TW200844511A - Polarizer - Google Patents

Abstract

This invention provides a polarizer with a great light polarization performance, a desirable optical characteristic, and a satisfactory thermal resistance. The light polarizer can retain strong adhesion and is not easily tearable or deformable under long-time use, providing users with high reliability. Two sides of the light polarizer are adhered with a norbornene resin film by an adhesive layer, wherein the norbornene resin film contains on the reverse side of the polarizer with an adhesive layer made of methacrylate-based polymer resin.

Description

200844511 IX. Description of the Invention [Technical Field to Which the Invention Is Ascribed] The present invention relates to a polarizing plate. More specifically, the present invention relates to a polarizing plate in which a norbornene-based resin film and a polarizing film are laminated. [Prior Art] A polarizing plate (polarizing film) used for a liquid crystal display or the like is usually formed of a substrate (optical film) excellent in transparency and a polarizing film (polarizer). Further, the polarizing plate may be formed of a film (retardation film) and a polarizing film which are obtained by extending an optical film and impart a phase difference function to transmitted light. In the past, an optical film used for a substrate of a polarizing plate or a retardation film was a polycarbonate film, a polyester film, an acetate film or the like. However, a polarizing plate using a polycarbonate film or a polyester film changes the phase difference imparted to the transmitted light due to a large photoelastic coefficient, a slight stress change, and the like, and the acetate film has low heat resistance and high water absorbability. With its polarizing plate, it will be subject to deformation problems depending on the environment. In addition, the norbornene-based resin is excellent in transparency, heat resistance, chemical resistance, and the like, and has been attracting attention as a material for various optical parts. Further, Patent Document 1 proposes a polarizing film in which a norbornene-based resin sheet is laminated as a protective layer on a polarizing film. However, when a polarizing plate having an optical film as a protective layer is incorporated in a liquid crystal display device, there is a problem that the element is peeled or deformed and changes in physical properties or optical characteristics after a long period of use. Further, the polarizing plate is usually incorporated into the liquid crystal display through the adhesive. -5- 200844511 For a long period of time, the adhesive layer is atomized, which impairs the optical characteristics of the polarizing plate. [Problem to be Solved by the Invention] The present invention provides a property having a good polarizing function and having optical characteristics, heat resistance, chemical resistance, and the like. It is excellent in the long-term use, and it is difficult to produce a polarizing plate which is excellent in durability, such as peeling and deformation, and has high reliability. [Means for Solving the Problems] As a result of reviewing the above-mentioned problems, the present inventors have found that the polarizing plate of the present invention has a good polarizing function, and its optical characteristics, heat resistance, chemical resistance, and the like are also excellent. It is excellent, and it is difficult to be excellent in durability, such as peeling and deformation, and has high reliability at the time of long-term use, and the present invention is completed. In other words, the present invention is specified by the matters described in the following [1] to [1]. [1] A polarizing plate characterized in that a norbornene-based resin film (a) and a norbornene-based resin film (b) are laminated on both surfaces of a polarizing film through an adhesive layer, wherein a norbornene-based film The resin film (b) is on the surface opposite to the polarizing film and has an adhesive layer containing a polymer derived from an alkyl (meth) acrylate. [2] The polarizing plate of [1], wherein the norbornene-based resin film -6 - 200844511 (a) is provided on the surface opposite to the polarizing film, and has a hard coat layer directly or through another layer. [3] The polarizing plate of [1], wherein the norbornene-based resin film is a norbornene obtained by (co)polymerizing a monomer containing at least one compound represented by the following formula (1) a norbornene-based resin film made of a resin;

(In the formula (1), R1 to R4 each independently represent a hydrogen atom, a halogen atom, or a monovalent group which may contain oxygen, nitrogen, sulfur or hydrazine; R1 and R2, or R3 and R4 may bond each other to form a sub- An alkyl group, or R1 and R2, R3 and R4, or R2 and R3 may be bonded to each other to form a monocyclic or polycyclic carbocyclic or heterocyclic ring; X represents an integer of 0 or 1 to 3, and y represents 〇 or 1) [4] The polarizing plate according to [1], wherein the adhesive layer has at least one polymer derived from an alkyl (meth) acrylate represented by the following formula (i); CH2 = CRCOOR, 200844511 ( In the formula (i), R represents a hydrogen atom or a methyl group; and an alkyl group of 12). [5] The polarizing plate according to [1], wherein the polymer of the enoate is a polymer having a molecular weight of 1,500,000 or more by colloidal osmosis chromatography. [6] The polarizing plate according to [1], wherein the resin film contains an ultraviolet absorber. [7] The polarizing plate of [1], wherein the particles are. [8] The polarizing plate of [1], wherein the moisture permeability is 300 (g. 25 pm/m rate is 1.0% by weight or less, and the transmittance is 90% or more. [9] The polarizing plate of [1], wherein The polarizing plate of the polarizing film is a polarizing plate of [1], wherein the film is a retardation film. [Effects of the Invention] The present invention provides a good polarizing, heat resistance, and chemical resistance. It is excellent in durability, such as exfoliation and deformation, and has the best form of the invention. R' represents a carbon number of 1 to at least one of the alkyl (meth) styrene polystyrene conversion weights. The norbornene hard coat layer contains a micro norbornene-based resin film 2·24h〇 or less, and the water-absorbing polarizing film is made of polyvinyl alcohol of 20% by weight or less. The norbornene-based resin has a thin function and its optical characteristics are long-term. A polarizing plate which is less likely to be used for reliability. -8- 200844511 Next, the present invention will be specifically described. <norbornene-based resin film> The norbornene-based resin film of the present invention is a norbornene-based resin film. Resin' A resin obtained by (co)polymerizing a monomer or a monomer composition (hereinafter, collectively referred to as a monomer composition) containing at least one norbornene-based compound, and further hydrogenating if necessary. The olefinic compound is not particularly limited as long as it is a compound having a norbornene skeleton, and is preferably a compound represented by the following formula (1).

(In the formula (1), R1 to R4 each independently represent a hydrogen atom, a halogen atom, or a monovalent group which may contain oxygen, nitrogen, sulfur or sand. R1 and R2, or R3 and R4 may be bonded to each other. An alkylene group is formed, or R1 and R2, R3 and R4, or R2 and R3 may be bonded to each other to form a monocyclic or polycyclic carbocyclic or heterocyclic ring. X represents an integer of 0 or 1 to 3, and y represents 0. Or 1). [Monomer composition] The norbornene fine compound contained in the composition is, for example, represented by the above formula (1). -9- 200844511 Further, in the above formula (1), R1 and R2, or R3 and R4 may be bonded to each other to form a sub-homogeneous group, or R1 and R2, R3 and r4, or r2 and R3 may be bonded to each other. A monocyclic or polycyclic carbocyclic or heterocyclic ring is formed. Here, "R1 and R2 are bonded to each other to form an alkylene group" means that either one of Ri and R2 is detached, and the remaining groups are bonded to each other by a double bond (the following formula (2)). The same is true for R3 and R4. Further, the carbocyclic or heterocyclic ring may be an alicyclic or aromatic ring. 〔化3〕

