TWI375863B - - Google Patents

Description

Nine, the invention description: [Technical field to which the invention pertains] .. Shuming is an intrinsic (four) resin composition containing a specific compound having an ethylenically unsaturated bond, and a (four) developable resin group. The organic light-sensitive resin composition in which the photopolymerization initiator is contained in the material I is used. [Prior Art] An alkali-developable photosensitive resin composition containing an in-progress developable resin composition containing a compound having an ethylenically unsaturated bond and a photopolymerization initiator, because it can be used for the test The developed photosensitive resin composition is polymerized and cured by ultraviolet rays or electron beams, and thus can be used for photocurable inks, photosensitive printing plates, printed wiring boards, various green agents, and the like. Recently, with the development of the thinness and the high functionality of the electronic device, the manufacturer has demanded that the microscopic pattern-developable developable photo-resin composition can be formed with high precision. ～ As the testable resin composition and the developable photosensitive photo-curable resin composition, the following patent documents are available! There has been proposed a photopolymerizable unsaturated compound and an inventor-developing photosensitive photoreceptor composition containing the compound. In Patent Document 2 below, there is proposed a polycarboxylic acid tree containing a Q group and A photosensitive resin composition containing the resin composition. Further, in Patent Document 3 below, an intrinsic soluble unsaturated resin and a radiation sensitive resin composition containing the resin are proposed. However, the above-mentioned well-developed electrophotographic photosensitive resin compositions have insufficient sensitivity, and it is difficult to obtain a suitable pattern shape or fine pattern. In the case of the above-mentioned manufacturer, an alkali-developable photosensitive resin composition which is excellent in transparency, adhesion, and alkali resistance and which can form a fine pattern with high precision is required. Patent Document 1: Japanese Patent No. 3,148,429, Patent Document 2: Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. 2003-89716. The problem to be solved is that, until now, an alkali-developable resin composition and an organic-developable photosensitive resin composition having sufficient sensitivity and obtaining a suitable pattern shape or fine pattern have not been developed. Therefore, an object of the present invention is to provide an alkali-developable resin composition and an alkali-developable photosensitive resin which are excellent in sensitivity, resolution, transparency, adhesion, and alkali resistance, and which can form a fine pattern with high precision. combination. SUMMARY OF THE INVENTION The present invention provides an alkali-developable resin composition, thereby achieving the above object, which is characterized in that it contains a reaction obtained by acetating a polyacid needle (D) with respect to an epoxy adduct. In the product, the above epoxy adduct has the following general formula (1): < epoxy resin (A) addition unsaturated monobasic acid (B) and selected from the group consisting of a benzoquinone compound, an alcohol compound, an amine compound, and a carboxylic acid The structure of the compound (C), the above epoxy adduct having the following structure: with respect to one epoxy group of the above epoxy resin (A), the above-mentioned unsaturated monobasic acid (B) is a ruthenium (MM.O) The above compound (the silky mercapto group, the alcoholic transatom group, the amine group or the slow group is 〇 to 〇9, and the above unsaturated monobasic acid 104737.doc 1375863 (B) and the sum of the above compounds (C) a structure in which a ratio of 〇·1 to a ratio is added; the esterification is based on one of the above-mentioned epoxy adducts, and the acid needle structure of the above polybasic acid anhydride (D) is 〇.1 to 1.0 The ratio is carried out. [Chemical 1]

(wherein Cy represents a cycloalkyl group having 3 to 10 carbon atoms, X represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group, or a carbon atom number of 3 to 1 Å. The cycloalkyl group, γ and z each independently represent an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 1 carbon atom, an alkenyl group having 2 to 1 carbon atom or a halogen atom, and the above alkyl group The above alkoxy group and the above-mentioned dilute group may also be substituted by a halogen atom 'n represents a number from 0 to 10, p represents a number from 0 to 5, and r represents a number from 〇 to 4). Further, the present invention provides an alkali-developable photosensitive resin composition containing the above-described alkali-developable resin composition and photopolymerization initiator, thereby achieving the above object. [Embodiment] Hereinafter, the alkali-developable resin composition of the present invention and the alkali-developable photosensitive I1 raw tree I 曰 composition will be described in detail based on preferred embodiments. The raw developing resin composition contains a reaction product, and the reaction product is obtained by reacting a polyether anhydride (D) with respect to an epoxy adduct of the epoxy adduct. The acid anhydride structure is a ratio of 〇1 to 1. The esterification is carried out. The epoxy adduct has an epoxy resin (Α) expressed by the above general formula (π) 'to make an unsaturated monobasic acid (Β) And a compound (c) selected from the group consisting of a phenol compound, an alcohol compound, an amine compound, and a carboxylic acid, and the carboxyl group of the above unsaturated monobasic acid (Β) is 0.1 to 1.0 with respect to one epoxy group of the above epoxy resin (oxime). The ratio of the phenolic hydroxyl group of the above compound (c) to the hydroxyl group, the amine group or the carboxyl group is from 0 to 0.9, and the sum of the component (B) and the component (C) becomes 〇1 to! The ratio of the ratios is added to the construction of I. The ratio of the carboxyl group of the above unsaturated monovalent 1 (B) to the epoxy group of the above epoxy resin (A) is preferably from 4 to 1 such as the above compound (the phenolic hydroxyl group, the alcoholic hydroxyl group, The ratio of the amine group or the carboxyl group is preferably from 〇 to 6 and the sum of the components (B) and (C) is preferably from ◦々 to 〇. Further, a hydroxyl group relative to the above epoxy adduct The ratio of the anhydride structure of the polybasic acid anhydride (1) is preferably from 0.4 to 1. ββ In the above general formula (1), 'as a cycloalkyl group having 3 to 1 Å of carbon atoms represented by fluorene, Τ exemplified by cyclopropyl group and ring Butyl, cyclodecyl, cyclohexyl, methylcyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, cyclodecyl, etc., as an alkyl group having 1 to 10 carbon atoms represented by 7 and fluorene Listed are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, tert-butyl, pentyl, isopentyl, tert-pentyl, hexyl, heptyl, octyl , isooctyl, trioctyl, 2-ethylhexyl, decyl, isodecyl, fluorenyl, isodecyl, monofluoromethyl, di "yl, trifluoromethyl, trifluoroethyl, all Fluoroethyl, etc., 104,737.doc •10·1,375,863, as the oxy group of the carbon atom number Η to Η), exemplified by methoxyethoxy, propoxy 'decyloxy, methoxyethyl, ethoxy Ethyl ethyl, propoxyethyl, methoxyethoxyethyl, ethoxyethoxyethyl, propoxyethoxyethyl ethyloxypropyl, etc., as carbon number 2 to (7) Examples of the dilute group include a vinyl group, an allyl group, a butenyl group, a propyl group, and the like. Examples of the dentate atom include fluorine, gas, bromine, and iodine. The epoxy resin (A) used in the preparation of the alkali-developable resin composition of the present invention has a triarylmonocycloalkylmethane skeleton, and thus the adhesion of the cured product to the substrate is improved. Since the properties, the strength, and the like are relatively good, it is considered that even when the non-hardened portion is removed by development, an image can be formed accurately even with a fine pattern. As the epoxy resin (A), it is preferred that Cy is a cyclohexyl group in the above general formula (); χ is a phenyl group; p and 犷 are oxime; and η is 〇 to 5', particularly 0 to 1. Specific examples of the epoxy resin (Α) represented by the above general formula (1) may be used.

