CN114236649A - Optical film, polarizing plate, and method for producing optical film - Google Patents
Optical film, polarizing plate, and method for producing optical film Download PDFInfo
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- CN114236649A CN114236649A CN202111050995.9A CN202111050995A CN114236649A CN 114236649 A CN114236649 A CN 114236649A CN 202111050995 A CN202111050995 A CN 202111050995A CN 114236649 A CN114236649 A CN 114236649A
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3083—Birefringent or phase retarding elements
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
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- Manufacturing & Machinery (AREA)
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- Polarising Elements (AREA)
- Polyesters Or Polycarbonates (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
Abstract
提供光学薄膜、偏光板和光学薄膜的制造方法。提供抑制加湿可靠性试验中的相位差变化、且抑制紫外区的耐候性试验中的色相的变化、进而粘接性优异的光学薄膜和包含该光学薄膜的偏光板。使用由具有规定范围的双折射的树脂构成、取向度为5％以上的光学薄膜。Provided are optical films, polarizing plates, and manufacturing methods of optical films. To provide an optical film and a polarizing plate including the optical film excellent in adhesiveness while suppressing the change in retardation in the humidification reliability test and suppressing the change in the hue in the weather resistance test in the ultraviolet region. An optical film composed of a resin having birefringence in a predetermined range and having an orientation degree of 5% or more is used.
Description
Technical Field
The present invention relates to an optical film, a polarizing plate, and a method for producing an optical film.
Background
In recent years, there is a demand in the display market for the purpose of prolonging the durability of a battery and further suppressing heat generation to lower the display luminance. Therefore, as a polarizing plate used for a display, a polarizing plate having high light transmittance is demanded. However, when such a polarizing plate having high light transmittance is used for a display, there is a problem that the appearance is deteriorated under a humidified condition.
Furthermore, in recent years, displays are increasingly used in environments exposed to ultraviolet light (for example, PID (public information display) and cellular phones), and particularly, a polarizing plate in which an optical film is disposed on a panel side has a problem that the color of the optical film is changed by ultraviolet light, which deteriorates the quality of the display.
Documents of the prior art
Patent document
Patent document 1: japanese patent No. 3325560
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made to solve the above conventional problems, and an object of the present invention is to provide an optical film which suppresses a change in retardation under a humidified condition, suppresses a change in hue in a weather resistance test in an ultraviolet region, and has excellent adhesiveness, and a polarizing plate including the optical film.
Means for solving the problems
The optical film according to the embodiment of the present invention is composed of a resin having a birefringence Δ nxy of 0.015 or more, has an orientation degree of 5% or more, an in-plane retardation Re (550) of 20nm or less, a retardation change rate after being held at 65 ℃ and 90% RH for 500 hours of 10% or less, and a b value change rate in a weather resistance test in an ultraviolet region of 1% or less.
In 1 embodiment, the resin includes a polycarbonate-based resin.
In 1 embodiment, the polycarbonate-based resin contains a structural unit derived from a dihydroxy compound represented by formula (4).
In 1 embodiment, the polycarbonate-based resin further comprises a structural unit derived from an alicyclic dihydroxy compound represented by the following general formula (II), R1The structure is represented by (IIb) below, and n is 0.
HOCH2-R1-CH2OH (II)
In 1 embodiment, the optical film has a thickness of 10 to 50 μm.
In another embodiment of the present invention, a polarizing plate is provided. The polarizing plate includes a polarizing material and the optical film attached to at least one surface of the polarizing material via an adhesive layer.
According to another aspect of the present invention, there is provided a method for manufacturing the above optical film. The manufacturing method comprises a film-making process with a linear velocity of 7-15 m/min.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the embodiment of the present invention, a resin film made of a specific resin and having a birefringence Δ nxy of 0.015 or more is formed under specific conditions, whereby the degree of orientation becomes a certain value or more, and as a result, an optical film which suppresses a change in retardation in a humidification reliability test, suppresses a change in hue in a weather resistance test in an ultraviolet region, and is excellent in adhesiveness can be realized.
Detailed Description
Embodiments of the present invention will be described below, but the present invention is not limited to these embodiments.
(definitions of terms and symbols)
The definitions of terms and symbols in the present specification are as follows.
(1) Refractive index (nx, ny, nz)
"nx" is a refractive index in a direction in which the in-plane refractive index is maximized (i.e., the slow axis direction), "ny" is a refractive index in a direction orthogonal to the slow axis in the plane (i.e., the fast axis direction), and "nz" is a refractive index in the thickness direction.
(2) In-plane retardation (Re)
"Re (. lamda)" is an in-plane retardation measured at 23 ℃ by light having a wavelength of. lamda.nm. For example, "Re (550)" is an in-plane retardation measured at 23 ℃ with light having a wavelength of 550 nm. When the thickness of the layer (film) is d (nm), Re (λ) is obtained by the formula Re (λ) ═ nx-ny × d.
(3) Birefringence (Δ nxy)
Birefringence Δ nxy is given by: Δ nxy ═ nx-ny.
A. Optical film
The optical film according to the embodiment of the present invention is formed of a resin. Typical examples of the resin include polycarbonate resins. Accordingly, the optical film according to the embodiment of the present invention is typically a polycarbonate resin film. Further, the optical film according to the embodiment of the present invention preferably does not contain an ultraviolet absorber. The optical film does not contain an ultraviolet absorber, and thus can maintain a neutral hue when applied to an image display device.
The birefringence Δ nxy of the resin constituting the optical film is typically 0.015 or more, preferably 0.018 or more. The upper limit of the birefringence Δ nxy of the resin may be, for example, 0.040. When a resin film made of a resin having such birefringence Δ nxy is formed at a linear velocity equal to or higher than a predetermined velocity, the degree of orientation is equal to or higher than a certain value, and as a result, a change in retardation can be significantly suppressed under humidified conditions.
