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Binaphthol based chromophores for the fabrication of blue organic light emitting diodes

Inactive Publication Date: 2004-07-22
RGT UNIV OF CALIFORNIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of these materials include their propensity for crystallization and difficulties in obtaining films by solution processing.
If the substrate has excessively low gas-barrier property, the organic electroluminescent device may disadvantageously deteriorate due to outside air passing through the substrate.
Usually, fluorescent dyes may not be applicable to such use because most fluorescent dyes have poor thin film forming ability.
Also, the intermolecular interaction between the fluorescent dyes may cause a decrease in luminous efficiency by quenching effect.
If the content is less than about 0.1% by weight, the dopant dye may fail to sufficiently contribute to the improvement of light emission efficiency of the device, whereas if the dye exceeds about 30% by weight, concentration quenching may occur to cause reduction of the light emission efficiency.

Method used

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  • Binaphthol based chromophores for the fabrication of blue organic light emitting diodes
  • Binaphthol based chromophores for the fabrication of blue organic light emitting diodes
  • Binaphthol based chromophores for the fabrication of blue organic light emitting diodes

Examples

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example 2

[0081] This example describes the synthesis and characterization of a binaphtyl compound of the formula (IV). 22

[0082] A round bottom flask was charged with 6,6'dibromo-2,2'dilaexyloxy-1-,1'binaphthyl (895 mg, 1.46 mmol), 1-pyrene boronic ester (1.2 g, 3.66 mmol, 2.5 equivs), sodium bicarbonate (845.3 mg, 7.31 mmol and Pds(PPh.sub.3).sub.4 (84.5 mg, 0.073 mmol, 0.05 equivs). The mixture was evacuated and refilled with Argon three times and dissolved in Toluene / THF / water (3:3:1). The solution was degassed three times and the mixture heated under Argon at 86.degree. C. for 48 hrs. After heating, the solution was cooled down, the solvent evaporated, water was added and the aqueous phase was extracted with chloroform three times. The combined organic phases were washed with brine, dried, evaporated and concentrated under vacuum to afford the crude product. The resulting solid was purified by flash column chromatography on silica gel (hexanes 75%, chloroform 25%) to afford the compound o...

example 3

[0085] This example provides a characterization of absorption and emission in solution and thin films of the compound of formula (III) or the compound of formula (IV). The PL, and absorption in solution were measured from chloroform solutions (10.sup.-6 and 4.times.10.sup.-6 M respectively). The thin films were prepared by vacuum evaporation. The results obtained are summarized in FIG. 1. In FIG. 1A, the absorption of the compound of formula (III) is shown in chloroform solution 2 and in the solid state 4. In FIG. 1B, the normalized PL of the compound of formula (III) is shown in solution 6 and in thin film 8. In FIG. 1C, the absorption of the compound of formula (IV) is shown in chloroform solution 10 and in the solid state 12. In FIG. ID, the normalized PL of the compound of formula (IV) is shown in solution 14 and in thin film 16. The compound of formula (III) in solution gave a blue emission (.lambda..sub.PL at 430 nm) under UV excitation at 351 nm. The quantum efficiency was 0....

example 4

[0086] This example demonstrates the fabrication of electroluminescent devices using blue emitting binaphthol compounds.

[0087] The devices were fabricated by vacuum evaporation of the organic layers (CuPc / .alpha.-NPD / EML / SAlq / Alq.sub.3) on glass / ITO substrate at about 10.sup.-6 Torr in the same chamber without breaking vacuum. The ITO layer on glass substrate was 120 nm thick, and a stripe pattern with a 2-mm wide ITO layer was etched by photolithographic techniques. The patterned ITO glass was previously ultrasonically cleaned using a detergent, rinsed in water and finished with UV-ozone method. The rates of deposition of the organic layers was between 1.0 and 2.3 .ANG. / s and the temperatures of deposition were within a range of 206-304.degree. C., depending on the layer. The cathode was deposited in another chamber with a metal shadow mask that defines a 2-mm stripe cathode pattern perpendicular to the ITO anode stripe 20. FIG. 2 is a top view of the device showing the 2-mm wide a...

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Abstract

A blue electroluminescent material based on a binaphtyl compound of the general formula (I). Particular embodiments having the general formula have good solubilities in common organic solvents, resist crystallization and can be sublimed in a device fabrication process. These properties enable the fabrication of organic electroluminescent devices.

Description

DESCRIPTION OF THE RELATED ART[0001] Semiconducting (conjugated) polymers, oligomers and small molecules have been studied as electroluminescent materials for use in light emitting displays since the early 1990s. Such emissive polymer displays offer a number of advantages, including high brightness at low operating voltage, low weight, thin profile and low power consumption over conventional display elements such as incandescent lamps and liquid crystal displays.[0002] The requirements of the electroluminescent layer for use in high efficiency, stable light emitting devices include the following:[0003] A. High Photoluminescence ("PL") Efficiency[0004] In an efficient luminescent medium, radiative recombination is favored over non-radiative recombination. PL efficiencies in excess of 10% are preferred; PL efficiencies in excess of 25% are still more preferred; and PL efficiencies in excess of 50% are still more preferred.[0005] B. B. Good Film Forming Ability[0006] Emissive organic m...

Claims

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Application Information

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IPC IPC(8): C07C43/20C07D209/02C07D209/86C07D215/14C07D217/24C07D219/14C07D223/26C07D235/20C07D241/42C07D263/56C07D263/57C07D265/38C07D271/10C07D271/107C07D277/66C07D321/10C07D321/12C07D401/10C07D471/04C09K11/06H01L51/00H01L51/30H01L51/50H05B33/14
CPCC07C43/202H05B33/14C07D209/86C07D215/14C07D217/24C07D219/14C07D223/26C07D235/20C07D241/42C07D263/57C07D265/38C07D271/107C07D277/66C07D321/10C07D321/12C07D401/10C07D471/04C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1048H01L51/0052H01L51/0053H01L51/0054H01L51/0055H01L51/0058H01L51/0062H01L51/0067H01L51/0071H01L51/0072H01L51/0078H01L51/0081H01L51/0094H01L51/5012H01L2251/308C07D209/02Y10S428/917H10K85/621H10K85/615H10K85/622H10K85/623H10K85/626H10K85/649H10K85/654H10K85/657H10K85/6572H10K85/311H10K85/324H10K85/40H10K50/11H10K2102/103
Inventor BAZAN, GUILLERMO C.BENMANSOUR, HADJAR
Owner RGT UNIV OF CALIFORNIA
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