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WO2016116518A1 - Molécules organiques notamment utilisées dans des composants optoélectroniques - Google Patents

Molécules organiques notamment utilisées dans des composants optoélectroniques Download PDF

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WO2016116518A1
WO2016116518A1 PCT/EP2016/051156 EP2016051156W WO2016116518A1 WO 2016116518 A1 WO2016116518 A1 WO 2016116518A1 EP 2016051156 W EP2016051156 W EP 2016051156W WO 2016116518 A1 WO2016116518 A1 WO 2016116518A1
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formula
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David Ambrosek
Michael Danz
Harald FLÜGGE
Jana Friedrichs
Tobias Grab
Andreas Jacob
Stefan Seifermann
Daniel Volz
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Cynora GmbH
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Cynora GmbH
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
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    • Y02E10/549—Organic PV cells

Definitions

  • the invention relates to purely organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic components.
  • OLED organic light-emitting diodes
  • OLEDs are usually realized in layer structures, which consist predominantly of organic materials.
  • layer structures consist predominantly of organic materials.
  • FIG. 1 The heart of such components is the emitter layer, in which usually emitting molecules are embedded in a matrix.
  • the energy contained in the excitons can be emitted by the corresponding emitters in the form of light, in this case speaking of electroluminescence.
  • An overview of the function of OLEDs can be found, for example, in H. Yersin, Top. Curr. Chem., 2004, 241, 1 and H. Yersin, "Highly Efficient OLEDs with Phosphorescent Materials”; Wiley-VCH, Weinheim, Germany, 2008.
  • a new generation of OLEDs is based on the utilization of delayed fluorescence (TADF: thermally activated delayed fluorescence or singlet harvesting).
  • TADF thermally activated delayed fluorescence or singlet harvesting
  • Cu (I) complexes can be used which, due to a small energy gap between the lowest triplet state ⁇ and the overlying singlet state Si (AE (Si-Ti)), can thermally recombine triplet exitones into a singlet state.
  • AE overlying singlet state Si
  • transition metal complexes purely organic molecules (without metal ion) can exploit this effect.
  • the invention relates in one aspect to purely organic molecules that can be used in optoelectronic devices.
  • Such organic molecules have a structure of the formula 1 or have a structure of the formula 1:
  • x 1, 2 or 3
  • y is 1, 2 or 3 with
  • the organic molecules have a structure of sub-formula 1 or have a structure of sub-formula 1:
  • Sub-formula 1 where: El is an element of Group 14 of the Periodic Table of the Elements, namely: Si, Ge, Sn or Pb;
  • R *** is independently at each occurrence a unit AF, a radical R * or has a structure of the formula 1a
  • e is 0 or 1;
  • b is 1, 2 or 3 or 4,
  • d 0, 1, 2, 3 or 4;
  • VP denotes the point of attachment to El or is R *, where always exactly one unit VP denotes a point of attachment and the remaining VPs are equal to R *;
  • the molecules according to the invention contain at least two units AF (AF1 and AF2) for which AF1 + AF2 applies and in the case where more than two chemical units are contained in one molecule, it holds that each further chemical entity AF is identical to AF1 or AF2 is;
  • AF are chemical entities comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system).
  • R *** each occurrence is independently a unit AF, a group R * or is selected from the group consisting of:
  • the unit AF is referred to as AF2, which in comparison to the respective other AF has a lower absolute value HOMO (and thus correspondingly a lower magnitude LUMO numerical value), from which follows (
  • separator S The part of the organic molecule according to formula 1 and sub-formula 1 which does not represent the chemical entities AF and which contains a Si atom, a Ge atom, a Sn atom or a Pb atom is also referred to as separator S.
  • the separator S prevents the units AF from being in conjugation with each other, at least one of the frontier orbitals (HOMO or LUMO) not being on the Si, Ge, Sn or Pb atom and, in particular, none of the frontier orbitals (HOMO or LUMO) lies on the Si, the Ge atom, the Sn or the Pb atom.
