EP4097090A1 - Dérivés de benzimidazole - Google Patents

Dérivés de benzimidazole

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Publication number
EP4097090A1
EP4097090A1 EP21702244.1A EP21702244A EP4097090A1 EP 4097090 A1 EP4097090 A1 EP 4097090A1 EP 21702244 A EP21702244 A EP 21702244A EP 4097090 A1 EP4097090 A1 EP 4097090A1
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European Patent Office
Prior art keywords
radicals
formula
formulas
compounds
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP21702244.1A
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German (de)
English (en)
Inventor
Philipp Stoessel
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of EP4097090A1 publication Critical patent/EP4097090A1/fr
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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
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    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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Definitions

  • the present invention relates to benzimidazole derivatives for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these benzimidazole derivatives.
  • organic electroluminescent devices in which organic semiconductors are used as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461, WO 98/27136, WO 2004/058911 A2, WO 2010/045729 A2 and KR 2019/0001967 A.
  • Organometallic complexes that exhibit phosphorescence are often used as emitting materials. For quantum mechanical reasons, the use of organometallic compounds as phosphorescence emitters can achieve up to four times the energy and power efficiency.
  • organic electroluminescent devices are known which comprise fluorescent emitters or emitters which exhibit TADF (thermally activated delayed fluorescence).
  • organic electroluminescent devices are not only determined by the emitters used.
  • the other materials used such as host / matrix materials, hole blocking materials, electron transport materials, hole transport materials and electron or exciton blocking materials, are of particular importance here. Improvements in these materials can lead to significant improvements in electroluminescent devices.
  • the compounds should have a high degree of color purity.
  • the object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which lead to good device properties when used in this device, and to provide the corresponding electronic device .
  • the compounds should have excellent processability, and the compounds should in particular show good solubility.
  • the compounds should lead to devices which have excellent color purity.
  • the compounds should be as easy to process as possible, in particular they should exhibit good solubility and film formation.
  • the compounds should exhibit increased oxidation stability and an improved glass transition temperature.
  • a further object can be seen in providing electronic devices with excellent performance as inexpensively as possible and of constant quality
  • the electronic devices should be able to be used or adapted for many purposes.
  • the performance of the electronic devices should be maintained over a wide temperature range.
  • the present invention relates to a compound comprising at least one structure of the formula (I), preferably a compound according to the formula (I),
  • Ring system with 5 to 60 aromatic ring atoms which can be substituted by one or more radicals R, or an aryloxy or heteroaryloxy group with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R;
  • Ar is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, which can be substituted by one or more radicals R, here the group Ar can form a ring system with at least one further group;
  • X stands for N, CR or C, if the group Ar forms a ring system through a bond, with the proviso that not more than two of the groups X in a cycle stand for N;
  • R 1 is on each occurrence, identically or differently, H, D, F, CI, Br, I,
  • R 2 is on each occurrence, identically or differently, selected from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical with 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, in which a or more H atoms can be replaced by D, F, CI, Br, I or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, two or more, preferably adjacent, substituents R 2 with one another form a ring system.
  • an aryl group contains 6 to 40 carbon atoms;
  • a fleteroaryl group contains 2 to 40 carbon atoms and at least one fleteroatom, with the proviso that the sum of carbon atoms and fleteroatoms is at least 5.
  • the fletero atoms are preferably selected from N, 0 and / or S.
  • an aryl group or fleteroaryl group is either a simple aromatic cycle, that is benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or fleteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc., understood.
  • Aromatics linked to one another by a single bond, such as biphenyl, on the other hand, are not referred to as an aryl or fleteroaryl group, but as an aromatic ring system.
  • An electron-poor fleteroaryl group within the meaning of the present invention is a fleteroaryl group which has at least one heteroaromatic six-membered ring with at least one nitrogen atom. Further aromatic or heteroaromatic five-membered rings or six-membered rings can also be fused onto this six-membered ring. Examples of electron-poor fleteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline or quinoxaline. For the purposes of this invention, an aromatic ring system contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system for the purposes of this invention contains 2 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and / or S.
  • An aromatic or heteroaromatic ring system in the context of this invention is understood to mean a system that does not necessarily contain only aryl or heteroaryl groups, but also contains several aryl - Or heteroaryl groups through a non-aromatic unit, such as. B. a C, N or O atom can be connected.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are to be understood as aromatic ring systems for the purposes of this invention, and also systems in which two or more aryl groups are linked, for example, by a short alkyl group.
  • the aromatic ring system is preferably selected from fluorene, 9,9'-spirobifluorene, 9,9-diarylamine or groups in which two or more aryl and / or heteroaryl groups are linked to one another by single bonds.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 20 C atoms, and in which individual H atoms or Chh groups are also substituted by the groups mentioned above can be, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, Cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cyclo-heptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,
  • alkoxy group having 1 to 40 carbon atoms is given to methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy , 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy are stood.
  • a thioalkyl group with 1 to 40 carbon atoms includes, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio,
  • 2-Ethylhexylthio trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cyclothiothio, octenylthynyl, butthiothiothio, propenylthio, cycloheptenynyl, butthiothiothio, octoheptenynyl, ethenylthio, ethenylthio , Hexinylthio, heptinylthio or octinylthio understood.
  • alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, it being possible for one or more non-adjacent CF groups to be replaced by the groups mentioned above; furthermore, one or more H atoms can also be replaced by D, F, CI, Br, I, CN or NO2, preferably F, CI or CN, more preferably F or CN, particularly preferably CN.
