The present invention provides: an acid generator which exhibits excellent solubility in a cationically curable compound; and a curable composition which is rapidly cured when subjected to a heat treatment, and which forms a cured product that exhibits excellent insulating properties. An acid generator according to the present invention contains a salt (1) of a cation that is represented by formula (c-1) and an anion that is represented by formula (a-1). In the formula (c-1), R1, R2and R3ff 11ff 12 represents a fluoroalkyl group, a fluoroaryl group or a fluoroalkyl-substituted aryl group; t represents an integer of 1 to 4; and u represents 0 or 1.
C07C 217/56 - Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
C07F 5/00 - Compounds containing elements of Groups 3 or 13 of the Periodic System
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
Provided is an acid generator that has superior solubility in cation-curable compounds. This acid generator includes: a salt (1) of a cation represented by formula (c-1) and a monovalent counter anion; and a salt (2) of a cation represented by formula (c-2) and a monovalent counter anion. The included percentage of the salt (2) is greater than or equal to 0.001 wt% but less than 5 wt%. In the formulas, R1, R2, and R3 represent identical or different C1-6 alkyl groups, and n represents an integer greater than or equal to 1.
C07C 217/56 - Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
C07F 5/00 - Compounds containing elements of Groups 3 or 13 of the Periodic System
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
Provided is a novel compound that has photosensitivity such that said compound rapidly decomposes and generates an acid when irradiated with light rays having a wavelength of 20 nm or lower. A sulfonium salt according to the present invention is represented by formula (1). In the formula, Rf1, Rf2, Rf11, and Rf12are identical to each other or different from each other, each of which represents a fluorine atom or a fluoroalkyl group. R1, R2, R3, R11, R12, R13, R21, R23, and R25are identical to each other or different from each other, each of which represents a hydrogen atom, a hydroxyl group, an alkyl group, or an iodine atom. R22and R24are identical to each other or different from each other, each of which represents a hydrogen atom, a hydroxyl group, an alkyl group, an iodine atom, a fluorine atom, or a fluoroalkyl group. X-represents a monovalent counter anion. At least one selected from R1, R2, R3, R11, R12, R13, and R21-R25 represents an iodine atom.
C07C 309/06 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
C07C 311/48 - Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
Provided are: a photoacid generator that effectively generates acid even when a substance such as a colorant which attenuates or blocks radiated light is present at a high concentration, the film thickness thereof is large, and a light source is visible light to infrared light, particularly infrared light having low energy; and a highly curable photosensitive composition using the photoacid generator. The present invention is a photoacid generator that is a metal complex having, as a ligand, a ring structure formed by bonding five-membered ring aromatic heterocyclic compounds directly or by π-conjugation, wherein a central metal has one or two axial ligands, and the axial ligand has an onium salt structure.
C07D 487/22 - Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups in which the condensed system contains four or more hetero rings
5.
COMPOUND, ACID GENERATOR COMPRISING SAID COMPOUND, PHOTORESIST, AND METHOD FOR MANUFACTURING ELECTRONIC DEVICE USING SAID PHOTORESIST
Provided is a novel compound which has such acid generating capability that the compound is decomposed by the irradiation with i line to generate a sulfonic acid and which can keep the acid generating capability thereof at a satisfactory level in the whole area of a resist layer even when the thickness of the resist layer is increased. The compound (1) according to the present invention is represented by formula (1). In formula (1), R1and R2each independently represent a hydrocarbon group that may have a substituent. R3represents a hydrogen atom, a OR13group or a R13group, in which the R13represents a hydrocarbon group that may have a substituent. R4represents a hydrogen atom or R14, in which the R14represents a hydrocarbon group that may have a substituent. The case where each of R3and R4 represents a hydrogen atom at the same time is excluded.
C07D 311/16 - Benzo [b] pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
C07D 311/18 - Benzo [b] pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
The present invention provides a novel compound which has photosensitivity to both h-rays and i-rays and is easily decomposed and generates a sulfonic acid, which is a strong acid, when irradiated with either h-rays or i-rays. A compound (1) according to the present invention is represented by formula (1). In formula (1), R1to R3 may be the same or different and each represent an optionally substituted hydrocarbon group. The compound (1) according to the present invention has a molar absorption coefficient of h-rays of, for example, 100 (mL/g∙cm) or more. In addition, the solubility thereof in propylene glycol monomethyl ether acetate at 25°C is, for example, 5% by weight or more.
C07D 311/14 - Benzo [b] pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
A negative photosensitive resin composition containing an epoxy group-containing resin and a cationic polymerization initiator which includes a sulfonium salt represented by General Formula (I0). In Formula (I0), R1 and R2 represent an aryl group, a heterocyclic hydrocarbon group, or an alkyl group. R3 to R5 are an alkyl group, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, a hydroxy(poly)alkyleneoxy group, or a halogen atom. k is an integer of 0 to 4, m is an integer of 0 to 3, and n is an integer of 1 to 4. A is a group represented by —S—, —O—, —SO—, —SO2—, or —CO—. X− represents a monovalent polyatomic anion
A negative photosensitive resin composition containing an epoxy group-containing resin and a cationic polymerization initiator which includes a sulfonium salt represented by General Formula (I0). In Formula (I0), R1 and R2 represent an aryl group, a heterocyclic hydrocarbon group, or an alkyl group. R3 to R5 are an alkyl group, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, a hydroxy(poly)alkyleneoxy group, or a halogen atom. k is an integer of 0 to 4, m is an integer of 0 to 3, and n is an integer of 1 to 4. A is a group represented by —S—, —O—, —SO—, —SO2—, or —CO—. X− represents a monovalent polyatomic anion
G03F 7/32 - Liquid compositions therefor, e.g. developers
G03F 7/00 - Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printed surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
8.
SULFONIUM SALT, PHOTOACID GENERATOR, CURABLE COMPOSITION, AND RESIST COMPOSITION
Provided are: a new sulfonium salt highly photosensitive to active energy ray, in particular, i-line or h-line; and a new photoacid generator which is highly photosensitive to i-line or h-line, and comprises a sulfonium salt that is highly soluble in a solvent and a cationically polymerizable compound such as an epoxy compound, and has excellent storage stability in the formulation. The present invention pertains to a sulfonium salt represented by general formula (1), and a photoacid generator comprising said sulfonium salt.
Provided are: a new sulfonium salt highly photosensitive to active energy ray, in particular, i-line or h-line; and a new photoacid generator which is highly photosensitive to i-line or h-line, and comprises a sulfonium salt that is highly soluble in a solvent and a cationically polymerizable compound such as an epoxy compound, and has excellent storage stability in the formulation. The present invention pertains to a sulfonium salt represented by general formula (1), and a photoacid generator comprising said sulfonium salt.
