EP4066289A1 - Verbindungen für elektronische vorrichtungen - Google Patents

Verbindungen für elektronische vorrichtungen

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Publication number
EP4066289A1
EP4066289A1 EP20790318.8A EP20790318A EP4066289A1 EP 4066289 A1 EP4066289 A1 EP 4066289A1 EP 20790318 A EP20790318 A EP 20790318A EP 4066289 A1 EP4066289 A1 EP 4066289A1
Authority
EP
European Patent Office
Prior art keywords
aromatic ring
groups
ring systems
substituted
radicals
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.)
Pending
Application number
EP20790318.8A
Other languages
German (de)
English (en)
French (fr)
Inventor
Elvira Montenegro
Teresa Mujica-Fernaud
Frank Voges
Amir Hossain Parham
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP4066289A1 publication Critical patent/EP4066289A1/de
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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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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    • C07D491/02—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 two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Definitions

  • the present application relates to fluorene derivatives in which one or both benzene rings of fluorene have been exchanged for a fleteroaryl ring.
  • the compounds are suitable for use in electronic devices.
  • Organic electronic devices which are organic semiconductor materials
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • the term OLEDs are understood to mean electronic devices which have one or more layers containing organic compounds and which emit light when an electrical voltage is applied.
  • the structure and the general functional principle of OLEDs are known to the person skilled in the art.
  • Emission layers and layers with a hole-transporting function have a great influence on the performance data of electronic devices.
  • New compounds are still being sought for use in these layers, in particular hole-transporting compounds and compounds which can serve as hole-transporting matrix material, in particular for phosphorescent emitters, in an emitting layer.
  • connections are sought in particular that have a high
  • a high stability of the connection is one A prerequisite for achieving a long service life for the electronic device.
  • triarylamine compounds such as spirobifluorenamines and fluorenamines are known as hole transport materials and hole transporting matrix materials for electronic devices.
  • Z is on each occurrence, identically or differently, selected from CR 1 and N;
  • X is selected identically or differently on each occurrence from 0, S and NAr °;
  • Ar 0 is selected identically or differently on each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 2 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted by radicals R 2;
  • R 6 is selected identically or differently on each occurrence from H, D, F, CI, Br, I, CN, alkyl or alkoxy groups with 1 to 20 carbon atoms, alkenyl or alkynyl groups with 2 to 20 carbon atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; where two or more radicals R 6 can be linked to one another and can form a ring; and wherein said alkyl, alkoxy, alkenyl and alkynyl groups, aromatic ring systems and heteroaromatic ring systems can be substituted by one or more radicals selected from F and CN; and in formulas (I) and (II) there is at least one substructure of the formula in question, which is selected from units R and the ring of the formula (I), at least one group A which corresponds to a formula (A), where a group A, if it is bonded to a unit R, is attached to a group Ar
  • Ar L is selected identically or differently on each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 3 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted by radicals R 3;
  • Ar 2 is selected identically or differently on each occurrence from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 3 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted by radicals R 3;
  • E is a single bond or a divalent group selected from C (R 4 ) 2, Si (R 4 ) 2 , N (R 4 ), O, and S;
  • an aryl group is either a single aromatic cycle, that is benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene or
  • a condensed aromatic polycycle consists of two or more individual aromatic rings condensed with one another. Condensation between cycles is to be understood as meaning that the cycles share at least one edge with one another.
  • an aryl group contains 6 to 40 aromatic ring atoms. Furthermore, an aryl group does not contain a fletero atom as an aromatic ring atom, but only carbon atoms.
  • a fleteroaryl group is understood to mean either a single heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a condensed heteroaromatic polycycle, for example quinoline or carbazole.
  • a heteroaromatic polycycle consists of two or more individual aromatic or heteroaromatic cycles condensed with one another, at least one of the aromatic and heteroaromatic cycles being a heteroaromatic cycle. Condensation between cycles is to be understood as meaning that the cycles share at least one edge with one another.
  • a heteroaryl group contains 5 to 40 aromatic ring atoms, at least one of which is a heteroatom.
  • the heteroatoms of the heteroaryl group are preferably selected from N, O and S.
  • An aryl or heteroaryl group which can be substituted by the above-mentioned radicals, is understood to mean in particular groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzphenanthrene Tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, 6,7-quinoline, benzo-7,8-quinoline, phenothiazin
  • An aromatic ring system in the context of this invention is a system which does not necessarily contain only aryl groups, but which can additionally contain one or more non-aromatic rings which are condensed with at least one aryl group. These non-aromatic rings contain only carbon atoms as
  • aromatic ring system also includes systems that consist of two or more aromatic ring systems that are connected to one another via single bonds, for example biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl and 3,5-diphenyl-1-phenyl.
  • aromatic ring system contains 6 to 40 carbon atoms and no heteroatoms in the ring system.
  • aromatic ring system does not include heteroaryl groups.
  • a heteroaromatic ring system corresponds to the above definition of an aromatic ring system, with the difference that it must contain at least one heteroatom as a ring atom.
  • the heteroaromatic ring system does not have to contain exclusively aryl groups and heteroaryl groups, but can also contain one or more non-aromatic rings which are fused with at least one aryl or heteroaryl group.
  • the non-aromatic rings can exclusively contain carbon atoms as ring atoms, or they can additionally contain one or more heteroatoms, the
  • Heteroatoms are preferably selected from N, O and S.
  • An example of such a heteroaromatic ring system is benzopyranyl.
