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EP4031549A1 - Composés hétérocycliques péri-condensés en tant que matériaux destinés à des dispositifs électroniques - Google Patents

Composés hétérocycliques péri-condensés en tant que matériaux destinés à des dispositifs électroniques

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Publication number
EP4031549A1
EP4031549A1 EP20771870.1A EP20771870A EP4031549A1 EP 4031549 A1 EP4031549 A1 EP 4031549A1 EP 20771870 A EP20771870 A EP 20771870A EP 4031549 A1 EP4031549 A1 EP 4031549A1
Authority
EP
European Patent Office
Prior art keywords
aromatic ring
radicals
groups
ring systems
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
EP20771870.1A
Other languages
German (de)
English (en)
Inventor
Amir Hossain Parham
Christian Ehrenreich
Jens ENGELHART
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 EP4031549A1 publication Critical patent/EP4031549A1/fr
Pending legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[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
    • 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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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/16—Peri-condensed systems
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Definitions

  • the present invention relates to materials for use in electronic devices and to electronic devices containing these materials.
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • the term OLEDs are understood to mean electronic devices which have one or more layers containing organic compounds and which emit light when an electrical voltage is applied.
  • the structure and the general functional principle of OLEDs are known to the person skilled in the art.
  • Phosphorescent organometallic complexes are often used as emitting materials in OLEDs.
  • OLEDs in particular also in the case of OLEDs that show triplet emission (phosphorescence), for example with regard to efficiency, operating voltage and service life.
  • the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
  • the other materials used, such as matrix materials, are of particular importance here. Improvements in these materials can therefore also lead to improvements in the OLED properties.
  • a known class of materials that are used as matrix materials for triplet emitters in OLEDs are, for example, aromatic lactams.
  • the object of the present invention is to provide compounds which are suitable for use in an OLED, in particular as matrix material for phosphorescent emitters or as electron transport material, and lead to good properties there.
  • OLEDs are suitable.
  • the OLEDs have a long service life, high efficiency and a low operating voltage.
  • These compounds and electronic devices, in particular organic electroluminescent devices, which contain these compounds, are therefore the subject matter of the present invention.
  • Y is selected identically or differently on each occurrence from N and CR 1 ;
  • Ar 1 is an aromatic ring system with 6 to 40 aromatic ring atoms which is substituted by radicals R 2 and which is fused to the radical of formula (I) via the three carbon atoms shown in formula (I), or a heteroaromatic ring system with 5 up to 40 aromatic ring atoms which is substituted by radicals R 2 and which is fused to the radical of formula (I) via the three carbon atoms shown in formula (I);
  • Z is selected identically or differently on each occurrence from CR 4 and N, or the unit ZZ stands for a unit according to formula (Ar 2 )
  • Ar 2 is selected from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 3 , and which include the unit CC, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with radicals R 3 are substituted, and which include the unit CC, and wherein the dashed lines are the bonds of the unit ZZ to the remainder of the formula;
  • R 0 is selected identically or differently on each occurrence from 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, alkenyl or alkynyl groups with 2 to 20 carbon atoms Atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroar
  • the CC unit in formula (Ar 2 ) is understood to mean two carbon atoms which are bonded directly to one another and are part of the aromatic or heteroaromatic ring.
  • AC O
  • Z CR 4
  • one Y CR 1
  • the other YN is:
  • 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.
  • 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 exists within the meaning of the present invention
  • 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 in each case be substituted by the abovementioned radicals, includes, in particular, groups understood, 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 Dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine
  • 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 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.
  • Ring system for the purposes of this invention contains 6 to 40 carbon atoms and none 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 exclusively contain aryl groups and heteroaryl groups, but it can also contain one or more non-aromatic rings which are linked with at least one aryl or
  • Heteroaryl group are condensed.
  • 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.
  • the heteroatoms of the heteroaromatic ring system are preferably selected from N, O and S.
  • heteromatic ring system and “aromatic ring system” according to the definition of the present application differ from one another in that an aromatic ring system cannot have a heteroatom as a ring atom, while a heteroaromatic ring system must have at least one heteroatom as a ring atom.
