TW201132692A - Polyamide or polyimide resin composition containing phosphine oxide, and cured article thereof - Google Patents

Abstract

The present invention relates to a photosensitive resin composition containing a phosphine oxide compound (A) represented by the following formula (1), a polyamide or polyimide resin composition, which is (B) component, obtained by bringing a diamine compound and a tetrabasic acid dianhydride into reaction, and a photosensitive agent (C) or a photo-polymerization initializer (D). The cured films obtained from the composition have excellent flame retardance, thermal resistance and humidity resistance, and excellent electrically insulation properties.

Description

[Technical Field] The present invention relates to a hardened resin composition of a phosphine oxide compound which uses a reactive compound which can be polymerized in various polymer materials for the purpose of incombustible polymer materials. . Specific examples thereof include materials for film formation, solder resists for printing (wiring circuit) substrates, other resist materials for performing inspection, adhesives, lenses, displays, optical fibers, optical waveguides, and holograms (ho 1 ogram) and so on. [Prior Art] Attempts have been made to make flame retardancy in a molded article, a material for forming a film, and the like. In the past, although it has been widely used as a flame retardant material of a dentate-based compound represented by a desert compound, it has been avoided in recent years due to an increase in environmental awareness. Research is being conducted on the use of flame retardant materials that can replace such breaking compounds. Usually, the filling compound is used alone in the resin composition or the like, but the hardening effect is not obtained due to the hardening of the resin composition or the bleed out over time (bieed Qut), and the heat and electrical properties of the cured product are obtained. Or concerns such as reduced mechanical properties. In order to solve such problems, it has been demanded to develop a reactive flame retardant which adds a filler compound to a skeleton such as a resin. Among them, as a polymerizable (meth)acrylic monomer containing phosphorus, a compound of a phosphoric acid type represented by the formula (2) is known (Patent Document υ).

322665 4 201132692 (wherein ^"^ means that the number of carbon atoms is ..., R4 represents a nitrogen atom or a sulfhydryl group ==, or may be different.) R !, r 2 may be the same as each other, and it is also expected to give several adverse effects. For example, ^(6) raw base) promotes hydrolysis by riding a metal such as a metal into a hardened material, or promotes it to be used for a circuit board for a long period of time, etc. The purpose of the circuit is to protect the circuit: acid base; 2. For use in long-term tree protection » - V inch <hardener liquid combination' will be used before use. At this time, in the _ and the product contains more acidic sputum, 彳 合 合 保存 保存 保存 保存After the application or after the application to the development, the reaction of the hardener is promoted, and there is a problem that it cannot be imaged. The phosphoric acid type compound which is crosslinked with the epoxy resin is high in humidity, and the condition: it will hydrolyze. Therefore, the (4) special money test is not suitable. In the case of the fluorinated phosphine having a hydroxyl group having excellent heat resistance and moisture resistance, an epoxy group is introduced and an ethylenically unsaturated group is introduced. • In the art, there is a problem that the phosphine oxide bleeds out from the resin composition when there is no sensitivity when the active energy ray is hardened. In order to impart flame retardancy to the resist material, it is also difficult to formulate reactive and inorganic extender pigments. In the resist material used for the flexible circuit board, since high flexibility is required, it is difficult to impart flame retardancy when a large amount of the body pigment is added. Patent Document 3 discloses a phosphine oxide compound (A) used in the present invention, and 322665 5 201132692 discloses a resin composition obtained from the compound (A) and a photopolymerization initiator. Patent Document 4 discloses a reactive compound (B) having two or more active energy ray-reactive functional groups (specifically, 'epoxy compound) and a photopolymerization initiator. A curable resin composition. The patent documents do not disclose a resin composition containing the phosphine oxide compound (A) and the polyamine compound or the polyamidiamine compound. Many photosensitive compositions using a polyamine compound or a polyimine compound are known. However, it has not been known to use a photosensitive composition which can satisfy the flame retardancy and high reliability and which is a polyamine compound or a polyimide compound. In order to use a resin composition of a polyamine compound or a polyimide compound, an alkali solubility can be patterned by development, and a carboxylic acid, a sulfonic acid, a phenolic hydroxyl group, etc. are usually introduced into a lunar frame, and another In order to improve solvent solubility, a method of introducing an aliphatic skeleton is generally considered, but the susceptibility of any of these methods may be lowered. [PRIOR ART DOCUMENT] [Patent Document 1] JP-A-2000-38398 [Patent Document 2] Japanese Laid-Open Patent Publication No. Hei No. Hei. [Problem to be Solved by the Invention] The object of the present invention is to provide the above-mentioned photosensitive phosphine oxide 6 322665 201132692 and In the photosensitive resin composition of the polyamine compound or the polyimine compound, the above phosphine oxide compound does not hydrolyze under high humidity and heat conditions, and the electrical property is not applicable to the specificity test, and is obtained. A resin composition of a cured layer having superior heat and moisture resistance is formed. [Means for Solving the Problem] The inventors of the present invention have conducted intensive studies on a photosensitive wax composition having both photosensitivity and excellent insulation properties over time, and have found a specific structure of a phosphine oxide compound. The above problems can be solved by the composition of (A) and polyglycine (polyglycine) or its imine, and thus the present invention has been completed. That is, the present invention relates to the following (1) to (15). (1) Contains the following formula (1)

(wherein, R represents a ruthenium atom or a fluorenyl group), the phosphine oxide compound (A), and the (B) component, a polyamine compound or a polyazide obtained by reacting a diamine compound with a tetrabasic acid dianhydride. A resin composition of an amine compound. (2) Contains the following formula (1)

A phosphine compound (A) represented by the formula (wherein R represents a hydrogen atom or a methyl group) and a polyamine compound obtained by reacting a diamine compound with a tetrabasic acid dianhydride as a component (B) of 322665 7 201132692 Or a photosensitive resin composition of a polyimine compound and a sensitizer (C) or a photopolymerization initiator (E). (3) The photosensitive resin composition according to the above (2), which comprises the gasified scaly compound (A), the component (B), and a sensitizer (〇) (4) the photosensitive material described in (1) or (2) above. The resin composition is a reactive compound (D) and a photopolymerization initiator (8) having two or more active energy ray-reactive functional groups in the phosphine oxide compound (A), the above-mentioned component (B) &amp; (5) The photosensitive resin composition according to the above (4), which contains a 2- to 6-functional (meth) acrylate compound as the reactive compound (D). (6) The above (4) or (5) The photosensitive resin composition according to the above-mentioned (4) to (6) is an acid-modified (methyl group) containing a polyfunctional epoxy compound as a curing agent. An acrylate compound is used as the reactive compound (D). (8) The resin composition according to any one of the above (1) to (?), which contains the phosphine oxide compound (A) in an amount of from 1 to 95% by mass and (Β) a component of from 5 to 99. quality%. (9) The resin composition of the above (1), or the photosensitive resin composition according to any one of the above (2) to (8). (10) The resin composition of the above (1), or the photosensitive resin composition according to any one of the above (2) to (8). (11) A photosensitive resin composition of the above (1) resin composition or any one of the above (2) to (8) which is an electrically insulating material. The resin composition of the above (1) or the photosensitive resin composition according to any one of the above (2) to (2) is a solder resist composition. (13) A cured layer of a resin composition or a cured layer of a photosensitive resin composition according to any one of the above (2) to (8). (14) A resin composition according to the scope of claim (1) The cured product of the photosensitive resin composition according to any one of the second to eighth aspects of the invention. [Effect of the invention] The present invention relates to high-humidity heat conditions. The phosphine oxide compound is not hydrolyzed, and is not applicable to a reliability test such as electrical characteristics, and can form a resin composition of a cured layer having excellent heat resistance and moisture resistance. The present invention does not use the above phosphine oxide compound in a large amount. In addition, it has sufficient flame retardancy, and it is possible to obtain a photosensitive composition which is excellent in heat resistance and moisture resistance and has good electrical insulating properties. The cured product of the photosensitive resin composition of the present invention is sufficiently satisfied. Metal dense The resin of the present invention is excellent in flame retardancy and heat resistance, and has excellent wettability and is excellent in electrical insulation and long-term reliability. Therefore, the photosensitive resin composition of the present invention is suitable as a material for forming a film. A composition for solder resist, a resist material which can be inspected for development, an adhesive, a lens, a display, an optical fiber, an optical waveguide, a hologram, etc. in the production of a printed circuit (wiring circuit). [Embodiment] Hereinafter, the present invention is made. DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a polyamidoamine compound (B-1) obtained by reacting a diamine compound and a tetrabasic acid dianhydride with the oxidized scaly compound (4) represented by the formula (1) and 322665 9 201132692 as a component (B). (Resin composition of the polyimine compound (B_2)) The phosphine oxide compound (A) represented by the formula (1) used in the present invention is known in the above Patent Document 3, and is known. It is obtained by reacting an alcohol compound of the formula (3) with a carboxylic acid compound having an ethylenically unsaturated group in the molecule (specifically, (meth)acrylic acid).

The alcohol compound represented by the formula (3) can be obtained by reacting a phosphorus-containing compound having at least one active hydrogen in the molecule of the formula (4) with furfural. As the compound, a commercially available product can be used, and for example, HCA (trade name) manufactured by Sanko Co., Ltd. is listed.

