TW201038681A - Polarizing plate having a silicone coated hardened film and a liquid crystal display device - Google Patents

Abstract

This invention provides a polarizing plate having a polarizing element protected by a protection film on at least one side of the polarizing element, the protection film being formed by a coated, hardened film of a curable resin composition which contains a silicone resin (A), the silicone resin (A) having, as a main component, a polyorganosilsesquioxane represented by formula (1) and having a cage type construction in the construction unit, [RSiO3/2]n (1) wherein R is an organic functional group having a (metha) aryloyl group, n is 8, 10 or 12. The polarizing plate of this invention exhibits excellent durability against humidity and heat, adherence, optical stability, process capability and surface hardness. By using the polarizing plate of this invention the display quality of such display devices as a liquid crystal projector and an automotive display unit can be improved and a stable graphic display can be maintained.

Description

[Technical Field] The present invention relates to a polarizing plate having a novel coating-cured film and a liquid crystal display using the same, and a manufacturing method thereof. [Prior Art] Generally, when a polarizing element (photo-polarizer) is produced, iodine or a dichroic dye of a dichroic dye is adsorbed and aligned in a polyvinyl alcohol (hereinafter abbreviated as PVA) resin, and then uniaxially It is obtained after stretching. In order to improve the strength, water resistance, moisture resistance, and the like, a cellulose triacetate (hereinafter referred to as TAC) may be used (the film formed as a support film and/or a protective film is bonded to the polarizing film via an adhesive layer). A polarizing plate formed on at least one side of the element is used in a liquid crystal display or the like. TAC has high light transmittance and low birefringence, so it can be applied to optical applications, and at the same time, it can be easily treated by alkali. In addition to the PVA-based resin, it is also advantageous for processing. Therefore, TAC has been widely used as a protective film for polarizing elements. However, due to the high moisture permeability of TAC, it may be degraded when used under high temperature and humidity conditions. In particular, when the thickness of the TAC film is made thinner, I will change the transmittance of light of the polarizing plate and polarized light in the environmental degradation test of the polarizing plate, especially in the durability test under the conditions of high temperature and high humidity. In order to solve such problems due to TAC, in the literature represented by Patent Documents 1 to 4, the use of an olefin film (cycloolefin) has been developed. Membrane A film made of an acrylic resin, a film made of an acrylic resin, or a film other than TAC such as a vinyl ester film is used as a polarizing plate of a protective film. 4 321811 201038681 Meanwhile, a film other than TAC has been disclosed regarding a # resin film. Invention (Patent Document 5). The adhesion between the other resin films of the type hc0ne) is poor. ^In the month of the invention, the technique of the material and the material element is followed by a technique of forming a dream on the side of the back side of the acid-removing film::: C: a technique in which a PVA-based adhesive and a polarizing element are used. No: Ο Ο :=Adhesion, damp heat durability and productivity requirements, the latter period: On the other hand, also on the thinning of the patent documents 6 to 9 t plate and the improvement of the durability of the material plate f on the polarized light P Human and β six supply, by 'not to make the film Vi such as: the right side of the coated energy line polymerizable compound 1 == (meth)acrylic monomer and photocurable prepolymer (A very ΓΓ = 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 A hard j-tree having a ruthenium-containing energy ray-polymerizable compound such as a bicyclic ring, a ruthenium group or a pentylene group, is disclosed in the patent document 8). After coating, it is hard to obtain a protective layer. A light plate which satisfies the requirements of adhesion or durability; and when it has a protective layer formed by only polymerizing and curing the energy ray polymerizable compound disclosed by the above, it is caused by the resin and composition of the protective layer. The wet heat durability of the polarizing plate is insufficient. [Prior Art Document] [Patent Document 1] Japanese Laid-Open Patent Publication No. 2007-316603 [Patent Document 2] Japanese Patent Application Laid-Open No. Hei 2 〇〇 8 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [Patent Document 5] WO 2008/066157 A1 [Patent Document 6] JP-A-2007-334307 [Patent Document 7] JP-A-2005-107238 [Patent Document 8] JP-A-2003-185842 [Patent Literature] 9] Japanese Laid-Open Patent Publication No. 2004-77579 [Problem to be Solved by the Invention] An object of the present invention is to improve a protective film of a polarizing element, in addition to achieving thin film formation of a protective film, and simultaneously improving a polarizing element and a protective film. Inter-adhesiveness' is a polarizing plate that achieves durability, especially improved wet heat durability. [Means for Solving the Problem] The inventors of the present invention have concentrated their efforts to solve the above problems. The results have been found to consist of a curable resin containing a compound resin having a specific silse Squi〇xane structure. When the coating cured film of the article is used as a protective film for a polarizing element, the adhesion of the cured film can be improved, and the light transmittance and the degree of polarization can be obtained even if it is used for a long period of time under both wet and high temperature conditions. The present invention is completed by a polarizing plate having stable optical characteristics. That is, the present invention relates to: (1) a polarizing plate ❺ having a curable resin group cut on one side or both sides of a polarizing element, and the present invention contains a formula (1) and In the structural single", the polyorganopyquid as the main component having a cage structure is cut as a main component, the fat (1) is 5 to 80% by weight, and the radical is 321811 6 201038681. The polymerizable unsaturated compound is 95 to 20% by weight, [RS i 〇 3/2] η (1) (wherein R is an organic functional group having a (meth)acryl fluorenyl group, and η is 8, 10 or 12); (2) a polarizing plate according to (1) above, wherein The content of the polyorganosilsesquioxane having a cage structure is 50 to 100% by weight based on the total amount of the fluorenone resin (Α); (3) The polarizing plate of the above (1) or (2), characterized The curable resin group composition contains (i) an anthrone resin (Α), and (ii) an oligomer having an amino phthalic acid ester bond capable of radical polymerization with an anthrone resin (Α) (B) (4) The polarizing plate according to (3) above, characterized in that the curable resin composition is a radical polymerizable unsaturated compound , in addition to the (iii) oligomer (B), and containing an unsaturated compound (C) copolymerizable with the fluorenone resin (A); 〇 (5) as in the polarizing plate of the above (4), Wherein the unsaturated compound (C) is an alicyclic di(meth)acrylate (C') represented by the following formula (2),

(wherein Z represents any one of (2a) or (2b), R' represents a hydrogen atom or 7 321811 201038681 fluorenyl); (6) as in any one of the above (3) to (5) The polarizing plate is characterized in that the polymer (B) contains at least one -r3-CR4 = CEh or -CR4 = CH2 in the molecule (wherein R represents an aliphatic carbon number of 1 to 6 of a divalent crosslinking group or - 〇C〇- group, R4 represents a hydrogen atom or a C1 to C6 alkyl group) and the number average molecular weight is 1, 〇〇〇 to 1〇, 〇〇〇 compound; (7) as above ( The polarizing plate according to any one of (4), which is characterized in that the dreaming I resin (a), the oligomer (B) and the mass are contained in a weight ratio of 5 to 80. 1 to 50: 10 to 80. (8) The polarizing plate according to any one of the above (1) to (7), which is characterized in that it has a curable resin composition on the surface of the polarizing element subjected to the treatment (9) The polarizing plate according to (8) above, wherein the decane coupling agent for the decane coupling treatment is a (fluorenyl)acrylic decane coupling agent; (10) as described in (1) above. (9) Any of them The polarizing plate is characterized in that: the polarizing element is formed of a polyvinyl alcohol-based resin film containing a dichroic dye; (11) The polarizing plate according to any one of the above (1) to (10), characterized in that: a cured film having a curable resin composition on one side of the element, and a laminated body on the other side; (12) The polarizing plate according to (11) above, wherein the support is a TAC or a ring-smoke polymer (13) A liquid crystal display comprising: the polarizing plate according to any one of (1) to (12) above; (14) the liquid crystal display according to (13) above, which is two In the above (11), the polarizer 321811 201038681 is placed on both sides of the liquid crystal cell, and is formed by the liquid crystal cell, and the hardened film of the fat composition becomes the outer side; (15) a curable resin composition, Containing: (i) an fluorenone resin (A) having a cage structure and having a cage structure in a structural unit as a main component of a polyorganosilsesquioxane, (ii) and an anthranone resin (A) a radically polymerized urethane bond having a number average molecular weight of 1,000 to 10,000 Polymer (B), q (iii), in addition to the above-mentioned polymer (B), an unsaturated compound (C) and (iv) photopolymerization initiator which can be copolymerized with the cerium-resin (A) radical. Wherein the total amount (by weight) of the second resin (A), the oligomer (B) and the unsaturated compound (C) is such that the content of the compound is from 1 to 55 by weight of the ketone resin (A) %, the oligomer (B) is 3 to 30% by weight, and the residual portion is an unsaturated compound (C), and the total amount (weight) of the photopolymerization initiator relative to the above (... to ^) is 1 to 6% by weight, [RSi〇3/2]n (1) (wherein R is an organic functional group having a (fluorenyl) acrylonitrile group, and η is 8, U or 12); (16) as described above And a curable resin composition of the formula (C), wherein at least 10% by weight of the formula (2) represented by the following formula (2) is used as the non-saturated compound (C) Saturated compound (c) ' 9 321811 (2) 201038681

