TW200936563A - Fluorine-containing compound, fluorine-containing polymer, and composition and film each containing the polymer - Google Patents

Abstract

Disclosed is a compound represented by formula (I). A polymer having excellent heat resistance and an alkali-developable photosensitive composition can be obtained from the compound (I). [In the formula (I), R1-R3 each represents a hydrogen atom, a fluorine atom or an aliphatic hydrocarbon group; R4-R6 each represents a single bond or an alkylene group; R7 represents a single bond or an aliphatic hydrocarbon group; R8 represents an aliphatic hydrocarbon group; and R9 represents a hydrogen atom or an aliphatic hydrocarbon group. In this connection, one of R1-R9 represents a fluorine atom or a group substituted by a fluorine atom.]

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fluorine-containing compound, a fluorine-containing polymer, and a composition and film containing the same. [Prior Art] It is known that a fluorine-containing polymer has excellent characteristics such as water repellency and oil repellency, and thus various fluorine-containing polymers and fluorine-containing monomers derived therefrom have been known. For example, JP-A-44-26M6 discloses (1) a method in which a fluorine-containing epoxide is reacted with a vinyl carboxylic acid to produce a fluorine-containing hydroxy unsaturated ester, and (2) the fluorine-containing hydroxy unsaturated ester is easily polymerized. And (3) the polymer imparts water repellency and oil repellency to the fiber product. Further, the embodiment 2 of the publication No. 44-26286 discloses a compound represented by the formula (a-1), and the example i is a compound represented by the formula (a-2).

However, Japanese Patent Publication No. 44_26286 discloses only that the polymer obtained from the fluorine-containing hydroxy unsaturated ester has water repellency and oil repellency, and does not disclose other characteristics of the polymer. SUMMARY OF THE INVENTION -5-200936563 [Disclosure of the Invention] One of the required properties of an optical material and an optical article is heat resistance. However, the polymer described in Japanese Patent Publication No. Sho 44-26286 discloses only good oil repellency, and this document does not disclose other characteristics such as heat resistance. After reviewing the heat resistance of the aforementioned polymer, it was found that the performance was poor. SUMMARY OF THE INVENTION An object of the present invention is to provide a polymer having high heat resistance and a novel fluorine-containing compound which can form the polymer. In order to achieve the foregoing object, the present inventors have completed the present invention after careful review. The present invention provides the following compounds and the like. The present invention provides a compound represented by the formula (I). [Chemical 2]

In the formula (I), R1 to R3 each independently represent a hydrogen atom, a fluorine atom, or an aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group. R4 to R6 are each independently a single bond, or a Ci-io extending base which may be substituted by a fluorine atom. R7 is a single bond or an aliphatic hydrocarbon group which may be substituted by a fluorine atom. R8 is a Ci-24 aliphatic hydrocarbon group which may be substituted by a fluorine atom. R9 is a hydrogen atom, or a Ci.24 aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group, or a Cl.24 aliphatic hydrocarbon group which is partially substituted with an oxygen atom. -6- 200936563 However, any one of R1 to R9 is a fluorine atom or a group substituted by a fluorine atom. In the present specification, "Ca.b" means a carbon number of a or more and b or less. Further, the compound represented by the formula (I) is abbreviated as "compound (I)". The compounds represented by other chemical formulas are also the same. The present invention further provides a polymer for use as a monomer constituting the compound represented by the formula (I). Preferably, in the above polymer, 1. In the compound represented by the formula (I), R8 is a polymer of a C i -24 aliphatic hydrocarbon group substituted by a fluorine atom, 2. Among the compounds represented by the formula (I) R9 is a polymer of a hydrogen atom. 3. A polymer of a copolymer of a compound represented by the formula (I) and a copolymerizable compound, 4. A compound copolymerizable with the compound represented by the formula (I) is propylene© A polymer of an acid ester, methacrylate or a mixture thereof. The present invention further provides a film formed by containing the above polymer. Further, the present invention provides a photosensitive composition comprising the above polymer (A), sensitizer (B), curing agent (C) and solvent (Η), 2. containing the above polymer (Α), and a curing agent ( C), photoacid generator (D) and solvent (Η), if necessary, an amine compound (Ε) photosensitive composition, 3. containing the above polymer (Α) 'polymerizable compound (F), light polymerization 200936563 A photosensitive composition containing a initiator (G) and a solvent (Η), 4. A curable composition containing the above polymer (Α), a curing agent (C), and a solvent (Η). A preferred sensitizer (Β) is a benzoquinonediazide compound. A preferred hardener (C) is a melamine compound. A preferred photoacid generator (D) is a ruthenium compound. The polymerizable compound (F) is preferably at least one selected from the group consisting of a polyfunctional acrylate compound and a methacrylate compound group. More preferably, the polymerizable compound (F) is at least one selected from the group consisting of a 5- to 6-functional acrylate compound and a 5- to 6-functional methacrylate compound. A preferred photopolymerization initiator (G) is a lanthanide compound. [Best Mode for Carrying Out the Invention] <Compound (I) > The fluorine-containing compound of the present invention is represented by the formula (I).

