Abstract: Provided is a method for producing a fluorine-containing polymer with little lot-to-lot variation in weight average molecular weight.

Abstract: Provided is a fluorine-containing polymer for use in a film-forming solution capable of forming a film that is less likely to leave a residue when immersed in a developer. The fluorine-containing polymer of the present invention contains a repeating unit represented by the following formula (1), and a repeating unit represented by the following formula (2) in an amount, expressed in parts per million based on a mass of the repeating unit of formula (1), of 1500 ppm or less: wherein R1 and R2 are each independently a hydrogen atom, a methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, or t-butyl group; R3 and R4 are each independently a hydrogen atom, a methyl group, or an ethyl group; R5 is a hydrogen atom or a trifluoromethyl group; and R6 is a hydrogen atom, a chlorine atom, a methyl group, or a trifluoromethyl group.

Abstract: The present invention is directed to a purification method for purifying a fluorine-containing polymerizable monomer of the formula (1), in which the fluorine-containing polymerizable monomer is purified by distillation in the coexistence of a phenolic compound A such as 6-tert-butyl-2,4-xylenol and a phenolic compound B such as 2,2?-methylene-bis(4-methyl-6-tert-butylphenol). By the combined use of the phenolic compound A and the phenolic compound B, it is possible to significantly suppress polymerization or oligomerization of the fluorine-containing polymerizable monomer even during industrial-production-scale distillation and efficiently purify the fluorine-containing polymerizable monomer by distillation.

Abstract: Provided is a fluorine-containing polymer which has no perfluoroalkyl group of 4 or more carbon atoms and which, when formed together with a photoacid generator into a film, shows water repellency after film formation, but becomes hydrophilic by the action of an acid generated under light irradiation, and thus serves as a pattern forming material capable of forming a film with high sensitivity and resolution. A fluorine-containing polymer according to the present invention has a repeating unit of the formula (1) where R1 is a hydrogen atom, a fluorine atom or a C1-C10 alkyl group; R2 to R5 are each independently a hydrogen atom or a C1-C10 alkyl group; X is a single bond or a divalent group; Y is a C1-C3 fluoroalkyl or carboxylate (—COOR) group; R is a C1-C3 fluoroalkyl group; and seven or less of hydrogen atoms contained in the substituent group may be substituted with fluorine.

Abstract: The selective film deposition method according to an embodiment of the present disclosure includes depositing a film of an organic matter represented by the following formula (1) on a substrate having a structure where a first surface region containing at least one of a metal or a metal oxide and a second surface region containing a nonmetallic inorganic material are both exposed, selectively in the first surface region than in the second surface region, wherein N represents a nitrogen atom; and R1 represents a C1-C30 hydrocarbon group optionally containing a hetero atom or a halogen atom, R2, R3, R4, and R5 each independently represent a hydrogen atom or a C1-C10 hydrocarbon group optionally containing a hetero atom or a halogen atom, where the hydrocarbon group covers a branched or cyclic hydrocarbon group when containing 3 or more carbon atoms.

Abstract: The present invention is directed to a purification method for purifying a fluorine-containing polymerizable monomer of the formula (1), in which the fluorine-containing polymerizable monomer is purified by distillation in the coexistence of a phenolic compound A such as 6-tert-butyl-2,4-xylenol and a phenolic compound B such as 2,2?-methylene-bis(4-methyl-6-tert-butylphenol). By the combined use of the phenolic compound A and the phenolic compound B, it is possible to significantly suppress polymerization or oligomerization of the fluorine-containing polymerizable monomer even during industrial-production-scale distillation and efficiently purify the fluorine-containing polymerizable monomer by distillation.

Abstract: Provided is a fluorine-containing polymer which has no perfluoroalkyl group of 4 or more carbon atoms and which, when formed together with a photoacid generator into a film, shows water repellency after film formation, but becomes hydrophilic by the action of an acid generated under light irradiation, and thus serves as a pattern forming material capable of forming a film with high sensitivity and resolution. A fluorine-containing polymer according to the present invention has a repeating unit of the formula (1) where R1 is a hydrogen atom, a fluorine atom or a C1-C10 alkyl group; R2 to R5 are each independently a hydrogen atom or a C1-C10 alkyl group; X is a single bond or a divalent group; Y is a C1-C3 fluoroalkyl or carboxylate (—COOR) group; R is a C1-C3 fluoroalkyl group; and seven or less of hydrogen atoms contained in the substituent group may be substituted with fluorine.

