Materials for organic electroluminescent devices

Abstract

The present invention relates to compounds of formula (1) suitable for use in electronic devices, in particular for use in organic electroluminescent devices, and to electronic devices comprising these compounds.

Description

[0001] The present invention relates to compounds of formula (1), to the use of said compounds in electronic devices, and to electronic devices comprising compounds of formula (1). Furthermore, the present invention relates to formulations comprising one or more compounds of formula (1).

[0002] Currently, intensive research is being carried out on the development of functional compounds for use in electronic devices. In particular, the aim is to develop compounds that enable electronic devices to achieve improved performance at one or more relevant points, such as the power efficiency and lifetime of the device, as well as the color coordinates of the emitted light.

[0003] According to the present invention, the term electronic device particularly refers to an organic integrated circuit (OIC), an organic field effect transistor (OFET), an organic thin film transistor (OTFT), an organic light emitting transistor (OLET), an organic solar cell (OSC), an organic optical detector, an organic photoreceptor, an organic field quenching device (OFQD), an organic light emitting electrochemical cell (OLEC), an organic laser diode (O-laser), and an organic light emitting diode (OLED).

[0004] Particularly interesting is the provision of compounds for use in the later-mentioned electronic devices called OLEDs. The general structure and functional principle of OLEDs are known to those skilled in the art and are described, for example, in US 4539507.

[0005] The performance data of OLEDs still need to be further improved, especially considering their wide commercial use, such as in display devices or as light sources. In this regard, particularly important are the lifetime, efficiency, and operating voltage of OLEDs, as well as the achieved color values. Especially in the case of blue-emitting OLEDs, there is potential for improvement in terms of the lifetime of the device, efficiency, and color purity of the emitter.

[0006] An important starting point for achieving said improvements is the selection of emitter compounds and host compounds used in electronic devices.

[0007] In the last decade, polycyclic aromatic compounds containing boron and nitrogen atoms have been described (for example, in US 2015 / 0236274 A1, CN 107501311 A, WO 2018 / 047639 A1, or WO 2020 / 208051). These compounds can be used as fluorescent emitters.

[0008] However, there is still a need for other fluorescent emitters, especially blue fluorescent emitters, which can be used in OLEDs and enable OLEDs to have very good performance in terms of lifetime, color emission, and efficiency. More particularly, there is a need for blue fluorescent emitters that combine very high efficiency, very good lifetime, suitable color coordinates, and high color purity.

[0009] In addition, in recent years, an organic electroluminescent device has been described which has a TADF compound as a photosensitizer in a light-emitting layer and a fluorescent compound having a high spatial shielding property with respect to its environment as a light emitter (for example, in WO 2015 / 135624). The TADF material corresponds to a thermally activated delayed fluorescence material. The TADF material is generally an organic material in which the energy gap between the lowest triplet state T 1 and the first excited singlet state S 1 is small enough that the S 1 state can be thermally reached from the T 1 state, as explained, for example, in H. Uoyama et al., Nature 2012, vol. 492, 234. Using a TADF compound as a photosensitizer in the device structure and transferring its energy to a fluorescent emitter enables an organic electroluminescent device that emits all light-emitting colors to be provided, so that the basic structure of a known fluorescent emitter can be used, but still exhibits the high efficiency of an electroluminescent device with TADF. This is also known as hyperfluorescence.

[0010] As an alternative, the prior art describes an organic electroluminescent device which contains, in a light-emitting layer, a phosphorescent organometallic complex that exhibits mixing of the S 1 state and the T 1 state due to large spin-orbit coupling as a photosensitizer, and contains a fluorescent compound as a light emitter, whereby the light emission decay time can be significantly shortened. This is also known as hyperphosphorescence.

[0011] Hyperfluorescence and hyperphosphorescence are also promising technologies for improving OLED performance, especially in deep blue light emission.

[0012] However, the performance data of OLEDs here still need to be further improved, especially considering wide commercial use, such as in display devices or as light sources. Of particular importance in this regard are the lifetime, efficiency, operating voltage, and achieved color values of the OLEDs, especially color purity.

[0013] An important starting point for achieving the above improvements in hyperfluorescence and hyperphosphorescence systems is the selection of fluorescent emitter compounds, preferably sterically hindered (also called shielded) fluorescent emitter compounds.

[0014] In WO 2015 / 135624, a sterically hindered fluorophore based on rubrene is described. However, there is still a need for other sterically hindered fluorophores, especially sterically hindered blue fluorophores, which enable OLEDs to have very good performance in terms of efficiency and color emission. More particularly, there is a need for a deep blue fluorophore that combines very high efficiency, very good lifetime, suitable color coordinates, and high color purity.

[0015] Furthermore, it is known that OLEDs can comprise different layers, which can be applied by vapor deposition in a vacuum chamber or by solution processing. Methods based on vapor deposition give good results, but such methods are complex and expensive. Therefore, there is also a need for OLED materials that can be easily and reliably solution processed. In this case, the materials should have good solubility in the solutions containing them. In addition, solution-processed OLED materials should be able to orient themselves in the deposited film, thereby improving the overall efficiency of the OLED. The term orientation here refers to the horizontal molecular orientation of the compound, as explained in Zhao et al., Horizontal molecular orientation in solution-processed organic light-emitting diodes, Appl. Phys. Lett. 106063301, 2015.

[0016] Accordingly, the technical object of the present invention is based on providing a fluorophore that exhibits prompt fluorescence and / or delayed fluorescence. The technical object of the present invention is also based on providing a sterically hindered fluorophore that can be combined with a photosensitizer compound for use in a hyperfluorescence or hyperphosphorescence system. The technical object of the present invention is also based on providing a compound that is suitable for use in an electronic device such as an OLED, more particularly as a fluorophore, and is suitable for vacuum processing or for solution processing.

[0017] Generally, there is a need for a stable fluorophore that exhibits deep blue emission. There is a need to improve the color purity of the prior art materials, and for the potential use in hyperphosphorescent devices, there is a need to improve the shielding factor (as disclosed in WO 2020 / 053314 A1). In particular, the full width at half maximum (FWHM) should be as narrow as possible.

[0018] In the research on novel compounds for use in electronic devices, it has now been found that compounds of formula (1) as defined below are very suitable for use in electronic devices. In particular, they achieve one or more, preferably all of the above-mentioned technical objects.

[0019] Accordingly, the present invention relates to a compound of formula (1),

[0020]

[0021] The symbols and notations used are subject to the following provisions:

[0022] X 2 represents CR, the same or different in each case 2 or N;

[0023] X A represents CR, the same or different in each case A or N;

[0024] Y is a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R in each case Y ;

[0025] R B represents CN, N(Ar), the same or different in each case 2 , C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R) 2 , Si(R) 3 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of said groups being optionally substituted by one or more groups R, wherein in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O, S or CONR and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R in each case, or an aryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups;

[0026] R 2 、R A 、R Ywhich, in each case independently, represents H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, NO 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which groups may be substituted by one or more groups R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, an aryloxy group having 5 to 60 aromatic ring atoms or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more groups R; where two adjacent groups selected from R Y , R 2 , R A may form a monocyclic or polycyclic aliphatic or aromatic ring system which may be substituted by one or more groups R;

[0027] R, which, in each case independently, represents H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, NO 2 , Si(R’) 3 , B(OR’) 2 , OSO 2 R’, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which groups may be substituted by one or more groups R’, where in each case one or more non-adjacent CH 2The group may be replaced by R’C=CR’, C≡C, Si(R’) 2 , Ge(R’) 2 , Sn(R’) 2 , C=O, C=S, C=Se, P(=O)(R’), SO, SO 2 , O, S or CONR’ and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , in each case an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R’, or an aryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R’, where two adjacent groups R may form an aliphatic or aromatic ring system, monocyclic or polycyclic, which may be substituted by one or more groups R’;

[0028] Ar is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms which may in each case also be substituted by one or more groups R’;

[0029] R’ is in each case the same or different and represents H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH 2 groups may be replaced by SO, SO 2 , O, S and one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms.

[0030] Adjacent substituents in the sense of the present invention are substituents which are bonded to atoms which are directly connected to one another or to the same atom.

[0031] Furthermore, the following definitions of chemical groups apply for the purposes of the present application:

[0032] An aryl group in the sense of the present invention contains 6 to 60 aromatic ring atoms, preferably 6 to 40 aromatic ring atoms, more preferably 6 to 20 aromatic ring atoms; a heteroaryl group in the sense of the present invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, where at least one is a heteroatom. The heteroatom is preferably selected from N, O and S. This represents the basic definition. If other preferences are indicated in the description of the present invention, for example other preferences regarding the number of aromatic ring atoms or heteroatoms present, then these preferences apply.

[0033] An aryl group or heteroaryl group herein refers to a simple aromatic ring, i.e., benzene, or a simple heteroaromatic ring, such as pyridine, pyrimidine or thiophene, or a fused (annelated) aromatic or heteroaromatic polycycle, such as naphthalene, phenanthrene, quinoline or carbazole. A fused (annelated) aromatic or heteroaromatic polycycle in the sense of the present application consists of two or more simple aromatic rings or heteroaromatic rings fused to each other.

[0034] An aryl or heteroaryl group that can be substituted by the groups mentioned above in each case and can be linked to an aromatic or heteroaromatic ring system via any desired position especially refers to a group derived from the following substances: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridinimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarbazole, 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.

[0035] An aryloxy group as defined according to the present invention refers to an aryl group as defined above bonded via an oxygen atom. A similar definition applies to a heteroaryloxy group.

[0036] An aralkyl group as defined according to the present invention refers to an alkyl group in which at least one hydrogen atom is replaced by an aryl group. A similar definition applies to a heteroaralkyl group.

[0037] An aromatic ring system in the sense of the present invention contains 6 to 60 C atoms in the ring system, preferably 6 to 40 C atoms, more preferably 6 to 20 C atoms. A heteroaromatic ring system in the sense of the present invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, where at least one is a heteroatom. The heteroatom is preferably selected from N, O and / or S. An aromatic or heteroaromatic ring system in the sense of the present invention is considered to refer to the following system: it does not necessarily contain only aryl or heteroaryl groups, but rather multiple aryl or heteroaryl groups can also be connected through non-aromatic units (preferably less than 10% of the non-H atoms) such as sp 3 -hybridized C, Si, N or O atoms, sp 2 -hybridized C or N atoms or sp-hybridized C atoms. Thus, for example, systems such as 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., and systems in which two or more aryl groups are connected, for example, by a straight-chain or cyclic alkyl, alkenyl or alkynyl group or by a silyl group, are also considered aromatic ring systems in the sense of the present invention. In addition, for example, systems in which two or more aryl or heteroaryl groups are connected to each other via a single bond, such as biphenyl, terphenyl or diphenyltriazine systems, should also be considered aromatic or heteroaromatic ring systems in the sense of the present invention.

[0038] An aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which can be substituted in each case by the groups mentioned above and can be attached to the aromatic or heteroaromatic group via any desired position, in particular refers to groups derived from the following substances or combinations of these groups: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, bibenzylidene, terphenyl, terbenzylidene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indeno[1,2-b]fluorene, trindene, isotrindene, spirotrindene, spiroisotrindene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indeno[1,2-b]carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo[5,6]quinoline, benzo[6,7]quinoline, benzo[7,8]quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridinimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaphenanthrene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluoranthene ring, 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.

