EP2941469A2 - Matériaux pour dispositifs électroniques - Google Patents

Matériaux pour dispositifs électroniques

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Publication number
EP2941469A2
EP2941469A2 EP13802887.3A EP13802887A EP2941469A2 EP 2941469 A2 EP2941469 A2 EP 2941469A2 EP 13802887 A EP13802887 A EP 13802887A EP 2941469 A2 EP2941469 A2 EP 2941469A2
Authority
EP
European Patent Office
Prior art keywords
group
formula
groups
atoms
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.)
Withdrawn
Application number
EP13802887.3A
Other languages
German (de)
English (en)
Inventor
Anja JATSCH
Christof Pflumm
Amir Hossain Parham
Thomas Eberle
Philipp Stoessel
Jonas Valentin Kroeber
Rouven LINGE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to EP13802887.3A priority Critical patent/EP2941469A2/fr
Publication of EP2941469A2 publication Critical patent/EP2941469A2/fr
Withdrawn legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
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    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • 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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    • H10K85/657—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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    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
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    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
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    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
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    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
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    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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Definitions

  • the present application relates to a compound of formula (I), (II) or (III) which is a carbazole and an electron-deficient
  • the compound may be used in an electronic device, preferably an organic electronic device. Furthermore, the present application relates to a process for the preparation of the compound.
  • organic electronic devices are understood as meaning in particular so-called organic electronic devices (organic electronic devices), which are organic
  • OLED optical light-emitting diode
  • organic emitter layers Lifetime and efficiency and operating voltage. An important role is played by organic emitter layers, in particular the matrix materials contained therein, and organic layers
  • Phosphorescent emitting layers in the context of the present application are those organic layers which contain at least one phosphorescent emitting compound (phosphorescent dopants).
  • phosphorescent emitter comprises compounds in which the light emission takes place by a spin-forbidden transition, for example a transition from an excited triplet state or a state with a higher spin quantum number, such as a quintet state.
  • a matrix material is included in a system comprising
  • Matrix material and a dopant understood that component whose proportion in the mixture is the larger. Accordingly, a dopant in a system containing a matrix material and a dopant is understood to mean the component whose proportion in the mixture is smaller.
  • Carbazole derivatives such as, for example, bis (carbazolyl) biphenyl, or carbazole compounds or indenocarbazole compounds, such as, for example, according to WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 2008/086851 as matrix materials for phosphorescent emitters, are frequently used in the prior art used.
  • triazine compounds eg. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746 used.
  • Z is the same or different CR 1 or N at each occurrence
  • aromatic ring atoms which may be substituted by one or more radicals R 2 , wherein two or more radicals R 1 may be linked together and form a ring;
  • R A is a group of formula (A)
  • R A is R, wherein at least one group R A pro
  • aromatic ring atoms which may be substituted by one or more radicals R 3 , wherein two or more radicals R 2 may be linked together and form a ring;
  • R 3 is the same or different at each occurrence, H, D, F or a
  • aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by D or F; two or more substituents R 3 may be linked together and form a ring;
  • Ar 1 is an aromatic ring system with 6 to 30 aromatic
  • Ring atoms which may be substituted by one or more radicals R 1 ;
  • T is a single bond or an aromatic
  • Ring atoms which may be substituted by one or more R 1 radicals.
  • the group Cbz is a carbazo group which may be extended with indeno groups to an indenocarbazole, in the context of the present application it is understood that in one or both of the six-membered rings of the carbazole indeno groups can be fused.
  • indeno groups one or two are preferably present.
  • two indeno groups are preferably not both attached to the same six-membered carbazole ring.
  • An indeno group is understood to mean the following structure:
  • Condensation of the indeno group is understood as meaning that it shares two ring atoms with two ring atoms of the six-membered carbazole.
  • These two ring atoms are preferably the ring atoms marked with * .
  • the condensation of Indeno phenomenon takes place at the
  • An aryl group in the sense of this invention contains 6 to 60 aromatic ring atoms;
  • a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are preferably selected from N, O and S. This is the basic definition. If other preferences are given in the description of the present invention, for example with respect to the number of aromatic ring atoms or the heteroatoms contained, these apply.
