KR20110131112A - Optical film - Google Patents

Abstract

PURPOSE: An optical film has high transmittance and high smoothness, and provided to polarizing-converse to thickness direction. CONSTITUTION: An optical film is manufactured by polymerizing of composition including polymerizable component. The composition comprises one component or more selected from the group consisting of polymers which can be obtained by polymerization of the monomers in the chemical formula 1. In the chemical formula 1 R1 is hydrogen or methyl, R2 is substituted or non-substituted C5-15 monovalent bridged hydrocarbon radical, and n1 is integer of 1-3.

Description

Optical film {OPTICAL FILM}

The present invention relates to an optical film.

An optical film is used for image display apparatuses, such as a liquid crystal display device. As such an optical film, JP 2010-116528 A discloses a urethane acrylate obtained by reacting polyhexamethylene carbonate diol, 1,4-cyclohexanedimethanol, isophorone diisocyanate and 2-hydroxyethyl acrylate. Disclosed are an optical film that is formed using a resin having a structural unit derived and a composition containing N-vinylcarbazole.

The present invention,

1 or more types chosen from the group which consists of a polymer obtained by superposing | polymerizing the monomer represented by <1> following formula (1) and the monomer represented by following formula (1),

Resin containing 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle in all the structural units.

An optical film obtained by superposing | polymerizing the polymerizable component contained in the composition containing:

Formula, R ¹ is a hydrogen atom or a methyl group, R ² is even have a substituent represents a good cross-linked monovalent cyclic hydrocarbon group of a carbon number of 5~15, -CH ₂ included the cross-linked polycyclic hydrocarbon groups - is -NR ³ -, May be substituted with -O-, -CO- or -S-, R ³ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, n ¹ represents an integer of 0 to 3;

The optical film as described in <1> whose <2> resin is 1 or more types chosen from the group which consists of a polycarbonate and polyether sulfone;

<3> R ¹ is, the optical film described in the group of <1> or <2>;

The optical film as described in any one of <1>-<3> in which a <4> composition contains a photoinitiator further;

<5> Retardation plate containing the optical film as described in any one of <1>-<4>;

1 or more types chosen from the group which consists of a polymer obtained by superposing | polymerizing the monomer represented by <6> following formula (1) and the monomer represented by following formula (1),

Resin containing 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle in all the structural units.

Composition comprising:

Formula, R ¹ is a hydrogen atom or a methyl group, R ² is even have a substituent represents a good cross-linked monovalent cyclic hydrocarbon group of a carbon number of 5~15, -CH ₂ included the cross-linked polycyclic hydrocarbon groups - is -NR ³ -, May be substituted with -O-, -CO- or -S-, R ³ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, n ¹ represents an integer of 0 to 3;

<7> Furthermore, the composition as described in <6> containing a photoinitiator;

<8> Furthermore, the composition as described in <6> or <7> containing a solvent;

<9> Polymer obtained by superposing | polymerizing the polymeric component contained in the composition in any one of <6>-<8>;

<10> After manufacturing the composition as described in <8> to the smooth surface, the manufacturing method of the optical film obtained by distilling a solvent off; And so on.

In this invention, an "optical film" is a film which can transmit light, and means the film which has an optical function. The optical function means refraction, birefringence, antireflection, enlarged viewing angle, light diffusion, brightness enhancement, and the like.

The optical film of this invention is obtained by superposing | polymerizing the polymerizable component contained in the composition of this invention.

The composition of the present invention is formula (1):

Selected from the group consisting of a monomer (hereinafter abbreviated as 'monomer (1)') and a polymer obtained by polymerizing a monomer represented by formula (1) (hereinafter abbreviated as 'polymer (1)'). With one or more kinds,

It is a composition containing resin (henceforth abbreviated as "resin 2") containing 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle in all the structural units.

In formula (1), R <^1> represents a hydrogen atom or a methyl group, Preferably it is a methyl group.

R <^2> represents the C5-C15 monovalent crosslinkable hydrocarbon group which may have a substituent. As an unsubstituted temporary exchange-type hydrocarbon group, group represented by a following formula is mentioned.

-CH ₂ -contained in the temporarily exchangeable hydrocarbon group may be substituted with -NR ^3- , -O-, -CO-, or -S-, and R ³ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Examples of the alkyl group having 1 to 3 carbon atoms include methyl group, ethyl group and propyl group. Examples of the group in which the -CH ₂ -contained in the crosslinkable hydrocarbon group is substituted with -NR ^3- , -O-, -CO- or -S- include an oxaadamantyl group, an oxoadamantyl group, and N-methylazanorbor And a 5-oxa-4-oxotricyclo [5.2.1.0 ^3,7 ] nonyl group.

Substituents which may be included in the temporary exchange-type hydrocarbon group include an alkyl group having 1 to 3 carbon atoms, a hydroxy group (-OH), an alkoxy group having 1 to 3 carbon atoms, an amino group, a nitro group, a carboxyl group (-COOH), and a sulfo group (-SO ₃ H). ), Chloro group (chlorine atom), bromo group (bromine atom) and iodine group (iodine atom). Examples of the alkyl group having 1 to 3 carbon atoms include methyl group, ethyl group and propyl group. As a C1-C3 alkoxy group, a methoxy group, an ethoxy group, and a propoxy group are mentioned. Examples of the temporary exchange-type hydrocarbon group substituted with these substituents include a hydroxyadamantyl group, a methoxyadamantyl group, a nitronorbornyl group, a carboxycitcyclocyclodecyl group and a chlorodicyclodecyl group.

It is preferable that R <^2> is the following group.

In formula (1), n <^1> represents the integer of 0-3, and 0 or 1 is preferable.

As a preferable monomer (1), the compound represented by Formula (1-1)-Formula (1-6) is mentioned. If monomer (1) is these compounds, the photoelastic coefficient of the optical film obtained will become small.

The polymer (1) may be a polymer obtained by polymerizing only the monomer (1) or a copolymer of the monomer (1) and monomers other than the monomer (1). As monomers other than the monomer (1), the monomer represented by Formula (A) mentioned later is mentioned.

