EP4423065A1 - Composés pour dispositifs électroniques - Google Patents

Composés pour dispositifs électroniques

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Publication number
EP4423065A1
EP4423065A1 EP22809746.5A EP22809746A EP4423065A1 EP 4423065 A1 EP4423065 A1 EP 4423065A1 EP 22809746 A EP22809746 A EP 22809746A EP 4423065 A1 EP4423065 A1 EP 4423065A1
Authority
EP
European Patent Office
Prior art keywords
groups
aromatic ring
substituted
ring systems
carbon atoms
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
EP22809746.5A
Other languages
German (de)
English (en)
Inventor
Elvira Montenegro
Jens ENGELHART
You-hyun KIM
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 EP4423065A1 publication Critical patent/EP4423065A1/fr
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
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    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
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    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
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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
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K50/18—Carrier blocking layers
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
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    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
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Definitions

  • the present application relates to fluorenylamines in which the fluorenyl group has at least two substituents on the benzene rings of the fluorene.
  • the compounds are suitable for use in electronic devices.
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • the term OLEDs is understood to mean electronic devices which have one or more layers containing organic compounds and emit light when an electrical voltage is applied.
  • the structure and general functional principle of OLEDs are known to those skilled in the art.
  • Emission layers and layers with a hole-transporting function have a major impact 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 which have a high glass transition temperature, high stability and high conductivity for holes.
  • a high stability of the connection is a prerequisite for achieving a long service life of the electronic device.
  • compounds are sought whose use in electronic devices to improve the performance of the Devices leads, in particular, to high efficiency, long service life and low operating voltage.
  • triarylamine compounds such as spirobifluoreneamines and fluoreneamines are known in the art as hole-transporting materials and hole-transporting matrix materials for electronic devices.
  • spirobifluoreneamines and fluoreneamines are known in the art as hole-transporting materials and hole-transporting matrix materials for electronic devices.
  • fluorene amines according to the formula below, which are characterized in that they have at least two substituents on the benzene rings of the fluorene, are extremely suitable for use in electronic devices. They are suitable in particular for use in OLEDs, again in particular for use therein as hole-transport materials and for use as hole-transporting matrix materials, in particular for phosphorescent emitters.
  • the compounds found lead to a long service life, high efficiency and low operating voltage, in particular high efficiency of the devices.
  • the compounds found also preferably have a high glass transition temperature, high stability, a low sublimation temperature, good solubility, good synthetic accessibility and high conductivity for holes.
  • the preferred properties of the compounds are due in part to their asymmetric structure, i.e. the three groups attached to the nitrogen atom are not all the same.
  • Particularly advantageous properties can be achieved if the compounds have one or more fluorenyl groups on the amine which are not substituted on their benzene rings and/or if they have heteroaromatic systems or aromatic systems other than fluorenyl on the amine.
  • the subject of the present application is a compound of a formula where the occurring variables are defined as follows:
  • Z 1 is C when a group R 1 or a group is bonded thereto and is otherwise on each occurrence the same or different selected from CR 2 and N;
  • Ar L is selected from aromatic ring systems having from 6 to 40 aromatic ring atoms substituted with R 3 groups and heteroaromatic ring systems having from 5 to 40 aromatic ring atoms substituted with R 3 groups;
  • Ar 1 is selected from aromatic ring systems having from 6 to 40 aromatic ring atoms substituted with R 4 groups and heteroaromatic ring systems having from 5 to 40 aromatic ring atoms substituted with R 4 groups;
  • Ar 2 is selected from aromatic ring systems having from 6 to 40 aromatic ring atoms substituted with R 4 groups and heteroaromatic ring systems having from 5 to 40 aromatic ring atoms substituted with R 4 groups;
  • R 1 is selected identically or differently on each occurrence from F, CN, N(R 7 ) 2 , straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic ring systems are each substituted with radicals R 7 ;
  • an aryl group is understood to mean either a single aromatic cycle, ie benzene, or a condensed aromatic polycycle, for example naphthalene, phenanthrene or anthracene.
  • a condensed aromatic polycycle consists of two or more individual aromatic cycles condensed with one another. Condensation between cycles is understood to mean that the cycles share at least one edge with one another.
