TWI377215B - - Google Patents

Description

137-7215 IX. Description of the Invention: [Technical Field] The present invention relates to a radiation sensing composition and a laminate obtained from the radiation sensing composition on a substrate, and more particularly, a radiation-sensitive composition for producing an electronic component such as a display element, an integrated circuit component, and a solid-state imaging device, a laminate having a resin film obtained from the radiation-sensitive composition on a substrate, a method for producing the same, and a method for producing the same And an electronic component composed of the laminate. [Prior Art] Various resin films are provided as electronic components such as display elements, integrated circuit elements 'solid-state imaging elements, color filters, and black matrixes, as protective films for preventing deterioration or damage thereof, for A flattening film for planarizing the surface or wiring of the device and an electrical insulating film for maintaining electrical insulation. Further, in the element such as the thin film transistor type liquid crystal display element or the integrated circuit element, in order to insulate the wiring between the wiring layers, a resin film as an interlayer insulating film is provided. Such a resin film requires various properties such as insulation properties, heat resistance, transparency, water absorption resistance, and chemical resistance. Recently, in such an electronic component, a material which can perform multilayer wiring, maintain high insulation between layers, and form a resin film having sufficient flatness is required. Therefore, a radiation-sensitive resin composition containing a crosslinking agent such as an alkali-soluble cyclic olefin resin having an ester group, a quinonediazide compound, and methylol melamine is proposed (Patent Document 1). However, it was found that the resin film obtained by using the radiation-sensing resin composition has a so-called low medium

2232-6917-PF 5 8 1 // η The electrical properties, heat resistance, flatness, transparency, and solvent resistance of the insulating film are good. When viewing the entire substrate, the thickness of the resin film formed is not fixed. Both of them are checked, and the storage stability of the polymer or the like is precipitated during storage, and problems occur.

Patent Document 2 discloses a radiation-sensitive resin composition comprising an alicyclic skeleton and comprising an acid-soluble resin, a radiation-sensitive acid generator, and a specific solvent. This invention attempts to form a good resistant having good sensitivity, resolution, developability, etc., particularly transparency with respect to radiation, etc., by a combination of a specific resin and a specific solvent. membrane. Further, Patent Document 3 proposes a radiation-sensitive resin composition comprising an alicyclic olefin resin, an acid generator, a crosslinking agent, and a solvent, characterized in that the solvent system contains at least a special ethylene glycol system. Compound. In the radiation-sensitive resin composition, the radiation-sensitive resin composition has higher performance required in the radiation-sensitive resin composition, in particular, in the resin-sensitive resin composition. The solubility stability of 臈 uniformity or the decrease in coating unevenness which affects light interference cannot be adequately handled. In addition, at the same time, because of environmental concerns, safer compounds must be used. In particular, a solvent which is contained in a radiation-sensitive resin composition in a large amount is required to use a less toxic solvent.

[Patent Document 1] Japanese Laid-Open Patent Publication No. Hei. No. 2003-156838. * [Summary of the Invention] '* [Problems to be Solved by the Invention] The present invention has been made to cope with the miniaturization, thinning, and improvement of safety of components in recent years; and to provide a good electrical property and good solubility stability. A radiation-sensing composition which is not coated with a high degree of safety and is highly safe, a laminate in which a resin film composed of the radiation-sensitive composition is formed on a substrate, and a method for producing the laminate are used as Question. [Means for Solving the Problem] The present inventors have made a thorough review of the above-mentioned problems, and as a result, found a cyclic olefin polymer containing a protic polar group, a radiation-sensitive composition, and a cross-linking. The radiation-sensitive composition contained in the crosslinking agent and the solvent is used in the use of 2-heptanone, cyclohexanone, internal glycol monodecyl ether acetate, diethylene glycol monoethyl ether or diethylene glycol ethylene glycol When a known solvent is used as a solvent, the solubility stability becomes insufficient, and coating unevenness is observed, and when diethylene glycol ethyl methyl group is used as a solvent, A radiation-sensitive composition having a high solubility stability, no uneven coating, and high safety; according to these opinions', the present invention has been completed. As described above, according to the present invention, a radiation sensing composition is provided which is a radiation sensing combination comprising a cyclic olefin polymer containing a protic polar group, a radiation sensing composition, a crosslinking agent, and a solvent. And a solvent comprising a dialkylene glycol dialkyl fluorene having 2,200,917,917-PF?8 137-7215 having two alkyl groups different from each other in the same molecule. In the radiation-sensitive composition of the present invention, it is preferred that the dialkylene glycol dialkyl fluorene having two alkyl groups different from each other in the same molecule have two different alkyl groups in the same molecule. The base of ethylene glycol dialkyl ruthenium. In the radiation-sensitive composition of the present invention, it is particularly preferred to have a diethylene glycol dialkyl ether-ethylidene glycol ethyl sulfonate bond having two alkyl groups different from each other in the same molecule. According to the present invention, there is further provided a laminate comprising a substrate and a resin film formed by using the radiation-sensing composition on the substrate. In the laminated system, a resin film can be formed on a substrate by using the above-described radiation-sensing composition, and then, if necessary, cross-linking the resin to obtain a laminate. In the laminate of the present invention, the resin film may be a patterned resin film. According to the present invention, there is still provided a method of forming a resin film on a substrate by using a radiation-sensitive composition, irradiating active radiation on the resin film, forming a latent image pattern in the resin film, and then contacting the developer film with the developer film, A method of manufacturing a laminate comprising a substrate formed by forming a patterned resin film on a substrate and a patterned resin film formed on the substrate. In the method for producing a laminate of the present invention, a resin crosslinking reaction can be carried out after forming a patterned resin film on a substrate. 2232-6917-PF 8 1377215 Further, by the present invention, an electronic component composed of the above laminated body is provided. [Effect of the Invention] According to the present invention, a radiation-sensitive composition capable of obtaining a resin film having good dissolution stability and extremely low coating unevenness is obtained. The laminated resin film in which the resin film is formed on the substrate by using the radiation-sensitive composition has excellent electrical characteristics and extremely small coating unevenness. Therefore, it is suitable as, for example, a display element, an integrated circuit element, or a solid-state imaging element. A protective film such as a color filter or a black matrix, a planarizing film for flattening the element table or wiring, and a film for maintaining electrical insulation: a film (including a thin transistor type liquid crystal) A material for an electronic component such as an interlayer insulating film of an electric cream insulating film or a fresh tin resist film of an integrated circuit component or a microlens or a spacer. [Embodiment] The radiation-sensitive composition of the present invention contains a proton-based polar group: a cyclic-difficient polymer, a radiation-sensitive composition, a crosslinking agent, and a solvent to contain a radiation-sensing composition. It is based on the use of specific compounds as a solvent. In the ring-shaped flue-cured poly(a) containing a protic polar group used in the present invention, the protic polar group is preferably an atom of the 15th and 6th groups of the periodic table in the hetero atom, more preferably the periodic table. The atoms of the first and second cycles of Groups 15 and 16 are particularly preferably oxygen atoms to directly bond to the atomic groups of the hydrogen atoms. A series of specific examples of protonic polar groups: having several groups, pot acid

