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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, electrical components, circuits, etc., can solve the problems of unbalanced carrier transport, limited device efficiency and stability, and reduced hole transport performance. Achieve carrier transport balance, maintain color purity, and improve luminous efficiency

Active Publication Date: 2018-11-30
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: Add dibenzothiophene (11g, 60mmol), iron powder (0.17g, 3mmol) and bromine (3.1mL, 60mmol) into a 100ml three-necked flask, and stir at room temperature under a nitrogen atmosphere for 16 After hours, the reaction was quenched with aqueous sodium bisulfite solution, followed by three extractions with dichloromethane, and the solvent was removed under reduced pressure to obtain a crude product, which was then purified by column with a yield of about 80%.

[0038] (2) Preparation of compound 2: Add compound 1 (3.3g, 12.5mmol) to a 100ml three-necked flask under nitrogen protection and dissolve it 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 remov...

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-boryl)-9,9-bis(4 -(2-Ethylhexyloxy)phenyl)fluorene (248.0mg, 0.3mmol), 2,7-dibromo-9,9-bis(4-(2-ethylhexyloxy)phenyl ) fluorene (175.8mg, 0.24mmol), and compound M3 (48.6mg, 0.06mmol) were dissolved in 10mL of toluene, and then tetraethylhydroxylamine aqueous solution (1ml, wt% = 25%), palladium acetate (1mg) and three Cyclohexylphosphine (2mg); after heating to 80°C for 24 hours, add phenylboronic acid (20mg) to block for 6 hours, then add bromobenzene (0.2ml) to block at 80°C for 6 hours; the reaction stops, and after cooling, the organic Phase precipitation in methanol (200ml), filtered, and dried, the crude product was extracted successively with methanol, acetone, and n-hexane, and the polymer was dissolved with toluene, and toluene was used as eluent, and column chromatography was carried out with neutral alumina Purification; concentrat...

Embodiment 2

[0061] Preparation of Polymer P2

[0062] Polymer P2 was synthesized under the same conditions as Polymer P1, except that:

[0063] Polymer P2: 2,7-bis(4,4,5,5-tetramethyl-1,3-dioxo-2-boryl)-9,9-bis(4-(2-ethylhexyl Alkoxy)phenyl)fluorene (248.0mg, 0.3mmol), 2,7-dibromo-9,9-bis(4-(2-ethylhexyloxy)phenyl)fluorene (175.8mg, 0.24 mmol), and compound M1 (41.7mg, 0.06mmol). 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. According to the invention, fluorene of a S,S-dioxydibenzothiophene unit is subjected to Suzuki polymerization to obtain the polyfluorene derivative having a side chain containing the S,S-dioxydibenzothiophene unit or a S-oxy-dibenzothiophene unit or dibenzothiophene and its derivative. The side chain of the polyfluorene derivative is modified with an electron transport unit, which is complementary to a main chain in which hole transport is dominant, and the main chain is not directly conjugated with the electrical-absorption S, S-dioxy-dibenzothiophene, the polymer simultaneously contains the electron transport unit and a hole transport unit, and the spectral purity and stability of the polymer are maintained. so that device efficiency is increased, good solubility is good, and the derivative an be used for the preparation of the light-emitting layer ofthe polymer light-emitting diode.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectricity, and specifically relates to polyfluorene derivatives, a light-emitting layer of a light-emitting diode and a preparation method thereof. Background technique [0002] In 1990, the Cavendish Laboratory of the University of Cambridge published the first polymer thin-film electroluminescent device prepared by conjugated polymer PPV, which officially opened the prelude to the research on polymer light-emitting diodes (PLEDs). Compared with small molecule LEDs, polymer LEDs 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 luminous color of conjugated polymers can be easily obtained through (3) The modification of the conjugated polymer can avoid crystallization, thereby improving the stability of the device. [0003] The PLED device is composed of a cathode, an anode, and an organic...

Claims

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Application Information

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Patent Type & Authority Applications(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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