  • An aryl group within the meaning of this invention contains 6 to 40 aromatic ring atoms. Furthermore, an aryl group does not contain a heteroatom 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 fused heteroaromatic polycycle, for example quinoline or carbazole.
  • a fused heteroaromatic polycycle consists of two or more individual aromatic or heteroaromatic cycles fused with one another, where at least one of the aromatic and heteroaromatic cycles is a heteroaromatic cycle. Condensation between cycles is understood to mean that the cycles share at least one edge with one another.
  • One Heteroaryl group in the context of this invention 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, 0 and S.
  • An aryl or heteroaryl group which can each be substituted with the above radicals, is understood to mean, in particular, groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, triphenylene, fluoranthene, benzanthracene, benzophenanthrene, 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, phenothi
  • An aromatic ring system within the meaning of this invention is a system which does not necessarily only contain aryl groups, but which can additionally contain one or more non-aromatic rings which are fused with at least one aryl group. These non-aromatic rings contain only carbon atoms as ring atoms. Examples of groups encompassed by this definition are tetrahydronaphthalene, fluorene and spirobifluorene.
  • the term 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.
  • An aromatic ring system within the meaning of this invention 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 need not contain exclusively aryl groups and heteroaryl groups, but may additionally contain one or more non-aromatic rings fused with at least one aryl or heteroaryl group.
  • the non-aromatic rings can contain only C atoms as ring atoms, or they can additionally contain one or more heteroatoms, where the heteroatoms are preferably selected from N, 0 and S.
  • An example of such a heteroaromatic ring system is benzopyranyl.
  • 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 4,6-diphenyl-2-triazinyl.
  • a heteroaromatic ring system within the meaning of this invention contains 5 to 40 ring atoms selected from carbon and heteroatoms, where at least one of the ring atoms is 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 thus 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 may exist as a ring atom of a non-aromatic heterocyclic ring or as a ring atom of an aromatic heterocyclic ring.
  • any aryl group is included within the term "aromatic ring system” and any heteroaryl group is included within 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, indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, indenocarbazole, or combinations of these groups.
  • 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 having 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, is preferably 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, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-but
  • the wording that two or more radicals can form a ring with one another is to be understood, inter alia, as meaning that the two radicals are linked to one another by a chemical bond.
  • the above formulation should also be understood to mean that if one of the two radicals is hydrogen, the second radical binds to the position to which the hydrogen atom was bonded, forming a ring.
  • the compound of formula (I) is preferably a monoamine, i.e. it preferably has a single amino group.
  • the compound of formula (I) is a diamine, i.e. it has two and not more than two amino groups.
  • a group R 2 in the formula (I) is -NAr 1 Ar 2 or is N(R 7 ) 2 , more preferably is -NAr 1 Ar 2 .
  • Z 1 is preferably equal to C when a group R 1 or the group is attached thereto, and is otherwise preferably equal to CR 2 .
  • no more than three groups Z 1 are equal to N, particularly preferred that no more than two groups Z 1 are N, most preferred that no more than one Z 1 group is N, and most preferred that no Z 1 group that is N is present.
  • the group is bonded in the 4-position of the fluorenyl group of formula (I).
  • the above group is attached in the 3-position of the fluorenyl group of formula (I).
  • the above group is attached in the 1-position of the fluorenyl group of formula (I).
  • the above group is attached at the 4-position of the fluorenyl group of the formula (I).
  • Ar L is preferably selected on each occurrence, identically or differently, from phenyl, biphenyl, naphthyl and fluorenyl, each of which is substituted by R 3 radicals; and very particularly particularly preferably selected from phenyl and biphenyl, most preferably phenyl which is substituted with radicals R 3 , where R 3 in this case is preferably selected the same or different on each occurrence from H and D and particularly preferably is H .
  • Ar L is preferably selected from the following groups each of which is substituted at the positions shown as unsubstituted with R 3 radicals, where R 3 in these cases is preferably identical or different from H and D and is particularly preferably H.
  • R 3 in these cases is preferably identical or different from H and D and is particularly preferably H.
  • the formulas Ar L -23 to Ar L -26, Ar L -37, Ar L -42, Ar L -47, and Ar L -58 are particularly preferred, and the formulas Ar are particularly preferred L -23 to Ar L -25.