[0039] For the purposes of the present invention, where individual hydrogen atoms or CH 2A straight-chain alkyl group having 1 to 40 C atoms, a branched or cyclic alkyl group having 3 to 40 C atoms, or an alkenyl or alkynyl group having 2 to 40 C atoms, wherein the group can be substituted by the groups mentioned above in the definition of the group, preferably refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl. An alkoxy or thioalkyl group having 1 to 40 C atoms preferably refers to methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, vinylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio.

[0040] For the purposes of the present application, the expression that two or more groups can form a ring with each other is considered to particularly mean that two groups are connected to each other by a chemical bond. This is illustrated by the following scheme:

[0041]

[0042] 。

[0043] However, in addition, the above-mentioned expression is also considered to mean that, in the case where one of the two groups represents hydrogen, the second group is bonded at the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following scheme:

[0044] 。

[0045] In a preferred embodiment, Y corresponds to a group of formula (Y1) or (Y2):

[0046]

[0047] wherein the symbols have the same meaning as above, the dashed line represents a bond connected to Y in formula (1), and

[0048] X Y represents CR Y or N, the same or different in each case.

[0049] In a preferred embodiment, at most two R Y are different from H, D or F.

[0050] In a preferred embodiment, in each 6-membered ring, at most two selected from X 2 、X A or X Y correspond to N.

[0051] In another embodiment, the group Y is selected from groups according to formula (Y2-1):

[0052]

[0053] wherein the symbols have the same meaning as above.

[0054] According to a preferred embodiment, the compound of formula (1) corresponds to a compound of formula (1-Y1),

[0055]

[0056] wherein the symbols have the same meaning as above, and

[0057] X Y represents CR Y or N, the same or different in each case.

[0058] According to a preferred embodiment, the compound of formula (1) is selected from compounds of formula (2),

[0059]

[0060] wherein the symbols have the same meaning as above.

[0061] Preferably, the compound of formula (2) corresponds to a compound of formula (2-Y2),

[0062]

[0063] wherein the symbols have the same meaning as above.

[0064] According to a highly preferred embodiment, the compound of formula (1) is selected from compounds of formula (3).

[0065]

[0066] wherein the symbols have the same meanings as above.

[0067] Preferably, the compound of formula (3) corresponds to the compound of formula (3-Y2),

[0068]

[0069] wherein the symbols have the same meanings as above.

[0070] According to a particularly preferred embodiment, the compound of formula (1) is selected from the compounds of formula (4),

[0071]

[0072] wherein the symbols and markings have the same meanings as above.

[0073] Preferably, the compound of formula (4) corresponds to the compound of formula (4-Y2) or (4-Y2-1),

[0074]

[0075] wherein the symbols have the same meanings as above.

[0076] Preferably, the group R B in each case represents, identically or differently, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 carbon atoms or an alkenyl or alkynyl group having 2 to 40, preferably 2 to 20, more preferably 1 to 10 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 carbon atoms, each of which groups may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O, S or CONR and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2Instead, or having an aromatic or heteroaromatic ring system with 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, the ring system being optionally substituted in each case by one or more groups R, or having an aralkyl or heteroaralkyl group with 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, the group being optionally substituted by one or more R groups.

[0077] More preferably, the group R B in each case the same or different represents a straight-chain alkyl or alkoxy group having 1 to 20, preferably 1 to 10 carbon atoms or an alkenyl or alkynyl group having 2 to 20, preferably 2 to 10 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20, preferably 3 to 10 carbon atoms, the groups each being optionally substituted by one or more groups R, where one or more H atoms may be replaced by D, F, Cl or CN, or having an aromatic ring system with 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, the ring system being optionally substituted in each case by one or more groups R, or having an aralkyl or heteroaralkyl group with 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, the group being optionally substituted by one or more R groups.

[0078] Very preferably, the group R B in each case the same or different

[0079] is selected from branched or cyclic alkyl groups represented by the following general formula (RS-a),

[0080]

[0081] (RS-a)

[0082] where

[0083] R 22 、R 23 、R 24 in each case the same or different is selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups are each optionally substituted by one or more groups R 25 and where the groups R 22 、R 23 、R 24 two or all of the groups R 22 、R 23 、R 24 may be linked to form a group which is optionally substituted by one or more groups R 25Substituted (poly)cyclic alkyl groups;

[0084] R 25 which is in each case the same or different and is selected from straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms;

[0085] with the proviso that in each case the group R 22 、R 23 and R 24 in at least one case is not H, with the proviso that in each case all the groups R 22 、R 23 and R 24 together have at least 4 carbon atoms, and with the proviso that in each case, if two of the groups R 22 、R 23 、R 24 are H, the remaining group is not straight-chain;

[0086] or is selected from branched or cyclic alkoxy groups represented by the following general formula (RS-b),

[0087]

[0088] (RS-b)

[0089] wherein

[0090] R 26 、R 27 、R 28 is in each case the same or different and is selected from H, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, wherein the above-mentioned groups may each be substituted by one or more groups R 25 as defined above, and wherein the groups R 26 、R 27 、R 28 in two cases or all the groups R 26 、R 27 、R 28 may be linked to form a (poly)cyclic alkyl group which may be substituted by one or more groups R 25 as defined above;

[0091] with the proviso that in each case only one of the groups R 26 、R 27 and R 28 may be H;

[0092] or is selected from aralkyl groups represented by the following general formula (RS-c),

[0093]

[0094] (RS-c)

[0095] wherein

[0096] R 29 、R 30 、R 31 are the same or different in each case and are selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein the above-mentioned groups may each be substituted by one or more groups R 32 or, in each case, an aromatic ring system having 6 to 30 aromatic ring atoms which may be substituted by one or more groups R 32 , and wherein two or all of the groups R 29 、R 30 、R 31 may be linked to form a (poly)cyclic alkyl group or an aromatic ring system which may each be substituted by one or more groups R 32 ;

[0097] R 32 is the same or different in each case and is selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms;

[0098] provided that in each case at least one of the groups R 29 、R 30 and R 31 is not H, and in each case at least one of the groups R 29 、R 30 and R 31 is an aromatic ring system having at least 6 aromatic ring atoms or contains an aromatic ring system having at least 6 aromatic ring atoms;

[0099] or is selected from aromatic ring systems represented by the following general formula (RS-d),

[0100]

[0101] (RS-d)

[0102] wherein

[0103] R 40 to R 44 are the same or different in each case and are selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein the above-mentioned groups may each be substituted by one or more groups R 32is replaced, or in each case may be replaced by one or more groups R 32 an aromatic ring system having 6 to 30 aromatic ring atoms, which is substituted, and wherein two or more of the groups R 40 to R 44 may be linked to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more groups R as defined above 32 .

[0104] Examples of suitable groups of formula (RS-a) to (RS-d) are groups (RS-1) to (RS-78):

[0105]

[0106]

[0107]

[0108] wherein the dashed bond represents the bonding of these groups to the structure of formula (1) and wherein the groups of formula (RS-1) to (RS-47) may also be substituted by at least one group R as defined above 25 and the groups (RS-48) to (RS-78) may also be substituted by at least one group R as defined above 32 .

[0109] Among the groups of formula (RS-1) to (RS-78), the preferred groups are (RS-62), (RS-64), (RS-65), (RS-67), (RS-70), (RS-77) and (RS-78).

[0110] Preferably, R 2 , R Y and R A in each case independently represent H, D, F, Cl, Br, I, CN, N(Ar) 2 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2、O, S or CONR and one or more of the H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 is replaced, an aromatic or heteroaromatic ring system having 5 to 60, preferably 1 to 40, more preferably 1 to 30, very preferably 1 to 18 aromatic ring atoms, the ring system in each case being optionally substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60, preferably 1 to 40, more preferably 1 to 30, very preferably 1 to 18 aromatic ring atoms, the group being optionally substituted by one or more R groups, where two adjacent groups selected from R Y 、R 2 、R A can form a monocyclic or polycyclic aliphatic or aromatic ring system optionally substituted by one or more groups R.

[0111] More preferably, R 2 、R Y and R A in each case independently represent H, D, F, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each group being optionally substituted by one or more groups R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, O or S and one or more of the H atoms may be replaced by D, F, an aromatic or heteroaromatic ring system having 5 to 60, preferably 1 to 40, more preferably 1 to 30, very preferably 1 to 18 aromatic ring atoms, the ring system in each case being optionally substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60, preferably 1 to 40, more preferably 1 to 30, very preferably 1 to 18 aromatic ring atoms, the group being optionally substituted by one or more R groups, where two adjacent groups selected from R Y 、R 2 、R A can form a monocyclic or polycyclic aliphatic or aromatic ring system optionally substituted by one or more groups R.

[0112] Very preferably, R 2 、R Y and R A in each case independently

[0113] represent H, D, F, CN; or

[0114] a group of formula (RS-a), a group of formula (RS-b), a group of formula (RS-c) or a group of formula (RS-d), wherein the groups of formula (RS-a), (RS-b), (RS-c) and (RS-d) have the same definitions as above, and wherein two adjacent groups among formula (RS-a), (RS-b), (RS-c) and (RS-d) may form a monocyclic or polycyclic aliphatic ring system or aromatic ring system; or

[0115] a group of formula (ArL-1),

[0116]

[0117] wherein the dashed bond in formula (ArL-1) represents the bonding to the structure of formula (1), wherein Ar 2 、Ar 3 in each case independently represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may in each case be substituted by one or more groups R; and wherein m is an integer selected from 1 to 10.

[0118] According to a preferred embodiment, at least one of the groups R 2 、R Y or R A represents a group of formula (RS-a), a group of formula (RS-b), a group of formula (RS-c) or a group of formula (RS-d), wherein the groups of formula (RS-a), (RS-b), (RS-c) and (RS-d) are as defined above.

[0119] According to a preferred embodiment, the groups R B and R A in each case independently are selected from the groups of formula (RS-a), (RS-b), (RS-c) and (RS-d), wherein the groups of formula (RS-a), (RS-b), (RS-c) and (RS-d) have the same definitions as above.

[0120] According to a preferred embodiment, at least one of the groups R, R Y 、R 2 or R A represents a group of formula (ArL-1) as defined above.

[0121] Preferably, the label m in the group of formula (ArL-1) is an integer selected from 1 to 6, very preferably an integer selected from 1 to 4.

[0122] In formula (ArL-1), the preferred group Ar 2 is selected from the groups of formula (Ar2-1) to (Ar2-25),

[0123]

[0124]

[0125] Wherein the dashed bond represents a bond to the structure of formula (1) and a bond to the group Ar 2 or Ar 3 and the groups of formulas (Ar2-1) to (Ar2-25) can be replaced at each free position by a group R having the same meaning as above, and wherein:

[0126] E 4 is selected from -B(R 0 )-, -C(R 0 ) 2 -, -C(R 0 ) 2 -C(R 0 ) 2 -, -Si(R 0 ) 2 -, -C(=O)-, -C(=NR 0 )-, -C=(C(R 0 )) 2 -, -O-, -S-, -S(=O)-, -SO 2 -, -N(R 0 )-, -P(R 0 )- and -P((=O)R 0 );

[0127] R 0 in each case independently represents H, D, F, CN, a linear alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, each of said groups being optionally substituted by one or more groups R, wherein in each case one or more non-adjacent CH 2 groups can be replaced by RC=CR, C≡C, C=O, C=S, SO, SO 2 , O or S and wherein one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 and an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, optionally substituted by one or more groups R in each case; wherein two adjacent substituents R 0 can form a monocyclic or polycyclic aliphatic or aromatic ring system optionally substituted by one or more groups R having the same meaning as above.