The following compounds Ν〇·丨 to ^^ are listed. · 9 compounds. Among them, the present invention is not limited to any of the following compounds. [Chemical 2] Compound No. 1

104737.doc 1375863 [Chemical 3] Compound No. 2

[Chemical 4] Compound No. 3

[Chemical 5] Compound No. 4 ♦

104737.doc -12- 1375863

Compound No. 5

Hey, CH,

[Chemical 7] Compound No. 6

OMe Ο ο . Ten 4τ〇

OMe [Chemical 8] Compound No. 7 Ο ο

104737.doc -13 - 1375863 [Chemical Formula 9] Compound No. 8

Compound No. 9

The reaction product obtained by esterifying the component (D) after the component (B) and the component (C) are added to the component (A) as contained in the alkali-developable resin composition of the present invention, for example, It can be produced by the method represented by the following reaction formula [Chemical Formula 11]. First, the unsaturated monobasic acid (2) as the component (B) and the phenol compound (3) as the component (C) are added to the epoxy resin (1) as the component (A), thereby obtaining A resin composition containing the compound (4) which is an epoxy adduct. Then, in the compound (4), the polybasic acid anhydride (5) as the component (D) is reacted to carry out an esterification reaction to obtain a resin composition containing the compound (6) which is a reaction product. Further, the compound (6) is reacted with the epoxy compound (7) as the component (E), and a resin composition containing the compound (8) of 104737.doc -14-1375863 can be obtained. [化11]

The method of obtaining the epoxy adduct represented by the above [Chemical U], that is, the compound (4), is not limited to the above method, and for example, when the compound (4) < r^0, it can be as follows [ The method (4) of reacting bisphenol (9) with a monoepoxy compound containing glycidyl methacrylate (10) is shown in the reaction formula of 12]. After the service 104737.doc -15· 1375863

[化 12]

The unsaturated element k (B) ' used for obtaining the alkali-developable resin composition of the present invention may, for example, be acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate. Ethylene diester, propyl fumarate by ethyl ester. Maleate, hydroxypropyl methacrylate, maleic acid vinegar, hydroxypropyl acrylate, maleate, dicyclopentadiene • Maleic acid ester and the like.

The phenol compound which can be used as the compound (C) for obtaining the alkali-developable resin composition of the present invention may, for example, be phenol, phenol, cresol, ethyl phenol, propyl phenol or cumylphenol. , tert-butylphenol, third amyl phenol, hexyl phenol, octyl phenol, isooctyl phenol, third octyl benzene, nonyl phenol, dodecyl phenol, octadecyl phenol, 2,4-di-tert-butylphenol, 2,5-di-tert-butylphenol, 3,5-di-tert-butylphenol, 2,4,6-tribromophenol, 4-(1 , 1,3,3-tetramethylbutyl) benzene, 2-(3,5-dimethylheptyl)phenylhydrazine, 4-(3,5-dimethylheptyl) stupid 104737.doc - 16 - 1375863 Phenol, indophenol and naphthol. The alcohol compound which can be used as the compound (c) for obtaining the alkali-developable resin composition of the present invention includes methanol, ethanol, propanol butanol, hexanol, heptanol, and octanol. , isopropanol, dibutyl. alcohol, 2·pentyl alcohol, 3·pentyl alcohol, 2-hexyl alcohol, 3-hexyl alcohol, 2-heptyl alcohol, 3-heptyl alcohol, 4—heptyl Alcohol '2-octyl alcohol, 3-octyl alcohol, 'octyl alcohol, tert-butyl alcohol, 2-mercaptobutane-2-ol, 2-methylpentane-2-ol, 2·^ Methyl hexane · 2 · alcohol and 2-decyl heptane-2-ol. As the amine compound which can be used as the compound (C) for obtaining the alkali-developable resin composition of the present invention, for example, mercaptoamine, ethylaminopropylamine, butylamine, pentylamine, hexyl group can be mentioned. Amine, heptylamine, octylamine, monomethylamine, diethylamine, dipropylamine, dibutylamine 'dipentylamine, dihexylamine, diheptylamine, dioctylamine, Porphyrin, piperidine, and the like. The carboxylic acid which can be used as the compound (C) for obtaining the alkali-developable resin composition of the present invention includes, for example, acetic acid, propionic acid, 2,2-di-(hydroxymethyl)propionic acid, and lactic acid. An acid, aromatic or alicyclic mono-acid such as butyric acid, caprylic acid, lauric acid, linoleic acid, ricinoleic acid, benzoic acid, toluic acid, cinnamic acid, phenylacetic acid, cyclohexane or carboxylic acid. • As the polybasic acid anhydride (D) for obtaining the alkali-developable resin composition of the present invention, acrolein anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, 2,2,3'3-diphenyl can be cited. A-tetracarboxylic anhydride, 3,3.,4,4._benzophenonetetracarboxylic anhydride'ethylene glycol double-dehydrated trimellitic acid vinegar, glycerol tri-dehydrated trimellitic acid vinegar, orthophthalic acid Anhydride, methyltetrahydrophthalic acid drunk, tetrahydrophthalic acid acid needle, diarrhea acid, methyl acid acid field, trialkyl tetra 104737.doc • 17- 1375863 hydrogen o-benzoic anhydride , hexahydronoic acid anhydride, 5-(2,5-dioxotetrahydroindolyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trialkyl four Hydrogen o-dimethic anhydride-maleic anhydride adduct, dodecyl succinic anhydride, methyl sulphonic acid and other anhydrides, 3,3,4,4,-biphenyltetracarboxylic dianhydride, 3 , 3,4,4,·diphenyltetrahydro acid dianhydride, 4,4,-oxy di-o-dicarboxylic acid dianhydride, 2,3,5-trimethylcyclopentyl acetic acid dianhydride, i a dianhydride such as 2,3,4-cyclopentanetetracarboxylic dianhydride or methylhexahydrophthalic anhydride; among these, it is preferably Acid anhydride, or a combination of the dianhydride with an acid anhydride. In the present invention, the epoxy compound (E) used to adjust the acid value can be used to improve the developability of the alkali-developable resin composition of the present invention. Examples of the epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, and isobutyl glycidol. Ether, second butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether 'mercapto glycidyl ether, decyl glycidyl ether, undecyl shrinkage Glycerol ether, lauryl glycidol mystery, dodecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, 2-ethylhexyl glycidol Ether, allyl glycidyl ether, propargyl glycidyl ether, p-methoxyethyl glycidyl ether, strepto glycidyl ether, p-methoxyglycidyl ether, p-butyl phenol glycidyl ether, toluene Glycidyl ether, 2-methyltolyl glycidyl ether, 4·nonylphenyl glycidyl ether, benzyl glycidyl ether, p-cumyl glycidyl ether, triphenyl f-glycidyl ether, methyl Acryl 2,3-epoxypropane , Epoxidized soybean oil, epoxidized linseed 104737.doc -18 - oil, glycidyl butyrate, 4-vinyl cyclohexene burning, alkylene oxide, cyclohexene association, and the like.