  • This heteroatom can be used 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 CH2 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-e
  • two or more radicals can form a ring with one another is to be understood in the context of the present application, inter alia, to mean that the two radicals are linked to one another by a chemical bond. Furthermore, the abovementioned formulation should also be understood to mean that, in the event that one of the two radicals represents hydrogen, the second radical binds to the position to which the hydrogen atom was bound to form a ring.
  • Ar 1 is preferably an aromatic ring system with 6 to 18 aromatic ring atoms which is substituted by radicals R 2 and which is fused to the radical of formula (I) via the three carbon atoms shown in formula (I), or a heteroaromatic ring system with 5 to 18 aromatic ring atoms which is substituted by radicals R 2 and which is fused to the radical of formula (I) via the three carbon atoms shown in formula (I).
  • Ar 1 is particularly preferably selected from benzene, pyridine, pyrimidine, pyridazine, naphthalene, quinoline, quinazoline, Phenanthrene, anthracene, triphenylene, fluorene, carbazole, dibenzofuran and dibenzothiophene, very particularly preferably benzene, pyridine, pyrimidine, carbazole, dibenzofuran and dibenzothiophene, most preferably benzene, which are each substituted by radicals R 2 and which have the three in formula ( I) carbon atoms shown are fused onto the remainder of the formula (I).
  • the unit ZZ is preferably a unit of the formula (Ar 2 )
  • Ar 2 is selected from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 3 , and which include the unit CC, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted with radicals R 3 , and which include the unit CC, and wherein the dashed lines are the bonds of the unit ZZ to the remainder of the formula.
  • Ar 2 is preferably selected from benzene, pyridine, pyrimidine, pyridazine, pyrazine, naphthalene, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, benzothiophene, benzofuran, indole and indane, each of which is substituted by radicals R 3 , and the Include unit CC in formula (Ar 2 ).
  • Ar 2 is particularly preferably selected from benzene, thiophene, furan, benzothiophene and benzofuran, very particularly preferably benzene, which are each substituted by radicals R 3 and which include the unit CC in formula (Ar 2 ).
  • the Y adjacent to the nitrogen atom in formula (I) is preferably CR 1 and the other Y is N. According to an alternative, likewise preferred embodiment, both groups Y are CR 1 .
  • R 1 is particularly preferably selected identically or differently on each occurrence from H, 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; wherein said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 5.
  • R 1 is very preferably selected identically or differently on each occurrence from H, N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted by radicals R 5.
  • Preferred aromatic and heteroaromatic ring systems and radicals N (R 5 ) 2 as groups R 1 are selected from the following groups:
  • R 5 has the meanings given above, the dashed bond represents the bond to the basic structure of the formula (I) and the following also applies:
  • Ar 3 is on each occurrence, identically or differently, a bivalent aromatic or heteroaromatic ring system with 6 to 12 aromatic ring atoms, which is in each case substituted by radicals R 5;
  • Ar 5 is on each occurrence, identically or differently, an aromatic ring system with 6 to 40 aromatic ring atoms which is substituted by radicals R 6 , or a heteroaromatic ring system with 6 to 40 aromatic ring atoms which is substituted by radicals R 6;
  • a 1 is on each occurrence, identically or differently, C (R 5 ) 2 , NR 5 , O or S; wherein in formulas (R-78) to (R-80) preferably in each case one A 1 is NR 5 , and the other A 1 is S;
  • At least one group R 1 is preferably present in formula (I), which is selected from N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 5 , and heteroaromatic ring systems with 5 to 40 aromatic ones Ring atoms which are substituted with radicals R 5.
  • At least one group R 1 is particularly preferably present in formula (I), which is selected from the above-mentioned groups R-1 to R-82.
  • R 2 is particularly preferably selected identically or differently on each occurrence from H, 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; wherein said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 5.
  • R 2 is very preferably selected identically or differently on each occurrence from H, N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted by radicals R 5.
  • Preferred aromatic and heteroaromatic ring systems and groups N (R 5 ) 2 as groups R 2 are selected from the above-mentioned groups R-1 to R-82.
  • At least one group R 2 is preferably present in formula (I), which is selected from N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 5 , and heteroaromatic ring systems with 5 to 40 aromatic ones Ring atoms which are substituted with radicals R 5.