[0128] Preferably, E 4 is selected from -C(R 0 ) 2 -, -Si(R0 ) 2 -, -O-, -S- or -N(R 0 )-, where the substituent R 0 has the same meaning as above.

[0129] Preferably, R 0 in each case represents, independently of one another, H, D, F, CN, a linear alkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, where each of these groups may be substituted by one or more groups R, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, where the ring system in each case may be substituted by one or more groups R; where two adjacent substituents R 0 may form a monocyclic or polycyclic aliphatic or aromatic ring system which may be substituted by one or more groups R having the same meaning as above. Suitable examples of groups R 0 are H, methyl, ethyl, propyl, butyl, substituted and unsubstituted phenyl, substituted and unsubstituted biphenyl, substituted and unsubstituted naphthyl and substituted and unsubstituted fluorene.

[0130] In formulas (Ar2-1) to (Ar2-25), the following formulas are preferred: (Ar2-1), (Ar2-2), (Ar2-3), (Ar2-18), (Ar2-19), (Ar2-20), (Ar2-21), (Ar2-22) and (Ar2-25).

[0131] Furthermore, in formula (ArL-1), preferably Ar 3 in each case represents, independently of one another, a group selected from formulas (Ar3-1) to (Ar3-27),

[0132]

[0133]

[0134]

[0135] where the dashed bond represents the bond to Ar 2 and where E 4 has the same meaning as above, and the groups of formulas (Ar3-1) to (Ar3-27) may be substituted at each free position by a group R having the same meaning as above.

[0136] Among formulas (Ar3-1) to (Ar2-27), the following formulas are preferred: (Ar3-1), (Ar3-2), (Ar3-23), (Ar3-24), (Ar3-25), and (Ar3-27).

[0137] According to a preferred embodiment, at least one of the groups Ar 2 represents a group of formula (Ar2-2) and / or at least one of the groups Ar 3 represents a group of formula (Ar3-2),

[0138]

[0139] wherein

[0140] the dashed bond in formula (Ar2-2) represents the bonding to the structure of formula (1) and the bonding to the group Ar 2 or Ar 3 ; and the dashed bond in formula (Ar3-2) represents the bonding to Ar 2 ; and E 4 has the same meaning as above; and the groups of formulas (Ar2-2) and (Ar3-2) can be substituted at each free position by a group R having the same meaning as above.

[0141] According to a highly preferred embodiment, at least one of the groups Ar 2 represents a group of formula (Ar2-2-1) and / or at least one of the groups Ar 3 represents a group of formula (Ar3-2-1),

[0142]

[0143] wherein

[0144] the dashed bond in formula (Ar2-2-1) represents the bonding to the structure of formula (1) and the bonding to the group Ar 2 or Ar 3 ;

[0145] the dashed bond in formula (Ar3-2-1) represents the bonding to Ar 2 ;

[0146] E 4 has the same meaning as above; and

[0147] the groups of formulas (Ar2-2-1) and (Ar3-2-1) can be substituted at each free position by a group R having the same meaning as above.

[0148] According to a particularly preferred embodiment, the group Ar 2at least one group represented by formula (Ar2-2-1b) and / or the group Ar 3 at least one group represented by formula (Ar3-2-1b),

[0149]

[0150] wherein

[0151] the dashed bond in formula (Ar2-2-1b) represents bonding to the structure of formula (1) and to the group Ar 2 or Ar 3 ;

[0152] the dashed bond in formula (Ar3-2-1b) represents bonding to Ar 2 ;

[0153] R 0 has the same meaning as above; and

[0154] the groups of formula (Ar2-2-1b) and (Ar3-2-1b) can be substituted at each free position by a group R having the same meaning as above.

[0155] Very suitable groups R 2 、R Y and R A are for example H, D, F, CN, substituted or unsubstituted straight-chain alkyl groups having 1 to 10 C atoms, more particularly methyl, ethyl, propyl, butyl, substituted or unsubstituted branched or cyclic alkyl groups having 3 to 10 C atoms, more particularly tert-butyl, and aromatic or heteroaromatic ring systems selected from the groups of formula (Ar1-1) to (Ar1-24),

[0156]

[0157]

[0158] wherein in formulae (Ar1-1) to (Ar1-24):

[0159] - the dashed bond represents bonding to the structure of formula (1);

[0160] - R N in formula (Ar1-14) represents in each case identically or differently H, D, a straight-chain alkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which groups can be substituted by one or more groups R, where in each case one or more non-adjacent CH 2The group can be replaced by RC=CR, C≡C, C=O, C=S, SO, SO 2 , O or S, and one or more H atoms can be replaced by D, F or CN, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, particularly preferably 5 to 18 aromatic ring atoms, the ring system in each case being replaceable by one or more groups R, where two adjacent substituents R N can form an aliphatic or aromatic ring system, which is monocyclic or polycyclic and can be replaced by one or more groups R, where R has the same meaning as above;

[0161] - R in formulas (Ar1-12) and (Ar1-21) to (Ar1-24) 0 in each case represents, identically or differently, H, D, F, CN, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms, the groups each being replaceable by one or more groups R, where in each case one or more non-adjacent CH 2 groups can be replaced by RC=CR, C≡C, C=O, C=S, SO, SO 2 , O or S and one or more H atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case can be replaced by one or more groups R; where two adjacent substituents R 0 can form an aliphatic or aromatic ring system, which is monocyclic or polycyclic and can be replaced by one or more groups R having the same meaning as above;

[0162] - The groups of formulas (Ar1-1) to (Ar1-24) can be replaced at each free position by a group R having the same meaning as above.

[0163] According to a particularly preferred embodiment, the compounds of formula (1) are selected from the compounds of formula (5),

[0164]

[0165] where:

[0166] R 40 , R 42 , R 44 in each case represents, identically or differently, H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups are each replaceable by one or more groups R 32 or in each case can be replaced by one or more groups R 32A substituted aromatic ring system having 6 to 30 aromatic ring atoms; wherein R 32 is as defined above;

[0167] provided that at least one of R 40 and R 42 and R 44 is not H;

[0168] and the other symbols have the same meanings as above.

[0169] Preferably, the compound of formula (5) corresponds to a compound of formula (5-Y2) or (5-Y2-1),

[0170]

[0171] wherein the symbols have the same meanings as above.

[0172] According to another particularly preferred embodiment, the compound of formula (1) is selected from compounds of formula (6),

[0173]

[0174] wherein:

[0175] R 41 and R 43 are each independently selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein the above-mentioned groups may each be substituted by one or more groups R 32 or, in each case, an aromatic ring system having 6 to 30 aromatic ring atoms which may be substituted by one or more groups R 32 wherein R 32 is as defined above;

[0176] provided that at least one of R 41 and R 43 is not H.

[0177] Preferably, the compound of formula (6) corresponds to a compound of formula (6-Y2) or (6-Y2-1),

[0178]

[0179] wherein the symbols have the same meanings as above.

[0180] Preferably, the group R 42In each case the same or different and selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 substituted, or in each case may be substituted by one or more groups R 32 substituted aromatic ring systems having 6 to 30 aromatic ring atoms, and the groups R 40 、R 44 in each case the same or different and selected from aromatic ring systems having 6 to 30 aromatic ring atoms which may in each case be substituted by one or more groups R 32 substituted.

[0181] According to a preferred embodiment, the groups R 40 、R 42 、R 44 in the formulas (5), (5-Y2) and (5-Y2-1) are in each case the same or different and selected from straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 substituted. More preferably, the groups R 40 、R 42 、R 44 in each case the same or different and selected from straight-chain alkyl groups having 1 to 10, preferably 1 to 5, more preferably 1 to 3 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 substituted. In this case, examples of suitable groups R 40 、R 42 、R 44 are methyl, ethyl and butyl.

[0182] According to another preferred embodiment, the groups R 40 、R 42 、R 44 in each case the same or different and selected from aromatic ring systems having 6 to 30 aromatic ring atoms which may in each case be substituted by one or more groups R 32 substituted. Preferably, the compounds of formula (1) are selected from the compounds of formulas (5-1), (5-2) and (5-3),

[0183]

[0184]

[0185] where

[0186] in each of the formulas (5-1), (5-2) and (5-3), with -R32 The phenyl group shown is unsubstituted or substituted by one or more groups R 32 substituted;

[0187] R 42 and R 44 are in each case the same or different and are selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 substituted; where R 32 is as defined above.

[0188] More preferably, the compounds of formulae (5-1), (5-2) and (5-3) correspond to the compounds of formulae (5-1-Y2), (5-2-Y2), (5-3-Y2), (5-1-Y2-1), (5-2-Y2-1) and (5-3-Y2-1),

[0189]

[0190]

[0191]

[0192] where the symbols have the same meaning as above.

[0193] In another preferred embodiment, formula (Y2-1) is a group according to formula (Y2-1a):

[0194]

[0195] where the symbols have the same meaning as above.

[0196] Preferably, the group R in each case is the same or different and represents H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , Si(R’) 3 , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, the said groups each being optionally substituted by one or more groups R’, where in each case one or more non-adjacent CH 2The group may be replaced by R’C=CR’, O or S and one or more H atoms may be replaced by D, F or CN, and in each case an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R’, or an aryloxy group having 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, said group being substitutable by one or more groups R’, where two adjacent groups R may form a monocyclic or polycyclic aliphatic or aromatic ring system which may be substituted by one or more groups R’. When R is selected from aromatic or heteroaromatic ring systems, R is preferably selected from aromatic or heteroaromatic ring systems having 5 to 40, preferably 5 to 30, more preferably 5 to 18 aromatic ring atoms, or from aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms corresponding to the group of formula (ArL-1) as defined above.

[0197] Preferably, the group Ar is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 18, preferably 6 to 18 aromatic ring atoms, said ring system being in each case further substitutable by one or more groups R’.

[0198] Preferably, R’ in each case is the same or different and represents H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 10 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 10 C atoms, where one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 5 to 18, preferably 6 to 18 C atoms.

[0199] The following compounds are examples of compounds of formula (1):

[0200]

[0201]

[0202]

[0203] The compounds according to the invention can be prepared by synthetic steps known to those skilled in the art such as bromination, Suzuki coupling, Ullmann coupling, Hartwig-Buchwald coupling and the like. Examples of suitable synthetic methods are described in general terms in Schemes 1, 2 and 3 below.

[0204] Solution 1

[0205]

[0206] where X 1 and X 2is a leaving group, preferably selected from halogens such as Br, Cl, I, preferably Br, wherein two groups R present in the same boronic acid or ester group may be bonded to each other to form a ring, wherein the symbols Y and R B have the same meanings as above, and wherein the compounds described in Scheme 1 may also be substituted by groups R Y , R 2 and R A as defined above. After coupling a suitable group to the N group, the compound of formula (1) can be synthesized according to Scheme 2 or Scheme 3.

[0207] Solution 2

[0208]

[0209] wherein X 1 and X 2 are leaving groups, preferably selected from halogens such as Br, Cl, I, preferably Br, wherein two groups R present in the same boronic acid or ester group may be bonded to each other to form a ring, wherein the symbols Y and R B have the same meanings as above, and wherein the compounds described in Scheme 2 may also be substituted by groups R Y , R 2 and R A as defined above.