2232-6917-PF 1377215 is a polar group of an oxygen atom such as a sulfonic acid group or a hydroxyl group; and a nitrogen atom having a primary amino group, a secondary amino group, a primary amide group, a secondary sulfonium group, and the like. A polar group; a polar group having a sulfur atom such as a thio group or the like. Even in these, it is preferable to have an oxygen atom, and more preferably a carboxyl group. In the present invention, the protic polar group contained in the cyclic olefin polymer containing a protic polar group is not particularly limited to the number, or a different type of protic polar group may be contained. In the present invention, the protic polar group contained in the cyclic olefin-based polymer containing a protic polar group may be bonded to a cyclic olefin monomer unit or may be bonded to a monomer unit other than the cyclic olefin monomer. However, it is preferred to incorporate a cyclic olefin monomer unit. In the present invention, the cyclic olefin polymer which is a portion other than the protic polar group constituting the cyclic rare hydrocarbon polymer containing a protic polar group (hereinafter referred to as "base portion") may be a cyclic olefin. Any of a single polymer and a copolymer, and a copolymer of a cyclic olefin and another monomer, and may also be a hydrogen additive of these: a cyclic olefin polymer system containing these protic polar groups It is possible to combine and use different ones of the components alone or in combination of two or more. The cyclic dilute-based polymer containing a protic polar group used in the present invention may be a polymer composed only of a monomer unit derived from a cyclic olefin monomer (a) containing a protic polar group. It may also be a monomer unit derived from a cyclic olefin monomer (a) containing a protic polar group and a monomer derived from another monomer which can be copolymerized to a cyclic olefin monomer (a) having a protic polar group. a copolymer composed of body units. 2232-6917-PF 10 1377215 The ratio of the monomer unit containing a protonic polar group and the monomer unit containing a protonic polar group used in the present invention to the monomer alone The monomer unit having a protic polar group/unit unit other than this is selected such that the weight ratio is usually IM/ο〇/90, preferably 90/10 to 20/80, more preferably 80//. 2〇~30/70 range. Specific examples of the cyclic olefin (a) containing a protic polar group are 5-hydroxycarboxybicyclo[221]heptyl-2-alkene, 5-methyl-5φ hydroxycarboxybicyclo[2.2.1] Heptyl-2-oxo, 5-carboxymethyl-5-hydroxycarboxybicyclo[2.2.1]heptyl-2-oxene, 5-exo-6-endo-hydroxycarboxybicyclo[2.2.1]g Base 2-olefin, 8-hydroxycarboxytetracyclo[4.4.0.12'5171°] 12-3 olefin, 8-methyl-8-hydroxycarboxytetracyclo[4.4. 0·12'517'1() ]12_3—olefin, 8-external-g_endo-di-propyl-carboxytetracyclo[4.4.0. 12517'丨]] 12-olefin olefin-containing cyclic olefin; 5-(4) Monohydroxyphenyl)bicyclo[2.2.1]heptyl-2-oxene, 5-methyl-5-(4-hydroxyphenyl)bicyclo[2.2.1]heptyl-2. Olefins, 8-(4-hydroxyphenyl)tetracyclo[4.4.0.12,517,丨°] dodeca-3-olefin, 8-mercapto- 8-(4-hydroxyphenyl)tetracyclo[4. 4 0.12, 517, 10] 12- 3 - a cyclic olefin containing a hydroxyl group such as an olefin, etc., even among these, it is preferably a cyclic hydrocarbon having a carboxyl group. . The cyclic rare hydrocarbons containing these protic polar groups may be used singly or in combination of two or more. The single system which can be copolymerized to the cyclic olefin monomer (a) having a protic polar group is a cyclic olefin having a polar group other than a protic polar group 2232-6917-PF 11 8 1377215 monomer (b) Any cyclic olefin monomer having no polar group (referred to as "a cyclic olefin monomer having a non-polar group") (c), and a monomer (d) other than a cyclic olefin. • Among these, 'preferably a cyclic olefin monomer (b) having a polar group other than a protic polar group and a cyclic olefin monomer (c) containing a nonpolar group, more preferably containing a protic polar group The polar olefin monomer (b) is a specific example of a polar group other than a protic polar group: ester® group (collectively, alkoxy sulfo group and aryloxy group), N-substituted Yttrium imino group, epoxy group, dentate atom, cyano group, thiol oxidized carboxyl group (an acid anhydride residue of diremediation), alkoxy group, slow base, tertiary amino group, sulfhydryl group, halogen atom, acryl Wait. Among these, 'preferably, an ester group, an N-substituted quinone group and a cyano group, more preferably an ester group and an N-substituted quinone group, particularly preferably an N-substituted arylimine group. As a series of cyclic olefins containing an ester group: for example, 5-acetic acid di-ruthenium [2-2.1] heptyl- 2 - dilute smoke, 5-methoxymethylbicyclo[2.2.1] heptyl- 2—olefin, 5-methyl-5-methoxycarboxybicyclo[2.2.1]heptyl-2-alkene, 8-acetic acid tetracyclo[4.4.0.12, 5171°]12:3— Olefin, 8-oxooxycarboxytetracyclo[4.4.0.12517,1°] 12-3 olefin, 8-ethoxylated tetracycline [4.4.〇.12,517,1°]121-3 Hydrocarbon, 8-11-propoxycarboxytetracyclo [4. 4. 0. 12.517, 丨 °] 12- 3 - dilute hydrocarbon, 8-isopropoxy carboxytetracycline [4. 4. 0 · 12.517, 1D] 12-1 olefin, 8_ η-butoxycarboxytetracyclo [4.4.0.12, 5171°] 12-1,3-olefin, 8-methyl- 8 2232-6917-PF 12 8 1377215-▼ oxygen Carboxyltetracycline [4.4.0. 12 517, "] Twelve _3 - a hydrocarbon, a benzyl 8-ethoxycarboxytetracyclo ring [4. 4. 0. 12·5ι7 ι°ι+ -. J D--3 - olefin, 8-aryl- 8-n-propoxy-heavyyltetracycline [4.4.0.12517, oxime. Tert-olefin, 8-f-yl-8-isopropoxycarboxytetracyclo[4 4 〇12- 3 olefin, 8-methyl-8-n-butoxy-smilyl fluorenyltetracycline [4 4. 〇. ΐ2·5ι71. ] Twelve _ 3 - olefin, 8 - ( 2. 2. 2 ~ = 麁 7 々 - fluoroethoxyl carboxy) tetracyclo [4.4.0.12 '517' 丨. ] 12- 3 - olefin, 8-methyl ~ 8 ~ (2.2.2 - trifluoroethoxy carboxyl) tetracyclic [4.4. 〇.12.4 7, 丨. ] Thirty 3 - dilute hydrocarbons, etc. Examples of the cyclic olefin group containing an N-substituted brewed imine group include, for example, a base group (5-n-cyclohexane 2,3-di-supplemental-based imine). As a series of cyclic olefins containing a cyano group: for example, s #r 〇-gas-based four aids [".ο·", "] twelve _3 - dilute hydrocarbons, 5-aryl bicyclo [22. A 2-olefin, etc. As a series of cyclic olefins containing a halogen atom, for example, 8-ring U.4.0.l2f. ] 12-3 - dilute hydrocarbons, 8 gas four r. , T丞 8 _ gas four rings [4.4·〇.ι2, 5ι71Ί 12-1 olefins, etc. The ring-shaped flue-cured tobacco having a polar group other than these protic polar groups may be used alone or in combination of two or more. Specific examples of the ring-monomer (4) containing a non-polar group - a ring [2. 2.1] heptyl-2 - a dilute hydrocarbon (common name: original illusion, 5 ethyl - 5 clothes [2. 2.1] Heptyl-2-oxo, 5-butyl-bis[2.2.1]heptyl-2-dihydrocarbon, 5-ethethylene-bicyclo[2 2"]heptyl