  • At least one group R 2 is particularly preferably present in formula (I), which is selected from the above-mentioned groups R-1 to R-82.
  • R 3 is particularly preferably selected identically or differently on each occurrence from H, 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; wherein said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 5.
  • R 3 is very preferably selected identically or differently on each occurrence from H, N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted by radicals R 5.
  • Preferred aromatic and heteroaromatic ring systems and groups N (R 5 ) 2 as groups R 3 are selected from the above-mentioned groups R-1 to R-82.
  • At least one group R 3 is preferably present in formula (I), which is selected from N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms which are substituted by radicals R 5, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms which are substituted by radicals R 5.
  • At least one group R 3 is particularly preferably present in formula (I), which is selected from the above-mentioned groups R-1 to R-82.
  • R 4 is particularly preferably selected identically or differently on each occurrence from H, 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; wherein said alkyl groups, said aromatic ring systems and said heteroaromatic ring systems are each substituted with radicals R 5.
  • R 4 is very preferably selected identically or differently on each occurrence from H, N (R 5 ) 2 , aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein the aromatic ring systems mentioned and the heteroaromatic ring systems mentioned are each substituted by radicals R 5.
  • Preferred aromatic and heteroaromatic ring systems and groups N (R 5 ) 2 as groups R 4 are selected from the above-mentioned groups R-1 to R-82.
  • formula (I) there is preferably either a) at least one group selected from the groups R 1 , R 2 , R 3 and R 4 , which is selected from aromatic ring systems with 7 to 40 aromatic ring atoms, each of which is substituted by radicals R 5 are; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; or at least two groups selected from groups R 1 , R 2 , R 3 and R 4 are present in formula (I) b) which are selected from aromatic ring systems having 6 to 40 aromatic ring atoms, each of which is substituted by radicals R 5 ; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5.
  • formula (I) there is preferably at least one group selected from the groups R 1 , R 2 , R 3 and R 4 , which is selected from aromatic ring systems having 7 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5.
  • R 1 , R 2 and R 3 is present in formula (I), which group is selected from aromatic ring systems with 7 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5.
  • At least one group selected from the groups R 1 , R 2 and R 3 is very particularly preferably present in formula (I), which group is selected from groups R-1 to R-81, as defined above. Most preferably, at least one group selected from the groups R 1 and R 2 is present in formula (I), which group is selected from groups R-1 to R-81, as defined above.
  • Y is preferably equal to N. Furthermore, it is preferred that T is equal to O. Furthermore, the preferred embodiments of the variables which are mentioned above with regard to formula (I) also apply to formula (I-A).
  • R 1-1 , R 2-1 and R 3-1 are selected from aromatic ring systems with 7 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5 , and are preferably selected from one of the groups R-1 to R-81.
  • Compounds of the formula (I) preferably correspond to one of the formulas (I-1) to (I-8) where A 2 is C (R 3 ) 2 , NR 3 , O or S; and where A 3 is C (R 2 ) 2 , NR 2 , O or S, and where X 1 is selected identically or differently on each occurrence from N and CR 2 and preferably is CR 2 , and where X 2 is in each case Occurrence identically or differently is selected from N and CR 3 and is preferably CR 3 and the other variables are defined as above; and wherein when Y is CR 1 , either a) at least one group selected from the groups R 1 , R 2 , R 3 and R 4 is present, which is selected from aromatic ring systems with 7 to 40 aromatic ring atoms, each with radicals R 5 are substituted; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; or b) at least two groups selected from
  • T is equal to O and that Y is equal to N.
  • the formulas (1-1), (I-7) and (I-8) are preferred, wherein X 1 is preferably CR 2 , X 2 is CR 3 , and Y is N in these formulas and T is O.
  • the formula (1-1) is most preferred, where preferably X 1 is CR 2 , X 2 is CR 3 , Y is N and T is O in this formula.
  • R 5 it is particularly preferred to (I-8) at least one group selected from the groups R 1 , R 2 , and R 3 is present, which is selected from groups R-1 to R-81, as defined above.
  • at least one group selected from the groups R 1 and R 2 which is selected from groups R-1 to R-81, as defined above, is very particularly preferably present.