  • the term “heteroaromatic ring system” is understood to mean systems which consist of two or more aromatic or heteroaromatic ring systems which are connected to one another via single bonds, such as, for example, 4,6-diphenyl-2-triazinyl.
  • a heteroaromatic ring system for the purposes of this invention contains 5 to 40 Ring atoms selected from carbon and heteroatoms, at least one of the ring atoms being a heteroatom.
  • the heteroatoms of the heteroaromatic ring system are preferably selected from N, O and S.
  • heteromatic ring system and “aromatic ring system” according to the definition of the present application differ from one another in that an aromatic ring system cannot have a heteroatom as a ring atom, while a heteroaromatic ring system must have at least one heteroatom as a ring atom.
  • This hetero atom can be present as a ring atom of a non-aromatic heterocyclic ring or as a ring atom of an aromatic heterocyclic ring.
  • each aryl group is from
  • aromatic ring system includes aromatic ring system, and each heteroaryl group is encompassed by the term “heteroaromatic ring system”.
  • An aromatic ring system with 6 to 40 aromatic ring atoms or a heteroaromatic ring system with 5 to 40 aromatic ring atoms are understood to mean in particular groups which are derived from the groups mentioned above under aryl groups and heteroaryl groups and from biphenyl, terphenyl, quaterphenyl, fluorene, spirobifluorene, Dihydrophenanthrene, dihydropyrene, tetrahydropyrene, indenofluoren, Truxen, Isotruxen, Spirotruxen, Spiroisotruxen, Indenocarbazole, or combinations of these groups.
  • a straight-chain alkyl group with 1 to 20 carbon atoms or a branched or cyclic alkyl group with 3 to 20 carbon atoms or an alkenyl or alkynyl group with 2 to 40 carbon atoms in which also individual H atoms or CH2 groups substituted by the groups mentioned above in the definition of the radicals 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, cyclopentyl, neo- Pentyl, n-hexyl, cyclohexyl, neo-hexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-e
  • Definition of the groups mentioned can be substituted, 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, 2,2,2-trifluoroethoxy,
  • the compound according to the application preferably corresponds to the formula (I).
  • the unit R in formula (I) and / or (II) preferably corresponds to the formula (R- the unit of the formula (R-1) being bonded to the remainder of the formula via the positions marked with *.
  • R ° is preferably chosen to be the same for each occurrence.
  • R ° is preferably the same or different on each occurrence, preferably the same, selected from F, CN, Si (R 5 ) 3, straight-chain alkyl groups with 1 to 20 carbon atoms, branched or cyclic alkyl groups with 3 to 20 carbon atoms, aromatic Ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said alkyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R 5.
  • R ° is particularly preferably the same or different on each occurrence, preferably the same, selected from straight-chain alkyl groups with 1 to 20 carbon atoms, branched or cyclic alkyl groups with 3 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic Ring systems with 5 to 40 aromatic ring atoms, said alkyl groups and said aromatic
  • Ring systems and the heteroaromatic ring systems mentioned are each substituted by radicals R 5.
  • R ° is very particularly preferred for each Appear identically or differently, preferably identically, selected from methyl and phenyl, each of which is substituted by radicals R 5 , R 5 preferably being H in this case.
  • X is preferably selected identically or differently on each occurrence from 0 and S, particularly preferably X is S.
  • the remaining groups are correspondingly equal to CR 1 .
  • Ar 0 is preferably selected identically or differently on each occurrence from aromatic ring systems having 6 to 40 aromatic ring atoms, each of which is substituted by radicals R 2.
  • Ar 0 is particularly preferably selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl,
  • Dibenzothiophenyl carbazolyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzofuranyl-substituted phenyl,
  • Phenyl carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, the groups mentioned being each substituted by radicals R 2.
  • Ar 0 is phenyl substituted with radicals R 2 , where R 2 is preferably H.
  • the group Ar 1 in question is preferably selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 2 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are Radicals R 2 are substituted; particularly preferably from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 2; very particularly preferably from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl,
  • Fluorenyl in particular 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzothiophenyl-substituted phenyl, carbazolyl-substituted phenyl, pyridyl Phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, the groups mentioned being each substituted by radicals R 2; the strongest preferably from phenyl which is substituted by radicals R 2 , where R 2 is preferably H.
  • Ar 1 is preferably selected identically or differently on each occurrence from H, D, straight-chain alkyl or alkoxy groups with 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups with 3 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, the alkyl groups, alkoxy groups, aromatic ring systems and heteroaromatic ring systems each being substituted by radicals R 2.
  • Ar 1 is particularly preferably selected identically or differently on each occurrence from aromatic ring systems having 6 to 40 aromatic ring atoms which are substituted by radicals R 2.
  • Ar 1 is very particularly preferably selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl , Dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl,
  • Ar 1 is phenyl substituted with radicals R 2 , where R 2 is preferably H.
  • Si (R 5 ) 3 straight-chain alkyl groups with 1 to 20 carbon atoms which can be deuterated, branched or cyclic alkyl groups with 3 to 20 carbon atoms which can be deuterated, aromatic ring systems with 6 to 40 aromatic ring atoms which are deuterated can be, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which can be deuterated, said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 5 , which are preferably H.
  • R 1 is very particularly preferably H.
  • Preferred groups R 1 are shown in the following table:
  • R 1 -1, R 1 -2, R 1 -143, R 1 -148, R 1 -149, R 1 -174 and R 1 -177 are particularly preferred.