[0210] Solution 3

[0211]

[0212] wherein X 1 and X 2 are leaving groups, preferably selected from halogens such as Br, Cl, I, preferably Br, wherein the symbols Y and R B have the same meanings as above, and wherein the compounds described in Scheme 3 may also be substituted by groups R Y , R 2 and R A as defined above.

[0213] Accordingly, the present invention relates to a method for synthesizing a compound according to the present invention, the method comprising the steps of: wherein the carbazole structure is substituted by at least one boronic acid or ester group, and a cyclization reaction occurs with an aromatic or heteroaromatic compound such that the aromatic or heteroaromatic compound bridges two 6-membered rings of the carbazole structure, thereby forming at least a 6-membered ring. Then a triarylamine is formed with the carbazole structure.

[0214] Accordingly, the present invention relates to a method for synthesizing a compound according to the present invention, the method comprising the steps of: wherein a previously formed triarylamine is substituted by at least two boric acid or ester groups, and wherein a cyclization reaction occurs such that the boric acid or ester groups form a 6-membered ring with adjacent aromatic or heteroaromatic groups present in the triarylamine.

[0215] Accordingly, the present invention relates to a method for synthesizing a compound according to the present invention, the method comprising the steps of: wherein a previously formed triarylamine is substituted by at least two boron-halogen compounds, and wherein a cyclization reaction occurs such that the boron-halogen compounds form a 6-membered ring with adjacent aromatic or heteroaromatic groups present in the triarylamine.

[0216] The present invention also relates to a polymer, oligomer or dendrimer, said polymer, oligomer or dendrimer containing one or more compounds according to formula (1), wherein one or more bonds connecting to said polymer, oligomer or dendrimer may be located at any position substituted by R 2 、R A 、R B 、R Y or R in formula (1).

[0217] For processing a compound according to the present invention from the liquid phase, for example by spin coating or by a printing method, a formulation of the compound according to the present invention is required. These formulations can be, for example, solutions, dispersions or emulsions. For this purpose, a mixture of two or more solvents is preferably used. Suitable and preferred solvents are, for example: toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorobenzene, dioxane, phenyltoluenes, especially 3-phenyltoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, α-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indan, methyl benzoate, NMP, p-cymene, phenyl ethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol monobutyl methyl ether, triethylene glycol monobutyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0218] Accordingly, in addition, the present invention relates to a formulation which comprises a compound according to the present invention and at least one other compound. The other compound may be, for example, a solvent, in particular one of the solvents mentioned above, or a mixture of these solvents. However, the other compound may also be at least one other organic or inorganic compound which is also used in electronic devices, such as a luminescent compound, in particular a phosphorescent dopant and / or another host material. Suitable luminescent compounds and other host materials are shown below in connection with organic electroluminescent devices. The other compound may also be a polymer.

[0219] The compounds and mixtures according to the present invention are suitable for use in electronic devices. An electronic device herein refers to a device which comprises at least one layer containing at least one organic compound. However, the components herein may also comprise inorganic materials or layers consisting entirely of inorganic materials.

[0220] Accordingly, the present invention also relates to the use of a compound or mixture according to the present invention in an electronic device, in particular in an organic electroluminescent device.

[0221] In addition, the present invention also relates to an electronic device which comprises at least one of the above-mentioned compounds or mixtures according to the present invention. The above-mentioned preferred options for the compounds also apply to the electronic device.

[0222] The electronic device is preferably selected from organic electroluminescent devices (OLED, PLED), organic integrated circuits (O-IC), organic field effect transistors (O-FET), organic thin film transistors (O-TFT), organic light emitting transistors (O-LET), organic solar cells (O-SC), organic dye-sensitized solar cells, organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQD), light emitting electrochemical cells (LEC), organic laser diodes (O-lasers) and "organic plasma luminescent devices" (D.M. Koller et al., Nature Photonics 2008, 1-4), preferably organic electroluminescent devices (OLED, PLED), in particular phosphorescent OLEDs.

[0223] The organic electroluminescent device includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also include other layers, such as in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. An intermediate layer having, for example, an exciton blocking function may also be introduced between two light-emitting layers. However, it should be noted that each of these layers does not necessarily exist. The organic electroluminescent device here may include one light-emitting layer or multiple light-emitting layers. If there are multiple light-emitting layers, these light-emitting layers preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in overall white emission, that is, various luminescent compounds capable of fluorescing or phosphorescing are used in the light-emitting layer. A system having three light-emitting layers is particularly preferred, in which the three layers exhibit blue, green, and orange or red emission (for the basic structure, see, for example, WO 2005 / 011013). These may be fluorescent or phosphorescent light-emitting layers, or a hybrid system in which fluorescent and phosphorescent light-emitting layers are combined with each other.

[0224] The compounds according to the invention shown above according to one embodiment can be used in various layers, depending on the exact structure and substitution.

[0225] An organic electroluminescent device preferably containing a compound of formula (1) or according to a preferred embodiment as a fluorescent emitter or a TADF (thermally activated delayed fluorescence) emitter. More particularly, a compound of formula (1) or according to a preferred embodiment is preferably used as a blue fluorescent emitter showing instantaneous fluorescence or as a blue TADF emitter.

[0226] According to another preferred embodiment of the invention, a compound of formula (1) or according to a preferred embodiment is used in a hyperfluorescence system as described, for example, in WO2015 / 135624, the hyperfluorescence system containing a compound of formula (1) as a fluorescent emitter and a photosensitizer compound selected from thermally activated delayed fluorescence compounds (TADF compounds), wherein the energy of the photosensitizer is transferred to the fluorescent emitter via Förster resonance energy transfer.

[0227] According to yet another preferred embodiment of the invention, a compound of formula (1) or according to a preferred embodiment is used in a hyperphosphorescence system as described, for example, in WO2001 / 08230A1, the hyperphosphorescence system containing a compound of formula (1) as a fluorescent emitter and a photosensitizer compound selected from phosphorescent compounds, wherein the energy of the photosensitizer is transferred to the fluorescent emitter via Förster resonance energy transfer.

[0228] Depending on the exact substitution, compounds of formula (1) can also be used in the electron transport layer and / or the electron blocking layer or exciton blocking layer and / or the hole transport layer. The preferred embodiments shown above also apply to the use of said materials in organic electronic devices.

[0229] The compounds of formula (1) are particularly suitable as blue light-emitting compounds. The relevant electronic device can comprise a light-emitting layer containing a compound according to the invention, or it can comprise two or more light-emitting layers. The other light-emitting layers here can contain one or more compounds according to the invention, or other compounds.

[0230] If a compound according to the invention is used as a fluorescent light-emitting body or a TADF light-emitting body in the light-emitting layer, it is preferably used in combination with one or more host materials. The host materials here refer to the materials present in the light-emitting layer, preferably as the main component, and which do not emit light during device operation.

[0231] Preferably, the glass transition temperature T of the host compound G is greater than 70 °C, more preferably greater than 90 °C, and most preferably greater than 110 °C.

[0232] The proportion of the light-emitting compound in the mixture of the light-emitting layer is between 0.1% and 50.0%, preferably between 0.5% and 20.0%, and particularly preferably between 1.0% and 10.0%. Correspondingly, the proportion of one or more host materials is between 50.0% and 99.9%, preferably between 80.0% and 99.5%, and particularly preferably between 90.0% and 99.0%.

[0233] For the purposes of this application, if the compound is applied from the gas phase, the indication of the proportion in % refers to volume %, and if the compound is applied from a solution, the indication of the proportion in % refers to weight %.

[0234] If a compound of formula (1) or a compound according to a preferred embodiment is used as a fluorescent emitter (prompt fluorescence) in the light-emitting layer, then the preferred host materials to be used in combination with the fluorescent emitter are selected from the following classes: oligoarylene compounds (such as 2,2’,7,7’-tetraphenylspirobifluorene according to EP 676461, or dinaphthylanthracene), in particular oligoarylene compounds containing fused aromatic groups; oligoarylene vinylene compounds (such as DPVBi or spiro-DPVBi according to EP 676461); polypod metal complexes (such as those according to WO 2004 / 081017); hole-conducting compounds (such as those according to WO2004 / 058911); electron-conducting compounds, in particular ketones, phosphine oxides, sulfoxides, etc. (such as those according to WO 2005 / 084081 and WO 2005 / 084082); atropisomers (such as those according to WO 2006 / 048268); boric acid derivatives (such as those according to WO2006 / 117052); or benzanthracenes (such as those according to WO 2008 / 145239). Particularly preferred host materials are selected from the following classes: oligoarylene compounds including naphthalene, anthracene, benzanthracene and / or pyrene, or atropisomers of these compounds; oligoarylene vinylene compounds; ketones; phosphine oxides; and sulfoxides. Highly particularly preferred host materials are selected from the following classes: oligoarylene compounds including anthracene, benzanthracene, benzophenanthrene and / or pyrene, or atropisomers of these compounds. Oligoarylene compounds in the sense of the present invention are considered to mean compounds in which at least three aryl or arylene groups are bonded to one another.

[0235] Particularly preferred host materials to be used in combination with the compound of formula (1) used as a fluorescent emitter in the light-emitting layer are described in the following table:

[0236]

[0237]

[0238]

[0239]

[0240] If a compound according to the present invention is used as a fluorescent light-emitting compound in the light-emitting layer, it can be used in combination with one or more other fluorescent light-emitting compounds.

[0241] In addition to the compounds according to the invention, preferred fluorescent emitters are selected from the class of arylamines. An arylamine in the sense of the present invention means a compound containing three substituted or unsubstituted aromatic or heteroaromatic ring systems directly bonded to nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a fused ring system, particularly preferably having at least 14 aromatic ring atoms. Preferred examples thereof are aromatic anthrylamines, aromatic anthryldiamines, aromatic pyrenylamines, aromatic pyrenyldiamines, aromatic chrysenylamines or aromatic chrysenyldiamines. An aromatic anthrylamine means a compound in which one diarylamino group is directly bonded to the anthracene group, preferably at the 9-position. An aromatic anthryldiamine means a compound in which two diarylamino groups are directly bonded to the anthracene group, preferably at the 9,10-positions. The aromatic pyrenylamines, pyrenyldiamines, chrysenylamines and chrysenyldiamines are defined analogously, where the diarylamino group is preferably bonded to the pyrene at the 1-position or 1,6-positions. Also preferred emitters are: indeno[1,2-b]fluoreneamines or indeno[1,2-b]fluorenediamines, for example according to WO 2006 / 108497 or WO2006 / 122630; benzo[ghi]indeno[1,2-b]fluoreneamines or benzo[ghi]indeno[1,2-b]fluorenediamines, for example according to WO 2008 / 006449; and dibenzo[def,pqr]indeno[1,2-b]fluoreneamines or dibenzo[def,pqr]indeno[1,2-b]fluorenediamines, for example according to WO 2007 / 140847; and indeno[1,2-b]fluorene derivatives containing fused aryl groups as disclosed in WO 2010 / 012328. Also preferred emitters are benzoanthracene derivatives as disclosed in WO 2015 / 158409, anthracene derivatives as disclosed in WO 2017 / 036573, fluorene dimers as in WO 2016 / 150544, or phenoxazine derivatives as disclosed in WO2017 / 028940 and WO 2017 / 028941. Also preferred are pyrenylarylamines as disclosed in WO 2012 / 048780 and WO 2013 / 185871. Also preferred are benzo[ghi]indeno[1,2-b]fluoreneamines as disclosed in WO 2014 / 037077, benzo[def]fluoreneamines as disclosed in WO 2014 / 106522, and indeno[1,2-b]fluorenes as disclosed in WO 2014 / 111269 or WO 2017 / 036574.

