Materials for organic electroluminescent devices

Abstract

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

Description

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

[0002] The development of functional compounds for electronic devices is currently 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 device power efficiency and lifetime, as well as the color coordinates of emission.

[0003] According to the present invention, the term electronic device is particularly considered to refer to organic integrated circuits (OIC), organic field-effect transistors (OFET), organic thin-film transistors (OTFT), organic light-emitting transistors (OLET), organic solar cells (OSC), organic optical detectors, organic photosensors, organic field quenching devices (OFQD), organic light-emitting electrochemical cells (OLEC), organic laser diodes (O-lasers), and organic electroluminescent devices (OLED).

[0004] 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.

[0005] 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.

[0006] A key starting point for achieving these improvements is the selection of the luminescent compound and the host compound used in the electronic device.

[0007] Blue fluorescent emitters known in the art are a variety of compounds. Arylamines containing one or more fused aryl groups are known in the art. Arylamines containing dibenzofuran groups (as disclosed in US2017 / 0012214) or indonodibenzofuran groups (as disclosed in CN 10753308) are also known in the art.

[0008] 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 with a sufficiently small band gap between their lowest triplet state T1 and first excited singlet state S1, allowing thermal excitation from the T1 state to the S1 state. For quantum statistical reasons, during electronic excitation in OLEDs, 75% of the excited states are in triplet states, while 25% are in singlet states. Since purely organic molecules typically cannot efficiently emit light from triplet states, 75% of the 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 molecule's first excited singlet state 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, it 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.

[0009] 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.

[0010] However, additional phosphors, especially blue phosphors, are still needed for OLEDs, which would result in very good characteristics 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.

[0011] Recently, organic electroluminescent devices (OLEDs) have been described that incorporate a TADF compound as a sensitizer and a fluorescent compound as a luminescent body with high steric shielding relative to its environment in the luminescent layer (e.g., in WO2015 / 135624). This device construction allows for the provision of organic electroluminescent devices that emit light in all emission colors, thereby utilizing the basic structure of known fluorescent luminescent bodies while still exhibiting the high efficiency of TADF-containing OLEDs. This is also known as superfluorescence.

[0012] As an alternative, existing technologies describe organic electroluminescent devices that include a phosphorescent organometallic complex as a sensitizer in the emitting layer. This sensitizer exhibits a mixture of S1 and T1 states due to large spin-orbit coupling, and includes a fluorescent compound as the emitting agent, thereby significantly shortening the emission decay time. This is also known as superphosphorescence.

[0013] Superfluorescence and superphosphorescence are also promising technologies for improving OLED performance, especially in deep blue emission.

[0014] 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 achievable color values, especially color purity.

[0015] A key starting point for achieving these improvements in superfluorescent and superphosphorescent systems is the selection of the phosphor compound, which can advantageously be a sterically hindered phosphor compound. For example, sterically hindered phosphors based on rubrene are described in WO 2015 / 135624.

[0016] Furthermore, it is known that OLEDs can comprise different layers, which can be applied by vapor deposition in a vacuum chamber or by processing from a solution. In the case of materials used to manufacture layers applied from a solution, the materials should have good solubility in the solution containing them.

[0017] This invention is based on the technical objective of providing a light emitter that displays transient fluorescence and / or delayed fluorescence. It is also based on the technical objective of providing a sterically hindered fluorescent light emitter that can be used in combination with a sensitizer compound in a superfluorescent or superphosphorescent system. Furthermore, this invention is based on the technical objective of providing compounds suitable for use as light emitters in electronic devices such as OLEDs and suitable for vacuum processing or solution processing.

[0018] In the study of novel compounds for electronic devices, compounds of formula (1) as defined below have been found to be highly suitable for use in electronic devices. In particular, they achieve one or more of the above-mentioned technical objectives, preferably all of them.

[0019] Therefore, this invention relates to compounds of formula (1),

[0020]

[0021] The following applies to the symbols and markings used:

[0022] X represents CR the same or different each time it appears. X Or N;

[0023] Y 1 Represents B(R) 0 ), Si(R) 0 2. C=O, C=NR N C = C(R) 0)2、O、S、S=O、

[0024] SO2, N(R) N ), P(R 0 ) or P(=O)R 0 ;

[0025] Y 2 Y 3 and Y 4 Represents B(R) in the same or different ways each time it appears. 0 ), C(R 0 )2、Si(R 0 2. C=O, C=NR N C = C(R) 0 )2, O, S, S=O, SO2, N(R N ), P(R 0 ) or P(=O)R 0 ;

[0026] R X R 0 R N Each occurrence may represent, in the same or different manner, H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R)2, N(Ar)2, 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, Ge( Aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, wherein the aromatic or heteroaromatic ring system is replaced by one or more groups R in each case, and one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2; aralkyl or heteroaromatic groups having 5 to 60 aromatic ring atoms, wherein the aralkyl or heteroaromatic groups may be replaced by one or more groups R; or aryloxy or heteroaromatic groups having 5 to 60 aromatic ring atoms, wherein the aryloxy or heteroaromatic groups may be replaced by one or more groups R; wherein two adjacent groups R X They can together form an aliphatic, aromatic, or heteroaromatic ring system, wherein the aliphatic, aromatic, or heteroaromatic ring system can be substituted by one or more groups R; and wherein two adjacent groups R 0They can be combined to form aliphatic, aromatic, or heteroaromatic ring systems, wherein the aliphatic, aromatic, or heteroaromatic ring system can be substituted by one or more groups R;

[0027] R, in each occurrence, may represent H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R′)2, N(Ar)2, 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 further classified by one or more groups R. ′ Substitution, wherein in each case one or more non-adjacent CH2 groups may be replaced by R ′ C = CR ′ C≡C, Si(R) ′ )2、Ge(R ′ )2、Sn(R ′ )2. C=O, C=S, C=Se, P(=O)(R ′ ), SO, SO2, O, S or CONR ′ An aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, wherein one or more H atoms may be replaced by D, F, Cl, Br, I, CN, or NO2, and said aromatic or heteroaromatic ring system may in each case be replaced by one or more R groups. ′ Substitution; wherein two adjacent substituents R can together form an aliphatic or aromatic ring system, which can be substituted by one or more groups R. ′ replace;

[0028] Ar, in each occurrence, is either identical or different, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which in each case may also be influenced by one or more R groups. ′ replace;

[0029] 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 20 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 20 C 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 aromatic ring atoms;

[0030] n, m, and p are either 0 or 1 each time they appear, and when n, m, or p is 0, the corresponding group Y... 2 Y 3 Or Y 4 It does not exist and is related to Y 2 Y 3 and Y 4 The bond is replaced by the group X.

[0031] 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.

[0032] In addition, the following definitions of chemical groups are applicable to the purposes of this application:

[0033] 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, then those preferred features apply.

[0034] Here, aryl groups or heteroaryl groups are 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.

