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WO2016046077A1 - Matériaux hôtes réticulables - Google Patents

Matériaux hôtes réticulables Download PDF

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Publication number
WO2016046077A1
WO2016046077A1 PCT/EP2015/071415 EP2015071415W WO2016046077A1 WO 2016046077 A1 WO2016046077 A1 WO 2016046077A1 EP 2015071415 W EP2015071415 W EP 2015071415W WO 2016046077 A1 WO2016046077 A1 WO 2016046077A1
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atoms
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substituted
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Daniel Volz
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Cynora GmbH
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Cynora GmbH
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Priority to CN202211174439.7A priority Critical patent/CN115572284A/zh
Priority to CN201580051943.XA priority patent/CN106715420A/zh
Priority to JP2017516447A priority patent/JP6826031B2/ja
Publication of WO2016046077A1 publication Critical patent/WO2016046077A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1483—Heterocyclic containing nitrogen and sulfur 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
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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 organic molecules of general formula 1 and their use as crosslinkable, liquid processable host materials in OLEDs (organic light-emitting diodes) and other opto-electronic components.
  • Organic electronic devices are increasingly being used in commercial products or are about to be launched on the market. Examples of already commercial products include organic or polymeric light-emitting diodes (OLEDs, PLEDs) in display and display devices.
  • Organic solar cells O-SCs
  • organic field-effect transistors O-FETs
  • organic thin-film transistors O-TFTs
  • organic switching elements O-ICs
  • organic optical amplifiers or organic laser diodes O-lasers
  • the compounds used are sometimes difficult to dissolve in common organic solvents, which makes their purification in the synthesis, but also the processing of the materials from solution and the cleaning of equipment in the manufacture of electronic devices difficult.
  • Electrode which can often be metallic or inorganic, but also composed of organic or polymeric conductive materials, (3) optionally one or more charge injection layer (s) to compensate for unevenness of the electrode, often from a or a plurality of conductive, doped polymer (s) is / are (4) at least one layer of an organic semiconductor, (5) optionally one or more further charge-transport or charge-blocking layer (s),
  • OLED organic light-emitting diodes
  • PLED Polymeric light emitting diodes
  • the above arrangement represents the general structure of an optoelectronic device, wherein different layers can be combined, so that in the simplest case there is an arrangement of two electrodes, between which an organic layer is located.
  • the organic semiconductor layer in this case fulfills all functions, including the emission of light.
  • Such a system is described, for example, in WO 9013148 A1 on the basis of poly (p-phenylenes).
  • OLEDs are not only determined by the emitters used.
  • the other materials used such as matrix materials, hole blocking materials, electron transport materials, hole transport materials and Elektronenpositioned. Exciton blocking materials of particular importance. Improvements to these materials can thus also lead to significant improvements in the OLED properties. Even for fluorescent OLEDs there is still room for improvement with these materials.
  • Ketones or phosphine oxides are used as matrix materials for phosphorescent emitters, inter alia, in the prior art.
  • these matrix materials as with other matrix materials, there is still room for improvement, in particular with regard to the efficiency and the lifetime of the device.
  • the present invention relates to the provision of compounds which are suitable for use in a fluorescent or phosphorescent or temperature-activated delayed-fluorescence OLED (TADF-OLED), in particular a phosphorescent or TADF-OLED
  • TADF-OLED temperature-activated delayed-fluorescence OLED
  • a phosphorescent or TADF-OLED for example, as a matrix material or as a hole transport EIektronenblockiermaterial or Exzononenblockiermaterial or as an electron transport or Lochblockiermaterial.
  • the invention is based on a development of a new crosslinking unit PG as a basic structure in crosslinkable organic semiconductors (Formula 1 a).
  • Such crosslinking units can be used in organic semiconductors, which thereby obtain crosslinking capabilities themselves.
  • the invention in a first aspect, relates to a crosslinking unit PG and its use in the crosslinking of organic semiconductors.
