JP2012021068A - Composition and optical film - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an optical film excellent in the resistance (moisture and heat resistance) when being stored in a high-humidity high-temperature condition; and to provide a composition suitable for fabrication of the same.SOLUTION: The composition includes a compound represented by formula (A), an antioxidant, and a photoinitiator. In the formula, Xdenotes -S- or the like; Ydenotes an aromatic hydrocarbon group or the like; Qand Qdenote a hydrogen atom or the like; Dand Ddenote -CO-O- or the like; Gand Gdenote an alicyclic hydrocarbon group or the like; and Land Ldenote a monovalent organic group or the like.

Description

  The present invention relates to a composition and an optical film.

  A member including an optical film such as a polarizing plate or a retardation plate is used in a flat panel display (FPD). As such an optical film, an optical film formed using a composition containing a polymerizable liquid crystal compound, a photopolymerization initiator, and a solvent is known. As such an optical film, for example, an optical film capable of uniform polarization conversion in a wide wavelength range has been proposed (see Patent Document 1 ([Claim 12])).

JP 2010-31223 A

  Conventional optical films are not always satisfactory in terms of resistance (moisture heat resistance) when stored under conditions of high humidity and high temperature.

  The composition of the present invention capable of solving the above-described problems is characterized by containing a compound represented by the formula (A), an antioxidant and a photopolymerization initiator.

Wherein (A), X ¹ is, -S -, - O- or -NR ¹ - represents a. R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms.
Q ¹ and Q ² are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic having 6 to 20 carbon atoms. Represents a hydrocarbon group, a halogen atom, a cyano group, a nitro group, —NR ² R ³ or —SR ² , and Q ¹ and Q ² may be bonded to each other to form an aromatic ring or an aromatic heterocyclic ring. . R ² and R ³ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, —CO—O—, —CS—O—, —CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —CR ⁶ R ⁷ —, —O—CR ^4. R ⁵ —, —CR ⁴ R ⁵ —O—CR ⁶ R ⁷ —, —CO—O—CR ⁴ R ⁵ —, —O—CO—CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —O—CO— CR ⁶ R ⁷ —, —CR ⁴ R ⁵ —CO—O—CR ⁶ R ⁷ —, —NR ⁴ —CR ⁵ R ⁶ — or —CO—NR ⁴ — is represented.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and —CH ₂ — contained in the alicyclic hydrocarbon group is —O—, — S— or —NH— may be substituted, and —CH (—) — contained in the alicyclic hydrocarbon group may be substituted with —N (—) —.
L ¹ and L ² each independently represent a monovalent organic group, and at least one selected from the group consisting of L ¹ and L ² represents a group having a polymerizable group. ]

L ¹ in the formula (A) is preferably a group represented by the formula (A1), and L ² in the formula (A) is preferably a group represented by the formula (A2).
P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) _l -E ^2- (A2)
Wherein (A1) and formula ^{(A2), B 1, B} 2, E 1 and E ^2, each ^{independently, -CR 11 R 12 -, -} CH 2 -CH 2 -, - O -, - S —, —CO—O—, —O—CO—O—, —CS—O—, —O—CS—O—, —CO—NR ¹¹ —, —O—CH ₂ —, —S—CH ₂ —. Or it represents a single bond.
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, and the alicyclic hydrocarbon —CH ₂ — contained in the group may be replaced by —O—, —S— or —NH—, and —CH (—) — contained in the alicyclic hydrocarbon group represents —N (-)-May be replaced.
k and l each independently represents an integer of 0 to 3. When k is an integer of 2 or more, the plurality of B ¹ and A ¹ may be the same as or different from each other. If l is an integer of 2 or more, a plurality of B ² and A ² may be the same or different from each other.
F ¹ and F ² represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ and P ² represent a hydrogen atom or a polymerizable group, and at least one is a polymerizable group.
R ¹¹ and R ¹² represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]

  The photopolymerization initiator is preferably an alkylphenone compound. As the alkylphenone compound, a compound represented by the formula (C-1) is preferable.

[In Formula (C-1), Q ³ represents a hydrogen atom or a methyl group. ]

  The antioxidant is preferably a phenolic antioxidant.

  The present invention also includes an optical film obtained by polymerizing a polymerizable component contained in the composition, and a retardation film obtained by polymerizing a polymerizable component contained in the composition. A polarizing plate having at least one selected from the group consisting of a retardation film, a flat panel display device having at least one selected from the group consisting of the optical film and the retardation film is also included.

  According to the present invention, an optical film excellent in moisture and heat resistance can be obtained.

It is a cross-sectional schematic diagram which shows an example of the polarizing plate which concerns on this invention. It is a cross-sectional schematic diagram which shows an example of the liquid crystal display device which concerns on this invention. It is a cross-sectional schematic diagram which shows an example of the organic electroluminescence display which concerns on this invention. It is a cross-sectional schematic diagram which shows an example of the color filter which concerns on this invention.

1. Composition The composition of the present invention comprises a compound represented by formula (A) (hereinafter sometimes referred to as “compound (A)”), an antioxidant (B) and a photopolymerization initiator (C).

1-1. Compound The composition of this invention contains a compound (A).

Wherein (A), X ¹ is, -S -, - O- or -NR ¹ - represents a. R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms.
Q ¹ and Q ² are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic having 6 to 20 carbon atoms. It represents a hydrocarbon group, a halogen atom, a cyano group, a nitro group, —NR ² R ³ or —SR ² , and Q ¹ and Q ² may be bonded to each other to form an aromatic ring or an aromatic heterocyclic ring. R ² and R ³ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, —CO—O—, —CS—O—, —CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —CR ⁶ R ⁷ —, —O—CR ^4. R ⁵ —, —CR ⁴ R ⁵ —O—CR ⁶ R ⁷ —, —CO—O—CR ⁴ R ⁵ —, —O—CO—CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —O—CO— CR ⁶ R ⁷ —, —CR ⁴ R ⁵ —CO—O—CR ⁶ R ⁷ —, —NR ⁴ —CR ⁵ R ⁶ — or —CO—NR ⁴ — is represented.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and —CH ₂ — contained in the alicyclic hydrocarbon group is —O—, — S— or —NH— may be substituted, and —CH (—) — contained in the alicyclic hydrocarbon group may be substituted with —N (—) —.
L ¹ and L ² each independently represent a monovalent organic group, and at least one selected from the group consisting of L ¹ and L ² represents a group having a polymerizable group. ]

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Etc. Among these, a C1-C4 alkyl group is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is especially preferable.

Examples of the aromatic hydrocarbon group represented by Y ¹ include monocyclic aromatic hydrocarbon groups such as phenyl groups; polycyclic aromatic hydrocarbon groups such as naphthyl groups, anthryl groups, phenanthryl groups, and biphenyl groups (condensation). And a polycyclic aromatic hydrocarbon group). Among these, a phenyl group and a naphthyl group are preferable, and a phenyl group is more preferable. Examples of the aromatic heterocyclic group represented by Y ¹ include monocyclic aromatic heterocyclic groups such as furyl group, pyrrolyl group, thienyl group, pyridinyl group, thiazolyl group; benzothiazolyl group, benzofuryl group, benzothienyl group, etc. And aromatic heterocyclic groups containing at least one hetero atom such as a nitrogen atom, oxygen atom, sulfur atom and the like such as a polycyclic aromatic heterocyclic group (including a condensed polycyclic aromatic heterocyclic group). . Among these, a furyl group, a thienyl group, a thiazolyl group, a benzothiazolyl group, a benzofuryl group, and a benzothienyl group are preferable.

The aromatic hydrocarbon group and aromatic heterocyclic group represented by Y ¹ may have a substituent (hereinafter referred to as substituent Z ¹ ). Examples of the substituent Z ¹ include a halogen atom, an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitro group, a nitroso group, a carboxy group, an alkylsulfinyl group having 1 to 6 carbon atoms, and an alkylsulfonyl group having 1 to 6 carbon atoms. , A C1-C6 fluoroalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 N-alkylamino group, a C2-C12 N, Examples thereof include N-dialkylamino groups, N-alkylsulfamoyl groups having 1 to 6 carbon atoms, and N, N-dialkylsulfamoyl groups having 2 to 12 carbon atoms.

Examples of the halogen atom as the substituent Z ^1, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a fluorine atom, a chlorine atom or a bromine atom.
Examples of the alkyl group that becomes the substituent Z ¹ include the alkyl groups exemplified as the R ¹ . Among these, a C1-C4 alkyl group is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is especially preferable.

Examples of the alkylsulfinyl group to be the substituent Z ¹ include methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, pentyl Examples thereof include a sulfinyl group and a hexylsulfinyl group. Among these, an alkylsulfinyl group having 1 to 4 carbon atoms is preferable, an alkylsulfinyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfinyl group is particularly preferable.

Examples of the alkylsulfonyl group to be the substituent Z ¹ include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, and pentyl. A sulfonyl group, a hexyl sulfonyl group, etc. are mentioned. Among these, an alkylsulfonyl group having 1 to 4 carbon atoms is preferable, an alkylsulfonyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfonyl group is particularly preferable.

Examples of the fluoroalkyl group that becomes the substituent Z ¹ include a fluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group. Among these, a C1-C4 fluoroalkyl group is preferable, a C1-C2 fluoroalkyl group is more preferable, and a trifluoromethyl group is especially preferable.

Examples of the alkoxy group as the substituent Z ¹ include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. Can be mentioned. Among these, an alkoxy group having 1 to 4 carbon atoms is preferable, an alkoxy group having 1 to 2 carbon atoms is more preferable, and a methoxy group is particularly preferable.

Examples of the alkylsulfanyl group to be substituted Z ¹ include methylsulfanyl group, ethylsulfanyl group, propylsulfanyl group, isopropylsulfanyl group, butylsulfanyl group, isobutylsulfanyl group, sec-butylsulfanyl group, tert-butylsulfanyl group, pentyl Examples thereof include a sulfanyl group and a hexylsulfanyl group. Among these, an alkylsulfanyl group having 1 to 4 carbon atoms is preferable, an alkylsulfanyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfanyl group is particularly preferable.

