EP4274827A1 - Matériaux pour dispositifs électroluminescents organiques - Google Patents

Matériaux pour dispositifs électroluminescents organiques

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Publication number
EP4274827A1
EP4274827A1 EP22700041.1A EP22700041A EP4274827A1 EP 4274827 A1 EP4274827 A1 EP 4274827A1 EP 22700041 A EP22700041 A EP 22700041A EP 4274827 A1 EP4274827 A1 EP 4274827A1
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EP
European Patent Office
Prior art keywords
group
radicals
aromatic
formula
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP22700041.1A
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German (de)
English (en)
Inventor
Amir Hossain Parham
Philipp Stoessel
Christian Ehrenreich
Jonas Valentin Kroeber
Christian EICKHOFF
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of EP4274827A1 publication Critical patent/EP4274827A1/fr
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
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    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • 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
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K2101/20—Delayed fluorescence emission

Definitions

  • the present invention relates to electronic devices, in particular organic electroluminescent devices containing triphenylene derivatives.
  • OLEDs organic electroluminescent devices
  • phosphorescent organometallic complexes are frequently used as emitting materials.
  • OLEDs organic electroluminescent devices
  • the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
  • the other materials used, such as matrix materials or charge transport materials, are also of particular importance here. Improvements in these materials can therefore also lead to improvements in the OLED properties.
  • Suitable matrix materials for OLEDs are, for example, triphenylene derivatives, such as e.g. B. disclosed in WO 2011/137157 or WO 2012/048781.
  • the object of the present invention is to provide compounds which are suitable for use in an OLED, in particular as matrix material for phosphorescent emitters or as electron transport material, and lead to improved properties there.
  • a further object of the present invention is to provide further organic semiconductors for organic electroluminescent devices in order to enable the person skilled in the art to have a greater choice of materials for the production of OLEDs.
  • the subject of the present invention is a compound according to formula (1), where the R radicals can occur more than once and the following applies to the symbols used:
  • Z is 0 or S
  • R* is a group of the following formula (2), where the dashed bond represents the bond to the backbone of formula (1),
  • X is the same or different on each occurrence CR or N or two adjacent X groups represent a group of the following formula (3), (4) or (5) with the proviso that at least two and at most three X groups represent N,
  • Y the same or different on each occurrence, is CR or N;
  • A is NR, O, S or CR2;
  • L is a single bond or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can be substituted by one or more R radicals;
  • CFl2 groups can be replaced by Si(R 1 ) 2 , C ⁇ O, NR 1 , O, S or CONR 1 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms , each of which may be substituted by one or more R 1 radicals; two radicals R can also form an aliphatic or heteroaliphatic ring system with one another;
  • R 2 is identical or different on each occurrence and is H, D, F, CN or an aliphatic, aromatic or heteroaromatic organic radical, in particular a hydrocarbon radical, having 1 to 20 carbon atoms in which one or more Fl atoms have also been replaced by F could be.
  • An aryl group within the meaning of this invention contains 6 to 40 carbon atoms and contains no fleteroatoms in the ring system.
  • a fleteroaryl group within the meaning of this invention contains 2 to 40 carbon atoms and at least one fleteroatom, with the proviso that the sum of carbon atoms and fleteroatoms is at least 5.
  • the fleteroatoms are preferably selected from N, O and/or S.
  • An aryl group or fleteroaryl group is either a simple aromatic cycle, i.e. benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc.
  • aromatics linked by a single bond such as biphenyl, are not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
  • An aromatic ring system within the meaning of this invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms in the ring system and contains no heteroatoms in the ring system.
  • a heteroaromatic ring system within the meaning of this invention contains 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, O and/or S.
  • systems such as fluorene or 9,9'-spirobifluorene should also be understood as aromatic ring systems in the context of this invention.
  • alkyl group is used as a generic term for linear, branched and cyclic alkyl groups.