[0242] In addition to the compounds according to the invention, examples of preferred fluorescent emitting compounds which can be used in combination with the compounds of the invention in the light-emitting layer or which can be used in another light-emitting layer of the same device are described in the following table:

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] If a compound of formula (1) or according to a preferred embodiment is used as the TADF emitter in the light-emitting layer, the preferred host materials used in combination with the TADF emitter are selected from the following classes: ketones, phosphine oxides, sulfoxides, and sulfones, such as those according to WO2004 / 013080, WO 2004 / 093207, WO 2006 / 005627, or WO 2010 / 006680; triarylamines; carbazole derivatives, such as CBP (N,N-dicarbazolylbiphenyl), m-CBP, or carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP2004 / 288381, EP 1205527, WO 2008 / 086851, or US 2009 / 0134784; dibenzofuran derivatives; indolocarbazole derivatives, such as those according to WO 2007 / 063754 or WO 2008 / 056746; indacarbazole derivatives, such as those according to WO 2010 / 136109 or WO 2011 / 000455; azacarbazoles, such as those according to EP1617710, EP 1617711, EP 1731584, JP 2005 / 347160; bipolar host materials, such as those according to WO2007 / 137725; silanes, such as those according to WO 2005 / 111172; borazoles or borates, such as those according to WO2006 / 117052; siladiazole derivatives, such as those according to WO 2010 / 054729; phosphadiazole derivatives, such as those according to WO 2010 / 054730; triazine derivatives, such as those according to WO 2010 / 015306, WO 2007 / 063754, or WO 2008 / 056746; pyrimidine derivatives; quinoxaline derivatives; Zn complexes, Al complexes, or Be complexes, such as those according to EP 652273 or WO 2009 / 062578; or bridged carbazole derivatives, such as those according to US 2009 / 0136779, WO 2010 / 050778, WO 2011 / 042107, or WO 2011 / 088877. Suitable host materials also include those disclosed in WO2015 / 135624. These are incorporated herein by reference. Mixtures of two or more of these host materials can also be used.

[0251] The host compound for the TADF emitter is preferably a charge-transporting compound, i.e., an electron-transporting compound or a hole-transporting compound, or a bipolar compound. In the context of the present application, the host compound used may also be a compound that is neither hole-transporting nor electron-transporting. The electron-transporting compound in the context of the present invention is a compound with LUMO ≤ -2.50 eV. Preferably, LUMO ≤ -2.60 eV, more preferably ≤ -2.65 eV, and most preferably ≤ -2.70 eV. LUMO is the lowest unoccupied molecular orbital. The value of LUMO of the compound is determined by quantum chemical calculations, as generally described in the Examples section hereinafter. The hole-transporting compound in the context of the present invention is a compound with HOMO ≥ -5.5 eV. HOMO is preferably ≥ -5.4 eV, more preferably ≥ -5.3 eV. HOMO is the highest occupied molecular orbital. The value of HOMO of the compound is determined by quantum chemical calculations, as generally described in the Examples section hereinafter. The bipolar compound in the context of the present invention is a compound that combines both hole-transporting and electron-transporting properties.

[0252] Suitable electron-conductive host compounds for the TADF emitter are selected from the following classes of substances: triazines; pyrimidines; lactams; metal complexes, especially Be, Zn, and Al complexes; aromatic ketones; aromatic phosphine oxides; phospholes; boroles substituted with at least one electron-conductive substituent; and quinoxalines. In a preferred embodiment of the present invention, the electron-conductive compound is a pure organic compound, i.e., a compound without metals.

[0253] Furthermore, in addition to the photosensitizer and the fluorescent emitter, the above-mentioned hyperfluorescence and hyperphosphorescence systems preferably contain at least one host material. In this case, it is preferred that the lowest triplet energy of the host compound is not more than 0.1 eV lower than the triplet energy of the photosensitizer compound.

[0254] Particularly preferably, T 1 (host) ≥ T 1 (photosensitizer).

[0255] More preferably: T 1 (host) - T 1 (photosensitizer) ≥ 0.1 eV;

[0256] Most preferably: T 1 (host) - T 1 (photosensitizer) ≥ 0.2 eV.

[0257] Here, T 1 (host) is the lowest triplet energy of the host compound, and T 1(Photosensitizer) is the lowest triplet energy of the photosensitizer compound. The triplet energy T of the matrix compound 1 (Matrix) is determined hereby by the edge of the photoluminescence spectrum measured on a pure film at 4 K. T 1 (Photosensitizer) is determined by the edge of the photoluminescence spectrum measured in a toluene solution at room temperature.

[0258] Suitable matrix materials for the hyperfluorescence or hyperphosphorescence system are the same as the matrix materials mentioned above, and more preferably are also the matrix materials preferably used for TADF materials.

[0259] Suitable phosphorescent emitters are particularly the following compounds: those that emit light when appropriately excited, preferably emit light in the visible light region, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, and particularly preferably greater than 56 and less than 80. The phosphorescent emitters used are preferably compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium, platinum or copper.

[0260] For the purposes of the present invention, all luminescent iridium, platinum or copper complexes are considered to be phosphorescent compounds.

[0261] Examples of the above phosphorescent emitters are disclosed in applications WO 2000 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191613, EP 1191612, EP 1191614, WO 2005 / 033244, WO 2005 / 019373 and US 2005 / 0258742. Generally, all phosphorescent complexes used for phosphorescent OLEDs according to the prior art and known to those skilled in the art in the field of organic electroluminescent devices are applicable to the devices according to the present invention. Those skilled in the art can also combine other phosphorescent complexes with the compounds according to the present invention in the OLED without creative efforts.

[0262] Preferred host materials for phosphorescent emitters are: aromatic ketones, aromatic phosphine oxides, aromatic sulfoxides or aromatic sulfones, such as those according to WO 2004 / 013080, WO 2004 / 093207, WO 2006 / 005627 or WO 2010 / 006680; triarylamines; carbazole derivatives, such as CBP (N,N-dicarbazolylbiphenyl) or carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP2004 / 288381, EP 1205527 or WO 2008 / 086851; indolocarbazole derivatives, such as those according to WO 2007 / 063754 or WO 2008 / 056746; indacarbazole derivatives, such as those according to WO 2010 / 136109, WO 2011 / 000455 or WO 2013 / 041176; azacarbazole derivatives, such as those according to EP 1617710, EP1617711, EP 1731584, JP 2005 / 347160; bipolar host materials, such as those according to WO 2007 / 137725; silanes, such as those according to WO 2005 / 111172; borazoles or borates, such as those according to WO 2006 / 117052; triazine derivatives, such as those according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746; zinc complexes, such as those according to EP 652273 or WO 2009 / 062578; siladiazoles or silatetrazoles derivatives, such as those according to WO 2010 / 054729; phosphadiazoles derivatives, such as those according to WO 2010 / 054730; bridged carbazole derivatives, such as those according to US 2009 / 0136779, WO 2010 / 050778, WO 2011 / 042107, WO 2011 / 088877 or WO2012 / 14308; terphenylidene derivatives, such as those according to WO 2012 / 048781; or lactams, such as those according to WO2011 / 116865 or WO 2011 / 137951.

[0263] More particularly, when a phosphorescent compound is employed in the above-described hyperphosphorescent system, the phosphorescent compound is preferably selected from phosphorescent organometallic complexes as described, for example, in WO 2015 / 091716. Also particularly preferred are phosphorescent organometallic complexes described in the following documents: WO 2000 / 70655, WO 2001 / 41512, WO 2002 / 02714, WO 2002 / 15645, EP 1191612, WO 2005 / 033244, WO 2005 / 019373, US 2005 / 0258742, WO 2006 / 056418, WO 2007 / 115970, WO 2007 / 115981, WO 2008 / 000727, WO 2009 / 050281, WO 2009 / 050290, WO 2011 / 051404, WO 2011 / 073149, WO 2012 / 121936, US 2012 / 0305894, WO 2012 / 170571, WO 2012 / 170461, WO 2012 / 170463, WO 2006 / 121811, WO 2007 / 095118, WO 2008 / 156879, WO 2008 / 156879, WO 2010 / 068876, WO 2011 / 106344, WO 2012 / 172482, EP3126371, WO 2015 / 014835, WO 2015 / 014944, WO 2016 / 020516, US 20160072081, WO 2010 / 086089, WO 2011 / 044988, WO 2014 / 008982, WO 2014 / 023377, WO 2014 / 094961, WO 2010 / 069442, WO 2012 / 163471, WO 2013 / 020631, US 20150243912, WO 2008 / 000726, WO 2010 / 015307, WO 2010 / 054731, WO 2010 / 054728, WO 2010 / 099852, WO 2011 / 032626, WO 2011 / 157339, WO 2012 / 007086, WO 2015 / 036074, WO 2015 / 104045, WO 2015 / 117718, WO 2016 / 015815, which are preferably iridium and platinum complexes.

[0264] Also particularly preferred are, for example, phosphorescent organometallic complexes with multidentate ligands as described in the following documents: WO 2004 / 081017, WO 2005 / 042550, US 2005 / 0170206, WO 2009 / 146770, WO 2010 / 102709, WO 2011 / 066898, WO 2016124304, WO 2017 / 032439, WO 2018 / 019688, EP 3184534 and WO2018 / 011186.

[0265] Also particularly preferred are, for example, phosphorescent binuclear organometallic complexes as described in the following documents: WO 2011 / 045337, US 20150171350, WO 2016 / 079169, WO 2018 / 019687, WO 2018 / 041769, WO 2018 / 054798, WO 2018 / 069196, WO 2018 / 069197, WO 2018 / 069273.

[0266] Also particularly preferred are, for example, copper complexes as described in the following documents: WO 2010 / 031485, US2013150581, WO 2013 / 017675, WO 2013 / 007707, WO 2013 / 001086, WO 2012 / 156378, WO2013 / 072508, EP 2543672.

[0267] Specific examples of the phosphorescent photosensitizer are Ir(ppy) 3 and its derivatives, and the structures listed below:

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276] Other specific examples of the phosphorescent photosensitizers are iridium and platinum complexes containing carbene ligands and the structures listed below, where homoleptic and heteroleptic complexes as well as meridional and facial isomers may be suitable:

[0277]

[0278]

[0279] Other specific examples of the phosphorescent photosensitizers are also copper complexes and the structures listed below:

[0280]

[0281] In addition to the compounds according to the present invention, suitable TADF compounds are those in which the energy gap between the lowest triplet state T 1 and the first excited singlet state S 1 is small enough such that the S 1 state can be thermally accessed from the T 1 state. Preferably, the energy gap between the lowest triplet state T 1 and the first excited singlet state S 1 of the TADF compound is ≤ 0.30 eV. More preferably, the energy gap between S 1 and T 1 is ≤ 0.20 eV, even more preferably ≤ 0.15 eV, particularly more preferably ≤ 0.10 eV, and even more particularly preferably ≤ 0.08 eV.