Examples of the N-alkylamino group as the substituent Z ¹ include an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, and an N-isobutylamino group. N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, N-hexylamino group and the like. Among these, an N-alkylamino group having 1 to 4 carbon atoms is preferable, an N-alkylamino group having 1 to 2 carbon atoms is more preferable, and an N-methylamino group is particularly preferable.

Examples of the N, N-dialkylamino group to be the substituent Z ¹ include N, N-dimethylamino group, N-methyl-N-ethylamino group, N, N-diethylamino group, and N, N-dipropylamino group. N, N-diisopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group, N, N-dihexylamino group and the like. Among these, an N, N-dialkylamino group having 2 to 8 carbon atoms is preferable, an N, N-dialkylamino group having 2 to 4 carbon atoms is more preferable, and an N, N-dimethylamino group is particularly preferable.

Examples of the N-alkylsulfamoyl group to be the substituent Z ¹ include N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N -Butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N-hexylsulfamoyl group Etc. Among these, an N-alkylsulfamoyl group having 1 to 4 carbon atoms is preferable, an N-alkylsulfamoyl group having 1 to 2 carbon atoms is more preferable, and an N-methylsulfamoyl group is particularly preferable.

Examples of the N, N-dialkylsulfamoyl group to be the substituent Z ¹ include N, N-dimethylsulfamoyl group, N-methyl-N-ethylsulfamoyl group, and N, N-diethylsulfamoyl group. N, N-dipropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N, N-dibutylsulfamoyl group, N, N-diisobutylsulfamoyl group, N, N-dipentylsulfamoyl group N, N-dihexylsulfamoyl group and the like. Among these, an N, N-dialkylsulfamoyl group having 2 to 8 carbon atoms is preferable, an N, N-dialkylsulfamoyl group having 2 to 4 carbon atoms is more preferable, and an N, N-dimethylsulfamoyl group is more preferable. Particularly preferred.

Examples of the substituent Z ¹ include a halogen atom, an alkyl group having 1 to 2 carbon atoms, a cyano group, a nitro group, an alkylsulfonyl group having 1 to 2 carbon atoms, a fluoroalkyl group having 1 to 2 carbon atoms, and 1 to 1 carbon atoms. 2 alkoxy groups, 1 to 2 carbon alkylsulfanyl groups, 1 to 2 carbon N-alkylamino groups, 2 to 4 carbon N, N-dialkylamino groups, 1 to 2 carbon alkylsulfurs A moyl group is preferred. The substituent Z ¹ is particularly a halogen atom, methyl group, cyano group, nitro group, sulfo group, carboxy group, trifluoromethyl group, methoxy group, methylsulfanyl group, N, N-dimethylamino group or N-methylamino group. Groups are preferred.

Examples of the monocyclic aromatic hydrocarbon group or monocyclic aromatic heterocyclic group which may have a substituent represented by Y ¹ include those represented by formula (Y-1) to formula (Y-6). And the group represented.

[In formula (Y-1) to formula (Y-6), * represents a bond, Z ¹ represents the same as the substituent Z ^1, and preferred groups are also the same as described above.
a1 is an integer of 0 to 5, a2 is an integer of 0 to 4, b1 is an integer of 0 to 3, b2 is an integer of 0 to 2, and R ⁸ represents a hydrogen atom or a methyl group.
When a1, a2, b1, and b2 are integers of 2 or more, the plurality of Z ¹ may be the same as or different from each other. ]

Y ¹ is particularly preferably a group represented by the formula (Y-1) or the formula (Y-3) from the viewpoint of the production process and cost.

The polycyclic aromatic hydrocarbon group or a monovalent polycyclic aromatic heterocyclic group represented by Y ^1, for example, a group represented by the formula (Y ¹ -1) ~ formula (Y ¹ -7) Is mentioned.

[In formula (Y ¹ -1) to formula (Y ¹ -7), * represents a bond, Z ¹ represents the same as the substituent Z ^1, and preferred groups are the same as described above.
V ¹ and V ² each independently represent —CO—, —S—, —NR ⁹ —, —O—, —Se— or —SO ₂ —. R ⁹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
W ^{1 to} W ⁵ each independently represent —CH═ or —N═.
However, at least one of V ¹ , V ² and W ^{1 to} W ⁵ represents a group containing S, N, O or Se.
a represents the integer of 0-3 each independently.
b represents the integer of 0-2 each independently.
When a and b are integers of 2 or more, the plurality of Z ¹ may be the same as or different from each other. ]

V ¹ and V ² are each independently preferably —S—, —NR ⁹ — or —O—, and W ^{1 to} W ⁵ are each independently preferably —CH═ or —N═.
Further, at least one of V ¹ , V ² and W ^{1 to} W ⁵ preferably represents a group containing S, N or O.
a is preferably 0 or 1, and b is preferably 0.

Furthermore, any group represented by the formula (Y ¹ -1) to the formula (Y ¹ -7) is a group represented by the formula (Y ² -1) to the formula (Y ² -6). Is preferred.

[In formula (Y ² -1) to formula (Y ² -6), *, Z ¹ , a, b, V ¹ , V ² and W ¹ represent the same meaning as described above. ]

As Z ^{1 in} formula (Y ² -1) to formula (Y ² -6), in particular, halogen atom, methyl group, ethyl group, isopropyl group, sec-butyl group, cyano group, nitro group, sulfo group, Nitroso group, carboxy group, trifluoromethyl group, methoxy group, methylsulfanyl group, N, N-dimethylamino group or N-methylamino group are preferred, halogen atom, methyl group, ethyl group, isopropyl group, sec-butyl group , A cyano group, a nitro group, and a trifluoromethyl group are more preferable, and a methyl group, an ethyl group, an isopropyl group, a sec-butyl group, a pentyl group, and a hexyl group are particularly preferable.

Examples of the aliphatic hydrocarbon group represented by Q ¹ and Q ² include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, 1- Methylbutyl group, 3-methylbutyl group, hexyl group, 1-methylpentyl group, 4-methylpentyl group, heptyl group, 1-methylhexyl group, 5-methylhexyl group, octyl group, 1-methylheptyl group, nonyl group, Examples include 1-methyloctyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, and eicosyl group. Among these, a C1-C12 alkyl group is preferable and a methyl group and an ethyl group are especially preferable.

Examples of the alicyclic hydrocarbon group represented by Q ¹ and Q ² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and the like. A cyclic alkyl group having a number of 3 to 12 is preferred.

Examples of the aromatic hydrocarbon group represented by Q ¹ and Q ² include a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and a 3-fluorenyl group. And an aromatic hydrocarbon group having 6 to 14 carbon atoms is preferred.

The aliphatic hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group represented by Q ¹ and Q ² may each have a substituent. Examples of the substituent include those exemplified as the aforementioned Y ¹ . The alkyl group having 1 to 6 carbon atoms represented by R ² and R ³ can be selected from the same groups as the above R ^1. Among them, an alkyl group having 1 to 4 carbon atoms is preferable, and a methyl group and an ethyl group are more preferable. A methyl group is particularly preferred.

Here, Q ¹ and Q ² may be bonded to each other to form an aromatic ring or an aromatic heterocyclic ring. As the ring structure formed by Q ¹ and Q ^2, those represented by the formula (Q) are preferable.

[In formula (Q), X ² represents a group selected from the same range as the group exemplified as X ¹ in formula (A). Y ² represents a group selected from the same range as the groups exemplified as Y ¹ in the formula (A). * Represents a bond. ]

Specific examples of the combination of X ¹ , Y ¹ , Q ¹ and Q ² include, for example, those represented by formula (ar-1) to formula (ar-135).

As the combination of X ¹ , Y ¹ , Q ¹ and Q ^{2 in} the compound (A), the formula (ar-86) is particularly preferable. When the compound is the above compound, the obtained optical film tends to have a high reverse wavelength dispersion of retardation. Therefore, it is easy to adjust the wavelength dispersibility of the optical film to a desired value by mixing with a liquid crystal compound exhibiting positive wavelength dispersibility.

In formula (A), D ¹ and D ² are —O—CO—, —O—CS—, —O—CR ⁴ R ⁵ —, —NR ⁴ —CR ⁵ R ⁶ — or —NR ⁴ —CO—. Is more preferable, * -O-CO-, * -O-CS-, * -O-CR ⁴ R ^5- , * -NR ⁴ -CR ⁵ R ⁶ -or * -NR ⁴ -CO-(* Represents a bond to the benzene ring to which Q ¹ and Q ² are bonded.), More preferably * —O—CO—, * —O—CS— or * —NR ⁴ —CO— (* represents Q ¹ and Q ² represent a bond with a benzene ring to which Q ² is bonded.

R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group.

The divalent alicyclic hydrocarbon group represented by G ¹ and G ² includes a monocyclic hydrocarbon group and a bridged cyclic hydrocarbon group, and is a 5-membered ring or a 6-membered ring. Is preferred. The alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a saturated alicyclic hydrocarbon group. The alicyclic hydrocarbon group may divalent contain a hetero atom represented by G ¹ and G ^2, for example, those represented by the formula (g-1) ~ formula (g-10).

The hydrogen atom contained in the divalent alicyclic hydrocarbon group represented by G ¹ and G ² may be substituted with a substituent (hereinafter referred to as substituent Z ² ). Examples of the substituent Z ² include alkyl groups having 1 to 4 carbon atoms such as a methyl group, ethyl group, isopropyl group, and tert-butyl group; alkoxy groups having 1 to 4 carbon atoms such as a methoxy group and an ethoxy group; C1-C4 fluoroalkyl group such as methyl group; C1-C4 fluoroalkoxy group such as trifluoromethoxy group; cyano group; nitro group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and the like It is done.

G ¹ and G ² are preferably a divalent alicyclic hydrocarbon group composed of a 6-membered ring represented by the formula (g-1). Among these, both G ¹ and G ² are more preferably a cyclohexane-1,4-diyl group, and particularly preferably a trans-cyclohexane-1,4-diyl group.

