Electron transport agents for organic electronic devices

a technology of electronic devices and electron transport agents, which is applied in the field of electron transport agents for organic electronic devices, can solve the problems of extremely short operating lifetimes of devices based on these materials, and exhibit short operating lifetimes

Inactive Publication Date: 2008-01-31
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, OLED devices employing PBD or TAZ often exhibit short operating lifetimes due to recrystallization of or aggregate formation by the PBD or TAZ, leading to phase separation and formation of charge carrier traps that inhibit emission.
However, operating lifetimes for devices based on these materials were found to be extremely short due to PBD aggregation (e.g., see Strukelj et al., Science, 267, 1969, (1995)).

Method used

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  • Electron transport agents for organic electronic devices
  • Electron transport agents for organic electronic devices
  • Electron transport agents for organic electronic devices

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 2-(2,5-Dichlorophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole

[0255]

Part A: Synthesis of Methyl 4-octoxybenzoate

[0256] Into a flask was introduced 251.0 g (1.65 mol) of methyl 4-hydroxybenzoate, 276.37 g (1.99 mol) potassium carbonate and 1200 g of acetone. This was refluxed for 45 min followed by the dropwise addition of 386.17 g (1.99 mol ) of 1-octylbromide over a 1 hour period. The reaction mixture was refluxed for two days. Filtration of the cooled reaction mixture and evaporation of the filtrate gave an oil. This was taken up in ethyl acetate and extracted with 5% NaOH (2×100 ml) followed by water (2×100 ml). The organic layer was dried (MgSO4), concentrated, and transferred to a 1 L three necked flask. The contents of the flask was subjected to high vacuum distillation to remove the excess 1-octylbromide. The pot residue was essentially pure methyl 4-octoxybenzoate (376g, 86%).

Part B: Synthesis of 4-Octoxybenzoyl Hydrazide

[0257] To the contents of the flask f...

example 2

Synthesis of 2-(4-tert-butylphenyl)-5-(2,5-dichlorophenyl)-1,3,4-oxadiazole

[0261]

Part A: Synthesis of N-(4-tert-Butylbenzoyl)-2,5-dichlorobenzohydrazide

[0262] 4-tert-Butylbenzoyl hydrazide (185 g, 0.96 mol) and triethylamine (97.37 g, 0.96 mol) freshly distilled from calcium hydride were added to 4 L of dichloromethane in a 10 L flask. To this was added with mechanical stirring 201.5 g of 2,4-dichlorobenzoyl chloride. No precipitation of the product was observed after three hours and the reaction was allowed to stir at room temperature until the next day. The product was precipitated by the addition of 4 L hexane. Filtration, hexane washing and drying at 80° C. in a forced air oven gave the product in 99% yield.

Part B: Synthesis of 2-(4-tert-butylphenyl)-5-(2,5-dichlorophenyl)-1,3,4-oxadiazole

[0263] Into a 2 L flask was introduced 200 g N-(4-tert-butylbenzoyl)-2,5-dichlorobenzohydrazide (0.55 mol) and 1378 ml phosphorus oxychloride (2267 g, 14.78 mol). This was refluxed for 8 hr...

example 3

Synthesis of 2-(2,5-Dibromophenyl)-5-[4-(octyloxy)phenyl]1,3,4-oxadiazole

[0264] This example describes the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]1,3,4-oxadiazole and also provides a general method for preparing a range of useful aryl oxadiazole dibromide intermediates useful in Suzuki coupling reactions.

Part A: Synthesis of 2,5-Dibromobenzoyl Chloride

[0265] By the general method of Part C of Example 1, the reaction of 50.0 g (0.1786 mol) 2,5-dibromobenzoic acid with 150 mL thionyl chloride gave after distillation 40 g of 2,5-dibromobenzoyl chloride.

Part B: Synthesis of 2,5-Dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide

[0266] By the general method of Part A, Example 2, 2,5-dibromobenzoyl chloride (57.43 g, 0.11925 mol), 4-octoxybenzoyl hydrazide (50.88 g, 0.1925 mol), and triethylamine (27 ml, 19.48 g, 0.1925 mol) were reacted in 800 ml methylene chloride to give a product. Re-crystallization of the product from DMF / water gave 79.38 g (78% yield) 2,5-dibromo-...

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Abstract

Compounds and compositions are provided that can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices. The compounds are non-polymeric and have an aromatic core conjugated to end capping groups. The aromatic core contains an arylene group having a pendant heteroaryl group that includes a —C═N— unit.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a divisional of U.S. Ser. No. 10 / 413,653, filed Apr. 15, 2003, now allowed, the disclosure of which is incorporated by reference in its entirety hereinTECHNICAL FIELD [0002] This invention relates to compounds, compositions, organic electronic devices, and methods for preparing organic electronic devices. More particularly, the invention relates to compounds and compositions that can be used as electron transport agents in organic electronic devices such as organic electroluminescent devices. BACKGROUND [0003] Organic electroluminescent (OEL) devices such as organic light emitting diodes (OLEDs) are desirable for use in electronic media because of their thin profile, low weight, capability of obtaining a wide variety of emission colors, and low driving voltage. OLEDs have potential use in applications such as backlighting of graphics, pixelated displays, and large emissive graphics. [0004] There is continuing researc...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): B05D5/12C07D271/10C07D271/107C07D413/14C07F7/08C09K11/06H01L51/00H01L51/50H05B33/10H05B33/14
CPCC07D271/107C07D413/14C07F7/0807H01L51/0035Y10S428/917H01L51/007H01L51/5012H01L51/5048H01L51/0067H10K85/111H10K85/6565H10K85/654H10K50/14H10K50/11C09K11/06H05B33/10
Inventor BENTSEN, JAMESGOPLEN, NICHOLASLI, YINGBOROBERTS, RALPH
Owner 3M INNOVATIVE PROPERTIES CO
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