WO2016116523A1 - Molécules organiques à utiliser en particulier dans des composants optoélectroniques - Google Patents

Molécules organiques à utiliser en particulier dans des composants optoélectroniques Download PDF

Info

Publication number
WO2016116523A1
WO2016116523A1 PCT/EP2016/051165 EP2016051165W WO2016116523A1 WO 2016116523 A1 WO2016116523 A1 WO 2016116523A1 EP 2016051165 W EP2016051165 W EP 2016051165W WO 2016116523 A1 WO2016116523 A1 WO 2016116523A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
formula
radicals
aromatic
Prior art date
Application number
PCT/EP2016/051165
Other languages
German (de)
English (en)
Inventor
David Ambrosek
Michael Danz
Harald FLÜGGE
Jana Friedrichs
Tobias Grab
Andreas Jacob
Stefan Seifermann
Daniel Volz
Original Assignee
Cynora 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 Cynora Gmbh filed Critical Cynora Gmbh
Publication of WO2016116523A1 publication Critical patent/WO2016116523A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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 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 which have a structure of formula 1 or have a structure of formula 1:
  • n is an integer of 1 to 3;
  • n is an integer from 1 to 3;
  • 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);
  • R *** is independently a radical R *, denotes the point of attachment to a chemical unit according to formula 1 b, denotes the point of attachment to another chemical unit of formula 1 a, or is naphthyl or a monocyclic aromatic system, wherein in the case of aromatic R *** between the aromatic part of R *** and the central N in formula 1 a exists only a direct link; and wherein each R *** radical may be functionalized with further R ** radicals;
  • R ** is, independently of one another, a radical R * and denotes the point of attachment to a chemical unit according to formula 1 b or to a chemical unit according to formula 1 a; where two or more substituents R ** can also together form a mono- or polycyclic, aliphatic or aromatic ring system; and wherein the contained unit (s) AF1 has or have a structure according to formula 1b;
  • Z is CR ** or N, with a maximum of 4 units Z being N at the same time;
  • o 0 or 1
  • p is 0 or 1;
  • q is 0 or 1
  • 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 ; It can have two or more Substituents R 3 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 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. This is the basic definition. If other preferences are given in the description of the present invention, for example with regard to the number of aromatic ring atoms or the heteroatoms contained therein, these 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 a non-aromatic moiety (especially less than 10% of the various atoms), such as.
  • an sp 3 -hybridized C, Si, or N atom, an sp 2 -hybridized C-, N- or O-atom, or an sp-hybridized carbon atom may be joined.
  • systems such as 9, T-diaryl fluorene, 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 connected 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 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
  • AF2 always has a lower HOMO value (compared to AF1) and thus a lower LUMO value 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 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 unit eV calculated with the BP86 functional (Becke, AD Phys Rev. A1988, 38, 3098-3100, Perdew, JP Phys Rev. B1986, 33, 8822-8827 ).
  • At least one of the chemical units AF2 has a structure according to formula 2a or 2b or 2c or 2d or 2e:
  • A is a radical R * or denotes the attachment to a group of the form AF1-AF2;
  • R ** and R * are as defined for Formula 1a and Formula 1b; and wherein the respective other unit (s) AF1 has / have a structure according to the formulas 2f to 2z.
  • Units Y are simultaneously an element-element single bond, or is NR **, where two units Y are not simultaneously NR **;
  • U is CR **, N, where a maximum of 3 units U are N at the same time, and no adjacent units U are N at the same time;
  • ALK is methyl, ethyl, propyl, / 'so-propyl, butyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl;
  • Formula 2x Formula 2y Formula 2z and where: M is H, D, ALK, phenyl, pyridyl, R **, CN, with a maximum of 4 units M being simultaneously CN;
  • R ** and R * are defined as in formulas 1a and 1b.
  • the unit (s) AF2 has a structure selected from one of the structures shown in Table 1;
  • Table 1 Examples of chemical entities AF2.
  • the unit (s) AF1 has a structure selected from the structures shown in Table 2;
  • Table 2 Units AF1 which may be contained in molecules of the invention.