  • alkenyl group and alkynyl group are used as generic terms for both linear, branched and cyclic alkenyl and alkynyl groups.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 40 carbon atoms, and in which individual H atoms or CH 2 groups are also substituted by the abovementioned groups can be, 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
  • An alkoxy group OR 1 having 1 to 40 carbon atoms is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-flexoxy, cyclohexyloxy, n-fleptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2- Ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
  • a thioalkyl group SR 1 having 1 to 40 carbon atoms is, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclo-octylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoroethylthio, 2,2,2- trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclopen
  • alkyl, alkoxy or thioalkyl groups according to the present invention can be straight-chain, branched or cyclic, it being possible for one or more non-adjacent CH 2 groups to be replaced by the groups mentioned above; furthermore, one or more Fl atoms can also be replaced by D, F, Cl, Br, I, CN or NO 2 , preferably F, Cl or CN, particularly preferably F or CN.
  • An aromatic or heteroaromatic ring system with 5-60 aromatic ring atoms which can be substituted by the abovementioned radicals and which can be linked via any position on the aromatic or heteroaromatic, 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-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene,
  • the group R* ie the group of formula (2), can either be attached to the ring to which no group Z is attached, so that giving the compounds of formula (6) below, or it may be attached to the same ring as the group Z to give the compounds of formula (7) below, where the radicals R can also occur more than once and the symbols used have the meanings given above.
  • Z is 0.
  • the compound of the formula (1) or the preferred embodiments contains a maximum of two substituents R which represent a group other than Fl or D, and more preferably a maximum of one substituent R represents a group other than Fl or D.
  • the substituents R, which are different from F1 and D, are preferably attached to a ring other than the group R*.
  • the compounds of the following formulas (6a-1) to (7b-4) are particularly preferred
  • the group L represents a single bond or a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which can each be substituted by one or more R radicals.
  • L particularly preferably represents a single bond or an aromatic ring system having 6 to 12 aromatic ring atoms which can be substituted by one or more R radicals, or a dibenzofuran or dibenzothiophene group which can be substituted by one or more R radicals.
  • L is very particularly preferably a single bond, a meta- or para-linked phenylene group or a dibenzofuran group.
  • the dibenzofuran or dibenzothiophene group is preferably in the 1,3, 1,6, 1,7, 1,8, 3,6, 3,8 or 3,9 position connected.
  • L can represent a dibenzofuran or dibenzothiophene group applies in particular when L represents a triazine group.
  • L stands for an aromatic or heteroaromatic ring system, this is preferably selected from the structures of the following formulas (L-1) to (L-26),
  • L particularly preferably represents a single bond or an optionally substituted phenylene or biphenyl group, ie a group of the formula (L-1) to (L-6), in particular (L-1), (L-2) or (L-6). ).
  • all X's, identical or different, are CR or N, with the proviso that at least two X's are N.
  • Preferred embodiments of the formula (8) are the groups of the following formulas (8a), (8b) and (8c), the groups of the formula (8a) being particularly preferred where the symbols used have the meanings given above and R, identically or differently on each occurrence, is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms which can be substituted by one or more R 1 radicals.
  • two adjacent X's are a group of the formula (3), (4) or (5), where Y is identical or different for CR, and of the remaining X's exactly two are X's N and the third X for CR, so that it is a structure according to one of the following formulas (9) to (18),
  • R can also occur more than once and exactly two X's are N.
  • Preferred embodiments of formulas (9) to (18) are the structures of the following formulas (9a) to (18a),
  • R is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms which can be substituted by one or more R 1 radicals.
  • A is 0 or NR.
  • R is the same or different on each occurrence for an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, by one or more R 1 radicals may be substituted.
  • R is particularly preferably the same or different on each occurrence, an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, in particular having 6 to 13 aromatic ring atoms Ring atoms, which may be substituted by one or more, preferably non-aromatic, radicals R 1 .
