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WO2025210013A1 - Composés pour dispositifs électroniques, en particulier composés pour oled - Google Patents

Composés pour dispositifs électroniques, en particulier composés pour oled

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Publication number
WO2025210013A1
WO2025210013A1 PCT/EP2025/058811 EP2025058811W WO2025210013A1 WO 2025210013 A1 WO2025210013 A1 WO 2025210013A1 EP 2025058811 W EP2025058811 W EP 2025058811W WO 2025210013 A1 WO2025210013 A1 WO 2025210013A1
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WIPO (PCT)
Prior art keywords
formula
radicals
group
atoms
aromatic
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Pending
Application number
PCT/EP2025/058811
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German (de)
English (en)
Inventor
Ilona STENGEL
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of WO2025210013A1 publication Critical patent/WO2025210013A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these materials.
  • Organic, organometallic, and/or polymeric semiconductors are becoming increasingly important. Due to their cost and performance, these semiconductors are used in many commercial products. Examples include organic charge transport materials (e.g., triarylamine-based hole transporters) in copiers, organic light-emitting diodes (OLEDs) in display devices, and organic photoreceptors in copiers.
  • organic solar cells O-SC
  • organic field-effect transistors O-FETs
  • O-TFTs organic thin-film transistors
  • O-ICs organic switching elements
  • O-lasers organic laser diodes
  • Electronic devices within the meaning of this invention are understood to be organic electronic devices that contain organic semiconductor materials as functional materials.
  • the electronic devices represent electroluminescent devices such as OLEDs.
  • OLEDs which use organic compounds as functional materials
  • OLEDs are electronic devices that have one or more layers comprising organic compounds and emit light when a voltage is applied.
  • electronic devices especially OLEDs, there is a great need to improve performance, particularly lifetime, efficiency, and operating voltage. No satisfactory solution has yet been found for these aspects.
  • Electronic devices typically comprise a cathode, an anode, and at least one functional, preferably emissive, layer. In addition to these layers, they may contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and/or charge generation layers.
  • the object of the present invention is to provide compounds which are suitable for use in an electronic device, in particular an OLED, in particular as host material, as material for hole-transport layers, and/or as material for electron-transport layers, and which lead to good properties there.
  • a further object of the present invention is to provide materials for electron-blocking layers or hole-blocking layers.
  • An electron-blocking layer is understood to be a layer which is arranged between the emitting layer and the hole-transport layer and reduces the passage of electrons.
  • a hole-blocking layer is understood to be a layer which is arranged between the emitting layer and the electron-transport layer and reduces the passage of holes. Due to their sufficiently high T1 value and suitable HOMO/LUMO levels, compounds according to the present application are outstandingly suitable for use as host material in an emitting layer, in particular a blue-emitting layer, and for use in a hole-blocking layer.
  • a further object of the present invention is to provide compounds whose ability to form exciplexes can be varied as needed.
  • the variation in the propensity to form exciplexes is achieved by substitution with suitable chemical residues.
  • the HOMO/LUMO levels of the compounds serving as electron-transporting host materials should be tunable with those of a hole-transporting host material and potential emitter or sensitizer compounds, whereby the compounds should have a suitable T1 level for this purpose.
  • a further object of the present invention is to provide emitter or sensitizer compounds that prevent exciplex formation with other materials through steric shielding.
  • steric shielding can be used in fluorescent emitter compounds to prevent unwanted Dexter transfer.
  • the group of formula (1) creates the steric shielding when bound to a corresponding compound, especially an emitter or sensitizer compound.
  • Another object of the present invention is to provide compounds which have sufficient solubility, in particular due to steric demand and twisting of the molecular structure, and which have a high glass transition temperature. Sufficient solubility is an important property to enable efficient synthesis and purification of the compounds. A high glass transition temperature is important for the vapor deposition process and film formation.
  • the compounds of the invention do not form undesirable exciplexes with emitter or sensitizer compounds in the emission layer.
  • the present invention relates to a compound containing one or more units according to formula (1),
  • W is C or Si and preferably C
  • X a is, identically or differently at each occurrence, N or CR a , where at most two of the groups X a per ring stand for N, preferably at most one of the groups X a per ring stands for N and particularly preferably all groups X a stand for CR a ;
  • X b is, identically or differently at each occurrence, N or CR b , where at most two of the groups X b per ring stand for N, preferably at most one of the groups X b per ring stands for N and particularly preferably all groups X b stand for CR b ;
  • R 2 is, at each occurrence, identically or differently, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more substituents R 2 may form a ring with one another.
  • Formula (1 ) is understood to mean a compound which, in addition to formula (1 ) may contain further molecular moieties. These may, for example, be chemical groups that do not fall under formula (1), such as transition metal complexes.
  • Compounds containing one or more units of formula (1) are exemplified by compounds 71 and 72 in the table of preferred embodiments of compounds according to the application.
  • the compound according to the application is preferably a single organic compound, whereby the term "organic compound" is not intended to exclude transition metal complexes.
  • the compound according to the present application preferably has a molecular weight of not more than 2000 Da, more preferably not more than 1500 Da, most preferably not more than 1000 Da.
  • the compound according to the application is a compound according to formula (1).
  • An aryl group within the meaning of this invention contains 6 to 40 C atoms; a heteroaryl group within the meaning of this invention contains 5 to 40 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • An aryl group or heteroaryl group is understood to be either a simple aromatic ring, i.e.
  • benzene or a simple heteroaromatic ring, for example pyridine, pyrimidine, thiophene, etc., or a condensed (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.
  • Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl groups, but as an aromatic ring system.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as a system which does not necessarily contain only aryl or heteroaryl groups, but in which several aryl or heteroaryl groups can also be linked by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as a C, N or O atom or carbonyl group.
