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Oxaspirofluorene triphenylamine derivative, preparation method and use thereof

A technology of oxaspirofluorene and triphenylamine, applied in the field of organic optoelectronic materials, can solve problems such as reducing the cost of organic phosphorescent devices, and achieve the effects of good resonance energy transfer and stability, reduction of singlet energy, and high-efficiency electroluminescence performance.

Inactive Publication Date: 2020-12-15
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To solve the problem of reducing the cost of organic phosphorescent devices

Method used

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  • Oxaspirofluorene triphenylamine derivative, preparation method and use thereof
  • Oxaspirofluorene triphenylamine derivative, preparation method and use thereof
  • Oxaspirofluorene triphenylamine derivative, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Step 1: Dissolve 4.23 grams of o-bromoiodobenzene in 80 mL of o-dichlorobenzene under the protection of argon, and add 1.83 grams of phenoxazine, 0.7 grams of cuprous iodide, 0.1 grams of 18-crown 6 ether and 5.0 grams of potassium carbonate in sequence. grams in a 200 ml reaction vial. After reflux for 48 hours under the protection of argon, the reaction solution was cooled to room temperature. The solvent was removed to dryness by a rotary evaporator. The reaction solid was dissolved in 80 mL of dichloromethane, and the organic layer was washed three times with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate and spin-dried. Silica gel was added to spin-dry the obtained solid, which was passed through the column with dichloromethane / petroleum ether=3:7 (volume ratio), and spin-dried to obtain 3.04 g of 2-bromooxatriphenylamine, with a yield of 90%. Step 2: Dissolve 1.52 g of 2-bromooxatriphenylamine in 80 mL of tetrahydrofuran under the pro...

Embodiment 2

[0050] Step 1: Same as Step 1 of Example 1.

[0051] Step 2: Same as Step 2 of Example 1.

[0052] Step 3: Dissolve 2.0 g of 2-bromooxaspirofluorenetriphenylamine in 80 mL of tetrahydrofuran under the protection of argon, cool to -78°C, and slowly add 2.0 mL of n-butyllithium into the solution through a constant pressure dropping funnel, React for 1 hour. Then 1.1 g of bis(trimethylphenyl)boron fluoride was dissolved in 40 mL of tetrahydrofuran under the protection of argon and added dropwise to the reaction solution. After 2 hours of reaction at low temperature, it was gradually raised to room temperature. After 12 hours of reaction, 5 mL of water was added to the reaction, and then the solvent was spin-dried under reduced pressure. The solid was dissolved in 80 mL of dichloromethane, and the organic layer was washed three times with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate and spin-dried. Pass through the column with dichloromethane / petro...

Embodiment 3

[0054] Step 1: Same as Step 1 of Example 1.

[0055] Step 2: Same as Step 2 of Example 1.

[0056] Step 3: Dissolve 1.52 g of 2-bromooxatriphenylamine in 80 mL of tetrahydrofuran under the protection of argon, cool to -78°C, slowly add 2.38 mL of n-butyllithium into the solution through a constant pressure dropping funnel, and react 1 Hour. Then 1.3 g of 3-bromofluorenone was dissolved in 40 mL of tetrahydrofuran under the protection of argon and added dropwise to the reaction solution. After 1 hour of reaction at low temperature, it was gradually raised to room temperature. After 12 hours of reaction, 5 mL of water was added to the reaction, and then the solvent was spin-dried under reduced pressure. The solid was dissolved in 80 mL of dichloromethane, and the organic layer was washed three times with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate and spin-dried. The solid obtained by spin-drying was dissolved in 45 mL of glacial acetic acid and...

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Abstract

The invention discloses an oxaspirofluorene triphenylamine derivative, a preparation method and its application. The oxacyclic spirofluorene triphenylamine derivative has a very small singlet-triplet energy level difference, thermal stability and space Cave transport properties. By effectively controlling the rigidity, conjugation degree and electron-withdrawing strength of the host material structure, the singlet-triplet energy level difference of the material can be precisely adjusted to reduce it, and the turn-on voltage of the device is significantly reduced. Moreover, the material in the present invention has excellent resonance energy transfer performance. Compared with commonly used phosphorescent host materials, the device performance and efficiency roll-off are qualitatively improved. In addition, under the doping condition of very low guest concentration (0.5 wt%), its power efficiency can still reach the highest efficiency (58 lumens per watt) based on this type of material. This result is instructive for reducing the production cost of organic phosphorescent light-emitting diodes by reducing the concentration.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to an oxaspirofluorene triphenylamine derivative, a preparation method and an application thereof. Background technique [0002] Organic electroluminescence is a self-luminous device. By sandwiching a light-emitting layer between a pair of electrodes and applying a voltage, electrons injected from the cathode (first electrode) and holes injected from the anode (second electrode) recombine at the light-emitting center. Molecular excitons are formed, and upon returning to the ground state, the molecular excitons release energy to emit light. Organic electroluminescent devices have the characteristics of low voltage, high brightness, good color purity, wide viewing angle, fast response, and good temperature adaptability, and are widely used in computer, mobile phone, MP3, TV and other electronic product displays. Organic electroluminescent materials...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/10C07F5/02C09K11/06H01L51/50H01L51/54H01L51/56
CPCC09K11/06C07D498/10C07F5/027C09K2211/1033C09K2211/1029C09K2211/1007C09K2211/1059H10K85/654H10K85/657H10K50/12H10K71/00
Inventor 廖良生蒋佐权王亚坤
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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