group L ¹ -Z in the above formulas, inter alia in (VIIa) to (VIIf), (VIIIa) to (VIIIn) or (IXa) to (IXr) is a hole transport group and / or an electron transport group or represents a hole transport group and / or an electron transport group.

wobei für die verwendeten Symbole gilt:

k

ist bei jedem Auftreten unabhängig 0 oder 1;

i

ist bei jedem Auftreten unabhängig 0,1 oder 2;

j

ist bei jedem Auftreten unabhängig 0, 1, 2 oder 3;

h

ist bei jedem Auftreten unabhängig 0, 1, 2, 3 oder 4;

die gestrichelte Bindung markiert die Anbindungsposition; und

Ar1,

R¹ weisen die zuvor, insbesondere für Formel (I) genannte Bedeutung auf.

It can further be provided that the symbol Z in formula L ¹ -Z or in a structure according to formulas (VIIa) to (VIIf), (VIIIa) to (VIIIn) and / or (IXa) to (IXr) stands for a group , which is selected from the formulas (Z-1) to (Z ¹ - 91)

where the following applies to the symbols used:

k

is independently 0 or 1 on each occurrence;

i

is independently 0, 1 or 2 on each occurrence;

j

is on each occurrence independently 0, 1, 2 or 3;

H

is on each occurrence independently 0, 1, 2, 3 or 4;

the dashed bond marks the attachment position; and

Ar1,

R ¹ have the meaning given above, in particular for formula (I).

The group L ¹ can preferably form a continuous conjugation with the group Z and the atom to which the group L ¹ or according to formula (L ¹ -Z) is bound. A continuous conjugation of the aromatic or heteroaromatic systems is formed as soon as direct bonds are formed between adjacent aromatic or heteroaromatic rings. A further link between the aforementioned conjugated groups, for example via an S, N or O atom or a carbonyl group, does not damage a conjugation.

In a further preferred embodiment of the invention, L ^{1 represents} a bond or an aromatic or heteroaromatic ring system with 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system with 6 to 12 carbon atoms, which can be substituted ^{by one or more radicals R 1} , but is preferably unsubstituted, where R ^{1 can have} the meaning given above, in particular for formula (I). ^{L 1} particularly preferably stands for an aromatic ring system with 6 to 10 aromatic ring atoms or a heteroaromatic ring system with 6 to 13 heteroaromatic ring atoms, which can in each case be ^{substituted by one or more radicals R 1} , but is preferably unsubstituted, where R ^{1 is} the above, can have in particular the meaning mentioned for formula (I).

Furthermore, the symbol L ¹ set out inter alia in formula (L ¹ -Z) preferably stands, identically or differently on each occurrence, for a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 Ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.

Furthermore, it can be provided that the group L ^{1 shown in formula (L 1} -Z) comprises an aromatic ring system with at most two condensed aromatic and / or heteroaromatic 6-membered rings, preferably no condensed aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and / or dibenzothienyl structures are preferred over naphthyl structures.

Structures which have no condensation, such as, for example, phenyl, biphenyl, terphenyl and / or quaterphenyl structures, are particularly preferred.

Examples of suitable aromatic or heteroaromatic ring systems L ¹ are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, especially branched terphenylene, quaterphenylene, especially branched quaterphenylene, fluorenylene, Spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, each of which ^{can be substituted by one or more radicals R 1} , but are preferably unsubstituted.

Furthermore, it can be provided that the ^{group L 1} set out, ^{inter alia, in formula (L 1} -Z) has at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.

wobei die gestrichelten Bindungen jeweils die Anbindungspositionen markieren, der Index k 0 oder 1 ist, der Index I 0, 1 oder 2 ist, der Index j bei jedem Auftreten unabhängig 0, 1, 2 oder 3 ist; der Index h bei jedem Auftreten unabhängig 0, 1, 2, 3 oder 4 ist, der Index g 0, 1, 2, 3, 4 oder 5 ist; das Symbol Y¹ O, S oder NR¹, vorzugsweise 0 oder S ist; und das Symbol R¹ die zuvor, insbesondere für Formel (I) genannte Bedeutung aufweist.Preference is given to compounds comprising structures of the formulas (VIIa) to (VIIf), (VIIIa) to (VIIIn) and / or (IXa) to (IXr) in which the group L ^{1 of} the structural element L ¹ -Z represents a bond or represents a group which is selected from the formulas (L ¹ -1) to (L ¹ -167)

where the dashed bonds mark the attachment positions, the index k is 0 or 1, the index I is 0, 1 or 2, the index j is independently 0, 1, 2 or 3 at each occurrence; the subscript h at each occurrence is independently 0, 1, 2, 3 or 4; the subscript g is 0, 1, 2, 3, 4 or 5; the symbol Y ^{1 is} O, S or NR ¹ , preferably 0 or S; and the symbol R ^{1 has} the meaning given above, in particular for formula (I).

It can preferably be provided that the sum of the indices k, I, g, h and j in the structures of the ^{formulas (L 1} -1) to (L ¹ -167) is in each case at most 3, preferably at most 2 and particularly preferably at most 1 .

Preferred compounds according to the invention with a group of the formula (L ¹ -Z) comprise a group L ¹ which represents a bond or which is selected from one of the formulas (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L1-167), preferably of the formula (L ¹ -1) to (L ¹ -54) and / or (L ¹ -92) to (L ¹ -167), especially preferably of the formula (L ¹ -1) to (L ¹ -29) and / or (L ¹ -92) to (L ¹ -167). Advantageously, the sum of the indices k, I, g, h and j in the structures of the formulas (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) , preferably of the formula (L ¹ -1) to (L ¹ -54) and / or (L ¹ -92) to (L ¹ -167), particularly preferably of the formula (L ¹ -1) to (L ¹ -29 ) and / or (L ¹ -92) to (L ¹ -167) are each at most 3, preferably at most 2 and particularly preferably at most 1.

The radicals R ¹ in the formulas (L ¹ -1) to (L ¹ -167) preferably do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system, with the ring atoms of the aryl group or heteroaryl group to which the radicals R ^{1 are bonded} . This includes the formation of a condensed ring system with possible substituents R ² , R ³ , which can be bonded to the radicals R ¹ and R ^{2, respectively.}

It can also be provided that the group Ar ¹ and / or R ^{1 is} selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2 -, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2-, 3- or 4- Dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, 1-, 2-, 3- or 4-carbazolyl, 1- or 2-naphthyl, anthracenyl, preferably 9-anthracenyl, phenanthrenyl and / or triphenylenyl, each through one or more R ² radicals can be substituted, but are preferably unsubstituted, with phenyl, spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, anthracene, phenanthrene, triphenylene groups being particularly preferred.

wobei für die verwendeten Symbole gilt:

Y1

ist O, S oder NR², vorzugsweise O oder S;

k

ist bei jedem Auftreten unabhängig 0 oder 1;

i

ist bei jedem Auftreten unabhängig 0, 1 oder 2;

j

ist bei jedem Auftreten unabhängig 0, 1, 2 oder 3;

h

ist bei jedem Auftreten unabhängig 0, 1, 2, 3 oder 4;

g

ist bei jedem Auftreten unabhängig 0, 1, 2, 3, 4 oder 5;

R2

weist die zuvor genannte, insbesondere für Formel (I) genannte Bedeutung auf und

die gestrichelte Bindung markiert die Anbindungsposition.Furthermore, it can be provided that in a structure according to formula (I), (II), (IIIa), (IIIb), (IVa), (IVb), (Va), (Vb), (VIa), (VIb) , (VIIa) to (VIIf), (VIIIa) to (VIIIn), (IXa) to (IXr), (L ¹ -1) to (L ¹ -163) and / or (Z-1) to (Z- 91) at least one radical R ¹ or Ar ^{1 represents} a group which is selected from the formulas (R ¹ -1) to (R ¹ - 179)

where the following applies to the symbols used:

Y1

is O, S or NR ² , preferably O or S;

k

is independently 0 or 1 on each occurrence;

i

is on each occurrence independently 0, 1 or 2;

j

is on each occurrence independently 0, 1, 2 or 3;

H

is on each occurrence independently 0, 1, 2, 3 or 4;

G

is on each occurrence independently 0, 1, 2, 3, 4 or 5;

R2

has the meaning given above, in particular for formula (I), and

the dashed bond marks the attachment position.

Of the aforementioned structures of the formulas (R ¹ -1) to (R ¹ -179), the groups of the formulas (R ¹ -1) to (R ¹ -177) are preferred, groups of the formulas (R ¹ -1) to (R ¹ -64) and (R ¹ -94) to (R ¹ -177) are particularly preferred and the groups of the formulas (R ¹ -1) to (R ¹ -64) and (R ¹ -115) to ( R ¹ -177) are very particularly preferred.

It can preferably be provided that the sum of the indices i, j, h and g in the structures of the formulas (R ¹ -1) to (R ¹ -179) is in each case at most 3, preferably at most 2 and particularly preferably at most 1.