  • T is preferably equal to O
  • Y is preferably equal to N
  • Y is preferably equal to CR 1
  • each of the above formulas there is preferably at least one group selected from the groups R 1 , R 2 and R 3 , which is selected from aromatic ring systems having 7 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, each of which is substituted by radicals R 5.
  • Particularly preferred is in the above mentioned formulas at least one group selected from the groups R 1 , R 2 , and R 3 , which is selected from groups R-1 to R-81, as defined above.
  • At least one group selected from the groups R 1 and R 2 which is selected from groups R-1 to R-81, as defined above, is very particularly preferably present in the abovementioned formulas.
  • formula (I-1-1) Most preferred among the above formulas is formula (I-1-1). Preferred variants of the formula (I-1-1) correspond to the following formulas:
  • R 1-1 and R 2-1 are selected from aromatic ring systems having 7 to 40 aromatic ring atoms, each of which is substituted by radicals R 5; and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are each substituted by radicals R 5 , and are preferably selected from one of the groups R-1 to R-81, and the other variables are defined as above and preferably correspond to their preferred embodiments .
  • T is O and that Y is N in the above-mentioned formulas.
  • the compounds of the formula (I) can be prepared by means of known synthetic steps in organic chemistry, such as, for example, bromination, Suzuki coupling and Hartwig-Buchwald coupling. Some preferred synthesis methods are shown below by way of example. These can be modified by the person skilled in the art within the scope of his general specialist knowledge and are not to be understood as limiting.
  • compounds of the formula (E-1) can be reacted with an aryl radical in a Suzuki coupling. This step is optional.
  • the NH group in the heteroaromatic ring of the compound is reacted with an aromatic which has a halogen atom in the benzyl position.
  • a ring closure reaction is then carried out with Pd catalysis, and the methylene group is then oxidized to a carbonyl group with an oxidizing agent.
  • a halogenation reaction preferably a bromination, can then optionally be carried out, followed by a coupling reaction, preferably a Suzuki or Hartwig-Buchwald coupling.
  • Ar aromatic or heteroaromatic ring
  • V halogen, preferably CI, Br or I
  • compounds of the formula (E-1) can be reacted with an aryl radical in a Suzuki coupling. This step is optional.
  • the NH group is im heteroaromatic ring of the compound reacted with an aryl or heteroaryl substituted acid halide.
  • a ring closure reaction is then carried out, preferably with tributyltin hydride (BusSnH) or Pd (PPh3) 4 plus base, for example potassium acetate.
  • This can optionally be followed by a halogenation reaction, preferably a bromination, followed by a coupling reaction, preferably a Suzuki or Hartwig-Buchwald coupling.
  • Ar aromatic or heteroaromatic ring
  • V halogen, preferably CI, Br or I
  • Compounds of the formula (E-3), some of which are commercially available, can be converted directly into a compound of the formula (I) in a Suzuki coupling with a boronic acid, in which both Groups Z are equal to CR 4 (Scheme 3).
  • V reactive group, preferably halogen, particularly preferably CI, Br or I
  • R organic radical n: 0-10
  • the present application thus provides a process for the preparation of a compound of the formula (I), characterized in that i) an imidazole or benzimidazole derivative is reacted with an aryl or heteroaryl compound which contains a benzylic halogen, preferably CI, Br, or I, and ii) a ring closure reaction is carried out under Pd catalysis, and iii) a methylene group in the ring formed is oxidized to a carbonyl group.
  • a benzylic halogen preferably CI, Br, or I
  • the aryl or heteroaryl compound with the benzylic halogen preferably has a further halogen substituent which is bonded directly to the aromatic or heteroaromatic ring, preferably in the ortho position to the group to which the benzylic halogen is bonded.
  • Steps i) to iii) are preferably carried out in the specified order and directly following one another.
  • the present application also relates to an alternative process for the preparation of a compound of the formula (I) thereby characterized in that iv) an imidazole or benzimidazole derivative is reacted with an aryl or heteroaryl compound which has a carboxylic acid halide group, preferably a carboxylic acid chloride group, carboxylic acid bromide group or carboxylic acid iodide group, and v) a ring closure reaction, preferably with a tin organyl or with Pd 0 , is performed.