C07C 309/06 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
Provided is an onium salt functioning as a photoacid generator. The photoacid generator can provide a chemically amplifiable photoresist composition when it is combined with a resin component whose solubility in alkali is increased by the action of an acid generated by active energy ray irradiation such as Light or electron beam irradiation. The present invention relates to an onium salt represented by the formula (1), containing an anion structure with a proportion of a facial isomer in a total of the facial isomer and a meridional isomer being 15.0% by weight or lower.
Provided is an onium salt functioning as a photoacid generator. The photoacid generator can provide a chemically amplifiable photoresist composition when it is combined with a resin component whose solubility in alkali is increased by the action of an acid generated by active energy ray irradiation such as Light or electron beam irradiation. The present invention relates to an onium salt represented by the formula (1), containing an anion structure with a proportion of a facial isomer in a total of the facial isomer and a meridional isomer being 15.0% by weight or lower.
[(R2)n+1-E]+[(R1)3(F)3P]− (1)
Provided are: a novel photoacid generator which has high photosensitivity to EUV, EB, X-ray and the like; and a resin composition for photolithography, the resin composition containing this photoacid generator. The present invention provides a photoacid generator (P) which is characterized by containing a selenonium salt represented by general formula (1). (In formula (1), each of X1, X2 and X3 independently represents a halogen atom, a hydroxy group, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, an arylthio group having 6 to 14 carbon atoms, or an arylseleno group having 6 to 14 carbon atoms (some or all of hydrogen atoms in the alkyl group, alkoxy group, aryl group, aryloxy group, arylthio group and arylseleno group may be substituted by fluorine atoms); each of y1, y2 and y3 independently represents a number from 0 to 5; and A represents a monovalent anion.)
Provided is a photosensitizer which has a specific structure, and has higher sensitivity than existing photosensitizers when light irradiation causes a rapid change from hydrophilicity to hydrophobicity. The present invention pertains to: a photosensitizer containing a metal complex which is represented by general formula (1) or general formula (2) and has a cyclic ligand that forms a ring structure in which pyrrole rings are linked directly or via π conjugation, and an axial ligand having an onium salt structure; an antibody conjugate to which said photosensitizer binds; a method of using said photosensitizer, the method being characterized in that the detachment of an axial ligand is promoted through irradiation with light having a wavelength of 500-1,500 nm; and a usage method in which said photosensitizer is used for therapeutic purpose.
C07D 487/22 - Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups in which the condensed system contains four or more hetero rings
A61K 47/68 - Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
C07F 9/6584 - Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
A61K 41/00 - Medicinal preparations obtained by treating materials with wave energy or particle radiation
12.
PHOTOACID GENERATOR, AND PHOTOSENSITIVE COMPOSITION USING SAME
Provided are: a photoacid generator that effectively generates acid even when there is a high concentration of a substance such as a colorant that attenuates or shields irradiated light, and even when the film thickness is great and a light source is visible light to infrared light, in particular, infrared light with low energy; and a highly curable photosensitive composition using the photoacid generator. The present invention is a photoacid generator that is a metal complex having, as a ligand, a ring structure formed by bonding five-membered ring aromatic heterocyclic compounds directly or by π-conjugation, wherein a central metal has one or two axial ligands, and the axial ligand has an onium salt structure.
C07F 19/00 - Metal compounds according to more than one of main groups
C08G 59/20 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the epoxy compounds used
G03F 7/038 - Macromolecular compounds which are rendered insoluble or differentially wettable
C07D 487/22 - Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups in which the condensed system contains four or more hetero rings
C07F 9/06 - Phosphorus compounds without P—C bonds
Provided are a novel sulfonium salt having high photosensitivity to g-rays or h-rays; a novel photoacid generator containing a sulfonium salt that has high photosensitivity to g-rays or h-rays, has high solubility in solvents and cationically polymerizable compounds such as epoxy compounds, and has an excellent storage stability in compositions containing the cationically polymerizable compounds; and the like. The present invention relates to a sulfonium salt represented by the formula (1), a photoacid generator containing the sulfonium salt, and the like.
Provided are a novel sulfonium salt having high photosensitivity to g-rays or h-rays; a novel photoacid generator containing a sulfonium salt that has high photosensitivity to g-rays or h-rays, has high solubility in solvents and cationically polymerizable compounds such as epoxy compounds, and has an excellent storage stability in compositions containing the cationically polymerizable compounds; and the like. The present invention relates to a sulfonium salt represented by the formula (1), a photoacid generator containing the sulfonium salt, and the like.
C07D 333/78 - Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
Provided is a highly active actinic-ray-sensitive acid generator which, upon irradiation with actinic rays, comes to have cationic-polymerization performance or crosslinking reaction performance and which enables curable compositions containing the acid generator to have satisfactory storage stability. This actinic-ray-sensitive acid generator comprises sulfonium salt (A), which is represented by general formula (1), and sulfonium salt (B), which is represented by general formula (2), and has a content of the sulfonium salt (B) of 0.01-2 mol% with respect to the total number of moles of the sulfonium salt (A) and the sulfonium salt (B).
The purpose of the present invention is to provide: a photoacid generator containing a sulfonamide compound which has a high decomposition rate in response to near-ultraviolet rays, generates a superacid bis-sulfonamide, and is highly soluble in a resist solvent; and a photolithography resin composition which contains the photoacid generator and is highly sensitive to near-ultraviolet rays. The present invention pertains to: a nonionic photoacid generator (A) characterized by containing a sulfonamide compound represented by general formula (1); and a photolithography resin composition (Q) containing the nonionic photoacid generator (A).
C07C 311/49 - Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
C07D 491/048 - Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
The present invention provides a useful photoacid generator which is used for a photocurable composition or a chemically amplified negative photoresist composition, and which is useful for yellowing resistance of these compositions. The present invention provides a photoacid generator which is characterized by containing a sulfonium salt (CA) represented by general formula (1) and a compound (S) represented by general formula (2), and which is also characterized in that if the total content of the sulfonium salt (CA) and the compound (S) is determined by high-speed liquid chromatography (HPLC) and the total area of the sulfonium salt (CA) and the compound (S) is taken as 100, the area ratio of the compound (S) is from 0.02 to 3.0.
