Polarizing plate

Abstract

To provide a polarizing plate capable of minimizing the reduction in polarizing performance of a polarizing film even when incorporated into the viewing side of an organic EL image display device, for example, and used outdoors.SOLUTION: A vertical polarizing plate (1) of the present invention comprises an ultraviolet absorbing film (2) and a polarizing film (4) having a dichroic dye vertically oriented therein, laminated in the described order, where the ultraviolet absorbing film (2) has a light transmittance (T300) of 1% or less at a 300 nm wavelength. a light transmittance (T380) of 10% or less at a 380 nm wavelength, a light transmittance (T400) of 20% or less at a 400 nm wavelength, and a light transmittance (T450) of 80% or greater at a 450 nm wavelength.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a polarizing plate. [Background technology]

[0002] A polarizing film is known that is made of a cured product obtained by curing a composition containing a polymerizable liquid crystal compound and a dichroic dye, and in which the dichroic dye is oriented in one direction (Patent Document 1).A polarizing plate in which a resin film is laminated on this polarizing film is also known.

[0003] This polarizing film has an absorption axis and a transmission axis based on the orientation of the dichroic dye, and absorbs polarized light components whose vibration plane is parallel to the absorption axis and transmits polarized light components whose vibration plane is perpendicular to the transmission axis. Such polarizing films, in which the dichroic dye is oriented in-plane and a resin film is laminated, are often incorporated into the viewing side of organic EL image display devices for outdoor use, for example. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2020-46622 Summary of the Invention [Problem to be solved by the invention]

[0005] However, it has been found that when an organic EL image display device incorporating a polarizing plate, in which a polarizing film and a resin film are laminated, is installed on the viewing side, the polarization performance is likely to deteriorate when used outdoors.

[0006] Therefore, the present inventors conducted extensive research to develop a polarizing plate that suppresses deterioration in the polarization performance of the polarizing film even when the polarizing plate is incorporated into the viewing side of an organic EL image display device and used outdoors, and as a result, they found that a polarizing plate in which an ultraviolet-absorbing film exhibiting a predetermined light transmittance is laminated on a polarizing film can solve these problems, thereby arriving at the present invention. [Means for solving the problem]

[0007] That is, the polarizing plate (1) of the present invention comprises an ultraviolet absorbing film (2) and a polarizing film (4) in which a dichroic dye is in-plane oriented; and a polarizing plate (1) in which the polarizing film (4) is laminated in this order. The ultraviolet absorbing film (2) is Light transmittance at a wavelength of 300 nm (T 300 ) is 1% or less, Light transmittance at a wavelength of 380 nm (T 380 ) is 10% or less, Light transmittance at a wavelength of 400 nm (T 400 ) is 20% or less, Light transmittance at a wavelength of 450 nm (T 450 ) is 80% or more When the light transmittance of the ultraviolet absorbing film (2) is within the above range, ultraviolet rays reaching the polarizing film (4) can be suppressed, and deterioration of the polarization performance can be suppressed.

[0008] The ultraviolet absorbing film (2) constituting the polarizing plate (1) of the present invention has a light transmittance (T 400 ) to the light transmittance at a wavelength of 450 nm (T 450 ) ratio (T 450 / T 400 ) is preferably 10 or more, more preferably 30 or more. 450 / T 400 ) is usually 100,000 or less. When the ultraviolet absorbing film (2) has such a ratio (T 450 / T 400 ), it is possible to sufficiently cut out the so-called near ultraviolet (400 nm), which is close to visible light among ultraviolet rays, while sufficiently transmitting light around 450 nm, which is close to ultraviolet among visible light. 450 / T 400 ) is 10 or greater, T 450 is more than 80%, so T 400 is less than 8%.

[0009] The dichroic dye oriented in the polarizing film (4) constituting the polarizing plate (1) of the present invention is represented by the formula (A) [ka] [wherein * indicates a linking moiety, R1 and R2 are each independently a halogen atom or a methyl group (-CH3), n and m each independently represent an integer of 0 to 4; R3 and R4 each independently represent an alkyl group which may have a substituent, or R3 and R4 combine with each other to form an alkenyl group. In the case of a dichroic dye containing a structure represented by the formula: wherein the polarizing performance has been prone to decrease when used outdoors, the effect of the present invention is more effectively exhibited.

[0010] The ultraviolet absorbing film (2) constituting the polarizing plate (1) of the present invention may comprise a resin film (21) and an ultraviolet absorbing layer (22) provided thereon. In this case, the resin film (21) Light transmittance at a wavelength of 300 nm (T 300F ) is 1% or less, Light transmittance at a wavelength of 380 nm (T 380F ) is 10% or less, Light transmittance at a wavelength of 450 nm (T 450F ) is over 80%, but Light transmittance at a wavelength of 400 nm (T 400F Even if the light transmittance (T 400A If the light transmittance (T) of the ultraviolet absorbing layer (22) is sufficiently small, the ultraviolet absorbing film (2) of the present invention can be satisfied. 400A) sufficiently small, it is desirable to blend an ultraviolet absorber that has a maximum absorption wavelength around 400 nm and can efficiently absorb near-ultraviolet rays. If the ultraviolet absorbing layer (22) contains such an ultraviolet absorber, the light reflectance on the surface tends to increase. For this reason, it is preferable that the ultraviolet absorbing layer (22) be provided on the polarizing film (4) side.

[0011] In the polarizing plate (1) of the present invention, it is preferable that an oxygen barrier layer (3) is interposed between the ultraviolet absorbing film (2) and the polarizing film (4). By interposing the oxygen barrier layer (3), deterioration of the dichroic dye polarizing performance can be effectively suppressed.

[0012] Here, the oxygen barrier layer (3) may be laminated directly to the ultraviolet absorbing film (2) or may be laminated only via an adhesive layer (not shown).Furthermore, the oxygen barrier layer (3) may be laminated directly to the polarizing film (4) or may be laminated only via an adhesive layer (not shown). The oxygen barrier layer (3) is usually a polyvinyl alcohol-based resin layer.

[0013] The polarizing plate (1) of the present invention may be formed into a circular polarizing plate (6) by laminating a retardation plate (5) on the polarizing film (4) on the side opposite to the ultraviolet absorbing film. [Effects of the Invention]

[0014] The polarizing plate (1) of the present invention can suppress the deterioration of the polarization performance. [Brief explanation of the drawings]

[0015] [Figure 1] FIG. 1 is a cross-sectional view schematically illustrating an example of a polarizing plate of the present invention. [Figure 2] FIG. 2 is a cross-sectional view schematically showing another example of the polarizing plate of the present invention. [Figure 3] FIG. 1 is a cross-sectional view schematically illustrating an example of a circularly polarizing plate in which a retardation plate is laminated on the polarizing plate of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0016] As shown in FIG. 1, the polarizing plate (1) of the present invention comprises an ultraviolet absorbing film (2) and a polarizing film (4) laminated in this order.

[0017] [UV absorbing film] The ultraviolet absorbing film (2) is a film that absorbs ultraviolet rays but transmits visible light. The ultraviolet absorbing film (2) may be a resin film obtained by molding a resin composition, for example, a thermoplastic resin containing an ultraviolet absorber, into a film. Such ultraviolet absorbing films may be commercially available.

[0018] The ultraviolet-absorbing film (2) may be a film in which an ultraviolet-absorbing layer (22) is formed on one or both sides of a resin film (21) made of a thermoplastic resin or the like, as shown in Fig. 2. The ultraviolet-absorbing layer (22) is, for example, a cured product layer of a curable composition in which an ultraviolet absorber is blended with a curable resin. Such a cured product layer can be formed by applying a curable resin composition onto a resin film to obtain a coating film, and then curing this coating film.

[0019] [Resin film] Examples of the resin film (21) include plastics such as polyolefins such as polyethylene, polypropylene, and norbornene-based polymers; cyclic olefin-based resins; polyvinyl alcohol; polyethylene terephthalate; polymethacrylic acid esters; polyacrylic acid esters; cellulose esters such as triacetyl cellulose, diacetyl cellulose, and cellulose acetate propionate; polyethylene naphthalate; polycarbonate; polysulfone; polyether sulfone; polyether ketone; polyphenylene sulfide; and polyphenylene oxide. Among these, a film substrate selected from triacetyl cellulose, cyclic olefin-based resins, polymethacrylic acid esters, and polyethylene terephthalate is more preferred from the viewpoint of transparency when used in optical film applications.

[0020] The thickness of the resin film (21) is usually 5 μm to 200 μm, preferably 7 μm to 100 μm, and more preferably 10 to 50 μm.

[0021] [Curable resin composition] [Curable resin] The curable resin constituting the curable resin composition is a resin that can form a cured product layer by curing with heat or light. Specific examples include organic hard coat materials such as organic silicone-based, melamine-based, epoxy-based, (meth)acrylic-based, and urethane (meth)acrylate-based materials, and inorganic hard coat materials such as silicon dioxide. Among these, urethane (meth)acrylate-based or polyfunctional (meth)acrylate-based curable resins are preferably used from the viewpoints of adhesion and hardness.

[0022] [Ultraviolet absorber] Examples of the ultraviolet absorber that can be incorporated into the curable resin composition include benzotriazole-based ultraviolet absorbers and hydroxyphenyltriazine-based ultraviolet absorbers.

[0023] The content of the ultraviolet absorber in the curable resin composition is usually 1 part by weight or more, preferably 3 parts by weight or more, and more preferably 5 parts by weight or more, relative to 100 parts by weight of the curable resin, in order to facilitate sufficient absorption of ultraviolet light, and usually 30 parts by weight or less, preferably 15 parts by weight or less, and more preferably 5 parts by weight or less, in order to facilitate avoiding the phenomenon known as bleed-out, in which the ultraviolet absorber seeps out of the ultraviolet absorbing layer.

[0024] [UV absorbing film composed of a resin film and a UV absorbing layer] As shown in FIG. 2, when the ultraviolet absorbing film (2) comprises a resin film (21) and an ultraviolet absorbing layer (22) provided thereon, the light transmittance (T 300F ) is 1% or less, and the light transmittance at a wavelength of 380 nm (T 380F ) is 10% or less, and the light transmittance at a wavelength of 450 nm (T450F ) is 80% or more, and the light transmittance at a wavelength of 400 nm (T 400F In this case, the light transmittance (T 400A If the light transmittance (T) is sufficiently small, the ultraviolet absorbing film (2) specified in the present invention can be satisfied. 400A When the ultraviolet absorbing layer (22) contains an ultraviolet absorber so as to sufficiently reduce the reflection of light on the polarizing plate surface, it is preferable that the ultraviolet absorbing layer (22) is provided on the polarizing film (4) side, since this can suppress light reflection on the polarizing plate surface, compared to when the ultraviolet absorbing layer (22) is provided on the opposite side to the polarizing film (4).

[0025] The ultraviolet absorbing film (2) may also be configured such that both sides of the ultraviolet absorbing layer (22) are laminated with the resin film (21) directly or via a pressure-sensitive adhesive layer.

[0026] [Oxygen Barrier Layer] As shown in Fig. 1, the polarizing plate (1) of the present invention may have an oxygen barrier layer (3) between the ultraviolet absorbing film (2) and the polarizing film (4). This oxygen barrier layer (3) is laminated directly to the ultraviolet absorbing film (2) or laminated only via an adhesive layer (not shown). Also, this oxygen barrier layer (3) is laminated directly to the polarizing film (4) or laminated only via an adhesive layer (not shown).

