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Macrocyclic aromatic-amine structured compound as well as preparation method and application thereof

A compound, ring-type technology, applied in the synthesis and application of hole transport materials, can solve the problems of destroying the uniformity and isotropy of the film, failing to disclose superior performance, and reducing device efficiency, and achieve stable color purity and photoelectricity. Efficiency, maximum fluorescence brightness improvement, easy hole injection effect

Inactive Publication Date: 2011-05-04
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as humans have higher and higher performance requirements for organic optoelectronic devices, simple triarylamine compounds have many shortcomings as hole transport materials: for example, in organic electroluminescent diodes (OLEDs), simple structure hole transport materials There is a tendency to crystallize, and after a period of preparation or use, it will destroy the uniformity and isotropy of the film, so as to destroy the good interfacial contact between the hole transport layer, the positive electrode and the organic layer, resulting in a decrease in the efficiency of the device and a long service life. Shortened (Chemical Progress, 2003, 15(6): 495.); In organic photoconductors, because the charge transport layer needs to be repeatedly contacted with toner, paper, cleaning blade, etc., the charge transport material cannot be used alone as a transport layer. It needs to be dispersed in a binder resin with good abrasion resistance and light transmission to improve mechanical strength
[0006] Patent CN101747286A discloses nano-aperture macrocyclic compounds that can be used for nano-inclusion and self-assembly constructed by structures containing triphenylamine and aliphatic hydrocarbons. This patent fails to disclose its superior performance as a hole material

Method used

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  • Macrocyclic aromatic-amine structured compound as well as preparation method and application thereof
  • Macrocyclic aromatic-amine structured compound as well as preparation method and application thereof
  • Macrocyclic aromatic-amine structured compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] compound a 4 Synthesis

[0107] In a 250mL single-necked flask, add 9mmol of magnesium chips and a piece of iodine, under the protection of an inert gas, stir and heat the magnesium chips, while slowly adding 10 mmol of 4-bromo-N-phenyl-N-p-methyl 50mL tetrahydrofuran solution of aniline, until the reaction of magnesium flakes is completed, slowly add 50mL tetrahydrofuran solution dissolved in 10mmol fluorenone dropwise, reflux for two hours after dropping, drop to room temperature, add dropwise 2M ammonium chloride solution to adjust the pH value to 7. The organic phase was separated, the inorganic phase was extracted three times with anhydrous ether, and combined with the organic phase. The combined organic phases were dried with an appropriate amount of anhydrous magnesium sulfate, the solvent was removed, and the chromatographic column was separated to obtain a yellow solid compound a 4 . The conversion rate was 71%.

[0108] 1 H NMR (500MHz, CDCl 3 , δ(ppm)):...

Embodiment 2

[0110] (TPAF) 3 Synthesis of macrocycles

[0111] In a 100mL one-necked flask, add compound a 40.6 g, add 80 mL of 1,3,5-mesitylene, drop 2 drops of methanesulfonic acid, then add a condenser, and react at 160°C for 20 hours under the protection of nitrogen. Cool down, remove the solvent, and separate and purify through a silica gel column to obtain a light yellow solid with a yield of 78%.

[0112] 1 H NMR (500MHz, CDCl 3 , δ (ppm)): 2.30 (s, 9H); 6.84 (d, J = 8.5Hz, 6H); 6.88 (d, J = 8.0Hz, 6H); 6.98 (d, J = 7.0Hz, 12H); 7.13~7.15(m, 12H); 7.31(t, J=8.0Hz, 6H); 7.37(t, J=8.0Hz, 6H); 7.49(d, J=8.0Hz, 6H); 7.77(t, J =7.0Hz, 6H). MS (MALDI-TOF) m / z: 1264.99 [M+H] + . Anal. Calcd. for (TPAF) 3 (C 96 h 69 N 3 ): C, 91.18; H, 5.50; N, 3.32. Found: C, 90.53; H, 5.89; N, 3.03.

Embodiment 3

[0114] compound a 5 Synthesis

[0115] In a 100mL single-necked flask, add 10mmol of N-(4-(p-tert-butylphenyl)-phenyl)-N-(4'-bromophenyl)aniline, add 50mL of dried tetrahydrofuran under nitrogen protection, and cool down To -78°C, slowly add 4.2mL of 2.5M butyllithium solution dropwise, and after 1 hour, slowly add dropwise 30mL tetrahydrofuran dissolved in 9.5mmol fluorenone, after the drop, keep the temperature at -78°C for 1 hour, and then spontaneously rise to Ambient temperature; slowly add 2M hydrochloric acid dropwise to bring the pH value to 7, after cooling, separate the organic phase, extract the inorganic phase with anhydrous ether three times, and combine with the organic phase. The combined organic phases were dried with anhydrous magnesium sulfate, the solvent was removed, and the chromatographic column was separated to obtain a yellow solid compound a 5 . The conversion rate was 69%.

[0116] 1 H NMR (500MHz, CDCl 3 , δ(ppm)): 1.35(s, 9H); 6.93(t, J=8.0Hz,...

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Abstract

The invention relates to a macrocyclic aromatic-amine structured compound as well as a preparation method and application thereof. The material is an electron-rich macrocyclic compound, the structure of which contains tertiary aromatic amine and fluorene structures. The designed and synthesized electron-rich mono-disperse tertiary-aromatic-amine macrocyclic compound has the structures shown in a general structural formula I or a structural formula II. The shown tertiary-aromatic-amine macrocyclic compound has difficultly-crystallized three-dimensional stable conformation and high glass transition temperature, can form a stable and uniform unformed film, has no fluorescence emission and lower oxidizing potential in a visible light region and is used as a hole-transporting material for a photoelectric conversion device under an equal testing condition, and the maximum fluorescence brightness of the compound is greatly improved compared with that of a traditional hole-transporting material 4,4'-di(N-phenyl-N-naphthyl)-biphenyl (NPB).

Description

technical field [0001] The invention belongs to the field of synthesis and application of hole transport materials, and more specifically relates to the synthesis of a class of monodisperse ring-type triarylamine oligomer hole transport materials and their application in the field of optoelectronics. Background technique [0002] On the triarylamine compound, on the one hand, the N atom attracts the electron cloud on the aromatic ring through the inductive effect, and on the other hand, due to the p-π conjugation effect, the unshared electron pair on the nitrogen is conjugated with the benzene ring, so that the triarylamine has a strong The ability to donate electrons, showing good electronpositivity, low ionization potential, and thus has a higher hole mobility than other hole-conducting materials. At the same time, because triarylamine compounds generally have good solubility properties, easy film formation and strong light stability. Therefore, it has been widely used as...

Claims

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Application Information

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IPC IPC(8): C07D255/04H01L51/54
Inventor 孔庆刚陈敏东郑有飞孙兴菊董婷刘凯王建科章翔宇朱静
Owner NANJING UNIV OF INFORMATION SCI & TECH
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