The polymer (1) is obtained by polymerizing, for example, the monomer which guide | induces the structural unit which comprises the polymer (1) by a well-known radical polymerization method. Known radical polymerization methods include solution polymerization, suspension polymerization, emulsion polymerization, and bulk polymerization. In view of ease of molecular weight adjustment and film-forming properties of the polymer (1), Legal is preferred. It is preferable that the polymer (1) is a random polymer from the transparency point of the optical film obtained. The polymer (1) may be a commercially available polymer.

Examples of the polymerization initiator used in the radical polymerization method include 2,2'-azobisisobutyronitrile, 2,2'-azobis (2-methylbutyronitrile), and 1,1'-azobis (cyclohexane-1). -Carbonitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl-2, Azo compounds such as 2'-azobis (2-methylpropionate) and 2,2'-azobis (2-hydroxymethylpropionitrile), lauryl peroxide, tert-butylhydroperoxide and benzoyl peroxide tert-butylperoxybenzoate, cumene hydroperoxide, diisopropylperoxydicarbonate, dipropylperoxydicarbonate, tert-butylperoxyneodecanoate, tert-butylperoxypivalate, ( Organic peroxides such as 3,5,5-trimethylhexanoyl) peroxide and inorganic peroxides such as potassium persulfate, ammonium persulfate and hydrogen peroxide. Moreover, the redox type initiator which used the thermal polymerization initiator and the reducing agent together can be mentioned as a polymerization initiator.

The solvent used for the solution polymerization method is not limited as long as it does not interfere with the polymerization. As a solvent, Ester solvents, such as aromatic hydrocarbon solvents, such as toluene and xylene, ethyl acetate, butyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether acetate, Alcohol solvents such as methanol, ethanol, propyl alcohol and isopropyl alcohol, and ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone and cyclohexanone.

In the solution polymerization method, the total amount of the monomers guiding the structural unit constituting the polymer (1) is preferably 10% by mass or more, more preferably 15% by mass or more and 50% by mass or less in the reaction solution, and 20% by mass. It is especially preferable that they are% or more and 40 mass% or less. If the total amount of the monomer which guides the structural unit which comprises the polymer (1) is in the said range, superposition | polymerization control and the viscosity of the resin solution obtained are also excellent.

When the polymer (1) is a copolymer of the monomer (1) and monomers other than the monomer (1), the structural unit derived from the monomer (1) is 40 mass% with respect to the total of all the structural units of the polymer (1). It is preferable that it is above, and it is more preferable that it is 50 mass% or more.

It is preferable that reaction temperature in a solution polymerization method is 15 degreeC or more and 120 degrees C or less, It is more preferable that they are 30 degreeC or more and 110 degrees C or less, It is especially preferable that they are 40 degreeC or more and 100 degrees C or less. If superposition | polymerization temperature is in the said range, superposition | polymerization control is excellent.

The number average molecular weight of the polymer (1) is preferably 1,000 or more and 1,000,000 or less, more preferably 2,000 or more and 800,000 or less, and particularly preferably 3,000 or more and 500,000 or less. When the number average molecular weight of the polymer (1) is in the above range, the polymer (1) is excellent in viscosity, film forming property, toughness and heat resistance.

At least 1 sort (s) of content chosen from the group which consists of monomer (1) and polymer (1) in the composition of this invention is at least 1 sort (s) chosen from the group which consists of monomer (1) and polymer (1), and resin (2 Regarding the total amount with c), it is preferably 5% by mass to 70% by mass, more preferably 7% by mass to 65% by mass, and particularly preferably 10% by mass to 60% by mass. If it is in the said range, the photoelastic coefficient of the optical film obtained will become small.

It is preferable that the composition of this invention contains monomer (1).

Resin (2) contained in the composition of this invention contains 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle in all the structural units. When content of the structural unit which has an aromatic ring or an aromatic heterocycle is this range, the photoelastic coefficient of the optical film obtained will become small. Content of the structural unit which has an aromatic ring or aromatic heterocycle in resin (2), Preferably it is 50 mol% or more and 100 mol% or less in all the structural units, More preferably, it is 80 mol% or more and 100 mol%. to be. If it is in the said range, the photoelastic coefficient of the optical film obtained will become small.

Examples of the aromatic ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, tetracene ring, chrysene ring, triphenylene ring, pyrene ring, pentacene ring, pisene ring, benzpyrene ring, perylene ring and coronene ring. , Benzene ring and naphthalene ring are preferred. As an aromatic heterocyclic ring, a furan ring, a pyrrole ring, a thiophene ring, a phosphol ring, an imidazole ring, a furin ring, a pyrazole ring, an indazole ring, an oxazole ring, a thiazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring And a ring containing at least one hetero atom selected from the group consisting of an oxygen atom such as a triazine ring, a nitrogen atom, a sulfur atom and a phosphorus atom as a ring constituent atom. The structural unit having an aromatic ring or an aromatic heterocycle may be a structural unit having a ring in which an aromatic ring and an aromatic heterocycle are condensed with each other. As such a condensed ring, a benzofuran ring, an isobenzofuran ring, an indole ring, an isoindole ring, a benzothiophene ring, a benzophosphol ring, a benzoimidazole ring, a benzoxazole ring, a benzoisoxazole ring, a benzothiazole ring, a quinoline ring , Isoquinoline ring, quinoxaline ring, carbazole ring, acridine ring, quinazoline ring and cinnoline ring.

As resin (2), resin obtained by addition polymerization, resin obtained by polycondensation, and resin obtained by ring-opening polymerization are mentioned.

Resin (2) obtained by addition polymerization is obtained by addition-polymerizing the monomer which has a polymerizable unsaturated double bond. As addition polymerization, radical polymerization, cationic polymerization, and anionic polymerization are mentioned. Of the structural units derived from the monomer having an aromatic ring or aromatic heterocycle and a polymerizable unsaturated double bond in all the structural units derived from the monomer having a polymerizable unsaturated double bond constituting the resin (2) obtained by addition polymerization. The ratio is 11 mol% or more and 100 mol% or less.

