WO2024094592A2 - Hétérocycles azotés pour dispositifs électroluminescents organiques - Google Patents

Hétérocycles azotés pour dispositifs électroluminescents organiques Download PDF

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WO2024094592A2
WO2024094592A2 PCT/EP2023/080184 EP2023080184W WO2024094592A2 WO 2024094592 A2 WO2024094592 A2 WO 2024094592A2 EP 2023080184 W EP2023080184 W EP 2023080184W WO 2024094592 A2 WO2024094592 A2 WO 2024094592A2
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group
radicals
aromatic
atoms
substituted
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Philipp Stoessel
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Merck Patent Gmbh
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Definitions

  • the present invention relates to nitrogen-containing heterocycles for use in electronic devices, in particular in organic electroluminescent devices, as well as electronic devices, in particular organic electroluminescent devices, containing these materials.
  • Electronic devices containing organic compounds are widely known and commercially available. These devices can, for example, each comprise 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.
  • these devices can, for example, each comprise 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.
  • there is a need for improvement with regard to the properties of these devices with the compounds used in the layers described above in particular having a major influence on the properties of the devices.
  • phosphorescent organometallic complexes are often used as emitting materials in organic electroluminescent devices. For quantum mechanical reasons, up to four times the energy and power efficiency is possible when organometallic compounds are used as phosphorescent emitters. In general, there is still room for improvement in electroluminescent devices, especially in electroluminescent devices that exhibit triplet emission (phosphorescence). The properties of phosphorescent electroluminescent devices are not only determined by the triplet emitters used. The other materials used, such as matrix materials, are also of particular importance here. Improvements to these materials can therefore also lead to significant improvements in the properties of the electroluminescent devices. Similar statements also apply to organic electroluminescent devices based on phosphorescent emitters or emitters exhibiting TADF (thermally activated delayed fluorescence).
  • TADF thermalally activated delayed fluorescence
  • EP 3 070 144 A1 and WO 2017/178864 A1 disclose nitrogen-containing heterocycles that can be used in organic electroluminescent devices. Compounds according to the present invention are not disclosed.
  • 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, as well as to provide the corresponding electronic device.
  • the object of the present invention is to provide compounds that lead to a long service life, good efficiency and low operating voltage.
  • the properties of the matrix materials in particular have a significant influence on the service life and efficiency of the organic electroluminescent device.
  • a further object of the present invention can be seen in providing compounds which are suitable for use in a phosphorescent or fluorescent electroluminescent device, in particular as a matrix material.
  • the compounds especially when used as matrix materials, as hole transport materials or as electron transport materials in organic electroluminescent devices, should lead to devices that have excellent lifetime and efficiency.
  • 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 formula (I), preferably a compound according to formula (I),
  • A stands on each occurrence, identically or differently, for B(R), B(Ar), P(R)O, P(Ar)O, C(R)2, C(Ar) 2 , Si(R) 2 , Si(Ar) 2 , Ge(R) 2 , Ge(Ar) 2 , Ti(R) 2 , Ti(Ar) 2 , Zr(R) 2 , Zr(Ar) 2 , Hf(R) 2 , Hf(Ar) 2 , SO2 or SO, preferably for B(R), B(Ar), P(R)O, P(Ar)O, C(R)2, C(Ar)2, Si(R)2, Si(Ar)2, Ge(R)2 or Ge(Ar)2, particularly preferably for C(R)2, C(Ar)2, Si(R)2, Si(Ar)2, Ge(R)2 or Ge(Ar)2, and very particularly preferably for Si(Ar)2 or Si(R)2;
  • Z stands at each occurrence, identically or differently, for N(R a ), N(Ar a ), O or S, preferably for N(R a ) or N(Ar a ) and particularly preferably for N(Ar a );
  • X 1 stands on each occurrence, identically or differently, for N or CR b , preferably for N, with the proviso that not more than two of the groups X 1 , X 2 , X 3 in a cycle stand for N, or the group X 1 forms with a group X 2 an aromatic or heteroaromatic ring system linked in the ortho position and having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R b ;
  • X 2 stands on each occurrence, identically or differently, for N or CR b, preferably for CR b , with the proviso that not more than two of the groups X 1 , X 2 , X 3 in a cycle stand for N;
  • X 3 represents, identically or differently at each occurrence, N or CR b , with the proviso that not more than two of the groups X 1 , X 2 , X 3 in a cycle represent N, or the group X 3 forms with a group X 2 an aromatic or heteroaromatic ring system linked in the ortho position and having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R b , where the group X 2 forms an aromatic or heteroaromatic ring system with at most one group X 1 or X 3 in a cycle;
  • Ar a is, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be substituted by one or more radicals R a ;
  • R 2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one 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, where two or more, preferably adjacent, substituents R 2 can form a ring system with one another.
  • An aryl group in the sense of this invention contains 6 to 40 C atoms; a heteroaryl group in the sense of this invention contains 3 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aryl group or heteroaryl group is understood to be either a simple aromatic cycle, i.e.
  • benzene or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.
  • Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
  • An electron-poor heteroaryl group in the sense of the present invention is a heteroaryl group which has at least one heteroaromatic six-membered ring with at least one nitrogen atom.
  • aromatic or heteroaromatic five-membered rings or six-membered rings can be fused to this six-membered ring.
  • electron-poor heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline or quinoxaline.
