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WO2025003084A1 - Composés dicyanoaryle pour dispositifs électroluminescents organiques - Google Patents

Composés dicyanoaryle pour dispositifs électroluminescents organiques Download PDF

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WO2025003084A1
WO2025003084A1 PCT/EP2024/067708 EP2024067708W WO2025003084A1 WO 2025003084 A1 WO2025003084 A1 WO 2025003084A1 EP 2024067708 W EP2024067708 W EP 2024067708W WO 2025003084 A1 WO2025003084 A1 WO 2025003084A1
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atoms
radicals
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aromatic ring
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Philipp Stoessel
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Merck Patent GmbH
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Merck Patent GmbH
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
    • 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
    • H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots

Definitions

  • the present invention relates to dicyanoaryl compounds for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, containing these materials.
  • phosphorescent organometallic complexes are often used as emitting materials. For quantum mechanical reasons, using organometallic compounds as phosphorescence emitters can result in up to four times the energy and power efficiency. In general, there is still room for improvement in electroluminescent devices, particularly in electroluminescent devices that exhibit triplet emission (phosphorescence).
  • the properties of phosphorescent electroluminescent devices are not only determined by the triplet emitters used.
  • the other materials used, such as matrix materials, are also of particular importance here. Improvements to these materials can therefore also lead to significant improvements in the properties of the electroluminescent devices.
  • electroluminescent devices comprise additional layers in addition to an emission layer, such as 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. These layers have a significant influence on the performance of electroluminescent devices.
  • electroluminescent devices that use fluorescent emitters or emitters that exhibit TADF are also known. These electroluminescent devices face corresponding challenges.
  • electroluminescent devices set out above are described in document DE 10 2020 123014 A1.
  • the compounds set out in DE 10 2020 123014 A1 relate in particular to materials that exhibit emission.
  • the object of the present invention is therefore to provide compounds which are suitable for use in an organic electronic device, in particular in an organic electroluminescent device, and which lead to good device properties when used in this device, as well as to provide the corresponding electronic device.
  • the object of the present invention is to provide compounds that lead to a long service life, good efficiency and low operating voltage.
  • Electron injection materials, electron transport materials and hole blocking materials in particular contribute to these properties.
  • the properties of the matrix materials, also referred to herein as host materials also have a significant influence on the service life and efficiency of the organic electroluminescent device.
  • a further object of the present invention can be seen in providing compounds which are suitable for use in a phosphorescent or fluorescent electroluminescent Devices, in particular as matrix material.
  • the compounds especially when used as host material, electron injection material, electron transport material or hole blocking material in organic electroluminescent devices, should lead to devices that exhibit excellent color purity.
  • the electronic devices should be able to be used or adapted for many purposes.
  • the performance of the electronic devices should be maintained over a wide temperature range.
  • the present invention relates to a compound according to formula (I),
  • the ring Ar z represents an aromatic ring system having 6 to 60 aromatic ring atoms, preferably 6 to 30 and particularly preferably 6 to 24 ring atoms, which may be substituted by one or more radicals R z , where the aromatic ring system may contain Si atoms or Ge atoms which are not directly linked to one another via a bond and the aromatic ring system may comprise one or more ring elements with one or two O atoms and 6 ring atoms, where an O atom is not directly linked to an O atom, Si atom or Ge atom via a bond; the index I represents an integer in the range from 1 to 10 and Ar CN represents a group of the following formula (Ar c )
  • Ar' is at each occurrence, identically or differently, an aromatic ring system having 6 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 1 , where two Ar' radicals which are bonded to the same C atom, Si atom or Ge atom may also be bridged to one another by a single bond or a bridge selected from C(R 1 )2, Si(R 1 )2 and Ge(R 1 )2;
  • Ar is, identically or differently at each occurrence, an aromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more radicals R 2 , where two radicals Ar” which are bonded to the same C atom, Si atom or Ge atom may also be bridged to one another by a single bond or a bridge selected from C(R 2 ) 2 , Si(R 2 ) 2 , and Ge(R 2 );
  • R 2 is selected on each occurrence, identically or differently, from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 C atoms or an aromatic ring system having 6 to 30 aromatic ring atoms, in which one or more H atoms can be replaced by D, F or CN and which can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, where two or more, preferably adjacent, substituents R 2 can form a ring system with one another; wherein the compound according to formula (I) does not comprise an anthracene group and a fluoranthene group.