L ¹ and L ² in the formula (A) are each independently a monovalent organic group, and L ¹ or L ² is a monovalent group having a polymerizable group.
The organic group L ¹ is preferably a group represented by the formula (A1), and L ² is preferably a group represented by the formula (A2).
P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) _l -E ^2- (A2)
Wherein (A1) and formula ^{(A2), B 1, B} 2, E 1 and E ^2, each ^{independently, -CR 11 R 12 -, -} CH 2 -CH 2 -, - O -, - S —, —CO—O—, —O—CO—O—, —CS—O—, —O—CS—O—, —CO—NR ¹¹ —, —O—CH ₂ —, —S—CH ₂ —. Or it represents a single bond.
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, and the alicyclic hydrocarbon —CH ₂ — contained in the group may be replaced by —O—, —S— or —NH—, and —CH (—) — contained in the alicyclic hydrocarbon group represents —N (-)-May be replaced.
k and l each independently represents an integer of 0 to 3. When k is an integer of 2 or more, the plurality of B ¹ and A ¹ may be the same as or different from each other. If l is an integer of 2 or more, a plurality of B ² and A ² may be the same or different from each other.
F ¹ and F ² represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ and P ² represent a hydrogen atom or a polymerizable group, and at least one is a polymerizable group.
R ¹¹ and R ¹² represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ]

The divalent alicyclic hydrocarbon group represented by A ¹ and A ² can be selected from the same range as exemplified as G ¹ and G ² , and the preferred embodiment is the same as G ¹ and G ^2. It is. In addition, the divalent aromatic hydrocarbon group represented by A ¹ and A ² may be monocyclic or polycyclic (polycyclic or condensed polycyclic in which a plurality of aromatic rings are linked by a single bond). Formula). Examples of the divalent aromatic hydrocarbon group represented by A ¹ and A ² include those represented by formula (a-1) to formula (a-8). In addition, the aromatic hydrocarbon group represented by A ¹ and A ² preferably has an axis of symmetry and a plane of symmetry.

The hydrogen atom contained in the alicyclic hydrocarbon group and aromatic hydrocarbon group represented by A ¹ and A ² may be substituted with a substituent. The substituent can be selected from the same range as that exemplified as the substituent Z ² .

A ¹ and A ² are each independently preferably a monocyclic 1,4-phenylene group or cyclohexane-1,4-diyl group, and in particular, since the production of the compound (A) is easy, A 1,4-phenylene group is preferred. Furthermore, A ¹ and A ² are preferably the same type of group because the compound (A) tends to be easily produced.

B ¹ and B ² are preferably the same type of group since the production of the compound (A) tends to be easy. In addition, when k and l are integers of 2 or more, since a plurality of B ¹ and B ² can more easily produce the compound (A), B ¹ and A ² bonded to only A ¹ can be obtained. It is preferable that B ² bonded to only each independently is —CH ₂ —CH ₂ —, —CO—O—, —CO—NH—, —O—CH ₂ — or a single bond. In particular, -CO-O- is preferable because it exhibits high liquid crystallinity. Further, B ¹ bonded to F ¹ and B ² bonded to F ² are each independently —O—, —CO—O—, —O—CO—O—, —CO—NH. -Or more preferably a single bond.

  It is preferable that k and l each independently represent an integer of 0 to 3, and k and l are more preferably 0 to 2. The total of k and l is preferably 5 or less, and more preferably 4 or less. When k and l are in the above ranges, the compound (A) tends to exhibit liquid crystallinity.

F ¹ and F ² are preferably an alkanediyl group having 1 to 12 carbon atoms, and more preferably a linear alkanediyl group. In particular, an unsubstituted alkanediyl group is preferred. A hydrogen atom contained in the alkanediyl group may be substituted with a halogen atom. Moreover, —CH ₂ — contained in the alkanediyl group may be substituted with —O— or —CO—.

P ¹ and P ² are a hydrogen atom or a polymerizable group, and at least one is a polymerizable group. Since the hardness of the obtained optical film tends to be excellent, it is preferable that both P ¹ and P ² are polymerizable groups.

Here, the polymerizable group means a substituent capable of polymerizing the compound (A). Specifically, a vinyl group, a vinyloxy group, a styryl group, a p- (2-phenylethenyl) phenyl group, Polymerizable group having ethylenically unsaturated group such as acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group, carboxy group, acetyl group, hydroxy group, carbamoyl group, alkylamino group having 1 to 4 carbon atoms, amino group And oxiranyl group, oxetanyl group, formyl group, isocyanato group, isothiocyanato group and the like.
As the polymerizable group, a radical polymerizable group and a cationic polymerizable group suitable for photopolymerization are preferable, and since they are particularly easy to handle and easy to manufacture, acryloyl group, methacryloyl group, acryloyl group are preferable. An oxy group and a methacryloyloxy group are preferred. Among them, the polymerizable group is preferably each independently an acryloyloxy group or a methacryloyloxy group, and particularly preferably an acryloyloxy group.

In the formula (A), D ¹ and D ² , G ¹ and G ^2, and L ¹ and L ² are the same, that is, -D ¹ -G ¹ -L ¹ and -D ² -G ² -L. ² preferably have the same structure.

* -D ¹ -G ¹ -L ¹ when L ¹ is a group represented by the formula (A1) (* represents a bond to the phenylene ring to which Q ¹ and Q ² are bonded.) specific examples of, and, if L ² is a group represented by the formula ^{(A2) * -D 2 -G 2} -L 2 (* is a phenylene ring to which Q ¹ and Q ² are attached Specific examples of (showing a bond) include groups represented by the following formulas (R-1) to (R-134).
In the formulas (R-1) to (R-134), n represents an integer of 2 to 12, preferably 3 to 10, and more preferably 4 to 8.

The compound (A) is preferably a compound that satisfies the formulas (1) and (2).
( _Nπ- 4) / 3 <k + 1 + 4 (1)
12 ≦ N _π ≦ 22 (2)
Wherein (1) and (2), is N _[pi, in formula (A), -D ¹ -G ¹ -L ^1, the aromatic ring within portion excluding the -D ² -G ² -L ² Represents the number of π electrons contained. k and l represent the same meaning as in formulas (A1) and (A2). ]

Examples of the compound (A) include the following compounds (i) to (xxvii). Incidentally, R1 in Table 1, the -D ¹ -G ¹ -L ^1, R2 represents -D ² -G ² -L ^2.

Among the above Table 1, the compound (xvi), the compound compound combinations such as X ¹ represents a group represented by the formula (ar-39), a combination of such X ¹ is a group represented by the formula (ar-40) Or a combination of X ^{1 and the} like is any of a mixture of a compound which is a group represented by the formula (ar-39) and a compound which is a group represented by the formula (ar-40). Similarly, compounds (xxvi), the compound combinations such as X ¹ is a group represented by the formula (ar-66), compound combinations such as X ¹ is a group represented by the formula (ar-67), or , X ^1, etc. means any one of a mixture of a compound which is a group represented by formula (ar-66) and a compound which is a group represented by formula (ar-67). Compound (xxvii), the compound combinations such as X ¹ is a group compound is a group represented by the formula (ar-68), a combination of such X ¹ represented by the formula (ar-69), or, X ¹ And the like are any of a mixture of a compound which is a group represented by formula (ar-68) and a compound which is a group represented by formula (ar-69).

  Specific examples of the compounds in Table 1 include the following compounds. Compound (i), Compound (iii), Compound (iv), Compound (v), Compound (viii), Compound (ix), Compound (x), Compound (xv), Compound (xvii), Compound (xviii) ), Compound (xix), Compound (xx), Compound (xxii), Compound (xxiii), Compound (xxiv) and Compound (xxv). The following chemical formula is intended to include all stereoisomers. In the compounds (i) to (xxv), it is preferred that all cyclohexane-1,4-diyl groups are trans-cyclohexane-1,4-diyl groups.

  Furthermore, examples of the compound (A) include compounds represented by the formulas (A1-1) to (A61-8). In the formula, * represents a bond, for example, the compound represented by the formula (A1-1) is a compound represented as follows.

  Compound (A) is a known organic synthesis reaction described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, New Experimental Chemistry Course, etc. (for example, condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Kashiyama reaction, Buchwald-Heartwig reaction, Friedel-Craft reaction, Heck reaction, Aldol reaction, etc. ) Can be manufactured by appropriately combining depending on the structure.

For example, when D ¹ and D ² of the compound (A) are * —O—CO—, first, the compound represented by the formula (1-1) and the compound represented by the formula (1-2) To obtain a compound represented by the formula (1-3).

[Wherein, X ¹ , Y ¹ , Q ¹ and Q ² represent the same meaning as in formula (A). ]

[Wherein, G ¹ , E ¹ , A ¹ , B ¹ , F ¹ , P ¹ and k represent the same meaning as described above. ]

[Wherein, X ¹ , Y ¹ , Q ¹ , Q ² , G ¹ , E ¹ , A ¹ , B ¹ , F ¹ , P ¹ and k represent the same meaning as described above. ]

  Next, the compound (A) can be produced by reacting the obtained compound represented by the formula (1-3) with the compound represented by the formula (1-4).

[Wherein, G ² , E ² , A ² , B ² , F ² , P ² and l represent the same meaning as described above. ]

  Reaction of a compound represented by formula (1-1) with a compound represented by formula (1-2), and a reaction between a compound represented by formula (1-3) and a compound represented by formula (1-4) The reaction is preferably carried out in the presence of a condensing agent.

  Examples of the condensing agent include 1-cyclohexyl-3- (2-morpholinoethyl) carbodiimide met-para-toluenesulfonate, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1-ethyl-3- ( Carbodiimides such as 3-dimethylaminopropyl) carbodiimide hydrochloride (commercially available as Water Soluble Carbodiimide), bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, bisisopropylcarbodiimide; 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazole, 1,1'-oxalyldiimidazole, diphenylphosphoryl azide, 1- (4-nitrobenzenesulfur Nil) -1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N , N, N ′, N′-tetramethyl-O— (N-succinimidyl) uronium tetrafluoroborate, N- (1,2,2,2-tetrachloroethoxycarbonyloxy) succinimide, N-carbobenzoxysuccinimide , O- (6-chlorobenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium tetrafluoroborate, O- (6-chlorobenzotriazol-1-yl) -N, N , N ′, N′-Tetramethyluronium hexafluorophor Sulfate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate, 2-chloro-1- Examples include methylpyridinium iodide, 2-chloro-1-methylpyridinium para-toluenesulfonate, 2-fluoro-1-methylpyridinium para-toluenesulfonate, and trichloroacetic acid pentachlorophenyl ester. Among them, from the viewpoint of reactivity, cost, and usable solvent, as the condensing agent, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide Hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, bisisopropylcarbodiimide, and 2,2′-carbonylbis-1H-imidazole are preferred.

