Materials for organic electroluminescent devices

Abstract

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

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202080075593.1 (corresponding international application number PCT / EP2020 / 081550), which was filed on November 12, 2019 and entitled “Materials for Organic Electroluminescent Devices”. Technical Field

[0002] This invention relates to compounds of formula (1), their use in electronic devices, and electronic devices comprising compounds of formula (1). The invention also relates to methods for preparing compounds of formula (1) and formulations comprising one or more compounds of formula (1). Background Technology

[0003] Currently, the development of functional compounds for electronic devices is a subject of in-depth research. In particular, the aim is to develop compounds to achieve improved performance of electronic devices at one or more relevant points, such as power efficiency and lifetime, as well as the color coordinates of emission.

[0004] According to the present invention, the term electronic device specifically refers to organic integrated circuit (OIC), organic field-effect transistor (OFET), organic thin-film transistor (OTFT), organic light-emitting transistor (OLET), organic solar cell (OSC), organic optical detector, organic photoreceptor, organic field quenching device (OFQD), organic light-emitting electrochemical cell (OLEC), organic laser diode (O-laser), and organic electroluminescent device (OLED).

[0005] Of particular interest are compounds provided for use in electronic devices referred to last as OLEDs. The general structure and functional principles of OLEDs are known to those skilled in the art and are described, for example, in US 4539507.

[0006] Performance data for OLEDs still requires further refinement, especially considering their wide range of commercial applications, such as in display devices or as light sources. Particularly important in this regard are the lifetime, efficiency, operating voltage, and achievable color values ​​of OLEDs. In particular, there is potential for improvement in the lifetime, efficiency, and color purity of blue-emitting OLEDs.

[0007] A key starting point for achieving these improvements is the selection of the luminescent compound and the host compound used in the electronic device.

[0008] Blue fluorescent emitters known from the prior art are a variety of compounds. Arylamines containing one or more fused aryl groups are known from the prior art. Arylamines containing dibenzofuran groups (as disclosed in US2017 / 0012214) or arylamines containing indenobicodibenzofuran groups (as disclosed in CN 10753308) are also known from the prior art.

[0009] Over the past decade, compounds exhibiting thermally activated delayed fluorescence (TADF) (e.g., H. Uoyama et al., Nature 2012, Vol. 492, 234) have been extensively studied. TADF materials are typically organic materials where the band gap between the lowest triplet state T1 and the first excited singlet state S1 is small enough to allow thermal excitation from the T1 state to the S1 state. For quantum statistical reasons, in OLEDs, 75% of excited states are in triplet states and 25% are in singlet states during electronic excitation. Since purely organic molecules typically cannot efficiently emit light from triplet states, 75% of excited states cannot be used for luminescence, meaning that, in principle, only 25% of the excitation energy can be converted into light. However, if the band gap between the lowest triplet state and the lowest excited singlet state is small enough, the first excited singlet state of the molecule can be reached from the triplet state through thermal excitation and can be thermally filled. Since this singlet state is a luminescent state capable of emitting fluorescence, this state can be used to generate light. Therefore, in principle, when pure organic materials are used as light emitters, up to 100% of electrical energy can be converted into light.

[0010] Recently, polycyclic aromatic compounds containing boron and nitrogen atoms have been described (e.g., in US2015 / 0236274A1, CN107501311A, WO2018 / 047639A1). These compounds can be used as phosphors, where fluorescence emission is primarily transient fluorescence, or as TADF compounds.

[0011] However, additional phosphors, especially blue phosphors, are still needed for OLEDs, which would result in very good properties in terms of lifetime, color emission, and efficiency. More specifically, blue phosphors combining very high efficiency, very good lifetime, suitable color coordinates, and high color purity are required.

[0012] Recently, organic electroluminescent devices (OLEDs) have been described that incorporate a TADF compound as a sensitizer and a fluorescent compound as a luminescent agent with high spatial shielding relative to its environment within the luminescent layer (e.g., in WO2015 / 135624). This device construction allows for the provision of organic electroluminescent devices emitting all colors of light, thereby utilizing the basic structure of known fluorescent luminescent agents while still exhibiting the high efficiency of TADF-based OLEDs. This is also known as superfluorescence.

[0013] As an alternative, existing technologies describe organic light-emitting devices (OLEDs) that include a phosphorescent organometallic complex as a sensitizer in the emitting layer. This phosphorescent organometallic complex exhibits a mixture of S1 and T1 states due to large spin-orbit coupling, and a fluorescent compound acts as the emitting element, thereby significantly shortening the emission decay time. This is also known as superphosphorescence.

[0014] Superfluorescence and superphosphorescence are also promising technologies for improving OLED performance, especially in deep blue emission.

[0015] However, further improvements to OLED performance data are still needed, especially considering its wide range of commercial applications, such as in display devices or as a light source. Of particular importance in this regard are OLED lifetime, efficiency, operating voltage, and the achieved color values, especially color purity.

[0016] A key starting point for achieving these improvements in superfluorescent and superphosphorescent systems is the selection of sterically hindered phosphorescent compounds.

[0017] In WO 2015 / 135624, a sterically hindered phosphor based on rubrene is described. However, there is still a need for other sterically hindered phosphors, particularly sterically hindered blue phosphors, which result in OLEDs exhibiting excellent properties in terms of efficiency and color emission. More specifically, a deep blue phosphor combining very high efficiency, very good lifetime, suitable color coordinates, and high color purity is required.

[0018] Furthermore, OLEDs are known to comprise different layers, which can be applied by vapor deposition in a vacuum chamber or by processing from solution. Vapor deposition-based methods yield good results, but such methods are complex and expensive. Therefore, there is also a need for OLED materials that can be easily and reliably processed from solution. In this case, the materials should have good solubility in the solution containing them. Additionally, OLED materials processed from solution should be able to self-orient in the deposited film to improve the overall efficiency of the OLED. The term orientation here refers to the horizontal molecular orientation of the compound, as explained by Zhao et al. in Horizontal molecular orientation in solution-processed organic light-emitting diodes, Appl. Phys. Lett. 106063301, 2015. Summary of the Invention

[0019] Therefore, this invention is based on the technical objective of providing a luminescent body exhibiting transient fluorescence and / or delayed fluorescence. This invention is also based on the technical objective of providing a sterically hindered fluorescent luminescent body that can be combined with a sensitizer compound for use in superfluorescence or superphosphorescence systems. This invention is further based on the technical objective of providing compounds suitable for use in electronic devices such as OLEDs, more particularly as luminescent bodies, and suitable for vacuum processing or solution processing.

[0020] In the study of novel compounds for use in electronic devices, compounds of formula (1) defined below have been found to be particularly suitable for use in electronic devices. In particular, they achieve one or more of the above-mentioned technical objectives, preferably all of them.

[0021] Therefore, the present invention relates to compounds of formula (1),

[0022]

[0023] The following applies to the symbols and markings used:

[0024] X 1 Representing CR in the same or different ways each time it appears. 1 Or N;

[0025] X 2 Representing CR in the same or different ways each time it appears. 2 Or N;

[0026] X A Representing CR in the same or different ways each time it appears. A Or N;

[0027] Y 1 Represents a single bond or selected from -C(R) Y )2-、-C(R Y )2-C(R Y )2-、-Si(R Y Divalent bridge bases of -O, -S, -S(=O)2- and -C(=O)-;

[0028] Y 2 Representative selected from -C(R) Y )2-、-C(R Y )2-C(R Y )2-、-Si(R Y Divalent bridge bases of -O, -S, -S(=O)2- and -C(=O)-;

[0029] R BEach occurrence may represent, in the same or different manner, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R)2, Si(R)3,2, OSO2R, 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 which may be substituted by one or more R groups, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si (R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R, or an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R, or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R;

[0030] R Y R NEach occurrence may represent, in the same or different manner, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, N(R)2, Si(R)3, B(OR)2, OSO2R, 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 which may be substituted by one or more R groups, wherein in each case one or more non-adjacent CH2 groups may be RC=C R, C≡C, Si(R)₂, Ge(R)₂, Sn(R)₂, C=O, C=S, C=Se, P(=O)(R), SO, SO₂, O, S, or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO₂, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R, or an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R, or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R; wherein two adjacent substituents R Y It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R';

[0031] R 1 R 2 R AEach occurrence may represent, in the same or different manner, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, OSO2R, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si(R)2, etc. Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S, or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R; an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R; or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R; wherein R is selected from... 1 R 2 R A Two adjacent groups can form a monocyclic or polycyclic aliphatic or aromatic ring system, which can be substituted by one or more groups R;

[0032] R, in each occurrence, may represent, in the same or different ways, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R', a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be R'C=CR', C≡C, Si(R')2, Ge(R´)2, Sn(R´)2, C=O, C=S, C=Se, P(=O)(R´), SO, SO2, O, S or CONR´ are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R´ in each case, or an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R´, wherein two adjacent groups R may form a monocyclic or polycyclic aliphatic ring system or aromatic ring system, wherein the aliphatic ring system or aromatic ring system may be substituted by one or more groups R´;

[0033] Ar is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which in each case may also be substituted by one or more groups R';

[0034] R´, in each occurrence, may represent H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S, and wherein 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 carbon atoms.

[0035] In the context of this invention, adjacent substituents are substituents that are bonded to atoms that are directly bonded to each other or substituents that are bonded to the same atom. Detailed Implementation

[0036] In addition, the following definitions of chemical groups are applicable to the purposes of this application:

[0037] In the context of this invention, an aryl group 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 context of this invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, wherein at least one of them is a heteroatom. The heteroatom is preferably selected from N, O, and S. This represents the basic definition. If other preferred features are indicated in the specification of this invention, for example, regarding the number of aromatic ring atoms or the presence of heteroatoms, these preferred features apply.

[0038] Aryl groups or heteroaryl groups are herein considered to refer to simple aromatic rings, i.e., benzene, or simple heteroaryl rings, such as pyridine, pyrimidine, or thiophene, or fused (enhanced) aromatic or heteroaryl polycyclic compounds, such as naphthalene, phenanthrene, quinoline, or carbazole. Fused (enhanced) aromatic or heteroaryl polycyclic compounds in the sense of this application consist of two or more simple aromatic or heteroaryl rings fused together.