  • An aryl group in the sense of this invention contains 6 to 40 C atoms.
  • An aryl group is understood to be either a simple aromatic cycle, i.e. benzene, or a condensed (fused) aryl group, for example naphthalene, phenanthrene, etc.
  • Aromatics linked to one another by a single bond, such as biphenyl, are not referred to as aryl groups, but as aromatic ring systems.
  • the present compound does not comprise an anthracene or fluoranthene group.
  • These groups are known in the art and comprise, in the case of anthracene, three linearly condensed aromatic 6-rings or, in the case of fluoranthene, two condensed aromatic 6-rings which are connected to another aromatic 6-ring via two bonds, thereby forming a 5-ring.
  • An aromatic ring system in the sense of this invention contains 6 to 60 C atoms in the ring system.
  • An aromatic ring system in the sense of this invention is to be understood as a system that does not necessarily only contain aryl groups, but in which several aryl groups can also be connected by a non-aromatic unit, such as a C, Si, Ge atom.
  • a non-aromatic unit such as a C, Si, Ge atom.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, stilbene, etc. are to be understood as aromatic ring systems in the sense of this invention, as are systems in which two or more aryl groups are connected, for example, by a short alkyl group.
  • the aromatic ring system is preferably selected from fluorene, 9,9'-spirobifluorene, 9,9-diarylamine or groups in which two or more aryl groups are linked to one another by single bonds.
  • aromatic ring system also includes ring systems that, in addition to one or more aryl groups, comprise one or more ring elements with one or two O atoms and 6 ring atoms.
  • an aliphatic hydrocarbon radical or an alkyl group which can contain 1 to 20 C atoms and in which individual H atoms or CH2 groups can also be substituted by the abovementioned groups is preferably the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, neo-pentyl, cyclopentyl, n-hexyl, neo-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethyl, ethy
  • alkyl 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 or CN, preferably F or CN.
  • An aromatic ring system with 6 - 60 or 6 to 40 aromatic ring atoms which can also be substituted with the above-mentioned radicals and which can be linked to the aromatic via any position, is understood to mean in particular groups which are derived from benzene, naphthalene, phenanthrene, pyrene, chrysene, biphenyl, biphenylene, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene or groups which are derived from combinations of these systems.
  • the phrase "two or more radicals can form a ring" is to be understood to mean, among other things, that the two radicals are linked to one another by a chemical bond with 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 bound, forming a ring. This is illustrated by the following scheme:
  • the group Ar z is selected from structures of
  • W is C, Si, Ge, preferably C or Si and particularly preferably C;
  • Z is C(R Z ) 2 , Si(R z )2, Ge(R z )2, 0, preferably C(R Z )2 or Si(R z )2, and particularly preferably C(R Z )2;
  • R z has the meaning given above, in particular in formula (I).
  • the group Ar z is selected from structures of the formulas (Ar z -1 a) to (Ar z -14b)
  • n, m is each independently 0 or 1, where 0 means that the group Y is not present and instead radicals R z are bonded to the corresponding carbon atoms;
  • W is C, Si, Ge, preferably C or Si and particularly preferably C;
  • Z is C(R Z ) 2 , Si(R z )2, Ge(R z )2 or 0, preferably C(R Z )2 or Si(R z )2, and particularly preferably C(R Z )2;
  • k is 0 or 1;
  • i is 0, 1 or 2, preferably 0 or 1;
  • j is 0, 1, 2 or 3, preferably 0 or 1;
  • h is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1;
  • g is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2, particularly preferably 0 or 1; and
  • R z has the meaning given above, in particular in formula (I).
  • the index I in formula (I) can be an integer in the range from 2 to 6, preferably 2 to 4.
  • the compound according to formula (I) has at least one fluorene group or one spiro group.
  • the compound may correspond to one of the following formulas (II-1) to (II-34):
  • the compounds (II-3), (II-8), (II-9), (11-12), (11-15), (II-25), (II-27), (II-29) and (11-31) are preferred, where in compounds according to formula (11-15) the group Y preferably stands for O, in compounds according to formula (II-25) at least one, preferably both of the groups Y preferably stands for 0, in compounds according to formula (II-29) the group W preferably stands for C and in compounds according to formula (11-31) the group W preferably stands for C.