  • An aromatic ring system in the sense of this invention contains 6 to 60 C atoms in the ring system.
  • a heteroaromatic ring system in the sense of this invention contains 3 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C 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 sense of this invention is to be understood as a system which does not necessarily only contain aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be connected by a non-aromatic unit, such as a C, N or O atom.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. are to be understood as aromatic ring systems in the sense of this invention, as are 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 CH2 groups can also be substituted by the abovementioned groups, 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, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,
  • An alkoxy group with 1 to 40 C atoms is preferably understood to mean 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.
  • a thioalkyl group with 1 to 40 C atoms is particularly understood to mean methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio,
  • 2-ethylhexylthio trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynylthio or octynylthio.
  • alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, where one or more non-adjacent CH2 groups can be replaced by the above-mentioned groups;
  • one or more H atoms can be replaced by D, F, CI, Br, I, CN or NO2, preferably F, CI or CN, more preferably F or CN, particularly preferably CN.
  • An aromatic or heteroaromatic ring system with 5 - 60 or 5 to 40 aromatic ring atoms, which can be substituted with the above-mentioned radicals and which can be linked to the aromatic or heteroaromatic via any position, is understood to mean in particular groups which are derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, is
  • two or more radicals can form a ring is understood in the context of the present description to mean, among other things, that the two radicals are linked to one another by a chemical bond with formal elimination of two hydrogen atoms. This is illustrated by the following scheme.
  • the compounds according to the invention can preferably comprise at least one structure of the formulas (1-1) to (1-11), and are particularly preferably selected from the compounds of the formulas (1-1) to (1-11),
  • Structures/compounds of the formulas (1-1) to (I-4) are preferred, structures/compounds of the formulas (1-1) and/or (I-2) are particularly preferred and structures/compounds of the formula (1-1 ) are particularly preferred.
  • the group Z stands for N(Ar a ), wherein preferred embodiments of the group Ar a are also explained below in connection with the group Ar, which can be part of the residue Z.
  • the group A stands for B(Ar), P(Ar)O, C(Ar)2, Si(Ar)2 or Ge(Ar)2, wherein preferred embodiments of the group Ar are also explained below in connection with the group Ar a , which can be part of the radical A.
  • the radical Ar, Ar a and/or R represents an aromatic or heteroaromatic ring system having 5 to 18, preferably 6 to 13 aromatic ring atoms, which may be substituted by one or more radicals R a or R c .
  • the group Ar and/or Ar a is selected, identically or differently on each occurrence, from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, anthacene, phenanthrene or triphenylene, which can each be substituted by one or more radicals R c or R a , preferably phenyl, biphenyl, fluorene, dibenzofuran, triphenylene, carbazole, indolocarbazole.
  • the group Ar a and/or the group Ar can preferably represent a phenyl group which is substituted by at least one radical R a or R c , wherein the substituent is in the ortho, meta, para position, relative to the nitrogen atom of the group N(Ar a ) or the B, P, C, Si or Ge atom of the group A.
  • R a or R c is a phenyl group
  • an ortho, meta, para biphenyl group can be formed.
  • the triazine group has two radicals R a and R c , respectively, which are not H or D, where the two radicals R a and R c , respectively, are preferably an aromatic or heteroaromatic ring system having 5 to 60, preferably 6 to 30 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 .
  • the group Ar a and/or the group Ar can preferably represent a phenyl group which is substituted by at least one radical R a or R c , where the substituents together with the phenyl group represented by the group Ar a and/or the group Ar are a fluorene radical which can be linked via the 1-, 2-, 3- or 4-position, a spirobifluorene radical which can be linked via the 1-,
  • the group A stands for C(R)2, Si(R)2 or Ge(R)2, where preferred radicals R are selected from straight-chain alkyl groups having 1 to 40 C atoms or alkenyl or alkynyl groups having 2 to 40 C atoms or branched or cyclic alkyl groups having 3 to 20 C atoms, where these groups can each be substituted by one or more radicals R c .
  • the structure/compound according to the present invention comprises at least one electron transport group and/or an electron-withdrawing radical.
  • Electron transport groups are widely known in the art and promote the ability of compounds to transport and/or conduct electrons. Examples of electron transport groups are pyridine, Pyrimidine, pyrazine, pyridazine, triazine, quinazoline, quinoxaline, quinoline, isoquinoline, imidazole and/or benzimidazole groups, with triazine groups being particularly preferred.
  • the electron-withdrawing radicals include in particular SO2, B(R), B(Ar), P(R)O, P(Ar)O, which can be present, for example, as group A.
  • the structure/compound according to the present invention has at least one hole transport group.
  • Hole transport groups are also known in the art, and these preferably comprise triarylamine or carbazole groups.
  • the present compounds are particularly suitable as host material for emitters, preferably as host material for singlet, triplet and TADF emitters, electron transport material, electron injection material, hole conductor material, hole injection material, electron blocking material, hole blocking material in an electronic device.
  • the specific properties of the compounds depend on the type and number of the respective functional groups.
  • Compounds which comprise one, two or more electron transport groups and/or electron-withdrawing radicals, but no hole transport group are particularly suitable as host material, electron transport material, electron injection material and/or hole blocking material.
  • Compounds which comprise one, two or more hole transport groups, but no electron transport group and/or electron-withdrawing radicals are particularly suitable as host material, hole conductor material, hole injection material and/or electron blocking material.
