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WO2016116504A1 - Molécules organiques à utiliser dans des composants optoélectroniques - Google Patents

Molécules organiques à utiliser dans des composants optoélectroniques Download PDF

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WO2016116504A1
WO2016116504A1 PCT/EP2016/051138 EP2016051138W WO2016116504A1 WO 2016116504 A1 WO2016116504 A1 WO 2016116504A1 EP 2016051138 W EP2016051138 W EP 2016051138W WO 2016116504 A1 WO2016116504 A1 WO 2016116504A1
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atoms
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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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Definitions

  • the invention relates to purely organic molecules, in particular with dibenzannel faced, nitrogen-containing 6- and 7-rings and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic devices.
  • 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 can exploit this effect.
  • Some such TADF materials have already been used in first optoelectronic devices.
  • the TADF materials often do not have sufficient long-term stability, sufficient thermal or sufficient chemical stability to water and oxygen in the optoelectronic components.
  • not all important emission colors are available.
  • some TADF materials are not vaporizable and therefore not suitable for use in commercial optoelectronic devices.
  • some TADF materials do not have adequate energy layers to the other materials used in the optoelectronic device (e.g., HOMO energies of TADF emitters greater than or equal to -5.9 eV). It is not possible to achieve sufficiently high efficiencies of the optoelectronic components with high current densities or high luminances with all TADF materials.
  • the syntheses of some TADF materials are expensive.
  • the invention relates in one aspect to the provision of organic molecules having a structure of formula 1 or having a structure of formula 1:
  • formula 1 AF1 is a first chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system);
  • AF2 is a second chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system);
  • Such organic molecules have an AF1 of the formula Ia or have an AF1 with a structure of the formula 1 a:
  • Y is O, S, NR *, PR *, AsR *, GeR * 2 , BR *, SiR * 2 , 1, 1 'cyclohexyl, methylene, S0 2 , 1, 2-phenylene, 1, 1-dicyanoethylene
  • C C (CN) 2 , CMe 2 , 2,2'-diphenyl ether fragment, 2,2'-diphenyl thioether fragment, 2,2'-benzophenone fragment, 2,2'-diphenylmethane fragment, 2, 2'-Diphenyl-dicyanomethan fragment, wherein fragment means that the attachment of these units takes place via their 2,2'-position to a quaternary carbon atom, for which Y stands in this case.
  • Y is selected from the group consisting of O, S, NR *, PR *, AsR *, GeR * 2 , BR *, SiR * 2 , 1, 1 'cyclohexyl, methylene, 1, 2-phenylene, 1, 1-dicyanoethylene, CMe 2, 2,2'-diphenyl ether fragment, 2,2'-diphenyl thioether fragment, 2,2'-benzophenone fragment, 2,2'-diphenylmethane fragment and 2,2 'diphenyl-dicyanomethane fragment.
  • Y is selected from the group consisting of O, S, NR *, PR *, AsR *, GeR * 2 , BR *, SiR * 2 , 1, 1 'cyclohexyl, methylene, 1, 2-phenylene, 1, 1-dicyanoethylene and CMe 2.
  • Y is selected from the group consisting of SO 2 , AsR *, GeR * 2 , BR *, 1,1-dicyanoethylene, 2,2'-benzophenone fragment and 2,2'-diphenyldicyanomethane fragment.
  • Y is selected from the group consisting of AsR *, GeR * 2 , BR *, 1,1-dicyanoethylene, 2,2'-benzophenone fragment, and 2,2'-diphenyl-dicyanomethane fragment.
  • R ** is either a radical R * or denotes the attachment position to the chemical moiety AF2; two or more substituents R ** may also together form a mono- or polycyclic aliphatic ring system; wherein the attachment to the chemical entity AF2 can also take place via an atom of the radical R ** or R *; and wherein in the molecule exactly one chemical unit AF2 is present.