[0027] [From UV absorbing film to oxygen barrier layer] The ultraviolet absorbing film to the oxygen barrier layer may be formed, for example, by a compound represented by the following formula (XI): [ka] It is preferable that the compound (XI) is represented by the following formula:

[0028] In the above formula (XI), A represents a methylene group, a secondary amino group, an oxygen atom, or a sulfur atom. From the viewpoint of exhibiting high light selective absorption, A preferably represents a methylene group, a secondary amino group, or an oxygen atom.

[0029] In the above formula (XI), R 1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. R 1 represents an alkyl group having preferably 1 to 8 carbon atoms, more preferably 1 to 5 carbon atoms, and even more preferably 1 to 3 carbon atoms, from the viewpoint of exhibiting high light-selective absorption. Here, when the alkyl group has at least one methylene group, at least one of the methylene groups may be substituted with an oxygen atom or a sulfur atom. Examples of such alkyl groups include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-hexyl group, an n-octyl group, an n-decyl group, a methoxy group, an ethoxy group, and an isopropoxy group.

[0030] In the above formula (XI), R 2 and R 3 R each independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. 2 and R 3 From the viewpoint of exhibiting high light selective absorption, each independently preferably represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, even more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

[0031] In the above formula (XI), R 4 represents an alkyl group having 3 to 50 carbon atoms, or an alkyl group having 3 to 50 carbon atoms and at least one methylene group, at least one of the methylene groups being substituted with an oxygen atom.

[0032] R 4 In terms of affinity with hydrophobic substances, solubility in hydrophobic solvents, and production economy, the alkyl group having 3 to 50 carbon atoms preferably has 8 to 45 (e.g., 10 to 45), more preferably 12 to 40, still more preferably 13 to 35, and particularly preferably 14 to 30 carbon atoms. A substituent may be bonded to the carbon atom on the alkyl group.

[0033] R 4 In the above, the alkyl group having 3 to 50 carbon atoms and at least one methylene group preferably has 3 to 40 carbon atoms, more preferably 4 to 35 carbon atoms, and particularly preferably 5 to 30 carbon atoms, from the viewpoints of affinity with hydrophobic substances, solubility in hydrophobic solvents, and production economy. In the alkyl group having 3 to 50 carbon atoms and at least one methylene group, at least one of the methylene groups is substituted with an oxygen atom, and examples thereof include an ethoxy group, a propoxy group, and a 2-methoxyethoxymethyl group. Other examples include polyethylene glycol groups such as a diethylene glycol group and a triethylene glycol group, and polypropylene glycols such as a dipropylene glycol group and a tripropylene glycol group.

[0034] Also, R 4 A substituent may be bonded to the carbon atom on the alkyl group. Examples of the substituent include a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, an alkylsulfinyl group having 1 to 6 carbon atoms, an alkylsulfonyl group having 1 to 6 carbon atoms, a carboxyl group, a fluoroalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an N-alkylamino group having 1 to 6 carbon atoms, an N,N-dialkylamino group having 2 to 12 carbon atoms, an N-alkylsulfamoyl group having 1 to 6 carbon atoms, and an N,N-dialkylsulfamoyl group having 2 to 12 carbon atoms.

[0035] R 4 When R is an alkyl group having 3 to 50 carbon atoms, in terms of affinity with hydrophobic substances and solubility in hydrophobic solvents, 4 is more preferably an alkyl group having a branched structure and having 3 to 12 carbon atoms, and even more preferably an alkyl group having a branched structure and having 6 to 10 carbon atoms.

[0036] Here, the alkyl group having a branched structure refers to an alkyl group in which at least one of the carbon atoms of the alkyl group is a tertiary carbon or a quaternary carbon. Specific examples of the alkyl group having a branched structure and 3 to 12 carbon atoms include alkyl groups having the following structure: [ka] * indicates a connecting part.

[0037] In the above formula (XI), X 1 represents an electron-withdrawing group. From the viewpoint of improving the light selective absorption, X 1 -NO2, -CN, -COR 8 , -COOR 9 , -OR 10 , halogen atoms (-F, -Cl, -Br, -I), -CSR 11 , -CSOR 12 , or -CSNR 13 is preferred, and a nitro group, a cyano group, or -COOR 9 is more preferred, and a cyano group or -COOR 9 More preferably, R 8 , R 9 , R 10 , R 11 , R 12 and R 13 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, for example, 2 to 5 carbon atoms, or a phenyl group.

[0038] In the above formula (XI), Y 1 -CO-, -COO-, -OCO-, -O-, -S-, -NR 5 -, -NR 6 CO-, -CONR 7 From the viewpoint of improving the selective light absorption, R preferably represents -CO-, -COO-, -OCO-, or -O-, and more preferably represents -CO-, -COO-, or -OCO-. 5 , R 6 and R 7each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, for example, 2 to 5 carbon atoms, or a phenyl group.

[0039] In a preferred embodiment of the present invention, the compound (XI) represented by the above formula (XI) is a compound represented by the following formula (XI-I): [ka] From the viewpoint of excellent solubility in various solvents and / or affinity with various compounds, it is preferable that the compound be represented by the following formula:

[0040] In the above formula (XI-I), R 4-1 represents an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 2 to 5 carbon atoms, and more preferably an alkyl group having 3 or 4 carbon atoms. n is an integer of 1 to 10, and from the viewpoint of excellent solubility in various solvents and / or affinity with various compounds, preferably an integer of 1 to 8, more preferably an integer of 1 to 6, for example, an integer of 1 to 4, particularly an integer of 1 to 3. When n is within the above range, the light absorption per part by mass is improved, and even if the amount of compound (XI) contained in the members constituting the optical laminate is small, the blue light blocking function can be exhibited. Furthermore, when compound (XI) is contained in a pressure-sensitive adhesive, for example, the pressure-sensitive adhesive function is unlikely to be impaired, and when compound (XI) is contained in a protective film, the optical function of the protective film is unlikely to be impaired. A, R 1 , R 2 and R 3 is the same as in the above formula (XI).

[0041] In a more preferred embodiment of the present invention, the compound represented by the above formula (XI-I) is represented by the following formula (XI-II): [ka] When the compound represented by formula (XI-I) is a compound represented by formula (XI-II), it has excellent solubility in various solvents and / or affinity with various compounds, making it easy to uniformly dissolve the compound in a solvent, and at the same time, it has excellent affinity with various compounds and exhibits amphiphilicity, so that when the compound is contained in a member constituting an optical laminate, it is less likely to bleed out and can stably exhibit a light-absorbing function.

[0042] In formula (XI-II), R 4-1 and n is the same as in formula (XI-I).

[0043] [Additives] The curable resin composition may contain various fillers as desired for the purposes of adjusting the refractive index, improving the flexural modulus, stabilizing the volume shrinkage rate, and further improving heat resistance, antistatic properties, antiglare properties, etc. The surface treatment layer may also contain additives such as an antioxidant, a light stabilizer, an antistatic agent, a leveling agent, and an antifoaming agent.

[0044] [Formation of coating film] The curable resin composition is usually diluted with a solvent and applied onto the resin film (21). After application, the solvent is volatilized and removed to form a coating film of the curable resin composition. Examples of solvents that can be used alone or in combination include known organic solvents, such as aromatic solvents such as toluene, xylene, and n-heptane; aliphatic solvents such as cyclohexane, methylcyclohexane, and ethylcyclohexane; ester solvents such as methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, and methyl lactate; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; and alcohol solvents such as methanol, ethanol, isopropyl alcohol, and n-propyl alcohol.

[0045] [Curing of coating film] By curing the coating film formed on the resin film (21) in this manner, an ultraviolet absorbing layer (22) is formed. As a result, as shown in FIG. 2, a polarizing plate (1) of the present invention can be obtained in which the ultraviolet absorbing film (2) includes the resin film (21) and the ultraviolet absorbing layer (22) provided on the polarizing film (4) side. To cure the coating film, a curing treatment appropriate for the curable resin used can be performed. Specifically, if the curable resin used is an ultraviolet-curable resin that cures upon irradiation with ultraviolet rays, ultraviolet light can be irradiated, and if the curable resin used is an electron-beam-curable resin that cures upon irradiation with electron beams, electron beams can be irradiated. If the curable resin used is a thermosetting resin that cures upon heating, the coating film can be heated. The irradiation intensity and irradiation time of the electron beam or ultraviolet light, and the heating temperature and heating time when curing by heating, are appropriately selected depending on the curable resin used.

[0046] [Ultraviolet absorbing layer] The thickness of the ultraviolet absorbing layer (22) that can be formed in this manner is usually 1 μm or more, preferably 1.5 μm or more, in terms of having sufficient strength and being able to absorb ultraviolet rays sufficiently, and is usually 10 μm or less, preferably 5 μm or less, in terms of thinning. The thickness of the ultraviolet absorbing layer (22) can be adjusted, for example, by the amount of solvent used for dilution; a larger amount of solvent makes it easier to make the layer thinner. A smaller amount of solvent used makes it easier to make the layer thicker. Furthermore, the thickness can be increased by applying an additional curable resin composition on the coating film obtained by drying.

[0047] [UV absorbing film] The thickness of the ultraviolet absorbing film (2) is the thickness of a single-layer film formed from a resin composition containing a thermoplastic resin and an ultraviolet absorber, or is the total thickness of the resin film (21) and the ultraviolet absorbing layer (22) when the ultraviolet absorbing film (2) is a film formed from a resin film (21) on the surface of the resin film (21). The thickness of the ultraviolet absorbing film (2) is usually 5 μm or more, preferably 7 μm or more, more preferably 10 μm or more, and usually 200 μm or less, preferably 100 μm or less, more preferably 50 μm or less.

[0048] [Oxygen Barrier Layer] The oxygen barrier layer (3) is a layer that blocks the permeation of oxygen (O2), and its oxygen permeability is usually 60 cm 3 / m 2 24hrs atm or less, preferably 50cm 3 / m 2 ·24hr·atm or less, more preferably 30cm 3 / m 2 24hrs atm or less. From the practical viewpoint of thickness, the lower limit is 0.001 cm 3 / m 2 24hrs atm or more, preferably 0.01cm 3 / m 2 24hrs·atm or more, preferably 0.05cm 3 / m 2 The oxygen barrier layer is usually transparent and colorless.

[0049] An example of such an oxygen barrier layer is a polyvinyl alcohol-based resin layer. The polyvinyl alcohol-based resin constituting the polyvinyl alcohol-based resin layer has a degree of saponification of usually 30 or more, preferably 70 or more, more preferably 90 or more, particularly preferably 95 or more, even more preferably 97 or more, and is usually 100 or less, because sufficient oxygen barrier performance can be easily obtained. The thickness of the oxygen barrier layer is usually 0.1 μm or more, preferably 0.5 μm or more, even more preferably 0.7 μm or more, because sufficient oxygen barrier performance can be easily obtained, and from the viewpoints of thinning and economy, it is usually 10 μm or less, preferably 5 μm or less, more preferably 3 μm or less, and especially preferably 1.5 μm or less.

[0050] [Formation of oxygen barrier layer (polyvinyl alcohol-based resin layer)] Such a polyvinyl alcohol-based resin layer can be formed, for example, by applying an aqueous solution of a polyvinyl alcohol-based resin to one side of the ultraviolet-absorbing film (2) and drying it by heating. The content of the polyvinyl alcohol-based resin in the aqueous solution is usually 0.5 to 20 parts, preferably 1 to 10 parts. The heating temperature is, for example, 70 to 100°C, and the heating time is, for example, 1 to 10 minutes.

[0051] When the ultraviolet absorbing film (2) is a resin film, a polyvinyl alcohol resin layer may be formed on one side of the resin film.