The carboxylic acid compound having an ethylenically unsaturated group in the molecule for producing the phosphine oxide compound (A) used in the present invention is a reactivity imparting an active energy ray in the phosphine oxide compound (A). Specifically, acrylic acid or mercaptoacrylic acid is cited. The phosphine oxide compound (A) used in the present invention can be produced by dehydrating condensation of the above alcohol compound with the above-mentioned mild acid compound in the presence of an acid catalyst to prepare 322665 10 201132692. The acid catalyst to be used may be arbitrarily selected from known ones such as sulfuric acid, methanesulfonic acid, p-formylsulfonic acid, etc., and is used in an amount of 0.1 to 10 mol%, preferably Mo, for the monocarboxylic acid compound. ear%. An azeotropic solvent can be used for the water formed by the distillation reaction. The azeotropic solvent is a solvent having a boiling point of 60 to 13 Torr, a point 'a solvent which can be easily separated from water, and preferably an aromatic hydrocarbon such as a hexane or an aromatic hydrocarbon such as benzene or toluene. An alicyclic hydrocarbon such as hexane. The 佶θ θ ° and the 篁 are arbitrary, and preferably 10 to 70% by mass based on the reaction mixture. The reverse U can be in the range of 60 to 130 ° C, but it is preferably from 75 to cut from shortening the reaction time and preventing the polymerization. c proceed. In the case of b +, commercially available (fluorenyl) acrylic acid or the like is generally added with a fluorene-based oxime and a polyaddition agent, but a polymerization inhibitor may be added during the reaction. The polymerization inhibitors are preferably gas rolls, p-methoxyphenylhydrazine, 2,4-difluorenyl groups, second butyl phenol, 3-hydroxy thiophenol, p-benzene rolls, 2, 5 - Dihydroxy-p-benzene stick, phenazine, and the like. 01至该质量质量。 The amount of the reaction mixture is 0.1 to 1% by mass. In the present invention, the polyamine compound (B-1) used as the component (B) may be any polyamine compound (B-1) which can be obtained by reacting a diamine compound with a tetrabasic dianhydride. use. Further, any known polyimine compound can be used as the polyimine compound (B-2). The polyimine compound (B-2) can be usually obtained by a dehydration ring-closure reaction of the above polyamine compound (B-1). The component (B) is preferably a solvent-soluble one which can form a film or layer of flame retardant 11 322665 201132692 by the resin composition of the present invention. In the present invention, by using the polyamine compound (B-1) or the polyamidimide compound (B-2) in combination with the phosphine oxide compound (A) represented by the above formula (1), it is possible to obtain flame retardancy and It is a high-reliability toughness hardener for electrical and electronic parts. That is, the combination of the indenyl or quinone imine group in the component (B) and the monofunctional phosphine oxide compound (A) constitutes a strong crosslinked structure. As a result, although the phosphine oxide compound (A) of the formula (1) itself is easily hydrolyzed, and the hydrolysis operation or bleeding out of the phosphine oxide compound (A) is suppressed, in the cured product of the resin composition of the present invention Gives long-term stability to flame retardancy and insulation. Therefore, the resin composition of the present invention can be used for an electronic or electrical component or the like, and a cured layer having high reliability can be imparted. In the present invention, when the molecular weight of the polyamidamine compound (B-1) or the polyamidimide compound (B-2) is within a certain range, the resin composition of the present invention is excellent in spreadability and solubility. Therefore, it is preferred. In general, the molecular weight of the polyamidamine compound (B-1) or the polyamidimide compound (B-2) is from 8,000 to 150,000 to 1,500 to 8,000 in the weight average molecular weight. range. If the molecular weight is too large, the spreadability, solubility, or developability may deteriorate. Further, if the molecular weight is too small, the obtained cured film becomes weak. The adjustment of the molecular weight of the polyamine compound (B-1) or the polyamidiamine compound (B-2) can be controlled by the molar ratio of the diamine to the tetrabasic dianhydride used. The molar amount of the molar amount of the diamines/the amount of the quaternary acid dianhydride is from 2 to 0.5, preferably from 1.1 to 0.9, which is a preferred molecular weight. In the present invention, the diamine compound used has two amine groups in one molecule, and is combined with a tetrabasic acid anhydride described later to form a polyamidated 12 322665 201132692 compound or a polyimine compound ( The ingredients of B) are used. The diamine compound to be used is not particularly limited and may be appropriately selected in accordance with the purpose of the resin composition of the present invention. Specific examples include linear aliphatic diamines such as ethylenediamine, propylenediamine, hexamethylenediamine, octadecylamine, and ninthylenediamine, preferably a linear chain of C5 to CIO. a cyclic aliphatic such as aliphatic diamine, cyclohexanediamine, isophoronediamine, norbornene diamine, dicyclohexanediamine, tricyclodecanediamine, diaminodicyclohexylmethane Monocyclic aromatic diamines such as diamines, phenylenediamine, dimethylphenylenediamine, biphenylenediamine, chlorin, bis(aminophenyl)ether, bis(methylamine) Phenyl)ether, bis(hydroxyaminophenyl)ether, 2 (carboxyaminophenyl)ether, bis(aminophenyl)sulfone, bis(aminophenyl)decane, bis(aminobenzene) a bicyclic aromatic diamine such as propane, bis(aminophenyl) sulfide, bis(aminophenyl)hexaphenanthine or naphthyldiamine, bis(aminotransphenyl)benzene, Tricyclic aromatic diamines such as bis(hydroxyaminophenoxy)benzene, bisaminophenyl bis[[aminophenoxy]phenyl]propane, bis[[aminophenoxy]benzene Polycyclic aromatic diamines such as sulfones and derivatives thereof. Other, other diamines such as organic quinone diamine may also be used. When a linear moon-shaped aliphatic monoamine, a cyclic aliphatic diamine, a bicyclic aromatic diamine, or a tricyclic aromatic diamine is used in the hair, the resin composition of the present invention is provided. The hardened material combines high levels of softness and flame retardancy. The preferred diamines are linear aliphatic diamines, and the aromatic ring is a benzene ring bicyclic or tricyclic aromatic diamine. More specifically, C5 to CIO linear aliphatic diamines such as hexamethylenediamine, octanediamine, dodecanediamine, 322665 13 201132692 2 amine-substituted benzene rings are directly bonded or bonded A bicyclic aromatic diamine to which a biphenyl group (preferably -S〇2-, -0-, -C(CF3)2-, etc.) is bonded or a tricyclic aromatic diamine further in a space with a benzene ring. The acyclic ring substituted with an amine group may be substituted with a hydroxyl group or the like in addition to the amine group. For example, biphenyldiamine, bis(aminophenyl)ether, bis(hydroxyaminophenyl)ether, bis(aminophenyl)anthracene, bis(hydroxyaminophenyl)sulfone, bis(amine group) Stupid) hexafluoropropane, bis(hydroxyaminophenyl) stupid, bis(transaminophenoxy)benzene, and the like. From the viewpoint of the flame retardancy and softness of the cured layer, it is preferred that the crosslinking group is a _s〇2_ diamine, more preferably a bis(aminophenyl) fluorene. The tetrabasic acid dianhydride used in the present invention is a dianhydride of a tetracarboxylic acid compound having four carboxyl groups in the oxime molecule. These are combined with the above-mentioned diamine compound and can be used as a component for constituting a polyamine compound or a polyimine compound. The tetrabasic acid dianhydride to be used is not particularly limited and may be appropriately selected in accordance with the purpose of the resin composition of the present invention. Specific examples thereof include monocyclic aromatic quaternary heptaic anhydride, diphenyltetracarboxylic anhydride, benzophenone tetracarboxylic dianhydride, naphthyltetrahydro acid if, and the like. Phenyl (tetra) tetrawei wild, diphenyl turning (four) liver, ethylene glycol double-biased diacid liver, hexanediol double-biased three-fold, diol dipyridinic acid y = (for example, hexanediol dipyridamole) a polycyclic aromatic tetrabasic acid such as a dicyclic aromatic tetrabasic acid dianhydride such as a bis-benzoic acid benzoic acid, a di-p-dicarboxylic acid g anhydrate, or a di-trimethylene trianhydride The dianhydrides and the butadiene tetrahydroanhydride may also be used to pass through the nuclear hydrogenation cyclic anhydrides. In the present invention, when it is used in the present invention, when a bicyclic s-aromatic tetrabasic acid or a weathering compound is used, it can have both high-level flexibility and flame retardancy. 322665 14 201132692 "Difficult tetrabasic acid two needles can be exemplified by: 2 benzene rings having a carboxylic acid needle group directly bonded or crosslinked groups (preferably _s 〇 2_, _ 〇 _, _ with CFA one) , _(〇CH2CH2)n-, etc.) linked bicyclic aromatic tetrabasic acid II. More preferably, the tetrabasic acid dianhydride may be, for example, diphenyltetracarboxylic anhydride or diphenylsulfonetetracarboxylic anhydride. Preferably, the (IV) amine compound (B-1) is a polyamine compound obtained by reacting the above-mentioned aromatic ring with a bicyclic or tricyclic aromatic diamine of a benzene ring and a bicyclic aromatic tetrahydro acid. a polyfluorene obtained by directly combining a dicyclic ring diamine with a bicyclic aromatic tetrabasic acid, or a compound bound by a muscle-crosslinking group or a -G-crosslinking group. An amine compound, preferably a compound in which at least one of a bicyclic aromatic diamine and a bicyclic aromatic tetrabasic acid dianhydride is directly bonded or bonded with a -S〇2-crosslinking group, for example, as a diamine component Using a bicyclic aromatic diamine (for bis (amine) ruthenium (IV)) or a bicyclic aromatic tetrabasic dianhydride (specifically diphenyl sulfonium tetracarboxylic anhydride) The polyamine compound (B_2) is preferably the polyimine compound (B-2) obtained by dehydration ring closure from the above preferred polyamine compound (B-1). In the resin composition of the present invention, the component (B) may be any one of the polyamine compound (B-1) and the polyamidiamine compound (B_2), and it is preferably determined according to the purpose. For example, in the case of a positive type, when the reliability under high temperature and high humidity (12 (TC, 85% relative humidity) does not need to be so long, the component (B) is used as the polyamine compound (B'l), It can be used as a resin composition with excellent imaging properties and can be obtained from a hardened layer with superior flame retardancy. Even if it is a little imaged 15 322665 201132692 Sex 'after as long as possible, at high temperature and high humidity (12〇 When high reliability is required in the case of ΐ and 85% relative humidity, the (B) component can be used as the polyimine compound (B-2) to obtain a long-term reliability which is flame retardant and has a remarkable superiority. Hardened layer. Also, if it is a negative type, even if the (B) component is The polyamine compound (B-1) or the polyimine compound (B_2) can achieve superior image development, flame retardancy and high reliability at high temperature and high humidity. The above diamines are reacted with a tetrabasic acid dianhydride to obtain a polyamidamine compound (B-I). The reaction can be carried out by a generally known method and reaction conditions. Further, the polyamine compound (B-ι) The dehydration condensation reaction can be carried out to form a polyimine compound (B-2). The reaction can also be carried out by a generally known method and reaction conditions. Synthesis of a polyamine compound (B-I) and a polyamidene compound ( When b_2), a suitable solvent can be used. The solvent which can be used is not particularly limited as long as it can dissolve the obtained polyamine compound (B-I) and the polyimine compound (B_2). Specifically, the polarity _ is used, for example, an amine-based solvent such as dimethyl ketoamine, dimethyl ethanoamine, N_; ketone, an ester solvent such as butyl s-butyl, or butyl diethylene glycol. B, alcohol is a 'valley. Among them, a ketone-based solvent or a S-based solvent is more preferable, and a ketone solvent such as N-methylpyrrolidone or butyrolactone is preferred, and N-methylpyrrolidone is preferred. For the entire composition (100% by mass) of the present invention, (A) component and (B) 322665 16 201132692 - each component of the component '(A) component (phosphorus oxide compound (A)) is from 1 to 95% by mass %. The component (B) (polyamine compound or polyimine compound (Β-2)) is 5 to 99% by mass, and is preferably 5 to 99% by mass, preferably 8 to 95% by mass. Further, the proportion of the entire composition of the present invention is not specified as the ratio of the total amount of the composition. The sensitizer (C) which can be used in the present invention is added for the purpose of inducing and reacting with the active energy ray, and for the purpose of changing the characteristics of the resin composition, specifically, the positive sensitizing property. For example, according to the active energy ray irradiation portion and the non-irradiation portion of the resin composition of the present invention, the solubility in the solvent or the alkaline aqueous solution can be changed, and patterning or the like can be performed. For example, by using the photosensitive agent (C)' which generates an acidic group with irradiation of light, the solubility of the illuminating portion to the developing solution of the alkaline aqueous solution or the like is improved, and the non-irradiating portion is still lacking in the developing liquid. Solubility imparts a so-called positive photosensitive property. Specifically, f ′ usually uses a quinonediazide compound as a positive sensitizing property. These can be obtained by subjecting a polyhydroxy compound having a plurality of phenolic hydroxyl groups to an esterification reaction with a naphthoquinonediazidesulfonic acid vapor compound or the like. For example, 1,2-naphthoquinone-2-diazide-5-sulfonate, anthracene, 2-naphthoquinone-2-diazide-4-sulfonate, 2, 3,4-three Hydroxybenzophenone and 6-diazo-dihydro-5-keto-naphthalene acid vinegar of 2,3,4,4-tetrahydroxydibenzophenone. Specific product names include PC_5, NT-200, 4NT-300 manufactured by Toyo Synthetic Industrial Co., Ltd., or DTEP-300 and DTEP-350 manufactured by Dade Chemical Co., Ltd. When the sensitizer (C) is used, it may be in the range of 0.5 to 50% by mass, preferably 1 to 30% by mass, more preferably 5 to 30% by mass in the entire composition (just mass 17 322665 201132692%) of the present invention. The scope is added as appropriate. In the present invention, a reactive compound having two or more active energy ray-reactive functional groups in one molecule may be used, and the curing reaction is carried out by irradiation with an active energy ray, so that the illuminating portion is insolubilized in the developing liquid. The non-irradiation portion can maintain the developability (solubility in the developing solution) of the developing solution (alkaline aqueous solution or organic solvent) because the curing reaction is not performed. Therefore, the reactive compound (D) imparts a negative photosensitive property to the resin composition of the present invention. The reactive compound (D) having two or more active energy ray-reactive functional groups in one molecule is used in combination with the above phosphine oxide compounds (A) and (B) to impart excellent flame retardancy and strong hardening. Things. Since there are two or more active energy ray-reactive functional groups in one molecule, a strong cross-linking structure is formed in combination with the (B) component and a monofunctional phosphine oxide compound (A), and the phosphine oxide is inhibited. The hydrolysis operation or exudation of the compound (A) can lead to long-term stability and flame retardancy and reliability. In the present invention, the 'active energy ray-reactive functional group is a functional group which can form a cross-linking bond by a reaction via an active energy ray. For example, a functional group which reacts by a radical generated by irradiation with an active energy ray may, for example, be a polymerizable unsaturated bond such as a (meth)acrylic group, a vinyl group or a vinyl ether group. An epoxy group such as an epoxy group or an oxetanyl group which is reacted by a cation generated by irradiation of an active energy ray, or an unsaturated group such as a vinyl ether group. In addition, the 'molecular group contains a glycidyl group (fluorenyl group) (iv) acid S, etc., and the functional group of both the radical and cation groups 322665 201132692 • Also, it has two or more active energies in one molecule. Linear Reactive Official. The reactive compound (D) of the energy base is used. However, in the present invention, an epoxy compound is used as a curing agent as described later. However, in many cases, the curing agent is usually used in combination of only one set until use, and is added to the present invention at the time of use. In the resin composition, the epoxy resin used as the curing agent is not contained in the reactive compound (D) in the resin composition of the present invention. The reactive compound (D) having two or more (fluorenyl)acrylic groups may, for example, be a (meth)acrylic acid ester having 2 to 6 (fluorenyl)propionic acid groups. Specifically, 'may be exemplified by butanediol di(indenyl) acrylate, hexanediol di(meth) acrylate, neopentyl glycol di(meth) acrylate, decanediol II ( Mercapto) acrylate, ethylene glycol di(meth) acrylate, diethylene ethyl di(meth) acrylate, polyethylene glycol bis(indenyl) acrylate, tris(fluorenyl) Acetyradyloxyethyl isocyanate, polypropylene glycol di(meth)acrylate; adipic acid epoxy di(methyl) acrylate, biguanide ethylene oxide di(methyl) Acrylate, hydrogenated bisphenol ethylene oxide (meth) acrylate, bisphenol bis(indenyl) acrylate; ε ~ caprolactone modified trans-trimethyl acetic acid neopentyl glycol di(indenyl) Acrylic acid S曰, £~caprolactone modified dipentaerythritol hexa(meth) acrylate, ε_caprolactone modified dipentaerythritol poly(meth) acrylate; dipentaerythritol Dimethyl pentaerythritol poly(2 to 6)(mercapto) acrylate, trimethylolpropane tri(meth)acrylate and trishydroxyethylpropane tris(decyl)propene oxime (meth)acrylate ester And such ethylene oxide adducts; pentaerythritol tri(meth)acrylate and its ethylene oxide adduct; pentaerythritol tetra(meth)acrylate and its ethylene oxide Additives; etc. (曱基) 322665 19 201132692 Acrylic acid. Examples of the reactive compound (D) having two or more vinyl groups include vinyl ethers such as ethylene glycol divinyl ether, styrenes such as divinylbenzene, and triallyl isocyanuric acid, and tridecylene. Other reactive compounds such as propyl isocyanurate, etc. The reactive compound (D) having two or more cyclic ether groups is usually not particularly limited as long as it has an epoxy group or an oxetanyl group. limit. Examples thereof include alkyl diglycidyl ethers such as butyl diglycidyl ether, bisphenol A diglycidyl ether, and 3,4-epoxycyclohexyldecyl-3,4-epoxycyclohexanecarboxylate. (Combined Carbide Co., Ltd. manufactures Cyracure UVR_611〇), 3, 4-epoxycyclohexylethyl_3, 4-epoxycyclohexanone, Ethyl Oxide ("ELR-4206" manufactured by Union Carbide Co., Ltd.), limonene dioxide ("Celloxide 3000" manufactured by Daicel Chemical Co., Ltd.), allyl cyclohexene dioxide, 3, 4-Epoxy-4-methylcyclohexyl-2-propanyl oxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) Cyclohexene-inter-secondic calcination, bis(3,4-epoxycyclohexyl)adipic acid vinegar ("Cyracure UVR-6128", etc. manufactured by Union Carbide Co., Ltd.), double (3,4- Epoxycyclohexyldecyl) adipate, bis(3,4-epoxycyclohexyl)ether, bis(3,4-epoxycyclohexylmethyl)ether, bis(3,4_ ring Oxycyclohexyl) diethyl onium oxide and the like. Other 'as the reactive compound (D), it is also possible to use a urethane (methyl) propionate having a combination of a (meth)acrylic group and a urethane in the same molecule, and the same in the same molecule. Polyester (meth) acrylate having a complex number of (meth) acrylate groups and ester bonds, and epoxy groups derived from epoxy resins having a plurality of 322665 20 201132692 • (meth) acrylate groups (Methyl) acetonide vinegar, such as a reactive oligomer used in combination or a compound having two or more active energy ray-reactive functional groups which impart an acid value. The urethane (meth) acrylate which can be used as the reactive compound (D) in the present invention is a sulfonate containing a thiol group and a polybasic oleic acid vinegar, and if necessary, other A reactant for alcohols. For example, a hydroxyalkyl (mercapto) acrylate such as hydroxyethyl (mercapto) acrylate, hydroxypropyl (meth) acrylate or hydroxybutyl (fluorenyl) acrylate, or glycerol mono(meth)acrylic acid Vinegar, glycerol di(methyl)(tetra) acid glycerol (mercapto) propane vinegar, neopentyl alcohol di(meth) acrylate, neopentyl alcohol tris(decyl) acrylate, dixin Tetraol (indenyl) acrylic acid, etc. (methyl) propyl acetoacetate with toluene diisocyanate, hexamethylene diisocyanate, trimethyl hexamethyl decyl diisocyanate @旨, isophorone diisocyanate, raw borneol diisocyanuric acid vinegar, xylene diisocyanate g, hydrogenated dimethyl benzene diisocyanate vinegar, dicyclohexyl sulphide The isocyanic acid is reacted with a polyisocyanate such as a trimeric isophthalic acid or a dimeric reaction product to form a glandular (meth)acrylic acid. The epoxy group (fluorenyl) acrylate vinegar which can be used as the reactive compound (D) in the present invention is a compound having an epoxy group and a acetoacetic acid compound of (meth)acrylic acid. For example, a clear varnish type epoxy (mercapto) acrylate, a cresol novolac type epoxy (meth) acrylate, a trihydroxy phthalate type epoxy group (fluorenyl) acrylate , dicyclopentadiene phenol type epoxy (meth) acrylate, bisphenol-A type epoxy (meth) acrylate, bisphenol oxime type epoxy (meth) acrylate, diphenol type Epoxy (fluorenyl) acrylic acid 322665 21 201132692 Ester, bisphenol-A novolak type epoxy (meth) acrylate, epoxy (meth) acrylate containing naphthalene skeleton, glyoxal epoxy The base (fluorenyl) acrylic acid S曰, the heterocyclic epoxy group (fluorenyl) acrylate, and the like, and the anhydride-modified epoxy propylene acid S. In the above, the reactive compound (D) may be a radically curable compound having a (fluorenyl)acrylic group, preferably a compound having a plurality of (fluorenyl)acrylic groups (also referred to as poly(fluorenyl). An acrylate compound) containing 2 to 6 (preferably) 3 to 6 (fluorenyl) acrylate compounds. Preferred examples of such compounds include: pentaerythritol poly(2 to 4) (meth) acrylate, dipentaerythritol to 6) (meth) acrylate, and the ε-into An ester adduct or an epoxy Ethylene adduct or the like. The number "poly" (2 to 4) and so on after "poly" indicates the number of "poly". Further, in the present specification, the (meth) acrylate is at least one selected from the group consisting of methacrylate and acrylate. The same performance is used in the same sense. The (meth) acrylate compound (also referred to as a 2 to 6 functional fluorenyl acrylate compound) having 2 to 6 of the above (meth) acrylate groups may, for example, be modified by ε-caprolactone. Dipentaerythritol hexa(meth) acrylate, caprolactone-modified dipentaerythritol poly(meth) acrylate, dipentaerythritol hexa(meth) acrylate, etc. (2 to 6) (meth)acrylic acid S曰, dimethylolpropane tri(meth)acrylate and trishydroxyethylpropane di(meth)acrylate and the ethylene oxide addition thereof Neopentyl alcohol tris(meth) acrylate and its ethylene oxide calcined adduct; pentaerythritol tetra(meth) acrylate and its ethylene oxide adduct. The above reactive compound (D) is a compound having 2 to 6 functional (meth) propylene 322665 22 201132692. The acid ester compound preferably has a content of about 50 to 100% by mass based on the total amount of the component (D). More preferably, it is 80 to 100% by mass, and the remainder is the above-mentioned reactive compound (D) other than the above. The aspect in which the component (D) is all of the polyfunctional (meth) acrylate compound is one of preferable embodiments. Further, in the case of the cation hardening type, since the epoxy group is reacted via a small amount of acid derived from the vaporized phosphine compound (A), it is necessary to form a two-liquid mixing type. The reactive compound (D) having two or more active energy ray-reactive functional groups can impart an acid value. For example, when the exposed portion is crosslinked by a crosslinking reaction using light, and the alkaline aqueous solution is used as a developing solution to elute the non-exposed portion and patterned, the alkaline aqueous solution development method can be used, and the acid value can be used by using The reactive compound (D) is one of the components (D), and the non-exposed portion is eluted through an aqueous test solution.