The norbornene stimulating compound represented by the above formula (1) may be used singly or in combination of two or more kinds. The norbornene-based compound represented by the above formula (1) may, for example, be the following compounds, but is not limited to such compounds. Bicyclo[2.2.1]hept-2-ene (norbornene) 5-methyl-bicyclo[2.2.1]hept-2-ene-5-ethyl--[2.2.1]hept-2 -5-Cyclohexyl-bicyclo[2.2.1]hept-2-ene-5-phenyl-bicyclo[2.2.1]hept-2-ene-5-(4-diphenyl)-bicyclo[2 ·1·1]hept-2-ene 5-methoxycarbonyl-bicyclo[2.2.1]hept-2-ene 5-phenoxycarbonyl-bicyclo[2.2.1]hept-2-ene-10 - 200844511 5 - The present oxyethyl ore group - _ mour [2.2.1] hept-2- stored 5 - phenyl decyloxy - a sorrow [2.2.1] hept-2-storage 5_methyl-5 -methoxycarbonyl-bicyclo[2.2.1]hept-2-ene 5-methyl-5-phenoxycarbonyl-bicyclo[2.2.1]hept-2-ene-5-methyl-5-benzene Oxyethyl carbonyl-bicyclo[2.2.1]hept-2-ene 5-vinyl-bicyclo[2.2.1]hept-2-ene 5-ethylene-bicyclo[2.2.1]heptane- 2-ene 5.5-dimethyl-bicyclo[2.2.1]hept-2-ene 5.6-dimethyl-bicyclo[2.2.1]hept-2-ene 5-fluoro-bicyclo[2.2.1] Hept-2-ene 5-chloro-bicyclo[2.2.1]hept-2-ene 5-bromo-bicyclo[2.2.1]hept-2-ene 5.6-difluoro-bicyclo[2.2.1]g 2-ene 5.6-dichloro-bicyclo[2.2.1]hept-2-ene 5.6-dibromo-bicyclo[2.2.1]hept-2-ene 5-hydroxy- Bicyclo [2·2·1]hept-2-ene 5-hydroxyethyl-bicyclo[2.2.1]hept-2-ene 5-cyano-bicyclo[2.2.1]hept-2-ene 5 -amino-bicyclo[2.2.1]hept-2-enetricyclo[4·3·0·12,5]non-3-ene tricyclo[4.4.0.I2,5]-f--* -3 - alkene 7-methyl-tricyclo[4.3.0.12,5]non-3-ene 7-ethyl-tricyclo[4.3.0.I2,5]non-3-ene 7-cyclohexyl-three环[4.3.0.12,5]癸-3-ene-11 - 200844511 7-Phenyl-tricyclo[4.3.0.12,5]non-3-ene 7-(4-biphenylyl)-tricyclo[4.3 .0.12,5]癸-3-ene 7,8-dimethyl-tricyclo[4.3.0.12,5]non-3-ene 7,8,9-trimethyl-tricyclo[4.3.0.12,5癸-3-ene-8-methyl·tricyclo[4.4.0.12,5]undec-3-ene 8-phenyl-tricyclo[4.4.0.I2,5]undec-3-ene 7, Fluorine Τ®3. - 二丈孩 [ 4.3.0. I2 ,5 〕癸-3 - 7 7-Chlorine-- TS9. 二土展( 4.3 . 0· I2 ,5 〕癸-3 7-Bromo-II垣(4.3 . 0. I2 ,5 ' ]癸-3 _7,8-dichloro'bicyclo[4. 3. 0. I2,5] 癸-3-ene 7,8,9·: trichloro 1 ·" —rra =im [ 4. 3 . 0.1 2,5 ]癸-3_ene 7-chloromethyl-tricyclo[ 4 • 3 • 0. ,12,5] 癸. -3-ene 7-Dichloromethyl-tricyclo[ ;4.3 ·0·12,5 ]. 癸· -3 -diluted 7-trichloromethyl---χTM. 二垣[ ;4 .3 .0.12 5 ] 癸_ 3 - burn 7-hydroxy-bicyclo[4·3 . 0· I2 ,5]癸-3-ene 7-truncyl-tricyclo[4. 3 ·0. I2 ,5]癸-3- ene 7_Amino-dirm vibration C 4. 3 · 0. I2 ,5]癸-3-ene tetracyclo[4.4 • 0 • I2,5 • 1 7J 1 0 ' ]12-3-Μ 五环[ 7.4 • 0 • I2,5 • I8,] 1 1 07,12] Fifteen, 3 - refining /, 垣 [ 8.4 • 0 • I2, 5 • 1 7,] ί 4 19,12.C I8,1 3十五15-3 -ene-8-methyltetram [4· 4. 0. I2 Λι7,1 〇] Twelve-3·ene 8-ethyl•tetra[4. 4. 0· I2 °) -3-ene 8-cyclohexyl-tetracyclo[4 • 4, .0. 12,5·1 7,10 ] -12 _ .3- ene 8-phenyl-tetracyclo[4. 4. 0. I2 Λι7,1 〇] Twelve-3 - ene-12- 200844511 8-(4-biphenylyl)-tetracyclo[4.4.0.12, 5.17,1()]dodec-3-ene 8-methoxycarbonyl -tetracycline [4·4·0·12'5.Γ,1()]dodec-3-ene 8-phenoxycarbonyl-tetracyclo[4·4·0.12'5·17'1() 】12-3-ene 8-phenoxyethylcarbonyl-tetracyclo[4.4·0·12'5·Γ,1()]dodec-3-ene 8-phenylcarbonyloxy-tetracyclo[ 4·4·0·12'5.17'1()]Dodec-3-ene 8-methyl-8-methoxycarbonyl-tetracyclo[4.4·0·12'5·17'1()] Di-3-ene 8-methyl-8-phenoxycarbonyl-tetracyclo[4·4.0·12,5·Γ,1()]dodec-3-ene 8-methyl-8-phenoxy Ethylcarbonyl-tetracyclo[4·4·0.12,5·17,1()]dodec-3-iso 8-vinyl-tetracyclo[4.4.0.12,5.17,1G]dodec-3-ene 8 -ethylene-tetracyclo[4·4·0·12,5·ΐ7,1()]dodec-3-ene 8,8-dimethyl-tetracyclo[4.4 · 0 · 1 2,5 · Hey, 1. 】 12-3 -ene 8,9-dimethyl-tetracyclo[4·4.0·12,5·Γ,1()]dodec-3-ene 8-fluoro-tetracyclo[4.4·0·12 '5·17,1()]dodec-3-ene 8-chloro-tetracyclo[4·4·0·12,5·17,1()]dodec-3-ene 8-bromo-tetracyclic [4 · 4 · 0 · 1 2 '5 · Γ '1 G] 12-3 -ene 8.8-dichloro-tetracyclo[4·4·0·12,5·17,1()]12- 3-ene-8-dichlorotetracyclo[4·4·0·12,5·17,1()]dodec-3-ene 8,8,9,9-tetrachloro-tetracyclo[4·4· 0·12,5·17,1()]dodec-3-ene 8-hydroxy-tetracyclo[4·4·0·12,5·Γ,1()]dodec-3-ene 8-hydroxyl Ethyl-tetracyclo[4·4·0·12,5·17,1()]dodec-3-ene-8-methyl-8-hydroxyethyl-tetracyclo[4·4·0.12'5· Γ,1()]dodec-3-ene 8-cyano-tetracyclo[4·4·0·12,5.17,1()]dodec-3-ene 8-amino-tetracyclo[4.4. 0.12, 5.17'1 ()] Dodec-3-ene-13- 200844511 The type and amount of the norbornene compound of the present invention can be appropriately selected depending on the desired properties. In the norbornene-based compound of the above formula (1), at least one structure having at least one atom selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom and a ruthenium atom is contained in the molecule (hereinafter referred to as "polar structure"). The compound is preferably excellent in adhesion or adhesion to other materials. In particular, in the above formula (1), R1 and R3 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, preferably at least one of them is a methyl group; and any of R2 or R4 is a group having a polar structure, and The other compound which is a hydrogen atom or a hydrocarbon group having a carbon number of 丨3 is preferable because the water absorption (wet) property of the obtained resin becomes low. Further, the norbornene-based compound having a polar structural group represented by the following formula (3) is preferably used because the heat resistance and water absorption (wet) are balanced. -(CH2) zCOOR (3) In the formula (3), R represents a substituted or unsubstituted hydrocarbon group having 1 to 15 carbon atoms, and z represents an integer of 〇 or 1 to 1 。. In the above formula (3), the smaller the z is, the higher the glass transition temperature of the hydride of the norbornene-based resin is, and the heat resistance is excellent. Therefore, z is preferably an integer of 〇 or 1 to 3, and A single system in which z is 0 is more preferable because of its ease of synthesis. Further, in the above formula (3), the more the number of carbon atoms, the more the water-absorbing (wet) property of the obtained norbornene-based resin tends to decrease, and the glass transition temperature of -14-4844511 tends to decrease, so From the viewpoint of maintaining heat resistance, a hydrocarbon group having 1 to 10 carbon atoms is preferable, and a hydrocarbon group having 1 to 6 carbon atoms is particularly preferable. In the above formula (1), an alkyl group having 1 to 3 carbon atoms bonded to a carbon atom bonded to the group represented by the above formula (3), particularly a methyl norbornene-based compound, is heat-resistant. It is preferable to balance with water absorption (wet). Further, in the above formula (1), X is fluorene or 1, y is a norbornene-based compound of ruthenium, and a norbornene-based resin having high reactivity and high recovery can be obtained, and high heat resistance can be obtained. The borneol-based resin hydride is even more suitable for industrial use. In order to obtain the norbornene-based resin of the present invention, the norbornene-based compound and the copolymerizable monomer are contained in the monomer composition for polymerization without detracting from the effects of the present invention. The above copolymerizable monomer may, for example, be a cyclic hydrocarbon alkene such as cyclobutene, cyclopentene, cycloheptene, cyclooctene or cyclododecene; 1,4-cyclooctadiene or bicyclodene; a non-conjugated cyclic polyene such as pentadiene or cyclododecatriene. These copolymerizable single systems may be used singly or in combination of two or more. [Polymerization method] The polymerization method of the norbornene-based resin of the present invention is not particularly limited as long as the monomer composition of the norbornene-based compound can be polymerized, for example, by ring-opening (co)polymerization (I) Or addition (co)polymerization (π) to carry out the polymerization. -15- 200844511 The so-called ring-opening (co)polymerization refers to ring-opening polymerization or ring-opening copolymerization, and the addition (co)polymerization refers to addition polymerization or addition copolymerization. (I) Ring-opening (co)polymerization (I-a) polymerization catalyst The polymerization of the monomer composition of the present invention is preferably carried out by ring-opening (co)polymerization in the presence of a substitution catalyst. The displacement catalyst is (A) at least one compound selected from compounds having W, Mo, and Re (hereinafter referred to as compound (A)), and (B) having a IA group element of the Deming periodic table (for example, Li). , Na, K, etc.), 11 human races (eg, ]^, €3, etc.), Group IIB elements (eg, Zn, Cd, Hg, etc.), Group IIIA elements (eg, B, A1, etc.), IVA a compound of halogen (for example, Si, Sn, Pb, etc.), or a group IVB element (for example, Ti, Zr, etc.), and consists of at least one compound having a bond of this element with carbon or a bond of this element to hydrogen. A polymerization catalyst formed by a combination of at least one selected compound (hereinafter referred to as compound (B)). Further, in order to increase the activity of the polymerization catalyst, an additive (C) described later may be further added. The compound (A) may, for example, be a halide of W, Mo or Re, an oxyhalide, an alkoxyhalide, a metal alkoxide, a carbonate, an (oxo)acetamidine salt, a carbonyl complex or an acetonitrile. Compounds, mirror-type complexes, and derivatives thereof, or combinations thereof, are seen from the point of polymerization activity and practicability - 16-200844511, and compounds of W and Mo are preferred, among which The halides, oxyhalides and alkoxyhalides are particularly preferred. Further, a mixture of two or more kinds of compounds which produce the above compound (A) can also be used. Further, these compounds can be modified by a suitable error-capping agent such as P(C6H5)5, C5H5N or the like. Examples of the compound (A) include WC16, WC15, WC14, WBr6, WF6, WI6, MoC15, MoC14, MoC13, ReCl3, WOCl4, MoOC13, ReOCls, ReOBr3, W(OC6H5)6, WCl2(〇C6H5)4, Mo ( OC2H5) 2C13, Mo(OC2H5)5, Mo02(acac)2, W(OCOR)5, W(0C2H5)2C13, W(CO)6, Mo(CO)6, Re2(CO)10,

ReOBr3 · P(C6H5)3, WC15 · P(C6H5)3, WC16 · C5H5N, W(CO)5.P(C6H5)3, W(CO)3·(CH3CN)3, etc. Among these compounds, MoC15, Mo(OC2H5)2C13, WC16, W(0C2H5)2C13 and the like are particularly preferable. Examples of the compound (B) include n-C4H5Li, n-CsHuNa, C5H5Na, CH3MgI, C2H5MgBr, CH3MgBr, n-C3H7MgCl, (C6H5)3A1, t-C4H9MgCl, CH2=CHCH2MgCl, (C2H5)2Zn, (C2H5)2Cd, CaZn(C2H5)4, (CH3)3B, (C2H5)3B, (n-C4H9)3B, (CH3)sA1, (CH3)2A1C1, (CH3)3A12C13,

