EP4041709A1 - Verbindungen für elektronische vorrichtungen - Google Patents

Verbindungen für elektronische vorrichtungen

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Publication number
EP4041709A1
EP4041709A1 EP20774934.2A EP20774934A EP4041709A1 EP 4041709 A1 EP4041709 A1 EP 4041709A1 EP 20774934 A EP20774934 A EP 20774934A EP 4041709 A1 EP4041709 A1 EP 4041709A1
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
EP20774934.2A
Other languages
German (de)
English (en)
French (fr)
Inventor
Elvira Montenegro
Teresa Mujica-Fernaud
Rachel TUFFIN
Frank Voges
Amir Hossain Parham
Alexander Christian Comely
Antoni MORAGAS SOLA
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 EP4041709A1 publication Critical patent/EP4041709A1/de
Pending legal-status Critical Current

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    • 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
    • C07D333/78—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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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • 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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    • C07D209/56—Ring systems containing three or more rings
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    • C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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Definitions

  • the present application relates to spirobifluorene derivatives in which one or more of the benzene rings is replaced with a heteroaryl ring.
  • the compounds are suitable for use in electronic devices.
  • Electronic devices in the context of this application are understood to mean so-called organic electronic devices which contain organic semiconductor materials as functional materials.
  • OLEDs organic electroluminescent devices.
  • OLEDs organic electroluminescent devices.
  • 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. In the case of electronic devices, in particular OLEDs, there is great interest in improving the performance data. A completely satisfactory solution has not yet been found on these points.
  • Emission layers and layers with a hole-transporting function have a major 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.
  • compounds are sought in particular that have a high glass transition temperature, high stability, and high conductivity for holes.
  • a high stability of the connection is one 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.
  • a group A is bound to a unit R, this means that no group R 1 or R 2 is bound to the relevant position, so that this position is free for binding to group A.
  • an aryl group is understood to mean either a single aromatic cycle, that is to say benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene or anthracene.
  • 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 hetero atom as an aromatic ring atom, but only carbon atoms.
  • a heteroaryl 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 condensed 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.
  • 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 in particular to mean 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, benzo-6,7-quinoline, benzo-7,8-quinoline,
  • an aromatic ring system 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 only contain carbon atoms as ring atoms. Examples of groups encompassed by this definition are tetrahydronaphthalene, fluorene and spirobifluorene.
  • aromatic ring system also includes systems which consist of two or more aromatic ring systems which are linked to one another via single bonds, for example biphenyl, terphenyl, 7-phenyl-2-fluorenyl, quaterphenyl and 3,5-diphenyl-1-phenyl.
  • an aromatic ring system contains 6 to 40 carbon atoms and no heteroatoms in the ring system.
  • the definition of “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 preferably being 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.
  • heteroatoms of the heteroaromatic ring system are preferably selected from N, O and S.
  • the terms “heteroaromatic 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 encompassed by the term “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 is 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 CH 2 groups can be substituted by the groups mentioned above in the definition of the radicals, 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-
  • An alkoxy or thioalkyl group with 1 to 20 carbon atoms in which individual H atoms or CH 2 groups can also be substituted by the groups mentioned above in the definition of the radicals are preferably methoxy, trifluoromethoxy, ethoxy, n- Propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methyl-butoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n- Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio,
  • precisely one unit R is particularly preferably selected from units of the formulas (R-2) and (R-3) and the remaining three units R correspond to the formula (R-1).
  • exactly one or exactly two units R in formula (I) correspond to formula (R-2), and the other units R correspond to formula (R-1).
  • Particularly preferably, exactly one unit R in formula (I) corresponds to formula (R-2), and the remaining three units R correspond to formula (R-1).
  • X is preferably selected identically or differently on each occurrence from O and S, particularly preferably X is S.
  • the remaining groups are correspondingly equal to CR 1 .
  • adjacent groups Z in a ring are not equal to N.
  • at most 3 groups Z in a formula (I) are equal to N, particularly preferably at most 2 groups Z in a formula (I) are equal to N, very particularly preferably at most one group Z in a formula (I) are equal to N, most strongly no group Z is equal to N.