[0039] In each case, aryl or heteroaryl groups that can be substituted by the aforementioned groups and can be linked to an aromatic or heteroaromatic ring system via any desired position are particularly considered to refer to groups derived from: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, leucine, perylene, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenyl, pentaphenyl, benzo[a]pyran, furan, benzo[a]furan, isobenzo[a]furan, dibenzo[a]furan, thiophene, benzo[a]thiophene, isobenzo[a]thiophene, dibenzo[a]thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthrene Azides, pyrazoles, indazoles, imidazoles, benzimidazoles, naphthiazoles, phenanthreneimidazoles, pyridiniumimidazoles, pyraziniumimidazoles, quinoxalineimazoles azole, benzo[ azole, naphtho azole, anthraquinone azole, phenanthrene azole, isotonic azole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthidine, azacarbazole, benzocarbline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3- diazole, 1,2,4- diazole, 1,2,5- diazole, 1,3,4- Diazole, 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, tetrazolium, 1,2,4,5-tetraazine, 1,2,3,4-tetraazine, 1,2,3,5-tetraazine, purine, pteridine, indoleazine, and benzothiadiazole.

[0040] According to the present invention, an aryloxy group is considered to be an aryl group as defined above, bonded via an oxygen atom. A similar definition applies to heteroaryloxy groups.

[0041] According to the definition of the present invention, an aralkyl group is considered to be an alkyl group in which at least one hydrogen atom is replaced by an aryl group. A similar definition applies to heteroaralkyl groups.

[0042] In the context of this invention, an aromatic ring system contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and more preferably 6 to 20 carbon atoms. A heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, and more preferably 5 to 20 aromatic ring atoms, wherein at least one of them is a heteroatom. The heteroatom is preferably selected from N, O, and / or S. An aromatic or heteroaromatic ring system in the context of this invention is intended to be considered as a system that does not necessarily contain only aryl or heteroaromatic groups, but in which multiple aryl or heteroaromatic groups can also be linked by non-aromatic units (preferably less than 10% of non-H atoms), such as sp... 3 Hybridized C, Si, N, or O atoms, sp 2 Hybridized C or N atoms or sp-hybridized carbon atoms. Therefore, systems such as 9,9'-spirodifluorene, 9,9'-diarylfluorene, triarylamines, diaryl ethers, piracene, etc., are also intended to be considered aromatic ring systems in the sense of this invention, where two or more aryl groups are linked, for example, by straight-chain or cyclic alkyl, alkenyl, or alkynyl groups or by silyl groups. Furthermore, systems where two or more aryl or heteroaryl groups are linked to each other via single bonds, such as systems like biphenyl, terphenyl, or diphenyltriazine, are also considered aromatic or heteroaromatic ring systems in the sense of this invention.

[0043] In each case, it can also be substituted by groups as defined above and can be connected to the aromatic or heteroaromatic group at any desired position. Aromatic or heteroaromatic ring systems having 5-60 aromatic ring atoms are particularly considered to refer to groups derived from the following substances: benzene, naphthalene, anthracene, benzo[a]anthracene, phenanthrene, benzo[a]phenanthrene, pyrene, celestene, perylene, fluoranthene, tetraphenyl, pentaphenyl, benzo[a]pyrene, biphenyl, diphenylide, terphenyl, diphenylide, tetraphenyl, fluorene, spirodifluorene, dihydrofluorene Phenanthrene, dihydropyrene, tetrahydropyrene, cis or trans indofluorene, trimer indo, isotrimer indo, spirotrimer indo, spiroisotrimer indo, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, indole-carbazole, indocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenanthrene Azides, pyrazoles, indazoles, imidazoles, benzimidazoles, naphthiazoles, phenanthreneimidazoles, pyridiniumimidazoles, pyraziniumimidazoles, quinoxalineimazoles azole, benzo[ azole, naphtho azole, anthraquinone azole, phenanthrene azole, isotonic Azole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazathane, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetrazapyrene, pyrazine, phenazine, phenazine Azides, phenothiazines, fluorescent rings, naphthidine, azacarbazole, benzo[a]carbline, phenanthroline, 1,2,3-triazoles, 1,2,4-triazoles, benzo[a]triazoles, 1,2,3- diazole, 1,2,4- diazole, 1,2,5- diazole, 1,3,4- Diazole, 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, tetrazolium, 1,2,4,5-tetraazine, 1,2,3,4-tetraazine, 1,2,3,5-tetraazine, purine, pteridine, indoleazine, and benzothiadiazole, or combinations of these groups.

[0044] For the purposes of this invention, wherein individual H atoms or CH2 groups may be replaced by groups mentioned above under the definition of groups, preferably straight-chain alkyl groups having 1 to 40 C atoms, branched or cyclic alkyl groups having 3 to 40 C atoms, or alkenyl or alkynyl groups having 2 to 40 C atoms, are considered to refer to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methyl Butyl, 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 ocynyl. Alkoxy or thioalkyl groups having 1 to 40 carbon atoms are preferably considered to be methyl methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio 3, tert-butylthio, n-pentylthio, sec-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethylenethio, propylenethio, butenethio, pentenethio, cyclopentenethio, hexenethio, cyclohexenethio, hepenethio, cycloheptenethio, octenenethio, cyclooctenenethio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, hepynylthio, or octyynylthio.

[0045] For the purposes of this application, the statement that two or more groups can form a ring with each other is intended to be considered specifically to mean that two groups are connected to each other by chemical bonds. This is exemplified by the following scheme:

[0046] .

[0047] Furthermore, however, the above statement is also intended to refer to a situation where one of the two groups represents hydrogen, and 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:

[0048] .

[0049] Preferably, Y 1 Represents a single bond or selected from -C(R) YDivalent bridge bases of -O, -S, -S(=O)2- and -C(=O)-. More preferably, Y 1 Represents a single bond or selected from -C(R) Y Divalent bridge bases of type 2, -O, or -S.

[0050] Preferably, Y 2 Representative selected from -C(R) Y Divalent bridge bases of -O, -S, -S(=O)2- and -C(=O)-. More preferably, Y 2 Representative -C(R) Y )2-、-O- or -S-.

[0051] According to a preferred embodiment, group Y 1 The compound representing a single bond and having formula (1) corresponds to the compound of formula (1-Y1).

[0052]

[0053] The symbols have the same meaning as described above.

[0054] According to another preferred embodiment, group Y 1 Representative group -C(R) Y )2- and the compounds of formula (1) correspond to the compounds of formula (1-Y2),

[0055] .

[0056] Preferably, the group R Y Each occurrence may represent H or D, a straight-chain alkyl group having 1 to 20, preferably 1 to 10 carbon atoms, or an alkenyl or ynyl group having 2 to 20, preferably 2 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 20, preferably 3 to 10 carbon atoms, each of which may be substituted by one or more groups R, or 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, each of which may be substituted by one or more groups R in each case; wherein two adjacent substituents R Y It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R. According to a preferred embodiment, two adjacent substituents R... Y Formation of a (RY-1) ring,

[0057]

[0058] Where Y 3Represents a single bond or selected from -C(R) Y )2-、-C(R Y )2-C(R Y )2-、-Si(R Y Divalent bridging groups of (RY-1), (RY-2), (RY-2), (RY-3), (RY-4), (RY-5), (RY-6), (RY-7), (RY-8), and (RY-9); wherein the groups of formula (RY-1) may be replaced by one or more groups R, and wherein the dashed bond indicates a bond to the structure of formula (1).

[0059] Preferably, Y 3 Represents a single bond or selected from -C(R) Y A divalent bridge base of -2, -O, or -S. More preferably, Y 3 Representing a single bond and group (RY-1) corresponding to group (RY-2):

[0060] .

[0061] If two adjacent substituents R Y Formulation (R) Y If the ring is -1), then the compound of formula (1) corresponds to the compound of formula (1-Y3).

[0062]

[0063] The symbols have the same meaning as described above.

[0064] According to a preferred embodiment, the group Y in formula (1-Y3) 2 Corresponding to the group -C(R) Y )2-, where two adjacent substituents R Y A ring of formula (RY-1) as described above is formed, thus the compound of formula (1-Y3) corresponds to the compound of formula (1-Y4).

[0065]

[0066] The symbols have the same meaning as described above.

[0067] According to a preferred embodiment, the compound of formula (1) is selected from the compound of formula (2).

[0068]

[0069] The symbols have the same meaning as described above.

[0070] Preferably, the compounds of formula (2) correspond to the compounds of formulas (2-Y1), (2-Y2), (2-Y3), and (2-Y4).

[0071]

[0072] .

[0073] According to a highly preferred embodiment, the compound of formula (1) is selected from the compounds of formula (3).

[0074]

[0075] The symbols have the same meaning as described above.

[0076] Preferably, the compounds of formula (3) correspond to the compounds of formulas (3-Y1), (3-Y2), (3-Y3), and (3-Y4).

[0077]

[0078]

[0079] The symbols have the same meaning as described above.

[0080] According to a particularly preferred embodiment, the compound of formula (1) is selected from the compounds of formula (4).

[0081]

[0082] The symbols have the same meaning as described above.

[0083] Preferably, the compounds of formula (4) correspond to the compounds of formulas (4-Y1), (4-Y2), (4-Y3), and (4-Y4).

[0084]

[0085] The symbols have the same meaning as described above.

[0086] Preferably, the group R BEach occurrence, whether identical or different, represents 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, wherein each of the alkyl, alkoxy, thioalkoxy, alkenyl, or alkynyl groups may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si(R)2, Ge(R)2, Sn( The following groups may be replaced by R, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S, or CONR, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, or an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, and very preferably 5 to 18 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be replaced by one or more groups R, or an aralkyl or heteroaromatic group having 5 to 60, preferably 5 to 40, more preferably 5 to 30, and very preferably 5 to 18 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be replaced by one or more groups R.