[0052] When the ultraviolet absorbing film (2) is a film in which an ultraviolet absorbing layer (22) is formed on one side of a resin film (21), the oxygen barrier layer (3) may be formed on the resin film (21) side or on the ultraviolet absorbing layer (22) side. The polyvinyl alcohol-based resin layer may be formed by applying an aqueous solution of the polyvinyl alcohol-based resin to one surface of the polarizing film (4) described below and drying it. It is preferable to subject the polarizing film (4) to a corona treatment in advance, as this can improve adhesion to the polyvinyl alcohol-based resin layer.

[0053] [UV transmittance from UV absorbing film to oxygen barrier layer] The light transmittance (T 380G ) is 10% or less, preferably 8% or less, more preferably 6% or less, particularly preferably 1% or less, and ideally 0 (zero)%. 380G By keeping T at 10% or less, it is possible to suppress the deterioration of polarization performance. 380G indicates the proportion of ultraviolet light (wavelength 380 nm) that is transmitted without being absorbed by the ultraviolet absorbing film (2) and the oxygen barrier layer (3) and reaches the polarizing film (4).

[0054] The light transmittance (T 400G) is preferably 10% or less, further preferably 5% or less, even more preferably 2% or less, particularly preferably 1% or less, and ideally 0 (zero)%, in order to further suppress deterioration of the polarization performance of the polarizing film (4).

[0055] On the other hand, the light transmittance (T 450G ) is ideally 100% so as not to inhibit blue light emission from the organic EL image display device, but is usually 70% or more, preferably 80% or more, more preferably 85% or more, and particularly preferably 88% or more.

[0056] [Polarizing film] The polarizing plate (1) of the present invention has a polarizing film (4). A dichroic dye is oriented within the polarizing film (4), which causes the polarizing film (4) to have an absorption axis in its plane and a transmission axis perpendicular to the absorption axis in its plane. Of the light incident on this polarizing film (4), polarized components whose vibration plane is parallel to the absorption axis are absorbed. Polarized components whose vibration plane is parallel to the transmission axis are transmitted. When the dichroic dye is oriented in its plane, the polarizing film (4) absorbs polarized components parallel to the absorption axis of light incident from the normal direction and transmits polarized components whose vibration plane is parallel to the transmission axis, functioning as a so-called linear polarizer.

[0057] [Polymerizable liquid crystal composition] The polarizing film (4) constituting the polarizing plate (1) of the present invention may be, for example, a cured layer made of a cured product of a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound having at least one polymerizable group and a dichroic dye.

[0058] [Polymerizable liquid crystal compound] In the polarizing plate (1) of the present invention, the polymerizable liquid crystal compound (hereinafter also referred to as "polymerizable liquid crystal compound (A)") contained in the polymerizable liquid crystal composition (hereinafter also referred to as "polymerizable liquid crystal composition (A)") forming the polarizing film (4) is a liquid crystal compound having at least one polymerizable group. Here, the polymerizable group refers to a group that can be involved in a polymerization reaction by an active radical generated from a polymerization initiator, an acid, or the like. Examples of the polymerizable group contained in the polymerizable liquid crystal compound (A) include a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group, a methacryloyloxy group, an oxiranyl group, and an oxetanyl group. Among these, a radically polymerizable group is preferred, an acryloyloxy group, a methacryloyloxy group, a vinyl group, or a vinyloxy group is more preferred, and an acryloyloxy group or a methacryloyloxy group is more preferred.

[0059] In the present invention, the polymerizable liquid crystal compound (A) is preferably a compound exhibiting smectic liquid crystallinity. By using a polymerizable liquid crystal compound exhibiting smectic liquid crystallinity, a polarizing film (4) with a high degree of orientational order can be formed. The liquid crystal state exhibited by the polymerizable liquid crystal compound (A) is a smectic phase (smectic liquid crystal state), and from the viewpoint of achieving a higher degree of orientational order, a high-order smectic phase (high-order smectic liquid crystal state) is more preferred. Here, the high-order smectic phase refers to a smectic B phase, a smectic D phase, a smectic E phase, a smectic F phase, a smectic G phase, a smectic H phase, a smectic I phase, a smectic J phase, a smectic K phase, or a smectic L phase. Among these, the smectic B phase, the smectic F phase, and the smectic I phase are more preferred. The liquid crystal property may be either thermotropic or lyotropic, but thermotropic liquid crystal is preferred because it allows precise control of the film thickness. The polymerizable liquid crystal compound (A) may be a monomer, or may be an oligomer or polymer in which a polymerizable group is polymerized.

[0060] The polymerizable liquid crystal compound (A) is not particularly limited as long as it is a liquid crystal compound having at least one polymerizable group, and any known polymerizable liquid crystal compound can be used, but a compound exhibiting smectic liquid crystallinity is preferred. Examples of such polymerizable liquid crystal compounds include a compound represented by the following formula (A1) (hereinafter also referred to as "polymerizable liquid crystal compound (A1)"). U 1 -V 1 -W 1 -(X 1 -Y 1 -) n -X 2 -W 2 -V 2 -U 2 (A1) [In formula (A1), X 1 and X 2 are each independently a divalent aromatic group or a divalent alicyclic hydrocarbon group, wherein a hydrogen atom contained in the divalent aromatic group or divalent alicyclic hydrocarbon group may be substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a nitro group, and a carbon atom constituting the divalent aromatic group or divalent alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom, provided that X 1 and X 2 At least one of the groups is an optionally substituted 1,4-phenylene group or an optionally substituted cyclohexane-1,4-diyl group. Y 1 is a single bond or a divalent linking group. n is 1 to 3, and when n is 2 or more, multiple X 1 may be the same or different. 2 Multiple X 1 In addition, when n is 2 or more, a plurality of Y 1 may be the same or different. From the viewpoint of liquid crystal properties, n is preferably 2 or more. U 1represents a hydrogen atom or a polymerizable group. U 2 represents a polymerizable group. W 1 and W 2 are each independently a single bond or a divalent linking group. V 1 and V 2 represent, independently of each other, an alkanediyl group having 1 to 20 carbon atoms which may have a substituent, and -CH2- constituting the alkanediyl group may be replaced by -O-, -CO-, -S- or -NH-.

[0061] In the polymerizable liquid crystal compound (A1), X 1 and X 2 are each independently preferably an optionally substituted 1,4-phenylene group or an optionally substituted cyclohexane-1,4-diyl group, and X 1 and X 2 At least one of these is an optionally substituted 1,4-phenylene group or an optionally substituted cyclohexane-1,4-diyl group, preferably a trans-cyclohexane-1,4-diyl group. The optionally substituted 1,4-phenylene group or the optionally substituted cyclohexane-1,4-diyl group may optionally have a substituent, such as an alkyl group having 1 to 4 carbon atoms, a cyano group, or a halogen atom, such as a chlorine atom or a fluorine atom. Preferably, the group is unsubstituted.

[0062] The polymerizable liquid crystal compound (A1) is a compound represented by the formula (A1) having the formula (A1-1): -(X 1 -Y 1 -) n -X 2 - (A1-1) [In the formula, X 1 , Y 1 , X 2 and n have the same meanings as above.] [hereinafter referred to as partial structure (A1-1)] is preferably an asymmetric structure in that smectic liquid crystallinity is easily exhibited.

[0063] The polymerizable liquid crystal compound (A1) in which the partial structure (A1-1) is an asymmetric structure is, for example, a compound in which n is 1 and one X 1 and X 2 and (A1) are different from each other in structure. n is 2 and two Y 1 are compounds having the same structure as each other, Two Xs 1 have the same structure as each other, and one X 2 These two X 1 a polymerizable liquid crystal compound (A1) having a structure different from that of Two Xs 1 Of the W 1 X binds to 1 But the other X 1 and X 2 The other X 1 and X 2 The above also includes polymerizable liquid crystal compounds (A1) having the same structure. moreover, n is 3 and there are three Y 1 are compounds having the same structure as each other, and three X 1 and one X 2 The polymerizable liquid crystal compound (A1) may be any one of the following three:

[0064] Y 1 -CH2CH2-, -CH2O-, -CH2CH2O-, -COO-, -OCOO-, single bond, -N=N-, -CR a =CR b -, -C≡C-, -CR a =N- or -CO-NR a - is preferred. a and R b are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 1is more preferably -CH2CH2-, -COO- or a single bond, and 1 If there is an X 2 Y bonded to 1 is more preferably -CH2CH2- or CH2O-. 1 and X 2 When all of Y are the same structure, two or more Y 1 It is preferable that there are plural Y 1 When the compound has an asymmetric structure, the compound tends to exhibit smectic liquid crystallinity.

[0065] U 2 is a polymerizable group. 1 is a hydrogen atom or a polymerizable group, preferably a polymerizable group. 1 and U 2 Preferably, both of U are polymerizable groups, and preferably both are radically polymerizable groups. Examples of the polymerizable group include the same groups as those exemplified above as the polymerizable group contained in the polymerizable liquid crystal compound (A). 1 and a polymerizable group represented by U 2 The polymerizable groups represented by may be different from each other, but are preferably the same type of group. The polymerizable groups may be in a polymerized state or an unpolymerized state, but are preferably in an unpolymerized state.

[0066] V 1 and V 2 Examples of the alkanediyl group represented by the formula (V) include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a decane-1,10-diyl group, a tetradecane-1,14-diyl group, and an icosane-1,20-diyl group. 1 and V 2 is preferably an alkanediyl group having 2 to 12 carbon atoms, and more preferably an alkanediyl group having 6 to 12 carbon atoms.

[0067] Examples of the substituent that the alkanediyl group may optionally have include a cyano group and a halogen atom, but the alkanediyl group is preferably unsubstituted, and more preferably an unsubstituted linear alkanediyl group.

[0068] W 1 and W 2 are each independently preferably a single bond, -O-, -S-, -COO- or -OCOO-, more preferably a single bond or -O-.

[0069] The polymerizable liquid crystal compound (A) is not particularly limited as long as it is a polymerizable liquid crystal compound having at least one polymerizable group, and known polymerizable liquid crystal compounds can be used, but it is preferable that it exhibits smectic liquid crystal properties. A structure that is likely to exhibit smectic liquid crystal properties preferably has an asymmetric molecular structure within the molecular structure. Specifically, it is more preferable that it is a polymerizable liquid crystal compound that exhibits smectic liquid crystal properties and has the partial structures (Aa) to (Ai) below. From the perspective of easily exhibiting higher-order smectic liquid crystal properties, it is more preferable that it has the partial structure (Aa), (Ab), or (Ac). In the following (Aa) to (Ai), * represents a bond (single bond). [ka]

[0070] Specific examples of the polymerizable liquid crystal compound (A) include compounds represented by formulae (A-1) to (A-25). When the polymerizable liquid crystal compound (A) has a cyclohexane-1,4-diyl group, the cyclohexane-1,4-diyl group is preferably a trans isomer. [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] [ka]

[0075] Among these, at least one selected from the group consisting of compounds represented by formula (A-2), formula (A-3), formula (A-4), formula (A-5), formula (A-6), formula (A-7), formula (A-8), formula (A-13), formula (A-14), formula (A-15), formula (A-16), and formula (A-17) is preferred. As the polymerizable liquid crystal compound (A), one compound may be used alone, or two or more compounds may be used in combination.

[0076] The polymerizable liquid crystal compound (A) can be produced by a known method, for example, as described in Lub et al., Recl. Trav. Chim. Pays-Bas, 115, 321-328 (1996), or Japanese Patent No. 4719156.