Examples of the monomer having an aromatic ring and a polymerizable unsaturated double bond include styrene, methyl styrene, styrene chloride, vinyl benzoic acid, vinyl phenol, vinyl naphthalene, vinyl anthracene, phenyl acrylate, phenyl methacrylate, naphthyl acrylate, naphthyl methacrylate, Benzyl acrylate, benzyl methacrylate and N-phenylmaleimide.

Examples of the monomer having an aromatic heterocycle and a polymerizable unsaturated double bond include vinylindole, vinylimidazole, vinylpyridine, vinylcarbazole and vinylphthalimide.

Resin (2) obtained by addition polymerization is a monomer having a polymerizable unsaturated double bond and not having an aromatic ring or an aromatic heterocycle, and a monomer having a polymerizable unsaturated double bond and having an aromatic ring or an aromatic heterocycle. A copolymer may be sufficient. As a monomer which has a polymerizable unsaturated double bond and does not have an aromatic ring or an aromatic heterocycle, the monomer which does not have an aromatic ring or an aromatic heterocycle is mentioned among the monomers (A) represented by Formula (A) mentioned later.

As resin (2) obtained by addition polymerization, polystyrene, polymethylstyrene, polystyrene chloride, polyvinyl benzoic acid, polyvinylpyrrolidone, polyvinyl indole, polyvinylphenol, polyvinyl naphthalene, polyvinyl anthracene, polyvinyl Midazole, polyvinylpyridine, polyvinylcarbazole, polyvinylphthalimide, phenyl polyacrylate, polymethacrylate phenyl, naphthyl polyacrylate, polynaphthacrylic acid naphthyl, benzyl polyacrylate, benzyl polymethacrylate, Styrene-maleic anhydride copolymer, styrene-butadiene copolymer and styrene-acrylonitrile copolymer.

As resin (2) obtained by polycondensation, polycarbonate, polyester (for example, polyethylene terephthalate, polybutylene terephthalate, etc.), polyether sulfone, polyurethane, polyurethane acrylate, polyurea, polyurethane urea, Polyurethaneurea acrylate, polyimide, polyamide, phenol resin and melamine resin.

It is preferable that resin (2) is polycarbonate or polyether sulfone from the point of the strength, workability, and heat resistance of the film obtained.

Polycarbonate is obtained by 1: 1 polycondensation of a diol compound and phosgene. When combining the structure derived from one diol compound (compound which has two hydroxyl groups (-OH)), and the structure derived from one phosgene combined with each other as one structural unit, resin (2) is resin ( 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle is contained in all the structural units of 2). In a polycarbonate, the structural unit which has an aromatic ring or an aromatic heterocycle is a structural unit containing the structure derived from the diol compound which has an aromatic ring or an aromatic heterocycle.

Examples of the diol compound having an aromatic ring or an aromatic heterocycle include catechol, resorcinol, hydroquinone, methylhydroquinone, phenylhydroquinone, 1,2-dihydroxynaphthalene, 1,3-dihydroxynaphthalene, 1,4-di Hydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2 , 7-dihydroxynaphthalene, 2,2'-biphenol, 4,4'-biphenol, 2,2-bis- (4-hydroxyphenyl) propane, 1,1-bis- (4-hydroxy Phenyl) methane, 4,4'-ethylidenebisphenol, 4,4'-dihydroxybenzophenone, 2,2'-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, 2,4'- Dihydroxybenzophenone, 2,2'-dihydroxydiphenylether, 4,4'-dihydroxydiphenylether, 3,3'-dihydroxydiphenylamine, 4,4'-dihydroxy Sidiphenyl sulfone, bis (4-hydroxy-3, 5- dimethylphenyl) sulfone, bis (4-hydroxyphenyl) sulfide, bis (4-hydroxy Hydroxy-3-methylphenyl) sulfide, 4,4'-dihydroxytetraphenylmethane, 1,1'-bis- (4-hydroxyphenyl) cyclohexane, 1,1'-bis- (4-hydroxy Hydroxyphenyl) -3,3 ', 5-trimethylcyclohexane, 9,9'-bis (4-hydroxyphenyl) fluorene, 9,9'-bis (4-hydroxy-3-methylphenyl) fluorene and 9,9'-bis (3-amino-4- hydroxyphenyl) fluorene is mentioned.

Examples of the polycarbonates include polycondensates of 2,2-bis- (4-hydroxyphenyl) propane and phosgene and polycondensates of 1,1-bis- (4-hydroxyphenyl) methane and phosgene.

Polyethersulfone is a resin having a main chain in which a divalent organic group is alternately bonded with -SO ₂ -and -O-, for example, a compound having two or more halogen atoms and -SO ₂ -and two or more hydroxy groups (-OH ) and compound having a -SO polycondensation or two or more hydroxy groups of the compound having a _2-2 and more are obtained by polycondensation of the compound having a halogen atom. When the structure derived from the compound which has the above-mentioned two or more halogen atoms, and the structure derived from the compound which has two or more hydroxyl groups are each one structural unit, the structure which has an aromatic ring or an aromatic heterocycle in all the structural units in resin. 11 mol% or more and 100 mol% or less of a unit are included.

As a compound which has an aromatic ring or an aromatic heterocycle, and has two or more hydroxyl groups, the diol compound which has the above-mentioned aromatic ring or aromatic heterocycle is mentioned. It has an aromatic ring or aromatic heterocyclic ring, and, -SO ₂ -, and Examples of the compound having at least two hydroxy groups (-OH), 4,4'- dihydroxydiphenyl sulfone and bis (4-hydroxy -3,5 -Dimethylphenyl) sulfone.