[0087] More preferably, group R B Each occurrence may represent, in the same or different manner, 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, each of which may be substituted by one or more groups R, wherein one or more H atoms may be substituted by D, F, Cl, or CN, or an aromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, wherein in each case the aromatic ring system may be substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60, preferably 5 to 40, more preferably 5 to 30, very preferably 5 to 18 aromatic ring atoms, wherein the aralkyl or heteroaralkyl group may be substituted by one or more groups R.

[0088] Very preferably, group R B Selected from the same or different sources each time it appears:

[0089] -A branched or cyclic alkyl group represented by the following general formula (RS-a),

[0090]

[0091] (RS-a)

[0092] in

[0093] R 22 R 23 R 24 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 25 Substitution, and wherein the group R 22 R 23 R 24 Two or all of the R groups in 22 R 23 R 24 It can be linked to form a (poly)cycloalkyl group, said (poly)cycloalkyl group being posterior to one or more groups R 25 replace;

[0094] R 25 Each time it appears, it 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, either identically or differently.

[0095] The condition is that each time it appears, group R... 22 R 23 and R 24 At least one of them is not H, provided that each time it appears, all groups R are present. 22 R 23 and R 24 Together they have at least 4 carbon atoms, and the condition is that each time they appear, if the group R 22 R 23 R 24 If two of them are H, then the remaining groups are not straight chains;

[0096] -Or a branched or cyclic alkoxy group represented by the following general formula (RS-b),

[0097]

[0098] (RS-b)

[0099] in

[0100] R 26 R 27 R 28 Each time it appears, it 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, wherein each of the above groups may be represented by one or more groups R as defined above.25 Substitution, and wherein the group R 26 R 27 R 28 Two or all of the R groups in 26 R 27 R 28 It can be linked to form a (poly)cycloalkyl group, which can be formed by one or more groups R as defined above. 25 replace;

[0101] The condition is that each time it appears, group R... 26 R 27 and R 28 Only one of them can be H;

[0102] -Or an aralkyl group represented by the following general formula (RS-c),

[0103]

[0104] (RS-c)

[0105] in

[0106] R 29 R 30 R 31 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Substitution, and wherein the group R 29 R 30 R 31 Two or all of them can be linked to form a (poly)cycloalkyl group or an aromatic ring system, each of which can be represented by one or more groups R. 32 replace;

[0107] R 32 Each time it appears, it is selected from the same or different straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, or aromatic ring systems having 6 to 24 aromatic ring atoms;

[0108] The condition is that each time it appears, group R... 29 R 30 and R 31 At least one of them is not H, and the condition is that each time it appears, the group R... 29 R 30 and R31 At least one of them 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;

[0109] -Or an aromatic ring system represented by the following general formula (RS-d),

[0110]

[0111] (RS-d)

[0112] in

[0113] R 40 To R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Substitution, and wherein the group R 40 To R 44 Two or more of them can be linked to form a (poly)cycloalkyl group or an aromatic ring system, each of which can be connected by one or more groups R as defined above. 32 replace.

[0114] Examples of suitable groups of formula (RS-a) to (RS-d) are groups (RS-1) to (RS-78):

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] The dashed lines represent the bonds between these groups and the structure of formula (1), and the groups of formulas (RS-1) to (RS-47) can also be bonded to at least one group R as defined above. 25 Substitution, and groups (RS-48) to (RS-78) may also be replaced by at least one group R as defined above. 32 replace.

[0125] Preferably, R 2 and R A Each occurrence may represent H, D, F, Cl, Br, I, CN, N(Ar)2, either identically or differently, having 1 to 40, preferably 1 to 20, more preferably 1 to 10 carbon atoms, of a straight-chain alkyl, alkoxy, or thioalkyl group, or having 3 to 40, preferably 3 to 20, more preferably 3 to 10 carbon atoms, of a branched or cyclic alkyl, alkoxy, or thioalkyl group, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C= S, C=Se, P(=O)(R), SO, SO2, O, S or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2. It is an aromatic or heteroaromatic ring system having 5 to 60, preferably 1 to 40, more preferably 1 to 30, and very preferably 1 to 18 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case, or an aralkyl or heteroaromatic group having 5 to 60, preferably 1 to 40, more preferably 1 to 30, and very preferably 1 to 18 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R.

[0126] More preferably, R 2 and R AEach occurrence may represent H, D, F, CN in the same or different manner, having 1 to 40, preferably 1 to 20, more preferably 1 to 10 carbon atoms, of a straight-chain alkyl, alkoxy, or thioalkyl group, or having 3 to 40, preferably 3 to 20, more preferably 3 to 10 carbon atoms, of a branched or cyclic alkyl, alkoxy, or thioalkyl group, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, O or S is replaced, and one or more H atoms may be replaced by D or F, having 5 to 60, preferably 1 to 40, more preferably 1 to 30, and very preferably 1 to 18 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted with one or more groups R in each case, or having 5 to 60, preferably 1 to 40, more preferably 1 to 30, and very preferably 1 to 18 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted with one or more groups R.

[0127] Most preferably, R 2 and R A The same or different meanings each time it appears:

[0128] -H, D, F, CN; or

[0129] - 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 formulas (RS-a), (RS-b), (RS-c), and (RS-d) have the same definition as in claim 6; or

[0130] - Groups of formula (ArL-1),

[0131]

[0132] In equation (ArL-1), the dashed bond represents the bond with the structure of equation (1), where Ar 2 Ar 3 Each occurrence may represent, in the same or different ways, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case; and wherein m is an integer selected from 1 to 10.

[0133] According to a preferred embodiment, group R 2 Or R AAt least one group representing formula (RS-a), formula (RS-b), formula (RS-c), or formula (RS-d), wherein the groups of formula (RS-a), (RS-b), (RS-c), and (RS-d) are as defined above.

[0134] According to a preferred embodiment, group R B and R A The groups selected from formulas (RS-a), (RS-b), (RS-c), and (RS-d) are the same or different each time they appear, wherein the groups of formulas (RS-a), (RS-b), (RS-c), and (RS-d) have the same definition as described above.

[0135] According to a preferred embodiment, groups R, R 2 Or R A At least one of them represents a group of formula (ArL-1) as defined above.

[0136] Preferably, the marker m in the group of formula (ArL-1) is an integer selected from 1 to 6, and very preferably from 1 to 4.

[0137] In formula (ArL-1), the preferred group is Ar. 2 Groups selected from formulas (Ar2-1) to (Ar2-25),

[0138]

[0139]

[0140] The dashed bond represents the structure of equation (1) and the Ar group. 2 Or Ar 3 The bonds are such that the groups of formulas (Ar2-1) to (Ar2-25) can be substituted at each free position by a group R, which has the same meaning as described above, and wherein:

[0141] E 4 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)-, -SO2-, -N(R 0 )-、-P(R 0 )- and -P((=O)R 0 )-;

[0142] R 0 Each occurrence may represent H, D, F, CN, a straight-chain alkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be substituted by RC=CR, C≡C, C=O, C=S, SO, SO2, O, or S, and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case one or more groups R may be substituted; wherein two adjacent substituents R 0 It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R, which have the same meaning as described above.

[0143] Preferably, E 4 Selected from -C(R) 0 )2-、-Si(R 0 )2-, -O-, -S- or -N(R) 0 )-, where the substituent R 0 It has the same meaning as above.

[0144] Preferably, R 0 Each occurrence may represent H, D, F, CN, having the same or different linear alkyl groups having 1 to 40, preferably 1 to 20, more preferably 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 40, preferably 3 to 20, more preferably 3 to 10 carbon atoms, each of which 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, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R; wherein two adjacent substituents R 0 It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R, wherein the groups R have the same meaning as described above. Suitable groups R 0 Examples include H, methyl, ethyl, propyl, butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted fluorene.

[0145] In equations (Ar2-1) to (Ar2-25), the following equation is preferred:

[0146] (Ar2-1), (Ar2-2), (Ar2-3), (Ar2-18), (Ar2-19), (Ar2-20), (Ar2-21), (Ar2-22) and (Ar2-25).

[0147] Furthermore, in formula (ArL-1), Ar is preferred. 3 The groups selected from formulas (Ar3-1) to (Ar3-27) may appear the same or different in each occurrence.

[0148]

[0149]

[0150] The dashed key represents Ar 2 The bond, and where E 4 Having the same meaning as above, and the groups of formulas (Ar3-1) to (Ar3-27) may be replaced by group R at each free position, wherein group R has the same meaning as above.

[0151] In equations (Ar3-1) to (Ar2-27), the following equation is preferred:

[0152] (Ar3-1), (Ar3-2), (Ar3-23), (Ar3-24), (Ar3-25) and (Ar3-27).

[0153] According to a preferred embodiment, at least one Ar group 2 The group represented by formula (Ar2-2) and / or at least one Ar group 3 The group represented by formula (Ar3-2)

[0154]

[0155] in

[0156] The dashed bond in formula (Ar2-2) represents the structure of formula (1) and the Ar group. 2 Or Ar 3 The bond; and the dashed bond in equation (Ar3-2) represents the bond with Ar 2 The bonding; and E 4 It has the same meaning as above; and the groups of formulas (Ar2-2) and (Ar3-2) can be replaced by group R at each free position, said group R having the same meaning as above.

[0157] According to a highly preferred embodiment, at least one Ar group 2 The group represented by formula (Ar2-2-1) and / or at least one Ar group3 The group represented by the formula (Ar3-2-1)

[0158]

[0159] in

[0160] The dashed bond in formula (Ar2-2-1) represents the structure of formula (1) and the Ar group. 2 Or Ar 3 Bonding;

[0161] The dashed key in equation (Ar3-2-1) represents the key to Ar. 2 Bonding;

[0162] E 4 It has the same meaning as above; and

[0163] The groups in formulas (Ar2-2-1) and (Ar3-2-1) can be replaced by a group R at each free position, wherein the group R has the same meaning as described above.

[0164] According to a particularly preferred embodiment, at least one Ar group 2 The group represented by formula (Ar2-2-1b) and / or at least one Ar group 3 The group represented by formula (Ar3-2-1b)

[0165]

[0166] in

[0167] The dashed bond in formula (Ar2-2-1b) represents the structure of formula (1) and the Ar group. 2 Or Ar 3 Bonding;

[0168] The dashed key in equation (Ar3-2-1b) represents the key to Ar. 2 Bonding;

[0169] R 0 It has the same meaning as above; and

[0170] The groups in formulas (Ar2-2-1b) and (Ar3-2-1b) can be replaced by a group R at each free position, wherein the group R has the same meaning as described above.