CH3A1C12, (C2H5)3A1, LiAl(C2H5)2, (C2H5)3A1-0(C2H5)2, (C2H5)2A1C1, C2H5A1C12, (C2H5)2A1H, (iso-C4H9)2AlH, (C 2 H 5 ) 2 A 1 OC 2 H 5 , ( i SO - C 4 H 9 ) 3 A 1 , ( C 2 H 5 ) 3 A 1 2 C 1 3 , (CH3) 4Ga, (CH3) 4Sn, (n_C4H9) 4Sn, ( C2H5) 3SiH, (n-C6Hi3)3Al, (n-C4Hi7)3Al, LiH, NaH, B2H6, NaBH4, -17- 200844511 A1H3, LiAlH4, BiH4 and TiH4. Further, a mixture of two or more kinds of compounds which form these compounds (B) can also be used. Among these compounds (B), (CH3)3A1, (CH3)2A1C1, (CH3)3A12C13, ch3aici2, (c2h5)3ai, (C2H5)2A1C1, (C2H5)15A1C115, C2H5A1C12, (C2H5)2A1H, (C2H5) 2A10C2H5, (C2H5)2A1CN, (C3H7)3A1, (iso-C4H9)3Al, (iso-C4H9)2AlH, (C6H13)3A1, (c8h17)3ai, (c6h5)5ai, etc. are preferred. The additive (C) which can be used together with the compound (A) and the compound (B) is preferably an alcohol, an aldehyde, a ketone, an amine or the like, and examples thereof are as follows (1) to (9). (1) Non-organometallic compounds such as boron, BF3, BC13, B(0-n-C4H9)3, (C2H5〇3)2, BF, B2〇3, H3B〇3, etc., Si(OC2H5) a non-organometallic compound of 4; (2) alcohols, hydrogen peroxides and peroxides; (3) water; (4) oxygen; (5) carbonyl compounds such as aldehydes and ketones and polymers thereof (6) cyclic ethers such as ethylene oxide, epichlorohydrin, oxetane, etc.; (7) N,N-diethylformamide, hydrazine, hydrazine dimethyl acetamide An amine such as anthraquinone, aniline, morpholine or piperidine; and an azo compound such as azobenzene; (8) Ν-nitrosodimethylamine, hydrazine-nitrosodiphenylamine, etc. Further, a nitroso compound; -18- 200844511 (9) a compound containing an S-C1 or N-C1 group such as trichloromelamine, N-chloroarene succinimide or phenylthiobenyl chloride. The molar ratio of the compound (A) to the total monomer to be subjected to the ring-opening (co)polymerization reaction is usually 1:500 to 1:50,000, preferably in terms of the amount of the catalyst to be used. It is desirable that the ratio of the compound (A) to the compound (B) is 1:1,000 to 1:10,000 (the compound (A): the compound (B)) has a metal atomic ratio of 1:1 to 1: 5 0, Preferably, it is desired to be 1: 2~1: 3 0. The ratio of the compound (A) to the compound (C) (compound (c): the compound (A)) is a molar ratio of 〇. 5: i~; [5: 1, preferably 0.05: 1~ 7: 1. (The polymerization solvent used in the ring-opening (co)polymerization reaction of the Ι-M polymerization solvent, if the monomer composition or the catalyst for supplying the ring-opening (co)polymerization is dissolved, and the catalyst does not lose activity, In order to dissolve the produced norbornene-based resin, there is no limitation. For example, alkane such as Wuyuan, Heyuan, Gengyuan, Xinyuan, Shuyuan, and decane; cyclohexane and ring Naphthenes such as heptane, cyclooctane, decalin, norbornane; aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, cumene; chlorobutane, bromohexane a halogenated alkane such as methyl chloride, dichloroethane, dibromohexane, chloroform or tetrachloroethylene; a halogenated aryl compound such as chlorobenzene; ethyl acetate, butyl acetate, iso-butyl acetate, and C Saturated carbonates such as methyl ester and dimethoxyethane; -19- 200844511 Ethers such as dibutyl ether, tetrahydrofuran, and dimethoxyethane are used singly or in combination of two or more. The polynorbornene compound, the solvent which can be copolymerized, and the solvent used may also be used to form a molecular weight. The solvent of the agent. The amount of the polymerization solvent used is the weight ratio of the polymerization solvent to the monomer composition for the opening and closing reaction (polymerization solvent: usually 1:1 to 10:1, preferably 1:1) ~5 : (Ic) The molecular weight of the norbornene-based resin obtained by the molecular weight modifier may be based on the polymerization temperature, the type of the polymerization catalyst, the polymerization solvent, or the molecular weight regulator may be coexisted in the reaction system. Suitable molecular weight modifiers include, for example, ethylene, propane, 1-pentene, 1-hexene, 1-heptene, 1-octene, i-pinene (X-olefins; and styrene, 4) An aromatic vinyl compound such as methyl styrene or 2-methyl 4-ethyl styrene, which is particularly preferably a butene or a 1-hexene. These molecular weight modifiers are used in combination of two or more kinds. The amount of the regulator used is for the ring opening (common monomer 1 mol, usually 0.005 ~ 〇 · 6 m, ~ 0.5 mol. (Id) other polymerization conditions. These are suitable The solvent is used as a dissolved ring (co)polymer composition in addition to or in place of the catalyst liquid. The polymerization is preferably carried out by a polymerization reaction of styrene, 1-butene or 1-decene, etc., in a single or mixed manner, preferably 0.011-20 - 200844511 norbornene-based resin. The ring-opening (co)polymerization reaction of the olefinic compound or the ring-opening (co)polymerization of the norbornene-based compound and the copolymerizable monomer may be carried out in a total of polybutadiene or polyisobutylene. a conjugated diene compound, a styrene-butadiene copolymer, an ethylene-non-conjugated diene copolymer, a polynorbornene, or the like, and an unsaturated hydrocarbon having two or more carbon-carbon double bonds in its main chain In the presence of a polymer or the like, a monomer composition containing a norbornene-based compound is subjected to ring-opening (co)polymerization (Π) addition (co)polymerization reaction by addition (co)polymerization of norbornene The production of a resin which can be produced by a conventional addition (co)polymerization reaction of a norbornene-based compound, which is a monomer composition containing a norbornene-based compound, and a polymerization catalyst is necessary. Use a polymerization solvent, if necessary, use molecular weight Agent, to effect an addition (co) polymerization. (Π-a) The polymerization catalyst used in the polymerization (co) polymerization reaction, for example, the pin, 錬, 铭, and titanium exemplified in the following (II_a-1) to (II-a-3) And a single catalyst or a multi-component catalyst such as chromium, but the polymerization catalyst of the present invention is not limited thereto. (ΙΙ-al) single catalyst system: [Pd(CH3CN)4] [BF4]2, [Pd(PhCN)4] [SbF6], -21 - 200844511 [(η3-crotonyl) Pd (ring Octyl-1,5-diene)][PF6], [(η3-crotonyl)Ni(cyclooctyl-1,5-diene)][B(3,5-(CF3)2C6F3)4] , [(η3-crotonyl)Ni(cyclooctyl-1,5-diene)][PF6], [(η3·allyl)Ni(cyclooctyl-1,5-diene)]B (C6F5)4], [(η3-crotonyl)Ni (cyclooctyl-1,5-diene)][SbF6], toluene·Ni(C6F5)2, benzo·Ni(C6F5)2, trimethyl a transition metal compound such as benzene·Ni(C6F5) 2 or ethyl ether·Ni(C6F5) 2 . (II-a-2) Multicomponent catalyst system <A>: A combination of a palladium complex having σ or σ, π bonds and an organoaluminum or a super acid salt can be mentioned. Specifically, it may be exemplified by di-μ-chloro-bis(6-methoxybicyclo[2.2.1]hept-2-ene-endo-5cj, 2π) Pd and by aluminum oxyaluminum (abbreviation) a combination of compounds selected for "MAO"), AgSbF6 and AgBF4, a combination of [(η3-aryl)PdCl]2 with AgSbFs or AgBF4, [(cyclosemisyl], 5_one) Pd(CH3)Cl a combination of PPh3 and NaB[3,5-(CF3)2C6H3]4, etc. (II-a-3) multicomponent catalyst system <B>: 〈B-1> is selected from a nickel compound, a transition metal compound of a cobalt compound, a titanium compound, and a zirconium compound, <B-2> a compound selected from the group consisting of super acid, Lewis acid, and ionic boron compound, and <B-3> an organoaluminum compound 3 -22- 200844511 a combination of. <B-1> Transition Metal Compound <B -1 -1> Nickel compound, cobalt compound nickel compound and cobalt compound, examples thereof include organic carbonates of nickel or cobalt, organic phosphites, organic phosphates, and organic sulfonic acids. A selected compound of a salt, a β-diketone compound or the like, more specifically, for example, nickel 2-ethylhexanecarboxylate, nickel naphthalate, cobalt naphthalate, nickel oleate, nickel dodecanoate, dodecane Cobalt acid, cobalt neodecanoate, nickel dibutyl phosphite, nickel dibutyl phosphate, nickel dioctyl phosphate, nickel salt of dibutyl phosphate, nickel dodecyl benzene sulfonate, ρ-toluene Examples of the nickel, the bis(acetonitrile) nickel, the bis(acetonitrile) nickel, and the like include the hexafluoroantimonic acid, tetrafluoroboric acid, trichloroacetic acid, hexafluoroacetone, and the like. A compound which is super acid and denatured. Further, a nickel diene or a triene coordination complex may, for example, be dichloro(1,5-cyclooctadiene)nickel; [(η3-crotonyl) (1,5-cyclooctadiene). Nickel hexafluorophosphate, its tetrafluoroborate complex, 肆[3,5-bis(trichloromethyl)]borate complex; (1,5,9-cyclododecatriene) Nickel; nickel (norbornadiene) nickel; nickel complex of bis(1,5-cyclooctadiene) nickel or the like. Further, a complex of nickel or cobalt coordinated by a ligand having an atom of ruthenium, osmium, iridium or the like, such as bis(triphenylphosphine)nickel dichloride or bis(triphenylphosphine) may be mentioned. Nickel dibromide, -23- 200844511 bis(triphenylphosphine)cobalt dibromide, bis[tris(2-methylphenyl)phosphine]nickel dichloride, bis[3-(4-methylphenyl) Phosphine] nickel dichloride, bis[N-(3-t-butyl salicyl) phenyl amination] nickel,

Ni[ PhC(0)CH](Ph) &gt;

Ni(OC(C6H4)PPh)(H)(PCy3),

Ni[0C(0)(C6H4)P](H)(PPh3), a reaction of bis(1,5-cyclooctadiene) nickel with PhC(0)CH=PPh3, [2,6-(i- Pr) 2C6H3N = CHC6H3(0)(Anth)](Ph)(PPh3) Nickel complex of Ni or the like (here, Anth is 9-fluorenyl, Ph is phenyl, and Cy is abbreviated as cyclohexyl). <B-1-2> Titanium, a chromium compound titanium, and a pin compound may, for example, be [t-BuNSiMe(Me4Cp)]TiCl2, (Me4Cp)(0-iPr2C6H3)2TiCl, (Me4Cp)TiCl3, (Me4Cp)Ti(OBu) 3, [t-BuNSiMe2Flu] TiMe2, [t-BuNSiMe2Flu]TiCl2

Et(Ind)2ZrCl2

Ph2C(Ind)(Cp)ZrCl2 'iPr(Cp)(Flu)ZrCl2, iPr(3-tert-But-Cp)(Ind)ZrCl2 'iPr(Cp)(Ind)ZrCl2, -24- 200844511