  • aromatic or heteroaromatic ring system with 5-60 or 5 to 40 aromatic ring atoms, which can be substituted by the above-mentioned radicals and which can be linked via any positions on the aromatic or fleteroaromatic, who in particular means groups that are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, tetrahydropyrene trans-indenofluoren, cis- or trans-indenocarbazole, cis- or trans -indolocarbazole, truxes
  • 1, 2,4-triazole benzotriazole, 1, 2,3-oxadiazole, 1, 2,4-oxadiazole, 1,2,5-oxadiazole, 1, 3,4-oxadiazole, 1, 2,3 -Thiadiazole, 1, 2,4-thiadiazole, 1, 2,5-thiadiazole, 1, 3,4-thiadiazole, 1, 3,5-triazine, 1, 2,4-triazine, 1, 2 , 3-triazine, tetrazole, 1, 2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived are of combinations of these systems.
  • the compounds according to the invention comprise a structure of the formulas (lilac), (IIIb), (Ille), (II Id) and (Ille), are preferably selected from the compounds of the formulas (lilac) , (lllb), (Ille), (II Id) and (Ille),
  • the compounds according to the invention comprise a structure of the formulas (IVa), (IVb), (IVc) and (IVd), preferably are selected from the compounds of the formulas (IVa), (IVb) , (IVc) and (IVd), where R and Ar have the meanings given above, in particular for formula (I), W, Y a and Y b have the meanings given above, in particular for formulas (IIIa) to (IIId), the index I 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the index j is 0, 1 or 2, preferably 0 or 1.
  • Structures / compounds of the formulas (IVa), (IVc) and (IVd) are preferred here and structures / compounds of the formulas (IVa) and (IVc) are particularly preferred.
  • the sum of the indices j, m and I in compounds of the formulas (purple) to (Ille) and / or (IVa) to (IVd) is at most 10, particularly preferably at most 8 and particularly preferably at most 6.
  • the group Ar is phenyl, biphenyl, terphenyl, Quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, which is phenanthrene with, phenylene, quinanthrene, or triphenoxhene, respectively one or more radicals R can be substituted, preferably phenyl, biphenyl, fluorene, carbazole, dibenzofuran, dibenzothi
  • the compounds particularly preferably comprise at least one structure of the formulas (Va) to (Ve), the compounds are preferably selected from the compounds of the formulas (Va) to (Ve),
  • Formula (Vc) Formula (Vd) where R has the meanings given above, in particular for formula (I), W, Y a and Y b have the meanings given above, in particular for formulas (IIa) to (IIc), the index I 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2 and the index j is 0, 1 or 2, preferably 0 or 1.
  • Structures / compounds of the formulas (Va), (Vb), (Vd) and (Ve) are preferred here and structures / compounds of the formulas (Va), (Vd) and (Ve) are particularly preferred.
  • the compounds particularly preferably comprise at least one structure of the formulas (Via) to (Vld), which are particularly preferred
  • the sum of the indices j, I and m is preferably at most 10, preferably at most 8 and particularly preferably at most 6.
  • radicals W represents N (R) or N (Ar), preferably N (Ar).
  • both radicals W represent N (R) or N (Ar), preferably N (Ar).
  • radicals W represents B (R) or B (Ar), preferably B (Ar).
  • both radicals W represent B (R) or B (Ar), preferably B (Ar).
  • radicals W are the same.
  • identical here means that the radicals R and Ar cannot be distinguished.
  • the radicals W are different.
  • at least one of the radicals W represents N (R) or N (Ar), preferably N (Ar), and is at least one of the radicals W B (Ar), B (R), O or S.
  • the compounds according to the invention comprise a structure of the formulas (Va-1) to (Vb-11), it being possible for the compounds according to the invention to be particularly preferably selected from the compounds of the formulas (Va-1) to (Vb-11),
  • the compounds according to the invention comprise a structure of the formulas (Vc-1) to (Vc-11), it being possible for the compounds according to the invention to be particularly preferably selected from the compounds of the formulas (Vc-1) to (Vc-11), Formula (Vc-11) where R has the meanings given above, in particular for formula (I), Y a has the meanings given above, in particular for formula (IIc), index I 0, 1, 2, 3, 4 or 5, is preferably 0, 1 or 2, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, the index n is 0, 1, 2 or 3, preferably 0, 1 or 2 and the index j is 0, 1 or 2, preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (Vla-1) to (Vlb-13), it being possible for the compounds according to the invention to be particularly preferably selected from the compounds of the formulas (Vla-1) to (Vlb-13), Formula (Vla-4) Formula (Vlb-4)
  • Formula (Vla-12) Formula (Vlb-12) where R has the meanings given above, in particular for formula (I), Y a has the meanings given above, in particular for formula (IIc), index I 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2 is, the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, the index n is 0, 1, 2 or 3, preferably 0, 1 or 2 and the index j is 0, 1 or 2 , is preferably 0 or 1.
  • Structures / compounds of the formulas (Vla-1), (Vla-2), (Vla-3), (Vlb-1), (Vla-12) and (Via13) are preferred and structures / compounds of the formulas (Vla- 1) and (Vla-3) are particularly preferred.
  • the sum of the indices j, I and m is at most 10, preferably at most 8 and particularly preferably at most 6.
