WO2020220414A1 - Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif d'affichage - Google Patents

Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif d'affichage Download PDF

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WO2020220414A1
WO2020220414A1 PCT/CN2019/088078 CN2019088078W WO2020220414A1 WO 2020220414 A1 WO2020220414 A1 WO 2020220414A1 CN 2019088078 W CN2019088078 W CN 2019088078W WO 2020220414 A1 WO2020220414 A1 WO 2020220414A1
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thermally activated
activated delayed
fluorescent material
delayed fluorescent
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王彦杰
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武汉华星光电半导体显示技术有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
    • C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Definitions

  • the invention relates to the technical field of organic electroluminescent materials, in particular to a thermally activated delayed fluorescent material, a preparation method thereof, and a display device.
  • Organic electroluminescence is a kind of luminescence phenomenon realized by the use of organic materials under the excitation of external electric field and current.
  • the layered OLED (Organic Light-Emitting Diode, organic light-emitting diode) structure has achieved higher brightness, higher external quantum efficiency and lower driving voltage, which has stimulated great interest in the research of OLED by scientific researchers. It is possible to realize commercialization.
  • OLED In recent years, due to its active light emission, large viewing angle, fast corresponding speed, wide temperature adaptation range, low driving voltage, low power consumption, high brightness, simple production process, light and thin, and flexible display, OLED displays And the lighting field shows great application prospects, attracting the attention of scientific researchers and companies.
  • the usual luminescent layer material consists of host and guest luminescent materials, and the luminous efficiency and lifetime of luminescent materials are two important indicators of the quality of luminescent materials.
  • Early OLED light-emitting materials were traditional fluorescent materials.
  • Adachi et al. proposed a pure organic light-emitting molecule with a "Thermally Activated Delayed Fluorescence" (TADF) mechanism.
  • TADF Thermally Activated Delayed Fluorescence
  • the molecule has a smaller minimum singlet state and triplet energy.
  • Level difference ( ⁇ EST) so that the triplet excitons can return to the singlet state through RISC, and then radiate to the ground state to emit light, so that single and triplet excitons can be used at the same time to realize excitons
  • the utilization rate of 100% without the participation of heavy metals.
  • the TADF material has a rich structure design, and most of its physical properties are easily adjusted to obtain high-efficiency and long-life organic light-emitting materials that meet the requirements.
  • the ⁇ - ⁇ stacking between molecules is serious, and the ⁇ - ⁇ stacking easily causes the material to aggregate, leading to luminescence quenching.
  • the usual solution is to suppress the aggregation of materials to quench the luminescence phenomenon by doping.
  • the phenomenon of aggregation and quenching still exists after the general molecular doping, and the doping ratio of the luminescent material is small, which will reduce the efficiency of the device. .
  • the purpose of the present invention is to provide a thermally activated delayed fluorescent material, a preparation method thereof, and a display device to solve the problem of serious accumulation of ⁇ - ⁇ between molecules in the thermally activated delayed fluorescent material in the prior art, and electron acceptor and electron donor
  • HOMO Occupied Molecular Orbital
  • LUMO Lowest Unoccupied Molecular Orbital
  • the present invention provides a thermally activated delayed fluorescent material, which includes an electron donor and an electron acceptor.
  • the electron donor includes at least two benzene rings and a seven-membered ring connected between the two benzene rings.
  • the molecular structure of the electron donor includes one of the following structures:
  • the molecular structure of the electron acceptor includes one of the following structures:
  • the present invention also provides a method for preparing thermally activated delayed fluorescent material, which includes the following steps:
  • Synthesis of the first target placing the electron donor, the electron acceptor, and the catalyst in a reaction vessel to obtain a reaction solution, fully reacting in an argon atmosphere to obtain a mixed solution, and the mixed solution contains the target produced by the reaction.
  • Extracting the first target cooling the mixed solution to room temperature, and extracting the target in the mixed solution.
  • Purifying the first target purifying the target to obtain the near-infrared photothermal activated delayed fluorescent material.
  • the catalyst is toluene, potassium carbonate and palladium tetrakistriphenylphosphine.
  • the electron acceptor, the electron donor, the toluene and the potassium carbonate are placed together in the reaction vessel, and then the reaction vessel is placed in an argon atmosphere, and the reaction vessel is added The palladium tetrakistriphenylphosphorus is used to obtain a reaction solution.
  • the step of extracting the target substance includes adding dichloromethane to the reaction solution for extraction, and drying after multiple extractions to obtain the target substance.
  • the step of purifying and treating the target substance includes using an eluent to purify the target substance for the first time by a silica gel column chromatography method to obtain the thermally activated delayed fluorescence material.