  • a non-aromatic unit preferably less than 10% of the atoms other than H
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., are also to be understood as aromatic ring systems within the meaning of this invention, as are systems in which two or more aryl groups are linked, for example, by a linear or cyclic alkyl group or by a silyl group.
  • Preferred aromatic or heteroaromatic ring systems are simple aryl or heteroaryl groups, as well as groups in which two or more aryl or heteroaryl groups are directly linked to one another, for example biphenyl, terphenyl, quaterphenyl, or bipyridine, as well as fluorene or spirobifluorene.
  • alkyl group is used as a generic term for both linear or branched alkyl groups and cyclic alkyl groups.
  • alkenyl group and alkynyl group are used as generic terms for both linear or branched alkenyl or alkynyl groups, as well as for cyclic alkenyl or alkynyl groups.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which may contain 1 to 40 C atoms and in which individual H atoms or CH2 groups may be substituted by the above-mentioned groups, preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n-hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-hepty
  • alkoxy group OR 1 with 1 to 40 carbon atoms, preference is given to 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, cyclo- heptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
  • alkyl, alkoxy, or thioalkyl groups according to the present invention can be straight-chain, branched, or cyclic, where one or more non-adjacent CH2 groups can be replaced by the above-mentioned groups; furthermore, one or more H atoms can also be replaced by D, F, Cl, Br, I, CN, or NO2, preferably D, F, Cl, or CN, particularly preferably D, F, or CN.
  • An aromatic or heteroaromatic ring system with 5 - 60 aromatic ring atoms, preferably 5 - 40 aromatic ring atoms, which may also be substituted by the above-mentioned radicals or a hydrocarbon radical and which may be linked to the aromatic or heteroaromatic ring via any desired positions, is understood to mean in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans- Indenofluorene, cis- or trans-lndenocarbazole, cis-
  • the phrase "two or more residues can form a ring" is understood to mean, among other things, that the two residues are linked by a chemical bond with the formal elimination of two hydrogen atoms. This is illustrated by the following scheme: Furthermore, the above formulation should also be understood to mean that if one of the two residues represents hydrogen, the second residue binds to the position to which the hydrogen atom was bonded, forming a ring. This is illustrated by the following scheme:
  • Y 1 represents O, S, NR d or C(R d ) 2 ;
  • exactly one of the groups R a and/or R b preferably exactly one of the groups R a , represents a group selected from structures of the formula -(L) q -(Z) S , as defined above, and is preferably defined according to the preferred embodiments set out above and below.
  • the group Z in formula -(L) q -(Z)s can be selected from structures of formulas (Z-20) to (Z-44),
  • L is, at each occurrence, identically or differently, a bivalent, trivalent or tetravalent aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, which may each be substituted by one or more radicals R c other than H, but is preferably unsubstituted or deuterated.
  • the compound according to the invention corresponds to one of the following formulas (3-1) to
  • the compound according to the invention corresponds to at least one of the following formulas (4-1) to (4-16):
  • X c is, at each occurrence, identically or differently, N, CR C or, in the event that this group binds to another group at this point, C, preferably CR C or C, where preferably at most 3 groups X c per ring represent N, particularly preferably at most 2 and very particularly preferably all groups X c represent CR C or C;
  • the group L c is selected from structures of the formulas (L c -14) to (L c -29)
  • the group L c can be selected from structures of the formulas (L c -30) to (L c -41 )
  • R c has the meaning given above, in particular for formulas (Z-1) to (Z-19).
  • the compounds according to the invention of formula (1) can be used as electron-transporting material or hole-transporting material, depending on the configuration of the radicals R a and/or R b .
  • Possible radicals R a and/or R b to be selected in order to achieve the desired properties of the compounds are generally known to the person skilled in the art, with electron-deficient heteroaryl groups as radicals R a and/or R b leading, in particular, to electron-transporting materials according to formula (1).
  • compounds according to the invention with electron-deficient heteroaryl groups can be used in hole-blocking layers, electron-transport layers, electron-injection layers and/or as host material in emitting layers.
  • At least one radical R a represents a structure of the formula -(L) q -(Z) S , preferably exactly one radical R a represents a structure of the formula -(L) q -(Z) S , where the indices q and s and the symbol Z have the meanings set out in the following table:
  • the compound corresponds to the above-mentioned formula (2), wherein exactly one radical selected from the radicals R a and R b represents a group selected from structures of the formula -(L) q -(Z) S , wherein q is 0 or 1, L is either absent or is carbazole substituted by radicals R c , in particular corresponds to formula (L c -25), s is 1, and Z is formula (Z-22); and wherein the further radicals selected from the radicals R a and R b are H or D, preferably H.
  • substituent means in particular that the radicals R, R a , R b , R c , R d , R 1 are not H. Furthermore, the substituents R, R a , R b , R c , R d , R 1 etc. can be the same or different if two or more substituents are present. In a preferred embodiment of the invention, the groups R, R a , R b , R c , R d do not contain any substituted or unsubstituted amino groups. The group R, R a , R b , R c , R d thus preferably does not contain any triarylamino groups, but may, for example, contain carbazole groups, i.e., heteroaryl groups containing nitrogen.
  • the compound according to the invention is substituted by aromatic or heteroaromatic groups R, R a , R b , R c , R d , R 1 or R 2 , it is preferred in one embodiment if these do not have any aryl or heteroaryl groups with more than two directly fused aromatic six-membered rings. Particularly preferably, the substituents do not have any aryl or heteroaryl groups with directly fused six-membered rings. This preference is based on the low T1 energy level of such structures.
  • Condensed aryl groups with more than two directly fused aromatic six-membered rings that are nevertheless also suitable according to the invention are phenanthrene and triphenylene, since due to their specific structure they do not have a low T1 energy level, even though they have more than two directly fused aromatic six-membered rings.