The degree of orientation of the optical film is 5% or more, preferably 5.5% or more, and more preferably 6% or more. The upper limit of the degree of orientation is, for example, 70%. When the degree of orientation of the optical film is in such a range, the adhesiveness of the optical film is good. The orientation degree in such a range can be achieved by forming the resin film at a linear velocity in a predetermined range. The above-mentioned degree of orientation is measured by, for example, X-ray diffraction (XRD).
The optical film has an in-plane retardation Re (550) of 20nm or less, preferably 15nm or less, and more preferably 10nm or less. The lower limit of the in-plane retardation may be, for example, 0 nm. That is, the optical film preferably has substantially optical isotropy. Such an in-plane retardation Re (550) of the optical film can be obtained by forming the resin film at a linear velocity in a predetermined range.
The change in retardation of the optical film after storage for 500 hours at a temperature of 65 ℃ and a humidity of 90% (humidification test) is preferably 10% or less, more preferably 8% or less. The lower limit may be, for example, 0.01%. The above-mentioned phase difference change (%) With | (Re)500-Re0)/Re0Expressed as | × 100 (%). Re0The in-plane retardation (nm), Re, of the optical film before the start of the test500The in-plane retardation (nm) of the optical film after the test was obtained. When the retardation of the optical film is changed in such a range, the following advantages can be obtained when the optical film is applied to an image display device: the color change due to the phase difference at each position on the image display device is reduced, and the occurrence of color unevenness on the display can be suppressed.
The change in b value in the weather resistance test of the above optical film in the ultraviolet region is suppressed. The rate of change in b value is 1% or less, preferably 0.95% or less. The lower limit of the variation rate of b value is, for example, 0%. That is, the optical film can be favorably used for applications requiring weather resistance. The optical film can obtain such advantages by containing a specific polycarbonate resin described later.
The thickness of the optical film is preferably 10 to 50 μm, more preferably 20 to 40 μm.
The optical film preferably has a moisture permeability of 250g/m224h or less, more preferably 150g/m224h or less. The lower limit may be, for example, 1g/m224 h. When the moisture permeability of the optical film is in such a range, there is an advantage that the change in retardation in a humidified environment can be suppressed.
The absolute value of the photoelastic coefficient of the optical film is preferably 2 × 10-11m2A value of not more than N, more preferably 2.0X 10-13m2/N～1.5×10-11m2More preferably 1.0X 10-12m2/N～1.2×10-11m2and/N. When the absolute value of the photoelastic coefficient is in such a range, the phase difference is less likely to change when a shrinkage stress is generated during heating. As a result, when the optical film is used for an image display device, thermal unevenness of the image display device can be prevented favorably.
According to the embodiment of the present invention, an optical film having an orientation degree in a specific range can be obtained by forming a film at a linear velocity in a predetermined range using a resin having a birefringence Δ nxy in a specific range as described above. The optical film satisfies a desired in-plane retardation (substantially optically isotropic), and further satisfies both suppression of a change in retardation in a humidification reliability test, suppression of a change in hue in a weather resistance test in an ultraviolet region, and good adhesion.
An optical film having substantial optical isotropy can be obtained by forming the resin film at a linear speed equal to or lower than a predetermined speed. However, when the linear velocity is equal to or lower than a constant velocity, the degree of orientation of the obtained optical film is lowered, which causes a change in retardation and a decrease in adhesiveness in the humidification reliability test. By setting the linear velocity to a constant velocity or higher, the degree of orientation of the optical film is improved, and a change in retardation in the humidification reliability test can be suppressed, thereby improving the adhesiveness. That is, by optimizing the range of the linear velocity, it is possible to achieve both desired in-plane retardation, suppression of retardation change in a humidification reliability test, and excellent adhesiveness. Such an optical film can be suitably used for, for example, PID (public information display), cellular phones.
B. Constituent Material
As described above, the optical film is typically a resin film containing a polycarbonate resin.
(polycarbonate resin)
The polycarbonate resin of the present invention comprises at least a structural unit derived from a dihydroxy compound having a bonding structure represented by the following structural formula (1) and produced by reacting a dihydroxy compound comprising at least-CH having at least one bonding structure in the molecule with a carbonic acid diester in the presence of a polymerization catalyst2-dihydroxy compounds of-O-.
The dihydroxy compound having a linkage structure represented by the formula (1) may be any compound having 2 alcoholic hydroxyl groups, having a structure containing a linking group-CH 2-O-in the molecule, and being capable of reacting with a carbonic acid diester in the presence of a polymerization catalyst to produce a polycarbonate, and a plurality of compounds may be used in combination. Further, as the dihydroxy compound used in the polycarbonate resin of the present invention, a dihydroxy compound not having a bonding structure represented by the structural formula (1) may be used in combination. Hereinafter, the dihydroxy compound having a bonding structure represented by the structural formula (1) may be abbreviated as the dihydroxy compound (a), and the dihydroxy compound having no bonding structure represented by the structural formula (1) may be abbreviated as the dihydroxy compound (B).
(dihydroxy Compound (A))
"linking group-CH" in dihydroxy Compound (A)2The term "O-" refers to a structure in which atoms other than hydrogen atom are bonded to each other to constitute a molecule. In the linking group, carbon atoms are most preferable as atoms capable of bonding to at least oxygen atoms or atoms capable of bonding to both carbon atoms and oxygen atoms. "linking group-CH" in dihydroxy Compound (A)2The number of-O- "is preferably 1 or more, more preferably 2 to 4.