Examples of the compound having an aromatic ring or an aromatic heterocycle and having two or more halogen atoms include 2,2'-bis (4-fluorophenyl) propane, 2,2'-bis- (4-chlorophenyl) propane, 2,2'-bis- (4-bromophenyl) propane, 2,2'-bis- (4-iodinephenyl) propane, 1,1'-bis- (4-fluorophenyl) methane, 1,1 '-Bis- (4-chlorophenyl) methane, 1,1'-bis- (4-bromophenyl) methane, 1,1'-bis- (4-iodinephenyl) methane, 4,4'-difluoro Robenzophenone, 4,4'-dichlorobenzophenone, 4,4'-dibromobenzophenone, 4,4'-diiobenzobenzophenone, 2,2'-difluorobenzophenone, 2,2'- Dichlorobenzophenone, 2,2'-dibromobenzophenone, 2,2'-diiodinebenzophenone, 2,4-difluorobenzophenone, 2,4-dichlorobenzophenone, 2,4-dibromo Benzophenone, 2,4-diiobenzobenzophenone, 2,4'-difluorobenzophenone, 2,4'-dichlorobenzophenone, 2,4'-dibromobenzophenone, 2,4'-diode Benzophenone, 2,2'-difluorodiphenylether, 2,2'-di Chlorodiphenyl ether, 2,2'-dibromodiphenyl ether, 2,2'-diiodi diphenyl ether, 4,4'-difluorodiphenyl ether, 4,4'-dichlorodiphenyl ether, 4, 4'-dibromodiphenel ether, 4,4'-diiodi diphenyl ether, 3,3'-difluorodiphenylamine, 3,3'-dichlorodiphenylamine, 3,3'-dibromodi Phenylamine, 3,3'-diiodidiphenylamine, bis (4-fluorophenyl) sulfide, bis (4-chlorophenyl) sulfide, bis (4-bromophenyl) sulfide, bis (4- Iodinephenyl) sulfide, bis (4-fluoro-3-methylphenyl) sulfide, bis (4-chloro-3-methylphenyl) sulfide, bis (4-bromo-3-methylphenyl) sulfide and bis (4 Iodine-3-methylphenyl) sulfide.

Examples of the compound having an aromatic ring or an aromatic heterocycle and further having —SO ₂ — and two or more halogen atoms include 4,4′-difluorodiphenyl sulfone, 4,4′-dichlorodiphenyl sulfone, 4,4 ′ -Dibromodiphenyl sulfone, 4,4'- diiodi diphenyl sulfone, bis (4-fluoro-3, 5- dimethylphenyl) sulfone, bis (4-chloro-3, 5- dimethylphenyl) sulfone, bis (4-bromo-3,5-dimethylphenyl) sulfone and bis (4-iodine-3,5-dimethylphenyl) sulfone are mentioned.

As polyether sulfone, resin obtained by making dichlorodiphenyl sulfone and bisphenol S react in presence of potassium carbonate, 50 mol% of 4,4'- dihydroxy benzophenone and 30 mol% of 4,4'- dichloro benzophene The resin obtained by making rice field and 20 mol% of 4,4'- dichloro diphenyl sulfone react in presence of potassium hydroxide, and resin of Unexamined-Japanese-Patent No. 1678805 are mentioned.

It is preferable that the number average molecular weight of resin (2) is 1,000 or more and 1,00,000 or less from a viewpoint of the viscosity of the resin (2), the solubility to a solvent, the toughness, workability, and optical characteristic of the optical film obtained. It is preferable that the weight average molecular weights of resin (2) are 1,000 or more and 3, O0,000 or less.

Content of resin (2) is 30 mass%-95 mass%, More preferably, with respect to the total amount of at least 1 sort (s) chosen from the group which consists of a monomer (1) and a polymer (1), and resin (2). Preferably it is 35 mass%-93 mass%, Especially preferably, it is 40 mass%-90 mass%. If it is in the said range, the photoelastic coefficient of the optical film obtained will become small.

It is preferable that the composition of this invention contains a photoinitiator (3). A photoinitiator is a compound which generate | occur | produces an active radical or an acid by light irradiation. Especially, the polymerization initiator which generate | occur | produces an active radical by light irradiation is more preferable.

As a photoinitiator, a benzoin compound, a benzophenone compound, an acetophenone compound, an acyl phosphine oxide compound, a triazine compound, an iodonium salt, and a sulfonium salt are mentioned.

As a benzoin compound, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether are mentioned. Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycar Carbonyl) benzophenone and 2,4,6-trimethylbenzophenone.

As the acetophenone compound, diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-mor Polynophenyl) butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1,2-diphenyl-2,2-dimethoxyethan-1-one, 2-hydride Hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenylketone and 2-hydroxy-2-methyl-1- [4- And oligomers of (1-methylvinyl) phenyl] propan-1-one.

Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide. Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4 -Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4 -Bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [ 2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) Tenyl] -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine Can be mentioned.

As the photopolymerization initiator (3), Irgacure 907, Irgacure 184, Irgacure 651, Irgacure 819, Irgacure 250, Irgacure 369, Irgacure OXE01, Irgacure OXE02 ( All of the above are manufactured by BASF Japan Co., Ltd., Seikuol BZ, Seikuol Z, Seikuol BEE (above, manufactured by Seiko Chemical Co., Ltd.), Kayacure BP100, Kayacure DETX-S, Kayacure CTX, Kayak Cure BMS (above, all Nihon Kayaku Co., Ltd.), UVI-6992 (manufactured by Dausa), Adeka Optoma SP-152, Adeka Optoma SP-170, Adeka Optoma N-1414, Adeka Optoma N-1606, Adeka Optoma N-1717, Adeka Optoma-N-1919 (above, all manufactured by ADEKA Co., Ltd.), TAZ-A, TAZ-PP (above, manufactured by Nippon Sieber Hegsa Co., Ltd.) and TAZ- Commercially available photoinitiators can also be used, such as 104 (manufactured by Sanwa Chemical Co., Ltd.).

Content of the photoinitiator (3) is 0.1 mass%-10 mass% normally with respect to the total amount of at least 1 sort (s) chosen from the group which consists of a monomer (1) and a polymer (1), and resin (2), Preferably Is 0.5 mass%-5 mass%. If it is in the said range, the transmittance | permeability of the optical film obtained will become high. Moreover, since the degree of polymerization of the monomer (1) etc. becomes high, the photoelastic coefficient of the optical film obtained can be made small.

The composition of this invention may contain the photosensitizer. In order to accelerate generation of radicals and acids from the photopolymerization initiator (3) and to perform polymerization of the monomer (1) with high sensitivity, it is used in combination with a photopolymerization initiator. As a photosensitizer, the anthracene compound which has substituents, such as xanthone compounds (for example, 2, 4- diethyl thioxanthone, 2-isopropyl thioxanthone, etc.), anthracene, an alkyl ether, such as xanthone and thioxanthone (Eg, dibutoxyanthracene and the like), phenothiazine, and rubrene.