  • Ti is determined as indicated in section 2) of the patent examples.
  • R, R a , R b , R c , R d and the associated groups do not comprise an aromatic or heteroaromatic ring system having three linearly condensed aromatic 6-membered rings, wherein preferably none of the radicals R, R a , R b , R c , R d comprises an aromatic or heteroaromatic ring system having three linearly condensed aromatic 6-membered rings.
  • R, R a , R b , R c , R d and the associated groups do not comprise any condensed aryl groups.
  • radicals which can be selected in particular from R a , R b , R c , R d , R 1 and/or R 2 , form a ring with each other, this ring can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic.
  • the radicals which form a ring be adjacent, ie these residues are bonded to the same carbon atom or to carbon atoms that are directly bonded to each other, or they can be further apart.
  • radicals R a , R b , R c , R d , R 1 and/or R 2 of the respective groups to which these radicals are bonded may optionally represent a bond, so that the associated groups, preferably rings or ring systems, can be directly connected to one another, so that a ring closure can be effected.
  • radicals or substituents R a , R b , R c , R d and R 1 according to the above formulas do not form a condensed aromatic or heteroaromatic ring system, preferably not a condensed ring system, with the ring atoms of the respective ring or ring system to which the radicals are bonded.
  • R is selected, identically or differently at each occurrence, from the group consisting of H, D, CN or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 , may be substituted.
  • all radicals R are the same or different on each occurrence and are selected from an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 18 aromatic ring atoms, which may each be substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 .
  • Suitable aromatic or heteroaromatic ring systems R, R a , R b , R c and R d are selected from phenyl, biphenyl, in particular ortho-, meta- or para-biphenyl, terphenyl, in particular ortho-, meta-, para- or branched terphenyl, quaterphenyl, in particular ortho-, meta-, para- or branched quaterphenyl, fluorene, which can be linked via the 1-, 2-, 3- or 4-position, spirobifluorene, which can be linked via the 1-, 2-, 3- or 4-position, naphthalene, which can be linked via the 1- or 2-position, indole, benzofuran, benzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, carbazole, which can be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which can be linked via the 1 -, 2-, 3- or
  • R, R a , R b , R c or R d represents a heteroaryl group, in particular triazine, pyrimidine or quinazoline, aromatic or heteroaromatic radicals R 1 on this heteroaryl group may also be preferred.
  • R, R c and/or R d when they represent an aromatic or heteroaromatic ring system, are preferably selected from the groups of the following formulas R-1 to R-186,
  • phenyl, biphenyl, terphenyl and quaterphenyl with linkage patterns as listed above for R-1 to R-35, where these structures may be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • the substituents R 1 which are bonded to this carbon atom are preferably identical or different on each occurrence and are a linear alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which may also be substituted by one or more radicals R 2 .
  • R 1 is very particularly preferably a methyl group or a phenyl group.
  • the radicals R 1 can also form a ring system with one another, resulting in a spiro system.
  • At least one of the radicals R, R c or R d represents an aromatic or heteroaromatic ring system which is selected from structures of the formulas R-1 to R-186.
  • the groups of the formulas R-1 to R-186 presented above also represent preferred substituents R a , R b if they represent an aromatic or heteroaromatic ring system, in which case the radicals R 1 are to be replaced by radicals R.
  • R a and/or R b is selected from structures of the formulas R-1 to R-186, wherein the radicals R 1 presented in formulas R-1 to R-186 are to be replaced by R.
  • the group L in formula -(L) q -(Z) s comprises bivalent, trivalent or tetravalent aromatic or heteroaromatic ring systems based on the groups R-1 to R-186, where p is 0 and the dashed bond represents the bond to the corresponding group and one, two or three R 1 represents the bond to the aromatic or heteroaromatic group after R-1 to R-186, in which case the radicals R 1 are to be replaced by radicals R c .
  • the group L in formula -(L) q -(Z) s comprises exactly one or two, particularly preferably, especially preferably exactly one aromatic or heteroaromatic ring systems based on the groups R-1 to R-186.
  • Ar' is identical or different on each occurrence and is an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, particularly preferably having 6 to 24 aromatic ring atoms and very particularly preferably having 6 to 13 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 .
  • R 1 is the same or different on each occurrence and is selected from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 C atoms or a branched or cyclic alkyl group having 3 to 10 C atoms, where the alkyl group may in each case be substituted by one or more radicals R 2 other than H, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 other than H; two or more radicals R 1 may here form an aliphatic ring system with one another.
  • R 1 is selected, identically or differently on each occurrence, from the group consisting of H, D, a straight-chain alkyl group having 1 to 6 C atoms, in particular having 1, 2, 3 or 4 C atoms, or a branched or cyclic alkyl group having 3 to 6 C atoms, where the alkyl group may be substituted by one or more radicals R 2 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which may be substituted by one or more radicals R 2 other than H.
  • R 2 is, identically or differently on each occurrence, H, D, CN, F, an alkyl group having 1 to 4 C atoms or an aryl group having 6 to 10 C atoms, which may be substituted by an alkyl group having 1 to 4 C atoms, but is preferably unsubstituted.
  • all radicals R 1 , insofar as they represent an aromatic or heteroaromatic ring system, or R 2 , insofar as they represent aromatic or heteroaromatic groups are selected from the groups R-1 to R-186, which, however, are then each substituted accordingly with R 2 , or the groups mentioned for R 2 .
  • all aromatic or heteroaromatic groups of the radicals R, R a , R b , R c , R d , R 1 or R 2 are selected from the corresponding groups R-1 to R-186.
  • the compounds according to the application are at least 50%, in particular at least 80%, particularly preferably fully (100%) deuterated.
  • the corresponding proportion of the hydrogen atoms present in the undeuterated compound is replaced by D atoms.