More specifically, examples of the dihydroxy compound (A) include 9, 9-bis (4- (2-hydroxyethoxy) phenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-methylphenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-isopropylphenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-isobutylphenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-tert-butylphenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-cyclohexylphenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-phenylphenyl) fluorene, 9-bis (2-hydroxyethoxy) -3-phenylphenyl) fluorene, and the like, Compounds having an aromatic group in a side chain and an ether group bonded to the aromatic group in a main chain, such as 9, 9-bis (4- (2-hydroxyethoxy) -3, 5-dimethylphenyl) fluorene, 9-bis (4- (2-hydroxyethoxy) -3-tert-butyl-6-methylphenyl) fluorene, and 9, 9-bis (4- (3-hydroxy-2, 2-dimethylpropoxy) phenyl) fluorene; bis [4- (2-hydroxyethoxy) phenyl ] methane, bis [4- (2-hydroxyethoxy) phenyl ] diphenylmethane, 1-bis [4- (2-hydroxyethoxy) phenyl ] ethane, 1-bis [4- (2-hydroxyethoxy) phenyl ] -1-phenylethane, 2-bis [4- (2-hydroxyethoxy) phenyl ] propane, 2-bis [4- (2-hydroxyethoxy) -3-methylphenyl ] propane, 2-bis [3, 5-dimethyl-4- (2-hydroxyethoxy) phenyl ] propane, 1-bis [4- (2-hydroxyethoxy) phenyl ] -3, 5-trimethylcyclohexane, 1-bis [4- (2-hydroxyethoxy) phenyl ] cyclohexane, 1, 4-bis [4- (2-hydroxyethoxy) phenyl ] cyclohexane, 1, 3-bis [4- (2-hydroxyethoxy) phenyl ] cyclohexane, 2-bis [4- (2-hydroxyethoxy) -3-phenylphenyl ] propane, 2-bis [ (2-hydroxyethoxy) -3-isopropylphenyl ] propane, 2-bis [ 3-tert-butyl-4- (2-hydroxyethoxy) phenyl ] propane, 2-bis [4- (2-hydroxyethoxy) phenyl ] butane, 2-bis [4- (2-hydroxyethoxy) phenyl ] -4-methylpentane, 2-bis [4- (2-hydroxyethoxy) phenyl ] pentane, Bis (hydroxyalkoxyaryl) alkanes such as exemplified by 2, 2-bis [4- (2-hydroxyethoxy) phenyl ] octane, 1-bis [4- (2-hydroxyethoxy) phenyl ] decane, 2-bis [ 3-bromo-4- (2-hydroxyethoxy) phenyl ] propane, and 2, 2-bis [ 3-cyclohexyl-4- (2-hydroxyethoxy) phenyl ] propane; bis (hydroxyalkoxyaryl) cycloalkanes such as 1, 1-bis [4- (2-hydroxyethoxy) phenyl ] cyclohexane, 1-bis [ 3-cyclohexyl-4- (2-hydroxyethoxy) phenyl ] cyclohexane, and 1, 1-bis [4- (2-hydroxyethoxy) phenyl ] cyclopentane; dihydroxyalkoxy diaryl ethers exemplified by 4,4 ' -bis (2-hydroxyethoxy) diphenyl ether and 4,4 ' -bis (2-hydroxyethoxy) -3,3 ' -dimethyldiphenyl ether; bishydroxyalkoxyaryl sulfides exemplified by 4,4 '-bis (2-hydroxyethoxyphenyl) sulfide and 4, 4' -bis [4- (2-dihydroxyethoxy) -3-methylphenyl ] sulfide; bishydroxyalkoxyarylsulfoxides exemplified by 4,4 '-bis (2-hydroxyethoxyphenyl) sulfoxide and 4, 4' -bis [4- (2-dihydroxyethoxy) -3-methylphenyl ] sulfoxide; bishydroxyalkoxyaryl sulfones such as exemplified by 4,4 '-bis (2-hydroxyethoxyphenyl) sulfone and 4, 4' -bis [4- (2-dihydroxyethoxy) -3-methylphenyl ] sulfone; 1, 4-bishydroxyethoxybenzene, 1, 3-bishydroxyethoxybenzene, 1, 2-bishydroxyethoxybenzene, 1, 3-bis [2- [4- (2-hydroxyethoxy) phenyl ] propyl ] benzene, 1, 4-bis [2- [4- (2-hydroxyethoxy) phenyl ] propyl ] benzene, 4' -bis (2-hydroxyethoxy) biphenyl, 1, 3-bis [4- (2-hydroxyethoxy) phenyl ] -5, 7-dimethyladamantane, an anhydrosugar alcohol represented by a dihydroxy compound represented by the following formula (4); and a compound having a cyclic ether structure such as spiroglycol represented by the following general formula (6), and these may be used alone or in combination of 2 or more.
These dihydroxy compounds (A) may be used alone or in combination of 2 or more. In the present invention, examples of the dihydroxy compound represented by the formula (4) include isosorbide, isomannide, and isoidide which are stereoisomeric, and 1 kind of these compounds may be used alone or 2 or more kinds may be used in combination.
Among the dihydroxy compounds (a), isosorbide obtained by dehydration condensation of sorbitol produced from various starches which are abundant in resources and easily available is most preferable from the viewpoints of easiness of obtaining and production, optical properties, and moldability. In the present invention, isosorbide is preferably used as the dihydroxy compound (a).
(dihydroxy Compound (B))
In the present invention, as the dihydroxy compound, a dihydroxy compound (B) which is a dihydroxy compound other than the dihydroxy compound (a) can be used. As the dihydroxy compound (B), for example, an alicyclic dihydroxy compound, an aliphatic dihydroxy compound, an oxyalkylene glycol, an aromatic dihydroxy compound, and a diol having a cyclic ether structure can be used as the dihydroxy compound forming the structural unit of the polycarbonate, together with the dihydroxy compound (A), for example, the dihydroxy compound represented by the formula (4).