2232-6917-PF 13 1377215 — 2—dilute hydrocarbon, 5-methylene-bicyclo[2. 2 chuanheptyl-2-ene, 5-ethenyl-bicyclo[2.2.1]heptyl-2 - olefin, tricyclo[4.3.0.12,5] deca- 3,7-diolefin (common name: dicyclopentadiene), tetracyclic [8.4.0.1^4. fifteen_3,57,1211_ Pentaolefin, tetracyclic U. 4_ 〇. I2·5.丨7·1〇]10__ 3 - olefin (common name: four-ring twelve-carbon roast), 8-hydrazine-four-ring [4. 4. 〇. l2,5. 17,丨. ] 12-3_ olefin, 8 ethyl-tetracyclo[4. 4. 0. I2·5. ]12_3_olefin, 8-methylene

- four rings [4.4.0.12.5.17, 丨. ] Twelve _3 olefin, 8-ethylene-tetracyclo [4.4. 〇. 12' 517'1. ] Twelve _3_olefin, 8_vinyl-tetracyclic [4.4.〇.125.17’1. ] 12-3 olefin, 8-propenyl-tetracyclo[4_4.0.ΐ2'5.ΐ7'1β] -12-olefin, pentacyclic [6. 5. L丨3'6. 〇2 '7. 〇9'13] fifteen-three, 10 - olefin, cyclopentene, cyclopentene, 1' 4 ~ methanol - 1,4, 4a, 5, 10, l〇a - hexahydroquinone, 8~phenyl-tetracyclo[4.4.0. I2,5.Γ.η]12-3 olefin, tetracyclo[9.2.).0.0 8]12-3, 5, 7, 12 — Tetraolefin (also known as 1,4 - methanol 1,4, 4a,9a - tetrahydrogen - 9H - 芴), five rings ^7·4·0.13'6·1" '13·02'7] fifteen 4,11 - Diene, pentacyclo[9. 2. 1. 〇2'丨' 〇3'8] penta-5, 12-diene, etc. These non-polar cyclic olefins may be used singly or in combination of two or more. As a representative example of the monomer (d) other than the cyclic olefin, a series of chain smoke is mentioned. As a series of chain-like hydrocarbons, for example, ethylene; propylene, 1 - butyl, 1 - pentyl, 1-hexene, 3-mercapto- 1 -butene, 3-methyl-1-pentene, 3 - B Base 1 - pentyl, 4 - methyl - 1 - pentyl, 4 - methyl - 1 - 14

2232-6917-PF 8 ^77215 dilute 4'4~~ dimethyl- 1 - hexaploate, 4, 4 - dimethyl - 1 - pentane, 4-ethyl-i-hexene, 3-ethyl- 1 Number of carbons such as monohexene, 1-octene, 1-terpene, 1-10-carbene, fluorene-tetradecene, 1-hexadecene, 1-octadecene, 1-10 rabbit 2 to 20 of α-anthracene; 1,4-hexane dilute hydrocarbon, 4-methyl-14-hexane diolefin, 5-methyl-ι 4-hexadiene, 1,7-octane diene, etc. Conjugated diolefins and the like. These single systems may be used singly or in combination of two or more. An ideal production method of the cyclic olefin compound containing a protic polar group used in the present invention is a method in which a cyclic olefin monomer (a) containing a protic polar group is polymerized and blended as needed. The method of hydrogen addition. The cyclic olefin monomer (a) containing a protic polar group may be blended as needed to obtain a cyclic olefin monomer (a) having a protic polar group and a ring copolymerizable with the protic polar group. The monomer of the olefin monomer (a) (the aforementioned monomer (b), (c) or (4)) is copolymerized. Further, the cyclic olefin-based polymer containing a protic polar group used in the present invention may be introduced into a protonic polar group by a conventional method in a cyclic smoky polymer which does not contain a protic polar group. After the base, a cyclic hydrocarbon polymer containing a protic polar group is obtained by a method of performing hydrogen addition. The hydrogen addition can be carried out with respect to the polymer before the proton polar group is introduced. 1 In the case of the above-mentioned cyclic dilute (tetra) polymer containing a protic polar group, the protic polar group may be a precursor thereof, or may be a chemical reaction such as decomposition or hydrolysis by light or heat. Precursor conversion

2232-6917-PF 15 1377215 becomes a protic polar group. For example, in the state where the protic polar group is a carboxyl group, an ester group may be used instead of the protic polar group. The cyclic olefin-based polymer which does not contain a protic polar group can be obtained by using the monomers (b) to (d) described in the month. At this time, it is of course also possible to use a monomer having a protic polar group in combination. As a variation for introducing a protic polar group, a compound having a protic polar group and a reactive carbon-carbon unsaturated bond in one molecule is usually used. Specific examples of such a compound include acrylic acid methacrylic acid, angelic acid, citric acid, oleic acid, elaidic acid, erucic acid, ebutyric acid, maleic acid, fumaric acid, and citraconic acid. An unsaturated carboxylic acid such as mesaconic acid, itaconic acid, atropic acid or cinnamic acid; dilute propyl alcohol, methyl vinyl methanol, crotonyl alcohol, methallyl alcohol, 1-phenyl Dilute-rn-propylene-bupropanol, 3-butene-propanol, 3-butene-2-alcohol, 3-monomethyl-3------------ —alcohol, 2_ ^:3—butan-2-alcohol, 2-methyl-3′butan-bupropanol, 4-^ol, 4-methyl-4-penta-butanol, 2-hexene- An unsaturated alcohol such as phenol or the like. The denaturation reaction can be carried out in the presence of a free radical generator. ", the usual method, usually, the polymerization method for each of the above monomers may be a ring-opening polymerization method or an additional polymerization method. ", 'Normal method', for example, 100 is used as a polymerization catalyst system, and a compound is suitably used. These polymerization catalysts can be used in combination with metal or the like which are singular or sulphate, respectively. The amount of the polymerization catalyst is either a combination of two or a combination of two substances: a mole ratio of a cyclic hydrocarbon, and a metal combination.