  • the aryl or heteroaryl compound with the carboxylic acid halide group preferably has a halogen substituent which is bonded directly to the aromatic or heteroaromatic ring, preferably in the ortho position to the carboxylic acid halide group.
  • Steps iv) and v) are preferably carried out in the specified order and directly following one another.
  • 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, (-) -Fenchon, 1, 2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1 -methylnaphthalene, 2-
  • Methylbenzothiazole 2-phenoxyethanol, 2-pyrrolidinone, 3-methyl anisole, 4-methyl anisole, 3,4-dimethyl anisole, 3,5-dimethyl anisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, Dodecylbenzene, ethylbenzoate, indane, NMP, p-cymene, phenetol, 1,4-diisopropylbenzene, dibenzyl ether,
  • Diethylene glycol butyl methyl ether triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis (3,4-dimethylphenyl) ethane, 2-methylbiphenyl, 3- methylbiphenyl, 1-methylbiphenyl, Ethyl naphthalene, ethyl octanoate, diethyl sebacate, octanoate, heptylbenzene, menthyl isovalerate, cyclohexylhexanoate or mixtures of these solvents.
  • the present invention therefore also provides a formulation containing a compound according to the invention and at least one further compound.
  • the further connection can for example be a
  • the further compound can, however, also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitting compound and / or a further matrix material.
  • Suitable emitting compounds and further matrix materials are listed below in connection with the organic electroluminescent device.
  • This further compound can also be polymeric.
  • the compounds according to the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device.
  • the present invention therefore also relates to the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • the compound according to the invention is defined as follows: Compound of a formula (I)
  • Y is selected identically or differently on each occurrence from N and CR 1 ;
  • Ar 1 is an aromatic ring system with 6 to 40 aromatic ring atoms which is substituted by radicals R 2 and which is fused to the radical of formula (I) via the three carbon atoms shown in formula (I), or a heteroaromatic ring system with 5 up to 40 aromatic ring atoms which is substituted by radicals R 2 and which is fused to the radical of formula (I) via the three carbon atoms shown in formula (I);
  • Z is selected identically or differently on each occurrence from CR 4 and N, or the unit ZZ stands for a unit according to formula (Ar 2 )
  • Ar 2 is selected from aromatic ring systems with 6 to 40 aromatic ring atoms, which are substituted by radicals R 3 , and which include the unit CC, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms, which are substituted by radicals R 3 , and the include the unit CC, and wherein the dashed lines are the bonds of the unit ZZ to the remainder of the formula;
  • R 0 is selected identically or differently on each occurrence from 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, alkenyl or alkynyl groups with 2 to 20 carbon atoms Atoms, aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic
  • alkenyl or alkynyl groups with 2 to 20 carbon atoms aromatic ring systems with 6 to 40 aromatic ring atoms, and heteroaromatic ring systems with 5 to 40 aromatic ring atoms; wherein said alkyl, alkoxy, alkenyl and alkynyl groups and said aromatic ring systems and heteroaromatic
  • Yet another subject matter of the present invention is an electronic device containing at least one compound of the formula (I) as defined above.
  • An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or layers that are made entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic niche field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O lasers) and “organic plasmon emitting devices”, but preferably organic electroluminescent devices (OLEDs), particularly preferably phosphorescent OLEDs .
  • OLEDs organic electroluminescent devices
  • O-ICs organic integrated circuits
  • O-FETs organic field-effect transistors
  • OF-TFTs organic thin-film transistors
  • O-LETs organic light-emitting transistors
  • O-SCs organic solar cells
  • the organic electroluminescent device contains a cathode, anode and at least one emitting layer. In addition to these layers, it can also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers,
  • the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers. If several emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H.
  • Various emitting compounds that can fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, the three layers showing blue, green and orange or red emission.
  • the organic electroluminescent device according to the invention can also be a tandem OLED, in particular for white-emitting OLEDs.
  • the compound according to the invention according to the embodiments listed above can be used in different layers, depending on the precise structure.
  • the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers, at least one emitting layer containing at least one compound according to the invention as matrix material.
  • the compound according to the invention can also be used in an electron transport layer and / or in a hole blocking layer and / or in a hole transport layer and / or in an exciton blocking layer.
  • the compound according to the invention is used as a matrix material for a phosphorescent compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters).