  • At least two radicals R form a condensed ring with the other groups to which the two radicals R bond, the two radicals R at least one structure of the formulas (RA-1) to (RA-12) shape
  • Formula RA-10 Formula RA-11 Formula RA-12 where R 1 has the meaning set out above, in particular for formula (I), the dashed bonds represent the attachment points to the atoms of the groups to which the two radicals R bond, and the other symbols have the following meaning:
  • Y c is on each occurrence, identically or differently, C (R 1 ) 2,
  • the at least two radicals R which form the structures of the formulas (RA-1) to (RA-12) and form a condensed ring, represent radicals R from adjacent X groups.
  • the at least two radicals R form a condensed ring with the other groups to which the two radicals R bond, the two radicals R preferably at least one of the structures of the formulas (RA-1a) to (RA- 4f)
  • Formula RA-4d Formula RA-4e
  • Formula RA-4f where the symbols R 1 , R 2 , R c and the indices s, and t have the meanings mentioned above, in particular for formulas (I), (RA-1) to (RA-12), and the index m 0, 1, 2, 3 or 4, preferably 0, 1 or 2.
  • At least two radicals R form a condensed ring with the other groups to which the two radicals R bond, the two radicals R forming structures of the formula (RB)
  • R 1 has the meaning given above, in particular for formula (I), the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y d C (R 1 ) 2 , N (R 1 ), N (Ar '), B (R 1 ), B (Ar'), O or S, preferably C (R 1 ) 2 , N (Ar ') or O, where Ar' is the above, has in particular the meaning mentioned for formula (I).
  • radicals R which form the structures of the formula (RB) and form a condensed ring, represent radicals R from adjacent X groups.
  • the compounds particularly preferably comprise at least one structure of the formulas (VIIa) to (VIIj); the compounds are particularly preferably selected from compounds of the formulas (VIIa) to (VIIj), the compounds having at least one condensed ring
  • the compounds according to the invention have at least two condensed rings, the condensed rings being identical and the part formed by two radicals R being represented by at least one structure of the formulas (RA-1) to (RA-12). Furthermore, it can be provided that the compounds according to the invention have at least two condensed rings, the condensed rings being different and the part formed by two radicals R can be represented by at least one structure of the formulas (RA-1) to (RA-12) .
  • the compounds according to the invention have at least two condensed rings, wherein the condensed rings are different and one of the two condensed rings has a part formed by two radicals R, which is defined by at least one of the structures of the formulas (RA-1 ) to (RA-12) can be represented and one of the two condensed rings has a part formed by two radicals R which can be represented by one of the structures of the formula (RB).
  • substituents R and R c , R 1 and R 2 according to the above formulas with the ring atoms of the ring system to which the R and R c , R 1 and R 2 are bonded, do not form a condensed aromatic or heteroaromatic ring system.
  • the substituents R and R c , R 1 and R 2 according to the above formulas with the ring atoms of the ring system to which the R and R c , R 1 and R 2 bond, apart from ring systems of the formula (RA- 1) to (RA-12) and preferred embodiments of these ring systems, or ring systems of the formula (RB), do not form a condensed ring system.
  • R 1 and / or R 2 form a ring system with one another, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic.
  • the radicals that form a ring system with one another can be adjacent, that is to say that these radicals are attached to the same carbon atom or to carbon atoms that are directly bonded to one another, are bound, or they can be further apart.
  • the ring systems provided with the substituents R, R c , R 1 and / or R 2 can also be connected to one another via a bond, so that ring closure can thereby be brought about.
  • each of the corresponding binding sites is preferably provided with a substituent R, R c , R 1 and / or R 2 .
  • a compound according to the invention is characterized by at least one of the structures according to formula (I), (Ila) to (Ild), (purple) to (Ille), (IVa) to (IVd), (Va) to (Ve) , (Via) to (Vld) and / or their preferred embodiments can be displayed.
  • Compounds according to the invention preferably comprising structures according to formula (I), (Ila) to (Ild), (purple) to (Ille), (IVa) to (IVd), (Va) to (Ve), (Via) to (Vld) and / or their preferred embodiments have a molecular weight of less than or equal to 5000 g / mol, preferably less than or equal to 4000 g / mol, particularly preferably less than or equal to 3000 g / mol, especially preferably less than or equal to 2000 g / mol and completely particularly preferably less than or equal to 1200 g / mol.
  • preferred compounds according to the invention are distinguished by the fact that they can be sublimed. These compounds generally have a molar mass of less than approx. 1200 g / mol.
  • Preferred aromatic or heteroaromatic ring systems Ar, R and / or Ar ' are selected from phenyl, biphenyl, especially ortho-, meta- or para-biphenyl, terphenyl, especially ortho-, meta-, para or branched terphenyl, quaterphenyl, especially ortho -, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which can be linked via the 1-,
  • 2-, 3- or 4-position can be linked, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which can be linked via the 1-, 2-, 3- or 4-position , Dibenzofuran, which can be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyridine, pyrimidine , Pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, Phenanthrene or triphenylene, each of which can be substituted by one or more radicals R 1.
  • At least one substituent R is selected from the group consisting of H, D or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-75, the substituents R preferably being either one Ring according to the structures of the formulas (RA-1) to (RA-12) or (RB) or the substituent R, identically or differently on each occurrence, is selected from the group consisting of H, D or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-75, and / or the group Ar ', identically or differently on each occurrence, is selected from the groups of the following formulas Ar-1 to Ar-75,
  • Ar 1 is on each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system with 6 to 18 aromatic ring atoms, which can in each case be substituted by one or more radicals R 1;
  • the substituent R 1 which is bonded to the nitrogen atom preferably stands for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which can also be substituted by one or more radicals R 2.
