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WO2018120970A1 - Colorant de lumière verte ayant une propriété d'émission induite par agrégation - Google Patents

Colorant de lumière verte ayant une propriété d'émission induite par agrégation Download PDF

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Publication number
WO2018120970A1
WO2018120970A1 PCT/CN2017/105309 CN2017105309W WO2018120970A1 WO 2018120970 A1 WO2018120970 A1 WO 2018120970A1 CN 2017105309 W CN2017105309 W CN 2017105309W WO 2018120970 A1 WO2018120970 A1 WO 2018120970A1
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Prior art keywords
dye
green
green light
light
reaction
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Ceased
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English (en)
Chinese (zh)
Inventor
周鹏程
戴雷
蔡丽菲
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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Guangdong Aglaia Optoelectronic Materials Co Ltd
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • 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
    • C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
    • C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur

Definitions

  • the invention relates to a novel organic color conversion film material for flat display, in particular to a kind of green light dye containing tetraphenylstyrene group having aggregation-inducing luminescent property, which is formed into a film by solution spin coating, and can be applied to a flat display.
  • flat panel displays With the continuous breakthrough of the display industry technology and the increasing market demand, flat panel displays have emerged rapidly with a series of advantages such as small size, light weight, low power consumption, low radiation, and good electromagnetic compatibility, becoming the mainstream of display technology in the 21st century. .
  • the coloring method of flat panel display plays a very important role in its production process. Its quality directly determines the color rendering effect, production cost and service life of flat panel display.
  • the mainstream technology for color display of flat panel display is to print red, green and blue fluorescent material preparation devices.
  • the mainstream technology for color display of flat panel display is to print red, green and blue fluorescent material preparation devices.
  • due to the large difference in lifetime and attenuation of the three primary color fluorescent materials it is easy to cause color cast of color display, and the three primary colors
  • the manufacturing process of the device is complicated and the cost is high.
  • people have proposed a new idea of color conversion, namely "blue source into color”.
  • the "Blue Source into Color” technology uses a blue phosphor with a single high brightness as the backlight.
  • the blue light emitted by the backlight is converted into red and green light after passing through the color conversion film, thereby realizing RGB full color display.
  • This technology not only greatly simplifies the production process of electroluminescent flat panel display, improves the color stability and uniformity of the display, but also significantly reduces the production cost of the display.
  • Materials for color conversion films can be classified into inorganic and organic materials. It has been found that, compared with inorganic phosphors, organic conversion materials not only have higher color conversion efficiency, but also have more saturated colors, so that a wider color gamut can be realized, and raw materials are cheap and easy to obtain, and molecular cutting and modification are easier. For better display.
  • the Leising team used the coumarin dye Coumarin 102 as the green light material, and Lumogen F300 used the red dye to disperse in the PMMA to prepare a green and red light conversion film, which achieved a red light conversion efficiency of more than 10%.
  • the domestic research team has also reported the preparation of organic light conversion films (Reference: Optoelectronics Letters, 2010, 6 (4), 245-248, CN105267059 A, CN103647003 A), which has obtained a wide color gamut and a light conversion rate. High organic light conversion film.
  • the organic fluorescent color conversion film generally disperses an organic fluorescent dye having different colors uniformly in a polymer solid film by ultraviolet curing or thermal curing, and then excites the organic fluorescent color conversion film with a high-brightness blue backlight.
  • the dye molecules realize the color transition, and the converted red, green and background blue light form three primary colors of light, and finally the full color display of the electroluminescent element can be realized.
  • the commonly used organic dye molecules tend to aggregate between the molecules to cause fluorescence quenching, and hardly emit light in the film state, so in these light conversion film materials, the organic dyes are generally at a very low concentration (thousandths of a thousand). Dispersed in a transparent polymer resin, too low a concentration tends to cause insufficient absorption of light by the film. To obtain a sufficient light conversion effect, the thickness of the film must be increased, thereby causing an increase in the thickness of the entire display panel.
  • AIE aggregation-induced luminescence
  • the present invention provides a green light dye molecule having aggregation-induced luminescence (AIE) properties, which is dispersed in a polymer resin such as methyl methacrylate (PMMA) to prepare a light conversion film.
  • AIE aggregation-induced luminescence
  • PMMA methyl methacrylate
  • the present invention applies such AIE type dye molecules to organic light conversion film materials.
  • a green light dye having aggregation-inducing luminescent properties having aggregation-inducing luminescent properties, the molecular structure of which is as described in formula (I),
  • R1 and R2 are independently represented by hydrogen, C1-C4 alkyl or alkoxy
  • Ar is independently represented by a carbon-carbon double bond or a triple bond or a C6-C20 benzene or heterocyclic ring of unregistered.
  • R1 and R2 are the same.
  • R1 and R2 are represented by hydrogen or tert-butyl.
  • the compound of the formula (I) is preferably a compound having the following structure:
  • a phenylmethane derivative is condensed with a benzophenone derivative to prepare a brominated tetrastyrene.
  • a boronic acid ester of tetrastyrene is prepared by a substitution reaction using butyllithium.
  • the target dye molecule GA1 is prepared by a Suzuki coupling reaction.
  • a diphenyl-substituted benzothiadiazole is prepared by a Suzuki coupling reaction.
  • the second step uses bromine to carry out the bromination reaction.
