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Poly(fluorene-co-s,s-dioxy-dibenzothiophene) derivatives containing anthracene derivatives in side chains, preparation method and application thereof

A technology of dibenzothiophene and anthracene derivatives is applied in the field of polyderivatives containing anthracene derivatives in side chains and their preparation fields, so as to achieve the effects of improving device stability, maintaining spectral purity and stability, and simplifying device preparation processes

Active Publication Date: 2019-12-03
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

[0003] In order to realize color display, high-efficiency luminescent materials emitting red, green, and blue primary colors are required. In the current polymer luminescent material system, the development of high-efficiency blue fluorescent polymers still faces great challenges.

Method used

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  • Poly(fluorene-co-s,s-dioxy-dibenzothiophene) derivatives containing anthracene derivatives in side chains, preparation method and application thereof
  • Poly(fluorene-co-s,s-dioxy-dibenzothiophene) derivatives containing anthracene derivatives in side chains, preparation method and application thereof
  • Poly(fluorene-co-s,s-dioxy-dibenzothiophene) derivatives containing anthracene derivatives in side chains, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of compound M1

[0040] Under nitrogen protection, 9,10-dibromoanthracene (3.36g, 10mmol), 1-naphthaleneboronic acid (1.72g, 10mmol), potassium carbonate (4.14g, 30mmol), tetrakis(triphenyl Phosphine) palladium (0.58 g, 0.5 mmol), 15 mL of distilled water and 100 mL of tetrahydrofuran were heated to 70 ° C for 12 hours. After the reaction was completed, tetrahydrofuran was distilled off under reduced pressure, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and after removing the organic phase solvent, the crude product was mixed with petroleum ether:dichloromethane=8:1 (v / v) The solvent was used as an eluent for column chromatography to obtain 2.53 g of off-white solid with a yield of 66% (mass spectrum: 382.0).

[0041] The chemical reaction equation is as follows:

[0042]

Embodiment 2

[0043] Embodiment 2: the preparation of compound M2

[0044] Under the protection of nitrogen, in a 150mL three-neck flask, M1 (1.92g, 5mmol) was dissolved in 50mL of anhydrous tetrahydrofuran, and the temperature was kept at 0°C for 20 minutes in an ice bath. Slowly add n-butyllithium solution (4mL, 8mmol) dropwise into the reaction flask, stir at 0°C for 1 hour after the dropwise addition, then inject 1,4-dibromobutane (2.16g, 10mmol) into the reaction flask , continue to react in an ice bath for 2 hours, and naturally rise to room temperature for 12 hours. Tetrahydrofuran was removed by distillation under reduced pressure, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and the organic phase solvent was removed by distillation under reduced pressure, then mixed with petroleum ether:dichloromethane=10:1 (v / v) The solvent was used as eluent and purified by column chromatography to obtain 1.54 g of off-white ...

Embodiment 3

[0047] Embodiment 3: the preparation of compound M3

[0048] Under nitrogen protection, add 2,7-dibromofluorene (1.30g, 4mmol), potassium hydroxide (1.68g, 30mmol) and 50mL tetrahydrofuran into a 150mL three-necked flask, stir at room temperature for 2 hours, then add M2 (4.39g , 10 mmol), heated to 70 ° C for 24 hours. After the reaction is complete, THF is removed by rotary evaporation, the product is extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and the organic phase solvent is removed by distillation under reduced pressure. ) mixed solvent as eluent and purified by column chromatography to obtain 2.41 g of light yellow-green solid with a yield of 58%, (mass spectrum: 1040.3).

[0049] The chemical reaction equation is as follows:

[0050]

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Abstract

The invention belongs to the field of organic photoelectric technology and discloses a poly (fluorene-co-S,S-dioxo-dibenzothiophene) derivative for a side chain anthracene-containing derivative, a preparation method and an application thereof. The structural formula of the derivative is shown as follows, wherein x1 is more than 0 but less than 0.5; x2 is more than 0 but less than 1; x1+x2 is lessthan or equal to 1; n is a repeated unit and n is equal to 10-1000; m is an integer within 0-10; R1 is a solubilizing group and is alkyl or naphthenic group with carbon number within 6-30 and alkyl oralkoxy substituted phenyl group with carbon number within 6-30; and Ar is anthracene derivative. According to the invention, an anthracene derivative main unit is introduced into the poly (fluorene-co-S,S-dioxo-dibenzothiophene) side chain and a singlet state exciton is generated in the manner of triplet state exciton quenching, so that the generating ratio of the singlet state exciton of the main unit is increased, and the generating ratio of the singlet state exciton of the polymer is increased in the manner of transferring energy through the subject and object, so that the illuminating efficiency of the material is increased.

Description

technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a poly(fluorene-co-S,S-dioxo-dibenzothiophene) derivative containing anthracene derivatives in a side chain, a preparation method and application thereof. Background technique [0002] Polymer light-emitting diodes (PLEDs) have the characteristics of solution processing, and large-area devices can be prepared by printing, printing, etc., and it is easy to prepare large-area devices, which has potential low-cost advantages. The PLED 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. Then the electrons and holes form excitons at the appropriate positions, the excitons migrate within a certain range, and finally the excitons jump to the ground state to emit light. [0003] In order to realize color display, high-efficiency lu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/50H01L51/54
Inventor 应磊彭沣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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