  • 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, spir
  • Ar 0 is phenyl substituted with radicals R 2 , where R 2 is preferably H.
  • Ar 1 is preferably selected from aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted with 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, spirobifluorenyl, indenofluorenyl, indenocarbazolyl, dibenzofuranyl, benzokurobenzothi
  • 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, fluorenyl-substituted phenyl, spirobifluorenyl-substituted, phenyl-substituted phenyl, dibenzofuranyl-substituted pheny
  • Ar 1 is phenyl substituted with radicals R 2 , where R 2 is preferably H.
  • R 1 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 , 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 in each case are substituted by 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 and R 1 -177 are particularly preferred.
  • R 2 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 , 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 in each case are substituted by radicals R 5 , which are preferably H.
  • R 2 is very particularly preferably H.
  • 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 2 and heteroaromatic ring systems with 5 to 20 aromatic ring atoms which radicals R 2 are substituted.
  • 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 2.
  • Ar L is very particularly preferably a divalent group derived from benzene, biphenyl or naphthalene, which is in each case substituted by one or more radicals R 2 , the radicals R 2 preferably being H in this case.
  • k is 0.
  • the above formulas are 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, 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, benzocarbazole, carbazole, benzofuran, benzothiophene, indole, quinoline, pyridine, pyridine, pyridine Pyrazine, pyridazine, and triazine, where the monovalent groups are each substituted with one or more radicals R 3.
  • 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, pyridine, pyrimidine, pyrazine, pyridazine and triazine, the groups each being substituted by one or more radicals R 3.
  • the groups Ar 2 are completely or partially deuterated.
  • Particularly preferred groups 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, benzofuranyl, benzothiophenyl, benzofused dibenzofuranyl, benzofused dibenzothiophenyl, naphthyl-substituted phenyl, fluorenyl-substituted phenyl, spirobifluorenyl-substituted, phenyl-substituted phenyl,
  • Ar 2 is the same or different selected 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 equal to 0 or 1, particularly preferably equal to 0.
  • 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:
  • the unit of formula (A) is selected from the following formulas:
  • 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 C atoms which can be deuterated, branched or cyclic alkyl groups with 3 to 20 C 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 ones Ring atoms which can be deuterated, the alkyl groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned each being substituted by radicals R 5 , which are preferably H.
  • R 3 is very particularly preferably equal to H.
  • R 4 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, the alkyl groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ones mentioned Ring systems are each substituted with radicals R 5 , which are preferably H.
  • R 4 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, the alkyl groups mentioned, the aromatic ring systems mentioned and the heteroaromatic ones mentioned 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) correspond to the formulas (I-A) to (ID),
  • the formula (IA) is preferred here.
  • the group A is bound to a unit (R-1), it is preferably bound in a position which corresponds to position 1, 2 or 4 on the spirobifluorene, preferably position 2 or 4. Positions 1, 2 and 4 are the following positions on the spirobifluoren skeleton:
  • Precisely one group A is preferably bonded per formula.
  • X is preferably equal to S or O, particularly preferably equal to S.
  • formulas (I-1) to (I-5), particularly preferably formulas (I-1) to (I-3), and formula (I-1) is very particularly preferred.
  • Preferred embodiments of the formulas (I-1) to (I-4) correspond to the following formulas:
  • Ar 0 is preferably phenyl which is substituted by radicals R 2 , R 2 being preferably H in these cases.
  • Ar 1 is preferably phenyl, which is substituted by radicals R 2 , R 2 being preferably H in these cases.
  • formulas (I-1S-1) to (I-3S-4), (I-1O-1) to (I-3O-4) and (I-1N-1) to (I -3N-5) preferred.
  • formulas (I-1S-1) to (I-4S-3) and (I-1O-1) to I-4O-3) are preferred.
  • the formulas (I-1S- 1) to (I-3S-4) and (I-1O-1) to (I-3O-4) are particularly preferred.
  • the formulas (I-1S-1) to (I-1S-4), (I-1O-1) to (I- 1O-4) and (I-1N-1) to (I-1N-) are also preferred 5).
  • the formulas (I-1S-1) to (I-1S-4) and (I-1O-1) to (I-1O-4) are particularly preferred.