  • an aryl group or heteroaryl group is either a simple aromatic cycle, ie benzene, or a simpler one
  • heteroaromatic cycle for example pyridine, pyrimidine or
  • heteroaromatic polycycle for example, naphthalene, phenanthrene, quinoline or carbazole understood.
  • a condensed (anneliierter) aromatic or heteroaromatic polycycle consists in the context of the present application of two or more condensed single aromatic or heteroaromatic cycles.
  • radicals can be substituted and which can be linked via any position on the aromatic or heteroaromatic, are
  • Phenanthridine benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyrimididazole, pyrazine imidazole, quinoxaline imidazole, oxazole, Benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole,
  • the invention will be understood to mean an aryl group as defined above which is attached via an oxygen atom.
  • An analogous definition applies to heteroaryloxy groups.
  • An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom. The heteroatoms are
  • an aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups are replaced by a non-aromatic unit (preferably less than 10% of the atoms other than H) , such as B.
  • a non-aromatic unit preferably less than 10% of the atoms other than H
  • an sp 3 - hybridized C, Si, N or O atom, an sp 2 -hybridized C or N atom or a sp-hybridized carbon atom may be connected.
  • systems such as 9,9'-spirobifluorene, 9,9'-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl, alkenyl or alkynyl group or linked by a silyl group.
  • systems in which two or more aryl or heteroaryl groups are linked together via single bonds are understood as aromatic or heteroaromatic ring systems in the context of this invention, such as systems such as
  • An aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms, which may be substituted in each case by radicals as defined above and which may be linked via any positions on the aromatic or heteroaromatic compounds, is understood in particular to mean groups derived from benzene, naphthalene .
  • alkoxy or thioalkyl group having 1 to 40 carbon atoms 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,
  • Hexinylthio, heptynylthio or octynylthio understood.
  • the two radicals are linked together by a chemical bond, under the formulation that two or more radicals can form a ring with one another. This is illustrated by the following scheme:
  • the compound of the formula (I), (II) or (III) preferably contains no condensed aryl or heteroaryl groups having more than 14 aromatic ring atoms, more preferably no aryl or heteroaryl groups having more than 10 aromatic ring atoms.
  • an index i per formula (A) is equal to one and the other index i is equal to zero. Further preferably, two or three groups X per six-membered ring are equal to N.
  • Ar 1 is preferably selected from an aromatic ring system having 6 to 18 aromatic ring atoms which may be substituted by one or more radicals R 1 .
  • Ar 1 is particularly preferably selected from phenyl optionally substituted by radicals R 1 , biphenyl, terphenyl, naphthyl, fluorenyl or spirobifluorenyl.
  • Groups of the formula (A) preferably correspond to one of the following formulas (A-) to (A-8)
  • Formula (A-7) Formula (A-8) wherein the occurring groups are as defined above, and wherein the dotted line denotes the bond to the rest of the formula.
  • the preferred embodiments given in the present application regarding the groups L 1 , E and R x are also preferred.
  • E 1 is the same at each occurrence. Furthermore, E 1 is preferably identical or different at each occurrence, O or S, particularly preferably O.
  • L 1 is furthermore preferably an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms, particularly preferably an aromatic ring system having 6 to 24 aromatic ring atoms, wherein the ring systems may be substituted with one or more R radicals.
  • the group L 1 comprises at least one meta or ortho-phenylene group which may be optionally substituted with one or more R 1 radicals.
  • Very particularly preferred groups L are selected from groups of the following formulas (L-1) to (L-18)
  • Formula (L-17) Formula (L-18) wherein the groups may be substituted at all free positions with radicals R 1 and wherein the dashed lines indicate the bonds to the rest of the compound in the event that the sum of the indices i is equal to 1 and only one group E is present. In the event that the sum of the indices i is equal to 2, so that there are two groups E 1 , preferably both groups E 1 are bonded to the same aryl group.
  • modified groups of the formulas (L-1) to (L-18) should be used which, instead of two dashed lines, have three dashed lines corresponding to the bonds to the rest of the formula.