  • the undeuterated compound is the corresponding compound in which none of the hydrogen atoms present is replaced by D, and which therefore contains no D.
  • all hydrogen atoms present are replaced by D atoms.
  • hydrogen atoms is to be understood as protium atoms.
  • part of the compound is completely undeuterated, and another part is largely or completely, preferably completely, deuterated.
  • at least one of the radicals R a and/or R b can represent a group selected from N(Ar)2 or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, wherein this group is largely or completely deuterated, and the other parts of the compound of formula (1) are completely undeuterated.
  • the above-described group which represents at least one of the radicals R a and/or R b , is completely undeuterated, and the remainder of the compound of formula (1) is largely or completely deuterated.
  • the alkyl groups in the compounds according to the application that are processed by vacuum evaporation preferably have no more than five carbon atoms, more preferably no more than four carbon atoms, and most preferably no more than one carbon atom.
  • Also suitable for compounds that are processed from solution are compounds that are substituted by alkyl groups, especially branched alkyl groups, with up to 10 carbon atoms, or that are substituted by oligoarylene groups, for example ortho-, meta-, para-, or branched terphenyl or quaterphenyl groups.
  • the compounds of the invention can be prepared according to synthesis steps known to the person skilled in the art, such as bromination, Suzuki coupling, Ullmann coupling, Heck reaction, Hartwig-Buchwald coupling, etc.
  • a further object of the present invention is therefore the use of a compound according to the invention in an electronic device.
  • 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 photodiodes (OPDs), organic 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).
  • 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 device is particularly preferably an organic electroluminescent device comprising a cathode, an anode, and at least one emitting layer, wherein at least one organic layer, which may be an emitting layer, hole-transport layer, electron-transport layer, hole-blocking layer, electron-blocking layer, or another functional layer, comprises at least one compound according to the invention.
  • the layer depends on the substitution of the compound.
  • the organic electroluminescent device may contain further layers, for example, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, charge generation layers, and/or organic or inorganic p/n junctions. Interlayers, which, for example, have an exciton-blocking function, may also be inserted between two emitting layers. It should be noted, however, that not every one of these layers is necessarily required.
  • the organic electroluminescent device may contain one emitting layer or it may contain multiple emitting layers. If multiple emitting layers are present, these preferably have a total of multiple emission maxima between 380 nm and 750 nm, resulting in an overall white emission, i.e., different emitting compounds that fluoresce or phosphoresce are used in the emitting layers. Systems with three emitting layers are particularly preferred, with the three layers exhibiting blue, green, and orange or red emission (the basic structure is described, for example, in WO 2005/011013).
  • the organic electroluminescent device according to the invention can also be a tandem OLED, in particular for white-emitting OLEDs.
  • the organic electroluminescent device may contain one emitting layer, or it may contain multiple emitting layers, with at least one organic layer of the device containing at least one compound according to the invention.
  • the compound according to the invention is preferably contained in an emitting layer of the device.
  • the compound according to the invention may also be contained in an electron-transport layer and/or in a hole-blocking layer and/or in a hole-transporting layer and/or in an exciton-blocking layer.
  • All luminescent complexes with transition metals or lanthanides are preferably considered as phosphorescent compounds, especially if they contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, Contain iridium, palladium, platinum, silver, gold, or europium, especially compounds containing indium, platinum, or copper.
  • all luminescent indium, platinum, or copper complexes are considered phosphorescent emitting compounds.
  • Examples of the emitters described above can be found for green and yellow emitters in applications US2025/002778A, US2024/425538A, US2024/349591 A, US2023/331757A, US2024/209013A, US2023/309374A, US2023/112032A, US2023/110705A, US2023/058719A, US2023/054166A, US2023/0225184A, US2023/203074A, US2022/0153769A, US2021/217969A, US2021/135130A, US2021/054010A, US2020/251666A, US2020/115406A, W02020/165064, US2019/280219A, US2018/0282356A, US2017/373259A, US2017/077425A, US2014/131676A, US2014/0231755A, US2010/0270916A, WO2010/028151, US2010/0244004, EP3623443A, EP4137551
  • the compound of formula (1) in an electronic device containing one or more fluorescent emitting compounds.
  • the compounds of formula (1) are used as electron-transporting material.
  • the compounds are preferably present in an electron-transport layer or a hole-blocking layer, or as an electron-conducting or bipolar host material in an emitting layer.
  • Use as an electron-conducting or bipolar host material in an emitting layer is particularly preferred.
  • Suitability as an electron-transporting material can be improved by the presence of appropriate groups, as described above.
  • An electron transport layer within the meaning of the present application is a layer with an electron-transporting function between the cathode and the emitting layer.
  • electron injection layers and hole blocking layers are understood to mean certain embodiments of electron transport layers.
  • an electron injection layer is an electron transport layer that directly borders the cathode or is separated from it only by a single coating of the cathode.
  • a hole-blocking layer is the electron-transport layer that directly borders the emitting layer on the cathode side.
  • the OLED according to the invention preferably comprises two, three, or four electron-transporting layers between the cathode and the emitting layer, of which preferably at least one, particularly preferably exactly one or two, contains a compound of formula (1).
  • the compound of formula (1) is used as an electron transport material in an electron transport layer, an electron injection layer or a hole blocking layer, the compound can be used as a pure material, i.e. in a proportion of 100% in the electron transport layer, or it can be used in combination with one or more other compounds.
  • the compounds of formula (1) are used as hole-transporting materials.
  • the compounds are preferably present in a hole-transporting layer or an electron-blocking layer, or as hole-conducting or bipolar host material in an emitting layer. Particular preference is given to using them as hole-conducting or bipolar host material in an emitting layer.
  • Their suitability as hole-transporting materials is improved by the presence of amino groups, as described above.
