WO2020215439A1 - Matériau à fluorescence retardée rouge activé thermiquement, procédé de préparation correspondant, et dispositif électroluminescent - Google Patents

Matériau à fluorescence retardée rouge activé thermiquement, procédé de préparation correspondant, et dispositif électroluminescent Download PDF

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WO2020215439A1
WO2020215439A1 PCT/CN2019/088780 CN2019088780W WO2020215439A1 WO 2020215439 A1 WO2020215439 A1 WO 2020215439A1 CN 2019088780 W CN2019088780 W CN 2019088780W WO 2020215439 A1 WO2020215439 A1 WO 2020215439A1
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thermally activated
activated delayed
delayed fluorescent
fluorescent material
electron
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PCT/CN2019/088780
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English (en)
Chinese (zh)
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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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Publication of WO2020215439A1 publication Critical patent/WO2020215439A1/fr

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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
    • C07D401/02—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 two hetero rings
    • C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C09K2211/1018—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 field of display technology, in particular to a red thermally activated delayed fluorescent material, a preparation method thereof, and an electroluminescent device.
  • OLEDs Organic light-emitting diodes
  • OLEDs due to active light emission, large viewing angle, fast response speed, wide temperature adaptation range, low driving voltage, low power consumption, high brightness, simple production process, light and thin, and can
  • the advantages of flexible display and other advantages have shown great application prospects in the field of OLED display and lighting, attracting the attention of scientific researchers and companies.
  • Samsung and LG have implemented OLEDs in mobile phones.
  • 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.
  • the ratio of singlet and triplet excitons is 1:3, while traditional fluorescent materials can only use singlet excitons to emit light. Therefore, traditional fluorescent
  • the OLED theoretical internal quantum efficiency of the material is 25%. Due to the spin-orbit coupling effect of heavy atoms, metal complex phosphorescent materials can achieve 100% utilization of singlet excitons and triplet excitons; and are now also used in red and green OLED display devices .
  • phosphorescent materials usually use heavy metals such as iridium, platinum, osmium and other precious metals, which are not only costly, but also highly toxic. In addition, efficient and long-life phosphorescent metal complex materials are still a great challenge.
  • red thermally activated delayed fluorescent materials TADF
  • ⁇ EST singlet and triplet energy difference
  • PLQY high photoluminescence quantum yield
  • EQE external quantum efficiency
  • the present invention provides a red thermally activated delayed fluorescent material, a preparation method thereof, and an electroluminescent device.
  • the red thermally activated delayed fluorescent molecules have rigid and large planar properties, which can effectively inhibit the reduction of the radiation transition rate due to the energy gap regulation.
  • the carbonyl group in the anthrylimide structure can increase the radiation transition rate of the molecule to obtain high Photoluminescence quantum yield (PLQY).
  • the present invention provides a red thermally activated delayed fluorescent material, including an electron donor and an electron acceptor, wherein the electron acceptor contains an anthrylimide structure.
  • the structure of the red thermally activated delayed fluorescent material is as follows:
  • the group R includes one of an alkyl group, an alkoxy group, and an aromatic group; and the group D is an electron donor.
  • the structure of the electron donor includes one of the following structures:
  • the present invention also provides a preparation method for preparing the red thermally activated delayed fluorescent material.
  • the preparation method includes the following steps: preparing an intermediate including an electron acceptor and an electron acceptor connected to the intermediate. The bromo group on the; the electron acceptor has an anthrylimide structure; the intermediate and the organic acid with the electron donor, the sodium tetrahydrofuran carbon solution are added to the three-necked flask, and carried out with argon Ventilate; add tetrakis(triphenylphosphorus) palladium to the three-necked flask, reflux for 24h at a temperature of 75°C-85°C, and cool to room temperature to obtain a mixed solution; use the mixed solution Dichloromethane was extracted several times, and washed with distilled water after each extraction to obtain an extract; the extract was dried with anhydrous sodium sulfate, filtered, spin-dried, and then column chromatography was performed with 200-300 mesh silica gel and used The elu
  • the step of preparing the intermediate includes adding 7-bromophenylisobenzopyran-1,3-dione, an organic amine with an R group, and ethanol to the application.
  • the group R includes one of an alkyl group, an alkoxy group, and an aromatic group; argon is passed into the Schranke flask, and the Schranke flask is heated under the protection of argon.