The alicyclic dihydroxy compound that can be used in the present invention is not particularly limited, and a compound generally having a five-membered ring structure or a six-membered ring structure is preferably used. Further, the six-membered ring structure may be fixed in a chair or boat shape by means of covalent bonds. The alicyclic dihydroxy compound has a five-membered ring or six-membered ring structure, and thus the heat resistance of the obtained polycarbonate can be improved. The number of carbon atoms contained in the alicyclic dihydroxy compound is usually 70 or less, preferably 50 or less, and more preferably 30 or less. The larger the value, the higher the heat resistance, but the synthesis or purification is difficult or the cost is expensive. The smaller the number of carbon atoms, the easier purification and acquisition.
Specific examples of the alicyclic dihydroxy compound containing a five-membered ring structure or a six-membered ring structure that can be used in the present invention include alicyclic dihydroxy compounds represented by the following general formula (II) or (III).
HOCH2-R1-CH2OH (II)
HO-R2-OH (III)
(in the formulae (II) and (III), R1、R2Each represents a C4-20 cycloalkylene group. )
The cyclohexanedimethanol which is the alicyclic dihydroxy compound represented by the above general formula (II) includes R in the general formula (II)1Using the following general formula (IIa) (wherein R is3An alkyl group having 1 to 12 carbon atoms or a hydrogen atom). Specific examples of such isomers include 1, 2-cyclohexanedimethanol, 1, 3-cyclohexanedimethanol and 1, 4-cyclohexanedimethanol.
The tricyclodecanedimethanol and pentacyclopentadecane dimethanol which are alicyclic dihydroxy compounds represented by the above general formula (II) include R in the general formula (II)1Various isomers represented by the following general formula (IIb) (wherein n represents 0 or 1).
The decalindimethanol or tricyclotetradecane dimethanol which is the alicyclic dihydroxy compound represented by the above general formula (II) includes R in the general formula (II)1Various isomers represented by the following general formula (IIc) (wherein m represents 0 or 1). Specific examples of such isomers include 2, 6-decahydronaphthalene dimethanol, 1, 5-decahydronaphthalene dimethanol, and 2, 3-decahydronaphthalene dimethanol.
The norbornanedimethanol which is the alicyclic dihydroxy compound represented by the above general formula (II) includes R in the general formula (II)1Various isomers represented by the following general formula (IId). Specific examples of such isomers include 2, 3-norbornanedimethanol and 2, 5-norbornanedimethanol.
Adamantanedimethanol as the alicyclic dihydroxy compound represented by the general formula (II) includes R in the general formula (II)1Various isomers represented by the following general formula (IIe). Specific examples of such isomers include 1, 3-adamantanedimethanol.
Further, the cyclohexanediols which are the alicyclic dihydroxy compounds represented by the above general formula (III) include R in the general formula (III)2Using the following general formula (IIIa) (wherein R3An alkyl group having 1 to 12 carbon atoms or a hydrogen atom). Specific examples of such isomers include 1, 2-cyclohexanediol, 1, 3-cyclohexanediol, 1, 4-cyclohexanediol, and 2-methyl-1, 4-cyclohexanediol.
The tricyclodecanediol and pentacyclopentadecane diol as the alicyclic dihydroxy compound represented by the above general formula (III) include R in the general formula (III)2Various isomers represented by the following general formula (IIIb) (wherein n represents 0 or 1).
The decahydronaphthalene diol or tricyclotetradecane diol as the alicyclic dihydroxy compound represented by the above general formula (III) includes R in the general formula (III)2Various isomers represented by the following general formula (IIIc) (wherein m represents 0 or 1). Specific examples of such isomers include 2, 6-decahydronaphthalene diol, 1, 5-decahydronaphthalene diol, and 2, 3-decahydronaphthalene diol.
The norbornanediol which is the alicyclic dihydroxy compound represented by the above general formula (III) includes R in the general formula (III)2Various isomers represented by the following general formula (IIId). Specific examples of such isomers include 2, 3-norbornanediol and 2, 5-norbornanediol.
The adamantanediol as the alicyclic dihydroxy compound represented by the above general formula (III) includes R in the general formula (III)2Various isomers represented by the following general formula (IIIe). Specific examples of such isomers include 1, 3-adamantanediol.
Among the specific examples of the alicyclic dihydroxy compound, cyclohexanedimethanol, tricyclodecanedimethanol, adamantanediol, and pentacyclopentadecane dimethanol are particularly preferable, and 1, 4-cyclohexanedimethanol, 1, 3-cyclohexanedimethanol, 1, 2-cyclohexanedimethanol, and tricyclodecanedimethanol are preferable from the viewpoint of ease of acquisition and ease of handling. In the present invention, tricyclodecanedimethanol is suitably used as the dihydroxy compound (B).
Examples of the aliphatic dihydroxy compound that can be used in the present invention include ethylene glycol, 1, 3-propanediol, 1, 2-propanediol, 1, 4-butanediol, 1, 3-butanediol, 1, 2-butanediol, 1, 5-heptanediol, and 1, 6-hexanediol. Examples of the oxyalkylene glycol usable in the present invention include diethylene glycol, triethylene glycol, tetraethylene glycol and polyethylene glycol.