  • a hole transport layer in the sense of the present application is a layer with a hole transporting function between the anode and the emitting layer.
  • the compound of formula (1) is used in an emitting layer as matrix material in combination with one or more emitting compounds fertilize, whereby the emitting compounds can be fluorescent or phosphorescent, preferably phosphorescent.
  • the proportion of matrix material in the emitting layer is between 50.0 and 99.9 vol.%, preferably between 80.0 and 99.5 vol.%, particularly preferably between 92.0 and 99.5 vol.% for fluorescent emitting layers and between 85.0 and 97.0 vol.% for phosphorescent emitting layers.
  • the proportion of the emitting compound is between 0.1 and 50.0 vol.%, preferably between 0.5 and 20.0 vol.%, particularly preferably between 0.5 and 8.0 vol.% for fluorescent emitting layers and between 3.0 and 15.0 vol.% for phosphorescent emitting layers.
  • An emitting layer of an organic electroluminescent device can also comprise systems containing a plurality of matrix materials (mixed matrix systems) and/or a plurality of emitting compounds.
  • the emitting compounds are generally those with the smaller proportion in the system, and the matrix materials are those with the larger proportion.
  • the proportion of a single matrix material in the system may be lower than the proportion of a single emitting compound.
  • the compounds of formula (1) are used as a component of mixed matrix systems.
  • the mixed matrix systems preferably consist of two or three different matrix materials, particularly preferably of 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.
  • the compound of formula (1) is preferably the matrix material with electron-transporting properties.
  • the desired electron-transporting and hole-transporting properties of the mixed matrix components can also be predominantly or completely a single mixed matrix component, with the further mixed matrix component(s) fulfilling other functions.
  • the two different matrix materials can be present in a ratio of 1:50 to 1:1, preferably 1:20 to 1:1, even more preferably 1:10 to 1:1, and most preferably 1:4 to 1:1.
  • Mixed matrix systems are preferably used in phosphorescent organic electroluminescent devices. A source for more detailed information on mixed matrix systems is the application WO 2010/108579.
  • the mixed matrix systems can contain one or more emitting compounds, preferably one or more phosphorescent compounds.
  • Mixed matrix systems are generally preferred for use in phosphorescent organic electroluminescent devices.
  • Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed matrix system are selected from the preferred matrix materials for phosphorescent compounds or the preferred matrix materials for fluorescent compounds mentioned below, depending on which type of emitting compound is used in the mixed matrix system.
  • Preferred phosphorescent compounds for use in mixed matrix systems are the same as those described above as generally preferred phosphorescent emitter materials.
  • Examples of preferred phosphorescent emitters are the compounds disclosed in the above-mentioned patent applications and publications.
  • Preferred green and yellow phosphorescent emitters are: 5
  • Preferred red phosphorescent emitters are:
  • Preferred fluorescent emitting compounds are selected from DABNA derivatives and other boron derivatives, in particular according to WO 2020/208051, WO 2015102118, WO 2016/152418, WO 2018/095397, WO 2019/004248, WO 2019/132040, US 2020/0161552 and WO 2021/089450.
  • Particularly preferred fluorescent emitters are the compounds shown in the following table: 5
  • electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides etc. (for example according to WO 2005/084081 and WO 2005/084082), atropisomers (for example according to WO 2006/048268), boronic acid derivatives (for example according to WO 2006/117052) or the benzanthracenes (for example according to WO 2008/145239).
  • Preferred matrix materials for phosphorescent compounds are, as well as compounds according to formula (1), aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, e.g. CBP (N,N-biscarbazolylbiphenyl) or WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, e.g. B.
  • aromatic ketones aromatic phosphine oxides or aromatic sulfoxides or sulfones
  • triarylamines e.g. CBP (N,N-biscarbazolylbiphenyl) or WO 2005/039246, US 2005/
  • indenocarbazole derivatives e.g. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, e.g. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, e.g. according to WO 2007/137725, silanes, e.g. according to WO 2005/111172, azaboroles or boronic esters, e.g. according to WO 2006/117052, triazine derivatives, e.g. B.
  • WO 2011/042107 WO 2011/060867, WO 2011/088877 and WO 2012/143080
  • triphenylene derivatives e.g. according to WO 2012/048781
  • lactams e.g. according to WO 2011/116865 or WO 2011/137951
  • dibenzofuran derivatives e.g. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565.
  • a further phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host, or a compound that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010/108579.
  • material mixtures in the emitting layer which, in addition to the compound of formula (1) as host material, contain one, two, or three further compounds selected from host materials and emitter materials.
  • the following compositions are particularly preferred in the emitting layer:
  • composition of the present invention preferably present in an emitting layer of the electronic device, in addition to the electron-transporting material, which is preferably a compound according to formula (1 ), further contains at least one further, preferably hole-transporting host material, which may also be a compound according to formula (1 ) or may be a compound which does not correspond to formula (1 ).
  • the at least one further host material is selected from the group of carbazole and triarylamine derivatives, more specifically biscarbazoles, bridged carbazoles, triarylamines, dibenzofuran-carbazole derivatives or dibenzofuran-amine derivatives, carbazolamines, and compounds containing a silicon and nitrogen-containing ring.
  • the at least one further host material is selected from compounds of formula (h-1) or (h-2): where:
  • K is Ar 4 or -L 5 -N(Ar 6 ) 2 ;
  • Z A is CR z or CR A ; or two adjacent groups Z A together form a fused ring;
  • R A is -L 3 -Ar 5 or -L 4 -N(Ar 6 )2;
  • L 4 , L 5 are, identically or differently on each occurrence, a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R';
  • L 3 is a single bond or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R', where a radical R' on L 3 may form a ring with a radical R z on the carbazole;
  • Ar 4 is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R';
  • Ar 5 is, on each occurrence, identically or differently, an unsubstituted or substituted heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more R';
  • E is independently at each occurrence a single bond or a group C(R°) 2 ;
  • Ar 6 is, at each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R", where two or more R" may together form an aromatic or heteroaromatic ring system;
  • R"' is, identically or differently at each occurrence, H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by D or F; two or more radicals R"' together may form a ring system. with the proviso that the compounds of the formulas (h-1) and (h-2) comprise at least one group Z A which stands for R A.