The next day, vinyl cyclohexane monooxide, oxygen oxidized stupid ethylene, decene oxide, methyl oxidized stupid ethoxylated propylene, the following compound No. 10, No. U The acid value of the solid content of the &&amplifier resin composition is preferably in the range of 60 to 120 mgKOH/g, and the epoxy compound (E) is used in an amount sufficient to satisfy the above. The choice of the sour 僧 丄 丄 & [Chem. 13]

Compound No. 1〇 [Chemical 14]

Compound No. 11 〇 The detectively developable resin composition of the present invention, # Further, a photopolymerization initiator can be added to prepare an alkali-developable photosensitive resin composition. The alkali-developable resin composition and the alkali-developable photosensitive resin composition of the present invention are usually used as a solution-like composition in which the following solvent capable of dissolving or dispersing the above-mentioned respective components is added as needed: for example, acetone , methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl cellosolve, ethyl cellosolve, propylene glycol monoterpene ether acetate, gas imitation, dioxane, hexane, g Alkane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol. The solvent-like composition preferably has a solvent content of from 3 to 9 % by weight, particularly preferably from 40 to 70% by weight. Adding the component (B) to the component (A) and the corresponding reaction product (the component of the component (D), and then the reaction product obtained by the reaction (E) component is required. The content is preferably from 1 to 8% by weight in the above-mentioned solution-like composition, and particularly preferably from 3 to 30% by weight. The above photopolymerization initiator used as the alkali-developable photosensitive resin composition of the present invention A previously known compound can be used, and examples thereof include a dimethyl ketone, a benzylbiphenylene group, a hydrazinyl group, a benzophenone, a benzyl bis ketal, 1-benzyl-1-dimethylaminomorpholinophenyl)propane, 2-morpholinyl-2-(4,-methylindenyl) benzhydrylpropane, thioxanthone, 1-gas -4-propoxy thioxanthone, isopropyl thioxanthone, diethyl thiopyridone, ethyl hydrazine, 4 _ 曱醯 曱醯 4,-methyl diphenyl thioether, benzoin butyl ether , 2-hydroxy-2-benzhydrylpropane, 2-hydroxy-2-(4,-isopropyl)benzhydrylpropane, 4-butylbenzylidenetrichloromethane, 4-phenoxy Stupid thiol dimethane, methyl benzyl carbazate, 1,7- Bis(9'-acridinyl)heptane, 9-n-butyl-3,6-bis(2'-morpholinylisobutyryl)carbazole, 2-methyl-1-[4-(methyl sulfide Phenyl]-2-morpholinylpropan-1-one, 2-methyl-4,6-bis(trimethylmethyl)-s-triazine, 2-phenyl.4,6-bis ( Tris-methyl)-s-triterpene, 2·naphthyl-4,6-bis(tris-methyl)-s-triazine, and the following compounds No. 12, No. 13, and the like. Compound No. 12

104737.doc 20· 1375863 (Formula t, X丨 represents a dentate atom or an alkyl group, Ri represents R, 〇R, COR, SR, CONRR, or CN, and R2 represents R, 〇R, c〇R, sr or NRR ', R3 represents R, OR, COR, (3) or NRR, and R and R| represent an alkyl group, an aryl group, an arylalkyl group or a heterocyclic group, which may also be substituted by a self atom and/or a heterocyclic group. The alkyl group and the alkyl group of the aralkyl group may be inserted into one selected from the group consisting of an unsaturated bond, an ether bond, a thioether bond, and an ester bond, and R and R may also form a ring together. n is 〇 to 5). Compound No. 13

(wherein X!, R, r2, R3, R and R are the same as the above compound N〇12, Xl• represents odoxin or burnt group, z represents an oxygen atom or a sulfur atom m and n respectively represent 1 To the number of 4, Ry means r, 〇R,