  • R is very particularly preferably selected from phenyl, d 5 -phenyl, meta- or para-biphenyl, dibenzofuran or carbazole, it being possible for these groups to be substituted by one or more radicals R 1 , but is preferably unsubstituted.
  • R is selected the same or different each time it occurs from the group consisting of H, D, F, CN, OR 1 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 C atoms or a branched or cyclic alkyl group with 3 to 10 C atoms, where the alkyl or alkenyl group can be substituted with one or more radicals R 1 , but is preferably unsubstituted, and where one or more non-adjacent CH 2 - groups can be replaced by O, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which can each be substituted by one or more radicals R 1 ; two R radicals can also form an aliphatic, aromatic or heteroaromatic ring system with one another.
  • R is particularly preferably selected identically or differently on each occurrence from the group consisting of H, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 6 carbon atoms, where the alkyl group can be substituted by one or more radicals R 1 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 , can be substituted.
  • R is very particularly preferably selected identically or differently on each occurrence from the group consisting of H, D or an aromatic one or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 , preferably non-aromatic radicals R 1 .
  • the substituents R which are bonded to the triphenylene skeleton are preferably identical or different on each occurrence selected from the group consisting of H, D or an aromatic ring system having 6 to 24 aromatic ring atoms, particularly preferably having 6 to 12 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R 1 , but is preferably unsubstituted.
  • the substituents R which are bonded to the triphenylene skeleton are particularly preferably H or D, in particular H.
  • Suitable aromatic or heteroaromatic ring systems R 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, carbazole, which can be linked via the 1-, 2-, 3- or 4-position, dibenzofuran, which can be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene, which can be linked via the 1-, 2-, 3- or 4-position, indenocarbazole, indolocarbazole, pyr
  • the groups R on the parent structure of the compound of the formula (1) are here if they represent an aromatic or heteroaromatic ring system and the groups R in the formulas (8) to (18a) are preferably selected from the groups of the following formulas R-1 to R-83,
  • R 1 has the meanings given above, the dashed bond represents the position of the bond of the group and the following also applies:
  • Ar is a bivalent aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, which can be substituted by one or more R 1 radicals;
  • a 1 is, identically or differently, on each occurrence C(R 1 )2, NR 1 , 0 or S;
  • groups R-1 to R-83 mentioned above have several groups A 1 , then all combinations from the definition of A 1 are suitable for this. Preferred embodiments are then those in which one group A 1 is NR 1 and the other group A 1 is C(R 1 ) 2 or in which both groups A 1 are NR 1 or in which both groups A 1 are 0 . In a particularly preferred embodiment of the invention, in groups R which have several groups A 1 , at least one group A 1 is C(R 1 ) 2 or NR 1 .
  • the substituent R 1 which is bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which can also be substituted by one or more R 2 radicals.
  • this substituent R 1 is identical or different on each occurrence for an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 12 aromatic ring atoms, which has no fused aryl groups or heteroaryl groups, in which two or more aromatic or heteroaromatic 6-ring groups are fused directly to one another, and which can each also be substituted by one or more radicals R 2 .
  • the substituents R 1 attached to this carbon atom are preferably the same or different each occurrence for a linear alkyl group with 1 to 10 carbon atoms or for a branched or cyclic alkyl group with 3 to 10 carbon atoms or for an aromatic or heteroaromatic ring system with 5 to 24 aromatic ring atoms, which is also denoted by one or more radicals R 2 can be substituted.
  • R 1 very particularly preferably represents a methyl group or a phenyl group.
  • the radicals R 1 can also form a ring system with one another, which leads to a spiro system.
  • the radicals R on the triphenylene backbone are identical or different each time they occur for H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, each with one or more radicals R 1 may be substituted.
  • R is particularly preferably identical or different on each occurrence for H or phenyl, in particular for H.
  • the compound according to the invention apart from the group R*, has no electron-deficient heteroaryl groups as substituents R, R 1 or R 2 .