2232-6917-PF 16 1377215 2' 000' 000, preferably 1:500~1:1, 〇〇〇, 〇〇〇, more ideal is summer: 1,000~1: 500, range of 〇〇〇 . The hydrogen addition of the polymer is usually carried out using a hydrogen addition catalyst. The hydrogen addition catalyst system can be used, for example, in the case of hydrogen addition of an olefin compound. Specifically, a uniform catalyst such as a Ziegler type, a noble metal complex catalyst, and a supported noble metal catalyst can be used. In these hydrogen-adding catalysts, it is preferable to carry out hydrogen addition by selectively causing a side reaction such as denaturation of a functional group and selectively carbon-carbon unsaturated bonds in the polymer. It is a noble metal complex catalyst of ruthenium, osmium or the like, and particularly preferably a highly electron-donating nitrogen-containing heterocyclic poly-fast compound or a phosphine-supported ruthenium catalyst. The weight average molecular weight (Mw) of the cyclic olefin-based polymer containing a protic polar group used in the present invention is usually 丨, 000 丨, 〇〇〇, 〇〇〇, preferably 1,500 to 100. , 〇〇〇, more ideal is 2, 〇〇〇~1〇, 〇〇〇 range. The molecular weight distribution of the cyclic olefin-based polymer containing a protic polar group used in the present invention is usually 4 or less, preferably 3 or less, in terms of a ratio of a weight average molecular weight to a number average molecular weight (Mw / Μη). More preferably, it is 2. 5 or less. The moth price system of the cyclic olefin polymer containing a protic polar group used in the present invention is usually 200 or less, preferably 5 Å or less, more preferably 10 or less. When the price of the cyclic olefin polymer containing a protic polar group is in this range, it has a particularly good heat resistance and is suitable. The radiation-sensing composition used in the present invention is a compound which can absorb a radiation of ultraviolet 2232-6917-PF 17 8 1377215 or an electron beam to cause a chemical reaction, and can control the protonic polarity used in the present invention. The alkali solubility of the cyclic olefin polymer. Examples of such a radiation-sensitive composition include, for example, an azide compound such as an styrene compound, a diarylsulfonium salt or a quinonediazide compound, but it is preferably an azide compound, particularly preferably ruthenium. A diazide compound. As the quinonediazide compound, for example, an ester compound between a quinonediazidesulfonate acid halide and a compound having a phenolic hydroxyl group can be used. As a series of brewed diazido sulfonic acid halides, 1,2-naphthoquinonediazide-5-sulfonic acid chloride, 1,2-naphthoquinonediazide-1,4-sulfonic acid chloride, 1,2-benzopyrenediazide-5-sulfonic acid chloride, and the like. As a representative example of a compound having a benzene group, 1,1,3 di(2,5-dimethyl-4-hydroxyphenyl)-3-phenylpropane, 4, 4, one [1] — [4-[1 -[4-hydroxyphenyl]_;ι_methylethyl]phenyl]ethylidene]bisphenol. ® as a series of compounds other than this with 2, 3, 4 and 2 basic benzophenones, 2, 3, 4, 4, tetra-tetrabenzopyrene, 2 - double (4-hydroxyphenyl)propane, tris(4-hydroxyphenyl)methane, tris(4-hydroxy-3-methoxyphenyl)ethane, 1,1,2,2-tetrakis(4-hydroxybenzene) Ethylene, an oligomer of a phenol resin, an oligomer obtained by copolymerizing a compound having one or more phenolic hydroxyl groups, and dicyclopentadiene, etc. These radiation-sensitive compositions may be individually or separately Two or more types of 2232-6917-PF 18 8 1377215 may be used in combination. The amount of the radiation-sensitive composition to be used is usually 1 to 1 part by weight, preferably 5 to 50 parts by weight, more preferably 1 to 1 part by weight, based on 1 part by weight of the cyclic olefin polymer containing a protic polar group. A range of from 1 to 40 parts by weight. When the amount of use of the radiation-sensitive composition is in this range, the agent for patterning the resin film formed on the substrate is such that the difference in solubility between the radiation-irradiated portion and the non-irradiated portion of the radiation becomes large, so that The patterning becomes easy, and the radiation sensitivity is also high. Therefore, it becomes ideal. In the present invention, as the crosslinking agent, a functional group having two or more, preferably three or more, protonic polar groups capable of reacting with a cyclic olefin polymer containing a protic polar group in the molecule is used. Examples of the functional group capable of reacting with a protic polar group include an amine group, a carboxyl group, a hydroxyl group, a valent oxy group, an isocyanate group, and the like, and an amine group, an epoxy group, an isocyanate group, and more preferably a ring. Oxygen. As a specific example of such a crosslinking agent, a series of aliphatic polyamines such as hexamethylenediamine; aromatics such as 4, 4'-diaminodiphenyl ether and diaminodiphenyl hydrazine; a polyamines; 2,6_bis(4,monoazidebenzylidene)cyclohexanone, 4'4 - a stack of gas-based diphenyl maples, etc.; aramid, polyhexamethylene Polyamines such as phthalimin, polyhexamethylene isodecylamine, etc. 'N,N,Ν', Ν', N", N"-(hexaalkyloxyfluorenyl) Melamines such as melamine; guanidine, Ν', Ν", Ν,,, (tetraalkoxymethyl) glycoluril, glycoluril; ethylene glycol bis(indenyl) propyl citrate, etc. Acetate compound; hexamethylene diisocyanate polyisocyanate, isophorone