  • the molecules according to the invention have a structure of the formula 3a or 3b or 3c or 3d or 3e or 3f or 3g or 3h or have a structure of the formula 3a or 3b or 3c or 3d or 3e or 3f or 3g or 3h;
  • J is CR * or is C when attached to the diarylamine moiety.
  • E is R * or is selected from:
  • RT is selected from H, CH 3, Ph, f-Bu, OMe, OPh; and wherein, moreover, the definitions given in formula 1, apply and R ** and R * are defined as in formula 1 a and 1 b.
  • Table 3 Examples of organic molecules (AF2) according to the invention n- (AF1) m which contain at least one unit AF2 from Table 1 and at least one unit AF1 from Table 2 and which optionally contain one or more of the radicals R * defined above.
  • n- (AF1) m which contain at least one unit AF2 from Table 1 and at least one unit AF1 from Table 2 and which optionally contain one or more of the radicals R * defined above.
  • the calculated values for the singlet-triplet distance in the geometry of the SO ground state are given in brackets under the corresponding molecular structure.
  • Table 4 Inventive organic molecules according to the scheme AF1-S-AF2, where S represents the direct bond between AF1 and AF2. In brackets the values for ⁇ , ALUMO and Gap are given.
  • organic molecules of the invention have one or more units AF1 selected from the structures 40, 61, 62, 68, 86, 113, 123, 150, 151, 152, 153, 154, 205, 209 , 244, 286, 288, 297, 303, 311, 313, 332, 358, 370, 371 of Table 2; the other unit (s) AF2 being selected from the structures of Table 1.
  • spectroscopic selection rules symmetric molecules
  • UV / VIS spectroscopy UV / VIS spectroscopy
  • quantum chemical calculation of the oscillator strength it can be predicted whether a quantum mechanical transition is allowed.
  • the aim is to have a decay time of ⁇ 300 ps, in particular ⁇ 100 ps or ⁇ 50 ps. With a long decay time of the (organic) emitter, saturation effects quickly occur at high current intensities, which adversely affects the component lifetime and prevents the achievement of high brightness levels.
  • a measure of the decay time is the AE (Si-T-i) distance. This is influenced by the overlap of HOMO and LUMO.
  • the size of the quantum mechanical overlap integral which can be calculated using the above-mentioned DFT method, can be controlled in a targeted manner. 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
  • 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
  • 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, especially 1 to 15, or 2 to 10 carbon atoms, and wherein the wavy line indicates the position via which the linker group 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.
  • the polymerisable functional units via a linker group of the formulas 12 to 17, which have a hydroxyl moiety are attached to an organic molecule of the formula 1 and the compounds resulting therefrom itself homopolymerized or copolymerized with other suitable monomers.
  • 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.
  • 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-Ti
  • Si lowest excited singlet
  • T-i triplet
  • 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 diode (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 field effect transistor, organic laser and down-conversion element.
  • OLED organic light emitting diode
  • 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 field effect transistor
  • organic laser and down-conversion element organic laser and down-conversion element
  • the optoelectronic component 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 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 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 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 (Ti) and singlet (Si) energy levels of the host material are higher in energy than the triplet (Ti) and singlet (Si) -Energieiveaus of the organic molecule, and wherein the organic molecule fluorescence or thermally activated delayed fluorescence (TADF) emitted, and an AE (Si-Ti) value between the lowest excited singlet (Si) and the underlying triplet (Ti) state of less than 0.2 eV, especially 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 processing the organic molecule by a vacuum evaporation method or from a solution.
  • the method comprises the step of applying the organic molecule to a support, 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. Examples
  • 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) , Synthesis instructions:
  • AAV4 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.
  • OLED organic light emitting diode