SR CONRR' or CN, R_2, denotes r, 〇R, c〇R, SR *NRR ' R3 denotes R, 〇R, COR, SR or NRR' ' R4 denotes a diol residue or a dithiol residue, respectively) . In the present invention, the content of the photopolymerization initiator is preferably 0 to the content of the solution-like oral solution in the pure __-fat composition towel of the present invention. 30% 〇/〇, particularly preferably 0.5 to 5% by weight. 104737.doc • 21 In the present invention, the developable resin composition and the alkali-developable photosensitive resin composition, and further, a monomer having a unsaturated bond, a bond transfer agent, and a surfactant can be used in combination. Wait. Examples of the monomer having the above unsaturated bond include acrylic acid-2·hydroxyethyl vinegar, propionic acid via propyl group, propyl «isobutyl S, η-octyl acrylate, and isooctyl acrylate. Ester, isodecyl acrylate, acrylic ketone, methoxyethyl acrylate, dimethylaminoethyl acrylate, propylene zinc hydride, 1'6-hexanediol diacrylate, tris(hydroxyl) Methyl)propane triacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, butyl methacrylate, t-butyl methacrylate, methacrylic acid ring Hexyl ester, tris(hydroxymethyl)propane trimethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, pentaerythritol tetrapropionate, pentaerythritol triacrylate, and the like. Examples of the chain transfer agent include thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-weiylpropionic acid, 3-propionylpropionic acid, 3-cyanobutyric acid, and hydrazine-(2- Glycosyl methionine, glycine acid, 2-sulfanyl final acid, 3-[indole-(2-sulfoethyl)amine-based]propionic acid, 3-[Ν-(2- sylylene Alkyl]propionic acid, hydrazine-(3-siliary propyl) alanine, 2-sodium sulfonate, acid- 3, succinyl-propionic acid, 4-sulfathyl-burning acid, ten Dialkyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propane diol, 1-mercapto-2-propanol, 3-disyl-2-butanol, hydrazine Phenyl, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, thioglycolic acid, tris(hydroxymethyl)propane tris(3-mercaptoproperate a sulfonate compound such as an acid ester or a pentaerythritol tetrakis(3-dithiopropionic acid vinegar), a disulfide compound obtained by oxidizing the mercapto compound, iodoacetic acid, iodopropionic acid, 2-104737.doc • 22-breaking ethanol 2, moth, money, propylene material moth compound, etc. 0 as the above surfactant, can use perfluoroalkyl phosphate, perfluoroalkyl hydrazine a fluorine surfactant such as a salt, an anionic surfactant such as a higher fatty acid alkali salt, an alkylsulfonate or an alkyl sulfate; a higher amine hydrogen is a cationic surfactant such as an acid f or a quaternary salt; A nonionic surfactant such as a glycol base scale, a polyethylene glycol fatty acid ester, a sorbitan fatty acid ester or a fatty acid monoglyceride, or an amphoteric surfactant 矽 oxygen surfactant or the like may be combined. Use these. In the alkali-developable resin composition and the alkali-developable photosensitive resin composition of the present invention, the properties of the cured product can be further improved by using the thermoplastic organic polymer. Examples of the thermoplastic organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly(meth)acrylic acid, and stupid ethylene (fluorenyl) propylene. Bake copolymers, (meth)acrylic acid-methyl methacrylate copolymer, polyvinyl butyral, cellulose ester, polypropylene decylamine, and saturated polyester. Further, in the alkali-developable resin composition and the alkali-developable photosensitive resin composition of the present invention, anisole, hydroquinone, pyrocatechol, and tert-butyl tea may be added as needed. A thermal polymerization inhibitor such as phenol or phenothiazine; a plasticizer; an adhesion promoter; a filler; an antifoaming agent; and a conventional additive such as a homogenizing agent. The alkali-developable photosensitive resin composition of the present invention can be suitably applied to a support substrate for metal, paper, plastic, etc. by a well-known method such as roll coating, curtain coating, various printing, and dipping. on. Further, 104737.doc -23- and other supporting groups m can also be transferred onto other supporting substrates, and the applicable method is not limited. The alkali-developable photosensitive resin composition of the present invention can be used for various applications such as a photocurable coating material, a photocurable adhesive, a printing plate, and a photoresist for a printed wiring board, and its use is not particularly limited. Further, as the light source for the active light used for curing the alkali-developable photosensitive resin composition of the present invention, light having a wavelength of 300 to 45 Å can be used, and for example, ultrahigh pressure mercury, mercury vapor arc, carbon arc, or the like can be used. Xenon arc and so on. EXAMPLES Hereinafter, the present invention will be described in detail with reference to examples and the like, but the present invention is not limited to the examples. [Example 1] Production of alkali-developable resin composition No. 1 <Step 1>1,1-bis(4·-hydroxyphenyl)-fluorene-(i"-biphenylcyclohexylmethane production 70.5 g of biphenylcyclohexyl ketone, 200.7 g of phenol and 1 〇.15 g of thioacetic acid were charged, and 40.0 g of trifluoromethanesulfonic acid was added dropwise at 18 ° C for 20 minutes. After reacting at 17 to 19 ° C for 18 hours, The reaction was stopped by adding 500 g of water, 5 g of toluene was added, and the organic layer was washed with water until the pH became 3 to 4. The organic layer was separated. Toluene, water and excess benzene were added. Toluene was added to the residue and filtered. The precipitated solid was washed with toluene to obtain 59.2 g of pale yellow crystals (yield 51%). The melting point of the pale yellow crystals was 239.5 ° C, and it was confirmed that the pale yellow crystals were the target. 2>1,1·bis(4'-epoxypropoxyphenyl)-1-(1"-biphenyl)_1_cyclo 104737.doc • 24- 1375863 Preparation of hexyl methane into 57.5 g step 1,1·bis(4,-hydroxyphenyl)^(^-biphenyl)-1-cyclohexylamine obtained in 1 and ruthenium 95.8 g of epoxy propylene, adding 〇6〇2 g benzyl tri B After ammonium chloride, the mixture was stirred at 64 ° C for 18 hours. Then, the temperature was lowered to 54 C, 43.0 g of a 24% by weight aqueous sodium hydroxide solution was dropped, and the mixture was stirred for 30 minutes to distill off the epichlorohydrin and water, and 216 g of methyl group was added. After washing with isobutyl ketone, 2.2 g of 24% by weight sodium hydroxide was added dropwise. After stirring at 8 Torr for 2 hours, it was cooled to room temperature and neutralized with 3 parts by weight of ❶/〇 of sodium monophosphate aqueous solution. The solvent was distilled off to obtain 57 g of a yellow solid (yield: 79%) (melting point: 64.2 ° C, epoxide equivalent 282, n = 0.04). The crystals of the yellow crystals were confirmed to be the object. <Step 3> Preparation of Resin Composition N〇. 1 Loaded with 43 g of the ι,ΐ-bis(4,-epoxypropoxyphenyl)-1-(1"-biphenyl)-1 obtained in Step 2 .-cyclohexyldecane (hereinafter, referred to as compound a), ug acrylic acid (hereinafter, referred to as compound b), 0.05 g of 2,6-di-t-butyl-p-cresol, 0.11 g of tetrabutyl acetate Ammonium and 23 g of propylene glycol _ 丨 monomethyl ether _2 acetate, stirred at 120 C for 16 hours. Cooled to room temperature, adding 35 § propylene glycol · 1-monomethyl ether 2 · acetate and 9.4 g benzene The carboxylic acid dianhydride (hereinafter referred to as the compound d-fluorene) was stirred at 120 ° C for 8 hours, and further 6 μg of tetrahydrophthalic anhydride (hereinafter referred to as compound d-2) was added at 120 ° C. The mixture was stirred for 4 hours, stirred at 1 ° C for 3 hours, and stirred at 8 ° C for 4 hours at 6 °C. After stirring for 6 hours and stirring at 40 ° for 11 hours, 29 g of propylene glycol]monomethyl ether-2·acetate was added, and the alkali-developable resin of the target was obtained by using a propylene glycol monomethyl ether-2•acetate solution. No. 1 (Mw = 4 Å, Mn = 21 Å, acid value (solid type 104737. doc - 25 - 1375863 minutes) 86 mg KOH / g). Further, the 'reaction product contained in the alkali-developable resin composition No. 1' can be obtained by adding the compound b as the component (B) to the component (a). One of the hydroxyl groups of the epoxy adduct of the compound a, the compound dd as the component and the acid anhydride of the compound d-2 are constructed in a ratio of 〇68 to the epoxy adduct and the compound d-oxime and the compound. D-2 was subjected to an esterification reaction. Further, the epoxy adduct has a structure in which one epoxy group of the compound a is added at a ratio of 1.0 to the drum base of the compound b. [Example 2] Production of alkali-developable resin composition No. 2 was charged with 43 g of 1,1-bis(4'-epoxypropoxyphenyl)-oxime (1"-biphenylcyclohexyl Methyl burn (Compound a), 11 g of pro-glycolic acid (Compound b), 〇.