  • index n is equal to 0, so that formula (I) corresponds to preferred formula (IA).
  • index n is 1, so that formula (I) corresponds to the preferred formula (IB), particularly preferably to the formula (IB-1):
  • Preferred groups Ar 1 and Ar 2 are chosen identically or differently on each occurrence from the radicals benzene, biphenyl, terphenyl, quaterphenyl, naphthyl, fluorenyl, in particular 9,9′-dimethylfluorenyl and 9,9′-diphenylfluorenyl, benzofluorenyl, spirobifluorenyl, indenofluorenyl , Indenocarbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl, and phenyl substituted with a group selected from naphthyl, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidyl and tri
  • Ar 1 and Ar 2 are selected identically or differently on each occurrence from benzene, biphenyl, terphenyl, quaterphenyl, naphthyl, spirobifluorenyl, indenocarbazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzofuranyl, benzothiophenyl, benzo-fused dibenzofuranyl, benzo-fused dibenzothiophenyl , and phenyl substituted with a group selected from naphthyl, spirobifluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidyl and triazinyl, wherein each of the above embodiments is substituted with R 4 groups.
  • Ar 1 and Ar 2 are chosen identically or differently on each occurrence from the following groups which are substituted in each of the positions shown as unsubstituted with R 4 radicals, the R 4 radicals in these cases preferably being H or D, particularly preferably H.
  • Particularly preferred among the abovementioned formulas are the formulas Ar-1, Ar- 2, Ar-3, Ar-5, Ar-48, Ar- 50, Ar-56, Ar-78, Ar-82, Ar-109, Ar-111 , Ar-114, Ar-117, Ar-140, Ar-141, Ar-149, Ar-257, Ar-261, Ar-262 and Ar-263.
  • At least one group is selected from the groups Ar 1 and Ar 2 , preferably both groups are selected from the groups Ar 1 and Ar 2 , equal to a formula selected from the formulas (Ar-A) and (Ar-B):
  • Formula (Ar-A) Formula (Ar-B) where the bond marked with * is the bond to the nitrogen atom of formula (I), and where R 4 in formula (Ar-A) is preferably chosen to be the same or different on each occurrence Alkyl groups with 1 to 40 carbon atoms, particularly preferably from methyl, ethyl, propyl, butyl, each of which can be substituted by one or more F atoms, in particular from methyl, which can be substituted by one or more F atoms.
  • At least one group selected from the groups Ar 1 and Ar 2 is the same as the following formula (Ar-A):
  • R 4 in formula (Ar-A) is preferably chosen identically or differently on each occurrence from alkyl groups with 1 to 40 C atoms, particularly preferably from methyl, ethyl, propyl, butyl, which can each be substituted by one or more F atoms, in particular from methyl, which can be substituted by one or more F atoms.
  • At least one group selected from the groups Ar 1 and Ar 2 is the same as the following formula (Ar-B):
  • At least one group selected from the groups Ar 1 and Ar 2 is the same as a formula selected from formulas Ar-139 to Ar-152, Ar-172 to Ar-174 and Ar-177, preferably selected from formulas Ar-141 and Ar-174, these preferably being unsubstituted on the benzene rings of the fluorenyl backbone, ie R 4 is H.
  • neither Ar 1 nor Ar 2 is selected from fluorenyl groups, more preferably neither Ar 1 nor Ar 2 contains fluorenyl groups.
  • At least one group selected from the groups Ar 1 and Ar 2 is a heteroaromatic ring system, in particular a heteroaryl group, having 5 to 40 aromatic ring atoms, which is substituted with radicals R 4 , in particular a heteroaromatic ring system, again in particular a heteroaryl group selected from the preferred embodiments for Ar 1 and Ar 2 given above.
  • Ar 1 and Ar 2 are chosen differently.
  • the three groups bonded to the nitrogen atom in formula (I) are different, groups not only meaning the groups bonded directly to the nitrogen atom, but the complete groups including their possible substituents. "Different" not only means that the groups have different molecular formulas, in which case the term molecular formula also includes H and D as different atoms, but also that they are different isomers, as is the case with o-biphenyl and p- Biphenyl is the case.
