Improved doping method for hole injection and transport layers

A technology of hole transport and ion doping, which is applied in the field of improved doping for hole injection and transport layers, which can solve problems such as difficult removal and undesired leakage current, and achieve improved current density and luminescence Effects of properties, formulation and construction flexibility, and overall lifespan increase

Active Publication Date: 2016-12-07
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, metal particles and nanoparticles may be formed upon doping, which are difficult to remove and may generate undesired leakage currents

Method used

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  • Improved doping method for hole injection and transport layers
  • Improved doping method for hole injection and transport layers
  • Improved doping method for hole injection and transport layers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0355]

[0356] Poly(3,4-bis(2-(2-poly(3-(3-(2-butoxyethoxy) base) propoxy) thiophene-2,5-diyl).

Embodiment 2

[0358] Synthesis of Butoxyethoxyethoxythiophene:

[0359]

[0360]A 1 L oven-dried 3 NRBF equipped with a condenser, gas inlet and thermometer was charged with 373 g of diethylene glycol butyl ether followed by the addition of 26.41 g of sodium metal. Stir under nitrogen until all sodium is dissolved. To this solution was added 125.5 g of 3-bromothiophene followed by 14.6236 g of Cu(I)I. The mixture was stirred at 100°C for 2.5 hours. Reaction completion was confirmed by GC-MS. 150 g of diethylene glycol butyl ether were vacuum distilled from the RM. The pot residue was diluted with 500 mL of hexane and filtered. The filtrate was washed with 400ml x2 water, followed by 250mL x4 saturated NH 4 Cl solution was washed, and then the organic layer was washed with 300 mL x 3 water. The organic layer was washed with anhydrous MgSO 4 Dried, filtered and concentrated on a rotary evaporator to give 168 g of material. This was vacuum distilled to yield 137.4 g of pure butoxyet...

Embodiment 3

[0370] Synthesis of 3-thienyloxy-3-(1-propanol)

[0371]

[0372] To oven-dried 1 L of 3NRBF equipped with condenser, nitrogen inlet, and thermometer adapter was added 496.7 g of 1,3-propanediol followed by 15.076 g of sodium metal. The reaction mixture was stirred under nitrogen until all sodium was dissolved. At 65° C., 71.79 g of 3-bromothiophene were added, followed by 8.386 g of copper(I) iodide. Stirring was continued at 120°C for 2.5 hours. GC-MS analysis of RM showed 98.8% complete. The reaction mixture was cooled to 35°C, then poured into 1 L of ice water containing 10 g of ammonium chloride. The mixture was neutralized with 1N HCl. Material was extracted from the mixture by washing it three times with 400 mL of MTBE. The combined organic layers were washed four times with 200 mL of saturated ammonium chloride solution, followed by three washes with 200 mL of DI water. The extract was subjected to anhydrous MgSO 4 Drying, filtration and evaporation of the so...

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Abstract

A method comprising reacting at least one first compound in neutral form with at least one ionic dopant in a first solvent system to provide a first doping reaction product; isolating the solid form of the first doping reaction product; and combining the isolated first doping reaction product with a neutral form of at least one conjugated polymer in a second solvent system to form an oxidized form comprising the conjugated polymer and a neutral form of the first compound The second doping reaction product. Advantages include better stability, ease of use, and lower metal content. Applications include organic electronics, including OLEDs.

Description

[0001] related application [0002] This application claims priority to US Provisional Application 61 / 542,868, filed October 4, 2011, and US Provisional Application 61 / 655,419, filed June 4, 2012, both of which are hereby incorporated by reference in their entirety. Background technique [0003] Although favorable progress is being made in energy-efficient devices such as organic-based organic light-emitting diodes (OLEDs), polymer light-emitting diodes (PLEDs), phosphorescent organic light-emitting diodes (PHOLEDs), and organic photovoltaic devices (OPVs), further research is still needed. Improved to provide better handling and performance for commercialization. For example, promising materials are conductive or conjugated polymers including, for example, polythiophenes. However, there may be issues with doping, purity, solubility, handling and / or instability. Also, it is important to have very good control over the solubility of alternating layers of polymers (eg, orthogo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01B1/12H05B33/10H05B33/18H01L51/00
CPCH01B1/122H01B1/127H05B33/18Y02E10/549C09K11/06C09K2211/1416C09K2211/1433C09K2211/1458C09K2211/1466C09K2211/1483C08F226/06C09D125/18C08F212/26C08F212/22H10K71/30H10K85/631H10K85/322H10K85/326H10K85/324H10K50/155C08F212/32C08F12/22C08F12/24C08F12/26H01B1/12
Inventor 文卡塔拉曼南·塞沙德里尼特·乔普拉
Owner NISSAN CHEM IND LTD
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