〇5 g 2,6-di-t-butyl-p-cresol, 0.11 g of tetrabutyl sulphate and 23 g of propylene glycol 1-monomethyl ether-2-acetate, stirred at 120 ° C for 16 hours. Cooled to room temperature 'added 35 g of propylene glycol-1-monomethyl ether-2-acetate and 16 g of biphenyltetracarboxylic acid Anhydride (compound d-Ι) was spoiled at 120 ° C for 8 hours. Further, 〇.7 g of tetrahydrophthalic anhydride (compound d-2) was added and stirred at 120 ° C for 4 hours at 100 Torr: Stirring for 3 hours, stirring at 80 ° C for 4 hours, at 60. Stirring for 6 hours, stirring at 40 ° C for 11 hours, adding 29 g of propylene glycol-1 · monomethyl ether-2-acetate to propylene glycol-1 - a monomethyl ether-2-acetate solution to obtain an alkali-developable resin composition No. 2 (Mw = 8100, Mn = 2900, acid value (solid content) 89 mgKOH/g) of the target product. The reaction product contained in the developable resin composition N 〇. 2, which can be obtained by the following means: Compound b as component (B) 104737.doc •26·1375863 is added to a hydroxyl group of the epoxy adduct of the compound of the component (a) as a component (D) And the anhydride structure of the compound d-2 is 0.74, and the epoxy adduct is esterified with the compound d-oxime and the compound d-2. Further, the above epoxy addition system has a relative to the compound a. An epoxy group having a structure in which the carboxyl group of the compound b is added in a ratio of 1.0. [Example 3] Production of an alkali-developable resin composition ν〇·3 was charged with 43 g of l'l-double ( 4'-Epoxypropoxyphenyl)biphenyl)cyclohexylmethane (compound a), 11 g of acrylic acid (compound..., 〇〇5 g 2,6-di-t-butyl-p-cresol 011 g of tetrabutylammonium acetate and 23 g of propylene glycol-1-monodecyl ether-2-acetate were stirred at 12 ° C for 16 hours, cooled to room temperature, and 35 g of propylene glycol-1·monomethyl ether was added. 2_acetate, 16 g of biphenyltetracarboxylic dianhydride (compound d-oxime) and 39 mg of tetra-n-butylammonium bromide, stirred at 12 ° C for 4 hours 'stirring at l ° ° C for 3 hours At 80t: stirring for 4 hours, stirring at 6 ° C for 6 hours, and stirring at 40 ° for 11 hours, adding 29 g of propylene glycol _ 1 -monomethyl ether-2-acetate to propylene glycol 丨 曱 monoterpene ether The acetate solution obtained the inventor-developable resin composition N〇. 3 (Mw = 8600, Mn = 3000, acid value (solid content) 87 mgKOH/g). Further, the reaction product contained in the 'experimental reproducible resin composition N 0. 3 can be obtained by adding the compound b as the component (B) to the component (A). One of the hydroxyl groups of the epoxy adduct of the structure of the compound & is a ratio of 0.71 of the acid anhydride structure of the compound cM as the component (D), and the epoxy adduct is esterified with the compound d-1. Further, the above epoxy addition product has a structure in which a ring of 104737.doc • 27·1375863 oxy group is added to the compound 2, and the carboxyl group of the compound b is added to 1.0. [Example 4] base Preparation of the developable resin composition No. 4 was charged with 43 g of 1,1-bis(4'-epoxypropoxyphenyl)-1-(1"-biphenyl)·1-cyclohexylmethane. (Compound a), 11 g of acrylic acid (compound b), 0.05 g of 2,6-di-t-butyl-p-cresol, 0.11 g of tetrabutylammonium acetate, and 23 g of propylene glycol-1-monomethyl ether-2 -acetate, stirred at 120 ° C for 16 hours" cooled to room temperature, adding 35 g of propylene glycol 1-1-decyl ether-2 · acetate and 1 〇 g of biphenyltetracarboxylic dianhydride (compound d-Ι ), stirring at 120 ° C for 8 hours. Further, 6 g of tetrahydrophthalic anhydride (compound d-2) was added, and the mixture was stirred at 120 ° C for 4 hours, at 10 ° C for 3 hours, at 80 ° C for 4 hours, and at 60 ° C for stirring. After stirring at 40 ° C for 11 hours at 6 hours, 6.3 g of cresyl glycidyl ether (compound e) was added, and the mixture was stirred at 120 ° C for 1 hour. Cool to 5 〇. 〇, adding 29 g of propylene glycol-1-monomethyl ether-2-acetate, and the propylene glycol 丨 曱 曱 曱 曱 _2 _2 • • • 乙酸 目的 目的 目的 目的 目的 目的 目的 目的 目的 目的 验 验 验 验 验 验 验 验 验 验 验 验 验. 4 (Mw = 4700, Mn = 2500, acid value (solid content) 45 mg K 〇 H / g). Further, the reaction product contained in the inventor-developable resin composition N 〇·4 has a structure in which a compound b as a component (B) is added to a compound & One of the hydroxyl groups of the epoxy adduct of the structure is a ratio of the compound cM of the component (D) and the anhydride k of the compound d-2 to a ratio of 'the epoxy adduct and the compound η and the compound d-2. The esterification reaction is further carried out in such a manner that the compound as the component (8) is derived from 0.36 of the county of the structure. Further, the above epoxy addition product has a structure in which an epoxy group of the compound a is added to the epoxy group of the compound b of 104737.doc -28-1375863. [Example 5] Production of alkali-developable resin composition ν〇·5 Addition of 43 g of 1,1-bis(4,-epoxypropoxyphenyl)·“〇"_biphenyl)_ "Cyclohexylmethane (compound a), 5.7 g of phenol (hereinafter referred to as the compound hydrazine and 25 g of propylene glycol-1-monomethane _2. acetate), heated to 115 ° C. Add 〇.2 g di-based Teng' was given a sample for 4 hours at 12 ° C, 50 g of propylene glycol _.ι_monomethyl ether-2-acetate was added, cooled to 5 〇. 48 added 48 mg 2,6-di-t-butyl butyl pair - cresol, 0.49 g of benzyltriethylammonium bromide and 6.6 g of acrylic acid (compound b) were stirred at 120 ° C for 5 hours and cooled to 50 ° C. 10.27 g of biphenyltetracarboxylic dianhydride (compound) was added. D-Ι), at 120T: stirring for 8 hours. Further, 6.23 g of tetrahydrophthalic anhydride (compound d-2) was added, and the mixture was stirred at 120 ° C for 4 hours and at 100 ° C for 3 hours at 8 °. The mixture was stirred for 4 hours at °C, stirred at 60 °C for 6 hours, and stirred at 40 °C for 11 hours. Cooled to 50. 〇, added 58.3 g of propylene glycol-1-single-seal-2-acetate to propylene glycol monomethyl Alkaline-developable resin group of the target obtained by the bond _2_acetate solution Material No. 5 (Mw=4300, Mn=2200, acid value (solid content) 87 mgKOH/g) » Further, the reaction product contained in the 'alkaline developing resin composition No. 5 can be used In the above-mentioned manner, a compound d having a compound b as a component (B) and a hydroxyl group as an epoxy adduct having a structure of a compound a as a component is added as a component. - The oxime and the anhydride of the compound d-2 are constructed in a ratio of 0.73, and the epoxy adduct is esterified with the compound d-1 and the compound d-2. Further, the above epoxy addition system has a relative compound One of the epoxy groups of a, the carboxyl group of the compound b is about 〇6, the phenolic hydroxy 104737.doc -29- 1375863 of the compound is 0.4, and the sum of the compound b and the compound c is ι·〇 [Example 6] The production of the in-progressive resin composition No. 6 was added with 43 g of 1,1-bis(4'-epoxypropoxyphenyl)_!·〇 "_biphenyl)N cyclohexylmethyl amide (compound a), 7.1 g benzene age (compound c) and 25 g propylene glycol-1-monodecyl ether-2-B The ester was heated to 115. 〇. After adding 2 g of triphenylphosphine to the mixture at 4 ° C for 4 hours, 50 g of propylene glycol-i-monomethyl ether-2-acetate was added and cooled to 50 °C. 48 mg of 2,6-di-t-butyl-p-p-methyl, 0.49 g of benzyltriethylammonium bromide and 5.5 g of acrylic acid (compound..., were stirred at 120 ° C for 5 hours and cooled to 50. (: Add 10.27 g of bisphosphonate dianhydride (compound d-Ι), stir at 12 (TC for 8 hours. Further, add 6.23 g of tetrahydrophthalic anhydride (compound d-2) at 120° C stir for 4 hours, stir at l ° ° C for 3 hours, stir at 80 ° C for 4 hours, stir at 6 (rC for 6 hours, mix at π ° C for π hours. Cool to 5 〇 it, add S83 g Propylene glycol 丨 丨 曱 -2- -2- ether, the acrylonitrile _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The acid value (solid content) is 86 mg KOH/g. Further, the reaction product contained in the 'experimental developing resin composition N 〇. 6 can be obtained by the following means: The component b of the component and the compound c as the component (C) are added to one of the epoxy groups of the structure of the θ a of the component (A), and the compound dl and the compound d as the component (1)) The acid anhydride structure of -2 is a ratio of 〇·7, and the epoxy adduct is esterified with the compound d·1 and the compound d-2. The above-mentioned cyclic adduct system has a relative ratio. An epoxy 104737.doc -30- 1375863 base of the substance a, 0.5 of the compound b of the compound b, 0.5 of the benzene-prone super group of the compound c, and the sum of the compound b and the compound c are 1. [Example 7] The production of the alkali-developable photosensitive resin composition No. 1 was added with respect to 14 g of the alkali-developable resin composition No. 1 ' obtained in Example 1. 5.9 g of tris(hydroxymethyl)propane triacrylate, 2.1 g of diphenyl hydrazine, and 78 g of ethyl cellosolve' were thoroughly stirred to obtain an alkali-developable photosensitive resin composition No. 1. [Example 8] The alkali-developable photosensitive resin composition N〇. 2 was produced in comparison with 14 g of the alkali-developable resin group obtained in Example 2; the compound N〇. 2' was added to 5.9 g of tris(methyl)propyl group. The tributyl acrylate, 21 g of benzophenone, and 78 g of ethyl cellosolve were sufficiently stirred to obtain an alkali-developable photosensitive resin composition No. 2. [Example 9] Alkaline development of photosensitive light The production of the resin composition Ν〇·3 was added to 8.1 g of the alkali-developable resin composition No. 1 ' obtained in 12 g of Example 1. Pentaerythritol hexaacrylate, I; g benzophenone 47 g ethyl cellosolve and 31 g of cyclohexanone were thoroughly stirred to obtain an invisible developing photosensitive resin composition N〇3. 〇] Production of face-developing photosensitive resin composition 4 relative to 7.2 g of the alkali-developable resin composition obtained in Example 丨