  • the presence of the separator S in the molecules according to the invention leads to a very small singlet-triplet distance, which allows emission by the TADF mechanism (Thermally Activated Delayed Fluorescence).
  • R 3 is independently selected for each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H Atoms may be replaced by F or CF 3 ; two or more substituents R 3 may also together form a mono- or polycyclic aliphatic ring system;
  • R 8 is independently selected in each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H atoms can be replaced by F or CF 3 ; two or more substituents R 8 may also together form a mono- or polycyclic aliphatic ring system;
  • An aryl group or heteroaryl group is understood to mean a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example naphthalene, phenanthrene, quinoline or carbazole.
  • a condensed (fused) aromatic or heteroaromatic polycycle consists in the context of the present application of two or more fused simple aromatic or heteroaromatic cycles.
  • An aryl or heteroaryl group which may be substituted in each case by the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic compounds is understood in particular to mean groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrenes, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; Pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, isoquinoline
  • 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 in particular selected from N, O and / or S.
  • 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 has several aryl or heteroaryl groups through a non-aromatic moiety (especially less than 10% of the various atoms), such as an sp3-hybridized C, Si, or N atom, an sp 2 -hybridized -, N or O atom or a sp-hybridized carbon atom, may be connected.
  • a non-aromatic moiety especially less than 10% of the various atoms
  • systems such as 9, 10-T-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc.
  • aromatic ring systems in the context of this invention, and systems in which two or more aryl groups are exemplified by a linear or cyclic alkyl, alkenyl or alkynyl groups or by a silyl group.
  • systems in which two or more aryl or heteroyrayl 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 biphenyl, terphenyl or diphenyltriazine.
  • aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case with radicals as defined above and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, naphthalene , Anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenyls, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydro-pyrene, cis- or trans- indenofluorene, truxene, isotruxene, spirotruxene, spiroiso
  • the energy values HOMO (AF1), HOMO (AF2), LUMO (AF1), LUMO (AF2) are calculated using the density functional theory (DFT), whereby the attachment positions of the ambifunctional units and the separators are saturated with a hydrogen atom according to their chemical valences.
  • DFT density functional theory
  • the limits given refer to orbital energies in eV calculated with the BP86 functional (Becke, A.D. Phys Rev. A1988, 38, 3098-3100, Perdew, J.P. Phys. Rev. B1986, 33, 8822-8827).
  • AF2 always has a lower HOMO value compared to AF1 (and correspondingly a lower LUMO number than AF1).
  • the organic molecules have a structure of the formula 2a to 2x or have a structure of the formulas 2a to 2z, wherein in each case the not designated as AF moiety represents the separator S.
  • G is independently CR * at each occurrence; J is independent of each occurrence CR * or the C-atom to which the unit AF is attached.
  • the chemical units AF2 have a structure of the formula 3a or have a structure of the formula 3a
  • the chemical units AF1 have a structure of the formula 3b or have a structure of the formula 3b.
  • n 0 or 1
  • n 0 or 1
  • o 0 or 1
  • X is selected from the group consisting of O, S, NR *, BR *, CR * 2 , and one
  • Y is independently O, S, NR ** or CR ** 2 at each occurrence, and two units Y are not simultaneously CR ** 2 or Y is equal to a CC single bond, and two units Y are not equal to one CC at a time Single bond;
  • X is equal to a CC single bond or is equal to CR ** 2 when M is equal to CR ** 2 ;
  • R ** is either a radical R * or the point of attachment of the AF to the separator S; two or more adjacent substituents R ** may also together form a mono- or polycyclic, aliphatic or aromatic ring system such as phenylene, naphthyl, anthracene and perylene, if the respective radicals R ** are R *.
  • R * is defined as in sub-formula 1.
  • p is 0 or 1;
  • q is 0 or 1
  • r is 0 or 1;
  • E is independently selected from the group consisting of each occurrence
  • Z is independently selected from the group consisting of each occurrence
  • T is selected from the group consisting of
  • R ** is either a radical R * or the point of attachment of the AF to the separator S; in this case, two or more adjacent substituents R ** can also form a mono- or polycyclic, aliphatic or aromatic ring system with one another, such as phenylene, naphthyl, anthracene and perylene, if the relevant radicals R ** are identical to R *.