  10-99.9 mass% is preferable with respect to solid content, as for content of a compound (A), 20-99 mass% is more preferable, 50-97 mass% is further more preferable, and 80-95 mass% is especially. preferable. When the content of the compound (A) is within the above range, uniform polarization conversion is possible in a wide wavelength range. Here, solid content means the quantity remove | excluding the solvent component mentioned later from the composition of this invention. A compound (A) may be used independently or may use 2 or more types together.

1-2. Antioxidant (B)
The composition of the present invention contains an antioxidant (B). Examples of the antioxidant include phenolic antioxidants, sulfur antioxidants, phosphorus antioxidants, and amine antioxidants. Among these, a phenolic antioxidant is preferable in that the optical film is less colored.

  Examples of the phenolic antioxidant include 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, and 2,6-dicyclohexyl-4-methyl. Phenol, 2,6-di-tert-amyl-4-methylphenol, 2,6-di-tert-octyl-4-n-propylphenol, 2,6-dicyclohexyl-4-n-octylphenol, 2-isopropyl- 4-methyl-6-tert-butylphenol, 2-tert-butyl-2-ethyl-6-tert-octylphenol, 2-isobutyl-4-ethyl-6-tert-hexylphenol, 2-cyclohexyl-4-n-butyl -6-isopropylphenol, dl-α-tocopherol, tert-butylhydro Non, 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 4,4′-butylidenebis (3-methyl-6-tert-butylphenol), 4,4′-thiobis (3-methyl-6) -Tert-butylphenol), 2,2'-thiobis (4-methyl-6-tert-butylphenol), 4,4'-methylenebis (2,6-di-tert-butylphenol), 2,2'-methylenebis [6 -(1-methylcyclohexyl) -p-cresol], 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2,2'-butylidenebis (2-tert-butyl-4-methylphenol) 2-tert-butyl-6- (3-tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylpheny Acrylate, 2- [1- (2-hydroxy-3,5-di-tert-pentylphenyl) ethyl] -4,6-di-tert-pentylphenyl acrylate, 1,1,3-tris (2-methyl -4-hydroxy-5-tert-butylphenyl) butane, triethylene glycol bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2,2-thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], N, N′-hexamethylenebis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-t rt-butyl-4-hydroxybenzylphosphonate diethyl ester, tris (2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl) isocyanurate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) ) Isocyanurate, tris [(3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxyethyl] isocyanurate, tris (4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl) isocyanurate 2,4-bis (n-octylthio) -6- (4-hydroxy-3,5-di-tert-butylanilino) -1,3,5-triazine, tetrakis [methylene-3- (3,5-di -Tert-butyl-4-hydroxyphenyl) propionate] methane, 2, '-Methylenebis (4-methyl-6-tert-butylphenol) terephthalate, 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 3 , 9-bis [1,1-dimethyl-2- {β- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy} ethyl] -2,4,8,10-tetraoxaspiro [ 5,5] undecane, 2,2-bis [4- (2- (3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)) ethoxyphenyl] propane, β- (3,5-di -Tert-butyl-4-hydroxyphenyl) propionic acid stearyl ester and the like.

  A commercial item may be used as said phenolic antioxidant. Examples of commercially available phenolic antioxidants include Sumilizer (registered trademark) BHT (2,6-di-tert-butyl-4-methylphenol), Sumilizer GM (2-tert-butyl-6- (3 -Tert-butyl-2-hydroxy-5-methylbenzyl) -4-methylphenyl acrylate), Sumilizer GS (F) (2- [1- (2-hydroxy-3,5-di-tert-pentylphenyl) ethyl ] -4,6-di-tert-pentylphenyl acrylate), Sumilizer GA-80 (3,9-bis [2- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy] -1,1-dimethylethyl] -2,4,8,10-tetraoxaspiro [5 · 5] undecane), Sumilyzer MDP- (2,2′-methylenebis (6-tert-butyl-4-methylphenol)), Sumilizer BBM-S (4,4′-butylidenebis (6-tert-butyl-3-methylphenol)), Sumilizer WX-R (4,4′-thiobis (6-tert-butyl-3-methylphenol)), Sumilizer L (S) (all manufactured by Sumitomo Chemical Co., Ltd.), Irganox (registered trademark) 1010 (tetrakis) [Methylene-3- (3 ′, 5′-di-tert-butyl-4′-hydroxyphenyl) propionate] methane), Irganox 1035 (2,2-thio [diethylbis-3 (3,5-di-tert) -Butyl-4-hydroxyphenyl) propionate]), Irganox 1076 (β- (3,5-di-tert-butyl) Til-4-hydroxyphenyl) propionic acid stearyl ester), Irganox 1098 (N, N ′-(1,6-hexanediyl) bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl)] Propionamide]), Irganox 1135 (octyl 3- (4-hydroxy-3,5-diisopropylphenyl) propionate), Irganox 1330 (1,3,5-trimethyl-2,4,6-tris (3 5-di-tert-butyl-4-hydroxybenzyl) benzene), Irganox 1726 (2,4-bis (dodecylthiomethyl) -6-methylphenol), Irganox 1425WL, Irganox 1520L (2,4-bis (Octylthiomethyl) -6-methylphenol), Irganox 245 3,6-dioxaoctane-1,8-diol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propanoate]), Irganox 259 (1,6-hexanediol bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate]), Irganox 3114 (Tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate), Irganox 565 (6 -(4-hydroxy-3,5-di-tert-butylanilino) -2,4-bis (octylthio) -1,3,5-triazine), Irganox 295, Irganox 3125 (Tris [(3,5- Di-t-butyl-4-hydroxyphenyl) propionyloxyethyl] isocyanurate) All manufactured by BASF Japan Ltd.), Cyanox 1790 (Tris (2,6-dimethyl-3-hydroxy-4-tert-butylbenzyl) isocyanurate) (Cyanox 1790, manufactured by Cytec), Vitamin E (dl-α-tocopherol) ) (Manufactured by Eisai). A phenolic antioxidant may be used independently and may use 2 or more types together.

  Examples of the sulfur-based antioxidant include dialkylthiodipropionates such as dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate; polyhydric alcohol esters of butylthiopropionic acid, octyl Polyhydric alcohol ester of thiopropionic acid, polyhydric alcohol ester of lauryl thiopropionic acid, polyhydric alcohol ester of stearyl thiopropionic acid (for example, glycerin, trimethylolethane, trimethylolpropane, penta Erythritol, trishydroxyethyl isocyanurate, etc.) and polyhydric alcohol esters of alkylthiopropionic acid such as pentaerythryltetrakis-3-laurylthiopropionate. It is.

  A commercially available product may be used as the sulfur-based antioxidant. Commercially available sulfur-based antioxidants include, for example, Sumilizer TPL-R (dilauryl-3,3′-thiodipropionate), Sumilizer TPM (dimyristyl-3,3′-thiodipropionate), and Sumilizer TPS. (Distearyl-3,3′-thiodipropionate), Sumilizer TP-D (pentaerythrityltetrakis (3-laurylthiopropionate), Sumilizer MB (2-mercaptobenzimidazole) (all of which are Sumitomo Chemical ( The sulfur type antioxidant may be used alone or in combination of two or more.

  Examples of the phosphorus antioxidant include trioctyl phosphite, trilauryl phosphite, tridecyl phosphite, (octyl) diphenyl phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tri Phenyl phosphite, Tris (butoxyethyl) phosphite, Tris (nonylphenyl) phosphite, Distearyl pentaerythritol diphosphite, Tetra (tridecyl) -1,1,3-tris (2-methyl-5-tert-butyl -4-hydroxyphenyl) butanediphosphite, tetra (C12-C15 mixed alkyl) -4,4'-isopropylidenediphenyl diphosphite, tetra (tridecyl) -4,4'-butylidenebis (3-methyl-6) -Tert-butylphenol) di Sphite, tris (3,5-di-tert-butyl-4-hydroxyphenyl) phosphite, tris (mono-dimixed nonylphenyl) phosphite, hydrogenated-4,4′-isopropylidene diphenol polyphosphite, Bis (octylphenyl) bis [4,4′-butylidenebis (3-methyl-6-tert-butylphenol)]-1,6-hexanediol diphosphite, phenyl (4,4′-isopropylidenediphenol) pentaerythritol Diphosphite, distearyl pentaerythritol diphosphite, tris [4,4′-isopropylidenebis (2-tert-butylphenol)] phosphite, di (isodecyl) phenyl phosphite, 4,4′-isopropylidenebis ( 2-tert-Butylpheno L) bis (nonylphenyl) phosphite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, bis (2,4-di-tert-butyl-6-methylphenyl) ethyl Phosphite, 2-[{2,4,8,10-tetra-tert-butyldibenz [d, f] [1.3.2] -dioxaphosphin-6-yl} oxy] -N, N- Bis [2-[{2,4,8,10-tetra-tert-butyldibenz [d, f] [1.3.2] -dioxaphosphin-6-yl} oxy] ethyl] ethanamine, 6- [3- (3-tert-Butyl-4-hydroxy-5-methylphenyl) propoxy] -2,4,8,10-tetra-tert-butyldibenz [d, f] [1.3.2] -dioxa Phosfepin etc. Is mentioned.

