WO2017216299A1 - Emitter molecules on the basis of dual-fluorescence benzene (poly)carboxylate acceptors - Google Patents

Abstract

The object of the present invention are compounds comprising at least one donor group and at least one acceptor group, as described herein, which are characterized by a pronounced CT character. The invention also relates to the use thereof as emitters in an optoelectronic component.

Description

 Emitter molecules based on dual fluorescent benzene (poly) carboxylate acceptors

The present invention relates to compounds as described herein, as well as their use as emitter or carrier material in an optoelectronic component.

The development of novel functional compounds for use in electronic devices is currently the subject of intense research. The aim here is the development and investigation of compounds that have not been used in electronic devices so far, as well as the development of compounds that allow an improved property profile of the devices.

The term optoelectronic component according to the present invention includes organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs), organic solar cells (OSCs), organic optical Detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices such as organic light-emitting diodes (OLEDs) understood.

The construction of organic electroluminescent devices (OLEDs) in which the compounds described herein can preferably be used as functional materials is known to the person skilled in the art and is described, inter alia, in patent publications US 4539507, US 5151629, EP 0676461 and WO 1998/27136.

In organic light-emitting diodes (OLEDs), electron-hole pairs form so-called excitons, which can return to the electronic ground state by emitting light quanta. This recombination is possible for many molecules exclusively from excited singlet states with spin quantum number S = 0. Since the generation of excitons follows the spin statistics under the electroluminescent operation of OLEDs, singlet and triplet excitations are formed in a ratio of 1: 3. The statistically more probable occupation of non-radiative triplet excitations is a major problem of the internal emission processes of organic emitter molecules for these fluorescent molecules. The integration of non-radiative triplet states into the emission process has therefore been of essential importance since the beginning of organic electronics.

The first generation of OLEDs was based exclusively on fluorescent emitter molecules that emit light from the excited singlet state Si and were therefore restricted to a quantum yield of 25% according to the spin statistics. In the second emitter generation, triplet states via phosphorescence were used for the light emission by targeted introduction of heavy atoms (heavy atom effect) and a resulting increase in spin-orbit coupling. It comes from a stimulated triplet state Ti, by reversing the spin to the transition to the ground state So. By a more long-lasting radiation process by this phosphorescent As a result, the internal quantum efficiency increases up to 100%.

In particular, iridium or other noble metal-containing molecular compounds which according to the prior art frequently carbazo derivatives, for example bis (carbazolyl) biphenyl, ketones continue (WO 2004/093207), phosphine oxides, sulfones (WO 2005/003253), triazine compounds such as Triazinyispirobifluoren (WO 2005 No. 053055 and WO 2010/05306) are used as phosphorescent emitters. In addition, however, metal complexes, such as bis (2-methyl-8-quinolinolato-N1, 08) - (1, 1 'biphenyl-4-olato) aluminum (BAIq) or bis [2- (2-benzothiazole) phenolatj zinc (II) used.

The present invention is classified in the third generation of emitter molecules. Pure organic compounds, which have a small internal energy barrier between Singuiett and triplet excitation, can thermally excite triplet excitons under spin reversal to radiant singlet states. Light-emitting organic compounds that follow this principle of the thermally activated "spin-flip" from non-radiative triplet to radiating singlet state are referred to as TADF emitters (thermally activated delayed fluorescence), from this third generation of organic emitter molecules It expects to provide long-lived blue emitters with improved efficiency even under increased current density, since TADF emitters represent purely organic compounds and their characteristics are largely determined by the geometry and choice of donor (D) and acceptor (A) groups a large field of possible molecular structures.

It should be noted, however, that the lifetime and stability of the TADF OLEDs shown to date are not marketable. In particular, industrially durable, efficient blue emitters with high quantum efficiency for OLEDs, which are also inexpensive to produce, are urgently needed. One reason is a lack of systematic analysis of the crucial parameters for controlling and forming the charge-separated CT (CT) state. The solution to this problem therefore requires new concepts.

It has now surprisingly been found in the context of the present invention that the compounds, as described herein, have a pronounced CT character and are outstandingly suitable for use in optoelectronic components, in particular as emitter materials.

The compounds described herein are characterized by a small energetic splitting between the lowest excited triplet and the lowest excited singlet, and in such materials, a thermally activated delayed fluorescence mechanism can exploit a backward triplet to singlet system transition to triplet states by thermal excitation in singlets to convict. These singlet states then contribute to radiative recombination, which increases the internal quantum efficiency beyond 25%. The donor (D) acceptor (A) structures described herein, in which benzene derivatives (benzene (poly) caboxylates, ketones, sulfones, phosphorous oxides, and benzonitriles) function as acceptor moieties, are particularly aimed at not exclusively, for stable and long-lasting emission in the blue spectral emission range.

In a first aspect, therefore, the present invention is directed to a compound comprising at least one donor group and at least one acceptor group of general structural formula (I)

wobei, in den Verbindungen gemäß Formel (I),

where, in the compounds according to formula (I),

Ry with each occurrence is independently selected from the group consisting of R CO 2 R ^X , COR ^x , SO 2 R ^X , P (O) (R ^X ) 2, and C = N, where R with each occurrence is independently selected from the group consisting of -CH 2 -, -CH 2 CH 2 - and a linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl group;

R ^x with each occurrence is independently selected from the group consisting of hydrogen,

Hydroxyl, methyl, ethyl, CF3, linear or branched, substituted or unsubstituted C3-C20

Alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted

Heteroaryl and NR ² R ³ , wherein R ² and R ³ are independently selected with each occurrence of

A group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C3-C20 alkyl or alkenyl, aryl and heteroaryl;

m is selected from 0, 1, 2, 3, 4 or 5;

n is selected from 0, 1, 2, 3, 4, 5 and 6; and

o is selected from 0, 1, 2, 3, 4, 5 and 6, where n + o> 1, where m + n + o = 6,

with the proviso that when o> 1, R is not COR ^x , S0 ₂ R ^x , P (0) (R ^x ) ₂ , or C = N;

wherein at least one R ^{x is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

In another aspect, the present invention is directed to the use of a compound as described herein in an opto-electronic device, such as an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-IC). FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quench device (O-LET). FQD), a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser) each as an emitter material, or as a material in which by thermal activation the triplet excitations are converted into singlet excitations, these singlets then being used to excite other embedded singlet emitters.

Finally, the present invention is also directed to an optoelectronic device containing at least one compound as described herein.

"At least one" as used herein means 1 or more, ie 1, 2, 3, 4, 5, 6, 7, 8, 9 or more. "At least one donor group" thus means, for example, at least one type of donor - group, ie that is, one kind of donor group or a mixture of several different donor groups may be meant.

The present invention relates to metal-free compounds which can be used both as emitter materials, in particular emitter materials emitting in the blue spectral range, in optoelectronic and electronic components.

From knowledge of CT formation, compounds can be constructed which have resonant locally excited (LE) triplet states and CT singlet states. This resonance condition maximizes the spin flip between the LE triplet and the CT singlet and thus, an increase in the quantum yield within the molecule.

The compounds disclosed herein have a strong CT character. As used herein, a compound includes at least one donor and at least one acceptor group.

An "acceptor group" as used herein refers to a chemical group having electron-withdrawing properties.

A "donor group" as used herein refers to a chemical group having electron-donating properties. In particular, such an electron-donating group may be an aryl or heteroaryl group as defined herein.

According to the present invention, a steric hinderance between donor and acceptor causes a strong twist about the donor-acceptor bond, so that a nearly perpendicular dihedral angle is established for this bond. This geometry ensures a spatial separation of the charge carrier densities of electrons and holes in the emitter molecules according to the invention.

However, the acceptor group, as defined herein, not only effects steric repulsion between donor and acceptor moieties in the emitter molecule, which minimizes π conjugation between donor and acceptor moieties and is indispensable to the TADF process, but possesses them beyond that intrinsic dual fluorescence. This dual fluorescence can be targeted to the charge-separated CT channel by selecting the donor group as defined herein (Figure 1). The gain is ensured by an increased transition dipole moment, which results in an increase in emission from the CT channel.

According to the present invention, the acceptor group is a benzene derivative, in particular a benzene (poly) carboxylate, a benzene ketone, a benzene sulfone, a benzene phosphorus oxide or a benzonitrile. Particularly preferred are benzene (poly) carboxylates.

In a first embodiment, therefore, the present invention is directed to a compound comprising at least one donor group and at least one acceptor group of general structural formula (I)

In the compounds according to formula (I), Ry is in each case independently selected from the group consisting of R ¹ CO ₂ R ^x , COR ^x , SO ₂ R ^x , P (O) (R ^x ) ₂ , and C = N, wherein R ¹ with each occurrence is independently selected from the group consisting of -CH 2 -, -CH 2 CH 2 - and a linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl group; R ^x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and NR ² R ³ , wherein R ² and R ³ with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C ³ -C 20 alkyl or alkenyl, aryl and heteroaryl; m is selected from 0, 1, 2, 3, 4 or 5; n is selected from 0, 1, 2, 3, 4, 5 and 6; and o is selected from 0, 1, 2, 3, 4, 5 and 6, where the sum of the indices n and o is that it is an integer greater than or equal to 1 (n + o> 1) , and where the sum of the indices m, n and o is equal to 6 (m + n + o = 6). Furthermore, the proviso holds that if o is greater than 1 (o> 1), Ry is not COR ^x , S0 ₂ R ^x , P (0) (R ^x ) ₂ , or C = N. In addition, for compounds of formula (I), the proviso that at least one R ^{x is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

In various embodiments of the compounds of the formula (I), n is at least 1, preferably 1, 2 or 3. In such embodiments, o may be 0 in particular.

