Multi-Arm Monomolecular White Light-Emitting Materials, Preparation Method and Application Thereof

Patent metadata

Field	Value
Publication number	US-2022009857-A1
Application number	US-202117231489-A
Country	US
Kind code	A1
Filing date	Apr 15, 2021
Priority date	Jul 9, 2020
Publication date	Jan 13, 2022
Grant date	—

Abstract

The present invention discloses multi-arm monomolecular white light-emitting materials, preparation method and application thereof. Benzene ring is used as a core, and penta-substituted pyrene and an electron-withdrawing group or an group electron-donating group Ar are used as arms to prepare the multi-arm monomolecular white light-emitting materials; wherein Ar is one of the electron-withdrawing groups such as nitro, cyano, tertiary amine cation, trifluoromethyl, trichloromethyl, sulfonic acid group, formyl, acyl, carboxyl, methoxy, pyridyl, diphenyl sulfone, triazinyl and anthracenedione; or one of the electron-donating groups such as pyrenyl, 9-carbazolyl, 2-thienyl, diphenylamino, tert-butyl diphenylamino, 9-phenoxazinyl, acridinyl, spiro-bifluorenyl, spirofluorenyl acridinyl, alkylamino, dialkylamino, amino and hydroxyl. The present invention simply combines a synthesis method to prepare multi-arm monomolecular white light-emitting materials with novel structure, high fluorescence quantum efficiency, excellent spectrum stability and electroluminescence performance and high color purity, and achieves the preparation of a highly efficient and spectrally stable electroluminescent devices with high color rendering index.

First claim

1 . A multi-arm monomolecular white light-emitting material, characterized by having the following general structural formula:

In the general structural formula, a benzene ring is used as a core, and penta-substituted pyrene and Ar are used as arms, wherein Ar is an electron-withdrawing group or an electron-donating group.

2 . The multi-arm monomolecular white light-emitting material according to claim 1 , characterized in that Ar is selected from one of the electron-withdrawing groups such as bromine, fluorine, nitro, cyano, tertiary amine cation, trifluoromethyl, trichloromethyl, sulfonic acid group, formyl, acyl, carboxyl, methoxy, pyridyl, diphenyl sulfone, triazinyl and anthracenedione.

3 . The multi-arm monomolecular white light-emitting material according to claim 1 , characterized by having the following structural formulas when Ar is an electron-withdrawing group including cyano, trifluoromethyl, pyridyl and triazinyl:

4 . The multi-arm monomolecular white light-emitting material according to claim 1 , characterized in that Ar is selected from one of the electron-donating groups such as pyrenyl, 9-carbazolyl, 2-thienyl, diphenylamino, tert-butyl diphenylamino, 9-phenoxazinyl, acridinyl, spiro-bifluorenyl, spirofluorenyl acridinyl, alkylamino, dialkylamino, amino and hydroxyl.

5 . The multi-arm monomolecular white light-emitting material according to claim 1 , characterized by having the following structural formulas when Ar is an electron-donating group including pyrenyl, 9-carbazolyl, 2-thienyl and spirofluorenyl acridinyl:

6 . A preparation method of a multi-arm monomolecular white light-emitting material according to any of claim 1 , characterized in that the multi-arm monomolecular white light-emitting material is prepared from the raw material of pentabromobenzene containing Ar functional group (Ph5Br—Ar) and 1-pyrenyl boronic acid ester through Suzuki coupling reaction, with the reaction equation as follows:

7 . The preparation method of a multi-arm monomolecular white light-emitting material according to claim 6 , characterized by comprising the following steps:
step 1: mixing a reactant of Ph5Br—Ar and 1-pyrenyl boronic acid ester, a catalyst tetrakis (triphenylphosphine) palladium, and a phase transfer catalyst tetrabutylammonium bromide in a dark place under nitrogen atmosphere, dissolving in potassium carbonate and toluene, and reacting at 90-110° C. for 24-72 h in a dark place; and step 2: after the reaction, cooling to room temperature, extracting the resulting mixed solution with an organic solvent DCM and a saturated salt solution, drying the separated organic layer, performing suction filtration, separating and purifying the mixture obtained by concentrating the solution through column chromatography, and drying to obtain a target product.

8 . The preparation method of a multi-arm monomolecular white light-emitting material according to claim 6 , characterized in that the molar ratio of Ph5Br—Ar to 1-pyrenyl boronic acid ester is 1:9-1:15.

9 . The volume ratio of potassium carbonate to toluene is 1:(2-3), and the molar mass ratio of tetrakis (triphenylphosphine) palladium catalyst to phase transfer catalyst tetrabutylammonium bromide to Ph5Br—Ar is (0.2-0.4):(0.1-0.3):1.

10 . A use of a multi-arm monomolecular white light-emitting material according to claim 1 , characterized in that the material is used as a functional layer material of optoelectronic devices including organic electroluminescent devices, flexible electronic devices and stretchable electronic devices.

Assignees

• Univ Nanjing Posts & Telecommunications

Inventors

• Lai Wenyong
• Song Wan
• Li Xiangchun
• Yan Yu
• Huang Wei

Classifications

• B01J31/0239

  Quaternary ammonium compounds · CPC title

• B01J31/2404

  Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring · CPC title

• B01J2531/985

  in a water / organic solvent system · CPC title

• B01J2531/824

  Palladium · CPC title

• B01J2231/4211

  Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group · CPC title