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Molecular glass chemical amplification photoresist based on metalloporphyrin and preparation method and application thereof

A metalloporphyrin and metal salt technology, applied in the field of photoresist, can solve problems such as uneven distribution, limited lithographic resolution and line edge roughness, difficult to adapt to high-resolution lithography, etc., to meet the requirements of lithography technology required effect

Active Publication Date: 2021-06-22
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the large molecular weight and uneven distribution of traditional polymer chemical amplification glue, the resolution and line edge roughness of lithography have been limited, and it is difficult to meet the requirements of high-resolution lithography

Method used

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  • Molecular glass chemical amplification photoresist based on metalloporphyrin and preparation method and application thereof
  • Molecular glass chemical amplification photoresist based on metalloporphyrin and preparation method and application thereof
  • Molecular glass chemical amplification photoresist based on metalloporphyrin and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: Photoresist composition based on 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl) porphyrin zinc compound

[0068] Photoresist composition:

[0069] (1) Substrate: 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl)porphyrin zinc (compound 1-D) 50mg

[0070] (2) Photoacid generator: 2.5mg

[0071] (3) Organic base: trioctylamine 0.125mg

[0072] (4) Organic solvent: propylene glycol methyl ether acetate (PGMEA) 1.0ml

[0073] (5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl)porphyrin zinc):

[0074]

[0075] Synthesis of Compound A:

[0076] Atmospheric pressure distillation of pyrrole, take 5 mL of distilled pure pyrrole, add 10 mL of propionic acid to dilute, set aside. Measure 4.5g of 4-methoxybenzaldehyde and 220mL of propionic acid into a 500mL three-necked bottle, stir rapidly, and heat to reflux; after the drug is completely dissolved, use a peristaltic pump to add the propionic acid solution of pyrrole drop by drop for about 30 minutes. Aft...

Embodiment 2

[0083] Example 2: Photoresist composition based on 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl) porphyrin zirconium compound

[0084] Photoresist composition:

[0085] (1) Substrate: 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl)porphyrin zirconium 50mg

[0086] (2) Photoacid generator: 2.5mg

[0087] (3) Organic base: trioctylamine 0.125mg

[0088] (4) Organic solvent: propylene glycol methyl ether acetate (PGMEA) 1.0ml

[0089] Wherein, 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl)porphyrin zirconium is prepared by the same method as compound 1-D in Example 1, except that anhydrous ZrCl 4 replace ZnCl 2 ·6H 2 O. HRMS(MALDI): theoretical value [M+H] + , 1167.3328; experimental value, 1167.3330.

Embodiment 3

[0090] Example 3: Photoresist composition based on 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl)porphyrin hafnium compound

[0091] Photoresist composition:

[0092] (1) Matrix: 50mg of hafnium 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl)porphyrin

[0093] (2) Photoacid Generator 2.5mg

[0094] (3) Organic base: trioctylamine 0.125mg

[0095] (4) Organic solvent: propylene glycol methyl ether acetate (PGMEA) 1.0ml

[0096] Among them, 5,10,15,20-tetrakis(4-tert-butylcarbonate phenyl) hafnium porphyrin is prepared by the same method as compound 1-D in Example 1, except that HfCl 4 Change ZnCl 2 ·6H 2 O. HRMS(MALDI): theoretical value [M+H] + , 1257.3736, experimental value, 1257.3738.

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Abstract

The invention belongs to the technical field of photoresists, and particularly relates to a molecular glass chemical amplification photoresist baed on metalloporphyrin as well as a preparation method and application thereof. A matrix component in the photoresist is a metalloporphyrin compound as shown in a formula (P) defined in the description. The matrix component is a stereosymmetric amorphous small molecule compound and can be dissolved in an organic solvent commonly used in the photoresist. The photoresist composition disclosed by the invention can be used for preparing a uniform thin film, and molecular glass serving as a matrix component is not separated out in a film preparation process. The thin film prepared from the photoresist composition disclosed by the invention has good resolution ratio, light sensitivity and adhesion, and is easy to store.

Description

technical field [0001] The invention belongs to the technical field of photoresist, and in particular relates to a molecular glass chemically amplified photoresist based on metalloporphyrin and its preparation method and application. Background technique [0002] Porphyrins are a class of highly conjugated heterocyclic compounds containing four pyrrole rings. When two of their protons are replaced by metals, they become metalloporphyrins. At the same time, the porphyrin ring is a closed and continuous planar molecule with a large π-conjugated system, which has good electron buffering properties and photoelectric properties. Porphyrin complexes widely exist in life in nature. Metalloporphyrin complexes formed by porphyrin ligands and metal ions have many unique physical, chemical and functional properties. Therefore, the synthesis, structure, properties and application research of porphyrin and its complexes have been paid attention to by people, and have been widely used in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22G03F7/039
CPCC07D487/22G03F7/039
Inventor 杨国强陈龙王亚飞玉佳婷胡睿郭旭东王双青
Owner INST OF CHEM CHINESE ACAD OF SCI
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