  • the eluent in the silica gel column chromatography method is petroleum ether and dichloromethane, and the volume ratio of the petroleum ether and the dichloromethane is 1:1.
  • the step of synthesizing the first target it further includes a step of forming an electron donor.
  • the step of forming an electron donor includes the following steps:
  • Synthesis of the second target placing the first compound, the second compound and the catalyst in a reaction vessel to obtain a reaction solution, and fully react in an argon atmosphere to obtain a mixed solution, and the mixed solution contains the target produced by the reaction.
  • Extracting the second target cooling the mixed solution to room temperature, and extracting the target in the mixed solution.
  • Purifying the second target purifying the target to obtain a third compound having the electron donor structure.
  • the structure of the first compound has at least two benzene rings and a seven-membered ring connected between the two benzene rings.
  • the second compound has at least one benzene ring in its structure.
  • the catalyst is tris(dibenzylideneacetone) dipalladium, tri-tert-butylphosphine ⁇ tetrafluoroborate, sodium tert-butoxide and toluene.
  • the present invention also provides a display device, which includes a substrate, a first electrode layer, an injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a second electrode layer.
  • the first electrode layer is provided on the substrate.
  • the injection layer is provided on the first electrode layer.
  • the hole transport layer is provided on the injection layer.
  • the light-emitting layer is provided on the hole transport layer.
  • the electron transport layer is provided on the light-emitting layer.
  • the second electrode layer is provided on the electron transport layer.
  • the light-emitting layer includes the thermally activated delayed fluorescent material as described above.
  • the material of the injection layer is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene.
  • the material of the hole transport layer is 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline]. Therefore, the material of the electron transport layer is 1,3,5-tris(3-(3-pyridyl)phenyl)benzene.
  • the advantages of the present invention are: a thermally activated delayed fluorescent material in the present invention, the two benzene rings in its molecular structure are connected by a saturated seven-membered ring, which can effectively inhibit the ⁇ - ⁇ stacking between molecules, thereby obtaining high Photoluminescence quantum efficiency (PLQY), and its electron donating ability is between diphenylamine and acridine, which can effectively reduce the overlap of HOMO and LUMO between the electron acceptor and the electron donor, and obtain the lowest singlet and
  • the thermally activated delayed fluorescent material with a small triple energy level difference greatly reduces the phenomenon of luminescence quenching and improves the working efficiency of the display device.
  • the preparation method of the thermally activated delayed fluorescent material in the present invention has simple process, easy purification and high yield.
  • the light-emitting layer contains the thermally activated delayed fluorescent material, so that the fluorescent efficiency of the light-emitting layer is higher and the stability is better, thereby also improving the luminous efficiency and service life of the display device.
  • Fig. 1 is a preparation process of thermally activated delayed fluorescent material in an embodiment of the present invention
  • Figure 2 is a preparation process of the step of forming an electron donor in an embodiment of the present invention
  • Figure 3 is a fluorescence emission spectrum of a thermally activated delayed fluorescent material in an embodiment of the present invention.
  • FIG. 4 is a layered structure diagram of a display device in an embodiment of the present invention.
  • Injection layer 103 Hole transport layer 104;
  • Electron transport layer 106 Light emitting layer 105; Electron transport layer 106;
  • the second electrode layer 107 The second electrode layer 107.
  • the molecular structure of the thermally activated delayed fluorescent material provided in the embodiment of the present invention is a D-A structure formed by the reaction of an electron donor (D) and an electron acceptor (A).
  • the molecular structure of the electron donor (D) includes at least two benzene rings and a seven-membered ring connected between the two benzene rings, and its molecular structure includes one of the following structures:
  • the molecular structure of the electron acceptor (A) includes one of the following structures:
  • thermoly activated delayed fluorescent materials of DA structure can be combined, and the thermally activated delayed fluorescent materials are used as luminescent guests.
  • organic electroluminescent devices organic electroluminescent devices with higher efficiency and performance can be prepared.
  • the embodiment of the present invention also provides a method for preparing the thermally activated delayed fluorescent material.
  • the compound with the electron donor (D) is 5-(4-bromophenyl)-5H-dibenzo[b,f]cycloheximide, which has the electron acceptor
  • the compound of (A) is 2-(4,4,5,5-tetramethyl-1,3,2-1,3,2-dioxoborolan-2-yl)-anthraquinone, the The molecular structural formula of the target thermally activated delayed fluorescent material prepared by the preparation method is:
  • the thermally activated delayed fluorescent material of this molecular structure is one of the above 24 kinds of thermally activated delayed fluorescent materials of D-A structure.