  • An electron-poor heteroaryl group is either a six-membered heteroaryl group with at least one nitrogen atom or a five-membered heteroaryl group with at least two heteroatoms, at least one of which is a nitrogen atom, it being possible for other aryl or heteroaryl groups to be fused to these groups.
  • R 1 is the same or different on each occurrence selected from the group consisting of H, D, F, CN, OR 2 , a straight-chain alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, where the alkyl or alkenyl group can be substituted by one or more radicals R 2 and where one or more non-adjacent CH2 groups are replaced by O can be, or an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which can each be substituted by one or more radicals R 2 ; two or more radicals R 1 together can be aliphatic form a ring system.
  • R 1 is identical or different on each occurrence selected from the group consisting of H, a straight-chain alkyl group having 1 to 6 carbon atoms, in particular having 1, 2, 3 or 4 carbon atoms, or one branched or cyclic alkyl group having 3 to 6 carbon 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, preferably with 6 to 13 aromatic ring atoms, each of which may be substituted by one or more R 2 radicals, but is preferably unsubstituted.
  • R 2 is the same or different on each occurrence of H, F, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms which is linked to an alkyl group having 1 to 4 carbon atoms. Atoms may be substituted, but is preferably unsubstituted.
  • the alkyl groups in compounds according to the invention which are processed by vacuum evaporation preferably have no more than five carbon atoms, particularly preferably no more than 4 carbon atoms, very particularly preferably no more than 1 carbon atom.
  • the compounds of the formula (1) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer which is directly adjacent to a phosphorescent layer, it is also preferred if the compound does not contain any Contains fused aryl or fleteroaryl groups in which more than two six-membered rings are fused directly to one another.
  • the groups R, R 1 and R 2 do not contain any fused aryl or fleteroaryl groups in which two or more six-membered rings are fused directly to one another.
  • An exception to this form phenanthrene, triphenylene, quinazoline, and quinoxaline which may be preferred due to their higher triplet energy despite the presence of fused aromatic six-membered rings.
  • Formulations of the compounds according to the invention are necessary for processing the compounds of the formula (1) or the preferred embodiments from the liquid phase, for example by spin coating or by printing processes.
  • a further subject of the present invention are therefore formulations containing at least one compound of the formula (1) or the preferred embodiments and at least one solvent.
  • These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this.
  • Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchone, 1,2,3,5-tetramethylbenzene,
  • 1,2,4,5-tetramethylbenzene 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, NMP, p-cymene, phenetole,
  • 1,4-diisopropylbenzene dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4- dimethylphenyl)ethane, 2-methylbiphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, Octyl octanoate, heptyl benzene, menthyl isovalerate, cyclohe
  • the compounds of the formula (1) or of the preferred embodiments listed above are used according to the invention in an electronic device, in particular in an organic electroluminescent device.
  • a further subject matter of the present invention is therefore the use of the compounds of the formula (1) or the preferred embodiments in an electronic device, in particular in an OLED.
  • an electronic device in particular an organic electroluminescent device containing at least one compound according to the invention.
  • An electronic device within the meaning of the present invention is a device which contains at least one layer which contains at least one organic compound.
  • the component can also contain inorganic materials or layers that are made up entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors ( O-LETs), organic solar cells (O-SCs), dye-sensitized organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs). ), organic laser diodes (O-lasers) and organic plasmon emitting devices, but preferably organic electroluminescent devices (OLEDs), particularly preferably phosphorescent OLEDs.
  • 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
  • DSSCs dye-sensitized
  • the organic electroluminescent device contains cathode, anode and at least one emitting layer. In addition to these layers, it can also contain other layers, for example one or each several 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. Likewise, interlayers can be introduced between two emitting layers, which have an exciton-blocking function, for example. However, it should be pointed out that each of these layers does not necessarily have to be present. In this case, the organic electroluminescent device can contain an emitting layer, or it can contain a plurality of emitting layers.
  • a plurality of emission layers are present, these preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, resulting in white emission overall, ie different emitting compounds which can fluoresce or phosphorescence 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 electroluminescence device according to the invention can also be a tandem OLED, in particular for white-emitting OLEDs.
