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Sulfonium salt photo-acid generator using stilbene as main body and preparation method thereof

A technology of stilbene and photoacid generator, which is applied in the fields of optomechanical equipment, photoengraving process of pattern surface, photosensitive material for optomechanical equipment, etc. The two-photon absorption cross-section value is small and other problems, to achieve the effect of good solubility, good acid production performance and high reaction yield

Inactive Publication Date: 2011-01-12
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the two-photon absorption cross-section of commercially available photoacid generators is very small, they cannot be applied to the field of two-photon lithography, which greatly limits their application in some application fields, such as three-dimensional microfabrication and micromechanical systems.

Method used

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  • Sulfonium salt photo-acid generator using stilbene as main body and preparation method thereof
  • Sulfonium salt photo-acid generator using stilbene as main body and preparation method thereof
  • Sulfonium salt photo-acid generator using stilbene as main body and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The initial substance is 4-hydroxybenzaldehyde, the intermediate 4-alkoxystyrene is obtained by Williamson reaction and Wittig reaction, and then it is connected with 4-bromoanisole sulfide by Heck reaction, and then the photogenerated stilbenes are obtained. Acid agent; R in the present embodiment 1 is ethoxy, R 2 is 4-cyanobenzyl, R 3 It is hexafluorophosphate, and its synthetic route is as follows:

[0031]

[0032] In the formula:

[0033] i: ethyl iodide, potassium carbonate, acetone, reflux for 4 hours;

[0034] ii: Methyl triphenylphosphine bromide, sodium hydride, dimethyl sulfoxide, room temperature, reaction for 2 hours;

[0035] iii: 4-bromoanisole sulfide, palladium acetate, triethanolamine, 120°C, react for 24 hours;

[0036] iv: Silver trifluoromethanesulfonate, 4-cyanobenzyl bromide, potassium hexafluorophosphate, dichloromethane, room temperature, react for 24 hours.

[0037] 1. Preparation of 4-ethoxybenzaldehyde

[0038] Dissolve 6.0g of 4-h...

Embodiment 2

[0049] The preparation method is the same as in Example 1, except that when preparing the target photoacid, 4-cyanobenzyl bromide is replaced by an equivalent amount of methyl iodide, and the remaining steps remain unchanged. After the treatment, the target photoacid generator substituted by methyl is synthesized. .

Embodiment 3

[0051] The preparation method is the same as in Example 1, except that ethyl iodide is replaced by methyl iodide when preparing alkoxybenzaldehyde, and the remaining steps are inconvenient. After careful treatment, the target photoacid generator substituted by 4-methoxy is synthesized.

[0052] Using Rhodamine B as the acid indicator and 365nm ultraviolet light as the excitation light source, the photoacid quantum yields of the substances in Example 1-Examples were measured to be 0.40, respectively.

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Abstract

The invention relates to a sulfonium salt photo-acid generator using stilbene as the main body and a preparation method thereof, which discloses a design and preparation method of a sulfonium salt photo-acid generator using stilbene chromophore as the main body and having two-photon absorption capability, in particular to a novel photo-acid generator synthesized by using stilbene as the conjugated chain bridge, adding various electron donors on para positions of the benzene ring and using sulfonium salts with different substituent groups as electron acceptors and a preparation method thereof. The photo-acid generator can be well dissolved in a common solvent such as dichloromethane, trichloromethane, acetone and tetrahydrofuran, and has the advantages of simple synthesis procedure, easy purification, high yield and the like. Because the photo-acid generator has a push-pull type molecular structure and the molecule indicates the two-photon absorption properties of the stilbene compound, the photo-acid generator has great application values in the fields of single-photon photoetching and two-photon photoetching.

Description

technical field [0001] The invention relates to a class of sulfonium salt photoacid generators mainly composed of stilbene and a preparation method thereof. Background technique [0002] Photoacid generators were gradually developed in the 1980s. Because of their good chemical amplification characteristics, they are widely used in chemical amplification imaging systems such as microlithography, scale integrated circuit manufacturing, microelectronics, and microfluidics. , optical data storage and other fields, it is one of the indispensable and important raw materials in the field of modern electronic information technology. Among them, sulfonium salts are a class of widely used photoacid generators. Because the two-photon absorption cross-section of commercially available photoacid generators is very small, they cannot be applied to the field of two-photon lithography, which greatly limits their application in some application fields, such as three-dimensional microfabrica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/004G03F7/039C07C381/12
Inventor 夏荣捷金明万德成浦鸿汀
Owner TONGJI UNIV
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