  • Si (R 5 ) 3 straight-chain alkyl groups with 1 to 20 carbon atoms which can be deuterated, branched or cyclic alkyl groups with 3 to 20 carbon atoms which can be deuterated, aromatic ring systems with 6 to 40 aromatic ring atoms which are deuterated can be, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which can be deuterated, said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 5 , which are preferably H.
  • R 2 is very particularly preferably H.
  • Preferably only one or two groups A are present in the compound according to formula (I) or (II), particularly preferably only one group A is present in the compound according to formula (I) or (II).
  • two groups A are present in the compound according to formula (I), they can either both be bonded to the unit R; or one group A is attached to the unit R and the other group A is bound to the aromatic six-membered ring; or both
  • Groups A are attached to the aromatic six-membered ring.
  • two groups A are present in the compound according to formula (II), they can either both be bonded to the same unit R; or one group A is bonded to a unit R and the other group A is bonded to the other unit R.
  • Ar L is preferably selected identically or differently on each occurrence from aromatic ring systems with 6 to 20 aromatic ring atoms which are substituted by radicals R 3 , and heteroaromatic ring systems with 5 to 20 aromatic ring atoms which are substituted by radicals R 3.
  • Particularly preferred groups Ar L are selected identically or differently on each occurrence from divalent groups derived from benzene, biphenyl, terphenyl, naphthalene, fluorene, indenofluorene, indenocarbazole, spirobifluorene, dibenzofuran, dibenzothiophene and carbazole, each of which is substituted by radicals R 3.
  • Ar L is very particularly preferably a divalent group derived from benzene, biphenyl or naphthalene, the is in each case substituted by one or more radicals R 3 , the radicals R 3 in this case preferably being H.
  • K is preferably equal to 0.
  • the formulas (Ar L -1), (Ar L -2), (Ar L -3), (Ar L -4), (Ar L -15), (Ar L -20), (Ar L - 25), (Ar L -36) are particularly preferred.
  • Ar 2 is preferably selected identically or differently on each occurrence from monovalent groups derived from benzene, biphenyl, terphenyl,
  • the groups Ar 2 can preferably be selected identically or differently on each occurrence from combinations of groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, fluorene, in particular 9,9'-dimethylfluorene and 9,9'-diphenylfluorene , 9-sila-fluorene, in particular 9,9'-dimethyl-9-silafluorene and 9,9'-diphenyl-9-silafluorene, benzofluorene, spirobifluorene, indenofluorene, indenocarbazole, dibenzofuran, dibenzothiophene, carbazole, benzofuran, benzothiophene, indole, Quinoline, pyr
  • the groups Ar 2 are completely or partially deuterated.
  • Ar 2 are selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl , Dibenzothiophenyl, carbazolyl,
  • Particularly preferred groups Ar 2 are selected identically or differently from the following formulas: where the groups at the positions shown unsubstituted are substituted by radicals R 3 , where R 3 in these positions is preferably H, and wherein the dashed bond is the bond to the amine nitrogen atom.
  • Ar 2 is very particularly preferably selected identically or differently from the formulas Ar-1, Ar-2, Ar-3, Ar-4, Ar-5, Ar-48, Ar-50, Ar-74, Ar-78, Ar- 82, Ar-107, Ar-108, Ar-117, Ar-134, Ar-139 and Ar-172.
  • the two groups Ar 2 in formula (A) are selected to be different.
  • E is preferably a single bond.
  • the sum of the indices m and n is preferably 0 or 1, particularly preferably 0, so that the groups E are omitted.
  • n 0, so that the relevant group E is omitted.
  • m is equal to 0, so that the relevant group E is omitted.
  • the subunit of formula (A) is selected from the following formulas: which are substituted in the free positions on the rings by radicals R 3 , these radicals R 3 preferably being H.
  • the unit which are substituted at the free positions on the rings by radicals R 3 these radicals R 3 preferably being Fl.
  • R 3 is particularly preferably selected identically or differently on each occurrence from H, D, Si (R 5 ) 3, straight-chain alkyl groups with 1 to 20 carbon atoms, which can be deuterated, branched or cyclic alkyl groups with 3 to 20 carbon atoms Atoms that can be deuterated, aromatic ring systems with 6 to 40 aromatic ring atoms that can be deuterated, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms that can be deuterated, said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are in each case substituted with radicals R 5 , which are preferably H.
  • R 3 is very particularly preferably H.
  • R 5 is particularly preferably selected identically or differently on each occurrence from H, D, Si (R 6 ) 3, straight-chain alkyl groups with 1 to 20 carbon atoms, which can be deuterated, branched or cyclic alkyl groups with 3 to 20 carbon atoms Atoms that can be deuterated, aromatic ring systems with 6 to 40 aromatic ring atoms that can be deuterated, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms that can be deuterated, said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 6 , which are preferably H.
  • R 5 is very particularly preferably H.
  • Preferred embodiments of the formula (I) and (II) correspond to the formulas (IA) to (IE) and (II-A) to (II-C) where the variables are defined as above and the group A, when attached to a moiety R, is attached either to a group Ar 1 or to a group Ar 0 .
  • the Formulas (IA), (IB) and (II-A) are preferred, in particular formulas (IA) and (IB).
  • formulas (1A) to (IE) are preferred, in particular formulas (1A) and (IB).
  • the above-mentioned preferred embodiments of the variable groups apply to the above-mentioned formulas.