  A commercially available product may be used as the phosphorus-based antioxidant. Commercially available phosphorus antioxidants include, for example, Sumilizer GP (6- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy] -2,4,8,10-tetra -Tert-butyl-dibenzo [d, f] [1,3,2] dioxaphosphepine) (manufactured by Sumitomo Chemical Co., Ltd.), Irgafos (registered trademark) 168 (tris (2,4-di -Tert-butylphenyl) phosphite), Irgaphos 12 (2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphos Fepin6-yl] oxy] -N, N-bis [2-[[2,4,8,10-tetrakis (1,1 dimethylethyl) dibenzo [d, f] [1,3,2,] di Oxaphosfepi -6-yl] oxy] -ethyl] ethanamine), Irgaphos 38 (all manufactured by BASF Japan Ltd.), ADK STAB 329K, ADK STAB PEP36 (cyclic neopentanetetraylbis (2,6-di-t-butyl) -4-methylphenyl) phosphite), Adekastab PEP-8 (distearyl pentaerythritol diphosphite) (all manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston 618, Weston 619G, Ultranox 626 ( As mentioned above, all are made from GE. A phosphorus antioxidant may be used independently and may use 2 or more types together.

  Examples of the amine-based antioxidant include N, N′-di-sec-butyl-p-phenylenediamine, N, N′-di-isopropyl-p-phenylenediamine, N, N′-bis (1, 4-dimethylpentyl) -p-phenylenediamine, N, N′-bis (1-ethyl-3-methylpentyl) -p-phenylenediamine, N, N′-bis (1-methylheptyl) -p-phenylenediamine N, N′-dicyclohexyl-p-phenylenediamine, N, N′-diphenyl-p-phenylenediamine, N, N′-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N′-phenyl -P-phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N- (1-methylheptyl) -N'-phenyl-p Phenylenediamine, N-cyclohexyl-N′-phenyl-p-phenylenediamine, 4- (p-toluenesulfamoyl) diphenylamine, N, N′-dimethyl-N, N′-di-secondary butyl-p-phenylene Examples thereof include diamine, diphenylamine, N-allyldiphenylamine, and alkylated diphenylamine.

  A commercially available product may be used as the amine-based antioxidant. Commercially available amine antioxidants include, for example, Sumilizer BPA (N, N'-di-sec-butyl-p-phenylenediamine), Sumilizer BPA-M1, Sumilizer 4ML (p-phenylenediamine derivative), Sumilizer 9A (alkalinized difinylamine) etc. are mentioned. An amine antioxidant may be used independently and may use 2 or more types together.

  Content of antioxidant (B) becomes like this. Preferably it is 0.01 mass%-10 mass% with respect to solid content, More preferably, it is 0.1 mass%-5 mass%. If it is in the said range, when superposing | polymerizing the polymeric component contained in a composition, it can suppress more disturbing the orientation of a compound (A).

1-3. Photopolymerization initiator (C)
The composition of this invention contains a photoinitiator. The photopolymerization initiator is a compound capable of generating an active radical by the action of light and initiating polymerization of the compound (A). Examples of the photopolymerization initiator include alkylphenone compounds, benzoin compounds, benzophenone compounds, and oxime compounds.

  Examples of the alkylphenone compound include α-aminoalkylphenone compounds, α-hydroxyalkylphenone compounds, and α-alkoxyalkylphenone compounds. Examples of the α-aminoalkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzyl. Butan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2- (4-methylphenylmethyl) butan-1-one, and the like are preferable, and 2-methyl-2-morpholino-1 is preferable. -(4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one and the like can be mentioned. The α-aminoalkylphenone compound may be a commercially available product such as Irgacure (registered trademark) 369, 379EG, 907 (above, manufactured by BASF Japan Ltd.), Sequol (registered trademark) BEE (manufactured by Seiko Chemical Co., Ltd.). Good.

  Examples of the α-hydroxyalkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propane- Examples include 1-one, 1-hydroxycyclohexyl phenyl ketone, and oligomers of 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one. As the α-hydroxyalkylphenone compound, commercially available products such as Irgacure 184, 2959, 127 (manufactured by BASF Japan Ltd.), Sequol Z (manufactured by Seiko Chemical Co., Ltd.) may be used. Examples of the α-alkoxyalkylphenone compound include diethoxyacetophenone and benzyldimethyl ketal. Commercially available products such as Irgacure 651 (above, manufactured by BASF Japan Ltd.) may be used as the α-alkoxyalkylphenone compound.

  The alkylphenone compound is preferably an α-aminoalkylphenone compound, and more preferably a compound represented by formula (C-1). When these compounds are used, the obtained optical film is excellent in heat resistance and moist heat resistance.

[In Formula (C-1), Q ³ represents a hydrogen atom or a methyl group. ]

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.
Examples of the benzophenone compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxy). Carbonyl) benzophenone, 2,4,6-trimethylbenzophenone and the like.
Examples of the oxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one- 2-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6 -{2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine and the like. Commercial products such as Irgacure OXE-01, OXE-02 (manufactured by BASF Japan), N-1919 (manufactured by ADEKA) may be used.

  As the photopolymerization initiator, the acetophenone compound, the benzoin compound, the benzophenone compound, the oxime compound, or the like may be used alone or in combination of two or more. Among these, it is preferable to use an acetophenone compound as a photopolymerization initiator. The amount of the acetophenone compound used is preferably 90 parts by mass or more with respect to the total amount of photopolymerization initiator, and more preferably the total amount of photopolymerization initiator is an acetophenone compound.

  The content of the photopolymerization initiator (C) is preferably 0.1% by mass to 30% by mass and more preferably 0.5% by mass to 10% by mass with respect to the solid content. If it is in the said range, when superposing | polymerizing the polymeric component contained in a composition, it can suppress more disturbing the orientation of a compound (A).

1-4. Liquid crystal compound (A ')
The composition of the present invention may contain a liquid crystal compound (A ′) different from the compound (A). Specific examples of the liquid crystal compound (A ′) include the liquid crystal manual (edited by the Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd., October 30, 2000), Chapter 3 of molecular structure and liquid crystallinity, 3.2 non-chiral. Examples thereof include rod-like liquid crystal molecules, 3.3 compounds described in chiral rod-like liquid crystal molecules, and compounds described in Japanese Patent Application Laid-Open No. 2010-31223, Japanese Patent Application No. 2010-121480, or Japanese Patent Application No. 2010-094858. Of these, compounds having a polymerizable group and exhibiting liquid crystallinity are preferred. The liquid crystal compound (A ′) may be used alone or in combination of two or more.

  Examples of the liquid crystal compound (A ′) include a compound represented by the formula (3) (hereinafter sometimes referred to as “compound (3)”).

^{P 11 -E 11 - (B 11} -A 11) t -B 12 -G (3)
[In Formula (3), A ¹¹ is an aromatic heterocycle which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or an oil which may have a substituent. Represents a cyclic hydrocarbon group.
B ¹¹ and B ¹² are each independently, -C≡C -, - CH = CH -, - CH 2 -CH 2 -, - O -, - S -, - CO -, - CO-O -, - CS -, - O-CO- O -, - CR 13 R 14 -, - CR 13 R 14 -CR 15 R 16 -, - O-CR 13 R 14 -, - CR 13 R 14 -O-CR 15 R ^{16 -, - CO-O-} CR 13 R 14 -, - O-CO-CR 13 R 14 -, - CR 13 R 14 -O-CO-CR 15 R 16 -, - CR 13 R 14 -CO-O —CR ¹⁵ R ¹⁶ —, —NR ¹³ —CR ¹⁴ R ¹⁵ —, —CH═N—, —N═N—, —CO—NR ¹⁶ —, —OCH ₂ —, —OCF ₂ —, —CH ₂ O _{-, - CF 2 O -,} - CH = represents a CH-CO-O- or a single bond. R < ¹³ > -R < ¹⁶ > represents a hydrogen atom or a C1-C4 alkyl group.
G is a hydrogen atom, a halogen atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a fluoroalkyl group having 1 to 13 carbon atoms, an N-alkylamino group having 1 to 13 carbon atoms, cyano group, a nitro group or a -E ¹² -P ^12.
E ¹¹ and E ¹² represent an alkanediyl group having 1 to 18 carbon atoms, and a hydrogen atom contained in the alkanediyl group may be substituted with a halogen atom, and —CH ₂ contained in the alkanediyl group -May be replaced by -O- or -CO-.
P ¹¹ and P ¹² represent a polymerizable group.
t represents an integer of 1 to 5. When t is an integer of 2 or more, the plurality of B ¹¹ and A ¹¹ may be the same as or different from each other. ]

Examples of the aromatic hydrocarbon ring represented by A ¹¹ include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrolin ring. , Thiazole ring and benzothiazole ring. Among these, a benzene ring, a thiazole ring or a benzothiazole ring is preferable. Examples of the aromatic hydrocarbon ring or aromatic heterocyclic ring represented by A ¹¹ include divalent groups represented by formula (Ar-1) to formula (Ar-11).

[In Formula (Ar-1) to Formula (Ar-11), X ³ represents a group selected from the same range as the group exemplified as X ¹ in Formula (A). When a plurality of X ¹ are present, they may be the same as or different from each other. Y ³ represents a group selected from the same range as the groups exemplified as Y ¹ in the formula (A). Z ³ represents a group selected from the same range as the group exemplified as Z ¹ in the formula (A).
W ^a and W ^b each independently represent a hydrogen atom, a cyano group, a methyl group, or a halogen atom.
m represents an integer of 0-6.
n represents an integer of 0 to 4.
o represents an integer of 0 to 2.
When m, n, and o are integers of 2 or more, the plurality of Z ³ may be the same as or different from each other. ]

Specific examples of the aromatic hydrocarbon ring or aromatic heterocyclic ring represented by A ¹¹ include the following groups.
For example, specific examples of the groups represented by formula (Ar-1) and formula (Ar-7) include the following groups.

Carbon number of the alicyclic hydrocarbon group represented by A ¹¹ is, for example, 3 to 18, preferably 5 to 12, and particularly preferably 5 or 6. Examples of the alicyclic hydrocarbon group represented by A ¹¹ include a cyclohexane-1,4-diyl group. Examples of the substituent that the alicyclic hydrocarbon group may have include a halogen atom, an alkyl group having 1 to 6 carbon atoms that may have a fluoro group, and carbon that may have a fluoro group. Examples of the alkoxy group, nitro group, and cyano group of formulas 1 to 6 are given.