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The present invention provides a useful photoacid generator which is contained in a photocurable composition, a chemically amplified positive photoresist composition and a chemically amplified negative photoresist composition, and which is useful for long-term storage stability of these compositions, especially for the achievement of a composition that has excellent long-term storage stability at low temperatures. The present invention is a photoacid generator which contains sulfonium salts represented by general formulae (1) to (3), and which is characterized in that the total area ratio of (2) and (3) is from 0.02 to 5.5 if the total area of (1) to (3) is taken as 100 when the contents of the sulfonium salts are determined by high-speed liquid chromatography (HPLC).
The present invention functions as a photoacid generator; and this photoacid generator provides a chemically amplified photoresist composition by being combined with a component that is a resin, the solubility of which in an alkali is increased by the action of an acid that is generated when irradiated with an active energy ray such as an electron beam or light, or the like. The present invention is an onium salt which is represented by general formula (1), wherein among two kinds of isomers of an anion structure, namely among facial isomers and meridional isomers, the proportion of the facial isomers is 15.0% by weight or less. (1): ((R2n+1n+1-E)+((R1333P)-
Provided is an epoxy resin composition that uses a curing accelerator that is an excellent curing accelerator for reactions between epoxy resins and curing agents and that does not produce free chlorine. The present invention is an epoxy resin composition comprising: a phosphonium salt (S) represented by general formula (1) and composed of a phosphonium cation (A) and an n-valent carboxylate anion (B); an epoxy resin (C); and a curing agent (D). [In formula (1), R1 to R3 are each independently a C6-12 aryl group; R4 is a C1-6 alkyl group; n represents an integer from 1-6; and Xn- represents an n-valent carboxylate anion.]
C08G 59/40 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the curing agents used
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
21.
SULFONIUM SALT, PHOTOACID GENERATOR, CURABLE COMPOSITION, AND RESIST COMPOSITION
Provided are: a novel sulfonium salt highly photosensitive to active energy rays, in particular, i-rays or h-rays; and a novel photoacid generator which is highly photosensitive to i-rays or h-rays, and contains a sulfonium salt that is highly soluble in a solvent and a cationically polymerizable compound such as an epoxy compound, and has excellent storage stability in the formulation. The present invention pertains to a sulfonium salt represented by general formula (1), and a photoacid generator characterized by containing said sulfonium salt.
Provided is an epoxy resin composition having good fluidity, and exhibiting excellent reliability for electronic components such as a semiconductor. The present invention is an epoxy resin composition containing an imidazolium salt (S), an epoxy resin (C), and a curing agent (D), the imidazolium salt (S) comprising an imidazolium cation (A) represented by the general formula (1) and at least one anion (B) selected from the group consisting of an carboxylate anion and a phenoxide anion. [In the formula (1), R1 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, or a butyl group; R2 and R3 each represent a methyl group, an ethyl group, a propyl group, or a butyl group, and may be either the same as or different from each other; and R4 and R5 each represent a hydrogen atom, a methyl group, or an ethyl group, and may be either the same as or different from each other.]
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The purpose of the present invention is to provide: a photocurable composition for nanoimprinting having excellent fine pattern formability, mold release properties, etching resistance, and application properties; and a pattern forming method using said composition. The present invention is a photocurable composition for nanoimprinting characterized by containing, as essential components, (A) an onium salt represented by general formula (1) or (2), (B) a cation-polymerizable hydrocarbon compound, and (C) an oligomer having an ethylenically unsaturated group. (1): A+n6-n6-n]-, (2): A+44 -[In formula (1), each Rf independently represent an alkyl group having 1-8 carbon atoms, an alkenyl group having 2-8 carbon atoms, or an aryl group having 6-10 carbon atoms, wherein in each of the groups, 80% or more of the hydrogen atoms bound to carbon atoms are substituted with fluorine atoms, and n is an integer of 1-5. In formula (2), R represents a phenyl group in which at least one hydrogen atom is substituted with a fluorine atom or a trifluoromethyl group. A+ is a monovalent iodonium cation or sulfonium cation.]
C08F 290/00 - Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
H01L 21/027 - Making masks on semiconductor bodies for further photolithographic processing, not provided for in group or
B29C 59/02 - Surface shaping, e.g. embossing; Apparatus therefor by mechanical means, e.g. pressing
25.
ACID GENERATOR AND CURABLE COMPOSITION CONTAINING SAME
The present invention provides: an acid generator which is suitable for the formation of a cured product that has excellent curability, heat resistance and thermal yellowing resistance; a curable composition which contains this acid generator; and a cured product which is obtained using this curable composition. The present invention is an acid generator which contains an onium salt represented by general formula (1). (In the formula, each of R1to R3independently represents an alkyl group having from 1 to 8 carbon atoms, an alkenyl group having from 2 to 8 carbon atoms or an optionally substituted phenyl group; some or all of hydrogen atoms bonded to at least one of the R1to R3groups are substituted by fluorine atoms, and from 30% to 70% of all hydrogen atoms bonded to the R1to R3groups are substituted by fluorine atoms; E represents an n-valent element selected from among S, I, N and P; n represents an integer from 1 to 3; and R4 represents an organic group bonded to E.)
The purpose of the present invention is to provide: a sulfonamide compound which has a high decomposition rate in response to near-ultraviolet rays and which generates a superacid bis-sulfonamide, and which is highly soluble in a resist solvent; a photoacid generator containing the sulfonamide compound; and a photolithography resin composition which contains the photoacid generator and which has high sensitivity to near-ultraviolet rays. The present invention is a sulfonamide compound (A) characterized by being represented by general formula (1) or (2).
C07C 311/49 - Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
C07D 221/14 - Aza-phenalenes, e.g. 1,8-naphthalimide
Provided are: a novel sulfonium salt which exhibits high photosensitivity to g rays or h rays; and a novel photoacid generator containing a sulfonium salt which exhibits high photosensitivity to g rays or h rays, high solubility in a solvent and a cationic polymerizable compound such as an epoxide, and excellent storage stability in such a formulation. The present invention is a sulfonium salt represented by general formula (1) and a photoacid generator characterized by containing said sulfonium salt.
C07C 309/04 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
C07C 309/06 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
C08G 59/40 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the curing agents used
Provided is an epoxy resin composition which uses a curing accelerator that is a superior curing accelerator for reactions between active ester compounds and epoxy resins and that does not produce free chlorine. The present invention is an epoxy resin composition that contains an epoxy resin (A), an active ester compound (B), and a curing accelerator (C), the composition being characterized by containing an imidazolium cation (D) where the curing accelerator (C) is represented by general formula (1), and an imidazolium salt (S) comprising an anion (E).