The radicals R ² in the formulas (R ¹ -1) to (R ¹ -179) preferably do not form a condensed aromatic or heteroaromatic ring system, preferably no condensed ring system, with the ring atoms of the aryl group or heteroaryl group to which the radicals R ^{2 are bonded} . This includes the formation of a condensed ring system with possible substituents R ³ which can be bonded to the radicals R ^2.

If the compound according to the invention is substituted by aromatic or heteroaromatic groups R ¹ or R ² , it is preferred, especially when they are configured as host material, electron transport material or hole transport material, if they do not contain aryl or heteroaryl groups with more than two aromatic groups directly condensed to one another Have six rings. The substituents particularly preferably have no aryl or heteroaryl groups with six-membered rings fused directly to one another. This preference is due to the low triplet energy of such structures. Condensed aryl groups with more than two aromatic six-membered rings condensed directly to one another, which are nevertheless also suitable according to the invention, are phenanthrene and triphenylene, since these too have a high triplet level.

In a further preferred embodiment of the invention, R ² , for example in a structure according to formula (I) and preferred embodiments of this structure or the structures in which reference is made to these formulas, is selected identically or differently on each occurrence from the group consisting of H, D, an aliphatic hydrocarbon radical with 1 to 10 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, particularly preferably with 5 to 13 aromatic ring atoms, which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, but is preferably unsubstituted.

In a further preferred embodiment of the invention, R ³ , for example in a structure according to formula (I) and preferred embodiments of this structure or the structures in which reference is made to these formulas, is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 10 carbon atoms, preferably with 1, 2, 3 or 4 carbon atoms, or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, preferably with 5 to 24 aromatic ring atoms, particularly preferably having 5 to 13 aromatic ring atoms, which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, but is preferably unsubstituted.

wobei Et eine Ethylgruppe darstellt und R^a H, C₁ bis C₆-Alkyl oder 1,1-Dimethyl-2-hydroxyethyl ist, R^b bei jedem Auftreten jeweils unabhängig, Halogen, C₁ bis C₄-Alkyl, C₁ bis C₄-Alkyloxy, C₁ bis C₄-Haloalkyloxy, C₁ bis C₄-Haloalkyl, C₃ bis C₇-Alkenyl, Amino, Carbonyl, Nitro, Methoxycarbonyl oder Aminocarbonyl ist, R^c bei jedem Auftreten jeweils unabhängig H, OH, C₁ bis C₆-Alkyl, Phenyl, Phenoxyl, C₁ bis C₄-Alkyloxy, und i 0, 1 oder 2 darstellt.It can preferably be provided that structures of the formulas (A), (B), (C) and (D) are excluded from protection

where Et represents an ethyl group and R ^{a is} H, C ₁ to C ₆ -alkyl or 1,1-dimethyl-2-hydroxyethyl, R ^b on each occurrence independently, halogen, C ₁ to C ₄ -alkyl, C ₁ to Is C ₄ alkyloxy, C ₁ to C ₄ haloalkyloxy, C ₁ to C ₄ haloalkyl, C ₃ to C ₇ alkenyl, amino, carbonyl, nitro, methoxycarbonyl or aminocarbonyl, R ^c is each Appear in each case independently H, OH, C ₁ to C ₆ -alkyl, phenyl, phenoxyl, C ₁ to C ₄ -alkyloxy, and i represents 0, 1 or 2.

Particularly preferred compounds according to the invention with structures of the formulas (I), (II), (Illa), (IVa) or (IVb), where a total of at most 4, preferably at most 2, radicals of the formula X are not CH or CD, with at least one The radical R comprises an electron transport group, preferably a triazine group, particularly preferably a group of the formula (L ¹ -Z), in which Z represents a group of the formula (Z-48) which has the following properties: R, not equal to H or D or Ar ¹ preferably in formula (L ¹ -Z): L ¹ preferably R ¹ -1 to R ¹ -177 R ¹ -1 to R ¹ -64 and (R ¹ -115) to (R ¹ -177) a bond or L ¹ -1 to L ¹ -167 a bond or (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) R ¹ -1 to R ¹ -177 R ¹ -1 to R ¹ -64 and (R ¹ -115) to (R ¹ -177) a bond or (L ¹ -1) to (L ¹ -29) or (L ¹ -92) to (L ¹ -167) a bond R ¹ -1 to R ¹ -4 R ¹ -1 a bond or L ¹ -1 to L ¹ -167 a bond or (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) R ¹ -1 to R ¹ -4 R ¹ -1 a bond or (L ¹ -1) to (L ¹ -29) or (L ¹ -92) to (L ¹ -167) a bond

Particularly preferred compounds according to the invention with structures of the formulas (I), (II), (IIIa), (IVa) or (IVb), where a total of at most 4, preferably at most 2, radicals of the formula X are not CH or CD, with at least one The radical R comprises a hole transport group, preferably a triarylamine or carbazole group, particularly preferably a group of the formula (L ¹ -Z), in which Z represents a group of the formula (Z-1) which has the following properties: R, not equal to H or D or Ar ¹ preferably in formula (L ¹ -Z): L ¹ preferably R ¹ -1 to R ¹ -177 R ¹ -1 to R ¹ -64 and (R ¹ -115) to (R ¹ -177) a bond or L ¹ -1 to L ¹ -167 a bond or (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) R ¹ -1 to R ¹ -177 R ¹ -1 to R ¹ -64 and (R ¹ -115) to (R ¹ -177) a bond or (L ¹ -1) to (L ¹ -29) or (L ¹ -92) to (L ¹ -167) a bond R ¹ -1 to R ¹ -4 R ¹ -1 a bond or L ¹ -1 to L ¹ -167 a bond or (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) R ¹ -1 to R ¹ -4 R ¹ -1 a bond or (L ¹ -1) to (L ¹ -29) or (L ¹ -92) to (L ¹ -167) a bond

Particularly preferred compounds according to the invention with structures of the formulas (I), (II), (IIIa), (IVa) or (IVb), where a total of at most 4, preferably at most 2, radicals of the formula X are not CH or CD, with at least one The radical R comprises a condensed aromatic ring system, preferably an anthracene, phenanthrene, triphenylene group, particularly preferably a group of the formula (L ¹ -Z), in which Z represents a group of the formula (Z-81) which has the following properties: R, not equal to H or D or Ar ¹ preferably in formula (L ¹ -Z): L ¹ preferably R ¹ -1 to R ¹ -177 R ¹ -1 to R ¹ -64 and (R ¹ -115) to (R ¹ -177) a bond or L ¹ -1 to L ¹ -167 a bond or (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) R ¹ -1 to R ¹ -177 R ¹ -1 to R ¹ -64 and (R ¹ -115) to (R ¹ -177) a bond or (L ¹ -1) to (L ¹ -29) or (L ¹ -92) to (L ¹ -167) a bond R ¹ -1 to R ¹ -4 R ¹ -1 a bond or L ¹ -1 to L ¹ -167 a bond or (L ¹ -1) to (L ¹ -78) and / or (L ¹ -92) to (L ¹ -167) R ¹ -1 to R ¹ -4 R ¹ -1 a bond or (L ¹ -1) to (L ¹ -29) or (L ¹ -92) to (L ¹ -167) a bond

1 2 3

4 5 6

7 8 9

10 11 12

13 14 15

16 17 18

19 20 21

22 23 Examples of suitable compounds according to the invention are the structures shown below according to the following formulas 1 to 23:

1 2 3

4th 5 6th

7th 8th 9

10 11 12th

13th 14th 15th

16 17th 18th

19th 20th 21

22nd 23

Preferred embodiments of compounds according to the invention are described in more detail in the examples, it being possible for these compounds to be used alone or in combination with others for all of the uses according to the invention.

Provided that the conditions mentioned in claim 1 are met, the preferred embodiments mentioned above can be combined with one another as desired. In a special one preferred embodiment of the invention, the above-mentioned preferred embodiments apply simultaneously.

The compounds according to the invention can in principle be prepared by various methods. However, the methods described below have proven to be particularly suitable.

The present invention therefore further provides a process for the preparation of the compounds comprising structures according to formula (I), in which a compound comprising at least one lactam group is linked to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction .

Suitable compounds comprising at least one lactam group can in many cases be obtained commercially, the starting compounds set out in the examples being obtainable by known processes, so reference is made to them.

Compounds comprising at least one nitrogen-containing heterocyclic group can be reacted with further aryl or heteroaryl compounds by known coupling reactions, the necessary conditions for this being known to the person skilled in the art and detailed information in the examples supporting the person skilled in the art for carrying out these reactions.

Particularly suitable and preferred coupling reactions, all of which lead to C-C linkages and / or C-N linkages, are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA. These reactions are well known, the examples providing further guidance to those skilled in the art.

In all of the following synthesis schemes, the compounds are shown with a small number of substituents to simplify the structures. This does not preclude the presence of any further substituents in the processes.