  • R * is defined as in sub-formula 1.
  • the units AF2 are selected from the structures of
  • Alk is methyl, ethyl, propyl / so-propyl, butyl, ferf-butyl, pentyl, hexyl, 2-ethylhexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl;
  • EZG is independently selected from the group consisting of each occurrence
  • FG independently of each occurrence is CN, H, D, alkyl, phenyl, pyridyl or denotes the point of attachment to the separator;
  • Sub-formula 31 Sub-formula 3m Sub-formula 3n Sub-formula 3o and where:
  • Het is NR **, O, S or S0 2 ;
  • D is N or CR **
  • Q is N or CR **, with a maximum of three units Q equal to N at a time; and wherein two adjacent units Q are not equal to N at the same time;
  • the units AF2 of the formula 3a are selected from the structures listed in Table 1, and the units AF1 of the formula 3b are selected from the structures of Table 2.
  • Table 1 List of chemical entities AF2. Possible connecting points of the chemical unit AF1 to a Se arator s are indicated by lowercase letters.
  • Table 2 List of chemical units AF1. Possible connecting points of the chemical unit AF1 to a separator s are indicated by lowercase letters.
  • the separator S is selected from the structures of the formulas 3.1 to 3.42, wherein # denotes the point at which the AF are bound to the separator and the molecule contains at least two different chemical entities AF.
  • Formula 3.39 Formula 3.40
  • Formula 3.42 where for the formulas 3.1 to 3.42 the definitions from sub-formula 1 and from the formulas 2a to 2z apply;
  • # denotes the locations at which the units AF are bound to the separator.
  • the separator S functionally distinguishes the organic molecules from prior art molecules, as the type of separation of AFs (or donors and acceptors) shown here is not yet known.
  • AFs or donors and acceptors
  • Known organic emitters usually consist of directly linked chemical units. Separation of the conjugated aromatic systems has not taken place so far, especially in connection with the localization of HOMO and LUMO on separate parts of the molecule.
  • That part of the molecule which does not represent the chemical units AF and which contains an Si atom, a Ge atom, an Sn atom or a Pb atom acts as a separator (see also formula 3.1 to formula 3.42).
  • the separator S prevents the units AF from being in conjugation with each other, at least one of the frontier orbitals (HOMO or LUMO) not being on the Si, Ge, Sn or Pb atom and, in particular, none of the frontier orbitals (HOMO or LUMO) on the Si, the Ge atom, the Sn or the Pb atom (see compounds A, B, C and Figures 4-9).
  • the presence of the separator S in the molecules according to the invention leads to a very small singlet-triplet distance, which allows emission by the TADF mechanism (Thermally Activated Delayed Fluorescence).
  • separators do not significantly alter the position of the HOMO or LUMO of the AFs shown in Table 1 and Table 2. Not significant in the context of this invention is a change of not more than +/- 0.4 eV. The calculation of such energies is known and works according to the manner described above by DFT calculation.
  • spectroscopic selection rules symmetric molecules or by measuring the extinction coefficient (UV / VIS spectroscopy) or quantum chemical calculation of the oscillator strength, it can be predicted whether a quantum mechanical transition is allowed.
  • the goal is a decay time of ⁇ 50 ps.
  • a measure of the decay time is the AE (Si-Ti) distance. This is influenced by the overlap of HOMO and LUMO.
  • the size of the quantum mechanical overlap integral which can be calculated by the above-mentioned DFT method, can be controlled in a targeted manner by selecting the separator. If it comes to the complete separation of HOMO and LUMO this has a value of 0. The probability of an efficient emission of the organic molecule decreases drastically. At a value of 1 there is no longer delayed fluorescence (TADF) but spontaneous emission.
  • TADF delayed fluorescence
  • the separators S shown in particular fulfill two essential functional features (see FIG. 1 ).