  • this substituent R 1 is the same or different on each occurrence for an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, in particular with 6 to 18 aromatic ring atoms, which has no condensed aryl groups and which has no condensed heteroaryl groups , in which two or more aromatic or heteroaromatic 6-ring groups are fused directly to one another, and which in each case can also be substituted by one or more radicals R 2.
  • Phenyl, biphenyl, terphenyl and quaterphenyl with Ver knüpfungsmustern as listed above for Ar-1 to Ar-11, these structures can be substituted by one or more radicals R 2 instead of R 1 , but are preferably unsubstituted.
  • Triazine, pyrimidine and quinazoline are also preferred, as listed above for Ar-47 to Ar-50, Ar-57 and Ar-58, it being possible for these structures to be substituted by one or more radicals R 2 instead of R 1.
  • Preferred groups Ar which are mentioned in particular in formulas (I), (lla) to (lld), (lilac) to (Ille), (IVa) to (IVd), are from structures of the formulas (Ar-1) to ( Ar-75), where the substituents R 1 are to be replaced by R.
  • the groups Ar mentioned in particular in formulas (I), (Ila) to (IIId), (Lila) to (Ille), (IVa) to (IVd) can preferably comprise substituents R 1 instead of R.
  • the compound according to the invention comprises a hole transport group, at least one of the groups Ar and / or R preferably comprising, preferably representing, a hole transport group.
  • the group Y a , Y b , Y c and / or Y d can represent or form a hole transport group.
  • one of the radicals Ar and / or R is a group selected from arylamino groups, preferably di- or triarylamino groups, heteroarylamino groups, preferably di- or triheteroarylamino groups, carbazole groups, carbazole groups being preferred. These groups can also be viewed as a hole-transporting group.
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Compounds according to the invention with structures of the formula (IIle) which have the following properties are also particularly preferred:
  • Particularly preferred embodiments of the compounds shown in the table presented above with structures of the formula (IIle), which particularly preferably have a group Ar-12 to Ar-16, a condensed ring, preferably a ring according to formulas (RA-1) to (RA-12), the formulas (RA-1a) to (RA-4f) and / or the formula (RB), with structures of the formulas (RA-1) to (RA-12), the formulas (RA- 1a) to (RA-4f) and / or the formula (RB) with Y d equal to N (Ar ') or 0, particularly preferably Y d N (Ar'), where Ar 'is the above, in particular for formula (I ) has the meaning mentioned, are particularly preferred.
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • a carbazole group is preferably formed here, so that, for example, in the structures Ar-13 to Ar16, the group A represents a radical N (R 1 ).
  • the structures Ar-12, Ar-17 already contain a carbazole group which is a preferred hole transport group.
  • a triaryl group can be formed by appropriate substitution.
  • the compound comprises an electron transport group, at least one of the groups Ar and / or R preferably comprising, preferably representing, an electron transport group.
  • Electron transport groups are well known in the art and promote the ability of compounds to transport and / or conduct electrons.
  • the group Y a , Y b , Y c and / or Y d can represent or form an electron transport group.
  • the at least one of the groups Ar and / or R comprises at least one structure selected from the group consisting of pyridines, pyrimidines, pyrazines, pyridazines, triazines, quinazolines, quinoxalines, Quinolines, isoquinolines, imidazoles and / or benzimidazoles is selected, with pyrimidines, triazines and quinazolines being particularly preferred.
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • Particularly preferred attachment points were set out above by the structures of formulas (VIIa) to (VIIj).
  • R is selected from the group consisting of H, D, F, CN, NO2, Si (R 1 ) 3, B (OR 1 ) 2, a straight-chain alkyl group 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, it being possible for the alkyl group to be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, each of which can be substituted by one or more radicals R 1.
  • R is selected from the group consisting of H, D, F, a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms , where the alkyl group can in each case be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which can each be substituted by one or more radicals R 1.
  • At least one substituent R is selected from the group consisting of H, D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted with one or more radicals R 1 , or a group N (Ar ') 2.
  • the substituents R either form a ring according to the structures of the formulas (RA-1) to (RA-12) or (RB) or R is selected, identically or differently on each occurrence, from the group consisting of H , D, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , or a group N (Ar ') 2.
  • R is selected from the group consisting of Fl or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, the can in each case be substituted by one or more radicals R 1.
  • R c is selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms, the alkyl group in each case can be substituted by one or more radicals R 2 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, which can each be substituted by one or more radicals R 2.
  • R c is selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, the alkyl group in each case can be substituted with one or more radicals R 1 , an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, which can be substituted with one or more radicals R 2.
  • R c is particularly preferably selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl group with 1 to 5 carbon atoms or a branched or cyclic alkyl group with 3 to 5 carbon atoms, the alkyl group each having one or more radicals R 2 can be substituted or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which can be substituted with one or more radicals R 2.
  • R c is selected identically or differently at each occurrence from the group consisting of a straight-chain alkyl group with 1 to 6 carbon atoms or a cyclic alkyl group with 3 to 6 carbon atoms, the alkyl group in each case with a or more radicals R 2 can be substituted, or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which in each case can be substituted by one or more radicals R 1; two radicals R c can also be with one another form a ring system.
  • R c is particularly preferably selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms or a branched or cyclic alkyl group with 3 to 6 carbon atoms, the alkyl group in each case may be substituted with one or more radicals R 1 , but is preferably unsubstituted, or an aromatic ring system with 6 to 12 aromatic ring atoms, in particular with 6 aromatic ring atoms, each of which is substituted by one or more, preferably non-aromatic radicals R 2 can be, but is preferably unsubstituted; two radicals R c here can form a ring system with one another.
