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Novel sulfonic acid derivative compound and novel naphthalic acid derivative compound

A technology of sulfonic acid derivatives and compounds, which is applied in the field of sulfonic acid derivative compounds, can solve the problems of properties, performance differences, insufficient compatibility and photosensitivity, etc., and achieve good photosensitivity

Active Publication Date: 2012-10-03
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no disclosure or revelation about the differences in properties and performance caused by the type of substitution, substitution position, etc.
[0007] The sulfonyloxyimides with naphthalimide groups described in the above-mentioned patent documents are used as photoacid generators used in photoresists, and are used in photosculpting resin compositions, coatings, coatings, etc. In the case of cationic polymerization initiators used in adhesives, inks, etc., the compatibility with organic components such as organic solvents and resin components and the photosensitivity on the long-wavelength side are not sufficient

Method used

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  • Novel sulfonic acid derivative compound and novel naphthalic acid derivative compound
  • Novel sulfonic acid derivative compound and novel naphthalic acid derivative compound
  • Novel sulfonic acid derivative compound and novel naphthalic acid derivative compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0133] [Example 1] Production of Compound A-1

[0134] Add 9.290g (0.0335mol) of 4-bromonaphthalic anhydride, 34.0g dimethyl sulfoxide, 4.140g (0.0369mol) of 1,4-diazabicyclo[2.2.2] into a 100ml four-necked flask Octane was stirred, and the inside of the system was set as a nitrogen atmosphere. 3.170 g (0.0352 mol) of butanethiol was added dropwise below 30°C, and stirred at 40°C for 5 hours. 70 ml of methanol was added to the reaction liquid, ice-cooled, stirred for 30 minutes, and the precipitated crystals were collected by filtration. This was dried to obtain yellow crystals of the target compound A-1. Yield 7.15 g (yield 74.6%), based on HPLC (column: Inertsil ODS-24.6 mm × 250 mm manufactured by GL Sciences Inc., solvent: acetonitrile / water = 7 / 3, L-7455 diode array manufactured by Hitachi, Ltd. The purity of detector detection wavelength (230nm) is 97.4%. Based on deuterated dimethyl sulfoxide solvent 1 The measurement results of H-NMR are shown in Table 1-1.

Embodiment 2

[0135] [Example 2] Production of compound I-1

[0136] 6.87 g (0.0240 mol) of compound A-1, 27.5 g of dimethylformamide, and 2.00 g (0.0288 mol) of hydroxylamine hydrochloride were added to a 100 ml four-necked flask, stirred, and a nitrogen atmosphere was set in the system. 2.40 g (0.0288 mol) of 48 weight% sodium hydroxide aqueous solution was dripped at 30 degreeC or less, and it stirred at room temperature for 2 hours. 27.5 ml of ion-exchanged water was added to the reaction liquid, ice-cooled, stirred for 30 minutes, 1.00 g (0.0096 mol) of 35% by weight aqueous hydrochloric acid was added, and stirred for 1 hour. The precipitated crystals were collected by filtration and dried to obtain yellow crystals of the target compound I-1. Yield 7.04 g (yield 97.4%), based on HPLC (column: Inertsil ODS-24.6 mm × 250 mm manufactured by GL Sciences Inc., solvent: acetonitrile / water = 7 / 3, L-7455 diode array manufactured by Hitachi, Ltd. The purity of the detector detection waveleng...

Embodiment 3

[0137] [Example 3] Production of Compound S-28

[0138]Add 3.01g (0.0100mol) of compound I-1, 17.7g of dichloroethane, and 1.26g (0.0125mol) of triethylamine into a 50ml four-necked flask, stir and dissolve, then set the system as a nitrogen atmosphere . 5.77 g (0.0110 mol) of 48 mass % d-camphorsulfonyl chloride dichloroethane solutions were dripped at 20 degreeC, and it stirred for 2 hours. 20 ml of ion-exchanged water and 10 ml of dichloromethane were added to the reaction solution and stirred, and the organic layer obtained by oil-water separation was washed twice with 20 ml of 0.5% by weight aqueous sodium hydroxide solution and 20 ml of 3% by weight aqueous hydrochloric acid solution. After washing once and four times with 30 ml of ion-exchanged water, the solvent was distilled off from the dichloromethane layer to obtain the target product as a yellow solid. Yield 4.696g (yield 90.9%), based on HPLC (column: CAPCELL PAK C8 DD 4.6mm×250mm manufactured by Shiseido, solv...

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PUM

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Abstract

Disclosed are a novel sulfonic acid derivative compound and a novel naphthalic acid derivative compound with high solubility in organic solvents, good light sensitivity, and suitability as a photoacid generator and a polymerization initiator. The sulfonic acid derivative compound is represented by formula (I) (wherein R01, R04, R05 and R06 represent a hydrogen atom, one of R02 and R03 represent a carbon number 4-18 alkoxy group which may be substituted with an alicyclic hydrocarbon group, a heterocyclic group or a halogen atom and which may have a branch, and R07 is a carbon number 1-18 aliphatic hydrocarbon group which may be substituted by a halogen atom and / or an alkylthio group carbon atoms).

Description

technical field [0001] The present invention relates to a novel sulfonic acid derivative compound, and specifically relates to a sulfonic acid derivative compound which is useful as a photoacid generator and a cationic polymerization initiator and imparts absorption characteristics and solubility. In addition, the present invention relates to a novel naphthalene dicarboxylic acid derivative capable of obtaining the aforementioned novel sulfonic acid derivative compound. Background technique [0002] Sulfonyloxyimide (sulfonyloxyimide) having a naphthalimide group as a radiation functional group is a substance that generates an acid when irradiated with energy rays such as light, and is used to form light used in electronic circuits such as semiconductors. A photoacid generator in a resist composition for etching, or a cationic polymerization initiator in a photopolymerizable composition such as a resin composition for photosculpting, a paint, a coating layer, an adhesive, an...

Claims

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Application Information

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IPC IPC(8): C07D221/14C07D311/92C07D405/12G03F7/004
CPCG03F7/0382G03F7/0045C07D221/14C07D311/92C07D405/12G03F7/0397G03F7/0046G03F7/038C09B57/08G03F7/0392G03F7/2004
Inventor 村井俊彦真壁由惠藤田昌平
Owner ADEKA CORP
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