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

Abstract: An object of the present invention is to provide a photosensitive resin composition having good liquid repellency. The photosensitive resin composition of the present invention at least contains a fluororesin having a crosslinking site, a solvent, and a photopolymerization initiator, and the fluororesin contains a repeating unit derived from a hydrocarbon having a fluorine atom.

Abstract: A calibration method includes acquiring medium information; specifying a type of medium by collating medium information with structure data; executing a first simulation of ejecting liquid by changing at least one of physical property conditions at least once for a structure model corresponding to a specified type of the medium; ejecting the liquid onto the medium; acquiring permeation information of the liquid ejected to the medium; estimating a physical property condition of the liquid by collating the permeation information with results of the first simulation; executing a second simulation of ejecting the liquid by changing at least one of ejection conditions at least once based on the estimated physical property condition; and displaying a plurality of virtual print results, which are virtual print results when printing is performed on the medium based on each of the ejection conditions, based on results of the second simulation.

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: An object of the present invention is to provide a photosensitive resin composition having good liquid repellency. The photosensitive resin composition of the present invention at least contains a fluororesin having a crosslinking site, a solvent, and a photopolymerization initiator, and the fluororesin contains a repeating unit derived from a hydrocarbon having a fluorine atom.

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: According to the present invention, there is provided a production process of a 2-fluoroacrylic ester including: a bromination step of converting a 2-fluoropropionic ester to a 2-bromo-2-fluoropropionic ester by reaction of the 2-fluoropropionic ester with a nitrogen-bromine bond-containing brominating agent in the presence of a radical initiator; and a dehydrobromination step of reacting the 2-bromo-2-fluoropropionic ester with a base. It is not necessary in this process to adopt very-low-temperature conditions and to use a stoichiometric amount of expensive reagent. The target 2-fluoroacrylic ester can be thus produced at low cost.

Abstract: According to the present invention, there is provided a production process of a 2-fluoroacrylic ester including: a bromination step of converting a 2-fluoropropionic ester to a 2-bromo-2-fluoropropionic ester by reaction of the 2-fluoropropionic ester with a nitrogen-bromine bond-containing brominating agent in the presence of a radical initiator; and a dehydrobromination step of reacting the 2-bromo-2-fluoropropionic ester with a base. It is not necessary in this process to adopt very-low-temperature conditions and to use a stoichiometric amount of expensive reagent. The target 2-fluoroacrylic ester can be thus produced at low cost.

Abstract: A coating material including a low-molecular or medium-molecular organic compound represented by general formula (1). (In the formula, R1 is a single bond, methylene, ethylene or oxygen; and R2 is a hydrogen atom, or a hydrocarbon group, a fluorine-containing alkyl group, a cyclic form containing an aromatic group or aliphatic group, which may contain hydroxy group, carboxyl group, amino group, amide group, imide group, glycidyl group, cyano group, fluorocarbinol group, sulfonic group or sulfonylamide group, and a complex thereof, and may contain a fluorine atom, oxygen atom, nitrogen atom, silicon atom or sulfur atom, and R2's of the same type or different type may be connected by an ester bond, amide bond, ether bond, thioether bond, thioester bond or urethane bond.). This compound can be derived from a diol compound and bicyclo[2.2.2]octane-2,3:5,6-tetracarboxylic anhydride.

Abstract: The present invention relates to a novel fluorine-containing cyclic compound that is derived from a norbornadiene and hexafluoroacetone and has an oxacyclopentane structure. This compound may be represented by the following formula (1) or (2). Furthermore, the present invention relates to a fluorine-containing polymer compound prepared by a polymerization or copolymerization using this fluorine-containing cyclic compound or its derivative. By using such fluorine-containing polymer compound, it is possible to provide a superior resist material and a fine pattern forming process using the same.

