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CN-117447333-B - Pyrenyl blue light material capable of emitting in narrow band, and preparation method and application thereof

CN117447333BCN 117447333 BCN117447333 BCN 117447333BCN-117447333-B

Abstract

The invention belongs to the field of synthesis of organic semiconductors, and discloses a pyrenyl blue light material capable of emitting in a narrow band, and a preparation method and application thereof. The pyrenyl blue light material emitted by the narrow band has a structure shown in a formula (1). The pyrene-based organic functional luminescent material prepared by taking the pyrene intermediate as a precursor has the advantages that biphenyl and triphenylamine or tetraphenylethylene are introduced into 1 and 3 positions of pyrene, and when triphenylamine is taken as a strong electron donating group, biphenyl units substituted at different positions are used for constructing a molecular conformation through space conjugation, and the tetraphenylethylene unit plays an important role in realizing AIE characteristics. The preparation method is simple, the reaction condition is mild, the yield is high, the prepared material has good thermal stability, the (deep) blue light emission and the solid quantum yield are more than 0.7, wherein the maximum peak width is up to 0.9, and the maximum half peak width is 20-50 nm. Suitable for high definition display light emitting devices, and the like.

Inventors

  • FENG XING
  • LIU WEI
  • LI SHAOLING
  • SONG XINYI
  • ZHANG CHENG

Assignees

  • 广东工业大学

Dates

Publication Date
20260512
Application Date
20230818

Claims (7)

  1. 1. A pyrenyl blue light material capable of emitting in a narrow band is characterized by having a structure shown in the following formula (1): When R 1 is When R 2 is When R 1 is When R 2 is When R 1 is When R 2 is
  2. 2. The preparation method of the narrow-band-emission pyrenyl blue light material as claimed in claim 1, which is characterized by comprising the following operation steps: (1) Adding a 7-tert-butyl-1-bromopyrene intermediate into a mixed solution of arylboronic acid and derivatives thereof, inorganic base, a solvent and a palladium catalyst in an inert atmosphere, stirring for 24-48 h at 90-100 ℃ to perform metal catalytic coupling reaction, and performing functional substitution on a 1-site of pyrene to prepare a precursor 7-tert-butyl-1-R 1 group pyrene, wherein the precursor 7-tert-butyl-1-R 1 group pyrene has a structure shown in the following formula (2): wherein R1 is (2) Adding 7-tert-butyl-1-R 1 group pyrene serving as a precursor obtained in the step (1) into a mixed solution of a brominating agent and a solvent in an inert atmosphere, stirring for 12-48 hours at 25-50 ℃ to perform bromination reaction, and performing halogenated substitution on a 3-site of pyrene to obtain a 7-tert-butyl-1-R 1 group substituted-3-halogenated pyrene intermediate, wherein the 7-tert-butyl-1-R 1 group substituted-3-halogenated pyrene intermediate has a structure shown in the following formula (3): Wherein R 3 is one of fluorine, chlorine, bromine or iodine; (3) And (3) adding the 7-tert-butyl-1-R 1 group substituted-3-halogenated pyrenyl intermediate into a mixed solution of aryl boric acid and derivatives thereof, inorganic base, solvent and palladium catalyst in an inert atmosphere, stirring for 24-48 h at 90-100 ℃ for metal catalytic coupling reaction, and performing functional substitution on the 3-site of pyrene to obtain the pyrenyl blue light material with narrow-band emission.
  3. 3. The preparation method of the catalyst composition is characterized in that the inert atmosphere in the step (1) is one or two of nitrogen and argon, the palladium catalyst is one or more of tetrakis (triphenylphosphine) palladium, palladium acetate or ditolylphosphine palladium dichloride, the inorganic base is one or more of potassium carbonate, sodium bicarbonate and potassium bicarbonate, the aryl boric acid and derivatives thereof are 2-biphenylboric acid, 3-biphenylboric acid or 4-biphenylboric acid, the mole ratio of the 7-tert-butyl-1-bromopyrene intermediate, the aryl boric acid and derivatives thereof and the inorganic base to the palladium catalyst is 1 (1-3): (2-10): (1-5), and the solvent is a mixture of water, ethanol and toluene with the volume ratio of (1-5): 1.
  4. 4. The preparation method of the catalyst composition is characterized in that the inert atmosphere in the step (3) is one or two of nitrogen and argon, the palladium catalyst is one or more of tetrakis (triphenylphosphine) palladium, palladium acetate and ditolylphosphine palladium dichloride, the inorganic base is one or more of potassium carbonate, sodium bicarbonate and potassium bicarbonate, the aryl boric acid and derivatives thereof are triphenylamine-3-boric acid pinacol ester, 4-boric acid triphenylamine, 1- (4-phenylboric acid pinacol ester) -1, 2-triphenylethylene or 3-biphenylboric acid, the 7-tert-butyl-1-R 1 group is substituted-3-halogenated pyrenyl intermediate, the aryl boric acid and derivatives thereof, the inorganic base and the palladium catalyst are in a molar ratio of 1 (1-3): (2-10): (1-5), and the solvent is a mixture of water, ethanol and toluene in a volume ratio of 1-5): (1-5): 1-5.
  5. 5. The preparation method of the flame retardant polyurethane foam is characterized in that the inert atmosphere in the step (2) is nitrogen or argon, the brominating agent is one or more of bromine water, NBS, BTMABr 3 , chlorine, fluorine and iodine, the solvent is one or more of dichloromethane, tetrahydrofuran, water and ethanol, and the mol ratio of the precursor 7-tert-butyl-1-R 1 group pyrene to the brominating agent is 1 (1-5).
  6. 6. Use of the narrow-band-emitted pyrenyl blue material according to claim 1 in an organic optoelectronic device.
  7. 7. The method according to claim 6, wherein the organic optoelectronic device comprises an organic light emitting diode, an organic field effect transistor, a solar cell or an organic laser.

