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Polyfluorene derivative, light-emitting layer of light-emitting diode and preparation method thereof

A technology of light-emitting diodes and derivatives, applied in semiconductor/solid-state device manufacturing, electric solid-state devices, semiconductor devices, etc., can solve the problem of reducing hole transport performance, unbalanced carrier transport, limited device efficiency and stability, etc. problems, to achieve the effect of improving luminous efficiency, carrier transport balance, and maintaining color purity

Active Publication Date: 2020-10-09
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

The reason is that the introduction of S,S-dioxy-dibenzothiophene unit can significantly reduce the HOMO energy level of the polymer and improve the hole injection while reducing the LUMO energy level of the polymer and improving the electron transport performance of the polymer. Potential barrier, which reduces the hole transport performance, makes the carrier transport unbalanced in the polymer, and the device efficiency and stability are limited

Method used

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  • Polyfluorene derivative, light-emitting layer of light-emitting diode and preparation method thereof
  • Polyfluorene derivative, light-emitting layer of light-emitting diode and preparation method thereof
  • Polyfluorene derivative, light-emitting layer of light-emitting diode and preparation method thereof

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preparation example Construction

[0036] Preparation of compound M1

[0037] (1) preparation of compound 1: in a 100ml there-necked flask, add dibenzothiophene (11g, 60mmol), iron powder (0.17g, 3mmol) and elemental bromine (3.1mL, 60mmol), under nitrogen atmosphere, stirring reaction 16 at room temperature hours, then the reaction was quenched with aqueous sodium bisulfite, followed by three extractions with dichloromethane, and the solvent was removed under reduced pressure to give the crude product, which was then purified by column in about 80% yield.

[0038] (2) Preparation of compound 2: under nitrogen protection, add compound 1 (3.3g, 12.5mmol) to a 100ml there-necked flask, dissolve in dry tetrahydrofuran, then add butyllithium (3.3g, 12.5mmol), under nitrogen atmosphere , stirred at -78 degrees Celsius for 2 hours, then added 1-bromo-n-hexane (7.4g, 45mmol) to continue the reaction for 1 hour, then added water to quench the reaction, then extracted three times with dichloromethane, and removed the so...

Embodiment 1

[0053] Preparation of polymer P1

[0054] Synthesis of polymer P1: under nitrogen protection, 2,7-bis(4,4,5,5-tetramethyl-1,3-dioxo-2-boranyl)-9,9-bis(4 -(2-Ethylhexaneoxy)phenyl)fluorene (248.0 mg, 0.3 mmol), 2,7-dibromo-9,9-bis(4-(2-ethylhexaneoxy)phenyl) ) fluorene (175.8 mg, 0.24 mmol), and compound M3 (48.6 mg, 0.06 mmol) were dissolved in 10 mL of toluene, and then tetraethylhydroxylamine aqueous solution (1 ml, wt%=25%), palladium acetate (1 mg) and tris Cyclohexylphosphine (2mg); heated to 80°C for reaction for 24 hours, then added phenylboronic acid (20mg) to cap for 6 hours, and then added bromobenzene (0.2ml) at 80°C to cap for 6 hours; the reaction stopped, after cooling, the organic The phase was precipitated in methanol (200ml), filtered and dried. The crude product was extracted with methanol, acetone, and n-hexane successively. The polymer was dissolved in toluene, and toluene was used as the eluent to perform column chromatography with neutral alumina. Purif...

Embodiment 2

[0061] Preparation of polymer P2

[0062] The synthesis conditions of polymer P2 are the same as those of polymer P1, the difference is:

[0063] Polymer P2: 2,7-bis(4,4,5,5-tetramethyl-1,3-dioxo-2-boranyl)-9,9-bis(4-(2-ethylhexyl) Alkoxy)phenyl)fluorene (248.0mg, 0.3mmol), 2,7-dibromo-9,9-bis(4-(2-ethylhexaneoxy)phenyl)fluorene (175.8mg, 0.24 mmol), and compound M1 (41.7 mg, 0.06 mmol). GPC: Mn=97KDa, PDI=3.21.

[0064]

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Abstract

The invention discloses a polyfluorene derivative, a light-emitting layer of a light-emitting diode and a preparation method thereof. In the present invention, the fluorene of S, S-dioxy-dibenzothiophene unit is subjected to Suzuki polymerization reaction to obtain the side chain containing S, S-dioxy-dibenzothiophene unit or S-oxygen-dibenzothiophene unit Or polyfluorene derivatives of dibenzothiophene and its derivatives. The present invention modifies the electron transport unit on the side chain of the polyfluorene derivative to complement the main chain dominated by hole transport, and the main chain is not directly conjugated with the charge-absorbing S,S-dioxo-dibenzothiophene , so that the polymer contains electron transport units and hole transport units at the same time, and maintains the spectral purity and stability of the polymer, which is conducive to the improvement of device efficiency, and has good solubility, and can be used in the light-emitting layer of polymer light-emitting diodes preparation.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and particularly relates to a polyfluorene derivative, a light-emitting layer of a light-emitting diode and a preparation method thereof. Background technique [0002] In 1990, the Cavendish Laboratory of Cambridge University published the first polymer thin film electroluminescent device prepared by conjugated polymer PPV, which officially opened the prelude to the research of polymer light emitting diode (PLED). Compared with small-molecule light-emitting diodes, polymer light-emitting diodes have the following advantages: (1) large-area thin films can be prepared by solution spin coating, roll-to-roll, etc.; (2) the electronic structure and emission color of conjugated polymers are easily passed through Changes in chemical structure and modification can be adjusted; (3) Conjugated polymers can be modified to avoid crystallization, thereby improving device stability. [0003] T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/02H01L51/50H01L51/54
CPCC08G61/02C08G2261/95C08G2261/512C08G2261/514C08G2261/411C08G2261/122C08G2261/3142C08G2261/145C08G2261/1424H10K85/151H10K50/11
Inventor 应磊钟知鸣彭沣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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