  • L 4 , L 5 are, identically or differently on each occurrence, a single bond or an aromatic or heteroaromatic ring system having 5 to 25, more preferably 5 to 20 and even more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R'.
  • L 3 is a single bond or an aromatic or heteroaromatic ring system with 5 to 25 aromatic ring atoms, more preferably 5 to 20 and even more preferably 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R', where a radical R' on L 3 may form a ring with a radical R z on the carbazole.
  • M is an aromatic ring system having 6 to 40 aromatic ring atoms or a heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more radicals R;
  • E 1 is independently at each occurrence a single bond or a group C( RO ) 2 ; where R° has the same meaning as above;
  • the at least one further host material is further selected from the compounds according to formula (H-1) and the preferred embodiments of this formula, according to the not yet published application PCT/EP2023/085990, see also below, from compounds of the above-mentioned formula (h-1 -3) and from compounds of the above-mentioned formula (h-1 -4).
  • Ar H is, at each occurrence, the same or different, selected from aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R H ';
  • R H ' is selected, identically or differently at each occurrence, from H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms, or a branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more CH 2 groups may be replaced by SO, SO 2 , O, or S, and where in each case one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms; n is 1 or 2; m is (2-n).
  • hole-transporting host material for use in combination with the compound according to the application, preferably in an emitting layer of the electronic device, are the compounds shown in the table on pages 22-28 of the not yet published application PCT/EP2023/085990.
  • the compound according to the invention is used as a hole-transporting host material (h-TMM).
  • h-TMM hole-transporting host material
  • e-TMM electron-transporting host material
  • Such eTMMs which are preferably used in combination with a compound according to the invention, in particular in the emitting layer, are preferably selected from compounds of the formulas (eTMMIa), (eTMMIb), (eTMMIc), (eTMMId) and (eTMMIe), I b)
  • X is, at each occurrence, the same or different, CR 7 or N, with the proviso that not more than two X per cycle represent N;
  • Ar 5 represents, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 ring atoms, which may be substituted by one or more radicals R 7 ;
  • R w is, identically or differently at each occurrence, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more H atoms may be replaced by D, F or CN, or an aromatic or heteroaromatic ring system having 5 to 40 ring atoms which may be replaced by one or more substituents selected from D, F, CN, a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, where one or more H atoms of the alkyl group on the aromatic or heteroaromatic ring system may be replaced by D, F or CN; the two radicals R w which bond to the same carbon atom can also form a ring system with one another;
  • A is, at each occurrence, the same or different, CR 7 or N, where a maximum of two A groups per cycle stand for N and where A stands for C when L 2 is bonded to this position;
  • L 2 is, at each occurrence, identically or differently, a single bond or an aromatic or heteroaromatic ring system having 5 to 24 ring atoms, each of which may be substituted by one or more radicals R 7 ;
  • L 3 is an aromatic ring system with 6 to 40 ring atoms or a heteroaromatic ring system with 5 to 40 ring atoms, which may be substituted by one or more radicals R 7 ; a3 is, at each occurrence, the same or different, 0, 1, 2, 3 or 4; b3 is, at each occurrence, the same or different, 0, 1, 2 or 3;
  • Ring B is derived from an aryl group having 6 to 20 ring atoms, which may be substituted with one or more substituents R#;
  • R# is, identically or differently at each occurrence, D, F, CN or an aromatic ring system having 6 to 24 ring atoms which may be substituted by one or more radicals R 6 ;
  • R 8 is, identically or differently at each occurrence, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 C atoms, in which one or more H atoms may be replaced by F;
  • Particularly preferred groups Ar 5 are, identically or differently on each occurrence, selected from phenyl, meta-biphenyl or N-carbazolyl, each of which may also be substituted by one or more radicals R 7. Furthermore, at least one and particularly preferably exactly one of the substituents bonded to the N-carbazolyl group or to Ar 5 is preferably a triphenylsilyl group.
  • the compound of the formula (eTMMIc*) particularly preferably has a group Ar 5 which is a phenyl group which is substituted in the meta position with a triphenylsilyl group.
  • the compound of formula (1) is used as host material in combination with a blue or green phosphorescent emitter, in particular with a blue phosphorescent emitter.
  • the at least one blue phosphorescent emitter is selected from platinum complexes.
  • the at least one blue phosphorescent emitter has a LUMO of -1.8 eV to -2.2 eV, and the at least one blue phosphorescent emitter preferably has a HOMO of -5.0 eV to -5.6 eV, as defined by quantum mechanical calculations.
  • HOMO and LUMO are determined as specified in Section 2) of the patent examples.
  • the energy of the lowest triplet state Ti of the at least one blue phosphorescent emitter is higher than 2.55 eV, more preferably >2.65 eV, even more preferably >2.75 eV, as defined by quantum mechanical calculations. Ti is determined as specified in section 2) of the patent examples.
  • E 50 represents, identically or differently at each occurrence, C(R co )2, NR N0 , O or S;
  • Ar 50 is, identically or differently at each occurrence, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may each also be substituted by one or more radicals R';
  • Ar 51 , Ar 52 , Ar 53 are identical or different and represent a condensed aryl or heteroaryl ring having 5 to 18 aromatic ring atoms, each of which may also be substituted by one or more radicals R';
  • Ar 51 , Ar 52 , Ar 53 identical or different, represent a condensed aryl or heteroaryl ring having 6 aromatic ring atoms, which may each also be substituted by one or more radicals R'.
