WO2023179092A1 - Dérivé de bore-azote fusionné au carbonyle, son procédé de préparation et son utilisation - Google Patents

Dérivé de bore-azote fusionné au carbonyle, son procédé de préparation et son utilisation Download PDF

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WO2023179092A1
WO2023179092A1 PCT/CN2022/137170 CN2022137170W WO2023179092A1 WO 2023179092 A1 WO2023179092 A1 WO 2023179092A1 CN 2022137170 W CN2022137170 W CN 2022137170W WO 2023179092 A1 WO2023179092 A1 WO 2023179092A1
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compound
boron
nitrogen
carbonyl
formula
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PCT/CN2022/137170
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Chinese (zh)
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张晓宏
程迎春
王凯
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苏州大学
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    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • 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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • 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
    • C09K2211/1014—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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
    • 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

Definitions

  • the invention belongs to the field of light-emitting devices and relates to a carbonyl-condensed boron-nitrogen derivative and its preparation method and application. Specifically, it is used in organic electroluminescent devices.
  • Organic light-emitting diodes are widely used in flexible screen displays, daily lighting and other fields. Research on developing organic light-emitting materials with higher color purity and reduction will be extremely important for enhancing high-definition and ultra-thin display technologies.
  • thermally activated delayed fluorescence (TADF) materials have become a current research hotspot due to their low cost and high efficiency.
  • Thermal-activated delayed fluorescent materials often achieve a smaller singlet triplet band gap ⁇ E ST by designing twisted donor-acceptor segments, but this inevitably leads to an increase in molecular relaxation, resulting in poor color purity.
  • Multiple resonance molecular design strategies proposed in recent years provide effective solutions for the development of devices with higher radiative transition rates, smaller half-peak widths, and higher color purity.
  • DABNA-1 (5,9-diphenyl-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene)
  • the boron-nitrogen (BN) system of the parent core uses QAO (quinolino[3,2,1-de]acridine-5,9-dione) as the parent core of the nitrogen dione structure, with 2a(5,9-dioxa-13b -boranaphtho[3,2,1-de]anthracene) is the boron oxygen molecular structure of the parent core.
  • QAO quinolino[3,2,1-de]acridine-5,9-dione
  • 2a(5,9-dioxa-13b -boranaphtho[3,2,1-de]anthracene) is the boron oxygen molecular structure of the parent core.
  • the boron-oxygen system is often designed as the acceptor fragment of the molecule, and the nitrogen-carbonyl system is increasingly ignored due to the obvious extension of the half-peak width in the device.
  • the current research on multiple resonances mainly focuses on the molecular structure with the BN system as the core.
  • the BN molecular system has achieved higher EQE (external quantum efficiency) and narrower FWHM (width at half maximum) after years of development, it faces serious efficiency roll-off problems, which hinders its commercial development.
  • EQE internal quantum efficiency
  • FWHM width at half maximum
  • the present invention aims to provide a carbonyl-fused boron-nitrogen derivative and its preparation method and application, so as to obtain an excellent device with high efficiency, high color purity and low efficiency roll-off and with commercial application potential.
  • the carbonyl-fused boron-nitrogen derivative is fused with a carbonyl group that affects the electron cloud distribution of its HOMO and LUMO energy levels on the basis of the boron-nitrogen structure.
  • boron-nitrogen derivative has the structure shown below:
  • X is selected from oxygen, sulfur, selenium, fluorenyl, silicon or diphenyl;
  • R 1 to R 6 are independently selected from hydrogen, cyano, methyl, tert-butyl, diphenylamine, 3,6-di-tert-butyldiphenylamine, carbazolyl, 3,6-di-tert-butylcarbazole base, phenothiazinyl, phenoxazinyl, triazinyl, fluorenonyl or 9,9'-spirobifluorenyl.
  • a second aspect of the present invention provides a method for preparing the above-mentioned carbonyl-fused boron-nitrogen derivative, including the following steps:
  • X 1 and X 2 are selected from fluorine, chlorine, bromine or iodine;
  • step S1 the coupling reaction is carried out in organic solvent I, the reaction temperature is 100-120°C, and the reaction time is 10-20h; preferably, the reaction temperature is 110°C, and the reaction time is 12h.
  • organic solvent I is selected from toluene, tetrahydrofuran, 1,4-dioxane or dimethyl sulfoxide solvent.
  • a catalyst ligand is added before the coupling reaction, and the catalyst ligand is tBu 3 P (tri-tert-butylphosphine), tBu 3 P-HBF 4 (tri-tert-butyl tetrafluoroborate).
  • phosphine tri-tert-butylphosphine
  • tBu 3 P-HBF 4 tri-tert-butyl tetrafluoroborate
  • phosphine) S-phos (2-dicyclohexylphosphonium-2',6'-dimethoxybiphenyl) or X-phos (2-dicyclohexylphosphonium-2',4',6'-triiso propylbiphenyl)
  • the molar ratio of catalyst ligand to palladium catalyst is 1-10:1.
  • the palladium catalyst is Pd(dba) 2 (bis(dibenzylacetyl)palladium), Pd 2 (dba) 3 (tris(dibenzylideneacetone) dipalladium) or Pd(OAc) 2 (acetic acid Palladium),