Examples of the aromatic dihydroxy compound that can be used in the present invention include 2, 2-bis (4-hydroxyphenyl) propane [ ═ bisphenol a ], 2-bis (4-hydroxy-3, 5-dimethylphenyl) propane, 2-bis (4-hydroxy-3, 5-diethylphenyl) propane, 2-bis (4-hydroxy- (3, 5-diphenyl) phenyl) propane, 2-bis (4-hydroxy-3, 5-dibromophenyl) propane, 2-bis (4-hydroxyphenyl) pentane, 2, 4' -dihydroxy-diphenylmethane, bis (4-hydroxyphenyl) methane, bis (4-hydroxy-5-nitrophenyl) methane, and mixtures thereof, 1, 1-bis (4-hydroxyphenyl) ethane, 3-bis (4-hydroxyphenyl) pentane, 1-bis (4-hydroxyphenyl) cyclohexane, bis (4-hydroxyphenyl) sulfone, 2,4 ' -dihydroxydiphenylsulfone, bis (4-hydroxyphenyl) sulfide, 4 ' -dihydroxydiphenyl ether, 4 ' -dihydroxy-3, 3 ' -dichlorodiphenyl ether, 4 ' -dihydroxy-2, 5-diethoxydiphenyl ether, 9-bis [4- (2-hydroxyethoxy) phenyl ] fluorene, 9-bis [4- (2-hydroxyethoxy-2-methyl) phenyl ] fluorene, 9-bis (4-hydroxyphenyl) fluorene, 9, 9-bis (4-hydroxy-2-methylphenyl) fluorene.
The glycols having a cyclic ether structure usable in the present invention include, for example, spiroglycols and dioxane glycols. The above-mentioned exemplary compounds are examples of alicyclic dihydroxy compounds, aliphatic dihydroxy compounds, oxyalkylene glycols, aromatic dihydroxy compounds, and glycols having a cyclic ether structure, which can be used in the present invention, but are not limited thereto at all. 1 or 2 or more of these compounds may be used together with the dihydroxy compound represented by formula (4).
By using these dihydroxy compounds (B), effects such as improvement in flexibility, improvement in heat resistance, and improvement in moldability according to the application can be obtained. The proportion of the dihydroxy compound (a), for example, the dihydroxy compound represented by formula (4), relative to the total dihydroxy compounds constituting the polycarbonate resin of the present invention is not particularly limited, but is preferably 10 mol% or more, more preferably 40 mol% or more, and still more preferably 60 mol% or more, and is preferably 90 mol% or less, more preferably 80 mol% or less, and still more preferably 70 mol% or less. If the content ratio of the structural unit derived from another dihydroxy compound is too large, the performance such as optical properties may be deteriorated.
When an alicyclic dihydroxy compound is used among the other dihydroxy compounds, the ratio of the total of the dihydroxy compound (a), the dihydroxy compound represented by formula (4) and the alicyclic dihydroxy compound to the total dihydroxy compounds constituting the polycarbonate is not particularly limited, but is preferably 80 mol% or more, more preferably 90 mol% or more, and still more preferably 95 mol% or more.
The content ratio of the structural unit derived from the dihydroxy compound (a), for example, the dihydroxy compound represented by formula (4), and the structural unit derived from the alicyclic dihydroxy compound in the polycarbonate resin of the present invention may be selected at any ratio, and the structural unit derived from the dihydroxy compound represented by formula (4): the structural unit derived from the alicyclic dihydroxy compound is preferably 1:99 to 99:1 (mol%), and the structural unit derived from the dihydroxy compound represented by formula (4): the structural unit derived from the alicyclic dihydroxy compound is particularly preferably 10:90 to 90:10 (mol%). When the structural unit derived from the dihydroxy compound represented by formula (4) is more and the structural unit derived from the alicyclic dihydroxy compound is less than the above range, coloring tends to be easy, whereas when the structural unit derived from the dihydroxy compound represented by formula (4) is less and the structural unit derived from the alicyclic dihydroxy compound is more, the molecular weight tends to be less likely to increase.
Further, when an aliphatic dihydroxy compound, an oxyalkylene glycol, an aromatic dihydroxy compound, or a diol having a cyclic ether structure is used, the ratio of the dihydroxy compound (a), for example, the dihydroxy compound represented by formula (4), and the total of these various dihydroxy compounds to the total of all dihydroxy compounds constituting the polycarbonate is not particularly limited, and may be selected at any ratio. The content ratio of the structural unit derived from the dihydroxy compound (a), for example, the dihydroxy compound represented by the formula (4) to the structural unit derived from each of these dihydroxy compounds is not particularly limited, and may be selected at any ratio.
The details of the polycarbonate-based resin are described in, for example, Japanese patent laid-open No. 2012-31370 (Japanese patent No. 5448264). The description of this patent document is incorporated herein by reference.
C. Method for producing optical film
The optical film is obtained by film-molding a resin such as the polycarbonate-based resin described in the item B. As a method for forming the thin film, any and appropriate forming method can be used. Specific examples thereof include extrusion molding, blow molding, casting coating (for example, casting), and calender molding. Among them, extrusion molding or cast coating which can improve the smoothness of the obtained film and can obtain good optical uniformity can be preferably used, and cast coating is more preferably used. The linear velocity of the casting coating method is preferably 7 to 15m/min, more preferably 7 to 12 m/min. An optical film having substantially optical isotropy can be obtained by forming the resin film described in item B at a linear speed equal to or lower than a predetermined speed. However, when the linear velocity is equal to or lower than a constant velocity, the degree of orientation of the obtained optical film is lowered, which causes a change in retardation and a decrease in adhesiveness in the humidification reliability test. When the linear velocity is set to a constant velocity or more, the degree of orientation of the optical film increases, and a change in retardation in the humidification reliability test can be suppressed, thereby improving the adhesiveness. That is, by performing casting film formation at a linear velocity in the above range, it is possible to achieve both desired in-plane retardation, suppression of retardation change in a humidification reliability test, and excellent adhesiveness. Further, by casting film formation at a linear velocity in the above range, film thickness unevenness in the MD direction (longitudinal direction) and retardation unevenness due to film thickness unevenness can be suppressed.
