EP4222792A1 - Composés pouvant être utilisés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques - Google Patents

Composés pouvant être utilisés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques

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Publication number
EP4222792A1
EP4222792A1 EP21805378.3A EP21805378A EP4222792A1 EP 4222792 A1 EP4222792 A1 EP 4222792A1 EP 21805378 A EP21805378 A EP 21805378A EP 4222792 A1 EP4222792 A1 EP 4222792A1
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Prior art keywords
radicals
group
substituted
compound
carbon atoms
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German (de)
English (en)
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Philipp Stoessel
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Merck Patent GmbH
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Merck Patent GmbH
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    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
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    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
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    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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    • C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H10K50/82—Cathodes
    • H10K50/824—Cathodes combined with auxiliary electrodes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to compounds for use in electronic devices, in particular in organic electroluminescent devices, and electronic devices, in particular organic electroluminescent devices, containing these compounds.
  • Organic electronic devices such as organic electroluminescent devices, generally include multiple layers of organic materials sandwiched between conductive thin film electrodes. When a voltage is applied to electrodes, holes and electrons are injected from an anode and a cathode, respectively. Holes and electrons can then combine into a bound state called an exciton. Excitons can decay, in particular in an emitting layer, with the emission of photons.
  • An electrode with a high sheet resistance is generally undesirable for use in organic electroluminescent devices because it produces a large current resistance (IR) drop when a device is used, which adversely affects the performance and efficiency of organic electroluminescent devices.
  • the IR drop can be compensated to some extent by increasing the power supply level.
  • the power supply level for a pixel is increased, the voltages supplied to other components are also increased to maintain proper operation of the device and are therefore disadvantageous.
  • the formation of bus conductor structures or auxiliary electrodes on the devices have been proposed as solutions.
  • such an auxiliary electrode can be produced by depositing a conductive coating which is electrically conductively connected to an electrode.
  • Such an auxiliary electrode can serve to conduct current more effectively to different areas of the device, thereby reducing the sheet resistance and associated IR drop of the electrode.
  • auxiliary electrode is typically provided on an OLED stack containing an anode, one or more organic layers and a cathode
  • the patterning of the auxiliary electrode is traditionally achieved using a shadow mask with mask openings through which a conductive coating is selectively deposited, for example by a physical vapor deposition (PVD) process.
  • PVD physical vapor deposition
  • these compounds which can be used in particular for structuring functional layers.
  • these compounds should be used for the production of improved auxiliary electrodes or the like structures can be used.
  • other properties of the organic electronic devices in particular their service life, their color purity, but also their efficiency and their operating voltage should not be adversely affected.
  • 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, and to provide the corresponding electronic device .
  • the compounds should have excellent processability, and the compounds should in particular have good solubility.
  • a further object of the present invention can be seen as providing compounds which are suitable for use in a phosphorescent or fluorescent electroluminescent device, in particular in an anti-settling layer.
  • a further object can be seen in providing electronic devices with excellent performance as cost-effectively as possible and with constant quality. Furthermore, the electronic devices should be able to be used or adapted for many purposes. In particular, the performance of the electronic devices should be maintained over a wide temperature range.
  • organic electronic devices preferably electroluminescent devices
  • organic electroluminescent devices which, in particular, relate to the Service life, color purity, efficiency and operating voltage have very good properties.
  • the present invention therefore relates to the use of a compound for structuring at least one functional layer of an organic electronic device, the compound comprising at least one fluorinated alkyl radical having at least two carbon atoms.
  • the term "structuring" refers here to the creation of a structure in or on a functional layer.
  • these structures can be used, for example, to produce electrically conductive units, in particular auxiliary electrodes, which bring about a reduction in the resistance of the electronic device and/or the operating voltage, with this being described above and below, so that reference is made thereto.
  • the fluorinated alkyl radical comprises at least 2 and particularly preferably at least 3 fluorine atoms.
  • the fluorinated alkyl radical preferably comprises at most 20, preferably at most 16, particularly preferably at most 12 and especially preferably at most 10 carbon atoms.
  • the fluorinated alkyl radical has a numerical ratio of fluorine atoms to carbon atoms of at least 0.5, preferably at least 0.75 and particularly preferably at least 1.
  • the fluorinated alkyl radical has a numerical ratio of hydrogen atoms to fluorine atoms of at most 1, preferably at most 0.75 and particularly preferably at most 0.5, the fluorinated alkyl radical particularly preferably being at most 10, preferably at most 6, particularly preferably comprises at most 4 and especially preferably no hydrogen atoms.
  • the fluorinated alkyl radical preferably comprises 2 to 20, particularly preferably 3 to 10, carbon atoms.
  • the fluorinated alkyl radical comprises or represents a cyclic group, with some of the carbon atoms preferably being bonded to at least two hydrogen atoms and some of the carbon atoms being bonded to at least two fluorine atoms.
  • the fluorinated alkyl radical is preferably linear or branched, particularly preferably linear, with some of the carbon atoms preferably being bonded to at least two hydrogen atoms and some of the carbon atoms being bonded to at least two fluorine atoms.
  • the fluorinated alkyl radical has a block structure, with part of the carbon atoms are bonded to at least two hydrogen atoms and a portion of the carbon atoms are bonded to at least two fluorine atoms.
  • block structure is known in the art and means that the fluorinated alkyl radical has block-like structures, it also being possible for a single CH 2 , CHF or CF 2 group to be regarded as a block.
  • the fluorinated alkyl radical has a structure of the formulas FA-1 to FA-16,
  • A is a group of the formula -(C x H 2x )-, -(C x H x D x )-, -(C x D 2x )-, where x is an integer ranging from 1 to 6, preferably 1 to 4, particularly preferably 1 or 2, where A is particularly preferably selected from -(CH 2 )-, -(CHD)- or -(CD 2 )-, -(CH 2 CH 2 )-, -(CHD-CHD )- or -(CD 2 CD 2 )- and especially preferably -(CH 2 )- or -(CH 2 CH 2 )-;
  • B is a group of the formula -(C y F 2y )-, -(C y F y H y )-, -(C y F y D y )-, where y is an integer ranging from 1 to 6, preferably 1 to 4, particularly preferably 1, 2 or 3, where B is particularly preferably selected from -(CF 2 CF 2 CF 2 )-, -(CFH-CFH-CFH)-, -(CFD-CFD-CFD)- , -(CF 2 CF 2 )-, -(CFH-CFH)-, -(CFD-CFD)-, -(CF 2 )-, -(CFH)- or -(CFD)-, and especially preferably -( CF 2 CF 2 )-, -(CF 2 CF 2 )-, or -(CF 2 )-;
  • E is selected from H, D or F, preferably F; a is an integer ranging from 1 to 6, preferably 1 to 4, more preferably 1 or 2; b is an integer ranging from 1 to 6, preferably 1 to 4, more preferably 1 or 2; where the structures of the formulas (FA-9) to (FA-16) can form a ring, but are preferably linear or branched, particularly preferably linear and are connected at two points to other groups of the compound, where the structures of the formulas (FA -1) to (FA-8) are preferred and the structures of the formulas (FA-1) to (FA-4) are particularly preferred.
  • the present invention preferably provides for the use of a compound comprising at least one structuring element of the formula (SE-I), (SE-II) and/or (SE-III).
  • group FA stands for a fluorinated alkyl radical with at least two carbon atoms, which can be substituted by one or more radicals R, but is preferably unsubstituted
  • the dashed bond represents the point of attachment, and the following also applies:
  • X is CR, N or C if a group is attached to X, preferably CR or C;
  • R 2 is selected identically or differently on each occurrence from the group consisting of H, D, F, CN, an aliphatic hydrocarbon radical having 1 to 20 carbon atoms or an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms in which one or more H atoms can be replaced by D, F, CI, Br, I or CN and can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms, with two or more, preferably adjacent, substituents R 2 together form a ring system.