(wherein, Z represents a group represented by (2a) or (2b), and R' represents a ruthenium atom or a methyl group); (17) A curable resin composition as described in (16) above, wherein the unsaturated compound ( C) is an alicyclic bis(indenyl) acrylate (C') represented by the formula (2) alone, or the alicyclic di(meth) acrylate (C') and an aliphatic polyfunctional group (fluorenyl group) ) Acrylic acid is used in combination. [Effects of the Invention] When the cured film of the curable resin composition of the present invention is used as a protective film for a polarizing element, even when the cured film is a thin coating film, the polarizing plate using the cured film as a protective film It can exhibit excellent heat and humidity resistance, and the adhesion between the protective film and the polarizing element is also good. Therefore, even if the polarizing plate is used for a long period of time under high humidity and heat conditions, the physical change such as shrinkage is small, the transmittance of light and the change in the degree of polarization are small, and the problem of adhesion is not caused. Therefore, the characteristics of the polarizing plate are long-term use which can be stabilized under severe conditions, and the polarizing plate is excellent in durability under severe conditions. At the same time, when the protective film is formed of a coating film, it is possible to omit the step of bonding the protective film, and to reduce the thickness of the adhesive without requiring an adhesive, and to grow it in comparison with the conventional protective film. On the occasion of the article, it also has the effect of easy 10 321811 201038681 curling into a wheel. Therefore, the polarizing plate of the present invention is easy to manufacture, and can be made to have a film thickness of the protective film, and the surface hardness, the heat and humidity resistance, and the effect of improving the display spot are excellent. The polarizing plate of the present invention can be used particularly as a liquid crystal projector having a durability requirement or a polarizing plate for a vehicle. [Embodiment] [Embodiment for Carrying Out the Invention] Hereinafter, the present invention will be described in detail. The polarizing plate of the present invention is characterized in that a coating cured film containing a curable resin composition of a specific fluorenone resin (A) is used as a protective film (or a support) of a polarizing element. Further, the coating cured film in the present specification means a film (or layer) obtained by hardening a coating film (or a coating layer). The polarizing plate of the present invention may be formed on both sides or on either side of the polarizing element and preferably as a surface-treated surface, and after coating the resin composition to form a coating film, the coating film is cured and cured. . Therefore, the coating cured film is usually directly adhered to the surface of the polarizing element without interposing the adhesive layer and other resin layers between the surface of the polarizing element 。. Meanwhile, "directly attached to the surface of the polarizing element" in the present specification means that the surface of the coating cured film and the surface of the polarizing element are not adhered to the adhesive layer and other resin layers, and the coating is also included. The cured film is directly attached to the surface of the surface-modified polarizing element. The coating cured film of the present invention may optionally have another resin layer interposed between the surface of the polarizing element and the surface of the polarizing element, and it is usually preferred to directly adhere to the surface of the polarizing element without interposing such a layer. The indole ketone resin (A) having a cage structure of a polyorganosilsesquioxane as a main component of the formula (1), which is used in the present invention, is represented by the following formula (1), and is based on WO 2004/085501A1. It is revealed that it can be easily obtained by the same industry. The curable resin composition used in the polarizing plate of the present invention is characterized by the following, which comprises a cetyl ketone resin (A) having a cage structure and a polyorganose sesquiterpene-oxygen group as a main component in a structural unit and radical polymerization. Sexually unsaturated compounds. More specifically, a curable resin composition contains (0) an anthrone resin (A) represented by the general formula (1) and having a polyorganosilsesquioxane having a cage structure as a main component in a structural unit ( Hereinafter, also referred to as an fluorenone resin (A)) of 5 to 80% by weight, and a radical polymerizable unsaturated compound of 95 to 20% by weight, [RS i 〇3/2] η (1 ) (wherein, R It is an organic functional group having a (fluorenyl) acrylonitrile group, and η is 8, 10 or 12). The radically polymerizable unsaturated compound may be used singly or in combination of two or more kinds. One of the desirable radically polymerizable unsaturated compounds may, for example, be an oligomer which is copolymerizable with the above fluorenone resin (fluorene) radical and has a urethane bond having a number average molecular weight of 1,000 or more ( Β) (hereinafter, also referred to as an oligomer (Β) or an amino phthalic acid 寡 oligomer), in a radically polymerizable unsaturated compound, an amino phthalate oligomer (Β) The content is usually in the range of 1 to 50% by weight. The urethane oligomer (Β) is contained in the above range. In the case of one of the radically polymerizable unsaturated compounds, the curable resin composition contains, in addition to the 12,321,811,201038681, the amino carboxylic acid vinegar oligomer (8), the residual portion thereof contains the succinyl ketone resin (1) radical a polymerized unsaturated compound (c) (hereinafter, 'also referred to as an unsaturated compound (c)). When the curable resin composition contains the above three compounds, the lithium resin (4), the polymer (8) The content of the unsaturated compound (6) is preferably a weight ratio of 5 to 80:1 to 50:10. The polarizing plate having a cured film having a curable resin composition containing the three kinds of the chemical substances is more preferable. The curable resin composition used in the present invention may contain any additives other than the above-mentioned three kinds of materials. It is usually preferred to use the above three components as the main component. The polarizing plate of the present invention is in the polarizing element. After coating the surface of the curable resin composition on the surface, it is obtained by subjecting it to radical polymerization by irradiation with an energy source such as light (for example, ultraviolet rays) to form a cured film. The coating is preferably straight. Coating on the surface of the polarizing element (including the decane coupling treatment surface), the cured film (or hardened layer) after curing is directly attached to the surface of the polarizing element. The "principal component" referred to in the present invention is relative to In the case where the total amount is at least 5% by weight or more, it is preferably 7% by weight or more, and "%" means % by weight unless otherwise noted. _ Anthrone resin (A used in the present invention) Included in the above formula (1): a cage-type oxirane containing a polyorganosilsesquioxane having a cage structure (also, a caged siloxane) as a main component in a structural unit 6〇至95重量义' and the residual part is a non-quinone type of alkaloid resin component. In the formula (1), 'R is an organic functional group having a (meth)acryloyl group, 13 321811 201038681 ideal R Can be cited

(Methyl) 3⁄4-alkenyloxy group represented by the following formula (4) (4) In the formula (4), 'm is j, and the formula (4) may be an integer R1疋 nitrogen atom or a methyl group. Also T is represented by CH2HC00-(CH2)m. Specific examples of the desired β include, for example, *3-methacryloxypropylpropyl, methacryloyloxymethyl and 3-propenyloxypropyl. The sylvestre sylvestre (A) has the above-mentioned organic functional group on the Shi Xi atom in the molecule. The specific structure of the cage-type polyorganic halve-bonded nucleus of 8, (1) or 12 in the above formula (1) includes the following structural formulas (5), (6) and the cage structure represented by Ό (also It can be referred to as T8, T10, and 12), respectively. Meanwhile, R in the following formula is the same as R in the formula (1). RSi-〇1