The usage-amount of a photosensitizer is 0.1 mass%-30 mass% normally with respect to the total amount of at least 1 sort (s) chosen from the group which consists of a monomer (1) and a polymer (1), and resin (2), Preferably it is 0.5 It is mass%-10 mass%. If it is in the said range, monomer (1) etc. can be superposed | polymerized with high sensitivity, and the optical film of a high transmittance can be obtained.

The composition of this invention may contain the compound represented by Formula (A) (hereinafter abbreviated as monomer (A)).

In formula (A), R <^3> is a hydrogen atom or a methyl group, Preferably it is a hydrogen atom.

In formula (A), R <^4> may have a C6-C20 monovalent alicyclic hydrocarbon group which may have a substituent, may have a C6-C20 monovalent aromatic hydrocarbon group or substituent which may have a substituent, and C4-C20 may have It is a monovalent heterocyclic group of 20.

Examples of the monovalent alicyclic hydrocarbon group having 6 to 20 carbon atoms include cyclohexyl group, cycloheptyl group, cyclooctyl group, decahydronaphthyl group, tricyclodecanyl group, isobornyl group, norborna group, and adamantyl group. .

As a C6-C20 monovalent aromatic hydrocarbon group, the group represented by a phenyl group, a naphthyl group, an anthryl group, and a following formula is mentioned.

Examples of the monovalent heterocyclic group having 4 to 20 carbon atoms include pyrrolyl group, furyl group, thienyl group, pyrazinyl group, pyrazolyl group, imidazolyl group, pyridyl group, piperidinyl group, piperazinyl group, tetrahydrofuranyl group, Indolyl group, thiazolyl group, and carbazolyl group are mentioned.

In addition, these groups may be condensed with each other. It is preferable that R <^4> is a C6-C20 monovalent aromatic hydrocarbon group or a C4-C20 monovalent heterocyclic group.

The alicyclic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may each have a substituent, and examples of the substituent include a hydroxy group (-OH); Alkyl groups having 1 to 12 carbon atoms such as methyl group, ethyl group, isopropyl group, tert-butyl group and octyl group; C1-C12 alkoxy groups, such as a methoxy group and an ethoxy group; C6-C12 aryl groups, such as a phenyl group, a naphthyl group, and a phenylphenyl group; Aralkyl groups having 7 to 12 carbon atoms such as benzyl group; Glycidyloxy group; C2-C4 acyl groups, such as an acetyl group; C1-C12 acyloxy groups, such as an acetyloxy group; Amino group; Amino groups substituted with one or two C1-C12 alkyl groups such as methylamino group, ethylamino group and dimethylamino group; Halogeno groups (halogen atoms) such as fluoro groups (fluorine atoms), chloro groups (chlorine atoms) and bromo groups (bromine atoms); Oxo group (= 0); And carboxyl groups (—CO ₂ H).

Examples of the monomer (A) wherein R ⁴ is an aromatic hydrocarbon group include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 2,4-dimethylstyrene, o-ethylstyrene, p-ethylstyrene, trimethylstyrene, and propyl. Styrene, tert-butyl styrene, cyclohexyl styrene, dodecyl styrene, hydroxy styrene, tert-butoxy styrene, vinyl benzoic acid, vinyl benzyl acetate, o-chloro styrene, p-chloro styrene, amino styrene, 4-vinyl phenylbenzene , 2-ethyl-4-benzyl styrene, 4- (phenylbutyl) styrene, 4-hydroxy-4'-vinyl biphenyl, vinyl naphthalene, and vinyl anthracene.

Examples of the monomer (A) wherein R ⁴ is a heterocyclic group include N-vinylpyrrolidone, N-vinylcarbazole, N-vinylpyridine, N-vinylphthalimide and N-vinylindole.

As the monomer (A), styrene, N-vinylcarbazole, vinylnaphthalene and vinylanthracene are preferable, and styrene and N-vinylcarbazole are more preferable. If it is these monomers, the optical film obtained can perform more uniform polarization conversion in a wide wavelength range.

Content of a monomer (A) is 0-40 mass% normally with respect to the quantity except the solvent and photoinitiator in the composition of this invention, Preferably it is 10-30 mass%, Especially preferably, it is 15-20 mass%. If it is in the said range, the optical film obtained can perform more uniform polarization conversion in a wide wavelength range.

Monomer (A) may be used independently or may use multiple types together.

The composition of the present invention may contain a compound represented by the formula (B) (hereinafter abbreviated as monomer (B)).

In formula (B), R <^5> is a hydrogen atom or a methyl group, Preferably it is a methyl group.

In formula (B), R <^6> is -OR <^7> or NR <^7> R <^8> , R <^7> is a hydrogen atom or a C1-C6 alkyl group, R <^8> is a C1-C6 alkyl group. Hydrogen atoms contained in the alkyl group is good, even if substituted with a hydroxy group (-OH) or carboxyl group (-CO ₂ H), -CH ₂ contained in the alkyl group - is, -O-, -CO-, -S- or It may be substituted with NH-.

Examples of the alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group and hexyl group.

Specific examples of the monomer (B) include acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl methacrylate and butyl acrylate. Butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, tert-butyl acrylate, tert-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2- (acrylic acid) Dimethylamino) ethyl, methacrylic acid 2- (dimethylamino) ethyl, glycerin monoacrylate and glycerin monomethacrylate.

As the monomer (B), methacrylic acid 2-hydroxyethyl, methacrylic acid 2- (dimethylamino) ethyl and glycerin monomethacrylate are preferable. If it is these monomers, polymerization degree can be made high and the transmittance | permeability and smoothness of the optical film obtained are high.

Content of monomer (B) is 0-50 mass% normally with respect to the quantity except the solvent and photoinitiator in the composition of this invention, Preferably it is 3-30 mass%, Especially preferably, it is 5-25 mass%. If it is in the said range, a polymerization degree can be made high by copolymerizing with monomer (1) etc., and the optical film of a high transmittance can be obtained.

