D-a type polymer containing s, s-dioxy-dibenzothiophene in the main chain and its preparation method and application

A dibenzothiophene and polymer technology, applied in the field of D-A polymer and its preparation, can solve problems such as limiting electroluminescence efficiency, and achieve the effects of benefiting device efficiency, increasing the generation ratio, and promoting the crossing process

Active Publication Date: 2020-03-24
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional polymer fluorescent materials can only utilize 25% of singlet excitons, and 75% of triplet excitonic energy is lost through non-radiative transitions, which makes the maximum internal quantum efficiency of traditional polymer fluorescent materials only 25%. limits its electroluminescent efficiency

Method used

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  • D-a type polymer containing s, s-dioxy-dibenzothiophene in the main chain and its preparation method and application
  • D-a type polymer containing s, s-dioxy-dibenzothiophene in the main chain and its preparation method and application
  • D-a type polymer containing s, s-dioxy-dibenzothiophene in the main chain and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of compound M1

[0035] (1) Preparation of compound 1

[0036] Add 2,8-dibromo-S, S-dioxy-dibenzothiophene (3.74g, 10mmol), aniline (2.79g, 30mmol), sodium tert-butoxide (4.81g, 50mmol) into a 100ml two-necked flask, Tris(dibenzylideneacetone)dipalladium (458 mg, 0.5 mmol), tri-tert-butylphosphine (101 mg, 0.5 mmol) and 50 ml of toluene were heated to 100° C. for 12 hours under nitrogen. After the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure, and the crude product was eluted with a mixed solvent of petroleum ether:dichloromethane=3:1 (v / v) Purified by solvent column chromatography to obtain 1.60 g of white solid with a yield of 40%, (mass spectrum: 398.2).

[0037] (2) Preparation of compound M1

[0038]Add compound 1 (398.5g, 10mmol), p-bromoiodobenzene (8.49g, 30mmol), sodium tert-bu...

Embodiment 2

[0041] Embodiment 2: the preparation of compound M2

[0042] Add 2,8-diiodo-S, S-dioxo-dibenzothiophene (4.68g, 10mmol), 3-bromocarbazole (6.15g, 25mmol), potassium carbonate (6.9g, 50mmol) into a 100ml two-necked flask ), cuprous iodide (95mg, 0.5mmol) and 50ml of toluene were heated to 100°C for 12 hours under nitrogen atmosphere. After the reaction was completed, the product was extracted with dichloromethane, the organic phase was washed with saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure, and the crude product was eluted with a mixed solvent of petroleum ether:dichloromethane=4:1 (v / v) Purified by solvent column chromatography to obtain 2.59 g of white solid with a yield of 37%, (mass spectrum: 704.0).

[0043] The chemical reaction equation is shown in formula (3):

[0044]

Embodiment 3

[0046] Preparation of compound M3

[0047] Under a nitrogen atmosphere, add 3,6-dibromocarbazole (3.25g, 10mmol), 2-ethylbromohexane (2.90g, 15mmol), potassium carbonate (4.14g, 30mmol) to a 300ml two-necked flask ) and 150ml N,N-dimethylformamide were stirred and reacted at 80°C for 12 hours. After cooling, the product was extracted with dichloromethane, washed five times with saturated aqueous sodium chloride solution until the water layer was clear, distilled off under reduced pressure to remove dichloromethane, and the crude product was purified by column chromatography using petroleum ether as eluent to obtain a colorless transparent liquid 3.94 g, yield 90%, (mass spectrum: 437.1).

[0048] Preparation of compound M4

[0049] Under nitrogen protection, add M3 (4.37g, 10mmol), pinacol diborate (6.35g, 25mmol), [1,1'-bis(diphenylphosphino)ferrocene] into a 300ml two-necked flask Palladium dichloride (0.49g, 0.5mmol), potassium acetate (3.92g, 40mmol) and 120ml of dioxan...

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Abstract

The invention discloses a D-A polymer whose main chain contains S,S-dioxo-dibenzothiophene, a preparation method and an application thereof. The present invention adopts electro-absorbing S,S-dioxo-dibenzothiophene units and donating units to carry out copolymerization to form D-A structure molecules, and obtains the main chain containing S,S-dioxo-dibenzothiophene D‑A polymers. In the present invention, the 2,8-position carbon atom of the S,S-dioxo-dibenzothiophene unit is connected to the donating nitrogen-containing aromatic heterocyclic unit through a C-N bond, and the D-A unit has a relatively large torsion angle. It is beneficial to reduce the conjugation degree of polymer molecules, realize the effective separation of HOMO and LUMO electron clouds, reduce the singlet-triplet energy level difference, promote the intramolecular reverse intersystem crossing process, and increase the singlet exciton generation ratio. It is conducive to the improvement of device efficiency. This type of D-A polymer containing S,S-dioxo-dibenzothiophene in the main chain has good solubility and can be used to prepare the light-emitting layer of the polymer light-emitting diode.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and specifically relates to a D-A type polymer containing S,S-dioxy-dibenzothiophene in the main chain, a preparation method and application thereof. Background technique [0002] In 1990, the Cavendish Laboratory of the University of Cambridge published a polymer thin-film electroluminescent device prepared by using conjugated polymer PPV, which officially opened the prelude to the research on polymer light-emitting diodes (PLEDs). Compared with small molecule light-emitting diodes, polymer light-emitting diodes have the following advantages: (1) large-area thin films can be prepared by printing, inkjet printing, etc.; (3) The modification of the conjugated polymer can avoid crystallization and improve the stability of the device. [0003] The PLED device is composed of a cathode, an anode, and an organic layer in the middle. The organic layer generally includes an electron trans...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54
CPCC08G61/124C08G61/126C08G2261/3241C08G2261/3243C08G2261/124C08G2261/1412C08G2261/95C08G2261/522C08G2261/411H10K85/113H10K50/11H10K2101/10
Inventor 应磊彭沣胡黎文黄飞曹镛
Owner 东莞伏安光电科技有限公司
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