  • R c is very particularly preferably selected identically or differently on each occurrence from the group consisting of a straight-chain alkyl group with 1, 2, 3 or 4 carbon atoms, or a branched alkyl group with 3 to 6 carbon atoms.
  • R c very particularly preferably represents a methyl group or a phenyl group, where two phenyl groups can together form a ring system, a methyl group being preferred over a phenyl group.
  • Preferred aromatic or heteroaromatic ring systems R, R c and Ar ' are selected from phenyl, biphenyl, especially ortho-, meta- or para-biphenyl, terphenyl, especially ortho-, meta-, para- or branched terphenyl, quaterphenyl, especially ortho -, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which is linked via the 1-, 2-, 3- or 4-position may be, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which can be linked via the 1-, 2 -, 3- or 4-position can be linked, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenoc
  • the structures Ar-1 to Ar-75 listed above are particularly preferred, structures of the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), ( Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75), preferred and structures of Formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) are particularly preferred are.
  • R are groups of the formula -Ar 4 -N (Ar 2 ) (Ar 3 ), where Ar 2 , Ar 3 and Ar 4, identically or differently on each occurrence, represent an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms stand, which can be substituted in each case with one or more radicals R 1.
  • the total number of aromatic ring atoms of Ar 2 , Ar 3 and Ar 4 is a maximum of 60 and preferably a maximum of 40.
  • Ar 4 and Ar 2 can be linked to one another and / or Ar 2 and Ar 3 to one another by a group selected from C (R 1 ) 2, NR 1 , O or S.
  • the linkage of Ar 4 and Ar 2 with one another or of Ar 2 and Ar 3 with one another is preferably carried out in each case ortho to the position of the linkage with the nitrogen atom.
  • none of the groups Ar 2 , Ar 3 or Ar 4 are connected to one another.
  • Ar 4 is preferably an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, preferably with 6 to 12 aromatic ring atoms, which can each be substituted with one or more radicals R 1 .
  • Ar 4 is particularly preferably selected from the group consisting of ortho-, meta- or para-phenylene or ortho-, meta- or para-biphenyl, which can each be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • Ar 4 is very particularly preferably an unsubstituted phenylene group.
  • Ar 2 and Ar 3 are preferably, identically or differently on each occurrence, an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, which can in each case be substituted by one or more radicals R 1.
  • Particularly preferred groups Ar 2 and Ar 3 are selected from the group consisting of benzene, ortho-, meta- or para-biphenyl, ortho-, meta-, para- or branched terphenyl, ortho-, meta -, para- or branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1-, 2-, 3- or 4-spirobifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-, 3- or 4-carbazole, 1-, 2-, 3- or 4-dibenzofuran, 1-, 2-, 3- or 4-dibenzothiophene, indenocarbazole, indolocarbazole, 2-
  • Ar 2 and Ar 3 are very particularly preferably selected from the group consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para or branched Ter - phenyl, quaterphenyl, especially ortho-, meta-, para- or ver branched quaterphenyl, fluorene, especially 1-, 2-, 3- or 4-fluorene, or spirobifluorene, especially 1-, 2-, 3- or 4- Spirobifluoren.
  • R 1 is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, a straight-chain alkyl group with 1 to 10 carbon atoms or a branched or cyclic alkyl group with 3 to 10 carbon atoms, where the alkyl group can be substituted by one or more radicals R 2 , or an aromatic or heteroaromatic ring system with 6 to 24 aromatic ring atoms, each of which can be substituted by one or more radicals R 2.
  • R 1 identically or differently on each occurrence, is selected from the group consisting of H, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group with 3 to 6 carbon atoms, where the alkyl group can be substituted with one or more radicals R 5 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system with 6 to 13 aromatic ring atoms, each by one or several radicals R 5 can be substituted, but is preferably unsubstituted.
  • R 2 identically or differently on each occurrence, is H, an alkyl group with 1 to 4 carbon atoms or an aryl group with 6 to 10 carbon atoms which is substituted by an alkyl group with 1 to 4 carbon atoms can be, but is preferably unsubstituted.
  • the alkyl groups preferably have no more than five carbon atoms, particularly preferably no more than 4 carbon atoms, very particularly preferably no more than 1 carbon atom.
  • compounds are also suitable which are substituted with alkyl groups, in particular branched alkyl groups, with up to 10 carbon atoms or which are substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups.
  • the compound has exactly two or exactly three structures according to formula (I), (Ila) to (Ild), (lilac) to (Ille), (IVa) to (IVd), (Va) to (Ve ), (Via) to (Vld) and / or their preferred embodiments.
  • the preferred embodiments mentioned above can be combined with one another as desired.
  • the above-mentioned preferred embodiments apply simultaneously.
  • the compounds according to the invention can in principle be prepared by various methods. However, the methods described below have proven to be particularly suitable.
  • the present invention therefore also provides a method for the preparation of the compounds according to the invention, in which a basic structure with two aromatic amino groups is synthesized and this is then synthesized by means of a nucleophilic aromatic substitution reaction, a nucleophilic addition reaction or a coupling reaction to form a compound according to the formula ( I) is implemented.
  • Suitable compounds comprising at least one basic structure with two aromatic amino groups can in many cases be obtained commercially, the starting compounds set out in the examples being obtainable by known processes, so reference is made to them.
  • Particularly suitable and preferred coupling reactions are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA. These reactions are well known, the examples providing further guidance to those skilled in the art.