[0171] Very suitable group R 2 and R AExamples include H, D, F, CN, substituted or unsubstituted straight-chain alkyl groups having 1 to 10 carbon atoms, more particularly methyl, ethyl, propyl, butyl, substituted or unsubstituted branched or cyclic alkyl groups having 3 to 10 carbon atoms, more particularly tert-butyl, and aromatic or heteroaromatic ring systems selected from formulas (Ar1-1) to (Ar1-24).

[0172]

[0173]

[0174] In equations (Ar1-1) to (Ar1-24):

[0175] - Dashed lines indicate bonds to the structure of equation (1);

[0176] R in equation (Ar1-14) N Each occurrence may represent H or 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 may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be substituted by RC=CR, C≡C, C=O, C=S, SO, SO2, O, or S, and wherein one or more H atoms may be substituted 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, wherein in each case one or more aromatic or heteroaromatic ring systems may be substituted by one or more groups R, wherein two adjacent substituents R N It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R, wherein the groups R have the same meaning as in claim 1;

[0177] R in equations (Ar1-12) and (Ar1-21) to (Ar1-24) 0Each occurrence may represent H, D, F, CN, a straight-chain alkyl group having 1 to 40 carbon atoms or a branched or cyclic alkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be substituted by RC=CR, C≡C, C=O, C=S, SO, SO2, O, or S, and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R; wherein two adjacent substituents R 0 It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R, wherein the groups R have the same meaning as described above;

[0178] The groups in formulas (Ar1-1) and (Ar1-24) can be replaced by a group R at each free position, wherein the group R has the same meaning as described above.

[0179] According to a particularly preferred embodiment, the compound of formula (1) is selected from the compounds of formula (5).

[0180]

[0181] in:

[0182] R 40 R 42 R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Replace; where R 32 As defined above;

[0183] The condition is R 40 R 42 R 44 At least one of them is not H;

[0184] And the other symbols have the same meaning as described above.

[0185] Preferably, the compounds of formula (5) correspond to the compounds of formulas (5-Y1), (5-Y2), (5-Y3), and (5-Y4).

[0186]

[0187] The symbols have the same meaning as described above.

[0188] According to another particularly preferred embodiment, the compound of formula (1) is selected from the compounds of formula (6).

[0189]

[0190] in:

[0191] R 41 R 43 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Replace; where R 32 As defined above;

[0192] The condition is R 41 R 43 At least one of them is not H.

[0193] Preferably, the compounds of formula (6) correspond to the compounds of formulas (6-Y1), (6-Y2), (6-Y3), and (6-Y4).

[0194]

[0195]

[0196] The symbols have the same meaning as described above.

[0197] Preferably, the group R 42 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, which in each case can be replaced by one or more groups R 32 Substitution, and group R 40 R 44 Each occurrence is either identical or different from an aromatic ring system having 6 to 30 aromatic ring atoms, which in each case may be selected by one or more groups R. 32 replace.

[0198] According to a preferred embodiment, the group R in formulas (5), (5-Y1), (5-Y2), (5-Y3) and (5-Y4) 40 R 42 R 44 In each case, the groups are selected, either identically or differently, from straight-chain alkyl groups having 1 to 10 carbon atoms, or from branched or cyclic alkyl groups having 3 to 10 carbon atoms, wherein each of the aforementioned groups may be converted by one or more groups R. 32 Substitution. More preferably, group R 40 R 42 R 44 Each occurrence thereof is identical or different and is selected from straight-chain alkyl groups having 1 to 10, preferably 1 to 5, more preferably 1 to 3 carbon atoms, wherein each of the above groups may be converted by one or more groups R 32 Substitution. In this case, the suitable group R... 40 R 42 R 44 Examples are methyl, ethyl, and butyl.

[0199] According to another preferred embodiment, group R 40 R 42 R 44 Each occurrence is either identical or different from an aromatic ring system having 6 to 30 aromatic ring atoms, which in each case may be selected by one or more groups R. 32 Substitution. Preferably, the compound of formula (1) is selected from the compounds of formulas (5-1), (5-2), and (5-3).

[0200]

[0201] in

[0202] In each of equations (5-1), (5-2), and (5-3), use -R 32 The phenyl group shown is unsubstituted or substituted with one or more R groups. 32 replace;

[0203] R 42 and R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Replace; where R 32 As defined above.

[0204] More preferably, the compounds of formulas (5-1), (5-2), and (5-3) correspond to the compounds of formulas (5-1-a) to (5-3-g).

[0205]

[0206]

[0207]

[0208] In each of equations (5-1-a) to (5-3-g), -R is used. 32 The phenyl group shown is unsubstituted or substituted with one or more R groups. 32 Replacement, where the symbols have the same meaning as described above.

[0209] Preferably, the group R, in each occurrence, represents H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, Si(R')3, either as always or differently, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 carbon atoms, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be substituted by R'C =CR´, O or S replaced, and one or more H atoms may be replaced by D, F or CN, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be replaced by one or more groups R´ in each case, 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, wherein the aryloxy group may be replaced by one or more groups R´, wherein two adjacent substituents R may form a monocyclic or polycyclic aliphatic or aromatic ring system, wherein the aliphatic or aromatic ring system may be replaced by one or more groups R´. When R is selected from aromatic and heteroaromatic ring systems, the aromatic and heteroaromatic ring systems are preferably selected from aromatic and heteroaromatic ring systems having 5 to 40, more 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.

[0210] Preferably, the Ar group, in each occurrence, is the same or different, an aromatic or heteroaromatic ring system having 5 to 18, preferably 6 to 18, aromatic ring atoms, which in each case may also be substituted by one or more R' groups.

[0211] Preferably, R ´Each time it appears, it may represent H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 10 carbon atoms, wherein 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, carbon atoms.

[0212] The following compounds are examples of compounds of formula (1):

[0213]

[0214]

[0215]

[0216]

[0217]

[0218] 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, etc. Examples of suitable synthetic methods are generally described in the following schemes 1 and 2.

[0219] Option 1

[0220]

[0221] Where X 1 and X 2 It is a leaving group, preferably selected from halogens. X 1 Preferably selected from Br, Cl, I, more preferably Br, X 2 Preferably selected from Br and Cl, more preferably Cl;

[0222] R is a group; two groups R present in the same boric acid or borate ester group can bond together to form a ring, with the symbols Y and R. B Having the same meaning as described above, and wherein the compound depicted in Scheme 1 can also be reacted with the group R as defined above. 1 R 2 and R A Replace; and

[0223] Y 1 Y 2 and R B It has the same meaning as above.

[0224] To process the compounds according to the invention from a liquid phase, for example by spin coating or printing, formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions, or emulsions. For this purpose, mixtures of two or more solvents are preferably used. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthol, veratrine, THF, methyl-THF, THP, chlorobenzene, dimethylbenzene, etc. Alkane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fonone, 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, decahydrogenated Naphthalene, dodecylbenzene, ethyl benzoate, indene, methyl benzoate, NMP, p-cymene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0225] Therefore, the present invention further relates to a formulation comprising the compound according to the invention and at least one additional compound. The additional compound may be, for example, a solvent, particularly one of the solvents described above or a mixture of these solvents. However, the additional compound may also be at least one other organic or inorganic compound also used in electronic devices, such as a luminescent compound, particularly a phosphorescent dopant, and / or an additional matrix material. Suitable luminescent compounds and additional matrix materials are described below in conjunction with organic electroluminescent devices. The additional compound may also be polymerized.

[0226] The compounds and mixtures according to the invention are suitable for use in electronic devices. An electronic device is herein considered to be a device comprising at least one layer containing at least one organic compound. However, the component may also comprise inorganic materials or include a layer composed entirely of inorganic materials.

[0227] Therefore, the present invention further relates to the use of compounds or mixtures according to the invention in electronic devices, particularly in organic electroluminescent devices.

[0228] The present invention also relates to electronic devices comprising at least one of the compounds or mixtures according to the invention as described above. The preferred embodiments stated above with respect to the compounds also apply to electronic devices.

[0229] The electronic devices are 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 photosensors, organic field quenching devices (O-FQD), light-emitting electrochemical cells (LEC), organic laser diodes (O-lasers), and "organic plasmon light-emitting devices" (DM Koller et al.). Nature Photonics 2008, 1-4), preferred organic electroluminescent devices (OLED, PLED), especially phosphorescent OLED.

[0230] Organic electroluminescent devices include a cathode, an anode, and at least one emitting layer. In addition to these layers, they may also include additional 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. Similarly, an intermediate layer having, for example, exciton blocking functionality can be introduced between two emitting layers. However, it should be noted that each of these layers is not necessarily required. Organic electroluminescent devices may include one or more emitting layers. If multiple emitting layers are present, these emitting layers preferably have a total of multiple emission maximum values ​​between 380 nm and 750 nm, thereby producing white light overall, i.e., multiple luminescent compounds capable of fluorescence or phosphorescence are used for the emitting layers. A system having three emitting layers is particularly preferred, wherein these three layers exhibit blue, green, and orange or red light emission (see, for example, WO2005 / 011013 for basic structures). These can be fluorescent emitting layers, phosphorescent emitting layers, or a hybrid system, wherein fluorescent and phosphorescent emitting layers are combined with each other.

[0231] Depending on the precise structure and substitutions, the compound according to the invention based on the above embodiments can be used in multiple layers.

[0232] Preferably, organic electroluminescent devices contain a compound of formula (1) or according to a preferred embodiment as a fluorescent emitter or a TADF (thermally activated delayed fluorescence) emitter. More specifically, the compound of formula (1) or according to a preferred embodiment is preferably used as a blue fluorescent emitter displaying transient fluorescence or as a blue TADF emitter.