  • not more than three groups Z per six-membered ring are equal to N, more preferably not more than two groups Z. Further preferably, no more than two adjacent groups Z are N. Furthermore, Z is preferably CR 1 .
  • Preferred groups Cbz correspond to the following formulas (Cbz-1) to (Cbz-3)
  • aromatic ring atoms which may be substituted in each case with one or more radicals R 2 , wherein two or more radicals R 1 may be linked together and form a ring.
  • R 1 is attached to the methylene group of an indeno group which is part of a group Cbz or indenocarbazole group of
  • Formula (II) is bonded, selected from a straight-chain alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein the above-mentioned groups each substituted with one or more radicals R 2 or the two radicals R 1 which bind to the same methylene group are linked together and form an alkyl ring with the methylene group, wherein the alkyl ring may be substituted in each case with one or more radicals R 2 .
  • alkyl rings represented by two radicals R 1 on a methylene group -C (R) 2 - in a group Cbz, the one Indenocarbazole group are selected from the following formulas (C-1) to (C-8)
  • both groups R A are preferably groups of the formula (A). However, for formula (II), one R A may also be a group of formula (A) and the other R A is R 1 .
  • R A can not be equal to R 1 but has to be formula (A)
  • Preferred compounds of the formula (I) correspond to one of the following formulas (1-1) to (I-24)
  • E is selected from O and S.
  • L 1 is selected from an aromatic or heteroaromatic ring system having 6 to 24
  • aromatic ring atoms more preferably an aromatic ring system having 6 to 24 aromatic ring atoms, wherein the
  • Ring systems with one or more radicals R 1 may be substituted.
  • R 1 is selected from groups of formulas (L-1) to (L-18) as defined above.
  • Preferred compounds of the formula (II) correspond to one of the following formulas (11-1) to (II-8)
  • R A is equal to R 1 or equal to a group of the formula
  • (A) can be.
  • R A in formulas (11-1) to (II-8) is a group of formula (A).
  • R A is chosen such that the two to the
  • Carbazole nitrogen atoms bonded groups are the same.
  • E 1 is selected from O and S.
  • L 1 is selected from an aromatic or heteroaromatic ring system having 6 to 24
  • aromatic ring atoms more preferably an aromatic ring system having 6 to 24 aromatic ring atoms, wherein the
  • Ring systems with one or more radicals R 1 may be substituted.
  • R 1 is selected from groups of formulas (L-1) to (L-18) as defined above.
  • T is a single bond or an aromatic or heteroaromatic
  • Ring system having 6 to 24 aromatic ring atoms, which may be substituted with one or more radicals R 1 . More preferably, T is a single bond.
  • the group T in each case binds to the group Cbz of the unit of the formula (I). Furthermore, it is preferred that the units of the formula (I) are in each case chosen the same in compounds of the formula (III).
  • E 1 is selected from O and S.
  • L 1 is selected from an aromatic or heteroaromatic ring system having 6 to 24
  • aromatic ring atoms more preferably an aromatic ring system having 6 to 24 aromatic ring atoms, wherein the
  • Ring systems with one or more radicals R 1 may be substituted.
  • R 1 is selected from groups of formulas (L-1) to (L-18) as defined above.
  • T is a single bond or an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms which may be substituted by one or more radicals R 1 , T in compounds of the formula (III-1) to (III-5) is particularly preferably one
  • the compounds of the invention can be prepared by known organic chemical synthesis methods. These include
  • Scheme 1 shows the synthesis of compounds of the invention containing an oxygen- or sulfur-functionalized, electron-deficient
  • a protected oxygen- or sulfur-functionalized linker is first coupled to a carbazole derivative in a Buchwald coupling. After deprotection, this is reacted with an electron-deficient heteroaromatic in a substitution reaction. In this case, a compound of the invention is obtained, which, however, can be further functionalized and modified.
  • Scheme 2 shows the synthesis of compounds having a nitrogen-functionalized electron-deficient heteroaryl group.
  • a halogen-substituted linker is first coupled to the carbazole derivative in a Buchwald coupling. Subsequently, in a second Buchwald reaction, the reaction is coupled with an amino group functionalized with an electron-deficient heteroaryl group.