2232-6917-PF 8 1377215 Isocyanate-based polyisocyanate, phenylene diisocyanate-based polyisocyanate-added water, isocyanate-based diisocyanate, etc. Methyl)cyclohexane, 1,4-di(hydroxymethyl)prolinane; 1,3,4-trihydroxycyclohexane; ring having an alicyclic skeleton and having more than 2 epoxy groups An oxygen compound having an oxyphenol phenolic skeleton and having an epoxy compound having two or more epoxy groups, an epoxy compound having a phenol phenolic aldehyde lattice and having two or more epoxy groups, having a bisphenol A skeleton and having two The epoxy compound of the above epoxy group has a poly-B-epoxy compound such as an epoxy compound having two or more epoxy groups and a naphthyl skeleton. Even among these, it is preferable that the polyfunctional epoxy compound is particularly excellent in coating film formability, and therefore it is preferable to have an alicyclic skeleton and have two or more epoxy groups, and more preferably have A polyfunctional epoxy compound having three or more epoxy groups. These crosslinking agents may be used singly or in combination of two or more kinds. The amount of the crosslinking agent used is usually 1 to 1 part by weight, preferably 10 to 70 parts by weight, more preferably 2 parts by weight, based on 1 part by weight of the cyclic olefin polymer containing a protic polar group. 〇~5〇 parts by weight. When the crosslinking agent position is in this range, heat resistance is highly improved. The radiation-sensitive composition of the present invention must use a dialkylene glycol dialkyl ether having two alkyl groups different from each other in the same molecule as a solvent. By using a dialkylene glycol dialkyl ether having two alkyl groups different from each other in the same molecule as a solvent, solubility stability can be improved to reduce coating unevenness. a dialkylene group having 2 alkyl groups different from each other in the same molecule 2232-6917-PF 2〇8 1377215 The ethylene glycol dialkyl group is preferably in the range of 1 to 4 carbon atoms. More ideally, it is a range of 1 to 3. • In addition, the number of carbons of an alkylene chain having two alkyl groups different from each other in the same molecule is preferably in the range of 1 to 4. The range is more ideally in the range of 2 to 3. Specific examples of the diethylene glycol dialkyl ether having two alkyl groups different from each other in the same molecule include diethylene glycol ethyl methyl ether and diethyl ethylene glycol thiol Base, diethylethylene glycol butyl group # ether, diethylene glycol ethyl propyl ether, diethylene glycol butyl ethyl mystery, ethylene glycol butyl propyl group, etc. Two ethylene glycol dialkyl ethers having two different alkyl groups in the same molecule; dipropylene glycol ethyl methyl ether, dipropylene glycol methyl propyl ether, dipropylene glycol butyl decyl ether, dipropylene a divinyl glycol dialkyl group having two alkyl groups different from each other in the same molecule, such as ethyl propyl group, dipropylene glycol butyl ethyl group, and ethylene glycol butyl propyl ether. Ether, etc. Among these, it is preferable to have two alkyl diethylene glycol dialkyl ethers in the same molecule, particularly preferably diethylene glycol. diol ethyl decyl ether. The amount of the dialkylene glycol disulfide having two alkyl groups different from each other in the same molecule is usually used in an amount of 100 parts by weight based on 100 parts by weight of the cyclic dilute polymer containing a protic polar group. 20 to 10, 〇〇〇 by weight, preferably 50 to 5,000 parts by weight, more preferably 1 〇〇 to 1, and 〇〇〇 by weight. In the present invention, a dialkylene glycol dialkyl ether having two alkyl groups different from each other in the same molecule, 2232-6917-PF 21 8 1377215, and another solvent may be used in combination. _ As a solvent series which can be used together, for example, a chain and a cyclic ketone such as methyl ethyl ketone, cyclohexanone, 2 heptanone 4-hydroxy-4-indenyl-2-heptanone, etc.; Alcohols such as ethanol, propanol, butanol, 3-methoxyl-3-mercaptopropanol; cyclic ethers such as tetrahydrofuran and dioxane; ethylene glycol monoethyl ether, ethylene B Glycol monopropyl ether, ethylene glycol monobutyl ether; propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, etc. monoalkylene glycol monoalkyl hydrazine; ethylene B Glycol monoterpene glycolic acid® 8曰, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monobutyl acetate, propylene glycol Monoalkylene glycol monoalkyl ether esters such as methyl ketone acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, etc. Alkyl glycol monoether acetates; ethylene glycol dimercapto ether, ethylene glycol monoethyl ether; propylene glycol dimethyl sulfonate, propylene glycol diethyl mystery, etc. Diethylene glycol dialkyl ether; diethylene glycol monomethyl shrine, ethylene glycol monoethyl sulfonate; dipropylene glycol monomethyl hydrazine, dipropylene glycol mono-ethyl ether, etc. Ethylene glycol monoalkyl ethers; ethylene glycol dimethyl ether, diethylene glycol diethyl ether; dipropylene glycol dimethyl ether, dipropylene glycol diethyl hydrazine, etc. in the same molecule Dialkylene glycol dialkyl ether having the same two alkyl groups; triethylene glycol monomethyl mystery 'triethylene diethyl alcohol monoethyl bond, tripropanol monomethyl , tripropylene glycol monoethyl ether, etc. of trialkylene glycol diacetate monoalkyl ether; triethylene glycol ethylene glycol test, triethylene glycol ethylene glycol diethyl ether, triethylene glycol ethyl ether Methyl shout; tripropylene glycol dimethyl mystery, tripropylene glycol diethyl sing, tripropylene glycol ethyl hydrazine 22

2232-6917-PF 8 1377215 trialkylene glycol dialkyl ethers such as alkyl ethers; aromatic hydrocarbons such as benzoquinone and diphenyl; ethyl acetate, butyl acetate, ethyl lactate, 2 monohydroxy-2-methylpropionic acid methyl, 2-hydroxymethylpropionic acid ethyl, ethoxyacetic acid ethyl, hydroxyacetic acid ethyl, 2-hydroxy-3-methylbutanoic acid methyl, 3 - methoxyacetic acid methyl, 3-methoxypropionic acid ethyl, 3-ethoxypropionic acid ethyl, 3-ethoxypropionate decyl, butyrolactone and the like; N - Methylformamide, N,N-dimercaptocaramine, n-methyl-2

Pyridoxine, N-methylacetamide, phthalamide such as N,N-dimethylacetamide; dimercaptoid code. These other solvent systems may be used alone or in combination of two or more. The radiation-sensitive composition of the present invention may contain a resin component other than the cyclic olefin-based polymer containing a protic polar group, or other compounding agent, etc., as needed. The other resin component may, for example, be a cyclic olefin polymer having no protic polar group, a styrene resin, a vinyl chloride resin, a propylene resin, a polyphenylene ether resin, or a polypropyne sulfide. Resin, polycarbonate resin, polyester resin, polyamide resin 'polyether oxime resin, polyfluorene resin, polyimide resin, rubber and elastomer. These other members may be used singly or in combination of two or more kinds, and the amount thereof is appropriately selected within a range not impairing the effects of the present invention. Examples of the other complexing agent include a sensitizer, a surfactant, a latent acid generator, an oxidation preventive, a light stabilizer, and an auxiliary agent.

2232-6917-PF 23 Charge inhibitor, defoamer, wisher's dye, etc. As the sensitizer, it is preferably 3 ('for example, (3,2-b) 14 芏 its flag phase ~ 鲖 '10H-pyridine-(3,2_b)-1,4-open thiazide, urine The oxazolidine red will be 1 Μ B in the urea, bus acid, phthalic anhydride, 1-hydroxy cumin = anhydride imine, etc. ― gas, tetraoxane (tetra), maleic acid surfactant System 佶 + shadow enhancement, etc., enumeration: such as (= after the line) prevention, oxidized ethylene stearyl hydrazine, polyoxyethylene: polyoxyethylene sulphate, sulphurized vinyl oleyl Polyethylene oxides such as ethers; polyoxyethylene ethoxylates, polyoxyethylene phthalic phenyl: polyethoxylated aryl ethoxylated dilaurate: ί ethylene oxide monostearic acid Non-ionic surfactants such as polyoxyethylene dialkyl vinegar such as vinegar, · a-type surfactant; Shih-class surfactant; (partial) acrylic copolymer-based surfactant, etc. (4) a cationic polymerization catalyst for producing an acid by heating for the purpose of improving the heat resistance and the chemical property of the radiation-sensitive composition of the present invention, It is a salt of salt, a benzothiazide, a salt, a salt, a salt, etc. Even among these, it is preferable to use a sulfonium salt and a benzothiazole salt.| As an oxidation preventive agent, it can use the normal polymer. Examples of the phenol-based oxidation inhibitor, the phosphorus-based oxidation inhibitor, the sulfur-based oxidation inhibitor, and the lactone-based oxidation inhibitor. Examples of the phenol-based oxidation inhibitor include 2'6-di-t-t (third)-butyl. Benzyl 4-nonylphenol, methoxyphenol, styrenated phenol, η-h octadecyl-3-(3,5,2-second-butyl- 4'-monophenyl)propionic acid g, 2', 2,·~_;π; 2232-6917-PF 24 (3) 7215