  • the sum of the indices k, i, j, h and g is at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.
  • At least one group R in formula (A c ) is an aromatic ring system with 6 to 24 aromatic ring atoms which may be substituted by one or more radicals R 1 , but is preferably unsubstituted and/or the group in formulas (II-1) to (II-33) the index j is 1, 2 or 3 and one of the radicals R represents an aromatic ring system having 6 to 24 aromatic ring atoms, which may each be substituted by one or more radicals R 1 , but is preferably unsubstituted.
  • the index I in formula (I) can be 1 and at least one, preferably at least two of the groups R in formula (A c ) represents an aromatic ring system having 6 to 24 aromatic ring atoms, which can each be substituted by one or more radicals R 1 , but is preferably unsubstituted.
  • the group Ar CN is selected from structures of the formulas (Ar c -1 ) to (Ar c -3) and/or the group in formulas (11-1 ) to (II-33) is selected from structures of the formulas
  • R a is F, H or D, preferably H or D;
  • R b is an aromatic ring system having 6 to 24 aromatic ring atoms, preferably 6 to 18 and particularly preferably 6 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , where R 1 has the meaning given above, in particular in formula (I), particularly preferably phenyl or biphenyl.
  • the compound according to formula (I) can comprise at least one group Ar CN according to formula (Ar c -3), preferably at least two groups according to formula (Ar c -3) in the event that the index I is at least 2.
  • the compound corresponds to one of the following formulas (III-1) to (III-64):
  • the compounds of the formulas (III-3), (III-11), (III-13), (III-14), (III-15), (III-16), (III-19), (III-20), (III-25), (III-26), (III-45), (III-46), (III-49), (III-50), (III-53), (III-54), (III-57) and ( (III-58) are preferred, where in compounds of the formula ((III-25) or (III-26) the group Y is preferably 0, in compounds of the formula (III-45), (III-46) at least one, preferably both of the groups Y is preferably 0, in compounds of the formula (III-53), (III-54) the group W is preferably C or Si and in compounds of the formula (III-57), ( (III-58) the group W is preferably C or Si.
  • the sum of the indices k, i, j, h and g is at most 10, preferably at most 8, particularly preferably at most 6 and particularly preferably at most 4.
  • the compound has a ring Ar z of the formula (Ar z -12) or of the formulas (Ar z -12a) to (Ar z -12e), where the group W is preferably Si.
  • the compound has a ring Ar z of the formula (Ar z -12) or of the formulas (Ar z -12a) to (Ar z -12e), in which the sum n + m is greater than or equal to 1, preferably 2, and wherein at least one, preferably both, of the Y groups represents a bond.
  • the compound has a ring Ar z of the formula (Ar z -12) or of the formulas (Ar z -12a) to (Ar z -12e), wherein the group W is preferably C.
  • the compound has a ring Ar z of the formula (Ar z -12) or of the formulas (Ar z -12a) to (Ar z -12e), wherein the group W is preferably C and wherein the sum n + m is greater than or equal to 1, preferably 2, and wherein at least one, preferably both, of the Y groups represents a bond.
  • the compound according to the invention does not comprise a tetraphenylmethyl radical in which the four phenyl groups of the radical are not connected via a ring structure.
  • the compound does not comprise a tetraarylmethyl radical in which the four aryl groups of the radical are not connected via a ring structure.
  • compounds with rings Ar z of the formula (Ar z -12) or formulas (Ar z -12a) to (Ar z -12e) in which the sum n + m is greater than or equal to 1 are preferred over compounds in which this sum 0.
  • the particular advantages that can be achieved by this embodiment include, in particular, a longer service life of the electronic devices.
  • connection According to a preferred embodiment, the compound excluded from protection be substituted by radicals R 1 .
  • the compound according to the invention is substituted with aromatic groups R, R z , R 1 or R 2 , it is preferred if these do not have any aryl groups with more than two aromatic six-membered rings condensed directly to one another.
  • the substituents particularly preferably have no aryl groups at all with six-membered rings condensed directly to one another. This preference is based on the low triplet energy of such structures.
  • Condensed aryl groups with more than two aromatic six-membered rings condensed directly to one another which are nevertheless also suitable according to the invention, are phenanthrene and triphenylene, since these also have a high triplet level.