A conversion results, for example, according to the following scheme, without any intention that this should result in a restriction. The sub-steps of the individual schemes can be combined as required.

The meaning of the symbols used in schemes 1 and 2 essentially corresponds to those defined for formula (I) or L ¹ -Z, with numbering being dispensed with for the sake of clarity.

The methods shown for the synthesis of the compounds according to the invention are to be understood as examples. The person skilled in the art can develop alternative synthetic routes within the scope of his general specialist knowledge.

The basics of the production processes set out above are known in principle from the literature for similar compounds and can easily be adapted by the person skilled in the art for the production of the compounds according to the invention. Further information can be found in the examples.

By these methods, optionally followed by purification, e.g. B. recrystallization or sublimation, the compounds according to the invention, comprising structures according to formula (I), can be obtained in high purity, preferably more than 99% (determined by means of ¹ H-NMR and / or HPLC).

The compounds according to the invention can also have suitable substituents, for example by longer alkyl groups (about 4 to 20 carbon atoms), in particular branched alkyl groups, or optionally substituted aryl groups, for example xylyl, mesityl or branched terphenyl or quaterphenyl groups, which have a Cause solubility in common organic solvents, so that the compounds are soluble, for example, in toluene or xylene at room temperature in sufficient concentration to be able to process the compounds from solution. These soluble compounds are particularly suitable for processing from solution, for example by printing processes. It should also be noted that the compounds according to the invention, comprising at least one structure of the formula (I), already have increased solubility in these solvents.

The compounds according to the invention can also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is possible in particular with compounds which are substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups such as olefins or oxetanes. These can be used as monomers for producing corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization takes place preferably via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups. The compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.

The invention therefore further relates to oligomers, polymers or dendrimers containing one or more of the above-listed structures of the formula (I) or compounds according to the invention, where one or more bonds of the compounds according to the invention or the structures of the formula (I) to the polymer, oligomer or dendrimer available. Depending on the linkage of the structures of the formula (I) or the compounds, these therefore form a side chain of the oligomer or polymer or are linked in the main chain. The polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated. The oligomers or polymers can be linear, branched or dendritic. The same preferences as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.

To produce the oligomers or polymers, the monomers according to the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units of the formula (I) or the preferred embodiments set out above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%. Suitable and preferred comonomers which form the polymer backbone are selected from fluorene (e.g. according to EP 842208 or WO 2000/022026 ), Spirobifluorenes (e.g. according to EP 707020 , EP 894107 or WO 2006/061181 ), Para-phenylenes (e.g. according to WO 92/18552 ), Carbazoles (e.g. according to WO 2004/070772 or WO 2004/113468 ), Thiophenes (e.g. according to EP 1028136 ), Dihydrophenanthrenes (e.g. according to WO 2005/014689 ), cis- and trans-indenofluorenes (e.g. according to WO 2004/041901 or WO 2004/113412 ), Ketones (e.g. according to WO 2005/040302 ), Phenanthrenes (e.g. according to WO 2005/104264 or WO 2007/017066 ) or several of these units. The polymers, oligomers and dendrimers can also contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.

Furthermore, compounds according to the invention which are distinguished by a high glass transition temperature are of particular interest. In this context, in particular compounds according to the invention comprising structures of the general formula (I) or the preferred embodiments set out above and below are preferred which have a glass transition temperature of at least 70 ° C., particularly preferably of at least 110 ° C., very particularly preferably of at least 125 ° C and particularly preferably of at least 150 ° C, determined according to DIN 51005 (version 2005-08).

For the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It can be preferred to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 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 -Dimethyl anisole, 3,5-dimethyl anisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, Dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether, Diethylenglycolbutylmethylether, Triethylenglycolbutylmethylether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, Tripropyleneglycoldimethylether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis (3,4-dimethylphenyl) ethane, hexamethylindane or mixtures of these solvents.

The present invention therefore also provides a formulation containing a compound according to the invention and at least one further compound. The further compound can be, for example, a solvent, in particular one of the solvents mentioned above or a mixture of these solvents. The further compound can, however, also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound, in particular a phosphorescent dopant, and / or a further matrix material. This further compound can also be polymeric.

The present invention therefore again further provides a composition containing a compound according to the invention and at least one further organically functional material. Functional materials are generally the organic or inorganic materials that are inserted between the anode and cathode. The organically functional material is preferably selected from the group consisting of fluorescent emitters, phosphorescent emitters, polypodal emitters, emitters which show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole transport materials, hole injection materials, electron blocking materials, hole blocking materials, wide -Band-gap materials and n-dopants.

According to a particular aspect of the present invention, the compounds according to the invention can be used as matrix material, in particular for phosphorescent emitters, matrix materials often being used in combination with further matrix materials.

The present invention therefore also relates to a composition containing at least one compound comprising structures according to formula (I) or the preferred embodiments set out above and below, as well as at least one further matrix material.

Another subject matter of the present is a composition containing at least one compound comprising at least one structure according to formula (I) or the preferred embodiments set out above and below and at least one wide-band gap material, where wide-band Gap material means a material as disclosed by U.S. 7,294,849 is understood. These systems show particularly advantageous performance data in electroluminescent devices.

The additional compound can preferably have a band gap of 2.5 eV or more, preferably 3.0 eV or more, very preferably 3.5 eV or more. The band gap can be calculated using the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO).

Molecular orbitals, especially the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), their energy levels and the energy of the lowest triplet state T ₁ or the lowest excited singlet state S _{1 of} the materials are determined using quantum chemical calculations. To calculate organic substances, a geometry optimization is first carried out using the “Ground State / Semi-empirical / Default Spin / AM1 / Charge 0 / Spin Singlet” method. This is followed by an energy bill based on the optimized geometry. The method "TD-SCF / DFT / Default Spin / B3PW91" is used with the basic set "6-31 G (d)" (Charge 0, Spin Singlet). The HOMO energy level HEh or LUMO energy level LEh in Hartree units is obtained from the energy bill.

• HOMO(eV) = ((HEh*27.212)-0.9899)/1.1206
• LUMO(eV) = ((LEh*27.212)-2.0041)/1.385

From this, the HOMO and LUMO energy levels calibrated using cyclic voltammetry measurements are determined in electron volts as follows:

• HOMO (eV) = ((HEh * 27.212) -0.9899) /1.1206
• LUMO (eV) = ((LEh * 27.212) -2.0041) /1.385

For the purposes of this application, these values are to be regarded as the HOMO or LUMO energy levels of the materials.

The lowest triplet state T ₁ is defined as the energy of the triplet state with the lowest energy, which results from the quantum chemical calculation described.

The lowest excited singlet state S ₁ is defined as the energy of the excited singlet state with the lowest energy, which results from the described quantum chemical calculation.

The method described here is independent of the software package used and always delivers the same results. Examples of programs often used for this purpose are "Gaussian09W" (Gaussian Inc.) and Q-Chem 4.1 (Q-Chem, Inc.).

The present invention also relates to a composition comprising at least one compound comprising structures according to formula (I) or the preferred embodiments set out above and below and at least one phosphorescent emitter, the term phosphorescent emitter also being understood as phosphorescent dopants.

In a system comprising a matrix material and a dopant, a dopant is understood to mean that component whose proportion in the mixture is the smaller. Correspondingly, a matrix material in a system comprising a matrix material and a dopant is understood to mean that component whose proportion in the mixture is the greater.

Preferred phosphorescent dopants for use in matrix systems, preferably mixed matrix systems, are the preferred phosphorescent dopants specified below.

The term phosphorescent dopants typically includes compounds in which the light emission occurs through a spin-forbidden transition, for example a transition from an excited triplet state or a state with a higher spin quantum number, for example a quintet state.

Particularly suitable phosphorescent compounds (= triplet emitters) are compounds which, when suitably excited, emit light, preferably in the visible range, and which 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, especially a metal with this atomic number. Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used as phosphorescence emitters, in particular compounds containing iridium or platinum. For the purposes of the present invention, all luminescent compounds which contain the metals mentioned above are regarded as phosphorescent compounds.

Examples of the emitters described above can be found in the applications WO 00/70655 , WO 2001/41512 , WO 2002/02714 , WO 2002/15645 , EP 1191613 , EP 1191612 , EP 1191614 , WO 05/033244 , WO 05/019373 , US 2005/0258742 , WO 2009/146770 , WO 2010/015307 , WO 2010/031485 , WO 2010/054731 , WO 2010/054728 , WO 2010/086089 , WO 2010/099852 , WO 2010/102709 , WO 2011/032626 , WO 2011/066898 , WO 2011/157339 , WO 2012/007086 , WO 2014/008982 , WO 2014/023377 , WO 2014/094961 , WO 2014/094960 , WO 2016/124304 , WO 2016/015815 , WO 2016/000803 , WO 2015117718 , WO 2015104045 and WO 2015036074 . In general, all phosphorescent complexes such as 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 electroluminescence are suitable, and the person skilled in the art can use further phosphorescent complexes without inventive effort.