  • 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 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 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 in particular N, O, and S. If other definitions are given at points in the description, for example with regard to the number of aromatic ring atoms or the heteroatoms contained therein, these other definitions apply.
  • 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 several aryl or heteroaryl groups by a non-aromatic moiety (in particular less than 10% of the various atoms), such as, for example, a sp3-hybridized C, Si or N atom, an sp 2 -hybridized C, N or O atom or a sp-hybridized carbon atom, may be connected.
  • systems such as 9, T-diaryl fluorene, triarylamine, diaryl ethers, stilbene, etc.
  • 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 by a silyl group are connected.
  • 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 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
  • connection of the chemical units AF1 and AF2 to each other takes place in one embodiment when selecting the AF1 from Table 1 and selecting the AF2 from Table 2 in each case over the lower case letters designated positions of each AF (Table 1 and Table 2).
  • AF2 always has a lower HOMO numerical value compared to AF1 (and correspondingly a LUMO numerical value lower in magnitude) than AF2 (
  • the organic molecules are characterized in that
  • 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 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).
  • the chemical entities AF1 and AF2 are linked to one another such that the electronic communication between them is interrupted. This disruption is characterized by localization of the HOMO and LUMO frontier orbits on separate parts of the molecule, allowing for a charge-transfer transition.
  • the electronic communication between the two chemical entities AF1 and AF2 via conjugated bonds is interrupted when the frontier orbitals HOMO and LUMO are located on separate parts of the molecule, allowing for a charge-transfer transition.
  • the localization of the frontier orbitals HOMO or LUMO is determined using the density functional theory (DFT) with the BP86 functional (Becke, AD Phys.Rev.A1988, 38, 3098-3100, Perdew, JP Phys. Rev. B1986, 33, 8822-8827 ):
  • the single electron wave function calculates the single electron density by squaring and integrates it over the space occupied by the part of the molecule.
  • This space can be determined from the atomic coordinates and van der Waals radii of the atoms. The resulting number corresponds to the proportion of orbital on the moiety. A majority separation of the frontier orbitals corresponds to an overlap parameter O in the range 0.1-20% to allow a batch transfer transition.
  • the organic molecules have a structure of the formula 2a-2c or have a structure of the formula 2a-2c, wherein
  • Formula 2a Formula 2b Formula 2c and R *, Y and AF2 are as defined above.
  • organic molecules AF1-AF2 are used, AF1 being selected from the following Table 1:
  • Table 1 List of the first chemical units AF1
  • organic molecules AF1-AF2 are used, with AF1 being selected from the following Table 1 a:
  • Table 1a List of the first chemical units AF1
  • organic molecules AF1-AF2 are used with AF2 selected from Table 2.
  • Table 2 List of the second chemical units AF2.
  • n 0 or 1
  • o 0 or 1
  • p is 0 or 1;
  • VG1 bridging group, is selected from the group consisting of
  • VG2 bridging group at each occurrence is independently selected from the group consisting of CR ** 2 , NR **, O, S and a CC single bond, where two units VG2 are not simultaneously equal to one CC single bond;
  • R ** is independently a residue R * at each occurrence and / or marks a point of attachment to the unit AF1, where exactly one R ** is a point of attachment to a unit AF1.
  • the unit AF2 has a structure of the formula 4 or has a structure of the formula 4
  • the unit AF2 of the organic molecule has a structure of the formula 4A1-4A7 or has a structure of the formula 4A1-4A7
  • X is C (R **) 2 , NR **, oxygen, sulfur; and, moreover, the definitions given for formula 3 apply.
  • the organic molecules have a structure of the formula 5a or have a structure of the formula 5a
  • X is CR * 2 , NR *, oxygen, sulfur, a direct bond, with a maximum of two wildcards X being simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecules have a structure of the formula 6a or have a structure of the formula 6a
  • X is CR * 2 , NR *, oxygen, sulfur, a direct bond, with a maximum of two wildcards X being simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecules have a structure of the formula 7a or have a structure of the formula 7a
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • Table 3 Examples of organic molecules according to the invention (AF1 -S-AF2). The naming of the molecules on the left contains the component from AF1 from Table 1, which is bound directly to a second chemical group AF2 (from Table 2), which is named on the right.