R3 (!) In the formula (I), R1 to R3 each independently represent a hydrogen atom, a fluorine atom, or a C]_13 aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group. (^-13 aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group, such as the group of the following (1) to (4). -8- 200936563 (ηalkyl (including linear, branched, and cyclic alkane) For example, methyl, ethyl, η-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, η-pentyl, η-hexyl, η-heptyl, η-octyl Base, n-fluorenyl, η-fluorenyl, cyclohexyl, (cyclohexyl)methyl. (2) Perfluoro-substituted hydrocarbyl group The perfluoro-substituted hydrocarbyl group includes the following groups (i) to (iii). Perfluoro linear alkyl group, for example, trifluoromethyl, perfluoroethyl, perfluoro-η-propyl, perfluoro-n-butyl, perfluoro-η-pentyl, perfluoro-n-hexyl, Perfluoro&lt;-η-heptyl, perfluoro-η-octyl, perfluoro-η-fluorenyl, perfluoro-η-fluorenyl. (ii) perfluoro-branched alkyl φ, for example, perfluoro- 1-methylethyl, perfluoro-2-methylpropyl, perfluoro-3-methylbutyl, perfluoro-4-methylpentyl, perfluoro-5-methylhexyl, perfluoro-6 -methylheptyl, perfluoro-7-methyloctyl, perfluoro-8-methylindenyl, perfluoro-9-methylindenyl. (iii) perfluorocyclic hydrocarbon group such as 'perfluorocyclohexyl Perfluoromonocyclic a perfluoro-crosslinked cyclic hydrocarbon group such as a perfluoroadamantyl group or a 2-perfluoroadamantyl group. 200936563 (3) Partial fluorine-substituted hydrocarbon group The partially fluorine-substituted hydrocarbon group includes the following groups (i) to (W). (i) a partially fluorine-substituted alkyl group such as 'monofluoromethyl group, difluoromethyl group. (Π) an alkyl group which may be substituted by a perfluoro linear alkyl group (hereinafter referred to as "perfluoro linear alkyl-substituted alkane" Base ") @ For example, (trifluoromethyl)methyl, 2-(trifluoromethyl)ethyl, (perfluoroethyl)methyl, 2-(perfluoroethyl)ethyl, (perfluoro- Η-propyl)methyl, 2-(perfluoro-η-propyl)ethyl, 2-(perfluoro-η-butyl)methyl, 2-(perfluoro-η-butyl)ethyl, (perfluoro-η-pentyl)methyl, 2-(perfluoro-η-pentyl)ethyl, (perfluoro-η-hexyl)methyl, 2-(perfluoro-η-hexyl)ethyl, (perfluoro-η-heptyl)methyl, 2-(perfluoro-η-heptyl)ethyl, (perfluoro-η-octyl)methyl, 2-(perfluoro-η-octyl) , (perfluoro-η-fluorenyl)methyl, 2-(perfluoro-η-fluorenyl)ethyl, (perfluoro- η η-fluorenyl)methyl, 2-(perfluoro-η-癸()) can be perfluoro-branched An alkyl-substituted alkyl group (hereinafter abbreviated as "perfluoro-branched alkyl-substituted alkyl group"), for example, (perfluoro-1-methylethyl)methyl, 2-(perfluoro-1-methyl-ethyl) Ethyl, (perfluoro-2-methylpropyl)methyl, 2-(perfluoro-2-methylpropyl)ethyl, (perfluoro-3-methylbutyl)methyl, 2 -(perfluoro-3-methylbutyl)ethyl, (perfluoro-4-methylpentyl)methyl, 2-(perfluoro--10-200936563 4-methylpentyl)ethyl, Perfluoro-5-methylhexyl)methyl, 2-(perfluoro-5-methylhexyl)ethyl, (perfluoro-6-methylheptyl)methyl, 2-(perfluoro-6-methyl Ethyl heptyl)ethyl, (perfluoro-7-methyloctyl)methyl, 2-(perfluoro-7-methyloctyl)ethyl, (perfluoro-8-methylindenyl)methyl 2-(Perfluoro-8-methylindenyl)ethyl, (perfluoro-9-methylindenyl)methyl, 2-(perfluoro-9-methylindenyl)ethyl. © (iv) an alkyl group which may be substituted by a perfluorocyclic hydrocarbon group, for example, an alkyl group which may be substituted by a perfluorocyclic alkyl group such as (perfluorocyclohexyl)methyl or 2-(perfluorocyclohexyl)ethyl; And (1-perfluoroadamantyl)methyl, 2-(1-perfluoroadamantyl)ethyl, (2-perfluoroadamantyl)methyl, 2-(2-perfluoroadamantyl)ethyl, etc. An alkyl group substituted with a perfluoro crosslinked cyclic hydrocarbon group. (4) a hydroxy-substituted alkyl group such as 'hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-n-propyl, 2-hydroxy-η-propyl, 3-hydroxy-n-propyl Base, 1-hydroxy-isopropyl, 2-hydroxy-isopropyl, 1-hydroxy-η-butyl, 2-hydroxy-η-butyl, 3-hydroxy-η-butyl, 4-hydroxy-η - butyl. R1 to R3 are preferably a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group. R1 and R2 are more preferably a nitrogen atom, and R3 is more preferably a hydrogen atom or a methyl group. In the formula (I), R4 and R6 are each independently a single bond or a C!-]alkyl group which may be substituted by a fluorine atom. The c, .i G alkyl group which may be substituted by a fluorine atom is, for example, the groups of the following (1) to (3). -11 - 200936563 (1) alkylene group, for example, methyl, ethyl, η-propyl, η-butylene, η-amyl, η-extension, η-heptyl, η - stretching octyl, η - stretching thiol, η - stretching thiol. (2) Perfluoroalkylene groups, for example, difluoromethyl, perfluoroextended ethyl, perfluoro-η-propyl, perfluoro-η-butylene, peroxy-η-exetyl, all Fluorine-n-extension hexyl, perfluoro-[eta]-t-heptyl, perfluoro-[eta]-exenyl, all-gas-[eta]-extension, perfluoro-[eta]-extension. (3) a partially fluorine-substituted alkylene group, for example, 2,2-difluoro-1,3-propanyl, 2,2,3,3-tetrafluoro-1,4-tert-butyl, 2,2,3 ,3,4,4-hexafluoro-1,5-exopentyl, 2,2,3,3,4,4,5,5-octafluoro-1,6-extension, 2,2,3, 3,4,4,5,5,6,6-decafluoro-1,7-extended heptyl, 2,2,3,3,4,4,5,5,6,6,7,7-ten Difluoro-1,8-exenyl, 2,2,3,3,4,4,5,5,6,6,7,7,8,8-tetradecafluoro-1,9-extension , 2,2,3,3,4,4,5,5,6,6, 7,7,8,8,9,9-hexadecafluoro-1,10-extension. R4 to R6 are preferably a single bond, a methyl group, an ethyl group and a propyl group. R4 to R6 are more preferably a single bond, and R5 is more preferably a methyl group. In the formula (I), R7 is a single bond, or an aliphatic hydrocarbon group which may be substituted by a fluorine atom (particularly an alkyl group which may be substituted by a fluorine atom). A Cb15 aliphatic group of R7 which may be substituted by a fluorine atom The hydrocarbon group is, for example, the group of the following (1) to (5). -12- 200936563 (1) A chain hydrocarbon group, for example, a methyl group, an ethyl group, a propyl group, an n-butylene group, a pentyl group , η-extension hexyl, n_extension, octyl, hydrazine, hydrazino, 1,1-dimethylexylethyl, 2-methylexylpropyl, methylene An alkyl group such as an alkyl group; and an extended alkenyl group such as a vinyl group or a propylene group; Q (2) a monocyclic hydrocarbon group such as a cyclic alkyl group such as a 1,2-cyclohexyl group; and an ls2 - ring a cycloalkenyl group such as a hexenyl group, etc. (3) a crosslinked cyclic hydrocarbon group of a 2-valent crosslinked cyclic hydrocarbon group such as norbornane, norbornene, adamantane and tetracyclo [6·2 · 1.13'6·02,7] A hydrogen atom in which two hydrogen atoms of a crosslinked cyclic hydrocarbon group such as a tetraethylene group are bonded to each other. 〇(4) Perfluoroalkylene group, for example, difluoromethyl group , perfluoroextended ethyl, perfluoro_η_propyl, perfluoro-η-butylene, perfluoro-η-exetyl, all _η_Extension, perfluoro-η-heptyl, perfluoro-η-exenyl, perfluoro-η-extension, perfluoro-η-extension, (5) partial fluorine substituted alkyl For example, 2,2-difluoro-1,3-propanyl, 2,2,3,3-tetrafluoro-1,4-butylene, 2,2,3,3,4,4-hexafluoro -1,5-Exopentyl, 2,2,3,3,4,4,5,5-octafluoro- -13- 200936563 1,6-extension, 2,2,3,3,4,4 ,5,5,6,6-decafluoro-1,7-exetylene, 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-1, 8·Extending octyl, 2,2,3,3,4,4,5,5,6,6,7,7,8-tetradecyl-1,9-extension, 2,2,3, 3,4,4,5,5,6,6, 7,7,8,8,9,9-hexadecafluoro-1,10-extended fluorenyl. R7 is preferably a methyl group and an ethyl group. In the formula (I), R8 is a Ch24 aliphatic hydrocarbon group. The hydrocarbon group may not be substituted by a fluorine atom, but is preferably substituted by a fluorine atom. The Ci-24 aliphatic hydrocarbon group substituted by a fluorine atom is as follows (1) to (1) to 2). (1) Perfluoro-substituted hydrocarbyl perfluoro-substituted hydrocarbyl group includes the following groups (i) to (iii). (i) Perfluoro linear alkyl group, for example, trifluoromethyl, perfluoroethane Base, perfluoro-η-propyl, perfluoro-n-butyl, perfluoro-η-pentyl, perfluoro-η-hexyl, perfluoro-η-heptyl, perfluoro-n - octyl, perfluoro-η-fluorenyl-perfluoro-η-fluorenyl, perfluoro-n-~j--•, ❹-fluorine-η--12-base, perfluoro-η-ten Three-hospital base, perfluoro-η-fourteen-yard base, perfluoro-η-fifteenth base, perfluoro-η-hexadecanthon, perfluoro-η-heptadecane, perfluoro-η-ten Eight courtyard base, perfluoro-η - nineteen yard base, perfluoro-η - twenty yard base, perfluoro-η- twenty-one alkyl. (Π) perfluoro-branched alkyl group, for example, perfluoro-1-methylethyl, perfluoro-2-methylpropyl, perfluoro-3-methylbutyl, perfluoro-4-methylpentyl , perfluoro-5-methylhexyl, perfluoro-6- -14- 200936563 methylheptyl, perfluoro-7-methyloctyl, perfluoro-8-methylindolemethylhydrazine, perfluoro -10 -methyl i--hospital, perfluoro-11. group, perfluoro-12-methyltridecyl, perfluoro-13-methyl decafluoro-14-methyl fifteen yards, all Fluor-15-methyl hexadecanylmethylheptadecyl, perfluoro-17-methyloctadecyl, all _9-yard, perfluoro-19-methyl 20-unit, perfluoro- 20-methyl. (Hi) perfluorocyclic hydrocarbon group, for example, a perfluorocyclic alkyl group such as a perfluorocyclohexyl group; a perfluoro crosslinked cyclic hydrocarbon group such as a 1- or 2-perfluoroadamantyl group. (2) Partial fluorine-substituted hydrocarbon group The partially fluorine-substituted hydrocarbon group includes the following (i) to (iv) (i) a partially fluorine-substituted alkyl group, for example, a monofluoromethyl group or a difluoromethyl group. (ii) a perfluoro linear alkyl-substituted alkyl group such as (trifluoromethyl)methyl, 2-(trifluoromethylperfluoroethyl)methyl, 2-(perfluoroethyl)ethyl, (permethyl, 2-(perfluoro-η-propyl)ethyl, (perfluoro-η-but-2-(perfluoro-η-butyl)ethyl, (perfluoro-η-pentyl)) Fluoro-η-pentyl)ethyl, (perfluoro-η-hexyl)methyl, 2-yl, peroxy-9- •methyldodecanetetraalkyl, all; perfluoro-16-i -18 -methyldecyl eicosylperfluoroadamantyl.) Ethyl, (fluoro-η-propyl)yl)methyl, yl, 2-(perfluoro-η-hex-15- 200936563 Ethyl, (perfluoro-η-heptyl)methyl, 2-(perfluoro-η-heptyl)ethyl, (perfluoro-η-octyl)methyl, 2-(perfluoro-η- Octyl)ethyl, (perfluoro-η-fluorenyl)methyl, 2-(perfluoro-η-fluorenyl)ethyl, (perfluoro-η-fluorenyl)methyl, 2-(perfluoro- Η-fluorenyl)ethyl, (perfluoro-η-undecyl)methyl, 2-(all-gas-η- eleven-yard)ethyl, (all gas-η-ten.-alkyl) Methyl, 2-(perfluoro-η-dodecyl)ethyl, (perfluoro-η-tridecyl)methyl, 2-(perfluoro-η- Trialkyl)ethyl, (perfluoro-η-tetradecyl)methyl, 2-(perfluoro-η-tetradecyl)ethyl, (perfluoro-@η-pentadecyl)methyl Base, 2-(perfluoro-η-pentadecyl)ethyl, (perfluoro-η-hexadecyl)methyl, 2-(perfluoro-η-hexadecyl)ethyl, (all Fluorine-η-heptadecyl)methyl, 2-(perfluoro-η-heptadecyl)ethyl, (perfluoro-η-octadecyl)methyl, 2-(perfluoro-η- Octadecyl)ethyl, (perfluoro-η-nonadecyl)methyl, 2-(perfluoro-η-nonadecyl)ethyl, (all gas-η - _ 十院基)甲Base, 2-(all gas-η-- ten yards) ethyl, (perfluoro-η-icosyl)methyl, 2-(perfluoro-η-icosyl)ethyl. ◎ (iii) perfluoro-branched alkyl-substituted alkyl group, for example, (perfluoro-1-methylethyl)methyl, 2-(perfluoro-methylethyl)ethyl, (perfluoro-2-methyl) Propyl)methyl, 2-(perfluoro-2-methylpropyl)ethyl, (perfluoro-3-methylbutyl)methyl, 2-(perfluoro-3-methylbutyl) Ethyl, (perfluoro-4-methylpentyl)methyl, 2-(perfluoro-4-methylpentyl)ethyl, (perfluoro-5-methyl) Methyl, 2-(perfluoro-5-methylhexyl)ethyl, (perfluoro-6-methylheptyl)methyl, 2-(-16-200936563 perfluoro-6-methylheptyl Ethyl, (perfluoro-7-methyloctyl)methyl, 2-(perfluoro-7-methyloctyl)ethyl, (perfluoro-8-methylindolyl)methyl, 2- (Perfluoro-8-methylindenyl)ethyl, (perfluoro-9-methylindenyl)methyl, 2-(perfluoro-9-methylindenyl)ethyl, (perfluoro-10- Methyl-monoalkyl)methyl, 2-(perfluoro-10-methylundecyl)ethyl, (perfluoro-11-methyldodecyl)methyl, 2-(perfluoro- 11-methyldodecyl)ethyl, (perfluoro-12-methyltridecyl)methyl, 2-(perfluoro-12-methyldecaltrialkyl)ethyl, (perfluoro -13-methyltetradecyl)methyl, 2-(perfluoro-13-methyltetradecyl)ethyl, (perfluoro_14-methylpentaphenyl)methyl, 2-( Perfluoro-14-methylpentadecyl)ethyl, (perfluoro-15-methylhexadecyl)methyl, 2-(perfluoro-15-methylhexadecyl)ethyl, ( Perfluoro-16-methylheptadecenyl)methyl, 2-(perfluoro-16-methylheptyl)ethyl, (perfluoro-17-methyl18) Methyl, 2-(perfluoro-17-methyloctadecyl)ethyl, (perfluoro-18-methylundecyl)methyl, 2_(perfluoro-18-methyl-19 Alkyl)ethyl, (perfluoro-19-methyldi-(decyl)methyl), 2-(perfluoro-19-methyleicyl)ethyl, (perfluoro-20-methyl) Undecyl)methyl, 2-(perfluoro-20-methylhexa-alkyl)ethyl. (iv) an alkyl group substituted with a perfluorocyclic hydrocarbon group, for example, an alkyl group substituted with a perfluorocyclic alkyl group such as (perfluorocyclohexyl)methyl or 2-(perfluorocyclohexyl)ethyl, (1- Perfluoroadamantyl)methyl, 2_(1-perfluoroadamantyl)ethyl, (2-perfluoroadamantyl)methyl, 2-(2-perfluoroadamantyl)ethyl, etc. Alkyl-substituted alkyl. -17- 200936563 R8 is preferably a perfluoro linear alkyl-substituted alkyl group or a perfluoro-branched alkyl-substituted alkyl group. The perfluoro linear alkyl-substituted alkyl group is preferably (trifluoromethyl)methyl, (perfluoroethyl)methyl '(perfluoro-η-propyl)methyl' (perfluoro-n- Butyl)methyl, (perfluoro-η-pentyl)methyl, (perfluoro-η-hexyl)methyl, (perfluoro-η-heptyl)methyl, (perfluoro-η-octyl) Methyl, (perfluoro. η-fluorenyl)methyl and (perfluoro-η-fluorenyl)methyl. The perfluoro-branched alkyl-substituted alkyl group is preferably (perfluoro-1-methylethyl)methyl, (perfluoro-2-methylpropyl)methyl, (perfluoro-3-methyl) Butyl)methyl, (perfluoro-4-methylpentyl)methyl, (perfluoro-5-methylhexyl)methyl, (perfluoro-6-methylheptyl)methyl, (all Fluoro-7-methyloctyl)methyl, (perfluoro-8-methylindolyl)methyl and (perfluoro-9-methylindenyl)methyl. More preferably, it is (perfluoro-1_methylethyl)methyl {-CH2CF(CF3)2}, and (perfluoro-3-methylbutyl)methyl {-CH2(CF2)2CF(CF3) 2}. R9 in the formula (I) is a hydrogen atom, or a ChM aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group (especially a &lt;^-24 aliphatic hydrocarbon group which may be substituted by a fluorine atom, that is, a hydrogen atom on a carbon atom) a Ci-24 aliphatic hydrocarbon group which may be substituted by a fluorine atom, or a <^-24 aliphatic hydrocarbon group in which one part of a methylene unit is substituted by an oxygen atom (i.e., a CbM aliphatic hydrocarbon group in which a carbon atom is substituted by an oxygen atom, for example, an alkane Oxy-substituted hydrocarbyl group, etc.). The hydrocarbon group which may be substituted by a fluorine atom, a hydroxyl group, an alkoxy group or the like is, for example, the groups of the following (1) to (4). (1) Hydrocarbyl group having no fluorine and hydroxyl group-18-200936563 For example, methyl group, ethyl group, η-propyl group, isopropyl group, η-butyl group, sec-butyl group, tert-butyl group, η-pentyl group , an alkyl group such as η-hexyl, η-heptyl, η-octyl, n-fluorenyl, η-fluorenyl, cyclohexyl, 1-methyl-1-cyclohexyl, (cyclohexyl)methyl (including A linear, branched, and cyclic alkyl group; a crosslinked cyclic hydrocarbon group such as 1-adamantyl, 2-methyl-2-adamantyl, or 2-ethyl-2-adamantyl. Φ ( 2 ) Perfluoro-substituted hydrocarbon group The perfluoro-substituted hydrocarbon group contains the groups of the following (i) to (iii). (i) a perfluoro linear alkyl group such as trifluoromethyl, perfluoroethyl, perfluoro-η-propyl, perfluoro-η-butyl, perfluoro-η-pentyl, perfluoro-η -hexyl, perfluoro-η-heptyl, perfluoro-n-octyl, perfluoro-η-fluorenyl, perfluoro-η-fluorenyl, perfluoro-η- eleven-yard, perfluoro-η- Dodecyl, perfluoro-η-tridecyl, perfluoro-η-tetradecyl, all-fluorene-n-firteen-yard, perfluoro-η-hexadecanthyl, perfluoro-η - Seventeen yards, perfluoro-η-eighteen yards, perfluoro-η-nonylnonyl, perfluoro-η- twenty-yard, perfluoro-η-icosyl. (Π) perfluoro-branched alkyl group, for example, perfluoro-1-methylethyl, perfluoro-2-methylpropyl, perfluoro-3-methylbutyl, perfluoro-4-methylpentyl , perfluoro-5-methylhexyl, perfluoro-6-methylheptyl, perfluoro-7-methyloctyl, perfluoro-8-methylindolyl, perfluoro-9-methylindolyl , perfluoro-10-methylundecyl, perfluoro-11-methyldodecane-19- 200936563, perfluoro-12-methyltridecyl, perfluoro-13-methyltetradecyl Alkyl, perfluoro-14-methylpentadecyl, perfluoro-15-methylhexadecyl, perfluoro-16-methylheptadecyl, perfluoro-17-methyloctadecyl , perfluoro-18-methylundecyl, perfluoro-19-methylicosyl, perfluoro-20-methylhexadecyl. (iii) a perfluorocyclic hydrocarbon group, for example, a perfluorocyclic alkyl group such as perfluorocyclohexyl; and a perfluorocrosslinked cyclic hydrocarbon group such as 1-perfluoroadamantyl or 2-perfluorogold. (3) Partial fluorine-substituted hydrocarbon group The partially fluorine-substituted hydrocarbon group contains the following groups (i) to (iv). (i) a partially fluorine-substituted alkyl group, for example, a monofluoromethyl group or a difluoromethyl group. (ii) a perfluoro linear alkyl-substituted alkyl group such as (trifluoromethyl)methyl, 2-(trifluoromethyl)ethyl, (perfluoroethyl)methyl, 2-(perfluoroethane) Ethyl, (perfluoro-η-propyl)methyl, 2-(perfluoro-η-propyl)ethyl, (perfluoro-η-butyl)methyl, 2-(perfluoro-η -butyl)ethyl, (perfluoro-η-pentyl)methyl, 2-(perfluoro-η-pentyl)ethyl, (perfluoro-η-hexyl)methyl, 2-(perfluoro- Η-hexyl)ethyl, (perfluoro-η-heptyl)methyl, 2-(perfluoro-η-heptyl)ethyl, (perfluoro-η-octyl)methyl, 2-(perfluoro -η-octyl)ethyl, (-20-200936563 perfluoro-η-fluorenyl)methyl, 2-(perfluoro-η-fluorenyl)ethyl, (perfluoro-η-fluorenyl)methyl , 2-(perfluoro-η-fluorenyl)ethyl, (perfluoro-η-undecyl)methyl, 2-(perfluoro-η-undecyl)ethyl, (perfluoro-η -dodecyl)methyl, 2-(perfluoro-η-dodecyl)ethyl, (perfluoro-η-tridecyl)methyl, 2-(perfluoro-η-tridecane Ethyl, (perfluoro-η-tetradecyl)methyl, 2-(perfluoro-η-tetradecyl)ethyl, (perfluoro-η-pentadecyl) ) methyl, 2-(perfluoro-η-pentadecyl)ethyl, (all gas-η-hexadecanyl)methyl, 2-(all gas-η-hexadecanyl)ethyl, (Perfluoro-η-heptadecyl)methyl, 2-(perfluoro-η-heptadecyl)ethyl, (perfluoro-η-octadecyl)methyl, 2-(perfluoro- Η-octadecyl)ethyl, (all gas-n-yttrium) methyl, 2-(all gas-n-yttrium) ethyl, (perfluoro-η-icosyl) )methyl, 2-(perfluoro-η-icosyl)ethyl, (perfluoro-η-icosyl)methyl, 2-(perfluoro-η-icosyl)ethyl base. 〇( iii ) perfluoro-branched alkyl-substituted alkyl group, for example, (perfluoro-1-methylethyl)methyl, 2-(perfluoro-1-methylethyl)ethyl, (perfluoro- 2-methylpropyl)methyl, 2-(perfluoro-2-methylpropyl)ethyl, (perfluoro-3-methylbutyl)methyl, 2-(perfluoro-3-methyl Butyl)ethyl, (perfluoro-4-methylpentyl)methyl, 2-(perfluoro-4-methylpentyl)ethyl, (perfluoro-5-methylhexyl)methyl, 2 -(perfluoro-5-methylhexyl)ethyl, (perfluoro-6-methylheptyl)methyl, 2-(perfluoro-6-methylheptyl)ethyl, (perfluoro-7-) Methyl octyl)methyl, 2-(allo-7-methylsemiyl)ethyl, (all-octa-8-methylindenyl)methyl, -21 - 200936563 2-(perfluoro-8- Methylmercapto)ethyl, (perfluoro-9-methylindenyl)methyl, 2-(perfluoro-9-methylindenyl)ethyl, (perfluoro-10-methylundecyl) )methyl, 2-(perfluoro-10-methylundecyl)ethyl, (perfluoro-11-methyldodecyl)methyl, 2-(perfluoro-11-methyl-12 Alkyl)ethyl, (perfluoro-12-methyltridecyl)methyl, 2-(perfluoro-12-methyltridecyl)ethyl, (perfluoro-13-A) Tetradecyl)methyl, 2-(perfluoro-13-methyltetradecyl)ethyl, (perfluoro-14-methylpentadecyl)methyl, 2-(perfluoro-14 -methylpentadecyl)ethyl, (perfluoro-15-methylhexadecyl)methyl, 2-(perfluoro-15-methylhexadecyl)ethyl, (perfluoro- 16-methylheptadecyl)methyl, 2-(perfluoro-16-methylheptadecyl)ethyl, (perfluoro-17-methyloctadecyl)methyl, 2-(all Fluorin 17-methyloctadecyl)ethyl, (perfluoro-18-methyl-ytyl)methyl, 2-(perfluoro-18-methylundecyl)ethyl, (all Fluoro-19-methyl eicosyl)methyl, 2-(perfluoro-19-methylicosyl)ethyl, (perfluoro-20-methylhexadecyl)methyl, 2 -(Perfluoro-2 0-methyleicyl)ethyl. © (iv) an alkyl group substituted with a perfluorocyclic hydrocarbon group, for example, an alkyl group substituted with a perfluorocyclic alkyl group such as (perfluorocyclohexyl)methyl or 2-(perfluorocyclohexyl)ethyl; 1-perfluoroadamantyl)methyl, 2-(1-perfluoroadamantyl)ethyl, (2-perfluoroadamantyl)methyl, 2-(2-perfluoroadamantyl)ethyl, etc. Crosslinked cyclic hydrocarbyl-substituted alkyl-22-200936563 (4) alkyl substituted by hydroxy or alkoxy group, for example, 2-hydroxyethyl, 2-hydroxypropyl, methoxymethyl, 2-(2- Methoxyethoxy)ethyl. R9 is preferably a hydrogen atom, a methyl group, a tert-butyl group, a 1-methyl-1-cyclohexyl group, a crosslinked cyclic hydrocarbon group, a perfluoro linear alkyl-substituted alkyl group, and a perfluoro-branched alkyl group. alkyl. The crosslinked cyclic hydrocarbon group is preferably 1-adamantyl, 2-methyl-2-adamantyl or 2-ethyl-2-adamantyl. A perfluoro linear alkyl-substituted alkyl group is preferred as (trifluoromethyl)methyl, (perfluoroethyl)methyl, (perfluoropropyl)methyl, (perfluorobutyl)methyl (Perfluoropentyl)methyl, (perfluorohexyl)methyl, (perfluoroheptyl)methyl, (perfluorooctyl)methyl, (perfluorodecyl)methyl and (perfluorodecyl) )methyl. The perfluoro-branched substituted alkyl group is preferably (perfluoro-1-methylethyl)methyl, (perfluoro-2-methylpropyl)methyl, (perfluoro-3-methylbutyl) Methyl, (perfluoro_4_methylpentyl)methyl, (perfluoro-5-methylhexyl)methyl, (all gas _6_methylheptyl)methyl, (perfluoro-7-) Methyl octyl)methyl, (all gas _8_ G methyl fluorenyl) methyl, (perfluoro. 9-methyl fluorenyl) methyl and. R9 is particularly preferably a hydrogen atom. The compound (I) is preferably a compound of the formula (2-1) to (I-3) which is represented by the formula (2). -23- 200936563

