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Sulfonium salt bonded phenol type molecular glass photoresist, preparation method and application thereof

A technology of photoresist and positive photoresist, which is applied in the field of photolithography and can solve problems such as pattern collapse, crossover, and lower resolution

Active Publication Date: 2018-06-12
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemically amplified photoresist has high contrast and resolution, and its etching resistance is also very good, but its unique post-baking process may cause excessive acid diffusion or delay effects, etc., resulting in pattern collapse or crossing, which reduces the resolution, increased roughness

Method used

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  • Sulfonium salt bonded phenol type molecular glass photoresist, preparation method and application thereof
  • Sulfonium salt bonded phenol type molecular glass photoresist, preparation method and application thereof
  • Sulfonium salt bonded phenol type molecular glass photoresist, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]1. Preparation of dimethyl-2,2-bis(4-hydroxy-3,5-bis(3,4-dihydroxyphenyl)phenyl)propylsulfonium chloride (1-B)

[0061]

[0062] Dissolve 3.3g of 2,2-bis(4-hydroxy-3,5-bis(3,4-dihydroxyphenyl)phenyl)propane(III) (5mmol) in 30mL of methanol solvent and add it to a 100mL three-necked flask , under the condition of ice-water bath, hydrogen chloride gas was fed continuously, 0.39 g dimethyl sulfoxide (5 mmol) dissolved in 10 mL methanol was added dropwise, and the mixture was kept at 0° C. and stirred for 2-3 hours. After the reaction was complete, spin the solution to dryness, add water and ethyl acetate for extraction, retain the aqueous phase, collect the aqueous phase after multiple extractions, spin dry, and dry in a vacuum oven at 50°C overnight to obtain a light yellow solid powder.

[0063] MALDI-TOF (C 41 h 37 ClO 10 S), m / z: 721.2.

[0064] 2. Preparation of dimethyl-2,2-bis(4-hydroxy-3,5-bis(3,4-dihydroxyphenyl)phenyl)propylsulfonium salt of perfluorobutane...

Embodiment 2

[0073] 1. Preparation of dimethyl-2,3,4,5-tetrakis(3,4-dihydroxyphenyl)thiophenesulfonium chloride (2-B)

[0074]

[0075] Dissolve 2.6g of 2,3,4,5-tetrakis(3,4-dihydroxyphenyl)thiophene (IV) (5mmol) in 30mL of methanol solvent, add it to a 100mL three-necked flask, and continuously feed Hydrogen chloride gas, 0.39 g of dimethyl sulfoxide (5 mmol) dissolved in 10 mL of methanol was added dropwise, and the mixture was kept at 0° C. and stirred for 2-3 hours. After the reaction was complete, spin the solution to dryness, add water and ethyl acetate for extraction, retain the aqueous phase, collect the aqueous phase after multiple extractions, spin dry, and dry in a vacuum oven at 50°C overnight to obtain a light yellow solid powder.

[0076] MALDI-TOF (C 30 h 25 ClO 8 S 2 ), m / z:577.4.

[0077] 2. Preparation of dimethyl-2,3,4,5-tetrakis(3,4-dihydroxyphenyl)thiophenesulfonium salt of perfluorobutanesulfonate (2-C)

[0078]

[0079] 3.1g dimethyl-2,3,4,5-tetrakis(3,4-...

Embodiment 3

[0088] The preparation of positive photoresist: the compound (1) that 40mg embodiment 1 is prepared is dissolved in 1mL PGMEA and is made into positive photoresist, spin-coats on the silicon chip after hydrophilic and hydrophobic treatment (spin-coating condition is : 500~1000rpm, 0~30s; 1000~2000rpm, 0~30s; 2000~3000rpm, 0~30s).

[0089] figure 1 It is a lithography result diagram of EUV lithography performed at the Shanghai Synchrotron Radiation Light Source 08U1B extreme ultraviolet lithography line station using the film prepared in Example 3.

[0090] The results show that the thickness of the film obtained by spin coating is 30-100nm, the film-forming performance is good, the thickness of the obtained film is uniform, and the photolithography pattern with a line width of 70nm to 30nm can be obtained uniformly.

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Abstract

The invention relates to a sulfonium salt bonded phenol type molecular glass photoresist, a preparation method and application thereof. The sulfonium salt bonded phenol type molecular glass photoresist is a stereoscopically asymmetrical amorphous small molecule compound, has relatively high melting point and glass-transition temperature (melting points being higher than 100 DEG C respectively), and can meet a photolithography requirement, so that the membrane structure is free of change during high-temperature baking. The compound can be individual or be compound with other photoresists, light-induced acid production agents and cross-linking agents into positive or negative photoresists, and a photoresist coating with uniform thickness can be obtained through a spin-coating method on a substrate. The formula of the photoresist can be used in modern photolithography such as 365 nm photolithography, 248 nm photolithography, 193 nm photolithography, extremely ultra-violet lithography andelectron beam lithography, and is particularly applicable to extreme ultra-violet lithography.

Description

technical field [0001] The invention relates to the technical field of photolithography, in particular to a glass photoresist bonded with benzene polyphenol molecules by sulfonium salts and a preparation method and application thereof. Background technique [0002] The integrated circuit industry has penetrated into various fields of modern life, especially the so-called 3C field, namely consumer electronics (consumer), computer (computer) and communication (communication). Its wide application and rapid development are inseparable from the upgrading of photolithography technology and the continuous follow-up of photoresist materials. [0003] Photoresist is a kind of mixed material sensitive to light or radiation. It is usually composed of photoresist main material, photosensitizer, solvent, acid-proof diffusing agent and other additives. The photoresist main material mainly includes film-forming resin , Molecular glass compounds, inorganic oxides, etc. After the photores...

Claims

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Application Information

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IPC IPC(8): C07C309/04C07C303/32C07D333/18G03F7/004G03F7/20
CPCC07C303/32C07C381/12C07D333/18G03F7/004G03F7/2004C07C309/04Y02P20/55
Inventor 杨国强袁华许箭彭晓曼王亮乾王双青
Owner INST OF CHEM CHINESE ACAD OF SCI
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