  • the structuring element according to formula (SE-I), (SE-II) and / or (SE-I 11) comprises exactly 1, 2, 3 or 4 groups FA, one or more of the groups FA optionally is given by one or more of the substituents R.
  • An aryl group within the meaning of this invention contains 6 to 40 carbon atoms; a heteroaryl group within the meaning of this invention contains 2 to 40 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5.
  • the heteroatoms are preferably selected from N, 0 and/or S.
  • An aryl group or heteroaryl group is either a simple aromatic cycle, i.e.
  • benzene or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc. or a fused (fused) aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.
  • aromatics linked to one another by a single bond such as biphenyl, are not referred to as aryl or heteroaryl groups, but as aromatic ring systems.
  • An electron-deficient heteroaryl group in the context of the present invention is a heteroaryl group which has at least one heteroaromatic six-membered ring with at least one nitrogen atom. Further aromatic or heteroaromatic five-membered rings or six-membered rings can be fused onto this six-membered ring. Examples of electron-deficient heteroaryl groups are pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, quinazoline or quinoxaline.
  • An aromatic ring system within the meaning of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system within the meaning of this invention contains 2 to 60 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.
  • An aromatic or heteroaromatic ring system in the context of this invention is to be understood as meaning a system which does not necessarily only contain aryl or heteroaryl groups, but in which also several aryl or heteroaryl groups by a non-aromatic moiety, such as. B. a C, N or O atom may be connected.
  • systems such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, etc. should also be understood as aromatic ring systems for the purposes of this invention, and also systems in which two or more aryl groups are linked, 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 and/or heteroaryl groups are linked to one another by single bonds.
  • an aliphatic hydrocarbon radical or an alkyl group or an alkenyl or alkynyl group which can contain 1 to 20 carbon atoms, and which also contains individual H atoms or CH 2 groups, are represented by the groups mentioned above can be substituted, 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 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-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
  • a thioalkyl group with 1 to 40 carbon atoms is, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio,
  • 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; one or more H- Atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 , preferably F, Cl or CN, more preferably F or CN, particularly preferably CN.
  • An aromatic or heteroaromatic ring system with 5 to 60 or 5 to 40 aromatic ring atoms, which can be substituted with 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-indeno-fluorene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotru
  • the group FA of the structuring element according to formula (SE-I), (SE-II) and / or (SE-III) has at least one of the structures of the formulas (FA-1) to (FA-16) includes, preferably corresponds to.
  • the structuring element of the formula (SE-I), (SE-II) and/or (SE-III) can be represented by a formula (SE-1) to (SE-21). is,
  • E is selected from H, D or F, preferably H or F;
  • Y 1 is identical or different on each occurrence, a bond, O, S, NR 3 or C( ⁇ O), preferably a bond, 0, S, NR 3 , particularly preferably a bond, 0 or S, particularly preferably a bond;
  • the structuring element of the formula (SE-I), (SE-II) and/or (SE-III) can be represented by a formula (SE-1a) to (SE-21a).
  • the symbol R has the meaning given above, in particular for formula (SE-I), (SE-II) and/or (SE-I 11), the symbols Y 1 and E and the indices a, b, c, x and y have the meanings mentioned above, in particular for formulas (SE-1) to (SE-21), the dashed bond indicates the attachment point and the following applies to the other symbols: m is 0, 1, 2, 3 or 4, preferably 0 , 1 or 2, particularly preferably 0 or 1; s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; v is 0, 1, 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2.
  • two R radicals together with the heteroaromatic or aromatic groups to which these R radicals are attached do not form a fused aromatic or heteroaromatic ring system, this including possible substituents R 1 , R 2 by which the R radicals may be substituted.
  • R 1 , R 2 by which the R radicals may be substituted.
  • the sum of the indices a and x is at most 10, preferably at most 7 and particularly preferably at most 5 and that of the indices b and y is at most 10, preferably at most 7 and particularly preferably at most 5.
  • This preference applies in particular to structures of the formulas (SE-1a) to (SE-21a) and the other preferred configurations of these structures and compounds that are described above and below.
  • At least two, preferably at least three, of the radicals R and/or R 1 are F or a fluorinated alkyl radical having 1 to 20 carbon atoms.
  • This preference applies in particular to structures of the formulas (SE-I), (SE-II), (SE-III), (SE-1) to (SE-21) and (SE-1a) to (SE-21a). ) and the other preferred configurations of these structures and compounds that are described above and below.
  • a compound that can be used with preference for use according to the invention preferably comprises at least one aromatic or heteroaromatic ring system with at least two, preferably with at least three, fused aromatic or heteroaromatic rings.
  • the aromatic or heteroaromatic ring system with two, preferably with three, fused aromatic or heteroaromatic rings is selected from the groups of the formulas (Ar-1) to (Ar-18) where X 'N or CR a , preferably CR a , L 1 is a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 , wherein the dashed binding marks the binding position and the following still applies:
  • L 1 is a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , where R 1 is the previously, in particular for formula (SE-I) , (SE-II) and/or (SE-III) has the meaning mentioned, R a has the meaning set out above, in particular for formulas (Ar-1) to (Ar-18), the dashed bond marks the attachment position and for the Indices: p is 0 or 1 ; e is 0, 1 or 2, preferably 0 or 1; j is independently 0, 1, 2 or 3 on each occurrence, preferably 0, 1 or 2, particularly preferably 0 or 1; Each occurrence of h is independently 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1; g is an integer in the range from 0 to 7, preferably 0, 1, 2, 3, 4, 5 or 6, particularly preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2.
  • the sum of the indices p, e, j, h and g in the structures of the formula (Ar′-1) to (Ar′-18) is at most 3, preferably at most 2 and particularly preferably at most 1 .
  • the compound comprises at least one radical selected from the group consisting of phenyls, fluorenes, indenofluorenes, spirobifluorenes, carbazoles, indenocarbazoles, indolocarbazoles, spirocarbazoles, pyrimidines, triazines, quinazolines, quinoxalines, pyridines, quinolines, iso- Quinolines, Lactams, Triarylamines, Dibenzofurans, Dibenzothienes, Imidazoles, Benzimidazoles, Benzoxazoles, Benzthiazoles, 5-Aryl-phenanthridin-6-one, 9, 10-Dehydrophenanthrene, Fluoranthene, Naphthalene, Phenanthrene, Triphenylene, Anthracene, Benzanthracene, Fluoradene, Pyrene, Perylenes, chrysenes, borazines, boronyls, flu
  • the compound comprises at least one radical which is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2- 3- or 4-fluorenyl, 9,9'-diarylfluorenyl 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4-dibenzofuranyl, 1-, 2- , 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1-, 2-, 3-, 4- or 9-carbazolyl, 1- or 2-napthyl, anthracenyl, preferably 9-anthracenyl, Trans and cis inden
  • the compound contains one or more crosslinkable groups.
  • the compound has a molecular weight of less than or equal to 5000 g/mol, preferably less than or equal to 4000 g/mol, particularly preferably less than or equal to 3000 g/mol, particularly preferably less than or equal to 2000 g/mol and very particularly preferably less than or equal to 1200 g/mol.
  • the compound preferably has a glass transition temperature of at least 100° C., particularly preferably at least 120° C., very particularly preferably at least 150° C. and particularly preferably at least 180° C., determined according to DIN 51005.
  • a further object of the present invention are new compounds which can be used to structure functional layers and are outstandingly suitable for the production of improved electronic devices.