  • Z is preferably equal to CR 1 and X is preferably equal to 0 or S, particularly preferably equal to S.
  • the compound of the formula (I) or (II) corresponds to one of the following formulas (1-1) to (I-3) or (11-1) to (II-6): where the variables are defined as above, and where at least one
  • Group A per formula is present which is bonded either to a ring or to a group Ar 1 or to a group Ar 0 as part of a group NAr ° as X.
  • the above formulas preferably apply the above preferred embodiments of the variables.
  • Z is preferably CR 1 .
  • X is preferably S or 0, particularly preferably S. Preferred among those mentioned above
  • Formulas are formulas (1-1) and (11-1), especially formula (1-1).
  • Ar 0 is preferably phenyl which is substituted by radicals R 2 , R 2 in these cases preferably being Fl.
  • Ar 1 is preferably phenyl which is substituted by radicals R 2 , R 2 in these cases preferably being Fl.
  • R ° is selected, identically or differently, preferably identically, on each occurrence from straight-chain alkyl groups with 1 to 20 carbon atoms, branched or cyclic alkyl groups with 3 to 20 carbon atoms, and aromatic ring systems with 6 to 40 aromatic ring atoms, said alkyl groups and said aromatic ring systems each being substituted by radicals R 5.
  • formulas (1-1 S-1) to (1-1 S-6) and (1-10-1) to (1-10-6) are particularly preferred.
  • the formulas (1-1 S-1) to (1-1 S-6) are very particularly preferred.
  • the compound according to the application therefore particularly preferably corresponds to a formula (1-1 S-1) to (1-1 S-6) or (1-10-1) to (1-10-6), where the following applies to the variables that occur:
  • Ar 1 is selected identically or differently on each occurrence from phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9'-dimethylfluorenyl and 9,9'-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl,
  • Dibenzothiophenyl carbazolyl, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzofuranyl-substituted phenyl, dibenzofuranyl-substituted phenyl,
  • Phenyl carbazolyl-substituted phenyl, pyridyl-substituted phenyl, pyrimidyl-substituted phenyl, and triazinyl-substituted phenyl, the groups mentioned being each substituted by radicals R 2;
  • R ° is the same or different on each occurrence, preferably the same, selected from straight-chain alkyl groups with 1 to 20 carbon atoms, branched or cyclic alkyl groups with 3 to 20 carbon atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, said alkyl groups and said aromatic
  • Ring systems and the said heteroaromatic ring systems are each substituted with radicals R 5;
  • R 1 is selected identically or differently on each occurrence from H, D, Si (R 5 ) 3, straight-chain alkyl groups with 1 to 20 carbon atoms which can be deuterated, branched or cyclic alkyl groups with 3 to 20 carbon atoms which Can be deuterated, aromatic ring systems with 6 to 40 aromatic ring atoms, which can be deuterated, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which can be deuterated, said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted by radicals R 5 , which are preferably H;
  • A is a unit of the formula (A)
  • Ar L is selected from divalent groups derived from benzene, biphenyl,
  • Ar 2 is selected identically or differently on each occurrence from monovalent groups derived from benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, fluorene, in particular 9,9'-dimethyl fluorene and 9,9'-diphenyl fluorene, 9-sila fluorene, in particular 9 , 9'-dimethyl-9-silafluorene and 9,9'-diphenyl-9-silafluorene, benzofluorene, spirobifluorene,
  • Groups are each substituted with one or more radicals R 3;
  • E is a single bond; m is 0 or 1; n is 0 or 1; k is 0 or 1; and the further variables are defined according to their broadest embodiment indicated above, preferably the preferred embodiments indicated above.
  • the compounds according to the application can be prepared by means of synthetic steps in organic chemistry known to the person skilled in the art, for example by means of metalation, addition of nucleophiles to carbonyl groups, Suzuki reaction and Hartwig-Buchwald reaction.
  • V is selected identically or differently on each occurrence from reactive groups, preferably CI, Br or I;
  • X is defined as above for formula (I) and (II);
  • Ar is on each occurrence, identically or differently, selected from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 2 , and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted by radicals R 2;
  • Hai is CI, Br, or I
  • R is an alkyl group with 1 to 20 carbon atoms, or a substituted or unsubstituted aromatic ring system with 6 to 40 aromatic ring atoms, or a substituted or unsubstituted heteroaromatic ring system with 5 to 40 aromatic ring atoms;
  • U is a reactive group, preferably a boronic acid group or a boronic ester group; i is 0, 1, 2 or 3; t is 0 or 1; where the compounds in the free positions on the benzene ring are each substituted by a radical R 1 , as defined above for formula (I) and (II).
  • the compounds obtained according to scheme 1a-1c and 2a-2c can be obtained by adding an organometallic reagent, preferably Grignard
  • Conditions are converted into fluorene derivatives in which one or both benzene rings are exchanged for a heteroaryl five-membered ring (pyrrole, furan or thiophene ring) (see schemes 3a to 3f below).
  • the carboxylic ester group cyclizes to form a methylene bridge between the heteroaromatic five-membered ring and the benzene ring.
  • the fluorene derivatives obtained in the reactions are referred to below as lnt-1 to lnt-6.
  • M is a metal and R-M is an organometallic reagent, preferably a Grignard reagent.
  • the intermediates lnt-1 to lnt-6 can either be via a Buchwald
  • the variables are as defined above, at least one index i is present, which is equal to 1, and A 'is a unit according to formula (A), where k is equal to 0, and A "is a unit according to formula (A), where k is equal to 1.