  • Preferred embodiments of the formula (I) correspond to the following formula (1-1): wherein the occurring groups and indices are as defined above and preferably correspond to their preferred embodiments given above, and wherein the group -[Ar L ] n -N is attached in position 1-, 3- or 4- of the fluorenyl group.
  • the groups R 4 on the benzene rings of the fluorenyl groups are H.
  • Such compounds exhibit better properties as OLED materials than compounds in which the benzene rings of the fluorenyl groups are substituted.
  • R 4 on the bridgeheads of the fluorenyl groups is chosen identically or differently each time it occurs from straight-chain alkyl groups having 1 to 20 carbon atoms and branched alkyl groups having 3 to 20 carbon atoms, the alkyl groups having radicals R 7 are substituted, and R 7 in these cases is preferably H, D or F, more preferably H.
  • E is a single bond. It is preferred that i is zero. It is preferred that k is zero. It is preferred that m is zero. It is particularly preferred that i, k and m are zero.
  • R 1 is selected identically or differently on each occurrence from straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; where said alkyl groups and said aromatic ring systems are each substituted with radicals R 7 , where R 7 is preferably H in this case.
  • R 1 is particularly preferably selected identically or differently on each occurrence from methyl, trifluoromethyl, tert-butyl and phenyl.
  • R 1 is preferably chosen to be the same on each occurrence. According to an alternative, likewise preferred embodiment, at least two R 1 are chosen differently.
  • p 2 and q equals 0.
  • p is 0 and q is 2.
  • p 3 and q equals 0.
  • p is equal to 0 and q is equal to 3.
  • p 4 and q equals 0.
  • p is 2 and q is 0.
  • p+q is at most 4, more preferably at most 3.
  • p+q 2.
  • formula (ld) wherein the occurring groups and indices are as defined above and preferably correspond to their preferred embodiments given above, and wherein the group -[Ar L ] n -N is attached in position 1-, 3- or 4- of the fluorenyl group, preferably in 4- Position.
  • formulas (Ia) and (Ic) are particularly preferred, and formula (Ia) is most preferred.
  • formulas (laa) and (lad) and (I-ca) and (lcd) are particularly preferred, most preferably formulas (laa) and (lad). According to a particularly preferred embodiment corresponds to the
  • R 2 is preferably selected identically or differently on each occurrence from H, D, F, CN, Si(R 7 ) 3 and -NAr 1 Ar 2 , R 2 is particularly preferably H.
  • R 5 is preferably selected identically or differently on each occurrence from straight-chain alkyl groups having 1 to 20 carbon atoms and branched or cyclic alkyl groups having 3 to 20 carbon atoms, the alkyl groups each being substituted by radicals R 7 .
  • R 7 is preferably chosen the same or different on each occurrence from H, D and F, and is very particularly the same as H.
  • R 5 is particularly preferably chosen the same or different on each occurrence from methyl, ethyl, isopropyl, n -propyl, tert-butyl, iso-butyl, n-butyl, cyclobutyl, cyclopentyl, cyclohexyl, CF3, -CD3, -CD2CD3, d7-n-propyl, d7-iso-propyl, d9-n-butyl, d9-tert -butyl, d9-isobutyl, d7-cyclobutyl, d9-cyclopentyl and d11-cyclohexyl, very particularly preferably R 5 is methyl.
  • R 5 is preferably chosen to be the same on each occurrence.
  • Each occurrence of R 7 is particularly preferably selected identically or differently from H, D, F, CN, straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ones Ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms.
  • R 7 is very particularly preferably H.
  • - Z 1 is equal to C if a group R 1 or the group is bound thereto and is otherwise equal to CR 2 ;
  • - Ar L is phenylene substituted by R 3 groups, in which case R 3 is H;
  • Ar 1 is selected from aromatic ring systems having 6 to 40 aromatic ring atoms substituted by R 4 groups and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted by R 4 groups;
  • Ar 2 is selected from aromatic ring systems having 6 to 40 aromatic ring atoms substituted by R 4 groups and heteroaromatic ring systems having 5 to 40 aromatic ring atoms substituted by R 4 groups;
  • R 1 is chosen identically or differently on each occurrence from straight-chain alkyl groups having 1 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms, and aromatic ring systems having 6 to 40 aromatic ring atoms; wherein said alkyl groups and said aromatic ring systems are each substituted with radicals R 7 , in which case R 7 is preferably H;
  • R 5 is chosen identically or differently on each occurrence from straight-chain alkyl groups having 1 to 20 carbon atoms, and branched or cyclic alkyl groups having 3 to 20 carbon atoms, the alkyl groups each being substituted by radicals R 7 ;
  • R 7 is chosen identically or differently on each occurrence from H, D, F, CN, 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;
  • - p is equal to 2 and q is equal to 0, or p is equal to 0 and q is equal to 2.