  • a further subject of the present invention are therefore compounds comprising at least one structure of the formula (I), preferably a compound of the formula (I), wherein the group FA 'stands for a fluorinated alkyl radical having at least two carbon atoms, which may be substituted by one or more radicals R, but is preferably unsubstituted, wherein the Symbol R has the meaning given above, in particular for formula (SE-I), (SE-II) and/or (SE-IH), and the following applies to the other symbols:
  • X 1 is CR b , N or C if the group L 2 is bonded to X 1 , preferably CR b or C;
  • X 2 is CR c , N or C if the group L 2 is bonded to X 2 , preferably CR c or C;
  • L 2 is a linking group, preferably a bond or an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30 aromatic ring atoms, which can be substituted by one or more radicals R 1 , where the symbol R 1 has the above, in particular for formula (SE-I), (SE-II) and/or (SE-III) has the meaning mentioned;
  • the compounds according to the invention comprise at least one structure of the formulas (I-1) to (I-7), it being possible for the compounds according to the invention to be selected particularly preferably from the compounds of the formulas (I- 1 ) to (I-7),
  • E is selected from H, D or F, preferably H or F;
  • Y 2 is identical or different on each occurrence, a bond, 0, S, NR 4 or C( ⁇ O), preferably a bond, 0, S, NR 4 , particularly preferably a bond, 0 or S, particularly preferably a bond;
  • the compounds according to the invention comprise a structure of the formulas (Ib-1) to (Ib-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (Ib-1) to (lb-7),
  • the symbols L 2 , R b and R c have the meanings given above, in particular for formula (I)
  • the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) have the meanings mentioned
  • the index s is 0, 1, 2, 3, 4, 5, 6 or 7, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (lc-1) to (lc-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (lc-1) to (lc-7),
  • the symbols L 2 , R b and R c have the meanings mentioned above, in particular for formula (I)
  • the symbol Y 2 and the index c have the meanings mentioned above, in particular for formulas (I-1) to (I-7).
  • the indices d and e have the meanings mentioned above, in particular for formulas (la-1) to (la-7)
  • the index s is 0, 1, 2, 3, 4, 5, 6 or 7, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • a preferred subject matter of the present invention is also a compound comprising at least one structure of the formula (II), preferably a compound of the formula (II), where the group FA 'stands for a fluorinated alkyl radical having at least two carbon atoms, which may be substituted by one or more radicals R, but is preferably unsubstituted, where the symbol R has the above, in particular for formula (SE-I), (SE-II ) and/or (SE-III) and the symbols L 2 , X 1 and X 2 have the meanings mentioned above, in particular for formula (I).
  • the compounds according to the invention comprise at least one structure of the formulas (II-1) to (II-7), it being possible for the compounds according to the invention to be selected particularly preferably from the compounds of the formulas (II- 1 ) to (II-7),
  • the compounds according to the invention comprise a structure of the formulas (IIa-1) to (IIa-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IIa-1) to (lla-7),
  • the compounds according to the invention comprise a structure of the formulas (IIb-1) to (IIb-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IIb-1) to (llb-7),
  • the symbols L 2 , R b and R c have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) mentioned meanings
  • the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3, or 4, especially preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (IIc-1) to (IIc-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IIc-1) to (llc-7), where the symbols L 2 , R b and R c have the meanings mentioned above, in particular for formula (I), the symbol Y 2 and the index c have the meanings mentioned above, in particular for formulas (I-1) to (I-7).
  • the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; and the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • a preferred subject matter of the present invention is also a compound comprising at least one structure of the formula (III), preferably a compound of the formula (III), where the group FA' is a fluorinated alkyl radical having at least two carbon atoms, which can be substituted by one or more radicals R, but is preferably unsubstituted, where the symbol R has the above, in particular for formula (SE-I), (SE- II) and/or (SE-IH) has the meaning mentioned, and the symbols L 2 , X 1 and X 2 have the meanings mentioned above, in particular for formula (I).
  • the compounds according to the invention comprise at least one structure of the formulas (III-1) to (III-7), it being possible for the compounds according to the invention to be selected particularly preferably from the compounds of the formulas (III- 1 ) to (III-7), where the symbols L 2 , X 1 and X 2 have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) have the meanings mentioned.
  • the compounds according to the invention comprise a structure of the formulas (IIIa-1) to (IIIa-7), in which case the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IIIa-1) to (lla-7),
  • the compounds according to the invention comprise a structure of the formulas (IIIb-1) to (IIIb-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IIIb-1) to (lllb-7),
  • the symbols L 2 , R b and R c have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings mentioned above, in particular for formulas (I-1) to (I-7), the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; and the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (IIIc-1) to (IIIc-7), where the compounds according to the invention can be particularly preferably selected from the compounds of the formulas (IIIc-1) to (lllc-7),
  • the symbols L 2 , R b and R c have the meanings mentioned above, in particular for formula (I)
  • the symbol Y 2 and the index c have the meanings mentioned above, in particular for formulas (I-1) to (I-7).
  • the indices d and e have the meanings mentioned above, in particular for formulas (la-1) to (la-7)
  • the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9 is preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • a preferred subject matter of the present invention is also a compound comprising at least one structure of the formula (IV), preferably a compound of the formula (IV), where the group FA 'stands for a fluorinated alkyl radical having at least two carbon atoms, which may be substituted by one or more radicals R, but is preferably unsubstituted, where the symbol R has the above, in particular for formula (SE-I), (SE -II) and/or (SE- III) has the meaning mentioned, and the symbols L 2 , X 1 and X 2 have the meanings mentioned above, in particular for formula (I).
  • the compounds according to the invention comprise at least one structure of the formulas (IV-1) to (IV-7), it being possible with particular preference for the compounds according to the invention to be selected from the compounds of the formulas (IV- 1 ) to (IV-7),
  • the compounds according to the invention comprise a structure of the formulas (IVa-1) to (IVa-7), in which case the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IVa-1) to (IVa-7),
  • the compounds according to the invention comprise a structure of the formulas (IVb-1) to (IVb-7), in which case the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IVb-1) to (IVb-7),
  • the symbols L 2 , R b and R c have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) mentioned meanings
  • the index w is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (IVc-1) to (IVc-7), where the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (IVc-1) to (IVc-7),
  • the symbols L 2 , R b and R c have the meanings mentioned above, in particular for formula (I), the symbol Y 2 and the index c have the meanings mentioned above, in particular for formulas (I-1) to (I-7).
  • the indices d and e previously, in particular for formulas (la-1) to (la-7) mentioned meanings, the index w is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2; and the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • a preferred subject matter of the present invention is also a compound comprising at least one structure of the formula (V), preferably a compound of the formula (V), where the group FA' is a fluorinated alkyl radical having at least two carbon atoms, which can be substituted by one or more radicals R, but is preferably unsubstituted, where the symbol R has the above, in particular for formula (SE-I), (SE- II) and/or (SE-IH) has the meaning mentioned, and the symbols L 2 , X 1 and X 2 have the meanings mentioned above, in particular for formula (I).
  • the compounds according to the invention comprise at least one structure of the formulas (V-1) to (V-7), it being possible for the compounds according to the invention to be selected particularly preferably from the compounds of the formulas (V- 1 ) to (V-7), where the symbols L 2 , X 1 and X 2 have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) have the meanings mentioned.
  • the compounds according to the invention comprise a structure of the formulas (Va-1) to (Va-7), in which case the compounds according to the invention can be particularly preferably selected from the compounds of the formulas (Va-1) to (Va-7),
  • the compounds according to the invention comprise a structure of the formulas (Vb-1) to (Vb-7), in which case the compounds according to the invention can be particularly preferably selected from the compounds of the formulas (Vb-1) to (Vb-7),
  • the symbols L 2 , R b and R c have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) mentioned meanings
  • the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, preferably 0, 1, 2, 3, or 4, especially preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (Vc-1) to (Vc-7), in which case the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (Vc-1) to (Vc-7),
  • the symbols L 2 , R b and R c have the meanings mentioned above, in particular for formula (I)
  • the symbol Y 2 and the index c have the meanings mentioned above, in particular for formulas (I-1) to (I-7).