[0035] In each case, aryl or heteroaryl groups that can be substituted by the aforementioned groups and can be linked to the aromatic or heteroaromatic ring system via any desired position are particularly considered to refer to groups derived from the following substances: benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, leucine, perylene, fluoranthene, benzo[a]anthene, benzo[a]phenanthrene, tetraphenylbenzene, pentaphenylbenzene, benzo[a]pyrene, 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, pyridinium imidazoles, pyrazinium imidazoles, quinoxaline imidazoles 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, indazine, and benzothiadiazole.

[0036] The aryloxy group defined according to the present invention is considered to be an aryl group as defined above, bonded via an oxygen atom. A similar definition applies to heteroaryloxy groups.

[0037] According to 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.

[0038] 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. In the context of this invention, an aromatic or heteroaromatic ring system 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 C 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, and systems in which 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 in which two or more aryl or heteroaryl groups are linked to each other via single bonds are also considered aromatic or heteroaromatic ring systems in the sense of this invention, for example, systems such as biphenyl, terphenyl, or diphenyltriazine.

[0039] 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, pyridinium imidazoles, pyrazinium imidazoles, quinoxaline imidazoles 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-tetraazaperylene, 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, indazine, and benzothiadiazole, or combinations of these groups.

[0040] For the purposes of this invention, individual H atoms or CH2 groups may be replaced by 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, preferably considered to be groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2- Methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, or 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, sec-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, 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.

[0041] For the purposes of this application, the statement that two or more groups can form a ring with each other is intended to be understood, in particular, to mean that two groups are connected to each other by chemical bonds. This is illustrated by the following scheme:

[0042]

[0043] However, the above statement is also intended to mean that, in cases where one of the two groups represents hydrogen, the second group is bonded at the site where the hydrogen atom is bonded, thus forming a ring. This is illustrated by the following scheme:

[0044]

[0045] Preferably, at least one of the markers n, m, or p is equal to 1.

[0046] The following combinations are preferred:

[0047] n is 0, m is 0 and p is 1;

[0048] n is 0, m is 1 and p is 0;

[0049] n is 1, m is 0 and p is 1;

[0050] n is 1, m is 1 and p is 0;

[0051] n is 1, m is 0 and p is 0;

[0052] n is 0, m is 1, p is 1;

[0053] n is 1, m is 1, and p is 1.

[0054] More preferably, m+p equals 1 or 2.

[0055] Preferably, the group Y 1 Represents B(R) 0 ), O, S or N (R) N ), more preferably representing O, S or N (R) N ), which is more preferably represented by N(R) N ).

[0056] Preferably, the group Y 2 Y 3 and Y 4 Represents B(R) in the same or different ways each time it appears. 0 ), C(R 0 )2、Si(R 0 2. C = O, O, S or N(R) N ), more preferably represented by C(R) 0 2. C = O, O, S or N(R) N ), which is more preferably represented by C(R) 0 )2 or N(R N Particularly preferred is that the compound of formula (1) contains at least one substance representing N(R). N The group Y) 2 Y 3 Or Y 4 .

[0057] Preferably, the compound of formula (1) is selected from the compounds of formulas (2) to (6).

[0058]

[0059] The symbols have the same meaning as described above.

[0060] More preferably, the compound of formula (1) is selected from the compounds of formulas (2-1) to (6-1).

[0061]

[0062] The symbols have the same meaning as described above.

[0063] Particularly preferably, the compound of formula (1) is selected from compounds of formulas (2-1-1) to (6-1-2).

[0064]

[0065] The symbols have the same meaning as described above.

[0066] Very particularly preferably, the compound of formula (1) is selected from compounds of formulas (2-1-1a) to (6-1-2a).

[0067]

[0068] The symbols have the same meaning as described above.

[0069] Preferably, in formulas (2-1-1a) to (6-1-2a), the symbol Y... 2 and Y 3 Selected from C(R) in the same or different ways each time it appears. 0 2. C = O, O, S and N(R) N More preferably C(R) 0 )2 and N(R N ), more preferably N(R) N ).

[0070] According to a preferred embodiment, the compound of formula (1) comprises at least one group R selected from the group consisting of... X R N Or R 0 ,

[0071] -A branched or cyclic alkyl group represented by the following general formula (RS-a),

[0072]

[0073] in

[0074] 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 surrounded by one or more groups R. 25 Substitution, and wherein the group R 22 R 23R 24 Both or all of the groups R 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;

[0075] 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 in the same or different manner.

[0076] 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 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 and R 24 If both of them are H, then the remaining groups are not straight chains;

[0077] -A branched or cyclic alkoxy group represented by the following general formula (RS-b),

[0078]

[0079] in

[0080] 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 surrounded by one or more groups R as defined above. 25 Substitution, and wherein the group R 26 R 27 R 28 Both or all of the groups R 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;

[0081] The condition is that group R appears each time. 26 R 27 and R 28 Only one of them can be H;

[0082] - An aralkyl group represented by the following general formula (RS-c),

[0083]

[0084] in

[0085] 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 surrounded 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 Both or all of them can be linked to form a (poly)cycloalkyl group or an aromatic ring system, each of which can be linked by one or more groups R. 32 replace;

[0086] R 32 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, or aromatic ring systems having 6 to 24 aromatic ring atoms;

[0087] 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 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

[0088] -Aromatic ring systems represented by the following general formula (RS-d),

[0089]

[0090] in

[0091] R 40 To R 44Each 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 surrounded 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 these groups may be linked to form a (poly)cycloalkyl group or an aromatic ring system, each of which may be linked by one or more groups R as defined above. 32 replace;

[0092] The dashed bond represents the corresponding group R. X R N Or R 0 Bonding to the rest of the structure.

[0093] Examples of suitable groups of formula (RS-a) to (RS-d) are groups (RS-1) to (RS-78):

[0094]

[0095]

[0096] The dashed lines indicate the bonding of these groups to 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 The substituted groups (RS-48) to (RS-78) can also be replaced by at least one group R as defined above. 32 replace.

[0097] According to a preferred embodiment, the compound of formula (1) comprises at least one group R selected from the group of formula (ArL-1). X R N Or R 0 ,

[0098]

[0099] In formula (ArL-1), the dashed bond represents the corresponding group R. X R N Or R 0 Bonding to the rest of the structure, where Ar 2 Ar 3Each occurrence represents, in the same or different manner, 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.

[0100] Preferably, the marker m in the group of formula (ArL-1) is an integer selected from 1 to 6, very preferably 1 to 4, and very more preferably 1 and 2.

[0101] In formula (ArL-1), the preferred group is Ar. 2 Groups selected from formulas (Ar2-1) to (Ar2-25),

[0102]

[0103]

[0104]

[0105] The dashed bond represents the structure of formula (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:

[0106] 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)-

[0107] -C(=NR 0 )-、-C=(C(R 0 ))2-, -O-, -S-, -S(=O)-, -SO2-, -N(R 0 )-、-P(R 0 )- and -P((=O)R 0 )-, preferably selected from -C(R 0 ) 2- 、-Si(R 0 ) 2- -O-, -S-, or -N(R) 0 )-;and

[0108] R 0 It has the same definition as above.