Explicit examples of phosphorescent dopants are listed in the following table.

According to a particular aspect of the present invention, the compounds according to the invention can be used as hole blocking material, preferably in a hole blocking layer, the compounds according to the invention used as hole blocking material comprising at least one electron transport group. In a preferred embodiment, the compounds according to the invention used as hole blocking material comprise fewer hole transport groups than electron transport groups, particularly preferably no hole transport groups.

It can further be provided that the compounds according to the invention are used as electron or exciton blocking material, preferably in an electron or exciton blocking layer, the as Compounds according to the invention used electron or exciton blocking material comprise at least one hole transport group. In a preferred embodiment, the compounds according to the invention used as electron or exciton blocking material comprise fewer electron transport groups than hole transport groups, particularly preferably no electron transport groups.

The compound described above, comprising structures of the formula (I) or the preferred embodiments listed above, can preferably be used as the active component in an electronic device. An electronic device is understood to mean a device which contains anode, cathode and at least one layer located between anode and cathode, this layer containing at least one organic or organometallic compound. The electronic device according to the invention thus contains anode, cathode and at least one intermediate layer which contains at least one compound comprising structures of the formula (I). Preferred electronic devices are selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting devices Transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), organic electrical sensors, light-emitting electrochemical cells (LECs), organic laser diodes (O- Laser) and "organic plasmon emitting devices" ( DM Koller et al., Nature Photonics 2008, 1-4 ), preferably organic electroluminescent devices (OLEDs, PLEDs), in particular phosphorescent OLEDs, containing in at least one layer at least one compound comprising structures of the formula (I). Organic electroluminescent devices are particularly preferred. Active components are generally the organic or inorganic materials which are introduced between anode and cathode, for example charge injection, charge transport or charge blocking materials, but in particular emission materials and matrix materials.

A preferred embodiment of the invention are organic electroluminescent devices. The organic electroluminescent device contains a cathode, anode and at least one emitting layer. In addition to these layers, it can also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers and / or organic or inorganic p / n junctions. It is possible that one or more hole transport layers are p-doped, for example with metal oxides such as MoO ₃ or WO ₃ or with (per) fluorinated electron-poor aromatics, and / or that one or more electron transport layers are n-doped. Likewise, interlayers can be introduced between two emitting layers which, for example, have an exciton-blocking function and / or control the charge balance in the electroluminescent device. It should be noted, however, that not all of these layers necessarily have to be present.

The organic electroluminescent device can contain an emitting layer or it can contain a plurality of emitting layers. If several emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Three-layer systems are particularly preferred, the three layers showing blue, green and orange or red emission (for the basic structure, see e.g. WO 2005/011013 ) or systems that have more than three emitting layers. It can also be a hybrid system in which one or more layers fluoresce and one or more other layers phosphoresce.

In a preferred embodiment of the invention, the organic electroluminescent device contains the compound according to the invention comprising structures according to formula (I) or the preferred embodiments listed above as matrix material, preferably as electron-conducting matrix material in one or more emitting layers, preferably in combination with a further matrix material, preferably a hole-conducting matrix material. In a further preferred embodiment of the invention, the further matrix material is a hole-transporting compound. In a further preferred embodiment of the invention, the further matrix material is an electron-conducting compound. In yet another preferred embodiment, the further matrix material is a compound with a large band gap which does not participate, or does not participate to a significant extent, in the transport of holes and electrons in the layer. An emitting layer comprises at least one emitting compound.

Suitable matrix materials which can be used in combination with the compounds according to formula (I) or according to the preferred embodiments are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080 , WO 2004/093207 , WO 2006/005627 or WO 2010/006680 , Triarylamines, especially monoamines, e.g. B. according to WO 2014/015935 , Carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl) or those in WO 2005/039246 , US 2005/0069729 , JP 2004/288381 , EP 1205527 or WO 2008/086851 disclosed carbazole derivatives, indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746 , Indenocarbazole derivatives, e.g. B. according to WO 2010/136109 and WO 2011/000455 , Azacarbazole derivatives, e.g. B. according to EP 1617710 , EP 1617711 , EP 1731584 , JP 2005/347160 , bipolar matrix materials, e.g. B. according to WO 2007/137725 , Silanes, e.g. B. according to WO 005/111172 , Azaboroles or boronic esters, e.g. B. according to WO 2006/117052 , Triazine derivatives, e.g. B. according to WO 2010/015306 , WO 2007/063754 or WO 2008/056746 , Zinc complexes, e.g. B. according to EP 652273 or WO 2009/062578 , Diazasilol or tetraazasilol derivatives, e.g. B. according to WO 2010/054729 , Diazaphosphole derivatives, e.g. B. according to WO 2010/054730 , bridged carbazole derivatives, e.g. B. according to US 2009/0136779 , WO 2010/050778 , WO 2011/042107 , WO 2011/088877 or WO 2012/143080 , Triphenylene derivatives, e.g. B. according to WO 2012/048781 , Lactams, e.g. B. according to WO 2011/116865 , WO 2011/137951 or WO 2013/064206 , or 4-spirocarbazole derivatives, e.g. B. according to WO 2014/094963 or the as yet undisclosed registration EP 14002104.9 . A further phosphorescent emitter, which emits with a shorter wave than the actual emitter, can also be present as a co-host in the mixture.

Preferred co-host materials are triarylamine derivatives, in particular monoamines, indenocarbazole derivatives, 4-spirocarbazole derivatives, lactams and carbazole derivatives.

It can also be preferred to use several different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material. Likewise preferred is the use of a mixture of a charge-transporting matrix material and an electrically inert matrix material which is not or not to a significant extent involved in charge transport, such as, for. B. in WO 2010/108579 described.

It is also preferred to use a mixture of two or more triplet emitters together with a matrix. The triplet emitter with the shorter-wave emission spectrum serves as a co-matrix for the triplet emitter with the longer-wave emission spectrum.

A compound according to the invention comprising structures according to formula (I) can particularly preferably be used in a preferred embodiment as matrix material in an emission layer of an organic electronic device, in particular in an organic electroluminescent device, for example in an OLED or OLEC. The matrix material containing compound comprising structures according to formula (I) or the preferred embodiments set out above and below is present in the electronic device in combination with one or more dopants, preferably phosphorescent dopants.

The proportion of the matrix material in the emitting layer is in this case between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferably between 92.0 and 99.5% by volume for fluorescent emitting layers and for phosphorescent emitting layers between 85.0 and 97.0% by volume.

Correspondingly, the proportion of the dopant is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume and particularly preferably between 0.5 and 8.0% by volume for fluorescent emitting layers and between 3.0 and 15.0% by volume for phosphorescent emitting layers. -%.

An emitting layer of an organic electroluminescent device can also contain systems comprising a plurality of matrix materials (mixed matrix systems) and / or a plurality of dopants. In this case too, the dopants are generally those materials whose proportion in the system is the smaller and the matrix materials are those materials whose proportion in the system is the greater. In individual cases, however, the proportion of an individual matrix material in the system can be smaller than the proportion of an individual dopant.

In a further preferred embodiment of the invention, the compound comprising structures according to formula (I) or the preferred embodiments set out above and below are used as a component of mixed matrix systems. The mixed matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials. One of the two materials is preferably a material with hole-transporting properties and the other material is a material with electron-transporting properties. The desired electron-transporting and hole-transporting properties of the mixed matrix components can, however also be combined mainly or completely in a single mixed-matrix component, the further or further mixed-matrix components fulfilling other functions. The two different matrix materials can be present in a 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. Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. More detailed information on mixed matrix systems can be found in the registration form WO 2010/108579 contain.

The present invention also relates to an electronic device, preferably an organic electroluminescent device, which comprises one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more hole-conducting layers as the hole-conducting compound.

In a preferred embodiment of the invention, the organic electroluminescent device contains the compound according to the invention comprising structures according to formula (I) or the preferred embodiments listed above and / or at least one oligomer, polymer or dendrimer according to the invention as an electron-conducting compound in an electron-conducting layer.

The present invention also relates to an electronic device, preferably an organic electroluminescent device, which contains one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in one or more electron transport layers, preferably in combination with a material which has a high dielectric constant , such as alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates in question (e.g. LiF, Li ₂ O, BaF ₂ , MgO, NaF, CsF, C _S2 CO ₃ , etc.) or organic alkali metal complexes, e.g. . B. Liq (lithium quinolinate), a combination of organic alkali metal complexes, preferably Liq with a compound according to the invention and / or an oligomer, polymer or dendrimer according to the invention is particularly preferred. The two different materials of the electron transport layer can be present in a ratio of 1:50 to 50: 1, preferably 1:10 to 10: 1, particularly preferably 1: 4 to 4: 1 and very particularly preferably 1: 2 to 2: 1 .