At this time, the acid value of the reactive compound (D) is usually from 30 to 15 MPa. K 〇 H / g ' is preferably from 60 to 11 〇 mg.KOH / g. When the acid value at this time is less than 3 〇 mg·KOH/g, the alkaline aqueous solution developability of the active energy ray-curable resin composition of the present invention is remarkably lowered, and in the worst case, there is a concern that development is impossible. Further, if the acid value exceeds 150 mg.KOH/g, the developability becomes too high and it is not easy to pattern. The reactive compound (D) which imparts an acid value is a compound which combines an active group having an active ruthenium-ray-reactive functional group and an acidic group such as a slow group or a pendant group. Columns are exemplified by acid-modified epoxy (meth) acrylate or acid-modified urea-fired (fluorenyl) acetoacetic acid-modified (fluorenyl) acrylate. The acid-modified (fluorenyl) acrylate compound is preferably an acid-modified epoxy (meth) acrylate compound in the present invention. 322665 23 201132692 The acid-reactive compound (D) can be obtained by, for example, adding an acid anhydride or the like to the above-mentioned reactive compound (D) to form an acid anhydride addition reaction type compound. Or a compound having an active energy ray-reactive functional group in a copolymerization group having a monomer such as (mercapto)acrylic acid or vinyl phenol, etc.: a method of polymerization (copolymer) When the compound is obtained). The acid salt of the reactive compound (D) which imparts the above acid value is not particularly limited, and may be used as long as it has an acid field structure in the molecule. , heat resistance, physical properties, and other superior succinic anhydride, phthalic anhydride, tetra-o-o-benzene, hydrolysis-resistant hexahydrophthalic acid needle, itaconic acid liver, 3-methyl, tetrahydrogen, needle, 4-A The above-described samaric anhydride in the reactive compound (D) which imparts the above acid value, is a hexahydrophthalic anhydride, a benzoic acid or a male. a reactive compound, which has a compound of the county, a modified pentylene pentoxide triacrylate, an acid modified phenol novolak type, a new acrylate, an acid modified cresol novolak type ring Oxygen (meth) (methyl) "phenylmethyl" (methyl) her;:, = -% pentane di(tetra) epoxy (meth) acrylate, acid modified double enzyme epoxy (Methyl)acrylic acid vinegar, acid modified bis(tetra) type epoxy group (designed, acid modified di-p-type epoxy (methyl) acetoacetate, acid modified; raw bismethyl) (tetra) acid 3 Alkyl (meth)propionic acid-containing, acid-modified oxalic acid-type epoxy acid-modified heterocyclic epoxy group (methyl) (10) acid vinegar, (IV) I A 31% oxy (methyl) propionate or the like. 322665 24 201132692 In the present invention, the acid anhydride-formed reactive compound (D) is preferably an acid-modified epoxy group (methyl) as described above. Acrylic vinegar. Acid-modified epoxy (meth) acrylate is more preferably an acid-modified diphenol-type epoxy (meth) acrylate. When using this compound, it can exert a more modified ring than other acids. Oxyl (methyl) Acrylate is more flame retardant. When the above reactive compound (D) contains an acid-modified (meth)propionic acid brewing compound, the acid-modified (mercapto) acrylate is contained in the total amount of the component (D). The compound is in the range of 30 to 80% by mass, preferably 50 to 80% by mass, and the remainder is the above-mentioned reactive compound (D) other than the above-mentioned reactive compound (D) which imparts the above acid value. The copolymer type compound, specifically, may be exemplified by a polymer or copolymer obtained by polymerizing or copolymerizing a (meth)acrylic acid containing a carboxylic acid or a vinylphenol having a phenol group alone or in combination with other monomers. Glycidyl (meth) acrylate or isocyanatoethyl (mercapto) acrylate grafted to introduce a compound of the energy-reactive functional group. The above anhydride addition compound and copolymer The type compound is suitably used depending on the use or development form, and any one of them is an acid solution which can be used for imparting an acid value to a resin, and any one of them can be used equally in the present invention. In the case of applications requiring hardness or long-term reliability such as electrical insulating materials, 'the acid anhydride having a high degree of freedom in resin structure before acid anhydride addition is preferred'. When softness, film forming property or price is required, The copolymer type is preferred. Among them, the 'functional group of the acid value' is more preferred than the phenol group. Because the 322665 25 201132692 is easy to obtain, has good imageability, and has good stability of the hardened material, it can be balanced. When the resin composition of the present invention using the reactive compound (D) is used as an electrical insulating material composition, the reactive compound (D) is preferably derived from an epoxy resin and has both in the active energy line in the same molecule. An epoxy group (fluorenyl) acrylate having a functional group functioning function and an acid-modified product thereof, which are excellent in hardness, insulation, and heat resistance which are required as an electrical insulating material. In the present invention, when the reactive compound (D) is used, the reactive compound (D) in the present invention (100% by mass) is from 10 to 80% by mass = preferably from 20 to 70% by mass, more preferably from 30 to 60% by mass. %, preferably ° is from ^ to 50% by mass. w The active energy ray-curable resin composition of the present invention may have two or more activities in one molecule by using the phosphine oxide compound (A), the polyamine compound or the polyimine compound as the component (B). The energy ray-reactive Luyue b-based reactive compound (D) is obtained by mixing. Better able. 2, the resin composition further contains a photosensitizer (C) or a photopolymerization initiator (e). In this case, the resin composition can be obtained by mixing the above-mentioned three components with a sensitizer (〇 or photopolymerization initiation). The order is not particularly arbitrarily, and may be carried out in any order, or may be sequentially mixed, or may be used together with a photopolymerization initiator (E). For example, benzoin, stupid, benzoin ether, benzoin propyl ether , benzoin isobutyl ether and other stupid factors. #乙酮, 2, 2-diethoxy-2-phenylacetophenone, 2, 2-diethoxy acetophenone, 1, 1-dioxabenzene-, 2-hydroxy-2-methyl-stupyl ketone, diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, I 疋 1 methyl 322665 26 201132692 -1 -[4-(indolyl)phenyl]-2-morphinyl-propane~1, | 玺4 剽 本 本 ; ;; 2-ethyl hydrazine, 2-tert-butyl fluorene, 2 - anthraquinones such as gas, 2, and euphorbia; 2, 4-diethylthioxanthone, 2-isopropylthiophene, (iv), gas oxime, thioxanthone, etc.; Ketal dimethyl ketal, ketal, -1-, ketal, benzophenone, benzophenone, 4-benzoquinone Base _4-methyldiphenyl squama* 4, benzophenone and other benzophenones; 2,4,6~=A 1 'one one * 7 base awkward ugly diphenyl A known general radical type photoreactive bow hair styling agent such as phosphine oxide, bis(2,4,6-trimethyl adenyl)-stano-based oxidized phosphine oxide, etc.