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
To provide an epoxy curing accelerator which has extremely high and stable heat resistance, and in which acceleration of a curing reaction can be suppressed; and to provide an epoxy resin composition which increases the reliability of a semiconductor device and has good curing properties through use of the epoxy curing accelerator, the epoxy resin composition has good fluidity and thoroughly fills the inside of a package, and voids are not prone to occur in the epoxy resin composition. The present invention is an epoxy resin curing accelerator (Q) characterized by including an imidazolium salt (S) comprising: an imidazolium cation (A) represented by general formula (1); and an anion (B) represented by general formula (2), (3), or (4); the melting point of the imidazolium salt (S) being 170°C or lower.
C07D 233/58 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
Provided are: a novel sulfonium salt having high photosensitivity to i-rays; and a novel photoacid generator, etc. comprising a sulfonium salt and having high photosensitivity to i-rays, and having high compatibility with cationically polymerizable compounds such as epoxy compounds, and excellent storage stability in formulations containing such compounds. The present invention pertains to: a sulfonium salt represented by general formula (1); and a photoacid generator, etc. characterized by containing the sulfonium salt. [In formula (1), R represents an alkyl group or an aryl group, substituents R1-R5 each independently represent an alkyl group, a hydroxyl group, an alkoxy group, an aryl group, an aryloxy group, a hydroxy (poly)alkyleneoxy group, or a halogen atom, and R6-R9 each independently represent an alkyl group, an aryl group, or a hydrogen atom. m1-m5 respectively represent the numbers of R1-R5, m1 and m4 represent an integer of 0-3, m2 and m5 represent an integer of 0-4, m3 represents an integer of 0-5, and X- represents a monovalent polyatomic anion.]
C07C 309/04 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
C07C 309/06 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
C07C 309/19 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
C07C 309/30 - Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
C07F 5/00 - Compounds containing elements of Groups 3 or 13 of the Periodic System
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The purpose of the present invention is to provide a non-ionic photoacid generator having a naphthalimide structure and having all of the properties of compatibility, high sensitivity, thermal stability, and base resistance required of high-resolution i-line photolithography resist materials. The present invention pertains to: a non-ionic photoacid generator (A) represented by general formula (1); and a photolithographic resin composition (Q) containing the non-ionic photoacid generator (A). [In formula (1), R1 is a C1-12 hydrocarbon group, a hydroxy group, an alkoxy group, an alkylthio group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or an alkyl carbonate group, one of R2-R6 is a C1-12 hydrocarbon group, a hydroxy group, an alkoxy group, an alkylthio group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or an alkyl carbonate group, the rest being hydrogen atoms, and Rf is a fluorine atom, or a C1-18 hydrocarbon group in which at least one hydrogen is substituted with fluorine.]
A sulfonium salt is formed of a sulfonium cation selected from a group indicated by general formulas (1), (2), and (3) and a gallate anion represented by formula (a). A photoacid generator is characterized in that said sulfonium salt is contained therein. An energy-ray curable composition contains the acid generator and a cationic polymerizable compound. A cured product is formed by curing these substances.
C08F 2/46 - Polymerisation initiated by wave energy or particle radiation
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08G 61/04 - Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
C07F 5/00 - Compounds containing elements of Groups 3 or 13 of the Periodic System
C07F 7/08 - Compounds having one or more C—Si linkages
C08G 59/40 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the curing agents used
C08K 5/45 - Heterocyclic compounds having sulfur in the ring
C08K 5/56 - Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.
C07D 209/88 - Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
C07D 279/20 - [b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
C07D 309/38 - Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
C07F 5/00 - Compounds containing elements of Groups 3 or 13 of the Periodic System
C07D 311/16 - Benzo [b] pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
35.
PHOTOACID GENERATOR AND RESIN COMPOSITION FOR PHOTOLITHOGRAPHY
The objective of the present invention is to provide a non-ionic photoacid generator having high photosensitivity to an i-line, and excellent heat-resistance stability, solubility in hydrophobic materials, and alkali developability. The present invention is a non-ionic photoacid generator (A) characterized by being represented by formula (1). [In formula (1), X is a monovalent organic group that is desorbed by the action of an acid and can be substituted by a hydrogen atom, and Rf is a C1-18 hydrocarbon group (all or part of the hydrogen may be replaced by fluorine).]
Provided are: a photo-base generator which upon reception of light, can efficiently generate an amine having high catalytic activity and which has no fear of metal corrosion; and a photosensitive composition containing the photo-base generator. The photo-base generator of the present invention is characterized by comprising an ammonium borate compound (A) represented by the general formula. [In the formula, R1 to R4 are each independently a C1-18 alkyl group, a phenyl group, or a naphthyl group, some of the hydrogen atoms of the phenyl or naphthyl group each having been optionally replaced with a C1-18 alkyl group, a C6-14 aryl group, etc.; R5 is a polyalkyleneoxy group, the terminal of the polyalkyleneoxy group being a hydrogen atom, a C1-4 alkyl group, or a phenyl group; R6 and R7 are each independently a methyl or ethyl group; Ar is a C6-14 aryl group; and Q is a divalent group through which the Ar is bonded to the cationic nitrogen atom.]
C08G 59/40 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the curing agents used
The purpose of the present invention is to provide: a curable composition for a nanoimprint, the curable composition having excellent fine pattern formability, mold release properties, and etching resistance; and a pattern formation method using the curable composition. The present invention is a curable composition for an optical nanoimprint characterized by containing, as required components, (A) an onium salt represented by formula (1), and (B) a cationically polymerizable hydrocarbon compound. (In formula (1), each Rf mutually independently represents a C1-8 alkyl group, a C2-8 alkenyl group, or a C6-10 aryl group, 80% or more of the hydrogen atoms bonded to carbon atoms of each group are substituted with fluorine atoms, n represents an integer from 1 to 5, and A+ represents a monovalent onium cation.)
Provided are the following: a sulfonium salt which does not contain a toxic metal and which exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt; a heat- or photo-acid generator characterized by containing the sulfonium salt; an energy ray-curable composition which uses a cationic polymerization initiator (acid generator) because a cured product obtained using the heat- or photo-acid generator contains no residual strong acid following a heat resistance test and therefore does not cause corrosion of a member and does not cause the problem of reduced transparency as a result of resin degradation; and a cured product of the composition. The present invention is a sulfonium salt comprising a sulfonium cation selected from the group represented by general formulae (1), (9), (10) and (11) and a gallate anion represented by formula (a); a heat- or photo-acid generator characterized by containing the sulfonium salt; a heat- or energy ray-curable composition which contains the acid generator and a cationically polymerizable compound; and a cured product obtained by curing same.