Examples of P ¹¹ and P ¹² include the same groups as P ¹ and P ² of the compound (A). Since it can be cured at a lower temperature, a photopolymerizable group is preferable, a radical polymerizable group or a cationic polymerizable group is preferable, and particularly easy to handle and easy to produce the compound (1). Groups represented by formulas (P-1) to (P-5) are preferred.

[In Formulas (P-1) to (P-5), R ^{17 to} R ²¹ each independently represents an alkyl group having 1 to 6 carbon atoms or a hydrogen atom. * Represents a bond to B ^11. ]

E ¹¹ and E ¹² are each an alkanediyl group having 1 to 18 carbon atoms, and preferably an alkanediyl group having 1 to 12 carbon atoms that is linear or has one branch.

  Examples of the compound (1) include the following.

  Content of a liquid crystal compound (A ') is 0-90 mass parts with respect to 100 mass parts of total amounts of a liquid crystal compound (A') and a compound (A), for example, Preferably it is 0-70 mass parts. More preferably, it is 0-40 mass parts.

  The wavelength dispersion characteristic of the optical film obtained by the composition of the present invention can be determined by the content of the structural unit derived from the compound (A) and the content of the structural unit derived from the liquid crystal compound (A ′). . When the content of the structural unit derived from the compound (A) in the optical film is increased, reverse wavelength dispersion characteristics are further exhibited. Specifically, about 2 to 5 types of compositions having different content of structural units derived from the compound (A) are prepared, and optical films having the same film thickness are produced for each composition, and the retardation value thereof is produced. Ask for. Then, from the result, the correlation between the content of the structural unit derived from the compound (A) and the retardation value of the optical film is obtained, and the desired retardation value is given to the optical film at the above film thickness from the obtained correlation. What is necessary is just to determine content of the structural unit derived from the compound (A) required in order to give.

1-5. Organic Solvent The composition of the present invention may contain a solvent. The organic solvent is an organic solvent that can dissolve the components of the composition such as the compound (A), and may be any solvent that is inert to the polymerization reaction. Specifically, methanol, ethanol, ethylene glycol, isopropyl Alcohols such as alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether or phenol; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate, ethyl lactate; Ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone and methyl isobutyl ketone; non-chlorine aliphatic hydrocarbons such as pentane, hexane and heptane ; Nitrile solvents such as acetonitrile; tetrahydrofuran, ether solvents such as dimethoxyethane: toluene, non-chlorinated aromatic hydrocarbon solvents such as xylene chloroform, chlorinated solvents such as chlorobenzene; and the like. These organic solvents may be used alone or in combination. Among the above organic solvents, alcohols, ester solvents, ketone solvents, non-chlorine aliphatic hydrocarbon solvents, and non-chlorine aromatic hydrocarbon solvents are preferable. In particular, the composition of the present invention is excellent in compatibility and can be dissolved in alcohols, ester solvents, ketone solvents, non-chlorine aliphatic hydrocarbon solvents, non-chlorine aromatic hydrocarbon solvents, chloroform, etc. Even without using a chlorine-based solvent, it can be dissolved and applied.

  In addition, when producing an optical film etc. using the composition of this invention, it is preferable that a composition contains the organic solvent from a viewpoint of the ease of film-forming. In this case, the usage-amount of a solvent becomes like this. Preferably it is 50 mass%-98 mass% with respect to the composition of this invention, More preferably, it is 50 mass%-95 mass%. In other words, the solid content concentration in the composition of the present invention is preferably 2% by mass to 50% by mass, and more preferably 5% by mass to 50% by mass.

  The composition of this invention may contain additives, such as a photosensitizer, a leveling agent, and a chiral agent, as needed.

1-6. Photosensitizer Examples of the photosensitizer include xanthones such as xanthone and thioxanthone; anthracene having a substituent such as anthracene and alkyl ether; phenothiazine and rubrene.
By using a photosensitizer, polymerization of the compound (A) or the like can be made highly sensitive. Moreover, as the usage-amount of a photosensitizer, it is 0.1 mass part-30 mass parts with respect to 100 mass parts of compounds (A), Preferably it is 0.5 mass part-10 mass parts.

1-7. Leveling agents Examples of the leveling agent include organic modified silicone oils, polyacrylates, and perfluoroalkyls. Specifically, for example, DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (all are manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341, X22-161A, KF6001 (all manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (all, Momentive Performance Materials Japan) Made by a limited liability company), Fluorinert (registered trademark) FC-72, FC-40, FC-43, FC-3283 (all above) (Manufactured by Tomo 3M Co., Ltd.), MegaFac (registered trademark) R-08, R-30, R-90, F-410, F-411, F-443, F-445, F -470, F-477, F-479, F-482, F-482 (all of which are manufactured by DIC Corporation), Ftop (trade name) EF301, EF303, EF351, EF352 (All from Mitsubishi Materials Electronics Chemical Co., Ltd.), Surflon (registered trademark) S-381, S-382, S-383, S-393, SC-101, SC-105, KH- 40, SA-100 (all are manufactured by AGC Seimi Chemical Co., Ltd.), trade names E1830, E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.), BM-1000, BM-1100, BYK-352, BYK-3 3, BYK-361N (both trade name: BM Chemie Co., Ltd.), and the like. These leveling agents may be used alone or in combination of two or more.

  By using a leveling agent, the retardation plate can be smoothed. Furthermore, in the production process of the retardation plate, the fluidity of the composition (A) can be controlled, and the crosslinking density of the retardation plate obtained by polymerizing the compound (A) or the like can be adjusted. Moreover, the usage-amount of a leveling agent is 0.1 mass part-30 mass parts with respect to 100 mass parts of compounds (A), Preferably it is 0.5 mass part-10 mass parts.

1-8. Chiral agent As the chiral agent, a known chiral agent (for example, described in Liquid Crystal Device Handbook, Chapter 3-4-3, TN, chiral agent for STN, 199 pages, edited by Japan Society for the Promotion of Science, 142nd Committee, 1989) Can be used.
The chiral agent generally contains an asymmetric carbon atom, but an axially asymmetric compound or a planar asymmetric compound containing no asymmetric carbon atom can also be used as the chiral agent. Examples of the axial asymmetric compound or the planar asymmetric compound include binaphthyl, helicene, paracyclophane, and derivatives thereof.
For example, JP 2007-269640 A, JP 2007-269639 A, JP 2007-176870 A, JP 2003-137879 A, JP 2000-51596 A, JP 2007-169178 A, A compound as disclosed in JP-T-9-506088 is exemplified, and preferably, paliocolor (registered trademark) LC756 manufactured by BASF Japan Ltd. is used.
The usage-amount of a chiral agent is 0.1 mass part-30 mass parts, for example with respect to 100 mass parts of compounds (A), for example, Preferably they are 1.0 mass part-25 mass parts. If it is in the said range, when superposing | polymerizing the polymeric component contained in a composition, it can suppress more disturbing the orientation of a compound (A).

2. Optical film The optical film of the present invention is obtained by polymerizing a polymerizable component contained in the composition of the present invention described above. The optical film of the present invention is a film that can transmit light and has an optical function. The optical function means refraction, birefringence and the like.

  The optical film of the present invention is excellent in transparency in the visible light region, and can be used as various display device members. The thickness of the optical film may be appropriately adjusted depending on the retardation value, but is preferably 0.1 μm to 10 μm, and more preferably 0.2 μm to 5 μm from the viewpoint of reducing photoelasticity.

  The optical film of the present invention may be used alone, but a plurality of the optical films of the present invention may be laminated and used in combination with other films. By using in combination with other films, it can be used for retardation films, viewing angle compensation films, viewing angle widening films, antireflection films, polarizing films, circularly polarizing films, elliptically polarizing films, brightness enhancement films, and the like.

  In particular, the optical film of the present invention has a VA (vertical alignment) mode, an IPS (in-plane switching) mode, an OCB (optically compensated bend) mode by changing the optical properties by changing the orientation state of the compound (A). , A TN (twisted nematic) mode, a STN (super twisted nematic) mode, and other retardation films for various liquid crystal display devices.

2-1. Retardation film A retardation film which is a kind of the optical film is one of the preferred embodiments of the present invention. The retardation film of the present invention is obtained by polymerizing a polymerizable component contained in the composition of the present invention. The retardation film is used for converting linearly polarized light into circularly polarized light or elliptically polarized light, or conversely converting circularly polarized light or elliptically polarized light into linearly polarized light, or changing the polarization direction of linearly polarized light.

As the retardation film, the refractive index in a slow axis direction in a plane n _x, the refractive index n _y in the direction (fast axis direction) perpendicular to the slow axis in the plane, the refractive index in the thickness direction If a _{n z, n x> n y} ≒ n z positive a _{plate, n x ≒ n y> n} z negative C _{plate, n x ≒ n y <n} z positive C plate, n _x ≠ n _y ≠ n _z positive O plate and negative O plate.

What is necessary is just to select the retardation value of the said retardation film suitably from the range of 30-300 nm by the display apparatus used.
When the retardation film is used as a broadband λ / 4 plate, Re (549) may be adjusted to 113 to 163 nm, preferably 130 to 150 nm. When used as a broadband λ / 2 plate, Re (549) may be adjusted to 250 to 300 nm, preferably 265 to 285 nm. When the phase difference value is the above value, it is preferable that light having a wide range of wavelengths can be uniformly polarized and converted. Here, the broadband λ / 4 plate is a phase difference plate that expresses a ¼ phase difference value for light of each wavelength, and the broadband λ / 2 plate is for light of each wavelength. It is a retardation plate that expresses a half of the retardation value.

In addition, a film thickness can be adjusted so that a desired phase difference may be given by adjusting suitably content of the compound (A) and liquid crystal compound in the composition of this invention. Since the retardation value (retardation value, Re (λ)) of the obtained film is determined as shown in Equation (4), Δn (λ) and film thickness are used to obtain the desired Re (λ). What is necessary is just to adjust d suitably.
Re (λ) = d × Δn (λ) (4)
(In the formula, Re (λ) represents a retardation value at a wavelength λnm, d represents a film thickness, and Δn (λ) represents a birefringence at a wavelength λnm.)