[0077] In the present invention, the polymerizable liquid crystal composition (A) may contain other polymerizable liquid crystal compounds than the polymerizable liquid crystal compound (A). However, from the viewpoint of obtaining a polarizing film with a high degree of alignment order, the proportion of the polymerizable liquid crystal compound (A) to the total mass of all polymerizable liquid crystal compounds contained in the polymerizable liquid crystal composition (A) is preferably 51 mass % or more, more preferably 70 mass % or more, and even more preferably 90 mass % or more.

[0078] Furthermore, when the polymerizable liquid crystal composition (A) contains two or more polymerizable liquid crystal compounds (A), at least one of them may be the polymerizable liquid crystal compound (A1), or all of them may be the polymerizable liquid crystal compound (A1). By combining multiple polymerizable liquid crystal compounds, it may be possible to temporarily maintain liquid crystallinity even at a temperature below the liquid crystal-crystalline phase transition temperature.

[0079] The content of the polymerizable liquid crystal compound in the polymerizable liquid crystal composition (A) is preferably 40 to 99.9 mass %, more preferably 60 to 99 mass %, and even more preferably 70 to 99 mass %, based on the solid content of the polymerizable liquid crystal composition (A). When the content of the polymerizable liquid crystal compound is within the above range, the alignment of the polymerizable liquid crystal compound tends to be high. In this specification, the solid content of the polymerizable liquid crystal composition (A) refers to the total amount of components excluding the solvent from the polymerizable liquid crystal composition (A).

[0080] [Dichroic dye] In the present invention, the polymerizable liquid crystal composition (A) forming the polarizing film (4) contains a dichroic dye. Here, the dichroic dye refers to a dye having a property in which the absorbance in the long axis direction of the molecule is different from the absorbance in the short axis direction. The dichroic dye that can be used in the present invention is not particularly limited as long as it has the above-mentioned property, and may be a dye or a pigment. Two or more dyes or pigments may be used in combination, or a dye and a pigment may be used in combination.

[0081] The dichroic dye is preferably an organic dichroic dye, and has a maximum absorption wavelength (λ ) in the range of 300 to 700 nm. MAX ) is more preferred. Examples of such dichroic dyes include acridine dyes, oxazine dyes, cyanine dyes, naphthalene dyes, azo dyes, and anthraquinone dyes.

[0082] Examples of azo dyes include monoazo dyes, bisazo dyes, trisazo dyes, tetrakisazo dyes, and stilbene azo dyes, and bisazo dyes and trisazo dyes are preferred, such as a compound represented by formula (I) (hereinafter also referred to as "compound (I)"). K 1 (-N=NK 2 ) p -N=NK 3 (I) [In formula (I), K 1 and K. 3 represent, independently of each other, an optionally substituted phenyl group, an optionally substituted naphthyl group, or an optionally substituted monovalent heterocyclic group. 2 represents a p-phenylene group which may have a substituent, a naphthalene-1,4-diyl group which may have a substituent, or a divalent heterocyclic group which may have a substituent. p represents an integer of 1 to 4. When p is an integer of 2 or more, a plurality of K 2 may be the same or different. The -N=N- bond may be replaced with a -C=C-, -COO-, -NHCO-, or -N=CH- bond as long as the compound exhibits absorption in the visible region.

[0083] Examples of monovalent heterocyclic groups include groups in which one hydrogen atom has been removed from a heterocyclic compound such as quinoline, thiazole, benzothiazole, thienothiazole, imidazole, benzimidazole, oxazole, benzoxazole, etc. Examples of divalent heterocyclic groups include groups in which two hydrogen atoms have been removed from the above heterocyclic compounds.

[0084] K 1 and K. 3 Phenyl, naphthyl and monovalent heterocyclic groups in the above formula, and K 2Examples of the substituent that the p-phenylene group, naphthalene-1,4-diyl group, and divalent heterocyclic group in the formula (I) may optionally have include an alkyl group having 1 to 4 carbon atoms; an alkoxy group having 1 to 4 carbon atoms, such as a methoxy group, an ethoxy group, or a butoxy group; a fluorinated alkyl group having 1 to 4 carbon atoms, such as a trifluoromethyl group; a cyano group; a nitro group; a halogen atom; and a substituted or unsubstituted amino group, such as an amino group, a diethylamino group, or a pyrrolidino group (a substituted amino group refers to an amino group having one or two alkyl groups having 1 to 6 carbon atoms, or an amino group in which two substituted alkyl groups are bonded to each other to form an alkanediyl group having 2 to 8 carbon atoms. An unsubstituted amino group is -NH2).

[0085] Among the compounds (I), compounds represented by any one of the following formulae (I-1) to (I-8) are preferred. [ka] [In formulas (I-1) to (I-8), B 1 ~B 30 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, a nitro group, a substituted or unsubstituted amino group (the substituted amino group and the unsubstituted amino group are defined above), a chlorine atom, or a trifluoromethyl group. n1 to n4 each independently represent an integer of 0 to 3. If n1 is 2 or more, multiple B 2 may be the same or different from each other, If n2 is 2 or more, multiple B 6 may be the same or different from each other, If n3 is 2 or more, multiple B 9 may be the same or different from each other, If n4 is 2 or more, multiple B 14 may be the same or different.]

[0086] The anthraquinone dye is preferably a compound represented by formula (I-9). [ka] [In formula (I-9), R 1 ~R 8 are, independently of each other, a hydrogen atom, -R x , -NH2, -NHR x , -NR x 2, -SR x or a halogen atom. R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.

[0087] The oxazone dye is preferably a compound represented by formula (I-10). [ka] [In formula (I-10), R 9 ~R 15 are, independently of each other, a hydrogen atom, -R x , -NH2, -NHR x , -NR x 2, -SR x or a halogen atom. R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms.

[0088] The acridine dye is preferably a compound represented by formula (I-11). TIFF2025158926000016.tif3980[In formula (I-11), R 16 ~R 23 are, independently of each other, a hydrogen atom, -R x , -NH2, -NHR x , -NR x 2, -SR x or a halogen atom. R x represents an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 12 carbon atoms. In formula (I-9), formula (I-10) and formula (I-11), Rx Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and examples of the aryl group having 6 to 12 carbon atoms include a phenyl group, a toluyl group, a xylyl group, and a naphthyl group.

[0089] As the cyanine dye, compounds represented by formula (I-12) and compounds represented by formula (I-13) are preferred. [ka] [In formula (I-12), D 1 and D 2 represent, independently of each other, a group represented by any one of formulae (I-12a) to (I-12d). [ka] n5 represents an integer from 1 to 3. [ka] [In formula (I-13), D 3 and D 4 represent, independently of each other, a group represented by any one of formulas (I-13a) to (I-13h). [ka] n6 represents an integer from 1 to 3.

[0090] Among these dichroic dyes, azo dyes have high linearity and are therefore suitable for producing polarizing films with excellent polarizing properties.

[0091] In the present invention, the weight average molecular weight of the dichroic dye is usually 300 to 2,000, and preferably 400 to 1,000.

[0092] The content of the dichroic dye in the polymerizable liquid crystal composition (A) can be appropriately determined depending on the type of dichroic dye used, but is preferably 0.1 to 50 parts by mass, more preferably 0.1 to 20 parts by mass, and even more preferably 0.1 to 12 parts by mass, relative to 100 parts by mass of the polymerizable liquid crystal compound. When the content of the dichroic dye is within the above range, the orientation of the polymerizable liquid crystal compound is unlikely to be disturbed, and a polarizing film having a high degree of orientational order can be obtained.

[0093] The dichroic dye is represented by the following formula (A): [ka] [wherein * indicates a linking moiety, R1 and R2 are each independently a halogen atom or a methyl group (-CH3), n and m each independently represent an integer of 0 to 4; R3 and R4 each independently represent an alkyl group which may have a substituent, or R3 and R4 combine with each other to form an alkenyl group. The dye containing the structure represented by the formula (I) is preferred because it can more effectively prevent the deterioration of the polarization performance due to outdoor use.

[0094] A cured layer made of a cured product of a polymerizable liquid crystal composition can be formed, for example, by forming an alignment film on a substrate film, applying the polymerizable liquid crystal composition thereon, orienting the polymerizable liquid crystal compound in the polymerizable liquid crystal composition in a liquid crystal state, for example, a smectic liquid crystal state, by heating or the like, and polymerizing it in this state. The polarizing film (4) may be the cured layer formed in this way alone, or may be a two-layer structure consisting of a cured layer and an alignment film.

[0095] [Circular polarizer] As shown in FIG. 3, the polarizing plate (1) of the present invention can be made into a circular polarizing plate (6) by laminating a retardation plate (5) on the side of the polarizing film (4) opposite to the ultraviolet absorbing film (2), usually via an adhesive layer (not shown).

[0096] [Retardation plate] The retardation plate (5) constituting the circular polarizing plate (6) may be, for example, a retardation plate that exhibits an in-plane retardation of 100 to 180 nm, preferably 120 to 160 nm, at a wavelength of 550 nm, and functions as a so-called λ / 4 plate. When the polarizing film (4) is a linear polarizing film, the angle between the slow axis of the retardation plate (5) and the absorption axis of the polarizing film (4) is ideally 45°, usually 40 to 50°, and preferably 43 to 47°.

[0097] The retardation plate (5) has an in-plane retardation (Re 550 ) at a wavelength of 450 nm (Re 450 ) ratio (Re 450 / Re 550 ) is preferably less than 1.00, more preferably 0.93 or less, particularly preferably 0.88 or less, and even more preferably 0.86 or less, and is usually 0.80 or more, preferably 0.82 or more. 450 / Re 550 ) is less than 1.00, that is, the retardation plate exhibits reverse wavelength dispersion, so that the retardation plate can function as a circular polarizer in a wider visible light range.

[0098] The retardation plate may be a stretched film that imparts retardation by stretching a polymer. However, from the viewpoint of thinning the polarizing plate, it is preferable that the retardation plate be made of a polymerizable liquid crystal composition (hereinafter also referred to as "polymerizable liquid crystal composition (B)") containing a polymer of a polymerizable liquid crystal compound. In the retardation plate, the polymerizable liquid crystal compound is usually polymerized in an aligned state. The polymerizable liquid crystal compound (hereinafter also referred to as "polymerizable liquid crystal compound (B)") that forms the retardation refers to a liquid crystal compound having a polymerizable functional group, particularly a photopolymerizable functional group. The photopolymerizable functional group refers to a group that can participate in a polymerization reaction by an active radical or acid generated from a photopolymerization initiator. Examples of the photopolymerizable functional group include a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group, a methacryloyloxy group, an oxiranyl group, and an oxetanyl group. Among them, acryloyloxy group, methacryloyloxy group, vinyloxy group, oxiranyl group, and oxetanyl group are preferred, and acryloyloxy group is more preferred. The liquid crystal property may be thermotropic liquid crystal or lyotropic liquid crystal, and the phase order structure may be nematic liquid crystal or smectic liquid crystal. As the polymerizable liquid crystal compound, only one type may be used, or two or more types may be used in combination.

[0099] From the viewpoints of facilitating film formation and imparting retardation represented by the formula (Y), the polymerizable liquid crystal compound (B) is preferably a compound having the following characteristics (a) to (d). (A) A compound having thermotropic liquid crystal properties; (a) The polymerizable liquid crystal compound has π electrons in the long axis direction (a). (c) It has π electrons in a direction intersecting the long axis direction (a) [intersecting direction (b)]. (D) The π electron density in the long axis direction (a) of a polymerizable liquid crystal compound defined by the following formula (i), where N(πa) is the total number of π electrons present in the long axis direction (a) and N(Aa) is the total number of molecular weights present in the long axis direction: D(πa)=N(πa) / N(Aa) (i) The π electron density in the cross direction (b) of the polymerizable liquid crystal compound is defined by the following formula (ii), where N(πb) is the total number of π electrons present in the cross direction (b) and N(Ab) is the total molecular weight present in the cross direction (b): D(πb)=N(πb) / N(Ab) (ii) But, 0≦[D(πa) / D(πb)]≦1 (i.e., the π electron density in the cross direction (b) is greater than the π electron density in the long axis direction (a)).