*0-SiR RSi· Ο

10—....... SiR Ο

I I (5) R&*-〇-l——SiR %, RS one—

0 0-SiR 321811 14 201038681

The fluorenone resin (A) used in the present invention can be produced by the method described in WO 2004/085501 A1 or the like. That is, the fluorenone resin (A) can be obtained by a method in which RSiX3 (wherein R is an organic functional group having a (fluorenyl) acrylonitrile group, and X represents a hydrolyzable group), in a polar solvent In the presence of an inert catalyst, the hydrolysis reaction is simultaneously caused to shrink, and the resulting hydrolyzed condensation product is obtained by recondensing in a non-polar solvent in the presence of a basic catalyst. The hydrolyzable group X is not particularly limited as long as it is a hydrolyzable group, and examples thereof include an alkoxy group, an ethoxy group, a chlorine atom and the like, and an alkoxy group is preferred. The alkoxy group may, for example, be an anthracenyloxy group, an ethoxy group, a n- and an iso-propoxy group, or a n-, iso- and a third butoxy group. Among them, the reactivity of the decyloxy group is high. 15 321811 201038681 To point out the ideal compound among the ruthenium compounds represented by RSiX3, methacryloxymethyltriethoxy decane, methacryloxymethyl decyltrimethoxy sulphate, and 3 - mercaptopropyl oxypropyl trichloromethane, 3-mercapto propylene methoxy propyl trimethoxy decane, 3-mercapto propylene methoxy propyl triethoxy oxime, 3 - propylene methoxy propyl trimethoxy oxalate and 3- propyl methoxy propyl trichloride. Among them, 3-methylpropenyloxypropyltrimethoxy-oxygen is readily available as a raw material. As the organic catalyst which can be used for the hydrolysis reaction, for example, an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide or hydroxide can be used, or tetradecyl hydroxide, tetraethylammonium hydroxide or tetrabutylate. An ammonium hydroxide salt such as ammonium hydroxide, benzyltrimethylammonium hydroxide or benzoyltriethylammonium hydroxide. Among these salts, tetrakisyl ammonium hydroxide is suitable for high catalytic activity. Alkaline catalysts are generally used as an aqueous solution. As for the hydrolysis reaction conditions, the reaction temperature is preferably from 〇 to 60 ° C ' and preferably from 20 to 40 ° C. If the reaction temperature is lower than 〇. In the case of hydrazine, the reaction rate is slowed, and the hydrolyzable group remains in an unreacted state, resulting in a reaction time which is too much. On the other hand, if it is higher than 6 (TC), the reaction speed is too fast to carry out a complicated condensation reaction, and as a result, the hydrolyzation condensation product is promoted to be high molecular weight. Meanwhile, the reaction time is preferably 2 hours or more. For 2 hours, the hydrolysis reaction will not proceed sufficiently, so that the hydrolyzed group remains in an unreacted state. In the hydrolysis reaction, water is necessary to be present. This can be supplied by an aqueous solution of an organic catalyst, or water can be additionally added. It is sufficient to hydrolyze the hydrolyzable group, and it is preferably a theoretical amount of 1.0 to 1.5 times. In addition, 321811 16 201038681 must use an organic polar solvent during hydrolysis, and can be used on an organic polar solvent. An alcohol such as methanol, ethanol or 2-propanol, or another organic polar solvent. It is preferred to use a lower alcohol having a carbon number of 1 to 6 which is soluble in water and to use 2-propanol. When a non-polar solvent is used, the reaction cannot be carried out due to the reaction, so that the hydrolysis reaction does not proceed sufficiently, and the unreacted alkoxy group remains, which is not preferable. After the hydrolysis reaction is completed, the water or the water must be reversed. Solvent separation. Separation of water or aqueous reaction solvent, f is carried out by means of reduced bulk evaporation, etc. In order to make the reaction product obtained by removing the solvent more sufficient to remove moisture or other impurities, a non-polar solvent may be added to dissolve the solvent. After the reaction product, the solution is washed with a saline solution or the like, and then dried by a drying agent such as anhydrous magnesium sulfate. The non-polar solvent can be separated from the thus obtained solution by evaporation or the like. The desired reaction product is recovered. However, 'as long as the non-polar solvent can be used as the solvent in the next reaction', there is no need for such separation. - In the surface reaction, a condensation reaction of the hydrolyzate is produced together with the hydrolysis. The accompanying reaction in the hydrolysis is usually a colorless viscous liquid which is formed in a quantity of two to two, GGG. The hydrolysis is limited to four (4) conditions, and the number average molecular weight is 1, and it is replaced by ' 〇 = Λ ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' There are not many ratios. There are cages: the compound of the structure is finished and the part of the compound is opened. It is not the 321811 17 201038681. The cage structure of the king is the main one. Therefore, the hydrolysis condensation product obtained by hydrolysis, Further, the sesquioxane of the cage structure can be selectively produced by heating in an organic solvent to heat the oxirane bond (referred to as recondensation) in the presence of a basic catalyst. After the separation of the agent, the above-mentioned recondensation reaction is carried out in the presence of a non-polar solvent and an inert catalyst. As for the reaction conditions of the recondensation reaction, the reaction temperature is preferably in the range of 100 to 200 ° C, and is 11 to 140. At the same time, when the reaction temperature is too low, sufficient driving force (drivingf〇rce) cannot be obtained to carry out the recondensation reaction, and the reaction cannot be carried out. If the reaction temperature is too high, it is necessary to cause the (mercapto) acrylonitrile group to cause auto-polymerization. Therefore, it is necessary to suppress the reaction temperature, or to add a polymerization inhibition reaction, etc., for 4 to 12 hours. The amount of the nonpolar solvent used may be any amount as long as it is sufficient to dissolve the hydrolysis reaction product. The amount of the alkaline catalyst used relative to the hydrolyzed shrinkage product is in the range of 〇.丨 to wt%. A non-polar solvent is a solvent which is insoluble or almost insoluble with water. It is generally preferred to be a hydrocarbon solvent. The hydrocarbon solvent is preferably a non-polar solvent such as toluene, benzene or xylene, and is preferably a toluene. As for the catalyst, the tester used in the hydrolysis reaction towel can be used. The catalyzed catalyst may be a metallurgical compound such as hydrogen hydroxide, oxyhydrogen, or cesium hydroxide, or tetradecyl hydroxepide, tetraethylammonium hydroxide, tetrakisperyl hydroxide, or methyl. Trimethyl hydroxide bond and stupid methyl triethyl chloride and other salts. Among them, a catalyst which is soluble in a non-polar bath such as tetrazolium is preferable. At the same time, in the recondensation, (4) the condensed product is cut, although it is preferable to use 321811 18 201038681 to be washed, dehydrated, and sprinkled. #& _ ,,, but can also be used without washing or dehydrating. At the time of this reaction, although the water is added to the muscles, it can be retained by the alkali (4): water is present, but it is not necessary to actively and simultaneously, if the water brought in by the solution is not sufficiently carried out. S often =: the base must be hydrolyzed above the theoretical amount, but == the water brought in by the liquid, you can fully carry out the water Ο after the conclusion of the second, after the 'catalyze the water to wash *, then you can The sesquiterpene oxide obtained by the sputum. Human 4:: and 2 times hemi-haloxane, although it may be different due to reaction conditions or hydrolysis (four) sorrow 'but the composition is several times the number of cages = 5% or more of the total, usually Miscellaneous, the rest of the two 曰 1 dragon type condensate. Several kinds of sesium type sesquioxanes are composed of: 疋 "the enthalpy 8 represented by the general formula (5) is 20 to 4 G%, and the above formula (6) shows that Τ 10 is 40 to 50%, and the rest is other The component is usually Τ12 of G(7) table tf. The halophilic mixture is placed in a crucible, and T8 is precipitated by needle crystal precipitation. The cage type in the fluorenone resin (A) used in the present invention. The sesquiterpene oxide may be a mixture of T8, T10 and T12, or may be one or one of them separated or concentrated. Meanwhile, the fluorenone resin (8) used in the present invention is not limited. The fluorenone resin obtained by the above-mentioned production method. The radical polymerizable and δ-form used in the curable resin composition are free-radical polymerizable with the reactive functional group in the fluorenone resin (A). There is no particular limitation. Usually, it is preferably a photopolymerizable double bond compound. Preferred examples of the compound include (indenyl)propane 32l8li 19 201038681 enoic acid-based compound. One of the ideal ones of the unsaturated compounds, the radically polymerizable amine The phthalate ester-polymer (B). The hardening resin composition is preferably a hardening agent containing at least one component of a radically polymerizable urethane polymer (B) radical polymerizable unsaturated compound. The content of the urethane polymer (B) is preferably 1% or more, usually 1 to 50%, and 2 to 40%, based on the total amount of the radically polymerizable unsaturated compound. Preferably, it is preferably from 3 to 40%, more preferably from about 3 to 301⁄2. Further, in other forms, it is preferably from 5 to 40%, and preferably from 5 to 30%, and from 5 to 20 More preferably, the amino phthalate oligomer (B) has a number average molecular weight of 1 in the molecule having at least one unsaturated group represented by -R3-CR4 = CH2 or -CR4 = CH2. An oligomer of the above amino phthalate linkage (amino phthalic acid oxime oligomer), and the number average molecular weight is preferably 2,000 or more, and more preferably 2,500 or more, usually 10, 〇〇〇 below. Meanwhile, R3 in the above formula represents a cross-linking group or an -OCO- group of aliphatic C1 to C6. As for a cross-linking group of aliphatic C1 to C6, it is preferably a lower one having a carbon number of 1 to 6. An alkyl group and a lower sulfhydryl group having a carbon number of 1 to 6. The ideal group of R3 is an -OCO- group or a methylene group, and is preferably an -OCO- group. R4 represents a hydrogen atom or a C1 to C6 alkyl group. The preferred R4 may, for example, be a hydrogen atom or a C1 to C3 alkyl group (preferably a methyl group). The ideal unsaturated group represented by the above formula may, for example, be at least one selected from the group consisting of (meth)acryloxyloxy groups ( a group in the group consisting of acryloxy or methacryloxy), allyl and vinyl, preferably propyleneoxy or methacryloxy. Therefore, amino phthalate The oligomer (B) is preferably an amino phthalate (meth) acrylate having an acryloxy group or a methacryloxy group. 20 321811 201038681, 'Aminomethyl methacrylate (8), which can be produced by the conventional method, and examples of the method thereof include polyhydric alcohol and polybasic isophthalic acid. *酉1 And a method in which a terminal has a polymerizable unsaturated group and a base-based compound. At the time of the synthesis, the urethane copolymer (B) used in the curable resin composition of the present invention can be obtained by appropriately adjusting the molecular weight of the raw material or the molar ratio at the time of the reaction. The polyhydric alcohol may, for example, be polycondensed by polycondensation with a polyhydric alcohol to obtain a polyfluorene alcohol, and the inner vinegar such as ε_hexine vinegar and 7-pentane vinegar may be opened and closed: (4) Multi-presence; polymerization of ring-shaped slits such as epoxy W, epoxy (tetra), and butyl bromide, argon-oxygenated tetrahydroanthracene, and alkyl-substituted tetrahydrofuran, or a total of two or more of these Polyurethane polyol of polymer, etc. Meanwhile, the above polyvalent isocyanate compound may be exemplified by 2, 4-toluene diisocyanine 2' 6-nonylbenzene diisocyanate, 4, 4' _ diphenylmethane diisocyanate f vinegar, hydrogenation 4, 4 , diphenylmethane diisocyanate S, benzodimethyl diisolactam day, phthalic acid dimethyl dimethyl diisocyanate, hexamethylene diisocyanate vinegar, bismuth phor Isocyanic acid vinegar, 1>5-extension Cai diiso-acid vinegar, tolidine diisocyanate, p-phenylene diisocyanate, trans-cyclohexanone to succinic acid, lysine Isocyanic acid vinegar, tetramethyl xylene diisocyanate t (tetra) ester triisocyanate, 丄6, η-deca-octane triisocyanate, 1,8-dicyanoacetic acid + isocyanate Methyl octyl, 1,3,6-hexamethylene triisocyanate: Shuanghua Gengyuan triisocyanate, trimethylhexamethylene diisocyanate, monopentadiene diisocyanate And norbornene diisocyanate. The above compound having a polymerizable unsaturated group and a hydroxyl group at the terminal may, for example, be 2-light ethyl ethyl (meth) acrylate vinegar or 2- propyl propyl group 322811 21 201038681 propylene roasted Sman vinegar, 2 - mercapto-3-phenoxypropyl (meth) acrylate vinegar, 2-(methyl) propylene methoxyethyl 2-hydroxyethyl phthalate, isovalerol tris (methyl Acrylate, 3-propenyloxyglycerol mono(meth)acrylate, 2-hydroxybutyl(meth)acrylate, 2-hydroxy-i-(meth)acryloxyl_3_(fluorenyl) Acryloxypropane, glycerol di(meth)acrylate, polypropylene glycol mono(meth)acrylate, polyethylene glycol mono(indenyl)acrylate, polyε_caprolactone mono(methyl) Acrylate, 4-hydroxybutyl (meth) acrylate, ε-caprolactone mono(indenyl) acrylate, and various epoxy (fluorenyl) acrylates. The urethane oligomer (Β) in the present invention is preferably an amino phthalate (meth) acrylate oligomer. The urethane (meth) acrylate oligomer can be obtained by using a (meth) acrylate having the above-exemplified hydroxy group when it has a polymerizable unsaturated group and a trans group as the above-mentioned intermediate terminal. Meanwhile, a commercially available product can be used as the oligomer (,), and for example, a urethane acrylate polymer UF-8〇〇1 (quantitative average molecular weight: 2,600) manufactured by Kyoeisha Chemical Co., Ltd. is preferably used. Or UF-503 (quantitative average molecular weight: 3,800). As for the ideal urethane oligomer (B), a number average molecular weight of about 1,000 to 10 is exemplified, and an amino phthalic acid of 〇〇〇 is intended to be an oligomer of (meth)acrylic acid. Amino phthalate (fluorenyl) having a number average molecular weight of about 2,000 to 10, preferably 2, 500 to 10,000, and a number average molecular weight of about 2,5 to 6,000. Acrylate oligomers are preferred. The radically polymerizable unsaturated compound other than the amino phthalate oligomer (B) is an unsaturated compound other than the oligomer (B), for example, an unsaturated compound copolymerizable with the fluorenone resin (A). (〇. Unsaturated compound (c), 321811 22 201038681 Although it is not limited as long as it satisfies the above conditions, it is unsaturated, and (6) contains at least 10 to 100% of an alicyclic unsaturated compound. The alicyclic unsaturated sulfonate is an alicyclic bis(indenyl) acrylate (C,) represented by the following general formula (2).