  • the reflux reaction is carried out, and the reaction time is 12-24 hours to obtain the first mixed solution; the first mixed solution is extracted with dichloromethane several times, and each extraction is washed with distilled water to obtain the first extract; The first extract is dried with anhydrous sodium sulfate, filtered, and spin-dried, and then column chromatography is performed with 200-300 mesh silica gel and eluted with eluent to obtain the intermediate.
  • the present invention also provides an electroluminescent device, which includes the red thermally activated delayed fluorescent material.
  • the electroluminescent device includes a first electrode; an electron injection layer provided on the first electrode; a hole transport layer provided on the electron injection layer; a light emitting layer , Arranged on the hole transport layer, the material used for the light emitting layer includes the red thermally activated delayed fluorescent material; an electron transport layer, arranged on the light emitting layer; a second electrode, arranged on the electron transport layer.
  • the light-emitting layer further includes 4,4'-N,N'-dicarbazole biphenyl.
  • the first electrode is an anode, and the material used is indium tin oxide; the second electrode is a cathode, and the material used is one of lithium fluoride or aluminum.
  • the material used for the electron injection layer is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene
  • the material used for the electron transport layer is 1,3,5-tris (3-(3-pyridyl) phenyl) benzene; the material used for the hole transport layer is 4,4'-cyclohexyl two [N, N-bis(4-methylphenyl)aniline].
  • the electron acceptor is an anthracene nucleus acceptor, that is, the electron acceptor contains an anthrylimide structure, so that the red thermally activated delayed fluorescent molecule has rigid and large plane characteristics, and can effectively inhibit the
  • the energy gap rule reduces the radiation transition rate, and the carbonyl group in the anthrylimide structure can increase the radiation transition rate of the molecule to obtain high photoluminescence quantum yield (PLQY).
  • the preparation method of the red thermally activated delayed fluorescent material of the present invention can effectively improve the synthesis efficiency.
  • the electroluminescent device of the present invention has the red thermally activated delayed fluorescent material of the present invention. Since the anthracene itself has a P-type delayed fluorescence characteristic in the anthrylimide structure, it can effectively suppress the efficiency roll-off of the device, thereby improving the electrical The efficiency of the electroluminescent device can effectively improve the luminous efficiency.
  • Fig. 1 is a fluorescence spectrum diagram of a red thermally activated delayed fluorescent material prepared by a preparation method in an embodiment of the present invention.
  • Fig. 2 is a structural diagram of an electroluminescent device in an embodiment of the present invention.
  • the red thermally activated delayed fluorescent material of the present invention includes an electron donor and an electron acceptor, wherein the electron acceptor contains an anthrylimide structure.
  • the red thermally activated delayed fluorescent material has the following general structural formula:
  • the group R includes one of an alkyl group, an alkoxy group, and an aromatic group; and the group D is an electron donor.
  • the structure of the electron donor includes one of the following structures;
  • red thermally activated delayed fluorescent material will be further explained below in conjunction with the preparation method of the red thermally activated delayed fluorescent material of the present invention.
  • the preparation of the target compound 1 (a red thermally activated delayed fluorescent material of the present invention) is taken as an example to illustrate the preparation method of the red thermally activated delayed fluorescent material of the present invention in detail.
  • the general structure of the target compound is as follows:
  • the preparation method of the red thermally activated delayed fluorescent material of the present invention includes the following steps:
  • An intermediate is prepared, the intermediate includes an electron acceptor and a bromo group connected to the electron acceptor; the electron acceptor has an anthrylimide structure; and the step of preparing the intermediate includes 7 -Bromophenylisobenzopyran-1,3-dione, organic amine with R group and ethanol are added to Schlenk bottle, said group R includes alkyl group, alkoxy group and aromatic group In one of them, in the preparation of target compound one, the organic amine of the R group is tert-butylamine. Pour argon gas into the Schlenk flask, and heat the Schrank flask under the protection of argon to perform reflux reaction.
  • the reaction time is 12-24 hours to obtain a first mixed solution; Extract with dichloromethane several times, wash with distilled water after each extraction to obtain the first extract; dry the first extract with anhydrous sodium sulfate, filter, spin dry, and then use 200-300 mesh silica gel Column chromatography and elution with eluent to obtain the intermediate: 7-bromo-2-tert-butyl-diphenylisoquinoline-1,3-dione.
  • the organic acid with the electron donor is 4-(9,9-dimethylacridine)-phenylboronic acid.
  • Tetrakis(triphenylphosphorus) palladium was added to the three-necked flask, and the reaction was refluxed at a temperature of 75° C.-85° C. for 24 hours, and a mixed solution was obtained after cooling to room temperature.
  • the mixed solution is extracted with dichloromethane several times, and washed with distilled water after each extraction to obtain an extract.