The monomer (B) may be used alone or in combination of two or more.

It is preferable that the composition of this invention contains a solvent. As the solvent, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, di Ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate, propylene glycol mono Ethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, methoxybutyl acetate, methoxy Ether solvents such as pentyl acetate, anisole, phenetole, methyl anisole;

Aromatic hydrocarbon solvents such as benzene, toluene, xylene and mesitylene;

Ketone solvents such as 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, and cyclohexanone;

Alcohol solvents such as methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin;

Ethyl acetate, butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl oxyacetate, oxy Ethyl acetate, butyl oxyacetate, methyl methoxy acetate, ethyl methoxy acetate, methoxy butyl acetate, methyl ethoxy acetate, ethyl ethoxy acetate, methyl 3-oxypropionate, ethyl 3-oxypropionate, methyl 3-methoxypropionate Ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, Ethyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, acetic acetic acid Butyl, ethyl acetoacetate, methyl 2-oxo-butanoic acid, 2-oxo-butanoic acid ethyl, 3-methoxybutyl acetate, ester solvents such as 3-methyl-3-methoxybutyl acetate, γ- lactone butyronitrile;

Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone; And

Dimethyl sulfoxide can be mentioned.

When the composition of this invention contains a solvent, content of a solvent is 30-95 mass% normally with respect to the composition of this invention, Preferably it is 40-90 mass%, Especially preferably, it is 50-80 mass%. If it is in the said range, a monomer and an initiator will melt | dissolve uniformly and the coating uniformity of a composition is excellent.

A solvent may be used independently or may use multiple types together.

The composition of this invention may contain the polymerization inhibitor, a leveling agent, and a plasticizer as needed.

Examples of polymerization inhibitors include hydroquinones such as hydroquinone, catechols such as butyl catechol, pyrogallols, radical scavengers such as 2,2,6,6-tetramethyl-1-piperidinyloxy radicals, thiophenols, (beta) -naphthylamine and (beta) -naphthol are mentioned.

The content of the polymerization inhibitor is preferably 0.1% by mass to 30% by mass, more preferably relative to the total amount of at least one selected from the group consisting of the monomer (1) and the polymer (1) and the resin (2). Is 0.5 mass%-10 mass%. If it is in the said range, a stable optical film can be obtained with a high transmittance.

Examples of the leveling agent include organic modified silicone oil leveling agents, polyacrylate leveling agents, and perfluoroalkyl leveling agents. Specifically, DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (above, manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341 (above, all Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (above, all Momentive Performance Materials Japan Corporation Manufacture), Florinat (brand name) FC-72, copper FC-40, copper FC-43, copper FC-3283 (all manufactured by Sumitomo 3M Co., Ltd.), mega pack (brand name) R-08, copper R- 30, East R-90, East F-410, East F-411, East F-443, East F-445, East F-470, East F-477, East F-479, East F-482, East F- 483 (above, all are manufactured by DIC Co., Ltd.), F-top (brand name) EF301, copper EF303, copper EF351, copper EF352 (above, all are manufactured by Misubishimaterialden Shigasei Co., Ltd.), saffron (brand name) S -381, copper S-382, copper S-383, copper S-393, copper SC-101, copper SC-105, KH-40, SA-100 (above, manufactured by AGC Seiko Chemical Co., Ltd.), Name E1830, E5844 copper ((Note) Daikin Fine Chemical Gen kyusyo, Ltd.) may be mentioned.

A leveling agent may be used independently or may use multiple types together.

By using a leveling agent, the film obtained can be made smoother. Moreover, at the time of film-forming, the fluidity | liquidity of the composition of this invention can be controlled, or the crosslinking density of the optical film of this invention can be adjusted.

The content of the leveling agent is usually 0.001% by mass to 2% by mass, preferably 0.0005% by mass to 1% by mass, with respect to the amount excluding the solvent from the composition of the present invention. If it is in the said range, an optical film smooth by high transmittance | permeability can be obtained.

Phosphoric acid ester, carboxylic acid ester, and glycolic acid ester are mentioned as a plasticizer. Examples of the phosphate esters include triphenyl phosphate (TPP), tricredil phosphate (TCP), credil diphenyl phosphate, octyl diphenyl phosphate, diphenyl biphenyl phosphate, trioctyl phosphate and tributyl phosphate.

As carboxylic acid ester, phthalic acid, such as dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), dioctyl phthalate (DOP), diphenyl phthalate (DPP), and diethylhexyl phthalate (DEHP) Citrate esters such as esters, O-acetyl citrate triethyl (OACTE), O-acetyl citrate tributyl (OACTB), acetyl triethyl citrate, acetyl tributyl citrate, butyl oleate, methyl ricinoleate, dibutyl sebacinate and many others Eggplant trimellitic acid ester is mentioned.

Examples of the glycolic acid esters include triacetin, tributyrin, butylphthalyl butyl glycolate, ethyl phthalyl ethyl glycolate, methyl phthalyl ethyl glycolate, butyl phthalyl butyl glycolate, trimethylol propane tribenzoate, and pentaerythritol tetra Benzoate, ditrimethylolpropane tetraacetate, ditrimethylol propane tetrapropionate, pentaerythritol tetraacetate, sorbitol hexaacetate, sorbitol hexapropionate, sorbitol triacetate tripropionate, inositol pentaacetate and sorbitan butylate The rate is mentioned.

As a plasticizer, (di) pentaerythritol esters of Unexamined-Japanese-Patent No. 11-124445, the glycerol ester of Unexamined-Japanese-Patent No. 11-246704, and the diglycerol of Unexamined-Japanese-Patent No. 2000-63560 are also mentioned. Ester, citric acid ester of Unexamined-Japanese-Patent No. 11-92574, substituted phenyl phosphate ester of Unexamined-Japanese-Patent No. 11-90946, etc. are mentioned.

