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Triphenylamine spirofluorene derivatives and uses thereof

A technology of fluorene spirotriphenylamine and its derivatives, which is applied in the field of organic photoelectric materials, can solve the problems of hindering wide application, low material stability, and low glass transition temperature, and achieve lower turn-on voltage, high-efficiency electroluminescence performance, The effect of device performance improvement

Active Publication Date: 2015-09-09
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the glass transition temperature of mCP is low, and the stability of the material itself is not high, which hinders its wide application.

Method used

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  • Triphenylamine spirofluorene derivatives and uses thereof
  • Triphenylamine spirofluorene derivatives and uses thereof
  • Triphenylamine spirofluorene derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Step 1: Dissolve 3.24 g of 2-bromotriphenylamine in 80 mL of tetrahydrofuran under argon protection, cool to -78 °C, slowly add 4.38 mL of n-butyllithium into the solution through a constant pressure dropping funnel, and react for 1 hour . Then 1.8 g of fluorenone 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 glacial acetic acid and 10 mL nicotinic acid, refluxed for 4 hours, cooled to room temperature, then suction filtered and rinsed th...

Embodiment 2

[0047] Step 1: Same as Step 1 of Example 1.

[0048] Step 2: Same as Step 2 of Example 1.

[0049] Step 3: Add 1.11 g of dibromocyclo-closed triphenylamine and 0.68 g of α-N heterocarbazole into a 50 ml flask, add catalyst Pd 2 (dba) 3 92 mg, 80 ml of toluene, 29 mg of tri-tert-butylphosphonium tetrafluoroborate, 30 mg of sodium tert-butoxide, reflux under argon protection for 12 hours, extract with dichloromethane after cooling, dry the organic layer with anhydrous sodium sulfate and spin Dry, pass through the column with dichloromethane / petroleum ether = 1:1 (volume ratio), and spin dry to obtain 1.31 g of SAFNDCZ, with a yield of 88.5%.

Embodiment 3

[0055] The compound SAFNDCZ of the present invention is used as the OLED device host material, FIrpic is a blue phosphorescent dye, and the device structure is:

[0056] ITO / HAT-CN(10nm) / TAPC(45nm) / SAFDCZ:FIrpic(20nm, 15vol% doping) / TmPyPB(40nm) / Liq(2nm) / Al(120nm).

[0057] The device preparation process is as follows: the ITO transparent conductive glass substrate is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, washed repeatedly with deionized water, acetone, and ethanol three times, and baked in a clean environment until the water is completely removed. Treat the ITO conductive glass with UV lamp and ozone. Place the treated ITO conductive glass in a vacuum chamber and evacuate to 3.0×10 -4 -4.0×10 -4 Pa, vacuum evaporated HAT-CN on ITO conductive glass as a hole injection layer (HIL), the evaporation rate is 0.25? / s, and the coating thickness is 10nm; vacuum evaporated TAPC on the hole injection layer as a hole Transport layer (HTL) a...

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Abstract

The invention discloses triphenylamine spirofluorene derivatives and uses thereof. The general chemical structure of the triphenylamine spirofluorene derivatives is shown in the specification, wherein triphenylamine spirofluorene is the main body, and A is carbazole, alpha-carboline, beta-carboline, gamma-carboline, pyridine, diphenylamine, dimethoxydiphenylamine, dimethyldiphenylamine or 3,6-di-tert-butylcarbazole. The derivatives are good in thermal stability and hole conductivity. By simple methods, the degree of conjugation of the main body material is effectively controlled, the molecular weights of compounds are increased, the triplet state energy level and the glass-transition temperature of a material are largely increased, and the threshold voltage is obviously reduced. Polarity can be adjusted by adjusting donor / acceptor electronic groups. The bipolar performance is improved by adjusting the intensity of the donor / acceptor electronic groups. Compared with common phosphorescence main body materials, performance of devices prepared from the derivatives is improved and the derivatives can be widely applied in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a fluorene spirotriphenylamine derivative and its application. 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, wide viewing angle, fast response, good temperature adaptability, etc., and are widely used in TVs, mobile phones, MP3 and other electronic product displays. [0003] Organic electroluminescent materials are generally divided into singlet fluorescent dy...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D471/04C07D221/20C09K11/06H01L51/54
CPCC09K11/06C07D221/20C07D401/14C07D471/04C09K2211/1029H10K85/6572H10K50/11
Inventor 廖良生蒋佐权王亚坤
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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