In various embodiments of the compounds of the formula (I), Ry with each occurrence is independently selected from the group consisting of R CO ₂ R ^x , COR ^x , SO ₂ R ^x , and P (O) (R ^x ) ₂ , in particular R ¹ C0 ₂ R ^x and COR ^x . In various embodiments of the compounds of the formula (I), R ^x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR ² R ³ .

In various embodiments, m is at least 1, preferably 1, 2, 3, 4 or 5. In such embodiments, R ^{x is} preferably a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl

A "C3-C20 alkyl group" as used herein refers to a linear or branched carbon group comprising from 3 to 20 carbon atoms, by way of example, without limitation, especially groups which are selected from the group consisting of propyl, isopropyl, c-propylene, n-butyl, sec-butyl, isobutyl and t-butyl groups, the above-mentioned groups each being substituted or unsubstituted, and when substituted, the substituents are preferably selected from the group consisting of halogens and pseudo-halogens (-CN, -N _3, -OCN, -NCO, -CNO, -SCN, -NCS, -SeCN).

A "C3-C20 alkenyl group" as used herein refers to a linear or branched carbon group comprising 3 to 20 carbon atoms and having at least one carbon-carbon unsaturated bond. By way of example, it is meant, in particular, groups which are selected from the group consisting of allyl, isobutenyl and isopentenyl, where the abovementioned groups may each be substituted or unsubstituted. When substituted, the substituents are preferably selected from the group consisting of halogens and pseudohalogens (-CN, -N ₃ , - OCN, -NCO, -CNO, -SCN, -NCS, -SeCN).

An "aryl" as used herein refers to either a monocyclic aromatic group such as phenyl or a fused (annealed, polynuclear) aromatic polycyclic group, for example, naphthalene or phenanthrenyl Significance of, but not limited to, two or more single (mononuclear) aromatic rings fused together, by way of example especially groups selected from the group consisting of phenyl, naphthyl, anthracene, phenanthrenyl, fluorenyl, pyrenyl, dihydropyrenyl, chrysenyl, peryienyl, Fluoranthenyi, Benzanthracenyi, Benzphenanthrenyi, tetracenyl, pentacenyl and benzpyrenyl, wherein the above groups, according to some embodiments, may each be substituted or unsubstituted .. When substituted, the substituents are preferably selected from the group from halogens and pseudohalogens (-CN, -N3, -OCN, -NCO, -CNO, -SCN, -NCS, -SeCN) and linear or branched alkyl or alkenyl groups having up to 20, preferably up to 6 carbon atoms. A "heating aryl" as used herein refers to either a monocyclic aromatic group or a fused (fused, polynuclear) aromatic polycyclic group as defined above containing at least one heteroatom, for example, selected from the non-limiting group consisting of O, S By way of example, in this context, in particular, groups are understood which are selected from the group consisting of furanyi, difuranyi, terfuranyl, benzofuranyi, isobenzofuranyl, dibenzofuranyl, thienyl, dithienyl, terthienyi, benzothienyi, isobenzothienyi, benzodithienyl, benzotrithienyl, Pyrrolyl, indolyl, isoindolyl, carbazolyi, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl, benzo-6,7-quinolinyl, benzo-7,8-quinolinyl, phenothiazinyl, phenoxazinyl, pyrazolyl, indazolyl, Imidazolyi, benzimidazolyl, naphthimidazolyl, phenanthrimidazolyl, pyridimidazolyl, pyrazole inimidazolyl, quinoxalinimidazolyl, oxazolyl, benzoxazolyl, naphthoxazolyl, anthroxazolyl, phenanthroxazolyl, isoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyi, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzpyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, naphthyridinyl, carbazolyi, benzocarbolinyi, Phenanthrolinyl, 1, 2,3-triazolyi, 1, 2,4-triazolyl, benzotriazolyi, 1, 2,3-oxadiazolyi, 1, 2,4-oxadiazolyi, 1, 2,5-oxadiazolyi, 1, 3,4- Oxadiazolyi, 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 2,5-thiadiazolyi, 1, 3,4-thiadiazolyl, 1, 3,5-triazinyl, 1, 2,4-triazinyl, 1, 2,3-triazinyl, tetrazolyi, 1, 2,4,5-tetrazinyl, 1, 2,3,4-tetrazinyl, 1, 2,3,5-tetrazinyl, purinyl, pteridinyl, indolizinyl and benzothiadiazolyl, and annelated Systems of the aforementioned with one another and / or with aryl groups, such as, for example, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, pyrenyl, dihydropyrenyl, chrysenyl, perylenyl, fluoranthenyl, benzanthracene, benzphenanthrenyl, Te tracenyi, pentacenyl and benzpyrenyl, which groups may be substituted or unsubstituted according to some embodiments. When substituted, the substituents are preferably selected from the above-described substituents described in connection with the aryl groups.

According to another embodiment of the present invention, the compound according to formula (I) is a compound of general structural formula II:

In compounds of formula (II), R with each occurrence is independently selected from the group consisting of -CH 2 -, -CH 2 CH 2 - and a linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl group; R ^x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and NR ² R ³ , wherein R ² and R ³ with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C ³ -C 20 alkyl or alkenyl, aryl and heteroaryl; m is selected from 0, 1, 2, 3, 4 or 5; n is selected from 0, 1, 2, 3, 4, 5 and 6; and o is selected from 0, 1, 2, 3, 4, 5 and 6, with the proviso that when o is greater than 1 (o> 1), R is not COR ^x , S0 ₂ R ^x , P (0 ) (R ^X ) 2, or C = N. In addition, for compounds of formula (II), the proviso that at least one R ^{x is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.

In various embodiments of the compounds of formula (II), n + o> 1 and m + n + o = 6. More preferably, n + o is 1, 2 or 3. In further preferred embodiments n is 1, 2 or 3 and o is 0.

In various embodiments of the compounds of the formula (II), R ^y with each occurrence is independently selected from the group consisting of R CO ₂ R ^x , COR ^x , SO ₂ R ^x , and P (O) (R ^x ) ₂ , in particular R C0 ₂ R ^x and COR ^x .

In various embodiments of the compounds of formula (II), R ^x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched, substituted or unsubstituted C ₃ -C 20 alkyl or alkenyl, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl and NR ² R ³ .

According to a further embodiment, it is a compound according to formula (I) or

(II) in which at least one of R ^x , R ² and R ³ , preferably R ^x , is a group represented by formula

(III) is:

In the groups according to formula (III) R, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} independently selected from the group consisting of hydrogen, bromine, methyloxy, methyl, ethyl, CF 3, linear or branched _C3-C2o alkyl or alkenyl and aryl; X is selected from the group consisting of S, SO ₂ , O, C = O, NH, N-CH ₃ , NCH ₂ CH ₃ , NR ⁹ , C (CH ₃ ) ₂ , C (CH ₂ CH ₃ ) ₂ , C (R ¹⁹ ) ₂ , Si (CH ₃ ) ₂ , Si (CH ₂ CH ₃ ) ₂ , Si (R ⁹ ) ₂ , O = P-O-R ¹⁹ , 0 = PR ¹⁹ , HP (CH ₃ ) ₂ , HP (CH ₂ CH ₃ ) ₂ and HP (R ¹⁹ ) ₂ , wherein R ¹⁹ with each occurrence is independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched C ₃ -C 20 alkyl or alkenyl and aryl ; or X is nothing, a direct carbon-carbon bond of the two aryl groups of the group of formula (III) to each other, or -CH ₂ -CH ₂ -; and represents the attachment site of the group of formula (III) to the rest of the molecule represented by formula (I) or (II).

In such embodiments, preferably R ^x or R ^{x is} attached directly to the central ring of the compound of formula (I) or (II) (ie, not R ^x in C0 ₂ R ^x , R ¹ C0 ₂ R ^x , COR ^x , S0 ₂ R ^x and P (0) (R ^x ) ₂ ), radicals of the formula (III). In various preferred embodiments, at least one R ^{x is} a compound of the formula (III), ie m is at least 1 and R ^x is a radical of the formula (III).

In various embodiments, X is nothing, ie the two aromatic rings of the compound of formula (III) are linked only through the N atom, but preferably X is a direct bond, S, O, C (CH ₃ ) 2, C (CH ₂ CH ₃ ) 2 or C (R ⁹ ) ₂ . In this case, R ^{19 is} preferably methyl, ethyl, linear or branched C 3 -C 20 alkyl or alkenyl or Ce-u aryl, in particular methyl or phenyl.

In one embodiment, for the groups of formula (III), the proviso is that when X is O, none of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ^{18 is} hydroxyl.

In another embodiment, in the groups of formula (III), at least one of R, _R 12 _R 13 _R 14 _R 15 _R 16 _R 17 _{and R} 18 is f f _-f -butyl. For corresponding emitter molecules, it could be shown that the introduction of ferf-butyl groups on the donor group led to improved solubilities and increased sublimation temperatures.