[0282] The energies of the lowest excited singlet state (S 1 ) and the lowest triplet state (T 1 ), as well as the HOMO and LUMO values, are determined by quantum chemical calculations. The Gaussian09 program package (revision D or later version) is used. The neutral ground state geometries of all pure organic molecules are optimized at the AM1 theoretical level. Subsequently, single-point calculations at the B3PW91 / 6-31G(d) level, including calculations of the lowest singlet and triplet excited states, are performed using TD-B3PW91 / 6-31G(d). The HOMO and LUMO values and the S 1 and T 1 excitation energies are taken from the single-point calculations at the B3PW91 / 6-31G(d) theoretical level.

[0283] Similarly, for organometallic compounds, the neutral ground state geometries are optimized at the HF / LANL2MB theoretical level. Subsequently, B3PW91 / 6-31G(d)+LANL2DZ (for all metal atoms: LANL2DZ, for all light elements: 6-31G(d)) is used to calculate the HOMO and LUMO values and the TD-DFT excitation energies.

[0284] The calculated HOMO (HEh) and LUMO (LEh) values are given in Hartree. The HOMO and LUMO energy levels calibrated by the reference cyclic voltammetry measurement are determined as follows in electron volts:

[0285] HOMO (eV) = ((HEh × 27.212) - 0.9899) / 1.1206,

[0286] LUMO (eV) = ((LEh × 27.212) - 2.0041) / 1.385.

[0287] These values are regarded as the HOMO and LUMO energy levels of the material in the sense of the present invention.

[0288] The lowest triplet state T 1 is defined as the energy of the lowest TD-DFT triplet excitation energy.

[0289] The lowest excited singlet state S 1 is defined as the energy of the lowest TD-DFT singlet excitation energy.

[0290] Preferably, the TADF compound is an organic compound. The organic compound in the context of the present invention is a carbonaceous compound without any metal. More particularly, the organic compound is formed by the elements C, H, D, B, Si, N, P, O, S, F, Cl, Br, and I.

[0291] The TADF compound is more preferably an aromatic compound having both donor and acceptor substituents, with only a slight spatial overlap between the LUMO and HOMO of the compound. The principles of interpretation of donor and acceptor substituents are known to those skilled in the art in principle. Suitable donor substituents are in particular diarylamino or diheteroarylamino groups and carbazole groups or carbazole derivatives, preferably each bonded to the aromatic compound via N. These groups may also have other substituents. Suitable acceptor substituents are in particular cyano groups and also, for example, electron-deficient heteroaryl groups, which may also have other substituents, such as substituted or unsubstituted triazine groups.

[0292] The preferred dopant concentration of the TADF compound in the light-emitting layer is described below. Due to the manufacturing differences of organic light-emitting devices, the dopant concentration in the case of manufacturing the light-emitting layer by vapor deposition is reported in volume %, and the dopant concentration in the case of manufacturing the light-emitting layer from a solution is reported in weight %. The dopant concentrations in volume % and weight % are generally very similar.

[0293] In a preferred embodiment of the present invention, in the case of manufacturing a light-emitting layer by vapor deposition, the TADF compound is present in the light-emitting layer at a dopant concentration of 1% to 70% by volume, more preferably 5% to 50% by volume, and even more preferably 5% to 30% by volume.

[0294] In a preferred embodiment of the present invention, in the case of manufacturing a light-emitting layer from a solution, the TADF compound is present in the light-emitting layer at a dopant concentration of 1% to 70% by weight, more preferably 5% to 50% by weight, and even more preferably 5% to 30% by weight.

[0295] General technical knowledge possessed by those skilled in the art includes knowledge of which materials are generally suitable as TADF compounds. The following documents disclose, by way of example, materials potentially suitable as TADF compounds:

[0296] - Tanaka et al., Chemistry of Materials 25(18), 3766 (2013).

[0297] - Lee et al., Journal of Materials Chemistry C 1(30), 4599 (2013).

[0298] - Zhang et al., Nature Photonics advance online publication, 1 (2014), doi: 10.1038 / nphoton.2014.12.

[0299] - Serevicius et al., Physical Chemistry Chemical Physics 15(38), 15850(2013).

[0300] - Li et al., Advanced Materials 25(24), 3319 (2013).

[0301] - Youn Lee et al., Applied Physics Letters 101(9), 093306 (2012).

[0302] - Nishimoto et al., Materials Horizons 1, 264 (2014), doi: 10.1039 / C3MH00079F.

[0303] - Valchanov et al., Organic Electronics, 14(11), 2727 (2013).

[0304] - Nasu et al., ChemComm, 49, 10385 (2013).

[0305] In addition, the following patent applications disclose potential TADF compounds: US 2019058130, WO 18155642, WO18117179 A1, US 2017047522, US 2016372682 A, US 2015041784, US 2014336379, US2014138669, WO 2013 / 154064, WO 2013 / 133359, WO 2013 / 161437, WO 2013 / 081088, WO2013 / 081088, WO 2013 / 011954, JP 2013 / 116975 and US 2012 / 0241732.

[0306] In addition, those skilled in the art can infer the design principles of TADF compounds from these publications. For example, Valchanov et al. demonstrated how the color of TADF compounds can be adjusted.

[0307] Examples of suitable molecules exhibiting TADF are the structures shown in the following table:

[0308]

[0309]

[0310] As mentioned above, the compound of formula (1) or according to a preferred embodiment can be used as a fluorescent emitter in combination with a photosensitizer in a hyperfluorescent or hyperphosphorescent system. In this case, the compound of formula (1) is preferably sterically shielded. For example, the compound of formula (1) corresponding to formulas (5) and (6), more particularly (5-1) to (5-3), is very suitable as a sterically shielded fluorescent emitter in combination with a photosensitizer selected from TADF compounds and phosphorescent compounds in a light-emitting layer. Preferably, the light-emitting layer further comprises at least one organic functional material selected from matrix materials.

[0311] The compound of formula (1) or according to a preferred embodiment may also be used in combination with other compounds selected from the following: HTM (hole transport material), HIM (hole injection material), HBM (hole blocking material), p-type dopant, ETM (electron transport material), EIM (electron injection material), EBM (electron blocking material), n-type dopant, fluorescent emitter, phosphorescent emitter, delayed fluorescence emitter, matrix material, host material, wide bandgap material, and quantum materials such as quantum dots and quantum rods.

[0312] The compound of formula (1) or according to a preferred embodiment may also be used in other layers, for example as a hole transport material in a hole injection layer or a hole transport layer or an electron blocking layer, or as a matrix material in a light-emitting layer.

[0313] The generally preferred classes of materials used as corresponding functional materials in the organic electroluminescent device according to the present invention are shown below.

[0314] Suitable charge transport materials for use in the hole injection layer or the hole transport layer or the electron blocking layer or the electron transport layer of the electronic device according to the present invention are, for example, the compounds disclosed by Y. Shirota et al., Chem. Rev. 2007, 107(4), 953 - 1010, or other materials used in these layers according to the prior art.

[0315] The materials that can be used for the electron transport layer are all the materials used as electron transport materials in the electron transport layer according to the prior art. Particularly suitable are aluminum complexes, such as Alq 3 ; zirconium complexes, such as Zrq 4 ; lithium complexes, such as LiQ; benzimidazole derivatives; triazine derivatives; pyrimidine derivatives; pyridine derivatives; pyrazine derivatives; quinoxaline derivatives; quinoline derivatives; oxadiazole derivatives; aromatic ketones; lactams; boranes; phosphadiazole derivatives and phosphine oxide derivatives. In addition, suitable materials are derivatives of the above-mentioned compounds, as disclosed in JP 2000 / 053957, WO 2003 / 060956, WO 2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300.

[0316] Preferred hole transport materials for use in the hole transport layer, hole injection layer or electron blocking layer in an electroluminescent device according to the present invention are indeno[1,2-b]fluoreneamine derivatives (such as those according to WO 06 / 122630 or WO 06 / 100896), amine derivatives disclosed in EP1661888, hexaazatriphenylene derivatives (such as those according to WO 01 / 049806), amine derivatives containing fused aromatic rings (such as those according to US 5,061,569), amine derivatives disclosed in WO 95 / 09147, monobenzylindeno[1,2-b]fluoreneamine (such as those according to WO 08 / 006449), dibenzylindeno[1,2-b]fluoreneamine (such as those according to WO 07 / 140847), spirobifluoreneamine (such as those according to WO 2012 / 034627 or WO 2013 / 120577), fluoreneamine (such as those according to applications EP 2875092, EP2875699 and EP 2875004), spirodibenzopyranamine (such as those according to WO 2013 / 083216) and dihydroacridine derivatives (such as those according to WO 2012 / 150001). Compounds according to the present invention can also be used as hole transport materials.

[0317] The cathode of the organic electroluminescent device preferably comprises a metal with a low work function, a metal alloy containing various metals or a multilayer structure, such as alkaline earth metals, alkali metals, main group metals or lanthanide elements (such as Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys containing an alkali metal or an alkaline earth metal and silver, such as an alloy containing magnesium and silver. In the case of a multilayer structure, in addition to the said metals, other metals with a relatively high work function such as Ag or Al can also be used, and in this case a combination of the said metals is usually used, such as Ca / Ag, Mg / Ag or Ba / Ag. It is also preferably possible to introduce a thin intermediate layer of a material with a high dielectric constant between the metal cathode and the organic semiconductor. Suitable for this purpose are alkali metal fluorides or alkaline earth metal fluorides, as well as the corresponding oxides or carbonates (such as LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, Cs 2 CO 3 etc.). In addition, for this purpose, lithium quinolate (LiQ) can be used. The layer thickness of this layer is preferably between 0.5 nm and 5 nm.

[0318] The anode preferably comprises a material with a high work function. Preferably, the work function of the anode is preferably more than 4.5 eV greater than that of vacuum. On the one hand, suitable for this purpose are metals with a high redox potential, such as Ag, Pt or Au. On the other hand, metal / metal oxide electrodes (such as Al / Ni / NiO x 、Al / PtO x)。For some applications, at least one of the electrodes must be transparent or partially transparent in order to facilitate the irradiation of the organic material (organic solar cell) or the coupled output of light (OLED, O-laser). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Also preferred are conductively doped organic materials, in particular conductively doped polymers.

[0319] Since the lifetime during the period according to the invention is shortened in the presence of water and / or air, the device is appropriately structured (depending on the application), equipped with contacts and finally sealed.

[0320] In a preferred embodiment, the organic light-emitting device according to the invention is characterized in that one or more layers are coated by means of sublimation, wherein the material is applied by vapor deposition in a vacuum sublimation unit at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, the initial pressure here can also be even lower, for example less than 10 -7 mbar.

[0321] Also preferred is an organic light-emitting device, which is characterized in that one or more layers are coated by means of OVPD (organic vapor deposition) or by means of carrier gas sublimation, wherein the material is applied at a pressure between 10 -5 mbar and 1 bar. A special case of this method is the OVJP (organic vapor jet printing) method, in which the material is applied directly through a nozzle and is thus structured (for example M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0322] Also preferred is an organic light-emitting device, which is characterized in that one or more layers are produced from a solution, for example by spin coating, or by any desired printing method, such as screen printing, flexographic printing, nozzle printing or offset printing, but particularly preferably LITI (light-induced thermal imaging, thermal transfer) or inkjet printing to produce one or more layers. Soluble compounds of formula (I) are required for this purpose. High solubility can be achieved by suitable substitution of the compounds.