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne une molécule organique et son utilisation dans des dispositifs optoélectroniques. Cette molécule présente une structure de formule (1) dans laquelle m représente un entier compris entre 1 et 3 et n représente un entier compris entre 1 et 3, la somme de m et de n étant égale à un nombre entier compris entre 2 et 4; AF1 étant différent de AF2; la ou les unités AF2 contenue(s) présentant/comprenant une structure de formule (1a) (formule (1a)), et la ou les unités AF1 contenue(s) présentant/comprenant une structure de formule (1b) (formule (1b)).
PCT/EP2016/051165 2015-01-20 2016-01-20 Molécules organiques à utiliser en particulier dans des composants optoélectroniques WO2016116523A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP15151870.1 2015-01-20
EP15151870 2015-01-20
DE102015107904.6 2015-05-20
DE102015107904 2015-05-20

Publications (1)

Publication Number Publication Date
WO2016116523A1 true WO2016116523A1 (fr) 2016-07-28

Family

ID=55345796

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2016/051165 WO2016116523A1 (fr) 2015-01-20 2016-01-20 Molécules organiques à utiliser en particulier dans des composants optoélectroniques

Country Status (1)

Country Link
WO (1) WO2016116523A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115322121A (zh) * 2022-09-06 2022-11-11 华中科技大学鄂州工业技术研究院 一种有机空穴传输材料及其制备得到的钙钛矿太阳能电池

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130228752A1 (en) * 2012-03-02 2013-09-05 Dong-Woo Shin Pyrene-based compound, organic light-emitting diode comprising the same and organic light-emitting apparatus comprising the same
WO2014011753A2 (fr) * 2012-07-10 2014-01-16 Georgia State University Research Foundation, Inc. Analogues d'anthraquinone et leurs procédés de fabrication et d'utilisation
WO2014057874A1 (fr) * 2012-10-12 2014-04-17 東レ株式会社 Dérivé de fluoranthène, matériau d'élément luminescent le contenant, et élément luminescent

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130228752A1 (en) * 2012-03-02 2013-09-05 Dong-Woo Shin Pyrene-based compound, organic light-emitting diode comprising the same and organic light-emitting apparatus comprising the same
WO2014011753A2 (fr) * 2012-07-10 2014-01-16 Georgia State University Research Foundation, Inc. Analogues d'anthraquinone et leurs procédés de fabrication et d'utilisation
WO2014057874A1 (fr) * 2012-10-12 2014-04-17 東レ株式会社 Dérivé de fluoranthène, matériau d'élément luminescent le contenant, et élément luminescent

Non-Patent Citations (24)

* Cited by examiner, † Cited by third party
Title
"TURBOMOLE V6.4 2012", 2007, TURBOMOLE GMBH
BECKE, A. D, PHYS. REV. A, vol. 38, 1988, pages 3098 - 3100
BECKE, A. D., PHYS. REV. A, vol. 38, 1988, pages 3098 - 3100
BECKE, A.D., J.CHEM.PHYS., vol. 98, 1993, pages 5648 - 5652
H. YERSIN, TOP. CURR. CHEM., vol. 241, 2004, pages 1
H. YERSIN: "Highly Efficient OLEDs with Phosphorescent Materials", 2008, WILEY-VCH
HÄSER, M.; AHLRICHS, R., J. COMPUT. CHEM., vol. 10, 1989, pages 104 - 111
IBRAHIM MUSTAFA EL-DEEB ET AL: "A New Efficient Convergent Synthesis of Conjugated Aryl-containing Dendrimers", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 31, no. 6, 20 June 2010 (2010-06-20), KR, pages 1757 - 1760, XP055270937, ISSN: 0253-2964, DOI: 10.5012/bkcs.2010.31.6.1757 *
LEE, C; YANG, W; PARR, R.G, PHYS. REV. B, vol. 37, 1988, pages 785 - 789
M. A. BALDO; D. F. O'BRIEN; M. E. THOMPSON; S. R. FORREST, PHYS. REV. B, vol. 60, 1999, pages 14422
PERDEW, J. P, PHYS. REV. B, vol. 33, 1986, pages 8822 - 8827
QISHENG ZHANG ET AL: "Anthraquinone-Based Intramolecular Charge-Transfer Compounds: Computational Molecular Design, Thermally Activated Delayed Fluorescence, and Highly Efficient Red Electroluminescence", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 136, no. 52, 3 December 2014 (2014-12-03), US, pages 18070 - 18081, XP055270946, ISSN: 0002-7863, DOI: 10.1021/ja510144h *
RAPPOPORT, D.; FURCHE, F., J. CHEM. PHYS, vol. 133, 2010, pages 134105,1 - 134105,11
RAPPOPORT, D.; FURCHE, F., J. CHEM. PHYS., vol. 133, 2010, pages 134105,1 - 134105,11
SIERKA, M.; HOGEKAMP, A.; AHLRICHS, R., J. CHEM. PHYS., vol. 118, 2003, pages 9136 - 9148
STEPHENS, P. J.; DEVLIN, F. J.; CHABALOWSKI, C. F.; FRISCH, M. J., J.PHYS.CHEM., vol. 98, 1994, pages 11623 - 11627
TANG ET AL., APPL. PHYS. LETT., vol. 51, 1987, pages 913
VOSKO, S. H.; WILK, L.; NUSAIR, M, CAN. J. PHYS., vol. 58, 1980, pages 1200 - 1211
WEIGEND, F.; AHLRICHS, R, PHYS. CHEM. CHEM. PHYS., vol. 7, 2005, pages 3297 - 3305
WEIGEND, F.; AHLRICHS, R., PHYS. CHEM. CHEM. PHYS., vol. 7, 2005, pages 3297 - 3305
WEIGEND, F.; HÄSER, M, THEOR. CHEM. ACC., vol. 97, 1997, pages 331 - 340
XUEJUN ZHAN ET AL: "Polyphenylbenzene as a Platform for Deep-Blue OLEDs: Aggregation Enhanced Emission and High External Quantum Efficiency of 3.98%", CHEMISTRY OF MATERIALS, vol. 27, no. 5, 10 March 2015 (2015-03-10), US, pages 1847 - 1854, XP055267611, ISSN: 0897-4756, DOI: 10.1021/acs.chemmater.5b00094 *
ZUJIN ZHAO ET AL: "High hole mobility of 1,2-bis[4'-(diphenylamino)biphenyl-4-yl]-1,2-diphenylethene in field effect transistor", CHEMICAL COMMUNICATIONS - CHEMCOM, vol. 47, no. 24, 1 January 2011 (2011-01-01), GB, pages 6924, XP055270912, ISSN: 1359-7345, DOI: 10.1039/c1cc12011e *
ZUJIN ZHAO ET AL: "Stereoselective Synthesis, Efficient Light Emission, and High Bipolar Charge Mobility of Chiasmatic Luminogens", ADVANCED MATERIALS, vol. 23, no. 45, 1 December 2011 (2011-12-01), DE, pages 5430 - 5435, XP055270939, ISSN: 0935-9648, DOI: 10.1002/adma.201102804 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115322121A (zh) * 2022-09-06 2022-11-11 华中科技大学鄂州工业技术研究院 一种有机空穴传输材料及其制备得到的钙钛矿太阳能电池
CN115322121B (zh) * 2022-09-06 2024-02-09 华中科技大学鄂州工业技术研究院 一种有机空穴传输材料及其制备得到的钙钛矿太阳能电池