An azo-based initiator such as azobisisobutyronitrile or a peroxide-inducing radical initiator such as a heat-sensitive peroxide can be used in combination. The agent may be used alone or in combination of two or more. When X is contained in the photopolymerization initiator (E), the content of the photopolymerization initiator (£:) is 〇·5 to 2〇% by mass, preferably 1 to 1% based on the entire composition (100% by mass) of the present invention. 10% by mass. Since the resin composition of the present invention has advantages and disadvantages for both the negative type and the positive type, it is preferably selected in accordance with the purpose of use of the resin composition or the production step for obtaining a cured product. In the present invention, since the phosphine oxide compound (A) has an active energy ray-reactive functional group, it is preferably a negative resin composition in order to exhibit the maximum effect of the present invention. Further, in the present invention, a hardener may be added in accordance with an appropriate use. The hardener of the present invention reacts with an acidic group contained in the resin in a material having a negative photosensitive property and intended for electrical insulation, thereby completing the task of forming a strong cured film. When the resin composition of the present invention is used as a solder resist composition, it can be made into a resin composition of the present invention containing a curing agent, and can be used as a hair styling agent which does not contain a hardening agent in a usual manner. Preferably, the method of mixing the hardeners into the two-liquid type of the present invention is preferably used. For example, when the solder resist composition is prepared, a two-liquid solution containing a main solution (resin composition) containing the above components (A), (8), and (9) and a hardener solution containing a % oxygen compound is prepared. The type of solder resist composition is preferred. (4) When the two liquids are mixed and a mixture of the two is prepared, it can be used to form a coating film or the like. In the present specification, the term "mixing" in "provisioning" or "provisioning" also includes mixing, and since it is used as a mixture (or mixture) mixed during use, it is also included. Mixing is a combination of groups. The above hardener may, for example, be an epoxy compound. The epoxy compound is arbitrarily selected depending on the purpose of use of the cured product or the desired properties, and a known general epoxy compound can be used arbitrarily. Specifically, it is an epoxy compound containing a monofunctional epoxy group and two or more epoxy groups in one molecule. It is preferred to use an epoxy compound containing two or more epoxy groups in one molecule. It is also possible that a stronger cured product can be obtained by using a monofunctional epoxy compound. The epoxy equivalent of the epoxy compounds is preferably in the range of up to 45 grams per eq, preferably from 180 to 350 g/eq. If the epoxy equivalent is too small, the obtained hardened material becomes weak, and if it is too large, the crosslinked portion is reduced, and the obtained hardened material becomes weak. Examples of the monofunctional epoxy group include phenyl glycidyl ether and glycidyl group 28 322665 201132692 • (fluorenyl) acrylate. • an epoxy compound (also referred to as a polyfunctional epoxy compound) having a plurality of (2 or more) epoxy groups in the molecule, and specific examples thereof include a novolak epoxy resin (for example, a phenol novolak type epoxy resin, Cresol novolak type epoxy resin, bisphenol-A novolac type epoxy resin), trihydroxyphenylmethane type oxygen tree month a, monocyclopentene-type epoxy resin, double-type A-type epoxy resin , bisphenol-F type epoxy resin, diphenol type epoxy resin, epoxy resin containing naphthalene skeleton, glyoxal type epoxy resin, heterocyclic epoxy resin, and the like. Examples of the phenol novolac type epoxy resin include Epicl 〇 Nrtm N-77 〇 (manufactured by DIC Co., Ltd.), DE N 438 (manufactured by Dow. Chemical Co., Ltd.), jER 154 (manufactured by Nippon Epoxy Co., Ltd.), and eppn. -201, re-306 (manufactured by Sakamoto Chemical Co., Ltd.), etc. The acid varnish-type epoxy resin may, for example, be: fertilizer (: 1^1^-695 (manufactured by the company), 〇〇-1028, EOCN-103S, EOCN-104S (Japanese medicine) (manufactured by the company), uvr-6650 (manufactured by Union Carbide Co., Ltd.), ESCN-195 (manufactured by Sumitomo Chemical Co., Ltd.), etc. The trihydroxyphenyl nonane type epoxy resin may, for example, be EPPN-503 , EPPN-502H, EPPN-501H (manufactured by Nippon Kayaku Co., Ltd.), TACTIX-742 (manufactured by Dow. Chemical Co., Ltd.), jER E1032H60 (manufactured by Nippon Epoxy Co., Ltd.), etc. Dicyclopentadiene Examples of the condensed epoxy resin include EPICLONRTM EXA-7200 (manufactured by DIC Co., Ltd.), TACTIX-556 (manufactured by Dow. Chemical Co., Ltd.), etc. Examples of the bisphenol type epoxy resin include: jER828, jER1001 (曰本环Manufactured by Oxygen Resin Co., Ltd., manufactured by UVR-6410C Union Carbide Corporation, 29 322665 201132692, DE R-331 (manufactured by Dow. Chemical Co., Ltd.), YD-8125 (manufactured by Dongdu Chemical Co., Ltd.), NER- 1202, NER_1302 (manufactured by Nippon Kayaku Co., Ltd.) and other bisphenol-A epoxy resin UVR-6490C manufactured by Union Carbide Corporation), YDF-8170 (Tohto Kasei (shares) Corporation), NER-7403, NER-7604C by Nippon Kayaku (shares) Corporation) -F bisphenol type epoxy resin. Examples of the diphenol type epoxy resin include a diphenol type epoxy resin such as NC-3000, NC-3000-H (manufactured by Nippon Kayaku Co., Ltd.), and γχ_4〇〇〇 (Japanese epoxy resin). The company is made of bisphenol-based epoxy resin, YL-6121 (manufactured by Sakamoto Epoxy Co., Ltd.). Examples of the bisphenol novolak-type epoxy resin include EPICLONRTMN-880 (manufactured by DIC Co., Ltd.), jER E157S75 (manufactured by Nippon Epoxy Resin Co., Ltd.), and the like. The epoxy resin containing a naphthalene skeleton may, for example, be NC-7 (manufactured by Nippon Kayaku Co., Ltd.) or EXA-4750 (manufactured by DIC Co., Ltd.). The ethanedialdehyde type epoxy resin may, for example, be GTR_18® (manufactured by Nippon Kayaku Co., Ltd.). Examples of the alicyclic epoxy resin include EHpE_315(R) (manufactured by Daisei Chemical Industry Co., Ltd.). Examples of the heterocyclic epoxy resin include TEPIC (manufactured by Nissan Chemical Industries Co., Ltd.). In the photosensitive resin composition of the present invention, the above-mentioned poly(methyl) propylene-sulfonated oxime and the above-mentioned polyfunctional epoxy resin as a curing agent are preferably used as a material functional ring. The oxygen resin is preferably a (iv) varnish epoxy resin or a di-anti-epoxy resin, from the viewpoint of purity, flame retardancy, and the like. Paint epoxy resin is better for visualization and flame retardancy. Look forward to the varnish resin or shop A secret varnish epoxy resin 322665 30 201132692 . Depending on the situation, it is better to use acid varnish resin. From the point of flame retardancy, it is preferred that the polyfunctional epoxy resin be in the form of a cresol novolak resin or a diphenol type epoxy resin. When the above-mentioned hardener is used, the hardener is 2 to 50% by mass, preferably 3 to 5% by mass, more preferably 4 to 30% by mass, more preferably 4 to 30% by mass, based on the total amount (100% by mass) of the composition of the present invention. It is 5 to 2% by mass. Further, the total amount of the (A) component, the (B) component, and the (〇) component is 1 part by mass, and the curing agent is usually used in an amount of about 5 to 60 parts by mass, preferably about 1 to 50. Share. If the amount is too small, the obtained cured product becomes weak, and if it is too much, it has an adverse effect on hardenability and the like. In the case where the photosensitive resin composition of the present invention is used for various purposes, the other components can be added to the upper limit of 7 mass% of the entire composition of the present invention. Other components include additives, coloring materials, pigment materials, and the like. The other ingredients that can be used are exemplified below. As the additive, for example, a thermosetting catalyst such as a trimeric amine, a thixotropic imparting agent such as a gas phase dioxane (aer〇S〇1), a coating agent such as an organic lanthanide system or a fluorine compound, or a coating agent can be used. A light-weighting agent such as hydrogen, a hydrogen roller, a formazan, a stabilizer, an antioxidant, and the like. Examples of the coloring pigment include organic pigments such as ugly phthalocyanines, azo-based and 嗤σ-fluorenone-based pigments, carbon black, and the like, and domain pigments such as titanium oxide. For the pigment material, for example, a so-called body material which is not intended for coloring can be used. For example, talc, barium sulfate, calcium carbonate, magnesium carbonate, titanium strontium, hydrogen hydroxide, cerium oxide, clay, or the like can be mentioned. Other resins which do not exhibit reactivity at the active energy ray may also be used. 31 322665 201132692 (inert polymer)' such as other epoxy resins, sulphur resins, urea burn resins, polyester resins, ketone furfural resins, indophenol trees Ester, diterpene resin, diallyl phthalate resin, styrene resin, guanamine resin, natural and synthetic rubber, acrylic resin, polyolefin resin and modified products thereof. These are preferably used within the range of 40% by mass or less of the entire composition of the present invention. For the purpose of adjusting the viscosity, the volatile solvent may be added in an amount of 70% by mass or more preferably 5% by mass based on the entire composition of the present invention. The content of the solvent is usually from 0 to 1000 parts by mass, preferably from 50 to 900 parts by mass, based on the solid content of the resin composition of the present invention or the photosensitive resin composition having no solvent, preferably from 50 to 900 parts by mass, more preferably Range of 150 to 900 parts by mass. The volatile solvent may, for example, be a solvent exemplified in the synthesis of the above polyamine compound or the polyanilide compound. Preferably, a ketone solvent such as butyl vinegar or N-mercaptopyrrolidine _ is mentioned. In general, the solvent is preferably used in an amount of from about 10 to 100 parts by mass based on 1 part by mass of the solid content of the resin composition of the present invention. Hereinafter, a preferred bear or sample of the photosensitive resin composition of the present invention described in the above-mentioned "method for solving the problem" (2) will be described. 1. The photosensitive oxidized resin composition contains 1 to 94% by mass of the above phosphine oxide compound (A), 5 to 98% by mass of the component (B), and a sensitizer (1 to 30% by mass or a photopolymerization initiator (E). (1) to 2% by mass of the photosensitive resin composition. The photosensitive resin composition according to the above 1, wherein the total content of the phosphine oxide compound (a) 32 322665 201132692 and the component (B) is 8〇 to 99. 5% by mass of the sensitizer (the content of the bismuth) is from 1 to 30% by mass. The photosensitive resin composition according to the above 1 contains the phosphine oxide compounds (A) and (B) as a whole of the photosensitive resin composition. The total content of the reactive compound (D) having two or more active energy ray-reactive functional groups in one molecule is from 10 to 80% by mass and the photopolymerization initiator (E) is from 1 to 10% by mass. The photosensitive resin composition according to the above-mentioned item 3 contains the phosphine oxide compound (A) in an amount of 5 to 20% by mass and the component (B) in a range of 5 to 40% by mass, and both of the photosensitive resin composition. The total content is 15 to 49% by mass, and the above reactive compound 50 to 75 mass% of the material (D) and 1 to 10 mass% of the photopolymerization initiator (E). 5. The photosensitive resin composition according to the above 3 or 4, as the reactive compound (D), contains 2 to 2% The total amount of the 6-functional (meth) acrylate compound is in the range of 50 to 100% by mass based on the total amount of the component (D), and the remainder is the above-mentioned reactive compound (D). In the photosensitive resin composition according to any one of the above, the acid-modified (meth) acrylate compound contained in the above 2- to 6-functional (meth) acrylate compound is based on the total amount of the component (D). In the range of 30 to 80% by mass, the remainder is the above-mentioned reactive compound (8). 7. The photosensitive resin composition according to the above 6, wherein the acid-modified (meth) acrylate compound is an acid-modified epoxy resin. 8. The photosensitive resin composition according to any one of the above 3 to 7, further comprising 33 322665 201132692 as an epoxy compound having a plurality of epoxy groups in the molecule of the hardener (multifunctional) Epoxide compound), relative to (A) component, (8) The total amount of the component (D) and the component (D) are prepared in a ratio of 5 to 60 parts by mass. 9. The photosensitive resin composition according to the above 1 to 8, wherein the solvent contains a solid relative to the resin grade. The total amount of 1 part by mass is from 5 to 900 parts by mass. 10. Any of the above items 1 to 9 or any of the above-mentioned "methods for solving the problem" (2) (4) to (7) The photosensitive resin composition described, (B) a polyamine compound (Η) obtained by reacting a bicyclic or tricyclic aromatic diamine of a benzene ring with a bicyclic aromatic tetratgU Imine compound (Β·~2). 11. The photosensitive resin composition according to any one of the above items (1) to (1) or (4) to (7) The monocyclic aromatic diamine is reacted with a bicyclic aromatic tetrabasic acid dianhydride, and the compound (Β-1) or the polySiimine compound (Β_2) is added, and at least one is prepared for crosslinking. The bicyclic aromatic diamine or the bicyclic aromatic tetrabasic acid combined with the -S〇2-crosslinking group. The photosensitive resin composition of Ban 2, the bicyclic aromatic diamine bonded with ~S〇2-crosslinking group is bis(aminophenyl)m crosslinked base ^2 ring aromatic tetraterpene 2 Sf Diphenyl fluoric anhydride. The photosensitive resin composition of any of the above-mentioned items is a novolak epoxy resin or a bisphenol epoxy tree. The photosensitive resin composition of any of the above 6 to 12 is 2 The hexafunctional (fluorenyl) acrylate compound is at least one 322665 34 201132692 'neopentitol poly(2 to 4) (meth) acrylate, dipentaerythritol poly (2 to • 6) (fluorenyl) The group of the propylene oxime ester and the modified e-caprolactone and the ethylene oxide modified product is contained in an amount of 10 to 50% by mass based on the total amount of the component (D). 15. The photosensitive resin composition according to the above 14, wherein at least one selected from the group consisting of neopentyl alcohol poly(2 to 4) (meth) acrylate, dipentaerythritol poly (2 to 6) (meth) propylene The acid group and the e-caprolactone modified product and the epoxy ethylene bromide modified group are ethylene oxide modified dipentaerythritol poly(2 to 6) (fluorenyl) The meaning of propyl benzoate. The photosensitive resin composition according to any one of the above items (2), (4) to (7), or the above In the resin composition according to the above aspect (1), the molecular weight of the polyamine compound or the polyimine compound (b_2) of the component (B) is 8,000 to 15 Å in the weight average molecular weight. , preferably in the range of 15' 000 to 8 〇, 〇〇〇. As described above, the photosensitive resin composition of the present invention can be used as a positive photosensitive resin composition by adding a photosensitive agent (C) or a photopolymerization initiator (E), or can be a negative photosensitive resin composition. By the irradiation of the resin composition/tongue energy line, a characteristic change can be produced. Specific examples of the active energy ray include electromagnetic waves such as ultraviolet rays, visible rays, infrared rays, X-rays, T-rays, and laser lines, and particle lines such as "lines, no wires, and electron beams. In consideration of the preferred use of the present invention, Preferably, the ultraviolet light, the laser light, the visible light or the electron beam is used. In the present invention, the material for forming means that the uncured composition is placed in a mold 35 322665 201132692 or extruded into a mold to form an object via active energy. The line is a positive or negative type, and is preferably a negative-type reaction molder or a material used for the purpose of forming a negative-type characteristic by irradiating a focus light such as a laser to an unhardened composition. As a preferable use, a so-called nanoimprint material which is formed by forming a flat sheet, a sealing material for protecting the element, and a "mold" which is subjected to microfabrication of the uncured composition, and a progress request are mentioned. The flame retardant and the electrical insulation of the halide are avoided. In the present invention, the material for forming a film is a material which is used for the purpose of coating the surface of the substrate. For specific applications, including flexo printing inks for gravure printing inks, screen printing inks, offset printing, etc., hard printing, protective coatings, protective covers (t〇pc〇ating), covers Light, (Overprint Varnishes), smear materials such as clear coating film, layered oils, various adhesives for optical disks, adhesion materials such as adhesives, solder resists, ruthenium corrosion, and resistive materials for micromachines. Further, after the film-forming anti-soak is temporarily applied to the release substrate, the so-called dry film which is adhered to the target material 2 to form a film is also a material for film formation. According to the present invention, the insulating material composition is formed on the substrate to form the film layer of the slave, and the electronic circuit or a part thereof is formed into a large resistance between the target object, even if a voltage is applied thereto. The current flowing current = 2 active energy curing resin composition. The specific application is applicable to the coating material of the flexible board or the interlayer insulating film of the multilayer substrate, the insulating material of the semiconductor component, the insulating film of the solid component or the molding material of the passivation film, and the semiconductor set = Medium 201132692 • Road or multilayer printed wiring board An interlayer insulating material, a solder resist used to protect the substrate, and the like. In particular, it is particularly suitable for a flexible substrate which requires high flame retardancy. The photosensitive resin composition of the present invention can impart not only high flame retardancy but also long-term insulation stability. The insulating material is a necessary portion to be electrically connected to a portion of the substrate that needs to be insulated, and such a pattern must be patterned in response to each need. At this time, there is a case where the pattern is formed by the printing method, but it is difficult to form a fine pattern, and it is not possible to form a substrate having a high density. By using the photosensitive resin composition of the present invention, the film layer of the composition is formed on the substrate, and then the active energy ray such as ultraviolet rays is partially irradiated, and the difference between the physical properties of the illuminating portion and the unirradiated portion is used to form a fine pattern. In addition, the photosensitive resin composition of the present invention can be used as an optical, electronic, or optical substrate such as a printed wiring board, an optoelectronic substrate, or an optical substrate. The preferred use is to utilize the characteristics of the flame retardant and the properties which are required to be used as a permanent resist for solder resists. By combining the phosphine oxide compound (A) used in the present invention and the polyamidamine compound (B-1) or the polyamidimide compound (B-2) as the component (B), it is possible to exhibit high flame retardancy, and When it combines with a reactive compound (D) and a photoinitiator (E), since it carries out reaction in a solder-proof material, it has the effect as a crosslinking agent. Therefore, high flame retardancy and flexibility can be coexisted without adding an extender pigment. The photosensitive resin composition of the present invention does not contain a dentate-based flame retardant and has a halide content of not more than 100 ppm, preferably less than 5 ppm by weight. 322665 37 201132692 The method of forming the film is not particularly limited, and a lithographic printing method such as a gravure printing method such as a gravure such as a gravure or a lithographic printing plate printing method such as a screen printing method, a roller coating method, a doctor blade coating method, and the like can be used. Curtain (four) coating, spin coating method, (four) coating various coating printing methods, flexographic and other convex embossing methods, offset printing and other lithographic plastic film coating, curtain coating, coating. Also included in the present invention is a cured product of the photosensitive resin composition of the present invention. The cured product of the present invention is such that it is hardened by irradiating the active energy ray in the sensory resin or the screaming matter of the present invention. The multilayer material of the present invention is a material obtained by forming a film of the resin composition of the present invention on a substrate and hardening it to have at least two or more layers. [Examples] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to the examples. Further, in the examples, unless otherwise specified, "injury" means quality damage, and "%" means mass%. Further, the measurement of the molecular weight of the polyamine compound and the polyimine compound is carried out by a gel filtration chromatography method using a 1 mM mM lithium bromide N-methylpyrrolidone solution as an eluent, and at this time, the molecular weight standard is Use polystyrene. The phosphine oxide compound (A) represented by the following formula (1) was synthesized according to the following Synthesis Example 1-1.