  • the compounds according to the application can be prepared by a person skilled in the art using known reactions of organic chemistry.
  • a biphenyl derivative is prepared in a first step (scheme 1A) in a Suzuki reaction between a phenyl-boronic acid derivative and a carboxylic acid ester-substituted and dihalo-substituted phenyl derivative, each having a halogen group and a carries carboxylic acid ester group.
  • X and Y are selected from reactive groups, preferably halogen atoms, particularly preferably CI, Br and I.
  • R is selected identically or differently on each occurrence from H, D and organic radicals, which are preferably selected from alkyl groups, aromatic ring systems and heteroaromatic ring systems.
  • the two groups R can each also be bonded to the other benzene ring of the fluorene.
  • halogen-substituted fluorene derivatives can be prepared by the following procedure: In a first step, as shown in Scheme 1B, a biphenyl derivative substituted with two reactive groups, preferably two halogen atoms, is prepared via a Suzuki reaction.
  • Scheme 1 B a biphenyl derivative substituted with two reactive groups, preferably two halogen atoms, is prepared via a Suzuki reaction.
  • variable groups are defined as above.
  • the biphenyl derivative obtained which carries two reactive groups, in particular two halogen atoms, is reacted with a carbonyl derivative and an organometallic, in particular BuLi.
  • the resulting intermediate is converted to a fluorenyl derivative under acidic conditions (H + ).
  • a fluorenyl derivative is obtained which has the reactive group in the 1, 3 or 4 position.
  • variable groups are defined as above, and R1 is an organic radical, preferably an alkyl group.
  • R1 is an organic radical, preferably an alkyl group.
  • the two groups R can each also be bonded to the other benzene ring of the fluorene.
  • the fluorenyl derivative obtained can be converted into a compound according to the application in several ways. Following the route shown in Scheme 3, the fluorenyl derivative is treated with a secondary amine in a Buchwald reaction. The 4-position, 1-position and 3-position variants of the amine on the fluorene are shown from top to bottom in the scheme.
  • Gi and G2 are selected from organic radicals, in particular aromatic ring systems and heteroaromatic ring systems, and the other variable groups are defined as above.
  • the fluorenyl derivative can be subjected to a Suzuki reaction with a boronic acid-substituted tri(het)arylamine according to the route shown in Scheme 4.
  • the 4-position, 1-position and 3-position variants of the amine on the fluorene are shown from top to bottom in the scheme.
  • ArL is selected from aromatic ring systems and heteroaromatic ring systems, and the other variable groups are defined as above.
  • the compound according to the application can also be prepared in the way shown in Scheme 5, in which first a Suzuki coupling takes place with a suitably substituted aromatic or heteroaromatic, and the resulting coupled compound is then reacted with a secondary amine in a Buchwald reaction.
  • the 4-position, 1-position and 3-position variants of the amine on the fluorene are shown from top to bottom in the scheme.
  • variable groups are defined as above.
  • the present application relates to a process for the preparation of a compound of the formula (I), characterized in that a fluorenyl compound which carries at least one reactive group is either a) reacted with a secondary amine in a Buchwald reaction, or b) in a Suzuki reaction with a boronic acid-substituted tertiary amine, or c) in a sequence of first i) Suzuki reaction with a boronic acid-substituted and halogen-substituted aromatic or heteroaromatic compound, and then ii) Buchwald reaction of the resulting intermediate with a secondary amine, is converted to a compound of formula (I).