  • the invention provides organic molecules of general formula 1,
  • Ar independently of one another an unsaturated or aromatic carbo- or heterocyclic unit having 5 to 30 ring atoms, selected from the group consisting of naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, tetracene, pentacene, benzpyrene , Furan, benzofuran, isobenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo -7,8-quinoline, phenothiazine, phenoxazine, pyrazole, in
  • D1 a donor group with electron-donating properties, having a structure of formula 1 a;
  • D2 a donor group with electron-donating properties, having a structure of formula 1 b;
  • n is an integer between 1 and 5;
  • o is an integer between 1 and 5;
  • PG are two identical or different polymerizable units that can be polymerized by thermal and / or acid or base catalyzed processes, UV irradiation in the presence or absence of a photoinitiator or by microwave radiation.
  • a functionalization takes place at the 3 and the 6-position of the structure.
  • Z is the same or different CR 2 or N at each occurrence
  • R and R 1 are the same or different at each occurrence, H, D, F, Cl, Br, I, B (OR 3 ) 2 , CHO,
  • Ring atoms which may be substituted by one or more radicals R 3 , or an aryloxy group having 6 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 3 , wherein two or more radicals R and R 1 may be linked together and can form a ring;
  • Substituents R 4 be linked together and form a ring
  • the group Ar of the organic molecule has, in one embodiment, the following structure
  • W is the same or different CR 1 or N at each occurrence (as defined above) and in particular at least one W is not equal to CR 1 .
  • the compounds according to the invention are PYD2-type compounds such as, for example
  • the compounds according to the invention are mCPy-type compounds, for example
  • the compounds according to the invention are DIHAPY-type compounds, for example
  • cross-linkable moiety and functional molecule in a single functional moiety minimizes the synthetic effort required to produce the materials since only one dibromocarbazole moiety must be introduced into the functional material rather than multiple moieties (see Example 3).
  • This dibromocarbazole residue can be easily and selectively converted by palladium-catalyzed cross-coupling reaction into the desired divinylcarbazole radical.
  • the electronic coupling between the two vinyl groups makes it easy to activate the material, allowing it to be crosslinked at lower temperatures or less UV dose compared to electronically decoupled divinyl-substituted systems, which is significantly gentler on the functional materials.
  • the increased delocalization decreases the activation barrier of the addition, so that it runs faster in the time average.
  • the properties of the components are changed by these processes in such a way that their energy levels shift and in the medium term a destruction of the component occurs.
  • parameters such as charge carrier mobility change negatively, resulting in problems with morphology, in particular phase separation, for example.
  • B. can lead to the crystallization of the host materials and / or the emitter molecules contained therein.
  • these protective groups can be split off in the long-term operation of the components, which leads to the problems just described.
  • unstable tertiary alkyl groups are replaced by more stable secondary alkyl groups.
  • the molecules according to the invention have donor groups D2 of the formula 1b, which have a planar structure, as a result of which the charge carrier mobility is markedly increased in comparison to molecules with unbridged arylamines.
  • Unbridged arylamines are significantly more unstable in comparison to the donor units according to the invention in OLEDs, since the unlinked aryl radicals can be split off relatively easily.
  • triplet energy is significantly higher for unbridged arylamines. With inappropriate triplet energy, the compounds are not suitable as host materials for thermally activated delayed fluorescence (TADF) emitters and phosphorescence emitters, especially not blue for the industrially significant color.
  • TADF thermally activated delayed fluorescence
  • polymerizable groups PG are optionally used in mirror-symmetric compounds.
  • two crosslinkable units PG in each case only one carbazole unit, the symmetry of these molecules is lowered ( Figure 3), whereby the solubility increases and the suitability for printing and coating processes is increased. By suppressing the crystallization, the film-forming properties are also improved.
  • two polymerizable groups PG are in conjugation and close proximity to each other.
  • at least two PG are necessary in the molecule.
  • the presence of exactly two polymerizable groups is preferred since, statistically, the likelihood of non-crosslinked units remaining as radicals after polymerization in the polymer film increases with the number of polymerizable groups PG in the molecule.
  • These radicals would act as so-called charge carrier traps in an optoelectronic device and would degrade its efficiency.
  • carbazole is used as the donor residue.