Further, a component of the unsaturated compound (C) other than the above alicyclic unsaturated compound may, for example, be a bond-unsaturated compound having a polymerizable unsaturated group or an aromatic group having a polymerizable unsaturated group. Family compound. In the alicyclic di(meth)acrylate (c,) represented by the formula (2), a specific compound when z is a group represented by (5), and a compound having r is hydrogen is a penta ring [6. M'u] pentadecyl dimethylol diacrylate, z is a specific compound of the group B^· represented by (10), and tricyclo[5 2 1 〇 2'6] decane dihydroxyl group having R as chlorine Diacrylate. In the present invention, the alicyclic unsaturated compound may contain a plurality of alicyclic di(methyl) propylene vinegar (C) represented by the formula (2). The alicyclic unsaturated 321811 23 201038681 compound is at least 50% or more, preferably 70% or more, more preferably 80% or more, and more preferably 90% or more, based on the total amount of the unsaturated compound (6). The entire amount of the unsaturated compound (C) may be all of the alicyclic unsaturated compound. In addition to the aforementioned alicyclic unsaturated compound, the component contained in the unsaturated compound (C), besides the amino phthalic acid ester (B), may be a polymer having a repeating number of about 2 to 20 in structural units. Reactive oligomers, with low molecular weight and low viscosity reactive monomers. Meanwhile, the component can be distinguished as a monofunctional unsaturated compound having only one unsaturated group and a polyfunctional unsaturated compound having two or more unsaturated groups. In order to obtain a good three-dimensional crosslinked product, the unsaturated compound (C) may optionally contain an alicyclic unsaturated compound other than the above (which is preferably an alicyclic formula represented by the formula (2). a polyfunctional unsaturated compound other than the acrylate (C')). When the heat resistance, strength, and the like of the copolymer are required, the polymerizable unsaturated bond in the unsaturated compound (C) is preferably an average of 1.1 or more and 1 or less per molecule, and is 1. More preferably 5 or more, and more preferably 1.6 or more. Therefore, by mixing a monofunctional unsaturated compound with a polyunsaturated compound having 2 to 5 unsaturated groups, or a polyfunctional unsaturated compound, the average number of functional groups can be suitably adjusted. When only the alicyclic bis(indenyl) acrylate (C ') of the above formula (2) is used as the unsaturated compound (C), the polymerizable unsaturated bond group has an average of 2 per molecule. As the aforementioned reactive oligomer, for example, epoxy acrylate, epoxidized oil acrylate, unsaturated polyester, polyester acrylate, poly 24 321811 201038681 B-, polyene/thiol, acrylic acid, t-butene, and ethyl methacrylate. Among the aforementioned reactive monomers, there are monofunctional monomers and polyfunctional monomers. The above-mentioned reactive monofunctional monomer may, for example, be styrene, ethylene acetate, N-ethyltetrahydro sulphate, (10) succinic acid, _acid 2-ethylhexyl acrylate, acrylic acid hexanoic acid, Acrylic cyclohexyl acrylate, n-decyl propyl acrylate, acetonide acetonate isobornyl ester, dicyclopentyloxy ethacrylate vinegar, phenoxyethyl acrylate and trifluoroethyl methacrylate. The above-mentioned reactive polyfunctional monomer is an unsaturated compound of the lipid-formed bis(methyl) acrylate (c) represented by the above formula (2), and examples thereof include tripropylene glycol dipropanoic acid. Vinegar, 1>6-hexanediol dipropylene vinegar vinegar, bismuth A-dehydroglyceryl ether diacrylate, tetraethylene glycol diacrylate, hydroxydimethylacetic acid neopentyl glycol diacrylate g, Tris(tetra)propylpropane triacetate, trimethyl methacrylate trimethyl acrylate, pentaerythritol trimethyl acetoacetate, pentaerythritol tetrapropyl vinegar, diisoamethylene A polyfunctional (meth)propionic acid vinegar compound of 2 to 6 oxo groups, such as alcohol triacrylate vinegar and diisopentaerythritol hexaacrylate. It is preferred to use a compound of (meth) acrylate having 2 to 3 functional groups, for example, trimethyl methacrylate or tris(methyl) propylene vinegar, isoindolinol di or tri (a) Base) acrylic acid vinegar and diisopentaerythritol di- or tri-(methyl)-acrylic acid vinegar, etc., among which trimethyl ketone tripropionate or diisopentaerythritol Triacrylate is preferred. = Saturated Compound (C) 'In addition to the above examples, various reaction/raw oligomers and monomers can also be used. (4) The formula (2) denotes the formula (4) of the formula (2) bis(methyl)-propionate, which is intended to be: ') a phase-reactive silk or lysate, in the present invention, 32181 25 201038681, the use of the compound It is preferable to use the compound of the formula (2), and it is possible to use it in a single unit or in combination of two or more types. The ideal compound of the unsaturated compound (c) may, for example, be a fluorene-based fluorenyl (C') represented by the above formula (2), or a monofunctional or polyfunctional (fluorenyl group; an olefinic compound). And an alicyclic two C ψ A ) @ $ fee gg (C) or a polyfunctional (fluorenyl) acrylate compound represented by the above formula (2) is preferred, and more specifically, the above formula is used alone. (2) an alicyclic mono(indenyl)acrylic acid _(c,) or an alicyclic mono(methyl)propyl benzoate (C,) and a polyfunctional (using the above formula (2) Methyl) acrylate compound. The curable resin composition used in the present invention is a resin composition containing 5 to 80% of the above fluorenone resin (A) and 95 to 20% of the radical polymerizable compound with respect to the entire composition, and contains any Additives. Examples of the optional additives include various additives including a photopolymerization initiator described later. It is preferred to contain a photopolymerization initiator. Meanwhile, the radically polymerizable compound ' preferably contains an amine phthalate condensate (both magical and the above unsaturated compound (C). Therefore, a good curable resin composition contains a linaloyl resin (magic, The curable resin composition of the amino acid sulfonate S (B) and the unsaturated compound (c) is preferably a total of 60 to 97% of the total composition of the curable resin composition. 'It is preferably 70 to 96% by weight, more preferably 80 to 95% by weight, and the residual portion is a photopolymerization initiator and other optional components. The base resin (A), amino phthalate The mixing ratio (weight ratio) of the components of the oligomer (β) and the above-mentioned unsaturation 32181 26 201038681 compound (c) is 5 to 8 Å: i to 50: 10 to 80, and is 1 〇 to 7〇: 5 to 3〇: 3〇 to 7〇...the range is better. If the ratio of the fluorenone resin (A) is less than 5%, the heat resistance and transparency of the cured coating film will be improved. It is not preferable because the physical property value such as water absorption is lowered, and at the same time, if the ratio of the fluorenone resin (A) exceeds 8%, the viscosity of the composition is caused. In addition, when the ratio of the amino carboxylic acid condensate (B) is from 1 to 5 %, the obtained polarizing plate is excellent in the winding property, and the strip can be made long. After processing, it is wound into a wheel shape. If the ratio of guanidinium hydroxy ruthenium phthalate (Β) exceeds 50%, the compatibility with the fluorenone resin is deteriorated, and it is difficult to obtain a uniform resin composition, so that it is difficult to obtain a uniform resin composition. The above range is preferred. The ratio of the amino phthalate chelating agent (Β) is preferably from 3 to 30% as described above, more preferably from about 3 to 20%, and optionally from 5 to 3% by weight or 5 to 20%, for example, when the proportion of the fluorenone resin (Α) is large, the obtained cured product has the physical property advantage as the fluorenone resin. Further, when the ratio of the unsaturated compound (c) is large, The obtained cured product has a physical property advantage as a resin formed of the unsaturated compound (c), and can improve a number of disadvantages due to the advantages of the fluorenone resin. Meanwhile, in the curable resin composition, such as an alicyclic When the unsaturated compound is contained in a large proportion in the unsaturated compound (C), the obtained cured product is excellent in low hygroscopicity. When the ratio of the non-alicyclic polyfunctional unsaturated compound is large, the obtained cured product is excellent in low linear expansion property. Therefore, it is preferred to appropriately change the composition ratio in accordance with the purpose of use. The curable resin composition used in the present invention In the total amount of the three components of the lipid (A), the amino phthalate copolymer (B), and the unsaturated compound (C), the composition ratio of each component is as follows. (a) Alkaloid resin (A): 10 to 70%, preferably 10 to 60%, more preferably 10 to 55%, urethane polymer (B): 3 to 40 %, unsaturated compound (C): 30 to 70%; (b) a preferred form is the case where the amino phthalate polymer (B) is from 3 to 30% in the above (a); (c) At the same time, in other forms, in the above (a) or (b), the unsaturated compound (C) is 40 to 70%; (d) at the same time, in other forms, In any one of (a) to (c), the urethane oligomer (B) is 5 to 30%, more preferably 5 to 20%; (e) simultaneously, at (a) to In the form of any of (d) The alicyclic bis(indenyl) acrylate (C ') represented by the formula (2) is from 10 to 100% based on the total amount of the unsaturated compound (C), and is preferably from 20 to 100%, and is relative to the When the total amount of the unsaturated compound (C) is the same, the other component contained in the unsaturated compound (C) is from 0 to 90%, and preferably from 0 to 80%. (f) In the form of the above (e), the alicyclic bis(indenyl) acrylate represented by the formula (2) can be obtained especially when a cured film having a low hygroscopicity is desired. C') is 50 to 100% (g) based on the total amount of the unsaturated compound (C), and in the form of the above (e), when a composition having excellent low linear expansion property is obtained, the general formula can be obtained. (2) The alicyclic bis(indenyl)propionate (C') 28 321811 201038681 =:= The total amount of the compound (C) is less than that, and the residual extraction can be made as 3 in other unsaturated compounds (6). In the ingredients. And (8) and _Li4(e)s(h) in any one of the states "is such that the component contained in the other unsaturated sigma (6) is a polyfunctional acryl vine compound in the form of an aliphatic polyfunctional (methyl) The form of the acrylate compound is preferred. The curable money composition is preferably a photocurable resin composition, and the composition is a photopolymerization initiator, a photoinitiator, and a sensitizer, and is an additive that promotes reaction by ultraviolet rays or the like. Usually the product should contain