  • the indices d and e have the meanings mentioned above, in particular for formulas (la-1) to (la-7)
  • the index v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9 is preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • a preferred subject matter of the present invention is also a compound comprising at least one structure of the formula (VI), preferably a compound of the formula (VI), wherein the group FA 'stands for a fluorinated alkyl radical having at least two carbon atoms, which may be substituted by one or more radicals R, but is preferably unsubstituted, wherein the
  • R has the meaning given above, in particular for formula (SE-I), (SE-II) and/or (SE-III), and the symbols L 2 , X 1 and X 2 have the meaning given above, in particular for formula (I ) have the meanings mentioned.
  • the compounds according to the invention comprise at least one structure of the formulas (VI-1) to (VI-7), it being possible for the compounds according to the invention to be selected particularly preferably from the compounds of the formulas (VI- 1 ) to (VI-7),
  • the compounds according to the invention comprise a structure of the formulas (Vla-1) to (Vla-7), in which case the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (Vla-1) to (Vla-7),
  • the compounds according to the invention comprise a structure of the formulas (Vlb-1) to (Vlb-7), in which case the compounds according to the invention can particularly preferably be selected from the compounds of the formulas (Vlb-1) to (Vlb-7), where the symbols L 2 , R b and R c have the meanings given above, in particular for formula (I), the symbols Y 2 and E and the indices a, b, c, x and y have the meanings given above, in particular for formulas (I -1) to (I-7) mentioned meanings, the index w is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, preferably 0, 1, 2, 3, or 4, particularly preferably 0, 1 or 2; and the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • the compounds according to the invention comprise a structure of the formulas (VIc-1) to (VIc-7), in which case the compounds according to the invention can be particularly preferably selected from the compounds of the formulas (VIc-1) to (Vlc-7),
  • the symbols L 2 , R b and R c have the meanings mentioned above, in particular for formula (I)
  • the symbol Y 2 and the index c have the meanings mentioned above, in particular for formulas (I-1) to (I-7).
  • the indices d and e have the meanings mentioned above, in particular for formulas (la-1) to (la-7)
  • the index w is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, preferably 0, 1, 2, 3 or 4, particularly preferably 0, 1 or 2
  • the index m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, particularly preferably 0 or 1.
  • two radicals R b form together with the heteroaromatic or aromatic groups to which these radicals R b bind, no fused aromatic or heteroaromatic ring system, this including possible substituents R 1 , R 2 , by which the radicals R b can be substituted.
  • the numerical ratio of fluorine atoms to carbon atoms in the group FA' is at least 0, 5, preferably at least 0.75 and more preferably at least 1.
  • the numerical ratio of hydrogen atoms to fluorine atoms in the group FA' is at most 1, preferably at most 0.75 and particularly preferably at most 0.5, the group FA' particularly preferably comprising at most 10, preferably at most 6, particularly preferably at most 4 and especially preferably no hydrogen atoms.
  • the group FA' has a maximum of 20, preferably a maximum of 16, particularly preferably at most 12 and especially preferably at most 10 carbon atoms.
  • the sum of the indices a and x is at most 10, preferably at most 7 and particularly preferably at most 5 and that of the indices b and y is at most 10, preferably at most 7 and particularly preferably at most 5.
  • This preference applies in particular to structures of the formulas (I-1) to (I-7), (Ib-1) to (Ib-7), (II-1) to (II-7), (IIb-1) to (IIb-7), (III-1) to (III-7), (IIIb-1) to (IIIb-7), (IV-1) to (IV-7), (IVb-1) to (IVb -7), (V-1) to (V-7), (Vb-1) to (Vb-7), (VI-1) to (VI-7) and (Vlb-1) to (Vlb-7 ) and the other preferred configurations of these structures and compounds that are described above and below.
  • a radical for example a radical R, R a , R b , R c , R 1 , R 2 , R 3 and/or R 4 has or represents a fluorinated alkyl radical having 1 to 20 carbon atoms
  • the fluorinated alkyl radical having 1 to 20 carbon atoms has a ratio of hydrogen atoms to fluorine atoms of at most 1, preferably at most 0.75 and particularly preferably at most 0.5
  • the fluorinated alkyl radical having 1 to 20 carbon atoms particularly preferably at most 10, preferably at most 6, particularly preferably at most 4, and particularly preferably comprises no hydrogen atoms.
  • a compound that can be used according to the invention can have a connecting group, this being set out in more detail, for example, in structures (Ar-1) to (Ar-18) and/or (Ar'-1) to (Ar'-18) as radical L 1 .
  • L 1 , L 2 represents a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably an aromatic ring system having 6 to 12 carbon atoms, which is substituted by one or more radicals R 1 may be substituted, but is preferably unsubstituted, where R 1 may have the meaning given above, in particular for formula (SE-I), (SE-II) and/or (SE-III).
  • L 1 , L 2 is particularly preferably an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, which can each be substituted by one or more radicals R 2 , but is preferably unsubstituted, where R 2 can have the meaning mentioned above, in particular for formula (SE-I), (SE-II) and/or (SE-III).
  • the group L 1 or L 2 comprises an aromatic ring system with at most two fused aromatic and/or heteroaromatic 6-rings, preferably no fused aromatic or heteroaromatic ring system. Accordingly, naphthyl structures are preferred over anthracene structures. Furthermore, fluorenyl, spirobifluorenyl, dibenzofuranyl and/or dibenzothienyl structures are preferred over naphthyl structures. Particularly preferred are structures that do not exhibit condensation, such as phenyl, biphenyl, terphenyl and/or quaterphenyl structures.
  • Suitable aromatic or heteroaromatic ring systems L 1 , L 2 are selected from the group consisting of ortho-, meta- or para-phenylene, ortho-, meta- or para-biphenylene, terphenylene, in particular branched terphenylene, quaterphenylene, in particular branched quaterphenylene , Fluorenylene, spirobifluorenylene, dibenzofuranylene, dibenzothienylene and carbazolylene, each of which may be substituted by one or more radicals R 1 , but are preferably unsubstituted.
  • the group L 1 or L 2 has at most 1 nitrogen atom, preferably at most 2 heteroatoms, particularly preferably at most one heteroatom and particularly preferably no heteroatom.
  • the compound comprises at least one linking group selected from formulas (L 1 -1 ) to (L 1 -74), or the residue L 1 in formulas (Ar-1 ) to (Ar-18) and/or (Ar'-1) to (Ar'-18) represents a bond or a group selected from the formulas (L 1 -1 ) to (L 1 -74), or the radical L 2 in formulas (I), (l-1) to (I-7), (la-1) to (la-7), (lb-1) to (lb-7), (lc- 1) to (lc-7), (II), (ll-1) to (II-7), (lla-1) to (lla-7), (llb-1) to (llb-7), ( llc-1 ) to (llc-7), (III), (lll-1 ) to (III-7), (llla-1 ) to (llla-7), (lllb-1 ) to (lllb-7) , (IIIc-1) to (IIIc-7), (III), (lll-1 ) to
  • the dashed bonds respectively mark the attachment positions
  • the subscript k is 0 or 1
  • the subscript I is 0, 1 or 2
  • the subscript j is independently 0, 1, 2 or 3 at each occurrence
  • the subscript h is independently 0, 1, 2, 3, or 4 on each occurrence
  • the subscript g is 0, 1, 2, 3, 4, or 5
  • the symbol Y' is O, S, BR 1 or NR 1 , preferably 0 or NR 1
  • the symbol R 1 has the meaning given above, in particular for formula (SE-I), (SE-II) and/or (SE-III).
  • the sum of the indices k, I, g, h and j in the structures of the formulas (L 1 -1 ) to (L 1 -74 ) is preferably not more than 3, preferably not more than 2 and particularly preferably not more than 1.
  • Preferred compounds having a group of the formulas (Ar-1) to (Ar-18) and/or (Ar'-1) to (Ar'-18) comprise a group L 1 selected from a bond or one of the formulas (L 1 -1 ) to (L 1 -46) and/or (L 1 - 57) to (L 1 -74), preferably of the formula (L 1 -1 ) to (L 1 -32) and/or ( L 1 -57) to (L 1 -74), especially preferably of the formula (L 1 -1) to (L 1 -10) and/or (L 1 - 57) to (L 1 -68).