2-2. Method for Producing Optical Film The optical film can be produced by applying a composition on a substrate, drying it, and polymerizing the compound (A) contained in the composition. Hereinafter, an example of the manufacturing method of an optical film is demonstrated.

2-2-1. Preparation of unpolymerized film An unpolymerized film is obtained by applying the composition onto a substrate and drying it. An alignment film may be formed on the substrate. When the unpolymerized film exhibits a liquid crystal phase such as a nematic phase, it has birefringence due to monodomain alignment.

  Examples of the coating method on the substrate include an extrusion coating method, a direct gravure coating method, a reverse gravure coating method, a CAP coating method, and a die coating method. Moreover, the method of apply | coating using coaters, such as a dip coater, a bar coater, a spin coater, etc. are mentioned.

  As said base material, glass, a plastic sheet, a plastic film, and a translucent film are preferable, for example. Examples of the translucent film include polyolefin films such as polyethylene, polypropylene, norbornene-based polymers, polyvinyl alcohol films, polyethylene terephthalate films, polymethacrylate films, polyacrylate films, cellulose ester films, polyethylene naphthalate films. , Polycarbonate film, polysulfone film, polyethersulfone film, polyetherketone film, polyphenylene sulfide film and polyphenylene oxide film.

  You may use the optical film of this invention in the state laminated | stacked with the said base material. By laminating the base material on the optical film, the optical film is prevented from being damaged when the film is bonded, when the film is transported, stored, or the like, and can be handled easily.

  When producing the optical film of the present invention, it is preferable to form an alignment film on the substrate and then apply the composition onto the alignment film. If such an alignment film is used, it is not necessary to control the refractive index by stretching the optical film, so that in-plane variation in birefringence is reduced. Therefore, it is possible to provide a large optical film that can cope with an increase in size of a flat panel display (FPD).

  It is preferable that the alignment film has solvent resistance that does not dissolve when the composition is applied, has heat resistance to solvent removal and liquid crystal alignment heat treatment, and does not peel off due to friction or the like during rubbing. It is preferable to consist of a composition containing an orientation polymer or an orientation polymer.

  Examples of the orientation polymer include polyamides and gelatins having an amide bond in the molecule, polyimides having an imide bond in the molecule and a hydrolyzate thereof, polyamic acid, polyvinyl alcohol, alkyl-modified polyvinyl alcohol, polyacrylamide, Polymers such as polyoxazole, polyethyleneimine, polystyrene, polyvinylpyrrolidone, polyacrylic acid and polyacrylic acid esters can be mentioned. These orientation polymers may be used alone, or two or more kinds thereof may be mixed or copolymerized. These polymers can be easily obtained by polycondensation such as dehydration and deamination, chain polymerization such as radical polymerization, anion polymerization, and cation polymerization, coordination polymerization, and ring-opening polymerization.

  These alignment polymers can be dissolved in a solvent and applied. The solvent is not particularly limited, and specifically, water; alcohol such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve and propylene glycol monomethyl ether; ethyl acetate, butyl acetate, ethylene glycol Ester solvents such as methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate and ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone and methyl isobutyl ketone; pentane, hexane, heptane, etc. Aliphatic hydrocarbon solvents; aromatic solvents such as toluene and xylene; nitrile solvents such as acetonitrile; tetrahydrofuran and dimeth Chlorinated solvents or chloroform and chlorobenzene; an ether solvent such as Shietan like. These organic solvents may be used alone or in combination.

  In order to form the alignment film, a commercially available alignment film material may be used as it is. Examples of commercially available alignment film materials include Sunever (registered trademark) (manufactured by Nissan Chemical Industries, Ltd.) and Optmer (registered trademark) (manufactured by JSR Corporation).

  As a method for forming an alignment film on the substrate, for example, a commercially available alignment film material or a compound serving as an alignment film material is applied as a solution on the substrate, and then annealed, An alignment film can be formed on the substrate.

  The thickness of the alignment film is, for example, 10 nm to 10000 nm, preferably 10 nm to 1000 nm. If the thickness of the alignment film is within the above range, the compound (A) can be aligned at a desired angle on the alignment film.

  The alignment film may be subjected to an alignment treatment such as rubbing or polarized UV irradiation as necessary. By performing these alignment treatments, the compound (A) can be aligned at a desired angle and direction. In addition, if masking is performed during rubbing or polarized UV irradiation, an alignment pattern can be produced on the resulting optical film. Examples of the method of rubbing the alignment film include a method in which a rubbing roll wound around a rubbing cloth is brought into contact with the alignment film conveyed on the stage.

2-2-2. Polymerization of an unpolymerized film An optical film is obtained by polymerizing a polymerizable component contained in the obtained unpolymerized film.
In the optical film, the orientation of the compound (A) is fixed, and the optical film is not easily affected by changes in birefringence due to heat.

  As a method for polymerizing the unpolymerized film, a photopolymerization method is used. According to the photopolymerization method, an unpolymerized film can be polymerized at a low temperature, and the heat resistance selection range of the substrate is expanded. The photopolymerization reaction is performed by irradiating an unpolymerized film with visible light, ultraviolet light, or laser light. In view of handling, ultraviolet light is particularly preferable.

  The removal of the solvent may be performed in parallel with the polymerization reaction, but it is preferable from the viewpoint of film formability to remove most of the solvent before the polymerization reaction. Examples of the removal method include natural drying, ventilation drying, reduced pressure drying, and heat drying. The temperature at which the solvent is removed by heating is preferably from 0 ° C to 250 ° C, more preferably from 50 ° C to 220 ° C, still more preferably from 80 ° C to 170 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. As long as the heating temperature and the heating time are within the above ranges, a substrate that does not necessarily have sufficient heat resistance can be used.

  After polymerizing the compound (A), the substrate is peeled to obtain a film in which the alignment film and the optical film of the present invention are laminated. Further, the alignment film is peeled off to obtain the optical film of the present invention. Can be obtained. Also, another substrate is bonded to the optical film of the present invention, and the previously laminated substrate is peeled off, or the previously laminated substrate and alignment film are peeled off to transfer Can also be done.

3. Polarizing plate The polarizing plate of the present invention has at least one optical film or retardation film described above.
As a polarizing plate of the present invention, as shown in FIGS. 1A to 1E, (1) a polarizing plate 4a (1) in which the optical film 1 of the present invention and a polarizing film layer 2 are directly laminated. FIG. 1 (a)); (2) Polarizing plate 4b (FIG. 1 (b)) in which the optical film 1 of the present invention and the polarizing film layer 2 are bonded together through an adhesive layer 3; The optical film 1 of the present invention and the optical film 1 ′ of the present invention are laminated, and the optical film 1 ′ of the present invention and the polarizing film layer 2 are further laminated (FIG. 1 (c)); (4) The optical film 1 of the present invention and the optical film 1 ′ of the present invention are bonded together via an adhesive layer 3, and a polarizing film layer 2 is laminated on the optical film 1 ′ of the present invention (see FIG. 1 (d)); and (5) an adhesive layer comprising the optical film 1 of the present invention and the optical film 1 ′ of the present invention. Through bonded, furthermore, a polarizing plate 4e of the optical film 1 of the present invention 'and the polarizing film layer 2 adhesive layer 3' was adhered through a (FIG. 1 (e)), and the like. Here, the adhesive generally refers to an adhesive and / or a pressure-sensitive adhesive. In the description of FIG. 1, the optical film may be only the optical film of the present invention, or may be one in which an alignment film is laminated on the optical film of the present invention. The optical film may be a laminate of an alignment film and a supporting substrate.

  The polarizing film layer 2 may be a film having a polarizing function. For example, a film obtained by stretching a polyvinyl alcohol film by adsorbing iodine or a dichroic dye, a film obtained by stretching a polyvinyl alcohol film, or iodine or two-color film. And a film on which a functional dye is adsorbed.

  Moreover, the polarizing film layer may be provided with the film used as a protective film as needed. Examples of the protective film include polyolefin films such as polyethylene, polypropylene and norbornene polymers, polyethylene terephthalate films, polymethacrylate films, polyacrylate films, cellulose ester films, polyethylene naphthalate films, polycarbonate films, and polysulfone films. , Polyethersulfone film, polyetherketone film, polyphenylene sulfide film and polyphenylene oxide film.

The adhesive used for the adhesive layer 3 and the adhesive layer 3 ′ is preferably an adhesive having high transparency and excellent heat resistance. As such an adhesive, for example, an acrylic adhesive, an epoxy adhesive, a urethane adhesive, or the like is used.
Moreover, in a polarizing plate, as shown in FIG.1 (c)-FIG.1 (e), you may bond together the 2 or more optical film of this invention directly or through an adhesive bond layer.

4). Flat panel display device The flat panel display device of the present invention includes the optical film or retardation film of the present invention. For example, a liquid crystal display including a liquid crystal panel in which the optical film of the present invention and a liquid crystal panel are bonded together. An organic EL display device including an apparatus or an organic electroluminescence (hereinafter also referred to as “EL”) panel in which the optical film of the present invention and a light emitting layer are bonded to each other can be given. As embodiments of the flat panel display device of the present invention, a liquid crystal display device and an organic EL display device will be described in detail below.

4-1. Liquid crystal display device Examples of the liquid crystal display device include a liquid crystal display device as shown in FIGS. 2 (a) and 2 (b). A liquid crystal display device 10a shown in FIG. 2 (a) is formed by bonding the polarizing plate 4 and the liquid crystal panel 6 of the present invention through an adhesive layer 5, and the liquid crystal display device shown in FIG. 2 (b). 10b is obtained by bonding the polarizing plate 4 of the present invention and the polarizing plate 4 ′ of the present invention to both surfaces of the liquid crystal panel 6 via the adhesive layer 5 and the adhesive layer 5 ′. According to the above configuration, by applying a voltage to the liquid crystal panel using an electrode (not shown), the orientation of the liquid crystal molecules changes, and black and white display can be performed.