No_ 1, adding 4.3 g of tris(hydroxyindenyl)propane triacrylate, 15 g of 2-methyl K[4-(indolyl)phenyl]_2-morpholinopropane·indolone and 87 g of ethyl The cellulolytic agent 'sufficient if mixed' to obtain an invisible developable photosensitive resin composition N〇. 4 〇104737.doc -31- [Example 11] Manufactured in an illustratively-developable photosensitive resin composition N〇5 20 g of the in-progress developable resin composition obtained in Example 1 N. 1 'Addition of 8.7 g of tris(hydroxymethyl)propane triacrylate, 46 g of an acrylic copolymer, and 1.7 g of 2-methyl-1- [4-(Methylthio)phenyl]_2-morpholinopropane-1-one and 65 g of ethyl cellosolve were stirred well to obtain an alkali-developable photosensitive resin composition No. 5. Further, 'the above-mentioned acrylic copolymer' is obtained by adding 2 parts by weight of mercapto acrylic acid, 15 parts by weight of mercapto acrylic acid by ethyl ester, ruthenium weight to damage methyl methacrylate, and 55 parts by weight of butyl methacrylate was dissolved in 3 parts by weight of ethyl cellosolve', 75 parts by weight of azobisisobutyronitrile was added under a nitrogen atmosphere, and reacted at 70 ° C for 5 hours. [Comparative Example 1] Production of alkaline developable resin composition Ν〇·7 was charged with 184 S bisphenol fluorene type epoxy resin (epoxy equivalent 231), 58 g of acrylic acid, 〇.26 g 2,6-di-third Butyl·p-cresol, 〇11 g tetrabutylammonium acetate, and 23 g propylene glycol-indole monodecyl ether-2·acetate at 12 Torr. Stir for 16 hours. After cooling to room temperature, 35 g of propylene glycol-i_monomethyl ether-2·acetate, 59 g of diammonium diacetate and 0.24 g of tetra-n-butyl bromide were added and stirred at uoi for 4 hours. Further, 20 g of tetrahydrophthalic anhydride was added, and the mixture was stirred at 12 ° C for 4 hours. The mixture was stirred for 3 hours, stirred at 8 ° C for 4 hours, and stirred at 60 ° for 6 hours at 4 °. After stirring for 11 hours, 9 μg of propylene glycol _ 1-monomethyl ether-2-acetate was added, and the inventor-developable resin composition of the object was obtained by using a propylene glycol _ 丨_monodecyl ether 2 -acetate solution. N〇. 7 (Mw=5000, Mn=2100, acid value (solid content) 92 7 mgK〇H/g). [Comparative Example 2] Production of alkaline developable resin composition n〇8 I04737.doc • 32·1375863 charged with 154 g of bisphenol A type epoxy resin (epoxy equivalent 19 Å), 59 g of yttrium yttrium · 26 g 2 , 6-t-butyl-p-oxime, 0.11 g of tetrabutylammonium acetate, and 23 g of propylene glycol-1·monomethyl ether·2-acetate at 12 Torr. 〇 stir “hours. Cool to room temperature” add 365 g propylene glycol-1-monomethyl ether-2-acetate, 67 g diphthalic anhydride and 0.24 g tetra-n-butyl bromide at 120. Stir for 4 hours, stir at 3 ° C for 3 hours, stir at 8 ° C for 4 hours, stir at 6 ° C for 6 hours, and at 40 ° C for 11 hours, add 90 g of propylene glycol _ 1-monomethyl ether -2-acetate, an inspectively developable resin composition of the object obtained by a propylene glycol monomethyl ether-2-acetate solution N〇. 8 (Mw=7500, Mn=2 00, acid value (solid form) (Part 1) 9 1 mg K〇H/g) [Comparative Example 3] Production of an alkali-developable resin composition N〇. 9 <Step 1> 1,1-bis(4'-hydroxyphenylbiphenyl) The production of ethane is 75 g of phenol and 50 g of 4-ethenylbiphenyl at 6 Torr. The hydrazine is heated and dissolved, and 5 g of 3-mercaptopropionic acid is added, and hydrogen chloride gas is blown while stirring for 24 hours, after which After the reaction was carried out for 72 hours, the mixture was washed with warm water, and then heated to 180 ° C under reduced pressure to distill off the evaporate. The residue was cooled with xylene, and the precipitated crystals were filtered and dried under reduced pressure. Obtained 65 g of pale yellow crystals (yield 68%). The melting point of the pale yellow crystal was 184 ° C, and it was confirmed that the yellow crystals were the target. <Step 2> 1,1-bis(4'-epoxypropoxyphenyl)-oxime Manufacture of _(1"biphenyl)ethane was charged with 37 g of ^-bis-hydroxyphenyl)-1-(1biphenyl)ethane obtained in Step 1, and 149.5 g of epoxy propylene, added 0.45 g of benzyltriethylammonium chloride was stirred at 64 ° C for 18 hours. Subsequently, the temperature was lowered to 54 ° C, and 104737.doc -33 - 32.6 g of a 24% by weight aqueous sodium hydroxide solution was dropped and stirred for 30 minutes. After de-evaporation and water addition of 14 g of methyl isobutyl ketone, water was washed, and 1.7 g of 24% by weight of sodium hydroxide was added dropwise. After stirring at 8 ° C for 2 hours, it was cooled to a temperature of 3% by weight of sodium monobromide aqueous solution, and washed with water to obtain 38.7 g of a yellow viscous liquid (yield 80%) (ring Oxygen equivalent 248 ' η = 〇 · 〇 4). It was confirmed that the yellow viscous liquid was the target. <Step 3> Preparation of Alkaline Developing Resin Composition Ν〇9 49.6 g of 1,1-bis(4,-epoxypropoxyphenyl), biphenyl group), 14.4 g Acrylic acid, 〇_〇5 g 2,6-di-t-butyl-p-nonylphenol, 0.14 g of tetrabutylammonium acetate, and 27.4 g of propylene glycol-1-monomethyl ether-2-acetic acid vinegar at 120. (: The mixture was stirred for 16 hours. After cooling to room temperature, 41.5 g of propylene glycol-1-monomethyl ether-2-acetate and 12.4 g of biphenyltetracarboxylic dianhydride were added, and the mixture was stirred at 120 ° C for 8 hours. Add 7.9 g of tetrahydrophthalic anhydride, stir at 120 ° C for 4 hours, stir at l ° °c for 3 hours, stir at 80 ° C for 4 hours, and mix at 60 ° C for 4 hours at 40 ° C. After the mixture was stirred for 11 hours, 34 g of propylene glycol-1-monodecyl ether-2-acetate was added to obtain an alkali-developable resin composition No. of the target substance in a propylene glycol_丨_monodecyl ether-2-acetate solution. . 9 (Mw=3700,