  • a compound of the invention is obtained, which, however, can be further functionalized and modified.
  • Hal halogen, preferably Br
  • Ar any aryl or heteroaryl group
  • another object of the invention is a process for the preparation of a compound of formula (I), (II) or (III), characterized in that at least one transition metal-catalyzed coupling reaction is used.
  • the transition metal-catalyzed coupling reaction is a Hartwig-Buchwald coupling, which is particularly preferably on
  • Nitrogen atom of the carbazole derivative takes place.
  • the electron-deficient heteroaryl group is introduced by a Hartwig-Buchwald reaction when substituted with an amino group and by a nucleophilic aromatic moiety
  • Suitable reactive leaving groups are, for example, bromine, iodine, chlorine, boronic acids, boronic esters, amines, alkenyl or alkynyl groups with terminal CC double bond or C-C triple bond, oxiranes, oxetanes, groups which have a cycloaddition, for example a 1, 3 or dipolar cycloaddition, as received
  • Another object of the invention are therefore oligomers, polymers or dendrimers containing one or more compounds according to
  • Formula (I), (II) or (III), wherein the binding (s) to the polymer, oligomer or dendrimer at any, in formula (I), (II) or (III) substituted with R 1 or R x substituted positions could be.
  • the compound is part of a side chain of the oligomer or polymer or constituent of the main chain.
  • An oligomer in the context of this invention is understood as meaning a compound which is composed of at least three monomer units.
  • a polymer in the context of the invention is understood to mean a compound which is composed of at least ten monomer units.
  • Dendrimers may be conjugated, partially conjugated or non-conjugated.
  • the oligomers or polymers of the invention may be linear, branched or dendritic.
  • the units of the formula (I), (II) or (III) may be linked directly to each other or they may have a divalent group, for example via a substituted or unsubstituted alkylene group, via a heteroatom or via a bivalent aromatic or heteroaromatic group linked together.
  • three or more units of the formula (I), (II) or (III) can have a trivalent or higher valent group, for example via a trivalent or higher valent aromatic or heteroaromatic group, to a branched or dendritic oligomer or Being polymer linked.
  • repeat units of the formula (I), (II) or (III) in oligomers, dendrimers and polymers have the same preferences as described above for compounds of the formula (I), (II) or (III).
  • the monomers according to the invention are homopolymerized or copolymerized with further monomers.
  • Suitable and preferred comonomers are selected from fluorenes (eg according to EP 842208 or WO 00/22026), spirobifluorenes (eg according to EP 707020, EP 894107 or WO 06/061181), paraphenylenes (eg. according to WO 1992/18552), carbazoles (eg according to WO 04/070772 or WO 2004/113468), thiophenes (eg according to fluorenes (eg according to EP 842208 or WO 00/22026), spirobifluorenes (eg according to EP 707020, EP 894107 or WO 06/061181), paraphenylenes (eg. according to WO 1992/18552), carbazoles (eg according to WO 04/070772 or WO 2004/113468), thiophenes (eg according to
  • EP 1028136 dihydrophenanthrenes (for example according to WO 2005/014689 or WO 2007/006383), cis and trans indenofluorenes (for example according to WO
  • ketones eg according to
  • WO 2005/040302 phenanthrenes (for example according to WO 2005/104264 or WO 2007/017066) or also several of these units.
  • the polymers, oligomers and dendrimers usually also contain further units, for example emitting (fluorescent or phosphorescent) units, such as.
  • Vinyltriarylamines for example according to WO 2007/068325
  • phosphorescent metal complexes for example according to WO 2006/003000
  • charge transport units in particular those based on tertiary amines.
  • the polymers, oligomers and dendrimers according to the invention have advantageous properties, in particular high lifetimes, high
  • the polymers and oligomers according to the invention are generally prepared by polymerization of one or more types of monomer, of which at least one monomer in the polymer leads to repeat units of the formula (I), (II) or (III).
  • Suitable polymerization reactions are known in the art and described in the literature.
  • Particularly suitable and preferred polymerization reactions which lead to C-C or C-N linkages are the following:
  • the present invention thus also provides a process for the preparation of the polymers, oligomers and dendrimers according to the invention, which is prepared by polymerization according to SUZUKI, polymerization according to YAMAMOTO, polymerization according to SILENCE or polymerization according to HARTWIG-BUCHWALD.