  • the HOMO energy is lower than the HOMO energy of the donor chemical unit AF and
  • the LUMO energy is higher than the LUMO energy of the acceptor chemical entity AF.
  • Table 3 Selected examples of inventive molecules according to formula 1 and according to sub-formula 1 and / or according to the formulas 2a to 2z. The calculated values for the Singlet-triplet distance in the geometry of the SO ground state are indicated in brackets under the corresponding molecular structure.
  • organic molecules according to the invention which result from the combination of the above-defined pairs of chemical entities AF1 and AF2, the separator S and the determination of the linkage, are shown in Table 4.
  • Further organic molecules can be obtained by combining said molecular units, wherein at least two different AF and a maximum of four AF can be contained in one molecule.
  • the naming of the molecules takes place according to the scheme AF2-S-AF1, with reference being made to Table 1 for the naming of the chemical unit AF2 and to Table 2 for the designation of the chemical units AF1.
  • Table 4 Organic molecules according to the invention according to the scheme AF2-S-AF1.
  • One molecule contains at least two different AFs, with the other AFs being identical to the two different AFs.
  • Each S is a separator S selected from the formulas 3-1 to 3-42. In brackets the values for ⁇ , ALUMO and Gap are given.
  • 6- S-28 (1.191.31 1.34) 6- S-29 (0.961.031.62) 6- S- 43 (1.771.680.98) 6- S-46 (2.361.201.45)
  • 6- S-86 (0.831.371.28) 6- S-110 (1.171.331.33) 6- S-112 (1.060.821.83) 6- S-119 (1.120.941.72)
  • 6- S-133 (1.881.451.20) 6- S-150 (2.701.331.33) 6- S-151 (2.61 1.581.07) 6- S-153 (2.631.431.23)
  • 6- S-177 (1.71 1.11 1.55) 6- S-192 (2.051.441.22) 6- S-198 (1.590.821.83) 6- S-217 (0.980.81 1.84) -S- -218 (0.950.991.67) 6- -S- -231 (2.101.551.10) 6- -S- 237 (1.311.351.30) 6- -S- 244 (1.370.971.69) -S 6- S- -430 (0.831.371.28) 6- S -440 (1.501.181.47) 6- S-441 (1.431.111.55) - -S- -27 (1.121.061.62) 7- -S- -28 (1.191.321.35) 7- -S- -29 (0.951.051.63) 7- -S- -43 (1.761.690.98) - -S- -46 (2.361.
  • 21 - s - 28 (1.071.351.47)
  • 21 - s - 29 (0.831.071.74)
  • 21 - s - 36 (1.231.860.95)
  • 64 - s - 28 (0.86 1.29 1.68)
  • 64- S- 36 (1.02 1.80 1.16)
  • 64 s - 43 (1.44 1.65 1.31)
  • 64 s - 46 (2.03 1.17 1.79)
  • 64 - s - 110 (0.83 1.30 1.66)
  • 64- S- 133 (1.54 1.43 1.53)
  • 64 s - 150 (2.36 1.30 1.66)
  • 64 s - 151 (2.27 1.56 1.40)
  • 71 - s - 27 (0.87 1.03 1.87)
  • 71-S- 28 (0.94 1.30 1.60)
  • 71 s - 36 (1.10 1.81 1.09)
  • 71 s - 43 (.51 1.67 1.23)
  • 71 - s - 46 (2.11 1.19 1.71)
  • 71- S- 110 (0.91 1.32 1.59)
  • 71 s - 112 (0.80 0.81 2.09)
  • 71 s - 119 (0.86 0.93 1.97)
  • 222 - s - 133 (1.011.062.06)
  • 222 - s - 150 (1.830.932.19)
  • 222 - s - 151 (1.741.191.93)
  • 222 - s - 152 (2.391.491.63)
  • 242 - s - 119 (0.831.632.01) 242 - s - 133 (1.582.141.50) 242 - s - 150 (2.402.011.62) 242 - s - 151 (2.312.271.37)
  • 242 - s - 152 (2,952,571.07) 242 - s - 153 (2.332.121.52) 242 - s - 154 (1.871.242.39) 242 - s - 166 (1.591.072.57)
  • 242 - s - 245 (0.991.432.21) 242 - s - 246 (1.332.001.64) 242 - s - 440 (1.211.871.77) 242 - s - 441 (1.141.801.84)
  • 360 - s - 133 (1.43 1.27 1.65)
  • 360 - s - 150 (2.25 1.14 1.78)
  • 360 - s - 151 (2.16 1.40 1.52)
  • 360 - s - 152 (2.80 1.70 1.22)
  • 360 - s - 153 (2.18 1.24 1.68) 360 - s - 177 (1.26 0.92 2.00) 360 - s - 192 (1.60 1.25 1.66) 360 - s - 231 (1.65 1.37 1.55)
  • 360 - s - 237 (0.86 1.17 1.75)
  • 360 - s - 246 (1.17 1.12 1.79)
  • 360 - s - 440 (1.06 1.00 1.92)