D. Polarizing plate
A polarizing plate typically includes a polarizing material and the optical film bonded to at least one surface of the polarizing material with an adhesive layer interposed therebetween. As described above, the optical film has excellent adhesion to the polarizer. The polarizer may have a protective layer on at least one surface of the polarizer. Further, the polarizing plate may have an adhesive layer and a spacer on the surface opposite to the viewing side. The polarizer, the protective layer, the adhesive layer, and the separator may employ a structure known in the art, and thus detailed description thereof is omitted.
The adhesive composition constituting the adhesive layer is typically an active energy ray-curable adhesive composition. The active energy ray-curable adhesive composition contains an active energy ray-curable compound.
The active energy ray-curable adhesive composition of the present invention is, for example, an active energy ray-curable adhesive composition containing, as curable components, active energy ray-curable compounds (a), (B) and (C), and contains an SP value of 29.0 (MJ/m) when the total amount of the composition is 100% by weight3)1/2 and 32.0 (MJ/m)3)0.0 to 4.0 wt% of an active energy ray-curable compound (A) having a molecular weight of not more than 1/2 and an SP value of 18.0 (MJ/m)3)1/2 above and below 21.0 (MJ/m)3)1/2, 5.0 to 98.0 wt% of the active energy ray-curable compound (B), and 21.0 SP value (MJ/m)3)1/2 and 26.0 (MJ/m)3)1/2 or less, 5.0 to 98.0 wt% of an active energy ray-curable compound (C). In the present invention, the "total amount of the composition" means the total amount of various initiators and/or additives in addition to the active energy ray-curable compound.
The active energy ray-curable compound (A) is not particularly limited as long as it has a radical-polymerizable group such as a (meth) acrylate group and has an SP value of 29.0 (MJ/m)3)1/2 and 32.0 (MJ/m)3)1/2, the following compounds can be used without limitation. Specific examples of the active energy ray-curable compound (A) include hydroxyethylpropylEnamides (SP value 29.5), N-methylolacrylamides (SP value 31.5), and the like. In the present invention, the (meth) acrylate group means an acrylate group and/or a methacrylate group.
The active energy ray-curable compound (B) is not particularly limited as long as it has a radical-polymerizable group such as a (meth) acrylate group and has an SP value of 18.0 (MJ/m)3)1/2 above and below 21.0 (MJ/m)3)1/2, can be used without limitation. Specific examples of the active energy ray-curable compound (B) include tripropylene glycol diacrylate (SP value 19.0), 1, 9-nonanediol diacrylate (SP value 19.2), tricyclodecane dimethanol diacrylate (SP value 20.3), cyclic trimethylolpropane formal acrylate (SP value 19.1), dioxane glycol diacrylate (SP value 19.4), and EO-modified diglycerol tetraacrylate (SP value 20.9). As the active energy ray-curable compound (B), commercially available products such as ARONIX M-220 (manufactured by Toyo chemical Co., Ltd., SP value 19.0), Light Acrylate 1,9ND-A (manufactured by KyowｃA Kagaku K.K., SP value 19.2), Light Acrylate DGE-4A (manufactured by KyowｃA Kagaku K.K., SP value 20.9), Light Acrylate DCP-A (manufactured by KyowｃA Kagaku K.K., SP value 20.3), SR-531 (manufactured by KyowｃA Kagaku K.K., SP value 19.1), CD-536 (manufactured by KyowｃA Kagaku K.K., SP value 19.4) and the like can be suitably used.
The active energy ray-curable compound (C) is not particularly limited as long as it has a radical-polymerizable group such as a (meth) acrylate group and has an SP value of 21.0 (MJ/m)3)1/2 and 26.0 (MJ/m)3)1/2, the following compounds can be used without limitation. Specific examples of the active energy ray-curable compound (C) include acryloylmorpholine (SP value 22.9), N-methoxymethylacrylamide (SP value 22.9), N-ethoxymethylacrylamide (SP value 22.3), and the like. As the active energy ray-curable compound (C), commercially available products can be suitably used, and examples thereof include ACMO (manufactured by KOHJIN Co., Ltd., SP value 22.9), Wasmer 2MA (manufactured by Chimaphilai K.K., SP value 22.9), Wasmer EMA (manufactured by Chimaphilai K.K., SP value 22.3), and Wasmer 3MA (manufactured by Chimaphilai K.K., SP value 22.3)22.4), etc.
The adhesive composition is described in detail in, for example, Japanese patent laid-open publication No. 2019-147865. The description of this patent document is incorporated herein by reference. By adhering the optical film to the adhesive layer made of the adhesive composition, the adhesiveness of the optical film becomes more excellent.
Examples
The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. The measurement method and evaluation method of each characteristic are as follows.
(1) In-plane retardation
The optical films obtained in examples and comparative examples were cut into a length of 4cm and a width of 4cm to obtain measurement samples. The in-plane retardation Re (550) was measured using a sample manufactured by Axometrics under the product name "Axoscan".
(2) Refractive index and birefringence Δ nxy
Measured with an Abbe refractometer (DR-M2, manufactured by Atago). The measurement was carried out at 23 ℃.
(3) Thickness of
The thickness of 10 μm or less was measured using an interference film thickness meter (available under the name "MCPD-9800" manufactured by Otsuka electronics Co., Ltd.). The thickness exceeding 10 μm was measured by using a digital micrometer (product name "KC-351C" manufactured by ANRITSU Co., Ltd.).
(4) Degree of orientation
The degree of orientation was determined by X-ray diffraction (XRD) using the optical thin films obtained in examples and comparative examples.
(5) Change of humidification phase difference
The optical films obtained in examples and comparative examples were cut into 5cm × 5cm, and an adhesive was applied to one surface of the optical film by a hand press roll, and the adhesive surface was applied to one surface of alkali glass to obtain a test piece. The test piece was stored in an oven at a temperature of 65 ℃ and a humidity of 90% for 500 hours (humidified test), and the phase difference change (%) before the start of the test and after the test was calculated. The case where the phase difference change was 10% or less was regarded as good, and the case where the phase difference change exceeded 10% was regarded as bad.