  • the dendrimers according to the invention can be prepared according to methods known to the person skilled in the art or in analogy thereto. Suitable methods are described in the literature, such as.
  • formulations of the compounds according to the invention are required. These formulations may be, for example, solutions, dispersions or emulsions. It may be preferable to use mixtures of two or more solvents for this purpose. Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene,
  • Methyl benzoate mesitylene, tetralin, veratrole, THF, methyl THF, THP, chlorobenzene, dioxane, phenoxytoluene, 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 .
  • Triethylene glycol dimethyl ether diethylene glycol monobutyl ether
  • Tripropylene glycol dimethyl ether Tripropylene glycol dimethyl ether, tetraethylene glycol dimethlyl ether, 2- Isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzoi,
  • the invention therefore further provides a formulation, in particular a solution, dispersion or emulsion containing at least one compound of the formula (I) or at least one polymer, oligomer or dendrimer comprising at least one unit of the formula (I) and at least one solvent, preferably one organic solvent.
  • a formulation in particular a solution, dispersion or emulsion containing at least one compound of the formula (I) or at least one polymer, oligomer or dendrimer comprising at least one unit of the formula (I) and at least one solvent, preferably one organic solvent.
  • the compounds according to the invention are suitable for use in electronic devices, in particular in organic electroluminescent devices (OLEDs).
  • OLEDs organic electroluminescent devices
  • the compounds can be used, inter alia, depending on the substitution, in different functions and / or layers. Preference is given to
  • Another object of the invention is the use of the
  • the electronic devices are preferably selected from the group consisting of organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and more preferably selected from organic electroluminescent devices (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
  • organic optical detectors organic photoreceptors
  • O-FQDs organic field quench devices
  • LECs organic laser diodes
  • O-lasers organic laser diodes
  • the invention furthermore relates to an electronic device comprising the anode, cathode and at least one organic layer, wherein the organic layer contains at least one compound of the formula (I), (II) or (III).
  • the electronic device is preferably selected from the abovementioned devices and particularly preferably an organic electroluminescent device (OLED).
  • the organic electroluminescent device may contain further layers. These are selected, for example, from one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers, exciton blocking layers, charge generation layers (IDMC 2003, Taiwan, Session 21 OLED (5), T. Matsumoto , T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphöton Organic EL Device Having Charge Generation Layer), outcoupling layers, and / or organic or inorganic p / n junctions. It should be noted, however, that not necessarily each of these layers must be present and the choice of layers always depends on the compounds used and in particular also on the fact that it is a fluorescent or phosphorescent electroluminescent device. The preferred ones used in the respective layers and functions
  • the sequence of the layers of the organic electroluminescent device is preferably as follows:
  • the organic electroluminescent device according to the invention may contain a plurality of emitting layers.
  • these emission layers particularly preferably have a total of a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H. in the emitting layers
  • the compounds according to the invention can also be present in the electron transport layer or in another layer. It should be noted that for the production of white light, instead of a plurality of color-emitting emitter compounds, a single used one
  • Emitter compound may be suitable, which in a broad
  • Wavelength range emitted Wavelength range emitted.
  • Formula (I), (II) or (III) in an electronic device containing one or more phosphorescent dopants is used.
  • the compound can be used in different layers, preferably in an electron transport layer or in an emitting layer.
  • phosphorescent emitter comprises compounds in which the light emission takes place by a spin-forbidden transition, for example a transition from an excited triplet state or a state with a higher spin quantum number, such as a quintet state.
  • phosphorescent dopants are particularly suitable
  • phosphorescent dopants compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium are preferably used, in particular compounds containing iridium, platinum or copper.
  • phosphorescent dopants can be found in applications WO 2000/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 2005/033244, WO 2005/019373 and US 2005/0258742 be removed.
  • all the phosphorescent complexes used in the prior art for phosphorescent OLEDs and as known to those skilled in the art of organic electroluminescent devices are suitable for use in the devices according to the invention.