  • the present application thus provides a process for the preparation of a compound of a formula (I), characterized in that in a first step a Suzuki coupling is carried out in which a heteroaromatic five-membered ring is coupled to a benzene ring which carries a carboxylic acid ester group; that in a second step by reaction with an organometallic reagent and subsequent ring closure reaction under acidic conditions, the carboxylic acid ester group cyclizes to form a methylene bridge between the heteroaromatic five-membered ring and the benzene ring; and that in a third step a compound of the formula (I) is obtained via a Buchwald coupling with an amine or via a Suzuki coupling with an amino-substi
  • the present application also relates to a process for the preparation of a compound of a formula (II), characterized in that a Suzuki coupling is carried out in a first step in which a heteroaromatic five-membered ring is coupled to a further heteroaromatic five-membered ring which carries a carboxylic acid ester group ; that in a second step by reaction with an organometallic reagent and subsequent ring closure reaction under acidic conditions the
  • Carboxylic acid ester group cyclizes to form a methylene bridge between the heteroaromatic five-membered ring and the further heteroaromatic five-membered ring; and that in a third step a compound of the formula (II) is obtained via a Buchwald coupling with an amine or via a Suzuki coupling with an amino-substituted aryl or heteroaryl compound.
  • reaction steps take place in the order given.
  • the above-described compounds according to the application in particular compounds which are substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic acid ester, can be used as monomers for producing corresponding oligomers, dendrimers or polymers.
  • Suitable reactive leaving groups are, for example, bromine, iodine, chlorine, boronic acids, boronic acid esters, amines, alkenyl or alkynyl groups with a terminal C-C double bond or CC triple bond, oxiranes, oxetanes, groups that require a cycloaddition, for example a 1,3- dipolar cycloaddition, such as dienes or azides, carboxylic acid derivatives, alcohols and silanes.
  • the invention therefore furthermore relates to oligomers, polymers or dendrimers containing one or more compounds of the formula (I) or (II), where the bond (s) to the polymer, oligomer or dendrimer are attached to any given in formula (I) or (II) ) positions substituted with R °, R 1 , R 2 , R 3 or R 4 can be located.
  • the compound is part of a side chain of the oligomer or polymer or part of the main chain.
  • an oligomer is understood to mean a compound which is built up from at least three monomer units.
  • a polymer in the context of the invention is understood to mean a compound which is built up from at least ten monomer units.
  • the polymers, oligomers or dendrimers according to the invention can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers according to the invention can be linear, branched or dendritic.
  • the units according to formula (I) or (II) can be linked directly to one another or they can be linked to one another via a divalent group, for example via a substituted or unsubstituted alkylene group, via a fleteroatom or via a divalent aromatic or heteroaromatic group be.
  • three or more units of the formula (I) or (II) can have a trivalent or higher-valent group, for example a trivalent or higher-valent aromatic group or heteroaromatic group, linked to form a branched or dendritic oligomer or polymer.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers.
  • Suitable and preferred comonomers are selected from fluorenes, spirobifluorenes, paraphenylenes, carbazoles, thiophenes, dihydrophenanthrenes, cis- and trans-indenofluorenes, ketones, phenanthrenes or several of these units.
  • the polymers, oligomers and dendrimers usually also contain other units, for example emitting (fluorescent or phosphorescent) units, such as. B.
  • the polymers, oligomers and dendrimers according to the invention have advantageous properties, in particular long lifetimes, high efficiencies and good color coordinates.
  • the polymers and oligomers according to the invention are generally produced by polymerizing one or more types of monomers, at least one of which leads to repeat units of the formula (I) or (II) in the polymer.
  • Suitable polymerization reactions are known to the person skilled in the art and are described in the literature.
  • Particularly suitable and preferred polymerization reactions that lead to CC or CN linkages are the following: (A) SUZUKI polymerization;
  • formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It can be preferred 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, especially 3-phenoxytoluene, (-) - fenchone, 1,2,3,5-tetramethylbenzene, 1, 2,4,5 -Tetramethylbenzene, 1-
  • Triethylene glycol dimethyl ether diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis (3,4-dimethylphenyl) ethane or mixtures of these solvents.
  • the invention therefore furthermore relates to a formulation, in particular a solution, dispersion or emulsion, containing at least one compound according to formula (I) or (II) or at least one polymer, oligomer or dendrimer containing at least one unit according to formula (I) or (II) ) and at least one solvent, preferably an organic solvent.
  • a formulation in particular a solution, dispersion or emulsion, containing at least one compound according to formula (I) or (II) or at least one polymer, oligomer or dendrimer containing at least one unit according to formula (I) or (II) ) and at least one solvent, preferably an organic solvent.
  • solvent preferably an organic solvent
  • the compound according to formula (I) or (II) is suitable for use in an electronic device, in particular an organic electro luminescent device (OLED).
  • OLED organic electro luminescent device
  • the compound of the formula (I) or (II) can be used in different functions and layers.
  • the invention therefore also relates to the use of a compound of the formula (I) or (II) in an electronic device.
  • the electronic device is preferably selected from the group consisting of organic integrated circuits (OLCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic light-emitting transistors (OLETs), organic solar cells (OSCs), organic optical Detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O lasers) and particularly preferably organic electroluminescent devices (OLEDs).