[0323] Also feasible is a hybrid method, in which, for example, one or more layers are applied from a solution and one or more other layers are applied by vapor deposition. Thus, for example, the light-emitting layer can be applied from a solution and the electron transport layer can be applied by vapor deposition.

[0324] These methods are generally known to those skilled in the art and can be applied by those skilled in the art to an organic light-emitting device comprising a compound according to the invention without creative effort.

[0325] According to the present invention, an electronic device comprising one or more compounds according to the present invention can be used in a display, as a light source in lighting applications, and as a light source in medical and / or cosmetic applications (such as phototherapy).

[0326] The present invention will now be explained in more detail by the following examples, but the present invention is not limited thereby.

[0327] A) Synthesis Examples

[0328] Example 1: Compound Int-1.1

[0329]

[0330] The synthesis of Int-1.1 is described in CN 110330481 A

[0044] .

[0331] The following compounds can be synthesized in a similar manner:

[0332]

[0333] Synthesis of Int-2.1

[0334]

[0335] The synthesis of Int-2.1 is described in CN 110330481 A

[0047] .

[0336] The following compounds can be synthesized in a similar manner:

[0337]

[0338] Synthesis of Int-3.1

[0339]

[0340] Int-3.1 is synthesized in the same manner as described in WO 2014146752 A1 for CAS 1628715-79-6.

[0341] The following compounds can be synthesized in a similar manner:

[0342]

[0343] Synthesis of Int-4.1

[0344]

[0345] Dissolve 2.0 g (4.21 mmol) of Int-3.1, 4.3 g (17 mmol) of 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane, 3.84 g (25.25 mmol) of cesium fluoride, and 623 mg (0.84 mmol) of PdCl 2 [P(Cy) 3 2 in 90 ml of toluene and heat at reflux temperature for 48 hours. After complete conversion of the reaction, cool the mixture to room temperature, filter through a fluted filter, and concentrate in vacuo. Crystallize the residue from heptane to obtain the product as a solid.

[0346] The following compounds can be synthesized in a similar manner:

[0347]

[0348]

[0349] Synthesis of Int-5.1

[0350]

[0351] Dilute 540 ml (540 mmol) of bromo(2,4,6-trimethylphenyl)magnesium (1 M solution in THF) in 600 ml of THF and reflux. Add a 200 ml THF solution of 50 g (180 mmol) of 1,3-dichloro-2-iodobenzene dropwise to the reaction mixture over one hour and reflux for four hours. Cool the reaction mixture to 0 °C and add 9.4 ml (184 mmol) of bromide dropwise while maintaining the temperature below 10 °C. Stir the reaction mixture at room temperature for 16 hours. Quench the reaction mixture carefully with 50 ml of aqueous sodium bisulfite solution. Separate the aqueous phase and extract with ethyl acetate. Wash the combined organic phases with water (1 × 300 ml) and with brine (1 × 300 ml), and concentrate in vacuo. Crystallize the residue from ethyl acetate to obtain the product as a solid.

[0352] Synthesis of Int-6.1

[0353]

[0354] Suspend 1.0 g of Int-4.1 (1.76 mmol) in 100 mL of toluene under an argon atmosphere. Add 1 mL of NEt 3 (7.12 mmol) and stir for 5 minutes, then add 2.34 g (17.5 mmol) of AlCl​3 。The resulting reaction mixture was stirred overnight at 110 °C. After cooling to room temperature, 50 mL of water and a 1:1 mixture of 100 mL of toluene and tetrahydrofuran were added, and the organic layer was washed four times with 50 mL of water. After drying the organic layer with MgSO 4 After drying the organic layer, the solvent was removed under reduced pressure, and the crude product could be used without further purification.

[0355] The crude product was dissolved in 300 mL of isopropanol and benzene (4:1) under an argon atmosphere. Using a Soxhlet extractor with 4 Å molecular sieves, the resulting reaction mixture was heated at reflux temperature for 4 days. After removing 50% of the solvent, the pale yellow solid precipitate was separated by filtration and then dried in vacuo.

[0356] The following compounds can be synthesized in a similar manner:

[0357]

[0358] Synthesis of Compound 1

[0359]

[0360] Under an argon atmosphere, 3.6 mg (9.2 mmol) of Int-5.1 was dissolved in 300 mL of diethyl ether. 4.0 mL (10 mmol, a 2.5 M hexane solution) of n-BuLi was added, and the reaction mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure at -40 °C, and then 1.9 g (4.2 mmol) of Int-6.1 was added. The solid was suspended in 5 mL of hexane, and the resulting mixture was heated at 80 °C for 2 hours. After filtering the reaction mixture, the solid residue was extracted four times with 100 mL of benzene, and the combined benzene layers were dried in vacuo. The product was further purified by crystallization from toluene to give a yellow solid.

[0361] The following compounds can be synthesized in a similar manner:

[0362]

[0363]

[0364] Photophysical Measurements

[0365] 1) Determination of the peak emission wavelength λ max of

[0366] To determine the peak emission wavelength of the fluorescent emitter, the fluorescent emitter was dissolved in toluene. A concentration of 1 mg / 100 mL was used. In a Hitachi F-4500 fluorescence spectrometer, the solution was excited with a wavelength matched to the material. The measurement was carried out at room temperature. The peak emission wavelength λ max is the wavelength of the first maximum of the emission spectrum. Usually, the first maximum is also the global maximum of the spectrum.

[0367] 2) Determination of the spectral width (full width at half maximum (FWHM))

[0368] To determine the spectral width of the fluorescent emitter, the wavelength values (X1, X2) at half of the maximum value of the peak emission wavelength (y = 0.5) were subtracted. The full width at half maximum was calculated according to formula (1):

[0369] FWHM = X2 - X1 (1)

[0370] The following properties of the fluorescent emitter were obtained according to the described method and are described in Table E-1.

[0371] Comparative example

[0372]

[0373] The synthesis of Comparative Example 1 is described in WO 2020208051. Comparative Example 2 can be obtained in a similar manner as described for Comparative Example 2 in WO 2020208051.

[0374] Table E-1: Properties of the fluorescent emitter

[0375]

[0376] Compared with Comparative Example 1, Compound 6 shows a color shift of 26 nm towards a lighter blue, which results in more suitable color coordinates for OLED devices. In addition, the results show that, without changing the substituents on boron, the terphenylidene units of Compounds 6 and 7 of the present invention show a narrower spectrum compared to Comparative Examples 1 and 2, and thus higher color purity. The compounds of the present invention combine good color coordinates and a small FWHM.

[0377] 3) Fabrication of OLED

[0378] The glass plate coated with structured ITO (50 nm, indium tin oxide) was wet cleaned (dishwasher, Merck Extran cleaner). Then the substrate was heated at 250 °C for 15 minutes under nitrogen.

[0379] All materials are thermally evaporated in a vacuum chamber. In this case, the light-emitting layer always consists of two materials. For example, the expression H-01(99%):C-6(1%) means that material H-01 is present in the light-emitting layer at a volume fraction of 99% and material compound 6 (C-6) is present at a volume fraction of 1%.

[0380] The OLED consists of the following layer sequence, which is applied to the heat-treated substrate: 20 nm HTM(95%):p-D(5%), 160 nm HTM, 20 nm light-emitting layer, 10 nm ETM, 20 nm ETM(50%):LiQ(50%), 1 nm LiQ, 100 nm aluminum. The composition of the light-emitting layer is given in Table E-2. The materials used for OLED fabrication are listed in Table E-3.

[0381] The OLED is characterized by standard methods. For this purpose, the electroluminescence spectrum is recorded and the current-voltage-luminance density characteristics (IUL) are measured. (The luminance density is measured perpendicular to the substrate.) The external quantum efficiency (EQE) is calculated as a function of the luminance density assuming Lambertian emission. The expression U100 refers to the voltage required for a luminance density of 100 cd / m². EQE100 refers to the external quantum efficiency at a working luminance density of 100 cd / m².

[0382] In addition, the CIE 1931 x and y color coordinates (CIE x and CIE y) are calculated from the electroluminescence spectrum. The OLED performance data are given in Table E-2.

[0383] Table E-2 shows that very good EQE and low voltage are obtained using the compound 3 (C-3) of the present invention as the emitter in the light-emitting layer. The OLED shows dark blue.

[0384] Table E-2: Composition of the light-emitting layer and OLED performance results for single-device experiments.

[0385]

[0386] Table E-3: Structures of the materials used for OLED fabrication

[0387]

Claims

1. A compound of formula (1), wherein the symbols and designations used are subject to the following provisions: X 2 which represents, the same or different in each case, CR 2 or N; X A which, in each case, independently represents CR A or N; Y is a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R Y in each case; R B which, in each case the same or different, represents CN, N(Ar) 2 , C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, N(R) 2 , Si(R) 3 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of said groups being optionally substituted by one or more groups R, wherein in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O, S or CONR and wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which is optionally substituted by one or more groups R, or an aryloxy group having 5 to 60 aromatic ring atoms which is optionally substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which is optionally substituted by one or more R groups; R 2 、R A 、R Y which, in each case independently, represents H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, NO 2 , Si(R) 3 , B(OR) 2 , OSO 2 R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which groups may be substituted by one or more groups R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R, an aryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups; where two adjacent groups selected from R Y , R 2 , R A may form a monocyclic or polycyclic aliphatic or aromatic ring system which may be substituted by one or more groups R; R represents, in each case identically or differently, H, D, F, Cl, Br, I, CHO, CN, N(Ar) 2 , C(=O)Ar, P(=O)(Ar) 2 , S(=O)Ar, S(=O) 2 Ar, NO 2 , Si(R’) 3 , B(OR’) 2 , OSO 2 R’, a straight-chain alkyl, alkoxy or thioalkyl group having from 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having from 3 to 40 C atoms, each of said groups being optionally substituted by one or more groups R’, where in each case one or more non-adjacent CH 2 groups may be replaced by R’C=CR’, C≡C, Si(R’) 2 , Ge(R’) 2 , Sn(R’) 2 , C=O, C=S, C=Se, P(=O)(R’), SO, SO 2 , O, S or CONR’ and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , an aromatic or heteroaromatic ring system having from 5 to 60 aromatic ring atoms, optionally substituted by one or more groups R’, or an aryloxy group having from 5 to 60 aromatic ring atoms, optionally substituted by one or more groups R’, where two adjacent groups R may form a monocyclic or polycyclic aliphatic or aromatic ring system, optionally substituted by one or more groups R’; Ar is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms which may in each case also be substituted by one or more groups R'; R’ is the same or different in each case and represents H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having from 1 to 20 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl group having from 3 to 20 C atoms, where in each case one or more non-adjacent CH 2 groups may be replaced by SO, SO 2 , O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having from 5 to 24 C atoms.

2. The compound according to claim 1, characterized in that the compound is selected from the compounds of formula (2), wherein the symbols have the same meaning as in claim 1.

3. The compound according to claim 1 or 2, characterized in that the compound is selected from the compounds of formula (3), wherein the symbols have the same meaning as in claim 1.

4. The compound according to one or more of the preceding claims, characterized in that group Y corresponds to a group of formula (Y1) or (Y2): 。 5. The compound according to one or more of the preceding claims, characterized in that R B which, in each case identically or differently, represents a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or an alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of said groups being optionally substituted by one or more groups R, where in each case one or more non-adjacent CH 2 groups may be replaced by RC=CR, C≡C, Si(R) 2 , Ge(R) 2 , Sn(R) 2 , C=O, C=S, C=Se, P(=O)(R), SO, SO 2 , O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which is optionally substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which is optionally substituted by one or more R groups.