-24- 200936563 【化5】

CF3

25- 200936563 【化6】 O GOOR95 O COOR91

P51 p61 r21 π'οΎ, ch2 COOR1 CF3 〒h2(H force cf strict~(CF2) 8 Rl1

91

R21 R41 R31, cf3 〒H2 (1-19) ; CF-(CF2)a R CF3 R21 R5^〇A^C〇〇R91 F_SCF2^

(1-18) ❿ , 11

»21 R1, 1 R31〇

Ji p51 p61 person ctryr'. Cf3 ch2 «-21) State CF2)a R1&lt; cf3 R21

R31( R«J COOR91 r3\ ,r5J .r6J_

Ch2 COOR31 (1-20) o »41 .R5, 1 /Rl CH2 is called (5)

COOR91 (1-22) ❹ 26- 200936563

In the formulae (I-1) to (1-30), R11 and R21 each independently represent a hydrogen atom or a fluorine atom. R11 and R21 are preferably a hydrogen atom. In the formulae (1-1) to (1-30), R31 is a hydrogen atom, a fluorine atom, a trifluoromethyl group or a methyl group, preferably a hydrogen atom or a methyl group. In the formulae (1-1) to (1-30), R41 and R61 are each independently a single bond, a methyl group, an ethyl group or an η-propyl group. R41 and R61 are preferably a single bond, and R51 is preferably a methyl group and an ethyl group. In the formulae (1-1) to (1-30), R91 is a hydrogen atom, tert-butyl, -27-200936563 1-methyl-1-cyclohexyl, 1-adamantyl, 2-methyl-2- Adamantyl, 2-ethyl-2-goldyl, (trifluoromethyl)methyl, (perfluoroethyl)methyl, (perfluoro-η-propyl)methyl, (perfluoro-η-butyl) Methyl, (perfluoro-η-pentyl)methyl, (perfluoro-η-hexyl)methyl, (perfluoro-η-heptyl)methyl, (perfluoro-η-octyl)methyl , (perfluoro-η-fluorenyl)methyl, (perfluoro-η-fluorenyl)methyl, (perfluoro-1-methylethyl)methyl, (perfluoro-2-methylpropyl) )methyl, (perfluoro-3-methylbutyl)methyl, (perfluoro-4-methylpentyl)methyl, (perfluoro-5-methylhexyl)methyl, (perfluoro-6) -methylheptyl)methyl, (perfluoro-7-methyloctyl)methyl, (perfluoro-8-methylindolyl)methyl, (perfluoro-9-methylindenyl)methyl Or methoxymethyl. R91 is preferably a hydrogen atom. In the formulae (1-1) to (1-30), a is an integer of from 0 to 19 (preferably from 0 to 7). In the formulae (1-1) to (1-2), b is an integer of 0 to 10 (preferably 0 to 6). In the formulae (1-1) to (1-30), c is an integer of from 0 to 21 (preferably from 1 to 8). In the formulae (1-7) to (1-8), d is an integer of 1 to 10 (preferably 2 to 4). In the formulae (1-13) to (1-14), e is an integer of 1 to 8 (preferably 2 to 4). In the formulae (1-1) to (1-30), R41 is preferably a single bond. Particularly preferred is a (meth) acrylate wherein R11 and R21 are a hydrogen atom, R31 is a hydrogen atom or a methyl group, and R41 is a single bond. -28- 200936563 In the present specification, ^(meth)acrylate" is represented by at least one selected from the group consisting of acrylate and methacrylate. Further, "(meth) acrylate" is equivalent to the above. The compound (I) is more preferably a methacrylate (R3 = methyl group) represented by the chemical formulas of Groups 1 to 48. Further, the compound (I) is more preferably an acrylate wherein R3 is a hydrogen atom in the chemical formulas of Groups 1 to 48. 〇 【化8】(Group 1)

COOH

COOH ^(CF^-CF cf3 cf3

o οη2-^ο COOH

O

ο

Cf3 (CF2)2-CF CF, 3 3 F F PF, C C

(CH2)2 I COOH

-29- 200936563 【化9】

Ο (CH2)31 I COOH

(CF2)4-CF o pp3 (CH2)3 gf3

COOH cf3 (CF2)6-CF cf3 -30- 200936563 Ο 【化10】 (Group 3)

10

〇 (CH^Lo—(

COOH (CF2) 4_F -31 - I. 200936563 【化1 1】 (Group 4) }-〇\

cb〇H

-32 200936563 【化1 2】 (Group 5)

.卞 (CH^-^O-Y CF3 COO^u Cv

(CH2)2 I

COOH (CF2)10-F

-33- 200936563 【化1 3】 (Group 6)

Q 〇 ) )-〇—( cf3

Ϋ́ΰο*Βϋ N^(CF2)2-CF

L〇j CP3

COdeT^-iCF^-CF

CIS CF,

Cf3 ch2—

CF3 (CF2)4-CF cf3

o (CH2)2 COOfBu

o

°L CF3 (CH^z^O (CF^-CF l〇〇fBu cf3

CF,

(CF2)4-CF cf3

o

p o (〇Η2)3[0 COOfBu

Ρ^3 ^2-CF i〇〇tBu , U Bu 3 PF3 (GF2)4-CF cf3

-34- 200936563 【化14】 (Group 7)

CF,

I〇〇, Bu l(CF2)2-f

(CH2)3 COO^u

PF3 (meaning (CF2)6-CF COO^u cf3

(CF2)2-F -35- 200936563 [Equation 1 5] (Group 8)

1.

Μ COC^Bu ^(C^e-F

-36 200936563

【化16】

-37- 200936563 【化1 7】 (隹10 groups) COOH 〇

CpO%u 〇.; Ο -ο

COOH 〇

C.OOfBu 〇 II

Cf3 CF CF3 ο

Cf3

(CF2)2-CF cf3 COOH 〇

CP〇fBu =〇 1 o

Cf3 (CF2)4-cf cf3

-38- 200936563 【化1 8】

-39- 200936563 [Chem. 1 9] (Group 12)

COOH 〇

〇

Ο cf3 CF CF3 COOJBu 〇 °

CF3

CF CF3

COOH eoofeu

o pF3 (cf2)2-cf cf3 L·-) \ PF3 Mcf2)2-cf CF, ❹

o qooh?

O

O- pf3 (CF2)4-CF cf3

C.OO’Bu 〇 Q II

o 〇—( CF3 (CF2)4-CF cf3 COOH 〇

C.OO^Bu 〇-&lt; PF3 (cf2)6-cf cf3

I

O-Λ pF3 (GF^-CF CF3

-40- 200936563

[化2 0]

(CF2)io-F

COOH 200936563 [Chem. 2 1] (Group 14)

3 (CF2)2 Vp I CF3 COOH COOH

(CF2)2 COOH COOH

O one -\ PF3 -cf 3

Pp3 (cf2)2-u-〇-( (CF2)6-CF I V丨 -42- 200936563 [Chem. 2 2] (Group 15)

o (CF2)3l〇

Cf2- 1

COOH

Q GF3 CF 'cf3

COOH

(CF2)2-F

(CF2)3I COOH

=〇

Cf3 (CF2)2-CF gf3 cf2—COOH / o (CF2)3 COOH =〇 CF3 (CF2)4-CF cf3

o cf2—^-o- COOH _/ ^(CF^e-F

O o

O CjiF2"-〇 COOH

O

o (CFzh·1-.I COOH

Cf3 (cf2)6-cf cf3 9 cf2—°-〇 COOH

(CF^e-F

(CF2)10-F ❿ -43- 200936563 【化2 3】

Ο -44 - 200936563 [Chem. 2 4] (Group 17)

Ο γ"2 ΟΟΟΈυ CFp-

CF (C% COO^u

CF3 o o cf3 CF CF3

L 〇 cf2— COO^u o

Ρρ3 (CF2)2-CF COOfBu cf3o (CF2)2

CF3 (CF2)2-CF cf3o o o cf2—^-o cod^u

o

o cf3 (? "also 1〇·^ Pp3 (CF2)4-CF COO(Bu ' (CF2)4 - CF cf3 cf3 ΐ ο

CF CF3 (^F2)2 Ο (CF2)6-CF COOfBu CF,

Cf3 (CF2)6-CF cf3 ❿ -45- 200936563 [Chem. 2 5] (Group 18)

Ο (CF^^-O-i, CF3

COOfBu ^(CF2)2~CF Ο

(CF2)3~^~°—\ CF3 COC^Bu MCF2)6-Cf CF3

-46 - 200936563 [Chem. 2 6] (Group 19)

(CF2)2 COO^u

Ο

o

(CF2)3l〇 (CF2)2-F COOfBu / V-(CF2)2-F

o oiCF^Xo-^000, BU / [(CW-F CO〇iBu o

〇

O

o

-(CF2)4-F o(CFzJz^-O COOfBu

O

O

(CF2)6-F

(CFJ produced o- GOOfBu ^-(CF2)6-F

O O

(CF2)2-1L〇^(, (CFzJa-JL-O-/COOfBu (i〇OfBu / F

O o

o (CF2)2

i o

(CF^-^-O-COOfBu (CF2)i〇-F coo^Bu -47- 200936563 [Chem. 2 7] Building 20 groups)

Ο COOH 〇

o 〇ep〇fBu 〇 Pf3V__JL CF , CF3

〇-( CF3 CF cf3

Ο

COOH 〇

o

〇-( cf3 (CF2)2-CF GOOfBu 〇 CF3 \ II

O o

CF3 COOH 〇

〇~( CF3 (CF2)4-CF COOfBu 0

(CF2)2-CF CF3

o o cf3

1L -o

CF,

(CF2)4-CF CF, COOH 〇

-〇-C cf3 (CF2)6-CF COOfBu 〇 CF3\ ~ J| q CF3 (cf2)6-cf cf3

-48- 200936563 [Chem. 2 8] (Group 21)

o

I Ο

COOH

Ο (CF2)2-Fy

o

COOfBu

(CF2)2-F

I

〇

o

(CF2)4-F

I

COOH

ο

o

COO*Bu

(CF2)4-F

I Ο 〇

(CF2)6-F

COOH

ο Ο

o

COC^Bu

(CF2)6-F

I

〇

o

(CF2) 8-F

COOH ❿

ο

I o

O

COOfBu

(CF2) 8-F

〇

o

(CF2) 10-F

COOH

I o

COO^u

(CF2)10-F -49- 200936563 [Chem. 2 9]

-50- 200936563 ❹ ❹ 【化3 0】 (Group 23)

(CF2)2-F (CF2)4-F (CF2)i〇-F -51 - 200936563 [Chemical 3 1] (笫24 groups)

Ο COOH COOH I H2CiF2C)2H2e- 1 〇

H2c(f2c>2h2c

CF3 CF bp3 y=0 COOH

PF3 (CF2)2-〇f CF3 COOH I: H2C(F2C)4H2Q- o

PFa CF COOH I h2c(f2c)6h2c- o

I o

CF3 CF CF3

〇〇H COOH I H2C(F2C)eH2C- o

/ CF3 COOH h2c(f2c)6h2c H2C(F2C)eH2C

CF3 (CF2)2-CF cf3 cf3 (CF2)2-CF cf3 ❹ cf3 CF cf3 cf3 (CF2>2-CF gf3 ❹ -52 200936563 [Chem. 3 2] (Group 25)

o

COOH H2C(F2C)2H2C-11-〇

O COOH H2C(F2C)2H2C· pF3(CFA-Cf cf3

CF3 (CF2)6-CF cf3 O =〇 COOH COOH 〇 °\ H2C(F2C)4H2C-lJ-〇 H2C(F2C)4H2C-1L〇-/ cf3 v-(cf2)4-cf cf3

° ?°0H o o

Cf3 (CFsJs-CF CF3 o COOH IH2C(F 2^)6Η2〇·

COOH

H2C(F2C)6H2C-li-〇 C (CFA-Cf υυ γυυπ 〇 H2C(F2C)eH2C-U-〇

CF3 COOH H2C(F2C)aH2Cl〇- CF3 -(CF2)4-CF cf3 o

Cf3 (CF2)6-CF CF3. o

O

PF3 (CF2)6-CF CF, ❹ -53- 200936563 [Chem. 3 3] (Group 26)

H2C(F2C)2H2C· COOH 0

〇 〇«2. (戸2〇)2&quot;2〇』~ COOH (CF2)2-F -〇

H2C(F2C)4H2C· 1 COOH

I ο

H2C(F2C)6H2C COOH o

H2C(F2C)4H2C COOH (CF2)2-Fo H2C(F2C)6H2C-GOOH (CF2)2-F

I o

(CF2)4-Fo (CF2)4-F

o -o

(CF2)4-F

o o

H2C(F2C)8H2C COOH

H2C(F2C)eH2C-COOH

(CF2)2-F

I o

(CF2)4-F

-54- 200936563 [Chem. 3 4] (Group 27)

i=〇 O

H2G(F2C)4H2G COOH

COOH

°\ H2C(F2C)2H2C· COOH (cf2)6-f ο h2c(f2c)4h2c

COOH (CF2)6-F H2C(F2C)6H2C COOH

H2C(F2C)eH2C COOH

-55- 200936563 [Chem. 3 5] (Group 28)

H2C(F2C)aH2C COOH

H2c(f2c)2h2c COOH H2C(F2C)4H2C COOH H2C(F2C)6H2C COOH

COQ!Bu H2C(F2C)2H2C (CF2)iq-F

〇 cooteu I H2C(F2C)4H2C(CFzho-F &gt; COO^Bu h2c(f2_2c- (CF.2)i〇-F

〇 COOfBu 'I H2C(F2C)eH2C (CF2)io~F

-56 200936563 【化3 6】 (Group 29) COOfBu 〇 H2i(F2C)4H2C 丄 Ο

COOfeu I H2C(F2C)2H2C

H2c(f2c)2h2c- H2C(F2C)6H2C- PF3

Gf3 (CF2)4-eF gf3 h2c(f2c)4h2c^-o

Ρρ3 (CF2)4-GF cf3

COOfBu I H2C(F2C)6H2C COO^Bu I H2C(F2C)8H2C

(CF2)2-CF cf3 COO^Bu I H2C(F2C)eH2C-cf3 (CF2)2-CF cf3 -o

Cf3 (CF2)4-CF cf3 cf3 (CF2)4-CF cf3 ❿ -57- 200936563 [Chem. 3 7] (30th_COOfBuI H2C(F2C)2H2C- ο

H2C(F2C)2H2C COO^u (CF2)6-CF

COO^ul H2C(F2C)6H2C-

o h2c(f2c)4h2c COOfBu COC^Bu I: H2C(F2C)4H2C

COOfBu1 H2C(F2C)eH2e- 1 〇 H2C(F2C)6H2C COOfBu CF3 (CF2)6-CF cf3 o H2C(F2C>aH2C-COOfBu o

o

(CF2)2-F ❹

❹ -58 200936563 【化3 8】 (Group 31)