[0109] According to a preferred embodiment, at least one Ar group in formula (ArL-1) 2 The group represented by formula (Ar2-2) and / or at least one Ar group 3 The group represented by formula (Ar3-2)

[0110]

[0111] in

[0112] 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.

[0113] 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 group 3 The group represented by the formula (Ar3-2-1)

[0114]

[0115] in

[0116] The dashed bond in formula (Ar2-2-1) represents the structure of formula (1) and the Ar group. 2 Or Ar 3 Bonding;

[0117] The dashed key in equation (Ar3-2-1) represents the key to Ar. 2 Bonding;

[0118] E 4 It has the same meaning as above; and

[0119] 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.

[0120] 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)

[0121]

[0122] in

[0123] The dashed bond in formula (Ar2-2-1b) represents the structure of formula (1) and the Ar group. 2 Or Ar 3 Bonding;

[0124] The dashed key in equation (Ar3-2-1b) represents the key to Ar. 2 Bonding;

[0125] R 0 It has the same meaning as above; and

[0126] 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.

[0127] Preferably, the group R 0 Representing the same or different times each time it appears.

[0128] -H, D;

[0129] - having 1 to 20, preferably 1 to 10, straight-chain alkyl groups, or having 3 to 20, preferably 3 to 10, branched or cyclic alkyl groups, each of which may be substituted by one or more groups R;

[0130] - 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 the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case;

[0131] - Groups as defined above in formulas (RS-a), (RS-b), (RS-c), or (RS-d); or

[0132] - Groups as defined above in formula (ArL-1);

[0133] Two adjacent groups R 0 They can be combined to form aliphatic, aromatic, or heteroaromatic ring systems, which can be substituted by one or more groups R.

[0134] Very preferably, group R 0 Representing the same or different times each time it appears.

[0135] -H;

[0136] - having 1 to 10, preferably 1 to 5, straight-chain alkyl groups, or having 3 to 10, preferably 3 to 5, branched or cyclic alkyl groups, each of which may be substituted by one or more groups R;

[0137] - An aromatic or heteroaromatic ring system having 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;

[0138] Two adjacent groups R 0 They can be combined to form aliphatic, aromatic, or heteroaromatic ring systems, which can be substituted by one or more groups R.

[0139] When two adjacent groups R 0 When they form a ring system together, they preferably form the formula (R) 0 -1) ring,

[0140]

[0141] Wherein (R) 0 The group of (-1) can be replaced by one or more groups R, and the dashed bond indicates a bond with the structure of formula (1).

[0142] Preferably, R X Representing the same or different times each time it appears.

[0143] -H, D, F, Cl, Br, I, CN or N(Ar)2;

[0144] - A straight-chain alkyl, alkoxy, or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more groups R, wherein in each case one or more non-adjacent CH2 groups may be substituted by 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 and wherein one or more H atoms may be substituted by D, F, Cl, Br, I, CN, or NO2;

[0145] - 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 the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case;

[0146] - Groups as defined above in formulas (RS-a), (RS-b), (RS-c), or (RS-d); or

[0147] - Groups as defined above in formula (ArL-1);

[0148] Two adjacent groups R X They can be combined to form aliphatic, aromatic, or heteroaromatic ring systems, which can be substituted by one or more groups R.

[0149] More preferably, R X Representing the same or different times each time it appears.

[0150] -H, D, F, or CN;

[0151] - having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms, of straight-chain alkyl or alkoxy groups, or having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, of branched or cyclic alkyl or alkoxy groups, each of which may be substituted by one or more groups R, and wherein one or more H atoms may be substituted by D or F;

[0152] - 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 the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case;

[0153] - Groups as defined above in formulas (RS-a), (RS-b), (RS-c), or (RS-d); or

[0154] - Groups as defined above in formula (ArL-1);

[0155] Two adjacent groups R X They can be combined to form aliphatic, aromatic, or heteroaromatic ring systems, which can be substituted by one or more groups R.

[0156] Very suitable group R X Examples include H, D, F, CN, substituted and unsubstituted straight-chain alkyl groups having 1 to 10 carbon atoms, more particularly methyl, ethyl, propyl, butyl, substituted and unsubstituted branched or cyclic alkyl groups having 3 to 10 carbon atoms, more particularly tert-butyl, and groups of formulas (Ar1-1) to (Ar1-24).

[0157]

[0158]

[0159] In equations (Ar1-1) to (Ar1-24):

[0160] - Dashed lines indicate bonds between groups and the rest of the structure;

[0161] -R N0 R C0 In each occurrence, the same or different groups are H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy, or thioalkoxy group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms, or a cyclic alkyl, alkoxy, or thioalkoxy 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 one or more non-adjacent CH2 groups may be substituted by (R)C=C(R), C≡C, O, or S, and wherein 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, 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 optionally two adjacent groups R C0 They can form monocyclic or polycyclic aliphatic, aromatic, or heterocyclic ring systems with each other;

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

[0163] Preferably, R N Representing the same or different meanings each time it appears.

[0164] -H, D;

[0165] - having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms, straight-chain alkyl groups, or having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, branched or cyclic alkyl groups, 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;

[0166] - 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 the aromatic or heteroaromatic ring system may be substituted by one or more groups R in each case;

[0167] - Groups as defined above in formulas (RS-a), (RS-b), (RS-c), or (RS-d); or

[0168] - Groups as defined above in formula (ArL-1).

[0169] More preferably, R N Representing the same or different meanings each time it appears.

[0170] - An aromatic or heteroaromatic ring system having 5 to 30, preferably 5 to 18, aromatic ring atoms, preferably selected from phenyl, biphenyl, terphenyl, tetraphenyl, fluorene, spirodifluorene, naphthalene, anthracene, phenanthrene, biphenylene oxide, fluoranthene, indole, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, indole-carbazole, indole-carbazole, phenanthrene-rhein, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinolone, benzopyridine, benzopyridazine, benzopyrimidine, quinazoline, benzimidazole, or a combination of two or three of these groups, each of which may be substituted by one or more groups R;

[0171] - Groups as defined above in formulas (RS-a), (RS-b), (RS-c), or (RS-d); or

[0172] - Groups as defined above in formula (ArL-1).

[0173] Very suitable group R N Examples are groups of formulas (Ar1-1) to (Ar1-24) as described above.