(wherein R represents an argon atom or a fluorenyl group) 38 322665 201132692 • Synthesis Example 1-1: Synthesis of phosphine oxide compound (A) - Put 9 in a 2L reactor equipped with a scrambler, a thermometer, and a condenser. 10-Dihydro-9-oxa-10-phosphaphenium-10-oxide (manufactured by Sanguang Co., Ltd., trade name: HCA) 216·2g (l. 〇mol) and phenylene benzene. 24.6 g at temperature Dissolved in 80 to 90 °C. Next, the polypyrene 〇g (1.0 mol) was slowly placed under stirring, and the reaction was carried out at a reaction temperature of 80 ° C to 90 ° C for 3 hours. The result was obtained as white crystals, 24.6 g. Next, the white crystals obtained were 24.6 g (l. 〇m〇l), acrylic acid 144.7 g (2.0 mol), toluene 400 g, p-nonoxyphenol ι·5 g and p-toluenesulfonic acid monohydrate. 14. 5 g of the same reactor as above was placed, and dehydration condensation reaction was carried out at 1 to 5 to 110 C for 13 hours. The obtained reaction solution was washed twice with an aqueous solution of sodium carbonate, washed once with 20% saline, and then distilled under reduced pressure to obtain a pale yellow liquid phosphine oxide compound (A) (formula) in which R = H) ((A)R=H) 267.9 g (yield 89.2%). The phosphine oxide compound (A) shows the following physical properties.