  • Phosphorescence in the context of this invention is understood to mean the luminescence from an excited state with a higher spin multiplicity, that is to say a spin state> 1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • the mixture of the compound according to the invention and the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 80 Vol .-% of the compound according to the invention based on the total mixture of emitter and matrix material.
  • the mixture accordingly contains between 1 and 99% by volume, preferably between 2 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 20% by volume of the emitter, based on the Total mixture of emitter and matrix material.
  • Another preferred embodiment of the present invention is the use of the compound according to the invention as a matrix material for a phosphorescent emitter in combination with a further matrix material.
  • Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g. B. CBP (N, N-biscarbazolylbiphenyl) or those in WO 2005/039246, US
  • bipolar matrix materials e.g. B. according to WO 2007/137725
  • silanes e.g. B. according to WO 2005/111172
  • azaboroles or boronic esters e.g. B. according to WO 2006/117052
  • triazine derivatives e.g. B. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877
  • zinc complexes e.g. B. according to EP 652273 or WO 2009/062578
  • diazasilol or tetraazasilol derivatives e.g. B.
  • WO 2010/054729 diazaphosphole derivatives, e.g. B. according to WO 2010/054730, bridged carbazole derivatives, e.g. B. according to WO 2011/042107, WO 2011/060867, WO 2011/088877 and WO 2012/143080, triphenylene derivatives, e.g. B. according to WO 2012/048781, or dibenzofuran derivatives, e.g. B. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565.
  • a further phosphorescent emitter which emits with a shorter wave than the actual emitter, can also be present as a co-host in the mixture, or a compound that does not participate or does not participate to a significant extent in the charge transport, as described, for example, in WO 2010/108579.
  • the materials are used in combination with a further matrix material.
  • Preferred co-matrix materials especially if the compound according to the invention is substituted with an electron-poor heteroaromatic ring system, are selected from the group of biscarbazoles, bridged carbazoles, triarylamines, dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives and carbazolamines.
  • Preferred biscarbazoles are the structures of the following formulas (21) and
  • a 4 is selected from C (R 5 ) 2 , NR 5 , O or S, and is preferably the same as C (R 5 ) 2 ;
  • Examples of suitable compounds according to formula (21) or (22) are the compounds shown below.
  • Preferred bridged carbazoles are the structures of the following formula (23), where A 4 and R 7 have the meanings given above and A 4 is preferably selected identically or differently on each occurrence from the group consisting of NR 5 and C (R 5 ) 2 .
  • Preferred dibenzofuran derivatives are the compounds of the following formula (24),
  • Formula (24) where the oxygen can also be replaced by sulfur, so that a dibenzothiophene is formed L stands for a single bond or an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which is substituted with radicals R 5 , and R 7 and Ar 4 as above Have the meanings mentioned.
  • the two groups Ar 4 , which bind to the same nitrogen atom, or a group Ar 4 and a group L, which bind to the same nitrogen atom, can also be connected to one another, for example to form a carbazole.
  • suitable dibenzofuran derivatives are the following
  • Preferred carbazolamines are the structures of the following formulas (25), (26) and (27), where L stands for an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms, which is substituted by radicals R 5 , and R 5 , R 7 and Ar 4 have the meanings given above.
  • Examples of suitable carbazolamine derivatives are the compounds shown below.
  • Preferred co-matrix materials especially when the compound according to the invention is substituted with an electron-rich heteroaromatic ring system, for example a carbazole group, are furthermore selected from the group consisting of triazine derivatives, pyrimidine derivatives and quinazoline derivatives.
  • Preferred triazine, quinazoline or pyrimidine derivatives which can be used as a mixture together with the compounds according to the invention, are the compounds of the following formulas (28), (29) and (30),
  • the triazine derivatives of the formula (28) and the quinazoline derivatives of the formula (30), in particular the triazine derivatives of the formula (28), are particularly preferred.
  • Ar 4 in formulas (28), (29) and (30) is, identically or differently, an aromatic or heteroaromatic ring system with 6 to 30 aromatic ring atoms, in particular with 6 to 24 aromatic ring atoms, on each occurrence , which is substituted with radicals R 5.