[0174] Preferably, the group R, in each occurrence, represents H, D, F, Cl, Br, I, CHO, CN, N(Ar)2, Si(R′)3, having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms, of a straight-chain alkyl, alkoxy, or thioalkyl group, or having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, of a branched or cyclic alkyl, alkoxy, or thioalkyl group, each of which may be one or more of the following: A plurality of groups R′ are substituted, wherein in each case one or more non-adjacent CH2 groups may be replaced by R′C=CR′, O or S and wherein 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 in each case one or more groups R′ are substituted, wherein two adjacent groups R can form a monocyclic or polycyclic aliphatic or aromatic ring system, wherein one or more aliphatic or aromatic ring system may be substituted by one or more groups R′. When R is selected from aromatic and heteroaromatic ring systems, it is preferably selected from aromatic and heteroaromatic ring systems having 5 to 40, preferably 5 to 30, more preferably 5 to 18 aromatic ring atoms, or selected from aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, corresponding to groups of formula (ArL-1) as defined above.

[0175] Preferably, the Ar group is, in each occurrence, an aromatic or heteroaromatic ring system having 5 to 18, preferably 6 to 18, aromatic ring atoms, and in each case may also be substituted by one or more R′ groups.

[0176] 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 C atoms, or a branched or cyclic alkyl, alkoxy, or thioalkyl group having 3 to 10 C 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 C atoms.

[0177] Examples of suitable compounds of formula (1) are the structures shown in the table below:

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] 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 described in general terms in Schemes 1 and 5 below.

[0184] Option 1

[0185]

[0186] Option 2

[0187]

[0188] Wherein R is a group and X1 to X4 are leaving groups, preferably selected from -OH and halogens (I, Br, Cl, F). More preferably, X1 is -OH, X2 is Br, X3 is Cl and X4 is I.

[0189] Option 3

[0190]

[0191] R, X2, and X3 have the same meaning as described above.

[0192] Option 4

[0193]

[0194] R, X2, and X3 have the same meaning as described above.

[0195] Option 5

[0196]

[0197] Wherein R is a group, and X2 and X5 are leaving groups, preferably selected from halogens (I, Br, Cl, F). More preferably, X2 is Br and X5 is F.

[0198] 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, it is preferable to use a mixture of two or more solvents. Suitable and preferred solvents include, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthol, veratrine, THF, methyl-THF, THP, chlorobenzene, dichlorobenzene, 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, naphthane, dodecyl Alkylbenzene, 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.

[0199] Therefore, the present invention also relates to formulations 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. Such additional compounds may also be polymerized.

[0200] The compounds and mixtures according to the invention are suitable for use in electronic devices. Electronic devices herein are considered to be devices comprising at least one layer containing at least one organic compound. However, the components herein may also comprise inorganic materials or layers composed entirely of inorganic materials.

[0201] Therefore, the present invention also relates to the use of compounds or mixtures according to the invention in electronic devices, particularly in organic electroluminescent devices.

[0202] Furthermore, the present invention also relates to electronic devices comprising at least one of the compounds or mixtures described above according to the present invention. The preferred features stated above regarding the compounds also apply to electronic devices.

[0203] 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" (DMKoller et al., Nature Photonics 2008, 1-4), with organic electroluminescent devices (OLED, PLED) being the most preferred, especially phosphorescent OLEDs.

[0204] 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 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 in each case. Similarly, an intermediate layer with, 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. The organic electroluminescent device described herein may include one or more emitting layers. If multiple emitting layers are present, these emitting layers preferably collectively have multiple luminescence 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 the three layers exhibit blue, green, and orange or red light emission (see, for example, WO2005 / 011013 for the basic structure). These can be fluorescent or phosphorescent emitting layers or a hybrid system in which fluorescent and phosphorescent emitting layers are combined with each other.

[0205] The compounds according to the present invention based on the above embodiments can be used in multiple layers, depending on the precise structure and substitutions.

[0206] 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 particularly, 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.

[0207] According to another preferred embodiment of the invention, formula (1) or the compound according to the preferred embodiment is used in a superfluorescent system as described, for example, in 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 transmitted via Foster. The resonant energy is transferred to the fluorescent light source.

[0208] According to another preferred embodiment of the invention, the compound of formula (1) or according to the preferred embodiment is used in a superphosphorescent system as described, for example, in 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.

[0209] The compound of formula (1) can also be used in electron transport layers and / or electron blocking or exciton blocking layers and / or hole transport layers, depending on precise substitution. The preferred embodiments described above are also applicable to the use of the material in organic electronic devices.

[0210] The compound of formula (1) is particularly suitable for use as a blue emitting compound. The electronic device involved may include a single emitting layer comprising the compound according to the invention, or it may include two or more emitting layers. Additional emitting layers herein may comprise one or more compounds according to the invention or other compounds.

[0211] 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.

[0212] 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 .

[0213] 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%.

[0214] For the purposes of this application, percentages expressed in % are considered to be volume% if the compound is applied from the gas phase and weight% if the compound is applied from a solution.

[0215] 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: oligoarylene (e.g., 2,2',7,7'-tetraphenylspirodifluorene or dinathyne anthracene according to EP676461), particularly oligoarylene containing fused aromatic groups, oligoarylene vinylidenes (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 arylene compounds, including naphthalene, anthracene, benzo[a]anthracene and / or pyrene or transisomers of these compounds, oligomeric arylene vinylides, ketones, phosphine oxides and sulfoxides. Very particularly preferred matrix materials are selected from the following categories: oligomeric arylene compounds, including anthracene, benzo[a]anthracene, benzo[a]phenanthrene and / or pyrene or transisomers of these compounds. In the context of this invention, oligomeric arylene compounds are intended to be considered as compounds in which at least three aryl or arylene groups are bonded to each other.

[0216] The particularly preferred matrix materials used in combination with the compound of formula (1) used as a phosphor in the luminescent layer are depicted in the table below:

[0217]

[0218]

[0219]

[0220]

[0221] 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.

[0222] In addition to the compounds according to the invention, preferred fluorescent emitters are selected from the arylamine class. For the purposes of this invention, arylamines 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 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 diarylamino group 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 group is preferably bonded to pyrene at position 1 or at positions 1 and 6. Other preferred luminescent agents are indenefluoreneamine or indenefluorene diamine, for example according to WO 2006 / 108497 or WO 2006 / 122630; benzo[a]indenefluoreneamine or benzo[a]indenefluorene diamine, for example according to WO 2008 / 006449; dibenzo[a]indenefluoreneamine or dibenzo[a]indenefluorene diamine, for example according to WO 2007 / 140847; and indenefluorene derivatives containing fused aryl groups disclosed in WO 2010 / 012328. Other preferred luminescent materials are benzene-anthracene derivatives as disclosed in WO 2015 / 158409, anthracene derivatives as disclosed in WO 2017 / 036573, fluorene dimers as disclosed in WO 2016 / 150544, or phenanthrene as disclosed in WO 2017 / 028940 and WO 2017 / 028941. Azide derivatives. Pyrene arylamines disclosed in WO 2012 / 048780 and WO 2013 / 185871 are also preferred. 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 are also preferred.