  • a fluorenyl compound which carries at least one reactive group is either a) reacted with a secondary amine in a Buchwald reaction, or b) in a Suzuki reaction with a boronic acid-substituted tertiary amine, or c) in a sequence of first i) Suzuki
  • the reactive group is preferably selected from CI, Br and I.
  • the fluorenyl compound mentioned above, which carries at least one reactive group is preferably prepared by reacting a halogen-substituted biphenyl compound with a carbonyl derivative, preferably a dialkylcarbonyl derivative, and an organometallic compound, preferably BuLi.
  • the abovementioned fluorenyl compound, which carries at least one reactive group is obtained by reacting a biphenyl compound, which carries a carboxylic acid ester group, with a Grignard reagent.
  • Formulations of the compounds according to the invention are required for the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) - fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4 -dimethylanisole, 3,5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decal
  • the subject matter of the invention is therefore also a formulation, in particular containing a solution, dispersion or emulsion at least one compound according to formula (I) and at least one solvent, preferably an organic solvent.
  • a solution, dispersion or emulsion at least one compound according to formula (I) and at least one solvent, preferably an organic solvent.
  • solvent preferably an organic solvent.
  • the compound of the formula (I) is suitable for use in an electronic device, in particular an organic electroluminescent device (OLED).
  • OLED organic electroluminescent device
  • the compound of formula (I) can be used in different functions and layers. Preference is given to 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.
  • a further subject of the invention is therefore 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 most 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
  • OFDs organic optical Detectors
  • organic photoreceptors organic photoreceptors
  • OFQDs organic field quench devices
  • OLEDs organic light-
  • the invention also relates to an electronic device containing at least one compound of the formula (I).
  • the electronic device is preferably selected from the devices mentioned above.
  • An organic electroluminescence device containing anode, cathode and at least one emitting layer is particularly preferred, characterized in that the device contains at least one organic layer which contains at least one compound of the formula (I).
  • An organic electroluminescent device containing an anode, cathode and at least one emitting one is preferred Layer, 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 which are arranged between the anode and the emitting layer, preferably hole-injection layer, hole-transporting layer and electron-blocking layer.
  • a hole injection layer is understood to be a layer that is directly adjacent to 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, and preferably also does 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 a high-energy LUMO and thereby prevents electrons from exiting the emissive layer.
  • the electronic device can also contain other 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, intermediate layers (interlayers), charge generation layers (charge generation layers) and/or organic or inorganic p/n transitions.
  • 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, intermediate layers (interlayers), charge generation layers (charge generation layers) and/or organic or inorganic p/n transitions.
  • each of these layers does not necessarily have to be present and the choice of layers always depends on the compounds used and, in particular, also on whether the electroluminescent device is fluorescent or phosphorescent.
  • 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-
  • the electronic device containing the compound of the formula (I) contains a plurality of emitting layers arranged one behind the other, each of which has different emission maxima between 380 nm and 750 nm. i.e. in the multiple emitting layers respectively different emitting compounds are used which fluoresce or phosphorescent and which emit blue, green, yellow, orange or red light.
  • the electronic device contains three emitting layers arranged one behind the other in the stack, of which one blue, one green and one orange or red, preferably red, emission in each case.
  • the blue emitting layer is a fluorescent layer and the green emitting layer is a phosphorescent layer and the red or orange emitting layer is a phosphorescent layer.
  • the compound according to the invention is preferably present in a hole-transporting layer or in the emitting layer. It should be noted that, instead of a plurality of emitter compounds emitting color, an individually used emitter compound which emits in a broad wavelength range can also be suitable for generating white light.
  • the compound of formula (I) is used as the hole transport material.
  • the emitting layer can be a fluorescent emitting layer, or it can be a be phosphorescent emitting layer.
  • the emitting layer is preferably a blue fluorescent layer or a green phosphorescent layer.
  • the device containing the compound of the formula (I) contains a phosphorescent emitting layer
  • this layer preferably 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.
  • the compound of the formula (I) is used as a hole-transport material in a hole-transport layer, a hole-injection layer or an electron-blocking layer, the compound can be used as a pure material, i.e. in a proportion of 100%, in the hole-transport layer, or it can be used in combination with one or several other connections are used.
  • 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 formula (I) and the one or more other hole-transporting compounds are preferably each present in an amount of at least 10%, more preferably each is present in an amount of at least 20%.