ϋ Photopolymerization initiator. When the polymerization initiator is formulated, the amount of addition is usually 0.1% with respect to 1 part by weight of the ketone resin (Α), the urethane carboxylic acid valerate (Β), and the unsaturated compound ([). It is preferably from qi to 4 parts by weight, and preferably from 1 to 4 parts by weight, to 10 parts by weight. It is preferably 1 to 6 parts by weight based on 100 parts by weight of the total. When the amount is less than 0.1 part by weight, the curing is insufficient, and the strength and rigidity of the obtained molded article are lowered. On the other hand, it is preferable that the amount of addition is 5 parts by weight or less, that is, there is no problem such as coloring. As the photopolymerization initiator, compounds such as acetophenones, benzoin, benzophenones, oxime ketones, and aCylph〇Sphine oxides can be used. Specifically, for example, trichloroacetophenone, diethoxyphenyridinium, 2,2-dimethoxyl-1,2-diphenyl phenylindole, 2-cyano-2-indenyl- 1-phenylpropanol-1-ketone, 1-cyclohexylphenylene, 2-methyl-1-(4-indolethiophenyl)-2-morphinylpropan-1-one, benzoin Anthracene, benzoquinonedidecyl acetal, dibenzophenone, bis(2,4,6-trimethyl adenyl)-phenylphosphine oxide, 2,4,6-trimethylphenylhydrazine Keto-diphenyl-phosphine oxide, 嗟 321321 29 201038681 ketone, 2, 4, 6-trimethylphenylnonyldiphenylphosphine oxide, nonylphenylglyoxylate, hydrazine, benzoate醯, 蒽醌 and Michelin (Michler, s ketone). Further, it is also possible to use a photoinitiator or a sensitizer in combination with a photopolymerization initiator to exert an effect. Further, the photopolymerization initiator may be preliminarily formulated in the curable resin composition, and may be added and mixed when the curable resin composition is applied as the case may be. In the above resin composition, various additives other than the above may be added insofar as the properties are not impaired. As the various additives, for example, an antioxidant, a light stabilizer, an ultraviolet absorber, an organic/inorganic filler, a plasticizer, a flame retardant, a heat stabilizer, a lubricant, an antistatic agent, a mold release agent, and a foaming agent may be mentioned. , nucleating agents, coloring agents, dispersing aids and resin components. A light stabilizer can be applied to compounds such as hindered amines. Specifically, for example, bis(1,2,2,6,6-pentamethyl-4-hexahydro-n-heptyl) azelaic acid vinegar, methyl 1' 2, 2, 6, 6-pentaquinone may be mentioned. Benzyl-4-hexahydro-n-bite sebacate, bis(1,2,2,6,6-pentamethyl-4-hexahydropyridyl){[3, 5_double (1, i Dimethylethyl) 4 benzylidene]methyl}butylmalonate and bis(2,2,β, tetradecyl-4-hexahydropyridinyl) sebacate and the like. As the ultraviolet absorber, a compound such as a benzotriazole compound, a triazine compound, a benzophenone compound, a salicylic acid compound, a cyanoacrylic acid ester compound, or a nickel compound can be used. Specifically, for example, 2-(2H-benzotriazol-2-yl)-6-(1-mercapto-1-phenylethyl)- 4-(1,i, 3' 3-tetradecyl) Butyl)phenol, phenylpropionic acid _3_(2{1_benzotriazol-2-yl)_5-(1,1-dimercaptoethyl)-4~hydroxy-C7_9 side chain and linear alkyl ester辛基_3_ 321811 30 201038681 Ο Ο [3-Tertibutyl-4-hydroxy_5_(5_chloro_211_benzotriazol-2-yl)benzimpropionate, phenylpropionic acid-3 -(2Η~ stupid triazole-2_yl)_5_(1,b dimethyl "ethyl)-4-hydroxy-C7-9 side chain and linear alkyl ester, 2_(2_hydroxy second Phenyl)-2-anthracene-benzotrisene, 2-(2,_trans-based _5, _methylphenyl) stupid = triazole, 2-(2,-hydroxy-3', 5'-two one Tributyl phenyl) _5_chlorobenzotriazole, 2-(2,-carbyl-3,-tert-butyl-5,-methylphenyl)-5-chlorobenzoxazole, 2-(2 ,-transcarbyl-3,,5,-di-p-third amylphenyl) gas benzotrisene, 2_(2_search-5-thanooctylphenyl)benzotriazole and 2,4 - Bis[2-hydroxy+butoxyphenyl]~6-(2,4-diethoxyphenyl)-1,3,5-triazine, and the like. Antioxidant, suitable for compounds such as hindered phenols. Specific examples thereof include, for example, pentaerythritol tetra [3~(3,5-di-t-butyl+silylphenyl)propionate, thiodiethene [3-(3,5-12). Tert-butyl- 4-pyridyl)propionate], octadecyl-3-(3,5-di-t-butyl-4-yl-phenyl)propionic acid vinegar and 4,6- Bis(octylthiomethyl)_o-guanidine and the like. The curable resin composition used in the present invention preferably contains at least one component selected from the group consisting of a UV-polymerizing initiator and an ultraviolet absorber, an antioxidant, and a light stabilizer, and is preferably contained in all of them. . The content of these components in the curable resin composition is usually 100 parts by weight based on the total of the total amount of the sulfonate, the urethane carboxylic acid oligomer (8) and the unsaturated compound (c). The ultraviolet absorber is 〇 to 8 parts by weight, preferably 0.1 to 6 parts by weight, and preferably 2 to 6 parts by weight, and the antioxidant and the photosensitizer are independently from 4 to 4 parts by weight, and Preferably, it is preferably 3 parts by weight, and preferably 5 parts by weight to 2 parts by weight. The polarizing element (polarizer) used in the polarizing plate of the present invention is not particularly limited as long as it has a function of polarizing the light of the light source, and an absorption type that absorbs light in a specific direction and is polarized can be used. Any one of a polarizing element and a reflective polarizing element that reflects light in a specific direction and is polarized. The absorbing element may be a uniaxially stretched hydrophilic polymer film such as a PVA film containing a dichroic dye such as a dye or a polyvalent iodide ion, or a uniaxially stretched film of the PVA film. After dehydrating with an acid before the axial stretching, a polarizing element forming a polyene structure can be obtained; and on an alignment film which is aligned as in a certain direction, a two color which exhibits a liquid crystal state of a lytropic type can be applied. A pigment solution, and then a polarizing element or the like obtained by removing the solvent. On the other hand, the reflective polarizing element may be, for example, a polarizing element formed of a laminate of a plurality of different birefringences; a polarizing element formed by combining a cholesteric liquid crystal having a selective reflection domain and a 1/4 wavelength plate; and A polarizing element or the like of a wire grid is provided. In order to obtain the effect of the present invention more effectively, the polarizing element to be used is preferably a uniaxially stretched hydrophilic polymer film element such as a PVA film containing a dichroic dye such as a dye or a polyvalent iodide ion which is excellent in polarizing characteristics. The obtained polarizing element or a depolarizing element which forms a polyene structure by acid dehydration before the uniaxial stretching of the PVA-based film. The above polarizing element can be manufactured by a conventional method. For example, when a polarizing element is formed of a PVA-based film containing a dichroic dye containing a dye and a polyvalent iodide ion, the PVA-based film is first immersed in warm water or the like, and then impregnated into a dyeing tank in which a dichroic dye is dissolved. After dyeing the film, the film is stretched in a uniaxial direction in a bath containing a crosslinking agent of boric acid or borax, and dried to obtain the polarizing element. Examples of the dye used in the dyeing include an iodine-potassium iodide aqueous solution, and an application of "functional coloring matter" (into Jiang Masahiro, CMC, 32 321811, 201038681), azo compounds, c. I, pages 98-100. .Direct Yellow-12, CIDirect Yellow-28, c. I. Direct Yellow-44, CI Direct > Light _26, c. L Direct Orange-39, CI Direct Orange-107, CI Direct Red-2 ' CI Direct Red-3b c. I. Direct Red-7.9, CI Direct Red-81, CI Direct Red-247, CI Direct Green-80, CI Direct Green-59, and Japan Special 2〇〇1_33627, Japan Special 2〇〇2_ 296417, Japanese Patent Laid-Open No. 2003-215338, WO 2004/092282, Japanese Unexamined 2001-〇564112, Japanese Special Open 2001-027708, Japanese Special Kaiping 11-218611, Japanese Special Kaiping u_21861〇, and Japanese Special Open An organic dye or the like described in Japanese Laid-Open Patent Publication No. 156759. In addition to the free acid, these dichroic dyes may also use alkali metal salts (for example, sodium salts, potassium salts, and lithium salts), ammonium salts, amine salts, and staggered salts (for example, copper salt, nickel). Salts such as the wrong salt and the wrong salt, etc.). The performance of the polarizing element can be adjusted by the dichroism of the dichroic dye or the stretching ratio at the time of stretching. The surface of the polarizing element may be subjected to any surface modification treatment to improve the adhesion to the curable resin composition. The surface of the present invention is preferably a surface-modified one. The above surface modification treatment may, for example, be a decane coupling treatment, a corona treatment, a plasma treatment, a glow discharge treatment, a flame treatment, an ozone treatment, (10) an ozone treatment, and an ultraviolet treatment. These treatments may be carried out singly or in combination of two or more. Preferably, the surface modification treatment is performed by applying the decane coupling treatment to the decane coupling from the surface of the adhesion, so that the decane coupling agent is carried out by a well-known method 32118 33 201038681, that is, the polarizing element is treated with the hydrolyzate of the broth coupling agent. The method of the surface. For example, after the decane coupling agent is hydrolyzed in water or an aqueous organic solvent, it is uniformly applied to the polarizing element, and then the solvent is removed by heating or the like. By the decane coupling treatment, the action of the decane compound on the surface of the polarizing element can be present, and the bonding strength between the cured film (layer) of the coating film and the polarizing element can be further enhanced. Examples of the decane coupling agent include various decane coupling agents such as (meth)acrylic acid, amine based and isocyanate. A (fluorenyl) acrylic decane coupling agent is preferably used in the present invention. As the (meth)acrylic decane coupling agent, specifically, for example, 3-propenyloxypropyltrimethoxydecane, 3-propenyloxypropyl-decyldimethoxy decane, 3-mercaptopropene醯oxypropyltrimethoxydecane, 3-methacryloxypropylmethyldimethoxydecane, 3-mercaptopropenyloxypropyltriethoxydecane, 3-mercaptopropene oxime Oxypropyl decyl diethoxy decane, mercapto propylene methoxymethyl tridecyl decane, methacryl decyl decyl triethoxy decane, and the like. As for the hydrolysis method of the above decane coupling agent, for example, a method of stirring the above-mentioned decane coupling agent in water or an aqueous organic solvent may be employed; and the above-mentioned decane conversion agent is divided while stirring water or an aqueous organic solvent. A method of adding a plurality of times; and a method of continuously adding the above-mentioned Shi Xixuan coupling agent while disturbing water or an aqueous organic solvent. Meanwhile, a method in which the above decane coupling agent is dissolved in an organic solvent to prepare a solution, and the solution is added to water or a water-containing organic solvent in accordance with the above method to carry out hydrolysis may be employed. When the decane coupling agent is hydrolyzed, an acid catalyst such as hydrochloric acid, sulfur 34 321811 201038681 acid, boric acid, oxalic acid, citric acid or acetic acid, or ammonia, urea, ethanolamine and tetramethylammonium hydroxide may be used as needed. Alkaline catalyst (hereinafter referred to as "catalyst"). The organic solvent used in the hydrolysis may be one which dissolves the decane coupling agent and has compatibility with water and a catalyst which is used as needed, or may be water in the presence of a surfactant. The catalyst may be uniformly dispersed in a state of being combined (microgelatinous). Specific examples of the above-mentioned organic solvent include alcohols such as decyl alcohol, ethanol, isopropanol, n-butanol tert-butanol, pentanol, ethylene glycol, propylene glycol, hydrazine, and 4-butanediol. Ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate; alkane or cycloalkane such as isooctane and hexane; dioxane and bismuth; and benzene And aromatic hydrocarbons such as toluene; These organic solvents may be used singly or in combination of two or more kinds thereof. Among the above-mentioned early organic solvents, alcohols are particularly preferable, and although organic solvents which are incompatible with the catalyst may be used, At this time, it is necessary to add an interface to the water to uniformly disperse the water and the catalyst. 钊, when the hydrolysis, the concentration of the decane coupling agent in the liquid containing the liquid coupling agent is preferably relative to the total capacity of the liquid contained in the silane coupling agent. It is preferably 〇L or more, and it is preferably U Mo/L or less. When using the above organic solvent, it is used together with an organic solvent (relative to the total capacity of the liquid: 3⁄4 degrees), preferably G. 1 mol, Preferably, when the concentration is 2 mol/Ux, the concentration of the water is less than /L, and preferably 25 mol or less. It is preferably 5. The organic solvent is not used in the present invention. The hydrolysis of the above-mentioned catalyst is carried out only in the water. In the case of using the above catalyst, although the concentration of the catalyst (concentration with respect to the total capacity of the liquid) cannot be generalized depending on the catalyst, it is preferably, for example, hydrazine. 8 mol / L or more. At the same time, the concentration of the catalyst should be 10 m / L or less, and preferably 9.4 m / L or less. The pH of the solution of the decane coupling agent is preferably adjusted in the range of pH 2 to 11 depending on the use of the Shi Xi burning composition. For example, an amine decane The aqueous solution of the coupling agent is stabilized in a weakly alkaline state, the pH is preferably in the range of 8 to 11, and preferably pH 9 to 10.5, and the ideal (meth)acrylic decane coupling agent in the present invention. The best time is 3. 0 to 4. 5, and the best is 3. 0 to 4.5. The reaction temperature of the above-mentioned Shixi burning coupling agent in the hydrolysis is preferably 5 ° C or more, preferably 10 ° C or more, more preferably 20 ° C or more, and the above reaction temperature is preferably 100 ° C. In the following, it is preferably 70 ° C or lower, more preferably 50 ° C or lower, and the hydrolysis can be accelerated as long as the reaction temperature is 0 ° C or higher, and the hydrolysis reaction can be easily controlled as long as it is 100 ° C or lower. The reaction time of the above decane coupling agent at the time of hydrolysis, and the conditions are preferably set according to the decane coupling agent to be used, although not limited, for example, 15 More preferably, it is preferably 20 minutes or more, and more preferably 25 minutes or more, and more preferably, the reaction time is preferably 100 hours or less, more preferably 20 hours or less, and more preferably 10 hours or less. As long as the reaction time is 15 minutes or longer, the hydrolysis reaction can be sufficiently carried out, and if it is less than 100 hours, the heat energy required for the heat treatment can be reduced, and the production can be improved: Nightmare 36 321811 201038681 So water is used as the hydrolysis of the mixture The best reaction conditions are: Eclipse 1 2 Mo Er 2 The concentration of the above decane coupling agent is 〇, Mo / "Zeng, in the ear range, the concentration of the catalyst is 〇8 Mo to Mo Er -, the reaction temperature is From the machine to the 9.4 reaction time of 25 minutes to 1M, within the range of the time of the inside and the 2 money coupling _ hydrolysate coated on the polarizing element is not particularly limited, the mouth 1 million, Ο ❾ cloth, A coating method that makes the surface smooth and has a uniform thickness. Specifically, it can be applied by using a strip or the like, a coating machine, a slit coater, a money transfer coating machine, and a (four) money heart-shaped transfer. (4) = heat treatment can be carried out according to a general method, and the treatment temperature is preferably = It is better to use the machine above, and better when it is above the order. At the same time, the processing temperature should be 1_ or less. When the reaction temperature is (TC or more, the solvent can be quickly evaporated, and the performance of the polarizing element can be reduced by the heat as long as it is just cm. The processing time of the heat treatment is also dependent on the processing temperature. The difference is usually from 2 minutes to 5 hours, and preferably from about 10 minutes to 2 hours. The above-mentioned curable resin composition used in the present invention may be applied to one side or both sides of the polarizing element. After hardening, a protective layer made of a cured product of the curable resin composition is formed, and the polarizing plate of the present invention is obtained: specifically, the resin reduced material may be diluted with a solvent directly or as needed. It is coated on one side or both sides of the polarizing element. It is preferably coated without solvent thinning 321811 37 201038681. When diluted with a solvent, the air interface of the coating film after removing the solvent by heating or the like is preferred. On the side surface, or in the case of no release, the air interface side surface of the coating film is directly subjected to a treatment such as masking or the like as needed. The ultraviolet ray is irradiated onto the coating film (resin layer) to harden the resin layer. Rear' The polarizing plate of the present invention can be obtained. The coating method of the resin composition is not particularly limited as long as it can maintain smoothness and thickness uniformity, and for example, a strip coater, a gravure coater, and a slit coater can be used. Coating method such as roll coater and spin coater. The energy line should be ultraviolet light, which can be irradiated in air or under nitrogen. For example, 'ultraviolet light with a wavelength of 10 to 400 nm is like a cumulative exposure of 1,000 to 20 When irradiated in the range of 000 mJ/cm 2 , the coating film can be hardened. As long as the wavelength of the light used is within the above range, there is no particular limitation 'especially, near ultraviolet rays having a wavelength of 200 to 400 nm can be applied. The source lamp may be, for example, a low pressure mercury lamp (output: 0.4 to 4 W/cm), a high pressure mercury lamp (40 to 16 〇 W/cm), an ultrahigh pressure mercury lamp (173 to 435 W/cm), a metal halide lamp (8 〇). Up to i60W/cm), pulsed xenon lamp (80 to 120W/cm) and electrodeless discharge lamp (80 to i2〇W/cm), etc. These UV lamps have their own spectral distribution characteristics, so they can be combined with light. Choose the type of starting agent Meanwhile, the thickness of the coating cured film (layer) of the resin composition is determined in accordance with a suitable purpose, and is usually selected in the range of about #·5 # m to 500. The ideal range as a protective film is about 3/zm to 200. Especially when looking at the thin plasticization of the protective film, it is about 4/zm to 40//m' and can be made 4/zm to 35#m, so that it is 4#111 to 25/zm More preferably. 38 321811 201038681 π-resin resin layer) is formed on at least the hardened layer of one side of the polarizing element (coated hardened vine protective polarizing element, or (9) formed on (9), but on both sides of the piece Formed (layered). The effect of the X-ray may be applied to the other surface of the support surface having the polarizing element on the surface of the one side surface of the polarizing element or the surface of the polarizing element on the one side surface of the one polarizing element. The support body is also referred to below as a support body. In Ο