  • the extract is dried with anhydrous sodium sulfate, filtered, and spin-dried, and then column chromatography is performed with 200-300 mesh silica gel and eluted with eluent to obtain the target compound one, which is a red color of the present invention.
  • the thermally activated delayed fluorescent material has a yield of 85%.
  • target compound two a red thermally activated delayed fluorescent material of the present invention
  • preparation method of the red thermally activated delayed fluorescent material of the present invention is described in detail.
  • the general structure of the target compound is as follows:
  • the preparation method of the red thermally activated delayed fluorescent material of the present invention includes the following steps:
  • An intermediate is prepared, the intermediate includes an electron acceptor and a bromo group connected to the electron acceptor; the electron acceptor has an anthrylimide structure; and the step of preparing the intermediate includes 7 -Bromophenylisobenzopyran-1,3-dione, organic amine with R group and ethanol are added to Schlenk bottle, said group R includes alkyl group, alkoxy group and aromatic group In one of them, in the preparation of the second target compound, the organic amine of the R group is p-tert-butylaniline. Pour argon gas into the Schlenk flask, and heat the Schrank flask under the protection of argon to perform reflux reaction.
  • the reaction time is 12-24 hours to obtain a first mixed solution; Extract with dichloromethane several times, wash with distilled water after each extraction to obtain the first extract; dry the first extract with anhydrous sodium sulfate, filter, spin dry, and then use 200-300 mesh silica gel Column chromatography and elution with eluent to obtain the intermediate: 7-bromo-2-tert-butyl-diphenylisoquinoline-1,3-dione.
  • the organic acid with the electron donor is 4-(9,9-dimethylacridine)-phenylboronic acid.
  • Tetrakis(triphenylphosphorus) palladium was added to the three-necked flask, and the reaction was refluxed at a temperature of 75° C.-85° C. for 24 hours, and a mixed solution was obtained after cooling to room temperature.
  • the mixed solution is extracted with dichloromethane several times, and washed with distilled water after each extraction to obtain an extract.
  • the extract is dried with anhydrous sodium sulfate, filtered, and spin-dried, and then column chromatography is performed with 200-300 mesh silica gel and eluted with eluent to obtain the target compound one, which is a red color of the present invention.
  • Thermally activated delayed fluorescent material with a yield of 88%
  • the red thermally activated delayed fluorescent material By preparing the red thermally activated delayed fluorescent material by the preparation method of this embodiment, the red thermally activated delayed fluorescent material can be effectively synthesized, and the synthesis efficiency can be improved.
  • the red thermally activated delayed fluorescent material obtained by the preparation method of this embodiment is subjected to spectral experiments and photophysical data detection . Obtain the fluorescence spectrum shown in Figure 1 and the photophysical data shown in Table 1.
  • Table 1 shows the photophysical data of the red thermally activated delayed fluorescent material of the present invention.
  • the effective wavelength range of the target compound 1 of the present invention is between 680-800 nm, and the effective wavelength range of the target compound 2 is between 700-850 nm. Therefore, the emission spectrum of the molecule can be adjusted within this range. It can be seen from Table 1 that the red thermally activated delayed fluorescent material of the present invention has a smaller minimum singlet state and triplet energy difference ( ⁇ E ST ).
  • the present invention also provides an electroluminescent device, which includes the red thermally activated delayed fluorescent material.
  • the electroluminescent device includes a first electrode 1, an electron injection layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a second electrode 6.
  • the electron injection layer 2 is provided on the first electrode 1;
  • the hole transport layer 3 is provided on the electron injection layer 2;
  • the light emitting layer 4 is provided on the hole transport layer 3 ,
  • the material used for the light-emitting layer 4 includes the red thermally activated delayed fluorescent material and 4,4'-N,N'-dicarbazole biphenyl, 4,4'-N,N'-dicarbazole biphenyl is The host molecule is doped with the red thermally activated delayed fluorescent material;
  • the electron transport layer 5 is provided on the light-emitting layer 4;
  • the second electrode 6 is provided on the electron transport layer 5.
  • the first electrode 1 is an anode, and the material used is indium tin oxide; the second electrode 6 is a cathode, and the material used is one of lithium fluoride or aluminum.
  • the material used for the electron transport layer 5 is 1,3,5-tris(3-(3-pyridyl)phenyl)benzene; the material used for the hole transport layer 3 is 4,4'-cyclohexylbis[N ,N-bis(4-methylphenyl)aniline], the material used for the electron injection layer 2 is 2,3,6,7,10,11-hexacyano-1,4,5,8,9, 12-hexaazatriphenylene.
  • Table 2 is a performance data table of the electroluminescent device 10 using target compound one or using target compound two.
  • the red thermally activated delayed fluorescent material is used in the light-emitting layer 4 to effectively manufacture a red electroluminescent device and improve the luminous efficiency of the red electroluminescent device.