  • a disadvantage of the known, unsubstituted carbazole units is the low HOMO energy. Depending on the substitution, this is -6.0 to -5.6 eV. This will adapt to commonly used Hole injection layers such as PEDOT: PSS, which often show a HOMO energy around -5.1 eV, make this difficult.
  • PEDOT: PSS commonly used Hole injection layers
  • the substituents increase the HOMO energy by 50 to 200 meV, which reduces this energy difference compared to unsubstituted carbazole derivatives.
  • One aspect of the invention is based on using the crosslinking unit in known organic semiconductors in order to vary the optoelectronic properties to the extent that the requirements for this material are optimally achieved in a component, depending on the intended use (HOMO and LUMO, T1, S1, hole transport , Electron transport, hole blocker, electron blocker, solubility, orthogonal solubility and crosslinkability to allow for a multilayer component of solution).
  • HOMO and LUMO, T1, S1, hole transport , Electron transport, hole blocker, electron blocker, solubility, orthogonal solubility and crosslinkability to allow for a multilayer component of solution In order to further establish these components in terms of luminous efficacy and lifetime, several high-purity organic layers are used in the component itself, each individual layer having a separate function (charge injection, charge transport, charge blocking layer, emission layer, electrode, etc.). These layers generally become one after the other applied in a high vacuum by sublimation on a corresponding substrate.
  • OLEDs organic light-emitting diodes
  • polymerizable groups causes the film previously made from solution to transform into an insoluble network. In this way, a further layer of solution can be applied to the already coated substrate without causing mixing at the interface and without dissolving the previously deposited layer.
  • the compounds of the invention allow the use of crosslinking processes by photochemical or thermal crosslinking, without which the production of efficient, durable liquid-processed OLEDs will not be possible.
  • One aspect of the invention is thus to provide novel ambipolar host materials which have improved performance, lifetime, and operating potential when used in an opto-electronic device by introducing two conjugated crosslinkable groups PG onto a functional donor moiety such as carbazole, phenoxazine, or phenothiazine.
  • a functional donor moiety such as carbazole, phenoxazine, or phenothiazine.
  • the invention relates to the use of an organic molecule of the type described herein in an emitting layer as matrix material (host material) for luminescent emitters and / or as electron transport material and / or as hole injection material and / or as hole blocking material in an optoelectronic component.
  • matrix material host material
  • hole injection material hole blocking material
  • the organic molecule of the type described herein is used in an emitting layer of an optoelectronic component, preferably in admixture with at least one further compound. It is preferred here that the organic molecule in the mixture represents the matrix material.
  • an organic molecule of the type described herein is used accordingly as a matrix material for luminescent emitters in an optoelectronic component.
  • An optoelectronic component according to the present invention is preferably selected from the group consisting of:
  • OLEDs organic light-emitting devices
  • Another aspect of the invention relates to mixtures containing at least one organic molecule of the type described herein and at least one luminescent emitter.
  • the invention relates to formulations comprising at least one organic molecule of the type described herein or a mixture described herein and at least one solvent.
  • the proportion of organic material as matrix material in optical light-emitting components, in particular in OLEDs is between 50% and 99%.
  • an optoelectronic device comprising an organic molecule of the type described herein.
  • an optoelectronic device according to the invention contains at least one anode to cathode layer comprising an organic molecule of the type described herein, for example as a luminescent emitter host material and / or as an electron transport material and / or as a hole injection material and / or as a hole blocking material.
  • the optoelectronic component may be selected from the group consisting of organic light-emitting component, organic diode, organic solar cell, organic transistor, organic light-emitting diode, light-emitting electrochemical cell, organic field effect transistor and organic laser.
  • the invention relates to a method of making an optoelectronic device using an organic molecule of the type described herein.
  • Part of such a process may be the application of an organic molecule of the invention to a carrier.
  • the application can optionally be carried out by evaporation in vacuo or wet-chemical.
  • the organic molecules according to the invention When used in optoelectronic components, the organic molecules according to the invention have in particular the following advantages over the prior art:
  • the charge carrier mobility in the component is improved in comparison to systems according to the prior art.