[0233] According to another preferred embodiment of the invention, the compound of formula (1) or according to the preferred embodiment is used in a superfluorescent system, as described in, for example, WO2015 / 135624, which comprises a compound of formula (1) as a phosphor and a sensitizer compound selected from thermally activated delayed fluorescence compounds (TADF compounds), wherein the energy of the sensitizer is transferred to the phosphor via Foster resonance energy transfer.

[0234] According to another preferred embodiment of the invention, the compound of formula (1) or the compound according to the preferred embodiment is used in a superphosphorescent system, as described in, for example, WO2001 / 08230A1, which comprises the compound of formula (1) as a phosphorescent emitter and a sensitizer compound selected from phosphorescent compounds, wherein the energy of the sensitizer is transferred to the phosphorescent emitter via Foster resonance energy transfer.

[0235] Depending on the precise substitution, the compounds of formula (1) can also be used in electron transport layers and / or electron blocking or exciton blocking layers and / or hole transport layers. The preferred embodiments described above are also applicable to the use of the materials in organic electronic devices.

[0236] The compounds of formula (1) are particularly suitable for use as blue emitting compounds. The electronic devices involved may include a single emitting layer comprising the compounds according to the invention, or may include two or more emitting layers. Additional emitting layers may herein include one or more compounds according to the invention or other compounds.

[0237] If the compound according to the invention is used as a phosphor or TADF emitter in the emitting layer, it is preferably used in combination with one or more matrix materials. The matrix material is hereby considered to be a material present in the emitting layer, preferably as a major component, and which does not emit light during device operation.

[0238] Preferably, the matrix compound has a glass transition temperature T greater than 70°C, more preferably greater than 90°C, and most preferably greater than 110°C. G .

[0239] The proportion of the luminescent compound in the luminescent layer mixture 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 matrix materials is between 50.0% and 99.9%, preferably between 80.0% and 99.5%, and particularly preferably between 90.0% and 99.0%.

[0240] For the purposes of this application, the description of proportions expressed as % is considered to be volume % if the compound is applied from the gas phase and weight % if the compound is applied from a solution.

[0241] If the compound of formula (1) or according to the preferred embodiment is used as a phosphor (temporal fluorescence) in the luminescent layer, the preferred matrix material used in combination with the phosphor is selected from the following categories: oligomeric aromatic subunits (e.g., 2,2',7,7'-tetraphenylspirodifluorene or dinathynethracene according to EP676461), particularly oligomeric aromatic subunits containing fused aromatic groups, oligomeric aromatic vinyl subunits (e.g., DVBBi or spiro-DPVBBi according to EP 676461), multi-legged metal complexes (e.g., according to WO 2004 / 081017), hole-conducting compounds (e.g., according to WO 2004 / 058911), electron-conducting compounds, particularly ketones, phosphine oxides, sulfoxides, etc. (e.g., according to WO 2005 / 084081 and WO 2005 / 084082), transisomers (e.g., according to WO 2006 / 048268), boric acid derivatives (e.g., according to WO 2006 / 048268), and boronic acid derivatives (e.g., according to WO 2004 / 081017). WO 2006 / 117052) or benzo[a]anthracene (e.g., according to WO 2008 / 145239). Particularly preferred matrix materials are selected from the following categories: oligomeric aromatic derivatives, including naphthalene, anthracene, benzo[a]anthracene and / or pyrene or trans-isomers of these compounds, oligomeric aromatic vinyl derivatives, ketones, phosphine oxides and sulfoxides. Very particularly preferred matrix materials are selected from the following categories: oligomeric aromatic derivatives, including anthracene, benzo[a]anthracene, benzo[a]phenanthrene and / or pyrene or trans-isomers of these compounds. Oligomeric aromatic derivatives are intended to be considered as compounds in which at least three aryl or aromatic derivative groups are bonded to each other.

[0242] Particularly preferred matrix materials used in combination with compounds of formula (1) used as phosphors in the luminescent layer are depicted in the table below:

[0243]

[0244]

[0245]

[0246] If the compound according to the invention is used as a fluorescent luminescent compound in the luminescent layer, it can be used in combination with one or more other fluorescent luminescent compounds.

[0247] In addition to the compounds according to the invention, preferred fluorescent emitters are selected from the arylamine class. Aromatic amines in the sense of the invention are considered to be compounds 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 a fused ring system having at least 14 aromatic ring atoms. Preferred examples are aromatic anthraceneamines, aromatic anthracene diamines, aromatic pyreneamines, aromatic pyrene diamines, aromatic pyrine amines, or aromatic pyrine diamines. Aromatic anthraceneamines are considered to be compounds in which one of the diarylamino groups is directly bonded to an anthracene group, preferably at position 9. Aromatic anthracene diamines are considered to be compounds in which two diarylamino groups are directly bonded to an anthracene group, preferably at positions 9 and 10. Aromatic pyreneamines, pyrene diamines, pyrine amines, and pyrine diamines are defined in a similar manner, wherein the diarylamino groups are preferably bonded to pyrene at position 1 or at positions 1 and 6. Other preferred luminescent agents are indenefluoreneamine or indenefluorenediamine, for example according to WO 2006 / 108497 or WO 2006 / 122630; benzo[a]indenefluoreneamine or benzo[a]indenefluorenediamine, for example according to WO 2008 / 006449; and dibenzo[a]indenefluoreneamine or dibenzo[a]indenefluorenediamine, for example according to WO 2007 / 140847; and indenefluorene derivatives containing fused aryl groups disclosed in WO 2010 / 012328. Another preferred luminescent material is a benzanthracene derivative as disclosed in WO 2015 / 158409, an anthracene derivative as disclosed in WO 2017 / 036573, a fluorene dimer as disclosed in WO 2016 / 150544, or a phenanthrene as disclosed in WO 2017 / 028940 and WO 2017 / 028941. Azide derivatives. Also preferred are pyrene arylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871. Also preferred are benzo[a]indofluoreneamine disclosed in WO 2014 / 037077, benzo[a]fluoreneamine disclosed in WO 2014 / 106522, and indofluorene disclosed in WO 2014 / 111269 or WO 2017 / 036574.

[0248] In addition to the compounds according to the invention, examples of preferred fluorescent luminescent compounds are described in the table below, which may be used in combination with the compounds of the invention in a luminescent layer or in another luminescent layer of the same device:

[0249]

[0250]

[0251]

[0252]

[0253]

[0254] If the compound of formula (1) or according to the preferred embodiment is used as the TADF emitter in the luminescent layer, the preferred matrix material used in combination with the TADF emitter is selected from the following categories: ketones, phosphine oxides, sulfoxides and 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-biscarbazole biphenyl), m-CBP or carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP 2004 / 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; indobenzocarbazole derivatives, for example according to WO 2010 / 136109 and WO 2011 / 000455; azacarbazole, for example according to EP 1617710, EP1617711, EP 1731584, JP 2005 / 347160; bipolar matrix materials, for example according to WO 2007 / 137725; silanes, for example according to WO 2005 / 111172; borazocyclopentane or borate esters, for example according to WO2006 / 117052; silylate derivatives, for example according to WO The following are applicable materials: phosphazacyclopentane derivatives, such as those according to WO 2010 / 054729; 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 EP652273 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 matrix materials are also those described in WO 2015 / 135624. These are incorporated herein by reference. A mixture of two or more of these matrix materials can also be used.

[0255] The matrix compound used for TADF light emitters is preferably a charge-transporting compound, i.e., an electron-transporting or hole-transporting compound, or a bipolar compound. In the context of this application, the matrix compound used may also be a compound that neither transports holes nor electrons. In the context of this invention, the electron-transporting compound is a compound with a LUMO ≤ -2.50 eV. Preferably, the LUMO ≤ -2.60 eV, more preferably ≤ -2.65 eV, and most preferably ≤ -2.70 eV. LUMO is the lowest unoccupied molecular orbital. The LUMO value of the compound is determined by quantum chemical calculations, as generally described in the Examples section below. In the context of this invention, the hole-transporting compound is a compound having a HOMO ≥ -5.5 eV. HOMO is preferably ≥ -5.4 eV, more preferably ≥ -5.3 eV. HOMO is the highest occupied molecular orbital. The HOMO value of the compound is determined by quantum chemical calculations, as generally described in the Examples section below. In the context of this invention, the bipolar compound is a compound that transports both holes and electrons.

[0256] The electron-conducting matrix compound suitable for TADF luminescent materials is selected from the following categories: triazine, pyrimidine, lactam, metal complexes, especially Be, Zn, and Al complexes, aromatic ketones, aromatic phosphine oxides, phosphonocyclopentanes, boronocyclopentanes substituted with at least one electron-conducting substituent, and quinoxaline. In a preferred embodiment of the invention, the conductive compound is a purely organic compound, i.e., a metal-free compound.

[0257] In addition to the sensitizer and the phosphor, the superfluorescent and superphosphorescent systems described above preferably contain at least one matrix material. In this case, it is preferable that the lowest triplet energy of the matrix compound is no more than 0.1 eV lower than the triplet energy of the sensitizer compound.

[0258] Particularly preferred is that T1 (matrix) ≥ T1 (sensitizer).

[0259] More preferably: T1 (matrix) - T1 (sensitizer) ≥ 0.1 eV;

[0260] More preferably: T1 (matrix) - T1 (sensitizer) ≥ 0.2 eV.

[0261] Here, T1(matrix) is the lowest triplet energy of the matrix compound, and T1(sensitizer) is the lowest triplet energy of the sensitizer compound. The triplet energy of T1(matrix) is determined here by the edge of the photoluminescence spectrum measured on a pure film at 4K. T1(sensitizer) is determined by the edge of the photoluminescence spectrum measured at room temperature in a toluene solution.

[0262] The matrix material suitable for superfluorescence or superphosphorescence systems is the same as the matrix material described above, and more preferably, it is also preferred to use the matrix material for TADF materials.

[0263] Suitable phosphorescent emitters, particularly those emitting light under suitable excitation, preferably in the visible light region, and additionally containing at least one compound 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.

[0264] For the purposes of this invention, all luminescent iridium, platinum, or copper complexes are considered phosphorescent compounds.