The viscous (40 ° C) 6300 CPS refractive index (20 ° C) 1.6145 H-NMR (as measured by Deuterochloroform solution) 4. 80ppm = 2H, 5. 60ppm = lH, 6. 16ppm = iH, 6. 4 5 ppm - 1H, 7 · 24 - 7 · 93 ppm = 8H Synthesis Example 2-1: Synthesis of Polyamine Compound i In a 1 L reactor equipped with a stirrer, a thermometer, and a condenser, a double (3-) as an amine compound was placed. Aminophenyl), 121 g (0.5 mol), as a solvent, N-decylpyrrolidone, the solid content of the target was 40% by weight 39 322665 201132692 (471 g). Further, 193 g (〇. 5 mol) of 3,3'' 4,4-diphenylfluorene tetraacic anhydride as a tetrabasic acid was placed here. Thereafter, the reaction was carried out at 10 Torr for 1 hour to obtain a polyamine compound (Poly-Al) solution (solid content: 40% by weight). The polyamine compound 1 (Poly-Al) has a weight average molecular weight of 65,000. Synthesis Example 2-2: Synthesis of Polyimine Compound (p〇1y_1) In 350 g (solid content: 140 g) of a solution of N-mercaptopyrrolidone of the polyamine compound KPoiy-A1) synthesized in Synthesis Example 2-1, Adjusting the solid fraction 'Additional N~methyl η to each of the 嗣 嗣 makes the solid fraction 25% (350g). After adding 10 g of Aben as a dehydration auxiliary agent, the azepine imidization reaction was carried out at 200 ° C for 20 hours while azeotroping with toluene to obtain a polyimine compound (Poly-I) solution (solid content: 25%). . The weight average molecular weight of the polyimine compound (Poly-I) was 730,000. Synthesis Example 2-3: Synthesis of Polyamine Compound 2 (Poly-A2) In a 1 L reactor equipped with a stirrer, a thermometer, and a condenser, bis(3-aminophenyl)sulfone 121 g as a diamine compound was further placed. (0. 5 mol), N-based "pyrrolidone" as a solvent, the solid content of the target was 4% by weight (471 g). Further, 147 g (0.5 mol) of a hydride of 33,4,4'-diphenyltetracarboxylic acid anhydride as a tetrabasic acid dianhydride was placed. After that, the reaction was carried out for 10 hours at TC to obtain a polyamine compound 2 (Poly-A2) solution (solid content of 40% by weight). The weight average molecular weight of the polyamine compound 2 (Poly-A2) was 68, 〇合成. Synthesis Example 2-4: Synthesis of Polyamine Compound 3 (Poly-A3) was placed in a 1 L reactor equipped with a stirrer, a thermometer and a condenser for 40 322665 201132692 • l 8-8 of a diamine compound Methylenediamine 36. lg (0.25 mol) and 1,3-bis(3-aminophenoxy)benzene 73. lg (〇. 25 mol), N-methyl-pyrrolidone 393 as a solvent 2克(0. The hydride of the 3,3,4,4,-diphenyltetracarboxylic anhydride as a tetrabasic acid dianhydride is added to the hydride. 5 mol). Thereafter, the reaction was carried out at 100 ° C for 1 hour to obtain a polyamine compound 3 (Poly-A3) solution (solid content of 40% by weight). The weight average molecular weight of the polyamine compound 3 (Poly-A3) 65, 〇〇〇. Example 1: Preparation and Evaluation of Composition for Positive Soldering Agent The phosphine oxide compound (A) obtained in the above Synthesis Example 1-1 ((A)R=H) 5 g, the above synthesis example Polyamine obtained in 2-1 or 2-3 75 g of a compound solution (solid content: 40% by weight) or 120 g of a poly-imine compound solution (solid content: 25%) obtained in the above Synthesis Example 2-2 and DTEP-350 as a sensitizer (C) (Dow-Chemical Co., Ltd.) Manufactured) 10 g of the photosensitive resin composition of the present invention (Examples 1-1 to 1-3) were mixed in the combination of Table 1. This was applied by screen printing on a copper circuit printed substrate to dry. The thickness of the coating film was dried by a hot air dryer of 8 (TC for 60 minutes. Next, the cover film on which the pattern was drawn was adhered, and ultraviolet rays were irradiated using an ultraviolet exposure apparatus (manufactured by USHIO: 5 〇〇w multiple light source). The solution was sprayed (spray pressure: 2. 2 MPa) using a 1% aqueous solution of tetradecyl ammonium hydroxide (temperature 30 t) as a developing solution. After washing with water, it was heat-treated at 150 ° C in a hot air dryer. In a minute, a copper circuit printed substrate having the cured layer of the present invention was obtained. 322665 201132692 The evaluation of the above-mentioned coating film development was carried out by the following method, and the results are shown in Table 1. The reliability of the hardened layer and the flame retardancy The evaluation is carried out in the following manner The results are shown in Table 1. Comparative Example 1: Preparation and evaluation of positive anti-corrosive composition For the phosphine oxide compound (A) of the present invention obtained without using the above synthesis example, or using hq-HQ (Sanguang Co., Ltd.) The flame retardant to be produced) was subjected to the same operation as in Example 5 except for 5 g, and a photosensitive resin composition for comparison (Comparative Examples 1-1 to 3) was obtained. The obtained resin composition was attached, and the same operation as in the above Example was carried out to form, develop, and harden a coating film to obtain a steel circuit printed substrate having a cured layer. Evaluation of film developability was carried out by the method shown below. The evaluation results are shown in Table 1. Further, the evaluation of the reliability and flame retardancy of the hardened layer was carried out by the following method, and the results are shown in Table i. (Development evaluation) The development performance is the time until the pattern shape is completely developed when the exposure portion of the pattern mask is developed, that is, the so-called break time is evaluated as the development property. (Unit: second). In addition, the one that has not been disconnected within ι2 〇 second is represented by X. (Reliability evaluation) Using a screen printing method on a polyimide substrate constituting a comb-shaped electrode having a line/space = 50/50/zm, each composition was formed into a coating film with a film thickness of about 25 after hardening, and In the same manner as above, ultraviolet irradiation was carried out to obtain a polyimide substrate having a cured layer. The polyimine substrate with the cured layer was placed in a high temperature bath of 120° 〇 85% relative humidity, plus 100V 42 322665 201132692 The resistance value was 1M. The electric house with a long time’ observation of the change of its resistance value from the beginning of the test,