  • Carbazole (10 mmol, 1, 00 equiv.) Is treated with sodium hydride (60% with paraffin, 500 mg, 13 mmol, 1.3 equiv.) And dissolved under nitrogen in portions with a total of 1 10 ml of dioxane. The rate of addition is adapted to the formation of hydrogen to avoid foaming. After complete addition, the reaction was held at r.t. for 15 min. stirred and then heated at reflux for 15 min. This formed a clear, yellow solution that fluoresces strongly under UV light (366 nm excitation). 2,6-Difluoropyridine (1.15 g, 10 mmol, 1.00 equiv.) Is added dropwise to the reaction mixture.
  • the fluorescence attenuates considerably under UV light.
  • the reaction mixture is heated to complete conversion of the starting materials (reaction control by HPLC, GC-MS or TLC, typically 4 h) at reflux. After cooling to room temperature, excess base is quenched by dropwise addition of 10 mL of water under nitrogen.
  • the reaction mixture was added to 200 ml of saturated sodium chloride solution and the crude product was separated by suction and washed with water (300 ml) and methanol (60 ml). The resulting solid was digested with 200 mL of hot toluene and the insoluble residue discarded.
  • the synthesis was carried out analogously to the first step, but using instead of carbazole dibromocarbazole and instead of 2,6-difluoropyridine, the reaction product of the first substitution step and instead of a clear yellow solution prior to addition of the 2,6-difluoropyridine, a suspension was present.
  • FIG. 1 By introducing two polymerizable groups which are conjugated via bridges such as carbazole, phenoxazine, phenothiazine and comparable annealed heterocycles, two possible growth positions for polymer chains are available in principle.
  • bridges such as carbazole, phenoxazine, phenothiazine and comparable annealed heterocycles
  • FIG. 2 Unsubstituted carbazoles are prone to a degradation path leading to the formation of 3,6-linked polymers. This is prevented by the introduction of substituents according to the invention.
  • FIG. 3 The introduction of the polymerizable units PG on one side of mirror-symmetrical compounds reduces the symmetry of these molecules, which increases the solubility and increases the suitability for printing and coating processes. By suppressing the crystallization, the film-forming properties are also improved.

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  • Photovoltaic Devices (AREA)

Abstract

L'invention concerne une molécule organique réticulable, comprenant une structure de formule (1) ainsi que l'utilisation de cette dernière, Ar = indépendamment les uns des autres un motif carbocyclique ou hétérocyclique aromatique ou insaturé comprenant 5 à 30 atomes de cycle, choisi dans le groupe constitué par la naphtaline, l'anthracène, le phénanthrène, le pyrène, le dihydropyrène, le chrysène, le pérylène, le fluoranthène, le benzanthracène, le tétracène, le pentacène, le benzopyrène, le furane, le benzofurane, l'isobenzofurane, le thiophène, le benzothiophène, l'isobenzothiophène, le dibenzothiophène, le pyrrole, l'indole, l'isoindole, le carbazole, la pyridine, la quinoléine, l'isoquinoléine, l'acridine, la phénanthridine, la benzo-5,6-quinoléine, la benzo-6,7-quinoléine, la benzo-7,8-quinoléine, la phénothiazine, la phénoxazine, le pyrazole, l'indazole, l'imidazole, le benzimidazole, le naphthimidazole, le phénanthrimidazole, le pyridimidazole, le pyrazine-imidazole, le quinoxalinimidazole, l'oxazole, le benzoxazole, le naphthoxazole, l'anthroxazole, le phénanthroxazole, l'isoxazole, l'isothiazole, le 1,3-thiazole, le benzothiazole, la pyridazine, la benzopyridazine, la pyrimidine, la benzpyrimidine, la quinoxaline, la pyrazine, la phénazine, la naphthyridine, l'azacarbazole, la