The task of the G row support or the protective film is not particularly limited as long as it is a tree furnace support having a different curable resin composition, and is usually composed of the above resin layer or film, and a layer or a film. The film formed of the cured product of the cured resin is a film formed of ultraviolet light or the like which is different from the fat composition, and is preferably made of TAR or TAC or a cyclic hydrocarbon polymer. In particular, the coating film hardened film layer is formed on the early surface of the polarizing mono- 2 dilute hydrocarbon polymer, and the film formed by the % smoky polymer is supported as a partial well technique. The polarizing plate of the present invention can improve the heat resistance and the moist heat resistance because it can be modified. === 'When the body is 'normally', it is followed by the hardening property of the polarizing element. (10) The purpose of the group of money (four) the hard layer of the film is _ = upper. When the polarizing plate of the present invention has a film such as TAC or a cyclic hydrocarbon polymer as the branch (4) on the other surface, the film side of the polarizing plate is preferably directed toward the liquid crystal cell side, and the polarizing plate is disposed. In the liquid crystal display. On the surface of the polarizing plate of the present invention (the surface of the cured film layer of the curable resin of the present invention or the other surface), Μ 39 321811 201038681 (anti-refraction) may be applied as needed. Various surface treatments such as AG (anti-glare: anti~giar^&gt; anti-reflection treatment, anti-fouling treatment such as water-repellent and oil-repellent, and anti-fingerprint treatment which is difficult to adhere or appear fingerprints.) The polarizing plate can suppress the dimensional change when the polarizing plate is used by the effect of the hardenable tree layer and the cured layer of the object. The polarizing plate of the present invention is placed in an environment of 100% for 24 hours. The size of the polarizing plate of the present invention is preferably less than 5%, and preferably less than 0.3%. The polarizing plate of the present invention can be disposed in the light path of the image display, for example. It is disposed at least on one side of the liquid crystal cell of the liquid crystal display, etc., and obtains the image display of the present invention, such as a liquid crystal display. Although the liquid crystal display may be different depending on the type of liquid crystal cell used, the present invention can be used in any case. Bright polarizing plate. For example, VA (vertical alignment), IPS (in panel switching), 0CB (optically compensated bend), tn (twist nematic ' twisted nematic The polarizing plate of the present invention is used in various types of liquid crystal displays such as the STN (super twist nematic type). In the polarizing plate of the present invention and the liquid crystal cell, a retardation film can also be inserted to improve The viewing angle characteristics or contrast. The type of the retardation film to be used varies depending on the type of the liquid crystal cell. For example, in the case of the VA type, a negative C-plate or a film in which an A-plate and a negative C-plate are combined may be used. In the case of ips, a biaxial-plate or a positive C-plate can be used. In the case of the TN type, a discotic liquid crystal (disctic LC)-immobilized film can be used, and in the STN type, a double can be used. Shaft - 40 321811 201038681 board. Same as the 'precursor board of the present invention can be applied to liquid day and day projectors, where? = Γ usually uses liquid crystal as a separate light source for red, green and blue Colored polarizing plate for cells. The invention The liquid crystal display can be Ο ❹ ❹ ❹ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ 。 。 。 。 。 。 。 。 。 。 。 。 In the above-mentioned liquid crystal cell-like arrangement 2, in the image display having the coating film hard invention on one side, for example, in the case of the hardening property of the present invention, the polarizing plate is oriented outward, for example, it is preferable to apply the cured film. (Layer), the coating cured film of the composition from the viewpoint of the liquid crystal cell The polarizing plate of the invention is disposed as a curable resin cell. Such a configuration can affect the two polarizing elements/supports and the like/liquid crystal (moisture), and suppress the penetration of the transparent member from the temperature or humidity in the environment without causing a decrease in adhesion. ' 'Under or polarization changes occur, but now. In a good case, the stable image can be simultaneously displayed for a long time, and the liquid crystal display element composed of the shadow of the present invention can also be disposed in the optical path of the secret display 711 by the polarizing element of the present invention. The liquid crystal display element of one surface of the polarizing plate of the present invention can be obtained by, for example, teaching at least one surface of the unit cell, and then applying a pressure-sensitive adhesive, and then obtaining the double-sided surface after the liquid surface is bonded to the surface. Preferably, the polarizing plate of the present invention is transparent and optically oriented. As for the pressure-sensitive adhesive at this time, it is only necessary. In other words, in the liquid crystal display such as a liquid crystal projector, when the polarizing plate of the present invention is disposed on both sides of the liquid crystal, the surface of the support can be arranged to face the light. On the entry side, the surface of the hardened resin composition of the curable resin composition of the present invention faces the emission side. [Examples] Hereinafter, the present invention will be described in more detail by way of examples, but the invention is not limited thereto. Moreover, the RTM attached to the top indicates the registered trademark. (Synthesis example) <Synthesis Example of Polyorganic Half-Band with Cage Structure> Synthesis Example of 2-Propanol (IPA) as a solvent in a reaction vessel equipped with a stirrer, a dropping funnel and a thermometer 40 ml of 3 g of a 5% aqueous solution of tetramethylammonium hydroxide (aqueous TMAH) as an alkaline catalyst. Add IPA 15ml and 3-mercapto propylene methoxy propyl trimethoxy decane in the dropping funnel (MTMS: Toray Dow Corning Silicone (SZ-6300)) 12. 69g While stirring the solution in the reaction vessel, the IPMS solution of MTMS was dropped into the reaction vessel at room temperature for 30 minutes. After the dropwise addition of the MTMS, the reaction mixture which was not heated was stirred for 2 hours, and after stirring for 2 hours, the solvent was removed under reduced pressure, and the obtained product was dissolved in 5 ml of toluene. The resulting solution was washed with a saturated saline solution until it was neutral, and anhydrous (4) water was used. After the anhydrous (four) magnesium noodles, the yoke liquid is hydrolyzed and condensed (double wei VIII 8. 6g. This douche is a colorless viscous liquid soluble in various organic solvents. Its &quot; With mixer, Dean _ Stark device (Dean-Stark 321811 42