  • Compounds which comprise one, two or more Hole transport groups and one, two or more electron transport groups and/or electron withdrawing residues are particularly suitable as host materials.
  • At least one, preferably all of the radicals R, R a is/are not equal to H, preferably not equal to H, D, OH, NO2, F, CI, Br, I.
  • the compounds according to the invention have a structure of the formulas (II-1) to
  • X a stands on each occurrence, identically or differently, for N, CR a or C, in the case that a group binds to the structure preferably for CR a or C with the proviso that not more than three of the groups X a in a cycle stand for N, where R a has the meaning given above, in particular for formula (I);
  • Structures/compounds of the formulas (II-1), (II-2) and (II-3) are preferred, structures/compounds of the formula (II-1) and (II-2) are particularly preferred and structures/compounds of the formula (II-1) are very particularly preferred.
  • X a stands for C if a group binds to the respective structure.
  • This group is in particular the ring structure shown in formulae (II-2) or (II-4) and provided with a radical Y.
  • This ring structure can bind here via a radical X a or via Y, where in the latter case Y stands for C(R a )-, Si(R a )-, Ge(R a )-.
  • At least one, preferably at least two and particularly preferably three groups X a per ring represent N, whereby these groups are preferably not adjacent.
  • These structures/compounds preferably comprise electron transport groups and are therefore particularly suitable as electron transport materials and/or matrix materials.
  • the compounds according to the invention comprise a structure of the formulas (III-1) to (III-12), wherein the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (III-1) to (III-12),
  • I is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2.
  • Structures/compounds of the formulas (III-1) to (III-8) are preferred, structures/compounds of the formulas (III-1), (III-2), (III-5) and (III-6) are particularly preferred and structures/compounds of the formulas (III-1) and (III-2) are very particularly preferred.
  • the sum of the indices j, m, n and I in structures/compounds of the formulas (II 1-1) to (III-12) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2.
  • the compounds according to the invention comprise a structure of the formulae (IV-1) to (IV-48), wherein the compounds according to the invention can particularly preferably be selected from the compounds of the formulae (IV-1) to (IV-48),
  • M stands at each occurrence, identically or differently, for C, Si, Ge, Ti, Zr or Hf, preferably for C, Si or Ge, particularly preferably for Si;
  • I is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2.
  • Structures/compounds of the formulae (IV-1) to (IV-8), (IV-13) to (IV-20), (IV-25), (IV-26), (IV-29), (IV-30) and (IV-38) are preferred, structures/compounds of the formulae (IV-1), (IV-2), (IV-5), (IV-6), (IV-13), (IV-14), (IV-25) and (IV-26) are particularly preferred and structures/compounds of the formulae (IV-1), (IV-2), (IV-13) and (IV-14) are very particularly preferred.
  • the sum of the indices j, m, n and I in structures/compounds of the formulas (IV-1) to (IV-48) is preferably at most 6, particularly preferably at most 4 and particularly preferably at most 2.
  • radicals which can be selected in particular from R, R a , R b , R c , 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 which form a ring system with one another can be adjacent, ie these radicals are bonded to the same carbon atom or to carbon atoms which are directly bonded to one another, or they can be further apart from one another.
  • the ring systems provided with the substituents R, R a , R b , R c , R 1 and/or R 2 can also be connected to one another via a bond, so that a ring closure can be brought about in this way.
  • At least two, preferably adjacent radicals R, R a , R b , R c form a condensed ring with the other groups to which the two radicals R, R a , R b , R c bind.
  • ring structures are formed which are described in the publication WO 2022/079068 A1 , filed on October 13, 2021 with the European Patent Office under the application number PCT7EP2021/078240 are described, whereby for disclosure purposes the description of the condensed ring structures set out in these publications, which are represented by the ring elements of the formulae (RA-1 ) to (RA-12), (RA-1 a) to (RA-4f) and/or (RB) on pages 37 to 40 of the publication
  • WO 2022/079068 A1 are incorporated into the present application by reference thereto.
  • the substituents R a , R b , R c , R 1 and R 2 do not form a condensed aromatic or heteroaromatic ring system, particularly preferably no ring system, with the ring atoms of the ring system to which the substituents R a , R b , R c , R 1 and R 2 are bonded.
  • At least one radical R a , R b , R c is selected, identically or differently on each occurrence, from the group consisting of H, D, a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20 C atoms or an aromatic or heteroaromatic ring system selected from the groups of the following formulas Ar-1 to Ar-76, or the radical R a , R b , R c is selected, identically or differently on each occurrence, 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-76, and/or the group Ar' is selected, identically or differently on each occurrence, from the groups of the following formulas Ar-1 to Ar-76,
  • Ar 1 is, identically or differently at each occurrence, a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which may each be substituted by one or more radicals R 1 ;
  • the substituent R 1 which is bonded to the nitrogen atom preferably represents an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2.
  • this substituent R 1 identical or different on each occurrence, represents an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 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 directly condensed to one another, and which may in each case also be substituted by one or more radicals R 2.
  • Phenyl, biphenyl, terphenyl and quaterphenyl are preferred. Preference is also given to triazine, pyrimidine and quinazoline, as listed above for Ar-47 to Ar-50, Ar-57 and Ar-58, where these structures can be substituted by one or more radicals R 2 instead of R 1 .
  • the substituents R 1 bonded to this carbon atom are preferably identical or different each occurrence represents a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2 .
  • R 1 most preferably represents a methyl group or a phenyl group.