Especially, as a plasticizer, a triphenyl phosphate, a tricredyl phosphate, a credyl diphenyl phosphate, a tributyl phosphate, a dimethyl phthalate, diethyl phthalate, a dibutyl phthalate, a dioctyl phthalate, a diethylhexyl phthalate, a triacetin, ethyl phthalyl Ethyl glycolate, trimethylol propane tribenzoate, pentaerythritol tetrabenzoate, ditrimethylol propane tetraacetate, pentaerythritol tetraacetate, sorbitol hexaacetate, sorbitol hexapropionate and sorbitol triacetate tripropionate are preferable. Triphenyl phosphate, diethyl phthalate, ethyl phthalyl ethyl glycolate, trimethylol propane tribenzoate, pentaerythritol tetrabenzoate, ditrimethylol propane tetraacetate, sorbitol hexaacetate, sorbide The hexahydro propionate and sorbitol triacetate tree propionate is more preferred.

As for content of a plasticizer, 0.1-30 mass% is preferable with respect to the quantity except the solvent in the composition of this invention. A plasticizer may be used independently or may use multiple types together.

The optical film of this invention is an optical film obtained by superposing | polymerizing the polymerizable component contained in the composition of this invention. It is preferable that this optical film is a stretched film further. The polymerization and stretching may be performed separately or simultaneously. In addition, when superposing | polymerizing and extending | stretching separately, you may extend | stretch after superposition | polymerization and may superpose | polymerize after extending | stretching. It is preferable that superposition | polymerization is photopolymerization. It is more preferable to form into a film the composition of this invention, to photopolymerize and extend the polymeric component contained in this composition, and to obtain an optical film.

As a method of film-forming the composition of this invention, the solvent casting method which casts the composition of this invention on the smooth surface, and distills a solvent, the melt-extrusion method which extrusion-extrudes the composition of this invention to a film form with a melt extrusion machine, etc. are mentioned. Can be. Since the solvent casting method can form easily, it is preferable.

As a method of polymerizing the polymerizable component contained in the composition of this invention, the method of irradiating ultraviolet-ray to the film-formed composition of this invention, etc. are mentioned. Examples of the source of ultraviolet light include fluorescent chemical lamps, black lights, low pressure mercury lamps, high pressure mercury lamps, ultrahigh pressure mercury lamps, metal halide lamps, solar rays, and electrodeless lamps. The irradiation intensity of ultraviolet light may be performed at a constant intensity at all times, or may change intensity during photopolymerization.

As a method of extending | stretching the film obtained from the composition of this invention, the extending | stretching method by a tenter method, the extending | stretching method by extending | stretching between rolls, etc. are mentioned. The stretching may be either uniaxial stretching or biaxial stretching, or longitudinal stretching or transverse stretching.

Examples of the uniaxial stretching include a uniaxial stretching method in the longitudinal direction by stretching between rolls and a uniaxial stretching method in the horizontal direction using a tenter, and the like. After extending the width and stretching in the longitudinal direction at the same time as the stretching in the longitudinal direction and stretching in the horizontal direction by stretching the guide rail, or stretching in the vertical direction by stretching between rolls, hold both ends with a tenter clip. The sequential biaxial stretching method etc. which extend | stretch to a horizontal direction using a burr are mentioned.

From a viewpoint of productivity, horizontal uniaxial stretching and biaxial stretching are preferable, and transverse uniaxial stretching is especially preferable.

By lateral uniaxial stretching or biaxial stretching, an optical film having optical biaxiality can be obtained. Here, optical biaxiality is n _x , n _y (where n _x > n _y ), and the refractive index in the thickness direction is n _z when the refractive indices of two straight directions in the film plane are respectively n _x ≠ n _y ≠ n The thing of the property to become _z .

The optical film which has optical biaxiality can perform uniform polarization conversion also about the thickness direction of an optical film.

When the optical elastic modulus of the optical film is small, good optical characteristics are exhibited, and when applied to a display device, the color tone is small and excellent black display is possible. Specifically, the photoelastic coefficient is preferably 50 × 10 ⁻¹² Pa ⁻¹ or less.

Since the photoelastic coefficient is small, the optical film of this invention is used as retardation plates, such as a (lambda) / 2 plate and a (lambda) / 4 plate, a viewing angle improvement film, etc. If the optical film is a λ / 4 plate, it can be combined with a linear polarizing plate to form a circular polarizing plate of an optical wavelength region, and if it is a λ / 2 plate, it can be combined with a linear polarizing plate to form a polarization rotating element of an optical wavelength region. These can be used in various liquid crystal display devices, cathode ray tube (CRT), touch panels, electroluminescence (EL) lamps, and the like, antireflection filters, liquid crystal projectors, and the like.

Example

Hereinafter, although an Example demonstrates this invention still in detail, this invention is not limited to these Examples. "%" And "part" in an example are the mass% and a mass part, respectively, unless there is particular notice.

Synthesis Example 1

In a reactor equipped with a stirrer, a thermometer and a reflux condenser, 20.64 parts of polyhexamethylene carbonate diol (average molecular weight 860), 5.19 parts of 1,4-cyclohexanedimethanol, 0.11 part of dibutyltin dilaurate and propylene glycol monomethyl ether 113.41 parts of acetate were added and 14.67 parts of isophorone diisocyanate were added dropwise under nitrogen stream stirring. After completion of the dropwise addition, the reaction was carried out at 90 ° C. for 5 hours under a nitrogen stream. Subsequently, 1.60 parts of 2-hydroxyethyl acrylate were put into the obtained reaction mixture, and it was made to react at 50 degreeC for 1 hour, and the urethane acrylate solution containing the urethane acrylate whose number average molecular weight is 4.Ox10 <^4> was obtained. . The urethane acrylate does not have a structural unit having an aromatic ring or an aromatic heterocycle.

The number average molecular weight was analyzed under the following analysis conditions using gel permeation chromatography (GPC) (manufactured by Tosoh Corporation, HLC-8220), and the value was polystyrene conversion.

Device HLC-8220 GPC (manufactured by Tosoh Corporation)

Guard column TSKguardcolumn SuperH-H (brand name)

Three column TSK-gel SuperHM-H (brand name) are connected in series

Column temperature 40 ℃

Solvent tetrahydrofuran

Flow rate 0.6 mL / min

Injection volume 50 μL

Detector RI, UV

Measurement sample concentration O.6 mass% (solvent: tetrahydrofuran)

Calibration Standards TSK STANDARD POLYSTYRENE A-500, A-1000, A-2500, A-5000, F-1, F-2, F-4, F-10, F-20, F-40, F-80 , F-128, F-288, F-380 (all brand names, Toso Corporation make)

[Preparation of composition]

(Examples 1 to 6)

The following components were mixed and the compositions 1-6 were prepared.

