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Toluylene-containing meta-substituted sulfonium salt photoproduction acid agent and preparation method thereof

A stilbene, photoacid generator technology, applied in the preparation of sulfonates, photosensitive materials for optomechanical equipment, etc., can solve problems such as structural limitations, and achieve improved yield, good acid production performance, and fewer steps. Effect

Inactive Publication Date: 2011-08-03
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Traditional commercial photoacid generators can only be used in relatively simple photolithography due to structural limitations

Method used

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  • Toluylene-containing meta-substituted sulfonium salt photoproduction acid agent and preparation method thereof
  • Toluylene-containing meta-substituted sulfonium salt photoproduction acid agent and preparation method thereof
  • Toluylene-containing meta-substituted sulfonium salt photoproduction acid agent and preparation method thereof

Examples

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Embodiment 1

[0032] In the invention, the initial substance 1 is N,N-dianilinobenzaldehyde, and the intermediate N,N-dianilinostyrene is obtained through the Wittig reaction; then the intermediate N,N-dianilinostyrene and 3-bromoanisole sulfide is coupled, and then obtains the photoacid generator of triphenylamines; The R 1 is 4-cyanobenzyl, R 2 For hexafluorophosphate as an example, the synthetic route used in the preparation method is as follows:

[0033]

[0034] In the formula:

[0035] i: Methyltriphenylphosphine bromide, potassium tert-butoxide, tetrahydrofuran, room temperature, react for 4 hours;

[0036] ii: Palladium acetate, triethanolamine, 3-bromoanisole sulfide, 120°C, react for 12 hours;

[0037] iii: Silver trifluoromethanesulfonate, 4-cyanobenzyl bromide, dichloromethane, room temperature, potassium hexafluorophosphate, react for 24 hours.

[0038] 1. Preparation of N,N-Dianilinostyrene

[0039] Under the protection of nitrogen, 10g of N,N-dianilinobenzaldehyde ...

Embodiment 2

[0047] The preparation method is the same as in Example 1, except that in the process of preparing N, N-dianilinostyrene, under the protection of nitrogen, solid potassium tert-butoxide is added to the system three times, and it should be fully recovered after each addition. Stir so that the temperature of the system is not higher than 10°C.

Embodiment 3

[0049] The preparation method is the same as in Example 1, except that when preparing the precursor, the solvent is changed to N,N-dimethylformamide and triethylamine, and the rest of the steps remain unchanged. After the treatment, the same precursor is synthesized.

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Abstract

The invention relates to a toluylene-containing meta-substituted sulfonium salt photoproduction acid agent and a preparation method thereof. Triphenylamine is used as an electron donor and coupled with a meta-substituted sulfonium salt electron acceptor through a toluylene structure so as to synthesize the photoproduction acid agent, and the electron donor and the meta-substituted sulfonium salt electron acceptor form D-phi-A type molecules through the toluylene structure so as to synthesize the high-performance photoproduction acid agent with double-photon absorption capacity. The photoproduction acid agent has good dissolubility in common solvents such as dichloromethane, trichloromethane, acetone and tetrahydrofuran, the synthesis steps are simple, purification is easy, and the yield is high. The photoproduction acid agent shows the photoproduction acid quantum yield of over 0.50 in an ultraviolet area. Moreover, under a shading condition, the photoproduction acid agent can be preserved for long time and has high chemical stability. The photoproduction acid agent has huge application value in the fields of single-photon lithography and double-photon lithography.

Description

technical field [0001] The invention relates to a class of photoacid generators containing stilbene meta-substituted sulfonium salts and a preparation method thereof. Background technique [0002] Photoacid generator is a high-efficiency chemical amplifier developed in the 1980s. It can dissociate to generate protons by absorbing photon energy, thereby triggering changes in the physicochemical properties of the exposed area. Since this acid generation mechanism is externally controllable, and this chemical amplification can greatly increase the rate of photochemical reactions, photoacid generators have been widely used in photoresist, computer-to-plate, acid-induced polymerization and avoidance in recent years. Light indicators and many other fields. Sulfonium salt-type photoacid generators, as one of them, are widely used, and various modification methods emerge in endlessly. [0003] Traditional commercial photoacid generators can only be used in relatively simple photo...

Claims

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Application Information

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IPC IPC(8): G03F7/004C07C381/12C07C309/06C07C303/32
Inventor 夏荣捷金明浦鸿汀万德成
Owner TONGJI UNIV
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