[0100] The polymerizable liquid crystal compound (B) satisfying the above (A) to (D) can form a nematic phase by, for example, applying it to an alignment film formed by rubbing treatment and heating it to a temperature equal to or higher than the phase transition temperature. In the nematic phase formed by the alignment of the polymerizable liquid crystal compound (B), the long axes of the polymerizable liquid crystal compounds are usually aligned so that they are parallel to each other, and these long axes are the alignment direction of the nematic phase.

[0101] The polymerizable liquid crystal compound (B) having the above characteristics generally exhibits reverse wavelength dispersion. Specific examples of the compound satisfying the above characteristics (a) to (d) include compounds represented by the following formula (II): [ka] The compounds represented by formula (II) can be used alone or in combination of two or more.

[0102] In formula (II), Ar represents a divalent aromatic group which may have a substituent. The aromatic group here refers to a group having a planar cyclic structure, and the number of π electrons in the cyclic structure is [4n+2] according to the Hückel rule. Here, n represents an integer. When a heteroatom such as -N= or -S- is included in the ring structure, the non-covalent electron pairs on these heteroatoms also satisfy the Hückel rule, and aromaticity is also included. The divalent aromatic group preferably contains at least one of a nitrogen atom, an oxygen atom, and a sulfur atom.

[0103] In formula (II), G 1 and G 2 each independently represents a divalent aromatic group or a divalent alicyclic hydrocarbon group, wherein a hydrogen atom contained in the divalent aromatic group or divalent alicyclic hydrocarbon group may be substituted with a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, or a nitro group, and a carbon atom constituting the divalent aromatic group or divalent alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom.

[0104] In formula (II), L 1 , L 2 , B 1 and B 2 are each independently a single bond or a divalent linking group.

[0105] In formula (II), k and l each independently represent an integer of 0 to 3, and satisfy the relationship 1≦k+l. When 2≦k+l, B 1 and B 2 , G 1 and G 2 may be the same as or different from each other.

[0106] In formula (II), E 1 and E 2 each independently represents an alkanediyl group having 1 to 17 carbon atoms, wherein a hydrogen atom contained in the alkanediyl group may be substituted with a halogen atom, and -CH2- contained in the alkanediyl group may be substituted with -O-, -S-, or -Si-. 1 and P 2 each independently represents a polymerizable group or a hydrogen atom, and at least one of them is a polymerizable group.

[0107] In formula (II), G 1 and G 2are each independently preferably a 1,4-phenylenediyl group optionally substituted with at least one substituent selected from the group consisting of a halogen atom and an alkyl group having 1 to 4 carbon atoms, or a 1,4-cyclohexanediyl group optionally substituted with at least one substituent selected from the group consisting of a halogen atom and an alkyl group having 1 to 4 carbon atoms, more preferably a 1,4-phenylenediyl group substituted with a methyl group, an unsubstituted 1,4-phenylenediyl group, or an unsubstituted 1,4-trans-cyclohexanediyl group, and particularly preferably an unsubstituted 1,4-phenylenediyl group or an unsubstituted 1,4-trans-cyclohexanediyl group. 1 and G 2 At least one of L is preferably a divalent alicyclic hydrocarbon group. 1 or L 2 G binds to 1 and G 2 It is more preferable that at least one of the groups is a divalent alicyclic hydrocarbon group.

[0108] In formula (II), L 1 and L 2 are each independently preferably a single bond, an alkylene group having 1 to 4 carbon atoms, -O-, -S-, -R a1 OR a2 -, -R a3 COOR a4 -, -R a5 OCOR a6 -, R a7 OC=OOR a8 -, -N=N-, -CR c =CR d -, or -C≡C-, where R a1 ~R a8 each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms, and R c and R d represents an alkyl group having 1 to 4 carbon atoms or a hydrogen atom. 1 and L 2 are each independently preferably a single bond, -OR a2-1 -, -CH2-, -CH2CH2-, -COOR a4-1-, or OCOR a6-1 -, where R a2-1 , R a4-1 , R a6-1 Each independently represents a single bond, -CH2-, or -CH2CH2-. 1 and L 2 are each independently more preferably a single bond, -O-, -CH2CH2-, -COO-, -COOCH2CH2-, or OCO-.

[0109] In one preferred embodiment of the present invention, G in formula (II) 1 and G 2 At least one of the divalent alicyclic hydrocarbon group is a divalent aromatic group Ar which may have a substituent and L which is -COO-. 1 and / or L 2 A polymerizable liquid crystal compound bonded by the formula: is used.

[0110] In formula (II), B 1 and B 2 are each independently preferably a single bond, an alkylene group having 1 to 4 carbon atoms, -O-, -S-, -R a9 OR a10 -, -R a11 COOR a12 -, -R a13 OCOR a14 - or R a15 OC=OOR a16 -, where R a9 ~R a16 each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms. B 1 and B 2 are each independently preferably a single bond, -OR a10-1 -, -CH2-, -CH2CH2-, -COOR a12-1 -, or OCOR a14-1 -, where R a10-1 , R a12-1 , R a14-1 Each independently represents a single bond, -CH2-, or -CH2CH2-. B 1 and B2 are each independently more preferably a single bond, -O-, -CH2CH2-, -COO-, -COOCH2CH2-, -OCO-, or OCOCH2CH2-.

[0111] In formula (II), k and l are preferably in the range of 2≦k+l≦6 from the viewpoint of exhibiting reverse wavelength dispersion, preferably k+l=4, and more preferably k=2 and l=2. It is more preferable that k=2 and l=2 because this results in a symmetric structure.

[0112] In formula (II), E 1 and E 2 are each independently preferably an alkanediyl group having 1 to 17 carbon atoms, more preferably an alkanediyl group having 4 to 12 carbon atoms.

[0113] In formula (II), P 1 or P 2 Examples of the polymerizable group represented by the formula (I) include an epoxy group, a vinyl group, a vinyloxy group, a 1-chlorovinyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group, a methacryloyloxy group, an oxiranyl group, and an oxetanyl group. Among these, an acryloyloxy group, a methacryloyloxy group, a vinyloxy group, an oxiranyl group, and an oxetanyl group are preferred, and an acryloyloxy group is more preferred.

[0114] In formula (II), Ar preferably has at least one selected from an aromatic hydrocarbon ring optionally having a substituent, an aromatic heterocyclic ring optionally having a substituent, and an electron-withdrawing group. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, and an anthracene ring, with a benzene ring and a naphthalene ring being preferred. Examples of the aromatic heterocyclic ring include a furan ring, a benzofuran ring, a pyrrole ring, an indole ring, a thiophene ring, a benzothiophene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a triazole ring, a triazine ring, a pyrroline ring, an imidazole ring, a pyrazole ring, a thiazole ring, a benzothiazole ring, a thienothiazole ring, an oxazole ring, a benzoxazole ring, and a phenanthroline ring. Among these, a thiazole ring, a benzothiazole ring, or a benzofuran ring is preferred, and a benzothiazole group is even more preferred. Furthermore, when Ar contains a nitrogen atom, the nitrogen atom preferably has π electrons.

[0115] In formula (II), the total number of π electrons contained in the divalent aromatic group represented by Ar is N π is preferably 8 or more, more preferably 10 or more, even more preferably 14 or more, and particularly preferably 16 or more. It is also preferably 30 or less, more preferably 26 or less, and even more preferably 24 or less.

[0116] Examples of the aromatic group represented by Ar include groups of the following formulae (Ar-1) to (Ar-23).

[0117] [ka]

[0118] In formulas (Ar-1) to (Ar-23), * represents a linking portion, and Z 0 , Z 1 and Z 2each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a cyano group, a nitro group, an alkylsulfinyl group having 1 to 12 carbon atoms, an alkylsulfonyl group having 1 to 12 carbon atoms, a carboxyl group, a fluoroalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, an N-alkylamino group having 1 to 12 carbon atoms, an N,N-dialkylamino group having 2 to 12 carbon atoms, an N-alkylsulfamoyl group having 1 to 12 carbon atoms, or an N,N-dialkylsulfamoyl group having 2 to 12 carbon atoms.

[0119] In formula (Ar-1) ~ formula (Ar-23), Q 1 and Q 2 are each independently -CR 2’ R 3’ -, -S-, -NH-, -NR 2’ represents -, -CO- or O-, and R 2’ and R 3’ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0120] In formula (Ar-1) ~ formula (Ar-23), J 1 and J. 2 each independently represents a carbon atom or a nitrogen atom.

[0121] In formula (Ar-1) ~ formula (Ar-23), Y 1 , Y 2 and Y 3 each independently represents an optionally substituted aromatic hydrocarbon group or an optionally substituted aromatic heterocyclic group.

[0122] In formulas (Ar-1) to (Ar-23), W 1 and W 2 each independently represents a hydrogen atom, a cyano group, a methyl group or a halogen atom; and m represents an integer of 0 to 6.

[0123] Y 1 , Y 2 and Y 3Examples of the aromatic hydrocarbon group in the formula (I) include aromatic hydrocarbon groups having 6 to 20 carbon atoms, such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and a biphenyl group, with a phenyl group and a naphthyl group being preferred, and a phenyl group being more preferred. Examples of the aromatic heterocyclic group include aromatic heterocyclic groups having 4 to 20 carbon atoms and containing at least one heteroatom, such as a nitrogen atom, an oxygen atom, or a sulfur atom, such as a furyl group, a pyrrolyl group, a thienyl group, a pyridinyl group, a thiazolyl group, and a benzothiazolyl group being preferred.

[0124] Y 1 and Y 2 may each independently be an optionally substituted polycyclic aromatic hydrocarbon group or polycyclic aromatic heterocyclic group. The polycyclic aromatic hydrocarbon group refers to a fused polycyclic aromatic hydrocarbon group or a group derived from an aromatic ring assembly. The polycyclic aromatic heterocyclic group refers to a fused polycyclic aromatic heterocyclic group or a group derived from an aromatic ring assembly.

[0125] In formula (Ar-1) ~ formula (Ar-23), Z 0 , Z 1 and Z 2 are each independently preferably a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, a cyano group, a nitro group, or an alkoxy group having 1 to 12 carbon atoms; Z 0 is more preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a cyano group, and Z 1 and Z 2 is more preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a cyano group.

[0126] In formula (Ar-1) ~ formula (Ar-23), Q 1 and Q 2 -NH-, -S-, -NR 2’ -, -O- are preferred, and R 2’ is preferably a hydrogen atom, and among these, -S-, -O-, and -NH- are particularly preferred.

[0127] Among the formulae (Ar-1) to (Ar-23), the formulae (Ar-6) and (Ar-7) are preferred from the viewpoint of molecular stability.

[0128] In formulas (Ar-17) to (Ar-23), Y 1 is the nitrogen atom to which it is bonded and Z 0 and Y may form an aromatic heterocyclic group together. Examples of the aromatic heterocyclic group include those mentioned above as aromatic heterocycles that Ar may have, such as a pyrrole ring, an imidazole ring, a pyrroline ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, an indole ring, a quinoline ring, an isoquinoline ring, a purine ring, and a pyrrolidine ring. This aromatic heterocyclic group may have a substituent. In addition, Y 1 is the nitrogen atom to which it is bonded and Z 0 and may be the aforementioned optionally substituted polycyclic aromatic hydrocarbon group or polycyclic aromatic heterocyclic group. Examples include a benzofuran ring, a benzothiazole ring, and a benzoxazole ring. The compound represented by formula (II) can be produced, for example, by the method described in JP-A-2010-31223.