In another embodiment, in the compounds according to formula (I) or (II) at least one of R ^x , R ² and R ^{3 is} a group represented by formula (III-1), (III-2), (III-3) , (III-4), (III-5) or (III-6):

(III-1) (III-2) (III-3)

 (III-4) (III-5) (III-6)

In the groups according to the formulas (III-1), (III-2), (III-3), (III-4), (III-5) and (III-6)> the attachment site of the respective group to the respective moiety of the molecule represented by formula (I) or (II).

Particularly preferred are the radicals of the formulas (III-2), (III-3), (III-4) and (III-5), very particularly preferably (III-5). In such embodiments, preferably R ^x or R ^{x is} attached directly to the central ring of the compound of formula (I) or (II) (ie, not R ^x in C0 ₂ R ^x , R CO ₂ R ^x , COR ^x , SO ₂ R ^x and P (O) (R ^x ) ₂ ), radicals of the formula (III-1) to (III-6), in particular (III-2), (III-3 ), (III-4) or (III-5), most preferably (III-5).

In various preferred embodiments of the compounds of the formula (I) and (II), at least one R ^{x is} a compound of the formula (III), ie m is at least 1 and R ^x is a radical of the formulas (III-1) to (III -6), in particular (III-2), (III-3), (III-4) or (III-5), most preferably (III-5).

The donors of formulas (III) and (III-1) to (III-6) can be used to realize a broad color spectrum while retaining acceptor functionality. In various embodiments, therefore, for example, in addition to or instead of the donors of the formula (III-5) or derivatives thereof with longer-chain alkyl radicals, those of the formulas (III-2), (III-3) or (III-4) are used. Different of these donors can also be combined if m> 1.

In a further embodiment of the present invention, the compound of the formula (I) or (II) is a compound represented by formula (IV), (V), (VI), (VII), (VIII), (IX), (X ), (XI), (XII), (XIII), (XIX) or

 (IV) (V) (VI)

 (X) (XI) (XII)

(XIII) (XIX) (XX) In the compounds of the formulas (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIX) and (XX) R ^x , R ² , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 are} each independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C ³ -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR ² R ³ , wherein R ² and R ³ with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C3-C20 alkyl or alkenyl, aryl and heteroaryl.

In various embodiments, compounds according to the formulas (IV), (V), (VI), (VII), (VIII),

(IX), (X), (XI), (XII), (XIII) and (XIX) preferably, in particular those according to the formulas (IV), (VI), (VII), (VIII), (IX), (XI) and (XII), more preferably those of the formulas (IV), (VI), (VII) and (VIII).

In various embodiments, R ² , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 are} each independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or Alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and NR ² R ³ , especially hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.

According to one embodiment, for compounds of the formulas (IV), (V), (VI), (VII), (VIII), (IX),

(X), (XI), (XII), (XIII), (XIX) and (XX) moreover the proviso that at least one of R ^x , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl. Preferably, at least one of R ² , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl. It is preferred that this is in the ortho-position to the / a C02R ^X, R C0 ₂ R ^x, COR ^x, S0 ₂ R ^x, or P (0) (R ^x). ₂

According to another embodiment, in the compounds represented by formulas (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII ), (XIX) and (XX) at least one of R ^x , R ² , R ³ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 represents} a group represented by formula (III) as defined herein or a group represented by formula (III-1), (III-2), (III-3), (III-4), (III-5) or (III-6) as defined herein. Preferably, at least one of R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 is} a group of formula (III), (III-1), (III-2), (III-3), (III -4), (III-5) or (III-6), more preferably (III-2), (III-3), (III-4) or (III-5), most preferably (III-5) , It is preferred that this group is ortho to the C0 ₂ R ^x , R C0 ₂ R ^x , COR ^x , S0 ₂ R ^x , or P (0) (R ^x ) ₂ .

In one embodiment, the group of formula (III) in this context is subject to the proviso that when X is O, none of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ and R ^{18 is} hydroxyl is.

In various preferred embodiments of the invention, in the compounds of the formulas (I) and (II) (1) n = 1, 2 or 3, preferably 1, and R ^x in the radical C02R ^{X is} methyl, ethyl or C3-20 alkyl, preferably methyl; and

(2) at least one, preferably 1, 2, 3, 4 or 5, particularly preferably 1, 2 or 3, directly attached to the ring radical (s) R ^{x is} a substituted or unsubstituted aryl or heteroaryl, in particular one of the formula (III), (III-2), (III-3), (III-4) or (III-5), particularly preferably (III-2), (III-3), (III-4), (III-5), most preferably (III-5);

In such embodiments, the radicals according to (2) are preferably in ortho position to the radicals (1). In such embodiments, preferably, there is no R 1 -CN.

According to a further embodiment, the compound according to the invention is a compound represented by formula (IV-1), (IV-2), (IV-3), (IV-4), (IV-5) or (IV- 6):

 (IV-5) (IV-6)

In verschiedenen Ausführungsformen betrifft die Erfindung auch Multimere der hierin beschriebenen Verbindungen. Diese sind dadurch gekennzeichnet, dass sie durch Dimerisierung oder Multimerisierung von mindestens zwei Verbindungen gemäß der Erfindung erhältlich sind, beispielsweise der Verbindungen der Formeln (I), (II), (IV)-(XX). In solchen Ausführungsformen ist mindestens ein R^x in einem der Reste C0₂R^x, R C0₂R^x, COR^x, S0₂R^x und P(0)(R^x)₂ eine bi- oder multivalente Gruppe, die die entsprechende Verbindung mit einer weiteren Verbindung gemäß der Erfindung verknüpft. In solchen Ausführungsformen ist der Rest R^x beispielsweise eine Methylen- (-CH₂-) oder andere Alkylengruppe, beispielsweise der Formel -(CH₂)_Z- mit z= 1-20. Alternativ kann R^x auch eine Aryl oder Alkenylgruppe sein, wie hierin definiert, mit dem Unterschied, dass diese bi- oder multivalent ist. Beispiele solcher Verbindungen sind: According to further embodiments, the compounds according to the invention are those of the formulas 1.1.1, 1.2.1, 1.2.2, 1.2.3, 1.2.4, 1.1.2, 2.1.1, 2.2.1, 2.2.2, 2.2.3, 1.1.3, 2.3.1, 2.4.1, 3.3.1 or 1.5.1:

In various embodiments, the invention also relates to multimers of the compounds described herein. These are characterized by being obtainable by dimerization or multimerization of at least two compounds according to the invention, for example the compounds of the formulas (I), (II), (IV) - (XX). In such embodiments, at least one R ^x in one of C0 ₂ R ^x , R C0 ₂ R ^x , COR ^x , S0 ₂ R ^x and P (0) (R ^x ) _{2 is} a bivalent or multivalent group containing the corresponding Link linked with another compound according to the invention. In such embodiments, the radical R ^{x is,} for example, a methylene (-CH ₂ -) or other alkylene group, for example of the formula - (CH ₂ ) _Z - with z = 1-20. Alternatively, R ^{x may} also be an aryl or alkenyl group as defined herein, with the difference being bi- or multivalent. Examples of such compounds are:

wobei hierin R dem R^x in einem der Reste C0₂R^x, R C0₂R^x, COR^x, S0₂R^x und P(0)(R^x)₂ und R² dem Rest der Verbindung der jeweiligen Formel (I), (II) oder (IV) entspricht. Besonders bevorzugt sind Dimere der Verbindungen der Formeln 1.1.1 und 2.2.2, wie oben in c) und d) gezeigt. Hierbei ist R (d.h. das R^xder Carboxylgruppe) beispielsweise -CH₂- oder -(CH₂)_Z- mit z= 2-20, vorzugsweise 2-4, oder ein Arylrest, wie beispielsweise -C6H4-.

wherein herein R is the R ^x in one of the radicals C0 ₂ R ^x , R C0 ₂ R ^x , COR ^x , S0 ₂ R ^x and P (0) (R ^x ) ₂ and R ^{2 is} the radical of the compound of the respective formula (I ), (II) or (IV). Particular preference is given to dimers of the compounds of the formulas 1.1.1 and 2.2.2, as shown above in c) and d). Here, R (ie the R ^{x of} the carboxyl group) is, for example, -CH ₂ - or - (CH ₂ ) _Z - with z = 2-20, preferably 2-4, or an aryl radical, such as -C6H4-.

Particularly preferred are di- and trimers, especially dimers. Incidentally, all particular embodiments disclosed herein in the context of the monomeric compounds of the invention are equally applicable to the dimers and multimers, and vice versa.

Figure 1 shows an exemplary comparison of absorbance and photoluminescence of the acceptor molecules disclosed herein, donor molecules, and emitter molecules composed thereof. Figure 1 a) shows absorption and photoluminescence of the acceptor methyl 2-aminobenzoate (2), the donor dimethylacridine (5), and the emitter (IV-5). For this purpose, the compounds were embedded in each case in a concentration of 2 wt .-% in polystyrene and carried out the measurements with the resulting thin films. In addition, emission was measured in different polar solvents for the emitter (IV-5). As can be seen in Figure 1 a), the CT character of the emitter (IV-5) is shown by the typical red shift of its emission with increasingly polar solvent. Embedded in polystyrene emits the emitter (IV-5) in the blue spectral range. Figure 1 b) shows the comparison of the absorption and photoluminescence of methyl 2-aminobenzoate (2) and the emitter (IV-5). The excitation in this case was 275 nm to allow emission from both channels. Here, the principle of enhancing the internal CT character of the benzoate acceptor becomes apparent. As the emission spectrum of the pure methyl 2-aminobenzoate (2) shows, dual fluorescence is present. The attachment of the dimethylacridine donor group to the benzoate acceptor significantly enhances CT emission while decreasing local singlet emission.

