Fluorene-based hole transport compound

A technology of hole transport and compound, which is applied in the field of fluorene-based hole transport compounds, can solve the problems of high energy consumption for preparation, affect device efficiency, and poor thermal stability, and achieve high luminous purity, high luminous efficiency, and good thermal stability sexual effect

Active Publication Date: 2014-10-08
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional hole injection materials, such as copper phthalocyanine (CuPc), are slow to degrade, consume high energy for preparation, are not conducive to environmental protection, and they absorb light, which affects the efficiency of devices
The original hole transport materials such as NPB have poor thermal stability, which also greatly affects the life of the device.

Method used

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  • Fluorene-based hole transport compound
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  • Fluorene-based hole transport compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Synthesis of Compound 2

[0063]

[0064] Synthesis of Compound 2-1

[0065] In the reaction flask, add fluorenone (9g, 50mmol) and water (30ml), heat to 80°C, slowly add liquid bromine (8.8g, 55mmol) into the reaction flask, react for 4 hours, add 100ml of water and 100ml of 10% Aqueous solution of sodium bisulfate. After filtration, the obtained solid was recrystallized with absolute ethanol to obtain 11 g of product with a yield of 85%.

[0066] Synthesis of compound 2-2

[0067] In the reaction flask, add compound 2-1 (2.58g, 10mmol) and 15ml tetrahydrofuran, add dropwise phenylmagnesium bromide Grignard reagent (12mmol) dissolved in tetrahydrofuran at 0°C, and slowly rise to room temperature after the addition is completed. Reaction 12 After 1 hour, dilute hydrochloric acid was added to adjust the pH to 7, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and the solvent was removed. The crude product was chromatographed on a silica gel co...

Embodiment 2

[0076] Synthesis of compound 22

[0077]

[0078] In the reaction flask, add compound 2-3 (0.5g, 0.89mmol), 4-triphenylamine borate (0.3g, 1mmol), tetrahydrofuran (10ml), tetrakis (triphenylphosphine) palladium (50mg), potassium carbonate aqueous solution (2mol / l, 5mL), heated under reflux under the protection of nitrogen to react overnight. Stop the reaction, extract three times with dichloromethane, combine the organic phases, and wash with water until neutral; separate the organic phases, add anhydrous magnesium sulfate to dry, filter with suction, and spin dry; silica gel column chromatography gives 340 mg of white solids, yield 52 %.

[0079] 1 H NMR (400MHz, CDCl 3 )δ7.76-7.80(m,2H),7.56-7.60(m,2H),7.35-7.45(m,4H),7.19-7.29(m,14H),6.89-7.13(m,18H).ESI, m / z: [M+H]+: 729.4. See NMR spectrum figure 2

Embodiment 3

[0081] Synthesis of compound 28

[0082]

[0083] In the reaction flask, add compound 2-3 (0.2g, 0.35mmol), 4-(1-naphthylanilino) phenylboronic acid (0.15g, 0.44mmol), tetrahydrofuran (10ml), tetrakis (triphenylphosphine) Palladium (10 mg), potassium carbonate aqueous solution (2 mol / l, 5 mL), heated to reflux under nitrogen protection overnight. Stop the reaction, extract three times with dichloromethane, combine the organic phases, and wash with water until neutral; separate the organic phases, add anhydrous magnesium sulfate to dry, filter with suction, and spin dry; silica gel column chromatography gives 170 mg of white solids, yield 63 %. 1 H NMR (400MHz, CDCl 3 )δ7.88-7.95(m,2H),7.74-7.90(m,3H),7.34-7.57(m,11H),7.19-7.28(m,11H),6.88-7.09(m,15H).ESI, m / z: [M+H]+: 779.4. See NMR spectrum image 3

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Abstract

The invention provides a fluorene-based hole transport compound with a structural formula (I) as shown in the specification. The compound has relatively good thermal stability, high luminous efficiency and high luminous purity, can be used for making organic light-emitting devices and is applied to the fields of organic solar cells, organic thin-film transistors or organic photoreceptors.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a fluorene-based hole transport compound. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, emissive layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light emitting layer through the hole transport layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as required. [0003] As a new type of display technology, organic electroluminescent devices have self-illumination, wide viewing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C211/58C07C209/10C07C209/68C07D307/91C07D209/88C07D333/76H01L51/54
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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