  • the preparation process is shown in Figure 1, and the specific preparation steps are as follows:
  • Step S10) Forming an electron donor (D):
  • the first compound iminodibenzyl and the second compound p-bromoiodobenzene react under the action of a catalyst to synthesize the compound 5-(4-bromo) having an electron donor (D) Phenyl)-5H-dibenzo[b,f]cycloheximine.
  • Step S20 Synthesis of the first target: in a 250mL three-necked flask, add 5-(4-bromophenyl)-5H-dibenzo[b,f]cyclohexanimine (3.49g, 10mmol), 2 -(4,4,5,5-tetramethyl-1,3,2-1,3,2-dioxoborolan-2-yl)-anthraquinone (3.34g, 10mmol), 50mL of toluene And 20mL of 2.5M potassium carbonate aqueous solution, and use argon for pumping.
  • 5-(4-bromophenyl)-5H-dibenzo[b,f]cyclohexanimine 3.49g, 10mmol
  • 2 -(4,4,5,5-tetramethyl-1,3,2-1,3,2-dioxoborolan-2-yl)-anthraquinone 3.34g, 10mmol
  • Step S30) Extract the first target; after the mixed solution is cooled to room temperature, it is extracted three times with dichloromethane and washed three times with water, and then the extract obtained after three extractions is dried and filtered with anhydrous sodium sulfate and spin-dried to obtain The first target.
  • Step S40 Purify the first target; use 200-300 mesh silica gel column chromatography, and use petroleum ether and dichloromethane (volume ratio of 1:1) as eluents to separate and purify the product, and finally obtain 4.05 g
  • the delayed fluorescent material is thermally activated, and the yield is 85%.
  • the compound with the electron donor (D) used is 5-(4-bromophenyl)-5H-dibenzo[b,f]cycloheximine, which has an electron acceptor
  • the compound of body (A) is 2-(4,4,5,5-tetramethyl-1,3,2-1,3,2-dioxoborolan-2-yl)-anthraquinone, but It is not limited to these two compounds. In other embodiments of the present invention, it can also be other compounds, but the preparation methods are basically the same, so they are not listed here.
  • the first compound and the second compound are reacted to synthesize a compound with an electron donor (D) under the action of a catalyst.
  • the preparation process of the step of forming an electron donor is as follows As shown in Figure 2, the specific preparation steps are as follows:
  • Step S11) Synthesis of the second target: In a 100mL Schlenk bottle, add iminodibenzyl (1.95g, 10mmol), p-bromoiodobenzene (4.24g, 10mmol), tris(dibenzylidene) Acetone) two palladium (0.18g, 0.2mmol), tri-tert-butylphosphine ⁇ tetrafluoroborate (0.23g, 0.8mmol) and sodium tert-butoxide (2.40g, 25mmol), then use argon for pumping , And adding 40 mL of anhydrous and oxygen-free toluene, the reaction solution is fully reacted in an argon atmosphere to obtain a mixed solution, and the mixed solution contains the second target produced by the reaction.
  • Step S12) Extract the second target; after the mixed solution is cooled to room temperature, it is extracted three times with dichloromethane and washed three times with water, and then the extract obtained after three extractions is dried, filtered and concentrated with anhydrous sodium sulfate to obtain the second Two target objects.
  • Step S13) Purify the second target; use 200-300 mesh silica gel column chromatography, and use petroleum ether and dichloromethane (volume ratio 1:1) as eluents to separate and purify the product to obtain 3.22 g
  • the compound 5-(4-bromophenyl)-5H-dibenzo[b,f]cycloheximine of the electron donor (D) has a yield of 92%.
  • the first compound is iminodibenzyl
  • the second compound is p-bromoiodobenzene, but it is not limited to these two compounds. In other embodiments of the present invention, it can be used as required. Adjusted to other compounds, but the preparation method is basically the same, so I won't list them all here.
  • the fluorescence emission spectrum of the thermally activated delayed fluorescent material prepared in the embodiment of the present invention is shown in FIG. 3. It is based on the calculated photoluminescence peak (PL Peak), lowest singlet state (S 1 ), lowest triplet energy level (T 1 ), lowest singlet and triplet energy level difference ( ⁇ EST), and photoluminescence peak calculated based on the B3LYP theory.
