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Phenol-derived photoacid generator as well as preparation method and application thereof

A technology of photoacid generator and phenol, which is applied in the preparation of sulfonic acid, photosensitive materials for optomechanical equipment, organic chemistry, etc., can solve the problems of acid diffusion and the inability to reduce the edge roughness and fineness, and achieve raw material Simple, easy to prepare and large-scale production, and the effect of improving graphic resolution

Pending Publication Date: 2022-04-29
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a large number of photoresist materials have been designed and developed, the existing PAG still cannot meet the needs of practical applications, especially due to the existence of acid diffusion problems, resulting in the inability to reduce the edge roughness and fineness

Method used

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  • Phenol-derived photoacid generator as well as preparation method and application thereof
  • Phenol-derived photoacid generator as well as preparation method and application thereof
  • Phenol-derived photoacid generator as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] This embodiment provides a Z + Photoacid generator I-1-Sul which is triphenylsulfonium salt and its synthesis method. The reaction scheme of the synthetic method of this photoacid generator is as follows:

[0043]

[0044] It specifically includes the following steps:

[0045]Synthesis 1-1: Add compound 1-bromoadamantane (10 g, 0.0465 mol) and phenol (35 g, 0.0342 mol) into a 250 ml three-neck flask. Under the protection of nitrogen, the temperature of the system was raised to 120° C., and the reaction was refluxed for 10 h. A large amount of HBr gas was generated during the reaction. After the reaction was completed, the reaction system was cooled to room temperature. The reaction solution was poured into 1000 ml of hot water, stirred, washed, and suction filtered. This operation was repeated 3 times, and the brown solid crude product was obtained after drying. After the above crude product was dried, it was subjected to dichloromethane column chromatography t...

Embodiment 2

[0051] This example provides a photoacid generator I-6-Sul whose cation is triphenylsulfonium salt and its synthesis method. The reaction scheme of the synthetic method of this photoacid generator is as follows:

[0052]

[0053] It specifically includes the following steps:

[0054] Synthesis 2-1: Add compound 1-adamantanol (10 g, 0.0657 mol), 2,3,5,6 tetrafluorophenol (10.9 g, 0.0657 mol) and 100 ml of dichloromethane into a 250 ml three-neck flask. Under nitrogen protection, methanesulfonic acid (5.8 ml, 0.0657 mol) was added, and 35 ml of dichloromethane solution containing 7 ml of acetic acid was added to the system with stirring, and the dropping time was controlled at 20 min. After completion, stir at room temperature for 48h. After the reaction is over, adjust the reaction solution to neutral. The reaction solution was poured into 400 ml of water, stirred, washed, separated, and dried over anhydrous sodium sulfate. The organic phase was concentrated and the solv...

Embodiment 3

[0059] This embodiment provides a photoacid generator I-1-Iod whose cation is diphenyliodonium salt and its synthesis method. The target molecule of this photoacid generator is as follows:

[0060]

[0061] Similar to Example 1, the cationic sulfonium salt in the target photoacid generator was replaced with iodonium salt, and the rest of the synthesis steps remained unchanged. The yield of target molecule IV in this example was 60.1%. 1 H NMR (CD 3 CN):δ7.6-7.9(m,-ArH-,10H),7.24(d,-ArH-,2H),6.78(d,-ArH-,2H),2.08(br,-CH-,3H) ,1.88(-CH 2 -,6H),1.76(-CH 2 -,6H).HRMS: 688.4.

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Abstract

The invention discloses a phenol-derived photoacid generator as well as a preparation method and application thereof, and belongs to the field of chemical synthesis and photoetching materials. The photoacid generator is a sulfur / iodonium salt photoacid generator of polyfluorosulfonate with bridged carbon aliphatic ring adamantane substituted phenol as a rigid structure and linked with a flexible carbon chain. The invention relates to a photoacid generator, in particular to a photoacid generator with a structure shown in a formula (I), and the compound is simple and easily available in raw materials, simple in synthetic route and convenient to prepare. The synthesized sulfonate anion has a large volume, compared with a single phenol substituted structure, the photoacid generator formed by introducing an adamantane structure has a larger molecular weight, and the introduction of a bridged carbon aliphatic ring improves the carbon content of the photoacid generator and improves the corrosion resistance. Meanwhile, the large-molecular-weight photoacid generator can further reduce diffusion of photoacid in the photoetching process of the photoresist in which the large-molecular-weight photoacid generator participates, so that the edge roughness is improved, the line width roughness is reduced, and the resolution is improved. .

Description

technical field [0001] The present invention relates to the fields of chemical synthesis and photolithographic materials, in particular to a class of sulfur / iodonium salt photoacid generators derived from phenol with bridged carbon aliphatic cycloadamantane polyfluorosulfonate as anion and its synthesis method , and use in related photoresists. Background technique [0002] Photolithography technology refers to the use of photolithographic materials, generally referred to as photoresist, to use its chemical sensitivity under the action of visible light, ultraviolet rays, electron beams, etc., to design on the mask through exposure, development, etching and other processes. The patterns or background graphics on the plate are transferred to the substrate, which is a microfabrication technology. [0003] Photolithographic materials are closely related to the development of lithographic technology. To a certain extent, the development of lithographic materials has played a dec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/11C07C303/22G03F7/004
CPCC07C309/11G03F7/004
Inventor 金明王永辉
Owner TONGJI UNIV
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