  • -1O-4-1 particularly preferred, very particularly preferred (I-1S-3-1), (I-1S-3- 2), (I-1S-3-3), (I-1S-4-1), (I-1S-4-2) and (I-1S-4-3).
  • compounds of the formula (I) correspond to one of the formulas (I-1S-1), (I-1S-2), (I-1S-3-1), (I-1S-3-2), ( I-1S-3-3), (I-1S-4-1), (I- 1S-4-2), (I-1S-4-3), (I-1O-1), (I- 1O-2), (I-1O-3-1), (I-1O-3-2), (I-1O-3-3), (I- 1O-4-1), (I-1O- 4-2) and (I-1O-4-3), the variables in these cases preferably corresponding to their preferred embodiments given above.
  • Ar 1 is particularly preferably phenyl which is substituted by R 2 radicals which are H.
  • Preferred compounds of the formula (I) are the following compounds:
  • the corresponding configuration isomers, in particular diasteromers or enantiomers of the compounds shown above are hereby also disclosed.
  • the compounds according to formula (I) 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.
  • a preferred process for the preparation of compounds of formula (I) is shown below.
  • the method is to be understood as exemplary and not restrictive. The person skilled in the art can deviate from the exemplary method shown and make changes within the scope of his Carry out general expert knowledge, if this is technically advantageous, in order to arrive at compounds of the formula (I).
  • an intermediate according to a formula (Int-2) is prepared by ring closure. This can be converted further in an arylation reaction to give an intermediate according to a formula (Int-3) (Scheme 1).
  • V is selected identically or differently on each occurrence from reactive groups, preferably Cl, Br or I;
  • X is defined as above for formula (I);
  • 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;
  • Hal is Cl, 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;
  • i is 0, 1 or 2; 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).
  • regioisomers of the formula (Int-3) in which the group X of the hetero five-membered ring is in an adjacent position can also be prepared in an analogous way to that shown in scheme 1 (formula (Int-3b) ).
  • Scheme 1b The variables are defined as for Scheme 1.
  • Scheme 1c regioisomers of the formula (Int-3) in which the group X of the hetero five-membered ring in a adjacent position is present (Formula (Int-3c)).
  • compounds of the formula (Int-4) can also be prepared by reacting a fluorenone derivative with an ortho-metalated heteroaryl-aryl derivative (Int-A1) (Scheme 2-1):
  • the variable groups for the compounds of the formulas (Int-4), (Int-A1) and (Int-5) are defined as above, where index t is 0 or 1 and preferably is 1, and where at least one index i is present, which is equal to 1, and wherein the formulas are substituted in the free positions on the benzene ring by a radical R 1.
  • This can be done analogously for compounds of the formula (Int-3b), whereby compounds of the formula (Int-4b) result, see scheme 2b.
  • Scheme 2b The variables occurring are defined as for scheme 2.
  • compounds of the formula (Int-4b) can also be prepared by reacting a fluorenone derivative with an ortho-metalated heteroaryl-aryl derivative (Int-A2) (scheme 2b-1):
  • 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 compound (Int-1) is converted into a compound (Int-2) via a ring closure reaction by the action of acid is transferred, and further characterized in that an ortho-metalated bisaryl is added in a further step and a further ring closure reaction is carried out, a compound (Int-4) or (Int-5) being formed, and further characterized in that in a further step a Suzuki clutch or a Hartwig-Buchwald Coupling is carried out to obtain a compound of a formula (I).
  • a transition metal-catalyzed arylation is carried out after the first step, the compound (Int-2) being converted into a compound (Int-3).
  • the present application also relates to a process for the preparation of a compound of a formula (I), characterized in that in a first step a compound (Int-1b) is converted into a compound (Int-3b) via a ring closure reaction by the action of acid or a compound (Int-1c) is converted into a compound (Int-3c), and further characterized in that an ortho-metalated bisaryl is added in a further step and a further ring closure reaction is carried out, with the compound (Int- 3b) a connection (Int-4b) and from the connection (Int-3c) a connection (Int-4c) arises, and further characterized in that a Suzuki coupling or a Hartwig-Buchwald coupling is carried out in a further step whereby a compound of a formula (I) is obtained.
  • the reaction steps take place in the order given.