  • the skilled person without inventive step further phosphorescent complexes in combination with the inventive
  • the compounds of the formula (I), (II) or (III) are used as matrix material in an emitting layer in combination with one or more dopants, preferably phosphorescent dopants.
  • a dopant is understood to mean that component whose proportion in the Mix the smaller one is.
  • a matrix material in a system comprising a matrix materal and a dopant is understood to mean the component whose proportion in the mixture is greater.
  • the proportion of the matrix material in the emitting layer is in this case between 50.0 and 99.9% by volume, preferably between 80.0 and 99.5% by volume and particularly preferred for fluorescent emitting layers between 92.0 and 99.5% by volume and for phosphorescent emitting layers between 85.0 and 97.0 vol.%.
  • the proportion of the dopant is between 0.1 and
  • An emitting layer of an organic electroluminescent device may also contain systems comprising a plurality of matrix materials (mixed-matrix systems) and / or multiple dopants. Also in this case, the dopants are generally those materials whose proportion in the system is smaller and the matrix materials are those materials whose proportion in the system is larger.
  • the dopants are generally those materials whose proportion in the system is smaller and the matrix materials are those materials whose proportion in the system is larger.
  • the proportion of a single matrix material in the system may be smaller than the proportion of a single dopant.
  • the compounds according to formula (I), (II) or (III) are used as a component of mixed-matrix systems.
  • the mixed-matrix systems preferably comprise two or three different matrix materials, more preferably two different matrix materials.
  • One of the two materials preferably provides a material with hole transporting
  • Matrix materials may be present in a ratio of 1:50 to 1: 1, preferably 1:20 to 1: 1, more preferably 1:10 to 1: 1 and most preferably 1: 4 to 1: 1. Preference is given to mixed-matrix systems in phosphorescent organic electroluminescent used devices. More detailed information on mixed-matrix systems is contained inter alia in the application WO 2010/108579.
  • the mixed-matrix systems may comprise one or more dopants.
  • the dopant compound or the dopant compounds may comprise one or more dopants.
  • the matrix components together according to the invention have a proportion of 0.1 to 50.0 vol .-% of the total mixture and preferably a proportion of 0.5 to 20.0 vol .-% of the total mixture. Accordingly, the matrix components together have a proportion of 50.0 to 99.9% by volume of the total mixture and preferably a proportion of 80.0 to 99.5% by volume of the total mixture.
  • Particularly suitable matrix materials which can be used in combination with the compounds according to the invention as matrix components of a mixed-matrix system are selected from the below-mentioned preferred matrix materials for phosphorescent dopants or the preferred matrix materials for fluorescent dopants, depending on the type of dopant in the mixed Matrix system is used.
  • Preferred phosphorescent dopants for use in mixed-matrix systems comprising the compounds according to the invention are the phosphorescent compounds listed in a table below
  • the compound of the formula (I), (II) or (III) is used as the electron transport material in an electron transport layer or electron injection layer or hole blocking layer.
  • the emitting layer may contain fluorescent and / or phosphorescent emitters.
  • Preferred fluorescent dopants are selected from the class of arylamines.
  • An arylamine or an aromatic amine in the context of this invention is understood as meaning a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen. At least one of these aromatic or heteroaromatic ring systems is preferably a fused ring system, more preferably at least 14 aromatic ring atoms.
  • Preferred examples of these are aromatic anthracene amines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysendiamines.
  • aromatic anthracene amine a compound in which a diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
  • An aromatic anthracenediamine is understood to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position.
  • Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, the diarylamino groups being preferably attached to the pyrene in the position or in the 1,6-position.
  • Further preferred dopants are indenofluoreneamines or -diamines, for example according to WO 2006/08497 or US Pat
  • WO 2006/122630 Benzoindenofluorenamine or diamines, for example according to WO 2008/006449, and dibenzoindenofluorenamine or -diamines, for example according to WO 2007/140847, as well as those described in WO
  • Aryl groups are preferred. Likewise preferred are the pyrene-arylamines disclosed in WO 2012/048780 and EP 12004426.8 not yet disclosed. Also preferred are those not yet disclosed
  • EP 12006239.3 disclosed benzoindenofluorene amines.