  • Suitable aromatic or heteroaromatic ring systems Ar 4 are the same as those listed above as structures R-1 to R-81.
  • Suitable triazine compounds which can be used as matrix materials together with the compounds according to the invention are the compounds shown in the table below.
  • Suitable quinazoline compounds are the compounds shown in the following table:
  • Particularly suitable phosphorescent compounds are compounds which, when appropriately excited, emit light, preferably in the visible range, and also 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 contain, in particular a metal with this atomic number.
  • Phosphorescence emitters are preferred Compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are used, in particular compounds containing iridium or platinum.
  • Examples of phosphorescent dopants are listed below.
  • indenofluorenamine derivatives In hole-transporting layers of the device, such as hole-injection layers, hole-transporting layers and electron-blocking layers, preference is given to indenofluorenamine derivatives, amine derivatives, hexaazatriphenylene derivatives, amine derivatives with condensed aromatics, monobenzoindenofluorenamine, Dibenzoindenofluorenamines, spirobifluorene amines, fluorene amines, spiro-dibenzopyran-amines, dihydroacridine derivatives, spirodibenzofurans and spirodibenzothiophenes, phenanthrene-diarylamines, spiro-tribenzotropolones, spirobifluorenes with meta-phenyldiamine groups, x-phenyldiamine, 10, spiro-phenyldiamine, -Dihydroanthrac-
  • the following compounds HT-1 to HT-13 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-13 are generally well suited for the above-mentioned uses in OLEDs of all types and designs
  • composition not only in OLEDs according to the present application. Processes for the preparation of these compounds and further relevant disclosures for the use of these compounds are disclosed in the laid-open specifications which are listed in brackets in the table under the respective compounds.
  • the compounds show good performance data in OLEDs, in particular good service life and good efficiency.
  • organic electroluminescent device characterized in that one or more layers with a
  • Sublimation process are coated.
  • the materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10 -7 mbar.
  • An organic electroluminescent device is likewise preferred, characterized in that one or more layers with the OVPD (Organic Vapor Phase Deposition) process or with the help of a carrier gas sublimation.
  • the materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • OVPD Organic Vapor Phase Deposition
  • OVJP Organic Vapor Jet Printing
  • an organic electroluminescent device characterized in that one or more layers of solution, such as, for. B. by spin coating, or with any printing process, such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • any printing process such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (inkjet printing) or nozzle printing.
  • Hybrid processes are also possible in which, for example, one or more layers are applied from solution and one or more additional layers are vapor-deposited. These methods are generally known to the person skilled in the art and can be applied by him to organic electroluminescent devices containing the compounds according to the invention without any inventive step.
  • Glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm are treated with an oxygen plasma, followed by an argon plasma, before coating. These plasma-treated glass platelets form the substrates on which the OLEDs are applied.
  • structured ITO indium tin oxide
  • the OLEDs basically have the following layer structure: substrate / optional interlayer (IL) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional 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 in Table 1.
  • the materials required to produce the OLEDs are shown in Table 2.
  • the data of the OLEDs are listed in Tables 3 and 4.
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is mixed with the matrix material or matrix materials in a certain volume proportion by co-vaporization.
  • IC1 EG1: TEG1 (45%: 45%: 10%) means that the material IC1 in a volume proportion of 45%, EG1 in a proportion of 45% and TEG1 in a proportion of 10% in the layer is present.
  • the electron transport layer can also consist of a mixture of two materials.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (SE, measured in cd / A) and the external quantum efficiency (EQE, measured in%) are calculated as a function of the luminance, calculated from the current-voltage-luminance-
  • Examples E1 to E9 as matrix material in the emission layer of phosphorescent green OLEDs used (Table 3). This results in low voltage and good efficiency.
  • the compounds EG8, EG9 and EG10 according to the invention are used in Examples E10 to E13 as matrix material in the emission layer of phosphorescent red OLEDs (Table 3). This results in low voltage and good efficiency.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés de formule (I), des procédés de production de ces composés, ainsi que des dispositifs électroniques un ou plusieurs de ces composés.
EP20771870.1A 2019-09-20 2020-09-17 Composés hétérocycliques péri-condensés en tant que matériaux destinés à des dispositifs électroniques Pending EP4031549A1 (fr)

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