Abstract: Disclosed is an industrial method for efficient production of an ?,?-difluoroaldehyde compound, which includes reaction of an ?,?-difluoroacetate with hydrogen gas (H2) in the presence of a ruthenium catalyst and a base. By the adoption of specific reaction conditions (catalyst, base, pressure etc.), it is possible to produce the target ?,?-difluoroaldehyde compound with a high conversion rate and high selectivity.

Abstract: Disclosed is an industrial method for efficient production of an ?,?-difluoroaldehyde compound, which includes reaction of an ?,?-difluoroacetate with hydrogen gas (H2) in the presence of a ruthenium catalyst and a base. By the adoption of specific reaction conditions (catalyst, base, pressure etc.), it is possible to produce the target ?,?-difluoroaldehyde compound with a high conversion rate and high selectivity.

Abstract: A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a “2,2-difluoroacetaldehyde-alcohol composite system” in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the “2,2-difluoroacetaldehyde-alcohol composite system” formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

Abstract: A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a “2,2-difluoroacetaldehyde-alcohol composite system” in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the “2,2-difluoroacetaldehyde-alcohol composite system” formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

Abstract: As shown by the following reaction formula, disclosed is a fluorine-containing hydroxyaldehyde production method, including the step of obtaining a fluorine-containing hydroxyaldehyde represented by the general formula (1) by reacting a fluorine-containing ketone represented by the general formula (4) and an aldehyde represented by the general formula (5) in the presence of an organic base selected from a heterocyclic compound which contains a nitrogen atom in its ring or a tertiary amine. By this production method, it is possible to obtain the fluorine-containing hydroxyaldehyde in a high yield. Furthermore, it is possible to easily obtain in high yields a fluorine-containing propanediol, which is a derivative of this fluorine-containing hydroxyaldehyde, and a fluorine-containing alcohol monomer by using the same.

Abstract: A method of stabilizing a fluorine-containing acid amplifier.

Abstract: As shown by the following reaction formula, disclosed is a fluorine-containing hydroxyaldehyde production method, including the step of obtaining a fluorine-containing hydroxyaldehyde represented by the general formula (1) by reacting a fluorine-containing ketone represented by the general formula (4) and an aldehyde represented by the general formula (5) in the presence of an organic base selected from a heterocyclic compound which contains a nitrogen atom in its ring or a tertiary amine. By this production method, it is possible to obtain the fluorine-containing hydroxyaldehyde in a high yield. Furthermore, it is possible to easily obtain in high yields a fluorine-containing propanediol, which is a derivative of this fluorine-containing hydroxyaldehyde, and a fluorine-containing alcohol monomer by using the same.

Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography.

Abstract: A method of stabilizing a fluorine-containing acid amplifier.

Abstract: According to the present invention, an ?-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an ?-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the ?-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the ?-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the ?-substituted acrylic acid.

Abstract: Disclosed is a process for producing ?-substituted norbornanyl acrylates efficiently on an industrial scale while suppressing the formation of by-products derived from intramolecular cyclization, excessive addition to acrylic acid etc. The ?-substituted norbornanyl acrylates are useful as norbornene resist monomers. In the disclosed process, an ?-substituted acrylic acid is directly reacted with a substituted norbornene in the presence of at least one acid catalyst selected from methanesulfonic acid and camphorsulfonic acid. It is possible in this reaction to suppress the formation of the by-products derived from intramolecular cyclication, excessive addition of the acid to the reaction product etc.

Abstract: According to the present invention, an ?-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an ?-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the ?-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the ?-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the ?-substituted acrylic acid.

Abstract: Aminoethanol is reacted with a fluoroalkylsulfonic anhydride to obtain a fluoroalkylsulfonylaminoethanol (first step: sulfonylamidation step). The fluoroalkylsulfonylaminoethanol is esterified with an ?-substituted acrylate derivative to obtain a desired fluoroalkylsulfonylaminoethyl ?-substituted-acrylate (second step: esterification step). Thus, the desired fluoroalkylsulfonylaminoethyl ?-substituted-acrylate having a higher purity can be produced in higher yield with higher operating efficiency than in conventional techniques.