Mn = 1900, acid value (solid content) 93 mgKOH/g). [Comparative Example 4] Alkaline-developable photosensitive resin composition N〇. 6 was produced in comparison with 14 g of the alkali-developable resin composition obtained in Comparative Example 1. N'. Acryl triacetate, 2.1 g of dibenzoic acid, and 78 g of ethyl cellosolve were stirred well to obtain an alkali-developable photosensitive resin composition N 〇. [Comparative Example 5] Alkali-developed photosensitive resin composition N〇. Production of 7104737.doc -34- 1375863 5.9 g was added to 14 g of the alkali-developable resin composition N〇8 obtained in Comparative Example 2. The bismuth (methyl) propyl trimethacrylate, 2.1 g of dibenzamide and 78 g of ethyl cellosolve were thoroughly stirred to obtain an alkali-developable photosensitive resin composition No. 7. [Comparative Example 6] Production of an alkali-developable photosensitive resin composition ν〇·8 5.9 g of di(light methyl)-propyl was added with respect to 14 g of the alkali-developable resin composition N〇9 obtained in Comparative Example 3. The triacetic acid vinegar, 2.1 g of dicumyl ketone and 78 g of ethyl cellosolve were thoroughly stirred to obtain an alkali-developable photosensitive resin composition N 〇. The obtained alkali-developable photosensitive resin compositions No. 1 to 8 were evaluated as described below. That is, the r-glycidoxypropyl methyl ethoxy decane was spin-coated on the substrate, and after being spin-dried well, the above-mentioned alkali-developable photosensitive resin composition No. 1 to 7 (1300 rpm) was spin-coated. , 50 seconds) and let it dry. After prebaking at 70 ° C for 20 minutes, a solution of 5 wt% of polyvinyl alcohol was applied to prepare an oxygen barrier film. After drying for 20 minutes at TC, using a specific mask, using an ultra-high pressure mercury lamp as a light source, the film was exposed to 25.5% by weight of sodium carbonate solution for 30 seconds, and washed well. Washed and dried. Thereafter, the pattern was fixed by baking at 230 C for 1 hour. The following evaluation was carried out on the obtained pattern. The results are shown in Table 1. <Sensitivity> The exposure amount was sufficient at 1 〇〇mj/cm 2 during exposure. If it is set to a, it will be insufficient at 100 mJ/cm2 and will be set to b at 2〇〇mJ/cm2. <Resolution> 104737.doc •35- 1375863 When the line width is less than 10 μιη during exposure and development Those who can form a good pattern are evaluated as A'. Those who can form a pattern well when the line width is 1 〇 to 30 μπι are evaluated as Β, and those who can form a pattern well when the line width must exceed 30 μηι or more are evaluated as C. <Adhesiveness> According to the test method of JIS D 0202, 'cross-cutting on a coating film to a base mesh shape', a peeling test was carried out by a transparent tape, and the peeling state of the base was visually evaluated. Oh, it will be true. The peeler is set to X. <Comparative> The film after heat treatment, a) is immersed in 5 wt% 2 NaOH (aq.) for 24 hours, b) at 4 wt% 2 KOH (aq.) The appearance of the post-impregnation was visually evaluated by submerging at 5 (TC for 10 minutes, c) in 1 wt% 2 NaOH (aq.) at 80 ° C for 5 minutes. When the appearance was not changed and the resist was not completely peeled off, it was found that the resist was floated or the peeling was confirmed to be X. [Table 1]