For the 以下 below Ω, ^ 〇t/IJ r The time of finding the point, which is shown in the table below to determine the long-term reliability of the circuit. (Flame-resistance evaluation) The flame retardancy is a non-dentate flame-retardant substrate RO-67G (thickness. 2 mm) manufactured by each Hitachi Chemical Co., Ltd.. The respective compositions obtained in the examples and the comparative examples were screen-printed to a single sheet. The surface 15#ιη thickness was completely applied, and the same operation as in the Example was applied to evaluate the flame retardancy according to the method of the UL test method after hardening. The evaluation criteria are as follows. ◎: Equivalent to UL V-〇 (the total burning time is less than 50 seconds when each of the five test months is fired) 〇: Equivalent to UL V-1 (the total burning time when each of the five test pieces is ignited twice) 50 to 250 seconds. No burning matter falls after the test) △: Equivalent to UL V-2 (the total burning time of each of the 5 test pieces is 2 to 50 seconds. The combustion is dropped after the test) X : No Will extinguish the fire by itself 43 322665 201132692 Table 1: Example 1, Comparative Example 1 Example of the flame retardant compound (B) component Example 1 (A) R = H Poly-Al Example 1_2 (A) R = H Poly-I Example 1-3 (A) R = H Poly-A2 Comparative Example 1-1 No Poly-Al Comparative Example 1-2 No Poly-I Comparative Example 1-3 HCA-HQ Poly-Al Example 2: Negative type Modulation of flux composition and evaluation of imaging reliability. Flammability 38 seconds 80 hours 48 seconds © 115 seconds 270 hours 41 seconds © 25 seconds 100 hours 47 seconds © 55 seconds 78 hours XX 78 hours X 50 seconds 22 hours 56 Seconds; 25 g of the polyphosphonium compound solution obtained in the above-mentioned synthesis example of the phosphine oxide compound (A), the above-mentioned Synthesis Example 2-1 or 2-3, or the polyimine compound obtained in the above Synthesis Example 2-2 40g solution Ethylene oxide-modified dipentaerythritol hexaacrylate of reactive compound (D) (manufactured by KAYARADrtm DPEA-12X 曰本化药股份有限公司) l〇g, acid-modified epoxy acrylate (acidification) : l〇〇mgK〇H/g, KAYARADRTMCCR-1159X manufactured by Nippon Kayaku Co., Ltd.) 30g, Irukachu as photopolymerization initiator (E)

