Organic electroluminescence or charge transmission material containing olefine acid ester side group and synthesis thereof

A technology of charge transport and enolate, which is applied in the direction of luminescent materials, electroluminescent light sources, electric light sources, etc., can solve the problems of short circuit, unreported research literature, and impure luminescence, etc., and achieve good solubility, simple reaction, The effect of chemical stability

Inactive Publication Date: 2012-06-06
DONGGUAN ANWELL DIGITAL MASCH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the spin-coating process of different organic layers, the solvent in the upper layer will often redissolve and lose the organic molecules that have been formed in the lower layer. Since the thickness of the organic coating layer is at the nanometer level, it is easy to form holes after being dissolved by the solvent, resulting in Phenomenon of impure light or short circuit
In order to make the organic layer of the spin-coated film no longer soluble in the solvent, the molecules of the organic layer can be photo-crosslinked and linked together with chemical bonds so that it is no longer soluble in the organic solvent, but there is no relevant research literature report

Method used

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  • Organic electroluminescence or charge transmission material containing olefine acid ester side group and synthesis thereof
  • Organic electroluminescence or charge transmission material containing olefine acid ester side group and synthesis thereof
  • Organic electroluminescence or charge transmission material containing olefine acid ester side group and synthesis thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: Luminescent material - the synthesis of 2-methacryloyloxymethyl perone and the process of photocross-linking synthesis are as follows:

[0017]

[0018] DMF is dimethylformamide; THF is tetrahydrofuran; MeOH is methanol; DCC is 1,3-dicyclohexylcarbodiimide; DMAP is 4-dimethylaminopyridine.

[0019] The process steps are:

[0020] (1) Synthesis of 2-formyl Piperium from Piperium

[0021] Add POCl to DMF (1.4-1.5g) at 0°C under nitrogen protection 3 (3.0 ~ 3.2g), and then the pernicket (3.9 ~ 4.3g) dissolved in 60ml of 1,2-dichloroethane was added to the reaction system. Heating to 50℃~70℃ for 4~6h. After cooling, 500 ml of water was added to the reaction system, and extracted with ethyl acetate. Na for organic layer 2 CO 3 Aqueous neutralization. After evaporating the solvent, the mixed solvent of toluene-ethyl acetate (volume ratio 9:1) was used as a developing solvent for silica gel chromatography, and the yield was 63%-68%.

[0022] (2) Synthe...

Embodiment 2

[0028] Example 2: The synthesis and photocross-linking process of charge transport material - methacryloyloxymethyl m-TDATA is as follows:

[0029]

[0030] The process steps are:

[0031] (1) Synthesis of aldehyde group m-TDATA

[0032] Add POCl to DMF (1.4-1.5g) at 0°C under nitrogen protection 3 (3.0~3.2g), and then m-TDATA (15.3~16g) dissolved in 250ml 1,2-dichloroethane was added to the reaction system. Heating to 50℃~70℃ for 4~6h. After cooling, 500 ml of water was added to the reaction system, and extracted with ethyl acetate. Na for organic layer 2 CO 3 Aqueous neutralization. After evaporating the solvent, the mixed solvent of toluene-ethyl acetate (volume ratio 9:1) was used as a developing solvent for silica gel chromatography, and the yield was 40%-47%.

[0033] (2) Synthesis of hydroxymethyl m-TDATA

[0034] NaBH was added to 150ml THF solution in which aldehyde group m-TDATA (8.9~9.5g) was dissolved at room temperature 4 (2.0~3.0g) aqueous solution (5...

Embodiment 3

[0039] Example 3: Synthesis and photocrosslinking of luminescent material - poly 9,9'dioctylfluorene-2-methacryloyloxybenzene The synthesis process is as follows:

[0040]

[0041] The process steps are:

[0042] (1) Synthesis of poly 9,9'dioctylfluorene-2-phenol

[0043] Dissolve 5.58g of dioctylfluorene bisboronate, 2.52g of 2,6-dibromophenol and 12-15mg of triphenylphosphorous palladium in 15-20ml of toluene and add 15-20ml of an aqueous solution in which 0.83-0.90g of potassium carbonate is dissolved , React in the dark at 85-90°C for 40-48 hours. After the reaction was completed, the reaction solution was poured into methanol for precipitation, and the precipitate was separated by centrifugation. Dissolve in chloroform, precipitate in methanol, repeat 5 times, and store in dry. Yield 78%~83%.

[0044] (2) Synthesis of poly 9,9'dioctylfluorene-2-hydroxypropoxybenzene

[0045] Add K 2 CO 3 (10.0~12.0g). Stir at 50°C for 12h. Methanol was added to precipitate, an...

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PUM

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Abstract

The invention relates to organic electroluminescence or charge transport material with side group of unsaturated ester. The general formula is (I), A is electroluminescence or charge transport material, organic semi- conductor main structure, such as piper, or m- TDATA, or poly fluorene benzene; R is alkyl. The synthesis method comprises following steps: introducing hydroxyl group for main structure A of organic semi- conductor, the ester reacting with hydroxyl to produce side group unsaturated ester, rotary coating and filming, crosslinking and curing with ultra- violet. The invention is characterized by low raw material cost, simple reaction, suitability for large- scale production, more stable chemical property and better solubility of product, good liquid processing property, insoluble of crosslinked molecule in organic solution and free from influence from rotary coating of solution on upper layer.

Description

technical field [0001] The invention belongs to the technical field of organic flat panel displays, and in particular relates to the structure and preparation method of photocrosslinkable organic electroluminescence or charge transport materials containing enolate side groups. Background technique [0002] Organic Light Emitting Display (OLED for short), which is a newly emerging category on mobile phone screens, MP3 and MP4 screens, is known as "dream display". OLED display technology is different from traditional LCD display methods. It does not require a backlight, and uses very thin organic material coatings and glass substrates. When an electric current passes through, these organic materials will emit light. Therefore, OLED screens can be made lighter and thinner, have a larger viewing angle, and can significantly save power. [0003] The structure of an OLED display typically has several layers of organic material between the metal cathode and the ITO anode. The mai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06H05B33/14
Inventor 徐宁王健赵宏斌郑飞璠
Owner DONGGUAN ANWELL DIGITAL MASCH CO LTD
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