[0265] Examples of the aforementioned 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 known to those skilled in the art in the field of organic electroluminescent devices, as used in phosphorescent OLEDs according to the prior art, are suitable for devices according to the invention. Those skilled in the art will also be able to combine other phosphorescent complexes with the compounds according to the invention for use in OLEDs without inventive effort.

[0266] Preferred matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides, or aromatic sulfoxides or 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-biscarbazole biphenyl) or carbazole derivatives disclosed in WO 2005 / 039246, US 2005 / 0069729, JP2004 / 288381, EP 1205527, or WO 2008 / 086851; indolecarbazole derivatives, such as those according to WO 2007 / 063754 or WO 2008 / 056746; indobenzocarbazole derivatives, such as those according to WO 2010 / 136109, WO2011 / 000455 or WO 2013 / 041176; azacarbazole derivatives, such as those according to EP 1617710, EP 1617711, EP1731584, JP 2005 / 347160; bipolar matrix materials, such as those according to WO 2007 / 137725; silanes, such as those according to WO 2005 / 111172; borazolacine or borate esters, 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 EP652273 or WO 2009 / 062578; silylated diazacyclopentane or silylated tetraazacyclopentane derivatives, such as those according to WO2010 / 054729; phosphorus diazacyclopentane 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 WO 2012 / 143080; triphenylene derivatives, such as those according to WO 2012 / 048781; or lactams, such as those according to WO 2011 / 116865 or WO 2011 / 137951.

[0267] More particularly, when the phosphorescent compound is used in the superphosphorescent system as described above, the phosphorescent compound is preferably selected from phosphorescent organometallic complexes, such as those described in WO2015 / 091716. Furthermore, phosphorescent organometallic complexes are particularly preferred, as described in WO2000 / 70655, WO2001 / 41512, WO2002 / 02714, WO2002 / 15645, EP1191612, WO2005 / 033244, WO2005 / 019373, US2005 / 0258742, WO2006 / 056418, WO2007 / 115970, WO2007 / 115981, WO2008 / 000727, and WO2009 / 05028. 1. WO2009 / 050290, WO2011 / 051404, WO2011 / 073149, WO2012 / 121936, US2012 / 0305894, WO2012 / 170571, WO2012 / 170 461. WO2012 / 170463, WO2006 / 121811, WO2007 / 095118, WO2008 / 156879, WO2008 / 156879, WO2010 / 068876, WO2011 / 106 344. WO2012 / 172482, EP3126371, WO2015 / 014835, WO2015 / 014944, WO2016 / 020516, US20160072081, WO2010 / 086089 , WO2011 / 044988, WO2014 / 008982, WO2014 / 023377, WO2014 / 094961, WO2010 / 069442, WO2012 / 163471, WO2013 / 020631 Among US20150243912, WO2008 / 000726, WO2010 / 015307, WO2010 / 054731, WO2010 / 054728, WO2010 / 099852, WO2011 / 032626, WO2011 / 157339, WO2012 / 007086, WO2015 / 036074, WO2015 / 104045, WO2015 / 117718, and WO2016 / 015815, the preferred composition is an iridium-platinum complex.

[0268] Phosphorescent organometallic complexes having multi-legged ligands are also particularly preferred, such as those described in, for example, WO2004 / 081017, WO2005 / 042550, US2005 / 0170206, WO2009 / 146770, WO2010 / 102709, WO2011 / 066898, WO2016124304, WO2017 / 032439, WO2018 / 019688, EP3184534 and WO2018 / 011186.

[0269] Phosphorescent binuclear organometallic complexes, such as those described in, for example, WO2011 / 045337, US20150171350, WO2016 / 079169, WO2018 / 019687, WO2018 / 041769, WO2018 / 054798, WO2018 / 069196, WO2018 / 069197, and WO2018 / 069273, are also particularly preferred.

[0270] Copper complexes are particularly preferred, such as those described in, for example, WO2010 / 031485, US2013150581, WO2013 / 017675, WO2013 / 007707, WO2013 / 001086, WO2012 / 156378, WO2013 / 072508, and EP2543672.

[0271] Specific examples of phosphorus photosensitizers are Ir(ppy)3 and its derivatives, as well as the structures listed below:

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278] Other specific examples of phosphorus photosensitizers are iridium and platinum complexes containing carbene ligands and the structures listed below, wherein homopolymeric and heteropolymeric complexes, as well as hydroxyl and planar isomers, can be suitable:

[0279]

[0280] Other specific examples of phosphorus photosensitizers include copper complexes and the structures listed below:

[0281]

[0282] In addition to the compounds according to the invention, suitable TADF compounds are those in which the band gap between the lowest triplet state T1 and the first excited singlet state S1 is sufficiently small such that the S1 state can be reached thermally from the T1 state. Preferably, the band gap between the lowest triplet state T1 and the first excited singlet state S1 in the TADF compound is ≤0.30 eV. More preferably, the band gap between S1 and T1 is ≤0.20 eV, even more preferably ≤0.15 eV, particularly more preferably ≤0.10 eV, and even more particularly preferably ≤0.08 eV.

[0283] The energies of the lowest excited singlet state (S1) and lowest triplet state (T1), as well as the HOMO and LUMO values, were determined by quantum chemical calculations. The Gaussian09 package (Revision D or later) was used. The neutral ground-state geometry of all purely organic molecules was optimized at the AM1 theoretical level. Subsequently, single-point calculations using B3PW91 / 6-31G(d) were performed, including calculations of the lowest singlet and triplet excited states using TD-B3PW91 / 6-31G(d). The HOMO and LUMO values, as well as the S1 and T1 excitation energies, were taken from these single-point calculations at the B3PW91 / 6-31G(d) theoretical level.

[0284] Similarly, for organometallic compounds, the neutral ground-state geometry was optimized at the HF / LANL2MB theoretical level. Subsequently, B3PW91 / 6-31G(d)+LANL2DZ (LANL2DZ for all metal atoms, 6-31G(d) for all low-weight elements) was used to calculate the HOMO and LUMO values ​​and the TD-DFT excitation energy.

[0285] The calculated HOMO (HEh) and LUMO (LEh) values ​​are given in Hartree units. The HOMO and LUMO energy levels, calibrated by cyclic voltammetry measurements, are thus determined in electron volts as follows:

[0286] HOMO(eV)=((HEh 27.212)-0.9899) / 1.1206

[0287] LUMO(eV)=((LEh 27.212)-2.0041) / 1.385

[0288] These values ​​are considered, in the context of this invention, to be the HOMO and LUMO energy levels of the material.

[0289] The lowest triplet T1 is defined as the energy of the lowest TD-DFT triplet excitation energy.

[0290] The lowest excitation singlet state S1 is defined as the energy of the lowest TD-DFT singlet state excitation energy.

[0291] Preferably, the TADF compound is an organic compound. In the context of this invention, an organic compound is a carbon-containing compound that does not contain any metals. More specifically, the organic compound is formed from the elements C, H, D, B, Si, N, P, O, S, F, Cl, Br, and I.

[0292] TADF compounds are more preferably aromatic compounds having donor and acceptor substituents, with only slight spatial overlap between the LUMO and HOMO of the compound. The nature of the donor and acceptor substituents is known in principle to those skilled in the art. Suitable donor substituents are, in particular, diarylamino or diheteroarylamino groups and carbazole groups or carbazole derivatives, each preferably bonded to the aromatic compound via an N-bond. These groups may also have further substitutions. Suitable acceptor substituents are, in particular, cyano groups, but also, for example, electron-deficient heteroaryl groups, which may also have further substitutions, such as substituted or unsubstituted triazine groups.

[0293] The preferred dopant concentration of the TADF compound in the emissive layer is described below. Due to variations in the fabrication of organic electroluminescent devices, the dopant concentration is reported as volume % when the emissive layer is fabricated by vapor deposition, and as weight % when the emissive layer is fabricated from solution. Dopant concentrations expressed as volume % and weight % are generally very similar.

[0294] In a preferred embodiment of the present invention, when the light-emitting layer is fabricated by vapor deposition, the TADF compound is present in the light-emitting layer at a dopant concentration of 1 vol% to 70 vol%, more preferably 5 vol% to 50 vol%, or even more preferably 5 vol% to 30 vol%.

[0295] In a preferred embodiment of the invention, when the light-emitting layer is manufactured from a solution, the TADF compound is present in the light-emitting layer at a dopant concentration of 1 wt% to 70 wt%, more preferably 5 wt% to 50 wt%, or even more preferably 5 wt% to 30 wt%.

[0296] General technical knowledge in the art includes knowledge of which materials are typically suitable as TADF compounds. For example, the following references disclose materials that may be suitable for use as TADF compounds:

[0297] -Tanaka et al., Chemistry of Materials 25(18), 3766 (2013).

[0298] -Lee et al., Journal of Materials Chemistry C 1(30), 4599 (2013).

[0299] -Zhang et al., Nature Photonics advance online publication, 1 (2014), doi: 10.1038 / nphoton.2014.12.

[0300] -Serevicius et al., Physical Chemistry Chemical Physics 15(38), 15850(2013).

[0301] -Li et al., Advanced Materials 25(24), 3319 (2013).

[0302] -Youn Lee et al., Applied Physics Letters 101(9), 093306 (2012).

[0303] -Nishimoto et al., Materials Horizons 1, 264 (2014), doi: 10.1039 / C3MH00079F.

[0304] -Valchanov et al., Organic Electronics, 14(11), 2727 (2013).

[0305] -Nasu et al., ChemComm, 49, 10385 (2013).

[0306] In addition, the following patent applications disclose potential TADF compounds: US2019058130, WO18155642, WO18117179A1, US2017047522, US2016372682A, US2015041784, US2014336379, US2014138669, WO 2013 / 154064, WO 2013 / 133359, WO 2013 / 161437, WO 2013 / 081088, WO 2013 / 081088, WO 2013 / 011954, JP 2013 / 116975 and US 2012 / 0241732.

[0307] Furthermore, those skilled in the art can infer the design principles of TADF compounds from these publications. For example, Valchanov et al. demonstrate how the color of TADF compounds can be adjusted.