  • the compound according to the invention comprises at most two, preferably at most one and particularly preferably no group with two or more condensed aromatic radicals.
  • radicals which can be selected in particular from R, R z , R 1 and/or R 2 , form a ring system with one another, this can be mono- or polycyclic, aliphatic or aromatic.
  • the radicals which form a ring system with one another can be adjacent, ie these radicals are bonded to the same carbon atom or to carbon atoms which are directly bonded to one another, or they can be further apart from one another.
  • the ring systems provided with the substituents R, R z , R 1 and/or R 2 can also be connected to one another via a bond, so that a ring closure can be brought about in this way.
  • the ring Ar z can form a continuous conjugation with the group Ar CN according to formula (I) or the preferred embodiments of this formula.
  • a continuous conjugation of the aromatic systems is formed as soon as direct bonds are formed between adjacent aromatic rings.
  • At least one radical R, R z is selected, identically or differently on each occurrence, from the group consisting of an aromatic ring system having 6 to 24 aromatic ring atoms, which can be substituted by one or more radicals R 1 , preferably at least one substituent R, R z is selected, identically or differently on each occurrence, from the group consisting of an aromatic ring system having 6 to 18 aromatic ring atoms, which can be substituted by one or more radicals R 1 .
  • At least one radical R, R z is selected, identically or differently on each occurrence, from phenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, naphthalyl, phenanthrenyl or triphenylenyl, which can each be substituted by one or more radicals R 1 .
  • At least one radical R, R z is selected, identically or differently on each occurrence, from the group consisting of an aromatic ring system selected from the groups of the following formulas Ar-1 to Ar-40 and/or the group Ar' is selected, identically or differently on each occurrence, from the groups of the following formulas Ar-1 to Ar-40
  • R 1 has the meanings given above, represents the dashed bond to the corresponding group and furthermore:
  • Ar 1 is, identically or differently at each occurrence, a bivalent aromatic ring system having 6 to 18 aromatic ring atoms, which may each be substituted by one or more radicals R 1 ;
  • the radical R, R z is the same or different on each occurrence and is selected from the group consisting of H, D, F, 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 1 , or an aromatic ring system having 6 to 60 aromatic ring atoms, preferably having 6 to 40 aromatic ring atoms. atoms, each of which may be substituted by one or more radicals R 1 .
  • Preferred aromatic ring systems represented by the substituents R, R z or Ar' or Ar“ 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, in particular 1- or -linked naphthalene, phenanthrene or triphenylene, each of which can be substituted by one or more radicals R, R 1 or R 2 .
  • the structures Ar-1 to Ar-40 listed above are particularly preferred, with structures of the formulae (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-31), (Ar-32), (Ar-33), (Ar-34), (Ar-35), (Ar-36) being preferred and structures of the formulae (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15) being preferred.
  • R 1 substituents R 1 are to be replaced by R 2 .
  • 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 , or an aromatic ring system having 6 to 24 aromatic ring atoms, which may in each case be substituted by one or more radicals R 2 .
  • R 1 is the same or different on each occurrence and is selected from the group consisting of H, 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 a aromatic ring system with 6 to 13 aromatic ring atoms, which may be substituted by one or more radicals R 2 , but is preferably unsubstituted.
  • R 2 is the same or different on each occurrence and is H, 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.
  • the alkyl groups preferably have no more than five C atoms, particularly preferably no more than 4 C atoms, very particularly preferably no more than 1 C atom.
  • compounds which are substituted with alkyl groups, in particular branched alkyl groups, with up to 10 C atoms or which are substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl or quaterphenyl groups, are also suitable.
  • the compounds according to the invention have a high degree of deuteration.
  • the degree of deuteration can be at least 50%, preferably at least 80%, especially preferably at least 90% and very particularly preferably at least 95%.
  • the degree of deuteration is determined from the numerical ratio of deuterium to the sum of deuterium and 1 H hydrogen (D/(D+H)*100).
  • the compounds are particularly preferably fully deuterated.