  • the target dye molecule GA2 is prepared by a Suzuki coupling reaction.
  • the light conversion film is composed of the above green light dye and a cured polymer resin.
  • the cured polymer resin is an acrylate, an epoxy resin or a polyurethane.
  • the light conversion film has a total thickness of from 1 to 100 ⁇ m.
  • the application is that the above green light dye and the cured polymer resin are dissolved in toluene, then spin-coated into a film, and dried after curing.
  • An organic light conversion film is prepared, fixed on a backlight, and applied to a flat display to realize full color display.
  • the curing preparation method is heat curing or ultraviolet curing.
  • the backlight is a blue light source
  • the cured polymer resin is a methyl methacrylate (PMMA) polymer resin.
  • the CCF film prepared with GA1 and GA2 has good absorption of background blue light ( ⁇ max ⁇ 450nm), the emitted light is green light, and the fluorescence of GA1 and GA2 in solution is weak (QY ⁇ 50%). It has strong fluorescence after being made into a solid or PMMA film.
  • the present invention applies AIE type dye molecules to organic light conversion film materials, and the dyes have great advantages in solid-state light emission applied to organic light conversion film materials. .
  • Figure 1 is a schematic diagram of the synthetic route of the green light dye GA1 of the present invention
  • Figure 2 is a schematic view showing the synthetic route of the green light dye GA2 of the present invention.
  • FIG. 3 UV-visible absorption spectrum of the green light dye GA1 of the present invention in toluene, dichloromethane and PMMA films and solid state
  • Figure 4 is a fluorescence emission spectrum of the green light dye GA1 of the present invention in a toluene, dichloromethane, and PMMA film and a solid state;
  • Figure 5 is an ultraviolet-visible absorption spectrum of the green light dye GA2 of the present invention in a toluene, dichloromethane, and PMMA film and a solid state;
  • Figure 6 is a fluorescence emission spectrum of the green light dye GA2 of the present invention in a toluene, dichloromethane, and PMMA film and a solid state;
  • Figure 7 is a light conversion film prepared by the green light dye GA1 of the present invention.
  • a phenylmethane derivative is condensed with a benzophenone derivative to prepare a brominated tetrastyrene.
  • a boronic acid ester of tetrastyrene is prepared by a substitution reaction using butyllithium.
  • the target dye molecule GA1 is prepared by a Suzuki coupling reaction.
  • a diphenyl-substituted benzothiadiazole is prepared by a Suzuki coupling reaction.
  • the second step uses bromine to carry out the bromination reaction.
  • the target dye molecule GA2 is prepared by a Suzuki coupling reaction.
  • Synthesis step Compound 1a (commercially available) (5.61 g, 20 mmol) was dissolved in anhydrous THF (100 mL) under nitrogen atmosphere. The reaction mixture was cooled to 0 ° C, and butyl lithium (2.2 M, 14 mL) was slowly added dropwise with stirring. After the completion of the dropwise addition, the mixture was stirred at low temperature for 1 hour, and then Compound 2a (commercially available) (10.45 g, 40 mmol) was added to the reaction mixture, and stirring was continued for 1 hour. The reaction was then allowed to warm to room temperature and stirred overnight.
  • Synthesis step the crude compound 3a obtained in the previous step was dissolved in anhydrous toluene (50 mL) under nitrogen atmosphere, then TSOH.H 2 O (380 mg, 2 mmol) was added to the reaction mixture, and the mixture was heated to reflux for 12 hours, and the compound was detected by TLC. The 3a reaction is complete.
  • Post-reaction treatment The reaction was stopped, and the reaction mixture was poured into water. EtOAc (EtOAc m.
  • the crude product was purified by column chromatography to yieldd pale yellow compound 4a (5.7 g, yield 54.5%).
  • Synthesis step Compound 4a (5.7 g, 10.9 mmol), Pd(dppf)Cl 2 (400 mg, 5%), bis-pinacol borate (4.2 g, 16.4 mmol), potassium acetate (2.1) under nitrogen. g, 21.8 mmol) was dissolved in anhydrous 1,4-dioxane (70 mL), and the reaction mixture was heated to reflux temperature for 12 hours under stirring, and the compound 4a was completely reacted by TLC.
  • Synthesis step To a 250 mL reaction flask was added compound 5a (627 mg, 1.1 mmol), compound 6a (commercially available) (147 mg, 0.5 mmol), Pd 2 (dba) 3 (51 mg, 5%), tri-tert-butylphosphine ( 22 mg, 10%), K 2 CO 3 (304 mg, 2.2 mmol), toluene (5 mL) and water (1 mL). The nitrogen gas was evacuated 3 times, and the temperature was raised to 100 ° C by heating. The temperature was maintained for 12 hours, and the compound 5a was completely reacted by TLC.
  • Synthesis step To a 250 mL reaction flask was added compound 6a (commercially available) (2.93 g, 10 mmol), compound 2b (commercially available) (2.68 g, 22 mmol), tetratriphenylphosphine palladium (1.15 g, 5%), K 2 CO 3 (4.14 g, 30 mmol), toluene (100 mL) and water (20 mL). The nitrogen gas was evacuated 3 times, and the temperature was raised to 80 ° C by heating. The temperature was maintained for 8 hours, and the compound 6a was completely reacted by TLC.
  • the photophysical properties of the green dyes GA1 and GA2 in the solution are to dissolve the corresponding dye in toluene or dichloromethane, the concentration of the solution is 1 ⁇ 10 -5 mol/L, and the dye-based CCF film is the dye and corresponding The proportion of PMMA is dissolved in toluene, spin-coated and then dried.
  • the photophysical properties of the dye film are determined by dissolving the dye in THF and spin-coating to prepare a film.
  • the CCF film prepared with GA1 and GA2 has good absorption of background blue light ( ⁇ max ⁇ 450nm), the emitted light is green light, and the fluorescence of GA1 and GA2 in solution is weak (QY ⁇ 50%).
  • the solid or PMMA film exhibits strong fluorescence and has typical AIE properties.
  • the present invention first applies AIE type dye molecules to organic light conversion film materials, and the dyes are strongly applied to organic light conversion film materials in solid state. Great advantage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un colorant de lumière verte ayant une propriété d'émission induite par agrégation. Le colorant de lumière verte a une structure représentée dans la formule (I). Un test sur les propriétés photophysiques du colorant de lumière verte montre qu'une molécule représentée dans la formule (I), lorsqu'elle est à l'état solide, a un rendement quantique fluorescent élevé et peut être appliquée à des matériaux de film de conversion de lumière à l'aide de lumière verte.
PCT/CN2017/105309 2016-12-27 2017-10-09 Colorant de lumière verte ayant une propriété d'émission induite par agrégation Ceased WO2018120970A1 (fr)