[0308] Examples of suitable molecules for TADF are the structures shown in the table below:

[0309]

[0310]

[0311] As described above, in superfluorescent or superphosphorescent systems, compounds of formula (1) or those according to preferred embodiments can be used as a combination of a phosphor and a sensitizer. In this case, compounds of formula (1) are preferably spatially shielding. For example, compounds of formula (1) corresponding to formulas (5) and (6), and more particularly (5-1) to (5-3), are well-suited for use as spatially shielding phosphors in the luminescent layer in combination with sensitizers selected from TADF compounds and phosphorescent compounds. Preferably, the luminescent layer further comprises at least one organic functional material selected from the matrix material.

[0312] The compound of formula (1) or according to the 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, phosphor, phosphorescent, delayed phosphor, matrix material, host material, wide bandgap material and quantum material, said quantum material being, for example, quantum dot and quantum rod.

[0313] Formula (1) or the compound according to the preferred embodiment can also be used in other layers, for example as a hole transport material in a hole injection or hole transport layer or an electron blocking layer, or as a matrix material in a light-emitting layer.

[0314] The preferred categories of materials used as corresponding functional materials in the organic electroluminescent devices according to the present invention are as follows.

[0315] Suitable charge transport materials that can be used in the hole injection or hole transport layer or electron blocking layer or electron transport layer of the electronic device according to the present invention are, for example, compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials used in these layers according to the prior art.

[0316] Materials that can be used in the electron transport layer are all materials used as electron transport materials in the electron transport layer according to existing technology. Particularly suitable are aluminum complexes, such as Alq3; zirconium complexes, such as Zrq4; lithium complexes, such as LiQ; benzimidazole derivatives; triazine derivatives; pyrimidine derivatives; pyridine derivatives; pyrazine derivatives; quinoxaline derivatives; and quinoline derivatives. Diazole derivatives, aromatic ketones, lactams, boranes, phosphazacyclopentane derivatives, and phosphine oxide derivatives. Furthermore, suitable materials are derivatives of the above compounds, such as those disclosed in JP 2000 / 053957, WO 2003 / 060956, WO2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300.

[0317] Preferred hole transport materials that can be used in the hole transport layer, hole injection layer, or electron blocking layer of the electroluminescent device according to the present invention are indene-fluoreneamine derivatives (e.g., according to WO 06 / 122630 or WO 06 / 100896), amine derivatives disclosed in EP1661888, hexaazatriphenylide derivatives (e.g., according to WO 01 / 049806), amine derivatives containing fused aromatic rings (e.g., according to US 5,061,569), amine derivatives disclosed in WO 95 / 09147, monobenzo[a]indenefluoreneamine (e.g., according to WO 08 / 006449), dibenzo[a]indenefluoreneamine (e.g., according to WO 07 / 140847), spirodifluoreneamine (e.g., according to WO 2012 / 034627 or WO 2013 / 120577), fluoreneamine (e.g., according to application EP1661888), amine derivatives disclosed in WO 01 / 049806, amine derivatives containing fused aromatic rings (e.g., according to US 5,061,569), amine derivatives disclosed in WO 95 / 09147, monobenzo[a]indenefluoreneamine (e.g., according to WO 08 / 006449), dibenzo[a]indenefluoreneamine (e.g., according to WO 07 / 140847), spirodifluoreneamine (e.g., according to WO 2012 / 034627 or WO 2013 / 120577), fluoreneamine (e.g., according to application EP1661888), amine derivatives containing fused aromatic ring Compounds according to the invention can also be used as hole transport materials. (Examples include 2875092, EP2875699 and EP 2875004), spirodibenzopyranamine (e.g. according to WO 2013 / 083216), and dihydroacridine derivatives (e.g. according to WO 2012 / 150001).

[0318] The cathode of an organic electroluminescent device preferably comprises: a metal with low work function, a metal alloy comprising various metals, or a multilayer structure, such as alkaline earth metals, alkali metals, main group metals, or lanthanides (e.g., Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Also suitable are alloys comprising alkali metals or alkaline earth metals and silver, such as alloys comprising magnesium and silver. In the case of a multilayer structure, in addition to the aforementioned metals, other metals with relatively high work functions, such as Ag and Al, can be used. In this case, combinations of metals, such as Ca / Ag, Mg / Ag, or Ag / Ag, are typically used. It is also preferable to introduce a thin interlayer of material with a high dielectric constant between the metal cathode and the organic semiconductor. Suitable for this purpose are, for example, alkali metal fluorides or alkaline earth metal fluorides, and the corresponding oxides or carbonates (e.g., LiF, Li₂O, BaF₂, MgO, NaF, CsF, Cs₂CO₃, etc.). Furthermore, lithium quinoline (LiQ) can be used for this purpose. The thickness of the layer is preferably between 0.5 nm and 5 nm.

[0319] The anode preferably comprises a material with a high work function. The anode preferably has a work function greater than 4.5 eV relative to vacuum. On one hand, metals with high redox potentials, such as Ag, Pt, or Au, are suitable for this purpose. On the other hand, metal / metal oxide electrodes (e.g., Al / Ni / NiO) are also preferred. x Al / PtO x For some applications, at least one of the electrodes must be transparent or partially transparent to facilitate the irradiation of organic materials (organic solar cells) or the coupling and output of light (OLEDs, O-lasers). The preferred anode material is a conductive mixed metal oxide. Indium tin oxide (ITO) or indium zinc oxide (IZO) is particularly preferred. Furthermore, conductive doped organic materials, especially conductive doped polymers, are preferred.

[0320] The device is appropriately (depending on the application) constructed to provide contact and ultimately seal, because the lifespan of the device according to the invention is shortened in the presence of water and / or air.

[0321] In a preferred embodiment, the organic electroluminescent device according to the invention is characterized by applying one or more layers by means of a sublimation process, wherein the material is sublimated in a vacuum sublimation unit at a concentration of less than 10... -5 millibars, preferably less than 10 -6 An initial pressure of millibars is applied via vapor deposition. However, this initial pressure can also be even lower, for example, less than 10. -7 millibar.

[0322] Such organic electroluminescent devices are also preferred, characterized by the application of one or more layers via OVPD (organic vapor deposition) or carrier gas sublimation, wherein the material is in a 10 -5 The pressure is applied between millibar and 1 bar. A specific example of this process is OVJP (Organic Vapor Jet Printing), in which material is applied directly through a nozzle and thus structured (e.g., MS Arnold, etc.). Applied Physics Lett. 2008, 92 , 053301).

[0323] Furthermore, an organic electroluminescent device is preferred, characterized in that one or more layers are manufactured from a solution, for example by spin coating, or by any desired printing process such as screen printing, flexographic printing, nozzle printing, or offset printing, but particularly preferably by LITI (photoinitiated thermal imaging, thermal transfer) or inkjet printing. For this purpose, a compound of soluble formula (I) is required. High solubility can be achieved through appropriate substitution of the compound.

[0324] It can also be a hybrid process, in which one or more layers are applied from a solution and one or more additional layers are applied by vapor deposition. Thus, for example, a light-emitting layer can be applied from a solution and an electron transport layer can be applied by vapor deposition.

[0325] These processes are generally known to those skilled in the art and can be applied to organic electroluminescent devices containing compounds according to the present invention without any inventive effort.

[0326] According to the present invention, electronic devices comprising one or more compounds according to the present invention can be used in displays, as light sources in lighting applications, and as light sources in medical and / or cosmetic applications (e.g., phototherapy).

[0327] The invention will now be explained in more detail through the following embodiments, but it is not intended to limit it thereto.

[0328] A) Synthetic Example

[0329] Example 1: Compound 1

[0330] The compound known from the literature has CAS number 1359015-54-5 ( J. Org. Chem. 2012, 77 (4), 2074-2079) reacts with trimethylphenylboronic acid (CAS 5980-97-2) in a Suzuki coupling reaction. The intermediate can be further reacted to a borate ester using the methods described in the literature [5] to give compound 1 of the present invention.

[0331]

[0332] B) OLED manufacturing

[0333] The compounds of the present invention can be used as triplet matrix materials in the emissive layer of OLEDs or as phosphors in the emissive layer of OLEDs.

[0334] Peak emission wavelength max The determination

[0335] To determine the peak emission wavelength of the phosphor, the phosphor was dissolved in toluene at a concentration of 1 mg / 100 mL. The solution was excited in a Hitachi F-4500 fluorescence spectrometer using a wavelength matched to the material. Measurements were performed at room temperature. Peak emission wavelength. max It is the wavelength of the first maximum value in the emission spectrum. Usually, the first maximum value is also the global maximum value of the spectrum.

[0336] Compound 1 emits blue light and can be used as a blue fluorescent light source in OLEDs.

Claims

1. A compound of formula (1), The following applies to the symbols and markings used: X 1 Representing CR in the same or different ways each time it appears. 1 Or N; X 2 Representing CR in the same or different ways each time it appears. 2 Or N; X A Representing CR in the same or different ways each time it appears. A Or N; Y 1 Represents a single bond or selected from -C(R) Y )2-、-C(R Y )2-C(R Y )2-、-Si(R Y Divalent bridge bases of -O, -S, -S(=O)2- and -C(=O)-; Y 2 Representative selected from -C(R) Y )2-、-C(R Y )2-C(R Y )2-、-Si(R Y Divalent bridge bases of -O, -S, -S(=O)2- and -C(=O)-; R B Each occurrence may represent, in the same or different manner, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R)2, Si(R)3,2, OSO2R, 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 which may be substituted by one or more R groups, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si (R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R, or an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R, or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R; R Y R N Each occurrence may represent, in the same or different manner, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, N(R)2, Si(R)3, B(OR)2, OSO2R, 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 which may be substituted by one or more R groups, wherein in each case one or more non-adjacent CH2 groups may be RC=C R, C≡C, Si(R)₂, Ge(R)₂, Sn(R)₂, C=O, C=S, C=Se, P(=O)(R), SO, SO₂, O, S, or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO₂, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R, or an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R, or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R; wherein two adjacent substituents R Y It can form monocyclic or polycyclic aliphatic or aromatic ring systems, which can be substituted by one or more groups R´; R 1 R 2 R A Each occurrence may represent, in the same or different manner, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R)3, B(OR)2, OSO2R, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si(R)2, etc. Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S, or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2; an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R; an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R; or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R; wherein R is selected from... 1 R 2 R A Two adjacent groups can form a monocyclic or polycyclic aliphatic or aromatic ring system, which can be substituted by one or more groups R; R, in each occurrence, may represent, in the same or different ways, H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, NO2, Si(R')3, B(OR')2, OSO2R', a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R', wherein in each case one or more non-adjacent CH2 groups may be R'C=CR', C≡C, or Si(R')2. The aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R' in each case, or an aryloxy group having 5 to 60 aromatic ring atoms, wherein the aryloxy group may be substituted by one or more groups R', wherein two adjacent groups R may form a monocyclic or polycyclic aliphatic ring system or aromatic ring system, wherein the aliphatic ring system or aromatic ring system may be substituted by one or more groups R'; Ar is, in each occurrence, the same or different, an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which in each case may also be substituted by one or more groups R'; R´, in each occurrence, may represent H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 20 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 carbon atoms, wherein in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, 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 carbon atoms.