  • R N0 represents, identically or differently at each occurrence, a radical selected from an aromatic or heteroaromatic ring system having 5 to 60, preferably 5 to 40, more preferably 5 to 30 and even more preferably 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R'.
  • Suitable charge transport materials which can be used in the hole injection or hole transport layer or in the electron barrier layer or in the electron transport layer of the electronic component according to the invention are, in addition to the compounds of formula (1), for example those described in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials which are used in these layers according to the prior art.
  • all materials that are used according to the prior art as hole-transport materials in the hole-transport layer can be used as materials for the hole-transport layer.
  • Aromatic amine compounds can be used.
  • Other compounds that are preferably used in hole-transporting layers of the OLEDs according to the invention are, in particular, indenofluorenamine derivatives (e.g. according to WO 2006/122630 or WO 2006/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (e.g.
  • WO 01/049806 amine derivatives with fused aromatics
  • WO 95/09147 monobenzoindenofluorenamines (for example according to WO 08/006449), dibenzoindenofluorenamines (for example according to WO 07/140847), spirobifluorenamines (for example according to WO 2012/034627 or WO 2013/120577), fluorenamines (for example according to WO 2014/015937, WO 2014/015938, WO 2014/015935 and WO 2015/082056), spirodibenzopyranamines (for example according to WO 2013/083216), dihydroacridine derivatives (for example according to WO 2012/150001), spirodibenzofurans and spirodibenzothiophenes (for example according to WO 2015/022051, WO 2016/102048 and WO 2016/131521),
  • the OLED according to the invention preferably comprises two or more different electron-transporting layers.
  • the compound of formula (1) can be used in none, in one or more, or in all electron-transporting layers.
  • the compound of formula (1) is used in exactly one or exactly two electron-transporting layers are used, and other compounds are used in the other electron-transporting layers present.
  • Other compounds that can be used in addition to the compounds of formula (1) are all materials that are used according to the state of the art as electron-transport materials in the electron-transport layer.
  • Particularly suitable are aluminum complexes, e.g. Alqs, zirconium complexes, e.g. Zrq4, lithium complexes, e.g.
  • Liq 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.
  • Further suitable materials are derivatives of the aforementioned compounds as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.
  • the device is structured, contacted and finally sealed accordingly (depending on the application) to exclude harmful influences from water and air.
  • an organic electroluminescent device characterized in that one or more layers are coated using a sublimation process.
  • the materials are vapor-deposited in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. However, it is also possible for the initial pressure to be even lower, for example, less than 10' 7 mbar.
  • an organic electroluminescent device characterized in that one or more layers are coated using the OVPD (Organic Vapor Phase Deposition) process or by carrier gas sublimation.
  • the materials are applied at a pressure between 10' 5 mbar and 1 bar.
  • a special case of this process is the OVJP (Organic Vapor Jet Printing) process, in which the materials are applied directly through a nozzle and thus patterned.
  • an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or by any printing process, such as screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), inkjet printing, or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.
  • hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are deposited by vapor deposition.
  • the electronic devices containing one or more compounds of formula (1) can be used in displays, as light sources in lighting applications and as light sources in medical and/or cosmetic applications (e.g. light therapy).
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are characterized by one or more of the following properties: 1 .
  • the compounds according to the invention lead to long service lives.
  • the compounds according to the invention lead to high efficiencies, in particular to a high EQE.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to the invention, in particular as matrix material, have a very high color purity.
  • Patent examples are provided.
  • CAS: 2622-60-8 (9.7 g, 50 mmol) is placed in a flask purged with dry nitrogen, and dry tetrahydrofuran (500 mL) is added. The contents of the flask are stirred and cooled to -50 °C.
  • N-Butyllithium (2.5 M in hexane, 21.0 mL, 53 mmol) is placed in a dropping funnel and then added dropwise over 15 minutes to the stirred mixture at -50 °C. The resulting solution is stirred at -50 °C for 1 hour.
  • CAS: 138479-49-9 (11.0 g, 50 mmol) is added to the mixture as a solid in one portion, the suspension is stirred, and warmed to room temperature for 1 hour.
  • the mixture is stirred at room temperature for 24 hours and then poured into a mixture of ice and water (500 mL).
  • the resulting suspension is evaporated at 40°C/150 mbar to remove the organic solvents from the mixture.
  • the contents of the flask are transferred to a beaker equipped with a magnetic stirrer, the suspension is stirred, and adjusted to pH 7.0 with 2M hydrochloric acid solution.
  • the suspension is stirred for 1 hour at pH 7.0.
  • the solid is separated by vacuum filtration and washed with water (3 x 50 mL) to obtain 18.3 g of solid.
  • the solid is stirred in acetone (200 mL) under reflux for 20 minutes and then cooled.
  • Trifluoromethanesulfonic acid (207 mL) is placed in a flask, and Intermediate 1 (20.7 g, 50 mmL) is added in portions over 30 minutes. The mixture is stirred for 1 hour under dry nitrogen to obtain a solution. The contents are then heated at 115 °C for 14 hours. The mixture is then cooled to room temperature and then further cooled in an ice/water bath. The mixture is slowly added in a steady stream to stirred ice (2 kg). The pH of the resulting suspension is adjusted to 7.5 with 2N sodium hydroxide solution. The suspension is stirred for 2 hours, the precipitate is separated by vacuum filtration, and the solid is washed with water (3 x 100 mL).
  • the solid is dried in a vacuum oven at 35 °C for 48 hours to obtain a crude solid (20.9 g).