  • the radicals R 1 may also form a ring system with one another, resulting in a spiro system.
  • R a , R b and R c are the same or different on each occurrence and are selected from the group consisting of H, D, F, CN, NO2, Si(R 1 ) s, B(OR 1 ) 2, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 .
  • radicals R a , R b and R c are the same or different on each occurrence and are selected from the group consisting of H, D, F, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 .
  • At least one radical R a , R b and R c preferably a substituent R a , R b and R c is selected, identically or differently on each occurrence, from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , or a group N(Ar')2, particularly preferably at least one substituent R a , R b and R c is the same or different on each occurrence and is selected from the group consisting of an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 .
  • the substituents R a , R b and R c either form a condensed ring or the radical R a , R b and R c is the same or different on each occurrence and is selected from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 , or a group N(Ar') 2.
  • the radical R a , R b and R c preferably the substituent R a , R b and R c are the same or different on each occurrence and are selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, which may each be substituted by one or more radicals R 1 .
  • At least one radical R a , R b and R c represents an aromatic or heteroaromatic ring system having 5 to 13 aromatic ring atoms, which can be substituted by one or more radicals R 1 .
  • At least one radical preferably a substituent R a , R b and R c is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, naphthalene, indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene or triphenylene, which can each be substituted by one or more radicals R 1 .
  • a substituent R a , R b and R c is selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, na
  • substituent means in particular that R a , R b and R c are not H, preferably not H and not D. Furthermore, the substituents R a , R b and R c can be the same or different if two or more substituents selected from the aromatic or heteroaromatic group mentioned.
  • Preferred aromatic or heteroaromatic ring systems which are represented by substituents R, R a , R b and R c or Ar, Ar a or Ar', are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular 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, naphthalene, in particular 1- or -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
  • Particularly preferred aromatic or heteroaromatic ring systems represented by substituents R, R a , R b and R c or Ar, Ar a or Ar' are the structures (Ar-1 ) to (Ar-76) listed above, with structures of the formulae (Ar-1 ), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar- 15), (Ar-16), (Ar-69), (Ar-70), (Ar-76) being preferred and structures of the formulas (Ar-1 ), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) being particularly preferred.
  • R a , R b , R c are groups of the formula -Ar 4 -N(Ar 2 )(Ar 3 ), where Ar 2 , Ar 3 and Ar 4 are the same or different on each occurrence and represent an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may each be substituted by 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 connected to one another and/or Ar 2 and Ar 3 can also be connected to one another by a single bond or a group selected from C(R 1 )2, NR 1 , O or S.
  • Ar 4 and Ar 2 are connected to one another or Ar 2 and Ar 3 are connected to one another ortho to the position of the connection to the nitrogen atom.
  • none of the groups Ar 2 , Ar 3 or Ar 4 are connected to one another.
  • Ar 4 is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, each of which may be substituted by one or more radicals R 1 .
  • Ar 4 is selected from the group consisting of ortho-, meta- or para-phenylene or ortho-, meta- or para-biphenyl, each of which may be substituted by one or more radicals R 1 , but is preferably unsubstituted.
  • Ar 4 is an unsubstituted phenylene group.
  • Ar 2 and Ar 3 are the same or different on each occurrence and are an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may each be substituted by one or more radicals R 1 .
  • Particularly preferred groups Ar 2 and Ar 3 are the same or different on each occurrence and 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-spiro-bifluorenyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-
  • Ar 2 and Ar 3 are particularly preferably selected, identically or differently on each occurrence, from the group consisting of benzene, biphenyl, in particular ortho-, meta- or para-biphenyl, Terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, in particular 1-, 2-, 3- or 4-fluorene, or spirobifluorene, in particular 1-, 2-, 3- or 4-spirobifluorene.
  • R 1 is the same or different on each occurrence and is selected from the group consisting of 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, where the alkyl group may in each case be substituted by one or more radicals R 2 , or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 .
  • R 1 is the same or different on each occurrence and is selected from the group consisting of H, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may be substituted by one or more radicals R 2 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 , but is preferably unsubstituted.
  • R 2 is the same or different on each occurrence and is H, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted.
  • the alkyl groups preferably have no more than five C atoms, particularly preferably no more than 4 C atoms, very particularly preferably no more than 1 C atom.
  • the structures/compounds according to the invention are deuterated.
  • the structures/compounds according to the invention preferably have a high degree of deuteration.
  • the degree of deuteration can be at least 50%, preferably at least 80%, especially preferably at least 90% and very particularly preferably at least 95%.
  • the degree of deuteration is determined from the numerical ratio of deuterium to the sum of deuterium and 1 H hydrogen (D/(D+H)*100).
  • the compounds are particularly preferably fully deuterated.
  • the compounds according to the invention are particularly suitable for use in blue-emitting electroluminescent devices. Depending on the layer, these require materials with a high triplet level. However, many substituents with condensed aromatic or heteroaromatic groups can lead to a reduction in the triplet level.
  • naphthyl structures are preferred over anthracene structures.
  • fluorenyl, spirobifluorenyl, dibenzofuranyl and/or dibenzothienyl structures are preferred over naphthyl structures.
  • the radical Ar, R does not comprise an anthracene group, preferably none of the radicals Ar, Ar a , R, R a , R b and R c , particularly preferably none of the radicals Ar, Ar a , R, R a , R b , R c , R 1 and R 2 comprises an anthracene group.