2. The compound according to claim 1, characterized in that... The compound is selected from compounds of formula (2). 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 compounds of formula (3). 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... R B Each occurrence, whether identical or different, 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 which may be substituted by one or more groups R, wherein in each case, one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si(R)2, Ge(R)2, S n(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S or CONR are substituted, and one or more H atoms may be substituted by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R, or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted by one or more groups R.

5. The compound according to one or more of the preceding claims, characterized in that... R B Each occurrence may represent, in the same or different manner, 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, each of which may be substituted by one or more groups R, wherein one or more H atoms may be substituted by D, F, Cl, or CN, or an aromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic ring system may be substituted by one or more groups R, or an aralkyl or heteroaralkyl group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaralkyl group may be substituted by one or more groups R.

6. The compound according to one or more of the preceding claims, characterized in that... R B Selected in the same or different ways each time it appears -A branched or cyclic alkyl group represented by the following general formula (RS-a), (RS-a) in R 22 R 23 R 24 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 25 Substitution, and wherein the group R 22 R 23 R 24 Two or all of the R groups in 22 R 23 R 24 It can be linked to form a (poly)cycloalkyl group, said (poly)cycloalkyl group being posterior to one or more groups R 25 replace; R 25 Each time it appears, it 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, either identically or differently. The condition is that each time it appears, group R... 22 R 23 and R 24 At least one of them is not H, provided that each time it appears, all groups R are present. 22 R 23 and R 24 Together they have at least 4 carbon atoms, and the condition is that each time they appear, if the group R 22 R 23 R 24 If two of them are H, then the remaining groups are not straight chains; - or a branched or cyclic alkoxy group represented by the following general formula (RS-b), (RS-b) in R 26 R 27 R 28 Each time it appears, it 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, wherein each of the above groups may be represented by one or more groups R as defined above. 25 Substitution, and wherein the group R 26 R 27 R 28 Two or all of the R groups in 26 R 27 R 28 It can be linked to form a (poly)cycloalkyl group, said (poly)cycloalkyl group being capable of being formed by one or more groups R as defined above. 25 replace; The condition is that each time it appears, group R... 26 R 27 and R 28 Only one of them can be H; - or an aralkyl group represented by the following general formula (RS-c), (RS-c) in R 29 R 30 R 31 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Substitution, and wherein the group R 29 R 30 R 31 Two or all of them can be linked to form a (poly)cycloalkyl group or an aromatic ring system, each of which can be represented by one or more groups R. 32 replace; R 32 Each time it appears, it is selected from the same or different straight-chain alkyl groups having 1 to 10 carbon atoms, or branched or cyclic alkyl groups having 3 to 10 carbon atoms, or aromatic ring systems having 6 to 24 aromatic ring atoms; The condition is that each time it appears, group R... 29 R 30 and R 31 At least one of them is not H, and the condition is that each time it appears, the group R... 29 R 30 and R 31 At least one of them 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 an aromatic ring system represented by the following general formula (RS-d), (RS-d) in R 40 To R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Substitution, and wherein the group R 40 To R 44 Two or more of them can be linked to form a (poly)cycloalkyl group or an aromatic ring system, each of which can be represented by one or more groups R as defined above. 32 replace.

7. The compound according to one or more of the preceding claims, characterized in that... R 2 and R A Each occurrence may represent, in the same or different manner, H, D, F, Cl, Br, I, CN, N(Ar)2, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be RC=CR, C≡C, Si(R)2, Ge(R)2, Sn( The aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted with one or more groups R in each case, or an aralkyl or heteroaromatic group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic group may be substituted with one or more groups R.

8. The compound according to one or more of the preceding claims, characterized in that... R 2 and R A Each instance may represent H, D, F, CN, a straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40 carbon atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40 carbon atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be substituted by RC=CR, C≡C, O, or S, and wherein one or more H atoms may be substituted by D or F, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R, or an aralkyl or heteroaromatic ring group having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic ring group 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 and R A Represents the same or different each time it appears. -H, D, F, CN; or - 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 formulas (RS-a), (RS-b), (RS-c), and (RS-d) have the same definition as in claim 6; or - Groups of formula (ArL-1), In equation (ArL-1), the dashed bond represents the bond with the structure of equation (1), where Ar 2 Ar 3 Each occurrence may represent, in the same or different ways, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case; and wherein m is an integer selected from 1 to 10.

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

11. The compound according to one or more of the preceding claims, characterized in that... R B and R A The groups selected from formulas (RS-a), (RS-b), (RS-c), and (RS-d) are the same or different each time they appear, wherein the groups of formulas (RS-a), (RS-b), (RS-c), and (RS-d) have the same definition as in claim 6.

12. The compound according to one or more of the preceding claims, characterized in that... The compound is selected from compounds of formula (5) or (6). Wherein group R A It has the same meaning as in claim 1; and In equation (5), R 40 R 42 R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Replace; where R 32 Same as defined in claim 6; The condition is R 40 R 42 R 44 At least one of them is not H; or In equation (6), R 41 R 43 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Replace; where R 32 Same as defined in claim 6; The condition is R 41 R 43 At least one of them is not H.

13. The compound according to claim 12, characterized in that, R 42 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Substitution, or an aromatic ring system having 6 to 30 aromatic ring atoms, wherein in each case the aromatic ring system may be replaced by one or more groups R 32 Replace, where R 32 Same as defined in claim 6; R 40 R 44 Each occurrence is either identical or different from an aromatic ring system having 6 to 30 aromatic ring atoms, which in each case may be selected by one or more groups R. 32 Replace; where R 32 Same as defined in claim 6.

14. The compound according to one or more of the preceding claims, characterized in that... The compounds are selected from those of formulas (5-1), (5-2), and (5-3). Wherein group R A It has the same meaning as in claim 1, and wherein, In each of equations (5-1), (5-2), and (5-3), use -R 32 The phenyl group shown is unsubstituted or substituted with one or more R groups. 32 replace; R 42 and R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Replace; where R 32 Same as defined in claim 6.

15. The compound according to one or more of the preceding claims, characterized in that... The compounds are selected from those of formulas (5-1-a) to (5-3-g). Wherein group R A R Y R has the same meaning as in claim 1, and wherein in each of formulas (5-1-a) to (5-3-g), -R is used. 32 The phenyl group shown is unsubstituted or substituted with one or more R groups. 32 replace; R 42 and R 44 Each occurrence thereof is selected from H, either identically or differently, of a straight-chain alkyl group having 1 to 10 carbon atoms, or of a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein each of the above groups may be converted by one or more groups R. 32 Replace; where R 32 Same as defined in claim 6.

16. The compound according to claim 12, characterized in that... Group R 40 R 42 R 44 Each occurrence thereof is selected, either identically or differently, 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, wherein each of the above groups may be represented by one or more groups R. 32 Replace; where R 32 Same as defined in claim 6.

17. A polymer, oligomer, or dendritic macromolecule comprising one or more compounds according to claim 1, wherein one or more bonds attached to the polymer, oligomer, or dendritic macromolecule may be located in formula (I) by R 1 R 2 R A R B Or R replaces any position.

18. A formulation comprising at least one compound according to one or more of claims 1 to 16 or at least one polymer, oligomer or dendritic macromolecule according to claim 17 and at least one solvent.

19. An electronic device comprising at least one compound according to one or more of claims 1 to 16 or at least one polymer, oligomer or dendritic macromolecule according to claim 17, wherein the electronic device is selected from organic electroluminescent devices, organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic solar cells, dye-sensitized organic solar cells, organic optical detectors, organic photosensors, organic field quenching devices, luminescent electrochemical cells, organic laser diodes and organic plasma light-emitting devices.

20. An organic electroluminescent device, said organic electroluminescent device comprising at least one compound according to one or more of claims 1 to 16 or at least one polymer, oligomer or dendritic macromolecule according to claim 17, characterized in that The compound according to one or more of claims 1 to 16 or the polymer, oligomer or dendritic macromolecule according to claim 17 is used as the luminescent agent in the luminescent layer.

21. The organic electroluminescent device according to claim 20, characterized in that... The compound according to one or more of claims 1 to 16 or the polymer, oligomer or dendritic macromolecule according to claim 17 is used as a phosphor in the luminescent layer, wherein the luminescent layer comprises at least one additional component selected from the matrix material.

22. The organic electroluminescent device according to claim 20, characterized in that... The compound according to one or more of claims 1 to 16 or the polymer, oligomer or dendritic macromolecule according to claim 17 is used as a photoluminescent material that displays thermally activated delayed fluorescence in a light-emitting layer, wherein the light-emitting layer comprises at least one additional component selected from the matrix material.

23. The organic electroluminescent device according to claim 20, characterized in that... The compound according to one or more of claims 1 to 16 or the polymer, oligomer or dendritic macromolecule according to claim 17 is used as a phosphor in the luminescent layer, wherein the luminescent layer contains at least one sensitizer selected from phosphorescent compounds and thermally activated delayed fluorescence compounds.

24. The organic electroluminescent device according to claim 23, characterized in that... The light-emitting layer also contains at least one organic functional material selected from the matrix material.

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