Similar Documents

Publication Publication Date Title
EP3247769B1 (fr) Molécules organiques substituées par un éther phénylique, en particulier pour une utilisation dans des composants optoélectroniques
EP3016952B1 (fr) Composés de lactame spirocondensés pour des dispositifs électroluminescents organiques
EP3033405A1 (fr) Matériaux destinés à des dispositifs électroniques
WO2015158411A1 (fr) Matières pour dispositifs électroniques
EP3247767B1 (fr) Molécules organiques à utiliser en particulier dans des composants optoélectroniques
WO2016116525A1 (fr) Molécules organiques, notamment pour une utilisation dans des composants opto-électroniques
EP3130015A1 (fr) Matériaux destinés à des dispositifs électroluminescents organiques
EP3247770A1 (fr) Molécules organiques destinées en particulier à être utilisées dans des composants optoélectroniques
WO2016116504A1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
WO2016074755A1 (fr) Matériaux pour dispositifs électroluminescents organiques
EP3247773A1 (fr) Molécules organiques pour une utilisation en particulier dans des composants optoélectroniques
DE102016113277A1 (de) Organische Moleküle zur Verwendung in optoelektronischen Bauelementen
EP3247771A1 (fr) Pyridines et leurs dérivés en tant que constituants utilisables dans des composants optoélectroniques
EP3197982A1 (fr) Matières pour dispositifs électroluminescents organiques
WO2016116522A1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
EP3247766B1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
WO2016116486A1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
EP3247772B1 (fr) Molécules organiques symétriques destinées à être utilisées dans des composants optoélectroniques
EP3247768B1 (fr) Molécules organiques substituées par naphthyl destinées à être utilisées dans des éléments de construction opto-électroniques
EP4122028A1 (fr) Composés hétérocycliques pour dispositifs électroluminescents organiques
WO2016116523A1 (fr) Molécules organiques à utiliser en particulier dans des composants optoélectroniques
EP3248230B1 (fr) Utilisation des molecules organiques dans des composants optelectroniques
EP3048155A1 (fr) Molécules organiques, en particulier destinées à être utilisées dans des composants optoélectroniques
WO2016116518A1 (fr) Molécules organiques notamment utilisées dans des composants optoélectroniques
WO2016116521A1 (fr) Molécules organiques à utiliser en particulier dans des composants optoélectroniques

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16703732

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16703732

Country of ref document: EP

Kind code of ref document: A1