  • OLCs organic integrated circuits
  • OFETs organic field-effect transistors
  • OTFTs organic thin-film transistors
  • OLETs organic light-emitting transistors
  • OSCs organic solar cells
  • OFDs organic optical Detectors
  • organic photoreceptors organic photoreceptors
  • OFQDs organic field quench devices
  • an organic electroluminescent device containing anode, cathode and at least one emitting layer characterized in that the device contains at least one organic layer which contains at least one compound according to formula (I) or (II).
  • An organic electroluminescent device containing anode, cathode and at least one emitting layer is preferred, characterized in that at least one organic layer in the device, selected from hole-transporting and emitting layers, contains at least one compound according to formula (I) or (II).
  • a hole-transporting layer is understood to mean all layers that are arranged between the anode and the emitting layer, preferably hole-injection layer, hole-transport layer, and electron-blocking layer.
  • a hole injection layer is understood here to be a layer which directly adjoins the anode.
  • a hole transport layer is understood to mean a layer that is present between the anode and the emitting layer, but does not directly adjoin the anode, preferably also not directly adjoin the emitting layer.
  • An electron blocking layer is understood to mean a layer which is present between the anode and the emitting layer and is directly adjacent to the emitting layer.
  • An electron blocking layer preferably has an energetically high LUMO and thereby prevents electrons from exiting the emitting layer.
  • the electronic device can also contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers, Electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, interlayers, charge generation layers and / or organic or inorganic p / n junctions. It should be pointed out, however, that each of these layers does not necessarily have to be present and the choice of the layers always depends on the compounds used and in particular also on the fact whether it is a fluorescent or phosphorescent electroluminescent device.
  • the sequence of layers of the electronic device is preferably as follows:
  • the organic electroluminescent device according to the invention can contain a plurality of emitting layers. These emission layers particularly preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H. in the emitting layers there are different emitting
  • Compounds used that can fluoresce or phosphoresce and that emit blue, green, yellow, orange or red light are particularly preferred, one of the three layers showing blue emission, one of the three layers showing green emission and one of the three layers showing orange or red emission.
  • the compounds according to the invention are preferably present in a hole-transporting layer or in the emitting layer. It should be noted that, instead of several color emitting emitter connections, an individually used emitter connection which emits in a broad wavelength range can also be suitable for generating white light.
  • the emitting layer can be a fluorescent emitting layer or it can be a phosphorescent emitting layer.
  • the emitting layer is preferably a blue fluorescent layer or a green phosphorescent layer.
  • the device containing the compound of formula (I) or (II) contains a phosphorescent emitting layer, it is preferred that this layer contains two or more, preferably exactly two, different matrix materials (mixed matrix system). Preferred embodiments of mixed matrix systems are described in more detail below.
  • a hole-transporting layer containing the compound of the formula (I) or (II) additionally contains one or more further hole-transporting compounds.
  • These further hole-transporting compounds are preferably selected from triarylamine compounds, particularly preferably from mono-triarylamine compounds. They are very particularly preferably selected from the preferred embodiments of hole transport materials given below.
  • the compound of the formula (I) or (II) and the one or more further hole-transporting compounds are preferably each present in a proportion of at least 10%, particularly preferably each present in a proportion of at least 20%.
  • a hole-transporting layer containing the compound of the formula (I) or (II) additionally contains one or more p-dopants.
  • Organic electron acceptor compounds which can oxidize one or more of the other compounds of the mixture are preferably used as p-dopants according to the present invention.
  • Particularly preferred p-dopants are quinodimethane compounds, azaindenofluorenediones, azaphenalenes, azatriphenylenes, I2, metal halides, preferably transition metal halides, metal oxides, preferably metal oxides containing at least one transition metal or a metal from main group 3, and transition metal complexes, preferably complexes of Cu, Co, Ni, Pd and Pt with ligands containing at least one oxygen atom as a binding site.
  • transition metal oxides as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re 2 07 , M0O3, WO3 and Re03 .
  • preference is given to complexes of bismuth in the Oxidation level (III), in particular bismuth (III) complexes with electron-poor ligands, in particular carboxylate ligands.
  • the p-dopants are preferably distributed largely uniformly in the p-doped layers. This can be achieved, for example, by co-evaporation of the p-dopant and the hole transport material matrix.
  • the p-dopant is preferably present in a proportion of 1 to 10% in the p-doped layer.
  • a hole injection layer is present in the device which corresponds to one of the following embodiments: a) it contains a triarylamine and a p-dopant; or b) it contains a single electron-poor material (electron acceptor).
  • the triarylamine is a mono-triarylamine, in particular one of the preferred triarylamine derivatives mentioned below.
  • the electron-poor material is a hexaazatriphenylene derivative, as described in US 2007/0092755.
  • the compound of the formula (I) or (II) can be contained in a hole injection layer, in a hole transport layer, and / or in an electron blocking layer of the device. If the connection is in a
  • a hole injection layer or a hole transport layer is present, it is preferably p-doped, that is to say it is mixed with a p-dopant, as described above, in the layer.
  • the compound of the formula (I) or (II) in one is preferred
  • Electron blocking layer included In this case it is preferably not p-doped. In this case, it is furthermore preferred than Single compound in the layer before, without adding another compound.
  • the compound of the formula (I) or (II) is used in an emitting layer as matrix material in combination with one or more emitting compounds, preferably phosphorescent emitting compounds.
  • the phosphorescent emitting compounds are preferably selected from red phosphorescent and green phosphorescent compounds.
  • the proportion of the matrix material in the emitting layer is in this case between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferably between 85.0 and 97.0% by volume.