Figure 2 shows the time-resolved fluorescence intensity of the emitters (IV-1) (DPA-MB), (IV-2) (Cz-MB), (IV-3) (PT-MB), and (IV-5) (DMAC -MB) at room temperature (T = 293 K) after excitation with a 150 ps laser pulse at a wavelength of 355 nm. The TADF mechanism is clearly demonstrated by the different cooldowns that occur.

Figure 3 shows the prompt and delayed fluorescence from the emitter (IV-3) (PT-MB) at room temperature (T = 293 K) after excitation with a 150 ps laser pulse at a wavelength of 355 nm. The prompt component was integrated after a delay of 2.25 ns with respect to the excitation pulse over 1 .7 ns. The delayed emission was integrated after 1 \ is over 1 \ is.

Figure 4 shows the time-resolved fluorescence intensity of the emitter (IV-2) Cz-MB at room temperature (T = 293 K) after excitation with a laser pulse of 150 ps at a wavelength of 355 nm. The prompt component was integrated after a delay of 2.25 ns with respect to the excitation pulse over 1 .7 ns. The delayed emission was integrated after 1 \ is over 1 \ is.

The present invention further relates to the use of at least one compound of the formula (I) or the specific embodiments disclosed herein in an optoelectronic component, for example an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field Effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, a organic photoreceptor, an organic field quench device (O-FQD), a light emitting electrochemical cell (LEC) or an organic laser diode (O-laser) each as an emitter material, or as a material in which thermal activation activates the triplet excitations into singlet excitations These singlets are then used to excite other embedded singlet emitters.

In various embodiments, the compounds of formula (I) as defined herein or the specific embodiments of the compounds disclosed herein are used as emitter material in the aforementioned optoelectronic devices.

The present invention furthermore relates to an optoelectronic component comprising at least one compound as described herein or at least one of the specific embodiments of the compounds disclosed herein.

Generally, in the elements described herein, several of the compounds described herein may also be used in combination.

In various embodiments, the optoelectronic device contains at least one compound as described herein, wherein the compound of general structural formula (I) emits electromagnetic radiation having a wavelength of 380 nm to 750 nm, or the compound of general structural formula (I) its singlet excitations to another transmits fluorescent emitter emitting at a wavelength of 380 nm to 750 nm.

In various embodiments, the emission of the compound of the general structural formula (I) or of the further fluorescent emitter takes place predominantly in the blue spectral range from 400 nm to 480 nm. In other embodiments, the emission of the compound of the general structural formula (I) or of the further fluorescent emitter takes place predominantly in the green spectral range from 480 nm to 580 nm. In still other embodiments, the emission of the compound of the general structural formula (I) or of the further fluorescent emitter takes place predominantly in the red spectral range from 580 nm to 750 nm.

In various embodiments, the optoelectronic device is OSCs having a photoactive organic layer. This photoactive layer includes low molecular weight compounds, oligomers, polymers or mixtures thereof as organic coating materials. On this thin-film component, a preferably opaque or semitransparent electrode is applied as the cover contact layer.

According to a further embodiment of the invention, the optoelectronic component is arranged on a flexibly designed substrate. For the purposes of the present invention, a flexible substrate is understood to be a substrate which ensures deformability as a result of external forces. As a result, such flexible substrates are also suitable for mounting on curved surfaces. Flexible substrates include, but are not limited to, plastic or metal foils.

In various embodiments, the coating is carried out for producing an optoelectronic component by means of vacuum processing of organic compounds according to the invention, so that advantageously can be dispensed for the production of optoelectronic device high temperature steps above 160 ° C, preferably the deposition at substrate temperatures below 90 ° C, more preferably at below 30 ° C. In various embodiments, therefore, the compounds used according to the invention for producing the optoelectronic component have a low evaporation temperature, preferably <300 ° C., particularly preferably <250 ° C. In various embodiments, however, the evaporation temperature is at least 120 ° C. It is particularly advantageous if the organic compounds according to the invention are sublimable in a high vacuum.

According to a further embodiment of the present invention, it can be provided that the coating for producing an optoelectronic component takes place by means of solvent processing of the compounds described herein. Advantageously, the availability of commercial spray robots makes this application process easily scalable to industry roll-to-roll standards.

In various embodiments, the optoelectronic component in the sense of the present invention is a generic solar cell. Such an optoelectronic component usually has a layer structure, wherein the respectively lowest and uppermost layer are formed as an electrode and counter electrode for electrical contacting. In various embodiments, the optoelectronic component is arranged on a substrate, such as, for example, glass, plastic (PET, etc.) or a metal strip. At least one organic layer comprising at least one organic compound is arranged between the substrate-near electrode and the counterelectrode. Organic compounds which may be used here are organic low molecular weight compounds, oligomers, polymers or mixtures. In various embodiments, the organic layer is a photoactive layer. In various embodiments of the photoactive layer, for example, in the form of a mixed layer of an electron donor and an electron acceptor material may be formed. Adjacent to the at least one photoactive layer can be arranged charge carrier transport layers. Depending on their configuration, these may preferably transport electrons (= negative charges) or holes (= positive charges) from or to the respective electrodes. In various embodiments, the optoelectronic component is designed as a tandem or multiple component. In this case, at least two optoelectronic components are deposited as a layer system one above the other. On or under the trained as contact basic and In various embodiments, cover layers may be followed by additional layers for coating or encapsulating the component or other components.

In one embodiment of the invention, the organic layer is formed as one or more thin layers of vacuum-processed low molecular weight compounds or organic polymers. A variety of vacuum-processed low molecular compounds and polymers based optoelectronic devices are known in the art (Walzer et al., Chemical reviews 2007, 107 (4), 1233-1271, Peumans et al., J. Appl. Phys , 93 (7), 3693-3722).

Preferably, the organic layer is deposited on a substrate using vacuum processable compounds of the inventive compounds described herein. In an alternative preferred embodiment of the present invention, the organic layer is wet-chemically deposited on a substrate using solutions.

Typical examples of optoelectronic devices containing compounds of the invention as described above are also provided. In such embodiments, the compound of the invention in various embodiments is selected from the group consisting of compounds of the formula (I) as defined herein, in particular compounds of the formulas (IV-1), (IV-2), (IV-3), ( IV-4), (IV-5) and (IV-6) as defined herein.

In various other embodiments of the present invention, the optoelectronic device containing at least one of the compounds of formula (I) as described herein is an organic light emitting diode (OLED).

The OLEDs according to the invention are basically composed of several layers, for example:

1. anode

 2nd hole conductor layer

 3. light-emitting layer

 4. Blocking layer for holes / excitons

 5. Electron conductor layer

 6. cathode

It is also possible from the above-mentioned structure different layer sequences, which are known in the art. For example, it is possible that the OLED does not have all of the mentioned layers, for example, an OLED having the layers (1.) (anode), (3.) (light-emitting layer), and (6.) (cathode) is also in which the functions of the layers (2) (hole conductor layer) and (4) (hole / exciton layer layer) and (5) (electron conductor layer) are taken over by the adjacent layers. OLEDs containing the layers (1.), (2.), (3.) and (6.) or the layers (1.), (3.), (4.), (5.) and (6 .) are also suitable. Furthermore you can the OLEDs between the anode (1.) and the hole conductor layer (2.) or between (2.) and (3.) have a block layer for electrons / excitons.

The compounds of the formula (I) can be used as emitter or matrix materials in the light-emitting layer.

The compounds of the formula (I) can be present in the light-emitting layer as the sole emitter and / or matrix material-without further additives. However, it is likewise possible that, in addition to the compounds of the formula (I) used according to the invention, further compounds are present in the light-emitting layer. For example, one or more fluorescent dyes may be present to alter the emission color of the emitter molecule present. Furthermore, a diluent material can be used. This diluent material may be a polymer, for example poly (N-vinyicarbazole) or polysilane. However, the diluent material may also be a small molecule, for example 4,4'-N, N'-dicarbazole biphenyl (CBP = CDP) or tertiary aromatic amines.

The individual of the abovementioned layers of the OLED can in turn be composed of 2 or more layers. For example, the hole-transporting layer may be composed of a layer into which holes are injected from the electrode and a layer that transports the holes away from the hole-injecting layer into the light-emitting layer. The electron-transporting layer may also consist of several layers, for example a layer in which electrons are injected through the electrode and a layer which receives electrons from the electron-injecting layer and transports them into the light-emitting layer. These mentioned layers are selected in each case according to criteria such as energy level, temperature resistance and charge carrier mobility, as well as energy difference of said layers with the organic layers or the metal electrodes. The person skilled in the art is able to choose the structure of the OLEDs in such a way that it is optimally adapted to the organic compounds used according to the invention as emitter substances.

To obtain particularly efficient OLEDs, the HOMO (highest occupied molecular orbital) of the hole-transposing layer should be aligned with the work function of the anode and the LUMO (lowest unoccupied molecular orbital) of the electron-transporting layer should be aligned with the work function of the cathode.