6. The compound according to one or more of the preceding claims, characterized in that R B which, in each case identically or differently, represents a straight-chain alkyl or alkoxy group having 1 to 20 carbon atoms or an alkenyl or alkynyl group having 2 to 20 carbon atoms or a branched or cyclic alkyl or alkoxy group having 3 to 20 carbon atoms, where each of said groups may be substituted by one or more groups R, where one or more H atoms may be replaced by D, F, Cl or CN, or an aromatic ring system having 5 to 60 aromatic ring atoms which may in each case be substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups.

7. The compound according to one or more of the preceding claims, characterized in that R B the same or different in each case selected from branched or cyclic alkyl groups represented by the following general formula (RS-a), (RS-a) wherein R 22 、R 23 、R 24 are the same or different in each case and are selected from H, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the groups mentioned above may each be substituted by one or more groups R 25 , and where the groups R 22 , R 23 , R 24 two or all of the groups R 22 , R 23 , R 24 may be linked to form a (poly)cyclic alkyl group which may be substituted by one or more groups R 25 ; R 25 independently selected in each case from straight-chain alkyl groups having 1 to 10 carbon atoms or branched or cyclic alkyl groups having 3 to 10 carbon atoms; provided that in each case the group R 22 , R 23 and R 24 is such that at least one of them is not H, provided that in each case the total of the groups R 22 , R 23 and R 24 together have at least 4 carbon atoms, and provided that in each case, if two of the groups R 22 , R 23 , R 24 are H, then the remaining group is not straight-chain; or selected from branched or cyclic alkoxy groups represented by the following general formula (RS-b), (RS-b) wherein R 26 、R 27 、R 28 which, in each case independently of one another, are selected from H, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the abovementioned groups may each be substituted by one or more groups R as defined above 25 and where the groups R 26 、R 27 、R 28 two or all of the groups R 26 、R 27 、R 28 may be linked to form (poly)cyclic alkyl groups which may be substituted by one or more groups R as defined above 25 ; Provided that in each case only one of the groups R 26 , R 27 and R 28 may be H; or selected from aralkyl groups represented by the following general formula (RS-c), (RS-c) wherein R 29 、R 30 、R 31 which are the same or different in each case and are selected from H, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 or, in each case, an aromatic ring system having 6 to 30 aromatic ring atoms which may be substituted by one or more groups R 32 and where two or all of the groups R 29 、R 30 、R 31 may be linked to form a (poly)cyclic alkyl group or an aromatic ring system, each of which may be substituted by one or more groups R 32 ; R 32 which, in each case independently of one another, is selected from straight-chain alkyl groups having 1 to 10 carbon atoms, branched or cyclic alkyl groups having 3 to 10 carbon atoms, or aromatic ring systems having 6 to 24 aromatic ring atoms; Provided that in each case the group R 29 , R 30 and R 31 at least one of which is not H and in each case the group R 29 , R 30 and R 31 at least one of which is an aromatic ring system having at least 6 aromatic ring atoms or contains an aromatic ring system having at least 6 aromatic ring atoms; or selected from aromatic ring systems represented by the following general formula (RS-d), (RS-d) wherein R 40 to R 44 which are the same or different in each case and are selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 or, in each case, an aromatic ring system having 6 to 30 aromatic ring atoms which may be substituted by one or more groups R 32 and where two or more of the groups R 40 to R 44 may be linked to form a (poly)cyclic alkyl group or an aromatic ring system which may each be substituted by one or more groups R 32 as defined above.

8. The compound according to one or more of the preceding claims, characterized in that R 2 , R Y and R A represents, in each case identically or differently, H, D, F, Cl, Br, I, CN, N(Ar) 2 , a linear alkyl, alkoxy or thioalkyl radical having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, in which in each case one or more non-adjacent CH 2 The group can be RC=CR, C≡C, Si(R) 2 、Ge(R) 2 Sn(R) 2 ,C=O,C=S,C=Se,P(=O)(R),SO,SO 2 , O, S or CONR and one or more of the H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 instead, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, or an aralkyl or heteroaralkyl radical having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more R radicals, wherein R Y , R 2 , R A Two adjacent groups in the R group may form a monocyclic or polycyclic aliphatic or aromatic ring system which may be substituted by one or more groups R.

9. The compound according to one or more of the preceding claims, characterized in that R 2 , R Y and R A represents, identically or differently in each case, H, D, F, CN, a straight-chain alkyl, alkoxy or thioalkyl radical having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkyl radical having 3 to 40 C atoms, which may each be substituted by one or more radicals R, wherein in each case one or more non-adjacent CH 2 A group which may be substituted by RC=CR, C≡C, O or S and in which one or more H atoms may be replaced by D, F, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more groups R in each case, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups, wherein R Y , R 2 , R A Two adjacent groups in the R group may form a monocyclic or polycyclic aliphatic or aromatic ring system which may be substituted by one or more groups R.

10. The compound according to one or more of the preceding claims, characterized in that R 2 、R Y and R A identical or different in each case represents H, D, F, CN; or represents a group of formula (RS-a), a group of formula (RS-b), a group of formula (RS-c) or a group of formula (RS-d), wherein the groups of formula (RS-a), (RS-b), (RS-c) and (RS-d) have the same definition as in claim 7, and wherein two adjacent groups of formula (RS-a), (RS-b), (RS-c) and (RS-d) may form a monocyclic or polycyclic aliphatic or aromatic ring system; or represents a group of formula (ArL-1), The dashed bond in formula (ArL-1) represents bonding to the structure of formula (1), where Ar 2 , Ar 3 in each case independently represents an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may in each case be substituted by one or more groups R; and where m is an integer selected from 1 to 10.

11. The compound according to one or more of the preceding claims, characterized in that the compound is selected from the compounds of formula (4), wherein the symbols have the same meaning as in claim 1.

12. The compound according to one or more of the preceding claims, characterized in that R B and R A are the same as or different from each other in each case and are selected from groups of the formulae (RS-a), (RS-b), (RS-c) and (RS-d), where the groups of the formulae (RS-a), (RS-b), (RS-c) and (RS-d) have the same definitions as in claim 7.

13. The compound according to one or more of the preceding claims, characterized in that the compound is selected from the compounds of formula (5) or (6), wherein the group R A has the same meaning as in claim 1, and wherein, in formula (5), R 40 、R 42 、R 44 which are the same or different in each case and are selected from H, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 or, in each case, an aromatic ring system having 6 to 30 aromatic ring atoms which may be substituted by one or more groups R 32 ; where R 32 has the same definition as in claim 6; The condition is that R 40 , R 42 , R 44 at least one of which is not H; or wherein, in formula (6), R 41 、R 43 which, in each case independently of one another, is selected from H, a straight-chain alkyl group having from 1 to 10 carbon atoms, or a branched or cyclic alkyl group having from 3 to 10 carbon atoms, where the groups mentioned above may each be substituted by one or more groups R 32 or, in each case, an aromatic ring system having from 6 to 30 aromatic ring atoms which is substituted by one or more groups R 32 ; where R 32 has the same definition as in claim 6; The condition is R 41 and R 43 at least one of which is not H.

14. The compound according to claim 13, characterized in that R 42 identical or different in each case and selected from H, a straight-chain alkyl group having from 1 to 10 carbon atoms, or a branched or cyclic alkyl group having from 3 to 10 carbon atoms, where the abovementioned groups may each be substituted by one or more groups R 32 substituted, or may in each case be substituted by one or more groups R 32 an aromatic ring system having from 6 to 30 aromatic ring atoms which is substituted by R 32 has the same definition as in claim 7; R 40 、R 44 are the same or different in each case and are selected from aromatic ring systems having 6 to 30 aromatic ring atoms which may in each case be substituted by one or more groups R 32 ; wherein R 32 has the same definition as in claim 7.

15. The compound according to one or more of the preceding claims, characterized in that the compound is selected from the compounds of formula (5-1), (5-2) and (5-3), wherein the group R A has the same meaning as in claim 1, and wherein In each of formulas (5-1), (5-2), and (5-3), -R 32 The phenyl group shown is unsubstituted or substituted by one or more groups R 32 substituted; R 42 and R 44 are the same or different in each case and are selected from H, a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 ; where R 32 has the same definition as in claim 7.

16. A compound according to one or more of the preceding claims, wherein the compound is selected from the compounds of formula (5-1-Y2) to (5-3-Y2), wherein the group R A , R Y and R have the same meanings as in claim 1, and In each of formulas (5-1-Yw) to (5-3-Yw), the phenyl group represented by -R 32 is unsubstituted or substituted by one or more groups R 32 substituted; R 42 and R 44 are the same or different in each case and are selected from H, straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 ; where R 32 has the same definition as in claim 7.

17. The compound according to claim 13, wherein Group R 40 , R 42 , R 44 are the same or different in each case and are selected from straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, where the above-mentioned groups may each be substituted by one or more groups R 32 , where R 32 has the same definition as in claim 7.

18. A polymer, oligomer or dendrimer, said polymer, oligomer or dendrimer containing one or more compounds according to claim 1, wherein one or more bonds connecting to said polymer, oligomer or dendrimer may be located at any position substituted by R 2 , R A , R B , R Y or R in formula (1).

19. A formulation comprising at least one compound according to one or more of claims 1 to 17 or at least one polymer, oligomer or dendrimer according to claim 18 and at least one solvent.

20. An electronic device comprising at least one compound according to one or more of claims 1 to 17 or at least one polymer, oligomer or dendrimer according to claim 18, the electronic device being selected from an organic electroluminescent device, an organic integrated circuit, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic solar cell, a dye-sensitized organic solar cell, an organic optical detector, an organic photoreceptor, an organic field quenching device, a light emitting electrochemical cell, an organic laser diode and an organic plasma light emitting device.

21. An organic electroluminescent device comprising at least one compound according to one or more of claims 1 to 17 or at least one polymer, oligomer or dendrimer according to claim 18, wherein the compound according to one or more of claims 1 to 17 or the polymer, oligomer or dendrimer according to claim 18 is used as a light emitter in the light emitting layer.

22. The organic electroluminescent device according to claim 21, wherein the compound according to one or more of claims 1 to 17 or the polymer, oligomer or dendrimer according to claim 18 is used as a fluorescent light emitter in the light emitting layer, wherein the light emitting layer comprises at least one other component selected from matrix materials.

23. The organic electroluminescent device according to claim 21, wherein the compound according to one or more of claims 1 to 17 or the polymer, oligomer or dendrimer according to claim 18 is used as a light emitter showing thermally activated delayed fluorescence in the light emitting layer, wherein the light emitting layer comprises at least one other component selected from matrix materials.

24. The organic electroluminescent device according to claim 21, wherein the compound according to one or more of claims 1 to 17 or the polymer, oligomer or dendrimer according to claim 18 is used as a fluorescent light emitter in the light emitting layer, wherein the light emitting layer comprises at least one photosensitizer selected from phosphorescent compounds and thermally activated delayed fluorescence compounds.

25. The organic electroluminescent device according to claim 24, wherein the light emitting layer further comprises at least one organic functional material selected from matrix materials.

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