  • the proportion of the emitting compound is between 0.1 and 50.0% by volume, preferably between 0.5 and 20.0% by volume and particularly preferably between 3.0 and 15.0% by volume.
  • An emitting layer of an organic electroluminescent device can also contain systems comprising several matrix materials (mixed matrix systems) and / or several emitting compounds.
  • the emitting compounds are generally those compounds whose proportion in the system is the smaller and the matrix materials are those compounds whose proportion in the system is the larger.
  • the proportion of a single matrix material in the system can be smaller than the proportion of a single emitting compound. It is preferred that the compounds according to formula (I) or (II) are used as a component of mixed matrix systems, preferably for phosphorescent emitters.
  • the mixed matrix systems preferably comprise two or three different matrix materials, particularly preferably two different matrix materials.
  • One of the two materials is preferably a material with hole-transporting properties and the other material is a material with electron-transporting properties. It is also preferred if one of the materials is selected from compounds with a large energy difference between HOMO and LUMO (wide-bandgap materials ).
  • the compound of the formula (I) or (II) preferably represents the matrix material with hole-transporting properties. Accordingly, if the compound of the formula (I) or (II) is used as a matrix material for a phosphorescent emitter in the emitting layer of an OLED is used, a second matrix compound is present in the emitting layer, which has electron-transporting properties.
  • the two different matrix materials can be present in a ratio of 1:50 to 1: 1, preferably 1:20 to 1: 1, particularly preferably 1:10 to 1: 1 and very particularly preferably 1: 4 to 1: 1.
  • the desired electron-transporting and hole-transporting properties of the mixed matrix components can, however, also mainly or completely be combined in a single mixed matrix component, the further or further mixed matrix components fulfilling different functions.
  • phosphorescent emitter typically includes compounds in which the light emission is prohibited by a spin
  • Transition takes place, for example a transition from an excited Triplet state or a state with a higher spin quantum number, for example a quintet state.
  • Particularly suitable phosphorescent emitters are compounds which, when suitably excited, emit light, preferably in the visible range, and which 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.
  • the phosphorescent emitters used are preferably compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds which contain iridium, platinum or copper.
  • Preferred fluorescent emitting compounds are selected from the class of the arylamines.
  • an arylamine or an aromatic amine is a compound understood, which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a condensed ring system, particularly preferably having at least 14 aromatic ring atoms.
  • Preferred examples of these are aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrene amines, aromatic pyrene diamines, aromatic chrysen amines or aromatic chrysene diamines.
  • aromatic anthracenamine is understood to mean a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position.
  • Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysen diamines are defined analogously thereto, the diarylamino groups on the pyrene preferably being bonded in the 1 position or in the 1,6 position.
  • emitting compounds are indenofluorenamines or diamines, benzoindenofluorenamines or diamines, and dibenzoindenofluorenamines or diamines, and indenofluoren derivatives with condensed aryl groups. Pyrene arylamines are also preferred. Benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines and fluorene derivatives which are linked with furan units or with thiophene units are likewise preferred.
  • Preferred matrix materials for fluorescent emitters are selected from the classes of oligoarylenes (e.g. 2,2 ', 7,7'-tetraphenyl spirobifluoren), in particular oligoarylenes containing condensed aromatic groups, oligoarylenvinylenes, polypodal metal complexes, hole-conducting Compounds of the electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides; the Atropisomers, boronic acid derivatives or benzanthracenes.
  • oligoarylenes e.g. 2,2 ', 7,7'-tetraphenyl spirobifluoren
  • oligoarylenes containing condensed aromatic groups oligoarylenvinylenes
  • polypodal metal complexes hole-conducting Compounds of the electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides
  • Particularly preferred matrix materials are selected from the classes of the oligoarylenes, containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, the oligoarylene vinylenes, the ketones, the phosphine oxides and the sulfoxides.
  • Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzphenanthrene and / or pyrene or atropisomers of these compounds.
  • an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another.
  • Matrix materials for phosphorescent emitters are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, triarylamines, carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl) or carbazole derivatives, indolocarbazole derivatives, indenocarbazole derivatives, aza carbazole derivatives, bipolar matrix materials, silanes, azaboroles or
  • Electron-transporting materials include but not limited to, butyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether, benzyl ether sulfonyl sulfonyl sulfonyl sulfonyl, benzyl, benzyl, benzyl ether, benzyl ether sulfate, benzyl ether sulfate, benzyl ether sulfate, benzyl ether sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl sulfonyl
  • Suitable electron-transporting materials are, for example, those described in Y. Shirota et al. , Chem. Rev. 2007, 107 (4), 953-1010 disclosed compounds or other materials as used in these layers according to the prior art.
  • materials for the electron transport layer all materials can be used which are used according to the prior art as electron transport materials in the electron transport layer.
  • Aluminum complexes for example Alq3, zirconium complexes, for example Zrq4, lithium complexes, for example Liq, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketone derivatives, lactams, boranes, diazaphospholones, and phosphinoxide derivatives.