The present invention also relates to an electronic device, preferably an organic electroluminescent device, which comprises one or more compounds according to the invention and / or at least one oligomer, polymer or dendrimer according to the invention in emitting layers, as matrix material, preferably in combination with a phosphorescent emitter.

Metals with a low work function, metal alloys or multilayer structures made of different metals are preferred as cathodes, such as alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.) . Furthermore, alloys of an alkali or alkaline earth metal and silver, for example an alloy of magnesium and silver, are suitable. In the case of multi-layer structures, other metals can also be used in addition to the metals mentioned, which have a relatively high work function, such as. B. Ag, in which case combinations of the metals such as Mg / Ag, Ca / Ag or Ba / Ag are then 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 (e.g. LiF, Li ₂ O, BaF ₂ , MgO, NaF, CsF, Cs ₂ COs, etc.) are suitable. Organic alkali metal complexes are also suitable for this purpose, e.g. B. Liq (lithium quinolinate). 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 the one hand, metals with a high redox potential are suitable for this, such as Ag, Pt or Au. On the other hand, metal / metal oxide electrodes (for example Al / Ni / NiO _x , Al / PtO _x ) can also be preferred. For some applications, at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (O-SC) or the extraction of light (OLED / PLED, 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, e.g. B. PEDOT, PANI or derivatives of these polymers. It is also preferred if a p-doped hole transport material is applied as a hole injection layer to the anode, metal oxides, for example MoOs or WO ₃ , or (per) fluorinated electron-poor aromatics being suitable as p-dopants. Further suitable p-dopants are HAT-CN (hexacyano-hexaazatriphenylene) or the compound NPD9 from Novaled. Such a layer simplifies the hole injection in materials with a deep HOMO, i.e. a HOMO with a large amount.

In general, all materials can be used in the further layers as are used for the layers according to the prior art, and the person skilled in the art can combine any of these materials in an electronic device with the materials according to the invention without any inventive step.

The device is structured accordingly (depending on the application), contacted and finally hermetically sealed, since the service life of such devices is drastically shortened in the presence of water and / or air.

Also preferred is an electronic device, in particular an organic electroluminescent device, which is characterized in that one or more layers are coated with a sublimation process. The materials are vapor-deposited in vacuum sublimation systems at an initial pressure of usually less than 10 ^-5 mbar, preferably less than 10 ^{-6 mbar.} It is also possible for the initial pressure to be even lower or even higher, for example less than 10 ^-7 mbar.

Also preferred is an electronic device, in particular an organic electroluminescent device, which is characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation. The materials are applied at a pressure between 10 ^-5 mbar and 1 bar. 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. MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301 ).

Also preferred is an electronic device, in particular an organic electroluminescent device, which is characterized in that one or more layers of solution, such as, for. B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, offset printing or nozzle printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (inkjet printing) can be produced. This requires soluble compounds, which can be obtained, for example, by suitable substitution.

The electronic device, in particular the organic electroluminescent device, can also be produced as a hybrid system in that one or more layers are applied from solution and one or more other layers are vapor-deposited. For example, it is possible to apply an emitting layer containing a compound according to the invention comprising structures according to formula (I) and a matrix material from solution and to evaporate a hole blocking layer and / or an electron transport layer thereon in a vacuum.

These methods are generally known to the person skilled in the art and can be applied by him without problems to electronic devices, in particular organic electroluminescent devices containing compounds according to the invention comprising structures according to formula (I) or the preferred embodiments listed above.

1. 1. Elektronische Vorrichtungen, insbesondere organische Elektrolumineszenzvorrichtungen enthaltend Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen, insbesondere als Hostmaterial oder als elektronenleitende und/oder lochleitende Materialien, weisen eine sehr gute Lebensdauer auf. Hierbei bewirken diese Verbindungen insbesondere einen geringen Roll-off, d.h. einen geringen Abfall der Leistungseffizienz der Vorrichtung bei hohen Leuchtdichten.
2. 2. Elektronische Vorrichtungen, insbesondere organische Elektrolumineszenzvorrichtungen enthaltend Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen als elektronenleitende Materialien, lochleitende Materialien und/oder Hostmaterialien weisen eine hervorragende Effizienz auf. Hierbei bewirken erfindungsgemäße Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen eine geringe Betriebsspannung bei Verwendung in elektronischen Vorrichtungen.
3. 3. Elektronische Vorrichtungen, insbesondere organische Elektrolumineszenzvorrichtungen enthaltend Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen weisen eine ausgezeichnete Farbreinheit auf.
4. 4. Die erfindungsgemäßen Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen zeigen eine sehr hohe Stabilität und Lebensdauer.
5. 5. Mit Verbindungen, Oligomere, Polymere oder Dendrimeren mit Strukturen gemäß Formel (I) bzw. den zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen kann in elektronischen Vorrichtungen, insbesondere organische Elektrolumineszenzvorrichtungen die Bildung von optischen Verlustkanäle vermieden werden. Hierdurch zeichnen sich diese Vorrichtungen durch eine hohe PL- und damit hohe EL-Effizienz von Emittern bzw. eine ausgezeichnete Energieübertragung der Matrices auf Dotanden aus.
6. 6. Die Verwendung von Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen in Schichten elektronischer Vorrichtungen, insbesondere organischer Elektrolumineszenzvorrichtungen führt zu einer hohen Mobilität der Elektron-Leiterstrukturen.
7. 7. Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevozugten Ausführungsformen zeichnen sich durch eine ausgezeichnete thermische Stabilität aus, wobei Verbindungen mit einer Molmasse von weniger als ca. 1200 g/mol gut sublimierbar sind.
8. 8. Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen weisen eine ausgezeichnete Glasfilmbildung auf.
9. 9. Verbindungen, Oligomere, Polymere oder Dendrimere mit Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen bilden aus Lösungen sehr gute Filme.
10. 10. Die Verbindungen, Oligomere, Polymere oder Dendrimere umfassend Strukturen gemäß Formel (I) bzw. die zuvor und nachfolgend ausgeführten bevorzugten Ausführungsformen weisen ein überraschend hohes Triplett-Niveau T₁ auf.

The electronic devices according to the invention, in particular organic electroluminescent devices, are distinguished by one or more of the following surprising advantages over the prior art:

1. 1. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below, in particular as host material or as electron-conducting and / or hole-conducting materials, have a very good service life on. In this case, these connections cause, in particular, a low roll-off, that is to say a small drop in the power efficiency of the device at high luminance levels.
2. 2. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below as electron-conducting materials, hole-conducting materials and / or host materials have excellent efficiency. Compounds, oligomers, polymers or dendrimers according to the invention with structures according to formula (I) or the preferred embodiments set out above and below bring about a low operating voltage when used in electronic devices.
3. 3. Electronic devices, in particular organic electroluminescent devices containing compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below have excellent color purity.
4. 4. The compounds, oligomers, polymers or dendrimers according to the invention with structures according to formula (I) or the preferred embodiments set out above and below show a very high stability and service life.
5. 5. With compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below, the formation of optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by a high PL and thus high EL efficiency of emitters and excellent energy transfer from the matrices to dopants.
6. 6. The use of compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below in layers of electronic devices, in particular organic electroluminescent devices, leads to a high mobility of the electron conductor structures.
7. 7. Compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below are distinguished by excellent thermal stability, with compounds having a molar mass of less than about 1200 g / mol being readily sublimable are.
8. 8. Compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below have excellent glass film formation.
9. 9. Compounds, oligomers, polymers or dendrimers with structures according to formula (I) or the preferred embodiments set out above and below form very good films from solutions.
10. 10. The compounds, oligomers, polymers or dendrimers comprising structures according to formula (I) or the preferred embodiments set out above and below have a surprisingly high triplet level T ₁ .

These advantages mentioned above are not accompanied by a deterioration in the other electronic properties.

The compounds and mixtures according to the invention are suitable for use in an electronic device. An electronic device is understood to mean a device which contains at least one layer which contains at least one organic compound. The component can, however, also contain inorganic materials or also layers which are composed entirely of inorganic materials.

The present invention therefore also relates to the use of the compounds or mixtures according to the invention in an electronic device, in particular in an organic electroluminescent device.

Another object of the present invention is the use of a compound according to the invention and / or an oligomer, polymer or dendrimer according to the invention in an electronic device as host material for phosphorescent emitters, electron transport material and / or hole transport material, preferably as host material for a red or green phosphorescent compound or as a hole transport material or electron transport material in an organic electroluminescent device with a fluorescent emitter.

Another object of the present invention is the use of a compound according to the invention and / or an oligomer, polymer or dendrimer according to the invention in an electronic device as a component of an electron transport layer, in particular in combination with a material with a high dielectric constant.