  • the permissibility of a quantum mechanical transition is, as is well known, accessible either by theoretically derivable spectroscopic selection rules (symmetric molecules) or by measuring the extinction coefficient (UV / VIS spectroscopy) or quantum chemical calculation of the oscillator strength, with permission characterized by a large oscillator strength.
  • the greater the oscillator strength the faster the associated process.
  • saturation effects quickly occur at high current intensities, which adversely affects the component lifetime and prevents the achievement of high brightness levels.
  • the quantum mechanical overlap integral increases so that the decay time drops to values below 50 ps. This is achieved by the AF1 according to the invention.
  • Organic molecules of the present invention are shown in Table 4 which result from combining the above-defined pairs of chemical entities AF1 and AF2 and establishing the linkage.
  • Other organic molecules can be obtained by combining the mentioned molecular units.
  • the naming of the molecules is carried out according to the scheme AF-S-AF, with respect to the naming of the chemical units AF1 on Table 1 and with respect to the naming of the chemical unit AF2 on Table 2, since the numbers used in Tables 1 and 2 also in Table 4. For the sake of clarity, the two numbers are separated by the letter S.
  • Table 4 Inventive organic molecules according to the scheme AF-S-AF. In brackets the values for AHOMO, ALUMO and Gap are given.
  • 53 - S - 1 15 (1.31 1.57 1.58)
  • 53 - S - 1 18 (0.92 0.99 2.16)
  • 53 - S - 1 19 (0.89 1.21 1.95)
  • 53 - S - 132 (0.86 0.92 2.24)
  • 53 - S-449 (0.96 1.53 1.62)
  • 53 - S-451 (1.30 2.14 1.01)
  • 53 - S-452 (1.35 1.80 1.36)
  • 53 - S-460 (1.08 1.88 1.28)
  • 71 - S - 20 (0.96 0.86 2.04)
  • 71 - S - 27 (0.87 1.03 1.87)
  • 71 - S - 28 (0.94 1.30 1.60)
  • 71 - S - 36 (.10 1.81 1.09)
  • 71 - S- 43 (1.51 1.67 1.23)
  • 71 - S- 46 (2.11 1.19 1.71)
  • 71 - S- 61 (0.85 1.01 1.90)
  • 71 - S- 65 (0.86 0.80 2.10)
  • 71 - S- 144 (0.95 1.35 1.55)
  • 71 - S - 150 (2.44 1.31 1.59)
  • 71 - S - 151 (2.35 1.57 1.33)
  • 71 - S - 152 (2.99 1.87 1.03)
  • 77 - S- 29 (1.15 1.23 1.42)
  • 77 - S- 40 (0.98 1.23 1.42)
  • 77 - S- 46 (2.56 1.40 1.26)
  • 77 - S- 61 (.30 1.22 1.44)
  • 77- S- 62 (.18 1.42 1.24)
  • 77- S- 65 (1.31 1.01 1.64)
  • 77- S- 68 (.02 0.97 1.68)
  • 77- S- 79 (.30 1.39 1.27)
  • 77 - S- 80 (.25 1.35 1.31) 77 - S- 81 (1.33 1.47 1.19) 77 - S- 82 (.06 1.66 1.00) 77 - S- 85 (.81 1.20 1.46)
  • 77 - S-233 (1.68 1.17 1.48)
  • 77 - S-234 (1.50 1.26 1.40)
  • 77 - S-237 (1.51 1.55 1.10)
  • 77 - S-238 (0.81 1.41 1.24)
  • 77 - S-462 (0.91 1.58 1.07) 77 - S-467 (0.91 0.98 1.68) 77 - S-468 (1.1 1 1.28 1.37) 77 - S-469 (1.20 1.71 0.95)
  • 337- S- 56 (1.21 1.24 2.07) 337- S- 61 (.19 1.76 1.55) 337- S- 62 (.07 1.96 1.35) 337- S- 65 (.20 1.55 1.76)
  • 337- S-454 (0.98 1.14 2.17) 337- S-455 (0.97 1.41 1.90) 337- S-457 (1.12 1.91 1.39) 337- S-459 (0.90 2.15 1.16) 337- S- 460 (1.39 2.35 0.96) 337- S-461 (1.1 1 2.11 1.20) 337- S-462 (0.80 2.12 1.19) 337- S-468 (1.00 1.82 1.49)
  • 354- S-205 (0.92 1.26 1.96)
  • 354- S-206 (0.91 2.18 1.05)
  • 354- S-207 (1.43 2.12 1.10)
  • 354- S-213 (1.36 1.16 2.07)
  • 354- S-231 (1.91 1.93 1.29)
  • 354- S-233 (1.29 1.36 1.87)
  • 354- S-234 (1.1 1 1.44 1.79)
  • 354- S-237 (1.12 1.73 1.49)