  • the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by means of 1 H-NMR and / or HPLC).
  • the compounds according to the invention can also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is possible in particular with compounds which are substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups such as olefins or oxetanes. These can be used as monomers for producing corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization takes place preferably via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups.
  • the compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.
  • the invention therefore further relates to oligomers, polymers or dendrimers containing one or more of the structures of the formula (I) listed above and preferred embodiments of this formula or compounds according to the invention, where one or more bonds of the compounds according to the invention or the structures of the formula (I) and preferred embodiments of this formula for the polymer, oligomer or dendrimer are present.
  • these therefore form a side chain of the oligomer or polymer or are linked in the main chain.
  • the polymers, oligomers or dendrimers can be conjugated or partially conjugated or be non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic. The same preferences as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units of the formula (I) or the preferred embodiments set out above and below are present in an amount of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%.
  • Suitable and preferred comonomers which form the polymer backbone are selected from fluorene (e.g. according to EP 842208 or WO 2000/022026), spirobifluoren (e.g. according to EP 707020, EP 894107 or WO 2006/061181), para phenylenes (e.g.
  • WO 92/18552 carbazoles (e.g. according to WO 2004/070772 or WO 2004/113468), thiophenes (e.g. according to EP 1028136), dihydrophenanthrenes (e.g. according to WO 2005/014689), cis- and trans-indenofluorenes (e.g. according to WO 2004/041901 or WO 2004/113412), ketones (e.g. according to WO 2005/040302), phenanthrenes (e.g. according to WO 2005 / 104264 or WO 2007/017066) or several of these units.
  • the polymers, oligomers and dendrimers can also contain further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.
  • compounds according to the invention which are distinguished by a high glass transition temperature are of particular interest.
  • compounds according to the invention are particularly preferred, comprising structures according to the formula (I) or the preferred embodiments set out above and below which have a glass transition temperature of at least 70 ° C., particularly preferably of at least 110 ° C., very particularly preferably of at least 125 ° C and particularly preferably at least 150 ° C, determined according to DIN 51005 (version 2005-08).
  • formulations of the compounds according to the invention are required for the processing of the compounds according to the invention from the liquid phase. These formulations can be, for example, solutions, dispersions or emulsions.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, ( -) - fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohe
  • the present invention therefore also provides a formulation or a composition containing at least one compound according to the invention and at least one further compound.
  • the further compound can be, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation.
  • the further compound can, however, also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitter and / or a matrix material, these compounds being different from the differentiate compounds according to the invention. Suitable emitters and matrix materials are listed below in connection with the organic electroluminescent device.
  • the further compound can also be polymeric.
  • the present invention therefore again further provides a composition containing a compound according to the invention and at least one further organically functional material.
  • Functional materials are generally the organic or inorganic materials that are inserted between the anode and cathode.
  • the organically functional material is preferably selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials, hole blocking materials, wide band Gap materials and n-dopants.
  • Another object of the present invention is the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device, preferably as host material, preferably as host material for phosphorescent emitters or as host material for emitters showing TADF (thermally activated delayed fluorescence) as Electron transport material is used as an electron injection material, as a hole transport material, as a hole injection material, as an electron blocking material and / or as a hole blocking material.
  • the compounds according to the invention can preferably be used as host material, preferably as host material for phosphorescent emitters or as host material for emitters which exhibit TADF (thermally activated delayed fluorescence), for blue-emitting emitters, in particular as blue-emitting phosphorescent emitters.
  • An electronic device containing at least one compound according to the invention.
  • An electronic device in the sense of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or layers that are made entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLED, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes Based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4); organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical Detectors, organic photo receptors, organic field quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescence devices (OLEDs, sOLED
  • the organic electroluminescent device contains a cathode, anode and at least one emitting layer. In addition to these layers, it can also contain other layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers and / or charge generation layers. Interlayers, which for example have an exciton-blocking function, can also be introduced between two emitting layers. It should be noted, however, that it is not necessary for each of these layers to be present.
  • the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers.
  • emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H.
  • Various emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, the three layers showing blue, green and orange or red emission.
  • the organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs.
  • the compound according to the invention can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device containing a compound of the formula (I) or the preferred embodiments set out above in an emitting layer as host material which provides hole-conducting properties, preferably as host material for blue emitters, particularly preferably blue triplet emitters.
  • the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
  • Phosphorescence in the context of this invention is understood to mean the luminescence from an excited state with a higher spin multiplicity, that is to say a spin state> 1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • the mixture of the compound according to the invention and the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 80% by volume. % of the compound according to the invention based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter based on the total mixture Emitter and matrix material.
  • connection according to the invention is used as the only matrix material (“single host”) for the phosphorescent emitter.
  • the organic electroluminescent device contains the compound according to the invention, preferably a compound comprising structures according to formula (I), (IIIa) to (IIId), (purple) to (Ille), (IVa) to (IVd), (Va) to (Ve) and / or (Via) to (Vld) or the preferred embodiments listed above as matrix material, preferably as hole-conducting matrix material in one or more emitting layers, preferably in combination with a further matrix material, preferably an electron-conducting matrix material.
  • the further matrix material is a hole-transporting compound.
  • the further matrix material is a compound with a large band gap which does not participate, or does not participate to a significant extent, in the transport of holes and electrons in the layer.
  • An emitting layer comprises at least one emitting compound.
  • Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl) or those in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, e.g. B.