O

〇 H2C(F2C)8H2C COOfBu H2C(F2C)2H2C COO^u h2c(f2c)4h2c COO^u H2C(F2C)sH2C C〇OfBu

H2c(f2c)2h2c COO^Bu (CF2)4-F h2c(f2c)4h2c COOfBu (CF2)4-F o H2C(F2C)8H2C 丄 o COOfBu (CF2)4-F -o

o H2C(F2C)6H2C-L〇 COOfBu (CF2)4-F

-59- 200936563 [Chem. 3 9] (Group 32)

Ο H2Q(F2C)2H2C 丄 0 COO^

O h2c(f2c)5h2c"-o COOfBu(CF2)e-F

O H2C(F2C)4H2C- C〇dlBu

H2C(F2C)4H2C coo^u (CF^8-f o

o (CF2)i〇-Fo (CF2)10-Fo

o h2c(f2c)6h2c 丄 o COO^u

o H2C(F2C)6H2C· COOfBu (CF2)e_F 1

(CF2) 10-F

oH2〇(F2C)eH2C-1L〇COOlBu

q h2c(f2c)8h2c COO^u (CF2)8-F

o

(CF2) 10-F

-60- 200936563 【化4 0】 (Group 33) 〇 COOH 〇

L0^ ρρ3 ^GF CF3

Ο ❹

ο cf3 (CF2)2-CF cf3 COOH 〇

COOHI

Q

COOH

o o—&lt; cf3 (CF2)4-CF gf3 o cf3 ^-(CFzig-CF CF3

❹ -61 - 200936563 【化4 1】

〇 -62- 200936563 【化4 2】 (Group 35)

Ο COOH 〇

Ο

ο cf3 CF gf3 ο ο

COOOu 〇 , JL

ο ο

PF3 CF CF3 Ο COOH 〇

o CF3 (CF2)2-CF cf3o COOfBu 〇

-〇

Cf3

(CF2)2-CF

o cf3 COOH 〇

COO^u 〇 〇-( PF3 \ II (CF2)4-eF CF,

〇—( CF3 (CF2)4-CF cf3

O

=〇

o COOH 〇

PF3C?°fB^ (CF2)6-CF / \-u Pp3 CF3 ( ) ^(CFsie-CF cf3

-63- 0 200936563 【化4 3】 (36th group)

-〇

i

COQH

(CF2)2-F

o

0 COO^Bu

(CF2)2^F

O

I

Ο

COOH

(CF2)4-F

o

COOfBu

(CF2)4-F

I

ο

o

COOH

(CF2)6-F

o

o COO^u

(CF2)6-F

o

Ο _IL

COOH

(CF2>8-F

o

COC^Bu

(CF2)e-F

O ❹

COOH

(CF2) 10-F

-o

COO^u

(CF2)10-F -64- 200936563 [Chem. 4 4] (Group 37) = 〇

c\— II

CF3 CF vcf3

ο

Cf3 (CF2)2-CF cf3o

Cf3

ο

o CF3 (CFA-CIf o

CF, cf3 (CF2)6-CF cf3

-65- 200936563 [Chem. 4 5] (Group 38)

(CF2)2-F (CiF2)4-F COOH

ο

Q

COOfBu

(CF2)2-F

I

Eoo{Bu

(CF2)4-F

o o

COO’Bu

(CF2)6-F o

o o

o \ ^(CF2)8-F COOH, o

o o COOfBu

(CF2)e-F

o \

o

(CF2)10-F o

COOH \ Mcf2)10-f COO^u -66- 200936563 [Chemical 4 6] (箄39 group)

Ο Ο C\〇〇H ?

COO^u 〇 Q, JL

〇—( gf3

(CF^-CF CF3 -〇—( pF3

(CF2)4-CF

COOH Q cf3 cf3 (CF2)6-CF cf3

67- 200936563 【化4 7】 (Group 40)

Ο

0 0 X.

(CF2)2-F COO’Bu 〇

(CF2)2-F

o Ο

οII

COOH

ϊ

π η X

(CF2)4-Fο (CF2)6-F COC^Bu

I

(CF2)4-F

o ο

ο COO^u

(CF2)6-F

o ο

(CF2) 8-F

COOH O _ II 〇 GOO^Bu

(CF2) 8-F

o

I Q Ο

(CF2) 10-F

COOH COO^u

O

(CF2)i〇-F -68- 200936563 【化4 8】 (Group 41) ❹ ❿

(CF2)6-CF -69- 200936563 [Chem. 4 9] (Group 42)

Ο Λ 〇

I

(CF2)2-F

COOH

ο COC^Bu

(CF2)2-F

-ο

(CF2)4-F ο

COOH

Ο COOfBu

(CF2)4-F

o ❿

I -o

^-(eF^B-F into MCF2)6-F COOH / COO’Bu,

o :〇 o o

o

I o

COOH

o

(CFzJe-F into ^-(CFzJb-F COO^U

o

A o o

◎ (CF2)10-F yCFAo-F COOH COO^u -70- 200936563 【化5 0】 (Group 43)

Ο 〇

TV COOH 〇

PF3 CF CF3 o COOfBu 7\

Λ COOH 〇 o

o PF3 (CF2)2-CF cf3

COO^U °

Cf3 o o 7\

I

O—( cf3 (CF2)2-CF cf3 COOH 9 \ ' II o

COOfBu

o o PF3 (CF2)4-CF cf3

TV o

COOH 〇 o

COO^u. o cf3 (CF2)4-CF cf3 /Cp3 /Γ (CF2)6-CF / \ cf3

-〇一C CF, (CF2)6-CF cf3 ❿ -71 - 200936563 【化5 1】

-72- 200936563 【化5 2】 (Group 45) 〇

-73- 200936563 [Chem. 5 3] (Group 46)

Ο 〇

ί

(CF2)2-F

COOH

Ο ^OOfBu

(CFzh-F

O •ο

ο (CF2)4

COOH

(CF2)4-F

o o

o o Ϊ o

ί

(CF2)6-F

COOH

o COO!Bu

(CF2)6-F o

o o

o

I

{CF2)8-F o

COOH

o COOfBu

(CF2) 8-F

o

I o

O

o o

(CF2)i〇-F

COOH COOfBu

(CF2)i〇-F -74- 200936563 ❹ 【化5 4】 (Group 47)

Cpt^Bu 〇 \ cpofeu 〇

COOH 〇 &gt; COOfBu 〇 -(CFA-cfF3 a/^7^(cF2)4-CFCF3 :〇 &gt;=0 bF3 O 〇 COOH 〇 〉 COOfBu 〇 〉 -〇々 cf3 CF3

(CF2)6-CF cf3

(CF2)6-CF cf3 ❿ -75- 200936563 【化5 5】

The compound (I) can be produced, for example, by the following method. First, a compound represented by the formula (a) (unsaturated vinegar having a hydroxyl group) is esterified with a compound represented by the formula (b) (dicarboxylic anhydride) or a compound represented by the formula (C) (dicarboxylic acid). A compound (carboxylic acid) in which R9 is a hydrogen atom can be produced. Further, by esterifying the C〇〇R9 group (R9 = H) of the compound (1), various compounds can be produced (〇 ° -76 - 200936563)

HOOC-R7-COOH (c) In the formulae (a) to (c), R1 to R8 are the same as those of the formula (I). The φ compound (a) is preferably 3-perfluoroalkyl-2-hydroxypropyl (meth)acrylate, more preferably 3-perfluoroalkyl-2-hydroxypropyl methacrylate. 3-(Perfluoroalkyl-2-hydroxypropyl)(meth)acrylate, such as 3-(perfluoroethyl)-2-hydroxypropyl (meth)acrylate, 3-(perfluorobutyl)(meth)acrylate 2-hydroxypropyl ester, 3-(perfluorohexyl)-2-hydroxypropyl (meth)acrylate, 3-(perfluorooctyl)-2-hydroxypropyl (meth)acrylate, (a) 3-(perfluoro-1-methylethyl)-2-hydroxypropyl acrylate, 3-(perfluoro-3-methylbutyl)-2-hydroxypropyl (meth)acrylate, hydrazine 3-(perfluoro-5-methylhexyl)-2-hydroxypropyl (meth)acrylate, and 3-(perfluoro-7-methyloctyl)-2-hydroxypropyl (meth)acrylate, etc. These can be obtained from Daikin's finished product sales (shares). Compound (b) such as succinic anhydride, 2,2-dimethylsuccinic anhydride, glutaric anhydride, 3-methylglutaric anhydride, perfluoroglutaric anhydride, maleic anhydride, itaconic anhydride, 2,3-nor Decane dicarboxylic anhydride, 2-northene-5,6-dicarboxylic anhydride, 12-cyclohexane dicarboxylic anhydride, 1,2,5,6-tetrahydrophthalic anhydride, 3,4,5,6- Tetrahydrophthalic anhydride and the like. The compound (c) contains a saturated aliphatic dicarboxylic acid, an unsaturated dicarboxylic acid, an alicyclic dicarboxylic acid, a crosslinked cyclic hydrocarbon dicarboxylic acid, a fluorine-containing saturated fat -77-200936563 aliphatic dicarboxylic acid. Aliphatic dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, 2,2-dimethylsuccinic acid, glutaric acid, 3-methylglutaric acid, adipic acid, pimelic acid, suberic acid, Azelaic acid, azelaic acid, dodecanedioic acid, decapine diacid, and the like. Unsaturated dicarboxylic acids such as maleic acid, itaconic acid and the like. The alicyclic dihydric acid is, for example, ' 1,2-cyclohexanedicarboxylic acid, 1,2,5,6-tetrahydrofurfuric acid, 3,4,5,6-tetrahydrofurfuric acid or the like. The cross-linked cyclic hydrocarbon dicarboxylic acid is, for example, 2,3-norbornane dicarboxylic acid, 2-northene-5,6-dicarboxylic acid or the like. The fluorine-containing saturated aliphatic dicarboxylic acid is, for example, perfluorosuccinic acid, perfluoroglutaric acid, perfluoroadipate, perfluorooctanedioic acid, orthofluorene dicarboxylic acid or the like. The above fluorine-containing saturated aliphatic dicarboxylic acid can be obtained, for example, from a large-scale finished product. The esterification reaction of the compound (a) with the compound (b) or the compound (c) can be carried out under the general conditions known in the art of organic synthesis. For example, the esterification reaction of the compound (a) with the compound (b) can be carried out while stirring under reflux of 4-dimethylaminopyridine and pyridine. The reaction mixture can be purified, for example, using toluene and hydrochloric acid in a liquid separation step. For example, the reaction of the compound (a) with the compound (c) can be carried out while stirring under reflux of concentrated sulfuric acid, magnesium sulfate and chloroform. The reaction mixture can be prepared, for example, by using a chloroform solution and a saturated aqueous solution of sodium carbonate in a liquid separation step. &lt;Polymer&gt; The polymer obtained from the compound (I) of the present invention has high heat resistance and has a low refractive index and high transparency. The polymer is represented by the formula (π) derived from the compound -78- 200936563

[Chem. 5 7] R1 R3 I I C—〇—* Re r2 ry〇-R5^R6-°yr7~coor9 (η) ο ο The description of R1 to R9 in the formula (II) and the preferred specific substance. The polymer is preferably a compound (I) which is a copolymer atom obtained by synthesizing two or more compounds (I), and R9 is a copolymer other than a hydrogen atom. Further, the polymer may be a compound in which one or more compounds are a compound (I) wherein R9 is a hydrogen atom, and a copolymer of each type. Other monomers such as the compound (I) are φ acrylate or the like. The polymer can be produced, for example, by a known polymerization method (e.g., bulk polymerization, solution thinning or emulsion polymerization, etc.) which is initiated by radical polymerization. The reaction pattern can be batch and continuous. The reaction container is not particularly limited, and may be, for example, a value-for-money or stainless steel container. The radical polymerization initiator is not particularly limited, and examples thereof include a compound (e.g., 2,2'-azobis(isobutyronitrile)), a redox compound, and the like. A suitable temperature for a radical polymerization initiator such as a polymerization temperature watt. A polymer of the formula (I), which may be, for example, a compound (I) in which R9 is a hydrogen compound (I) (particularly other than a single (meth) group of 5 or more, a free radical, a suspension or a suspension Polymerization, semi-continuous or: glass container, azo-based or peroxide-based, -79-200936563 Polymerization solvent or dispersant such as ethyl acetate, butyl acetate, etc. a solvent; a ketone solvent such as acetone or methyl isobutyl ketone; an aromatic solvent such as toluene; a hydrocarbon solvent such as cyclohexan; an alcohol solvent such as isoamyl alcohol or ethylene glycol monomethyl; or water. , a furan solvent, an ether, a cyclic ether, a fluorocarbon, a perfluoroether, etc. These solvents or dispersants may be used singly or in combination of two or more kinds. The number average molecular weight (??) of the polymer is polyphenylene. The ethylene conversion is generally 2,000 to 100,000, preferably 4, 〇〇〇 to 15,000. The degree of dispersion (weight average molecular weight / number average molecular weight) is not particularly limited and may be selected, for example, from a wide range of 2 to 60. Film&gt; Next, the use of the polymer of the present invention will be described. The use of the compound is basically a coating application. Generally, the polymer of the present invention is dissolved in an organic solvent as a coating material to form a film. More specifically, the polymer of the present invention is dissolved in an organic solvent to form a coating material. After that, the coating material is applied to the support, and the organic solvent is removed to form the film of the present invention. The organic solvent to be used may be one which can dissolve the polymer, and for example, acetone or A can be used. Ketones such as ketoethyl ketone, cyclohexanone, methyl isoamyl ketone, and 2-heptanone; ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene glycol a polyvalent alcohol such as propylene glycol monoacetate, dipropylene glycol, or dipropylene glycol monoacetate, methyl ether, monopropyl ether, monobutyl ether or monophenyl ether or a derivative thereof; dioxanoic acid Cycloethers; methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl-80-200936563 ester, methyl pyruvate, ethyl pyruvate, methyl methoxypropionate, ethoxy An ester such as ethyl propyl propionate; an aromatic solvent such as xylene or toluene; furan, A fluorine-based solvent such as a pyrene, a perfluoro compound or a hexafluoroisopropanol; a pine-based petroleum gas oil solvent or a paraffin-based solvent which improves the high boiling point weak solvent for coating properties. These may be used alone or in combination of two or more. The anti-reflection film can be formed into a monolayer by coating the polymer of the present invention on a surface of a glass, a plastic, a liquid crystal panel, a plasma display panel, an electroluminescence panel or the like in an extremely thin film form. Or a combination of films having other refractive indices. &lt;Composition&gt; The present invention also provides a composition containing the above fluoropolymer. The composition of the present invention can be classified into a film by lithography. a photosensitive composition and a curable composition for non-image development (non-photosensitive composition). Any of the compositions of the present invention contains the above polymer, and thus can have high heat resistance, low refractive index, and high transparency. Film of sex. Since the fluoropolymer contains a fluorine atom, physical properties different from those of a general polymer (e.g., high drainage, high oil repellency, low pollution, high heat resistance, low refractive index, high transparency, etc.) can be expected. Therefore, when the photolithography utilizes a fluorine-containing polymer, a molded article having a new feature can be provided. However, alkali-developable fluoropolymers are almost non-existent. Therefore, one of the objects of the present invention is to provide a photosensitive composition containing a novel fluoropolymer which can be alkali-developed. The photosensitive composition of the present invention can be used, for example, to form a photoresist. The photoresist composition of the present invention is preferably a polymer compound containing a polymer compound which is soluble in an alkaline aqueous solution by an action of an acid, and a positive photoresist composition of an acid generator. In particular, the photoresist composition of the present invention is suitably used as a positive-type photoresist composition for F2 lasers in the vacuum ultraviolet field represented by the recent 193 nm ArF excimer laser which is micronized by a semiconductor and 157 nm. This can be achieved by introducing an acid labile group (e.g., t_Bu group or the like) which can be used into R9 of the formula (II). The photoacid generator used in the positive resist composition is not particularly limited.