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

Abstract

L'invention concerne un matériau à fluorescence retardée rouge activé thermiquement, un procédé de préparation correspondant, et un dispositif électroluminescent. Le matériau à fluorescence retardée rouge activé thermiquement comprend un donneur d'électrons et un accepteur d'électrons, et l'accepteur d'électrons comprend une structure d'anthrylimide. La structure d'anthrylimide dans l'accepteur d'électrons permet à des molécules à fluorescence retardée rouge activées thermiquement d'avoir des caractéristiques planaires rigides et élevées, et peut inhiber de manière efficace la réduction de la vitesse de transition par rayonnement provoquée par la loi d'écart énergétique ; de plus, le carbonyle dans la structure d'anthrylimide peut augmenter la vitesse de transition par rayonnement des molécules ; ce qui permet d'obtenir un rendement quantique de photoluminescence (PLQY) élevé.
PCT/CN2019/088780 2019-04-26 2019-05-28 Matériau à fluorescence retardée rouge activé thermiquement, procédé de préparation correspondant, et dispositif électroluminescent WO2020215439A1 (fr)

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CN201910342009.3A CN109970711B (zh) 2019-04-26 2019-04-26 红色热激活延迟荧光材料及其制备方法、电致发光器件

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CN114436941A (zh) * 2022-01-25 2022-05-06 东南大学成贤学院 一种可溶液加工的激基复合物主体材料、制备方法及应用

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CN110372701A (zh) * 2019-07-09 2019-10-25 武汉华星光电半导体显示技术有限公司 一种热活化延迟荧光分子及其制备方法、电致热激活延迟荧光器件
CN111116470A (zh) * 2020-01-02 2020-05-08 深圳大学 聚集态诱导室温磷光橙红色电致发光化合物及其制备方法和应用
CN114989080B (zh) * 2022-05-23 2023-12-22 井冈山大学 一种荧光化合物及其制备方法和应用以及一种荧光试条

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