  • 360 - s - 441 (0.99 0.92 1.99)
  • 385 - s - 482 (0.87 1.89 1.37) 385 - s - 483 (0.91 1.97 1.30) 389 - s - 27 (.51 2.00 1.23) 389 - s - 28 (.58 2.27 0.96)
  • 406 - s - 358 (1.06 1.87 1.80) 406 - s - 379 (0.94 1.64 2.04) 406 - s - 391 (0.95 1.62 2.05) 406 - s - 430 (0.89 2.46 1.22) 406- S-440 (1.56 2.26 1.41) 406- S-441 (1.49 2.19 1.49) 410- S-27 (1.26 2.29 1.49) 410- S-28 (1.32 2.56 1.22)
  • further radicals R are added to the chemically substitutable positions of the organic molecules thus obtained in order to increase the solubility of the emitters and / or to allow the polymerizability without significantly changing the electronic properties of the molecule, so that even when using R an emitter is present, wherein
  • R 3 is independently selected for each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H Atoms may be replaced by F or CF 3 ; two or more substituents R 3 may also together form a mono- or polycyclic aliphatic ring system;
  • Polymerizable radicals are those radicals which carry polymerizable functional units which can be homopolymerized with themselves or copolymerized with other monomers.
  • the molecules of the invention can be obtained as a polymer having the following repeating units of the formulas 4 and 5, which can be used as polymers in the light-emitting layer of the optoelectronic component.
  • L1 and L2 represent the same or different linker groups having 0 to 20, more preferably 1 to 15, or 2 to 10 carbon atoms, and wherein the wavy line indicates the position via which the linker group bonds to the organic molecule of the Formula 1 or sub-formula 1 is connected.
  • the linker group L1 and / or L2 has a form -X-L3-, where X is O or S and L3 is a linker group selected from the group consisting of a substituted and unsubstituted alkylene group (linear, branched or cyclic) and a substituted and unsubstituted arylene group, in particular a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group, whereby combinations are possible.
  • the polymerizable functional units are attached to the organic molecule of the formula 1 or the sub-formula 1 via a linker group of the formulas 12 to 17 having a hydroxyl moiety and those thereof resulting compounds are homopolymerized with themselves or copolymerized with other suitable monomers.
  • Formula 12 Formula 13 Formula 14 Formula 15 Formula 16 Formula 17 Polymers which have a unit according to formula 4 or formula 5 can either exclusively comprise repeat units having a structure of general formula 4 or 5 or repeat units having a different structure. Examples of repeat units having other structures include moieties resulting from corresponding monomers typically used or used in copolymerizations. Examples of such repeat units resulting from monomers are repeat units having unsaturated moieties such as ethylene or styrene.
  • AE Si-T-i
  • Si lowest excited singlet
  • T-i triplet
  • a further embodiment of the invention relates to the use of a separator S in the form of a neutral chemical entity for providing an organic molecule according to the invention, wherein at least one first chemical entity AF1 comprising a conjugated system, in particular at least six conjugated ⁇ -electrons in conjugation and at least one second chemical unit AF2, comprising a conjugated system, in particular at least six conjugated ⁇ -electrons, covalently linked via the separator S such that the separator S is a direct electronic interaction via conjugated bonds between the conjugate system of the first chemical unit AF1 and the Conjugated system of the second chemical unit AF2 prevented.
