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Electroluminescent polymers, organic EL devices and displays

A luminescence and polymer technology, applied in electroluminescent light sources, electrical components, electric light sources, etc., can solve the problems of thermal properties such as glass transition temperature reduction, component life reduction, and changes

Active Publication Date: 2006-11-22
DEXERIALS CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, 1) has the following problems: when forming a film from a solvent-soluble precursor, defects in the film are generated due to leaving components, or the number of film-forming steps is increased
[0006] 2) When an organic group that imparts solubility is introduced or 3) when a zigzag structure is introduced, the conjugated polymer exhibits a liquid crystal phase or easily generates an aggregation structure such as an intermolecular complex, causing a red shift in the emission wavelength
Also, in these cases there is also the issue of changes in thermal properties such as lower glass transition temperature
Therefore, the luminous color changes due to the change of the aggregation structure that occurs during film formation. In addition, after film formation, the form (morphological properties) of the π-conjugated polymer changes depending on the operating environment, resulting in the hue of the luminescent color. Changes or issues with reduced component life
This problem becomes a very serious problem in π-conjugated polymers used in automotive indicators and displays used in automobiles where the ambient temperature frequently rises rapidly.

Method used

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  • Electroluminescent polymers, organic EL devices and displays
  • Electroluminescent polymers, organic EL devices and displays
  • Electroluminescent polymers, organic EL devices and displays

Examples

Experimental program
Comparison scheme
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Embodiment

[0056] The present invention will be described more specifically by way of examples below.

reference example 1

[0058] (Synthesis of 2,7-dibromo-9,9-dioctylfluorene)

[0059]

[0060] Add 10.0g (30.9mmol) 2,7-dibromofluorene, 19.7g (102.0mmol) 1-bromooctane, 25ml dimethyl sulfoxide, 24.9g (623mmol ) sodium hydroxide, 50ml of water, heated to 80°C. After confirming the dissolution of 2,7-dibromofluorene, 608 mg (2.66 mmol) of benzyltriethylammonium chloride was added, followed by heating and stirring for 20 hours.

[0061] The obtained reaction solution was extracted with hexane, and the extract was dried, and the hexane was distilled off, and then excess 1-bromooctane was distilled off under reduced pressure under heating. Next, the resulting residue was purified by column chromatography (carrier: silica gel, elution solvent: hexane), and 2,7-dibromo-9,9-dioctylfluorene was isolated as colorless crystals (yield: 14.3 g ( 26.1 mmol), yield 84.5%). The resulting compound was identified by 1 H-NMR, 13 C-NMR performed.

[0062] 1 H-NMR (CDCl 3 , δ): 7.58-7.40 (M, 6H), 1.90 (t, J ...

reference example 2

[0065] (Synthesis of 2,7-dibromo-9,9-bis(2-ethylhexyl)fluorene)

[0066]

[0067] Add 29.3g (90.4mmol) 2,7-dibromofluorene, 75ml dimethyl sulfoxide, 60.0g (311mmol) 1-bromo-2-ethylhexane, 150ml 12.5M sodium hydroxide in a 1000ml eggplant-shaped flask Aqueous solution was stirred, and 1.20 g (5.27 mmol) of benzyltriethylammonium chloride was added thereto. At this point the organic phase was reddish purple. Next, the mixture was stirred at 90°C for two nights, extracted with diethyl ether, and the extract was washed with water and dried.

[0068] Concentrate the dry extract, add 50ml dimethyl sulfoxide, 29.2g (151mmol) 1-bromo-2-ethylhexane, 100ml 12.5M aqueous sodium hydroxide solution to the concentrated solution, stir, add 1.20g (5.27 mmol) benzyltriethylammonium chloride. The mixture was then stirred at 90° C. for 4 days, at which time the organic phase was reddish-purple. Then it was stirred at 90°C for two nights, extracted with diethyl ether, washed and dried.

...

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Abstract

Novel electroluminescent polymers which little form cohesion structure in film formation and little cause morphologic change even after film formation and which exhibit stable EL characteristics. The polymers comprise binaphthyl derivative structural units represented by the general formula (1a) and aryl structural units represented by the general formula (1b): (1a) (1b) wherein Ar is an aryl structural unit capable of forming an electroluminescent pi-conjugated polymer; R<1>, R<2>, R<3>, and R<4> may each independently take various substituents; each moiety represented by both a dotted line and a solid line represents an unsaturated double bond or a saturated single bond; m and p are each independently 0 to 2; n and o are each independently 0 to 8; x is the mole fraction of the binaphthyl derivative structural units; and y is the mole fraction of the aryl structural units.

Description

technical field [0001] The present invention relates to an EL polymer useful as a light-emitting layer material of an organic electroluminescent (EL) element, an organic EL element using the EL polymer, and a display device using the organic EL element. Background technique [0002] Conventionally, poly(p-phenylene vinylene) (PPV), poly(p-phenylene) (PPP), poly(9,9-dialkylfluorene) have been used as organic EL materials for the light-emitting layer of organic EL elements. (PDAF) and other π-conjugated polymers (Y. Ohmori et al., Jpn. J. Appl. Phys., 1991, 30, L1941). [0003] However, in these π-conjugated polymers, the proportion of aromatic rings in the polymer is very high, and their solubility in organic solvents is insufficient. These π-conjugated polymers may not be suitable for spin coating or various methods when forming films. Simple film-forming methods such as printing methods (such as inkjet methods). [0004] Therefore, when forming a π-conjugated polymer into...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/10H01L51/50C09K11/06H01L51/00H05B33/14
CPCC08G61/10C09K11/06C09K2211/1416H05B33/14H10K85/115H10K85/111H10K85/151H10K50/11
Inventor 月冈美幸须永友康石井淳一柳堀进
Owner DEXERIALS CORP
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