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A copolymer luminescent material containing fluorinated side groups and its preparation method and application

A technology of luminescent materials and copolymers, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., to achieve the effect of simple synthesis method, good planarity, and large conjugate length

Active Publication Date: 2020-09-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a copolymer luminescent material containing fluorinated side group units in view of the problems faced by the current polymer light emitting diode (PLED)

Method used

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  • A copolymer luminescent material containing fluorinated side groups and its preparation method and application
  • A copolymer luminescent material containing fluorinated side groups and its preparation method and application
  • A copolymer luminescent material containing fluorinated side groups and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of PFSO1:

[0049] (1) Under a nitrogen atmosphere, 2,7-dibromo-(9,9-diphenylhydroxy)fluorene (2g, 3.94mol), C 8 h 8 f 9 I (3.96g, 9.84mmol), K 2 CO 3 (2.18g, 15.74mmol) and 100ml of N'N-dimethylacetamide were added to a 250ml two-necked flask, heated to 80°C for 12 hours, then returned to room temperature, extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, no dried over magnesium sulfate. After distillation under reduced pressure, the crude product was purified with a silica gel column, the eluent was a mixed solvent of dichloromethane and petroleum ether (1:5 by volume), recrystallized from ethanol, and finally a white solid was obtained as compound M1 with a yield of 80%. 1 H NMR, 13 CNMR, 18 The F NMR spectra are as follows figure 1 , figure 2 and image 3 As shown, the analysis is known as the target product. The chemical reaction equation is as follows:

[0050]

[0051](2) Under an argon atmosphere, a...

Embodiment 2

[0054] Preparation of PFSO2:

[0055] Under an argon atmosphere, add M1 (49.32mg, 46.69μmol), M5 (17.46mg, 46.69μmol), M3 (76.82mg, 140.06μmol) and M4 (150.00mg, 233.44μmol) into a 50ml two-necked bottle, and then add 8ml Trifluorotoluene was completely dissolved, pumped and ventilated three times, then quickly added palladium acetate (2.10 mg, 9.34 μmol) and tricyclohexylphosphine (5.24 mg, 18.68 μmol), pumped and ventilated three times, and then added 2ml of tetraethyl hydroxide ammonium, heated to 80°C, and reacted for 24 hours. Then add 30 mg of phenylboronic acid for capping, and after 12 hours, use 0.3 ml of bromobenzene for capping and continue the reaction for 12 hours; add the product dropwise to precipitate in methanol, stir, filter, and then dissolve the crude product in 30 mL of In toluene, use 200-300 mesh silica gel as the stationary phase, and use toluene as the eluent for column chromatography. After the solvent is concentrated under reduced pressure, it is pr...

Embodiment 3

[0058] Preparation of PFSO3:

[0059] (1) Under nitrogen atmosphere, 2,7-dibromofluorene (2.00g, 6.17mmol), C 8 h 8 f 9 I (6.2g, 15.43mmol), sodium hydroxide (24g, 1.04mol), tetrabutylammonium bromide (200mg, 0.62mmol) and 100ml of toluene were added to a 250ml two-necked flask, heated to 180°C for 12 hours, and recovered At room temperature, extract with ethyl acetate, wash with saturated aqueous sodium chloride, and dry over anhydrous magnesium sulfate. After distillation under reduced pressure, the crude product was purified with a silica gel column, the eluent was a mixed solvent of dichloromethane and petroleum ether (1:5 by volume), recrystallized from methanol, and finally a white solid was obtained as compound M6 with a yield of 67%. 1 H NMR, 13 CNMR, 18 F NMR analysis was the target product. The chemical reaction equation is as follows:

[0060]

[0061] (2) Under an argon atmosphere, add M6 (40.73mg, 46.69μmol), M5 (17.46mg, 46.69μmol), M3 (76.82mg, 140.06μ...

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Abstract

The invention discloses a copolymer luminescent material containing fluorinated side groups, a preparation method and application thereof. The fluorinated side group-containing copolymer luminescent material has a relatively high fluorescence quantum yield due to its large conjugation length, good planarity, and good interface property, which is beneficial to improving the device efficiency of the material; at the same time , the synthesis method of the fluorinated side group copolymer light-emitting material is simple, and has good solubility, film-forming property and film shape stability. The light-emitting layer based on this material does not need annealing treatment when preparing organic light-emitting devices, so that The process is simpler.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a copolymer luminescent material containing fluorinated side groups and its preparation method and application. Background technique [0002] Organic light-emitting diode (O / PLED) emerged as a new generation of flat panel display technology. Compared with traditional cathode ray diodes, it has the advantages of light weight, high-efficiency light emission, energy saving and environmental protection, flexible display and low processing cost, and has a wide range of applications. prospect. Although organic / high-resolution light-emitting diodes have made breakthroughs in organic flat-panel displays and white lighting, the degree of industrialization is far below people's expectations, and there are still many key issues to be solved in this field of research. Mainly, there are still major fundamental problems in the optimization of luminescent ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54C09K11/06
CPCC09K11/06C08G61/126C08G2261/18C08G2261/3229C08G2261/323C08G2261/3223C08G2261/3224C08G2261/3221C08G2261/3142C08G2261/124C08G2261/146C08G2261/95C08G2261/52C09K2211/1458H10K85/113H10K50/11
Inventor 应磊王小君郭婷彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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