The present invention again further provides an electronic device containing at least one of the above-mentioned compounds or mixtures according to the invention. The preferences set out above for the connection also apply to the electronic devices. Electronic device is particularly preferably selected from the group consisting of organic electroluminescent devices (OLEDs, PLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O -SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), organic electrical sensors, light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and "organic plasmon emitting devices" ( DM Koller et al., Nature Photonics 2008, 1-4 ), preferably organic electroluminescent devices (OLEDs, PLEDs), in particular phosphorescent OLEDs.

In a further embodiment of the invention, the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, ie the emitting layer is directly adjacent to the hole injection layer or the anode and / or the emitting layer is directly adjacent the electron transport layer or the electron injection layer or the cathode, such as in FIG WO 2005/053051 described. Furthermore, it is possible to use a metal complex, which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport or hole injection material, e.g. B. in WO 2009/030981 described.

In the further layers of the organic electroluminescent device according to the invention, all materials can be used as they are usually used according to the prior art. The person skilled in the art can therefore use all materials known for organic electroluminescent devices in combination with the compounds according to the invention of the formula (I) or in accordance with the preferred embodiments, without inventive intervention.

When used in organic electroluminescent devices, the compounds according to the invention generally have very good properties. In particular, when the compounds according to the invention are used in organic electroluminescent devices, the service life is significantly better compared to similar compounds according to the prior art. The further properties of the organic electroluminescent device, in particular the efficiency and the voltage, are also better or at least comparable.

It should be noted that variations of the embodiments described in the present invention fall within the scope of this invention. Each feature disclosed in the present invention can, unless this is explicitly excluded, be replaced by alternative features that serve the same, an equivalent or a similar purpose. Thus, unless otherwise stated, each feature disclosed in the present invention is to be regarded as an example of a generic series or an equivalent or similar feature.

All features of the present invention can be combined with one another in any way, unless certain features and / or steps are mutually exclusive. This is particularly true of preferred features of the present invention. Likewise, features of non-essential combinations can be used separately (and not in combination).

It should also be understood that many of the features, and particularly those of the preferred embodiments of the present invention, are to be considered inventive in themselves and not merely to be considered part of the embodiments of the present invention. Independent protection may be sought for these features in addition to or as an alternative to any presently claimed invention.

The teaching on technical action disclosed with the present invention can be abstracted and combined with other examples.

The invention is illustrated in more detail by the following examples, without wishing to restrict it thereby.

The person skilled in the art can use the descriptions to produce further electronic devices according to the invention without inventive activity and thus carry out the invention in the entire claimed range.

Examples

Unless otherwise stated, the following syntheses are carried out under a protective gas atmosphere in dried solvents. The starting materials can be obtained from ALDRICH. The numbers for the starting materials known from the literature, some of which are given in square brackets, are the corresponding CAS numbers.

Synthesis examples

3- (4'-Chloro-biphenyl-2-yl) -3-hydroxy-1-phenyl-1,3-dihydro-indol-2-ones

54.0 g (202 mmol; 1.55 eq) of 2-bromo-4'-chlorobipheynl [CAS 179526-95-5] in 250 mL of dry THF [CAS 109-99-9] are placed in a 1L flask under protective gas. dissolved and slowly added dropwise to 5.00 g (206 mmol, 1.58 eq) magnesium turnings [7439-95-4] so that the resulting solution boils. It is stirred under reflux for 2 hours. After cooling, the resulting solution of the organyl magnesium is slowly at -11 ° C to a solution of 29.0 g (130 mmol, 1.00 eq) 1-phenyl-1H-indole-2,3-dione [CAS 723-89- 7] in 350 mL dry THF [CAS 109-99-9]. The resulting solution is thawed and stirred for a further 48 hours at room temperature. While cooling with ice, the mixture is quenched by adding hydrochloric acid (15.3 mL, 37%) and water (400 mL). After phase separation, the aqueous phase is extracted with ethyl acetate (300 mL) [CAS 141-78-6] and the combined organic phases are washed with water (300 mL). After drying over sodium sulfate [CAS 7757-82-6], the solvent is removed in vacuo. The residue is dissolved in dichloromethane [CAS 75-09-2] and precipitated by adding heptane. After filtration, the product is obtained as a yellowish filter residue (32.0 g; 77.6 mmol; 60% of theory).

54% 2a

58% 3a

71% 4a

70% 5a

48% 6a

45% 7a

52% The following compounds can be obtained in the same way: No. Educt 1 Educt 2 product yield 1a

54% 2a

58% 3a

71% 4a

70% 5a

48% 6a

45% 7a

52%

2-chloro-1'-phenyl-spiro [fluorene-9,3'-indoline] -2'-ones

In a 1L flask, 31.5 g (76.5 mmol; 1.00 eq) 3- (4'-chloro-biphenyl-2-yl) -3-hydroxy-1-phenyl-1,3-dihydro- indol-2-ones and 2.94 g (15.5 mmol; 20 mol%) toluenesulfonic acid monohydrate [CAS 6192-52-5] in 500 mL toluene [CAS 108-88-3] and suspended at 115 ° C stirred for 5 hours. When the conversion is complete, the mixture is cooled to room temperature and the reaction solution is concentrated. The crude product is taken up in ethyl acetate (500 mL) [CAS 141-78-6] and successively with a saturated aqueous solution of Sodium hydrogen carbonate (2 x 200 mL) and water (2 x 250 mL). After filtration through silica gel and precipitation with heptane, 29.8 g (75.7 mmol; 99% of theory) of the product are obtained as a beige solid.

94% 2b

90% 3b

89% 4b

85% 5b

74% 6b

76% 7b

86% The following compounds can be obtained analogously: No. Educt 1 product yield 1b

94% 2 B

90% 3b

89% 4b

85% 5b

74% 6b

76% 7b

86%

1'-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) spiro [fluorene-9,3'-indoline] -2'-ones

29.6 g (75.1 mmol; 1.00 eq) of 2-chloro-1'-phenylspiro [fluorene-9,3'-indoline] -2'-ones and 20.8 g (81.8 mmol, 1.09 eq) bis (pinacolato) -diborane [CAS 73183-34-3] dissolved in 350 ml dry dioxane [CAS 123-91-1] and degassed for 30 minutes. Then 14.6 g (149 mmol, 2.00 eq) potassium acetate [CAS 127-08-2] and 2.77 g (3.75 mmol, 5 mol%) trans-dichlorobis (tricyclohexylphosphine) palladium (II) -Complex [CAS 29934-17-6] was added and the batch was heated to 90 ° C. overnight. After the reaction has ended, ethyl acetate (100 mL) and water (300 mL) are added and the phases are separated. After extraction with ethyl acetate and washing with water, the solvent of the combined organic phases is removed in vacuo. The crude product is dissolved in DCM and precipitated by adding heptane. Filtration gives the product (30.4 g; 62.6 mmol; 83% of theory) as a yellow solid.

76% 2c

81% 3c

68% 4c

72% The following compounds can be obtained in the same way: No. Educt 1 product yield 1c

76% 2c

81% 3c

68% 4c

72%

2- [3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl] -1'-phenyl-spiro [fluorene-9,3'-indoline] -2'-ones

21,8 g (44,9 mmol; 1,05 eq.) 1'-Phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,3'-indoline]-2'-one, 16,6 g (42,7 mmol; 1,00 eq.) 2-(3-Bromo-phenyl)-4,6-diphenyl-[1,3,5]triazin und 21,1 g (215 mmol; 5,04 eq.) Trikaliumphosphat [CAS 14593-46-5] in 250 mL Dioxan [CAS 123-91-1] suspendiert. Zu dieser Suspension werden 3,51 g (4,80 mmol; 11 mol%) Dichloro[1,1'-bis(diphenylphosphino)ferrocen]palladium(II) (Pd(dppf)₂Cl₂) [CAS 72287-26-4] zugegeben und die Reaktionsmischung wird 16 h unter Rückfluss erhitzt. Das Reaktionsgemisch wird auf Raumtemperatur abgekühlt und das Lösemittel unter vermindertem Druck so weit entfernt, dass ein Feststoff ausfällt. Der Feststoff wird isoliert und mittels Umkristallisation aus Toluol und Säulenchromatographie (Eluent: Heptan/THF) sowie abschließender Sublimation im Hochvakuum aufgereinigt. Die Ausbeute des Produkts beträgt 1,92 g (2,88 mmol; 7% der Theorie)

21.8 g (44.9 mmol; 1.05 eq.) 1'-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) spiro [fluorene- 9,3'-indoline] -2'-ones, 16.6 g (42.7 mmol; 1.00 eq.) 2- (3-bromophenyl) -4,6-diphenyl- [1,3, 5] triazine and 21.1 g (215 mmol; 5.04 eq.) Tripotassium phosphate [CAS 14593-46-5] suspended in 250 mL dioxane [CAS 123-91-1]. 3.51 g (4.80 mmol; 11 mol%) of dichloro [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) (Pd (dppf) ₂ Cl ₂ ) [CAS 72287-26- are added to this suspension 4] was added and the reaction mixture was refluxed for 16 h. The reaction mixture is cooled to room temperature and the solvent is removed under reduced pressure to such an extent that a solid precipitates out. The solid is isolated and purified by recrystallization from toluene and column chromatography (eluent: heptane / THF) and subsequent sublimation in a high vacuum. The yield of the product is 1.92 g (2.88 mmol; 7% of theory)