Me2Si(Ind)2ZrCl2

Cp2ZrCl2, (Cp is a cyclopentadienyl group, Ind is a fluorenyl group, and Flu is abbreviated as a fluorenyl group), etc. <B-2> super acid, a Lewis acid compound, and an ionic boron compound super acid may, for example, be hexafluoroantimonic acid. , hexafluorophosphoric acid, hexafluoroantimonic acid, trifluoroacetic acid, fluorinated sulfuric acid, trifluoromethanesulfonic acid, tetrafluoroboric acid, hydrazine (pentafluorophenyl)boronic acid, hydrazine [3,5-bis(trifluoromethyl)benzene Boric acid, P-toluenesulfonic acid, pentafluoropropionic acid, and the like. The Lewis acid compound may, for example, be a complex of boron trifluoride with an ether, an amine, a phenol or the like, an ether of aluminum trifluoride, an amine, a phenol or the like, a quinone (pentafluorophenyl) borane, or a ginseng. a boron compound such as [3,5-bis(trifluoromethyl)phenyl]borane; aluminum trichloride, aluminum tribromide, ethyl aluminum dichloride, ethyl aluminum sesquichloride, diethyl Aluminum compound such as aluminum fluoride or tris(pentafluorophenyl)aluminum; hexafluoroacetone, hexachloroacetone, tetrachlorophenyl hydrazine, hexafluoromethyl ethyl ketone, etc., organic acid halide showing Lewis acid; titanium tetrachloride , ruthenium pentafluoride, etc., showing Lewis acid compounds. Examples of the ionic boron compound include triphenylcarbenium (pentafluorophenyl) borate, triphenylcarbohydrate [3,5-bis(trifluoromethyl)phenyl]borate, and triphenylcarbon. Keyuanium (2,4,6-trifluorophenyl)borate, -25- 200844511 triphenylcarbenyltetraphenylborate, tributylammonium ruthenium (pentafluorophenyl)borate, N,N- Dimethylanilinium quinone (pentafluorophenyl)borate, N,N-diethylanilinium quinone (pentafluorophenyl)borate, N,N-diphenylanilinium quinone (pentafluorophenyl) Borate, etc. <B-3> organoaluminum compound organoaluminum compound such as methylaluminoxane, alumoxane, butylaluminoxane, etc.; alkylaluminoxane compound; trimethylaluminum, triethyl Aluminium alkyl compound such as aluminum, triisobutyl aluminum, diisobutyl aluminum mirror coal, diethyl aluminum chloride, diethyl aluminum fluoride, ethyl aluminum sesquichloride, ethyl aluminum dichloride And an alkylaluminum compound to be halogenated; a mixture of the above alkyl aluminoxane compound and the above-mentioned alkyl aluminum compound, and the like can be given. The components of these polymerization catalysts are, for example, used in the following ranges: 过渡 With respect to the monomer 1 mole, the transition metal compound <B-1> is 0.02 to 1 〇〇 millimolar. When the organoaluminum compound <B-3> is used (multi-component catalyst systems <A> and <B>), the organoaluminum compound <B- relative to the metal atom of the transition metal compound <B-1> is 1 mol. 3> is 1 to 5,000 m. Furthermore, if a super acid, a Lewis acid or an ionic boron compound <B-2> (multi-component catalyst system <B>) is used, a metal atom 1 mol relative to the transition metal compound <B-1> , using these compounds 0.1 to 100 moles. -26- 200844511 (Π-b) Polymerization solvent used in the polymerization (co)polymerization reaction, if it is a monomer composition or a polymerization catalyst which can provide addition (co)polymerization, and the catalyst Further, the active norbornene-based resin is not deactivated, and is not particularly limited, and examples thereof include an alicyclic hydrocarbon solvent such as cyclohexane, cyclopentane or methylcyclopentane; and hexane; An aliphatic hydrocarbon solvent such as heptane or octane: an aromatic hydrocarbon solvent such as toluene, benzene, xylene or trimethylbenzene; dichloromethane, 1,2-dichloroethane, 1,1-dichloroethane A halogenated hydrocarbon solvent such as an alkane, tetrachloroethane, chlorobenzene or dichlorobenzene. These may be used alone or in combination of two or more. (11-C) Molecular Weight Modifier The molecular weight of the norbornene-based resin of the present invention can be adjusted by adding hydrogen or an α-olefin as a molecular weight modifier in an addition (co)polymerization reaction system. . The molecular weight of the resulting norbornene-based resin increases as the molecular weight regulator is added. [Hydrogenation reaction] The norbornene-based resin obtained by the ring-opening (co)polymerization (I) has an olefinic unsaturated bond in the norbornene-based resin. Further, in the addition (co)polymerization reaction (11), the norbornene-based resin may have an olefinic unsaturated bond in the norbornene-based resin. The olefinic unsaturated bond present in the norbornene-based resin causes the deterioration of the olefinic unsaturated bond and the hydrogenation of the bond by causing deterioration of the colored or colloidal -27-200844511 or the like. good. In general, the hydrogenation reaction method is to add a conventional hydrogenation catalyst to a norbornene-based resin solution containing an olefinic unsaturated, usually at a pressure of 300 to 300, preferably 3 to 200, and a hydrogen gas at 0 to 200. °C is preferably carried out at a temperature of 20 to 180 °C. The hydrogenation ratio of the hydrogenated norbornene-based resin is usually 50% or more, preferably 70% or more, more preferably 90% or more, and 98% by weight, measured at 500 MHz and 1H_. The above is particularly good, and it is better to be 99% or more. The higher the rate, the more stable the heat or light of the hydrogenated norbornene-based resin is, and when it is used as a molded body, it is preferable to obtain a stable after a long period of time. When the norbornene-based resin obtained by the hydrogenation reaction has an aromatic group in the norbornene, the aromatic group does not cause deterioration due to colloidalization or the like, even in mechanical properties or optical properties. It has such an advantageous effect that such an aromatic group does not require hydrogenation. As the hydrogenation catalyst used in the hydrogenation reaction, those used in the hydrogenation reaction of a general olefinic compound can be used. The hydrogenation catalyst may be exemplified by a heterogeneous catalyst and a homogeneous catalyst. The heterogeneous catalyst may be a solid catalyst in which a noble metal catalyst such as palladium, platinum, nickel or rhodium is supported on a support such as graphite, cerium oxide, alumina or oxygen. The homogeneous catalyst is exemplified by nickel naphthalate/base aluminum, nickel acetonitrile acetic acid/triethylaluminum, cobalt octylate/η-butyllithium, and is superior to hydrogenation by NMR. The color of the tree or the combination of the same system, such as titanium triethyl-28-200844511, titanium dichloride / diethyl aluminum monochloride, barium acetate, chlorine (triphenylphosphine), dichlorohydrazine (triphenylphosphine) hydrazine, hydrogen chlorohydrin (triphenylphosphine) hydrazine, dichlorocarbonyl ginseng (triphenylphosphine) hydrazine, and the like. These catalysts may be in powder or granule form. The hydrogenation catalyst is usually used in a ratio of a weight ratio of the ring-opened norbornene-based resin to the hydrogenation catalyst (open-ring norbornene-based resin: hydrogenation catalyst) of 1:1χ10_6 to 1:2. . [Ultraviolet absorber] The norbornene-based resin of the present invention may be added with an ultraviolet absorber. The ultraviolet ray absorbing agent can suppress the generation of active radical species which cause deterioration of the norbornene-based resin by absorbing ultraviolet rays, and prevent coloring or transparency which is caused by deterioration from deteriorating, and hinder ultraviolet ray transmission to the polarizing film. 'has the role of preventing deterioration of the polarizing film. The ultraviolet absorber is preferably a benzotriazole derivative. The melting point of the benzotriazole derivative is preferably from Tg - 35 ° C to Tg + 75 ° C to Tg- relative to the glass transition temperature of the norbornene-based resin (hereinafter referred to as "Tg"). 3 0 ° C ~ Tg + 70 ° C is particularly good. If the melting point of the benzotriazole derivative is lower than Tg-35 ° C, the volatility of the benzotriazole derivative increases, and the benzotriazole derivative and its decomposition product adhere to the norbornene-based resin film or Problems with film forming machines and the like. Further, when the melting point of the benzotriazole derivative is higher than Tg +75 ° C, the benzotriazole derivative is formed on the surface of the norbornene-based resin film during film formation, and will be formed during the cooling process. Because it has a high melting point and is incompatible, it solidifies on the surface and adheres to the roll or the surface of the borneol-based resin film. The benzotriazole derivative may, for example, be 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-[211-benzotriazol-2-yl Phenol], 2-( 2H-1,2,3-benzotriazol-2-yl)-4,6-di-tert-butylphenol, 2-(2-carbo- 5-tert-butyl Phenyl)-2H-benzotriazine, 2-(3,5-mono-butyl-2-phenylphenyl)benzotriazine, 2-[2'-hydroxy-3,,5' - bis-(〇1,〇1-dimethylbenzyl)phenyl]-211-benzotriazine, 2-[ 2,-hydroxy-3'-( 1-methyl-1-phenyl Base)-5,-(1,1,3,3-tetramethylbutyl)-benzotriazole and the like. Among these, in particular, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-[2H-benzotriazol-2-yl]phenol] is used. It is better. Further, the ultraviolet absorber of the present invention may be an ultraviolet absorber other than the benzotriazole derivative. UV absorbers which can be used are, for example, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, hydrazine-3-methyl-3-(3,5-di tert-butyl) 4-hydroxyphenyl)propionate]methane, and the like. The amount of the ultraviolet absorber to be added is usually 0.1 to part by weight, preferably 0.1 to 5 parts by weight, based on 1 part by weight of the norbornene-based resin. When the amount of the ultraviolet absorber added is less than 0.1 part by weight, a sufficient ultraviolet absorbing effect is not observed, and it is difficult to exhibit the effects of the present invention. On the other hand, when it exceeds 20 parts by weight, the resulting norbornene-based resin film will have a low transmittance in the visible light field. Further, the proportion of the benzotriazole derivative in the total ultraviolet absorbing agent is usually 10% by weight or more, preferably 50% by weight or more, based on -30 to 200844511. [Other Additives] The norbornene-based resin of the present invention may further contain an additive such as an antioxidant without impairing the scope of the present invention. The antioxidant may, for example, be 2,6-di-t-butyl-4-methylphenol or 2,2'-dioxy-3,3'-di-t-butyl-5,5'-dimethyl Diphenyl phenyl phthalocyanine [methyl-3-(3,5-di-t-butyl-4.hydroxyphenyl)propionic acid j and the like. Further, when a norbornene film is produced by casting, which will be described later, a resin film is formed by adding a leveling agent or an antifoaming agent. These additives may be added together with the norbornene-based resin in the production of the norbornene-based resin of the present invention, or may be added before the production of the resin. Further, the amount of addition may be appropriately selected, but it is usually (parts by weight, preferably desirably 5 to 2.0 parts by weight) based on 1 part by weight of the norbornene-based resin. [Norbornene-based resin The characteristics of the norbornene-based resin of the present invention are preferably chloroform at 30 ° C [11] 1 heart is preferably 2. 2~2. (^1/^, more preferably 〇.35~, wherein 0.4~0.85dl/g is particularly good; the polystyrene-converted number average molecular weight measured by the colloidal permeable layer) (Μη: the effect of the ester) methane storage resin is easy to manufacture, the resin film borneol is selected, ). 01 ~ 5.0 intrinsic viscosity l.Odl / g analysis (GPC) is preferably • 31 - 200844511 5000 to 1 million, more preferably 10,000 to 500,000, of which 15,000 to 250,000 is particularly good; weight average molecular weight (Mw) is 10,000 to 2 million, preferably 20,000 to 1 million, and 30,000 to 500,000 is particularly good. When the intrinsic viscosity [η]inh, the number average molecular weight, and the weight average molecular weight fall within the above range, mechanical strength can be obtained. An excellent, non-destructible norbornene-based resin film. Further, the glass transition temperature (Tg) of norbornene-based resin It is usually 120 ° C or higher, preferably 130 ° C or higher. When the Tg falls within the above range, a norbornene-based resin film 0 having high reliability even after long-term use can be obtained [Manufacture of norbornene-based resin film) [Method] The norbornene-based resin film of the present invention is obtained by directly melt-molding a norbornene-based resin or a resin composition containing a norbornene-based resin and the above-mentioned additive, or by dissolving in a solvent and then casting (casting molding). (I) The norbornene-based resin film of the present invention is melt-molded, and a norbornene-based resin or a resin composition containing a norbornene-based resin and the above-mentioned additive is produced by melt-extrusion molding. II) Casting The norbornene-based resin film of the present invention is a liquid resin composition in which a norbornene resin and a solvent which are required to be dissolved in a solvent are dissolved in a solvent-32-200844511 'cast on a suitable substrate Manufactured by removing the solvent and then removing the solvent. For example, the liquid tree can be coated on a substrate such as a steel belt (steel belt), a steel drum (steel Drum) or a polyester film. After the composition is dried, the amount of residual solvent in the norbornene-based resin film obtained by casting the norbornene-based resin film 〇 by the peeling of the coating film from the substrate is preferably as small as possible. Usually, it is 3% by weight or less, preferably 1% by weight or less, and more preferably 5% by weight or less. If the amount of residual solvent falls within the above range, the temporal deformation or characteristic change of the film is difficult to occur, and The norbornene-based resin film having the desired function is obtained. [Characteristics of the norbornene-based resin film] The thickness of the norbornene-based resin film of the present invention is not particularly limited, but is usually 5 to 500 μm, preferably 10 ~150μιη, while 20~ΙΟΟμιη is even better. When the thickness of the film is within the above range, a norbornene-based resin film having sufficient strength can be obtained, and a norbornene-based resin film excellent in birefringence, transparency, and appearance can be obtained. In addition, the moisture permeability of the norbornene-based resin film of the present invention is measured at a temperature of 40 ° C and a relative humidity of 90% RH, and is usually measured according to the wet-sensing method of JIS K7 129. 