(6) Parallel hue a and b values
The parallel hue a value and the parallel hue b value of the optical films obtained in examples and comparative examples were obtained. The measurement was carried out using a spectrophotometer (product name "V-7100" manufactured by Nippon Kayaku Co., Ltd.). The case where the change rate of the b value before the charging into the ultraviolet fading tester (apparatus name; ultraviolet fading tester U48, Suga Test Instruments Co., Ltd., manufactured by Ltd.) and the b value after the charging for 100 hours was 1% or less was regarded as good, and the case where the change rate exceeded 1% was regarded as bad.
(7) Adhesion Property
The optical films obtained in examples and comparative examples were bonded to a polarizer to obtain a laminate. The laminate thus obtained was cut into a size of 200mm in the direction parallel to the stretching direction of the polarizer and 15mm in the orthogonal direction, and the laminate was attached to a glass plate. Then, a slit was made between the optical film and the polarizer with a cutter, and the optical film and the polarizer were peeled off at a peeling speed of 1000mm/min in a 90-degree direction by a TENSILON universal tester RTC (manufactured by A & D), and the peel strength (N/15mm) was measured. The case where the peel strength was 1N/15mm or more was regarded as good, and the case where the peel strength was less than 1N/15mm was regarded as bad.
[ example 1]
In a reaction vessel, 47.19 parts by mass of tricyclodecanedimethanol (hereinafter, sometimes abbreviated as "TCDDM"), 175.1 parts by mass of diphenyl carbonate (hereinafter, sometimes abbreviated as "DPC") and 0.979 parts by mass of a 0.2 mass% aqueous solution of cesium carbonate as a catalyst were charged to 81.98 parts by mass of isosorbide (hereinafter, sometimes abbreviated as "ISB"), and the heating bath temperature was heated to 150 ℃ in a nitrogen atmosphere, and the raw materials were dissolved with stirring as necessary (about 15 minutes) as a first step of the reaction. Then, the pressure was set to 13.3kPa from the normal pressure, and the generated phenol was taken out of the reaction vessel while increasing the temperature of the heating tank to 190 ℃ over 1 hour. After the entire reaction vessel was maintained at 190 ℃ for 15 minutes, the pressure in the reaction vessel was set to 6.67kPa as a second step, the temperature in the heating tank was increased to 230 ℃ over 15 minutes, and the produced phenol was taken out of the reaction vessel. Since the stirring torque of the stirrer was gradually increased, it took 8 minutes to raise the temperature to 250 ℃, and the pressure in the reaction vessel was set to 0.200kPa or less to remove the generated phenol. After the predetermined stirring torque was reached, the reaction was terminated, and the resultant reaction product was extruded into water to obtain pellets of a polycarbonate resin. The birefringence Δ nxy of the obtained polycarbonate resin was 0.015. The obtained polycarbonate resin was vacuum-dried at 100 ℃ for 12 hours, and then an optical film made of the polycarbonate resin was produced at a film-forming linear velocity of 7m/min using a film-forming apparatus equipped with a single-screw extruder (manufactured by Toshiba mechanical Co., Ltd., cylinder set temperature: 250 ℃), a T die (width 1700mm, set temperature: 250 ℃), a casting roll (set temperature: 60 ℃) and a winder. The obtained optical film had an orientation degree of 7.4%, an in-plane retardation Re (550) of 6nm, and a thickness of 40 μm. The obtained optical films were subjected to the evaluations (5) to (7) above. The results are shown in Table 1.
[ example 2]
An optical film was obtained in the same manner as in example 1 except that the film forming line speed was set to 8m/min and the thickness was set to 30 μm. The obtained optical film had an orientation degree of 5.7% and an in-plane retardation Re (550) of 3 nm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
[ example 3]
An optical film was obtained in the same manner as in example 1 except that the birefringence Δ nxy of the polycarbonate resin was 0.018, the film formation linear velocity was 10m/min, and the thickness was 20 μm. The obtained optical film had an orientation degree of 6.1% and an in-plane retardation Re (550) of 2 nm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
[ example 4]
An optical film was obtained in the same manner as in example 1 except that the birefringence Δ nxy of the polycarbonate resin was 0.024, the film forming linear velocity was 12m/min, and the thickness was 20 μm. The obtained optical film had an orientation degree of 8.1% and an in-plane retardation Re (550) of 2 nm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
Comparative example 1
An optical film was obtained in the same manner as in example 1 except that the birefringence Δ nxy of the polycarbonate resin was 0.016 and the film forming line speed was 5 m/min. The obtained optical film had an orientation degree of 4.8% and an in-plane retardation Re (550) of 5 nm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
Comparative example 2
An optical film was obtained in the same manner as in example 1 except that a Triacetylcellulose (TAC) film (product of konica minolta co., ltd., trade name "KC 4 UA") having a birefringence Δ nxy of 0.018 was used and the linear velocity was set to 15 m/min. The obtained optical film had an orientation degree of 5.1% and an in-plane retardation Re (550) of 2 nm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
Comparative example 3
(polymerization of polyester carbonate-based resin)
Polymerization was carried out using a batch polymerization apparatus comprising 2 vertical reactors equipped with stirring blades and a reflux cooler controlled at 100 ℃. Adding bis [9- (2-phenoxycarbonylethyl) fluoren-9-yl]29.60 parts by mass (0.046mol) of methane, 29.21 parts by mass (0.200mol) of Isosorbide (ISB), 42.28 parts by mass (0.139mol) of Spiroglycol (SPG), 63.77 parts by mass (0.298mol) of diphenyl carbonate (DPC), and 1.19 × 10 parts by mass of calcium acetate monohydrate as a catalyst-2Mass portion (6.78X 10)-5mol). After the inside of the reactor was replaced with nitrogen gas under reduced pressure, the reactor was heated with a heat medium, and stirring was started when the inside temperature reached 100 ℃. 40 minutes after the start of the temperature increase, the internal temperature was controlled to 220 ℃ and the pressure reduction was started while maintaining the internal temperature, and the pressure was set to 13.3kPa after 90 minutes from the start of the temperature increase to 220 ℃. Phenol vapor by-produced together with the polymerization reaction was introduced into a reflux condenser at 100 ℃, a few amounts of monomer components contained in the phenol vapor were returned to the reactor, and the uncondensed phenol vapor was introduced into a condenser at 45 ℃ and recovered. After nitrogen gas was introduced into the 1 st reactor and the pressure was once returned to atmospheric pressure,the reaction liquid after oligomerization in the 1 st reactor was transferred to the 2 nd reactor. Subsequently, the temperature increase and pressure reduction in the 2 nd reactor were started, and the internal temperature and pressure were set to 240 ℃ and 0.2kPa for 50 minutes. Then, the polymerization was allowed to proceed until a predetermined stirring power was reached. When the predetermined power was reached, nitrogen gas was introduced into the reactor to recover the pressure, the polyester carbonate resin thus produced was extruded into water, and the strand was cut to obtain pellets. The birefringence Δ nxy of the obtained polycarbonate resin was 0.012.