benzocarboline, la phénanthroline, le 1,2,3-triazole, le 1,2,4-triazole, le benzotriazole, le 1,2,3-oxadiazole, le 1,2,4-oxadiazole, le 1,2,5-oxadiazole, le 1,3,4-oxadiazole, le 1,2,3-thiadiazole, le 1,2,4-thiadiazole, le 1,2,5-thiadiazole, le 1,3,4-thiadiazole, la 1,3,5-triazine, la 1,2,4-triazine, la 1,2,3-triazine, le tétrazole, le 1,2,3,4-oxatriazole, le 1,2,3,4-oxatriazole, la 1,2,4,5-tétrazine, la 1,2,3,4-tétrazine, la 1,2,3,5-tétrazine, la purine, la ptéridine, l'indolizine, le benzothiadiazole, l'indénocarbazole, l'indénofluorène, le spirobifluorène et l'indolocarbazole ; D1 = un groupe donneur, comprenant une structure de formule (1a) ; formule (1a) et D2 = un groupe donneur, comprenant une structure de formule (1b)
PCT/EP2015/071415 2014-09-25 2015-09-18 Matériaux hôtes réticulables Ceased WO2016046077A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016116517A1 (fr) * 2015-01-20 2016-07-28 Cynora Gmbh Pyridines et leurs dérivés en tant que constituants utilisables dans des composants optoélectroniques
DE102016108327B3 (de) * 2016-05-04 2017-03-02 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen
CN106611823A (zh) * 2017-01-19 2017-05-03 江西冠能光电材料有限公司 一种可交联有机半导体主体材料及其有机发光二极管应用
CN106784359A (zh) * 2017-01-19 2017-05-31 江西冠能光电材料有限公司 可交联平衡电荷注入有机半导体及其有机发光二极管应用
US20180173070A1 (en) * 2015-06-19 2018-06-21 Satoshi Yamamoto Electrochromic compound, electrochromic composition, and electrochromic display element
WO2018113785A1 (fr) * 2016-12-22 2018-06-28 广州华睿光电材料有限公司 Polymère contenant un groupe de réticulation furane et utilisation associée
CN109564980A (zh) * 2016-07-26 2019-04-02 日立化成株式会社 有机电子材料
WO2019202342A1 (fr) * 2018-04-20 2019-10-24 University Court Of The University Of St Andrews Composés hétérocycliques présentant une fluorescence retardée activée thermiquement (tadf) et leur utilisation dans des dispositifs électroluminescents
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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
WO1990013148A1 (fr) 1989-04-20 1990-11-01 Cambridge Research And Innovation Limited Dispositifs electroluminescents
US5151629A (en) 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
EP0676461A2 (fr) 1994-04-07 1995-10-11 Hoechst Aktiengesellschaft Composés spiro et leur application comme matières électroluminescentes
WO1998027136A1 (fr) 1996-12-16 1998-06-25 Aventis Research & Technologies Gmbh & Co Kg POLY(p-ARYLENEVINYLENES) A SUBSTITUTION ARYLE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION DANS DES COMPOSANTS ELECTROLUMINESCENTS
US20060083943A1 (en) * 2002-03-04 2006-04-20 Neil Maxted Phosphorescent compositions and organic light emitting devices containing therm
WO2011093309A1 (fr) * 2010-01-28 2011-08-04 コニカミノルタホールディングス株式会社 Élément de conversion photoélectrique organique
WO2014132636A1 (fr) * 2013-03-01 2014-09-04 出光興産株式会社 Monomère polymérisable, matériau pour dispositif organique comprenant ledit polymère, matériau d'injection/de transport de trou, matériau pour élément électroluminescent organique et élément électroluminescent organique
WO2015022987A1 (fr) * 2013-08-16 2015-02-19 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif électronique, dispositif électroluminescent et matériau électroluminescent

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006092943A1 (fr) * 2005-03-02 2006-09-08 Konica Minolta Holdings, Inc. Dispositif électroluminescent organique, affichage et dispositif d’éclairage
JP5676993B2 (ja) * 2009-09-30 2015-02-25 キヤノン株式会社 記録媒体
DE102009053382A1 (de) * 2009-11-14 2011-05-19 Merck Patent Gmbh Materialien für elektronische Vorrichtungen
JP2012043912A (ja) * 2010-08-17 2012-03-01 Fujifilm Corp 有機電界発光素子用材料、該有機電界発光素子用材料を含む組成物、並びに、該組成物により形成された膜、及び有機電界発光素子