[0223] Examples of preferred fluorescent luminescent compounds, other than those according to the invention, that can be used in combination with the compounds of the invention in a light-emitting layer or in another light-emitting layer of the same device, are described in the following table:

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] 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, such as those according to WO 2010 / 136109 or WO 2011 / 000455; azacarbazole derivatives, such as those according to EP1617710, EP 1617711, EP 1731584, JP 2005 / 347160; bipolar matrix materials, such as those according to WO2007 / 137725; silanes, such as those according to WO 2005 / 111172; borazocyclopentane or borate esters, such as those according to WO2006 / 117052; silylatedazacyclopentane derivatives, such as those according to WO 2010 / 054729; phosphorus diazacyclopentane derivatives, such as those according to WO The following are acceptable matrix materials: those of WO 2010 / 054730; triazine derivatives, such as those according to WO 2010 / 015306, WO 2007 / 063754 or WO 2008 / 056746; pyrimidine derivatives, quinoxaline derivatives, Zn complexes, Al complexes or Be complexes, such as those according to EP 652273 or WO 2009 / 062578; or bridged carbazole derivatives, such as those according to US2009 / 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. Mixtures of two or more of these matrix materials may also be used.

[0231] The matrix compound used for TADF light emitters is preferably charge-transporting, i.e., electron-transporting or hole-transporting, 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.

[0232] 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 electron-conducting compound is a purely organic compound, i.e., a metal-free compound.

[0233] 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.

[0234] Particularly preferred is that T1 (matrix) ≥ T1 (sensitizer).

[0235] More preferably: T1 (matrix) - T1 (sensitizer) ≥ 0.1 eV;

[0236] The preferred option is: T1 (matrix) - T1 (sensitizer) ≥ 0.2 eV.

[0237] 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.

[0238] 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.

[0239] Suitable phosphorescent emitters, particularly those emitting light upon 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.

[0240] For the purposes of this invention, all luminescent iridium, platinum, or copper complexes are considered phosphorescent compounds.

[0241] 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 US2005 / 0258742. Generally, all phosphorescent complexes known to those skilled in the art for use in phosphorescent OLEDs and in the field of organic electroluminescent devices are suitable for use in the devices according to the present invention. Those skilled in the art will also be able to combine other phosphorescent complexes with the compounds according to the present invention for use in OLEDs without inventive effort.

[0242] 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, US2005 / 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 US2009 / 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.

[0243] 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.

[0244] Furthermore, phosphorescent organometallic complexes having multi-legged ligands are 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.

[0245] Furthermore, 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 particularly preferred.

[0246] Furthermore, copper complexes are particularly preferred, as described in, for example, WO2010 / 031485, US2013150581, WO2013 / 017675, WO2013 / 007707, WO2013 / 001086, WO2012 / 156378, WO2013 / 072508, and EP2543672.

[0247] Specific examples of phosphorus photosensitizers are Ir(ppy)3 and its derivatives, as well as the structures listed below:

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] 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, may be suitable:

[0256]

[0257] Other specific examples of phosphorus photosensitizers include copper complexes and the structures listed below:

[0258]

[0259] 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.

[0260] 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.

[0261] 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)) was used for all low-weight elements to calculate the HOMO and LUMO values ​​and the TD-DFT excitation energy.

[0262] 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:

[0263] HOMO(eV)=((HEh*27.212)-0.9899) / 1.1206

[0264] LUMO(eV)=((LEh*27.212)-2.0041) / 1.385

[0265] These values ​​are considered, in the context of this invention, to be the HOMO and LUMO energy levels of the material.

[0266] The lowest triplet T1 is defined as the energy of the lowest TD-DFT triplet excitation energy.

[0267] The lowest excited singlet state S1 is defined as the energy of the lowest TD-DFT singlet state excitation energy.

[0268] 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.

[0269] 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 diarylheterarylamino 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.

[0270] 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 produced by vapor deposition, and as weight % when the emissive layer is produced from solution. Dopant concentrations expressed as volume % and weight % are generally very similar.

[0271] In a preferred embodiment of the 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%, and even more preferably 5 vol% to 30 vol%.

[0272] In a preferred embodiment of the invention, when the luminescent layer is manufactured from a solution, the TADF compound is present in the luminescent layer at a dopant concentration of 1 wt% to 70 wt%, more preferably 5 wt% to 50 wt%, and even more preferably 5 wt% to 30 wt%.

[0273] 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:

[0274] -Tanaka et al., Chemistry of Materials 25(18), 3766(2013).

[0275] -Lee et al., Journal of Materials Chemistry C 1(30), 4599(2013).

[0276] -Zhang et al., Nature Photonics advance online publication, 1(2014), doi:10.1038 / nphoton.2014.12.

[0277] -Serevicius et al., Physical Chemistry Chemical Physics 15(38), 15850(2013).

[0278] -Li et al., Advanced Materials 25(24), 3319(2013).

[0279] -Youn Lee et al., Applied Physics Letters 101(9), 093306(2012).

[0280] -Nishimoto et al., Materials Horizons 1, 264 (2014), doi:10.1039 / C3MH00079F.

[0281] -Valchanov et al., Organic Electronics, 14(11), 2727(2013).

[0282] -Nasu et al., ChemComm, 49, 10385 (2013).

[0283] 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 US2012 / 0241732.

[0284] 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.

[0285] Examples of suitable molecules for TADF are the structures shown in the table below:

[0286]

[0287]

[0288]

[0289] 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, it is preferred that the compound of formula (1) is 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 includes at least one organic functional material selected from the matrix material.

[0290] 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.

[0291] 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.

[0292] The general preferred categories of materials used as corresponding functional materials in the organic electroluminescent devices according to the present invention are as follows.

[0293] Suitable charge transport materials that can be used in the hole injection layer, hole transport layer, 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.

[0294] Materials that can be used in electron transport layers are all materials used as electron transport materials in electron transport layers 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, WO 2004 / 028217, WO 2004 / 080975, and WO 2010 / 072300.

[0295] 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 disclosed in WO 06 / 122630 or WO 06 / 100896), amine derivatives disclosed in WO 06 / 122630 or WO 06 / 10089 ... Compounds according to the invention can also be used as hole transport materials. These include compounds such as 2875092, EP2875699 and EP 2875004, spirodibenzopyranamine (e.g. according to WO 2013 / 083216), and dihydroacridine derivatives (e.g. according to WO 2012 / 150001).

[0296] The cathode of an organic electroluminescent device preferably comprises a metal with a low work function, a metal alloy comprising various metals, or a multilayer structure, such as alkaline earth metals, alkali metals, 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 or 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 this layer is preferably between 0.5 nm and 5 nm.

[0297] 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. Suitable for this purpose are metals with high redox potentials, such as Ag, Pt, or Au. On the other hand, metal / metal oxide electrodes (e.g., Al / Ni / NiO) are also suitable. x Al / PtO x Alternatively, it can be preferred. 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 here is a conductive mixed metal oxide. Indium tin oxide (ITO) or zinc indium oxide (IZO) is particularly preferred. Furthermore, conductive doped organic materials, especially conductive doped polymers, are preferred.

[0298] The device is appropriately (depending on the application) structured to provide contact connections and ultimately seal, because the lifespan of the device according to the invention is shortened in the presence of water and / or air.