Any one of the acid generators of the chemically-reinforced photoresist can be selected. Q Such acid generators are, for example, bisacesulfonium diazomethanes, nitrobenzyl derivatives, sulfonium salts, halogen-containing triazine compounds, cyano group-containing sulfonate compounds, and other hydrazines. a sulfonate compound or the like. These acid generators may be used singly or in combination of two or more. The photoresist pattern can be formed from the photoresist composition using previous photo resistive techniques. For example, first, a solution of a photoresist composition is applied onto a support such as a circuit board by a spin coater or the like, and after drying to form a photosensitive layer, excimer laser light is irradiated through a desired mask pattern using an exposure apparatus or the like. , then heat. The development process is carried out by using, for example, a developing solution such as an aqueous alkaline solution of 0.1 to 1% by mass of a tetramethylammonium hydroxide aqueous solution. This technology faithfully captures the mask pattern. The foregoing photoresist composition may further contain a mixed additive such as an additional resin, a quenching agent, a solubility inhibitor, a plasticizer, a stabilizer, a colorant, a surfactant, a tackifier, and a flattening agent. Various additives such as a solvent, an antifoaming agent, a compatibilizing agent, an adhesive, and an antioxidant. Preferred compositions of the invention are described in more detail below. Preferably, the composition of the present invention is -82-200936563, comprising 1 - a photosensitive composition comprising the polymer (A), the sensitizer (b), the hardener (C) and the solvent (?) of the present invention (hereinafter referred to as "Photosensitive composition 1"), 2·containing the polymer (Α) of the present invention, a curing agent (C), a photoacid generator (D), a solvent (Η) and, if necessary, an amine compound (ε) Photosensitive composition (hereinafter referred to as "photosensitive composition 2"), 〇 3. Containing the polymer (Α) of the present invention, a polymerizable compound (F), a photopolymerization initiator (G), and a solvent (Η) Photosensitive composition (hereinafter referred to as "photosensitive composition 3"), 4. Containing the polymer (Α) of the present invention, a curing agent (C), a solvent (Η), and an amine compound (Ε) if necessary The curable composition (hereinafter referred to as "curable composition 4"). The photosensitive compositions 1 to 3 and the curable composition 4 of the present invention can exhibit physical properties different from those of the general composition (for example, high drainage, high oil repellency, low pollution, high heat resistance, low refractive index, high Transparency, etc.). Further, the coating films obtained from the photosensitive compositions 1 to 3 and the curable composition 4 of the present invention have a low refractive index and high transparency. Further, the photosensitive compositions 1 to 3 of the present invention contain not only a fluorine-containing polymer but also very excellent alkali developability. The polymer (Α) contained in the composition of the present invention is the above. The components other than the polymer (Α) contained in the photosensitive compositions 1 to 3 and the curable composition 4 of the present invention will be described in order below. -83-200936563 &lt;Photosensitive composition The photosensitive composition 1 of the present invention contains the polymer (A), the sensitizer (B), the curing agent (C), and the solvent (Η) ° &lt;sensitizer (Β) &gt The sensitizer (Β) used may be known in the field of photosensitive compositions. A representative sensitizer (Β) is a benzoquinonediazide compound (particularly a naphthoquinonediazide compound). The preferred naphthoquinonediazide compound is an n-naphthoquinonediazidesulfonic acid compound (for example, 〇-naphthoquinonediazide-5-sulfonic acid, 〇-naphthoquinonediazide-4-sulfonic acid, etc.), and more An ester of a phenol (preferably a polyvalent phenol having three or more phenolic hydroxyl groups) or the like. A polyvalent phenol such as (i) a compound in which a benzene ring having one or more hydroxyl groups is bonded via a carbonyl group (hereinafter referred to as "hydroxybenzene-containing ring") (ii) is bonded to an alkyl group (preferably a formazan) a compound containing a hydroxybenzene ring, and (iii) a dihydropyran ring and a first hydrogen-containing benzene ring condensed ring, the dihydropyran ring portion of the condensed ring is bonded to the second hydrogen group A compound of a phenyl ring.多 The polyvalent phenol of the above (i) is, for example, di, tri, tetra or pentahydroxybenzophenone (preferably, such as 2,3,4,4,-tetrahydroxybenzophenone, etc.). The polyvalent phenol of the above (ii) is a compound represented by the formulae (101) to (107). -84- 200936563

【化5 8】

The polyvalent phenol of the above (iii) is a compound represented by the formulae (108) to (111). -85- 200936563 【化5 9】

The polyvalent phenol is preferably classified into the above (iii), and more preferably a compound (1 1 〇 ). &lt;Hardener (C) &gt; The hardener (C) used may be a compound having a thermosetting effect, such as a melamine compound. A preferred melamine compound is represented by the formula (III). [化6 0] r300oh2c

Ch2or302 Nx CH2OR303 r305oh2c/N, ch2or304 (in) -86- 200936563 In the formula (III), R3G° to R3°5 are each independently hydrogenated c!_12 alkyl or branched C3-10 alkyl. However, the total number of R3QQs is less than four. Linear C!-12 alkyl such as 'methyl, ethyl, η-propyl, η-pentyl, η-hexyl, η-heptyl, η-octyl, η-fluorenyl, undecyl, Η-dodecyl group or the like, preferably, such as methyl, ethyl, η-butyl, η-pentyl or η-hexyl, etc., linear C丨·6 alkyl hydrazine, branched C3_1Q alkyl group, Butyl group, sec-butyl group, 2-ethyl-η-hexyl group or the like is preferably a branched C3-5 alkyl group such as isobutyl group or see-butyl group. The melamine compound represented by the formula (?) is preferably methyl melamine, hexaethoxymethyl melamine, hexapropyl melamine or hexabutoxymethyl melamine. More preferably, it is hexamelamine (also known as hexamethoxymethylol melamine) methyl melamine. ® hardener (c) can be guanine such as tetramethoxymethylbenzoethoxymethylbenzoguanamine, tetrapropoxymethylbenzoyloxymethylbenzoguanamine An amine compound, and a compound represented by the formula (IV-6). Atom, a straight chain r3()5 hydrogen primordium, η-butyl η-fluorenyl group, η-group, η-propyl tert-butyl group, , tert-butyl, hexamethoxyoxymethyltrimethoxymethyl and hexaethoxyguanine, tetrahydroamine, tetrabutyl IV-1) to formula -87- 200936563 [Chem. 6 1]

(IV-t) CH,

(IV-2&gt; H3COH2C CH2OCH3 N8 N 〇 0=4 W〇 H3COH2Cx /CH20CH3

Vi κι N N

N^IM Γ J H3COH2G CH20CH3 (IV-3) (IV-4)

H3C〇H2C, ί CH2〇CH3 〇, N人N〆

H3COH2C\ human/CHzOCHs IJNN, N' C2H5 (IV-5) (IV-6) &lt;content of polymer (A), sensitizer (B) and hardener (C)&gt; Polymerization in photosensitive composition 1 The content of the substance (A), the sensitizer (B), and the hardener (C) (the total amount of the polymer (A), the sensitizer (B), and the hardener (C) in an amount of 100 parts by mass) are each as follows. . 〇 Polymer (A): preferably from 30 to 70 parts by mass, more preferably from 40 to 60 parts by mass. The sensitizer (B): preferably from 1 Torr to 60 parts by mass, more preferably from 20 to 5 Å by mass. The hardener (C): preferably from 5 to 30 parts by mass, more preferably from 10 to 20 parts by mass. When the amount of the polymer (A) is in the above range, it has sufficient solubility to the developing solution, and the developing process is less likely to cause a decrease in the film, and it is preferable to reduce the amount of exposure when the image is lithographically formed. When the amount of the photosensitive agent (B) is in the above range, the film can be reduced during the development of the pattern, and the exposure time when the pattern is formed by the photolithography can be shortened. When the amount of the curing agent (C) is in the above range, the amount of exposure can be reduced when the pattern is formed by photolithography. The pattern after development is also good in shape, and the mechanical strength of the pattern after heating and hardening is also sufficient. e &lt;Photosensitive Composition&gt; The photosensitive composition 2 of the present invention contains the polymer (A), the hardened 5 ((C), the photoacid generator (D), the solvent (Η), and, if necessary, the amine system The compound (Ε). The hardener (C) is as described above. &lt;Photoacid generator (D) &gt; The photoacid generator (D) may be various known photoacid generators, such as an iodine iodine salt compound, Sulfuric acid salt compound, organohalogen compound (haloalkyl-s-triazine compound, etc.), sulfonate compound, diphosgene compound, diazomethanesulfonate compound, sulfonium sulfonate compound, lanthanide A compound such as a photoacid generator (D) is a quinone compound. A quinone compound such as α-(4-toluenesulfonyloxyimino)benzyl cyanide or α-(4-toluenesulfonate) Amidino)-4-methoxybenzyl cyanide, α-(nonylsulfonyloxyimido)-4-methoxybenzyl cyanide, α-trifluoromethanesulfonyloxyimide 4-methoxybenzyl cyanide, a-(1-hexanesulfonyloxyimino)-4-methoxybenzyl cyanide, α-naphthalenesulfonyloxyimide-89- 200936563 base-4-methoxy Benzyl cyanide, α-(4-toluenesulfonyloxyimino)-4- N-diethylanilinyl cyanide, α-(4-toluenesulfonyloxyimino)-3,4 a cyanide such as dimethoxybenzyl cyanide or α-(4-toluenesulfonyloxyimido)-4·thienyl cyanide; α-(4-toluenesulfonyloxyimino) )-α_(4-methoxyphenyl)acetonitrile, (5-p-toluenesulfonyloxyimino-5-oxime-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile, (5 - sulfonyloxyimino- 5Η-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile, (5-η-propoxyimino-5-thiophen-2-indenyl) )-(2-methylphenyl)acetonitrile, (5-η-octyloxyimino-5-nonylsulfonyloxyimino-5-thiophene-2-ylidene)-(2-methyl Acetonitrile such as phenyl)acetonitrile. &lt;Content of polymer (Α), hardener (C) and photoacid generator (D)&gt; Polymer (A) and hardener (C) in photosensitive composition 2 And the content of the photoacid generator (D) (relative to the total mass parts of the polymer (A), the hardener (C), and the photoacid generator (D)) are each as described below for the content of the ruthenium polymer (A) : preferably 60 to 95 The mass fraction is more preferably 70 to 90 parts by mass. The content of the hardener (C): preferably from 1 to 35 parts by mass, more preferably from 5 to 30 parts by mass. The content of the photoacid generator (D): preferably It is 1 to 15 parts by mass, more preferably 3 to 10 parts by mass. When the amount of the polymer (A) is in the above range, it has sufficient solubility to the developing liquid, and it is not easy to cause film reduction during the image forming process. The lithography-90-200936563 reduces the amount of exposure when forming a pattern. When the amount of the curing agent (C) is in the above range, when the photosensitive composition 2 is formed into a pattern, the pattern shape which is excellent in exposure can be reduced, and the pattern can be heat-cured to obtain sufficient mechanical strength. When the content of the photoacid generator (D) is in the above range, the product 2 is cured to obtain good strength and surface smoothness. &lt;Amine compound (E) &gt; The photosensitive composition 2 of the present invention may further contain an amine. ? . When an amine compound is used, the long-term storage of the photosensitive composition does not greatly change the amount of exposure when performing photolithography. In the case of the composition, it is possible to reduce the size of the pattern due to the occurrence of photoacid during the exposure. Applicable to the former, which can exert the effect of the stability of exposure, '3_Amino-1-propanol, 1-amino-2-propanol, 2-amino-2-methyl-1-propanol, Amino alcohols such as 2-amino-2-methyl-1,3-propanediamine-1-butanol; U-diazabicyclo 1,8-diazabicyclo[5·4. A compound having a diazabicyclic structure such as -7-undecene or 1,5-diazaindole-5-ene. It is suitable for the amine 4-nitroaniline, ethylenediamine, tetramethylammonium, 4,4'-diamino-1,2-diphenylethane, which can exert dimensional stability effects. 4,4,-diamine a diphenylmethane, 4,4'-diamino-3,3,-diethyldiphenyl tablet lithography from the present amount. Further, after the image is formed, the photosensitive group 艮 compound (E) is used before and after the amine group J (D) is used as an inactive amine compound such as 1-propanol or 2-amine alcohol. 3-methyl-2-[2.2.2]octane, heterobicyclo[4.3 _0]-based compounds such as, hexamethylenediamine, g-3,3 dimethylmethane, 4,4'--91 - 200936563 Diamino-3,3',5,5'-tetraethyl-diphenylmethane, 8-quinolinol, benzimidazole, 2-hydroxybenzimidazole, 2-hydroxyquinazoline, 4 -Methoxybenzylidene-4'-η-butylaniline, decyl salicylamine, salicylanilide, 1,8-bis(indole, fluorene-dimethylamino)naphthalene, 1,2 -diazine (pyridazine), piperidine, ρ-amino-benzoic acid, oxime-ethionylethylamine, 2-methyl-6-nitroaniline, 5-amino-2-methylphenol , 4-η-butoxyaniline, 3-ethoxy-η-propylamine, 4-methylcyclohexylamine, 4-tert-butylcyclohexylamine, monopyridine (imidazole, acridine, 4 -methylpyridine, 4-methylimidazole, 2-dimethylaminopyridine, 2-methylaminopyridine, 1,6-lutidine, etc.), dipyridines (dipyridine, 2, 2 '-dipyridyl Amine, di-2-pyridinone, 1,2-bis(2-pyridyl)ethane, 1,2-bis(4-pyridyl)ethane, 1,3-bis(4-pyridyl)propane 1,2-bis(2-pyridyl)ethene, iota,2-bis(4-pyridyl)ethene, 1,2-bis(4-pyridyloxy)ethane, 4,4'-dipyridine Base sulfide, 4,4'-dipyridyl disulfide, 1,2-bis(4-pyridyl)ethylene, 2,2'-dipyridylmethylamine, 3,3'-dipyridylmethylamine Etc.), ammonium salts (tetramethylammonium hydroxide 'tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetra-hexyl guanidinoammonium hydroxide, tetra-n-octyl ammonium Hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, choline, etc.). When the amine compound (E) is used, the content thereof is preferably from 0.1 to 1 part by mass, more preferably from 5 to 5 parts by mass, per part by mass of the photoacid generator (D). Photosensitive Composition 3 &gt; -92- 200936563 The photosensitive composition 3 of the present invention contains the polymer (A) compound (F), a photopolymerization initiator (G), and a solvent (H) &lt; a polymerizable compound (F) &gt; The polymerizable compound (F) used may be a monofunctional or polyfunctional (meth) propyl group having an ethyl sulfenyl compound (for example, N-vinylpyrrolidone), etc., preferably a methyl) acrylonitrile group. . Further, it is preferable to use a polyfunctional (meth) acrylate compound having two or more (more preferably three or more) acryl fluorenyl groups. The compound (F) may be used singly or in combination of two or more kinds. Monofunctional (meth) acrylate compounds such as 2-hydroxy) acrylate, 2-hydroxy-3-phenoxypropyl (methyl) propyl hydroxyalkyl (meth) acrylate; a (meth) acrylate having an etherified content, such as a olefinic acid ester, a 2-ethylhexyl carbitol (meth) acrylate, an oxyethoxy group, an ethyl (meth) acrylate; Long-chain alkyl (meth) acrylate (meth) acrylate such as lauryl (meth) acrylate (meth) acrylate, and caprolactone (meth) acrylate heterocyclic (meth) acrylate Ethoxylated nonylphenol ((meth) acrylate such as a olefinic acid ester, a propoxylated nonyl phenol (meth) acrylate, etc. a bifunctional (meth) acrylate compound such as 1 , 3-butyryl) acrylate, 1,6-hexanediol di(meth)acrylic acid alkyl di(meth)acrylate; neopentyl glycol di(methyl, polymerizable ethylene as having (acid) Ester compound (methyl). Polymerizable ethyl (methyl methacrylate), 2- 2- 2-ethanediol , stearyl ester; tetrahydroester, etc. having methyl) propylene having aromatic diol di(ester) linear acrylic acid-93-200936563 ester, propoxylated neopentyl glycol di(meth) acrylate, ethoxylate Branched alkyl di(meth)acrylate such as neopentyl glycol di(meth)acrylate or 3-methylpentanediol di(meth)acrylate; ethylene glycol di(methyl) Alkylene glycol such as acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol diacrylate Di(meth)acrylate; bis((meth)acryloxyethyl)ether of bisphenol A; ethoxylated bisphenol A-di(meth)acrylate, etc. Acrylate compound such as trimethylolpropane tri(meth)acrylate 'pentaerythritol tri(meth)acrylate or the like branched alkyl tri(meth)acrylate; tris(2-hydroxyethyl) Trimeric isocyanate tri(meth)acrylate; ethoxylated trimethylolpropane tri(meth)acrylate, propoxy Alkoxylated branched alkyl tri(meth)acrylate such as trimethylolpropane tri(meth)acrylate; pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, Dipentaerythritol hexa(meth) acrylate, tripentaerythritol tetra (meth) acrylate, tripentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, Pentaerythritol (meth) acrylates such as tripentaerythritol octa (meth) acrylate; reactants of pentaerythritol tri(meth) acrylate and anhydride; reactant of dipentaerythritol penta (meth) acrylate and anhydride, tripentaerythritol a reaction of pentaerythritol (meth) acrylate with an acid anhydride such as a reaction of hepta (meth) acrylate with an acid anhydride; a caprolactone-modified trimethylolpropane tri(meth) acrylate, caprolactone-modified pentaerythritol Tris(A-94-200936563) acrylate, caprolactone modified tris(2-hydroxyethyl)trimeric isocyanate tri(meth)acrylate, Ester-modified pentaerythritol tetra(meth) acrylate, caprolactone-modified dipentaerythritol penta(methyl) propyl acrylate, caprolactone-modified dipentaerythritol hexa(meth) acrylate, caprolactone modified Pentaerythritol tetra(meth)acrylate, caprolactone modified tripentaerythritol penta (meth) acrylate, caprolactone modified tripellitate hexa(meth) acrylate, caprolactone modified pentaerythritol heptyl (methyl) Caprolactone-modified polyfunctional (meth) acrylate such as acrylate or hexanolide modified trimellititol octa (meth) acrylate; reaction of caprolactone with pentaerythritol tri(meth) acrylate and anhydride a caprolactone-modified polycaprolactone such as a reaction of caprolactone-modified dipentaerythritol penta(meth)acrylate with an acid anhydride, a reaction of caprolactone-modified tripentaerythritol hepta(meth)acrylate and an acid anhydride (A) a reaction of an acrylate with an acid anhydride or the like. Preferred polyfunctional (meth) acrylate compounds such as tetrafunctional (meth) acrylate compounds (for example, tripentaerythritol tetrakis(meth) propylene phthalate), pentafunctional (meth) acrylate compounds (for example, dipentaerythritol) a reaction of penta (meth) acrylate, tripentaerythritol penta (meth) acrylate, dipentaerythritol penta (meth) acrylate with an acid anhydride, caprolactone-modified dipentaerythritol penta (meth) acrylate, Reaction of ester-modified tripentaerythritol penta (meth) acrylate, caprolactone-modified dipentaerythritol penta(meth) acrylate with an acid anhydride; in particular, tripentaerythritol penta(meth) acrylate), 6-functional (A) Acrylate compound (for example, dipentaerythritol hexa(meth) acrylate, tripentaerythritol hexa(meth) acrylate, caprolactone-modified dipentaerythritol hexa(meth) acrylate-95-200936563, caprolactone modification Triquat pentaerythritol hexa(meth) acrylate; especially dipentaerythritol hexa(meth) acrylate, tripentaerythritol hexa(meth) acrylate ), And 7 of the above polyfunctional (meth) acrylate compound (e.g., tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate). More preferably, the 5- to 6-functional (meth) acrylate compound is particularly preferably dipentaerythritol hexa(meth) acrylate. &lt;Photopolymerization Initiator (G) &gt; q Photopolymerization Initiator (G), for example, an anthraquinone compound, an acetophenone compound, a diimidazole compound, a triazine compound, and a mercaptophosphine oxide compound (Comparative) Preferably, it is a lanthanide compound) (hereinafter referred to as a first photopolymerization initiator). The photopolymerization initiators may be used singly or in combination of two or more. Specific examples of the lanthanoid compound, for example, 〇-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, a compound represented by the formula (V-1), and a formula (V-2) The compound represented, etc. The compound (V -1 ) is sold under the trade name "〇 IRGACURE ΟΧΕ 01", such as Jiba. 【化6 2】