The anode (1) is an electrode that provides positive charge carriers. For example, it may be constructed of materials including a metal, a mixture of various metals, a metal alloy, a metal oxide, or a mixture of various metal oxides. Alternatively, the anode may be a conductive polymer. Suitable metals include the metals of groups 11, 4 and 5 of the Periodic Table of the Elements and the transition metals of groups 9 and 10. When the anode is to be transparent, mixed metal oxides of groups 12, 13 and 14 of the Periodic Table of the Elements are generally used , for example indium tin oxide (ITO). It is too possible that the anode (1) contains an organic material, for example polyaniline, as described, for example, in Nature, Vol. 357, 477-479 (1992). At least either the anode or the cathode should be at least partially transparent in order to be able to decouple the light formed. The material used for the anode (1.) is preferably ITO.

Suitable hole conductor materials for the layer (2) of the OLEDs according to the invention are disclosed, for example, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, Vol. 18, pages 837 to 860, 1996. Both hole transporting molecules and polymers can be used as hole transport material. Commonly used hole-transporting molecules are selected from the group consisting of tris- [N- (1-naphthyl) -N- (phenylamino)] triphenylamine (1-naphDATA), 4,4'-bis [N- (1-naphthyl) -N-phenyl-amino] biphenyl (α-NPD), N, N'-diphenyl-N, N'-bis (3-methylphenyl) - [1, 1'-biphenyi] -4,4'-diamine (TPD ), 1, 1-bis [(di-4-tolylamino) phenyl] cyclohexane (TAPC), N, N'-bis (4-meihylphenyl) -N, N'-bis (4-ethylphenyl) - [1, r- (3,3'-dimethyl) biphenyl] -4,4'-diamine (ETPD), tetrakis- (3-methyl-phenyl) -N, N, N ', N'-2,5-phenylenediamine (PDA), a-Phenyi-4-N, N-diphenylaminostyrene (TPS), p- (diethylamino) -benzaldehyde diphenyihydrazone (DEH), triphenyiamine (TPA), bis [4- (N, N-diethylamino) -2-methylphenyi] (4- methylphenyl) methane (MPMP), 1-phenyl-3- [p- (diethylamino) styryl] -5- [p- (diethylamino) phenyl] pyrazoline (PPR or DEASP), 1,2-trans-bis (9H -carbazol-9-yl) cyclobutane (DCZB), N, N, N ', N'-tetrakis (4-methylphenyl) - (1, r-biphenyl) -4,4'-diamine (TTB), 4,4 ', 4 "-tris (N, N-diphenylamino) triphenylamine (TDTA), porphyrin compounds n and phthalocyanines such as copper phthalocyanines. Usually used hole-transporting polymers are selected from the group consisting of polyvinylcarbazoien, (phenyidimethyl) polysilanes and Poiyaniiinen. It is also possible to obtain hole transporting polymers by doping hole transporting molecules into polymers such as polystyrene and polycarbonate. Suitable hole-transporting molecules are the molecules already mentioned above.

Furthermore, in various embodiments, carbene complexes can be used as hole conductor materials, wherein the band gap of the at least one hole conductor material is generally greater than the band gap of the emitter material used. In the context of the present application, band gap is to be understood as the triplet energy. Suitable carbene complexes are e.g. Carbene complexes, as described in WO 2005/019373 A2, WO 2006/056418 A2 and WO 2005/1 13704 and in the older, not previously published European applications EP 061 12228.9 and EP 061 12198.4.

The light-emitting layer (3) contains at least one emitter material. In principle, it may be a fluorescence or phosphorescence emitter, suitable emitter materials being known to the person skilled in the art. Preferably, the at least one emitter material is a fluorescent emitter having a strong delayed component or a phosphorescence emitter. At least one of the emitter materials contained in the light-emitting layer (3) is a compound of the formula (I) as described herein. In addition, at least one compound of the formula (I) can additionally be used as matrix material. Alternatively, commonly used in the art Matrix materials known in the art. Exemplary matrix materials are selected from the classes of the oligoarylenes (for example 2,2 ', 7,7'-tetraphenylpirobifluorene or dinaphthylanthracene), in particular the oligoarylenes containing fused aromatic groups such as anthracene, benzanthracene, benzphenanthrene, phenanthrene, tetracene, coronene, chrysene, fluorene , Spirofluoren, perylene, phthaloperyiene, naphthaloperylene, decacyclene, rubrene, the oligoarylenvinyienes (eg DPVBi = 4,4'-bis (2,2-diphenylethenyl) -1, r-biphenyi) or spiro-DPVBi according to EP 676461), or the polypodal metal complexes, in particular metal complexes of 8-hydroxyquinoline, eg AIGb (= aluminum (III) tris (8-hydroxyquinoline)) or bis (2-methyl-8-quinolinolato) -4- (phenylphenolinolato) aluminum. In general, suitable matrix materials are known to the person skilled in the art, for example, by Organic Light-Emitting Materials and Devices (Optica! Science and Engineering Series, Ed .: Z. Li, H. Meng, CRC Press Inc., 2006).

The block layer for holes / excitons (4) can typically comprise hole blocker materials used in OLEDs, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (bathocuproine, (BCP)), bis (2-methyl 8-quinolinato) -4-phenyl-phenylatoaluminum (lil) (BAIq), phenothiazine S, S-dioxide derivatives and 1,3,5-tris (N-phenyl-2-benzylimidazole) -benzene) (TPBI) where TPBI and BAIq are also suitable as electron-conducting materials. In a further embodiment, compounds containing aromatic or heteroaromatic groups containing carbonyl groups via groups as disclosed in WO2006 / 100298 can be used as a blocking layer for holes / excitons (4) or as matrix materials in the light-emitting layer (FIG. 3.) are used.

In various embodiments, the present invention relates to an OLED according to the invention comprising the layers (1.) anode, (2.) hole conductor layer, (3.) light-emitting layer, (4.) block layer for holes / excitons, (5.) electron conductor layer and (6.) Cathode, and optionally further layers, wherein the light-emitting layer (3.) contains at least one compound of formula (I).

Suitable electron donor materials for layer (5.) of the OLEDs of the invention comprise chelated metals such as tris (8-quinolinolato) aluminum (Al 2 O 3), bis (2-methyl-8-quinolinato) -4-phenylphenylatoaluminum (III ) (BAiq), phenanthroiin based compounds such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (DDPA = BCP) or 4,7-diphenyl-1,10-phenanthroline (DPA) and azole compounds such as 2 (4-biphenylyi) -5- (4-t-butylphenyl) -1, 3,4-oxadiazole (PBD) and 3- (4-biphenyiyl) -4-phenyl-5- (4-t-butylphenyi) - 1, 2,4-triazole (TAZ) and 2,2 ', 2 "- (1, 3,5-phenylene) tris [1-phenyl-1H-benzimidazole] (TPBI) Both to facilitate electron transport and as a buffer layer or as a barrier layer to avoid quenching of the exciton at the interfaces of the layers of the OLED Preferably, layer (5.) improves the mobility of the electrons and reduces quenching of the exciton. Preferably suitable Eiekt Ronbergerite materials are TPBI and BAIq. Of the materials mentioned above as hole conductor materials and electron conductor materials, some may fulfill several functions. For example, some of the electron-conducting materials are simultaneously hole-blocking materials if they have a deep HOMO. These can be z. B. in the block layer for holes / excitons (4th) are used. However, it is also possible that the function as a hole / exciton blocker of the layer (5.) is taken over, so that the layer (4.) can be omitted.

The charge transport layers can also be electronically doped in order to improve the transport properties of the materials used, on the one hand to make the layer thicknesses more generous (avoidance of pinholes / short circuits) and on the other hand to minimize the operating voltage of the device. For example, the hole conductor materials can be doped with electron acceptors, for example phthalocyanines or arylamines such as TPD or TDTA can be doped with tetrafluorotetracyanchinodimethane (F4-TCNQ). The electron conductor materials may be doped, for example, with alkali metals, for example Alqn with lithium. The electronic doping is known to the person skilled in the art and described, for example, in W. Gao, A. Kahn, J. Appi. Phys. , Vol. 94, no. 1, 2003 (p-doped organic layers); Werner, F. Li, K. Harada, M. Pfeiffer, T. Fritz, K. Leo. Appl. Phys. Lett, Vol. 82, no. 25, 2003 and Pfeiffer et al., Organic Electronics, 2003, 4, 89-103.

The cathode (6) is an electrode for introducing electrons or negative charge carriers. Suitable materials for the cathode are selected from the group consisting of alkali metals of group Ia, for example Li, Cs, alkaline earth metals of group IIa, for example calcium, barium or magnesium, metals of group IIb of the Periodic Table of the Elements (old ILJPAC version) comprising the lanthanides and actinides, for example samarium. Furthermore, metals such as aluminum or indium, as well as combinations of all the metals mentioned can be used. Furthermore, lithium-containing organometallic compounds or LiF can be applied between the organic layer and the cathode to reduce the operating voltage.

The OLED according to the present invention may additionally contain further layers which are known to the person skilled in the art. For example, a layer can be applied between the layer (2) and the light-emitting layer (3), which facilitates the transport of the positive charge and / or adapts the band gap of the layers to one another. Alternatively, this further layer can serve as a protective layer. In an analogous manner, additional layers may be present between the light-emitting layer (3) and the layer (4) to facilitate the transport of the negative charge and / or to match the bandgap between the layers. Alternatively, this layer can serve as a protective layer.