  • the radicals Ar, R do not comprise an aromatic or heteroaromatic ring system, which has three linearly condensed aromatic 6 rings, wherein preferably none of the radicals Ar, Ar a , R, R a , R b and R c , particularly preferably none of the radicals Ar, Ar a , R, R a , R b , R c , R 1 and R 2 comprises an aromatic or heteroaromatic ring system which has three linearly condensed aromatic 6 rings.
  • the compound according to the invention is substituted with aromatic or heteroaromatic groups R a , R b , R c , R 1 or R 2 , it is preferred if these do not have any aryl or heteroaryl groups with more than two aromatic six-membered rings condensed directly to one another.
  • the substituents particularly preferably have no aryl or heteroaryl groups with directly condensed six-membered rings at all. This preference is based on the low triplet energy of such structures.
  • Condensed aryl groups with more than two aromatic six-membered rings condensed directly to one another, which are nevertheless also very suitable according to the invention, are phenanthrene and triphenylene, since these also have a high triplet level.
  • none of the radicals Ar, Ar a , R, R a , R b and R c preferably none of the radicals Ar, Ar a , R, R a , R b , R c , R 1 and R 2 comprises or forms a fluorenone group.
  • a fluorenone comprises a 5-membered ring with a CO group to which two aromatic 6-membered rings are fused.
  • the compounds of formula (I) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer that directly borders a phosphorescent layer, it is further preferred if the compound does not contain any condensed aryl or heteroaryl groups in which more than two six-membered rings are directly condensed to one another.
  • An exception to this are phenanthrene and triphenylene, which can be preferred due to their high triplet energy despite the presence of condensed aromatic six-membered rings.
  • the compound comprises exactly two or exactly three structures according to formula (I), (1-1) to (1-11), (11-1) to (II-8), (111-1) to (111-12) and/or (IV-1) to (IV-48).
  • the compounds are selected from compounds of the formula (D-1), where the group L 1 represents a connecting group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R a , and the other symbols used have the meanings given above, in particular for formula (I), where the group L 1 forms a bond to the basic structure instead of a hydrogen atom or a substituent, preferably the group L 1 binds to the radicals Z, A.
  • the group L 1 represents a connecting group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R a , and the other symbols used have the meanings given above, in particular for formula (I), where the group L 1 forms a bond to the basic structure instead of a hydrogen atom or a substituent, preferably the group L 1 binds to the radicals
  • L 1 is a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which may be substituted by one or more radicals R a , but is preferably unsubstituted, where R a may have the meaning given above, in particular for formula (I).
  • L 1 is particularly preferably an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be substituted by one or more radicals R 1 , but is preferably unsubstituted. is substituted, where R 1 can have the meaning given above, in particular for formula (I).
  • the symbol L 1 set out inter alia in formula (D1) preferably stands, identically or differently on each occurrence, for a bond or an aryl or heteroaryl radical having 5 to 24 ring atoms, preferably 6 to 13 ring atoms, particularly preferably 6 to 10 ring atoms, so that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly, ie via an atom of the aromatic or heteroaromatic group, to the respective atom of the further group.
  • the group L 1 shown in formula (D1) comprises an aromatic ring system with at most four, preferably at most three, particularly preferably at most two fused aromatic and/or heteroaromatic 6-membered rings, preferably no fused aromatic or heteroaromatic ring system.
  • Suitable aromatic or heteroaromatic ring systems L 1 are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene, fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, which may each be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • a compound according to the invention can be represented by at least one of the structures according to formulas (I), (1-1) to (1-11), (11-1) to (II-8), (111-1) to (111-12) and/or (IV-1) to (IV-48).
  • compounds according to the invention preferably comprising structures according to formulas (I), (1-1) to (1-11), (11-1) to (II-8), (111-1) to (111-12) and/or (IV-1) to (IV-48) 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, more preferably less than or equal to 1200 g/mol and most preferably less than or equal to 900 g/mol.
  • preferred compounds according to the invention are characterized in that they are sublimable. These compounds generally have a molecular weight of less than about 1200 g/mol.
  • the compound comprising structures according to formula (I), preferably the compound according to formula (I) or a preferred embodiment of this structure/compound is not in direct contact with a metal atom, preferably does not represent a ligand for a metal complex.
  • the basic structure of the compounds according to the invention can be prepared according to the methods outlined in the following schemes.
  • the individual synthesis steps such as coupling reactions that lead to C-C linkages and/or C-N linkages, are known in principle to the person skilled in the art. These include reactions according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA.
  • compounds according to the invention can be prepared in three steps from building blocks known from the literature, N-benzylated 2-chloroimidazoles (1 ) and anilines (2) (Scheme 1 ).
  • step 1 N,N-bisbenzylated bis(2-imidazolyl)amines (3) in the presence of lithium tert-butoxide in m-xylon at 120 °C according to W. Sang et al., Adv. Synth. Catal., 2021 , 363, 1408 Then, according to AA Haddach et al, Tetrahedron Letters, 2002, 43, 399, the benzyl protective groups are split off by the action of potassium tert-butoxide and oxygen in DMSO/THF (step 2), whereby the free bis(2-imidazolyl)amines (4) are obtained.
  • the splitting can be carried out by hydrogenolysis according to reactions known to those skilled in the art, eg in the system tetrahydrofuran/methanol/Pd-carbon/H2.
