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Conjugated polymer containing sulfonic group substituted triarylamine and use thereof

A technology of conjugated polymers and triarylamines, applied in the field of organic compounds, can solve the problems of no preparation, application limitations of cross-linked hole transport materials, difficulty in initiator impurities, etc., and achieve good thermal stability and electrochemical stability properties, device fabrication process is simple and easy, excellent hole transport effect

Inactive Publication Date: 2010-04-14
GUANG ZHOU NEW VISION OPTO ELECTRONICS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The above-mentioned invention does not relate to the preparation and related information of triarylamine monomers and polymers containing polar groups or ionic groups, and the obtained polymers are generally soluble in non-polar organic solvents. The disadvantage is that The resulting polymer has similar solubility to commonly used luminescent materials
Such a process is relatively simple and easy to control, but its disadvantage is that it is prone to miscibility between adjacent interfaces during the preparation of the device.
[0024] The above-mentioned triarylamine-containing and cross-linkable hole transport materials generally have lower performance after cross-linking than before cross-linking, which may be caused by side reactions during the cross-linking process and volume shrinkage after cross-linking. caused by tiny cracks
But its disadvantage is that it is generally necessary to add a small amount of initiators in the crosslinking reaction. These initiators are difficult to be completely removed as impurities and are easy to become traps for hole quenching.
In addition, the degree of cross-linking is difficult to control, and the reproducibility of the reaction is poor
The tiny cracks formed during the cross-linking process are likely to cause device leakage and reduce the service life of the device
These defects limit the application of the above-mentioned cross-linked hole transport materials.

Method used

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  • Conjugated polymer containing sulfonic group substituted triarylamine and use thereof
  • Conjugated polymer containing sulfonic group substituted triarylamine and use thereof
  • Conjugated polymer containing sulfonic group substituted triarylamine and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1: preparation 4,4'-dibromotriphenylamine

[0075] 4,4'-Dibromotriphenylamine was prepared according to the method published in "Syn. Met" (Syn. Met) 122 (2001) 363. Weigh triphenylamine (4.9 g, 20 mmol) and measure N, N-dimethylformamide (DMF) 100 ml into a 250 ml three-necked flask, and dissolve completely after stirring, and add to this solution at room temperature N-bromosuccinimide (NBS) (7.12 g, 40 mmol) was added to it, and after two days of reaction at room temperature, the solvent was evaporated under reduced pressure below 70°C, and column separation was carried out after extraction with water and dichloromethane. After distilling off the solvent, 7.9 g of the product was obtained, a yield of 98%. 1HNMR, 13CNMR and GC-MASS tests show that it is the target product 4,4'-dibromotriphenylamine. Its chemical reaction equation is as follows:

[0076]

Embodiment 2

[0077] Embodiment 2: Preparation has the triarylamine compound of substituent

[0078] Preparation of triarylamine compounds with substituents Take the preparation of N,N-diphenyl-(4-trifluoromethyl)aniline as an example, prepare N,N-diphenyl- (4-Trifluoromethyl)aniline. Weigh into diphenylamine (15.57 grams, 92 mmoles) in the there-necked flask of 500 milliliters, (4-trifluoromethyl) iodobenzene (31.43 grams, 115 mmoles), palladium acetate (404 mgs, 1.8 mmoles), Tri-o-cresylphosphine (1.19 g, 3.9 mmol), sodium tert-butoxide (12.50 g, 130 mmol) and dry purified toluene (200 mL). The suspension was stirred at reflux for 12 hours under an inert atmosphere. Thereafter, it was filtered, and the solvent was distilled off, followed by column separation using toluene as an eluent. After distilling off the solvent, 23.16 g of the product were obtained, a yield of 80%. 1HNMR, 13CNMR and GC-MASS tests showed that it was the target product N,N-diphenyl-(4-trifluoromethyl)aniline. It...

Embodiment 3

[0081] Embodiment 3: Preparation of dibromo-substituted triarylamine compound

[0082] Preparation of dibromo-substituted triarylamine compound Taking N,N-di-p-bromophenyl-(4-trifluoromethyl)aniline as an example, it was prepared according to the method disclosed in the world patent WO 0166618 in 2000. Under nitrogen protection, N, N-diphenyl-(4-trifluoromethyl)aniline (23.16 g, 74 mmol) was weighed and dissolved in 200 ml of anhydrous DMF, and NBS ( 27.6 g, 155 mmol) in 200 mL of DMF and keeping the internal temperature of the reaction below 20 °C. After 1 hour the reaction was complete and it was poured into 3 liters of water. The crude product precipitated out, was filtered and recrystallized several times from petroleum ether-diethyl ether (volume ratio 80 / 100) to give the product 15.2 g. 1HNMR, 13CNMR and GC-MASS tests showed that it was the target product N,N-di-p-bromophenyl-(4-trifluoromethyl)aniline. Its chemical reaction equation is as follows:

[0083]

[008...

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Abstract

The invention discloses a conjugated polymer substituted by sulfonic group with triarylamines compound composition, which includes nonpolar substituent groups of monomer A and C and triarylamine monomer B substituted by sulfonic group; the said conjugated polymer can improve radioluminescence efficiency of devices such as luminescent device, photovoltaic device and so on as hole transport layer.

Description

technical field [0001] The invention relates to an organic compound, especially a conjugated polymer containing sulfonic acid group-substituted triarylamine compound components. [0002] The invention also relates to the use of said polymers. Background technique [0003] Organic light-emitting diodes (OLEDs) can be prepared from small molecules [US4,539,507], conjugated polymers [WO 90 / 13148] and dendrimers [WO 99 / 21935]. The simplest OLED structure is a single-layer sandwich structure, which consists of an anode, a cathode, and an organic light-emitting layer, and the light-emitting layer is sandwiched between two electrodes, the cathode and the cathode. After an appropriate forward bias is applied between the anode and the cathode, holes and electrons are injected into the device from the anode and the cathode respectively, recombine in the light-emitting layer and generate excitons, and release energy in the form of light radiation. In order to achieve a better device ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/02H05B33/22
Inventor 曹镛石伟范素芹杨伟
Owner GUANG ZHOU NEW VISION OPTO ELECTRONICS TECH
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