An acetophenone-based compound such as diethoxyethyl benzene, 2-hydroxy-2-methyl-96-200936563-l-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy- 1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2-morpholinyl (4-thiol) Phenyl)propan-1-one, 2-methyl-1-(4-methylthiophenyl)-2-morpholinylpropan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinylphenyl)butan-1-one, 2-(2-methylbenzyl)-2-methylamino-1-(4-cylinylphenyl)- Ding Yuan-1-嗣, 2-(3-methylbenzyl)-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2·(4 - Methyl decyl)-2 -monomethylamino-1-( 4·-morphinylphenyl)-butan-1-one, 2-(2-ethylbenzyl)-2-dimethyl Amino-1-(4-morpholinylphenyl)-butan-1-one, 2-(2-propylbenzyl)-2-dimethylamino-1-(4-morpholinylbenzene Butyl-1-butanone, 2-(2-butylbenzyl)-2-dimethylamino-1-(4-cylinylphenyl)-butyl--1-嗣' 2- (2,3 - _methylbenzyl)-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(2,4-dimethyl 2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(2-chlorobenzyl)-2-dimethylamino-1- (4-morpholinyl phenyl)-butan-1-one, 2-(2-bromobenzyl)-2-dimethylamino-1-(4-morpholinylphenyl)-butane 1-ketone, 2-(3-chlorobenzyl)-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(4-chlorobenzyl -2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(3-bromobenzyl)-2-dimethylamino-1-( 4-morpholinylphenyl)-butan-1-one, 2-(4-bromobenzyl)-2-methylamino-1-(4-morphinylphenyl)-butyl-house-1 -嗣, 2_(2-methoxybenzyl)-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(3-methoxybenzyl 2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(4-methoxybenzyl)-2-dimethylamino- -97- 200936563 1-( 4 -morpholinylphenyl)-butan-1-one, 2·(2-methyl-4-methoxyl)-2-methylamino-1- (4-morphinylphenyl)· dingyuan _丨-ketone, 2_(2-methyl-4-bromoindolyl)·2-dimethylamino 4-(4-morpholinylphenyl)_ Butan-1-one, 2-(2-bromo-4- Methoxybenzyl)_2·dimethylamino 丨—( 4 —morpholinylphenyl)-butan-1-one, 2-hydroxy-2-methyl-i_[4-(1-methyl Vinyl)phenyl]propan-1-one and the like. Diimidazole-based compounds such as 2,2,-bis(2-chlorophenyl)-4,4,5,5,-tetraphenyldiimidazole, 2,2,-bis(2,3-dichlorobenzene _4,4,5,5,_tetraphenyldiimene (for example, JP-A-6-75372 and JP-A-6-75373, etc.), 2,2'-bis(2-chlorophenyl)- 4,4,,5,5,-tetra(institutional oxy-based)-M-indole, 2,2'-bis(2-chlorophenyl)-4,4,5,5,-tetra(dialkyloxy) Phenyl)diimidazole, 2,2'-bis(2-chlorophenyl)_4,4,5,5,-tetrakis(trialkoxyphenyl)diimidazole (for example, refer to Japanese Patent No. 48_3 84〇3) No. 62-174204, etc., and a diphenyl sulfonium compound substituted with a phenyloxycarbonyl group at the 4, 4, 5, 5, _ position (for example, refer to JP-A-7-10913) No. bulletin, etc.). Triazine-based compounds such as 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) -6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperidin-nt triple exposure '2,4-double (two Chloromethyl)-6-(4-methoxyphenylethyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methyl) Furan·2—yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3 ,5-triazine, 2,4-bis(trichloromethyl)-6_[2_(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine , 2,4-bis(tri-98-200936563 chloromethyl-6-[2-(3,4-dimethoxyphenyl)vinyl]-mercaptophosphine oxide compound such as 2, 4 6-trimethylbenzene phosphine oxide, etc. The photopolymerization initiator (G) (the first photopolymerization initiator such as a quinone ketone compound, a diimidazole compound, a triazine compound, or a compound compound) The second photopolymerization initiator may be used in one type of the second photopolymerization initiator, for example, a compound, an acetophenone compound, or a thioxanthone compound. , oxime, etc. benzoin compounds such as benzoin, benzoin formic acid, ether, benzoin isopropyl ether, and benzoin isobutyl ether, etc. Acetophenone compounds such as acetophenone, hydrazine -Phenyl phenyl benzophenone benzoacetophenone, 4-phenylhydrazinyl-4,-methyldiphenyl sulfide, tetrakis (tert-butyl carbon monoxide) acetophenone, and 2,4,6_ Triterpene ketone, etc. Thiophenone compounds such as 2-isopropylthioxanthone, 4-isoketone, 2,4·diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro Thioxanthene, etc. Lanthanide compounds such as 9,10-dimethoxyanthracene, 2-ethyl-oxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethyl Oxygen 3 The second photopolymerization initiator is in addition to the above-exemplified compounds 10-butyl-2-chloroacridone, benzyl (= "i,2-diphenylethane"), methyl phenylglyoxylate, Ferrocene compound, 2-B, 5-diene, etc., diphenylbenzene, phenethyl fluorene or two kinds of bismuth compounds: phenylene acetophenone methyl ester, α-β), , &quot;,-methyl phenyl propyl thioxanthene-4-propoxy 9,10-dimethyl sulfonium and the like. Further, it may be -1,2-dione oxime, -99-200936563 9,10-phenanthrenequinone, anthracene, and the like. Further, the second photopolymerization initiator may be a compound having a group capable of generating chain shift, as described in JP-A-2002-544205. Such a compound is, for example, a compound represented by the formula (VI-1) to the formula (VI-6). [Chemical 6 3] h2 C-C -S-(CH2)3 h3cooc H2Gx)c-c-o-(chy2 G4Hg-S-CH2 h2c

o ch3 II 1 7 CCN p (VF-1) CH, O ch3 11 I CCN 0 (VI-2) o II H cn-ch2-s C4H9-S-CH2 h2c ύ a CH2—s CHg o ch3 11 I SCN 0 o gh3 II I Plant CCN I , ch3 (VI-3) b (VI-4)

