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Fluorene spirotriphenylamine derivatives and uses thereof

A compound and device technology, applied in the field of fluorene spirotriphenylamine derivatives, can solve the problems that hinder wide application, low material stability, low glass transition temperature, etc., and achieve lower turn-on voltage, high-efficiency electroluminescent performance, and device The effect of performance improvement

Active Publication Date: 2018-01-05
维思普新材料(苏州)有限公司
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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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  • Fluorene spirotriphenylamine derivatives and uses thereof
  • Fluorene spirotriphenylamine derivatives and uses thereof
  • Fluorene spirotriphenylamine 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 spinning was dissolved in 45 mL of glacial acetic acid and 10 mL of nicotinic acid, refluxed for 4 hours, cooled to room temperature, then suction filtered and washed ...

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, HAT-CN was vacuum-deposited on ITO conductive glass as a hole injection layer (HIL), the evaporation rate was 0.25Å / s, and the coating thickness was 10nm; TAPC was vacuum-deposited on the hole injection layer as a hole Transport layer...

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Abstract

The invention discloses fluorene spirotriphenylamine derivatives and their uses. The chemical structure of the fluorene spirotriphenylamine derivatives is as follows: wherein, fluorene spirotriphenylamine is the main body; A is carbazole, α‑N heterocarbazole, β -N-heterocarbazole, γ-N-heterocarbazole, pyridine, diphenylamine, dimethoxydiphenylamine, dimethyldiphenylamine or 3,6-di-tert-butylcarbazole. The fluorene spirotriphenylamine derivatives of the present invention have good thermal stability and hole conductivity. Through a simple method, the conjugation degree of the host material can be effectively controlled, the molecular weight of the compound can be increased, and the triplet energy level and glass transition of the material can be improved. The temperature has been greatly increased and the turn-on voltage has been significantly reduced. The polarity can be adjusted by pushing / pull electron groups, and the bipolar performance can be improved by adjusting the strength of its push-pull electron groups. Compared with the commonly used phosphorescent host materials, the device performance has been improved, and it can be widely used in organic electroluminescence. Glowing field.

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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Patent Type & Authority Patents(China)
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 维思普新材料(苏州)有限公司
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