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CN201611224162.9 2016-12-27
CN201611224162.9A CN106867507A (zh) 2016-12-27 2016-12-27 一种具有聚集诱导发光性质的绿光染料

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113308129A (zh) * 2020-02-26 2021-08-27 四川大学 同质多晶的对称二四苯乙烯荧光染料制备及其性能
CN114621159A (zh) * 2022-04-06 2022-06-14 电子科技大学 基于苯并噻二唑的荧光材料、荧光聚合物、荧光纳米粒子以及制备方法和应用
CN115448936A (zh) * 2022-08-19 2022-12-09 三峡大学 N,o-杂环化合物及其合成与应用

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CN106867507A (zh) * 2016-12-27 2017-06-20 广东阿格蕾雅光电材料有限公司 一种具有聚集诱导发光性质的绿光染料
CN106811191A (zh) * 2016-12-27 2017-06-09 广东阿格蕾雅光电材料有限公司 含有聚集诱导发光性质的绿光染料的光转换膜
CN110343081B (zh) * 2019-07-31 2022-09-27 湘潭大学 一种具有聚集诱导发光性质的荧光酸酐类化合物及其制备方法和应用
CN114106015B (zh) * 2021-10-11 2022-12-13 深圳大学 近红外二区发射聚集诱导发光材料及制备方法、应用
CN116854660A (zh) * 2023-05-25 2023-10-10 南京工业大学 水溶性有机荧光分子及其制备方法和在指纹检测中的应用
CN120398792A (zh) * 2025-04-27 2025-08-01 香港中文大学（深圳） 一种高荧光量子产率聚集诱导发光材料及其制备方法和应用

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CN106867507A (zh) * 2016-12-27 2017-06-20 广东阿格蕾雅光电材料有限公司 一种具有聚集诱导发光性质的绿光染料

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CN104673275A (zh) * 2013-10-15 2015-06-03 香港科技大学深圳研究院 一种激活发光材料及其制备方法
CN104877665A (zh) * 2013-12-19 2015-09-02 香港科技大学深圳研究院 具有聚集诱导发光特性的发光材料及其制备方法和应用
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CN106867507A (zh) * 2016-12-27 2017-06-20 广东阿格蕾雅光电材料有限公司 一种具有聚集诱导发光性质的绿光染料

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113308129A (zh) * 2020-02-26 2021-08-27 四川大学 同质多晶的对称二四苯乙烯荧光染料制备及其性能
CN113308129B (zh) * 2020-02-26 2022-01-14 四川大学 同质多晶的对称二四苯乙烯荧光化合物制备方法及其晶体
CN114621159A (zh) * 2022-04-06 2022-06-14 电子科技大学 基于苯并噻二唑的荧光材料、荧光聚合物、荧光纳米粒子以及制备方法和应用
CN114621159B (zh) * 2022-04-06 2023-04-18 电子科技大学 基于苯并噻二唑的荧光材料、荧光聚合物、荧光纳米粒子以及制备方法和应用
CN115448936A (zh) * 2022-08-19 2022-12-09 三峡大学 N,o-杂环化合物及其合成与应用

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