Alkaline-developable photosensitive resin composition sensitivity resolution adhesiveness test No. 1 (Example 7) a A 〇〇 No. 2 (Example 8) a A o 〇 No. 3 (Example 9) a A 〇〇 No. 4 (Example 10) a A oo No. 5 (Example 11) a A o 0 No. 6 (Comparative Example 4) b CXX No. 7 (Comparative Example 5) b CXX No, 8 ( Comparative Example 6) b CXX The alkali-developable photosensitive resin composition of Examples 7 to 11 was high in sensitivity and good in resolution, and the adhesion between the obtained coating system and the substrate was 104737.doc * 36 · 1375863

Good alkali resistance. On the other hand, in the alkali-developable photosensitive resin compositions of Comparative Examples 4 to 6, since the sensitivity is low, it is necessary to increase the amount of exposure, and the resolution of the line is reduced, and if the line width is not 30 μm or more, it cannot be formed. The adhesion and alkali resistance of the obtained coating film to the substrate were not as expected. Industrial Applicability The alkali-developable photosensitive resin composition of the present invention is excellent in transparency, adhesiveness, alkali resistance, and the like, and can form a fine pattern with high precision. 104737.doc 37.

Claims (1)

1375863 Patent Application No. 094,130,706, the entire disclosure of the entire disclosure of Japanese Patent Application No. (J.J.J.J.J.J.J.JJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJJ In the case of a reaction product obtained by esterifying a polybasic acid anhydride (D), the epoxy adduct has an epoxy resin (A) represented by the following general formula (1), an unsaturated monobasic acid (B), and a phenol selected from phenol. a structure of a compound (C) which is a compound, an alcohol compound, an amine compound, and a carboxylic acid, and the above-mentioned cyclic oxime adduct' has a structure in which one of the above epoxy groups is unsaturated with respect to one epoxy group of the above epoxy resin (A) The acid (b) is an aliphatic group of 0.1 to 1.0 of the above compound (C), a phenolic hydroxyl group, an alcoholic trans group, an amine group or a thiol group of 0 to 0.9, and the above unsaturated monobasic acid (b) has a structure in which a carboxyl group and a phenolic hydroxyl group, an alcoholic hydroxyl group, an amine group or a carboxyl group of the compound (C) are added in a ratio of 0.1 to 1.0, and the above S is determined to be relative to the above ring One of the oxygen adducts, with the above polybasic acid anhydride (D The anhydride structure is made at a ratio of 〇.1 to 1. ;; (wherein Cy represents a cycloalkyl group having 3 to 10 carbon atoms, X represents a hydrogen atom, a phenyl group which may be substituted by an alkyl group or an alkoxy group having 1 to 1 carbon atom, or a carbon atom number of 3 to 10 The cycloalkyl group, γ and z each independently represent a carbon atom 104737-1010709.doc 1375863 an alkyl group of 1 to 10, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or a halogen. The atom, the above alkyl group, the above alkoxy group and the above alkenyl group may also be substituted by a halogen atom, n represents a number of 〇 to 1 ,, p represents a number of 0 to 5, and r represents a number of 〇 to 4). 2. The alkali-developable resin composition of claim 1, wherein the epoxy compound (E) is further reacted in the reaction product. 3. The alkali-developable resin composition according to claim 1 or 2, wherein in the above general formula (I), Cy is a cyclohexyl group, X is a phenyl group, and p and r are fluorene. An alkali-developable photosensitive resin composition containing the alkali-developable resin composition of claim i and a photopolymerization initiator. 104737-i010709.doc