C07D 209/88 - Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
C07D 279/20 - [b, e]-condensed with two six-membered rings with hydrogen atoms directly attached to the ring nitrogen atom
C07D 311/16 - Benzo [b] pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
Because a sulfonium salt that does not contain a toxic metal and that exhibits polymerization performance and crosslinking reaction performance equal to or greater than those of a tetrakis (pentafluorophenyl) borate salt, a photoacid generator characterized in that said sulfonium salt is contained therein, and a cured product in which this substance is used do not leave a strong acid after, in particular, a heat resistance test, the present invention provides an energy-ray curable composition and a cured product that utilize a cationic polymerization initiator (acid generator), which does not cause corrosion of a member and does not cause a problem of transparency reduction due to deterioration of a resin. The present invention is: a sulfonium salt formed of a sulfonium cation selected from a group indicated by general formulas (1), (2), and (3) and a gallate anion represented by formula (a); a photoacid generator that is characterized in that said sulfonium salt is contained therein; an energy-ray curable composition containing said acid generator and a cationically polymerizable compound; and a cured product formed by curing these substances.
C07F 7/08 - Compounds having one or more C—Si linkages
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The purpose of the present invention is to provide a novel sulfonium salt having high photosensitivity to the i-line. The sulfonium salt according to the present invention is represented by formula (1). [In the formula, R1-R8 each independently represent an alkyl group, a hydroxyl group, an alkoxy group, an aryl group, an aryloxy group, a hydroxy(poly)alkyleneoxy group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom, and R9-R14 each independently represent an alkyl group, a hydroxyl group, an alkoxy group, an aryl group, an aryloxy group, a hydroxy(poly)alkyleneoxy group, a cyano group, a nitro group, or a halogen atom. n1-n4 represent an integer of 0 or 1 (note that zero indicates a direct bond between rings), m1-m6 respectively represent the total numbers of R9-R14, m1, m4, and m6 represent an integer of 0-4, m2 and m5 represent an integer of 0-3, m3 represents an integer of 0-5, and X- represents a monovalent polyatomic anion.]
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
C08L 25/18 - Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
C08L 33/00 - Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters,; Compositions of derivatives of such polymers
C08L 61/04 - Condensation polymers of aldehydes or ketones with phenols only
The purpose of the present invention is to provide a photosensitive compound which has superior curability in all cases where: (1) a substance such as a coloring agent that attenuates or blocks illuminating light is present at a high concentration in the photosensitive compound; (2) the photosensitive compound is thick and attenuates illumination; and (3) an illuminating light source emits visible light to infrared light, particularly infrared light having low energy. The photosensitive compound according to the present invention is characterized by containing, as essential components, (A) an onium salt represented by general formula (1), (B) a sensitizer, and (C) a cationic polymerizable compound having a nitrogen atom. (In formula (1), each Rf independently represents an alkyl group having 1-8 carbon atoms, an alkenyl group having 2-8 carbon atoms, or an aryl group having 6-10 carbon atoms, 80% or more of the hydrogen atoms bonded to the carbon atoms of each group being substituted with a fluorine atom, n represents an integer of 1-5, and A+ represents a monovalent onium cation.)
C08G 73/00 - Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen or carbon, not provided for in groups
The purpose of the present invention is to provide a non-ionic photoacid generator which has high optical sensitivity to i rays, while having excellent thermal stability, excellent solubility in hydrophobic materials and excellent alkali developability. The present invention provides: a non-ionic photoacid generator (A) which is characterized by being represented by general formula (1); and a resin composition (Q) for photolithography, which contains this non-ionic photoacid generator (A). (In formula (1), X represents a divalent organic group; Y represents a functional group having an active hydrogen; and R represents a hydrocarbon group having 1-18 carbon atoms (wherein some or all of the hydrogen atoms may be substituted by fluorine atoms).)
Provided is an epoxy resin curing accelerator having exceptional fluidity during mold filling as well as high catalytic activity and exceptional curability. The present invention is an epoxy resin curing accelerator (Q) characterized by including a phosphonium salt (S) that comprises a quaternary phosphonium (A) represented by general formula (1) and an anion of an organic phenol compound (B) represented by general formula (2), the organic phenol compound (B) represented by general formula (2), and an organic phenol compound (C) represented by general formula (3). [In formula (1), R1-R3 represent C6-12 aryl groups, and R4 represents a C1-8 alkyl group or the like. In formula (2), R5-R8 are the same or different and each represent hydrogen, a C1-4 alkyl group, or the like, and R9 represents a C1-18 alkyl group or the like. In formula (3), R10 represents hydrogen, a C1-18 alkyl group, or the like, and R11 represents a C6-50 functional group containing a phenol group.]
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
44.
Sulfonate compound, photoacid generator, and resin composition for photolithography
Provided are: a non-ionic photoacid generator containing a sulfonate compound having a high photosensitivity to i lines, exhibiting excellent heat-resistance stability, and exhibiting excellent solubility in a hydrophobic material; and a resin composition for photolithography containing the same. The present invention is a sulfonate compound characterized by being represented by general formula (1).
[In formula (1), R1 represents an aryl group having 6 to 18 carbon atoms or a heterocyclic hydrocarbon group having 4 to 20 carbon atoms. R2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, or an aryl group having 6 to 18 carbon atoms. R3 represents a hydrocarbon group having 1 to 18 carbon atoms (in which some or all hydrogen atoms may be substituted with fluorine).]
G03F 7/038 - Macromolecular compounds which are rendered insoluble or differentially wettable
C07C 309/73 - Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
C07D 311/12 - Benzo [b] pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
The purpose of the present invention is to provide a photosensitive composition having excellent curability even when a colorant or other substance for attenuating or blocking radiated light is present at a high concentration, the film thickness thereof is large, and the light source is visible-to-infrared light, particularly infrared light having low energy. The present invention is a photosensitive composition characterized by containing as essential components (A) an onium salt represented by general formula (1), (B) a sensitizer, and (C) a radial polymerizable compound. (In formula (1), Rf each independently represents a C1-8 alkyl group, a C2-8 alkenyl group, or a C6-10 aryl group, 80% or more of hydrogen atoms bonded to the carbon atoms of each group being substituted with fluorine atoms, n represents an integer of 1 to 5, and A+ represents a monovalent onium cation.)
Provided are a heat- or energy ray-curable composition for members that require optical properties, containing an onium gallate salt having a specific structure; and a cured article obtained by curing the same. The invention is a heat- or energy ray-curable composition containing a cationic polymerizable compound and an acid generator including an onium gallate salt represented by general formula (1). [In formula (1), R1-R4 are each independently a C1-18 alkyl group or Ar; however, at least one is Ar; Ar is a C6-14 (not including the number of carbon atoms in the following substituents) aryl group; some of the hydrogen atoms in the aryl group may be substituted by C1-18 alkyl groups or the like; E represents an element of valence n of group 15 to group 17 (IUPAC notation); n is an integer of 1-3; and R5 is an organic group bonded to E.]