  • a hole-transporting layer containing the compound of the formula (I) additionally contains one or more p-dopants.
  • p-dopants such organic ones are preferred as p-dopants
  • Electron acceptor compounds used which can oxidize one or more of the other compounds of the mixture.
  • 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 of 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 Re2O?, MoOs, WO3 and ReOs.
  • Complexes of bismuth in the oxidation state (III), in particular bismuth(III) complexes with electron-poor ligands, in particular carboxylate ligands, are further preferred.
  • the p-dopants are preferably present in a largely uniform distribution 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 the p-doped layer in a proportion of 1 to 10%.
  • the device contains a hole injection layer which corresponds to one of the following embodiments: a) it contains a triarylamine and a p-dopant; or b) it contains a single electron-deficient material (electron acceptor).
  • the triarylamine is a mono-triarylamine, in particular one of the preferred triarylamine derivatives mentioned further below.
  • the electron-poor material is a hexaazatriphenylene derivative, as described in US 2007/0092755.
  • the compound of 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. If the compound is present in a hole injection layer or in a hole transport layer, it is preferably p-doped, ie it is present in the layer mixed with a p-dopant, as described above.
  • the compound of the formula (I) is particularly preferably contained in an electron blocking layer. In this case, it is preferably not p-doped. Furthermore, in this case it is preferably present as an individual compound in the layer, without admixture of a further 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 a plurality of matrix materials (mixed matrix systems) and/or a plurality of 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 greater. In individual cases, however, the share of an individual Matrix material in the system to be smaller than the proportion of a single emitting compound.
  • the compounds of the 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 in a mixed matrix system 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 also be combined mainly or completely in a single mixed matrix component, with the further or the further mixed matrix components fulfilling other functions.
  • phosphorescent emitters typically includes compounds in which the light emission by a spin-forbidden Transition occurs, for example a transition from a triplet excited 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 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.
  • Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, indium, palladium, platinum, silver, gold or europium are preferably used as phosphorescent emitters, in particular compounds containing indium, platinum or copper.
  • Preferred fluorescent emitting compounds are selected from the class of arylamines.
  • An arylamine or an aromatic amine in the context of this invention is understood as meaning a compound 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 a fused ring system, especially 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 chrysenediamines.
  • aromatic anthracene amine is understood to mean a compound in which a diarylamino group is attached 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 chrysenediamines 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 indenofluorene derivatives with condensed aryl groups. Also preferred are pyrene arylamines. Also preferred are benzoindenofluorene amines, benzofluorene amines, extended benzoindenofluorenes, phenoxazines, and fluorene derivatives linked to furan moieties or to thiophene moieties.
  • Preferred matrix materials for fluorescent emitters are selected from the classes of oligoarylenes (eg 2,2',7,7'-tetraphenylspirobifluorene), in particular oligoarylenes containing fused aromatic groups, oligoarylenevinylenes, polypodal metal complexes, hole-conducting compounds , the electron-conducting compounds, especially ketones, phosphine oxides, and sulfoxides; the atropisomers, the boronic acid derivatives or the benzanthracenes.
  • oligoarylenes eg 2,2',7,7'-tetraphenylspirobifluorene
  • oligoarylenes containing fused aromatic groups e.g 2,2',7,7'-tetraphenylspirobifluorene
  • oligoarylenes containing fused aromatic groups e.g 2,2',7,7'-tetraphenylspirobifluorene
  • Particularly preferred matrix materials are selected from the classes of oligoarylenes containing naphthalene, anthracene, benzanthracene and/or pyrene or atropisomers of these compounds, oligoarylenevinylenes, ketones, phosphine oxides and sulfoxides.
  • Very particularly preferred matrix materials are selected from the classes of oligoarylenes containing anthracene, benzanthracene, benzophenanthrene and/or pyrene or atropisomers of these compounds.
  • oligoarylene should be understood to mean a compound in which at least three aryl or arylene groups are bonded to one another.
  • preferred 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
  • carbazole derivatives indolocarbazole derivatives, indenocarbazole derivatives, azacarbazole derivatives, bipolar matrix materials, silanes, azaboroles or boron esters, triazine derivatives, zinc complexes, diazasilol or tetraazasilol derivatives, diazaphosphole derivatives, bridged carbazole -Derivatives, triphenylene derivatives, or lactams.