[0299] In a preferred embodiment, the organic electroluminescent device according to the invention is characterized by applying one or more layers via 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, the initial pressure can also be lower, for example, less than 10. -7 millibar.

[0300] Such organic electroluminescent devices are also preferred, characterized by the application of one or more layers via an OVPD (organic vapor deposition) process or by means of carrier gas sublimation, wherein the material is in a 10 -5 The pressure is applied between millibar and 1 bar. A special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the material is applied directly through the nozzle and thus structured (e.g., MS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).

[0301] Furthermore, such organic electroluminescent devices are 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 soluble compound of formula (I) is required. High solubility can be achieved through appropriate substitution of the compound.

[0302] 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.

[0303] These methods are generally known to those skilled in the art and can be applied by them to organic electroluminescent devices containing compounds according to the present invention without creative effort.

[0304] 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).

[0305] The invention will now be explained in more detail through the following embodiments, but it is not intended to limit it thereto.

[0306] A) Synthetic Example

[0307] Unless otherwise stated, the following synthesis was carried out in a dry solvent under a protective gas atmosphere. Solvents and reagents are available from Sigma-Aldrich or ABCR. The CAS numbers of compounds known from the literature are also indicated below. Compounds according to the invention can be synthesized by synthetic methods known to those skilled in the art.

[0308] a) 1,6-Dibromo-5,10-bis(2-chlorophenyl)boranethracene

[0309]

[0310] A suspension of 21.0 g (57.4 mmol) of 1,6-dibromo-5,10-dihydro-5,10-dihydroxy-boronanthracene was added to 2000 mL of benzene in a glass tube fitted with a PTFE stopcock. Then, 29.0 g (11 mL, 120 mmol) of BBr3 was added to the solution at room temperature. The resulting clear solution was heated to 80 °C, the tube was sealed, and this temperature was maintained for 6 hours. The mixture was stirred overnight at room temperature, after which a small amount of solid precipitated. The supernatant was then transferred through the tube to a Schlenk tube and placed under vacuum to remove all volatile vapors.

[0311] The solid residue was mixed with 50 ml of heptane and kept in an ultrasonic bath, then connected to a vacuum again to remove the remaining BBr3.

[0312] The residue was recrystallized into hot hexane. The residue was then dissolved in toluene and cooled to -78°C.

[0313] 236 mL (118 mmol) of bromine (2-chlorophenyl-magnesium (0.5 M THF solution) was added to the solution. The reaction mixture was heated to room temperature overnight and then quenched with saturated NH4Cl aqueous solution. The two liquid phases were separated, the aqueous phase was extracted with CHCl3 (3 × 150 mL), the combined organic phases were dried over MgSO4, concentrated under vacuum and purified by column chromatography (silica gel, CHCl3:n-hexane = 1:9), and finally purified by sublimation.

[0314] The yield was 19g (34mmol), which is 60% of the theoretical value.

[0315] The following compounds can be obtained similarly:

[0316]

[0317] b) Cycloning (Buchwald)

[0318]

[0319] 11 g (20 mmol) of 1,6-dibromo-5,10-bis(2-chlorophenyl)borane, 0.95 g (1 mmol) of tris(dibenzylacetone)dipalladium, 4 mL (1 M) of t-Bu3P in toluene, and 4.6 g (48 mmol) of sodium tert-butoxide were added to 200 mL of toluene. Then, 1.8 g (16 mmol) of aniline was added to the mixture. The mixture was then heated to 110 °C and held for 20 hours, then cooled to room temperature and 100 mL of water was added. The aqueous phase was then extracted with acetate, and the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from toluene and heptane / methanol and finally purified by sublimation.

[0320] The yield was 3.3g (8.64mmol), which is 43% of the theoretical value. 1 The purity after H-NMR was approximately 87%.

[0321] The following compounds can be obtained similarly:

[0322]

[0323] c) N1,N4-bis(3-bromo-2-chloro-phenyl)-N1,N4-diphenyl-phenyl-1,4-diamine

[0324]

[0325] 10 g (34.7 mmol, 1 equivalent) of N,N'-diphenyl-1,4-phenylenediamine was mixed with 91 g (340 mmol, 10 equivalents) of 1,3-dibromo-2-chlorobenzene and 10 g (111 mmol, 3 equivalents) of sodium tert-butoxide in 150 mL of anhydrous toluene in a 2 L four-necked flask and degassed for 30 min. Then, 310 mg (1.3 mmol, 0.04 eq) of palladium(II) acetate and 1.5 g (2.7 mmol, 0.08 eq) of DPPF were added, and the mixture was heated under reflux overnight. When the reaction was complete, the batch was cooled to room temperature and extracted with 500 mL of water. The aqueous phase was then washed three times with toluene, and the combined organic phases were dried over sodium sulfate and the solvent was removed using a rotary evaporator. The brown residue was mixed with about 200 mL of toluene and filtered through silica gel. Further purification was performed by recrystallization from toluene / heptane.

[0326] The yield was 19.9 g (31 mmol), which is 81% of the theoretical value. 1 The purity after H-NMR was approximately 89%.

[0327] The following compounds can be obtained similarly:

[0328]

[0329] d)N3-[4-(N-(3-anilino-2-chloro-phenyl)anilino)phenyl]-2-chloro-N1,N3-diphenyl-phenyl-1,3-diamine

[0330]

[0331] 19.1 g (30 mmol, 1 equivalent) of N1,N4-bis(3-bromo-2-chloro-phenyl)-N1,N4-diphenyl-phenyl-1,4-diamine, 8.3 g (90 mmol, 3 equivalent) of aniline, and 8 g (90 mmol, 3 equivalent) of sodium tert-butoxide were placed in 150 mL of anhydrous toluene in a 2 L four-necked flask and degassed for 30 min. Then, 286 mg (1.2 mmol, 0.04 equivalent) of palladium(II) acetate and 1.3 g (2.4 mmol, 0.08 equivalent) of DPPF were added, and the mixture was heated under reflux overnight. After the reaction was complete, the batch was cooled to room temperature and extracted with 500 mL of water. The aqueous phase was then washed three times with toluene, and the combined organic phases were dried over sodium sulfate and the solvent removed by rotary evaporation. The brown residue was absorbed in approximately 200 mL of toluene and filtered through silica gel. For further purification, recrystallization from toluene / heptane was performed.

[0332] The yield was 17.8 g (26 mmol), which is 90% of the theoretical value. 1 The purity after H-NMR was approximately 88%.