  • the solid is suspended in dichloromethane (100 mL), treated with alumina (activated, neutral, Brockmann activity I, 0.05-0.15 mm, 50 g), and the slurry is evaporated in vacuo. It is purified by alumina column chromatography and then recrystallized from toluene. The precipitate is collected by vacuum filtration and dried overnight in a vacuum oven at 40 °C to afford the target compound as white crystals (5.2 g, 26%).
  • CAS: 1198007-13-4 (9.6 g, 35 mmol) is placed in a flask purged with dry nitrogen. Dry tetrahydrofuran (175 mL) is added via cannula. The contents of the flask are stirred to obtain a clear solution, which is then cooled to -70 °C in a liquid nitrogen-acetone bath. 2M lithium diisopropylamide solution (in THF/heptane/ethylbenzene) (21.0 mL, 42 mmol) is transferred to the dropping funnel and then added dropwise to the stirred mixture at -70 °C. The resulting solution is stirred at 70 °C for 4 hours.
  • CAS: 138479-49-9 (7.7 g, 35 mmol) is added in one portion, the suspension is stirred at -70 °C for 1 hour, and then warmed to room temperature. The mixture was stirred overnight at room temperature and then poured into a mixture of ice and water (500 mL). The resulting suspension was evaporated at 40 °C/150 mbar to remove the organic solvents from the mixture. The contents of the flask were transferred to a beaker, the suspension was stirred, and adjusted to pH 7.0 with 2M hydrochloric acid solution. The suspension was stirred for 1 hour at pH 7.0. The solid was collected by vacuum filtration and washed with water (3 x 50 mL). 22.2 g of crude solid was obtained.
  • Trifluoromethanesulfonic acid 85 ml is placed in a flask, and intermediate 3 (8.4 g, 17 mmol) is added in portions over 10 minutes. The mixture is stirred for 15 minutes under dry nitrogen. The contents are then heated to 50 °C for 92 hours. The mixture is allowed to cool to room temperature and then cooled further in an ice-water bath. The mixture is slowly and added in a steady stream to stirred ice (750 g). The pH of the resulting suspension was adjusted to 7.5 with 2N sodium hydroxide solution. The suspension was stirred for 2 hours, the precipitate was separated by vacuum filtration, and washed with water (3 x 100 mL).
  • the solid was dried in a vacuum oven at 35 °C for 24 hours to obtain 8.1 g of a crude solid.
  • the solid was purified by alumina column chromatography using ethyl acetate/heptane as eluent. The precipitate from the main fraction was then recrystallized from dichloromethane/heptane.
  • the target compound was obtained as a white crystalline solid (68 mg, 1%).
  • CAS: 2622-60-8 (3.00 g, 15.4 mmol) is placed in a flask purged with dry argon. Dry tetrahydrofuran (75 mL) is added via cannula. The contents of the flask are stirred to obtain a clear solution, which is then cooled to -70 °C in a liquid nitrogen/acetone bath. 2M lithium diisopropylamide solution (in THF/heptane/ethylbenzene) (9.2 mL, 18.4 mmol) is transferred to the dropping funnel and then added dropwise to the stirred mixture at -70 °C. The resulting solution is stirred at 70 °C for 4 hours.
  • Trifluoromethanesulfonic acid 50 mL was placed in a flask under argon and purged for 10 minutes with an argon stream.
  • Intermediate 5 (5.00 g, 9.97 mmol) was added in portions.
  • the contents were then heated to 115 °C for 60 hours.
  • the mixture was allowed to cool to room temperature and then slowly added to an ice/water mixture.
  • the pH of the resulting suspension was adjusted to 7.5 with 2N sodium hydroxide solution.
  • the precipitate was removed by vacuum filtration and washed with water (3 x 50 mL).
  • the crude product was purified by silica gel column chromatography using dichloromethane as the solvent.
  • the product of the main fraction was triturated with ethyl acetate.
  • the target compound was obtained as a light yellow solid (1.50 g, 3.09 mmol, 31%).
  • CAS: 18628-07-4 (140 mg; 0.42 mmol) is dissolved in dry o-xylene (2.00 ml) and dry tetrahydrofuran (2.00 ml) in a heated and argon-purged, closed vessel and cooled with an ice bath. Methylmagnesium chloride is added dropwise as a 3 molar solution in THF (0.15 ml; 0.46 mmol) and stirred for 2 hours.
  • TD-DFT singlet and triplet excitations are then calculated using the same method (B3LYP/6-31 G(d)) and the optimized ground-state geometry.
  • the default settings for SCF and gradient convergence are used.
  • the calculation is performed analogously to that described above, with the difference that the basis set "LanL2DZ” is used for the metal atom and "6-31 G(d)" as the basis set for the ligands.
  • the lowest triplet state Ti is defined as the energy of the triplet state with the lowest energy, resulting from the described quantum chemical calculation.
  • the lowest excited singlet state Si is defined as the energy of the excited singlet state with the lowest energy, resulting from the described quantum chemical calculation.
  • Compound 1, compound 2 and compound 3 can be used as high T1 host and/or blocking materials in blue phosphorescent and hyperphosphorescent OLEDs.
  • compound 1 achieves good performance data when used as an electron-transporting host material in combination with a hole-transporting host material and a blue-emitting compound.
  • the spiro-BimBim core structure of compounds 1, 2, and 3 has a higher T1 energy than the spiro-bifluorene core structure well-known in OLED materials. It also has a higher T1 energy than the previously published spiro-Bim-fluorene core structure (see below).

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Abstract

La présente invention concerne des matériaux pour OLED, des procédés de fabrication desdits matériaux, et l'utilisation desdits matériaux dans des OLED.
PCT/EP2025/058811 2024-04-04 2025-04-01 Composés pour dispositifs électroniques, en particulier composés pour oled Pending WO2025210013A1 (fr)

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