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
C07F 9/06 - Phosphorus compounds without P—C bonds
C07C 279/04 - Derivatives of guanidine, i.e. compounds containing the group the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
C07D 233/54 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
C07D 409/06 - Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
G03F 7/038 - Macromolecular compounds which are rendered insoluble or differentially wettable
C07D 233/58 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
C07D 233/60 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
48.
SULFONIUM BORATE SALT, ACID GENERATING AGENT AND CURABLE COMPOSITION
Provided is a sulfonium borate salt that is free from highly toxic elements such as Sb, has a high sensitivity to active energy rays such as heat or light, and shows an excellent storage stability when blended with a cationic polymerizable compound such as an epoxy compound. The sulfonium borate salt according to the present invention that is represented by general formula (1); and an acid generating agent, etc. characterized by comprising the sulfonium borate salt. In general formula (1): R1 represents an alkyl group; and R2 represents a benzyl group represented by general formula (2).
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
Provided is an epoxy resin curing accelerator which exhibits excellent fluidity when filled into a mold, while having high catalytic activity and excellent curability. The present invention is an epoxy resin curing accelerator (Q) which is characterized by containing: a phosphonium salt (S) that is composed of a quaternary phosphonium (A) represented by general formula (1) and an anion of an organic carboxylic acid (B) represented by general formula (2); and an organic phenolic compound (C) represented by general formula (3). (In formula (1), each of R1-R3 represents an aryl group having 6-12 carbon atoms; and R4 represents an alkyl group having 1-8 carbon atoms or an aryl group having 6-12 carbon atoms. In formula (2), R5-R7 may be the same or different, and each represents a hydroxyl group, a carboxyl group, a hydrogen atom or an alkyl group having 1-4 carbon atoms; and R8 represents a hydroxyl group or a carboxyl group. In formula (3), R9-R11 may be the same or different, and each represents a hydroxyl group, a carboxyl group, a hydrogen atom or an alkyl group having 1-4 carbon atoms.)
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
C07C 57/34 - Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
C07C 59/52 - Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
Provided are: a non-ionic photoacid generator containing a sulfonate compound having a high photosensitivity to i lines, exhibiting excellent heat-resistance stability, and exhibiting excellent solubility in a hydrophobic material; and a photolithographic resin composition containing the same. The present invention is a sulfonate compound characterized by being represented by general formula (1). [In formula (1), R1 represents a C6-18 aryl group or a C4-20 heterocyclic hydrocarbon group. R2 represents a hydrogen atom, a C1-18 alkyl group, a C2-18 alkenyl group, a C2-18 alkynyl group, or a C6-18 aryl group. R3 represents a C1-18 hydrocarbon group (in which some or all hydrogen atoms may be substituted with fluorine).]
G03F 7/038 - Macromolecular compounds which are rendered insoluble or differentially wettable
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
51.
IMIDE SULFONATE COMPOUND, PHOTOACID GENERATOR, AND RESIN COMPOSITION FOR PHOTOLITHOGRAPHY
Provided are: a non-ionic photoacid generator including an imide sulfonate compound and having high light sensitivity to an i-line, excellent thermal stability, and excellent solubility in a hydrophobic material; and a resin composition for photolithography including the same. The present invention is an imide sulfonate compound represented by general formula (1). [In formula (1), R1 to R8 is each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 18 carbon atoms, a fluoroalkyl group having 1 to 18 carbon atoms, etc. At least two of R1 to R8 may be joined to form a ring structure. R9 is a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent (a part or all of the hydrogen may be substituted with fluorine).]
Provided are a photobase generator having higher sensitivity to light than do conventional photobase generators, and a photosensitive resin composition containing the photobase generator. The present invention is a photobase generator characterized in containing a salt represented by general formula (1). (In formula (1), R1-R4 are mutually independent groups represented by general formula (2), C1-18 alkyl groups, or Ar, with at least one being a group represented by general formula (2); in formula (2), (D) is a divalent group bonded on at least one side to elemental boron, and Ar1 is the same as the aforementioned Ar; and Q+ is a monovalent onium cation.)
C07C 279/04 - Derivatives of guanidine, i.e. compounds containing the group the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
C07D 233/58 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
C07D 233/60 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
Provided is a non-ionic photoacid generator having high i-line photosensitivity, excellent heat-resistant stability, and excellent solubility in hydrophobic materials. The present invention is a non-ionic photoacid generator (A) that is characterized by being expressed by general formula (1). [In formula (1), R1 and R2 each independently represents an alkyl group having 1-18 carbons or a fluoroalkyl group having 1-18 carbons, an alkenyl group having 2-18 carbons, an alkynyl group having 2-18 carbons, an aryl group having 6-18 carbons, a silyl group, or the like; m and n respectively represent the number of R1s and R2s, each number being an integer from 0 to 3, and the total number (m+n) of R1s and R2s being an integer from 1 to 6. The m number of R1s and the n number of R2s may each be the same or different. R3 represents a hydrocarbon having 1-18 carbons (wherein one part or all of the hydrogen may be substituted by fluorine).]
Provided is a novel sulfonium salt that has high solubility in a solvent and has high light sensitivity to, especially, light having a wavelength not longer than deep-UV (254 nm) and a novel photo-acid generator comprising the sulfonium salt. The invention relates to a sulfonium salt represented by the following general formula (1) and a novel photo-acid generator comprising the sulfonium salt.
−represents a monovalent counter anion.
C07C 281/12 - Compounds containing any of the groups e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being part of a ring other than a six-membered aromatic ring
C07C 309/06 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
C07C 309/19 - Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
C07C 311/48 - Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
C07C 317/04 - Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
Provided are: a photobase generator which has higher sensitivity to light compared with conventional photobase generators and can exert a high effect when used in combination with a sensitizer; and a photosensitive resin composition which contains the photobase generator. The present invention is a photobase generator characterized by comprising an ammonium salt represented by general formula (1). [In formula (1), R1 to R4 independently represent an alkyl group having 1 to 18 carbon atoms or Ar, wherein at least one of R1 to R4 represents Ar; Ar represents an aryl group having 6 to 14 carbon atoms (excluding carbon atoms contained in a substituent as mentioned below), wherein some of hydrogen atoms in the aryl group may be independently substituted by an alkyl group having 1 to 18 carbon atoms or the like; Y+ represents an ammonio group represented by general formula (2) or (3); and E represents a hydrogen atom or a group represented by general formula (5).]