Description

Pyrenyl blue light material capable of emitting in narrow band, and preparation method and application thereof Technical Field The invention belongs to the field of synthesis of organic semiconductor photoelectric materials, and particularly relates to a pyrenyl blue light material capable of emitting in a narrow band, and a preparation method and application thereof. Background An Organic Light Emitting Diode (OLED) is an electroluminescent device having the ability to generate light within an organic emissive layer under an external voltage. Today OLEDs have been widely used in the field of cell phones, smart watches, cameras, etc. The OLED has a series of advantages of self-luminescence, low-voltage direct current drive, full solidification, wide viewing angle, light weight, simple composition and process, and the like, and compared with a liquid crystal display, the OLED does not need a backlight source, has large viewing angle and low power, has response speed which can reach 1000 times of that of the liquid crystal display, has lower manufacturing cost than that of the liquid crystal display with the same resolution, and has wide application prospect. The performance of the organic luminescent material determines the performance and the service life of the OLED device, and is a core technology for realizing the high-performance OLED device, and the molecular structure, the stacking mode, the aggregation morphology and the like of the organic semiconductor luminescent material can obviously influence the luminescent behavior of the material. Many organic luminophores exhibit distinct luminescent behavior from molecular level to an aggregated state. In some cases, luminescence may be attenuated or quenched at high concentrations, referred to as "aggregation-induced quenching (ACQ)". In contrast to ACQ, aggregation-induced emission (AIE) is a phenomenon in which a light-emitting material exhibits enhanced emission in an aggregated state, and is mainly because the limited intramolecular rotation prevents a channel of non-radiative transition, and excitons in an excited state can release energy only by radiation, thereby improving the light-emitting intensity of the AIE material in a solid state. Due to their unique properties, AIE molecules can be used in doped or undoped OLED devices with high efficiency, high luminance and low efficiency roll-off. According to the wide color gamut standard of BT 2020, the emission spectra of the three primary colors red (R), green (G), blue (B) light materials require a smaller full width at half maximum, which is a key to improving high definition display. Therefore, from a material perspective, the development of organic light-emitting materials with narrow-band emission is critical to the color purity of optoelectronic devices. However, the strong vibration coupling between the ground state and the excited state of the conventional organic light emitting material results in a wider half-width of the light emission spectrum, and thus, the design and synthesis of an organic light emitting material having narrow-band emission is of great significance for realizing an OLED device for high-definition display. Disclosure of Invention In order to solve the defects and shortcomings in the prior art, the invention takes pyrene as a core, designs and designs the pyrene-based blue light material with narrow-band emission through chemical synthesis, and the luminescent material has good thermal stability, a maximum emission peak of less than 470nm and a solid quantum yield of more than 0.7, wherein the maximum half-peak width is up to 0.9, the maximum half-peak width is less than 50nm, the minimum half-peak width is 33nm, and the luminescent material has higher color purity and is favorable for realizing narrow-band blue light emission. The invention further aims to provide a preparation method of the pyrenyl blue light material capable of emitting in the narrow band. It is still another object of the present invention to provide the use of the above-described narrow-band-emitting pyrenyl blue material. The aim of the invention is achieved by the following technical scheme: A narrow-band-emitted pyrenyl blue material having a structure represented by the following formula (1): When R 1 is When R 2 is When R 1 isWhen R 2 is When R 1 isWhen R 2 is The specific structural formula of the pyrenyl blue light material emitted by the narrow band is as follows: The preparation method of the pyrenyl blue light material capable of emitting narrow bands comprises the following operation steps: (1) Adding a 7-tert-butyl-1-bromopyrene intermediate into a mixed solution of arylboronic acid and derivatives thereof, inorganic base, a solvent and a palladium catalyst in an inert atmosphere, stirring for 24-48 h at 90-100 ℃ to perform metal catalytic coupling reaction, and performing functional substitution on a 1-site of pyrene to prepare a precursor 7-tert-butyl-1-R 1 group pyrene, wherein the p