I 201038681 (apparatus)) and a reaction vessel of a condenser were charged with 20.65 g of sesquiterpene oxide, 82 ml of toluene and 3 〇g of a 1% by weight TMAH aqueous solution, and heated to distill off water. After heating to 13 (TC, the recondensation reaction was carried out at the reflux temperature of toluene. At this time, the temperature of the reaction solution was 1 〇 8. 〇. After the benzene was refluxed and mixed for 2 hours, the reaction was completed. After the reaction bath was washed with water until neutral, it was dehydrated with anhydrous magnesium sulfate. The anhydrous magnesium sulfate was separated and concentrated, and the sputum was concentrated to obtain a cage of the desired product. The obtained cage type sesquiterpene is a colorless viscous liquid of various organic solvents. /, liquid = liquid chromatograph separates the reactants after the recondensation reaction, and then performs mass 1 analysis. It is confirmed that the knives of the above structural formulas (5), (8), and (7) have molecular ions with recorded ions attached thereto. The composition ratio is T8: T10. T12 and others are approximately 2:4: 丨: 3, which is confirmed to be available. The cage-type structure is a core component of the linoleic acid resin. Example 1 Preparation of 〇(1) Curable resin composition The caged decylated polyphenyl sesquioxalate having a methacryloxy group obtained in the synthesis example Oxygen burning: 30 parts by weight, urethane acrylate acrylic oligomer ( Rongshe Chemical Co., Ltd., trade name: ϋ{Γ_5〇3): 5 parts by weight of dicyclopentene diacrylate (tricyclo[5. 2· 1. 〇2,6]) decane dihydroxyl Di acrylate): 65 parts by weight, 1-hydroxycyclohexyl phenyl ketone: 2 parts by weight, bis(2,4,6-dimethylphenyl nonylphenylphosphine oxide: hydrazine parts by weight, ultraviolet absorption Agent (manufactured by Ciba Specialty Chemicals, trade name: Tinuvin 384-2): 4 parts by weight, bis 2, 2, 6, 6-pentamethyl _4_ 321811 43 201038681 hexahydropyridyl) sebacic acid Ester: 1 part by weight, and pentaerythritol tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate]: 1 part by weight of the mixture, the hardening of the present invention is obtained Resin composition. The composition of the curable resin composition of each of the examples is as shown in Table 1 below, and (2) the light-emitting treatment of the polarizing element is carried out on a glass plate by an acrylic pressure-sensitive adhesive (() Polatechno's 'AD-R0C', a PSA-based adhesive which is obtained by stretching an alkali-treated TAC, and further using a PVA-based adhesive to stretch a PVA-based resin film. The SHC is laminated on the TAC surface with a PVA device. The unlaminated surface of the laminated polarizing element is subjected to a enthalpy coupling treatment. At the same time, the 'Shi Xi Shao _ _ processing is carried out as follows. Three parts by weight of 3-propenyloxypropyltrimethoxydecane (clacane coupling agent) was dissolved in 100 parts by weight of water. To the solution was added a 1% by weight aqueous solution of vinegar as a catalyst until the solution of the solution became 4. 〇, and hydrolysis was carried out at 25 C for 3 minutes. An aqueous solution of the dehydrolyzate was applied by a spin coater under the conditions of 1, 〇〇 _ and 60 seconds to laminate the undeposited surface of the polarizing element on the TAC surface. Then, in a hot air circulating furnace, 5 (TC is used for 30 minutes to remove the solvent, and then the surface of the polarizing element can be surface-fired. (3) Formation of the cured film = using a coating machine The hardenable rhythm composition obtained in (1) is coated on the bisector (4) treated surface obtained in the above 4 (2), and the film thickness after hardening is 2 〇 _. The ultraviolet ray is irradiated with a high pressure mercury lamp, 321811 201038681 « The resin composition is cured to form a cured film of the coating film, and the cumulative irradiation amount is 1..i, 200 inJ/cm2. As a result, the cured film layer of the curable resin composition of the present invention can be obtained in order. (Cerane coupling treatment surface) polarizing element (no decane coupling treatment surface) / PVA type adhesive / TA c / adhesive / glass of the polarizing plate of the present invention. Example 2 In Example 1, coating was obtained by a spin coater The curable resin composition was produced in the same manner as in Example 之外 except that the film thickness after hardening was 5 # m, and the cured layer formed of the hard deuterated resin composition of the present invention was obtained. Board. 3, as shown in Table 1 below, in Example 1, except that 50 parts by weight of a cage-type decylated polyphenylene oxybendane having a methacryloxy group obtained in the synthesis example was used; a substituted amine group A Acid ester acrylate oligomer (manufactured by Kyoeisha Chemical Co., Ltd., trade name: UF-503), 5 parts by weight of urethane acrylate oligoacrylate (manufactured by Kyoeisha Chemical Co., Ltd., product Name: UF-8001) l parts by weight; and substituted dicyclopentyl diacrylate (tricyclo[5. 2. 1. 〇2,6]) decane dimethylol diacrylate) 65 parts by weight Dicyclopentyldiacrylic acid vinegar (tricyclo[5. 2. 1. 〇2'6]) 癸 二 二 曱 二 diacetic acid vinegar) 20 parts by weight and trimethyl methacrylate triacrylate 20 weight In the same manner as in Example 1, except that the curable resin composition of the present invention was obtained, the polarizing plate of the invention was produced. Example 4 As shown in Table 1 below, in Example 1, 25 parts by weight of a cage-type decylated polyphenylsesquioxane having a mercaptopropenyloxy group obtained in Synthesis Example 32181 45 201038681 was used; Substituted amino phthalate acrylate oligomer (manufactured by Kyoeisha Chemical Co., Ltd., trade name: UF-503) 5 parts by weight of amino phthalate acrylate oligomer (Kyoeisha Chemical Co., Ltd.) , trade name: UF-8001) 10 parts by weight; and substituted dicyclopentyl diacrylate (tricyclo[5. 2. 1. 02'6]) decane dimethylol diacrylate) 65 parts by weight 15 parts by weight of dicyclopentyl diacrylate (tricyclo[5.2.1.02'6]) decane dihydroxymethyl diacrylate) and 50 parts by weight of diisopentyl alcohol triacrylate, thereby obtaining the present invention A polarizing plate of the invention was produced in the same manner as in Example 1 except for the curable resin composition. Example 5 As shown in Table 1 below, in Example 1, except that 20 parts by weight of a cage-type decylated polyphenylsesquioxane having a methacryloxy group obtained in the synthesis example was used; an amine group Acid ester acrylate oligomer (manufactured by Kyoeisha Chemical Co., Ltd., trade name: UF-503) 12 parts by weight; and substituted dicyclopentyl diacrylate (tricyclic [5. 2. 1. 02'6) ]) decane dihydroxydecyl diacrylate) 65 parts by weight of dicyclopentyl diacrylate (tricyclo[5. 2. 1. 02'6]) decane dihydroxydecyl diacrylate) 32 weight A polarizing plate of the present invention was produced in the same manner as in Example 1 except that 36 parts by weight of diisopentyl alcohol triacrylate was used and the curable resin composition of the present invention was obtained. The compositions of the curable resin compositions of the present invention obtained in Examples 1 to 5 are shown in Table 1. 46 321811 201038681 [Table 1] ------- Example 1 2 3 4 5 Anthranone Resin (A) Compound 30 obtained by Synthesis Example 30 50 25 20 Concentrate (B) Amino acid oligosaccharide Polymer UF-503 5 5 12 urethane condensate UF-8001 10 10 unsaturated compound (C) dicyclopentyl diacrylate (tricyclo[5. 2. 1. 02'6] decane Dimethylol diacrylate) 65 65 20 15 32 Trimethylolpropane triacrylate 20 ----- 50 ------- 36 Diisodecyl alcohol triacrylic acid SI photopolymerization initiator 1 -hydroxycyclohexyl phenyl ketone 2 2 2 2 2 bis(2,4,6-trimethylbenzylidene)-phenylphosphine oxide 1 1 1 1 1 UV absorber Tinuvin 384-2 4 4 4 4 4 light stabilizer bis (1, 2, 2, 6, 6-pentamethyl-4-hexahydropiperidyl) sebacate 1 1 1 - 1 1 1 antioxidant isovaerythritol tetra [3- (3,5-di-t-butyl-4-hydroxyphenyl)propionate 1 1 1 - 1 Example 6 Except that a PVA-based resin film adsorbed with iodine (iodo-multivalent ion) was used to stretch 〇 The pre-advanced component ((P) made by Polatechno 'SKN with pva component) as the polarizing component Example 1 The same method for preparing a polarizing plate of the present invention. Example 7 A polarizing element (manufactured by P〇latechno, a pva element for SKN) which is obtained by stretching a PVA-based resin film which adsorbs iodine (iodo-multivalent ion) is used as a polarizing element. The polarizing plate of the invention was produced in the same manner as in Example 3. Example 8 321811 47 201038681 In addition to a polarizing element (PVA element manufactured by Polatechno, SKN) manufactured by stretching a PVA-based resin film adsorbed with iodine (iodo-multivalent ion) as a polarizing element, The polarizing plate of the invention was produced in the same manner as in Example 4. Example 9 A polarizing element (a PVA element manufactured by Polatechno, a PVA element for SKN) which was obtained by stretching a PVA-based resin film adsorbed with iodine (iodo-polyvalent ion) was used as the polarizing element, and the rest was in accordance with Example 5. The polarizing plate of the invention was produced in the same manner. Example 10 In Example 1, except that a cycloolefin film (Zeonor, manufactured by Zeon Co., Ltd.) was used in place of the TAC film and stretched using a PVA-based resin film of adsorbed moth (moth polyvalent ion) A polarizing plate of the invention was produced in the same manner as in Example 之外 except that a polarizing element (manufactured by P〇latechn Co., Ltd., a PVA element for SKN) was used as the polarizing element. Comparative Example 1 According to the description of Example 0 of WO2008-066157, the cage-type cerium-oxygenated polyphenyl sesquioxane having a methacryloxy group obtained in the above-mentioned synthesis example: 30 parts by weight, an amine group Phthalate acrylate oligomer (manufactured by Kyoeisha Chemical Co., Ltd., trade name: UF-503): 5 parts by weight of dicyclopentyl diacrylate (tricyclo[5.2.1.02,6]) decane Dimethylol diacrylate): cation parts by weight and 1-cyclohexyl phenyl ketone: 2 parts by weight of an anthrone resin composition, which is cast on a PET film and then subjected to light irradiation (high pressure) Mercury lamp, wavelength 320nm, irradiation time 3 seconds) and hardened, can obtain a film thickness of 2 〇〇 # m 321811 48 201038681. A decane coupling agent (trade name: ΚΒΕ-9007, manufactured by Shin-Etsu Chemical Co., Ltd.) was coated on the film to have a thickness of 1. 〇#m' after drying to obtain a polarizing plate for forming a decane coupling agent layer. After the protective film, the protective film is bonded to the polarizing element formed of the PVA film by a PVA-based adhesive, and the polarizing plate is obtained after drying. Comparative Example 2 In addition to 50 parts by weight of KAYARADrtm-MANDA (manufactured by Nippon Chemical Co., Ltd., hydroxyindole trimethylglycolic acid neopentyl glycol diacrylate), KAYARADTM-TMPTA (Nippon Chemical Co., Ltd., III) 50 parts by weight of hydroxymethylpropane triacrylate) and 5 parts by weight of a resin composition uniformly mixed with DarocurRTM 1173 (photopolymerization initiator, manufactured by Ciba Specialty Chemicals Co., Ltd.) to replace the curable resin obtained in Example 1. The rest of the composition was produced into a polarizing plate by the same operation as in Example 6. Test Example 1 Q <Evaluation Test of Adhesion> The test samples for peeling were used at one end of the polarizing plates obtained in Examples 1 to 5 and Comparative Example 1, and the peeled polarizing element and the protective film were stretched while being peeled off. At an angle of 90 ° C, the blade was inserted into the back surface while confirming the adhesion of both surfaces with an optical magnifying glass to confirm whether or not the film was peeled off. In the polarizing plates obtained in Examples 1 to 5, in the bonding surface between the polarizing element and the cured film of the coating film, the blade was not inserted, and if it was hard to be inserted into the blade, the cured film of the coating film was broken, so that the coating film was formed. The cured film cannot be peeled off from the surface of the polarizing element. 321811 49 201038681 On the other hand, in Comparative Example 1, since the blade was inserted into the subsequent surface by the above method, the subsequent cured film was easily peeled off from the surface of the polarizing element. Test Example 2 &lt;Evaluation Test of Moisture and Heat Resistance&gt; After measuring the initial transmittance and the initial polarization degree of the polarizing plates obtained in Examples 6 to 10 and Comparative Example 2, each polarizing plate was subjected to 85 ° C and 85% RH. After 72 hours under the damp heat test conditions, the transmittance and the degree of polarization after the damp heat test were measured. The obtained measurement results are shown in Table 2. [Table 2] Initial transmittance (3⁄4) Initial polarization (%) Transmittance after wet heat test (%) Polarization after wet heat test (%) Example 6 41. 76 99. 98 44. 71 99. 24 Implementation Example 7 41.44 99. 99 44. 56 99. 41 Example 8 41. 86 99. 99 45. 12 99. 09 Example 9 41. 39 99. 99 44, 89 98. 67 Example 10 41. 70 99. 99 44.48 99. 63 Comparative Example 2 41. 74 99. 98 72. 31 45. 32 From the above examples and comparative examples, it is known that at least on one side of the polarizing element, there is a polyorganic half which has a cage structure. In the polarizing plate of the present invention, the polarizing plate of the curable resin composition of the polymerizable resin compound containing a siloxane component as a main component, the polarizing plate of the present invention can be made thinner than 5/m. The adhesion is good, and the long-term stability after the constant temperature and humidity test is also high. [Industrial Applicability] The polarizing plate of the present invention can be made thinner in accordance with the protective film, and at the same time, the heat resistance of the film is also excellent. Further, even when used under severe conditions, the protective film (layer_) is not peeled off, the shrinkage of the polarizing plate is small, and the deterioration of optical characteristics such as the degree of polarization is small. Further, the polarizing plate of the present invention has a feature that the process can be simplified and the long article can be easily curled. Therefore, the polarizing plate of the present invention can be applied to a polarizing plate of a liquid crystal display used under normal conditions, and can also be applied to a polarizing plate such as a liquid crystal projector used under severe conditions. Further, since a cycloolefin film is used as a support on one surface of the polarizing element, it is of course possible to improve the durability of the polarizing plate of the present invention. In addition, since the hardened film or the like of the curable resin composition of the present invention can exhibit the above-described excellent characteristics by using a protective film or the like of the above polarizing film, it can be applied to members for electric/electronics and the like. Protective film and other uses. [Simple description of the diagram] None. [Main component symbol description] None. 51 321811