~ bis (4~ fluorenyl-6-tert-butyl phenol), 2_t-butyl- 6~(3'-third-tert-butyl~5, fluorenyl- 2, monohydroxybenzyl ) a 4-methyl methacrylate, 4,4, monobutylene-bis-(3-methyl-6-second-butylbenzene), 4,4'-thio-double (3-曱) Base 6 - 2 - butyl phenol), pentaerythritol tetra [3- (3, 5-di-tert-triphenyl-4-hydroxy) propionate], alkylated bisphenol, and the like. Examples of the phosphorus-based oxidation preventing agent include triphenylphosphite and tris(nonylphenyl)phosphite. As a series of sulfur-based oxidation inhibitors, dilauryl thiodipropionic acid and the like are mentioned. Even among these, from the viewpoint of yellowing during heating, it is preferable that the divalent butyl group is oxidized, even if it is in it, it is preferably tris-butyl-4-hydroxyphenyl. The preventive agent tetraol tetrakis [3-(3,5-di-dipropionate). The light stabilizer may be a benzophenone, a salicylate, a benzotriazole, or a cyanoacrylate. Any one of a UV absorber such as a metal-missing salt system, a hindered amine system (HALS), or the like, and a radical which generates light due to light. Even among these, it is preferable that the HALS has a piperidine structure. The compound of the present invention has less coloration and good stability in the radiation-sensitive composition of the present invention. As a specific compound series, bis(2,2 6 6 -tetramethyl~4-piperidinyl)sebacate, 1 , 2, 2, 6, 6 - pentamethyl-4 piperidine / 12 yards 1,2, 3, 4 butyl sulphide acid, bis (1-octyl oxidized 2, 2, 6,6-tetramethyl- 4 piperidyl) sebacate, etc. As a further auxiliary agent, for example, a functional decane coupling agent, etc., as a specific example thereof For three Yue Yue silicon oxy benzoic acid group, r - methylpropan dilute stuffed trimethoxy Silane, vinyl triacetoxy Silane, owned by group B

2232-6917-PF 25 1377215, r-cyclohexyl)ethyldimethoxydecane, r-isocyanate propyltriethoxydecaneoxypropoxypropyltrimethoxydecane, (3,4-epoxycycloyltrimethyl) The radiation-sensitive composition of the present invention may be a cyclic olefin polymer containing a protic polar group, a radiation-sensitive composition, and a crosslinking agent, and may be added to other components as needed. It is produced by dispersing or dissolving a solvent containing a diamethylene glycol dialkyl ether having two alkyl groups different in the same molecule, and is dissolved or dispersed in a solvent. The method of the various components can be carried out according to a conventional method, for example, by stirring using a stirrer and a magnetic stirrer or by using a high-speed homogenizer, a dispersion, a star agitator, a two-axis mixer, a ball mill, a three-roller, or the like. The radiation-sensing composition is preferably used after being dissolved or dispersed in a solvent, for example, after being filtered using a filter having a pore size of 5%. The solid content concentration of the radiation-sensitive composition of the present invention is usually from 1 to 70% by weight, preferably from 5 to 50% by weight, more preferably from 1 to 4% by weight. The solid content concentration is in the range. In the case of the present invention, the laminated system of the present invention is composed of a substrate and a resin film formed by using the radiation-sensitive composition of the present invention on the substrate. In the invention, for example, a printed circuit board, a chip substrate, a glass substrate, a plastic substrate, etc. can be used. Further, in the field of displays, a thin crystal type liquid crystal display element is formed in a glass substrate or a plastic substrate to be used. Color filters, black matrix, etc. 26

2232-6917-PF 8 137-7215 The thickness of the resin film is usually in the range of 〇1 to 100, preferably 0.5 to 50 Am, more preferably 0.5 to 30/zm. The layered system of the present invention can be obtained by using a radiation-sensitive composition of the present invention to form a resin film on a substrate, and then blending the resin film as needed. The method of forming the resin film on the substrate is not particularly limited, and for example, a method such as a coating method or a film deposition method can be used. The coating method is, for example, a method in which the radiation-sensitive composition is applied to a substrate, followed by heating and drying, and removing the solvent, followed by blending as needed. As a method of applying the radiation-sensitive composition to the substrate, for example, a spray method, a spin coating method, a roll coating method, a mold coating method, a doctor blade method, a spin coating method, a rod coating method, or the like may be employed. Various methods such as screen printing. The heating and drying conditions are different depending on the type or blending ratio of the various components, but it can be usually 30 to 15 (TC, preferably 60 to 120 t, usually 0.5 to 90 minutes, preferably 1 to 6 minutes, More preferably, it is 1 to 3 minutes. The film deposition method is, for example, after the radiation-sensitive composition is applied onto a substrate such as a resin film or a metal film, and then the solvent is removed by heating and drying to obtain a B-seat film. A method of laminating the B pedestal film on a substrate. The heat drying condition is different depending on the type or blending ratio of the various components, but it can be usually 30 to 150 ° C, preferably 60 to 120 ° C, usually 〇 5 to 90 minutes, preferably 1 to 60 minutes, more preferably 1 to 30 minutes. For film lamination, a pressure laminator, a press, a vacuum laminator, a vacuum press, a roll laminator, etc. may be used. Press machine to enter 27