In various embodiments, in addition to the layers (1) to (6), the OLED according to the invention contains at least one of the further layers mentioned below: A hole injection layer between the anode (1.) and the hole-transporting layer (2.); a block layer for electrons between the hole-transposing layer (2) and the light-emitting layer (3); an electron injection layer between the electron-transporting layer (5) and the cathode (6).

The person skilled in the art knows how to select suitable materials (for example based on electrochemical investigations). Suitable materials for the individual layers are known to those skilled in the art and e.g. in WO 00/70655.

Furthermore, it is possible that some or all of the layers used in the OLED according to the invention are surface-treated in order to increase the efficiency of the charge carrier transport. The selection of the materials for each of said layers is preferably determined by obtaining an OLED having a high efficiency and lifetime.

The preparation of the OLEDs according to the invention can be carried out by methods known to the person skilled in the art. In general, the inventive OLED is produced by sequential vapor deposition (vapor deposition) of the individual layers onto a suitable substrate. Suitable substrates are for example glass, inorganic semiconductors or polymer films. For vapor deposition, conventional techniques can be used such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) and others. In an alternative method, the organic layers of the OLED can be applied from solutions or dispersions in suitable solvents using coating techniques known to those skilled in the art.

In general, the various layers have the following thicknesses: anode (1.) 50 to 500 nm, preferably 100 to 200 nm; Hole-conducting layer (2) 5 to 100 nm, preferably 20 to 80 nm, light-emitting layer (3) 1 to 100 nm, preferably 10 to 80 nm, block layer for holes / excitons (4) 2 to 100 nm, preferably 5 to 50 nm, electron-conducting layer (5) 5 to 100 nm, preferably 20 to 80 nm, cathode (6) 20 to 1000 nm, preferably 30 to 500 nm. The relative position of the recombination zone of holes and electrons in the inventive OLED with respect to the cathode and thus the emission spectrum of the OLED u. a. be affected by the relative thickness of each layer. This means that the thickness of the electron transport layer should preferably be selected such that the position of the recombination zone is matched to the optical resonator property of the diode and thus to the emission wavelength of the emitter. The ratio of the layer thicknesses of the individual layers in the OLED depends on the materials used. The layer thicknesses of optionally used additional layers are known to the person skilled in the art. It is possible that the electron-conducting layer and / or the hole-conducting layer have larger thicknesses than the indicated layer thicknesses when they are electrically doped.

According to the invention, the light-emitting layer and / or at least one of the further layers optionally present in the OLED according to the invention contains at least one compound of the general formula (I). While the at least one compound of the general formula (I) is present in the light-emitting layer as emitter and / or matrix material, the at least one compound of the general formula (I) in the at least one further layer of the inventive OLED can each alone or together with at least one of the other suitable for the corresponding layers above materials are used. It is also possible for the light-emitting layer to contain, in addition to the compound of the formula (I), one or more further emitter and / or matrix materials.

The efficiency of the OLEDs of the invention may be e.g. be improved by optimizing the individual layers. For example, highly efficient cathodes such as Ca or Ba, optionally in combination with an intermediate layer of LiF, can be used. Shaped substrates and new hole-transporting materials that bring about a reduction in the operating voltage or an increase in quantum efficiency are also usable in the OLEDs according to the invention. Furthermore, additional layers may be present in the OLEDs to adjust the energy levels of the various layers and to facilitate electroluminescence.

The OLEDs according to the invention can be used in all devices in which electroluminescence is useful. Suitable devices are preferably selected from stationary and mobile screens and lighting units. Stationary screens are e.g. Screens of computers, televisions, screens in printers, kitchen appliances and billboards, lights and signboards. Mobile screens are e.g. Screens in cell phones, laptops, digital cameras, vehicles, and destination displays on buses and trains.

Furthermore, the compounds of the formula (I) can be used in various embodiments in OLEDs with inverse structure. The construction of inverse OLEDs and the materials usually used therein are known to the person skilled in the art.

All documents cited are incorporated herein by reference in their entirety. Other embodiments can be found in the following examples, without the invention being limited to these.

It is to be understood and intended that all embodiments disclosed herein in connection with the described compounds are equally applicable to the described uses and methods, and vice versa. Such embodiments are therefore also within the scope of the present invention. Examples of synthetic methods

Example 1: Donor Synthesis

 (1) (2) (3)

MeMgBr

 (5)

 Methyl 2-aminobenzoate (2)

 In a 500 ml round bottom flask, 2- (phenylamino) benzoic acid (1) (20 g, 0.146 mol) was dissolved in methanol and stirred in an ice bath for 10 minutes. Subsequently, SOCl 2 (42 ml, 0.584 mol) was added dropwise at 0 ° C. and stirred under reflux (90 ° C.) for 12 hours. Thereafter, the reaction mixture was rinsed with distilled water and the product methyl 2-aminobenzoate (2) extracted with ethyl acetate. The organic phase was dried with MgSCU and concentrated on a rotary evaporator. The product (2) was purified by column chromatography with ethyl acetate. The yield was 17.5 g of a partially crystalline substance.

¹ H NMR (300 MHz, CDC) δ (ppm): 7.79-7.75 (m, 1H), 7.21-7.14 (m, 1H), 6.59-6.52 ( m, 2H), 5.64 (s, 1H), 3.78 (s, 3H).

¹³ C NMR (126 MHz, CDCl 3) δ = 168.54, 150.38, 134.04, 131, 16, 1 16.62, 1 16.21, 1.10.67, 51, 47 FT-IR (ATR ), v (cm- ¹ ): 3481, 3371, 1691, 1615, 1578, 1455, 1435, 1294, 1245, 750. MS (ESI) m / z: 152 ([M ⁺ ] +1). Methyl 2-phenylaminobenzoate (3)

Into a 250 ml two-neck round bottom flask were added methyl 2-aminobenzoate (2) (15 g, 0.10 mol), bromobenzene (15.6 g, 0.10 mol), Pd (OAc) ₂ , (0.45 g, 2.02 mmol), K 2 CO 3 (27 g, 0.202 mol), BIN AP (1.25 g, 2.02 mmol) and 50 mL toluene under argon. The mixture was stirred at 70 ° C overnight. After cooling, the inorganic residues were filtered off and the solution was evaporated. The product methyl 2-phenylaminobenzoate (3) was purified by column chromatography with hexane / ethyl acetate (10/1) as dried. The yield was 10.42 g (46%) of viscous, transparent substance. ¹ H NMR (500 MHz, CDC) δ = 9.5 (s, 1H), 7.98 (dd, J = 8 Hz, J = 1.3 Hz, 1H), 7.38-7.24 (m , 6H), 7.10 (t, J = 7.3 Hz, 1H), 6.74 (ddd, J = 8.1, 6.9, 1, 3 Hz, 1H), 3.91 ( s, 3H).

FT-IR (ATR), v (cm ¹ ): 3319, 2949, 1686, 1591, 1515, 1453, 1258, 747.

2- (2-anilinophenyl) propan-2-ol (4)

 Into a heated Schlenk flask was added methyl 2- (phenylamino) benzoate (3) (5.89 g, 0.026 mol) in 100 mL of concentrated THF under nitrogen and cooled to 0 ° C. Subsequently, 40 ml (0.12 mol) of a 3 M MeMgBr solution in diethyl ether were added dropwise and stirred for 15 hours under reflux in a nitrogen atmosphere. The reaction mixture was prepared with a saturated ammonium chloride solution, the organic phase separated, washed with aqueous brine, dried over MgSO4 and concentrated on a rotary evaporator under reduced pressure. The product 2- (2-anilinophenyl) propan-2-ol (4) obtained was used without additional purification for the subsequent synthesis.

FT-IR (ATR), v (cm- ¹ ): 3351, 2976, 1589, 1513, 1496, 1454, 131 1, 745. 9,9-Dimethyl-10H-acridine (5)

 To the previously obtained oily substance (4) was added 6 ml of concentrated sulfuric acid, and the mixture was stirred for one hour at room temperature under nitrogen. After dilution with water (200 ml), aqueous ammonia (10% (v / v)) was added to pH7. The mixture was then added to water (50 ml) and extracted with ethyl acetate (150 ml). The purified organic phase was rinsed with saturated sodium carbonate, brine and water, dried with MgSCU and concentrated on a rotary evaporator under reduced pressure. The product 9,9-dimethyl-10H-acridine (5) was purified by column chromatography with chloroform / isohexane (1/1). Yield: 3.13 g of yellowish crystals.

¹ H NMR (500 MHz, CDCb) δ = 7.38-7.24 (m, 6H), 7, 10 (t, J = 7.3 Hz, 1H), 6.74 (ddd, J = 8 , 1, 6, 9, 1, 3 Hz, 1 H), 1, 6 (s, 3H).

¹³ C NMR (126 MHz, CDCl 3) δ = 138.42, 129.09, 126.69, 125.44, 120.58, 1 13.39, 36, 15, 30.56. FT-IR (ATR), v (cm ¹ ): 3358, 3062, 2966, 2917, 1607, 1507, 1481, 1453, 1319, 744. MS (ESI) m / z: 210.4 ([M ⁺ ] + 1 ).