  • the base is sodium tert-butoxide, potassium tert-butoxide, sodium carbonate, potassium carbonate or cesium carbonate.
  • step S1
  • step S2 the specific operation of step S2 is as follows: under a protective atmosphere, add anhydrous tert-butylbenzene solvent or mesitylene solvent to the compound II, add organic lithium at -50 ⁇ -30°C, 50 React at -70°C for 0.8-2h; add boron tribromide at -50 ⁇ -30°C, react at room temperature (25 ⁇ 5°C) for 0.8-2h; add N,N-diisobutyrate under ice bath (around 0°C) Propylethylamine, react at 120-140°C for 10-20 hours to obtain the boron nitrogen compound.
  • the protective atmosphere is nitrogen, argon or helium.
  • the organic lithium is tert-butyllithium or n-butyllithium.
  • step S2 the molar ratio of organic lithium, boron tribromide, N,N-diisopropylethylamine and compound II is 1-10:1-10:1-10:1.
  • step S3 the oxidation reaction is performed in a mixed solvent of organic solvent II and water.
  • organic solvent II is dichloromethane and/or 1,4-dioxane.
  • step S3 is performed under a protective atmosphere.
  • step S3 the molar ratio of 2,3-dichloro-5,6-dicyanobenzoquinone to the boron nitrogen compound is 5-20:1.
  • a third aspect of the present invention provides the use of the above-mentioned carbonyl-fused boron-nitrogen derivative in organic electroluminescent devices.
  • the present invention introduces carbonyl groups on the basis of B/N molecules and proposes a preparation method for a new type of carbonyl-fused boron-nitrogen derivatives. and its application in organic electroluminescent devices.
  • the optoelectronic devices prepared by it can also achieve the goals of high efficiency, high color purity and low efficiency roll-off.
  • the results show that the introduction of carbonyl groups in BNOCZ not only enhances the SOC of S1 (first singlet state) and T2 (second triplet state), improves k RISC (3 ⁇ 10 6 s -1 ), but also ensures a smaller device half width.
  • This system expands the TADF material molecule library, promotes the application of organic light-emitting diodes with high efficiency, high color purity and low efficiency roll-off, and enables the design of thermally activated delayed fluorescence OLEDs (organic light-emitting diodes) closer to commercial needs in the future. Materials provide a certain foundation.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device in a test example.
  • Example 1 is used as the preparation and performance evaluation of organic electroluminescent devices doped with fluorescent dyes.
  • a glass plate with an indium tin oxide (ITO) transparent electrode is used as the substrate.
  • the substrate is striped and has a width of 3mm.
  • the surface was treated with ozone ultraviolet light.
  • Each layer was vacuum evaporated on the washed substrate using a vacuum evaporation method to produce an organic electroluminescent device with a light-emitting area of 9 mm2 as shown in the cross-sectional view in Figure 1.
  • the aforementioned glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1 ⁇ 10 -4 Pa. Then, on the glass substrate shown as 1 in FIG. 1 , a hole transport layer 2 , an electron blocking layer 3 , a light emitting layer 4 and an electron transport layer 5 are sequentially formed as organic compound layers, and then a cathode layer 6 is formed.
  • TAPC 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline]
  • TCTA 4,4 was vacuum evaporated with a film thickness of 10 nm ',4"-tris(carbazol-9-yl)triphenylamine
  • mCP 1,3-di-9-carbazolylbenzene
  • the film is formed by resistance heating.
  • the heating compound is vacuum evaporated at a film formation rate of 0.3-0.5nm.
  • a metal mask is arranged orthogonal to the ITO stripes to form the film cathode 6.
  • the cathode layer 6 is formed with a thickness of 1nm and 100nm respectively.
  • the film thickness is a two-layer structure formed by vacuum evaporation of lithium fluoride and aluminum. Each film thickness is measured with a stylus type film thickness meter (DEKTAK).
  • the device is sealed in a nitrogen atmosphere glove with a water and oxygen concentration of 1 ppm or less. Inside the box. A glass sealing cover and the aforementioned film-forming substrate epoxy ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used for sealing.
  • the luminescence performance was evaluated using a Spectrascan PR650 luminance meter, and the current-voltage characteristics were measured using a computer-controlled Keithley 2400 digital source meter.
  • the CIE color coordinate value, maximum brightness (cd/m 2 ), external quantum efficiency (%), and power efficiency (lm/W) with changes in applied DC voltage were measured.
  • the measured values of the fabricated device were (0.222, 0.703), 11100cd/m 2 , 24.1% and 71.3lm/W.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Sont divulgués un dérivé de bore-azote fusionné au carbonyle, son procédé de préparation et son utilisation. Le dérivé de bore-azote fusionné au carbonyle est formé par fusion d'une structure bore-azote avec un groupe carbonyle qui affecte les distributions de nuage d'électrons de celle-ci aux niveaux HOMO et LUMO. L'invention concerne son procédé de préparation et son utilisation dans un dispositif électroluminescent organique. Le système étend une bibliothèque moléculaire de matériau TADF, favorise l'application d'une diode électroluminescente organique ayant une efficacité élevée, une pureté de couleur élevée et un décollement à faible efficacité, et fournit une certaine base pour permettre de concevoir un matériau OLED à fluorescence retardée activé thermiquement qui répond mieux aux exigences de commercialisation dans le futur.
PCT/CN2022/137170 2022-03-22 2022-12-07 Dérivé de bore-azote fusionné au carbonyle, son procédé de préparation et son utilisation WO2023179092A1 (fr)