  • first chemical entity AF1 comprising a conjugated system, in particular at least six conjugated ⁇ -electrons in conjugation
  • at least one second chemical unit AF2 comprising a conjugated system, in particular at least six conjugated ⁇ -electrons
  • the invention relates in one aspect to the use of an organic molecule according to the invention as a luminescent emitter and / or as a host material and / or as an electron transport material and / or as a hole injection material and / or as a hole blocking material in an optoelectronic component, which is produced in particular by a vacuum evaporation method or from solution , wherein the optoelectronic component is in particular selected from the group consisting of:
  • OLEDs Organic light emitting diodes
  • the proportion of the organic molecule according to the invention on the luminescent emitter and / or host material and / or electron transport material and / or hole injection material and / or hole blocking material in one embodiment is 1% to 99% (wt%), in particular the proportion of the emitter in optical light-emitting components especially in OLEDs, between 5% and 80%.
  • the invention relates in a further aspect to optoelectronic components comprising an organic molecule according to the invention, wherein the optoelectronic component is in particular formed as a component selected from the group consisting of organic light emitting component (OLED), light emitting electrochemical cell, OLED sensor, in particular in non-hermetically shielded gas and vapor sensors, organic diode, organic solar cell, organic transistor, organic light emitting diode, organic field effect transistor, organic laser and downconversion element.
  • OLED organic light emitting component
  • OLED light emitting electrochemical cell
  • OLED sensor in particular in non-hermetically shielded gas and vapor sensors
  • organic diode organic solar cell
  • organic transistor organic light emitting diode
  • organic field effect transistor organic laser and downconversion element
  • One embodiment relates to the optoelectronic component according to the invention comprising a substrate, an anode and a cathode, wherein the anode and the cathode are applied to the substrate, and at least one light-emitting layer which is arranged between anode and cathode and which contains an organic molecule according to the invention.
  • the organic molecule is used as the emission material in an emission layer, wherein it can be used in combination with at least one host material or, in particular, as a pure layer.
  • the proportion of the organic molecule as emission material in an emission layer in optical light-emitting components, in particular in OLEDs is between 5% and 80% (% by weight).
  • the light-emitting layer having an organic molecule according to the invention is applied to a substrate.
  • the invention relates to an optoelectronic component in which the light-emitting layer comprises only an organic molecule according to the invention in 100% concentration, wherein the anode and the cathode is applied to the substrate, and the light-emitting layer between the anode and cathode is applied.
  • the optoelectronic component has at least one host material, in particular the excited singlet state (Si) and / or the excited triplet state (Ti) of the at least one host material being higher than the excited singlet state (Si) and / or the excited triplet state ( ⁇ ) of the organic molecule, and wherein the anode and the cathode are deposited on the substrate, and the light emitting layer is disposed between the anode and the cathode.
  • the optoelectronic component comprises a substrate, an anode, a cathode and at least one hole injecting and an electron injecting layer and at least one light emitting layer, wherein the at least one light emitting layer comprises an organic molecule according to the invention and a host material whose triplet ( ⁇ ) and singlet (Si) energy levels are higher than the triplet (Ti) and singlet (Si) energy levels of the organic molecule, and where the anode and cathode are deposited on the substrate, and the hole and electron injecting Layer between the anode and cathode is applied and the light-emitting layer between holes and electron injecting layer is applied.
  • the at least one light emitting layer comprises an organic molecule according to the invention and a host material whose triplet ( ⁇ ) and singlet (Si) energy levels are higher than the triplet (Ti) and singlet (Si) energy levels of the organic molecule, and where the anode and cathode are deposited on the substrate, and the
  • the optoelectronic component comprises a substrate, an anode, a cathode and at least one hole-injecting and an electron-injecting layer, and at least one hole-transporting and one electron-transporting layer, and at least one light-emitting layer, wherein the at least one light-emitting layer
  • the organic molecule and a host material whose triplet (Ti) and singlet (Si) energy levels are higher in energy than the triplet (Ti) and singlet (Si) energy levels of the organic molecule, and wherein the anode and the cathode the substrate is deposited, and the hole and electron injecting layer is disposed between the anode and the cathode, and the hole and electron transporting layer is interposed between the hole and electron injecting layers, and the light emitting layer is interposed between hole and electron tran athletic layer is applied.