  • indenocarbazole derivatives e.g. B. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, e.g. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, e.g. B. according to WO 2007/137725, silanes, e.g. B. according to WO 2005/111172, aza borole or boronic ester, z. B. according to WO 2006/117052, triazine derivatives, e.g. B.
  • connection can be used as a co-host which does not participate or does not participate to a significant extent in the charge transport, as described, for example, in WO 2010/108579.
  • compounds are suitable which have a large band gap and themselves do not, or at least not to a significant extent, participate in the charge transport of the emitting layer.
  • Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680.
  • Phosphorescence in the context of this invention is understood to mean the luminescence from an excited state with a higher spin multiplicity, that is to say a spin state> 1, in particular from an excited triplet state.
  • a spin state> 1 in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • Particularly suitable phosphorescent compounds are compounds which, with suitable excitation, emit light, preferably in the visible range, and also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 , especially a metal with this atomic number.
  • Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used as phosphorescent emitters, in particular compounds containing iridium or platinum.
  • Examples of the phosphorescent organometallic complexes described above can be found in the applications WO00 / 70655, W02001 / 41512, W02002 / 02714, WO2002 / 15645, EP1191612, W02005 / 033244, W02005 / 019373, US2005 / 0258742, W020070, W02007 / 115098 , W02008 / 000727, W02009 / 050281, W02009 / 050290, WO2011 / 051404, WO2011 / 073149, WO2012 / 121936, US2012 / 0305894, WO2012 / 170571, WO2012 / 170461, WO2012 / 170463, W02006 / 121811, W02007 / 095118, W02008 / 156879.
  • phosphorescent emitters are organometallic complexes with polypodal ligands as described in W02004081017, W02005042550, US20050170206, W02009 / 146770, WO201 0/102709, WO2011 / 066898, WO2016124304, WO2017032439, WO2018 / 2016348, WO2013184539, WO2018 / 2016348 / 193243 and WO 2015 / 091716A1.
  • WO201 6/079169 WO2018 / 019687, WO2018 / 041769, WO2018 / 054798, WO201 8/069196, WO2018 / 069197, WO2018 / 069273.
  • Examples of suitable phosphorescent palladium complexes are described in WO2014 / 109814.
  • the compounds according to the invention are also particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, such as those used, for. As described in WO 98/24271, US 2011/0248247 and US 2012/0223633. In these multi-colored display components, an additional blue emission layer is vapor-deposited over the entire surface of all pixels, including those with a color different from blue.
  • a compound according to the invention can preferably be used in combination with a TADF emitter, as set out above.
  • TADF thermally activated delayed fluorescence
  • AE singlet-triplet distance
  • a further connection can be provided in the matrix in addition to the emitter, which has a strong spin-orbit coupling, so that the spatial proximity and the possible interaction between the An inter-system crossing is made possible for molecules, or the spin-orbit coupling is generated via a metal atom contained in the emitter.
  • the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, ie the emitting layer directly adjoins the hole injection layer or the anode, and / or the emitting layer directly adjoins the electron transport layer or the electron injection layer or the cathode, as described, for example, in WO 2005/053051.
  • a metal complex which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport or hole injection material, such as. B. described in WO 2009/030981.
  • An organic electroluminescent device is also preferred, characterized in that one or more layers are coated with a sublimation process.
  • the materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10 5 mbar, preferably less than 10 6 mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10 7 mbar.
  • An organic electroluminescent device is likewise preferred, characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) process or with the aid of a carrier gas sublimation.
  • the materials are applied at a pressure between 10 5 mbar and 1 bar.
  • OVPD Organic Vapor Phase Deposition
  • OVJP Organic Vapor Jet Printing
  • an organic electroluminescent device characterized in that one or more layers of solution, such as B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • B. screen printing flexographic printing
  • offset printing offset printing
  • LITI Light Induced Thermal Imaging
  • ink-jet printing inkjet printing
  • nozzle printing nozzle printing.
  • Formulations for applying a compound according to formula (I) or their or their preferred embodiments set out above are new.
  • the present invention therefore also relates to formulations containing at least one solvent and a compound according to formula (I) or their preferred embodiments set out above.
  • Hybrid methods are also possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art in particular by an improved service life.
  • the other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least as good.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art in particular by an improved efficiency and / or operating voltage and a longer service life.
  • the electronic devices according to the invention are distinguished by a or more of the following surprising advantages over the
  • Electronic devices in particular organic electroluminescent devices containing compounds according to the invention, oligomers, polymers or dendrimers, or the preferred embodiments set out above and below, in particular as electron-conducting materials, as hole transport materials or as matrix materials, particularly preferably as hole transport materials or as matrix materials, have a very good Lifetime on.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to the invention, oligomers, polymers or dendrimers, or the preferred embodiments set out above and below, in particular as electron transport materials, hole transport materials and / or as host materials, particularly preferably as hole transport materials and / or as host materials excellent efficiency.
  • the efficiency is significantly higher compared to analogous compounds which do not contain a structure according to the invention.
  • the compounds, oligomers, polymers or dendrimers according to the invention or the preferred embodiments set out above and below bring about a low operating voltage when used in electronic devices. In particular, these connections cause a low roll-off, i.e. a small drop in the power efficiency of the device at high luminance levels.
  • the compounds comprising structures according to formula (I), preferably compounds of the formula (I) or the preferred embodiments set out above and below, have a high triplet level Ti.
  • the following syntheses are carried out under a protective gas atmosphere in dried solvents.
  • the metal complexes are also handled with exclusion of light or under yellow light.
  • the solvents and reagents can e.g. B. from Sigma-ALDRICH or ABCR.