(Irgacure) RTM907 (manufactured by Ciba Specialty Chemicals Co., Ltd.) 3g, KAYACURERTM DETX-SHP (manufactured by Nippon Kayaku Co., Ltd.) 〇·5g, 8g of cresol novolac type epoxy resin as a curing agent, and the present invention is obtained. The active energy ray-hardening type is known as a composition. This was applied to the copper circuit printing substrate by screen printing so that the thickness after drying was 25 #m, and the coating film was 8 inches. (The hot air dryer was dried for 60 minutes, and the same operation as in Example , was carried out to obtain a copper circuit printed substrate having the cured layer of the present invention. Evaluation of coating film developability, reliability of hardened layer, and flame retardancy The evaluation was carried out in the same manner as in Example 1. The results are shown in Table 2. 322665 44 201132692 - Example 3: Preparation and Evaluation of Composition for Negative Solder Resistant The reactive compound of the present invention obtained in the above Synthesis Example (A) 1 g, 25 g of the polyamine solution obtained in the above Synthesis Example 2-4, polyethylene glycol diacrylate as the reactive compound (D), (manufactured by KAYARADRT MPEG-400 DAX Nippon Kayaku Co., Ltd.) L〇g, acid-modified epoxy acrylate (KAYARAD ZCR-1569X solid fraction 65% (propylene glycol - 酉 酉 酉 ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) Yilu

Kaqiu 907 (&gt; manufactured by Baline Chemical Co., Ltd.) 3g, KAYACURERTMDETX-SHP (manufactured by Nippon Kayaku Co., Ltd.) 〇. 5g, diphenol type epoxy resin 8g as a curing agent, N-A as a solvent 5 g of the pyrrolidone was mixed to obtain an active energy ray-curable resin composition of the present invention having a solid content of 30%. This was applied to a copper circuit printed substrate by screen printing so as to have a thickness of 25 mm after drying, and the coating film was dried in a hot air dryer for 60 minutes. Thereafter, the same operation as in Example 1 was carried out to obtain a copper circuit printed substrate having the cured layer of the present invention. The evaluation of the film development property, the U of the hardened layer, and the evaluation of the flame retardancy were carried out in the same manner as in Example 1. The results are shown in Table 2. Example 2: Preparation and evaluation of a composition for a negative-type solder resist For a reactive compound (A) of the present invention obtained without using the above synthesis example or using a HCA-HQ (flammable agent manufactured by Sanguang Co., Ltd.) ) Other than 5 g 'Other photosensitive resin compositions were obtained according to Example 2. The results are shown in Table 2. 45 322665 201132692 Table 2: Example 2, Comparative Example 2 Example of flame retardant compound (B) Component development reliability Flammability Example 2-1 (A) R = H Poly-Al 18 seconds 140 hours ◎ ( 45 seconds) Example 2-2 (A) R = H Poly-I 30 seconds 130 hours ◎ (40 seconds) Example 3-1 (A) R = H Poly-A3 15 seconds 240 hours ◎ (37 seconds) Comparison Example 2-1 No Poly-Al 25 seconds 150 hours X Comparative Example 2-2 No Poly-I 45 seconds 170 hours X Comparative Example 2-3 HCA-HQ Poly-Al 50 seconds 33 hours △ (59 seconds) Comparative Example 2_4 (A) R = H, 10 seconds, 150 hours, X. From the above results, it is confirmed that the phosphine oxide compound (A) and the component (B) of the present invention (polyamine compound or polyimine compound) can be used in combination. A resin composition that is superior in flame retardancy, reliability, and development. [Industrial Applicability] The photosensitive resin composition of the present invention has basic characteristics as a solder resist, and is particularly excellent in flame retardancy, reliability, and development. The basic characteristics of the superior flame retardancy, reliability, and development are the photosensitive resin compositions of the present invention which are not only required for photosensitive solder resists but also for other purposes for the purpose of flame retardancy. Regardless of the use, it can be suitably used in a wide range of applications. [Simple description of the diagram] None [Key component symbol description] None 46 322665

Claims (1)

201132692 VII. Patent application scope: I A resin composition obtained by reacting a phosphine oxide compound (A) represented by the following formula (1) and a diamine compound and a tetrabasic acid dianhydride as a component (B). Polyamine compound or polyimine compound, (wherein R represents a hydrogen atom or a fluorenyl group). 2. A photosensitive resin composition comprising a phosphine oxide compound (A) represented by the following formula (1) and a polyamine obtained by reacting a diamine compound with a tetrabasic acid dianhydride as a component (B) a compound or a polyimine compound and a sensitizer (C) or a photopolymerization initiator (E), (wherein R represents a hydrogen atom or a fluorenyl group). 3. The photosensitive resin composition according to claim 2, which comprises the phosphine oxide compound (A), the component (B), and the sensitizer (C). 4. The photosensitive resin composition according to claim 2, which comprises the phosphine oxide compound (A), the component (B), and one or more active energy ray-reactive functional groups in one molecule. Reactive Compound 1 322665 201132692 (D) and photopolymerization initiator (E). The photosensitive resin composition according to claim 4, which contains a 2 to 6-functional (fluorenyl) acrylate compound as the above reactive compound (D). 6. The photosensitive resin composition according to item 4 of the patent application, wherein the polyfunctional epoxy compound as a curing agent is additionally blended. 7. The photosensitive resin composition according to the fourth aspect of the invention, wherein the acid-modified (fluorenyl) acrylate compound is contained as the reactive compound (D) 〇8. In the resin composition, the phosphine oxide compound (A) is contained in an amount of from 1 to 95% by mass of the phosphine compound (A) and from 5 to 99% by mass of the component (B). 9. The resin composition according to any one of the preceding claims, wherein the photosensitive resin composition according to any one of claims 2 to 8 is a molding material. 10. The resin composition according to any one of the preceding claims, wherein the photosensitive resin composition according to any one of claims 2 to 8 is a film forming material. The resin composition according to any one of claims 2 to 8, wherein the photosensitive resin composition is an electrically insulating material. 12. The resin composition according to any one of the preceding claims, wherein the photosensitive resin composition according to any one of claims 2 to 8 is a solder resist composition. 2 322665 201132692 13. A multi-layer material characterized by having a resin composition as described in claim 1 or a curing of the photosensitive resin composition according to any one of items 2 to 8. Layer of matter. A cured product which is a cured product of the resin composition described in claim 1 of the patent application. A cured product of the photosensitive resin composition according to any one of claims 2 to 8. 3 322665 201132692 . IV. Designated representative map: There is no schema in this case (1) The representative representative map of this case is: (). * (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 322665