00 ( g · 25 μm / m 2 · 24 hr ) or less, preferably 5 to 200 (g * 25 pm / m 2 * 24 hr), and particularly preferably 50 to 150 (g · 25 μm η / m 2 · 24 hr). If the moisture permeability exceeds 300 (g · 25μιη / m2 · 2 4hr), the water will immerse in the polarizing film inside the polarizing plate under high temperature and high humidity, resulting in deterioration of optical characteristics. -33- 200844511 Poor. When the moisture permeability is 5 to 2 〇〇 (§.25 0111/1112.24111*), when the polarizing plate is manufactured, the moisture of the polarizing film is dried smoothly, and the water does not immerse in the polarizing film, so the optical characteristics are not caused by the long time. It is better to deteriorate. Further, the moisture permeability in the present invention can be measured by preparing a sample having a film thickness of 25 μm. The water absorption of the norbornene-based resin film of the present invention is usually 1.0% by weight or less, preferably 0.8% by weight or less, and more preferably 0.5% by weight or less. When the water absorption rate exceeds 1.0% by weight, the optical characteristics are deteriorated due to water absorption of the polarizing film, which is not preferable. The norbornene-based resin film of the present invention has a light transmittance of usually 80% or more, preferably 85% or more, and more preferably 90% or more. When the transmittance is less than 80%, the monomer transmittance of the polarizing plate is lowered, so that the brightness of the liquid crystal display element is insufficient, which is not preferable. [Retardation film and its production method] At least one of the norbornene-based resin films of the present invention is a retardation film obtained by performing an extension treatment. The above stretching treatment method may be a method of performing one-axis stretching or biaxial stretching of the resin film. In the case of the one-axis stretching treatment, the stretching speed is usually from 1 to 5,000%/min, preferably from 50 to 1,000%/min, and from 100 to 1, more preferably 〇〇〇%/min. In the case of the biaxial stretching treatment, a method of performing the elongation treatment in two directions or a method of extending the treatment in a direction different from the direction of the stretching treatment after the one-axis stretching treatment can be applied. In this case, the angle of intersection of -34 - 200844511 of the two extension axes may be appropriately selected depending on the characteristics required for the objective optical film (phase difference film), and is not particularly limited, and is usually in the range of 60 to 120 degrees. Further, the stretching speed is usually from 1 to 5,000%/min, preferably from 50 to 1,000%/min, more preferably from 100 to 1,000%/min, and particularly preferably from 100 to 50,000%/min. Further, the temperature at which the angles may be the same or different from each other in the extending direction is not particularly limited, but is generally Tg ± 3 (rc, based on the glass transition temperature (Tg) of the norbornene based resin used. Preferably, Tgi: 15C, and more preferably Tg-5 to Tg + 15 ° C. By setting the elongation treatment temperature within the above range, the phase difference unevenness on the obtained stretched film can be suppressed, and It is preferable to easily control the point of the ellipsoid of the refractive index. The stretching ratio can be appropriately determined according to the characteristics required of the optical film of the object, and there is no particular limitation, which is usually 1 · 〇1~1 〇 times, Preferably, it is 1.03~5 times, more preferably 1~〇3~3 times. If the stretching ratio is within the above range, the phase difference of the obtained stretched film can be easily controlled. The stretched film can be directly placed and cooled, and can be kept at Tg. -20 ° C ~ Tg temperature atmosphere for at least 10 seconds or more, preferably 30 seconds to 60 minutes, more preferably 1 to 60 After that, it is further cooled, whereby a retardation film having a small change in the phase difference of the transmitted light with a small change in time can be obtained. After the above operation, the film subjected to the stretching treatment can be imparted with the result of the molecular alignment of the stretching treatment. Through the optical phase difference, the phase difference can be controlled according to the stretching ratio, the stretching temperature, or the thickness of the film, etc. The thickness of the norbornene-based resin film used as the retardation film is not limited to -35-200844511, and is usually 5 to 500 μm η is preferably 10 to 150 μm, and more preferably 20 to ΙΟΟ μπι. Further, the norbornene-based resin film of the present invention may be subjected to surface treatment for the purpose of improving adhesion to an adhesive layer to be described later. The surface treatment may include primer treatment, plasma treatment, corona treatment, inspection treatment, coating treatment, etc. Among the above surface treatments, in particular, by performing corona treatment, norbornene may be used. The resin film and the adhesive layer are strongly adhered to each other. The corona treatment condition at this time is preferably 1 to 1 000 W/m 2 /min, and 10 to 100 W/m 2 /min. If the amount of irradiation falls within the above range, the treatment effect is as close as possible to the inside of the film, and sufficient surface modification effect can be obtained without deteriorating the film. Moreover, the corona treatment is not limited to the adhesive layer. The opposite side, the opposite side of the surface can also be implemented. &lt;Polarizing film and method for producing the same&gt; The polarizing film of the present invention has a function of dividing the incident light into two polarizing components perpendicular to each other, and passing only one of them and absorbing or dispersing other components. Particularly limited, any type of polarizing film street can be used. The polarizing film of the present invention may, for example, be a polyvinyl alcohol (hereinafter referred to as "PVA") or an iodine-based polarizing film, or a PVA dye-based polarizing film in which a dichroic dye is adsorbed and aligned on a PVA-based film, and a PVA-based film. The dehydration reaction or the dehydrochlorination reaction of the polyvinyl chloride film to form a polyolefin-based polarizing film of a polyene, and a surface of the PVA-based film comprising a modified PVA having a cationic group in the molecule, and/or an inner portion thereof A polarizing film of a dichroic dye or the like. Among these, a PVA·iodine-based polarizing film is preferred. -36- 200844511 The method for producing the polarizing film of the present invention is not particularly limited, and a conventional method can be applied. For example, a method in which a PV A-based film is stretched to adsorb iodide ions, a method in which a PVA-based film is dyed by a dichroic dye, and a method in which a PVA-based film is stretched and then dyed with a dichroic dye; and a PVA-based method; A method in which a dichroic dye is printed on a film and then stretched; a method in which a PVA-based film is stretched, and a dichroic dye is printed. More specifically, iodine is dissolved in a potassium iodide solution to form a high-order iodide ion, and the ion is adsorbed on the PVA film to be stretched, followed by a bath temperature of 30 to 4 in a 1 to 5 wt% aqueous boric acid solution. (A method of producing a polarizing film after immersing in TC; or subjecting the PVA film to boric acid treatment in the same manner as described above and extending in the axial direction by 3 to 7 times, and then in a bath temperature of 0.05 to 5% by weight of the dichroic dye aqueous solution; The method of producing a polarizing film by immersing the dye after immersion at 40 to 100 ° C, followed by drying at 80 to 100 ° C, and the like. The thickness of the polarizing film of the present invention is not particularly limited, and is generally 1 〇 50 50 μm, preferably The water absorbing film of the present invention is preferably 20% by weight or less, preferably 15% by weight or less. The polarizing film of the present invention can be directly used in the production of the polarizing plate of the present invention. It can be used after corona discharge treatment and plasma treatment on the interface with the adhesive layer. &lt;Adhesive layer and method for producing the same&gt; The adhesive of the present invention is used for a film of a norbornene-based resin and a polarizing film. The adhesive is not particularly limited, but an ultraviolet curable adhesive such as an ultraviolet polymer-37-200844511 polymer and/or an ultraviolet polymerizable monomer and an ultraviolet polymer composition; a polyvinyl alcohol water-soluble pseudo alcohol or a polyamine is particularly preferred. A water-based adhesive such as an ethyl urethane resin or an epoxy curing agent. &lt;Hard coat layer and method for producing the same&gt; The hard coat layer of the present invention is laminated on a norbornene-based resin to prevent surface damage of the norbornene-based resin, and is formed by dispersing fine particles and having anti-glare Layer players are better. The hard coat treatment may be carried out on both sides or one side of the film, and the hard coat layer is preferably formed on the surface on the opposite side of the norbornene-based resin film (a). The hard coat layer is preferably a hard coat film in which a hard coat treatment agent having an average particle diameter of 5 μη fine particles is dispersed in an active energy ray-curable resin such as a melamine-based ethyl acrylate resin, an alkyd resin or an acrylic resin resin. . Among the above-mentioned line-curable resins, the acrylic resin is most preferable because it has an effect of improving the adhesion. Further, the fine particles used herein are preferably cerium oxide particles or particles, and the cerium oxide may be colloidal cerium oxide or soot. Here, the soot cerium oxide refers to a high-purity (99.9% or more) anhydrous water in the form of particles of an industrial system (average primary particle diameter: 7 nm to 3 μm, and 1 to 380 m 2 / g). In the oxygen/hydrogen furnace of antimony tetrachloride, the surface of the film prepared by the hydrolysis method of 1 ° C or less, or the surface of the film of the polyethylene solution, etc. Membrane resin, amine, Shixia tree: 50 nm ~ active energy, conductive layer, acrylic polyphosphonium oxide, etc. with minimum specific surface area oxidation, high temperature -38- 200844511 cerium oxide can use surface stanol group via hydrophobicity The processor is preferably a hydrophobic treatment. The proportion of the cerium oxide particles is preferably from 1 to 20 parts by weight based on 100 parts by weight of the resin. If the amount of cerium oxide particles is too small, the anti-glare effect is poor, and if too much, the light transmittance or the film strength will be lowered. When the hardened film is formed, the active energy ray-curable resin and the fine particles may be prepared by adding a mixture of various additives such as an antistatic agent and a polymerization initiator to a general solvent. The solid form is divided into 20 to 80% by weight on one side of the optical film, and the general solution coating method is used for gravure coating, reverse roll coating, spray coating, slot extrusion or screen printing. In the method of drying, the thickness after drying and hardening is 1 to 15 μm, and after curing by heating, it is hardened by ultraviolet irradiation or electron beam irradiation. After the hard coating layer is formed first, the adhesion surface of the coated surface is corona discharge, ultraviolet irradiation, plasma treatment, splash etching treatment, primer treatment, etc., and the adhesion between the transparent film and the hard coating layer can be further improved. Sex. &lt;Adhesive layer and method for producing the same&gt; The adhesive layer of the present invention contains a polymer derived from an alkyl (meth) acrylate. A preferred polymer contains at least one polymer derived from an alkyl (meth) acrylate represented by the following formula (i). CH2=CRCOOR, -39- 200844511 (In the formula (i), R represents a chlorine atom or a methyl group, and R' represents an alkyl group having an atomic number of 1 to 12). In the above formula (i), R' is represented. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, an η-propyl group, an i-propyl group, an η-butyl group, an i-butyl group, a t-butyl group, and an η-pentyl group. Η-hexyl, η-heptyl, η-octyl, η-fluorenyl, η-fluorenyl, η·undecyl, η-dodecyl, etc., among these, especially η-butyl It is better. Further, the alkyl (meth) acrylate represented by the above formula (i) may contain one type or two or more types as a monomer. The polymer contained in the adhesive layer of the present invention may contain a monomer other than the alkyl (meth) acrylate. The single system other than the alkyl (meth) acrylate is preferably unsaturated carbonic acid, and examples thereof include α·β-unsaturated carbonic acid such as acrylic acid, methacrylic acid, itaconic acid, and the like; 2-hydroxyethyl (methyl group) Other (meth) acrylates such as acrylate, 2-hydroxypropyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, glycidyl (meth) acrylate, etc.; Other compounds having an ethylenically unsaturated double bond such as vinyl acetate, vinyl propionate, acrylonitrile, styrene, vinyl toluene, and the like can be given. The polymer constituting the adhesive layer of the present invention has a weight average molecular weight in terms of polystyrene measured by GPC, preferably 1 or more, more preferably 1,500,000 or more. Among them, 1,500,000 to 5,000,000 is even better, and particularly preferably 1,500,000 to 3,000,000. When a polymer having a molecular weight of 1,500,000 or more is contained, adhesion to a norbornene-based resin film can be improved, and foaming or peeling does not occur even after storage for a long period of time under high temperature and high humidity, and long-term reliability is obtained. Excellent polarizing plate. Further, the glass transition temperature (Tg) of the polymer constituting the adhesive layer is preferably -50 ° C or more, and particularly preferably -50 ° C to -25 ° C. The thickness of the adhesive layer of the present invention is not particularly limited and is usually 5 to 50 μm, preferably 10 to 40 μm, and more preferably 20 to 30 μm. If the thickness of the adhesive layer is less than 5 μm, it may not be able to float or peel off as the volume of the polarizing plate changes. If it exceeds 50 μm, the optical characteristics may deteriorate. The adhesive layer of the present invention is obtained by applying an adhesive composition obtained by adding a curing agent and an organic solvent to the above polymer as needed, followed by drying. When the polarizing plate is attached to the substrate through the adhesive layer, the adhesive layer is placed on the substrate, and if necessary, it can be pressed while being heated to proceed. The above-mentioned curing agent is preferably exemplified by an isocyanate compound <A>, an epoxy compound <B>, an aldehyde compound <C>, an amine compound <D> and the like. Examples of the <A> isocyanate compound include tolylene diisocyanate, toluene diisocyanate hydride, toluene diisocyanate adduct of trimethylmethylpropane, and xylene diisocyanate adduct of trimethylolpropane. Triphenylmethane triisocyanate, methylene bis(4-phenylmethane) triisocyanate, isophorone diisocyanate, and the like. Examples of the epoxy compound include bisphenol A·epichlorohydrin epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerol diglycidyl ether, and C III. Alcohol triglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether, diglycidyl aniline, diglycidylamine, N, N, N', N'-four Glycidyl-m-xylylenediamine, 1,3-bis(N,N'-diglycidylaminomethyl)cyclohexane, and the like. -41 - 200844511 <C> The aldehyde compound may, for example, be glyoxal, malondialdehyde, butyl dimalealdehyde, glutaraldehyde, formaldehyde, acetaldehyde or benzaldehyde. The <D> amine compound may, for example, be hexamethylenediamine, triethyldiethyleneimine, hexamethylenetetramine, diethylenetriamine, triethyltetramine phorone diamine, amine resin, melamine Resin, etc. &lt;Polarizing Plate and Method of Producing the Same&gt; The polarizing plate of the present invention is a polarizing plate which is passed through the subsequent layer of the polarizing film and is followed by the norbornene-based resin film. The olefinic resin film is preferably one in which at least one layer is a triazole derivative containing a UV absorber, and the norbornene-based resin on the hard coat side is preferably a film containing a UV absorber, and particularly preferably a two-sided drop. The borneol resin film is all those containing an ultraviolet absorber. The method for producing the polarizing plate of the present invention is not particularly limited, and a uniform adhesive is applied to one surface of the norbornene-based resin film or the polarizing film, and a norbornene-based resin film or a polarizing film is applied to the coated surface. Thereafter, it is bonded by a roller or the like, and heating or exposure may be performed as needed. 5微米。 In this case, the thickness of the adhesive layer after drying is more than 0. 