  • connection according to the embodiments listed above can be used in different layers, depending on the precise structure. Preference is given to an organic electroluminescent device containing a compound of the formula (1) or the preferred embodiments outlined above in an emitting layer as matrix material for phosphorescent or fluorescent emitters or for emitters that exhibit TADF (thermally activated delayed fluorescence), in particular as Matrix material for phosphorescent emitters.
  • the organic electroluminescent device can contain an emitting layer or it can contain a plurality of emitting layers, with at least one emitting layer containing at least one compound according to the invention as matrix material.
  • the compound according to the invention can also be used in an electron transport layer and/or in a hole-blocking layer.
  • the compound is used as 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 is understood to mean luminescence from an excited state with a higher spin multiplicity, ie a spin state>1, in particular from an excited triplet state.
  • all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
  • the mixture of the compound of the formula (1) or the preferred embodiments and the emitting compound contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 80% by volume of the compound of the formula (1) or of the preferred embodiments, based on the total mixture of emitter and matrix material.
  • the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, particularly preferably between 3 and 40% by volume, in particular between 5 and 20% by volume, of the emitter, based on the total mixture emitter and matrix material.
  • a further preferred embodiment of the present invention is the use of the compound of the formula (1) or of the preferred embodiments as matrix material for a phosphorescent emitter in combination with a further matrix material.
  • Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, z. B. CBP (N,N-biscarbazolylbiphenyl) or in WO 2005/039246, US 2005/0069729,
  • JP 2004/288381 EP 1205527, WO 2008/086851 or WO 2013/041176, indolocarbazole derivatives, e.g. B. according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, z. B. 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. B. according to WO 2007/137725, silanes, z. B.
  • azaboroles or boron esters z. B. according to WO 2006/117052, triazine derivatives, z. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877, zinc complexes, e.g. B. according to EP 652273 or WO 2009/062578, diazasilol or tetraazasilol derivatives, z. B. according to WO 2010/054729, diazaphosphole derivatives, z. B. according to WO 2010/054730, bridged carbazole derivatives, z. B.
  • WO 2011/042107 WO 2011/060867, WO 2011/088877 and WO 2012/143080
  • triphenylene derivatives z. B. according to WO 2012/048781
  • dibenzofuran derivatives z. according to WO 2015/169412
  • WO 2016/015810 WO 2016/023608, WO 2017/148564 or WO 2017/148565.
  • another phosphorescent emitter which emits at a shorter wavelength than the actual emitter, can be present as a co-host in the mixture, or a compound that does not participate, or does not participate to a significant extent, in charge transport, as for example in WO 2010/108579 described.
  • the materials are used in combination with another matrix material.
  • the compounds of the formula (1) or the preferred embodiments are electron-poor compounds.
  • Preferred co-matrix materials are therefore hole-transporting compounds, which are preferably selected from the group of arylamine or carbazole derivatives.
  • Preferred biscarbazoles are the structures of the following formulas (19) to (25),
  • a 1 has the meanings given above and Ar 1 is selected identically or differently on each occurrence from an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more R 1 radicals.
  • a 1 is CR2.
  • Preferred embodiments of Ar 1 are the preferred structures listed above for aromatic or heteroaromatic radicals R, in particular the groups (R-1) to (R-83).
  • Preferred embodiments of the compounds of the formulas (19) to (25) are the compounds of the following formulas (19a) to (25a),
  • Examples of suitable compounds of the formulas (19) to (25) are the compounds shown below.
  • Preferred bridged carbazoles are the structures of the following formula (26),
  • a 1 and R have the meanings given above and A 1 is preferably selected identically or differently on each occurrence from the group consisting of NR 1 , where R 1 is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, which with a or more radicals R 2 can be substituted, and C(R 1 ) 2.
