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Spiroindene compounds and preparation and application thereof

A technology of a compound, spiroindene, applied in the field of organic light-emitting materials, can solve the problems that affect the development of full-color OLED white light devices, low color life, low luminous efficiency, etc., and achieve improved shape stability, high luminous quantum efficiency, vitrification The effect of high temperature

Active Publication Date: 2018-05-29
长沙道尔顿电子材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current blue-light materials have disadvantages such as low luminous efficiency, low color purity, poor thermal stability, and low color life. These key problems have not been effectively resolved, which in turn affects full-color OLEDs and white light devices. Technological research and industrialization development pace

Method used

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  • Spiroindene compounds and preparation and application thereof
  • Spiroindene compounds and preparation and application thereof
  • Spiroindene compounds and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of compound 1-A

[0067] (1) Synthesis of 9-(1,2,2-triphenylvinyl)-9H-fluorene-9-ol

[0068] Under the protection of an inert gas, add 2g (0.006mol) triphenylbromide to a 100mL Schuck bottle, inject 120mL of anhydrous tetrahydrofuran solvent, stir for 15min after dissolving, and then inject 2.8mL (0.007mol, 2.5mol / L) The hexane solution of butyllithium was stirred and reacted for 1 hour, and then 1.26 g (0.007 mol) of 9H-fluoren-9-one was added, and the reaction was continued for 8 hours. After the reaction was completed, 0.1 mL of water was injected to quench the reaction, the solvent was spin-dried and purified by chromatographic chromatography for the next reaction.

[0069] (2) Preparation of structural formula 1-A compound

[0070] Under the protection of an inert gas, add 0.0011 mol of the above crude product to a 100 mL two-necked flask, add 30 mL of dichloromethane solvent and 0.0056 mol of stannous chloride. React at room temperature for three hour...

Embodiment 2

[0072] Synthesis of compound 1-B

[0073] The specific steps are the same as in Example 1, only the raw material 9H-fluoren-9-one in (1) is changed to 11H-benzo[b]fluoren-11-one

Embodiment 3

[0075] Synthesis of Compound 1-C

[0076] The specific steps are the same as in Example 1, except that the raw material 9H-fluoren-9-one in (1) is changed to 11H-benzo[a]fluoren-11-one.

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Abstract

The invention discloses organic light-emitting materials with reversible photochromism property. The organic functional materials are a series of spiroindene compounds; when being irradiated with ultraviolet light, the compounds can be photochromic in both solution and solid states, that is to say, a color can be changed from an original color to orange yellow or pink, and the original color of the compounds can be restored after illumination is removed. In addition, the compounds disclosed by the invention have excellent fluorescence properties in the range of visible light wavelengths, the emission wavelengths can be regulated by conjugation modification and substituent modification, and the materials are high in fluorescence quantum yield and high in glow brightness, and can be used inmanufacture of organic light-emitting diode elements.

Description

technical field [0001] The invention relates to the field of functional materials, in particular to organic luminescent materials with photochromic properties. Background technique [0002] The spiro compound has a rigid structure and a stable structure, and has important applications in medicine, pesticides, luminescent materials, and polymer adhesives. In the fields of biology and medicine, many spiro compounds are organic intermediates of medicines and pesticides, and have been proved to have physiological and biological activities. In the field of materials, spiro compounds are the main type of organic molecular light-emitting materials, which can be widely used in organic electroluminescence, organic field effect transistors, organic integrated circuits, organic thin-film transistors, nonlinear optics, solar cells, biosensing, etc. field. [0003] The phenomenon of photochromism means that a compound will undergo a photochemical reaction under the light of a certain w...

Claims

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Application Information

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IPC IPC(8): C07C15/04C07C25/22C07C255/52C07C43/21C07C1/20C07C17/35C07C253/30C07C41/18C09K9/02C09K11/06H01L51/54
CPCC09K9/02C09K11/06C07C15/04C07C25/22C07C43/21C07C255/52C07B2200/07C09K2211/1011C09K2211/1007H10K85/623H10K85/625H10K85/624
Inventor 曾泽兵陈娴周志彪向建南罗胜联
Owner 长沙道尔顿电子材料有限公司
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