C07D 233/58 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
C07D 233/61 - Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
56.
SULFONIUM SALT, PHOTOACID GENERATOR, CURABLE COMPOSITION, AND RESIST COMPOSITION
The present invention provides: a novel sulfonium salt having high i-ray photosensitivity; and a novel sulfonium-salt-containing photoacid generator, etc. having high i-ray photosensitivity, strong compatibility with cationically polymerizable compounds such as epoxy compounds, and exceptional storage stability as a formulation. The present invention is a sulfonium salt expressed by general formula (1) and a photoacid generator, etc. characterized in containing the sulfonium salt (R represents an alkyl or aryl group; R1 through R3 independently represent an alkyl group, hydroxyl group, alkoxy group, aryl group, aryloxy group, hydroxyl(poly)alkyleneoxy group, cyano group, nitro group, or halogen atom; m1 through m3 each represent the number of groups R1 through R3; m1 represents an integer of 0 to 4; m2 and m3 represent integers of 0 to 5; and X- represents a monovalent polyatomic anion).
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
Provided are: a nonionic photo-acid generator having high photosensitivity to i-line, excellent heat resistance stability and excellent solubility in a hydrophobic material; and a resin composition for photolithography, which contains the nonionic photo-acid generator. The present invention relates to: (A) a nonionic photo-acid generator characterized by being represented by general formula (1); and (Q) a resin composition for photolithography, which contains the nonionic photo-acid generator (A). [In formula (1), x represents an integer of 1 to 8; y represents an integer of 3 to 17; R represents a phenyl group, a biphenyl group or a naphthyl group, each of which may have a substituent (T); and L represents -O-, -S-, -SO-, -SO2-, -CO-, -COO-, -CONH-, an alkylene group having 1 to 3 carbon atoms, -CH=CH-, -C≡C- or a phenylene group.]
Provided is an epoxy resin curing accelerator for transparent materials, which does not contain water nor a halogen and an alkali metal that are impurities, and has excellent moisture resistance. This epoxy resin curing accelerator therefore does not erode a metal even under high temperature, high humidity conditions, is not susceptible to coloring when cured at high temperatures, and enables a cured epoxy product to undergo less discoloration over time. The present invention is an epoxy resin curing accelerator which is composed of a quaternary phosphonium sulfonate represented by general formula (1). (In the formula, each of R1-R5 independently represents a hydrogen atom, a linear or branched alkyl group having 1-4 carbon atoms or an alkoxy group having 1-4 carbon atoms; R6 represents an alkyl group having 1-16 carbon atoms; and X- represents an anionic residue of an organic sulfonic acid.)
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
Provided is a curing accelerator that is capable of reducing the melt viscosity and increasing the liquid flowability of an epoxy resin composition for semiconductor sealing and also capable of increasing the initial hardness during curing and improving mold release properties. The present invention is an epoxy resin curing accelerator which contains (A) a quaternary phosphonium compound represented by general formula (1) and (B) a phenolic resin that provides a phenoxide ion as an anion of the quaternary phosphonium compound. (In the formula, R1 to R5 each independently represent a hydrogen atom, a straight chain or branched chain alkyl group having 1-4 carbon atoms or an alkoxy group having 1-4 carbon atoms.)
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
60.
Sulfonium salt, photo-acid generator, and photosensitive resin composition
G03F 7/028 - Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
C07C 331/00 - Derivatives of thiocyanic acid or of isothiocyanic acid
Disclosed is a catalyst for the production of a polyurethane resin, which is capable of maintaining good fillability into a mold or good applicability to a base by maintaining sufficiently long working life (pot life) of a resin, while enabling rapid curing of the resin after a certain period of time. Specifically disclosed is a catalyst for the production of a polyurethane resin, which is characterized by being a salt (E) that uses a cycloamidine (C) represented by general formula (1) in combination with one or more acids selected from the group consisting of acids (A1) having pKa1 of 8-11 and one or more acids selected from the group consisting of acids (A2) having pKa1 of 4-6. The catalyst for the production of a polyurethane resin is also characterized in that the content of the acids (A1) is 0.2-0.8 mole per 1 mole of the cycloamidine (C), the content of the acids (A2) is 0.2-0.8 mole per 1 mole of the cycloamidine (C), and the content of acids (A1 + A2) is 0.8-1.2 moles per 1 mole of the cycloamidine (C). (In general formula (1), m represents an integer of 2-6, and a hydrogen atom in the methylene group may be substituted by an organic group.)
G03F 7/029 - Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
C07D 495/00 - Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
C07D 335/04 - Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
63.
PHOTOACID GENERATOR, PHOTOCURABLE COMPOSITION AND CURED PRODUCT OF SAME
Disclosed is an acid generator which contains a sulfonium salt having high i-line photosensitivity, excellent compatibility with cationically polymerizable compounds and excellent post-formulation storage stability. A photoacid generator comprises formula (1) and formula (2). (R1-R9 represent an alkyl, a hydroxyl, an alkoxyl, an alkylcarbonyl, an arylcarbonyl, an alkoxycarbonyl, an aryloxycarbonyl, an arylthiocarbonyl, an acyloxy, an arylthio, an alkylthio, an aryl, a heterocyclic hydrocarbon group, an aryloxy, an alkylsulfinyl, an arylsulfinyl, an alkylsulfonyl, an arylsulfonyl, a hydroxy(poly)alkyleneoxy, an optionally substituted amino, a cyano, a nitro, or a halogen, m1-m9 each represent the number of groups R1-R9, A1 represents S or SO, and X¯ represents a monovalent polyatomic anion.)
Provided is a catalyst for the production of polyurethane resin, which has a sufficiently long working life (pot life) and therefore exhibits excellent mold-filling properties and excellent applicability to a substrate, and which can achieve rapid cure after the lapse of a certain time. The catalyst is characterized by comprising a salt (E) which comprises a cycloamidine (C) represented by general formula (1), a weak acid (WA) having a pKa1 of 4 to 11, and a strong acid (SA) having a pKa1 of 2 or lower, and in which the content of (WA) is 0.2 to 0.8mol per mol of (C), the content of (SA) is 0.2 to 0.8 mol per mol of (C), and the content of (WA+SA) is 0.8 to 1.2mol per mol of (C). In general formula (1), m is an integer of 2 to 6; and each methylene hydrogen may be substituted by an organic group.