  • ) and/or (L 1 -57) to (L 1 - 68) are each at most 3, preferably at most 2 and particularly preferably at most 1.
  • Preferred compounds having a structure of the formulas (I), (l-1) to (I-7), (la-1) to (la-7), (lb-1) to (lb-7), (lc- 1) to (lc-7), (II), (ll-1) to (II-7), (lla-1) to (lla-7), (llb-1) to (llb-7), ( llc-1 ) to (llc-7), (III), (lll-1 ) to (III-7), (llla-1 ) to (llla-7), (lllb-1 ) to (lllb-7) , (IIIc-1) to (IIIc-7), (IV), (IV-1) to (IV-7), (IVa-1) to (IVa-7), (IVb-1) to (IVb- 7), (IVc-1) to (IVc-7), (V), (V-1) to (V-7), (Va-1) to (Va-7), (Vb-1) to ( Vb-7), (Vc-1) to (Vc-7), (VI), (VI-1)
  • ) and/or (L 1 -57) to (L 1 -68) are each at most 3, preferably at most 2 and particularly preferably at most 1.
  • radicals which can be selected in particular from R, R a , R b , R c , R 1 , R 2 , R 3 and/or R 4 , form a ring system with one another, this can be mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic.
  • 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 bonded directly to one another, or they can be further be distant from each other.
  • each of the corresponding binding sites is preferably provided with a substituent R, R a , R b , R c , R 1 , R 2 , R 3 and/or R 4 .
  • the substituents R, R a , R b , R c , R 1 , R 2 , R 3 and/or R 4 of the structures presented above and below do not form a fused aromatic or heteroaromatic ring system, preferably not a fused ring system .
  • At least one of the radicals R, R a , R b and/or R c is selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 9,9'-diaryl-fluorenyl 1-, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1-, 2-, 3- or 4 -dibenzofuranyl, 1-, 2-, 3- or 4-dibenzothienyl, pyrenyl, triazinyl, imidazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1-, 2-, 3-, 4- or 9-carbazolyl, 1- or 2-napthyl , anthracenyl,
  • Preferred aromatic or heteroaromatic ring systems R , Ra, Rb , Rc , Ar' and/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 can be linked, naphthalene, in particular 1- or 2-linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which is linked via the 1-, 2-, 3-, 4- or 9-position may be, dibenzofuran which may be linked via the 1-, 2-, 3- or 4-position, dibenzothiophene which may be linked via
  • R, R a , R b , R c is the same or different on each occurrence selected from the group consisting of H, D, F, CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , a straight-chain alkyl group having 1 to 20 carbon atoms or a branched or cyclic alkyl group having 3 to 20 carbon atoms, the alkyl group in each case with can be substituted by one or more radicals R 1 , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, preferably having 5 to 40 aromatic ring atoms, which can each be substituted by one or more radicals R 1 .
  • the substituent R, R a , R b , R c 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 20 carbon atoms or a branched one or cyclic alkyl group with 3 to 20 carbon atoms, where each alkyl group can be substituted with one or more radicals R 1 , or an aromatic or heteroaromatic ring system with 5 to 60 aromatic ring atoms, preferably with 5 to 40 aromatic ring atoms, that each may be substituted by one or more R 1 radicals.
  • At least one substituent substituent R, R a , R b , R c is selected identically or differently on each occurrence from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which may be substituted with one or more R 1 groups, or a group N(Ar') 2 .
  • the substituent R, R a , R b , R c is the same or different on each occurrence selected from the group consisting of H, D, an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms, which with one or more radicals R 1 , or a group N(Ar') 2 .
  • Substituent R, R a , R b , R c is particularly preferably the same or different on each occurrence selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably with 6 to 13 aromatic ring atoms, each of which can be substituted by one or more radicals R 1 .
  • Preferred aromatic or heteroaromatic ring systems of the substituents R, R a , R b , R c , R 1 , R 3 , R 4 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 via the 1-, 2-, 3- or 4- Position can be linked, spirobifluorene, which can be linked via the 1 -, 2-, 3- or 4-position, naphthalene, in particular 1 - or 2- linked naphthalene, indole, benzofuran, benzothiophene, carbazole, which via the 1 - , 2-, 3- or 4-position, dibenzofuran, which can be linked via the 1-, 2-, 3- or 4-position
  • R 1 -1 to R 1 -43 listed below are particularly preferred, with structures of the formulas R 1 -1 , R 1 -3 , R 1 -4 , R 1 -10 , R 1 -11 , R 1 -12 , R 1 - 13, R 1 -14, R 1 -16, R 1 -17, R 1 -18, R 1 -19, R 1 -20, R 1 -21 and/or R 1 -22 are particularly preferred .
  • R 1 -1 to R 1 -43 it should be noted that these are represented with a substituent R 2 . In the case of the ring systems R, R a , R b , R c these substituents R 2 are to be replaced by R 1 .
  • R 1 , R 3 , R 4 are particularly preferably selected from the group consisting of H, D, F, CN, N(Ar") 2 , a straight-chain alkyl group with 1 to 8 carbon atoms, preferably with 1 , 2, 3 or 4 carbon atoms, or a branched or cyclic alkyl group having 3 to 8 carbon atoms, preferably having 3 or 4 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms, preferably having 2, 3 or 4 carbon atoms, each of which can be substituted by one or more R 2 radicals, but is preferably unsubstituted, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, particularly preferably having 6 to 13 aromatic ring atoms, each of which may be substituted by one or more non-aromatic radicals R 1 , R 3 , R 4 , but is preferably unsubstituted; optional
  • the substituents R 1 , R 3 , R 4 are very particularly preferably selected from the group consisting of H or an aromatic or heteroaromatic ring system having 6 to 18 aromatic ring atoms, preferably having 6 to 13 aromatic ring atoms, each with one or more non-aromatic radicals R 2 may be substituted, but is preferably unsubstituted.
  • substituents R 1 are selected from the group consisting of phenyl, ortho-, meta- or para-biphenyl, terphenyl, in particular branched terphenyl, quaterphenyl, in particular branched quaterphenyl, 1-, 2-, 3- or 4-fluorenyl, 1 -, 2-, 3- or 4-spirobifluorenyl, pyridyl, pyrimidinyl, 1 -, 2-, 3- or 4-dibenzofuranyl, 1 -, 2-, 3- or 4-dibenzothienyl, 1 -, 2-, 3 - or 4- Carbazolyl and indenocarbazolyl, which can each be substituted by one or more radicals R 2 , but are preferably unsubstituted.
  • the substituents R 1 , R 3 , R 4 of a ring system with other ring atoms of the ring system do not form a fused aromatic or heteroaromatic ring system, preferably not a fused ring system.
  • R 1 or Ar stands for a group selected from the formulas (R 1 -1) to (R 1 -43), or in a structure according to formula (Ar-1 ) to (Ar-18) and/or (Ar'-1 ) to (Ar'-18) at least one R 1 is a group selected from the formulas (R 1 -1 ) to (R 1 - 43 ), or in a structure according to formulas (I), (l-1) to (I-7), (la-1) to (la-7), (lb-1) to (lb-7), (lc -1) to (lc-7), (II), (ll-1) to (II-7), (lla-1) to (lla-7), (llb-1) to (llb-7), (llc-1) to (llc-7), (II), (ll-1) to (II-7), (lla-1) to (lla-7), (llb-1) to (llb-7), (llc-1) to (llc-7), (II), (ll-1) to (II
  • R 1 is a group selected from the formulas (R 1 -1 ) to (R 1 - 43),
  • Y is O, S or NR 2 , preferably O or S; k is independently 0 or 1 on each occurrence; i is independently 0, 1 or 2 for each occurrence; j is independently 0, 1, 2, or 3 on each occurrence; h is independently 0, 1, 2, 3 or 4 on each occurrence; g is independently 0, 1, 2, 3, 4 or 5 on each occurrence; R 2 has the meaning given above, in particular for formula (SE-I), (SE-II) and/or (SE-IH), and the dashed bond marks the attachment position.