  • the present application also relates to a process for the preparation of a compound of a formula (I), characterized in that, in a first step, an ortho-metalated heteroaryl-aryl derivative (Int-A1), (Int-A2) or (Int- A3) is reacted with a fluorenone derivative and a ring closure reaction is carried out, a compound selected from compounds of the formulas (Int-4), (Int-4b) and (Int-4c) being formed, and further characterized in that in one a further step a Suzuki coupling or a Hartwig-Buchwald coupling is carried out, a compound of a formula (I) being obtained.
  • Suitable reactive leaving groups are, for example, bromine, iodine, chlorine, boronic acids, boronic acid esters, amines, alkenyl or alkynyl groups with a terminal CC double bond or C -C 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 further relates to oligomers, polymers or dendrimers containing one or more compounds of the formula (I), where the bond (s) to the polymer, oligomer or dendrimer are attached to any, in formula (I) with R 1 , R 2 , R 3 or R 4 substituted positions 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 of the formula (I) 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 heteroatom or via a divalent aromatic or heteroaromatic group.
  • branched and dendritic structures can for example three or more units of the formula (I) can be linked via a trivalent or higher-valent group, for example via a trivalent or higher-valent aromatic or heteroaromatic group, to form a branched or dendritic oligomer or polymer.
  • a trivalent or higher-valent group for example via a trivalent or higher-valent aromatic or heteroaromatic group
  • the same preferences apply as described above for compounds of the formula (I).
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers.
  • Suitable and preferred comonomers are selected from fluorene, spirobifluorene, 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.
  • 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 prepared by polymerizing one or more types of monomer, at least one monomer of which leads to repeating units of the formula (I) 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 which lead to CC or CN linkages are the following: (A) SUZUKI polymerization; (B) YAMAMOTO polymerization; (C) STILLE polymerization; and (D) HARTWIG-BUCHWALD 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-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3 , 4-dimethylanisole, 3,5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decal
  • the invention therefore furthermore relates to a formulation, in particular a solution, dispersion or emulsion, containing at least one compound of the formula (I) or at least one polymer, oligomer or dendrimer containing at least one unit of the formula (I) and at least one solvent, preferably one organic solvent.
  • a formulation in particular a solution, dispersion or emulsion, containing at least one compound of the formula (I) or at least one polymer, oligomer or dendrimer containing at least one unit of the formula (I) and at least one solvent, preferably one organic solvent.
  • a formulation in particular a solution, dispersion or emulsion, containing at least one compound of the formula (I) or at least one polymer, oligomer or dendrimer containing at least one unit of the formula (I) and at least one solvent, preferably one organic solvent.
  • OLED organic electroluminescent device
  • the compound of the formula (I) can be used in different functions and layers.
  • the use as a hole-transporting material in a hole-transporting layer and / or as a matrix material in an emitting layer, particularly preferably in combination with a phosphorescent emitter, is preferred.
  • the invention therefore also relates to the use of a compound of the formula (I) in an electronic device.
  • the electronic device is preferably selected from the group consisting of organic integrated circuits (OICs), 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).
  • OICs organic integrated circuits
  • OFETs organic field effect transistors
  • OFTs organic thin-film transistors
  • OLETs organic light-emitting transistors
  • OSCs organic solar cells
  • OFQDs organic field quench devices
  • OLEDs organic light-emitting electrochemical cells
  • the invention also relates to an electronic device containing at least one compound of the formula (I).
  • the electronic device preferably selected from the devices mentioned above.
  • 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).
  • 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).
  • 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 mean a layer which directly adjoins the anode.
  • a hole transport layer is understood to mean a layer which 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 that 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.
  • hole injection layers 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, on whether it is a fluorescent or phosphorescent electroluminescent device.
  • the sequence of the layers of the electronic device is preferably as follows: -Anode- -Hole injection layer- -Hole transport layer- -optional further hole transport layers- -emitting layer- -optional hole blocking layer- -electron transport layer- -electron injection layer- -Cathode-. It should again be pointed out that not all of the layers mentioned need to be present and / or that additional layers can also be present.
  • the organic electroluminescent device according to the invention can contain a plurality of emitting layers.