H2C

H3COOC \-C2-S-(CH2)3-

(VF5) CH3 ch3

H2\ h2 C-C -S-(CH2)3_S H3COOC

0 CH2 ChU /==\ II I / 3 /~C~?~N\ (VI-6> c2h5 ch3 &lt;Polymer (A), polymerizable compound (F) and photopolymerization initiator (G) &gt; Content of polymer (A), polymerizable compound (F) -100-200936563 and photopolymerization initiator (G) in photosensitive composition 3 (relative to polymer (a), polymerizable compound (F) and The amount of the photopolymerization initiator (g) in a total amount of 00 parts by mass is as follows. The polymer (A): preferably 15 to 8 parts by mass, more preferably 50 to 80 parts by mass. It is preferably 15 to 80 parts by mass, more preferably 15 to 35 parts by mass. The photopolymerization initiator (G): preferably 1 to 15 parts by mass, more preferably 3 to 10 parts by mass. In the case of the photopolymerization initiator and the second photopolymerization initiator, the content of the photopolymerization initiator (G) is the total amount of the second photopolymerization initiator and the second photopolymerization initiator. When the amount of the polymer (A) is in the above range It has sufficient solubility for the developing solution', and the developing process is not easy to cause film reduction, and the exposure amount when forming a pattern by photolithography can be reduced. ® The amount of the polymerizable compound (F) is the above range When the amount of the photopolymerization initiator (G) is within the above range, the photolithography initiator (G) can be reduced in the form of a photolithographic image by increasing the sensitivity of the photosensitive composition, the strength, smoothness, and mechanical strength of the coating film and the pattern. The amount of exposure at the time of the pattern is good, and a good pattern shape can be obtained after the image is formed, and the mechanical strength of the pattern is also sufficient after heat curing the pattern. &lt;Sclerosing Composition 4&gt; The curable composition of the present invention 4 Containing polymer (a), hardener-101-200936563 (c), solvent (Η) and, if necessary, amine compound (E). The description of hardener (C) and amine compound (E) is as described above. In essence, the curable composition of the present invention does not contain a sensitizer, a photopolymerization initiator, and a photoacid generator&lt;content of the polymer (A) and the hardener (C)&gt; a polymer in the curable composition 4 (A) The content of the curing agent (C) and the photoacid generator (D) (in terms of the total amount of the polymer (A) and the curing agent (C) in an amount of 1 part by mass) is as follows. Polymer (A) Content: preferably 70 to 98 parts by mass, more preferably 80 to 95 parts by mass. Content of hardener (C): preferably 2 to 30 parts by mass, more preferably 5 to 20 parts by mass. &lt;Photosensitive composition 1 to 3 and curable composition 4&gt;&lt;SolventH&gt; Photosensitive compositions 1 to 3 and curable composition 4 Each component can be dissolved or dispersed in the solvent (H). The solvent (H) can be appropriately selected depending on the solubility of each component, the coating property of the composition, etc. Solvent (Η), for example, ethylene glycol (methyl cellosolve, Ethyl cellosolve, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol dimethyl ether, ethylene glycol monoisopropyl ether, etc., propylene glycol (propylene glycol monomethyl ether, Propylene glycol monomethyl ether acetate, etc., Ν-methylpyrrolidone, γ-butyrolactone, dimethyl sulfoxide, hydrazine, hydrazine-dimethylformamide 'ketones (4-hydroxy-4-methyl - 2- -102- 200936563 Pentanone (alias diacetone alcohol), cyclohexanone, etc.), carboxylic acid esters (ethyl acetate, η-butyl acetate, ethyl pyruvate, ethyl lactate, lactate n-butyl Ester, etc.). These solvents may be used alone or in combination of two or more. The content of the solvent (Η) may be 40 to 95% by mass, preferably 70 to 90% by mass, based on the entire composition. When the amount of the solvent is in the above range, the composition can have a good coating property to form a uniform coating film. ® &lt;Other Additives (J) &gt; Further, if necessary, the photosensitive compositions 1 to 3 and the curable composition 4 of the present invention may contain other additives (J) (e.g., surfactants, polymers, etc.) Polymer composition, etc.). The surfactant comprises a polyoxyalkylene surfactant [for example, all of the polyoxyalkylene DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, 29SHPA, SH30PA, polyether modified eucalyptus S Η 8 4 0 0 (above雷 矽 矽 矽 ( ΚΡ ΚΡ, ΚΡ 321, ΚΡ 3 22, ΚΡ 3 23, © κρ324, ΚΡ 326, ΚΡ 340, ΚΡ 341 (above is Shin-Etsu Chemicals), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (above, such as Diy Toshiba polyoxyalkylene (manufactured)), a surfactant containing a siloxane coupling, etc.]; a fluorine-based surfactant [such as Flora FC 4 3 0, FC 4 3 1 (above is Sumitomo 3Μ (share) system), Mi Jiafan (registered trademark) F142D, F171, F172, F173, F177, F183, R30 (above is the Dainippon Ink Chemical Industry Co., Ltd.), Yev EF301 &gt; EF303, EF351, EF352 (above is New Akita Chemicals Co., Ltd.), Saffron S381, S3 82, -103- 200936563 SC101, SC105 (above is Asahi Glass Co., Ltd., E5844 (Dajin Chemical) Research Institute (share) system, BM-1000, BM-1100C A surfactant having a fluorocarbon chain, etc., manufactured by BM Chemie Co., Ltd.; a polyoxyalkylene surfactant having a fluorine atom [Mega Fan R〇8, BL20, F475, F4 77, F443 (above a surfactant having a siloxane chain or a fluorocarbon chain, etc., etc., etc. These surfactants may be used singly or in combination of two or more. When a surfactant is used, it is photosensitive. When the total amount of the material is 1% by mass, the amount thereof may be 0.0005 mass% to 0.6 mass%, preferably about 0.001 mass% to 0.5 mass%. When the amount of the surfactant used is in the above range, the photosensitive composition is coated. A flat coating film is easily obtained. Other polymer components such as an alkali-soluble polymer having a carboxyl group. The alkali-soluble copolymer having a carboxyl group is specifically, for example, (meth)acrylic acid/methyl(meth)acrylate. Copolymer, (meth)acrylic acid/benzyl (meth) acrylate copolymer, (meth) acrylate/2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate copolymer, ( Methyl acrylate / A (Meth)acrylate/polystyrene high monomer copolymer, (meth)acrylic acid/methyl(meth)acrylate/polymethylmethacrylate high monomer copolymer, (meth)acrylic acid/ Benzyl (meth) acrylate / polystyrene high monomer copolymer, (meth) acrylate / benzyl (meth) acrylate / polymethyl methacrylate high monomer copolymer, (methyl) Acrylic acid/2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polystyrene high monomer copolymer, (meth) acrylate / 2-hydroxyethyl (meth) acrylate / Benzyl (meth) acrylate / poly-104- 200936563 methyl methacrylate high monomer copolymer, methacrylic acid / styrene / benzyl (meth) acrylate / N-phenyl malayan Amine copolymer '(meth)acrylic acid / succinic acid mono(2-propenyloxyethyl) / styrene / benzyl (meth) acrylate / N-phenyl maleimide copolymer, (A Acrylic acid/succinic acid mono(2-propenyloxyethyl)/styrene/allyl (meth) acrylate/N-phenylmaleimide Product (meth) acrylic acid / benzyl (meth) acrylate / N- phenylmaleimide (PEI) / styrene / [Phi] a glycerol (meth) acrylate copolymer and the like. These other polymer components may be used singly or in combination of two or more kinds. The photosensitive compositions 1 to 3 and the curable composition 4 of the present invention may further contain other additives or additional components (for example, an epoxy resin, an oxetane compound, an ultraviolet absorber, or the like without detracting from the effects of the present invention). Antioxidants, chelating agents, etc.). Further, the composition of the present invention may contain a functional substance for the purpose of use. For example, a filter or the like can be produced, and the composition of the present invention may contain a pigment, a pigment, or the like. The photosensitive compositions 1 to 3 of the present invention can be used in a wide range of fields, for example, in the manufacture of optical components such as semiconductor elements, optical elements, printed boards, printing plates, liquid crystal display panels, and electric display panels. Used for photoresist film. Further, it is not limited to development (drawing), and can also be used for non-development purposes (e.g., protective film, flattening film, etc.). The curable composition 4 of the present invention can be used in a wide range of fields, for example, as a protective film or a flattening film for manufacturing semiconductor elements, optical elements, printed boards, printing plates, liquid crystal display panels, plasma display panels, and the like. Next, the process of forming a film from the photosensitive composition of the present invention -105-200936563 by photolithography, and the process of forming a film from the curable composition 4 of the present invention will be sequentially described. &lt;Photosensitive Compositions 1 to 3 by Photolithography> The photosensitive compositions 1 to 3 of the present invention are preferably prepared by mixing filters in a solvent and generally filtering them with a filter having a poise size of 0·2 μm or less. And got it. The uniformity in coating the photosensitive composition can be improved after filtration. When the pattern is formed by the photosensitive compositions 1 to 3 of the present invention by photolithography, for example, the following steps can be carried out. (1) a step of applying a photosensitive composition onto a support (2) a step of removing a solvent (3) a step of exposing the coating film obtained by coating according to a mask pattern corresponding to a target pattern (4) The developing step (5) is a step of applying ultraviolet rays to the obtained pattern (6). When the step of heating the pattern is applied to the photosensitive composition, it is preferred to mix the components of the photosensitive composition in advance with a solvent. Filter with a filter having a poise size of 0.2 μηη or less. The uniformity in coating the photosensitive composition can be improved after filtration. The support for coating the photosensitive composition can be appropriately set depending on the application, such as a circuit board for forming an image sensor such as a solid-state element such as a CCD or a CMOS, a transparent glass plate, a quartz circuit board, or the like. The method of forming the coating film of the photosensitive composition on the support is not particularly limited, and a spin coating method, a roll coating method, a bar coating method, a die coating method, a dip-106-200936563 coating method, and a casting coating can be suitably employed. General coating methods such as a method, a roll coating method, a slit & spin coating method, and a slit coating method. After the photosensitive composition is applied to the support, the volatile component such as a solvent can be removed by heating (for example, heating at 70 to 120 ° C) to form a coating film. When the coating film is exposed, the corresponding target pattern is introduced. The pattern of the mask illuminates the film. The light used is, for example, the g line, the h line, the i line, etc., and the φ can be an exposure machine such as a g line stepper, an h line stepper, or an i line stepper. The amount of light to be irradiated in the field of irradiation can be appropriately selected depending on the type (A) of the polymer, the kind and content of other components, and the like. When the photosensitive compositions 1 and 2 of the present invention are used, the obtained coating film can be heated. When heated, the coating film can be hardened by the action of the hardener (C) to increase the mechanical strength of the coating film. The heating temperature during heating is, for example, 80 to 150 °C. The development may be carried out by a method in which the support of the coating film is contacted with a general developing solution. The developing solution is not particularly limited, and for example, an aqueous alkali solution (preferably 〇 is a tetramethylammonium hydroxide aqueous solution) or the like can be used. The necessary imaging solution can be mixed with a surfactant. The imaging solution is removed and then washed to remove the imaging solution to form a pattern. It can also be rinsed with a rinse solution and then washed with water. This rinsing process removes the residue of the photosensitive composition remaining on the support at the time of development. Thus, the pattern can be formed by the coating film. Ultraviolet light is applied to the resulting pattern. The photosensitive component remaining on the pattern is decomposed by ultraviolet irradiation. The pattern is heated by irradiating the pattern with ultraviolet light. The mechanical strength of the pattern can be increased by heating. The heating temperature is generally from 100 to 220. (: When the heating temperature -107 - 200936563 degrees is in the above range, the curing can be sufficiently performed. Further, after the photosensitive compositions 1 to 3 of the present invention are applied to the support, they can be cured without being patterned. The coating film has excellent characteristics (planarization characteristics) for releasing the coating surface difference, and can be used as a flat film and a protective film. &lt;Forming a film with the curable composition 4&gt; Applying the curable composition 4 of the present invention to After the support, a protective film or the like can be formed by thermal curing. When the curable composition is applied, it is preferred to mix the components of the curable composition in a solvent in advance, and the poise size is about 0 · 2 μηι or less. The filter is filtered. The uniformity of the coating of the curable composition can be improved after filtration. The support for the coating of the curable composition can be appropriately set according to the application. The method of forming the coating film of the curable composition on the support The support and the coating film formation method may be the same as those of the photosensitive composition. After the curable composition 4 of the present invention is applied to a support, heating may be utilized (for example, 70 to 12) 0 °C heating), etc. The present invention will be described in more detail by way of examples, but the invention is not limited to the following examples, which may be appropriately within the scope of the above or the following. The change implementations are all included in the technical scope of the present invention. -108- 200936563 In the examples, the "%" and "parts" of the content or the amount of use are indicated by the following means: "% by mass" and "parts by mass" Synthesis Example 1 (Synthesis of Compound (I -1 -1 )) 6.6 g (65 mmol) of acesulfame anhydride, 4-dimethylamino group [J ratio steep 0.36 g (2.9 mmol), and pyridine 52 g were added to the compound (a_3). L〇.〇g (3 2mm〇l, Dajinhua finished product sales (stock) system), stir under reflux for 2.5 〇 hours. Secondly, the reaction solution is cooled to room temperature, add toluene 1 OOrnL, then hydrochloric acid 50 mL and The organic layer was washed twice with 50 mL of water, and the organic layer was taken out, dried over magnesium sulfate and filtered. The activated carbon was added to the filtrate and stirred at 60 ° C for 1 hour, and then filtered with diatomaceous earth. After removing the solvent, it was dried at 60 ° C under reduced pressure to give a compound ( 1 -1 -1 ) (methacrylate containing fluorine and carboxyl groups) U.9g° [Chem. 6 4]

【化6 5】

-109-200936563 The structure of the compound (1-1-1) was determined by 1H-NMR (Ex_270; manufactured by Nippon Electronics Co., Ltd.). 1H-NMR (2 70MHz, δ 値 (ppm, TMS basis), CDCI3, room temperature); 1_95 (3H, s), 2.4-2.7 (6H, m), 4·1-4·4 (2Η' m) 5.4 -5.6 (1Η, m), 5.63 (1Η, d, J=l.〇Hz), 6.12 (1Η, d, J = 1.0Hz), 9.29 (1 H, bs). Synthesis Example 2 (Synthetic Polymer Aa) 14.0 g of methyl isobutyl ketone was placed in a 50 〇 mL 4-neck flask equipped with a dropping funnel, a Dimrod cooling tube, a thermometer and a mechanical stirrer, and nitrogen was stirred under stirring. After flowing through the flask for 1 minute, the temperature was directly raised to 90. (:. Compound (1-1-1) Π.9g (29mmol), 2,2'-azobis(isobutyronitrile) 0.140g (0.85mmol) and methyl isobutyl ketone 50g were placed in a 200 mL beaker The mixture was stirred at room temperature to obtain a homogenous solution. After the solution was added to the dropping funnel, it was dropped into a 4-neck flask maintained at 90 ° C for 1 hour. After the completion of the dropping, the 4-necked flask was kept at 9 ( After stirring for 4 hours at TC, a colorless solution was obtained. After cooling the mixture in a 4-neck flask to room temperature, the obtained colorless solution was transferred to a 1 L eggplant flask, and the solvent was distilled off by a rotary evaporator, and then dried under reduced pressure at 60 ° C. The polymer Aa was 11.8 g. The number average molecular weight (?n) of the polymer Aa was 11,800, the weight average molecular weight (Mw) was 510,00, and the degree of dispersion (Mw/Mn) was 44. The weight average of the aforementioned polymer Aa The molecular weight (Mw) and the number average molecular weight (Μη) are measured by the GPC method (in terms of polystyrene) under the following conditions: -110- 200936563 Apparatus·· K2479 (Shimadzu Corporation)

Column: SHIMADZU Shim-pack GPC-80M

Column temperature: 40 °C Solvent: THF (tetrahydrofuran)

Flow rate: 1.0 mL/min Tester: RI Test solvent: 2% THF solution ❹ Synthesis Example 3 (Synthesis Compound (1-1-2)) Succinic anhydride 4.9 g (49 mmol), 4-dimethyl 0.31 g (2.5 mmol) of pyrithione and 5 1 g of pyridoxine Add compound (a-1) 1 O.Og (24 mmol, manufactured by Daikin Chemicals Co., Ltd., CAS Ν ο. 1 6 0 8 3 - 7 9 - 7 ), and stirred for 3.5 hours under reflux. Next, the reaction liquid was cooled to room temperature, and 100 mL of toluene was added, and the organic layer was washed twice with 50 mL of hydrochloric acid. The organic layer was taken out, dried over magnesium sulfate, and filtered. Activated carbon was added to the filtrate, stirred at 6 ° C for 1 hour, and then filtered through diatomaceous earth. The solvent was distilled off from the filtrate by a rotary evaporator, and then dried under reduced pressure at 6 ° C to give Compound (I-1 - 2) (meth. [6 6]

Cf3, (?f2)2 /CF (a-1) cf3 -111 - 200936563 [Chem. 6 7]

The structure of the compound (I-1 · 2 ) was determined by 1 h-NMR (ECA-500; manufactured by Nippon Electronics Co., Ltd.). W-NMRyOOMHz, δ 値 (ppm, TMS basis), DMSO, room temperature); 1.94 (3H, s), 2.3-2.8 (6H, m)' 4.1-4·3 (1Η, m), 4.3 -4· 5(1Η, m), 5·5-5·7(1Η, m), 5.62(1Η, s), 6·12(1Η, s), 9.29(1Η 'bs) ° Synthesis Example 4 (Synthesis Polymer Ab) 13.0 g of methyl isobutyl ketone was placed in a 500 mL 4-neck flask equipped with a dropping funnel, a Dimrod cooling tube, a thermometer and a mechanical stirrer, and nitrogen was circulated in the flask while stirring. After a minute, heat up directly to 90. Compound (1-1-2) 12.lg (24mmol), 2,2'-azobis(isobutyronitrile) 0.120g (0.73mmol) and methyl isobutyl ketone 45g were placed in a 200 mL beaker. Stir under temperature to a homogeneous solution. After the solution was added to a dropping funnel, it was dropped into a 4-neck flask kept at 90 ° C for 1 hour. After the completion of the dropping, the flask was stirred at 90 ° C for 5 hours to obtain a colorless solution. After the inside of the 4-necked flask was cooled to room temperature, the obtained colorless solution was transferred to a 1 L eggplant type flask, and the solvent was distilled off by a rotary evaporator, followed by drying under reduced pressure at 60 ° C to obtain a polymer Ab 12.3 g. The number average molecular weight (?n) of the polymer Ab was 200936563, 9,300 'the weight average molecular weight (Mw) was 53, and the degree of dispersion (Mw/Mn) was 5.7. Further, the molecular weight of the polymer Ab was measured by the same method as the polymer Aa. Synthesis Example 5 (Synthetic Polymer Ac) Methyl isobutyl ketone (20 g) was placed in a 500 mL 4 □ flask equipped with a dropping funnel, a Dimrod cooling tube, a thermometer and a mechanical stirrer, and the stomach 0 was mixed. After circulating nitrogen gas through the flask for 15 minutes, the temperature was directly raised to 90. (:. Compound (a-1) 10.1g (24mmol), 2,2,-azobis(isobutyronitrile) 0_40g (2.4mmol) and methyl isobutyl ketone 1 0 · 0g were added to 2 0 0 m In a beaker, stir at room temperature to obtain a homogeneous solution. After adding the solution to the dropping funnel, the solution was dropped into a 4-neck flask maintained at 90 ° C for 1 hour. After the dripping, the flask was kept at 90 °. After stirring at ° C for 4 hours, a colorless solution was obtained. After cooling the flask to room temperature, the obtained colorless solution was transferred to a 1 L eggplant flask, and the solvent was distilled off by a rotary evaporator, and then decompressed at 60 ° C. After drying, a polyacetate Ac 9.9 g was obtained. The number average molecular weight (?n) of the polymer Ac was 3,8 Å, the weight average molecular weight (Mw) was 6,300, and the degree of dispersion (Mw/Mn) was 1.65. Further, the molecular weight of the polymer Ac was measured by the method of the polymer Aa, 100 parts of the polymer Aa of the mixed solid component of Example 1 (polymer), and 400 parts of the solvent of propylene glycol monomethyl ether acetate, and the pore diameter was 0.2 μm. The membrane filter was filtered to obtain a polymer Aa solution. -113 200936563 In addition to the polymer Aa substituted with the polymer Aa, the other polymer Aa obtained a polymer Ab solution. In addition to the polymer Aa substituted with the polymer Aa, and the solvent amount was changed to 200 parts, the other polymer Aa was obtained as the polymer Ac liquid. The polymer Aa to the polymer Ac liquid was evaluated by the following method, and the coating was obtained therefrom. The properties (refractive index, average light transmittance, heat resistance, and development) of the film were as shown in Table 1. (1) Refractive index The polymer solution was applied to a circuit board by spin coating to have a film thickness. After 1.0 μm, the film was heated at 90 ° C for 1 minute to remove volatile components to form a coating film. The refractive index of the coating film at 550 nm was measured using a spectroscopic ellipsometer (M-22 0; manufactured by JASCO Corporation). (2) Average light transmittance The polymer solution is applied to a quartz plate by spin coating to a film thickness of Ι.Ομιη, and then placed on a hot plate and heated at 90 ° C for 1 minute to remove volatile components. The coating film was formed, and the coating film was irradiated with 200 mJ/cm 2 of ultraviolet light of 300 to 45 nm, and then heated at 180 ° C for 3 minutes, and a wavelength of 400 to 70 nm was measured using a spectrophotometer (DU-64®; manufactured by BECKMAN). A light transmittance spectrum, and then calculate the average light transmittance. The average light transmittance is preferably higher. (3) Heat resistance (3 -1 ) Average 値 of the absolute difference of the light rate difference -114- 200936563 The polymer solution was applied to a quartz plate by a spin coating method to a film thickness of 1.0 μm, and then placed on a hot plate and heated at 90 ° C for 1 minute to remove the volatile matter. The composition was formed into a coating film, and the coating film was irradiated with ultraviolet light of 200 mJ/cm 2 of 300 to 450 nm, and then heated at 1,800 ° C for 3 minutes to obtain a coating film. The light transmittance spectrum of 400 to 700 nm of the coating film was measured using a spectrophotometer (DU-640; manufactured by BECKMAN Co., Ltd.) to obtain a spectrum A. After heating the coating film at 240 ° C for 60 minutes, a wavelength-transmittance spectrum of 400 to 700 nm f) was measured to obtain a spectrum B. The absolute enthalpy of the difference in transmittance between the spectrum A and the spectrum B at each measurement wavelength of 400 to 700 nm was calculated, and the average enthalpy was used as an index of heat resistance. The average enthalpy is preferably less before and after heating (3-2). Whether the coating film is bounced after heating at 240 ° C. After heating at 240 ° C for 60 minutes as described above, it is visually observed whether or not the coating film is bounced. "Coating film opening" means that the coating film on the quartz plate is condensed into a bead shape by heating. (4) Imaging (when no UV irradiation is required) The polymer solution is applied to a circuit board by spin coating to a film thickness of 1 μm, and then heated at 90 ° C for 1 minute to remove volatile components. Coating film. The film thickness of the obtained coating film was measured using an optical interference type film thickness meter (VM1200; manufactured by Dainippon Screen Co., Ltd.). The film thickness is I. The coating film was heated at 11 ° C for 1 minute, and then immersed in a developing solution (-115-200936563 2.38% of tetramethylammonium hydroxide aqueous solution) for 1 minute, washed with water, dried, and then the film thickness was measured. The film thickness is d2. Substituting the film thickness illusion and d2 into the following formula, and obtaining the residual film rate of the image 1 〇