  • R 1 , R 3 , R 4 is identical or different on each occurrence selected from the group consisting of H, D, F, CN, a straight-chain alkyl group having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, it being possible for each alkyl group to be substituted by one or more R 2 radicals, or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, each of which is substituted by one or more R 2 radicals can be.
  • R 1 , R 3 , R 4 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 C atoms, or a branched or cyclic alkyl group with 3 to 6 C atoms, where the alkyl group can be substituted with one or more radicals R 2 , but is preferably unsubstituted, or an aromatic or heteroaromatic ring system 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 identical or different on each occurrence and is H, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms which is substituted with an alkyl group having 1 to 4 carbon atoms may be, but is preferably unsubstituted.
  • all of the alkyl groups preferably have no more than five carbon atoms, particularly preferably no more than 4 carbon atoms particularly preferably not more than 1 carbon atom.
  • compounds which are substituted with alkyl groups in particular branched alkyl groups, having up to 10 carbon atoms or which are substituted with oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl - or quaterphenyl groups, are substituted.
  • Preferred compounds which can be used according to the invention and/or compounds according to the invention preferably have a sublimation temperature which is preferably in the range from 150 to 400° C., particularly preferably in the range from 180 to 360° C. and especially preferably in the range from 220 to 340° C., measured according to DIN 51006.
  • the sublimation temperature results from the vacuum TGA measurement, in which a material is sublimated or evaporated in a targeted manner.
  • the measurement can be carried out using a TG 209 F1 Libra device from Netzsch with the following measurement conditions: Sample weight: 1 mg Crucible: open aluminum crucible Heating rate: 5 K/min Temperature range: 105-550°C
  • Atmosphere vacuum 10-2 mbar (regulated)
  • the compound has at least two, preferably at least three, four or more, particularly preferably exactly two or exactly three structuring elements according to the previously defined formula (SE-I), (SE-II), (SE-III) and /or at least two, preferably at least three, four or more, particularly preferably exactly two or exactly three structures according to the formulas (I), (I-1) to (I-7), (Ia-1) to (Ia -7), (lb-1 ) to (lb-7), (lc-1 ) to (lc-7),
  • a compound according to the invention is represented by at least one of the structures of the formulas (I), (I-1) to (I-7), (Ia-1) to (Ia-7), (Ib-1) to ( lb-7), (lc-1) to (lc-7), (II), (ll-1) to (II-7), (lla-1) to (lla-7), (llb-1) to (llb-7), (llc-1) to (llc-7), (III), (lll-1) to (III-7), (llla-1) to (llla-7), (lllb- 1) to (IIIb-7), (IIIc-1) to (IIIc-7), (IV), (IV-1) to (IV-7), (IVa-1) to (IVa-7), ( IVb-1) to (IVb-7), (IVc-1) to (IVc-7), (V), (V-1) to (V-7), (Va-1) to (Va-7) , (Vb-1) to (Vb-7), (Vc-1) to (IVc-7), (V
  • compounds according to the invention preferably comprising structures of the formulas (I), (I-1) to ( I-7), (la-1) to (la-7), (lb-1) to (lb-7), (lc-1) to (lc-7), (II), (ll-1) to (II-7), (lla-1) to (lla-7), (llb-1) to (llb-7), (llc-1) to (llc-7), (III), (lll- 1) to (III-7), (IIIa-1) to (IIIa-7), (IIIb-1) to (IIIb -7), (IIIc-1) to (IIIc-7), (IV), (IV-1) to (IV-7), (IVa-1) to (IVa-7), (IVb-1) to (IVb-7), (IVc-1) to (IVc-7), (V), (V-1) to (V-7), (Va-1) to (Va-7), (Vb-1 ) to (Vb-7), (Vc-1) to (Vc-7), (VI), (VI-1) to
  • preferred compounds according to the invention are characterized in that they can be sublimated. These compounds generally have a molecular weight of less than about 1200 g/mol.
  • the preferred embodiments mentioned above can be combined with one another as desired.
  • the preferred embodiments mentioned above apply simultaneously.
  • the compounds which can be used according to the invention and the new compounds according to the invention can in principle be prepared by various processes. However, the methods described below have proven to be particularly suitable.
  • a further subject of the present invention is therefore a process for preparing the compounds according to the invention, in which a compound comprising at least one fluorinated alkyl radical having at least two carbon atoms is linked to a compound comprising at least one aromatic or heteroaromatic group in a coupling reaction .
  • Suitable compounds comprising at least one fluorinated alkyl radical having at least two carbon atoms can often be obtained commercially, the starting compounds set out in the examples being obtainable by known processes, so that reference is made thereto.
  • Particularly suitable and preferred coupling reactions are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA. These reactions are well known and the examples provide further guidance to those skilled in the art.
  • Particularly suitable compounds can be made with the following aryl bromides, listed via CAS number, with the boron esters S: S1, S2, S3, S4, S5, S6, S7, S8, S9, S10, S11, S12, S13, S14, S15 , S16, S17, S18, S9, S20, S21 , S22, S23, S24 are obtained, the boron esters S: S1 , S2, S3, S4, S5, S6, S7, S8, S9, S10, S11 , S12, S13, S14, S15, S16, S17, S18, S9, S20, S21, S22, S23, S24 are set out in more detail in the examples.
  • the compounds according to the invention are produced in yields of about 50-90%, the regiochemistry of the CC coupling being clearly determined by the position of the coupling partners, aryl bromide and aryl boronic acid. If the aryl bromides are di, tri, tetra, etc. bromides, the stoichiometry is adjusted accordingly so that all Br functions react with CC coupling:
  • the compounds according to the invention can be obtained in high purity, preferably more than 99% (determined by means of 1 H-NMR and/or HPLC).
  • the compounds according to the invention or the compounds which can be used according to the invention can also be mixed with a polymer. It is also possible to covalently incorporate these compounds into a polymer. This is possible in particular with compounds which are substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic esters, or with reactive, polymerizable groups such as olefins or oxetanes. This 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.
  • the compounds and polymers according to the invention can be used as a crosslinked or uncrosslinked layer.
  • the invention therefore also relates to oligomers, polymers or dendrimers containing one or more of the structures of the formulas (I), (II), (III), (IV), (V), (VI) and preferred embodiments of these formulas listed above Compounds according to the invention, wherein one or more bonds of the compounds according to the invention or the structures of the formulas (I), (II), (III), (IV), (V), (VI) and preferred embodiments of this formula to the polymer, oligomer or dendrimer available.
  • oligomers or dendrimers can be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers can be linear, branched or dendritic. The same preferences as described above apply to the repeating units of the compounds according to the invention in oligomers, dendrimers and polymers.
  • the monomers according to the invention are homopolymerized or copolymerized with other monomers.
  • Copolymers are preferred in which the units of the formulas (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below account for 0.01 to 99.9 mol%, preferably 5 to 90 mol%, more preferably 20 to 80 mol% are present.
  • Suitable and preferred comonomers that form the polymer backbone are selected from fluorenes (e.g. according to EP 842208 or WO 2000/022026), spirobifluorenes (e.g.
  • the polymers, oligomers and dendrimers can also 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 distinguished by a high glass transition temperature are of particular interest.
  • compounds according to the invention comprising structures of the formulas (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below, which one Glass transition temperature of at least 70°C, particularly preferably at least 110°C, very particularly preferably at least 125°C and particularly preferably at least 150°C, determined according to DIN 51005 (version 2005-08).
  • Formulations of the compounds according to the invention are required for the processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing processes. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this.
  • Suitable and preferred solvents are toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrol, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 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, ⁇ -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, do
  • a further object of the present invention is therefore a formulation or a composition containing at least one compound according to the invention and at least one further compound.