[0333] The following compounds can be obtained similarly:

[0334]

[0335]

[0336] e) Cycloforming (Buchwald)

[0337]

[0338] In a 2 L four-necked flask, 13.26 g (20 mmol, 1 equivalent) of N3-[4-(N-(3-anilino-2-chloro-phenyl)anilino)phenyl]-2-chloro-N1,N3-diphenyl-phenyl-1,3-diamine was mixed with 4.7 g (20 mmol, 3 equivalents) of 1-,4-dibromobenzene and 5.3 g (60 mmol, 3 equivalents) of sodium tert-butoxide in 150 mL of anhydrous toluene and degassed for 30 min. Then, 0.73 g (0.8 mmol, 0.04 eq) of Pd(dba)2 and 2.9 mL (1-M toluene solution, 0.6 mmol, 0.08 equivalents) of tri-tert-butylphosphine were added to the mixture, and the mixture was heated under reflux overnight. When the reaction was complete, the mixture was cooled to room temperature and extracted with 500 mL of water. The aqueous phase was then washed three times with toluene, and the combined organic phases were dried over sodium sulfate and the solvent was removed by rotary evaporation. The brown residue was mixed with approximately 200 ml of toluene and filtered through silica gel. For further purification, recrystallization was performed from toluene / heptane.

[0339] The yield was 6g (8.2mmol), which is 41% of the theoretical value. 1 The purity after H-NMR was approximately 88%.

[0340] f) Complexation

[0341]

[0342] Compound (e)

[0343] A pentane solution of 31.6 mL (1.70 M, 53.7 mmol) of tert-butyllithium was slowly added to a solution of 33 g (44.7 mmol) of compound (e) in 150 mL of tert-butylbenzene at -30 °C under a nitrogen atmosphere. After stirring at 60 °C for 2 hours, the pentane was removed under vacuum. 5.1 mL (53.9 mmol) of boron tribromide was added at -30 °C, and the reaction mixture was stirred at room temperature for 0.5 hours. Then, 15.6 mL (91.1 mmol) of N-diisopropylethylamine was added at 0 °C, and the reaction mixture was heated to room temperature. After stirring at 120 °C for 3 hours, the reaction mixture was cooled to room temperature. An aqueous solution of 13.0 g of sodium acetate in 100 mL of water and 50 mL of ethyl acetate was added to the reaction mixture. The aqueous layer was separated and extracted with 100 mL of ethyl acetate. The combined organic phases were concentrated under vacuum. The residue was dissolved in toluene and filtered through a silica gel filter (eluent: toluene). The solvent was removed under vacuum.

[0344] The residue was recrystallized from toluene / heptane and finally purified by sublimation.

[0345] The yield was 9.2g (13.4mmol), which is 30% of the theoretical value. 1 The purity after H-NMR was approximately 99.9%.

[0346] The following compounds can be obtained similarly:

[0347]

[0348]

[0349] g) 2,3-Dibromo-N1,N1,N4,N4-Tetraphenyl-phenyl-1,4-diamine

[0350]

[0351] 33 g (200 mmol, 2 equivalences) of diphenylenediamine was placed in a 2 L four-necked flask and mixed with 48 g (100 mmol, 3 equivalences) of 2,3-dibromo-1,4-diiodobenzene and 28 g (300 mmol, 1 equivalence) of sodium tert-butoxide in 150 mL of anhydrous toluene and degassed for 30 min. Then, 1.34 g (6 mmol, 0.03 eq) of Pd(OAc)₂ and 5.78 g (10 mmol, 0.05 eq) of Xantphos were added and the mixture was heated overnight to 110 °C. When the reaction was complete, the mixture was cooled to room temperature and extracted with 500 mL of water. The aqueous phase was then washed three times with toluene, and the combined organic phases were dried over sodium sulfate and the solvent was removed by rotary evaporation. The brown residue was mixed with about 200 mL of toluene and filtered through silica gel. For further purification, recrystallization was performed from toluene / heptane.

[0352] The yield was 39 g (69 mmol), equivalent to 71% of the theoretical value. The purity after 1H NMR was approximately 87%.

[0353] h)2,3-Bis(dimethylsilyl)-N1,N1,N4,N4-Tetraphenyl-phenyl-1,4-diamine

[0354]

[0355] A hexane solution of n-BuLi (13.2 ml, 1.6 M, 21 mmol) was added dropwise to 5.7 g (10 mmol) of 2,3-dibromo-N1,N1,N4,N4-tetraphenyl-phenyl-1,4-diamine in 50 ml of freshly distilled THF at -78 °C. The reaction mixture was then stirred for 1.5 hours and 2.6 ml (24 mmol) of dichlorosilane was added.

[0356] The reaction mixture was heated overnight at room temperature with stirring. The mixture was then quenched with water (15 ml) and extracted with CH₂Cl₂ (3 × 50 ml). The organic phase was dried over anhydrous Na₂SO₄ and concentrated under vacuum. The crude product was purified by silica gel rapid column chromatography.

[0357] The yield was 4.8g (9.1mmol), which is 91% of the theoretical value. 1 The purity after H-NMR was approximately 87%.

[0358] i) Cycloning

[0359]

[0360] 26 g (50 mmol) of 2,3-bis(dimethylsilyl)-N1,N1,N4,N4-tetraphenyl-phenyl-1,4-diamine, 32 ml (250 mmol) of 3,3-dimethyl-1-butene, 230 mg (0.25 mmol) of RhCl(PPh3)3, and 500 ml of 1,4-diphenyl-phenyl-1,4-diamine were added. The mixture of alkanes was stirred at 135°C for 24 hours. The solvent was then removed under vacuum, and the products were separated by silica gel column chromatography.

[0361] The yield was 23.9 g (45 mmol), which is 93% of the theoretical value. 1 The purity after H-NMR was approximately 91%.

[0362] j) Cycloning

[0363]

[0364] Compound (i)

[0365] At room temperature, 10 mL (26.4 g, 105 mmol) of BBr3 was added to a solution of 10.4 g (20 mmol) of compound (i) in 200 mL of anhydrous CH2Cl2. After stirring at the same temperature for 4.5 hours, the mixture was concentrated under vacuum at 50 °C.

[0366] The resulting mixture was dissolved in 70 mL of anhydrous toluene. At 0 °C, 20 mL (1 M solution, 20 mmol) of a freshly prepared 1,2-phenylenedilithium solution synthesized from diiodobenzene and t-BuLi in THF was added to the solution. After stirring at 50 °C for 20 hours, the mixture was mixed with a saturated aqueous NH₄Cl solution. The organic layer was separated, and the aqueous layer was extracted three times with CH₂Cl₂. The combined organic phases were dried over Na₂SO₄, filtered, and concentrated under reduced pressure.

[0367] The product was recrystallized in toluene and finally purified by sublimation.

[0368] The yield was 8g (15.9mmol), which is 80% of the theoretical value. 1 The purity after H-NMR was approximately 99.9%.

[0369] B) OLED manufacturing

[0370] OLED manufacturing is based on processes described, for example, in WO 04 / 058911 and adapted to individual conditions (e.g., layer thickness variations to achieve optimal efficiency or color).

