Photoresist acid-producing resin monomer containing adamantane structure and synthesis method thereof

A synthesis method and resin monomer technology, which are applied in the field of photoresist acid-generating resin containing adamantane structure and its synthesis field, can solve the problem of low resolution of photolithographic patterns, achieve improved resolution, and improve edge side Roughness, the effect of improving edge roughness

Inactive Publication Date: 2020-05-12
上海博栋化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, due to the specific structure of the acid-sensitive resin monomer in the existing photoresist, there is a problem of low photolithographic pattern resolution

Method used

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  • Photoresist acid-producing resin monomer containing adamantane structure and synthesis method thereof
  • Photoresist acid-producing resin monomer containing adamantane structure and synthesis method thereof
  • Photoresist acid-producing resin monomer containing adamantane structure and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] This embodiment provides a photoresist acid-generating resin monomer containing an adamantane structure, and the reaction scheme of the synthesis method of the photoresist acid-generating resin monomer is as follows:

[0033]

[0034]

[0035] It specifically includes the following steps:

[0036] S1. After dispersing dibenzothiophene oxide (100g, 499mmol) and p-methoxybenzoic acid (76g, 499mmol) in dichloromethane (1.5L), cool to 0°C with an ice-water bath, and slowly Add Eaton's reagent (750mL), then take it out from the ice-water bath, stir at room temperature for 16 hours, cool the reaction solution to 0°C, slowly add water (1.5L) to quench, keep the temperature below 25°C, and filter to remove the precipitate Separate the aqueous phase and the organic phase, extract the aqueous phase with ethyl acetate (500mL*3), wash the organic phase with water (500mL), and slowly add an aqueous solution of potassium bromide (119g, 1mol) to the organic phase under stirring ...

Embodiment 2

[0043] This embodiment provides a photoresist acid-generating resin monomer containing an adamantane structure, and the reaction scheme of the synthesis method of the photoresist acid-generating resin monomer is as follows:

[0044]

[0045] It specifically includes the following steps:

[0046] S1, 1,1,2,2-tetrafluoro-2-(2-hydroxyethoxy)ethane-1-sodium sulfonate (20g, 76mmol) and triethylamine (24g, 237mmol) were added to dichloro methane (350mL), and cooled to 0°C with an ice-water bath, then slowly added acryloyl chloride (6.8g, 75mmol) dropwise, then, warmed up to room temperature and stirred for three hours, then slowly added water ( 100 mL), the aqueous phase was extracted with dichloromethane (50 mL*3), the organic phase was combined, the organic phase was washed three times with saturated brine (100 mL*3), concentrated and spin-dried to obtain compound A3 (formula A3, 17.1 g).

[0047] S2. Add the third intermediate (formula 1-4, 10.2g, 16mmol) obtained in the abov...

Embodiment 3

[0049] This embodiment provides a photoresist acid-generating resin monomer containing an adamantane structure, and the reaction scheme of the synthesis method of the photoresist acid-generating resin monomer is as follows:

[0050]

[0051] It specifically includes the following steps:

[0052] S1, under the protection of nitrogen, after adding magnesium chips (6.3g, 259mmol) in ether (80mL), add a small grain of iodine tablet, then, slowly add tert-butyl bromide (35g, 255mmol) ether ( 250mL) solution, when the reaction solution boils, the color of iodine disappears, and the dropwise addition is completed. Then, the temperature is raised to keep the reaction solution refluxed for half an hour, cooled with ice water, and dropwise added 2,6-adamantanedione 1-1 (20g, 122mmol) in ether (100mL) solution, keep the reaction solution slightly boiling, after the dropwise addition, continue to stir for half an hour at room temperature, cool the reaction solution with ice water, slow...

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Abstract

The invention discloses a photoresist acid-producing resin monomer containing an adamantane structure and a synthetic method thereof, belonging to the fields of chemical synthesis and photoetching materials. The photoresist acid-producing resin monomer has a structural general formula which is described in the specification. In the structural general formula, R1 is an alkyl group or a cycloalkyl group; R2 is one selected from the group consisting of a covalent bond, an alkyl group, a fluoroalkyl group, an oxygen atom-containing alkyl group and an oxygen atom-containing fluoroalkyl group; and R3 is hydrogen or a methyl group. The photoresist acid-producing resin monomer provided by the invention has the following advantages: through combination of a photoinduced acid-producing agent with resin, acid diffusion of the photoinduced acid-producing agent in the post-exposure drying process can be effectively prevented, and the edge roughness of a photoetching pattern is improved; in addition, the cation part of the resin monomer also has a degradable group, and the dissolving speed difference of the resin monomer in a developing solution before and after exposure is increased, so the resolution ratio is improved.

Description

technical field [0001] The invention relates to the fields of chemical synthesis and photolithography materials, in particular to a photoresist acid-generating resin monomer containing an adamantane structure and a synthesis method thereof. Background technique [0002] Photolithography technology refers to the chemical sensitivity of photoresist materials (especially photoresist) under the action of visible light, ultraviolet rays, electron beams, etc., through exposure, development, etching and other processes, the design on the mask plate Graphics microfabrication technology that transfers graphics to the substrate. [0003] Photolithographic materials (especially photoresist), also known as photoresist, are the most critical functional chemical materials involved in photolithography technology. The main components are resin, photoacid generator, and corresponding additives and Solvents, such materials are chemically sensitive to light (including visible light, ultraviol...

Claims

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Application Information

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IPC IPC(8): C07D333/76G03F7/027
CPCC07D333/76G03F7/027
Inventor 李嫚嫚蒋小惠毕景峰郭颖王尹卓
Owner 上海博栋化学科技有限公司
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