  • compounds according to the invention preferably compounds according to formulas (II-1) to (II-34) and/or (III-1) to (III-64) have a molecular weight of less than or equal to 4000 g/mol, preferably less than or equal to 3000 g/mol, particularly preferably less than or equal to 2000 g/mol, especially preferably less than or equal to 1500 g/mol, more especially preferably less than or equal to 1200 g/mol and very particularly preferably less than or equal to 900 g/mol.
  • preferred compounds according to the invention are characterized in that they are sublimable. These compounds generally have a molecular weight of less than about 1200 g/mol.
  • the compounds according to the invention preferably compounds according to formulas (II-1) to (II-34) and/or (III-1) to (III-64) have a molecular weight of greater than or equal to 300 g/mol, preferably greater than or equal to 400 g/mol, particularly preferably greater than or equal to 500 g/mol. This improves the sublimability of the compounds.
  • the compounds according to the invention preferably compounds according to formulae (II-1) to (II-34) and/or (III-1) to (III-64) comprise at least 4, preferably 5 and particularly preferably 6 aryl radicals, which are preferably linked via a single bond.
  • This configuration achieves a particularly efficient and easily controllable sublimation of the compounds.
  • the compound may not comprise a phenyl group with three or more CN residues, preferably no phenyl or naphthalyl group with three or more CN residues and particularly preferably no aryl group with three or more CN residues.
  • the basic structure of the compounds according to the invention can be prepared using the methods outlined in the following schemes.
  • the individual synthesis steps, such as coupling reactions that lead to CC bonds, are known in principle to those skilled in the art. These include reactions according to SUZUKI, YAMAMOTO, NEGISHI and HIYAMA. Further information on the synthesis of the inventive
  • the compounds according to the invention can be prepared in one step starting from 1-halo-2,6-dicyanobenzenes and arylboronic acids or their esters in a Suzuki-type C-C coupling, see Scheme 1.
  • Typical catalyst systems for the Suzuki coupling can be combinations of palladium compounds and phosphines known from the literature, such as triarylphosphines, SPhos, XPhos, RuPhos, AdaPhos, etc.
  • typical bases can be alkali-alkaline earth carbonates, phosphates, hydroxides, fluorides, and solvents for single-phase reactions can be DMSO, DMF, DMAc, NMP, THF, dioxane or for two-phase mixtures of water with THF, dioxane, glyme, alcohols, toluene, etc.
  • Alternative coupling processes such as the Negish or Grignard cross coupling can also be used.
  • the compounds of the invention can be prepared by the process described in the literature starting from the corresponding 1,3-dicyanobenzenes are shown under “CH activation”, see NE
  • the scheme (1 ) is to be understood as an example, so that other groups X are also suitable, as set out in the prior art.
  • a further object of the present invention is therefore a process for preparing a compound according to the invention, wherein a dicyanophenyl compound is synthesized and at least one aromatic radical is introduced, preferably by means of a nucleophilic aromatic substitution reaction or a coupling reaction.
  • the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by 1 H-NMR and/or HPLC).
  • the compounds according to the invention can also be mixed with a polymer. It is also possible to incorporate these compounds covalently into a polymer. This is particularly possible with compounds which are substituted with reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid esters, or with reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers to produce corresponding oligomers, dendrimers or polymers. The oligomerization or polymerization preferably takes place via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is also possible to crosslink the polymers via such groups.
  • reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic acid esters
  • reactive, polymerizable groups such as olefins or oxetanes.
  • the compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.
  • the invention therefore further relates to oligomers, polymers or dendrimers containing one or more of the above-listed compounds of the formula (I) and preferred embodiments of these compounds, where instead of a hydrogen atom or a substituent, one or more bonds of the compounds to the polymer, oligomer or dendrimer are present.
  • these therefore form a side chain of the oligomer or polymer or are linked in the main chain.
  • the polymers, oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic. The same preferences apply to the repeat units of the compounds according to the invention in oligomers, dendrimers and polymers as described above.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers. Preference is given to copolymers in which the units according to formula (I) or the preferred embodiments set out above and below are present in amounts of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%.
  • Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (e.g. according to EP 842208 or WO 2000/022026), spirobifluorenes (e.g. according to EP 707020, EP 894107 or WO 2006/061181), para-phenylenes (e.g.