  • the optoelectronic component has at least one host material made of a material according to formula
  • the light-emitting layer contains fluorescent or phosphorescent materials, which may be selected from formula 1 or sub-formula 1.
  • an organic molecule according to formula 1 or sub-formula 1 and a functional material for example in the form of a further emitter material, a host material, or another organic molecule which forms an exciplex with the molecule according to formula 1 or sub-formula 1, an exciplex.
  • Functional materials include, for example, host materials such as MCP, electron transport materials such as TPBI, and hole transport materials such as N PD or MTDATA.
  • Exciplexes are adducts of electronically excited and electronically grounded molecules capable of emitting light.
  • the emission is characterized by thermally activated delayed fluorescence (TADF).
  • TADF thermally activated delayed fluorescence
  • organic molecules according to formula 1 or sub-formula 1 are used as charge transport layer.
  • the invention in one aspect relates to a light-emitting material comprising an organic molecule and a host material according to the invention, wherein the triplet ( ⁇ ) and singlet (Si) energy levels of the host material are higher in energy than the triplet (Ti) and singlet (Si) Energy levels of the organic molecule, and wherein the organic molecule emits fluorescence or thermally activated delayed fluorescence (TADF), and an AE (Si-Ti) value between the lowest excited singlet (Si) and the underlying triplet (Ti) - Condition of less than 0.2 eV, in particular less than 0, 1 eV has.
  • TADF thermally activated delayed fluorescence
  • One aspect of the invention relates to a method for producing an optoelectronic component comprising an organic molecule according to the invention.
  • the method comprises the step of processing the organic molecule by a vacuum evaporation process or from a solution.
  • the method comprises applying the organic molecule to a carrier, the application being carried out in particular wet-chemically, by means of colloidal suspension or by means of sublimation.
  • One aspect of the invention relates to a method for changing the emission and / or absorption properties of an electronic component, wherein an organic molecule according to the invention is introduced into a matrix material for conducting electrons or holes in an optoelectronic component.
  • the invention additionally relates to the use of a molecule according to the invention for converting UV radiation or blue light into visible light, in particular into green, yellow or red light (down conversion), in particular in an optoelectronic component of the type described here ,
  • the invention relates to an application in which at least one material according to formula 1 or sub-formula 1 is excited to glow by external energetic excitation.
  • the external stimulation can be electronic or optical or radioactive.
  • BP86 functional (Becke, AD Phys Rev. A1988, 38, 3098-3100, Perdew, JP Phys Rev. B1986, 33, 8822-8827) was used, with the resolution-of-identity Approach (RI) (Sierka, M., Hogekamp, A., Ahlrichs, RJ Chem. Phys., 2003, 18, 9136-9148; Becke, AD, J. Chem. Phys., 98 (1993) 5648-5652; Lee, C; Yang, W; Parr, RG Phys. Rev. B 37 (1988) 785-789).
  • RI resolution-of-identity Approach
  • Excitation energies were determined in the BP86-optimized structure by the time-dependent DFT method (TD-DFT) using the B3LYP functional (Becke, AD, J. Chem. Phys. 98 (1993) 5648-5652, Lee, C; Yang, W; Parr, RG Phys Rev. B 37 (1988) 785-789; Vosko, SH; Wilk, L; Nusair, M. Can. J. Phys. 58 (1980) 1200-121 1; Stephens, PJ Devlin, FJ; Chabalowski, CF; Frisch, MJJ Phys. Chem 98 (1994) 1 1623-1 1627).