  • step 3 after deprotonation of the bis(2-imidazolyl)amines (4) with n-BuLi, coupling with the electrophiles E takes place.
  • N-benzylated 2-chloro-imidazoles and 3-chloro-pyrazoles as well as 3-chloro-benzpyrazoles can be reacted analogously.
  • a further object of the present invention is therefore a process for preparing a compound according to the invention, wherein a basic structure with an aromatic amino group is synthesized and at least one aromatic or heteroaromatic radical is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.
  • the at least one aromatic or heteroaromatic radical represents an imidazole or benzimidazole compound, wherein the imidazole or benzimidazole compound is symmetrical with respect to the two nitrogen atoms.
  • This design can in particular avoid the formation of isomers, since the intermediates described above can show tautomerism.
  • the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 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 particularly possible 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 to produce corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization preferably takes place 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 above-listed structures of the formula (I) 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 to 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, partially conjugated or non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic. The same preferences apply to the repeat units of the compounds according to the invention in oligomers, dendrimers and polymers as described above.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers.
  • Copolymers are preferred, the units according to formula (I) or the preferred embodiments described above and below being present in amounts 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 fluorenes (e.g. according to EP 842208 or WO 2000/022026), spirobifluorenes (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 even several of these units.
  • the polymers, oligomers and dendrimers can 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 characterized by a high glass transition temperature.
  • compounds according to the invention are particularly preferred which comprise structures according to 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 especially preferably of at least 150 °C, determined according to DIN 51005 (version 2005-08).
  • formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this purpose.
  • 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, in particular 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, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, Decalin,
  • a further subject matter of the present invention is therefore a formulation or a composition comprising 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 also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and/or a further matrix material.
  • At least one further compound is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters which exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials and hole blocking materials, preferably host materials.
  • a further subject 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.
  • the compound according to the invention is used in an electronic device as a host material, electron transport material, electron injection material, Hole conductor material, hole injection material, electron blocking material, hole blocking material is used.
  • a compound according to the invention is used as a host material, electron transport material, electron injection material or hole blocking material and this compound according to the invention comprises at least one electron transport group and/or one electron-withdrawing radical, wherein preferred electron transport groups and/or electron-withdrawing radicals have been defined previously.
  • a compound according to the invention is used as a host material, hole conductor material, hole injection material or electron blocking material and this compound according to the invention has at least one hole transport group, wherein preferred electron transport groups and/or electron-withdrawing radicals have been previously defined.
  • a compound according to the invention is used as host material and this compound according to the invention comprises both at least one hole transport group and at least one electron transport group and/or an electron-withdrawing radical.
  • 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 which are made entirely of inorganic materials.
  • the electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes on 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 photoreceptors, organic field quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, OLEDs,
  • the organic electroluminescent device contains a cathode, an anode and at least one emitting layer. In addition to these layers, it can contain further 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 can also be introduced between two emitting layers, which, for example, have an exciton blocking function. However, it should be noted that not all of these layers necessarily have to be present.
  • the organic electroluminescent device can contain one emitting layer, or it can contain several emitting layers.
  • emitting 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 different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Particularly preferred are systems with three emitting layers, where the three layers show blue, green and orange or red emission.
  • the inventive The organic electroluminescent device 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 according to formula (I) or the preferred embodiments described above in an emitting layer as host material for fluorescent emitters, phosphorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron transport layer, electron injection layer and/or in a hole transport layer, hole injection layer and/or in an exciton blocking layer and/or in a hole blocking layer.
  • TADF thermalally activated delayed fluorescence
  • the compound according to the invention is particularly preferably used as a matrix material for phosphorescent emitters, in particular for red, orange, green, yellow or blue phosphorescent emitters, in an emitting layer, as an electron transport or hole blocking material in an electron transport or hole blocking layer or as a hole transport or electron blocking material in a hole transport or electron blocking layer.
  • phosphorescent emitters in particular for red, orange, green, yellow or blue phosphorescent emitters, in an emitting layer, as an electron transport or hole blocking material in an electron transport or hole blocking layer or as a hole transport or electron blocking material in a hole transport or electron blocking layer.
  • 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 sense of this invention is understood to mean luminescence from an excited state with a higher spin multiplicity, i.e. 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 considered phosphorescent compounds.
  • the mixture of the compound according to the invention and the emitting compound contains between 99 and 1 vol.%, preferably between 98 and 10 vol.%, particularly preferably between 97 and 60 vol.%, in particular between 95 and 80 vol.% 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 vol.%, preferably between 2 and 90 vol.%, particularly preferably between 3 and 40 vol.%, in particular between 5 and 20 vol.% of the emitter, based on the total mixture of emitter and matrix material.
  • the compound according to the invention is used as the only matrix material (“single host”) for the phosphorescent emitter.
  • a further embodiment of the present invention is the use of the compound according to the invention as a matrix material for a phosphorescent emitter in combination with a further matrix material.
  • 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. 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
  • CBP 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. according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, e.g. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, e.g. B.
  • EP 1617710, EP 1617711, EP 1731584, JP 2005/347160 bipolar matrix materials, e.g. according to WO 2007/137725, silanes, e.g. according to WO 2005/111172, azaboroles or boronate esters, e.g. according to WO 2006/117052, triazine derivatives, e.g. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877, zinc complexes, e.g.