  • Suitable matrix materials are materials of different substance classes.
  • Preferred matrix materials are selected from the classes of the oligoarylenes (for example 2,2 ', 7,7'-tetraphenylspirobifluorene according to EP 676461 or dinaphthylanthracene), in particular the
  • Oligoarylenevinylenes eg DPVBi or spiro-DPVBi according to EP 676461
  • the polypodal metal complexes eg according to WO 2004/081017)
  • the hole-conducting compounds eg according to WO 2004/058911
  • the electron-conducting compounds in particular ketones, phosphine oxides, sulfoxides, etc.
  • the atropisomers for example according to WO 2006/048268
  • the boronic acid derivatives for example according to WO 2006 / 117052
  • the benzanthracenes eg according to WO 2008/145239.
  • Particularly preferred matrix materials are
  • an oligoarylene is to be understood as meaning a compound in which at least three aryl or arylene groups are bonded to one another.
  • Preferred matrix materials for phosphorescent emitters are, in addition to the compounds according to the invention, aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, eg. B.
  • WO 2010/136109 WO 201 1/000455 or WO 2013/041176, Azacarbazolderivate, z. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for. B. according to WO 2007/137725, silanes, z. B. according to WO 2005/1 1 72, azaborole or boronic esters, z. B. according to WO 2006/117052, triazine derivatives, z. B. according to WO 2010/015306, WO 2007/063754 or WO
  • Suitable charge transport materials as used in the hole injection or hole transport layer or in the electron transport layer of the
  • materials for the electron transport layer in addition to the compounds according to the invention, it is possible to use all materials which are used according to the prior art as electron transport materials in the electron transport layer.
  • aluminum complexes for example Alq 3
  • zirconium complexes for example Zrq
  • benzimidazole derivatives triazine derivatives, Pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.
  • Further suitable materials are derivatives of the abovementioned compounds, as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.
  • Preferred hole transport materials which can be used in a hole transport, hole injection or electron blocking layer in the electroluminescent device according to the invention are indenofluorenamine derivatives (for example according to WO 06/122630 or WO 06/100896) which are disclosed in EP 1661888 Amine derivatives, hexaazatriphenylene derivatives (eg according to WO 01/049806), amine derivatives with condensed aromatics (eg according to US Pat. No. 5,061,569), the amine derivatives disclosed in WO 95/09147, monobenzoindofluorenamines (eg according to WO 08 / 006449)
  • Dibenzoindenofluoreneamines eg according to WO 07/140847
  • spirobifluorene amines eg according to WO 2012/034627 or WO 2013/120577
  • fluorene amines eg according to the not yet disclosed applications
  • EP 12005369.9, EP 12005370.7 and EP 12005371.5 spiro-dibenzopyran amines (eg according to WO 2013/083216) and dihydroacridine derivatives (eg according to WO 2012/150001).
  • low work function metals, metal alloys or multilayer structures of various metals are preferable, such as
  • Alkaline earth metals alkali metals, main group metals or lanthanides (eg Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.).
  • alloys of an alkali or alkaline earth metal and silver for example an alloy of magnesium and silver.
  • further metals which have a relatively high work function, such as, for example, As Ag or Al, which then usually combinations of metals, such as Ca / Ag, Mg / Ag or Ba / Ag are used. It may also be preferred to provide a thin intermediate layer of a high material between a metallic cathode and the organic semiconductor
  • dielectric constant For this example comes Alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates in question (eg LiF, Li 2 O, BaF 2 , MgO, NaF, CsF, CS 2 CO 3, etc.). Furthermore, lithium quinolinate (LiQ) can be used for this purpose.
  • the layer thickness of this layer is preferably between 0.5 and 5 nm.
  • the anode high workfunction materials are preferred.
  • the anode has a work function greater than 4.5 eV. Vacuum up.
  • metals with a high redox potential such as Ag, Pt or Au, are suitable for this purpose.
  • metal / metal oxide electrodes eg Al / Ni / NiO x , Al / PtO x ) may also be preferred. For some applications, at least one of the electrodes must be transparent or
  • anode material is conductive mixed metal oxides.