[0371] A glass substrate coated with structured ITO (indium tin oxide) forms the substrate of the OLED. In principle, the OLED has the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL1) 60nm / hole transport layer (HTL2) 20nm / emitting layer (EML) 30nm / electron transport layer (ETL) 20nm, and finally, a cathode. All materials are applied in a vacuum chamber via thermal vapor deposition. The emitting layer here always consists of at least one matrix material (host material) and a light-emitting dopant (emitter), which is mixed with one or more matrix materials in a specific volume ratio through co-evaporation. The cathode is formed from a 1nm thin LiF layer and a 100nm Al layer deposited thereon. Table 1 shows the chemical structures of the materials used to construct the OLED.

[0372] The OLED was characterized using standard methods. For this purpose, electroluminescence spectra were measured, and efficiency (in cd / A), power efficiency (in lm / W), and operating voltage (V) as a function of luminescence density were calculated from the current-voltage-luminescence density characteristics exhibiting Lambertian radiation. Electroluminescence spectra were obtained at 1000 cd / m². 2 The luminous density was determined, and the CIE 1931 x and y color coordinates were established. The lifetime was defined as 6000 cd / m². 2 (For blue OLED) or 25000 cd / m 2 The time after dividing the initial luminous density (for green OLEDs) by 2.

[0373] Tables 2 and 3 summarize the results for some OLEDs (Examples E1 to E10). The compounds of Examples E1 and E2 were used as the host materials of the present invention or as light-emitting materials for green light emission. The compounds of Examples E4, E5, E6, E7, E9, and E10 were used as the host materials of the present invention or as blue light-emitting materials.

[0374] The results summarized in Tables 2 and 3 show that the OLED of the present invention results in a significantly improved lifetime compared to OLEDs using current technology. Furthermore, as indicated by the darker blue coordinates, comparable or even higher efficiency is achieved compared to OLEDs using current technology.

[0375] Table 1

[0376]

[0377]

[0378] Table 2

[0379]

[0380] Table 3

[0381]

Claims

1. A compound of formula (1), The following applies to the symbols and markings used: X represents CR the same or different each time it appears. X ; Y 1 Represents N(R) N ); Y 2 Y 3 and Y 4 Represents C(R) in the same or different ways each time it appears. 0 2. C=O, or N(R) N ), and there exists at least one representative N(R) N The group Y) 2 Y 3 Or Y 4 ; R X Each occurrence may represent, in the same or different manner, H, D, F, CN, N(Ar)2, Si(R)3, a straight-chain alkyl or alkoxy group having 1 to 10 C atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, each of which may be substituted by one or more groups R, wherein one or more H atoms may be substituted by D or F, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R; R 0 Each time it appears, it may represent H or D, a straight-chain alkyl group having 1 to 10 C atoms, or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which may be substituted by one or more groups R, wherein one or more H atoms may be substituted by D, or an aromatic or heteroaromatic ring system having 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; Two groups R bonded to the same atom 0 They can together form an aromatic ring system, which can be substituted by one or more groups R; R N Each time it appears, it may represent H, D, a straight-chain alkyl group having 1 to 10 C atoms, or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which may be substituted by one or more groups R, wherein one or more H atoms may be substituted by D or F, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic ring system may be substituted by one or more groups R; R represents H, D, F, CN, N(Ar)2, Si(R) in each occurrence, either the same or different. ´ 3, a straight-chain alkyl group having 1 to 10 C atoms, or a branched or cyclic alkyl group having 3 to 10 C atoms, each of which may be substituted by one or more groups R', wherein one or more H atoms may be substituted by D or F, or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, wherein in each case the aromatic or heteroaromatic 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 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more groups R'; R´ in each occurrence represents, in the same or different, H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms, or a branched or cyclic alkyl group having 3 to 10 C atoms, wherein in each case one or more H atoms may be replaced by D or F, or an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms. n, m, and p are either 0 or 1 each time they appear, and when n, m, or p is 0, the corresponding group Y... 2 Y 3 Or Y 4 It does not exist and is related to Y 2 Y 3 and Y 4 The linked group is replaced by group X, provided that m + p equals 1 or 2. The condition is to exclude the following compounds: ， ， ， ， ， ， ， ， ， ， ， ,and .

2. The compound according to claim 1, characterized in that... Y 2 Y 3 and Y 4 Represents C(R) in the same or different ways each time it appears. 0 )2 or N(R N ).

3. The compound according to claim 1 or 2, characterized in that... The compound is selected from compounds of formulas (2) to (5). The symbols have the same meaning as in claim 1.

4. The compound according to claim 1 or 2, characterized in that... The compound is selected from compounds (2-1-1) to (5-1-1). The symbols have the same meaning as in claim 1.

5. The compound according to claim 1 or 2, characterized in that... The compound contains at least one R group selected from the following groups. X R N Or R 0 : -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 surrounded by 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 in the same or different manner. The condition is that group R appears each time. 22 R 23 and R 24 At least one of them is not H, provided that all groups R appear in each occurrence. 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 and R 24 If both of them are H, then the remaining groups are not straight chains; - 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 surrounded 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; - Aryl groups 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 surrounded 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; R 32 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, 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 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 -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 surrounded 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; The dashed bond represents the corresponding group R. X R N Or R 0 Bonding to the rest of the structure.

6. The compound according to claim 1 or 2, characterized in that... The compound contains at least one group R selected from the formula (ArL-1). X R N Or R 0 , In formula (ArL-1), the dashed bond represents the corresponding group R. X R N Or R 0 Bonding to the rest of the structure, where Ar 2 Ar 3 Each occurrence represents, in the same or different manner, an aromatic or heteroaromatic ring system having 5 to 20 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 2.

7. A polymer comprising one or more compounds according to claim 1, wherein one or more bonds constituting the polymer may be located in formula (1) by R X R 0 R N Or R replaces any position.

8. A formulation comprising at least one compound according to any one of claims 1 to 6 or at least one polymer according to claim 7 and at least one solvent.

9. An electronic device comprising at least one compound according to any one of claims 1 to 6 or at least one polymer according to claim 7 in its light-emitting layer, wherein the electronic device is an organic electroluminescent device.

10. An organic electroluminescent device, said organic electroluminescent device comprising at least one compound according to any one of claims 1 to 6 or at least one polymer according to claim 7, characterized in that... The compound according to any one of claims 1 to 6 or the polymer according to claim 7 is used as the light emitter in the light-emitting layer.

11. The organic electroluminescent device according to claim 10, characterized in that... The compound according to any one of claims 1 to 6 or the polymer according to claim 7 is used as a phosphor in the luminescent layer, wherein the luminescent layer comprises at least one other component selected from the matrix material.

12. The organic electroluminescent device according to claim 10, characterized in that... The compound according to any one of claims 1 to 6 or the polymer according to claim 7 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 other component selected from the matrix material.

13. The organic electroluminescent device according to claim 10, characterized in that... The compound according to any one of claims 1 to 6 or the polymer according to claim 7 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.

14. The organic electroluminescent device according to claim 13, characterized in that... The light-emitting layer also contains at least one organic functional material selected from the matrix material.

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