  • WO 92/18552 carbazoles (e.g. according to WO 2004/070772 or WO 2004/113468), thiophenes (e.g. according to EP 1028136), dihydrophenanthrenes (e.g. according to WO 2005/014689), cis- and trans-indenofluorenes (e.g. according to WO 2004/041901 or WO 2004/113412), ketones (e.g. according to WO 2005/040302), phenanthrenes (e.g. according to WO 2005/104264 or WO 2007/017066) or several of these units.
  • carbazoles e.g. according to WO 2004/070772 or WO 2004/113468
  • thiophenes e.g. according to EP 1028136
  • dihydrophenanthrenes e.g. according to WO 2005/014689
  • cis- and trans-indenofluorenes e.g. according to WO
  • the polymers, oligomers and dendrimers can contain further units, for example hole transport units, in particular those based on triarylamines, and/or electron transport units.
  • compounds according to the invention which are characterized by a high glass transition temperature.
  • compounds according to the invention are particularly preferred which comprise structures according to the formula (I) or the preferred embodiments set out above and below which have a glass transition temperature of at least 70 °C, particularly preferably of at least 110 °C, very particularly preferably of at least 125 °C and especially preferably of at least 150 °C, determined according to DIN 51005 (version 2005-08).
  • formulations of the compounds according to the invention are required. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable 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, in particular 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butylbenzoate, cumene, cyclohexanol, cyclohexanone, Cyclohexylbenzene, decalin, do
  • a further subject matter of the present invention is therefore a formulation or a composition comprising at least one compound according to the invention and at least one further compound.
  • the further compound can, for example, be a solvent, in particular one of the abovementioned solvents or a mixture of these solvents. If the further compound comprises a solvent, this mixture is referred to herein as a formulation.
  • 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.
  • At least one further compound is selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters which exhibit TADF, host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocking materials and hole blocking materials, preferably host materials.
  • the present invention further relates to the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • the compounds according to the invention are used in an electronic device as host material, electron injection material, electron transport material or hole blocking material, particularly preferably as electron injection material, electron transport material or hole blocking material.
  • An electronic device containing at least one compound according to the invention.
  • An electronic device in the sense 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 which are made entirely of inorganic materials.
  • the electronic device is selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), “organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1- 4); 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), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs) and organic electrical sensors, preferably organic electroluminescent devices (OLEDs, OLEDs,
  • the organic electroluminescent device contains a cathode, an anode and at least one emitting layer. In addition to these layers, it can 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. Interlayers can also be introduced between two emitting layers, which, for example, have an exciton blocking function. It should be noted, however, that not all of these layers necessarily have to be present.
  • the organic electroluminescent device can contain one emitting layer, or it can contain several emitting layers.
  • emission layers are present, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that a total of white emission results, ie different emitting compounds that can fluoresce or phosphoresce are used in the emitting layers.
  • Systems with three emitting layers are particularly preferred, with the three layers showing blue, green and orange or red emission.
  • the organic electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs.
  • the compound according to the invention can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device containing a compound according to formula (I) or the preferred embodiments described above in an emitting layer as a matrix material for phosphorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), in particular for phosphorescent emitters. Furthermore, the compound according to the invention can also be used in an electron transport layer and/or in a hole blocking layer.
  • the compound according to the invention is particularly preferably used as a matrix material for phosphorescent emitters, in particular for red, orange, blue, green or yellow, preferably for blue or green phosphorescent emitters, in an emitting layer, as a host material, electron transport material, electron injection material or hole blocking material.
  • the organic electroluminescent device comprises at least one emission layer and at least one electron transport layer and the electron transport layer contains the compound according to the present invention.
  • 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 sense of this invention means the luminescence from an excited State with higher spin multiplicity, i.e. a spin state > 1, in particular from an excited triplet state.
  • a spin state > 1 in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all indium, 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 vol.%, preferably between 98 and 10 vol.%, particularly preferably between 97 and 60 vol.%, in particular between 95 and 80 vol.% of the compound according to the invention, based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99 vol.%, preferably between 2 and 90 vol.%, particularly preferably between 3 and 40 vol.%, in particular between 5 and 20 vol.% of the emitter, based on the total mixture of emitter and matrix material.
  • the compound according to the invention is used as the only matrix material (“single host”) for the phosphorescent emitter.
  • a further 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. 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
  • CBP CBP (N,N-biscarbazolylbiphenyl) or those in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, e.g. according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, e.g. according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, e.g. B.