2232-6917-PF 8 1377215 • Line. In the present invention, the known film system may be a patterned resin crucible (hereinafter referred to as "patterned resin film"). - A laminated body of the present invention, in particular, a laminated system in which a patterned resin film is formed on a substrate, is used as various electronic components. The resin film patterned on the substrate can be formed as follows. First, as described above, in the resin film formed on the substrate, the latent image of the desired pattern is formed by irradiating the active radiation. "If the active radiation system can activate the radiation-sensitive compound, the radiation-sensitive composition can be changed. There is no particular limitation on the solubility. Specifically, a single-wavelength ultraviolet ray such as ultraviolet rays, g-rays or i-rays, KrF excimer laser light, ArF excimer laser light or the like; a particle line of an electron beam or the like can be used. In order to form the latent image pattern by selectively irradiating these actinic radiation patterns in a pattern, it is possible to illuminate the purple--external line and the uterine ray by a conventional mask method by, for example, reducing the projection exposure apparatus or the like. A method of light such as i-ray, KrF excimer laser light, or ArF excimer laser light, or a method of drawing by a particle line such as an electron beam. In the state where light is used as the active radiation, the light may be a single wavelength light or a mixed wavelength light. The irradiation conditions are appropriately selected in accordance with the active radiation to be used. However, for example, in the case of using light having a wavelength of 200 to 450 nm, the irradiation system is usually 10 to 1 〇〇〇mJ/cm 2 , preferably 50 to 500 mJ / The range of cm2 is determined by the irradiation time and illuminance. After the active radiation 2232-6917-PF 28 1377215 is irradiated as described above, the resin film is heated to a temperature of about 6 to 130 ° C for about 1 to 2 minutes. Next, development is performed on the latent image pattern formed on the resin film to make it remarkable. In the present invention, such a process is referred to as "patterning", and the patterned resin film is referred to as a "patterned resin film". As the developer, an aqueous solution of a basic compound is usually used. The basic compound may be an inorganic compound or an organic compound. Specific examples of these compounds include alkali metal salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium citrate, and sodium citrate; aqueous ammonia; primary amines such as ethylamine and n-propylamine; a secondary amine such as a base amine or a di-n-propylamine; a tertiary amine such as triethylamine or methyldiethylamine; tetramethylammonium hydroxide, tetraethylhydroxyammonium, tetrabutylhydroxyammonium, or a cholesterium a salt such as a base; alkalamine such as dimethylethanolamine or triethanolamine; a quinone, a piperidine, a 1,8-dioxin ring [5.4 〇] ten _ 7 - a dilute smoke, a u-two &quot a cyclic amine such as a quinone ring [4. 3. 〇] 九-5-olefin or N-methylpyrrolidone. The test compound may be used alone or in combination of two or more. As the aqueous medium for the water-repellent solution, a water-soluble organic solvent such as ?, methanol or ethanol can be used. The aqueous solution may be added with an appropriate amount of a surfactant or the like. As a method of contacting the developer with a latent image of the tree having a latent image, a method such as a drop method, a spray method, a π/Χ method, or the like is used. The development conditions are selected in the field 〇~1〇〇. θ 1n on〇iU〇(: preferably 5~55°c, more ideally 疋10~3〇C range 'in the range of 通* 30~180 seconds. In this way, it becomes A s β After the patterned resin film for the purpose of π + , is formed on the substrate, it is required to be bonded to the substrate, the back surface of the substrate, and the substrate.

2232-6917-PF 29 1377215 Development of the end of the fishing, the purpose of this, the substrate can be rinsed by the rinse. After the rinsing treatment, the residual rinsing liquid is removed by compressing air or compressing nitrogen. Further, in order to passivate the radiation-sensitive compound in order to meet the need, it is also possible to irradiate the active radiation on the entire surface of the substrate having the patterned resin film. For the irradiation of the active radiation, a method exemplified by the formation of the aforementioned latent image pattern can be utilized. The resin film can be heated at the same time as the irradiation or the irradiation. As a series of heating methods, for example, a method of heating a substrate in a heating plate or an oven. The temperature is usually in the range of 100 to 3001, preferably 120 to φ 200 °C. After the patterned resin film is formed on the substrate, the resin is crosslinked. The cross-linking of the patterned resin film formed on the substrate can be selected in accordance with the type of the crosslinking agent, but it is usually carried out by heating. The heating method can be carried out, for example, using a hot plate, an oven, or the like. The heating temperature is usually 180 to 250 t, and the heating time is appropriately selected by the size or thickness of the resin film and the use of a machine or the like. For example, in the state where a hot plate is used, it is usually 5 to 60 minutes. In the state, the call usually becomes a range of 30 to 90 minutes. The heating system can be carried out under an inert gas atmosphere as needed. The inert gas system may contain no oxygen and does not oxidize the resin film, and examples thereof include nitrogen, argon, helium, neon, gas, nitrogen, and the like. Even among these, nitrogen and nitrogen are preferred, and gas is particularly preferred. In particular, the inert gas having an oxygen content of (M% by volume or less, preferably Q (tetra)% or less), particularly nitrogen may be used. These inert gas systems may be used singly or in combination of two or more kinds. 30

2232-6917-PF

(S, the following is a list. The reference is made to the synthesis example and the examples, and the parts and % of each of the examples are not particularly limited, and the characteristics are defined by the present invention. Evaluation by the method. [The weight average molecular weight (heart) and the number average molecular weight (Mn) of the polymer] The polyisoprene converted molecule [hydrogenation rate] was determined by the gelation chromatography method. The ratio of the hydrogen number of the hydrogen-carbon double bond Mohr number to the carbon-carbon double bond Mohr number before hydrogen addition was determined by NMR spectroscopy. [Iodine price] Measured according to J IS K 0 0 7 Ο B [Safety of Solvent] The LDso value obtained by using the acute toxicity test by oral application of a solvent to a mouse is judged by the following criteria. In addition, the value is based on product safety data. In the case of propylene glycol monomethyl ether acetate, it is a distributor of Diecell Chemical Industry Co., Ltd., and it is a distributor of Toho Chemical Industry Co., Ltd.. 〇: 5, OOOmg/kg or more X: less than 5, OOOmg / kg [Solubility stability] The contents of the radiation-sensing composition were individually stored in an environment of -20 ° C and 5 ° C for 1 day. The presence or absence of the sediment was observed and judged on the basis of the following criteria. 2232-6917-PF 31 1377215 〇. Under any environmental conditions of -20C and 5 ° C, no sediment was observed after storage. △: After -20 ° C, after storage, the precipitate was observed, but • Yes, no sediments were observed after storage under 5 C ambient conditions. X: After storage at -20 ° C ambient conditions and 5. (: After storage of environmental conditions, sediments were observed [Formation and coating unevenness of the radiation-sensitive composition resin film] After 50 ml of the radiation-sensitive composition was dropped on a glass substrate with a low-reflection Cr film of 550 x 6 50 x 0.7 mm, and then spin-coated, The hot plate was dried at 95 ° C for 2 minutes to form a coated substrate having a film thickness. The interference line inspection lamp HCN052NA (manufactured by Toshiba Corporation) was irradiated onto the coated substrate by the state of the interference line. And observe the traces of the residual dripping solution, "drop marks" and spin When the solution is applied, the unevenness of the line shape generated when the solution is diffused is "unevenness of the line", and the determination is made by the following criteria. These unevenness are all shown in the micro film of the undetectable area of the thickness meter. Thickness difference. _ 〇: No unevenness was observed. △: Only traces of dripping were observed. X. Both traces and uneven lines were observed. [Dielectric properties of resin film] on the substrate Using a rotator (manufactured by Mika Sa Co., Ltd.), after applying the radiation-sensing composition, by heating the plate, it is dried at 95 ° C for -12 seconds, and film formation is performed by touch. When the needle-type film thickness meter (manufactured by Tencoal Co., Ltd.) was used for measurement, it was 3 to 1 2, and the film 2232-6917-PF 32 1377215 was not subjected to exposure treatment, and it was in a tetramethylammonium hydroxide 0.3% aqueous solution at 23°. C, after 100 seconds of immersion to perform development processing, the rinsing treatment was performed for 1 minute by ultrapure water. Then, the light intensity of 365 nm was irradiated to ultraviolet light of 5 mW/cm 2 over the entire surface of the resin film. Passivation of radiation sensing compounds. Then, heating was carried out for 1 hour by a heating plate of 23 (rc). An aluminum film of 〇3/m was formed on the resin film, and a dielectric constant of 1 MHz was measured in an environment of 23. According to the dielectric constant, the determination is made based on the following criteria: 〇: The dielectric constant is less than 3. X: The dielectric constant is 3 or more [Synthetic Example] 8-hydroxycarbonyltetracyclo[4. 4_ 0. I2.5. 17, 丨 °] 12- 3 - olefin 6 parts by weight, N - stupid one (5 - raw spinane - 2, 3 - dicarboxy quinone imine) 4 〇 parts by weight, 1 - 1.3 parts by weight of alkene, 1,3-dimethylimidazolidinyl- 2 -(tricyclohexylphosphine)benzylidene dichloride hydrazine 5 parts by weight and tetrahydrofurfuran 400 parts by weight, charged to nitrogen The replaced glass was placed in a pressure-resistant reactor, stirred, and reacted at 70 ° C for 2 hours to obtain a polymer solution A (solid content concentration: about 20%) » Transfer a portion of the polymer solution A To the high pressure error attached to the mixer at 150 ° C, hydrogen is dissolved at a pressure of 4 MPa, and the reaction is carried out for 5 hours to obtain a polymer containing a hydrogenated polymer (hydrogenation rate of 100%). Liquid B (solid content concentration: about 20%). A heat-resistant container in which 1 part by weight of activated carbon powder is added to 100 parts by weight of the polymer solution B, placed in an autoclave, stirred, and, at 33