[0129] The content of the polymerizable liquid crystal compound (B) in the polymerizable liquid crystal composition (B) constituting the retardation film is, for example, 70 to 99.5 parts by mass, preferably 80 to 99 parts by mass, and more preferably 90 to 98 parts by mass, relative to 100 parts by mass of the solid content of the polymerizable liquid crystal composition (B). When the content is within the above range, the retardation film tends to have high alignment. Here, the solid content refers to the total amount of components excluding volatile components such as solvents from the polymerizable liquid crystal composition (B).

[0130] The polymerizable liquid crystal composition (B) may contain a polymerization initiator for initiating the polymerization reaction of the polymerizable liquid crystal compound (B). The polymerization initiator may be appropriately selected from those conventionally used in the art and may be a thermal polymerization initiator or a photopolymerization initiator. However, a photopolymerization initiator is preferred because it can initiate the polymerization reaction under lower temperature conditions. Suitable examples of the photopolymerization initiator usable in the polymerizable liquid crystal composition (A) include those previously exemplified. Furthermore, the polymerizable liquid crystal composition (B) may optionally contain a photosensitizer, a leveling agent, and additives such as those exemplified for the polymerizable liquid crystal composition (A). Examples of the photosensitizer and leveling agent include those previously exemplified for the polymerizable liquid crystal composition (A).

[0131] The retardation film can be obtained, for example, by applying a composition (hereinafter also referred to as a "composition for forming a retardation film") prepared by adding a solvent to a polymerizable liquid crystal composition (B) containing a polymerizable liquid crystal compound (B) and, if necessary, a polymerization initiator, additives, etc., followed by mixing and stirring the composition, onto a substrate or an alignment film, removing the solvent by drying, and curing the polymerizable liquid crystal compound (B) in the resulting coating film by heating and / or active energy rays. Examples of the substrate and / or alignment film used to prepare the retardation film include those similar to those exemplified above as those usable in preparing the polarizer of the present invention.

[0132] The solvent used in the composition for forming a retardation film, the method for applying the composition for forming a retardation film, the conditions for curing with active energy rays, and the like may all be the same as those that can be employed in the method for producing a polarizer of the present invention.

[0133] The thickness of the retardation film can be appropriately selected depending on the display device to which it is applied, but from the viewpoint of thinning and flexibility, it is preferably 0.1 to 10 μm, more preferably 1 to 5 μm, and even more preferably 1 to 3 μm.

[0134] The polarizing plate (1) of the present invention may have a resin film laminated on the outer side of the ultraviolet absorbing film (2), i.e., on the side opposite to the polarizing film (4), via a pressure-sensitive adhesive layer, etc. By laminating a resin film on the outer side, the effects of the present invention can be more effectively exhibited. [Example]

[0135] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0136] Example 1 [Preparation of Polymerizable Liquid Crystal Composition (A)] <Preparation of Polarizer-Forming Composition> A polarizer-forming composition was obtained by mixing the following components and stirring for 1 hour at 80° C. The dichroic dye used was an azo dye described in the examples of JP-A-2013-101328.

[0137] [Polymerizable liquid crystal compound] [ka] (A-6) 90 copies [ka] (A-7) 10 copies

[0138] [Dichroic dye] Azo dyes; [ka] (Dichroic dye A) 2.5 parts [ka] (Dichroic dye B) 2.5 parts [ka] (Dichroic dye C) 2.5 parts

[0139] [Polymerization initiator] 6 parts of 2-dimethylamino-2-benzyl-1-(4-morpholinophenyl)butan-1-one (Irgacure 369; manufactured by Chiba Specialty Chemicals Co., Ltd.) [Leveling Agent] Polyacrylate compound (BYK-361N; manufactured by BYK-Chemie) 1.2 parts 〔solvent〕 o-xylene 400 parts

[0140] A polarizing film was formed in the same manner as described in paragraphs 0201 to 0203 of JP-A-2020-46622 by the following procedure.

[0141] [Preparation of photo-alignment film on substrate] [Preparation of composition for forming photo-alignment film] The following components described in JP 2013-033249 A were mixed, and the resulting mixture was stirred at 80° C. for 1 hour to obtain a composition for forming a photoalignment film.

[0142] [Photo-alignable polymer] [ka] 2nd part 〔solvent〕 o-xylene 98 parts

[0143] [Preparation of a substrate film with a photo-alignment film] A triacetyl cellulose film (KC4UY, manufactured by Konica Minolta, Inc.) was used as the substrate film. A hard coat layer was formed on the surface of this substrate film, followed by corona treatment. The composition for forming a photo-alignment film was then applied and dried at 120°C to obtain a dry coating. Polarized UV light was irradiated onto this dry coating to form a photo-alignment film (alignment film), resulting in a film with a photo-alignment film. The layer structure of this film with a photo-alignment film was substrate film (KC4UY) / hard coat layer / photo-alignment film. The polarized UV treatment was carried out using a UV irradiation device (SPOT CURE SP-7, manufactured by Ushio Inc.) at an intensity of 100 mJ measured at a wavelength of 365 nm.

[0144] [Preparation of Polarizing Film] The polarizer-forming composition was applied to the substrate film with the photoalignment layer obtained as described above by a bar coating method (#9 30 mm / s), and the polymerizable liquid crystal compound was subjected to phase transition to a liquid phase by heating and drying in a drying oven at 120°C for 1 minute, and then cooled to room temperature to cause the polymerizable liquid crystal compound to undergo phase transition to a smectic liquid crystal state. Next, a UV irradiation device (SPOT CURE SP-7; manufactured by Ushio Inc.) was used to apply an exposure dose of 1000 mJ / cm. 2 A layer formed from a polarizing film-forming composition was irradiated with ultraviolet light (365 nm standard) to polymerize the polymerizable liquid crystal compound contained in the dried film while maintaining the smectic liquid crystal state of the polymerizable liquid crystal compound, forming a polarizing film from the dried film. The thickness of the polarizing film was measured using a laser microscope (OLS3000, manufactured by Olympus Corporation) and found to be 2.3 μm. Thus obtained was a polarizer film comprising a polarizing film and a substrate film. X-ray diffraction measurement of this polarizer film was performed using an X'Pert PRO MPD X-ray diffractometer (manufactured by Spectris Inc.) by irradiating X-rays from the absorption axis direction of the polarizer film. A sharp diffraction peak (Bragg peak) with a peak full width at half maximum (FWHM) of approximately 0.17° was observed near 2θ = 20.2°. The order period (d) calculated from the peak position was approximately 4.4 Å, confirming the formation of a structure reflecting a high-order smectic phase. The polarizing film formed was formed on one side of the substrate film (KC4UY). The layer structure of the obtained polarizer film was substrate film (KC4UY) / hard coat layer / polarizing film (photo-alignment film / cured product layer) (4).

[0145] [Formation of oxygen barrier layer] An oxygen barrier layer was formed on the polarizing film obtained above by the following procedure.

[0146] [Preparation of curable composition (1) for forming oxygen barrier layer] 3.8 parts by mass of polyvinyl alcohol ("Z200" manufactured by Mitsubishi Chemical Corporation) was dissolved in 100 parts by mass of pure water and mixed to prepare a curable composition (1) for forming an oxygen barrier layer. The curable composition for forming an oxygen barrier layer (1) prepared above was applied to the polarizing film (4) formed on one side of the substrate film (KC4UY) as described above, followed by drying at 100°C for 1.5 minutes to form an oxygen barrier layer (3) on the polarizing film (4). The thickness of this oxygen barrier layer was approximately 1.0 µm. The layer structure of the polarizer film with the oxygen barrier layer (3) formed thereon was substrate film (KC4UY) / hard coat layer / polarizing film (photoalignment film / cured product layer) (4) / oxygen barrier layer (3).

[0147] [Preparation of UV-absorbing film (A)] As the ultraviolet absorbing film (A), a film was obtained and used, in which an ultraviolet absorbing layer (thickness 1 μm) was formed on one side of a cycloolefin resin (COP) film ("ZEONORFILM G+" manufactured by ZEON Corporation). The light transmittance (T 300 ) is 0.1% or less, and the light transmittance at a wavelength of 380 nm (T 380 ) is 1.1%, and the light transmittance at a wavelength of 400 nm (T 400 The light transmittance (T) of this ultraviolet absorbing film (A) at a wavelength of 450 nm was 20%. 450 ) is 95%, and T 450 / T 400 was 5.

[0148] Such an ultraviolet absorbing film (A) can be produced, for example, by subjecting one side of a cycloolefin resin film (COP film) (ZEONORFILM G+) to a corona discharge treatment, obtaining a photoselective absorbing compound (1) by the method described in paragraphs 0151-0153 and 0155 of JP 2019-8292 A, preparing an active energy ray-curable resin composition A1 by the method described in paragraph 0155, applying the active energy ray-curable resin composition A1 to the corona discharge-treated surface of the cycloolefin resin film (ZEONORFILM G+) subjected to the corona discharge treatment described above using a bar coater, and irradiating the cycloolefin resin film (ZEONORFILM G+) with ultraviolet light using a belt conveyor-equipped ultraviolet irradiation device (using an "H Bulb" ultraviolet lamp manufactured by Fusion UV Systems). An ultraviolet absorbing layer can be formed on one side of the cycloolefin resin film (ZEONORFILM G+). By adjusting the concentration of the active energy ray-curable resin composition A1, the thickness of the ultraviolet absorbing layer can be adjusted, and the transmittance of the ultraviolet absorbing film at each wavelength can be adjusted. This ultraviolet absorbing film (A) (2) has a layer structure of a COP film (ZEONORFILM G+) (21) / ultraviolet absorbing layer (22).

[0149] [Preparation of Pressure-Sensitive Adhesive Layer] [Preparation of acrylic resin solution] A reaction vessel equipped with a condenser, nitrogen inlet, thermometer, and stirrer was charged with a mixed solution of 100 parts ethyl acetate, 99.0 parts butyl acrylate, 0.5 parts 2-hydroxyethyl acrylate, and 0.5 parts acrylic acid. The air in the vessel was purged with nitrogen gas to remove oxygen, and the internal temperature was raised to 55°C. A solution of 0.12 parts azobisisobutyronitrile (polymerization initiator) in 10 parts ethyl acetate was then added in its entirety. After the addition of the polymerization initiator, the temperature was maintained for 1 hour. Ethyl acetate was then continuously added to the reaction vessel at a rate of 17.3 parts / hour while maintaining the internal temperature at 54-56°C. When the (meth)acrylic resin concentration reached 35% by mass, the ethyl acetate addition was stopped. The temperature was maintained for 6 hours after the start of the ethyl acetate addition. Finally, ethyl acetate was added to adjust the (meth)acrylic resin concentration to 20% by mass, preparing an acrylic resin solution. The resulting acrylic resin had a weight-average molecular weight Mw of 1.7 million and a molecular weight distribution Mw / Mn of 3.9. Mw and Mn were measured in terms of standard polystyrene using two Tosoh Corporation "TSKgel GMHHR-H(S)" columns connected in series in a GPC system, tetrahydrofuran as the eluent, a sample concentration of 2 mg / mL, a sample introduction amount of 100 μL, a temperature of 40°C, and a flow rate of 1 mL / min.

