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A class of polyfluorene derivatives containing siloxane side chains suitable for inkjet printing process and its preparation method and application

An inkjet printing technology containing siloxane, which is applied in the field of polyfluorene derivatives containing siloxane side chains and its preparation, can solve the problems of high ink viscosity, easy blockage of nozzles, and large molecular weight, and achieve low cost, The effect of simple structure and excellent photoelectric performance

Active Publication Date: 2021-10-08
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] For polymeric organic semiconductor materials, due to the large molecular weight, the prepared ink has high viscosity, and there are disadvantages such as no ejection, tailing and easy nozzle clogging during the printing process.

Method used

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  • A class of polyfluorene derivatives containing siloxane side chains suitable for inkjet printing process and its preparation method and application
  • A class of polyfluorene derivatives containing siloxane side chains suitable for inkjet printing process and its preparation method and application
  • A class of polyfluorene derivatives containing siloxane side chains suitable for inkjet printing process and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: the preparation of polymer P1

[0058] (1) Preparation of compound M1: Add purchased fluorene (1.66g, 10mmol), 4-bromo-1-butene (3.24g, 24mmol), potassium hydroxide (1.41g, 25mmol) and DMSO (60ml), stirred at room temperature under nitrogen protection for 8 hours. After the reaction was completed, it was poured into 200ml of deionized water, and the organic phase was extracted three times with 100mL of chloroform, then dried by adding anhydrous magnesium sulfate, purified with a silica gel column after evaporating chloroform (eluent is n-hexane), and obtained 2.14g of a white solid. Yield 78%.

[0059] (2) Preparation of compound M2: Add compound M1 (2.74g, 10mmol) into a 200ml two-necked bottle, purchased 1,1,1,3,5,5,5-heptamethyltrisiloxane (5.34g , 24mmol), Castel catalyst (2mL) and toluene (100ml), heated to 50°C under nitrogen protection, and stirred for 24 hours. After the reaction was completed, the mixture was concentrated under vacuum, and the ...

Embodiment 2

[0067] Embodiment 2: the preparation of polymer P2

[0068] (1) Synthesis of compound M8: 2,7-dibromofluorenone (33.80g, 100mmol), phenol (28.23g, 300mmol), methanesulfonic acid (33.64g, 350mmol) and four Carbon chloride (300ml) was heated under reflux at 80°C and stirred for 24 hours under the protection of nitrogen. Suction filtration after cooling, the filter residue was washed twice with distilled water (150ml) and dichloromethane (150ml) successively, and then further purified with a silica gel column (the eluent was petroleum ether:ethyl acetate=8:1) to obtain a white solid 42.30 g, yield 83%. 1 H NMR (500MHz, DMSO) δ (ppm): 9.40 (s, 2H), 7.90 (d, J = 8.1Hz, 2H), 7.58 (dd, J = 8.1, 1.8Hz, 2H), 7.48 (d, J =1.7Hz, 2H), 6.92-6.84(m, 4H), 6.69-6.61(m, 4H).

[0069](2) Synthesis of compound M9: Add compound M8 (25.41g, 50mmol), potassium carbonate (20.7g, 150mmol) and N,N-dimethylformamide (150ml) into a 300ml two-necked bottle, under nitrogen protection, Heat to 90°C and...

Embodiment 3

[0074] Embodiment 3: the preparation of polymer light-emitting diode

[0075] Take the pre-made indium tin oxide (ITO) glass with a sheet resistance of 10Ω, ultrasonically clean it with acetone, detergent, deionized water and isopropanol in sequence, and treat it with plasma for 1.5 minutes; spin-coat the ITO doped with polystyrene A polyethoxythiophene (PEDOT:PSS=1:6, w / w) film of ethylene sulfonic acid with a thickness of 40 nm; the PEDOT:PSS film was dried in a vacuum oven at 75°C for 12 hours; subsequently spin-coated with PEDOT: The indium tin oxide (ITO) glass of PSS was transferred into a glove box filled with nitrogen to spin-coat the hole transport layer and the light-emitting layer; the chlorobenzene solution (5mg / mL) of polyvinylcarbazole (PVK) was spin-coated on PEDOT:PSS The surface of the film has a thickness of 20nm as the hole transport layer; then the xylene solution (10mg / mL) of the polymer P0, P1 or P2 is spin-coated on the surface of the PVK film with a thi...

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Abstract

The invention belongs to the technical field of organic optoelectronics, and discloses a polyfluorene derivative containing siloxane side chains suitable for an inkjet printing process, a preparation method and an application thereof. The structure of the polyfluorene derivatives containing siloxane side chains of the present invention is as follows. The polyfluorene derivatives containing siloxane side chains of the present invention have a simple structure, low cost, and are conducive to mass production. excellent. In the present invention, loosely structured siloxane groups are connected to the side chains of polyfluorene derivatives, which can reduce the viscosity and surface tension after being configured into ink, so that they can be used for inkjet printing to prepare organic electronic devices, such as organic thin film transistors, organic Light-emitting transistors, organic solar cells, organic photodiodes, organic phototransistors, organic light-emitting electrochemical cells, organic electroluminescent diode devices.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a polyfluorene derivative containing siloxane side chains suitable for an inkjet printing process and a preparation method and application thereof. Background technique [0002] An organic light-emitting diode (OLED) device is composed of a cathode, an anode, and an organic layer (including an electron transport layer, a light-emitting layer, a hole transport layer, etc.) sandwiched in the middle. The working mechanism of the device is: electrons and holes are injected from the cathode and anode respectively, And migrate in the functional layer respectively, then the electrons and holes form excitons at appropriate positions, the excitons migrate within a certain range, and finally the excitons transition to the ground state to emit light. [0003] Compared with large-area film-forming methods such as spin coating and pulling, inkjet printing technolog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09D11/30
CPCC08G61/126C09D11/30C08G2261/122C08G2261/144C08G2261/3142C08G2261/3243C08G2261/411C08G2261/92C08G2261/91C08G2261/95Y02E10/549
Inventor 应磊钟知鸣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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