  • Alq3, zirconium complexes for example Zrq4
  • lithium complexes for example Liq
  • benzimidazole derivatives for example Liq
  • benzimidazole derivatives triazine derivatives
  • pyrimidine derivatives pyridine derivatives
  • pyrazine derivatives quinoxaline derivatives
  • quinoline derivatives quinoline derivatives
  • oxadiazole derivatives aromatic ketone derivatives
  • lactams boranes, diazaphospho
  • indenofluorenamine derivatives amine derivatives, hexaazatriphenylene derivatives, amine derivatives with condensed aromatics, monobenzoindenofluorenamines, dibenzoindenofluorenamines, spirobifluorene amines, fluoreno-amines, Amines, spiro-dibenzopyran-amines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene-diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, spiro-bisacridines, xanthene-spiro-diarylamines with diarylamine groups and 9,10-spiro
  • the following compounds HT-1 to HT-7 are suitable for use in a layer with a hole-transporting function, in particular in a hole-injection layer, a hole-transport layer and / or an electron blocking layer, or for use in an emitting layer as a matrix material, in particular as a matrix material in a emitting layer containing one or more phosphorescent emitters:
  • the compounds HT-1 to HT-7 are generally well suited for the abovementioned uses in OLEDs of any type and composition, not just in OLEDs according to the present application. Processes for the preparation of these compounds and further relevant disclosures for the use of these compounds are disclosed in the laid-open specifications which are listed in brackets in the table under the respective compounds. The compounds show good performance data in OLEDs, in particular good service life and good efficiency.
  • metal alloys or multilayer structures made of different metals are preferred, such as alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Furthermore, alloys of an alkali or alkaline earth metal and silver, for example an alloy of
  • Magnesium and silver In the case of multi-layer structures, other metals can also be used in addition to the metals mentioned, which have a relatively high work function, such as. B. Ag or AI, then in Usually combinations of metals such as Ca / Ag, Mg / Ag or Ba / Ag can be used. It can also be preferred to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor. For example, alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. LiF, LhO, BaF2, MgO, NaF, CsF, CS2CO3, etc.) come into consideration. Lithium quinolinate (LiQ) can also be used for this. The layer thickness of this layer is preferably between 0.5 and 5 nm.
  • the anode preferably has a work function greater than 4.5 eV vs. vacuum.
  • metals with a high redox potential are suitable for this, such as Ag, Pt or Au.
  • metal / metal oxide electrodes for example Al / Ni / NiO x , Al / PtO x
  • at least one of the electrodes must be transparent or partially transparent in order to enable either the irradiation of the organic material (organic solar cell) or the extraction of light (OLED, O-LASER).
  • Preferred anode materials here are conductive mixed metal oxides. Indium-tin-
  • ITO Indium-Zinc Oxide
  • IZO Indium-Zinc Oxide
  • conductive, doped organic materials in particular conductive doped polymers, are preferred.
  • the anode can also consist of several layers, for example an inner layer made of ITO and an outer layer made of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
  • the electronic device is characterized in that one or more layers are coated using a sublimation process.
  • the materials are used 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 that the initial pressure is even lower, for example less than 10 7 mbar.
  • An electronic device is also 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.
  • OVJP Organic Vapor Jet Printing
  • the materials are applied directly through a nozzle and structured in this way (e.g. BMS Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
  • an electronic 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, nozzle printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (inkjet printing) can be produced. Soluble compounds according to formula (I) or (II) are necessary for this. High solubility can be achieved by suitable substitution of the compounds.
  • one or more layers of solution and one or more layers are applied by a sublimation process.
  • the device After the layers have been applied, the device is structured, contacted and finally sealed, depending on the application, in order to exclude the damaging effects of water and air.
  • the electronic devices containing one or more compounds of the formula (I) or (II) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications.
  • the OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / electron transport layer, optionally with a second layer (ETL) / electron injection layer (EIL) and finally a cathode .
  • the cathode is formed by a 100 nm thick aluminum layer.
  • the emission layer consists of at least one matrix material (host material) and an emitting dopant, which the matrix material or the matrix materials by co-evaporation in a certain Volume fraction is added.
  • a specification such as H: SEB (95%: 5%) means that the material H is present in a volume fraction of 95% and SEB in a fraction of 5% in the layer.
  • the electron transport layer and the hole injection layer also consist of a mixture of two materials.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the external quantum efficiency (EQE, measured in%) as a function of the luminance, calculated from current-voltage-luminance characteristics assuming a Lambertian radiation characteristic, and the service life are determined.
  • the specification EQE @ 10mA / cm 2 denotes the external quantum efficiency that is achieved at 10 mA / cm 2 .
  • the specification U @ 10 mA / cm 2 denotes the
  • the service life LT is defined as the time after which the luminance drops from the initial luminance to a certain percentage when operating with a constant current density.
  • An indication of LT80 means that the specified service life corresponds to the time after which the luminance has dropped to 80% of its initial value.
  • the specification @ 60 or 40 mA / cm 2 means that the relevant service life is measured at 60 or 40 mA / cm 2.
  • OLEDs according to the invention containing a compound of the formula (I) in the EBL of green phosphorescent OLEDs
  • OLEDs can be produced which contain one of the compounds HTM-2 to HTM-5 instead of the compound HTM-1:
  • OLEDs according to the invention containing a compound of the formula (I) in the EBL of blue fluorescent OLEDs Devices as shown in the following table are manufactured: In the device setup shown above, the connections according to the invention give very good efficiencies and lifetimes for the OLEDs:
  • OLEDs can be produced which contain one of the compounds HTM-2 to HTM-5 instead of the compound HTM-1:
  • OLEDs according to the invention containing a compound of the formula (I) in the HIL and HTL of blue fluorescent OLEDs
  • OLEDs can be produced which contain one of the compounds HTM-2 to HTM-5 instead of the compound HTM-1:

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