  • the respective information in square brackets or the numbers given for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds which can have several enantiomeric, diastereomeric or tautomeric forms, one form is shown as a representative.
  • the mixture is stirred for a further 15 minutes, 200 ml of ice water are added dropwise to the suspension with thorough stirring, the solid is filtered off with suction, washed three times with 100 ml of water each time, suctioned dry and then dried in vacuo at 60.degree.
  • the 2-chloro-benzimidazolium hexafluorophosphate obtained in this way is suspended in 150 ml of acetonitrile, and then 14.1 g [130 mmol] of o-phenylenediamine [95-54-5] and 50 ml of triethylamine are added and the mixture is stirred at 50 ° C. for 8 h .
  • the reaction mixture is poured into 500 ml of ice water with thorough stirring, the precipitated solid is filtered off with suction, washed three times with 100 ml of water and twice with 50 ml of methanol each time and dried in vacuo.
  • the crude product is flash chromatographed, silica gel, n-Fleptan / EA (ethyl acetate), automatic column machine Torrent from A. Semrau. Yield: 12.5 g (33 mmol) 33%; Purity: approx. 95% according to 1 FI-NMR.
  • the compounds S100 to S107 are encompassed by the scope of protection of the present invention. These compounds represent valuable intermediate products for the production of stable hole conductors, electron conductors and host materials, as has been explained in detail above.
  • compounds with N-H bonds show a relatively low stability when used directly in a device.
  • the compound A108 obtained via the synthesis route set out above has no N-H bond and can thus be used directly for the production of a device.
  • OLEDs according to the invention and OLEDs according to the prior art are produced by a general method according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).
  • the OLEDs basically have the following layer structure: substrate / hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm / hole transport layer 1 (HTL1) consisting of HTM1, 170 nm for blue devices, 215 nm for green / yellow devices, 110 nm for red devices / hole transport layer 2 (HTL2) / emission layer (EML) / hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL from ETM2) and finally a cathode .
  • the cathode is formed by a 100 nm thick aluminum layer.
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is added to the matrix material or the matrix materials by co-evaporation in a certain volume proportion.
  • a specification like M1: M2: lr (L1) (55%: 35%: 10%) means that the material M1 in a volume fraction of 55%, M2 in a volume fraction of 35% and I r (L 1) in a volume fraction of 10% is present in the layer.
  • the electron transport layer can also consist of a mixture of two materials.
  • Table 1 The exact structure of the OLEDs is shown in Table 1.
  • the materials used to produce the OLEDs are shown in Table 4.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra are generated with a luminous density of 1000 cd / m 2 was determined and the CIE 1931 x and y color coordinates were calculated from this.
  • the compounds according to the invention can be used, inter alia, as hole transport material in HTL, as hole-conducting host material hTMM or electron-conducting host material eTMM in the emission layer EML of a phosphorescent OLED and as electron transport material in ETL.
  • the results of the OLEDs are summarized in Table 2.
  • the compounds according to the invention can also be processed from solution, where they lead to OLEDs which are considerably simpler in terms of process technology, compared to the vacuum-processed OLEDs, with nevertheless good properties.
  • the production of such components is based on the production of polymer light-emitting diodes (PLEDs), which has already been described many times in the literature (e.g. in WO 2004/037887).
  • the structure consists of substrate / ITO / hole injection layer (60 nm) / interlayer (20 nm) / emission layer (60 nm) / hole blocking layer (10 nm) / electron transport layer (40 nm) / cathode.
  • substrates from Technoprint are used, on which the ITO structure (indium tin oxide, a transparent, conductive anode) is applied.
  • the substrates are cleaned in the clean room with DI water and a detergent (Deconex 15 PF) and then activated by a UV / ozone plasma treatment.
  • a 20 nm hole injection layer PEDOT: PSS from Clevios TM
  • the required spin rate depends on the degree of dilution and the specific spin coater geometry.
  • the substrates are for 30 Baked minutes at 200 ° C on a hot plate.
  • the interlayer used is used for hole transport, in which case HL-X from Merck is used.
  • the interlayer can also be replaced by one or more layers, which only have to meet the condition through the downstream processing step of the EML-
  • the triplet emitters according to the invention are dissolved together with the matrix materials in toluene or chlorobenzene.
  • the typical solids content of such solutions is between 16 and 25 g / L if, as here, the layer thickness typical for a device is
  • the solution-processed devices contain an emission layer Ma: Mb: lr (w%: x%: z%) or Ma: Mb: Mc: lr (w%: x%: y%: z%), see table 3.
  • the emission layer is centrifuged in an inert gas atmosphere, in the present case argon, and baked out at 160 ° C. for 10 minutes.
  • ETM2 (50%)) vapor-deposited (vapor-deposition systems from Lesker oa, typical vapor-deposition pressure 5 x 10 6 mbar). Finally, a cathode made of aluminum (100 nm) (high-purity metal from Aldrich) is vapor-deposited. In order to protect the device from air and humidity, the device is finally encapsulated and then characterized. The OLED examples mentioned have not yet been optimized. Table 3 summarizes the data obtained.
  • HTL2 EBL (Electron Blocking Layer)
  • EML Electrode
  • HBL Hol Blocking Layer
  • EQE Extra Quantum Efficacy

Abstract

L'invention concerne des dérivés de benzimidazole qui sont appropriés pour être utilisés dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant lesdits composés.
EP21702244.1A 2020-01-29 2021-01-27 Dérivés de benzimidazole Pending EP4097090A1 (fr)

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