  • Preferred dibenzofuran derivatives are the compounds of the following formula (27), where the oxygen can also be replaced by sulfur, so that a dibenzothiophene is formed, and L, R and Ar 1 have the meanings given above.
  • the two groups Ar 1 which bind to the same nitrogen atom, or one group Ar 1 and one group L, which bind to the same nitrogen atom, can also be connected to one another, for example to form a carbazole.
  • suitable dibenzofuran derivatives are the compounds shown below.
  • Preferred carbazole amines are the structures of the following formulas (28), (29) and (30), where L, R and Ar 1 have the meanings given above.
  • Examples of suitable carbazolamine derivatives are the compounds shown below.
  • Particularly suitable phosphorescent compounds are compounds which, when suitably excited, emit light, preferably in the visible range, and also at least one atom with an atomic number greater than 20, preferably greater than 38 and less than 84, particularly preferably greater than 56 and less than 80 included, in particular a metal with this atomic number.
  • phosphorescence emitters preference is given to using compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds which
  • WO 2016/124304 WO 2017/032439, WO 2018/011186 and WO 2018/041769, WO 2019/020538, WO 2018/178001, WO 2019/115423 and WO 2019/158453.
  • all phosphorescent complexes are suitable as are used according to the prior art for phosphorescent OLEDs and as are known to the person skilled in the field of organic electroluminescence, and the person skilled in the art can use further phosphorescent complexes without any inventive step.
  • the further layers of the organic electroluminescent device according to the invention it is possible to use all the materials which are customarily used in accordance with the prior art. The person skilled in the art can therefore use all materials known for organic electroluminescent devices in combination with the compounds of the formula (1) or the preferred embodiments described above without any inventive step.
  • an organic electroluminescence device characterized in that one or more layers are coated using a sublimation process.
  • the materials are vapour-deposited in vacuum sublimation systems at an initial pressure of less than 10 -5 mbar, preferably less than 10 -6 mbar. However, it is also possible for the initial pressure to be even lower, for example less than 10 -7 mbar.
  • An organic electroluminescent device is also preferred, characterized in that one or more layers are coated using the OVPD (organic vapor phase deposition) method or with the aid of carrier gas sublimation.
  • the materials are applied at a pressure between 10 -5 mbar and 1 bar.
  • OVPD organic vapor phase deposition
  • 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 structured.
  • an organic electroluminescent device characterized in that one or more layers of solution, such as. B. by spin coating, or with any printing method, such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (ink jet printing) or nozzle printing.
  • any printing method such as. B. screen printing, flexographic printing, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (ink jet printing) or nozzle printing.
  • This requires soluble compounds, which are obtained, for example, by suitable substitution.
  • Hybrid processes are also possible, in which, for example, one or more layers are applied from solution and one or more further layers are vapor-deposited.
  • OLEDs containing the compounds of the formula (1) as matrix material for phosphorescent emitters lead to long service lives. This applies in particular when the compounds are used as matrix material for a phosphorescent emitter. In particular, the OLEDs show an improved service life compared to OLEDs with matrix materials which, although they have the same bridged triphenylene basic structure, have a different substitution pattern and no substituent R*.
  • OLEDs containing the compounds of the formula (1) lead to high efficiencies. This applies in particular when the compounds are used as matrix material for a phosphorescent emitter.
  • OLEDs containing the compounds of the formula (1) lead to low operating voltages. This applies in particular when the compounds are used as matrix material for a phosphorescent emitter.
  • the compounds according to the invention can also be used with very good properties in an electron transport layer, also in combination with a fluorescent emission layer, or in a hole blocking layer are used.
  • improved efficiency is obtained with a simultaneously lower operating voltage.
  • toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc. can be used
  • Pd(PCy3)2Cl2 or Pd2(dba)3 with S-Phos (1:3) can also be used as a catalyst system.
  • hot extraction can also be used for purification; other common solvents such as ethanol, butanol, acetone, ethyl acetate, acetonitrile, toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane can be used for recrystallization or hot extraction or high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc. can be used for recrystallization. Presentation of the compounds according to the invention
  • Toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane or high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc. can be used for recrystallization.