  • 354- S-286 (0.95 1.02 2.20) 354- S-289 (1.00 0.81 2.41) 354- S-290 (1.03 1.44 1.79) 354- S-291 (2.17 1.84 1.38)
  • 354- S-342 (2.91 1.86 1.36)
  • 354- S-358 (0.81 1.17 2.05)
  • 354- S- 367 (1.44 1.81 1.42)
  • 354- S-371 (2.60 1.95 1.27)
  • further residues R are added to the chemically substitutable positions of the organic molecules so 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 is an emitter, where
  • R 3 in each occurrence is identical or different H, deuterium, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which one or more H atoms replaced by F or CF 3 could be; 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 8 and 9, 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, especially 1 to 15, or 2 to 10 carbon atoms, and wherein the wavy line indicates the position by which the linker group bonds to the organic molecule of the 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.
  • R 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 ; It can have two or more Substituents R can also form a mono- or polycyclic aliphatic ring system with one another, furthermore R can be: a linear alkoxy or thioalkoxy group with 1 to 40 C atoms or a linear alkenyl or alkinyl group with 2 to 40 C atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms.
  • the polymerisable functional units via a linker group of the formulas 16 to 21, which have a hydroxyl moiety are attached to an organic molecule of the formula 1 and the resulting compounds with themselves homopolymerized or copolymerized with other suitable monomers.
  • Polymers having a unit according to formula 8 or formula 9 can either exclusively comprise repeat units having a structure of general formula 8 or 9, or repeat units having a different structure.
  • repeat units having other structures include moieties resulting from corresponding monomers typically used or used in copolymerizations.
  • Examples of such repeating units, which consist of Monomers are repeating units having unsaturated moieties such as ethylene or styrene.
  • AE Si-T "i) value between the lowest excited singlet (Si) and the underlying triplet (T-i) state of less than 0.2 eV, in particular less than 0.1 eV, and / or
  • 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 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 diode (OLED), light-emitting electrochemical cell, OLED sensor, in particular in non-hermetically externally shielded gas and vapor sensors, organic diode, organic solar cell, organic transistor, organic field effect transistor, organic laser and down-conversion Element.
  • OLED organic light-emitting diode
  • OLED sensor light-emitting electrochemical cell
  • OLED sensor in particular in non-hermetically externally shielded gas and vapor sensors
  • organic diode organic solar cell
  • organic transistor organic field effect transistor
  • organic laser and down-conversion Element organic laser and down-conversion 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 (Ti) 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 in energy than the triplet ( ⁇ ) 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 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 applied, and the hole and electron injecting layer is applied between anode and cathode, and the hole and electron transporting layer is applied between hole and electron injecting layer, and the light emitting layer between holes and electronentr is applied ansportierende layer.
