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Spirofluorene organic laser material based on trifluoromethyl benzene functionalization, microcrystal preparation and application

A technology of trifluoromethylbenzene and trifluoromethylbenzene group, which is applied in the field of organic electroluminescence, can solve the problems of poor repeatability and interference, and achieves low ASE threshold, regular morphology and high yield Effect

Pending Publication Date: 2021-07-09
NANJING VOCATIONAL UNIV OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The currently reported organic solid-state laser devices are mainly through the thin film state, the morphology, structure and crystallinity of the thin film are disturbed by the external environment, and the repeatability is not very good. Based on this, the organic microcrystalline structure is used to control the microcrystalline Crystal preparation technology, the resonant cavity is changed from an external cavity to a built-in cavity structure of the gain medium. Through the control of the microcrystalline morphology, the structure of the built-in resonant cavity is changed, and the performance of the laser is adjusted, which improves the performance of the organic laser. Reduce and promote the development of organic laser

Method used

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  • Spirofluorene organic laser material based on trifluoromethyl benzene functionalization, microcrystal preparation and application
  • Spirofluorene organic laser material based on trifluoromethyl benzene functionalization, microcrystal preparation and application
  • Spirofluorene organic laser material based on trifluoromethyl benzene functionalization, microcrystal preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of Example 1 Precursor 1, 2 and 3

[0029] The structures of precursors 1, 2 and 3 are shown below:

[0030]

[0031] The synthesis methods of precursors 1, 2 and 3 are the same. Here, the synthesis of precursor 1 is taken as an example. The specific synthesis route and steps are as follows:

[0032]

[0033] 2,7-Dibromospirofluorene (2.37g, 5mmol), bis-pinacol borate (3.04g, 12mmol), Pd(OAc) 2 (0.11g, 0.5mmol), dppf (0.55g, 1mmol), KOAc (1.47g, 15mmol) were placed in a 100mL two-necked round bottom flask, and the air in the flask was replaced with nitrogen three times. Add 1,4-dioxane (50 mL), heat to 90° C., and react for 6 hours. Add water to quench the reaction, extract with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, remove the solvent by rotary evaporation, and separate by column chromatography to obtain precursor 1 (2.61 g, 92%).

Embodiment 2

[0034] Embodiment 2 Synthesis of trifluoromethylbenzene-based organic laser materials 1, 2 and 3 based on spirofluorene

[0035] Its structural formula is as follows:

[0036]

Embodiment 3

[0037] Example 3 The synthesis methods of spirofluorene-based trifluoromethylbenzene-based organic laser materials 1, 2 and 3 are the same. Here, the synthesis of spirofluorene-based trifluoromethylbenzene-based organic laser materials 1 is an example. The specific synthesis route and Proceed as follows:

[0038]

[0039] 3,5-bistrifluoromethylbromobenzene (0.64g, 2.2mmol), precursor 1 (0.57g, 1.0mmol), Pd(PPh 3 ) 4 (0.115g, 0.1mmol), placed in a 100mL two-necked round-bottomed flask and replaced the air in the bottle with nitrogen three times. Join K 2 CO 3 Solution (2M, 2.0 mL), toluene / tetrahydrofuran (1:1, 20 mL) which was bubbled with nitrogen for 2 hours in advance was added to the reaction system. Heat to 90, react for 24 hours. Add water to quench the reaction, extract with dichloromethane, dry the organic layer over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and separate by column chromatography to obtain an organic laser material 1 ba...

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Abstract

The invention provides a spirofluorene organic laser material based on trifluoromethyl benzene functionalization. The material is characterized in that the compound takes two trifluoromethyl phenyl groups as end-capping groups and is bridged through n spirofluorene groups, and in the general formula I, R1 and R2 independently represent a straight chain, a ring-shaped chain, a branched alkyl chain and an alkoxy chain containing hydrogen or 1-12 carbon atoms, and n is 1, 2 or 3. By changing the spirofluorene groups in the middle and substituent groups on the spirofluorene groups, a molecular pi conjugated system, a topological structure, an electronic structure and solubility are regulated and controlled, and the photoelectric characteristics of the material are regulated. The structure is simple, the light and heat stability is good, the synthesis process is simple, the yield is very high, and industrialization is facilitated. The preparation of the organic microcrystal material does not need any surfactant, and the organic microcrystal material is regular in morphology and low in ASE threshold value, and can be applied to the organic electronic field of organic laser gain media and the like.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to the preparation and application of a trifluoromethylbenzene functionalized spirofluorene organic laser material and microcrystals. Background technique [0002] Because of its advantages such as high brightness and good monochromaticity, laser, as a new type of light source, is widely used in research fields such as chemistry, physics and biology. At present, lasers can be divided into organic lasers and inorganic lasers according to laser materials. In 1974, lasing based on pure anthracene crystals was reported, and in 1992, American scientist Daniel Moses reported laser emission based on solution-state MEH-PPV pure substances. Organic laser gain media, due to their simple preparation, low cost, and easy structure modification, have attracted widespread attention in recent years, and various organic laser materials from ultraviolet to infrared spectra have b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/263C07C22/04C07D311/96C07D335/04C09K11/06H01S3/213
CPCC07C17/263C07C22/04C07D311/96C07D335/04C09K11/06H01S3/213C07B2200/13C07C2603/94C09K2211/1011C09K2211/1007C09K2211/1088C09K2211/1092
Inventor 刘玉玉欧昌金许卫锋周璐解令海杨战民
Owner NANJING VOCATIONAL UNIV OF IND TECH