Cavity transfer material with triphenylamine-bipyridyl structure and preparation method thereof

A hole transport material, triphenylamine technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as unfavorable commercial applications, poor film-forming properties of small molecular compounds, etc., to expand design ideas, The effect of good fluorescence lifetime and simple preparation process

Inactive Publication Date: 2011-09-14
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these small molecular compounds have poor film-forming properties, and these hole transport materials

Method used

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  • Cavity transfer material with triphenylamine-bipyridyl structure and preparation method thereof
  • Cavity transfer material with triphenylamine-bipyridyl structure and preparation method thereof
  • Cavity transfer material with triphenylamine-bipyridyl structure and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0047] Examples 1-3 are 4-methyl-4'-(2-(4-(N,N-dimethylphenyl)amino)phenyl)vinyl-2,2'-bipyridine (S1)

[0048] The synthetic route is as follows:

[0049]

Embodiment 1

[0050] Example 1: Synthesis of 4-methyl-4'-(2-(4-(N,N-di-p-methylphenyl)amino)phenyl)vinyl-2,2'-bipyridine (S1)

[0051] N 2 Under protection, add 0.42g (1.35mmol) triphenylamine aldehyde compound 1, 0.48g (1.5mmol) Horner reagent (compound 7) and 60mL dry tetrahydrofuran to a 250mL four-neck flask, stir until completely dissolved, then cool down in an ice bath to At 0°C, 0.33 g (3 mmol) of potassium tert-butoxide in tetrahydrofuran was slowly added dropwise, and the molar ratio of compound 1, Horner's reagent and potassium tert-butoxide was 1:1.1:2.2. The reaction solution was stirred for 6 hours in an ice bath, then the solvent was removed by rotary evaporation, dissolved in dichloromethane, washed twice with water, and washed with anhydrous MgSO 4 After drying, the solvent was removed by rotary evaporation, and the crude product was separated by column chromatography (cyclohexane / ethyl acetate=5:1) to obtain 0.44 g of the target product S1, with a yield of 70%. 1 H NMR (C...

Embodiment 2

[0052] Example 2: Synthesis of 4-methyl-4'-(2-(4-(N,N-di-p-methylphenyl)amino)phenyl)vinyl-2,2'-bipyridine (S1)

[0053] N 2 Under protection, add 0.42g (1.35mmol) triphenylamine aldehyde compound 1, 0.48g (1.5mmol) Horner reagent (compound 7) and 60mL dry tetrahydrofuran to a 250mL four-neck flask, stir until completely dissolved, then cool down in an ice bath to At 0°C, 0.25 g (2.25 mmol) of potassium tert-butoxide in tetrahydrofuran was slowly added dropwise. The molar ratio of compound 1, Horner's reagent and potassium tert-butoxide was 1:1.1:1.65. The reaction solution was stirred for 8 hours in an ice bath, then the solvent was removed by rotary evaporation, dissolved in dichloromethane, washed twice with water, and then washed with anhydrous MgSO 4 After drying, the solvent was removed by rotary evaporation, and the crude product was separated by column chromatography (cyclohexane / ethyl acetate=5:1) to obtain 0.38 g of the target product S1 with a yield of 61%. 1 H NM...

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Abstract

The invention relates to the field of photoelectric materials, in particular to a cavity transfer material with a triphenylamine-bipyridyl structure and a preparation method thereof. The method comprises the following steps of: adding corresponding triphenylamine aldehyde, a Hornet reagent and dry tetrahydrofuran into a reactor under the protection of N2; stirring until all the materials are dissolved and cooling to 0 DEG C in an ice bath; dropwise adding a tetrahydrofuran solution of potassium tert-butoxide; fully stirring and reacting reaction liquid under an ice bath condition and removing a solvent by performing rotary steaming; dissolving with dichloromethane; washing twice with water and drying with anhydrous MgSO4; removing a solvent by performing rotary steaming; and separating a crude product with column chromatography to obtain a target product (the structural formula is shown in the specification). The invention provides a novel cavity transfer material with a triphenylamine-bipyridyl structure as well as a preparation method and photoelectric property research thereof. By adopting the cavity transfer material, the research contents of a small molecular cavity transfer material are enriched and the design concept of the novel cavity transfer material is expanded. The cavity transfer material plays important theoretical and practical roles in researching organic photoelectric cavity transfer materials.

Description

technical field [0001] The invention relates to the field of photoelectric materials, in particular to hole transport materials containing triphenylamine and bipyridine structures and a preparation method, and their photoelectric properties are studied at the same time. This type of hole transport material has good solubility properties, and is suitable for the preparation of large-area solid films by economical and simple spin coating methods. The material has excellent thermal properties and reasonable highest molecular orbital energy levels. Relevant performance tests show that this type of material Suitable for use as a hole transport material. Background technique [0002] Hole transport materials are important functional raw materials for the preparation of photoelectric conversion devices, and are mainly used in organic photoconductors (OPCs), organic electroluminescent devices (OLEDs) and dye-sensitized solar cells (DSSCs). In the function-separated organic photocon...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/38
Inventor 李祥高吕海军王世荣高文正
Owner TIANJIN UNIV
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