Monomer (1): 10 parts of the compound shown in Table 1

Resin (2): 138 parts of solution (A)

Photoinitiator (3): 0.4 parts of phenyl (1-hydroxycyclohexyl) ketones (Irgacure 184; BASF Japan)

Solvent: Chloroform 20 parts

Leveling Agent: Megapak F-477 (manufactured by DIC Corporation) 0.1 part

Solution (A): polybisphenol A carbonate (content of the structural unit which has an aromatic ring or aromatic heterocycle in all the structural units: 100 mol%) (Sigma Aldrich Japan Co., Ltd. make, weight average molecular weight = 64,000, Tg = 150 ℃) Chloroform solution (solid content: 15%)

(Examples 7-12)

The following components were mixed and the compositions 7-12 were prepared.

Monomer (1): 10 parts of the compound shown in Table 1

Resin (2): 80 parts of solution (B)

Photopolymerization initiator (3): 0.4 parts of Irgacure 184 (manufactured by BASF Japan)

Solvent: 20 parts of N, N-dimethylformamide / cyclohexanone / 2-butanone mixed solvent (mixing ratio is 20:80:25 by volume ratio)

Leveling Agent: Megapak F-477 (manufactured by DIC Corporation) 0.1 part

Solution (B): N of a polyether sulfone compound (content of the structural unit which has an aromatic ring or aromatic heterocycle in all the structural units: 100 mol%) (brand name: Sumika Excel PFS 4800P, the Sumitomo Chemical Co., Ltd. product). N-dimethylformamide / cyclohexanone / 2-butanone mixed solvent (mixing ratio is 20:80:25 by volume) solution (solid content: 25%)

TABLE 1

[Production of optical film]

Compositions 1 to 12 were applied onto a release film made of polyethylene terephthalate (thickness 188 μm) with an applicator (gap width: 500 μm), and then left in a closed container for 5 minutes at room temperature, followed by 10 minutes at 40 ° C. After drying at 80 ° C. for 15 minutes, 600 mJ / cm 2 (365 nm standard) light irradiation was performed with a high-pressure mercury lamp. After light irradiation, it removed from the release film and obtained the optical film.

(Comparative Example 1)

66.7 parts of urethane acrylate solutions prepared in Synthesis Example 1, 7 parts of N-vinylcarbazole, 3 parts of photopolymerization initiator (Irgacure 184, manufactured by Chivas Specialty Chemicals Co., Ltd.), propylene glycol monomethyl ether 20.0 parts of acetate were mixed to prepare a solution. The solution was applied on a release film made of polyethylene terephthalate with an applicator (gap width: 700 μm), and then dried at 80 ° C. for 15 minutes, followed by UV irradiation (high pressure mercury lamp: 650 mJ / cm 2 per pass: 365 nm), and further stretched 3.0-times using the temperature control autograph drawing machine, and obtained the optical film.

[Measurement of photoelastic coefficient]

The sheet | seat of 150 mm x 600 mm size is cut out from the obtained optical film, and it is 5 points in the range of 0 N-50 N at room temperature using an automatic birefringence meter (KOBRA-WR, product of Oshigeisokugiki Co., Ltd.). The in-plane phase difference value Re at the time of changing tension was measured, respectively, and the photoelastic coefficient was calculated | required from the inclination of the approximated straight line created according to the following formula. The results are shown in Table 2.

Re / d = C

Where d is the thickness of the optical film, sigma is the tension, and C is the photoelastic coefficient.

Table 2

It was confirmed that the optical film of the Example has a small photoelastic coefficient.

Since the optical film of this invention has small photoelastic coefficient, the display apparatus provided with the optical film of this invention has little hue change, and the outstanding black display is attained.

Claims (10)

1 or more types chosen from the group which consists of a polymer obtained by superposing | polymerizing the monomer represented by following formula (1) and the monomer represented by following formula (1),
Resin containing 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle in all the structural units.
An optical film obtained by superposing | polymerizing the polymerizable component contained in the composition containing:

Formula, R ¹ is a hydrogen atom or a methyl group, R ² is even have a substituent represents a good cross-linked monovalent cyclic hydrocarbon group of a carbon number of 5~15, -CH ₂ included the cross-linked polycyclic hydrocarbon groups - is -NR ³ -, It may be substituted by -O-, -CO- or -S-, R <^3> represents a hydrogen atom or a C1-C3 alkyl group, n <^1> represents the integer of 0-3. The optical film of claim 1, wherein the resin is at least one selected from the group consisting of polycarbonate and polyether sulfone. The optical film of claim 1, wherein R ¹ is a methyl group. The optical film of claim 1, wherein the composition further comprises a photopolymerization initiator. Retardation plate containing the optical film as described in any one of Claims 1-4. 1 or more types chosen from the group which consists of a polymer obtained by superposing | polymerizing the monomer represented by following formula (1) and the monomer represented by following formula (1),
Resin containing 11 mol% or more and 100 mol% or less of the structural unit which has an aromatic ring or an aromatic heterocycle in all the structural units.
Composition comprising:

Formula, R ¹ is a hydrogen atom or a methyl group, R ² is even have a substituent represents a good cross-linked monovalent cyclic hydrocarbon group of a carbon number of 5~15, -CH ₂ included the cross-linked polycyclic hydrocarbon groups - is -NR ³ -, It may be substituted by -O-, -CO- or -S-, R <^3> represents a hydrogen atom or a C1-C3 alkyl group, n <^1> represents the integer of 0-3. The composition of claim 6 further comprising a photopolymerization initiator. The composition according to claim 6 or 7, further comprising a solvent. The polymer obtained by superposing | polymerizing the polymerizable component contained in the composition of Claim 6. The manufacturing method of the optical film obtained by distilling a solvent, after casting the composition of Claim 8 to the smooth surface.