2232-6917-PF 8 1377215 15rc, the gas was dissolved for 3 hours at a pressure of a, and the dissolved activated carbon was taken out by a fluorine crucible having a pore size of 0.2/Z m to obtain a polymer solution. The knife is filtered without any delay. The human solution is injected into the ethanol to solidify and dry to form a faint, polymer. M"550 of the obtained polymer obtained from polyisoprene. , Μη is 3,2 0 0. And 'Iodine price is 1. [Example 1]

1 part by weight of the polymer obtained in Synthesis Example 1 and 5 parts by weight of diethylene glycol ethyl methyl hydrazine as a bismuth medium, and 4, 4' one as 12 = diazide compound ( ^—[4-[丨-[4-hydroxyphenyl]-1-methylethyl]phenyl]ethylidene]bisphenol (1 mole) and 1>2-naphthoquinonediazide-- 5-sulfonic acid vapor (2.5 mol) condensate weight part, polyfunctional epoxy compound containing alicyclic structure as cross-linking agent (molecular weight 2,700, epoxy number 15, Diecell chemical industry) 20 parts by weight of EHPE3150), 1 part by weight of r-glycidoxypropyltrimethoxydecane as a secondary auxiliary agent, and an anthrone-based surfactant (KP-341, manufactured by Shin-Etsu Chemical Co., Ltd.) After mixing and dissolving, the mixture was filtered through a filter made of polytetrafluoroethylene having a pore size of 0.45 #m to prepare a radiation-sensitive composition. For the radiation-sensitive composition, the dissolution stability and the coating were not evaluated. The average dielectric constant. The results are shown in Table 1. [Comparative Examples 1 to 4] In addition to the substitution of diethylene glycol ethyl methyl Further, propylene glycol monomethyl ether acetate (Comparative Example 1), diethylene glycol dimethyl ether (Comparative Example 2), diethylene glycol diethyl ether (Comparative Example 3), and 2223- were respectively used. 6917-PF 34 1377215

A radiation-sensitive composition was prepared in the same manner as in Example 1 except that a mixed solvent of 1:4 (weight ratio) between ethylene glycol monoethyl ether and propylene glycol monoethyl ether (Comparative Example 4) was used. With respect to the radiation-sensitive composition, dissolution stability, coating unevenness, and dielectric constant were evaluated. The results are shown in Table 1. [Table 1] Solvent (: *1) Safety Dissolution Stability Coating Uneven Dielectric Coefficient Example 1 DEGEME 〇〇〇〇Comparative Example 1 PGMEA 〇XX*2 〇Comparative Example 2 DEGDME X 〇〇〇Comparative Example 3 DEGDME X 〇Δ 〇Comparative Example 4 DEGEE 〇〇X 〇PGEE X

[Notes in Table 1] *1 DEGEME: Diethylene glycol ethyl methyl ether PGMEA: Propylene glycol monomethyl ether acetate DEGDME: Diethylene glycol dimethyl ether DEGDEE: Diethylene glycol diethylene glycol The base ether DEGEE: diethylene glycol monoethyl ether PGEE: propylene glycol monoethyl ether* 2 has poor solubility stability, and insoluble matter is present in the coating film. From the results of Table 1, it is known that the state of diethylene glycol ethyl decyl ether which is a dialkylene glycol dialkyl ether having two alkyl groups different from each other in the same molecule is used. Next, a radiation-sensitive composition having no problem in safety, good dissolution stability, and no uneven coating was obtained, and 2232-6917-PF 35 8 1377215 was used to obtain a resin film having good dielectric properties. It is known that, in contrast to the use of a solvent other than this, the radiation-sensing composition obtained is safe, e has a problem, and any of the dissolution stability and coating unevenness are caused. . Display unsatisfied knot [Simple diagram description] None [Main component symbol description] None

2232-6917-PF 36

Claims (1)

Ι3Π215 April, 2011, Amendment Replacement Page / No. 094106968 X. Patent Application Range: 1. A radiation-sensitive composition 'from a cyclic olefin polymer containing a protic polar group, a radiation-sensitive composition, a crosslinking agent And a solvent composition comprising: a dialkylene glycol dialkyl ether having two mutually different alkyl groups in the same molecule, wherein the two molecules have two mutually in the same molecule The different alkyl diethylene glycol dialkyl ethers are diethylene glycol ethyl methyl ether. 2. The radiation-sensitive composition according to claim 1, wherein the protic polar group is a carboxyl group. 3. A layered body comprising: a substrate and a layer formed on the substrate by a resin film formed by using the radiation-sensitive composition according to the scope of the invention; Integral. 4. The laminate according to claim 3, wherein the resin film is a patterned resin film. A method for producing a laminate, comprising: forming a substrate on a substrate by using a radiation-sensitive composition according to claim 1 or 2, and forming the substrate 6. The method of producing a laminate according to the fifth aspect of the invention, wherein the resin film is formed on the substrate, and then the resin is crosslinked. 7. A method of manufacturing a laminate according to the scope of the patent application, 2232^6917-PF1 37. The replacement page of April 26, 101, is a substrate and a patterned resin film formed on the substrate. The composition is obtained by using the radiation-sensitive composition according to claim 1 or 2; forming a resin film on the substrate; irradiating the active film on the resin film; forming a latent image pattern in the resin film; and then forming a resin film Contacting the developing solution; visualizing the latent image pattern; forming a patterned resin film on the substrate 8. The method for producing a laminate according to the sixth aspect of the patent application is to form a patterned resin film on a substrate.仃 仃 专利 乂 乂 乂 乂 专利 专利 专利 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 9. 2232-6917-PF1 38