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Material for organic electroluminescence element, and organic electroluminescence element

An electroluminescent element and electroluminescent technology, applied in the directions of luminescent materials, electrical components, electro-solid devices, etc., can solve the problems of insufficient component efficiency and durability characteristics, and achieve high charge transfer characteristics, high driving stability, high performance effects

Pending Publication Date: 2020-11-20
NIPPON STEEL CHEM &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, although polymers having a carbazole structure in the side chain are disclosed in Patent Document 2 and Non-Patent Document 1, the properties such as efficiency and durability of the device are not sufficient, and further improvement is required.

Method used

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  • Material for organic electroluminescence element, and organic electroluminescence element
  • Material for organic electroluminescence element, and organic electroluminescence element
  • Material for organic electroluminescence element, and organic electroluminescence element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0145] Hereinafter, the present invention will be described in more detail using examples, but the present invention is not limited to these examples, and can be implemented in various forms as long as the gist thereof is not exceeded.

[0146] Molecular weight and molecular weight distribution determination of polymers

[0147] The molecular weight and molecular weight distribution of the synthesized polymer were measured using GPC (manufactured by Tosoh, HLC-8120GPC), solvent: tetrahydrofuran (THF), flow rate: 1.0 ml / min, column temperature: 40°C. The molecular weight of the polymer was calculated as a polystyrene-equivalent molecular weight using a calibration curve based on monodisperse polystyrene.

[0148] Solubility Evaluation of Polymers

[0149] The solubility of the synthesized polymer was evaluated by the following method. It was mixed with toluene so as to have a concentration of 0.5 wt%, and subjected to ultrasonic treatment at room temperature for 30 minutes. ...

Synthetic example 1

[0152] Polymer A is synthesized via Intermediate A, Polymerization Intermediates A, B.

[0153] (Synthesis of Intermediate A)

[0154]

[0155] Under nitrogen atmosphere, add carbazole 5.02g (30.0mmol), 3,5-dibromoiodobenzene 14.12g (39.0mmol), copper iodide 0.17g (0.9mmol), tripotassium phosphate 31.86g (150.1mmol), reverse Formula-1,2-cyclohexanediamine 1.37g (12.0mmol), 1,4-two 50ml of alkane was stirred. Then, it heated to 120 degreeC, and stirred for 24 hours. After cooling the reaction solution to room temperature, inorganic substances were filtered off. The filtrate was dried under reduced pressure, and purified by column chromatography to obtain 8.51 g (21.2 mmol, yield 70.7%) of Intermediate A as a pale yellow powder.

[0156] (Synthesis of Polymer A)

[0157]

[0158] Step 1) Add 2.0g (5.0mmol) of intermediate A, 1.65g (5.0mmol) of 1,3-benzenediboronic acid bispinacol ester, 0.17g (0.15mmol) of palladium tetrakistriphenylphosphine, 3.45 g (24.9 mmol) of ...

Synthetic example 2

[0162] Polymer B was synthesized via intermediates B, C, D, E and polymerization intermediates C, D.

[0163] (Synthesis of Intermediate B)

[0164]

[0165] Add 5.00 g (20.0 mmol) of 2,6-dibromotoluene, 12.19 g (48.0 mmol) of diboron bis pinacol ester, and [1,1'-bis(diphenylphosphino)ferrocene under a nitrogen atmosphere. ] Palladium (II) dichloride dichloromethane adduct 0.98g (1.2mmol), potassium acetate 11.78g (120.0mmol), di 100ml of alkane was stirred. Then, it heated to 130 degreeC, and stirred for 6 hours. The reaction solution was cooled to room temperature, and after adding water and stirring, the organic layer was recovered. Magnesium sulfate and activated carbon were added and stirred, and the solid matter was filtered out. The solvent was distilled off under reduced pressure, and the filtrate was concentrated, followed by recrystallization from hexane to obtain 4.78 g (13.9 mmol, yield 69.4%) of Intermediate B as a light brown powder.

[0166] (Synthesis ...

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Abstract

Provided is a polymer for an organic electroluminescence element having high luminous efficiency and high durability, and that can also be applied to a wet process. An organic electroluminescence element in which an anode, an organic layer, and a cathode are laminated on a substrate, wherein said organic electroluminescence element is characterized in that a material that contains a polymer for anorganic electroluminescence element on a polyphenylene main chain having a tricyclic condensed heterocyclic structure on a side chain is used for at least one layer of the organic layer.

Description

technical field [0001] The present invention relates to a polymer for an organic electroluminescent element and an organic electroluminescent element (hereinafter referred to as an organic EL element), and specifically relates to an organic EL using a polyphenylene group having a specific condensed aromatic heterocyclic structure Component materials. Background technique [0002] In addition to the characteristics of high contrast, high-speed response, and low power consumption, organic EL also has the characteristics of thin, lightweight, flexible structure, and design. It is practical in the fields of displays and lighting. On the other hand, there is still room for improvement in terms of brightness, efficiency, life, and cost, and various researches and developments on materials and device structures are underway. [0003] In order to maximize the characteristics of organic EL elements, it is necessary to recombine the holes and electrons generated from the electrodes w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C08G61/12C09K11/06H10K99/00
CPCC09K11/06C08G61/12H10K85/111H10K50/18H10K50/15H10K50/11H10K2101/10H10K50/181C09K2211/1018C08G2261/95H10K71/12
Inventor 林健太郎长浜拓男池永裕士
Owner NIPPON STEEL CHEM &MATERIAL CO LTD
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