(production of optical film)
After the obtained polyester carbonate resin (pellets) was dried under vacuum at 80 ℃ for 5 hours, a film-forming apparatus equipped with a single-screw extruder (manufactured by Toshiba mechanical Co., Ltd., cylinder set temperature: 270 ℃), a T die (width 1700mm, set temperature: 270 ℃), a casting roll (set temperature: 75 ℃) and a winder was used to form a long optical film having a thickness of 40 μm at a film-forming line speed of 8 m/min. The obtained optical film had an orientation degree of 4.3% and an in-plane retardation Re (550) of 7 nm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
Comparative example 4
A cellulose triacetate film having a thickness of 40 μm was subjected to brushing treatment and then coated. The obtained optical film had an in-plane retardation Re (550) of 3nm and a thickness of 2 μm. The obtained optical film was subjected to the same evaluation as in example 1. The results are shown in Table 1.
[ TABLE 1]
As is apparent from table 1, the optical film of the examples of the present invention is excellent in all of the changes in the retardation under humidification, the weather resistance and the adhesiveness. This is presumably achieved by forming a resin film containing a specific polycarbonate resin having a specific birefringence Δ nxy at a specific linear velocity. Further, as is clear from comparison of examples 1 to 4 with comparative example 4, by using an optical film containing no ultraviolet absorber, a change in hue in the weather resistance test can be suppressed.
Industrial applicability
The optical film and the polarizing plate according to the embodiment of the present invention are suitably used for an image display device.
Claims (7)
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| TW200808520A (en) * | 2006-06-22 | 2008-02-16 | Jsr Corp | Optical film, manufacturing method thereof, polarizing plate and liquid crystal panel |
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| JP2006113203A (en) * | 2004-10-13 | 2006-04-27 | Nitto Denko Corp | Laminated optical film, elliptically polarizing plate, and image display device |
| TWI467251B (en) | 2008-11-07 | 2015-01-01 | Teijin Chemicals Ltd | Phase difference film |
| EP2371877B1 (en) | 2008-11-28 | 2026-04-29 | Mitsubishi Chemical Corporation | Polycarbonate resin, polycarbonate resin composition, optical film, and polycarbonate resin molded article |
| WO2015141592A1 (en) * | 2014-03-20 | 2015-09-24 | 帝人株式会社 | Polycarbonate resin and optical film |
| JP6867161B2 (en) | 2014-07-31 | 2021-04-28 | 三菱瓦斯化学株式会社 | An optical film, a laminated optical film containing the optical film, and a method for manufacturing the optical film. |
| JP6565597B2 (en) | 2014-10-28 | 2019-08-28 | 三菱ケミカル株式会社 | Polycarbonate resin, molded product and optical film |
| JP5922292B1 (en) * | 2015-02-16 | 2016-05-24 | 住友化学株式会社 | Curable adhesive composition and polarizing plate using the same |
| WO2016199509A1 (en) | 2015-06-10 | 2016-12-15 | コニカミノルタ株式会社 | High-orientation film having different type of resin unevenly distributed on surface thereof, method for producing same, and polarizing plate, liquid crystal display device, decorative film and gas barrier film each manufactured using same |
| JP7163066B2 (en) * | 2018-05-22 | 2022-10-31 | 日東電工株式会社 | Circularly polarizing plate and image display device |
| WO2020137409A1 (en) * | 2018-12-27 | 2020-07-02 | 日本ゼオン株式会社 | Optically anisotropic laminate, method for manufacturing same, circularly polarizing plate, and image display device |
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| JP2006241446A (en) * | 2005-02-02 | 2006-09-14 | Mitsubishi Gas Chem Co Inc | Polyester film, method for producing the same, and use thereof |
| TW200808520A (en) * | 2006-06-22 | 2008-02-16 | Jsr Corp | Optical film, manufacturing method thereof, polarizing plate and liquid crystal panel |
| CN102666677A (en) * | 2009-11-19 | 2012-09-12 | 三菱化学株式会社 | Polycarbonate resin film, transparent film and manufacturing method thereof |
| JP2020033418A (en) * | 2018-08-28 | 2020-03-05 | 日東電工株式会社 | Base material for surface protective film, production method of the base material, surface protective film using the base material, and optical film with surface productive film |
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