  • Electron-transporting materials are Electron-transporting materials:
  • Suitable electron-transporting materials are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010 or other materials such as are used in these layers according to the prior art.
  • Aluminum complexes for example Alqs, 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 ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives are particularly suitable.
  • Preferred electron transport and electron injecting materials are the compounds shown in the table on page 122 to page 123 of WO2020/127176.
  • Hole Transporting Materials are the compounds shown in the table on page 122 to page 123 of WO2020/127176.
  • Other 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, spirobifluorene amines, fluorene amines, spiro Dibenzopyran amines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, spiro-bisacridines, xanthene diarylamines, and 9,10-dihydroanthracene spiro compounds with diarylamino groups.
  • 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 lanthanides (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, Etc.). Also suitable are alloys of an alkali or alkaline earth metal and silver, for example an alloy of magnesium and silver.
  • other metals can also be used which have a relatively high work function, such as e.g. B.
  • a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor may also be preferable to introduce a thin intermediate layer of a material with a high dielectric constant between a metallic cathode and the organic semiconductor.
  • Lithium quinolinate (LiQ) can also be used for this.
  • 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 of greater than 4.5 eV vs. vacuum.
  • metals with a high redox potential such as Ag, Pt or Au, are suitable for this.
  • metal/metal oxide electrodes eg Al/Ni/NiOx, Al/PtOx
  • at least one of the electrodes must be transparent or partially transparent in order to allow 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 oxide (ITO) or indium zinc oxide (IZO) are particularly preferred.
  • 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 vapour-deposited in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10′ 7 mbar.
  • An electronic device is also preferred, characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) method or with the aid of carrier gas sublimation.
  • the materials are applied at a pressure of 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 method, 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 (ink jet printing). Soluble compounds according to formula (I) are necessary for this. High solubility can be achieved by suitable substitution of the compounds.
  • any printing method 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 (ink jet printing).
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink jet printing
  • one or more layers are applied from 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) can be used in displays, as light sources in lighting applications and as light sources in medical and/or cosmetic applications.
  • reaction mixture is slowly allowed to warm to room temperature, the reaction is stopped with NH4Cl and then concentrated on a rotary evaporator.
  • the solid is quenched in 500 mL toluene and then 720 mg (3.8 mmol) p-toluenesulfonic acid are added.
  • the batch is heated under reflux for 6 hours, then allowed to cool to room temperature and treated with water.
  • the precipitated solid is filtered off and washed with heptane (31.1 g, 93% yield).
  • the OLEDs have the following layer structure: suprimlebstrat / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / 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 is shown below.
  • the materials required to produce the OLEDs are shown in a table below.
  • a fluorene derivative is used as the “HTM” material of the HIL and the HTL.
  • NDP-9 from Novaled AG, Dresden, is used as p-dopant.
  • the emission layer consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is added to the matrix material or matrix materials by co-evaporation in a specific volume fraction.
  • a specification such as H:SEB (95%:5%) means that the material H is present in the layer in a volume fraction of 95% and SEB in a fraction of 5%.
  • the electron transport layer and the hole injection layer also consist of a mixture of two materials.
  • the OLEDs are characterized by default.
  • 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 refers to the external quantum efficiency that is achieved at 10mA/cm 2 .
  • the service life LT is defined as the time after which the luminance drops from the starting luminance to a certain percentage during operation with constant current density.
  • An indication of LT90 means that the specified service life corresponds to the time after which the luminance has dropped to 90% of its initial value.
  • the Specification @80 mA/cm 2 means that the service life in question is measured at 80 mA/cm 2 .
  • connections according to the application can be used in the EBL, as shown below for connections 4a, 5n, 4c and 5d:

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  • Physics & Mathematics (AREA)
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  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electroluminescent Light Sources (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

La présente invention concerne un composé de formule (I), l'utilisation du composé dans des dispositifs électroniques, des procédés de fabrication du composé, et des dispositifs électroniques contenant le composé.
EP22809746.5A 2021-10-29 2022-10-26 Composés pour dispositifs électroniques Pending EP4423065A1 (fr)

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