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • the anode can also consist of several layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide,
  • Molybdenum oxide or vanadium oxide are examples of Molybdenum oxide or vanadium oxide.
  • the device is structured accordingly (depending on the application), contacted and finally sealed, since the life of the devices according to the invention is shortened in the presence of water and / or air.
  • Organic electroluminescent device characterized in that one or more layers are coated by a sublimation process. In this case, “6 mbar evaporated. However, it is also possible that the initial pressure is even lower, for example less than 10", the materials in vacuum sublimation at an initial pressure less 1fJ 5 mbar, preferably less than 10 7 mbar. Also preferred is an organic electroluminescent device, characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation. The materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
  • OVPD Organic Vapor Phase Deposition
  • OVJP Organic Vapor Jet Printing
  • 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. B. by spin coating, or with any printing process, such.
  • screen printing flexographic printing, Nozzle Printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or ink-jet printing (ink jet printing), are produced.
  • LITI Light Induced Thermal Imaging, thermal transfer printing
  • ink-jet printing ink jet printing
  • Solubility can be achieved by suitable substitution of the compounds. It is furthermore preferred for one or more layers of solution and one or more layers to be used for producing an organic electroluminescent device according to the invention
  • Light sources in medical and / or cosmetic applications e.g., light therapy
  • the reaction mixture is added to 300 ml of ice and warmed to room temperature with stirring.
  • the precipitated solid is filtered and washed with 300 mL of ethanol and 300 mL of n-heptane.
  • the solid is recrystallized from toluene and then under high vacuum (3-10 "6 bar) sublimated The purity is 99.9% (HPLC)
  • the yield was 8 g (13.2 mmol; 21%).
  • the OLEDs have the following layer structure: substrate / hole transport layer (HTL) / intermediate layer (IL) / electron blocking layer (EBL) / emission layer (EML) / optional hole blocking layer (HBL) / electron transport layer (ETL) and finally a cathode.
  • the cathode is formed by a 100 nm thick aluminum layer.
  • Table 1 The exact structure of the OLEDs is shown in Table 1. The to
  • the emission layer always consists of at least one matrix material (host material, host material) and an emitting dopant (dopant, emitter), which is admixed to the matrix material or the matrix materials by co-evaporation in a specific volume fraction.
  • An indication such as 6g: IC2: TEG1 (55%: 35%: 10%) means that the material contains 6g in a volume fraction of 55%, IC2 in a proportion of 35% and TEG1 in a proportion of 10% in the layer is present.
  • the electron transport layer may consist of a mixture of two materials.
  • the OLEDs are characterized by default. For this, the electroluminescence spectra, the current efficiency (measured in cd / A), the power efficiency (measured in Im / W) and the external quantum efficiency (EQE, measured in percent) as a function of the luminance, calculated from current-voltage-luminance characteristics ( IUL characteristics) assuming a lambertian radiation characteristic.
  • Electroluminescence spectra are determined at a luminance of 1000 cd / m 2 and from this the CIE 1931 x and y color coordinates are calculated.
  • the indication LH 000 in Table 2 indicates the voltage that is used for a
  • Luminance of 1000 cd / m 2 is needed.
  • EQE1000 refers to external quantum efficiency at an operating luminance of 1000 cd / m 2 .
  • Example V1 is a comparative example according to the prior art; examples E1-E11 show data of OLEDs with materials according to the invention.
  • the compounds 3a, 3b, 3c, 3e, 3g, 3i, 6a, 6b, 6e, 6f and 6g according to the invention are used as matrix materials for phosphorescent emitters in the OLEDs shown in Table 1 (devices E1 to E11).
  • the compounds according to the invention give very good values in terms of service life, efficiency and operating voltage
  • the compound 6e or 6a according to the invention gives a power efficiency which is more than 30% or 25% higher than with
  • V1 SpA1 HATCN SpMA1 SdT1 TER1 - ST1: LiQ

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne composé de formule (I), (II) ou (III). Ce composé peut être utilisé dans un dispositif électronique, de préférence dans un dispositif électronique organique.
EP13802887.3A 2013-01-03 2013-12-10 Matériaux pour dispositifs électroniques Withdrawn EP2941469A2 (fr)

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