  • emission layers particularly preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie different emitting compounds are used in the emitting layers which can fluoresce or phosphoresce and which are blue, green, yellow, orange or red Emit light.
  • Three-layer systems that is to say systems with three emitting layers, are particularly preferred, one of the three layers showing blue, one of the three layers green 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.
  • an emitter connection which is used individually and which emits in a broad wavelength range can also be suitable for generating white light.
  • the compound of formula (I) be used as a hole transport material.
  • 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. If the device containing the compound of the formula (I) 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) 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) 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) 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 are also preferred as dopants, preferably oxides of rhenium, molybdenum and tungsten, particularly preferably Re2O7, MoO3, WO3 and ReO3.
  • 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.
  • the following compounds are particularly preferred as p-dopants:
  • 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) can be contained in a hole injection layer, in a hole transport layer and / or in an electron blocking layer of the device.
  • the compound is present in a hole injection layer or in a hole transport layer, 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) is preferably contained in an electron blocking layer. In this case, it is preferably not p-doped. In this case, it is also preferred to be Single compound in the layer before, without adding another compound.
  • the compound of the formula (I) 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 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. In this case too, 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 an individual matrix material in the system can be smaller than the proportion of an individual emitting compound.
  • the compounds according to formula (I) 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) preferably represents the matrix material with hole-transporting properties.
  • the compound of the formula (I) is used as a matrix material for a phosphorescent emitter in the emitting layer of an OLED, a second matrix compound 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 emitters typically includes compounds in which the light emission occurs through a spin-forbidden transition, for example a transition from an excited one 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.
  • all luminescent iridium, platinum or copper complexes are regarded as phosphorescent compounds.
  • all phosphorescent complexes as used in the prior art for phosphorescent OLEDs and as known to the person skilled in the art in the field of organic electroluminescent devices are suitable for use in the devices according to the invention. Further examples of suitable phosphorescent emitters are shown in the following table: NNN Ir NF 2 ONN Ir NF 2 FNNO Ir OF 2 NNN Ir ONONN Pt NSSSNNN Pt SSS
  • Fluorescent emitters are selected from the class of the arylamines.
  • An arylamine or an aromatic amine in the context of this invention is understood to mean a compound which has three substituted or unsubstituted aromatic or contains heteroaromatic ring systems bound 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 pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysendiamines.
  • 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, pyrene diamines, chrysenamines and chrysen diamines are defined analogously, 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.
  • Matrix materials for fluorescent emitters Preferred matrix materials for fluorescent emitters are selected from the classes of oligoarylenes (e.g.
  • 2,2 ', 7,7'-tetraphenylspirobifluorenes in particular oligoarylenes containing condensed aromatic groups, oligoarylenevinylenes, polypodal Metal complexes, the hole-conducting compounds, the electron-conducting compounds, in particular ketones, phosphine oxides, and sulfoxides; the atropisomers, the boronic acid derivatives or the benzanthracenes.
  • Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and / or pyrene or atropisomers of these compounds, oligoarylene vinylenes, ketones, phosphine oxides and 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 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.
  • Electron-transporting materials Suitable electron-transporting materials are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev.
  • materials for the electron transport layer all materials can be used which, according to the prior art, as electron transport materials can be used in the electron transport layer.
  • materials for the electron transport layer all materials can be used which, according to the prior art, as electron transport materials can be used in the electron transport layer.
  • Particularly suitable are 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, diazaphosphine derivatives, and phosphine oxide derivatives.
  • Preferred electron transporting compounds are shown in the following table:
  • Hole-transporting materials Further compounds which, in addition to the compounds of the formula (I), are preferably used in hole-transporting layers of the OLEDs according to the invention are indenofluorenamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with condensed aromatics, monobenzoindenofluorenamines, dibenzoindenofluorenamines, spirobifluorenamines, fluoro-fluorene amines , Spiro-dibenzopyran-amines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene-diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, spiro-bisacridines, xanthene-spiranthene-diarylamines with.
  • Preferred hole transporting compounds
  • the following compounds HT-1 to HT-10 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-10 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 connections show good performance data in OLEDs, in particular good service life and good efficiency.