  • diazasilole or tetra-azasilole derivatives e.g. according to WO 2010/054729
  • diazaphosphole derivatives e.g. according to WO 2010/054730
  • bridged carbazole derivatives e.g. according to WO 2011/042107, WO 2011/060867, WO 2011/088877 and WO 2012/143080
  • triphenylene derivatives e.g. according to WO 2012/048781
  • dibenzofuran derivatives e.g. B. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565 or biscarbazoles, e.g. according to JP 3139321 B2.
  • a compound containing a structure/compound according to formula (I) or the preferred embodiments set out above, which is used as host material is preferably in combination: with one or more phosphorescent materials (triplet emitters); and/or
  • TADF Thermally Activated Delayed Fluorescence
  • a hyperfluorescence system as described in WO 2012/133188 and/or a hyperphosphorescence system as in US 2017271611 is preferably formed.
  • This combination represents a preferred composition according to the present invention.
  • WO 2015/091716 A1 and WO 2016/193243 A1 disclose OLEDs that contain both a phosphorescent compound and a fluorescent emitter in the emission layer, with the energy being transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence).
  • host materials have higher singlet and triplet energies compared to the emitters, so that the energy of the host material is transferred to the emitter as optimally as possible.
  • the systems disclosed in the prior art have precisely such an energy relationship.
  • the present invention also relates to electronic devices containing an organic layer, preferably a light-emitting layer, wherein the organic layer comprises:
  • a second compound as co-host material optionally a sensitizer; and a fluorescent emitter, wherein the sensitizer is a phosphorescent compound (triplet emitter) or a TADF compound.
  • Preferred emitters that can be used in combination with a compound according to the invention are described, among others, by Sungho Nam et al., Adv. Sci. 2021, 2100586 and Eungdo Kin et al., Sci. Adv. 2022, 8, eabq 1641.
  • triplet emitters or triplet emitter classes also called sensitizers in connection with hyperphosphorescence systems
  • emitters 2 and 3 on page 21 are preferred; in CN 109111487, with the compounds set out on pages 76 and 77 being preferred; in US 2020/0140471, with the compounds set out on pages 166 to 175 being preferred; in KR2020108705, with the compounds set out on pages 8 to 14 being preferred; in US 2019/0119312, wherein the compounds set out on pages 114 to 121 are preferred; and in US 2020/0411775, wherein the compounds set out on pages 123 to 128 are preferred.
  • WO 2021/090932 preferred fluorescent emitters or classes of fluorescent emitters are described in WO 2021/090932, wherein the compounds set out on pages 129 to 133, 157 to 166, 171 to 187, 200 to 211, 222 to 227, 236 to 252, 255 are preferred; in WO 2020/054676, wherein the compounds set out on pages 44 to 104 are preferred; in WO 2020/017931, wherein the compounds set out on pages 17 to 39 are preferred; in WO 2020/218079, wherein the compounds set out on pages 64 to 258 are preferred; in WO 2018/212169, wherein the compounds set out on pages 33 to 42 Compounds are preferred; in WO 2019/235452, wherein the compounds set out on pages 46 to 168 are preferred; in US 10,249,832, wherein the compounds set out on pages 19 to 106 are preferred; and in WO 2021/014001, wherein the compounds set out on pages 107 to 129 are preferred.
  • another phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host material. Particularly good results are achieved when a red phosphorescent emitter is used as the emitter and a yellow phosphorescent emitter is used as the co-host material in combination with the compound according to the invention.
  • a compound which does not participate, or does not participate to a significant extent, in charge transport can be used as co-host material, as described, for example, in WO 2010/108579.
  • compounds which have a large band gap and do not participate themselves, or at least not to a significant extent, in the charge transport of the emitting layer are suitable as co-matrix material in combination with the compound according to the invention.
  • Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680.
  • compounds according to the invention without special functional groups, for example hole transport groups and/or electron transport groups have advantageous properties.
  • Particularly suitable as phosphorescent compounds are compounds which emit light, preferably in the visible range, when suitably excited 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, in particular a metal with this atomic number.
  • Preferred phosphorescent emitters are compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, particularly compounds containing indium or platinum.
  • Examples of the emitters described above can be found in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/102709, WO 2011/032626, WO 2011/066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/117718, WO 2016/015815, WO 2016/124304, WO 2017/032439 and
  • Examples of phosphorescent dopants are listed in the following table.
  • the compounds according to the invention are also particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, as described, for example, in WO 98/24271, US 2011/0248247 and US 2012/0223633.
  • an additional blue emission layer is vapor-deposited over the entire surface of all pixels, including those with a color other than blue.
  • 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 is directly adjacent to the hole injection layer or the anode, and/or the emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described for example in WO 2005/053051.
  • a metal complex that 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, as described for example in WO 2009/030981.
  • an organic electroluminescent device characterized in that one or more layers are coated using 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 characterized in that one or more layers are coated using the OVPD (Organic Vapour Phase Deposition) method or with the aid of carrier gas sublimation.
  • the materials are applied at a pressure between 10' 5 mbar and 1 bar.
  • OVPD Organic Vapour Phase Deposition
  • OVJP Organic Vapour Jet Printing
  • an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or using any printing method, such as screen printing, flexographic printing, offset printing, LITI (light induced thermal imaging, thermal transfer printing), ink-jet printing or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.
  • Formulations for applying a compound according to formula (I) or the preferred embodiments thereof set out above are novel.