  • the further connection can be, for example, a solvent, in particular one of the abovementioned solvents or a mixture of these solvents. If the further compound comprises a solvent, then this mixture is referred to herein as a formulation.
  • the further compound can also be at least one further organic or inorganic compound which is also used in the electronic device, for example an emitter and/or a matrix material, these compounds differing from the compounds according to the invention. Suitable emitters and matrix materials are listed below in connection with the organic electroluminescent device.
  • the further connection can also be polymeric.
  • compositions containing a compound according to the invention and at least one further organically functional material.
  • Functional materials are generally the organic or inorganic materials that are placed between the anode and the cathode.
  • the organically functional material is preferably selected from the group consisting of fluorescent emitters, phosphorescent emitters, emitters that show TADF (thermally activated delayed fluorescence), host materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, Electron blocking materials, hole blocking materials, wide band gap materials and n-dopants.
  • An electronic device containing at least one connection 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 also layers which are made up entirely of inorganic materials.
  • the electronic device is preferably selected from the group consisting of
  • the electronic device is particularly preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLED, PLEDs, LECs, etc.), preferably organic light-emitting diodes (OLEDs), organic light small molecule-based emitting diodes (sOLEDs), organic polymer-based light-emitting diodes (PLEDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), organic plasmon emitting devices (D. M.
  • OLEDs organic electroluminescent devices
  • sOLED organic light small molecule-based emitting diodes
  • PLEDs organic polymer-based light-emitting diodes
  • LECs organic laser diodes
  • O-lasers organic laser diodes
  • 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
  • O-FQDs Organic Optical Detectors
  • organic photoreceptors organic field quench devices
  • O-FQDs organic electrical sensors
  • OLEDs organic electroluminescent devices
  • sOLED, PLEDs, LECs, etc. particularly preferably organic light-emitting diodes (OLEDs), organic light-emitting diodes Based on small molecules (sOLEDs), organic light-emitting diodes based on polymers (PLEDs), in particular phosphorescent OLEDs.
  • a preferred embodiment of an electronic device comprises at least one, preferably precisely one, anti-settling layer.
  • a layer preventing settling has the effect that layers subsequently applied to this layer have a poor preferably do not form or settle at all.
  • a deposit prevention layer is preferably not continuous or closed, but preferably has a structure. Substances applied subsequently, for example metals, can come into contact with previously applied layers as a result of this structure.
  • a deposit prevention layer is used, for example, to produce auxiliary electrodes, which are explained in more detail above and below, and which bring about a reduction in the resistance of an electronic device.
  • the anti-deposition layer can be produced, for example, via a shadow mask with mask openings. It is particularly advantageous here that the mask used in this way can be easily cleaned and reused. Solvents suitable for this purpose have been set out above, so that reference is made thereto, with NMP preferably being able to be used. If appropriate, the solvent can be used at elevated temperature.
  • a preferred electronic device contains at least one compound whose use is defined above, a compound comprising at least one structure according to the formulas (I), (l-1) to (I-7), (la-1) to (la-7) , (lb-1) to (lb-7), (lc-1) to (lc-7), (II), (ll-1) to (II-7), (lla-1) to (lla- 7), (llb-1) to (llb-7), (llc-1) to (llc-7), (III), (lll-1) to (III-7), (llla-1) to ( llla-7), (lllb-1) to (lllb-7), (lllc-1) to (lllc-7), (IV), (IV-1) to (IV-7), (IVa-1) to (IVa-7), (IVb-1) to (IVb-7), (IVc-1) to (IVc-7), (V), (V-1) to (V-7), (Va- 1) to (Va-7), (Vb-1) to (IVb-7), (
  • the anti-settling layer preferably consists of one or more of the compounds whose use is defined above, of one or more of the compounds comprising at least one structure according to the formulas (I), (l-1) to (I-7), (la-1) to (la-7), (lb-1) to (lb-7), (lc-1) to (lc-7), (II), (ll-1) to (II-7), (lla- 1) to (lla-7), (llb-1) to (llb-7), (llc-1) to (llc-7), (III), (lll-1) to (III-7), ( IIIa-1) to (IIIa-7), (IIIb-1) to (IIIb-7), (IIIc-1) to (IIIc-7), (IV), (IV-1) to (IV-7) , (IVa-1) to (IVa-7), (IVb-1) to (IVb-7), (IVc-1) to (IVc-7), (V), (V-1) to (V- 7), (Va-1) to (Va-7), (Vb-1) to
  • the anti-settling layer particularly preferably consists of one or more of the compounds whose use is defined above or of one or more of the compounds comprising at least one structure according to the formulas (I), (I-1) to (I-7), ( la-1) to (la-7), (lb-1) to (lb-7), (lc-1) to (lc-7), (II), (ll-1) to (II-7) , (lla-1) to (lla-7), (llb-1) to (llb-7), (llc-1) to (llc-7), (III), (lll-1) to (III- 7), (IIIa-1) to (IIIa-7), (IIIb-1) to (IIIb-7), (IIIc-1) to (IIIc-7), (IV), (IV-1) to ( IV-7), (IVa-1) to (IVa-7), (IVb-1) to (IVb-7), (IVc-1) to (IVc-7), (V), (V-1) to (V-7), (Va-1) to (Va-7), (Vb-1)
  • the anti-settling layer can be obtained at a deposition rate preferably ranging from 0.1 to 100 angstroms/second (A/s), more preferably in the range of 1 to 50 A/s and especially preferably in the range of 2 to 20 A/s.
  • the measurement is typically carried out with a tooled (calibrated) quartz crystal.
  • An electronic device includes cathode, anode and at least one functional layer.
  • an electronic device according to the invention preferably contains a deposit prevention layer, as is described in more detail above and below.
  • This anti-deposition layer serves in particular to produce an electrically conductive structure, preferably an auxiliary electrode. It can preferably be provided that the anti-deposition layer serves to produce an auxiliary cathode.
  • the deposit prevention layer can be provided between the emission layer and the cathode.
  • all materials that are used to produce an anode or cathode can be used as electrically conductive substances which are used, for example, to produce electrically conductive units, in particular auxiliary electrodes. These materials are preferably applied by vaporization methods, so that metals, metal alloys or semi-metals are preferably used. Preferred metals, metal alloys or semi-metals are characterized by good volatility and high conductivity.
  • alkali metals in particular Li, Na, K
  • alkaline earth metals especially Be, Mg, Ca, Sr, Ba
  • Group 3 metals in particular Al, Ga, In
  • Group 4 metals or semimetals in particular Si, Ge, Sn
  • Bi transition metals, preferably Cu, Ag, Au, Zn
  • Lanthanides preferably Yb.
  • These metals can be used individually or as an alloy of 2, 3, 4 or more components.
  • These alloys can be obtained, inter alia, by co-evaporation or evaporation of the mixture at the eutectic point, so that these alloys are obtained directly as a structured layer in the manufacture of the electronic device.
  • Preferred materials in particular metals or metal alloys, which can be used to produce preferred cathodes, are distinguished by a work function which is preferably in the range from 1.7 to 5.5 eV, particularly preferably in the range from 2.0 to 5. 0 eV, especially preferably in the range of 2.5 to 4.5 eV.
  • the electrically conductive structure preferably the auxiliary electrode
  • the electrically conductive structure can be obtained with a deposition rate which is preferably in a range from 0.1 to 100 angstroms/second (A/s), particularly preferably in the range from 1 to 50 A/s and especially preferably in the range of 2 to 20 A/s.
  • the measurement is typically carried out with a tooled (calibrated) quartz crystal.
  • the organic electroluminescent device contains cathode, anode and at least one emitting layer. In addition to these layers, it can also contain further layers, for example one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, 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 electroluminescent device according to the invention can also be a tandem electroluminescent device, in particular for white-emitting OLEDs.
  • a preferred mixture of an emitter and a matrix material 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 Matrix material 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.
