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Polymer compound and polymer light-emitting device

一种高分子化合物、发光元件的技术,应用在高分子化合物,高分子发光元件领域,能够解决效率和寿命不令人满意等问题

Inactive Publication Date: 2012-05-02
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when conventional polymer compounds are used in light-emitting devices, the balance between the efficiency and lifetime of the device is not satisfactory

Method used

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  • Polymer compound and polymer light-emitting device
  • Polymer compound and polymer light-emitting device
  • Polymer compound and polymer light-emitting device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0262] (Synthesis of Compound E and Compound F)

[0263] -Synthesis of Compound A-

[0264] Under an inert atmosphere, add 5.00 (29mmol) of 1-naphthylboronic acid, 6.46g (35mmol) of 2-bromobenzaldehyde, 10.0g (73mmol) of potassium carbonate, 36ml of toluene and 36ml of ion-exchanged water to a 300ml three-necked flask. While stirring, argon was blown for 20 minutes. Then, 16.8 mg (0.15 mmol) of tetrakis(triphenylphosphine)palladium was added, and argon was blown for 10 minutes while stirring at room temperature. The temperature was raised to 100°C, and the reaction was carried out for 25 hours. After cooling to room temperature, the organic layer was extracted with toluene, and the obtained organic layer was dried over sodium sulfate, and the solvent was distilled off. The compound thus obtained is purified with a silica gel column using a mixed solvent of toluene:cyclohexane=1:2 (volume ratio) as a developing solvent to obtain the following formula:

[0265] Compo...

Synthetic example 2

[0300]

[0301] Under an argon atmosphere, 17.0 g (28.4 mmol) of compound E synthesized in the same manner as above, 19.4 g (28.0 mmol) of compound F synthesized in the same manner as above, and 311 mL of toluene were added to a 1 L three-neck flask connected to a Dimroth condenser. , and then the gas in the container was replaced with nitrogen by blowing nitrogen. After raising the temperature to 45°C, 19 mg of palladium acetate and 118 mg of tris(o-methoxyphenyl)phosphine were added, and after stirring at 45°C for 5 minutes, 25.9 mL of a 33% by weight bis(tetraethylammonium)carbonate aqueous solution was added. , stirred at 114°C for 24 hours. Then, 5.27 g (30.8 mmol) of 4-bromotoluene was added and stirred at 114° C. for 1 hour, and then 5.48 g (30.8 mmol) of 4-tert-butylphenylboronic acid was added and stirred at 114° C. for 1 hour. Cool to 65 DEG C, wash 2 times with 5% by weight sodium diethyldithiocarbamate aqueous solution, wash 2 times with 2N hydrochloric acid, wa...

Synthetic example 3

[0305]

[0306] Under an argon atmosphere, polymer 1 (1.0 g, 2.28 mmol in terms of benzofluorene repeating units) and 50 mL of chloroform were placed in a 100 mL flask, stirred and dissolved at room temperature, and then 3.5 mL of trifluoroacetic acid was added in sequence. , 91 µL of bromine (1.78 mmol, 78 mol% relative to the benzofluorene unit), and stirred for 6 hours under light shielding. The reactant was dropped into 250 mL of methanol under stirring to cause precipitation. The obtained precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain 1.09 g of a polymer. The polymer was placed in a 100 mL flask under an argon atmosphere, 50 mL of chloroform was charged therein, stirred and dissolved at room temperature, and then 3.4 mL of trifluoroacetic acid and 41 μL of bromine (0.80 mmol, relative to the benzofluorene unit 36 mol%), stirred for 17 hours under light shielding. The reactant was dropped into 250 mL of methanol under stirrin...

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Abstract

Disclosed is a polymer compound having a conjugated polymer main chain and a side chain selected from the following (a)-(c). (a) A side chain having an electron transport property. The value of the LUMO energy of this side chain is different from that of the LUMO energy of the conjugated polymer main chain, and the absolute value of the difference is 0.3 eV or less. (b) A side chain having a holetransport property. The value of the HOMO energy of this side chain is different from that of the HOMO energy of the conjugated polymer main chain, and the absolute value of the difference is 0.3 eV or less. (c) A side chain having an electron transport property and a hole transport property. The value of the LUMO energy of this side chain is different from that of the LUMO energy of the conjugated polymer main chain, and the absolute value of the difference is 0.3 eV or less. The value of the HOMO energy of this side chain is different from that of the HOMO energy of the conjugated polymer main chain, and the absolute value of the difference is 0.3 eV or less.

Description

technical field [0001] The present invention relates to a polymer compound and a polymer light-emitting device (polymer LED) using the polymer compound. Background technique [0002] High-molecular-weight light-emitting materials are usually soluble in solvents, so they can be used to form organic layers in light-emitting elements by coating methods, which meet the requirements of large-area elements. Therefore, in recent years, various polymer compounds that can serve as polymer light-emitting materials and polymer light-emitting devices using the polymer compounds have been proposed (for example, Advanced Materials Vol. 121737-1750 (2000)). [0003] The light-emitting element preferably has high stability, that is, long life, and high luminous efficiency, that is, high luminance per unit current. However, when conventional polymer compounds are used in light-emitting devices, the balance between the device's efficiency and lifetime is not satisfactory. Contents of the i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/02C09K11/06H01L51/50
CPCH01L51/5012C09K2211/1029H01L51/006C09K2211/1048C09K2211/1096C09K2211/1416C08G61/02H05B33/14C09K11/06H01L51/0039H01L51/0043C09K2211/1466C09K2211/1059C09K2211/1014C09K2211/1044H10K85/115H10K85/151H10K85/633H10K50/11H10K85/631H10K50/15H10K50/16
Inventor 大内一荣上谷保则中园明子
Owner SUMITOMO CHEM CO LTD