  • Luminous quantum efficiency (PLQY) is shown in Table 1:
  • the two benzene rings in the molecular structure are connected by a saturated seven-membered ring, which can effectively inhibit the ⁇ - ⁇ stacking between molecules, thereby obtaining high photoinduced Luminous quantum efficiency (PLQY), and its electron donating ability is between diphenylamine and acridine, which can effectively reduce the overlap of HOMO and LUMO between the electron acceptor and the electron donor, and obtain the lowest singlet and triplet energy
  • PLQY photoinduced Luminous quantum efficiency
  • acridine is between diphenylamine and acridine, which can effectively reduce the overlap of HOMO and LUMO between the electron acceptor and the electron donor, and obtain the lowest singlet and triplet energy
  • the thermally activated delayed fluorescent material with a small level difference greatly reduces the phenomenon of luminescence quenching and improves the working efficiency of the display device.
  • the method for preparing a thermally activated delayed fluorescent material provided in the embodiment of the present invention has a simple process, easy purification and high yield.
  • An embodiment of the present invention also provides a display device.
  • the display device includes a substrate 101, a first electrode layer 102, an injection layer 103, a hole transport layer 104, and a light emitting layer 105. , An electron transport layer 106 and a second electrode layer 107.
  • the substrate 101 is a glass substrate for protecting the overall structure of the display device 100.
  • the first electrode layer 102 is disposed on the substrate 101, and is made of indium tin oxide transparent conductive glass for transmitting current.
  • the injection layer 103 is disposed on the first electrode layer 102, and its material is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaaza Triphenylene (HATCH) is used to effectively inject hole energy from the first electrode layer 102 into the device.
  • HATCH 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaaza Triphenylene
  • the hole transport layer 104 is provided on the injection layer 103, and its material is 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), which is used to The holes injected from the electrode are transported to the light-emitting layer 105.
  • the light-emitting layer 105 is disposed on the hole transport layer 104, and its material includes the thermally activated delayed fluorescent material, which converts electrical energy into light energy, thereby providing a light source for the display device 100.
  • the electron transport layer 106 is provided on the light-emitting layer 105, and its material is 1,3,5-tris(3-(3-pyridyl)phenyl)benzene (Tm3PyPB) for electrons injected from the electrode To the light-emitting layer 105.
  • the second electrode layer 107 is disposed on the electron transport layer 106, and its material is lithium fluoride or aluminum.
  • the applied voltage energy will drive electrons and holes to be injected into the light-emitting layer 104 from the hole transport layer 103 and the electron transport layer 105 respectively, and in the When the light-emitting layer 104 meets and combines, the so-called electron-hole recombination is formed.
  • a chemical molecule is excited by external energy, if the electron spin is paired with the ground state electron, it is a singlet state, and the light released is so-called fluorescence. Conversely, if the spins of the excited state electrons and the ground state electrons are not paired and parallel, it is called a triplet state, and the light emitted is so-called phosphorescence.
  • a performance test was performed on the final product display device 100 containing the thermally activated delayed fluorescent material. This test mainly detects the highest brightness, electroluminescence peak (EL Peak) and the maximum external quantum efficiency. The specific data is shown in Table 2.
  • the current, brightness, and voltage characteristics of the device are completed by the Keithley source measurement system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with a calibrated silicon photodiode, and the electroluminescence spectrum is measured by the French JY company SPEX CCD3000 spectrometer Yes, all measurements are done in room temperature atmosphere.
  • the Keithley source measurement system Kelvin 2400 Sourcemeter, Keithley 2000 Currentmeter
  • the electroluminescence spectrum is measured by the French JY company SPEX CCD3000 spectrometer Yes, all measurements are done in room temperature atmosphere.
  • the near-infrared photothermally activated delayed fluorescent material of the present invention has excellent light-emitting performance, and the light-emitting layer 105 made of it has higher fluorescent efficiency and better stability, thereby also improving the light-emitting efficiency of the display device 100 and Service life.
  • the light-emitting layer of the display device contains the thermally activated delayed fluorescent material, so that the fluorescent efficiency of the light-emitting layer is higher, and the stability is better, thereby also improving the display device The luminous efficiency and service life.

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Abstract

L'invention concerne un matériau à fluorescence retardée activé thermiquement, un procédé de préparation correspondant et un dispositif d'affichage. Le matériau à fluorescence retardée activé thermiquement comprend un donneur d'électrons et un accepteur d'électrons, le donneur d'électrons comprenant au moins deux cycles benzéniques et un cycle à sept chaînons lié entre les deux cycles benzéniques. Le procédé de préparation implique des processus simples, une purification facile et produit un haut rendement. Une couche luminescente dans le dispositif d'affichage contient le matériau à fluorescence retardée activé thermiquement.
PCT/CN2019/088078 2019-04-29 2019-05-23 Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif d'affichage WO2020220414A1 (fr)

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