  • Suitable matrix materials are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, for example according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, for example 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, for example according to WO 2007/063754 or WO 2008/056746 according to example WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776, azacarbazole derivatives, for example according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for example according to WO
  • a compound can be used as a co-host that does not participate, or does not participate to a significant extent, in charge transport, as described, for example, in WO 2010/108579.
  • Particularly suitable as co-matrix material are compounds which have a large band gap and do not themselves participate in the charge transport of the emitting layer, or at least not to a significant extent.
  • Such materials are preferably pure hydrocarbons. Examples of such materials can be found, for example, in WO 2009/124627 or in WO 2010/006680.
  • an emitter is preferably used in combination with one or more phosphorescent materials (triplet emitters) and/or a compound that represents a TADF (thermally activated delayed fluorescence) host material.
  • a hyperfluorescence and/or hyperphosphorescence system is preferably formed here.
  • WO 2015/091716 A1 and WO 2016/193243 A1 disclose OLEDs which contain both a phosphorescent compound and a fluorescent emitter in the emission layer, with the energy being transferred from the phosphorescent compound to the fluorescent emitter (hyperphosphorescence).
  • the phosphorescent compound behaves like a host material.
  • host materials have higher singlet and triplet energies compared to the emitters, so that the energy of the host material can also be transferred to the emitter as optimally as possible.
  • the systems disclosed in the prior art have just such an energy relation.
  • Phosphorescence within the meaning of this invention is understood as meaning 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.
  • 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.
  • the phosphorescence emitters used are preferably 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.
  • Examples of the emitters described above can be found in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/ 0258742 WO 2009/146770 WO 2010/015307 WO 2010/031485 WO 2010/054731 WO 2010/054728 WO 2010/086089 WO 2010/099852 WO 2010/102709 WO 2010/099852 066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/104045, WO 2015/12018/12015/ WO 2016/124304, WO 2017/032439, WO 2018/011186, WO 2018/001990
  • thermally activated delayed fluorescence (TADF) is described, for example, by BH Uoyama et al., Nature 2012, Vol. 492, 234.
  • TADF thermally activated delayed fluorescence
  • a comparatively small singlet-triplet distance ⁇ E(S 1 -T 1 ) of, for example, less than about 2000 cm -1 is necessary in the emitter.
  • another connection can be provided in the matrix, which has a strong spin-orbit coupling, so that the spatial proximity and the interaction between the molecules are enabled to cross between systems, or the spin-orbit coupling is generated via a metal atom contained in the emitter.
  • the organic electroluminescent device according to the invention contains no separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i. H. the emitting layer directly adjoins the hole injection layer or the anode, and/or the emitting layer directly adjoins 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 hole transport or hole injection material, such as, for example, B. described in WO 2009/030981.
  • the deposit prevention layer is preferably not continuous, so that the electrodes are in direct contact with the other layers via the applied metal.
  • organic electroluminescent device In 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 the materials known for organic electroluminescence devices in combination with the compounds which can be used according to the invention or the compounds according to the invention or the preferred embodiments described above without any inventive activity.
  • 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 of between 10'5 mbar and 1 bar.
  • OVJP Organic Vapor Jet Printing
  • 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.
  • Formulations for applying a compound of the formula (I), (II), (III), (IV), (V), (VI) or its or their preferred embodiments described above are new.
  • a further subject matter of the present invention is therefore a formulation , containing at least one solvent and a compound of the formula (I) or their preferred embodiments set out above.
  • 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. These methods are generally known to the person skilled in the art and can be applied to organic electroluminescent devices containing the compounds according to the invention without any inventive step.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished in particular by an improved service life compared to the prior art.
  • the other electronic properties of the electroluminescent devices, such as efficiency or operating voltage, remain at least as good.
  • the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished, compared with the prior art, in particular by improved efficiency and/or operating voltage and a longer service life.
  • the electronic devices according to the invention are characterized by one or more of the following surprising advantages over the prior art:
  • the compounds that can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below can have very different evaporation rates. velocities can be applied via gas deposition processes. As a result, preferred electronic devices can be manufactured very simply, securely and inexpensively.
  • the compounds which can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below can be applied to very different layers Gas deposition processes are applied and show an excellent structuring ability for different metal / metal alloys. This allows preferred electronic Devices with very different structures can be produced very simply, safely and inexpensively.
  • the compounds which can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below are distinguished by excellent solubility in many solvents. As a result, the shadow masks that are preferably used for structuring can be cleaned easily and inexpensively.
  • the shadow masks previously used for structuring have to be produced individually for each electronic device and are correspondingly expensive. If these masks are used in order to structure evaporated metal, these masks become unusable after a short time, since deposited metal leads to a reduction in size or to a closure of the openings provided in the mask. This metal deposited on the mask cannot be removed from the mask.
  • these devices are characterized by a high PL and thus high EL Efficiency of emitters and excellent energy transfer from matrices to dopants.
  • Compounds which can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below exhibit excellent glass film formation.
  • Electronic devices, in particular organic electroluminescent devices containing compounds that can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below can very have narrow emission bands with low FWHM values (Full Width Half Maximum) and enable a particularly pure color emission, recognizable by the small CIE y values.
  • devices according to the invention can have a low roll-off, ie a low drop in the Having power efficiency of the device at high luminances.
  • Electronic devices in particular organic electroluminescent devices containing compounds which can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments for structuring set out above and below of at least one functional layer can have excellent efficiency. It should be noted here that using the compounds that can be used according to the invention or compounds of the formula (I), (II), (III), (IV), (V), (VI) or the preferred embodiments described above and below have no negative effects have on the efficiency. Furthermore, the compounds that can be used according to the invention or compounds of the formula (I) or the preferred embodiments explained above and below contribute indirectly to a low operating voltage in electronic devices via the production of an electrically conductive structure.
  • the solvents and reagents can e.g. B. from Sigma-ALDRICH or ABCR.
  • the respective information in square brackets or the numbers given for individual compounds relate to the CAS numbers of the compounds known from the literature. In the case of compounds which can have several enantiomeric, diastereomeric or tautomeric forms, one form is shown as a representative.
  • the solid is filtered off with suction, washed twice with 200 ml of water and twice with 100 ml of methanol and dried in vacuo.
  • the solid is taken up in 300 ml of dichloromethane, filtered through a silica gel bed pre-slurried with DCM, the filtrate is mixed with 200 ml of methanol and concentrated in vacuo to a volume of about 100 ml.
  • the crystallized product is filtered off and dried in vacuo. Cleaning is via three times hot extraction crystallization from acetonitrile or by chromatography on silica gel and subsequent fractional sublimation. Yield: 30.6 g (68 mmol) 68%; Purity: > 99.5% according to HPLC.
  • suitable components are first produced - as described below - and then subjected to a measurement of the difference in transmission.
  • the transmission is high (>90%) in the areas in which the compounds according to the invention have prevented metal deposition, ie structuring has taken place.
  • Electron conductors which are applied by co-evaporation, as well as other organic functional materials can be used (see table).
  • the layer thicknesses are tracked using a referenced (geoloted) quartz oscillator, as is customary in OLED device construction according to the SdT.
  • the metal deposit is characterized by means of a relative transmission measurement with light with a wavelength of 500-550 nm.

Abstract

La présente invention concerne l'utilisation de composés pour la structuration d'au moins une couche fonctionnelle d'un dispositif électronique organique. La présente invention concerne également des composés préférés appropriés pour être utilisés dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des dispositifs électroluminescents organiques, contenant lesdits composés.
EP21805378.3A 2020-09-30 2021-09-28 Composés pouvant être utilisés pour la structuration de couches fonctionnelles de dispositifs électroluminescents organiques Pending EP4222792A1 (fr)

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WO2022069421A1 (fr) 2022-04-07
CN116508417A (zh) 2023-07-28
US20230371363A1 (en) 2023-11-16
KR20230077741A (ko) 2023-06-01
TW202222748A (zh) 2022-06-16

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