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Aromatic sulfonium salt compound

A technology of aromatic sulfonium salts and compounds, applied in organic chemistry, instruments, optomechanical equipment, etc., can solve problems such as difficult patterning, insufficient developability, insufficient solubility of aromatic sulfonium salt compounds, etc., and achieve curability Excellent, high-resolution results

Active Publication Date: 2012-05-23
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of these aromatic sulfonium salt compounds is insufficient, especially when used as a negative resist, the developability is insufficient, so it is difficult to perform fine patterning

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0084] [Example 1-1] Synthesis of trifluoromethanesulfonate of compound No.1

[0085] 72.11 g (0.735 mol) of concentrated sulfuric acid was added to a 200 ml four-necked flask, nitrogen substitution was performed, and it cooled until the inner temperature became 10 degreeC. Add 11.24 g (0.048 mol) of bis(hydroxyphenyl) sulfoxide, dropwise add 12.33 g (0.04 mol) of 3-fluoro-4-phenylthio-benzophenone dissolved in 12.33 g of chlorobenzene, and Stirring was carried out at 30°C for 3 hours. Next, 120 g of ice water, 120 g of methanol, and 120 g of toluene were mixed in a 1 L beaker, and the reaction liquid was added thereto, stirred for 1 hour, and left still. The upper layer was removed, and 200 ml of dichloromethane and 7.49 g (0.048 mol) of lithium trifluoromethanesulfonate were added to the lower layer, followed by stirring for 1.5 hours. The dichloromethane layer was washed 3 times with 120 g of water, and the solvent was distilled off, and the obtained crude product was pur...

Embodiment 1-2

[0088] [Example 1-2] Synthesis of Antimony Hexafluoride Salt of Compound No.1

[0089] Except using KSbF instead of lithium triflate 6 Except 13.19 g (0.048 mol), it synthesized similarly to Example 1-1, and obtained the antimony hexafluoride salt of compound No. 1 (yield 6.49 g, yield 21.3%, and HPLC purity 93.2%).

[0090] [chemical 7]

[0091]

Embodiment 1-3

[0092] [Example 1-3] Synthesis of trifluoromethanesulfonate of compound No.3

[0093] Synthesis of 3,4-difluoro-6-methoxybenzophenone

[0094] In a 200ml four-necked flask, add 28.00ml of tetrachloroethane, 15.97g (0.111 mole) of 3,4-difluoroanisole, 0.50g (3.67×10 -3mol) and 20.00 g (0.142 mol) of benzoyl chloride were stirred, replaced with nitrogen, and heated at an internal temperature of 150° C. for 8 hours. Next, 200 ml of toluene and 100 ml of water were mixed in a 1 L beaker, and the reaction liquid was added thereto and stirred. 50 ml of water was added to the toluene layer, and the pH was adjusted to 10 with NaOH, followed by washing with 50 ml of water four times. The toluene layer was concentrated, and 20 ml of hexane was added to precipitate crystals. This was filtered and dried to obtain 3,4-difluoro-6-methoxybenzophenone (yield 9.00 g, yield 32.7%, HPLC purity 98.1%).

[0095] Synthesis of 3-fluoro-6-methoxy-4-phenylthiobenzophenone

[0096] Add 2.73 g (0...

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Abstract

Disclosed are: a photoacid generator having excellent developing properties, a cationic polymerisation initiator having excellent curability, and a resist composition and a cationic polymer composition using the above. Specifically disclosed are: an aromatic sulfonium salt compound represented by general formula (1), a photoacid generator and a cationic polymerisation initiator using said aromatic sulfonium salt compound, and a resist compound and a cationic polymer composition containing the above. (Within formula (1) R1-R19 represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group having 1-18 carbon atoms which may be substituted by a hydroxyl group, an alkoxy group having 1-18 carbon atoms which may be substituted by a hydroxyl group, or a thioalkoxy group having 1-18 carbon atoms which may be substituted by a hydroxyl group; An represents a monovalent anion; and at least one from among R1-R19 is a substituent group selected from the group comprising: a hydroxyl group, an ester group having 1-12 carbon atoms which is substituted by a hydroxyl group, an alkoxy group having 1-18 carbon atoms which is substituted by a hydroxyl group, and a thioalkoxy group having 1-18 carbon atoms which is substituted by a hydroxyl group).

Description

technical field [0001] The present invention relates to a novel aromatic sulfonium salt compound, and more specifically, to an aromatic sulfonium salt compound, a photo-acid generator and a cationic polymerization initiator using the same, and a resist containing the same Compositions and cationically polymerizable compositions. Background technique [0002] Sulfonium salt compounds are substances that generate acids when irradiated with energy rays such as light, and are used as photoacid generators in resist compositions for photolithography used in the formation of electronic circuits such as semiconductors, and as stereophoto Cationic polymerization initiators and the like in photopolymerizable compositions such as stereolithographic resin compositions, paints, coating agents, and adhesives. [0003] Patent Documents 1 and 2 disclose aromatic sulfonium salt compounds, photopolymerization initiators composed of them, energy ray-curable compositions containing them, and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/12C08K5/42C08L101/00G03F7/004
CPCG03F7/0045C07C381/12C07C309/06C08K5/375C09B69/004C08K5/42G03F7/004G03F7/0042
Inventor 真壁由惠奥山雄太
Owner ADEKA CORP