JP5591052B2 (ja) * 2010-09-30 2014-09-17 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子
JP5866902B2 (ja) * 2011-09-12 2016-02-24 国立大学法人山形大学 カルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子
US9553274B2 (en) * 2013-07-16 2017-01-24 Universal Display Corporation Organic electroluminescent materials and devices

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539507A (en) 1983-03-25 1985-09-03 Eastman Kodak Company Organic electroluminescent devices having improved power conversion efficiencies
WO1990013148A1 (fr) 1989-04-20 1990-11-01 Cambridge Research And Innovation Limited Dispositifs electroluminescents
US5151629A (en) 1991-08-01 1992-09-29 Eastman Kodak Company Blue emitting internal junction organic electroluminescent device (I)
EP0676461A2 (fr) 1994-04-07 1995-10-11 Hoechst Aktiengesellschaft Composés spiro et leur application comme matières électroluminescentes
WO1998027136A1 (fr) 1996-12-16 1998-06-25 Aventis Research & Technologies Gmbh & Co Kg POLY(p-ARYLENEVINYLENES) A SUBSTITUTION ARYLE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION DANS DES COMPOSANTS ELECTROLUMINESCENTS
US20060083943A1 (en) * 2002-03-04 2006-04-20 Neil Maxted Phosphorescent compositions and organic light emitting devices containing therm
WO2011093309A1 (fr) * 2010-01-28 2011-08-04 コニカミノルタホールディングス株式会社 Élément de conversion photoélectrique organique
WO2014132636A1 (fr) * 2013-03-01 2014-09-04 出光興産株式会社 Monomère polymérisable, matériau pour dispositif organique comprenant ledit polymère, matériau d'injection/de transport de trou, matériau pour élément électroluminescent organique et élément électroluminescent organique
WO2015022987A1 (fr) * 2013-08-16 2015-02-19 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif électronique, dispositif électroluminescent et matériau électroluminescent

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DONGWOOK KIM ET AL: "Design of Efficient Ambipolar Host Materials for Organic Blue Electrophosphorescence: Theoretical Characterization of Hosts Based on Carbazole Derivatives", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 44, 25 September 2011 (2011-09-25), pages 17895 - 17900, XP055122541, ISSN: 0002-7863, DOI: 10.1021/ja207554h *
TETRAHEDRON, vol. 54, 1998, pages 12707 - 12714

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US10544361B2 (en) 2015-01-20 2020-01-28 Cynora Gmbh Pyridines and derivatives thereof as components for use in optoelectronic components
US10935862B2 (en) 2015-06-19 2021-03-02 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, and electrochromic display element
US10534236B2 (en) * 2015-06-19 2020-01-14 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, and electrochromic display element
US20180173070A1 (en) * 2015-06-19 2018-06-21 Satoshi Yamamoto Electrochromic compound, electrochromic composition, and electrochromic display element
DE102016108327B3 (de) * 2016-05-04 2017-03-02 Cynora Gmbh Organische Moleküle, insbesondere zur Verwendung in organischen optoelektronischen Vorrichtungen
CN109564980A (zh) * 2016-07-26 2019-04-02 日立化成株式会社 有机电子材料
JPWO2018021381A1 (ja) * 2016-07-26 2019-05-16 日立化成株式会社 有機エレクトロニクス材料
EP3493286A4 (fr) * 2016-07-26 2020-04-01 Hitachi Chemical Company, Ltd. Matériau électronique organique
WO2018113785A1 (fr) * 2016-12-22 2018-06-28 广州华睿光电材料有限公司 Polymère contenant un groupe de réticulation furane et utilisation associée
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US11289654B2 (en) 2016-12-22 2022-03-29 Guangzhou Chinaray Optoelectronic Materials Ltd. Polymers containing furanyl crosslinkable groups and uses thereof
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CN106611823A (zh) * 2017-01-19 2017-05-03 江西冠能光电材料有限公司 一种可交联有机半导体主体材料及其有机发光二极管应用
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