[0150] [Preparation of Pressure-Sensitive Adhesive Composition] To 80 parts of the solid content of the acrylic resin solution obtained above, 20 parts (solid content) of a bifunctional acrylate (obtained from Shin-Nakamura Chemical Co., Ltd.; product number "A-DOG"), 2.5 parts (active ingredient basis) of a crosslinker (manufactured by Tosoh Corporation: product name "Coronate L" (an ethyl acetate solution of a trimethylolpropane adduct of tolylene diisocyanate (solid content concentration 75% by mass)), 1.5 parts of a photopolymerization initiator (manufactured by Ciba Specialty Chemicals: product name "Irgacure 500"), and 0.3 parts of a silane coupling agent (manufactured by Shin-Etsu Chemical Co., Ltd.: product name "KBM-403") were added, and ethyl acetate was further added to adjust the solid content to 13%, thereby obtaining a pressure-sensitive adhesive composition. A-DOG is a diacrylate of the acetal compound of hydroxypivalaldehyde and trimethylolpropane.

[0151] [Preparation of Adhesive Sheet] The adhesive composition prepared above was applied to the release-treated surface of a separate film (PET Separate Film 1) made of a polyethylene terephthalate film subjected to a release treatment [“PLZ-383030” obtained from Lintec Corporation] using an applicator so that the thickness after drying would be 5 μm, and dried at 100° C. for 1 minute to produce an adhesive layer (adhesive sheet). Next, the surface of the obtained adhesive layer on the side opposite to PET Separator Film 1 was bonded to the release-treated surface of a separate film (PET Separate Film 2 [“PLR-381031” obtained from Lintec Corporation]) made of a polyethylene terephthalate film subjected to a release treatment. Subsequently, ultraviolet rays were irradiated under the following UV irradiation conditions to produce an adhesive sheet (1). The adhesive sheet had a layer structure of PET Separate Film 1 / Adhesive Layer / PET Separate Film 2. [UV Irradiation Conditions] · Use of H bulb of Fusion UV Lamp System (manufactured by Fusion UV Systems) · Integrated light quantity: 250 mJ / cm 2

[0152] [Preparation of Polarizing Plate (1)] On the oxygen barrier layer (3) formed further thereon of the polarizing film (4) formed on the base film (KC4UY) above, the ultraviolet absorption film (2) obtained above was laminated on the cycloolefin-based resin film (Zeonor Film G+) side through the adhesive layer obtained by peeling off PET Separate Film 1 and PET Separate Film 2 from the above adhesive sheet to obtain a polarizing plate (1). The layer structure of this polarizing plate (1) is Ultraviolet Absorption Film (A) (2) [Ultraviolet Absorption Layer (22) / COP Film (21)] / Adhesive Layer / Oxygen Barrier Layer (3) / Polarizing Film [Cured Product Layer / Photoalignment Film] (4) / Hard Coat Layer / Base Film (KC4UY) is as follows.

[0153] [Preparation of Retardation Plate]

[0154] [Preparation of composition for forming horizontal alignment film] Five parts of a photo-alignment material (weight average molecular weight: 30,000) having the following structure and 95 parts of cyclopentanone (solvent) were mixed as components, and the resulting mixture was stirred at 80°C for 1 hour to obtain a composition for forming a horizontal alignment film. [ka]

[0155] [Preparation of polymerizable liquid crystal compound] Polymerizable liquid crystal compound (X1) and polymerizable liquid crystal compound (X2) having the following molecular structures were prepared. Polymerizable liquid crystal compound (X1) was produced according to the method described in JP-A-2010-31223. Polymerizable liquid crystal compound (X2) was produced according to the method described in JP-A-2009-173893. These polymerizable liquid crystal compounds are collectively referred to as polymerizable liquid crystal compound 3.

[0156] Polymerizable liquid crystal compound (X1) [ka] Polymerizable liquid crystal compound (X2) [ka]

[0157] A solution was obtained by dissolving 1 mg of polymerizable liquid crystal compound (X1) in 50 mL of tetrahydrofuran. The obtained solution was placed as a measurement sample in a measurement cell with an optical path length of 1 cm, and then the measurement cell was set in an ultraviolet-visible spectrophotometer (Shimadzu Corporation, "UV-2450") to measure the absorption spectrum. The wavelength at which the maximum absorbance was obtained was read from the obtained absorption spectrum, and the maximum absorption wavelength λmax in the wavelength range of 300 to 400 nm was found to be 350 nm.

[0158] [Preparation of polymerizable liquid crystal composition for forming horizontally aligned retardation film ii (polymerizable liquid crystal composition (B))] Polymerizable liquid crystal compound (X1) and polymerizable liquid crystal compound (X2) were mixed in a mass ratio of 90:10 to obtain a mixture. To 100 parts by mass of the obtained mixture, 0.1 parts by mass of a leveling agent "BYK-361N" (manufactured by BM Chemie) and 6 parts by mass of 2-dimethylamino-2-benzyl-1-(4-morpholinophenyl)butan-1-one ("Irgacure (registered trademark) 369 (Irg369)" manufactured by BASF Japan Ltd.) were added as a photopolymerization initiator. Furthermore, N-methyl-2-pyrrolidone (NMP) was added to obtain a solids concentration of 13%. The mixture was stirred at 80°C for 1 hour to obtain a polymerizable liquid crystal composition for forming a horizontally aligned retardation film ii (polymerizable liquid crystal composition (B)).

[0159] [Preparation of horizontally aligned retardation film II (retardation plate)] After corona treatment was performed on a cycloolefin resin film (COP film) (ZF-14-50) manufactured by Zeon Corporation, the composition for forming a horizontal alignment film was applied with a bar coater, dried at 80°C for 1 minute, and then irradiated with a polarized UV irradiation device (SPOT CURE SP-9; manufactured by Ushio Inc.) with an integrated light intensity of 100 mJ / cm at a wavelength of 313 nm. 2 The film was exposed to polarized UV light at 80° C. to obtain a horizontal alignment film (alignment film). The thickness of the obtained horizontal alignment film (alignment film) was measured with an ellipsometer and found to be 200 nm. Subsequently, a polymerizable liquid crystal composition for forming a horizontally aligned retardation film ii (polymerizable liquid crystal composition (B)) was applied onto the horizontal alignment film (alignment film) using a bar coater, and heated at 120°C for 60 seconds. After that, ultraviolet light was irradiated from the surface onto which the polymerizable liquid crystal composition for forming a horizontally aligned retardation film ii was applied using a high-pressure mercury lamp (Uniquer VB-15201BY-A, manufactured by Ushio Inc.) (under a nitrogen atmosphere, cumulative light intensity at a wavelength of 365 nm: 500 mJ / cm 2 ) to form a cured layer on the alignment film on the COP film (ZF-14-50), thereby forming a horizontally aligned retardation film ii (retardation plate (COP film (ZF-14-50) / horizontal alignment film / cured layer) (5)).

[0160] [Preparation of circularly polarizing plate (A)] The substrate film (KC4UY) was peeled off from the polarizing plate (1) obtained above to expose the hard coat layer. The horizontally aligned retardation film ii (retardation plate (5)) formed on the COP film (ZF-14-50) above was attached to the hard coat layer exposed above on the cured layer side via an adhesive layer similar to the adhesive layer described above, and the COP film (ZF-14-50) was peeled off to expose the alignment layer, and an adhesive layer similar to the adhesive layer described above was attached thereon to obtain a circular polarizing plate (A) (6). The layer structure of this circular polarizing plate (A) (6) is as follows: UV-absorbing film (A) (2) [UV-absorbing layer (22) / COP film (21)] / adhesive layer / oxygen barrier layer (3) / polarizing film [cured layer / photo-alignment film] (4) / hard coat layer / adhesive layer / retardation film (5) [cured layer / horizontal alignment film] / adhesive layer The polarizing film (4) and the retardation plate (5) were attached so that the absorption axis of the polarizing film (4) and the slow axis of the retardation plate (5) crossed each other at an angle of 45° in the plane.

[0161] Example 2 A circularly polarizing plate (B) was obtained in the same manner as in Example 1, except that a COP film (ZEONOR FILM G+) with a 2 μm-thick ultraviolet absorbing layer formed on one side thereof was used as the ultraviolet absorbing film (B)(2) instead of the ultraviolet absorbing film (A)(2). This ultraviolet absorbing film (B)(2) was Light transmittance T at a wavelength of 300 nm 300 is less than 0.1% Light transmittance T at a wavelength of 380 nm 380 is less than 0.1% Light transmittance T at a wavelength of 400 nm 400 is 4.6%, Light transmittance T at a wavelength of 450 nm 450 is 90% T 450 / T 400 was 20.

[0162] Example 3 A circularly polarizing plate (C) was obtained in the same manner as in Example 1, except that a COP film (ZEONOR FILM G+) with a 3 μm thick ultraviolet absorbing layer formed on one side thereof was used as the ultraviolet absorbing film (C)(2) instead of the ultraviolet absorbing film (A)(2). This ultraviolet absorbing film (C)(2) was Light transmittance T at a wavelength of 300 nm 300 is less than 0.1% Light transmittance T at a wavelength of 380 nm 380 is less than 0.1% Light transmittance T at a wavelength of 400 nm 400 is 2.6% Light transmittance T at a wavelength of 450 nm 450 is 89% T 450 / T 400 was 34.

[0163] Example 4 A circularly polarizing plate (D) was obtained in the same manner as in Example 1, except that a COP film (ZEONOR FILM G+) with a 4 μm thick ultraviolet absorbing layer formed on one side thereof was used as the ultraviolet absorbing film (D)(2) instead of the ultraviolet absorbing film (A)(2). This ultraviolet absorbing film (D)(2) was Light transmittance T at a wavelength of 300 nm 300 is less than 0.1% Light transmittance T at a wavelength of 380 nm 380 is less than 0.1% Light transmittance T at a wavelength of 400 nm 400 is 1.5%, Light transmittance T at a wavelength of 450 nm 450 is 89% T 450 / T 400 was 60.

[0164] Example 5 A circularly polarizing plate (E) was obtained in the same manner as in Example 1, except that a COP film (ZEONOR FILM G+) with a 5 μm thick ultraviolet absorbing layer formed on one side thereof was used as the ultraviolet absorbing film (E)(2) instead of the ultraviolet absorbing film (A)(2). This ultraviolet absorbing film (E)(2) was Light transmittance T at a wavelength of 300 nm 300 is less than 0.1% Light transmittance T at a wavelength of 380 nm 380 is less than 0.1% Light transmittance T at a wavelength of 400 nm 400 is 0.2%, Light transmittance T at a wavelength of 450 nm 450 is 89% T 450 / T 400 was 474.

[0165] Example 6 A circularly polarizing plate (D) was obtained by the same procedure as in Example 4. A COP film (ZEONORFILM G+) was further laminated on the COP film (ZEONORFILM G+) (21) side of the ultraviolet absorbing film (2) of this circularly polarizing plate (D) [a laminate structure of a COP film (ZEONORFILM G+) (21) and an ultraviolet absorbing layer (4 μm) (22)] via the same adhesive layer as above, to obtain a circularly polarizing plate (F). The layer structure of this circularly polarizing plate (F) is as follows: COP film (ZEONOR Film G+) / adhesive layer / UV-absorbing film (A) (2) [UV-absorbing layer (22) / COP film (21)] / adhesive layer / oxygen barrier layer (3) / polarizing film [cured layer / photo-alignment film] (4) / hard coat layer / adhesive layer / retardation film (5) [cured layer / horizontal alignment film] / adhesive layer is.

[0166] Example 7 In the preparation of the polarizing plate, the ultraviolet absorbing film (2) was laminated on the oxygen barrier layer (3) via a pressure-sensitive adhesive layer, but on the ultraviolet absorbing layer (22) side, in the same manner as in Example 4, to obtain a circularly polarizing plate (G). The layer structure of this circularly polarizing plate (G) was as follows: UV-absorbing film (A) (2) [COP film (21) / UV-absorbing layer (22)] / adhesive layer / oxygen barrier layer (3) / polarizing film [cured layer / photo-alignment film] (4) / hard coat layer / adhesive layer / retardation film (5) [cured layer / horizontal alignment film] / adhesive layer is.