  • a further subject matter of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or the preferred embodiments thereof set out above.
  • hybrid processes are possible in which, for example, one or more layers are applied from solution and one or more further 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 improved efficiency and/or operating voltage. Furthermore, these compounds and the organic electroluminescent devices obtainable therefrom have an improved service life. In a particular variant, the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art in Technology is characterized in particular by a low refractive index (RI). Furthermore, preferred compounds according to the invention show a high triplet Ti level, so that these compounds are particularly suitable as host material for blue-emitting triplet emitters.
  • RI refractive index
  • the electronic devices according to the invention are characterized by one or more of the following surprising advantages over the prior art:
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments set out above and below, in particular as matrix material, as electron-conducting materials or as hole-conducting materials, have excellent efficiency.
  • compounds according to the invention according to formula (I) or the preferred embodiments set out above and below result in a low operating voltage when used in electronic devices.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments set out above and below, in particular as matrix material, as electron-conducting materials or as hole-conducting materials, have a very good service life. In this case, these compounds in particular cause a low roll-off, i.e. a small drop in the power efficiency of the device at high luminance levels.
  • optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by a high PL and thus high EL efficiency of emitters or an excellent energy transfer from the matrices to dopants.
  • the following syntheses are carried out under a protective gas atmosphere in dried solvents, unless otherwise stated.
  • the metal complexes are also handled in the absence of light or under yellow light.
  • the solvents and reagents can be obtained from Sigma-ALDRICH or ABCR, for example.
  • the respective information in square brackets or the numbers given for individual compounds refer to the CAS numbers of the compounds known from the literature. For compounds containing several can have enantiomeric, diastereomeric or tautomeric forms, one form is shown representatively.
  • the product thus obtained is purified by repeated hot extraction crystallization (usual organic solvents or their combinations, preferably acetonitrile-DCM, 1:3 to 3:1 vv) and fractional sublimation or tempering Purified under high vacuum. Yield: 2.91 g (7.1 mmol) 71%; Purity: approx. 99.9% according to HPLC.
  • OLEDs according to the invention as well as OLEDs according to the prior art is carried out according to a general process according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).
  • the following examples present the results of various OLEDs.
  • Cleaned glass plates (cleaned in a Miele laboratory dishwasher, Merck Extran cleaner) coated with structured ITO (indium tin oxide) with a thickness of 50 nm are pretreated with UV ozone for 25 minutes (UV ozone generator PR-100, UVP). These coated glass plates form the substrates onto which the OLEDs are applied.
  • the compounds according to the invention can be used in the hole injection layer (HIL), hole transport layer (HTL) and in the electron blocking layer (EBL). All materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emitting dopant (dopant, emitter) D, which is mixed into the matrix material or materials by co-evaporation in a certain volume proportion.
  • a specification such as SMB:D (97:3%) means that the material SMB is present in the layer in a volume proportion of 97% and the dopant D in a proportion of 3%.
  • the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in Table 5 or refer to the synthesis examples presented above.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic, as well as the service life.
  • the EQE in (%) and the voltage in (V) are given at a luminance of 1000 cd/m 2.
  • the service life is determined at an initial luminance of 10000 cd/m 2.
  • the measured time in which the brightness of the reference has dropped to 80% of the initial brightness is set to 100%.
  • the service life of the OLED components containing The compounds according to the invention are given in percent for reference.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • Electron blocking layer see Table 1
  • Emission layer see Table 1
  • Electron transport layer see Table 1
  • Electron injection layer made of ETM2, 1 nm
  • Aluminium cathode 100 nm
  • the compounds A according to the invention can be used in the hole injection layer (HIL), the hole transport layer (HTL), the electron blocking layer (EBL) and in the emission layer (EML) as matrix material (host material) M (see Table 5) or A (see materials according to the invention).
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EML emission layer
  • all materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is mixed into the matrix material or materials by co-evaporation in a certain volume proportion.
  • a specification such as M1:M2:lr (55%:35%:10%) means that the material M1 is present in the layer in a volume proportion of 55%, M2 in a volume proportion of 35% and Ir in a volume proportion of 10%.
  • the electron transport layer can also consist of a mixture of two materials.
  • the exact structure of the OLEDs can be found in Table 3. The materials used to prepare the OLEDs are shown in Table 5 or refer to the synthesis examples presented previously.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic, as well as the service life.
  • the EQE in (%) and the voltage in (V) are given at a luminance of 1000 cd/m 2
  • the service life is determined at an initial luminance of 1000 cd/m 2 for blue and red and 10000 cd/m 2 for green and yellow.
  • the measured time in which the brightness of the reference has dropped to 80% of the initial brightness is set to 100%.
  • the lifetime of the OLED components containing the compounds according to the invention is given as a percentage of the respective reference.
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • Electron blocking layer see Table 3
  • Emission layer see Table 3
  • HBL Hole blocking layer
  • Electron transport layer made of ETM1:ETM2 (50%:50%), 30 nm
  • Electron injection layer made of ETM2, 1 nm
  • Aluminium cathode 100 nm
  • EBM2 M4 1206465-62-4 2009314-82-1

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Abstract

La présente invention concerne des hétérocycles azotés appropriés pour être utilisés dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant lesdits hétérocycles.
PCT/EP2023/080184 2022-11-01 2023-10-30 Hétérocycles azotés pour dispositifs électroluminescents organiques WO2024094592A2 (fr)

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