15% 2e

12% 3e

15% 4e

10% 5e

9% 6e

18% 7e

11% 8e

15% 8e

13% The following compounds can be obtained in the same way: No. Educt 1 Educt 2 product yield 1e

15% 2e

12% 3e

15% 4e

10% 5e

9% 6e

18% 7e

11% 8e

15% 8e

13%

4- (N- (9,9-dimethylfluoren-4-yl) -4-phenyl-anilino) -1'-phenyl-spiro [fluorene-9,3'-indoline] -2'-ones

15.2 g (38.7 mmol; 1.02 eq.) 4-chloro-1'-phenyl-spiro [fluorene-9,3'-indoline] -2'-ones, 14.0 g (37.9 mmol; 1.00 eq.) Biphenyl-4-yl- (9,9-dimethyl-9H-fluoren-4-yl) -amine [CAS 1421789-16-3] and 5.10 g (42.7 mmol; 1.10 eq.) Sodium tert-butoxide [CAS 865-47-4] are placed in 220 mL toluene [CAS 108-88-3] and inertized for 30 minutes in a stream of argon. Then 778 mg (1.90 mmol; 5 mol%) of dicyclohexyl- (2 ', 6'-dimethoxy-biphenyl-2-yl) -phosphane (SPhos) [CAS 657408-07-6], 255 mg (1, 14 mmol; 3 mol%) palladium acetate [CAS 3375-31-3] was added and the mixture was refluxed for 42 hours. After complete conversion and cooling to room temperature, 400 mL water are added to the reaction. After the phases have been separated and the aqueous phase is extracted with toluene [CAS 108-88-3], the combined organic phases are concentrated and the crude product is precipitated by adding heptane. The precipitated solid is isolated. Purification by means of recrystallization and vacuum sublimation gives the desired product (5.26 g; 7.32 mmol; 19% of theory).

22% 2f

13% 3f

15% 4f

23% 5f

24% The following compounds can be obtained in the same way: No. Educt 1 Educt 2 product yield 1f

22% 2f

13% 3f

15% 4f

23% 5f

24%

1'-phenyl-2,6'-bis (9-phenylcarbazol-3-yl) spiro [fluorene-9,3'-indoline-2'-ones

14.7 g (34.3 mmol; 1.00 eq.) 2,6'-dichloro-1'-phenyl-spiro [fluorene-9,3'-indoline] -2'-one, 23.7 g ( 82.4 mmol; 2.40 eq.) (9-phenylcarbazol-3-yl) boronic acid [CAS 854952-58-2] and 36.4 g (172 mmol; 5.00 eq.) Tripotassium phosphate [CAS 7778- 53-2] suspended in 210 mL toluene [CAS 108-88-3] and 20 mL water and inertized for 45 minutes in a stream of argon. 987 mg (2.40 mmol; 7 mol%) of dicyclohexyl- (2 ', 6'-dimethoxy-biphenyl-2-yl) -phosphane (SPhos) [CAS 657408-07-6] and 385 mg ( 1.72 mmol; 5 mol%) palladium acetate [CAS 3375-31-3] was added and the reaction mixture was refluxed for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed with 400 mL water and then concentrated to dryness. The resulting solid is dissolved in DCM and added liked by EtOH. The precipitated solid is isolated and recrystallized from toluene and finally sublimed in a high vacuum. The yield is 6.45 g (7.66 mmol, 22% of theory).

24% 2g

18% 3g

31% 4g

25% 5g

28% The following compounds can be obtained in the same way: No. Educt 1 Educt 2 product yield 19th

24% 2g

18% 3g

31% 4g

25% 5g

28%

The compounds according to the invention can in particular be used in the emission layer, the electron transport layer and / or hole blocking layer. OLEDs containing these compounds have very good operating voltages, lifetimes, stabilities and very high efficiencies. Furthermore, the compounds according to the invention have very good film-forming properties. OLEDs containing these compounds are also distinguished by excellent color balance. The observable technical effects are advantageous compared to those of other compounds from the prior art.

With an appropriate configuration, for example through suitable substitution, the compounds according to the invention can also be used as hole conductors in the emission layer, the hole transport layer and / or the electron blocking layer. OLEDs containing these compounds have very good operating voltages, lifetimes, stabilities and very high efficiencies. Furthermore, the compounds according to the invention have very good film-forming properties. OLEDs containing these compounds are also distinguished by excellent color balance. The observable technical effects are advantageous compared to those of other compounds from the prior art.

QUOTES INCLUDED IN THE DESCRIPTION

This list of the documents listed by the applicant was generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

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Claims (17)

A compound comprising at least one structure of the formula (I), preferably a compound according to the formula (1),

where the following applies to the symbols used: X is on each occurrence, identically or differently, N or CR, preferably CR; V is a group of the formula -C (= O) NR- or - NRC (= O) -, Y is a bond or a bridge selected from B (R), C (R) ₂ , Si (R) ₂ , C = O, C = NR, C = C (R) ₂ , O, S, Se, S = O, SO ₂ , N (R), P (R), and P (= O) R; R is on each occurrence, identically or differently, H, D, OH, F, Cl, Br, I, CN, NO ₂ , N (Ar) ₂ , N (R ¹ ) ₂ , C (= O) Ar, C (= O) R ¹ , P (= O) (Ar) ₂ , P (Ar) ₂ , B (Ar) ₂ , B (OR ¹ ) ₂ , Si (Ar) ₃ , Si (R ¹ ) ₃ , a straight chain alkyl -, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms or an alkenyl or alkynyl group with 2 to 40 carbon atoms, each with a or more radicals R ² can be substituted, one or more non-adjacent CH ₂ groups by -R ¹ C = CR ¹ -, -C = C-, Si (R ¹ ) ₂ , Ar Ge (R ¹ ) ₂ , Sn (R ¹ ) ₂ , C = O, C = S, C = Se, -C (= O) O-, -C (= O) NR ¹ -, C = NR ¹ , NR ¹ , P (= O ) (R ¹ ), -O-, -S-, -Se-, SO or SO ₂ can be replaced and one or more H atoms being replaced by D, F, Cl, Br, I, CN or NO ₂ can, or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, each of which is substituted ^{by one or more radicals R 1} can, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which ^{can be substituted by one or more radicals R 1} , or an aralkyl or heteroaralkyl group with 5 to 60 aromatic ring atoms, which are substituted ^{by one or more radicals R 1} can, or a combination of these systems; two or more, preferably adjacent, radicals R ^{1 here} can form a ring system with one another; is at each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which ^{can be substituted by one or more radicals R 1} , two radicals Ar, which can be attached to the same Si atom, N atom, P atom or B-atom bond, also through a single bond or a bridge, selected from B (R ¹ ), C (R ¹ ) 2, Si (R ¹ ) 2, C = O, C = NR ¹ , C = C (R ¹ ) ₂ , O, S, Se, S = O, SO ₂ , N (R ¹ ), P (R ¹ ) and P (= O) R ¹ , be bridged to one another; R ¹ is on each occurrence, identically or differently, H, D, OH, F, Cl, Br, I, CN, NO ₂ , N (Ar ¹ ) ₂ , N (R ² ) ₂ , C (= O) Ar ¹ , C (= O) R ² , P (= O) (Ar ¹ ) ₂ , P (Ar ¹ ) ₂ , B (Ar ¹ ) ₂ , B (OR ² ) ₂ , Si (Ar ¹ ) ₃ , Si (R ² ) ₃ , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms or an alkenyl or alkynyl group with 2 to 40 carbon atoms Atoms, each of which can be substituted by one or more radicals R ² , one or more non-adjacent CH ₂ groups being replaced by -R ² C = CR ² -, -C = C-, Si (R ² ) ₂ , Ge (R ² ) ₂ , Sn (R ² ) ₂ , C = O, C = S, C = Se, C = NR ² , -C (= O) O-, -C (= O) NR ² -, NR ² , P (= O) (R ² ), -O-, -S-, -Se-, Ar ¹ SO or SO ₂ can be replaced and one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO ₂ can be replaced, or an aromatic or heteroaromatic ring system with 5 to 40 aromatic ring atoms, each by one or more radicals R ² can be substituted, or an aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms, which ^{can be substituted by one or more radicals R 2} , or an aralkyl or heteroaralkyl group with 5 to 40 aromatic ring atoms, which can be substituted with one or more radicals R ² can be substituted, or a combination of these systems; two or more, preferably adjacent, radicals R ^{1 here} can form a ring system with one another; is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which ^{can be substituted by one or more radicals R 2} , two radicals Ar ¹ attached to the same Si atom, N atom, P -Atom or B-atom bond, also through a single bond or a bridge, selected from B (R ² ), C (R ² ) ₂ , Si (R ² ) ₂ , C = O, C = NR ² , C = C (R ² ) ₂ , O, S, Se, S = O, SO ₂ , N (R ² ), P (R ² ) and P (= O) R ² , be bridged to one another; R ² is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CN, B (OR ³ ) ₂ , NO ₂ , C (= O) R ³ , CR ³ = C (R ³ ) ² , C (= O) OR ³ , C (= O) N (R ³ ) 2, Si (R ³ ) ₃ , P (R ³ ) ₂ , B (R ³ ) ₂ , N (R ³ ) ₂ , NO ₂ , P (= O) (R ³ ) ₂ , OSO ₂ R ³ , OR ³ , S (= O) R ³ , S (= O) ₂ R ³ , a straight-chain alkyl, alkoxy or thioalkoxy group with 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group with 3 to 40 carbon atoms, each of which ^{can be substituted by one or more radicals R 3} , one or more non-adjacent CH ₂ groups being replaced by -R ³ C = CR ³ -, -C = C-, Si (R ³ ) ₂ , Ge (R ³ ) ₂ , Sn (R ³ ) ₂ , C = O, C = S, C = NR ³ , -C ( = O) O-, -C (= O) NR ³ -, NR ³ , P (= O) (R ³ ), -O-, -S-, -Se-, SO or S0 ₂ can be replaced and where one or more H atoms can be replaced by D, F, CI, Br, I, CN or NO ₂ , or an aromatic or R ³ heteroaromatic ring system with 5 to 40 aromatic ring atoms, each of which is substituted ^{by one or more radicals R 3} can be, or an aryloxy or heteroaryloxy group with 5 to 40 aromatic ring atoms, which ^{can be substituted by one or more radicals R 3} , or a combination of these systems; two or more, preferably adjacent, substituents R ^{2 can} also form one with one another; is on each occurrence, identically or differently, selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms in which one or more H Atoms can be replaced by D, F, Cl, Br, I or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; two or more, preferably adjacent, substituents R ^{3 can} also form one with one another. Connection according to Claim 1 , comprising at least one structure of the formula (II), preferably selected from the compounds of the formula (II)