  • 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, aza- boroles or boronates, e.g. according to WO 2006/117052, triazine derivatives, e.g. 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.
  • diazasilole or tetraazasilole derivatives e.g. according to WO 2010/054729, diazaphosphole derivatives, e.g. 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. according to WO 2012/048781, dibenzofuran derivatives, e.g. according to WO 2015/169412, WO 2016/015810, WO 2016/023608, WO 2017/148564 or WO 2017/148565 or biscarbazoles, e.g. according to JP 3139321 B2.
  • the concentration of a compound according to formula (I), as previously described or preferably described, in the mixture according to the invention or in the light-emitting layer of the device according to the invention is usually in the range from 10 wt.% to 95 wt.%, preferably in the range from 15 wt.% to 90 wt.%, more preferably in the range from 15 wt.% to 80 wt.%, even more preferably in the range from 20 wt.% to 70 wt.%, very particularly preferably in the range from 40 wt.% to 80 wt.% and most preferably in the range from 50 wt.% to 70 wt.%, based on the entire mixture or based on the entire composition of the light-emitting layer.
  • another phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present in the mixture as a co-host. Particularly good results are achieved when a red phosphorescent emitter is used as the emitter and a yellow phosphorescent emitter is used as the co-host in combination with the compound according to the invention.
  • a compound that does not participate, or does not participate to a significant extent, in charge transport can be used as a co-host, as described, for example, in WO 2010/108579.
  • compounds that have a large band gap are suitable as co-matrix material in combination with the compound according to the invention. and do not participate themselves, or at least not to a significant extent, in the charge transport of the emitting layer.
  • Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680.
  • compounds according to the invention without special functional groups, for example hole transport groups and/or electron transport groups have advantageous properties.
  • phosphorescent compounds which emit light, preferably in the visible range, when suitably excited and which also contain at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80, in particular a metal with this atomic number.
  • phosphorescent emitters are compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds which contain iridium or platinum.
  • phosphorescent emitter typically includes compounds in which the light emission occurs through a spin-forbidden transition from an excited state with a higher spin multiplicity, i.e. a spin state > 1, for example through a transition from a triplet state or a state with an even higher spin quantum number, for example a quintet state.
  • a transition from a triplet state is understood here.
  • Examples of phosphorescent dopants are listed in the following table.
  • the compounds according to the invention are also particularly suitable as matrix materials for phosphorescent emitters in organic electroluminescent devices, as described, for example, in WO 98/24271, US 2011/0248247 and US 2012/0223633.
  • an additional blue emission layer is vapor-deposited over the entire surface of all pixels, including those with a color other than blue.
  • the organic electroluminescent device according to the invention does not contain a separate hole injection layer and/or hole transport layer and/or hole blocking layer.
  • layer and/or electron transport layer ie the emitting layer is directly adjacent to the hole injection layer or the anode, and/or the emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode, as described for example in WO 2005/053051.
  • a metal complex which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport or hole injection material, as described for example in WO 2009/030981.
  • 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 Vapour Phase Deposition) method or with the aid of carrier gas sublimation. The materials are applied at a pressure between 10' 5 mbar and 1 bar.
  • OVPD Organic Vapour Phase Deposition
  • a special case of this method is the OVJP (Organic Vapour Jet Printing) method, in which the materials are applied directly through a nozzle and thus structured.
  • an organic electroluminescent device characterized in that one or more layers are produced from solution, such as by spin coating, or using any printing method, such as screen printing, flexographic printing, offset printing, LITI (light induced thermal imaging, thermal transfer printing), ink-jet printing or nozzle printing. Soluble compounds are required for this, which are obtained, for example, by suitable substitution.
  • Formulations for applying a compound according to formula (I) or the preferred embodiments thereof set out above are novel.
  • a further subject matter of the present invention is therefore a formulation comprising at least one solvent and a compound according to formula (I) or the preferred embodiments thereof set out above.
  • hybrid processes are possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art in particular by improved efficiency or operating voltage.
  • the other electronic properties of the electroluminescent devices, such as the service life, remain at least as good.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished from the prior art in particular by improved efficiency and/or operating voltage and longer service life.
  • these compounds and the organic electroluminescent devices obtainable therefrom show Electroluminescent devices have a low refractive index (RI).