0 1~50μηη, more preferably 0.01 to 30μπι, particularly preferably 0.3 μηη. If the thickness of the adhesive layer after drying maintains the transparency of the polarizing plate in the above-described range, and the norbornene-based resin film and the film system are followed by a very sufficient adhesion, it is difficult to cause aldehydes, amines, and the like among the layers. The above-mentioned ice-forming benzophenone film is an olefin-based film, for example, a coating film is preferably laminated, and the film is preferably in the range of 15 to 4 〇t, and the bonding temperature is usually in the range of 15 to 4 〇t. It is usually in the range of 1 5 to 3 0 °c. When an ultraviolet curable adhesive is used as the adhesive, the exposure treatment is carried out after bonding, and the adhesive is cured. The exposure light source at this time is not particularly limited, and is preferably ultraviolet light. Further, the exposure amount is preferably from 1 to 2000 mJ. The polarizing plate of the present invention has excellent polarizing performance, and is excellent in properties such as heat resistance and chemical resistance, and is difficult to cause peeling, deformation, change in polarization degree, etc. even after long-term use, and has high reliability and durability. Excellent. Such a polarizing plate is preferably used for a liquid crystal display device or the like. [Embodiment] [Embodiment] Next, the present invention will be described in detail by way of examples, but the present invention is not limited thereto. In addition, the following "parts" means "parts by weight" unless otherwise specified. Further, the measurement of the glass transition temperature, the moisture permeability, the water absorption rate, the transmittance, and the degree of polarization, and the moisture resistance test, the dry heat test, and the uv test were carried out according to the following methods. [Glass transition temperature] Using a differential scanning calorimeter (DSC) manufactured by Seiko Instruments Co., Ltd., the glass transition temperature was measured at a temperature rise rate of 20 ° C /min under a nitrogen atmosphere -43 - 200844511 [transparent humidity] The film thickness was 25 μm The film was cut out to a size of 10 cm x 10 cm, and the moisture permeability was measured according to JIS K7129 moisture sensing method under the conditions of a measurement temperature of 40 ° C and a relative humidity of 90% RH using L8 0-4000 manufactured by LYSSY. [Water absorption rate] The sample was immersed in water at 23 ° C for 1 week in accordance with ASTM D5 70, and the change in weight before and after the immersion was measured. [Transmittance and Monomer Permeability] The transmittance and monomer transmittance were measured using a spectrophotometer V73 00 manufactured by JASCO Corporation. [Polarization degree] The degree of polarization was measured using a spectrophotometer V73 00 manufactured by JASCO Corporation. [Damp heat test 1] After 500 hours of storage at a temperature of 80 ° C and a relative humidity of 95%, the degree of polarization was measured, and the amount of change in the degree of polarization (= {b [the degree of polarization after the damp heat test] / [initial degree of polarization) 〕} X 1 〇〇 (%)) is evaluated on the basis of the following criteria. A: The amount of change in the degree of polarization is less than 0.5% -44- 200844511 B: The amount of change in the degree of polarization is 0.5% or more and less than 2% C: The amount of change in the degree of polarization is 2% or more (dry heat test 1) at temperature After 500 hours of storage at 95 °C, the degree of change in polarization, measured by the degree of polarization (= { 1 - [polarity after wet heat test] / [initial polarization]} X 1 0 0 ( % )) After that, it is evaluated on the basis of the following criteria. A: The amount of change in the degree of polarization is less than 〇. 5 % B : The amount of change in the degree of polarization is 0.5% or more and less than 2% C: The amount of change in the degree of polarization is 2% or more (UV test 1) by polarizing plate On the upper side of the single side, the fading tester (Fade-o-meter) manufactured by s UGA Tester Co., Ltd. was used to measure the degree of polarization by the change of the degree of polarization after 1 hour of irradiation with a graphite arc lamp. The amount (two { 1 - [polarity after wet heat test] / [initial polarization]} X 1 00 (%)) was evaluated based on the following criteria. A: The amount of change in the degree of polarization is less than 0.5%. B: The amount of change in the degree of polarization is 〇·5% or more and less than 2%. C: The amount of change in the degree of polarization is 2% or more (adhesion of the adhesive layer). On the adhesive surface of the board, the glass plate was bonded to the test piece by means of a plate-making machine in a manner of not inserting air bubbles -45-200844511. The test piece was placed in stainless steel, and placed at a constant temperature tester at 95 ° C or a constant temperature and humidity of 85 ° C 8 5 % RH for 500 hours, and the following evaluation was carried out. Peelability: The change in appearance was observed with the naked eye. Foaming property: The change in appearance was observed with the naked eye. The evaluation criteria are as follows. Peelability A: less than 〇. 5 mm peeling B: 0 · 5~1 · 0 mm peeling C: peeling foaming property exceeding 1.0 mm A: no air bubble of diameter 20 μm or more B: a little diameter 2 0~4 0 μηι bubbles C: There are many bubbles with a diameter of 20~40 μηι &lt;Synthesis Example&gt; 87.5 parts of 8-methyl-8-methoxycarbonyltetracyclo[4·4·0·12'5·17'1() diene and bicyclo [2.2.1] g- 2 parts of 2-ene, 1·molecular weight modifier), and 8 parts of toluene (ring-opening copolymerization agent) 75 parts were placed in a reaction vessel substituted with nitrogen, and this was dissolved to 60 °C. Next, in the solution in the reaction vessel, a solution of triethyl toluene (1.5 mol/1) 0·62 parts and t-butanol/methyl hexachloride (t-butanol: methanol: tungsten = 0.35) were added. Mohr: 0.3 | Moore) toluene solution (concentration 〇. 〇 5 mol / 1) 3.7 parts, so that the test machine on the stent] -3 - decahexene (polymerization solution heating base aluminum alcohol modification I ear: 1 This is a norbornene-based resin solution obtained by subjecting to a ring-opening (co)polymerization reaction by heating and stirring at 80 ° C for 3 hours. The polymerization conversion ratio in this polymerization reaction is 9 7%. 4,000 parts of the norbornene-based resin solution obtained above was placed in a high-pressure boiler, and 0.48 parts of RuHCl(C0)[P(C6H5)3]3 was added to the norbornene-based resin solution at a hydrogen pressure of 1 〇〇kg / The hydrogenation reaction is carried out by heating and stirring for 3 hours under the condition of a reaction temperature of 1 60 ° C. After cooling the obtained reaction solution (hydrogenated norbornene-based resin solution), hydrogen pressure is released, and the reaction solution is poured into a large amount of methanol. The coagulated solids are separated and recovered and dried to obtain a hydrogenated norbornene-based tree. The norbornene-based resin has a Tg of 140 ° C. Further, Mn, Mw, and Mw/Mn in terms of polystyrene measured by GPC are 24,000, 67,000, and 2.8, respectively, and the intrinsic viscosity (ηίη1) is 0.49. Dl/g. &lt;Production Example 1 &gt; [Preparation of norbornene-based resin film-1] Using a 2-axis extruder, 2, 2'- as a UV absorber was added to the norbornene-based resin. Methyl bis[4-(1,3,3,3·tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol] (melting point 199. 〇) 1 · 3 parts, After melt-kneading at 270 °C, it was introduced into a 70 0mm wide coat-shaped die by a two-shaft discharge type gear pump through a polymer filter (aperture 5 Km) heated to 28 (TC). The norbornene-based resin from the die falls into a casting roll of 25 Ommcp and is pressed, and the two cooling rolls horizontally arranged on the die-rolling roll are sequentially pressed and peeled off, and the obtained-47-200844511 4 0 A norbornene-based resin film having a thickness of μηι was subjected to corona discharge treatment on the obtained norbornene-based resin film under the conditions of 150 W/m 2 /mirx to obtain a norbornene-based resin film-1. The obtained norbornene-based resin The film-1 has a moisture permeability of 75 (g · 25 μm / m 2 · 24 hr) and a light transmittance of 380 nm of 2%. &lt;Production Example 2 &gt; [Preparation of norbornene-based resin film-2] The pellet of the norbornene-based resin was melt-kneaded at 270 ° C, and then passed through a two-axis discharge type gear pump. The polymer filter (pore size 5 μιη) heated at 280 °C was introduced into a 700 mm wide coat hanger die. The norbornene resin from the die falls into a casting roll of 25 Ommcp and is pressed, and the two cooling rolls horizontally arranged on the casting roll are sequentially pressed and peeled off to obtain a thickness of 40 μηι. A borneol-based resin film. The obtained norbornene-based resin film was subjected to corona discharge treatment to obtain a norbornene-based resin film-2. The norbornene-based resin film-2 had a moisture permeability of 75 (g · 25 μm / m 2 · 24 h 、 and a light transmittance of 380 nm of 91%. &lt;Production Example 3 &gt; [Preparation of norbornene-based resin film] The norbornene-based resin film-1 obtained in Production Example 1 was heated in a sheet frame to T g + 1 〇 ° C 1 3 5 ° C 'and extending 1.00 times in the longitudinal direction of the film in the longitudinal direction of the film, and then obtaining a -48-200844511 retardation film (norbornene-based resin film-3) in the transverse direction of the film in-plane direction. The obtained norbornene-based resin film-3 had a moisture permeability of 75 (g · 25 μm / m 2 · 24 hr) and a light transmittance of 2 80 nm at a wavelength of 3 80 nm. Further, the phase difference (R0) at a wavelength of 5 90 nm is 6 Onm. &lt;Production Example 4 &gt; [Production of Polarizing Film] Polyvinyl alcohol (hereinafter abbreviated as "PVA") was formed by an aqueous solution having an iodine concentration of 3% by weight and a potassium iodide concentration of 5% by weight. In the dyeing bath at a temperature of 30 ° C, the pre-stretching process was carried out at a stretching ratio of 3 times, and then at a temperature of 5 5 ° C in an aqueous solution having a boric acid concentration of 5% by weight and a potassium iodide concentration of 8% by weight. In the joint bath, after the post-stretching process was performed at a stretching ratio of 2 times, a polarizing film was obtained by a drying treatment. &lt;Preparation Example 1 (Preparation of Adhesive)&gt; 丨63 _ 03045 (molecular weight: 22, hydrazine, alkalinity: 88 mol%, manufactured by Wako Pure Chemical Industries, Ltd.) In addition, water was added to prepare an aqueous solution having a solid concentration of 7 wt%. In addition, 100 parts of WLS-201 (solid content concentration: 35 wt%) manufactured by Dainippon Ink Chemicals Co., Ltd., a polyurethane resin, is a large Japanese ink industry with a polyepoxy curing agent. 5 parts of CR_5L (active ingredient 1 〇〇 ° / item) manufactured by the company, diluted with water, and prepared with an aqueous solution having a solid concentration of 20% by weight. The obtained aqueous solution of the polyurethane resin is mixed with the aqueous solution of the polyethylene glycol-based resin in a weight ratio of 1:1 (the ratio of the solid component weight: 49 to 200844511 is 80:20) to prepare a solid concentration. It is 15% by weight of an adhesive. &lt;Preparation Example 2 (Preparation of Adhesive Composition-1)&gt; 95 parts of η-butyl acrylate, 5 parts of acrylic acid, and A Α-6 of methacrylic acid (A group having a methacryl fluorenyl group on the terminal group) 15 parts of methyl acrylate macromonomer, manufactured by Toagosei Co., Ltd., and ethyl acetate as a solvent to obtain a graft polymer solution having an average molecular weight of 1,500,000. 1.5 parts of CORONATEL (toluene diisocyanate of trimethylolpropane, manufactured by Esoteric Polyurethane Co., Ltd.) was added in an amount of 1 part by weight based on the solid content of the obtained graft polymer solution. The adhesive composition-1 having a solid concentration of 35% by weight was prepared. &lt;Preparation Example 3 (Preparation of Adhesive Composition-2)&gt; In Preparation Example 2, except that 40 parts of 2-ethylhexyl acrylate, 50 parts of vinyl acetate, and 1 part by weight of acrylic acid were used as a monomer The rest of the procedure was carried out in the same manner as in Preparation Example 2 to prepare the adhesive composition-2. &lt;Preparation Example 4 (Preparation of hard coat layer forming agent)&gt; 100 parts of ethyl urethane acrylate obtained from pentaerythritol-based propylene acrylate and water-added xylene diisocyanate, isocyanuric acid-parameter [2_(propylene) 20 parts of decyloxy)ethyl], 40% by weight of oxidized sand particles having an average particle diameter of 1 to 3 μm for the total solid content, and 1-hydroxycyclohexylphenyl group as a photopolymerization initiator for the total solid content The ketone was 3% by weight, and was diluted with a mixed solvent of butyl acetate/methyl-50-200844511 (ethyl ketone (weight ratio of 1/2) to a solid content concentration of 45% by weight to prepare a hard coat layer forming agent. &lt;Example 1&gt; The adhesive obtained in Preparation Example 1 was applied to both surfaces of the polarizing film obtained in Production Example 4 at a thickness of 1 μm to form a film (a) / a polarizing film / a film (b) The laminate was laminated with a norbornene-based resin film β1/polarizing film/norbornhoid-based resin film-2. In addition, the hard coat material obtained in Preparation Example 4 was applied to the surface of the film of the norbornene-based resin film-1 which is on the opposite side to the polarizing film, by 1 〇〇. Heating 1 minute to dry the coating film' Then, irradiating the ultraviolet light with a total amount of light of 300 mJ/cm2 with a complex metal lamp to form a hard coating layer of 3 μη thick. Thereafter, a norbornene-based resin film corresponding to the film (b) (2) The adhesive composition-1 obtained in Preparation Example 2 was applied to the surface opposite to the polarizing film and dried, and then the adhesive layer was laminated. Thus, a polarizing plate was produced. Norbornene-based resin film-1 The physical properties of the norbornene-based resin film _2 are shown in Table 1 ', and the degree of polarization of the polarizing plate and various test results are shown in Table 2. <Example 2 &gt; Polarized light obtained in Production Example 4 On both surfaces of the film, the adhesive agent obtained in Preparation Example 1 was produced in the same manner as in Example i except that the film was laminated in the form of norbornene-based resin film-1/polarizing film/norbornene-based resin film_1. The polarizing plate. The polarizing degree of the polarizing plate and various test results are shown in Table 2. -5 1 - 200844511 &lt;Example 3&gt; The adhesive obtained in Preparation Example 1 was passed through both sides of the polarizing film obtained in Production Example 4 except for the norbornene-based resin film-2/polarizing film/norbornene-based resin film- A polarizing plate was produced in the same manner as in Example 1 except that the lamination was carried out in the same manner as in Example 2. The polarizing degrees of the polarizing plates and various test results are shown in Table 2. &lt;Example 4&gt; The adhesive obtained in Preparation Example 1 was passed through both sides of the polarizing film obtained in Production Example 4 except for the norbornene-based resin film-1 / polarizing film / norbornene-based resin film - A polarizing plate was produced in the same manner as in Example 1 except that the lamination was carried out in the same manner as in Example 3. The polarizing degrees of the polarizing plates and various test results are shown in Table 2. &lt;Comparative Example 1&gt; A norbornene resin film in which the polarizing plate produced in Example 1 was replaced with a cellulose triacetate film (hereinafter referred to as "TAC film") having a thickness of 40 μm, which was made of cellulose triacetate, was used. A polarizing plate was produced in the same manner as in Example 1 except for 1. The various physical properties of the T A C film are shown in Table 1 ' and the polarization of the polarizing plate and various test results are shown in Table 2. &lt;Comparative Example 2&gt; A polarizing plate was produced in the same manner as in Example 2, except that a - AC film of -52-200844511 norbornene resin film-1 was used instead of the polarizing plate produced in Example 2. The polarizing degrees of the polarizing plates and various test results are shown in Table 2. &lt;Comparative Example 3&gt; A polarizing plate was produced in the same manner as in Example 1 except that the adhesive composition-2 was used instead of the adhesive composition-1. The degree of polarization of the polarizing plate and various test results are shown in Table 2. [Table 1] ^ Film-1 Film-2 Film-3 TAC film Moisture permeability g_25pm/m2-24hr 75 75 75 700 Water absorption % 0.2 0.2 0.2 4.0 Transmittance Γ380ηιη1(%) 2 91 2 5 [Table 2]