[0167] Example 8 [Preparation of pressure-sensitive adhesive layer (22) containing selective light absorption compound] A photoselective compound-containing pressure-sensitive adhesive layer (22) was prepared as a "pressure-sensitive adhesive sheet" in the same manner as described in paragraphs 0247, 0258, 0259, 0260, 0280, 0289, and 0292 of JP 2017-12020430 A.

[0168] [Preparation of UV-absorbing film (H)(2)] This photoselective compound-containing pressure-sensitive adhesive layer (22) was attached to one side of a COP film (ZEONORFILM G+) (21) to obtain an ultraviolet absorbing film (H). Light transmittance T at a wavelength of 300 nm 300 is less than 0.1% Light transmittance T at a wavelength of 380 nm 380 is less than 0.1% Light transmittance T at a wavelength of 400 nm 400 is less than 0.1% Light transmittance T at a wavelength of 450 nm 450 is 91% T 450 / T 400 was 3800.

[0169] [Creating a circular polarizing plate (H)] A polarizing plate (2) was obtained in the same manner as in Example 1, except that the polarizing film (4) was formed on a substrate film (KC4UY) in the same manner as in Example 1, and an oxygen barrier layer (3) was formed on the polarizing film (4), and the ultraviolet absorbing film (H) was laminated on the photoselective compound-containing pressure-sensitive adhesive layer (22) side to obtain a polarizing plate (1). The layer structure of this polarizing plate (2) was as follows: UV-absorbing film (H) (2) [COP film (21) / photoselective compound-containing adhesive layer (22)] / oxygen barrier layer (3) / polarizing film [cured material layer / photoalignment film] (4) / hard coat layer / substrate film (KC4UY) is.

[0170] A circularly polarizing plate (H) was obtained in the same manner as in Example 1, except that the polarizing plate (2) obtained above was used instead of the polarizing plate (1) obtained in Example 1. The layer structure of this circularly polarizing plate (H) was as follows: UV-absorbing film (H) (2) [COP film (21) / photoselective compound-containing adhesive layer (22)] / oxygen barrier layer (3) / polarizing film [cured layer / photoalignment film] (4) / hard coat layer / adhesive layer / retardation film (5) [cured layer / horizontal alignment film] / adhesive layer is.

[0171] Comparative Example 1 [Formation of photo-alignment film on substrate film] A triacetyl cellulose film (KC4UY, manufactured by Konica Minolta, Inc.) was used as the substrate film. After corona treatment was applied to the surface of this substrate film, the composition for forming a horizontal alignment film obtained in Example 1 was applied and dried at 120°C to obtain a dried film. Modified UV was irradiated onto this dried film to form a photo-alignment film (alignment film), resulting in a film with a photo-alignment film. The layer structure of this film with a photo-alignment film was substrate film (KC4UY) / photo-alignment film (2). Polarized UV was irradiated using a UV irradiation device (SPOT CURE SP-7, manufactured by Ushio Inc.) under conditions of an intensity of 100 mJ at a wavelength of 365 nm.

[0172] [Formation of polarizing film] A polarizing film was obtained by forming a polarizing film on the photo-alignment film (2) formed on the substrate film in the same manner as in Example 1, except that the photo-alignment film-attached film obtained above was used instead of the substrate film with the photo-alignment film obtained in Example 1. The layer structure of this polarizing film was substrate film (KC4UY) / polarizing film (photo-alignment film (2) / cured product layer) (4').

[0173] [Formation of polyvinyl alcohol layer (PVA-OC)] A polyvinyl alcohol layer (PVA-OC) was formed on the polarizing membrane of the polarizing film obtained above by the following procedure.

[0174] A curable composition (1) was obtained by mixing 3.0 parts by mass of a polyvinyl alcohol film ("Kuraray Poval KL318" manufactured by Kuraray Co., Ltd.) and 1.5 parts by mass (solid content equivalent) of a water-soluble polyamide epoxy resin ("Sumirez Resin 650" manufactured by Sumika Chemtex Co., Ltd., solid content concentration: 30% by mass).

[0175] The polarizing film side of the polarizing film obtained above was subjected to a corona treatment, and then the curable composition (1) obtained above was applied using a bar coater so that the thickness after drying would be 0.5 μm, and the applied layer was dried at 100°C to form a polyvinyl alcohol layer (PVA-OC) on the polarizing film.

[0176] [Formation of cured layer (UV-OC)] A cured layer (UV-OC) was formed on the polyvinyl alcohol layer (PVA-OC) formed above by the following procedure.

[0177] The following alicyclic epoxy compound, oxetane compound, photocationic polymerization initiator, and silicone leveling agent were mixed to obtain a curable composition.

[0178] Alicyclic epoxy compound [Celloxide 2021P (Daicel Chemical Industries, Ltd.)] 32.5 parts by mass Alicyclic epoxy compound [EHPE3150 (manufactured by Daicel Chemical Industries, Ltd.)] 17.5 parts by mass Oxetane compound [OXT-221 (manufactured by Toagosei Co., Ltd.)] 50 parts by mass 2.5 parts by mass of cationic photopolymerization initiator [CPI-100P (San-Apro Co., Ltd.)] Silicone leveling agent [SH710 (Dow Corning Toray Co., Ltd.)] 0.25 parts by mass

[0179] This curable composition was applied onto the polyvinyl alcohol layer (PVA-OC) formed above using a bar coater so that the thickness after curing would be 1.5 μm. Then, a UV irradiation device [SPOT CURE SP-7 (manufactured by Ushio Inc.)] was used to apply an exposure dose of 500 mJ / cm. 2 The coated surface was irradiated with ultraviolet light (365 nm standard) to cure the curable composition coated above, thereby forming a cured product layer (UV-OC).

[0180] [Preparation of Circularly Polarizing Plate] The horizontally aligned retardation film ii (retardation plate (5)) obtained in Example 1 was laminated on the cured layer side of the cured product layer (UV-OC) formed above via an adhesive layer, and the COP film (ZF-14-50) was peeled off to expose the alignment layer, and an adhesive layer was laminated on top of that to obtain a circular polarizer. The layer structure of this circular polarizer was base film (KC4UY) / polarizing film (photo-alignment film / polarizing film) / polyvinyl alcohol layer (PVA-OC) / cured product layer (UV-OC) / adhesive layer / retardation plate (cured layer / horizontal alignment film) / adhesive layer.

[0181] Comparative Example 2 A film (ultraviolet absorbing film (J)) was obtained and used, in which an ultraviolet absorbing layer (thickness 1 μm) was formed on one side of a cycloolefin resin film ("ZEONORFILM ZF14" manufactured by ZEON Corporation). The light transmittance (T 300 ) is 5.2%, and the light transmittance at a wavelength of 380 nm (T 380 ) is 1.1%, and the light transmittance at a wavelength of 400 nm (T 400 ) is 20%, and the light transmittance at a wavelength of 450 nm (T 450 ) is 94.8%, and T 450 / T 400 was 5.

[0182] A circularly polarizing plate (J) was obtained in the same manner as in Example 1, except that the ultraviolet absorbing film (J) obtained above was used instead of the ultraviolet absorbing film (A).

[0183] 〔evaluation〕 [Light resistance test]

[0184] Each circular polarizer prepared in each of the above examples was attached to an inorganic glass plate via the adhesive on the retardation film (5) side to prepare a sample for durability test evaluation. The ultraviolet absorbing film side was set as the light source side in a xenon weather resistance tester (device name: Atlas Ci4400, manufactured by DJK Corporation), and the output at a wavelength of 420 nm was set to 2.4 W / m 2 The sample was left in the above conditions for 80 hours and 240 hours. Evaluation was carried out for the following items according to the following criteria.

[0185] [Evaluation items and results] [Appearance in transmitted light] After the light resistance test was carried out by the above-described method, the durability test evaluation sample was illuminated from the inorganic glass surface side by a backlight and visually observed from the circular polarizing plate side (front direction). If the sample showed almost no color change in the transmitted light after both 80 hours and 240 hours, it was rated A. If almost no color change is observed after 80 hours, and slight color change is observed after 240 hours, the grade is B. If slight discoloration is observed after 80 hours and significant discoloration is observed after 240 hours, the product is rated C. If significant discoloration was observed at the 80-hour mark, the sample was rated D and the durability test was discontinued.

[0186] [Appearance on an aluminum reflector] An aluminum foil was attached to one side of the inorganic glass plate via an adhesive to obtain an aluminum reflector. Then, the circular polarizer prepared in each example was attached to the aluminum reflector via the adhesive layer on the retardation plate (5) side to obtain a sample, and the sample was visually observed from the front. When viewed from the front, the circular polarizer was rated as B if it appeared black with a slight bluish tint, and as A if it appeared black with almost no tint.

[0187] The results are shown in Tables 1 and 2.

[0188]

Table 1

[0189]

Table 2

Claims

1. an ultraviolet absorbing film; a polarizing film in which a dichroic dye is oriented, and a polarizing plate in which the polarizing film is laminated in this order; The ultraviolet absorbing film is Light transmittance at a wavelength of 300 nm (T ３００ ) is 1% or less, Light transmittance at a wavelength of 380 nm (T ３８０ ) is 10% or less, Light transmittance at a wavelength of 400 nm (T ４００ ) is 20% or less, Light transmittance at a wavelength of 450 nm (T ４５０ ) is 80% or more A polarizing plate characterized by:

2. The ultraviolet absorbing film has a light transmittance (T ４００ ) to the light transmittance at a wavelength of 450 nm (T ４５０ ) ratio (T ４５０ / T ４００ 2. The polarizing plate according to claim 1, wherein the value of (a) is 10 or more.

3. The dichroic dye is represented by formula (A) 【Chemical 1】 [wherein * indicates a linking moiety, R1 and R2 each independently represent a halogen atom or a methyl group (-CH ３ ) and n and m each independently represent an integer of 0 to 4; R3 and R4 each independently represent an alkyl group which may have a substituent, or R3 and R4 combine with each other to form an alkenyl group.

3. The polarizing plate according to claim 1, wherein the dye contains a structure represented by the formula:

4. the ultraviolet absorbing film includes a resin film and an ultraviolet absorbing layer provided on the polarizing film side of the resin film, The resin film is Light transmittance at a wavelength of 300 nm (T ３００Ｆ ) is 1% or less, Light transmittance at a wavelength of 380 nm (T ３８０Ｆ ) is 10% or less, Light transmittance at a wavelength of 400 nm (T ４００Ｆ ) exceeds 20%, Light transmittance at a wavelength of 450 nm (T ４５０Ｆ ) is 80% or more The polarizing plate according to claim 1 or 2.

5. 3. The polarizing plate according to claim 1, further comprising an oxygen barrier layer between the ultraviolet absorbing film and the polarizing film.

6. the oxygen barrier layer is laminated directly to the ultraviolet absorbing film or laminated only via a pressure-sensitive adhesive layer, 6. The polarizing plate according to claim 5, wherein the oxygen barrier layer is laminated directly to the polarizing film or laminated only via an adhesive layer.

7. 7. The polarizing plate according to claim 5, wherein the oxygen barrier layer is a polyvinyl alcohol-based resin layer.

8. 8. A circularly polarizing plate comprising the polarizing film of claim 1 and a retardation plate laminated on the polarizing film on the opposite side of the polarizing film from the ultraviolet absorbing film.

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