Provided is a photosensitive resin composition which is efficiently activated by light having a wavelength of from 350 nm to 500 nm and has excellent thick-film curability and deep curability. The photosensitive resin composition contains: (A) a photobase generator which is a compound represented by formula (1) or (2) and generates a base by irradiation of an active light ray; (B) a thermal radical polymerization initiator; and (C) a radical polymerizable substance. In formulae (1) and (2), Ar represents an aromatic hydrocarbon group or a heterocyclic group, which has at least one benzene skeleton and may be substituted by a halogen atom or the like; R1 and R2 each independently represent an alkyl group having 1 to 20 carbon atoms or the like; m represents an integer of 2 to 4; R3 to R5 each independently represent an alkyl group having 1 to 20 carbon atoms, a phenyl group, or a naphthyl group, which may be substituted by a halogen atom or the like; and X- represents an anion.
A sulfonium salt which is highly sensitive to i-line. The sulfonium salt is represented by formula (1). [In formula (1), R1 to R6 each independently represents an alkyl, hydroxy, an alkoxy, an alkylcarbonyl, an arylcarbonyl, an alkoxycarbonyl, an aryloxycarbonyl, an arylthiocarbonyl, an acyloxy, an arylthio, an alkylthio, an aryl, a heterocyclic hydrocarbon group, an aryloxy, an alkylsulfinyl, an arylsulfinyl, an alkylsulfonyl, an arylsulfonyl, a hydroxy(poly)alkyleneoxy, optionally substituted amino, cyano, nitro, or a halogen atom; m1 to m6 respectively indicate the number of R1s to the number of R6s; m1, m4, and m6 each is an integer of 0-5; m2, m3, and m5 each is an integer of 0-4; and X- represents a monovalent polyatomic anion.]
C08F 2/50 - Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
G03F 7/038 - Macromolecular compounds which are rendered insoluble or differentially wettable
G03F 7/039 - Macromolecular compounds which are photodegradable, e.g. positive electron resists
C08L 25/00 - Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
C08L 33/00 - Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters,; Compositions of derivatives of such polymers
C08L 61/00 - Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
67.
PHOSPHONIUM SALT, PHOTOACID GENERATOR, PHOTO-CURABLE COMPOSITION, AND CURED PRODUCT OF THE PHOTO-CURABLE COMPOSITION
Disclosed is a phosphonium salt which has sufficient photosensitivity to an active energy ray such as visible light, ultraviolet ray, electron beam and X-ray. Specifically disclosed is a phosphonium salt represented by formula (1). In the formula, R1 represents a group represented by formula (2); R2 and R3 independently represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X- represents a univalent polyatomic anion; R4 to R6 independently represent an alkyl group or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by –S-, -O-, -SO-, -SO2- or –CO-.
Provided is a photobase generator that can efficiently generate amines (tertiary amine and amidine) having high catalytic activity when exposed to light with wavelengths of 350−500nm (especially 400−500nm). The photobase generator is characterized by being represented by general formulas (1) or (2). Y+ is a quaternary ammonio group indicated by general formulas (3) to (5), and X- is a counter anion selected from among a borate anion, a phenolate anion, and a carboxylate anion.
C07C 211/63 - Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
C07D 453/02 - Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
69.
ACTINIC ENERGY RADIATION NEGATIVE-WORKING PHOTORESIST COMPOSITION AND CURED PRODUCT THEREOF
Disclosed is an actinic energy radiation negative-working photoresist composition that is free from any toxic element, has good thermal stability, and has excellent resolution. The composition comprises a salt of an oniumfluorinated alkylfluorophosphoric acid, as a cation polymerization initiator represented by formula (4), wherein A represents a group VIA or VIIA (CAS notation) element having a valence of m; m = 1 to 2, n = 0 to 3, R represents an organic group, D represents a formula (5), E represents a group having a divalent group, G represents -O-, -S-, -SO-, -SO2-, -NH-, -NR'-, -CO-, -COO-, -CONH, an alkylene having 1 to 3 carbon atoms or phenylene, a = 0 to 5, X- represents a formula (6), Rf represents an alkyl in which not less than 80% of hydrogen atoms have been substituted by a fluorine atom, and b = 1 to 5. The composition further comprises a cation-polymerizable compound, and a solvent.
To obtain a polymerization initiator (acid generating agent) having excellent power for initiation of cationic polymerization without containing arsenic or antimony.
Provided is a specific onium salt or transition metal complex salt of a fluorinated alkyl fluorophosphoric acid.
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
71.
METHOD FOR PRODUCING FLUORINATED SULFONIUM ALKYLFLUOROPHOSPHATE
Disclosed is a method for efficiently producing a fluorinated alkylfluorophosphoric acid salt of an aryl sulfonium at low cost without requiring an extremely excessive amount of acid. Specifically disclosed is a method for producing a sulfonium salt represented by the formula (3) below wherein an aryl compound Ar-H and a compound represented by the formula (1) below (wherein R1 and R2 respectively represent an optionally substituted hydrocarbon group or a heterocyclic group, or alternatively R1 and R2 are bonded together directly or via -O-, -S-, -SO-, -SO2-, -NH-, -NR’-, -CO-, -COO-, -CONH-, an alkylene having 1-3 carbon atoms or a phenylene and form an optionally substituted ring structure with R’ being a C1-5 alkyl or a C6-10 aryl) are reacted with each other in the presence of an acid represented by the formula (2) below (wherein Rf represents an alkyl in which 80% or more of hydrogen atoms are substituted by fluorine atoms, and a represents a number of 1-5) and a dehydrating agent.
A hardening accelerator for epoxy resins which comprises a salt formed from a diazabicyclic compound represented by the formula (1): (wherein one or more of the hydrogen atoms of the methylene groups may be replaced with an organic group; and m is an integer of 2-6) and a biphenylene-based phenolic resin represented by the formula (2): (wherein the hydroxyphenyl and biphenylene groups may be substituted by an organic group or a halogen atom; and n is an integer of 0-10) and/or a dicyclopentadiene-based phenolic resin represented by the formula (3): (wherein the hydroxyphenyl groups may be substituted by an organic group or a halogen atom; and n is an integer of 0-10).
C08G 59/40 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the curing agents used
73.
NOVEL FLUORINATED ALKYLFLUOROPHOSPHORIC ACID SALT OF ONIUM AND TRANSITION METAL COMPLEX
⏧PBOBLEMS] To provide a polymerization initiator having excellent ability to initiate a cationic polymerization, which does not contain arsenic or antimony. ⏧MEANS FOR SOLVING PROBLEMS] An onium salt or a transition metal complex salt of a specific fluorinated alkylfluorophosphoric acid.
C08G 59/68 - Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups characterised by the catalysts used
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