Example 2 Synthesis of Emitters IV-1, IV-2, IV-3, IV-4, IV-5 and IV-6

D = donor

 Methyl 2-iodobenzoate (6)

 10 g of ice, 12 g of distilled water and 20.4 g (1 1, 2 ml) of concentrated sulfuric acid were added to a 500 ml beaker cooled externally with ice and brine, and stirred. Subsequently, 20 g (0.13 mol) of methyl anthranylate (2) was added rapidly. The solidifying white paste was diluted with 12 ml of water and cooled to 0-5 ° C temperature. Thereafter, a solution of 1 1, 55 g (0, 16 mol) of sodium nitrite in 12 ml of water was added slowly in portions. The temperature must not exceed 7 ° C. The end of the nitrosation was determined with Kl starch paper. The resulting diazonium salt was cooled to -5 ° C over 10 minutes and then to a preheated to 40 ° C mixture of 22.4 g Kl solution in 40 ml of distilled water, 6.5 g of sodium hydrosulfite and concentrated sulfuric acid in a 500 ml Three-necked round bottom flask with reflux condenser added. This mixture was stirred at 40 ° C for 5 minutes and then at 80 ° C for one hour. The black reaction mixture was cooled to room temperature and rinsed with 20 mL of 20% H2SO4, 20 mL NaHSCU, water and brine. The separated organic phase was diluted with 30 ml of ethyl acetate, dried over MgSO4, filtered off and completely evaporated. The yield was 26 g (76%) of orange methyl 2-iodobenzoate (6).

¹ H NMR (500 MHz, DMSO) 5 = 8.01 (dd, J = 7.9, 1, 0, 1 H), 7.71 (dd, J = 7.7, 1, 7, 1 H) , 7.51 (td, J = 7.6, 1, 2, 1H), 7.30-7.26 (m, 1H).

¹³ C NMR (126 MHz, DMSO) δ = 167.04, 140.55, 135.83, 132.94, 130.23, 128.27, 94.24, 52.52. MS (ESI) m / z: 263 ([M ⁺ ] +1).

Methyl 2- (N-phenylanilino) benzoate ((IV-1) (DPA-MB)

 (Iv-1)

Methyl 2-aminobenzoate (14.38 g, 0.097 mol), bromobenzene (18.29 g, 0.1-16 mol), activated K2CO3 (9.37 g, 0.07 mol) and dichlorobenzene (50 mL) were added a 250 ml Schlenk flask was added. The reaction mixture was deoxygenated several times with a vacuum pump before adding Cu (5.2 g, 0.078 mol) and Cul (0.61 g, 3.5 mmol) under N 2 atmosphere. The reaction mixture was stirred overnight at 190 ° C and then filtered. The obtained Solid was washed with toluene. The crude product was dissolved in diethyl ether and crystallized overnight. 7 g of transparent crystals were obtained (24%).

¹ H NMR (300 MHz, CDCb) δ = 7.73 (dd, J = 7.9, 1.5, 1H), 7.45 (t, J = 7.2, 3.6, 1H), 7 , 32-7.17 (m, 7H), 7.09-6.94 (m, 6H), 3.47 (s, 3H).

¹³ C NMR (126 MHz, CDCls) δ = 167.86, 147.72, 146.58, 132.64, 131.21, 129.06, 129.0, 128.93, 124.24, 122.79 , 122,24, 51,78.

MS (ESI) m / z: 304.1 ([M ⁺ ] +1).

FT-IR (ATR), v (cm ¹ ): 3054, 2948, 2917, 1709, 15861507, 1480, 1446, 1300, 750, 696. Methyl-2-carbazol-9-yl-benzoate (IV-2) (Cz- MB)

 (IV-2)

 Into a 100 ml Schlenk flask were added 1.28 g (7.6 mmol) of carbazole, 2 g (7.6 mmol) of methyl 2-iodobenzoate (6), 2.1 g (15.6 mmol) of activated potassium carbonate and 25 ml Added 1,2-dichlorobenzene. The resulting reaction mixture was degassed three times with a vacuum pump, and then 0.96 g (15.2 mmol) of copper and 0.06 g (0.3 mmol) of copper iodide (I) were added under nitrogen. The reaction mixture was then stirred at 190 ° C. for 12 hours, cooled, filtered off and rinsed with toluene. The filtrate was further concentrated under reduced pressure. The resulting product was dissolved in diethyl ether and crystallized overnight. The crystals formed were filtered off and rinsed with acetonitrile. The yield was 1.15 g (50%) of colorless crystals. H NMR (500 MHz, CDCl3) δ = 8.15-8.12 (m, 1H), 8.12-8.10 (m, 1H), 7.75 (td, J = 7.7, 1, 6, 1H), 7.60 (dd, J = 12.1, 4.5, 1H), 7.37 (ddd, J = 8.3, 7.2, 1.2, 1H), 7.27 (dd, J = 11.1, 4.2, 1H), 7.14 - 7.11 (m, 1H), 3.19 (s, 1H).

¹³ C NMR (126 MHz, CDCb) δ = 166.44, 141.56, 139.42, 136.91, 133.35, 131.98, 130.10, 130.04, 128.28, 125.93 , 125.77, 123.28, 123.25, 120.27, 120.26, 119.78, 119.36, 110.54, 109.27, 52.09

MS (ESI) m / z: 302.1 ([M ⁺ ] +1).

Methyl 2-phenothiazin-10-yl benzoate (IV-3) (PT-MB)

 (IV-3)

 Phenothiazine (1, 52 g, 7.6 mmol), methyl 2-iodobenzoate (6) (2 g, 7.6 mmol), activated K 2 CO 3 (1, 06 g, 7.6 mmol) and dichlorobenzene (25 mL) were added to a 100 ml Schlenk flask. The reaction mixture was deoxygenated several times with a vacuum pump before adding Cu (0.96 g, 15.2 mmol) and Cul (0.06 g, 0.3 mmol) under N 2 atmosphere. Subsequently, the reaction mixture was stirred for 12 hours at 190 ° C and filtered. The remaining solid was washed with toluene and the mixture was concentrated under reduced pressure. The viscous crude product was dissolved in 20 ml of diethyl ether and crystallized overnight. The resulting yellow crystals were washed with acetone tril, after which the yield was 1.54 g (61%).

¹ H NMR (500 MHz, CDC) δ = 8, 17 (d, J = 7.5, 1H), 7.77 (t, J = 7.3, 1H), 7.59 (td, J = 7.7, 1, 2, 1H), 7.47 (d, J = 7β, 1H), 6.99-6.91 (m, 2H), 6.78 (s, 4H), 5 , 97 (d, J = 6.8, 2H), 3.74 (s, 3H).

¹³ C NMR (126 MHz, CDCb) δ = 166.04, 143.47, 140.01, 134.22, 133.67, 132.85, 132, 14, 128.77, 126.69, 126.46 , 122, 16, 1 19.10, 1 15.09, 52.49.

MS (ESI) m / z: 334, 1 ([M ⁺ ] +1). Methyl 2-phenoxazin-10-yl benzoate (IV-4) (PXZ-MB)

 (IV-4)

 Phenoxazine (0.879 g, 4.8 mmol), methyl 2-iodobenzoate (6) (1.25 g, 4.8 mmol), activated K 2 CO 3 (0.66 g, 4.8 mmol) and dichlorobenzene (25 mL) were added to a 100 ml Schlenk flask. The reaction mixture was deoxygenated several times with a vacuum pump before adding Cu (0.61 g, 9.6 mmol) and Cul (0.036 g, 0.19 mmol) under N 2 atmosphere. Subsequently, the reaction mixture was stirred for 12 hours at 190 ° C and filtered. The remaining solid was filtered off and washed with toluene. The mixture was concentrated under reduced pressure and the crude product crystallized out. The resulting yellow crystals were dissolved in a 1: 1 mixture of dichloromethane and hexane and purified by column chromatography. The result was 1.14 g of a yellow crystalline substance (75%).

¹ H NMR (500 MHz, CDCl 3) δ = 8.15 (dd, J = 7.8, 1, 6, 1 H), 7.75 (td, J = 7.7, 1, 6, 1 H) , 7.57 (td, J = 7, 7, 1, 2, 1 H), 7.41 (dd, J = 7β, 1, 0, 1 H), 6.68 (dd, J = 7β, 1, 5, 2H), 6.62 (td, J = 7.6 , 1, 5, 2H), 6.56 (td, J = 7.7, 1, 6, 2H), 5.79 (dd, J = 7.9, 1, 5, 2H), 3.72 ( s, 3H).

¹³ C NMR (126 MHz, CDC) δ = 165.74 (s), 143.80 (s), 138.47 (s), 134.65 (s), 134.02 (s), 133.29 ( s), 133.09 (s), 131, 59 (s), 128.82 (s), 123, 13 (s), 121, 21 (s), 1 15.36 (s), 1.12.84 (s), 77.25 (s), 77.00 (s), 76.75 (s), 52.51 (s).

MS (ESI) m / z: 318, 1 ([M ⁺ ] +1).