Abstract: The present invention relates to a polymerizable monomer represented by the general formula (1), wherein R1 is a hydrogen atom, a halogen atom, a hydrocarbon group or a fluorine-containing alkyl group; R2 is a straight-chain or branched alkyl group, a cyclic alkyl group, an aromatic group, or a substituent having at least two of these groups, the R2 being optionally partially fluorinated; R3 is a hydrogen atom, a hydrocarbon group that is optionally branched, a fluorine-containing alkyl group, or a cyclic group having an aromatic or alicyclic structure, the R3 optionally containing a bond of an oxygen atom or carbonyl group; and n is an integer of 1-2.

Abstract: The present invention relates to a polymerizable acrylate compound represented by the general formula (1): (in the formula, R1 represents a hydrogen atom, halogen atom, hydrocarbon group or fluorine-containing alkyl group, R2 and R3 may be different or identical, and each of them independently is a hydrogen atom, fluorine atom, hydrocarbon group optionally branched, fluorine-containing alkyl group, aromatic group, or cyclic structure containing an aliphatic group and may contain oxygen or carbonyl bond) and a polymer compound obtained by using the same.

Abstract: A coating material including a low-molecular or medium-molecular organic compound represented by general formula (1). (In the formula, R1 is a single bond, methylene, ethylene or oxygen; and R2 is a hydrogen atom, or a hydrocarbon group, a fluorine-containing alkyl group, a cyclic form containing an aromatic group or aliphatic group, which may contain hydroxy group, carboxyl group, amino group, amide group, imide group, glycidyl group, cyano group, fluorocarbinol group, sulfonic group or sulfonylamide group, and a complex thereof, and may contain a fluorine atom, oxygen atom, nitrogen atom, silicon atom or sulfur atom, and R2's of the same type or different type may be connected by an ester bond, amide bond, ether bond, thioether bond, thioester bond or urethane bond.). This compound can be derived from a diol compound and bicyclo[2.2.2]octane-2,3:5,6-tetracarboxylic anhydride.

Abstract: A resist protective coating material is provided comprising an ?-trifluoromethylacrylic acid/norbornene copolymer having cyclic perfluoroalkyl groups as pendant. In a pattern-forming process, the material forms on a resist film a protective coating which is water-insoluble, dissolvable in alkaline developer and immiscible with the resist film, allowing for effective implementation of immersion lithography.

Abstract: There is provided a novel polyester compound having in its main polymer chain an aliphatic cyclic structure with carboxylic acids or carboxylic acid ester groups as represented by the chemical formula (1), a resist material containing the polyester compound and a patterning method using the resist material.

Abstract: The present invention relates to a novel fluorine-containing cyclic compound that is derived from a norbornadiene and hexafluoroacetone and has an oxacyclopentane structure. This compound may be represented by the following formula (1) or (2). Furthermore, the present invention relates to a fluorine-containing polymer compound prepared by a polymerization or copolymerization using this fluorine-containing cyclic compound or its derivative. By using such fluorine-containing polymer compound, it is possible to provide a superior resist material and a fine pattern forming process using the same.

Abstract: The present invention relates to a top coat composition, which is characterized in that it is applied to a photoresist top surface by using a polymer containing at least one structure represented by the formula [1], [2] or [3]. It is possible to produce a top coat composition solution by dissolving this top coat composition in an organic solvent. These top coat composition and top coat composition solution can be used in immersion lithography.

Abstract: A process for producing an ?-substituted acrylic norbornanyl compound represented by the formula [3] includes reacting an ?-substituted acrylic acid anhydride represented by the formula [1] with a substituted norbornanyl alcohol represented by the formula [2]. wherein R1 represents a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, or perfluoroethyl group, and wherein one of R2, R3 and R4 is a CF3C(CF3)(OH)CH2— group, and each of the other two of R2, R3 and R4 is a hydrogen.

Abstract: There is provided a novel polyester compound having in its main polymer chain an aliphatic cyclic structure with carboxylic acids or carboxylic acid ester groups as represented by the chemical formula (1), a resist material containing the polyester compound and a patterning method using the resist material.