Claims (1)

201038681 VII. Patent application scope: 1. A polarizing plate comprising a hardened resin composition having a curable resin composition on one or both sides of a polarizing element, the curable resin composition containing the formula (1) And in the structural unit, the fluorenone resin (A) having a cage structure of polyorganosiloxanes as a main component (A) 5 to 80% by weight and the radical polymerizable unsaturated compound 95 to 20% by weight, [RS 1 〇3/2] η (1) (wherein R is an organic functional group having a (fluorenyl) acryl fluorenyl group, and η is 8, 10 or 12). 2. The polarizing plate of claim 1, wherein the polyorganosiloxanes having a cage structure are contained in an amount of from 50 to 100% by weight based on the total amount of the fluorenone resin (Α). 3. The polarizing plate of claim 1, wherein the curable resin composition contains (i) an anthrone resin (Α), and (ii) an amine group capable of radical polymerization with an anthrone resin (Α) The oligomer of the formate bond (B) is used as a radically polymerizable unsaturated compound. 4. The polarizing plate of claim 3, wherein the curable resin composition is a radically polymerizable unsaturated compound, in addition to (iii) the oligomer (B), and contains Ketone resin (A) Free-radical copolymerized unsaturated compound (C). 5. The polarizing plate of claim 4, wherein the unsaturated compound (C) is an alicyclic bis(indenyl)acrylate (C') represented by the following formula (2), 52 321811 201038681 C2) (wherein Z represents any of the groups represented by (2a) or (2b), and r represents a hydrogen atom or a mercapto group). 6. The polarizing plate of claim 3, wherein the oligomer (6) contains at least one -R -CR = CH2 or -CR4 = CH2 in the knife (wherein r3 represents an aliphatic carbon number of 1 to A compound having a divalent crosslinking group of 6 or an -OCO- group, P represents an unsaturated group represented by a halogen atom or a C1 to C6 alkyl group and having a number average molecular weight of 1, 〇〇〇 to 1 〇, 〇〇〇. 7. The polarizing plate of claim 4, wherein the fluorenone resin (A), the oligomer (B), and the unsaturated compound are contained in a weight ratio of 5 to 8 Å: j to 50: 10 to 80 ( c). The polarizing plate according to any one of the items of the present invention, wherein the surface of the polarizing element which is subjected to the light-breaking treatment is provided with a hardening resin composition. 9. The polarizing plate of the eighth aspect of the patent application, wherein the cerium-burning coupling agent for the decane coupling treatment is a (meth)acrylic decane coupling agent. The polarizing plate of claim 1, wherein the polarizing element is formed of a polyvinyl alcohol-based resin film containing a dichroic dye. U. The polarizing plate of claim 2, wherein one of the polarizing elements 321811 53 201038681 has a cured film of a curable resin composition on the other surface and a support on the other side. 12. The polarizing plate of claim 5, wherein the support body is a film formed of TAC or a cyclic olefin polymer. 13. - A liquid money display device characterized by having a polarizing plate of any one of the patent applications from the 12th to the 12th. 14. A liquid crystal display according to claim 13 of the patent application, wherein two polarizing plates of the U-application patent range are clamped to the liquid crystal cell and disposed on both sides of the 'cursive resin composition'. The film is a composition of the first two kinds of chemical resins, and contains: (1) a compound represented by the formula (1). The number of average molecules 1 in the free-radical polymerization of the phase resin (A) and the phase resin (A) having the cage structure of the polyorganosilsesquioxane as the main component 1, 〇〇〇 to 10, _ urethane bond oligomer (8), t) in addition to the above-mentioned polymer (8), can be combined with the external tree (A) free volume /, polymerization Unsaturated compound (C) and (1) photopolymerization initiator, wherein:::, the compound (A), the oligomer (8) and the unsaturated compound (6), the heart (weight) 'these compounds The content is 10 to 55% by weight of the resin (A), 3 to 30% by weight of the oligomer (B), and the residual portion is the unsaturated compound (c), and the photopolymerization initiator is relative to The total (I) to I() of the above (A) to (C) is 1 321 811 54 201038681 to 6% by weight, CRS i 〇 3/2] n ( 1 ) (wherein R is (meth) propylene The organic functional group of the fluorenyl group, η is 8 10 or 12). And compound (C), The curable resin composition of claim 15, wherein at least 1% by weight of the alicyclic di(methyl) group represented by the following formula (2) is contained in an amount of at least 1% by weight based on the total amount of the unsaturated compound (C) Acrylic vinegar (c,) is not saturated (wherein Z represents any one represented by (2a) or (2b), and R represents a hydrogen atom or a methyl group). 17. The curable resin composition of claim 16, wherein the unsaturated compound (c) is an alicyclic di-methyl)acrylic acid S (C') represented by the formula (2). Or the alicyclic di(meth) acrylate (〇盥 肪 aliphatic polyfunctional (meth) acrylate can be used together. ^ 321811 55 201038681 IV. Designated representative figure: There is no drawing in this case. The picture is: ( ) Figure - (2) The symbol of the symbol of this representative figure is simple: ❹ 5. If there is a chemical formula in this case, please reveal the chemical formula that best shows the characteristics of the invention: [RS i 〇3/2] n ( 1) 〇3 321811 201038681 (Please do not change the format and order of this manual, please do not fill in the ※ part) ※ ※Application number: Μ 〖. Fighting ^ ^ "200101: ※Application date: 赃. · Classification:灰灰. (10)F献q赞i?月丨壮-------- 〇f &gt; I. Invention name) (Chinese / English) Polarizing plate with fluorenone-coated hardened film and using the polarizing plate LCD display gel%% ” POLARIZING PLATE HAVING A SILICONE COATED HARDENE D FILM AND A LIQUID CRYSTAL DISPLAY DEVICE _ , /jra V I. Abstract: ο The present invention relates to the use of a coating cured film or the like having a composition of a curable resin as a polarizing light on at least one side of a polarizing element. A polarizing plate made of a protective film of a component, the curable resin composition characterized by containing a polyorganopene oxide having a cage structure as a main component in the structural unit and having a cage structure. Ketone resin (Α). The wet heat durability, adhesion, optical property stability, workability and surface hardness of the polarizing plate of the present invention are excellent. For example, the use of the polarizing plate of the present invention can improve, for example, a liquid crystal projector. The display quality of the display is maintained while maintaining a stable image display. [Rsi〇3/2]B (1); a弋 'R疋 denotes an organic functional group having a (meth)acryloyl group, η is δ, 1〇 Or 12). 321811 1 201038681 (The format and order of this manual should not be changed at all, please do not fill in the ※ part of the mark) ' ※Application number: Μ 〖. Fighting ^ ^ "200101: ※Application date: 赃. :Mystery. (10)F q赞i?月丨壮-------- 〇f &gt; I. Invention name) (Chinese/English) Polarizing plate with an anthrone-based coating hardening film and a liquid crystal display using the polarizing plate % ” POLARIZING PLATE HAVING A SILICONE COATED HARDENED FILM AND A LIQUID CRYSTAL DISPLAY DEVICE _ , /jra V I. Abstract of the Invention: ο The present invention relates to the use of a curable resin at least on one side of a polarizing element. A polarizing plate which is a protective film of a polarizing element, such as a coating cured film of a composition, and the curable resin composition is characterized by containing a polyorganic compound having a cage structure and represented by (1) Anthrone resin (Α) containing aspirin as a main component. The wet heat durability, the adhesion, the optical property stability, the workability, and the surface hardness of the polarizing plate of the present invention are excellent. For the use of the polarizing plate of the present invention, for example, the display quality of a liquid crystal projector 7-display can be improved. Maintain a stable image display. [Rsi 〇 3/2] B (1); a ’ ' R 疋 denotes an organic functional group having a (meth) acryl fluorenyl group, and η is δ, 1 〇 or 12). 321811 1