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CN202210284023.4A CN114773366B (zh) 2022-03-22 2022-03-22 一种羰基稠合的硼氮衍生物及其制备方法和应用
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CN115806563A (zh) * 2021-09-13 2023-03-17 广东阿格蕾雅光电材料有限公司 一类含b-n的有机电致发光材料及其在电致发光器件中的应用
CN114773366B (zh) * 2022-03-22 2023-11-28 苏州大学 一种羰基稠合的硼氮衍生物及其制备方法和应用
CN115433217B (zh) * 2022-08-12 2023-08-25 苏州大学 一种咔唑稠合的硼氮衍生物及其制备方法和应用
CN117683055A (zh) * 2022-08-26 2024-03-12 江苏三月科技股份有限公司 一种含有二苯基取代萘并吡咯结构的含硼有机化合物及其有机电致发光器件

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WO2019235402A1 (fr) * 2018-06-04 2019-12-12 学校法人関西学院 Composés aromatiques polycycliques et polymères de ceux-ci
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
CN112480154A (zh) * 2020-11-26 2021-03-12 深圳大学 一种手性热活化延迟荧光材料及其圆偏振电致发光器件
CN114773366A (zh) * 2022-03-22 2022-07-22 苏州大学 一种羰基稠合的硼氮衍生物及其制备方法和应用

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CN114149458B (zh) * 2021-11-29 2023-01-06 苏州大学 一种b/n类有机电致发光材料及其制备方法与应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019235402A1 (fr) * 2018-06-04 2019-12-12 学校法人関西学院 Composés aromatiques polycycliques et polymères de ceux-ci
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
CN112480154A (zh) * 2020-11-26 2021-03-12 深圳大学 一种手性热活化延迟荧光材料及其圆偏振电致发光器件
CN114773366A (zh) * 2022-03-22 2022-07-22 苏州大学 一种羰基稠合的硼氮衍生物及其制备方法和应用

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