When the development residual film ratio ir/OMz/delOO is used for applications requiring lithographic characteristics, the development residual film ratio 1 is preferably approximately 〇%. r Table 1] ____ Average Transmittance Heat Resistant 14 Residual Film Rate 1 Refractive Index Transmittance Absolute 値 Average 値 Heated After Coating Film Blast Polymer Aa 1.42 100% 0.2% No 0% Polymer Ab 1.40 100% 0.1% No 2% Polymer Ac 1.39 100% Not detectable 99% Example 2 (Photosensitive composition 1) Mixed polymer Aa: 49 parts, sensitizer (B) formula (1 1 〇) 40 parts of ester of phenol compound and quinone-naphthoquinonediazide-5-sulfonic acid, 11 parts of hexamethoxymethylmelamine of hardener (C), 4-hydroxy-4-methyl of solvent (H) After 400 parts of 2-pentanone, it was filtered through a membrane filter having a pore size of 2 μm to obtain a photosensitive composition 1 a. [{k fi «1

-116- 200936563 In addition to the replacement of the polymer Aa with the polymer Ab, the other photosensitive composition 1 a obtained the photosensitive composition 1 b. In addition to the polymer Aa substituted with the polymer Aa, the other photosensitive composition 1a obtained the photosensitive composition 1c. The characteristics (developability, refractive index, and average light transmittance) of the photosensitive compositions la to lc and their coating films were evaluated by the following methods. The results are shown in Table 2. (1) Developing property The residual film ratio of the image in the absence of the ultraviolet irradiation process was measured by the same method as in the example except that the polymer solution was replaced with a photosensitive composition. The residual image rate 2 in the case of including the ultraviolet irradiation process was measured by the following method. [When the ultraviolet irradiation process is included] The photosensitive composition is applied to a tantalum circuit board by a spin coating method to have a film thickness of 1 μm, and then heated at 9 (rc for 1 minute to remove volatile components to form a coating film. The wavelength is 30,000. After the obtained coating film was irradiated to an ultraviolet light of 45 μm to 2 μm/cm 2 , the film thickness was measured using an optical interference type film thickness meter (VM 1 200; manufactured by Dainippon Screen Co., Ltd.). D3. The film after heating with ultraviolet light at 110 ° C, and then immersed in a developing solution (2 · 3 8 ° / tetramethylammonium hydroxide aqueous solution) for 1 minute, followed by water washing * stomach dry 're-measure The film thickness is d4. The film thickness h and &amp; are substituted into the following formula to obtain the residual film rate of the image 2 -117-200936563 image residual film rate 2 (%) = d4/d3xl00 ( 2) Refractive index The photosensitive composition is applied to a circuit board by spin coating, and heated at 90 ° C for 1 minute to remove volatile components to form a coating film. Secondly, it is irradiated with ultraviolet light of 200 mJ/cm 2 at a wavelength of 300 to 450 nm. The obtained coating film was heated at i8 ° C for 3 minutes, and the film coated by the above-mentioned 180 ° C heating film was spin-coated to be adjusted to Ι.Ομηη. A spectroscopic ellipsometer (M-220; manufactured by JASCO Corporation) measures the refractive index of the coated film at 550 nm, and the refractive index is preferably lower. (3) The average transmittance is replaced by a photosensitive composition. In addition to the polymer liquid, the average light transmittance was measured in the same manner as in Example 1. The average light transmittance was preferably higher. [Table 2] Residual film rate I*2 Residual film rate 2" Refractive index average light transmittance Photosensitive composition la 93% 0% 1.43 99% Photosensitive composition lb 94% 0% 1.41 99% Photosensitive composition lc 96% 95% 1.40 99% * 1 Except for the residual film during ultraviolet irradiation The ratio *2 includes the residual film rate at the time of the ultraviolet irradiation process. The photosensitive compositions la and lb are each the present invention comprising the polymer Aa and the polymer Ab obtained from the compound (1) and the compound (1-1-2). Further, the photosensitive composition 1 c is a comparative example containing the polymer Ac obtained from the compound (a · 3 ) -118- 200936563. From the results of Table 1, the photosensitive composition of the present invention 1 a And the coating film obtained by 1 b is immersed in the developing liquid after ultraviolet irradiation, and it melts and disappears, and the photosensitive composition of the comparative example is lc. The obtained coating film is almost always immersed in the developing solution. Therefore, the photosensitive compositions 1 a and 1 b of the present invention have excellent developability, and are coated by the photosensitive compositions la and lb of the present invention. The film has a low refractive index and a high average light transmittance. 实施 Example 3 (Photosensitive composition 2) Mixed polymer Aa: 82 parts, hardener (C) hexamethoxymethyl melamine 13 parts, photoacid generator (D) 5 parts of α-(4-toluenesulfonyloxyimino)-α-(4-methoxyphenyl)acetonitrile represented by the following formula, and 2-amino group of an amine compound (Ε) After 0.15 parts of -2-methyl-1-propanol and 4 parts of propylene glycol monomethyl ether acetate of a solvent, the mixture was filtered through a membrane filter having a pore diameter of 〇 2 μm to obtain a photosensitive composition 2a. ❹ 【化6 9】

The photosensitive composition 2b was obtained in the same photosensitive composition 2a except that the polymer Aa was substituted with the polymer Aa. The photosensitive composition 2c was obtained in the same photosensitive composition 2a except that the polymer Aa was substituted for the polymer Aa. -119-200936563 The characteristics (developing property 'refractive index and average light transmittance) of the photosensitive compositions 2a to 2c and their coating films were evaluated in the same manner as in the example 2, and the results are shown in Table 3. [Table 3] Development residual film rate 1" Development residual film rate 2*2 Refractive index 3s average light transmittance Photosensitive composition 2a 0% 93% 1.42 99% Photosensitive composition 2b 0% 94% 1.40 -- ---- 99% Photosensitive composition 2c 98% 98% 1.39 99% * 1 Residual film rate when UV-free irradiation is not included *2 Image retention residual film rate during UV irradiation process Photosensitive composition 2a And 2b are each an example of the invention containing the polymer Aa and the polymer Ab obtained from the compound (丨)] and the compound (1-1-2). Further, the photosensitive composition 2c is a comparative example containing the polymer Ac obtained from the compound (&amp;-3). As is apparent from the results of Table 1, the unexposed coating film obtained by the photosensitive compositions 2a and 2b of the present invention was obtained by immersing in the developing solution and dissolving and disappearing, and obtained from the photosensitive composition 2 c of the comparative example. The unexposed coating film remains almost immersed in the developing solution. Therefore, the photosensitive compositions 2a and 2b of the present invention have excellent developability. Further, the coating film obtained by the photosensitive compositions 2a and 2b of the present invention has a low refractive index and a high average light transmittance. Example 4 (Photosensitive composition 3) Mixed polymer Aa: 66 parts, 29 parts of dipentaerythritol hexaacrylate of polymerizable compound (F), and IRGACURE OXE01 of photopolymerization initiator (G) 5 parts of solvent (H) propylene glycol monomethyl ether-120-200936563 After 400 parts of acetate, the mixture was filtered through a membrane filter having a pore size of 2 μm to obtain a photosensitive composition 3 a. In addition to the replacement of the polymer A a with the polymer A b , the other photosensitive composition 3 a obtained the photosensitive composition 3 b. The photosensitive composition 3 a obtained a photosensitive composition 3 ^ except that the polymer Aa was substituted with the polymer Ac. The characteristics (developability, refractive index, and average light transmittance) of the photosensitive compositions 33 to 3c and their coating films were evaluated in the same manner as in Example 2, and the results are shown in Table 4. [Table 4] Development residual film ratio Γ1 Development residual film ratio 2*2 Refractive index average transmittance Photosensitive composition 3a 0% 94% 1.43 100% Photosensitive composition 3b 0% 95% 1.40 100% Photosensitivity Composition 3c 99% 98% 1.40 100% * 1 Remaining residual film ratio in the absence of ultraviolet irradiation* 2 Including the residual film ratio at the time of ultraviolet irradiation ❹ The photosensitive compositions 3a and 3b are each contained Examples of the invention of the polymer Aa and the polymer Ab obtained by the compound) and the compound (1-1-2). Further, the photosensitive composition 3c is a comparative example containing the polymer Ac obtained from the compound (a-3). As a result of the results of Table 1, the unexposed coating film obtained by the photosensitive compositions 3a and 3b of the present invention was immersed in the developing solution to be dissolved and disappeared, and the photosensitive composition 3 c of the comparative example was obtained. The exposure coating film is almost left even when immersed in the developing solution. Therefore, the photosensitive compositions 3a and 3b of the present invention have excellent developability. Further, the coating film obtained by the photosensitive compositions 3a and 3b of the present invention has a low refractive index and a high average transmittance of -121 - 200936563. Example 5 (Curable composition 4) Mixed polymer Aa: 95 parts, hardener (c) hexamethoxymethyl melamine 5 parts, solvent (H) propylene glycol monomethyl ether acetate 400 parts The membrane filter having a pore size of 0.2 μm was filtered to obtain a hardenable composition. The other hardening composition 4a has a curable composition 4b except that the polymer Aa is substituted with the polymer Aa. The characteristics (refractive index and average light transmittance) of the coating film obtained from the curable compositions 4 a and 4 b were evaluated in the same manner as in Example 2 except that the photosensitive composition was replaced by a curable composition. The coating film obtained from the curable composition 4 a has a low refractive index (i. 4 2 ) and a high average light transmittance (99%). The coating film obtained from the curable composition 4b has a low refractive index (丨.4〇) and a high average light transmittance (99%). [Industrial Applicability] The polymer of the present invention is preferably used as an optical product such as a solid-state imaging device, a liquid crystal display, or a filter protective film, or an optical material for the optical article (for example, a transparent coating agent, a photoresist underlayer film, A resin component for a material for a microlens, a transparent coating agent suitable for a microlens upper film or an underlayer film, or the like. The coating film obtained from the photosensitive composition or the curable composition of the present invention has a low refractive index and high transparency. Further, the photosensitive composition of the present invention can be alkali-developed. Therefore, the photosensitive composition or the curable composition of the present invention is -122-200936563, a protective film or the like; a material such as a microlens; a protective film for a solid-state imaging device, a liquid crystal display, a filter, or the like; And a transparent coating agent for forming an upper layer or a base film of the microlens; and the like.

-123

Claims (1)

200936563 X. Patent application garden 1. A compound which is a compound represented by formula (I), [Chemical 1] [In the formula (I), R1 to R3 are each independently a hydrogen atom, a fluorine atom, or an aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group; and R4 to R6 are each independently a single bond or may be substituted by a fluorine atom. ^·10 alkylene; R7 is a single bond, or a ci-i5 aliphatic hydrocarbon group which may be substituted by a fluorine atom; R8 is a -24 aliphatic hydrocarbon group which may be substituted by a fluorine atom; R9 is a hydrogen atom or may be a fluorine atom Or a hydroxy-substituted Cl-24 aliphatic hydrocarbon group, or a Cl-24 aliphatic hydrocarbon group in which one of the methylene units is partially substituted by an oxygen atom; but any one of R1 to R9 is a fluorine atom or a group substituted by a fluorine atom] 0 2 A polymer which is a constituent monomer represented by the formula (1) of the first aspect of the patent application 'Chemical 2' People crR5 咕. Person R7-COOR9 [In the formula (I), R1 to R3 are each independently a hydrogen atom, a fluorine atom, or a Cl_13 aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group; -124- 200936563 R4 to R6 are each independently a single bond, or may be fluorine An atom-substituted Ci-i alkyl group; R7 is a single bond or a C?15 aliphatic hydrocarbon group which may be substituted by a fluorine atom; R8 is a <^-24 aliphatic hydrocarbon group which may be substituted by a fluorine atom; R9 is a hydrogen atom, or a Ci-24 aliphatic hydrocarbon group which may be substituted by a fluorine atom or a hydroxyl group, or a C^24 aliphatic hydrocarbon group partially substituted with an oxygen atom; or any one of R1 to R9 is a fluorine atom or a fluorine atom-substituted group] 〇3. The polymer of claim 2, wherein, in the compound represented by the formula (I), R8 is a ChN aliphatic hydrocarbon group 取代4 substituted by a fluorine atom. A polymer of 2, wherein, in the compound represented by the formula (I), R9 is a hydrogen atom. 5. A polymer according to claim 2, which is a copolymer of a compound represented by the formula (I) and a copolymerizable compound. 6. The polymer of claim 5, wherein the compound copolymerizable with the compound represented by the formula (I) is an acrylate, a methacrylate or a mixture thereof. 7. A film which is formed by containing a polymer according to any one of claims 2 to 6. A photosensitive composition comprising the polymer (a), the sensitizer (B), the hardener (C), and the solvent (Η) according to any one of claims 2 to 6. -125- 200936563 9. The photosensitive composition of claim 8 wherein the photosensitive agent (B) is a benzoquinonediazide compound. 10. The photosensitive composition of claim 8 wherein the hardener (C) is a melamine compound. A photosensitive composition comprising the polymer (A), the hardener (C), the photoacid generator (D) and the solvent (Η) according to any one of claims 2 to 6. Φ 1 2. The photosensitive composition of claim U, wherein the photoacid generator (D) is an anthracene compound. A photosensitive composition according to item 11 of the patent application, which further contains an amine compound (Ε). 14. The photosensitive composition of claim 11, wherein the hardener (C) is a melamine compound. A photosensitive composition containing a polymer (Α), a polymerizable compound (F) ©, a photopolymerization initiator (G), and a solvent, as in any one of claims 2 to 6 (Η). The photosensitive composition of claim 15, wherein the polymerizable compound (F) is at least one selected from the group consisting of a polyfunctional acrylate compound and a polyfunctional methacrylate compound. . 1 7 - The photosensitive composition of claim 16 wherein the polymerizable compound (F) is selected from the group consisting of '5 to 6 functional acrylate compounds and 5 to 6 functional methacrylate compounds At least 丨1 8 · The photosensitive composition of claim 15 of the patent application, wherein -126-200936563 photopolymerization initiator (G) is a lanthanide compound. A hardening composition comprising the polymer (A), the hardener (C) and the solvent (Η) according to any one of claims 2 to 6. A sclerosing composition according to claim 19, wherein the hardener (C) is a melamine compound. -127- 200936563 VII. Designated representative map: (1) The representative representative of the case is: No (2), the representative symbol of the representative figure is a simple description: No. 8. If there is a chemical formula in this case, please reveal the best display invention. Chemical formula of the formula: Formula I ❹