  • the optoelectronic component has at least one host material made from a material according to formula 1.
  • the light-emitting layer contains fluorescent or phosphorescent materials which have a structure of formula 1.
  • the optoelectronic component form an organic molecule according to formula 1 and a functional material, for example in the form of another emitter material, a host material, or another organic molecule which is used to form an exciplex with the molecule of formula 1 is capable of an exciplex.
  • Functional materials include, for example, host materials such as MCP, electron transport materials such as TPBI and hole transport materials such as NPD 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 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 than the triplet (Ti) and singlet (Si) energies.
  • 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 processing the organic molecule by a vacuum evaporation method 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 with a structure according to formula 1 is excited to emit by external energetic excitation.
  • the external stimulation can be electronic or optical or radioactive.
  • the optoelectronic component form an organic molecule according to formula 1 and a functional material, for example in the form of another emitter material, a host material, or another organic molecule which is used to form an exciplex with the molecule of formula 1 is capable of an exciplex.
  • Functional materials include host materials such as MCP, electron transport materials such as TPBI and hole transport materials such as NPD or MTDATA.
  • Exciplexes are adducts of electronically excited and electronically grounded molecules capable of emitting light.
  • 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 using 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, since 2007, http://www.turbomole.com) ,

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Abstract

L'invention concerne des molécules organiques, à utiliser en particulier dans des composants optoélectroniques, tels que des OLED. Selon l'invention, ladite molécule organique présente une structure de formule 1. Dans la formule 1, AF1 désigne une première unité chimique comprenant un système conjugué, AF2 désigne une seconde unité chimique comprenant un système conjugué, AF1 étant différent de AF2, et AF1 comportant une structure de formule 1a ou étant constitué d'une structure de formule 1a.
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CN106467531A (zh) * 2016-08-19 2017-03-01 江苏三月光电科技有限公司 一种以含氮五元杂环为核心的化合物及其应用
CN106467531B (zh) * 2016-08-19 2019-04-19 江苏三月光电科技有限公司 一种以含氮五元杂环为核心的化合物及其应用
CN106831745B (zh) * 2016-12-30 2020-01-14 上海天马有机发光显示技术有限公司 一种有机电致发光材料以及有机光电装置
CN106831745A (zh) * 2016-12-30 2017-06-13 上海天马有机发光显示技术有限公司 一种有机电致发光材料以及有机光电装置
US20170256718A1 (en) * 2016-12-30 2017-09-07 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent material and organic optoelectronic device
US10538700B2 (en) 2016-12-30 2020-01-21 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent material and organic optoelectronic device
US10535824B2 (en) 2016-12-30 2020-01-14 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent material and organic optoelectronic device
US10385059B2 (en) 2016-12-30 2019-08-20 Shanghai Tianma AM-OLED Co., Ltd. Organic electroluminescent material and organic optoelectronic device
US10510972B2 (en) 2017-03-09 2019-12-17 Shanghai Tianma AM-OLED Co., Ltd. OLED display panel and a display device comprising the same
WO2019053067A1 (fr) * 2017-09-13 2019-03-21 Cynora Gmbh Molécules organiques, destinées en particulier à une utilisation dans des dispositifs optoélectroniques
US11563187B2 (en) 2017-11-15 2023-01-24 Samsung Display Co., Ltd. Nitrogen-containing compound-containing compound and organic electroluminescence device including the same
CN109678851A (zh) * 2019-01-31 2019-04-26 武汉华星光电半导体显示技术有限公司 热激活延迟荧光材料、有机电致发光器件及显示面板
CN109734649A (zh) * 2019-02-19 2019-05-10 中国科学院化学研究所 一种基于芳酰亚胺的有机小分子高效室温磷光材料及其制备与应用
CN109734649B (zh) * 2019-02-19 2020-06-16 中国科学院化学研究所 一种基于芳酰亚胺的有机小分子高效室温磷光材料及其制备与应用

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