Example 1 Example 2 Example 3 Example 4 Comparative Example 1 Comparative Example 2 Comparative Example 3 Film (a) 1 1 2 1 TAC TAC 1 (b) 2 1 2 3 2 TAC 2 Water absorption (%) 1.9 2.0 1.9 1.9 2.7 3.4 1.9 Polarization 99.99 99.99 99.99 99.99 99.99 99.99 99.99 Damp heat test AAAACCA Dry heat test AAAAAAA UV resistance test AABAAAA adhesive Adhesive peeling AAAAAAC Foaming AAAAAAB &lt;Production Example 5 &gt; [Norbornene resin film -4 - 200844511 Using a 2-axis extruder" relative to 100 parts of the norbornene-based resin obtained in the synthesis example, (pentaerythritol-yl-3-(3,5-di-t-butyl) 4-[4-hydroxyphenyl)propionate: melting point 1 1 5 °C) 〇. 3 parts with benzotriazole compound (2,2'-methylene bis[4-(1,1,353-four) Methyl butyl)-6-(211-benzotriazol-2-yl)phenol) · melting point 199 ° C) 1.5 parts melt-kneaded at 270 ° C, extruded on a strand, cooled with water After that, a small ball was obtained by a feeder ruder. The obtained pellets were subjected to cyclic dehumidification drying at 10 ° C for 3 hours under nitrogen, and then transferred to a hopper using a uniaxial extruder having a screw diameter of 75 mmp at a resin temperature. It was melted at 270 °C. The molten resin was introduced into a 700 mm wide coat hanger die by a two-shaft discharge type gear pump at a ratio of 30 kg/hr through a polymer filter (pore size 5 μm) heated to 28 (TC). The pressure difference between the inlet and outlet is 3 MP a. In addition, the heater of the die is made of aluminum cast heater, set to 250 °C, and the front tip lip is also provided with a lip heater to control the die. The tip lip temperature is 250 ± 0.4 ° C. The lip tip opening degree is set in the width direction 〇. 5 mm 'micro adjustment system on the melt extrusion outflow side set on the line thickness gauge to determine the thickness unevenness. The extruded resin is pressed into the vertical wiring direction of the casting roll of 25 Ommcp (surface roughness: 0. 1 #), and the two cooling rolls which are horizontally disposed on the winding roll axis are sequentially pressed and peeled off. 'Removed under a tension of 4 kgf to obtain a norbornene resin film-4 having a thickness of 80 // m. -54- 200844511 &lt;Production Example 6 &gt; [Production of norbornene-based resin film-5 〕 After the norbornene-based resin film-4 is heated to 145 ° C, the vertical axis is extended. The stretched film (norbornene-based resin film-5) was obtained by a factor of 1. 3, and the obtained norbornene-based resin film-5 had a thickness of 70 μm and a total light transmittance of 93%, and was used by the prince measuring machine. The "KOBRA-21ADH" measured by the "KOBRA-21ADH" has a phase difference of 141 nm at a wavelength of 590 nm. [Production Example 7 &gt; [Preparation of norbornene-based resin film-6] Except that a benzotriazole-based compound is not used, In the same manner as in Example 5, a norbornene-based resin film-6 having a thickness of 80 μm was obtained. <Production Example 8 &gt; [Preparation of norbornene-based resin film-7] The norbornene-based resin film-6 was heated to After 145 ° C, the longitudinal axis was extended by 1.3 times to obtain a stretched film (norbornene-based resin film-7). The obtained norbornene-based resin film-7 had a thickness of 70 μm and a total light transmittance. 93%, "KOBRA-2 1 ADH" manufactured by Oji Scientific Instruments Co., Ltd. has a phase difference of 145 nm at a wavelength of 5 90 nm. &lt;Preparation Example 5 (Modulation of Adhesive Composition 3)&gt; 206 parts of acetone, 210 parts of butyl acrylate and 1.2 parts of acrylic acid were placed in place of nitrogen In the reaction vessel, after the solution is heated to 5 5 ° C, add -55-200844511 to dissolve 2,2 '-azobis(2,4-dimethylvaleronitrile) 0.0 2 1 part as a starter 5 parts of acetone solution. At this time, the concentration of the monomer was 5 Ο %. After stirring for 1 hour, the acetone was dropped for 8 hours at a temperature of 55 ° C to make the monomer concentration of 35 %. Thereafter, after stirring at a reaction temperature of 5 5 ° C for 3 hours, ethyl acetate was added to prepare a monomer concentration to 20%. The obtained polymer solution had a viscosity of 1,800 mPa·s, and the polymer had a weight average molecular weight of about 1,570,000 in terms of polystyrene of GPC. To 100 parts of the solid content of the obtained polymer solution, 4 parts of an isocyanate crosslinking agent and 4 parts of a decane coupling agent were added, and the mixture was sufficiently stirred and defoamed to obtain an adhesive composition 3. The obtained adhesive composition 3 was applied to a release-treated polyethylene terephthalate film (manufactured by LINTEC Co., Ltd.) with a thickness of 25 μm after drying using an applicator (app 1 icat 〇r ). The release name of the product name: ΡΕΤ381 1 ) was then dried at 90 ° C for 1 minute to obtain an adhesive sheet. &lt;Preparation Example 6 (Preparation of Adhesive Composition 4)&gt; A polymer solution was obtained in the same manner as in Preparation Example 5 except that the amount of the initiator added was 0.14 8 parts. The obtained polymer solution had a viscosity of 1,95 mPa·s, and a weight average molecular weight of about 780,000 ° in terms of polystyrene of GPC. In the obtained polymer solution, an isocyanate-based parent-linked agent and sand were added in the same manner as in Preparation Example 5. The hospital coupling agent was thoroughly stirred and defoamed to obtain an adhesive composition 4. Using the obtained adhesive composition 4, the adhesive sheet was obtained in the same manner as in Preparation Example 5. -56-200844511 &lt;Examples 5 to 10, Comparative Examples 4 to 5 &gt; On both surfaces of the polarizing film obtained in Production Example 4, the film obtained in Preparation Example 1 was passed through the film obtained in Preparation Example 1 The film (a) / polarizing film / film (b) was combined as shown in Table 3. In the film X in the table, a cellulose resin film "TDY80uL" manufactured by Fuji Film Co., Ltd. was used. The film X had a moisture permeability of 700 (g·25 μm/m 2⁄2 • 2 4 hr) and a thickness of 80 μm. The monomer transmittance and the degree of polarization of the obtained polarizing plate are shown in Table 3. On the surface of the film (b) of the polarizing film, the adhesive surface of the adhesive sheet obtained in Preparation Example 5 or 6 was bonded by a plate maker, and then aged at 23 ° C x 6 5 % for 7 days. A polarizing plate with an adhesive layer. The obtained polarizing plate was subjected to the damp heat test 2, the dry heat test 2, and the UV resistance test 2 under the following conditions, and the measurement of the degree of polarization and the presence or absence of the peeling of the adhesive layer were visually evaluated. The degree of polarization was evaluated by the following reference (1) by the amount of change in the degree of polarization before and after the endurance test shown by the following formula. Further, the floating peeling of the adhesive layer was evaluated by the following criteria (2). The results are shown in Table 3. &lt;Damp heat test 2 &gt; After bonding a polarizing plate having an adhesive layer to a glass for LCD, 'evaluation was carried out for 500 hours in an environment of a temperature of 85 ° C and a relative humidity of 85 % -57-200844511 &lt; Dry heat test 2 &gt; After bonding a polarizing plate having an adhesive layer to the glass for LCD, it was stored in an environment of 95 ° C for 500 hours and then evaluated. &lt;UV-resistant test 2&gt; After the polarizing plate having the adhesive layer was bonded to the glass for LCD, 'the upper surface of the polarizing plate (the surface of the film (a) below) was used for fading by SUGA Tester Co., Ltd. The test machine was evaluated by irradiating ultraviolet rays for 1,000 hours by a graphite arc lamp. "Base (1)" 〇: The amount of change in the degree of polarization is less than 0.5% △: The amount of change in the degree of polarization is less than 5% in 〇.5% or more. X: The amount of change in the degree of polarization is 2.0% or more. The amount of change] = (1 - [polarity after test] / [initial polarization]) xl 〇〇 (%) "Standard (2)" 〇 · · No floating, peeling, foaming △ on the adhesive layer : From the end of the adhesive layer to the inside of the surface, 1 to 2 floats, peeling, and foaming can be found. X: 3 or more floats, peeling, and foaming can be found on the adhesive layer. -58- 200844511 [Table 3]