  • Metals with a low work function, metal alloys or multilayer structures made of different metals are preferred as the cathode of the electronic device, such as alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g.
  • alloys of an alkali or alkaline earth metal and silver for example an alloy of magnesium and silver
  • other metals can also be used in addition to the metals mentioned, which have a relatively high work function, such as. B. Ag or Al, in which case combinations of metals, such as Ca / Ag, Mg / Ag or Ba / Ag, are usually 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.
  • alkali metal or alkaline earth metal fluorides but also the corresponding oxides or carbonates (e.g. LiF, Li2O, BaF2, MgO, NaF, CsF, Cs2CO3, etc.) come into consideration.
  • Lithium quinolinate (LiQ) can also be used for this purpose.
  • the layer thickness of this layer is preferably between 0.5 and 5 nm. Materials with a high work function are preferred as the anode.
  • 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 are conductive mixed metal oxides. Indium-tin- Oxide (ITO) or Indium-Zinc Oxide (IZO).
  • ITO Indium-tin- 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 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 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.
  • OVPD Organic Vapor Phase Deposition
  • the materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which 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.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink-jet printing
  • Soluble compounds according to formula (I) are necessary for this. High solubility can be achieved by suitable substitution of the compounds. It is further preferred that, for the production of an electronic device according to the invention, one or more layers of solution and one or more layers are applied by a sublimation process. 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. According to the invention, the electronic devices comprising one or more compounds of the formula (I) can be used in displays, as light sources in lighting applications and as light sources in medical and / or cosmetic applications.
  • the solution is degassed and saturated with N 2. Then it is mixed with 1 g (5.1 mmol) S-Phos and 1.6 g (1.7 mmol) Pd2 (dba) 3 and then 4.1 g sodium tert-butoxide (42.7 mmol) admitted.
  • the reaction mixture is heated to boiling overnight under a protective atmosphere. The mixture is then distributed between toluene and water, the organic phase is washed three times with water and dried over Na2SO4 and concentrated using a rotary evaporator. After the crude product has been filtered through silica gel with toluene, the residue that remains is recrystallized from heptane / toluene. The substance is then sublimed in a high vacuum, purity is 99.9%. The yield is 8 g (30% of theory). The following connections are made in the same way:
  • the OLEDs basically have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) and finally a cathode.
  • the cathode is formed by a 100 nm thick aluminum layer.
  • the exact structure of the OLEDs can be found in the following tables.
  • the materials used to produce the OLEDs are shown in a table below.
  • An anthracene derivative is used as material HA, and a spirobifluorene diamine is used as SEB-A.
  • a derivative of Ir (PPy) 3 is used as the emitter TEG-A. All materials are thermally vapor deposited in a vacuum chamber.
  • the emission layer consists of at least one matrix material (host material) and an emitting dopant, which is the matrix material or is added to the matrix materials by co-evaporation in a certain volume proportion.
  • a specification like 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 structures of the materials used in the OLEDs are shown in Table 3.
  • 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 / cm2 denotes the external quantum efficiency that is achieved at 10mA / cm2.
  • the specification U @ 10 mA / cm 2 denotes the operating voltage at 10 mA / cm 2 .
  • the service life LT is defined as the time after which the luminance drops from the initial luminance to a certain proportion 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 @ 80 or 60 ,.40 mA / cm 2 in this case means that the lifetime concerned at 80 ,.60 ,.40 mA / cm 2 is measured. 2) OLEDs according to the invention containing a compound of the formula (I) in the EBL of green phosphorescent OLEDs devices as shown in the following table are produced:
  • the connections according to the invention give very good efficiencies and lifetimes for the OLEDs: Devices are also manufactured as shown in the following table: This results in very good efficiencies and lifetimes for the OLEDs: 3) 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 produced: In the device setup shown above, the connections according to the invention give very good efficiencies and lifetimes for the OLEDs: Devices are also manufactured as shown in the following table: This results in very good efficiencies and lifetimes for the OLEDs: 4) OLEDs according to the invention containing a compound of the formula (I) in which HIL and HTL are produced by blue fluorescent OLEDs devices as shown in the following table: In the device setup shown above, the connections according to the invention give very good efficiencies and lifetimes for the OLEDs:

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