  • Toluene, xylene, dichloromethane, methanol, tetrahydrofuran, n-butyl acetate, 1,4-dioxane or high boilers such as dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, etc. can be used for recrystallization.
  • Glass flakes coated with structured ITO (indium tin oxide) with a thickness of 50 nm are first treated with an oxygen plasma, followed by an argon plasma, before coating. These plasma-treated glass flakes form the substrates on which the OLEDs are applied.
  • structured ITO indium tin oxide
  • OLEDs have the following layer structure: substrate / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) / optional electron injection layer (EIL). ) and finally a cathode.
  • the cathode is formed by a 100 nm thick aluminum layer.
  • the precise structure of the OLEDs can be found in Tables 1, 3 and 5. The materials required to produce the OLEDs are shown in Table 7 unless they have already been described previously.
  • the device data of the OLEDs are in Table 2,
  • Examples V1 to V7 are comparative examples.
  • Examples E1a-g, E2a-g, E3a-f, E4a-f E5a-e, E6a-c, E7a, E7b show data from OLEDs according to the invention.
  • the emission layer always consists of at least two matrix materials and an emitting dopant (dopant, emitter), which is co-evaporated into the matrix material or matrix materials added to a specific volume.
  • a specification such as P1a:H1:TE2 (32%:60%:8%) means that the material P1a accounts for 32% by volume, H1 for 60% by volume and TE2 for 8% by volume in the layer present.
  • the electron transport layer can also consist of a mixture of two materials.
  • the electroluminescence spectra are determined at a luminance of 1000 cd/m 2 and the CIE 1931 x and y color coordinates are calculated therefrom.
  • the information U10 in Tables 2 and 6 designates the voltage that is required for a current density of 10 mA/cm 2 .
  • EQE10 denotes the external quantum efficiency achieved at 10 mA/cm 2 .
  • the service life LD is defined as the time after which the luminance, measured in cd/m 2 in the forward direction, falls from the initial luminance to a certain proportion L1 when operated with a constant current density jo.
  • the specification U1000 in Table 4 designates the voltage required for a luminance of 1000 cd/m 2 .
  • EQE1000 designates the external quantum efficiency that can be achieved at 1000 cd/m 2 .
  • the service life LD is defined as the time after which the luminance drops from the initial luminance to a certain proportion L1 when operated with a constant current density jo.
  • the materials according to the invention become more blue fluorescent in examples E1a-g, E2a-g, E3a-f, E4a-f E5a-e as matrix materials in the emission layer of green or red phosphorescent OLEDs, in examples E6a-c as hole-blocking material in the hole-blocking layer OLEDs and in Examples E7a and E7b used as electron transport materials in the electron transport layer of blue fluorescent OLEDs.
  • E1a-g, E2a-g, E3a-f, E4a-f E5a-e as matrix materials in the emission layer of green or red phosphorescent OLEDs
  • examples E6a-c as hole-blocking material in the hole-blocking layer OLEDs
  • Examples E7a and E7b used as electron transport materials in the electron transport layer of blue fluorescent OLEDs As a comparison from the prior art come the Materials SdT1, SdT2, SdT3 and SdT4 in combination with the host materials H1, H2 and H3 in the comparative examples V
  • the examples according to the invention each show a clear advantage in the service life of the OLED and for the blue fluorescent OLEDs in examples 6a-c, 7a and b Compared to the V6 and V7, there is an advantage in terms of operating voltage and efficiency with otherwise comparable performance data for the OLED.
  • Table 4 Data of OLEDs for red emission
  • Table 5 Structure of the OLEDs for blue emission

Abstract

La présente invention concerne des composés qui se prêtent à une utilisation dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant ces composés.
EP22700041.1A 2021-01-05 2022-01-03 Matériaux pour dispositifs électroluminescents organiques Pending EP4274827A1 (fr)

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