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Polymer, organic electroluminescence element material, composition for organic electroluminescence element, organic electroluminescence element, display device, and lighting device

An organic electric field and light-emitting element technology, applied in the field of polymers, can solve the problems of difficult stacking, poor driving stability, not reaching the practical level, etc., and achieve the effects of high driving stability, high hole transport capacity, and high electrochemical stability.

Active Publication Date: 2012-11-21
MITSUBISHI RAYON CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, wet film formation method is difficult to laminate
Therefore, compared with devices made by the vacuum evaporation method, the driving stability of the devices made by the wet film-forming method is poor, and all but some of them are not at a practical level.
In particular, in the wet film-forming method, although two-layer lamination can be performed using organic solvents, aqueous solvents, etc., it is difficult to perform three-layer or more lamination.

Method used

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  • Polymer, organic electroluminescence element material, composition for organic electroluminescence element, organic electroluminescence element, display device, and lighting device
  • Polymer, organic electroluminescence element material, composition for organic electroluminescence element, organic electroluminescence element, display device, and lighting device
  • Polymer, organic electroluminescence element material, composition for organic electroluminescence element, organic electroluminescence element, display device, and lighting device

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1)

[0375] (Synthesis Example 1) Synthesis of Polymer 1

[0376] Synthesis of Intermediate 1

[0377]

[0378] 4,4'-(1,3-Dimethylbutylidene)diphenol (15g, 55.48mmol), triethylamine (22.46g, 221.92mmol), dichloromethane (150ml) were added under nitrogen atmosphere, and the mixture was dissolved at 0 Stir at °C. To this was added trifluoromethanesulfonic acid anhydride (37.56 g, 133.16 mmol), and the mixture was stirred at room temperature for 6 hours. Water and 1N hydrochloric acid were added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was washed with a mixed solution of water and 1N hydrochloric acid, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / dichloromethane=3 / 1) to obtain Intermediate 1 (19.1 g, yield 64%).

[0379] Synthesis of Intermediate 2

[0380]

[0381] A suspension of Intermediate 1 (19.1 g, 35.73 mmol)...

Synthetic example 2)

[0395] (Synthesis Example 2) Synthesis of Polymer 2

[0396]

[0397] Aniline (0.6575 g, 0.706 mmol), monomer 2 (0.0457 g, 0.234 mmol), monomer 3 (2.000 g, 3.647 mmol), sodium tert-butoxide (2.24 g, 23.3 mmol), toluene (19 ml) were added The inside of the system was fully replaced with nitrogen and heated to 60°C (solution A). To a solution of tris(dibenzylideneacetone)dipalladium chloroform complex (0.075g, 0.0729mmol) in 5ml of toluene was added tri-tert-butylphosphine (0.118g, 0.584mmol) and warmed to 60°C (solution B). Solution B was added to solution A in a nitrogen stream, and the reaction was heated under reflux for 2.0 hours. The disappearance of aniline and monomers 2 and 3 was confirmed, and 4,4'-dibromobenzene (1.104 g, 3.538 mmol) was added. The mixture was heated to reflux for 40 minutes, the reaction solution was allowed to cool, and the reaction solution was added dropwise to 300 ml of ethanol to precipitate polymer 2 into crystals.

[0398] The filtered p...

Embodiment 1)

[0404] make figure 1 The organic electroluminescent element shown.

[0405] The anode 2 is formed by patterning a product (sputtered product, sheet resistance 15Ω) with a 150 nm transparent conductive film of indium tin oxide (ITO) formed on a glass substrate into stripes with a width of 2 mm using a common photolithography technique. The patterned ITO substrate was cleaned in the order of ultrasonic cleaning with acetone, water cleaning with pure water, and ultrasonic cleaning with isopropanol, dried under nitrogen flow, and finally, ultraviolet ozone cleaning was performed.

[0406] First, a polymer (weight average molecular weight: 70,000, number average molecular weight: 40,000) represented by the following structural formula (H8) and 4-isopropyl-4'-methyldiphenyl iodide represented by the structural formula (A1) were prepared A coating solution for forming a hole injection layer of tetrakis(pentafluorophenyl)borate and ethyl benzoate. This coating liquid was formed int...

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Abstract

The present invention intends to provide a polymer which has a high singlet excited level and triplet excited level, is excellent in charge transportability and electrochemical stability, is capable of being laminated, causes less decomposition and is capable of providing a homogeneous film guality, and an organic electroluminescent element material and a composition for an organic electroluminescent element, and, to provide an organic electroluminescent element which has a high emission efficiency, is capable of low voltage driving and has a high driving stability, and a display and a lighting. The present invention relates to a polymer having a repeating unit represented by the following general formula (1) and a crosslinking group (in the general formula (1), Ar11 to Ar13 each independently represent a bivalent aromatic group, Ar14 and Ar15 each independently represent an aromatic group, Ar16 and Ar17 each independently represent a direct bond or a bivalent aromatic group, R11 and R12 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, or an aromatic group, and r represents an integer of 0 to 5, R11 and R12 may join to each other to form a ring structure. The crosslinking group may also be contained in the repetitive unit represented by the following general formula (1)).

Description

technical field [0001] The present invention relates to polymers, in particular to polymers useful as hole injection layers and hole transport layers of organic electroluminescence devices, organic electroluminescence device materials containing the polymers, compositions for organic electroluminescence devices, and organic electroluminescence devices A light-emitting element, and a display device and a lighting device having the organic electroluminescent element. Background technique [0002] In recent years, development of an electroluminescence element using an organic thin film (ie, an organic electroluminescence element) has been carried out. As a formation method of the organic thin film in an organic electroluminescent element, a vacuum vapor deposition method and a wet film formation method are mentioned, for example. [0003] The wet film-forming method has advantages such as no need for a vacuum process, easy to increase the area, and easy mixing of a plurality o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02H01L51/50
CPCH01L51/0035H01L51/0039C08G73/026H01L51/5016H10K85/111H10K50/11H10K2101/10H10K85/115
Inventor 饭田宏一朗五郎丸英贵李延军马场达志冈本智美
Owner MITSUBISHI RAYON CO LTD
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