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N-para-sulfonium salt substituted pyrazoline derivative, photocurable composition and preparation method

A technology of sulfonium salt and pyrazoline, which is applied in the field of organic chemistry of new materials, can solve problems such as large difficulties in industrial production, small absorption peak absorption wavelength, and unsatisfactory application, so as to achieve reduction in raw material costs, simple method, and low cost Effect

Inactive Publication Date: 2020-07-10
ZHEJIANG YANGFAN NEW MATERIALS
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the conjugated system of sulfonium salts that have been commercially used at present is relatively small, so that the absorption wavelength of its main absorption peak is relatively small, which cannot meet its application in the long-wavelength field.
The currently designed and synthesized sulfonium salts with larger wavelength absorption peaks are mainly sulfonium salts (X.Y.Wu, M. Jin, J.C.Xie, J.P.Malvel, D.C.Wan, Chemistry-A European Journal, 2017, 23(62):15783-15789), in order to enable the sulfonium salt to have good absorption at long wavelengths (>350nm) , this type of sulfonium salt needs to have a larger conjugated structure, and the synthesis of this larger conjugated structure is more difficult, there are many steps and the yield is low, and the industrial production is more difficult

Method used

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  • N-para-sulfonium salt substituted pyrazoline derivative, photocurable composition and preparation method
  • N-para-sulfonium salt substituted pyrazoline derivative, photocurable composition and preparation method
  • N-para-sulfonium salt substituted pyrazoline derivative, photocurable composition and preparation method

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preparation example Construction

[0092] [Preparation method of N-parasulfonium salt substituted pyrazoline derivatives]

[0093] The preparation method of N-para-position sulfonium salt substituted pyrazoline derivatives of the present invention comprises the following steps (c):

[0094]

[0095] In the aforementioned step (c), the compound shown in formula (I)-b and R 5 , R 6 Replace sulfoxide with Metal + x - The expressed metal element compound reaction obtains the N-para-position sulfonium salt substituted pyrazoline derivative shown in formula (I),

[0096] The R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , n, y, X - The definition of is the same as the definition in the N-para-sulfonium salt substituted pyrazoline derivative shown in the aforementioned formula (I).

[0097] The aforementioned "metal element-containing compound" is referred to as Metal + x - Indicates that it consists of a monovalent metal cation and X - Indicated anion composition.

[0098] As an example of the aforementioned st...

Embodiment 1

[0143]Example 1: Anion is synthesized as PF according to the following route 6 - Target molecule (I)-1

[0144]

[0145] (a) Sodium hydroxide, absolute ethanol, normal temperature, 2h;

[0146] (b) Sodium hydroxide, absolute ethanol, 80°C, 2h;

[0147] (c) Methanesulfonic acid, phosphorus pentoxide, protected from light, room temperature, 6h;

[0148] (d) Potassium hexafluorophosphate aqueous solution, room temperature.

[0149] 1. Synthesis of 1,3-diphenyl-2-en-1-one

[0150] Add acetophenone (24.00 g, 0.20 mol), benzaldehyde (21.20 g, 0.20 mol) and absolute ethanol (60 mL) into a 500 mL three-necked flask containing a magnetic rotor, and stir at room temperature. Then an aqueous solution of sodium hydroxide (16 g, 0.40 mol, 20 mL) was prepared and added dropwise to the reaction system through a constant pressure dropping funnel. After the addition was completed, the reaction was carried out for 2 hours, and the reaction process was monitored by a silica gel chromato...

Embodiment 2

[0157] Example 2: Anion is synthesized as PF according to the following route 6 - Synthesis of Target Molecule (I)-5

[0158]

[0159] (a) Sodium hydroxide, absolute ethanol, normal temperature, 2h;

[0160] (b) Sodium hydroxide, absolute ethanol, 80°C, 2h;

[0161] (c) Acetic anhydride, acetonitrile, potassium hexafluorophosphate, 98% H 2 SO 4 , 5-10℃, 3h

[0162] 1. Synthesis of 3-phenyl-1-(2-furyl)-2-en-1-one

[0163] The product was obtained by reacting 2-acetylfuran with benzaldehyde, the method was the same as in Example 1, and the yield was 89.7%. HRMS for C 13 h 10 o 2 : 198.0731 (calculated value), 198.0728 (actual value).

[0164] 2. Synthesis of 1-phenyl-3-(2-furyl)-5-phenylpyrazoline

[0165] The product was obtained by reacting 3-phenyl-1-(2-furyl)-2-en-1-one with phenylhydrazine. The method was the same as in Example 1, and the yield was 88.4%. HRMS for C 19 h 16 N 2 O: 288.1313 (calculated value), 288.1318 (actual value).

[0166] 3. Synthesis...

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Abstract

The invention relates to an N-para-sulfonium salt substituted pyrazoline derivative shown as the following formula (I) in the specification, a photocurable composition, and a preparation method of theN-para-sulfonium salt substituted pyrazoline derivative shown as the following formula (I). The N-para-sulfonium salt substituted pyrazoline derivative shown as formula (I) has good absorption at a wavelength of 350nm or above, and compared with a 5-substituted sulfonium salt, the N-para-sulfonium salt substituted pyrazoline derivative has the advantages of simpler and more convenient molecule synthesis steps and reduced cost of raw materials, and is more suitable for industrial production and application.

Description

technical field [0001] The invention belongs to the field of organic chemistry of new materials, and in particular relates to the preparation of N-parasulfonium salt-substituted pyrazoline derivatives. Background technique [0002] In the early 1980s, Ito of IBM first proposed a chemically amplified resist (H.Ito, C.G.Wilson, J.M.S.Frechet, Process of 1982 Symposium on VLSI Technology, 1982, 1:86-87). After more than 30 years of development, chemically amplified resists have been widely recognized and applied in the field of imaging materials. The chemical amplification system has become the basic choice of high-sensitivity resist. In chemically amplified resists, photoacid generators have been extensively studied. Due to the good chemical amplification effect of photoacid generators, it is not only widely used in the field of imaging materials, but also in the fields of two-dimensional and three-dimensional microlithography technology, scale integrated circuit manufacturi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06C07D405/04C07D409/04C07D403/04C07D405/14C07D403/14C07D417/04C08F2/50C08G59/68
CPCC07D231/06C07D403/04C07D403/14C07D405/04C07D405/14C07D409/04C07D417/04C08F2/50C08G59/687
Inventor 吴红辉汤文杰金明葛前建张辛宇陈世雄樊彬
Owner ZHEJIANG YANGFAN NEW MATERIALS
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