where the symbols V and X correspond to those in Claim 1 have mentioned meaning. Connection according to Claim 1 or 2 , comprising at least one structure of the formula (IIIa) or (IIIb), preferably selected from the compounds of the formula (IIIa) or (IIIb)

where the symbols X and R correspond to those in Claim 1 Have the meaning mentioned, the structure according to formula (IIIa) being preferred. Compound according to at least one of the preceding claims, characterized in that the radical R bonded to the N atom in group V comprises an aromatic or heteroaromatic radical, preferably the N atom bonds to an aromatic or heteroaromatic radical. Compound according to at least one of the preceding claims, comprising at least one structure of the formula (VIa) or (VIb), preferably selected from the compounds of the formula (VIa) or (VIb)

where R is the in Claim 1 Have the meaning mentioned and m is 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2, identically or differently on each occurrence. Compound according to at least one of the preceding claims, characterized in that at least one group R in the formulas (I), (II), (IIIa), (IIIb), (VIa) or (VIb) stands for a group which is represented by the Formula L ¹ -Z can be represented, wherein L ^{1 represents} a bond or an aromatic or heteroaromatic ring system with 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted ^{by one or more radicals R 1 , ZR 1} , Ar or a Represents a group of the formula Z ^a or Z ^b , in which the symbols Ar and R ^{1 represent} the in Claim 1 mentioned have meaning and Z ^a or Z ^b

mean, in which W on each occurrence, identically or differently, represents an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which ^{can be substituted by one or more radicals R 1} , a nitrogen atom, a boron atom, a phosphorus atom or a phosphine oxide group, the dashed bond the connection position is marked and the symbols Ar and R ^{1 correspond to} the in Claim 1 called have meaning. Connection according to Claim 6 , comprising at least one structure of the formula (VIIa), (VIIb), (VIIc), (VIId), (VIIe) or (VIIf), preferably selected from the compounds of the formula (VIIa), (VIIb), (VIIc), (VIId), (VIIe) or (VIIf)

where the symbol X representsN, CR or C, if the group -L ¹ -Z is bonded to X, and the symbol R represents the in Claim 1 mentioned meaning and the group -L ¹ -Z in Claim 6 have mentioned. Connection according to Claim 6 or 7th , comprising at least one structure of the formula (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf), (VIIIg), (VIIIh), (VIIIi), (VIIIj), (VIIIk) , (VIII l), (VIIIm) or (VIIIn), preferably selected from the compounds of the formula (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe), (VIIIf), (VIIIg), ( VIIIh), (VIIIi), (VIIIj), (VIIIk), (VIII l), (VIIIm) or (VIIIn)

where the symbols Ar and R ^{1 correspond to} those in Claim 1 mentioned meaning and the group -L1-Z in Claim 6 have, m is independently 0, 1, 2, 3, or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2, and n is independently 0, 1, 2, or 3 each occurrence , preferably 0.1 or 2, particularly preferably 0 or 1, compounds with groups of the formulas (VIIIa), (VIIIb), (VIIIc), (VIIId), (VIIIe) or (VIIIf) being preferred. Connection according to at least one of the Claims 6 to 8th , comprising at least one structure of the formula (IXa), (IXb), (IXc), (IXd), (IXe), (IXf), (IXg), (IXh), (IXi), (IXj), (IXk) , (IXI), (IXm), (IXn), (IXo), (IXp), (IXq) or (IXr), preferably selected from the compounds of the formula (IXa), (IXb), (IXc), (IXd ), (IXe), (IXf), (IXg), (IXh), (IXi), (IXj), (IXk), (IXI), (IXm), (IXn), (IXo), (IXp), (IXq) or (IXr)

where the symbols Ar and R ^{1 correspond to} those in Claim 1 and the group -L1-Z have that mentioned in claim 22, m is independently 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, particularly preferably 0, 1 or 2, and n is 0, 1, 2, or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, where compounds with groups of the formulas (IXa), (IXb), (IXc), (IXd), (IXg), (IXh), (IXo), (IXp), (IXq) or (IXr) are preferred. Connection according to at least one of the preceding Claims 6 to 9 , characterized in that Z in formula L ¹ -Z or in a structure according to formulas (VIIa) to (VIIf), (VIIIa) to (VIIIn) and / or (IXa) to (IXp) represents a group which is selected is derived from the formulas (Z-1) to (Z ¹ - 91)

where the following applies to the symbols used: k is independently 0 or 1 at each occurrence; I is independently 0, 1 or 2 on each occurrence; j is independently 0, 1, 2 or 3 on each occurrence; h is independently 0, 1, 2, 3 or 4 on each occurrence; the dashed bond marks the attachment position; and Ar ¹ , R ¹ have the in Claim 1 mentioned meaning, wherein the presence of an NN bond is preferably excluded. Compounds according to at least one of the preceding Claims 7 to 10 , characterized in that the group L1 in formula L ¹ -Z or the structural element L ¹ -Z according to formulas (VIIa) to (VIIf), (VIIIa) to (VIIIn) and / or (IXa) to (IXr) for a Bond or a group which is selected from the formulas (L ¹ -1) to (L ¹ -163)

where the dashed bonds mark the attachment positions, the index k is 0 or 1, the index I is 0, 1 or 2, the index j is independently 0, 1, 2 or 3 at each occurrence; the subscript h at each occurrence is independently 0, 1, 2, 3 or 4; the subscript g is 0, 1, 2, 3, 4 or 5; the symbol Y ^{1 is} O, S or NR ¹ , preferably 0 or S; and the symbol R ¹ the in Claim 1 has mentioned meaning. Oligomer, polymer or dendrimer containing one or more compounds according to one of the Claims 1 to 11 , with one or more bonds of the compounds to the polymer, oligomer or dendrimer being present instead of a hydrogen atom or a substituent. Composition containing at least one compound according to one or more of the Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, polypodal emitters, emitters which show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials and hole blocking materials. Formulation containing at least one compound according to one or more of the Claims 1 to 11 or an oligomer, polymer or dendrimer according to Claim 12 or a composition according to claim 38 and at least one solvent. Using a connection according to one or more of the Claims 1 to 11 , an oligomer, polymer or dendrimer Claim 12 or a composition according to Claim 13 in an electronic device as host material, preferably as host material for a green or red phosphorescent compound, hole transport material or electron transport material. A method for producing a compound according to one or more of the Claims 1 to 11 , an oligomer, polymer or dendrimer Claim 12 , characterized in that a compound comprising at least one lactam group is linked to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction. Electronic device containing at least one connection according to one or more of the Claims 1 to 11 , an oligomer, polymer or dendrimer Claim 12 or a composition according to Claim 13 , wherein the electronic device is preferably selected from the group consisting of organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field quench devices , light-emitting electrochemical cells or organic laser diodes.