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Ruthenium polypyridine complex as well as preparation method and application thereof

A technology of ruthenium polypyridine and complexes, which is applied in the field of photoacid generators, and can solve the problems of large dosage of raw materials, large amount of raw materials, and low efficiency

Active Publication Date: 2020-10-27
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The first object of the present invention is to provide a ruthenium polypyridine complex, which can be used as a photoacid generator, which can solve the problem that the existing photoacid generator needs to be subjected to ultraviolet light to produce acid, and the The problem of long reaction time, large dosage of raw materials and low efficiency
[0006] The third object of the present invention is to provide a photoacid generator, which can solve the problem that the existing photoacid generator needs to produce acid by ultraviolet light, and the acid generation reaction time is long, and the required raw material measurement is large. The problem of inefficiency

Method used

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  • Ruthenium polypyridine complex as well as preparation method and application thereof
  • Ruthenium polypyridine complex as well as preparation method and application thereof
  • Ruthenium polypyridine complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] A ruthenium polypyridine complex of the formula,

[0044]

[0045] Its preparation comprises the following steps:

[0046] RuCl 3 ·xH 2 O (50mg, 0.19mmol) and 4,4'-dichloromethyl-2,2'-bipyridine (bcm-bpy) (152mg, 0.6mmol) in DMF solvent N 2 Reflux overnight under atmosphere and spin dry the solvent. Compound 3 was purified by silica gel column, the eluent was CH 3 CN / H 2 O / KNO 3 (10:4:1), the product was dissolved in water, and with NH 4 PF 6 Precipitate out. Refer to attached figure 1 and 2 . 1 H NMR (400MHz, CD 3 CN)δ8.49(s,6H),7.61(d,J=5.8Hz,6H),7.37(d,J=5.9Hz,6H),4.73(s,12H).HR ESI-MS:m / z =429.9834for(M-2PF 6 - ) 2+ .

[0047]The prepared above-mentioned ruthenium polypyridine complex was dissolved in water to a concentration of 10 μM, and irradiated with visible light with a wavelength of 520 nm, and the light intensity was 10 mW / cm 2 , the light time is 50s, and the photoacid efficiency is 50%. as attached image 3 It can be seen that the pH...

Embodiment 2

[0049] A ruthenium polypyridine complex of the formula,

[0050]

[0051] Its preparation comprises the following steps:

[0052] RuCl 3 ·xH 2 O (100mg, 0.38mmol) and LiCl (106mg), bpy (113mg, 0.8 mmol ) in DMF solvent N 2 Reflux overnight under atmosphere and spin dry the solvent. Add acetone to the obtained product, place it overnight in a refrigerator at 4°C, and filter to obtain a solid (intermediate, Ru(bpy) 2 Cl 2 ), 100mg Ru(bpy) 2 Cl 2 (0.19mmol) and bcm-bpy (50.6mg, 0.2 mmol ) in DMF solvent N 2 Reflux overnight under atmosphere and spin dry the solvent. Compound 1 was purified by silica gel column, the eluent was CH 3 CN / H 2 O / KNO 3 (10:4:1), the product was dissolved in water, and with NH 4 PF 6 sink out.

[0053] The prepared above-mentioned ruthenium polypyridine complex was dissolved in water to a concentration of 10 μM, and irradiated with visible light with a wavelength of 520 nm, and the light intensity was 10 mW / cm 2 , the light time is ...

Embodiment 3

[0055] A ruthenium polypyridine complex of the formula,

[0056]

[0057] Its preparation comprises the following steps:

[0058] RuCl 3 ·xH 2 O (100mg, 0.38mmol) and LiCl (106mg), bcm-bpy (204mg, 0.8mmol) in DMF solvent N 2 Reflux overnight under atmosphere and spin dry the solvent. Add acetone to the obtained product, place it overnight in a refrigerator at 4°C, and filter to obtain a solid (intermediate, Ru(bcm-bpy) 2 Cl 2 ), 100mg Ru(bcm-bpy) 2 Cl 2 (0.15mmol) and bpy (22.7mg, 0.16 mmol ) in DMF solvent N 2 Reflux overnight under atmosphere and spin dry the solvent. Compound 3 was purified by silica gel column, the eluent was CH 3 CN / H 2 O / KNO 3 (10:4:1), the product was dissolved in water, and with NH 4 PF 6 sink out.

[0059] The prepared above-mentioned ruthenium polypyridine complex was dissolved in water to a concentration of 10 μM, and irradiated with visible light with a wavelength of 520 nm, and the light intensity was 10 mW / cm 2 , the light tim...

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Abstract

The invention discloses a ruthenium polypyridine complex, the structure of the ruthenium polypyridine complex is shown as a formula 1, the ruthenium polypyridine complex is used as a photoacid generator, and the problems that the existing photoacid generator needs to be irradiated by ultraviolet light to generate acid, the acid generation reaction time is long, the dosage of required raw materialsis large and the efficiency is low can be solved. The invention also discloses a preparation method and application of the ruthenium polypyridine complex.

Description

technical field [0001] The invention relates to the technical field of photoacid generators. More specifically, it relates to a ruthenium polypyridine complex and its preparation method and application. Background technique [0002] Photoacid generators (Photoacid generators, PAGs) are a class of molecules that can generate acids under light of a certain wavelength. Photoacid generators are widely used in the field of photoresist (Photoresist). The principle of photoresist is that the solubility of photoresist changes after being irradiated by the above light source. In integrated circuits and semiconductor accessories, photoacid generators can improve the photoresist system. Sensitivity, improve image quality. There have been a large number of documents and patents related reports on photoacid generators. For example, in the Chinese invention patent application publication document with publication number CN108496113A and the Chinese invention patent application publicati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/26C07F15/00G03F7/004
CPCC07D213/26C07F15/0053G03F7/004Y02P20/55
Inventor 王雪松田纳周前雄
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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