  • def2-SV (P) base sets Weigend, F., Ahlrichs, R. Phys. Chem. Chem. Phys., 2005, 7, 3297-3305, Rappoport, D .; Furche, FJ Chem. Phys. 2010, 133, 134105 / 1-134105 / 1
  • All DFT calculations were performed with the Turbomole program package (version 6.5) (TURBOMOLE V6.4 2012, University of Düsseldorf and Anlagens scholar Düsseldorf GmbH, 1989-2007, TURBOMOLE GmbH, 2007, http://www.turbomole.com).
  • AAV1 Arylation of Ph 3 SiCl or Ph 3 GeCl
  • Diethyl ether 7 mL per mmol of aryl halide.
  • the solution was cooled to -78 ° C and n-butyllithium (2.5 M in hexane, 1.1 equiv.) was added dropwise with stirring.
  • a solution of chlorotriphenylsilane or chlorotriphenylgerman 1.2 equiv.
  • AAV2 Arylation of Ph 2 SiCl 2 or Ph 2 GeCl 2
  • AAV3 Arylation of SiCI 4 and GeCl 4 to SiAr 4 and GeAr 4, respectively
  • AAV4 Synthesis of bis (carbazolyl) SiCl 2 derivatives (protocol slightly modified according to: J. Organomet. Chem. 1988, 350, 217-226.)
  • AAV8 Introduction of cyano groups
  • the corresponding aryl bromide or iodide and CuCN in the desired stoichiometric ratio (1, 25 mmol CuCN per mmol to be substituted halide atom) are suspended in absolute DMF.
  • the mixture is heated to 150 ° C until complete reaction.
  • the copper salts contained are precipitated by addition of dichloromethane and then filtered off. The filtrate is freed from the solvent under reduced pressure and the residue is purified by recrystallization or by MPLC.
  • the sample concentration corresponded to 10mg / ml, given in toluene or chlorobenzene.
  • the concentration of the optically neutral host polymer PMMA corresponded to 10 mg / mL, prepared in toluene or chlorobenzene.
  • the film preparation was carried out from a mixture of the PMMA solution and the sample solution in the volumetric ratio 90:10.
  • Steady-state emission spectroscopy was performed with a Horiba Scientific FluoroMax-4 fluorescence spectrometer equipped with a 150 W xenon-arc lamp, excitation and emission monochromators and a Hamamatsu R928 photomultiplier tube, and a TCSPC option. Emission and excitation spectra were corrected by standard correction curves.
  • Emission decay times were also measured on this system using the TCSPC method with the FM-2013 accessory and a TCSPC hub from Horiba Yvon Jobin.
  • Excitation sources NanoLED 370 (wavelength: 371 nm, pulse duration: 1 .1 ns), NanoLED 290 (wavelength: 294 nm, pulse duration: ⁇ 1 ns), SpectraLED 310 (wavelength: 314 nm), SpectraLED 355 (wavelength: 355 nm).
  • the photoluminescence quantum yield (PLQY) was measured by means of an Absolute PL Quantum Yield Measurement C9920-03G system from Hamamatsu Photonics. This consists of a 150 W xenon gas discharge lamp, automatically adjustable Czerny-Turner monochromators (250-950 nm) and an Ulbricht sphere with highly reflecting Spektralon coating (a Teflon derivative), which has a fiber optic cable with a PMA-12 multichannel detector BT (back thinned) CCD chip with 1024 x 122 pixels (size 24 x 24 pm) is connected. The evaluation of the quantum efficiency and the CIE coordinates took place with the help of the software U6039-05 version 3.6.0
  • PLQY was determined for polymer films, solutions and powder samples according to the following protocol:
  • the reference material is anthracenes in ethanol of known concentration.
  • OLED organic light emitting diode

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Abstract

La présente invention concerne des molécules organiques notamment utilisées dans des composants optoélectroniques tels que des OLED. Selon l'invention, ladite molécule organique présente une structure de sous-formule 1.
PCT/EP2016/051156 2015-01-20 2016-01-20 Molécules organiques notamment utilisées dans des composants optoélectroniques Ceased WO2016116518A1 (fr)

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