Comparative Example 5 6 7 8 9 10 4 5 Polarized plate layer constitutes a thin position a) 4 4 4 4 6 4 6 X Film (b) 4 5 6 7 6 4 XX Adhesive 3 3 3 3 3 4 3 3 Initial characteristic monomer transmittance 41.2 41.0 41.6 41.4 41.5 41.4 41.6 41.7 Polarization 99.99 99.99 99.99 99.99 99.99 99.99 99.99 99.99 Adhesive layer damp heat test 2 Reference (1) 〇〇〇〇〇〇Δ X Reference (2 〇〇〇〇〇Δ XX Dry heat test 2 Reference (1) 〇〇〇〇〇〇〇〇Standard (2) 〇〇〇〇〇Δ XX Resistance to UY Test 2 Reference (1) 〇〇〇〇X 〇XX Reference (2) 〇〇〇〇〇〇XX -59 -

Claims (1)

200844511 X. Patent Application No. 1 · A polarizing plate characterized in that a norbornene-based resin film (a) and a norbornene-based resin film (b) are laminated on both sides of a polarizing film through an adhesive layer, wherein The norbornene-based resin film (b) is on the surface opposite to the polarizing film, and has an adhesive layer containing a polymer derived from an alkyl (meth) acrylate. 2. The polarizing plate of claim 1, wherein the norbornene-based resin film (a) is on the surface opposite to the polarizing film, and has a hard coat layer directly or through another layer. 3. The polarizing plate of the first aspect of the invention, wherein the norbornene-based resin film is obtained by (co)polymerizing a monomer containing at least one compound represented by the following formula (1). Norbornene-based resin film formed from borneol-based resin; [Chemical 1] R1 (In the formula (1), R1 to R4 each independently represent a hydrogen atom, a halogen atom, or a monovalent group which may contain oxygen, nitrogen, sulfur or hydrazine; R1 and R2, or R3 and R4 may bond each other to form a sub- An alkyl group, or R1 and R2, R3 and R4, or R2 and R3 may be bonded to each other to form a monocyclic or polycyclic carbocyclic or heterocyclic ring; -60- 200844511 X represents an integer of 〇 or 1-3, y represents 0 or 1). 4. The polarizing plate of claim 1, wherein the adhesive layer has at least one polymer derived from a hospital (meth) acrylate represented by the following formula (i); CH2 II CRCOROR, . (1) (In the formula (i), R represents a hydrogen atom or a methyl group; and R' represents an alkyl group having 1 to 12 carbon atoms). 5. The polarizing plate of claim 1, wherein the polymer derived from the alkyl (meth) acrylate is a polymer having a weight average molecular weight of 1,500,000 or more in terms of colloidal permeation chromatography. . 6. The polarizing plate of claim 1, wherein at least one of the norbornene-based resin films contains an ultraviolet absorber. 7. The polarizing plate of claim 1, wherein the hard coat layer contains fine particles. 8. The polarizing plate of claim 1, wherein the norbornene resin film satisfies the moisture permeability of 300 (g · 25 μmη / m2 · 24 hr) or less, the water absorption rate of 1.0% by weight or less, and the transmittance of 90%. the above. 9. The polarizing plate of claim 1, wherein the polarizing film is made of a polyvinyl alcohol-based resin, and the water absorption of the polarizing film is 20% by weight or less. 10. The polarizing plate of claim 1, wherein the norbornene-based resin film is a retardation film. -61 - 200844511 For the diagrams of the map elements, the map refers to the table: the representative map of the case, ', and the set one and two ^ ((7, Wu Ming said single eight, if the case has a chemical formula, please reveal the most able to show the characteristics of the invention Chemical formula 1