Methyl 2- (9,9-dimethylacridin-10-yl) benzoate (IV-5) (DMAC-MB)

 (IV-5)

 9,9-Dimethyl-10H-acridine (5) (1 g, 4.8 mmol), methyl 2-iodobenzoate (6) (1.25 g, 4.8 mmol), activated K 2 CO 3 (0.66 g, 4.8 mmol) and dichlorobenzene (25 ml) were charged to a 100 ml Schlenk flask. The reaction mixture was deoxygenated several times with a vacuum pump before adding Cu (0.61 g, 9.6 mmol) and Cul (0.036 g, 0.19 mmol) under N 2 atmosphere. Subsequently, the reaction mixture was stirred at 190 ° C for 12 hours. The solid remaining after filtration was washed with toluene and Tetrah yd rofu ran. The solution was concentrated under reduced pressure and the crude product was purified by column chromatography with a 1: 1 mixture of chloroform and hexane as eluent. There was obtained 0.95 g of a yellow crystalline material (58%).

¹ H NMR (500 MHz, CDC) δ = 8, 18 (dd, J = 7.8, 1, 6, 1 H), 7.78 (td, J = 7.7, 1, 7, 1 H) , 7.61 (td, J = 7.7, 1, 3, 1H), 7.46 (dd, J = 7.5, 1, 8, 2H), 7.35 (dd, J = 7, 8, 1, 1, 1 H), 6.99-6.85 (m, 4H), 6.07 (dd, J = 8.0, 1, 4, 2H), 3.56 (s, 3H) , 1, 80-1, 66 (m, 6H).

¹³ C NMR (126 MHz, CDCl3) δ = 166.07 (s), 140.82 (s), 140.55 (s), 134.72 (s), 133.54 (s), 132.87 ( s), 132.46 (s), 129.70 (s), 128.69 (s), 126.49 (s), 125.77 (s), 120.48 (s), 1 13.65 ( s), 52.46 (s), 35.99 (s).

MS (ESI) m / z: 344.2 ([M ⁺ ] +1).

2,2 '(N- (methylbenzenecarboxyl-2-yl)) iminodibenzyl (IV-6) (IDB-MB)

 (IV-6)

 Iminodibenzyl (1.48 g, 7.6 mmol), methyl 2-iodobenzoate (6) (2 g, 7.6 mmol), activated K 2 CO 3 (1.06 g, 7.6 mmol) and dichlorobenzene (25 mL) were added in a 100 ml Schlenk flask was added. The reaction mixture was deoxygenated several times with a vacuum pump before adding Cu (0.96 g, 15.2 mmol) and CuI (0.06 g, 0.3 mmol) under N 2 atmosphere. The reaction mixture was stirred overnight at 190 ° C and then filtered. The resulting solid was washed with toluene and the filtrate was concentrated under reduced pressure. The dark viscous crude product was dissolved in a 1: 1 mixture of dichloromethane and isohexane as eluent and purified by column chromatography. The yield was 0.5 g of transparent crystals (20%).

¹ H NMR (500 MHz, CDC) δ = 7.41 (dt, J = 7.9, 3.9, 1H), 7.28-7.19 (m, 5H), 7.16-7, 08 (m, 5H), 6.86 (td, J = 7.6, 1, 0, 1H), 3.30 (s, 3H), 3, 18 (s, 4H)

¹³ C NMR (126 MHz, CDCb) δ = 169.37, 145, 19, 144.76, 137.68, 131, 22, 130.71, 130.39, 126.67, 126.60, 125.95 , 120.78, 1 18.80, 1 18.07.

MS (ESI) m / z: 330.2 ([M ⁺ ] +1).

Claims

claims 1 . A compound comprising at least one donor group and at least one acceptor group of general structural formula (I)

where, in the compounds according to formula (I), Ry with each occurrence is independently selected from the group consisting of R CO 2 R ^X , COR ^x , SO 2 R ^X , P (O) (R ^X ) 2, and C = N, where R with each occurrence is independently selected from the group consisting of -CH 2 -, -CH 2 CH 2 - and a linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl group; R ^x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR ² R ³ , wherein R ² and R ³ with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C ³ -C 20 alkyl or alkenyl, aryl and heteroaryl;  m is selected from 0, 1, 2, 3, 4 or 5;  n is selected from 0, 1, 2, 3, 4, 5 and 6; and  o is selected from 0, 1, 2, 3, 4, 5 and 6, where n + o> 1, where m + n + o = 6, with the proviso that when o> 1, Ry is not COR ^x , S0 ₂ R ^x , P (0) (R ^x ) ₂ , or C = N; wherein at least one R ^{x is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl. The compound according to claim 1, wherein n is at least 1. The compound according to claim 1 or 2, wherein the compound of the formula (I) is a compound of the general structural formula (II):

where, in compounds according to formula (II), R with each occurrence is independently selected from the group consisting of -CH 2 -, -CH 2 CH 2 - and a linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl group; R ^x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR ² R ³ , wherein R ² and R ³ with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C ³ -C 20 alkyl or alkenyl, aryl and heteroaryl;  m is selected from 0, 1, 2, 3, 4 or 5;  n is selected from 0, 1, 2, 3, 4, 5 and 6; and  o is selected from 0, 1, 2, 3, 4, 5 and 6, where n + o> 1, where m + n + o = 6; wherein at least one R ^{x is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl. 4. The compound according to any one of claims 1 or 3, wherein, in the compounds of formula (I) or (II), at least one of R ^x , R ² and R ^{3 is} a group represented by formula (III):

where, in the groups according to formula (III), R, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ^{8 are} independently selected from the group consisting of hydrogen, bromine, methyloxy, methyl, ethyl, CF 3, linear or branched C 3 -C 20 alkyl or Alkenyl and aryl; X is selected from the group consisting of S, SO 2, O, C = O, NH, N-CH ₃ , NCH ₂ CH ₃ , NR ⁹ , C (CH ₃ ) ₂ , C (CH ₂ CH ₃ ) 2, C (R ¹⁹ ) ₂ , Si (CH ₃ ) ₂ , Si (CH ₂ CH ₃ ) 2, Si (R ¹⁹ ) ₂ , 0 = P-O-R ¹⁹ , 0 = PR ¹⁹ , HP (CH ₃ ) ₂ , HP (CH ₂ CH ₃ ) 2 and HP (R ⁹ ) 2, wherein R ⁹ with each occurrence is independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched C 3 -C 20 alkyl or alkenyl, and aryl; or X is nothing, a direct carbon-carbon bond of the two aryl groups of the group of formula (II) to each other, or -CH 2 -CH 2 -; and the attachment site of the group of formula (III) to the compound of formula (I) or (II). 5. The compound according to claim 4, wherein, in the compounds of the formula (I) or (II), at least one of R ^x , R ² and R ^{3 represents} a group represented by formula (III-1), (III-2) , (III-3), (III-4), (III-5) or (III-6) is:

(III-1) (III-2) (III-3)

(III-4) (III-5) (III-6) wherein represents the point of attachment of the respective group to the compound of formula (I) or (II). The compound according to claim 4 or 5, wherein at least one R ^x which is directly bonded to the ring in formula (I) or (II) represents a group represented by formula (III), (III-1), (II-2 ), (III-3), (III-4), (III-5) or (III-6). The compound according to any one of the preceding claims, wherein the compound of the formula (I) or (II) represents a compound represented by formula (IV), (V), (VI), (VII), (VIII), (IX), ( X) (XI), (XII), (XIII), (XIX) or (XX) is:

wherein, in the compounds of the formulas (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), (XII), (XIII), (XIX ) and (XX), R ^x , R ² , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 are} each independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 Alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR ² R ³ , wherein R ² and R ³ with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C ³ -C 20 Alkyl or alkenyl, aryl and heteroaryl, with the proviso that at least one of R ^x , R ² , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ^{26 is} selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl. 8. The compound according to claim 7, wherein, in the compounds represented by the formulas (IV), (V), (VI), (VII), (VIII), (IX), (X), (XI), ( XII), (XIII), (XIX) and (XX), at least one of R ^x , R ² , R ³ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ , preferably at least one of R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ , a group represented by formula (III) according to claim 4 or a group represented by formula (III-1), (III-2), (III-3 ), (III-4), (III-5) or (III-6) according to claim 5. The compound of any of the preceding claims, wherein the compound is a compound represented by one of the following formulas:

(IV-5) (IV-6)

10. A compound, characterized in that it is obtainable by dimerization or multimerization of at least two compounds according to claims 1 to 9. 1 1. Use of a compound according to any one of claims 1 to 10 in an optoelectronic component, such as an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), a organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quenching device (O-FQD) light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser) each as an emitter material, or as a material in which the triplet excitations are converted into singlet excitations by thermal activation, these singlets are then used to excite other embedded singlet emitter. 12. Optoelectronic component containing at least one compound according to one of claims 1 to 10. 13. The optoelectronic component according to claim 12, comprising at least one compound according to any one of claims 1 to 10, wherein the compound of general structural formula (I) emits electromagnetic radiation having a wavelength of 380 nm to 750 nm, or the compound of the general structural formula ( I) transmits their singlet excitations to another fluorescent emitter emitting at a wavelength of 380 nm to 750 nm. 14. The optoelectronic component according to claim 13, wherein the emission takes place predominantly in the blue spectral range from 400 nm to 480 nm. 15. The optoelectronic component according to claim 13, wherein the emission takes place predominantly in the green spectral range from 480 nm to 580 nm. 16. The optoelectronic component according to claim 13, wherein the emission takes place predominantly in the red spectral range from 580 nm to 750 nm.