  • the electronic devices according to the invention are characterized by one or more of the following surprising advantages over the prior art:
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials, have excellent efficiency.
  • compounds according to the invention according to formula (I) or the preferred embodiments set out above and below result in a low operating voltage when used in electronic devices.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments described above and below, in particular as matrix material or as electron-conducting materials, have a very good service life. In this case, these compounds in particular cause a low roll-off, i.e. a small drop in the power efficiency of the device at high luminances.
  • Electronic devices in particular organic electroluminescent devices containing compounds according to formula (I) or the preferred embodiments set out above and below, in particular as matrix material or as electron-conducting materials have very low refractive indices.
  • optical loss channels can be avoided in electronic devices, in particular organic electroluminescent devices. As a result, these devices are characterized by a high PL and thus high EL efficiency of emitters or an excellent energy transfer from the matrices to dopants.
  • Semrau and/or repeated hot extraction crystallization (usual organic solvents or combinations thereof, preferably acetonitrile-DCM, 1:3 to 3:1 vv) and fractional sublimation or annealing under high vacuum. Yield: 14.7 g (32 mmol) 64%; Purity: approx. 99.9% according to HPLC.
  • OLEDs according to the invention as well as OLEDs according to the prior art is carried out according to a general process according to WO 2004/058911, which is adapted to the conditions described here (layer thickness variation, materials used).
  • the compounds B according to the invention can be used in the hole blocking layer (HBL) and the electron transport layer (ETL). All materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer (EML) always consists of at least one matrix material (host material) SMB (see Table 1) and an emitting dopant (dopant, emitter) D, which is mixed into the matrix material or matrix materials by co-evaporation in a certain volume proportion.
  • a specification such as SMB:D (97%:3%) means that the material SMB is present in the layer in a volume proportion of 97% and the dopant D in a proportion of 3%.
  • the electron transport layer can also consist of a mixture of two materials, see Table 1. The materials used to produce the OLEDs are shown in Table 5.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic.
  • the EQE in (%) and the voltage in (V) are specified at a luminance of 1000 cd/m 2
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer
  • EBL electron blocking layer
  • EML emission layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • Electron injection layer made of ETM2, 1 nm aluminum cathode, 100 nm
  • the compounds B according to the invention can be used in the hole blocking layer (HBL), the electron transport layer (ETL) and in the emission layer (EML) as electron-conducting matrix material (host material) (eTMM).
  • HBL hole blocking layer
  • ETL electron transport layer
  • EML emission layer
  • all materials are thermally vapor-deposited in a vacuum chamber.
  • the emission layer always consists of at least one or more matrix materials M and a phosphorescent dopant Ir, which is added to the matrix material or materials by co-evaporation in a certain volume proportion.
  • a specification such as M1:M2:lr (55%:35%:10%) means that the material M1 is present in the layer in a volume proportion of 55%, M2 in a volume proportion of 35% and lr in a volume proportion of 10%.
  • the electron transport layer can also consist of a mixture of two materials.
  • Table 3 The materials used to manufacture the OLEDs are shown in Table 5.
  • the OLEDs are characterized as standard.
  • the electroluminescence spectra, the current efficiency (measured in cd/A), the power efficiency (measured in Im/W) and the external quantum efficiency (EQE, measured in percent) are determined as a function of the luminance, calculated from current-voltage-luminance characteristics (IUL characteristics) assuming a Lambertian radiation characteristic.
  • the EQE in (%) and the voltage in (V) are specified at a luminance of 1000 cd/m 2
  • the OLEDs have the following layer structure:
  • HIL Hole injection layer made of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm
  • HTL Hole transport layer made of HTM1, 180 nm for blue, 50 nm for green, yellow and red
  • EBL electron blocking layer
  • EML emission layer
  • HBL hole blocking layer
  • ETL electron transport layer
  • Electron injection layer made of ETM2, 1 nm

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Abstract

La présente invention concerne des composés dicyanoaryle destinés à être utilisés dans des dispositifs électroniques, en particulier dans des dispositifs électroluminescents organiques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, qui contiennent ces matériaux.
PCT/EP2024/067708 2023-06-28 2024-06-25 Composés dicyanoaryle pour dispositifs électroluminescents organiques Pending WO2025003084A1 (fr)

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