4-2. Organic EL Display Device Examples of the organic EL display device include the organic EL display device shown in FIG. Examples of the organic EL display device include an organic EL display device 11 in which the polarizing plate 4 of the present invention and the organic EL panel 7 are bonded together through an adhesive layer 5. The organic EL panel 7 is at least one layer made of a conductive organic compound. According to the above configuration, when a voltage is applied to the organic EL panel using an electrode (not shown), the compound contained in the light emitting layer of the organic EL panel emits light, and black and white display can be performed.
In the organic EL display device 11, the polarizing plate 4 preferably functions as a broadband circular polarizing plate. If it functions as a broadband circularly polarizing plate, reflection of external light can be prevented on the surface of the organic EL display device 11.

5. Color Filter The optical filter of the present invention can be used as a color filter by laminating a color filter layer. An example of the color filter is the configuration shown in FIG. The color filter 14 is formed by forming a color filter layer 13 on the optical film 12 of the present invention. The color filter layer 13 is a layer having a function of absorbing specific light in the visible light region. For example, the color filter layer 13 is a layer that converts white light into light of a color such as red, blue, or green.

  An example of a method for manufacturing the color filter 14 will be described. First, an alignment film material is applied onto a substrate, and a rubbing process or a polarized UV process is performed to form an alignment film. Next, on the obtained alignment film, the composition of the present invention in which the concentration of the compound (A) is adjusted so that the obtained optical film exhibits a desired wavelength dispersion characteristic is obtained. The film is formed by applying while adjusting the thickness so as to obtain a phase difference value. Next, the color filter layer 13 is formed on the obtained optical film 12 of the present invention. The optical film 12 of the present invention may be a patterned optical film having a plurality of regions having different orientations of the compound (A). The patterned optical film can be obtained by performing the rubbing treatment or the polarized UV treatment through a mask.

  The present invention will be described more specifically with reference to the following examples. However, the present invention is not limited to the following examples, and may be appropriately modified and implemented within a range that can meet the purpose described above and below. All of which are within the scope of the present invention. In the examples, “%” and “part” are mass% and part by mass unless otherwise specified.

1. Synthesis Example Compound (A11-1) was synthesized according to the following scheme.

1-1. "Synthesis of 4,6-dimethylbenzofuran-2-carboxylic acid"
146.6 g of 4,6-dimethylsalicylaldehyde and 330.7 g of potassium carbonate were dispersed in 700 mL of N, N′-dimethylacetamide. After the dispersion was heated to 80 ° C., 190.5 g of tert-butyl bromoacetate was added dropwise over 30 minutes. The mixture was reacted at 130 ° C. for 2 hours. After cooling the reaction solution to room temperature, 600 mL of methyl isobutyl ketone was added, and the mixture was separated with 1200 mL of pure water. Further, the organic layer was washed twice with 1000 mL of pure water to recover the organic layer. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 240 g of acetic acid, 72 g of an aqueous hydrobromic acid solution was added, and the mixture was stirred at 40 ° C. for 1 hour. After cooling to room temperature, 150 g of 1N (1 mol / L) -hydrochloric acid was added, and the precipitated white powder was collected by filtration. The obtained white powder was further washed with 1N-hydrochloric acid and then vacuum-dried to obtain 81.7 g of 4,6-dimethylbenzofuran-2-carboxylic acid as a yellow powder. The yield was 44% based on 4,6-dimethylsalicylaldehyde.

1-2. “Synthesis of Compound (11-a)”
80 g of 4,6-dimethylbenzofuran-2-carboxylic acid, 96.6 g of 2,5-dimethoxyaniline and 400 g of chloroform were mixed. After cooling the obtained suspension in an ice bath, a mixed solution of 18.7-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 88.7 g and chloroform 300 g was added over 4 hours, For 48 hours. The obtained mixed solution was concentrated, and a mixed solution of 1N-hydrochloric acid and water-methanol (water 2 parts by volume, methanol 1 part by volume) was added to cause crystallization. The resulting precipitate was collected by filtration and a mixed solution of water-methanol (water 2 parts by volume, methanol 1 part by volume) was added. The precipitated pale yellow precipitate was collected by filtration, washed with a mixed solution of water-methanol (water 2 parts by volume, methanol 1 part by volume), and vacuum-dried to obtain 124.2 g of compound (11-a) as a pale yellow powder. It was. The yield was 91% based on 4,6-dimethylbenzofuran-2-carboxylic acid.

1-3. “Synthesis of Compound (11-b)”
Compound (11-a) 123 g, 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide (Lawson reagent) 9.2 g and toluene 1200 g were mixed. The resulting mixture was heated to 110 ° C. and reacted for 8 hours. After cooling to room temperature, the solution was separated with a 1N sodium hydroxide aqueous solution. The organic layer was collected and 800 mL of n-heptane was added. The precipitated yellow precipitate was collected by filtration, washed with n-heptane, and vacuum dried to obtain 109.2 g of compound (11-b) as a bright yellow powder. The yield was 85% based on the compound (11-a).

1-4. “Synthesis of Compound (11-c)”
60 g of the compound (11-b), 53.8 g of potassium hydroxide and 1000 g of water were mixed, and the resulting mixture was stirred under ice cooling. Subsequently, 133 g of potassium ferricyanide and 51 g of methanol were added and reacted. The reaction was allowed to proceed for 36 hours at room temperature, and the precipitated yellow precipitate was collected by filtration. The precipitate collected by filtration was washed with a mixed solvent of n-heptane-toluene (3 parts by volume of n-heptane, 1 part by volume of toluene), and the resulting yellow powder was dried under vacuum to obtain a compound (11-c) as a yellow solid 51.3 g was obtained. The yield was 86% based on the compound (11-b).

1-5. “Synthesis of Compound (11-d)”
40 g of compound (11-c) and 400 g of pyridinium chloride (10 times mass) were mixed, heated to 180 ° C., and reacted for 3 hours. The resulting mixture was added to ice and the resulting precipitate was collected by filtration. After rinsing with water, it was washed with toluene and vacuum-dried to obtain 36.6 g of a yellow solid containing compound (11-d) as a main component. The yield was 99% based on the compound (11-c).

1-6. “Synthesis of Compound (R-1a)”
The compound (R-1a) was synthesized with reference to paragraph 0244 of JP2010-31223A.

1-7. “Synthesis of Compound (A11-1)”
35 g of compound (11-d), 98.8 g of compound (R-1a), 1.37 g of dimethylaminopyridine and 700 mL of toluene were mixed. 55.6 g of N, N′-dicyclohexylcarbodiimide was added to the resulting mixture under ice cooling. The resulting reaction solution was reacted at room temperature overnight, filtered through silica gel, and then concentrated under reduced pressure. Methanol was added to the residue for crystallization. The crystals were collected by filtration, redissolved in chloroform, added with 2.3 g of activated carbon, and stirred at room temperature for 1 hour. The solution was filtered, and the filtrate was concentrated under reduced pressure using an evaporator until the volume was reduced to 1/3. Methanol was added with stirring, and the resulting white precipitate was collected by filtration, washed with heptane, and dried in vacuo to give compound (A11 14.5) was obtained as white powder. The yield was 60% based on the compound (11-d).

2. Preparation of composition Each component shown in Table 1 was mixed, and the resulting solution was stirred at 80 ° C for 1 hour, and then cooled to room temperature to prepare a composition.

  A11-1, v-1, B-1, B-2, C-1 to C-10, and BYK361N in the table represent the following compounds.

Compound (A);
A11-1: Compound (A11-1) obtained in Synthesis Example 1
v-1: Compound represented by the formula (v-1)

Photopolymerization initiator (B);
B-1: Compound represented by formula (B-1) (Irgacure 369; manufactured by BASF Japan Ltd.)

B-2: Compound represented by formula (B-2) (Irgacure 819; manufactured by BASF Japan Ltd.)

Antioxidant (C);
C-1: 2,6-bis (1,1-dimethylethyl) -4-methylphenol (manufactured by Tokyo Chemical Industry)
C-2: Sumilizer GM (phenolic antioxidant; manufactured by Sumitomo Chemical Co., Ltd.)
C-3: Sumilizer GS-F (phenolic antioxidant; manufactured by Sumitomo Chemical Co., Ltd.)
C-4: Sumilizer GA-80 (phenolic antioxidant; manufactured by Sumitomo Chemical Co., Ltd.)
C-5: Irganox 1010 (phenolic antioxidant; manufactured by BASF Japan Ltd.)
C-6: Irganox 3114 (phenolic antioxidant; manufactured by BASF Japan Ltd.)
C-7: Sumilizer TPL-R (sulfur antioxidant; manufactured by Sumitomo Chemical Co., Ltd.)
C-8: Sumilizer TPM (sulfur-based antioxidant; manufactured by Sumitomo Chemical Co., Ltd.)
C-9: Sumilizer GP (phosphorus antioxidant; manufactured by Sumitomo Chemical Co., Ltd.)
C-10: Irganox 168 (phosphorus antioxidant; manufactured by BASF Japan Ltd.)
Leveling agent;
BYK361N (by Big Chemie Japan)

3. Preparation of optical film A 2% by weight aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 fully saponified, manufactured by Wako Pure Chemical Industries, Ltd.) was applied to a glass substrate by spin coating, and then heated and dried at 120 ° C for 60 minutes. A polyvinyl alcohol film having a thickness of 89 nm was obtained on a glass substrate. Subsequently, the surface of the polyvinyl alcohol film was rubbed. The composition was applied to the obtained polyvinyl alcohol film by spin coating, and dried on a hot plate at 140 ° C. for 1 minute. Then, 2400 mJ / cm < ² > (365 nm reference | standard) was irradiated using UV exposure apparatus (Unicure; Ushio Electric Co., Ltd. product), heating at 80 degreeC, and the optical film was obtained.

3-1. Measurement of retardation value The front retardation value of the obtained optical film was measured using a measuring instrument (KOBRA-WR, manufactured by Oji Scientific Instruments). In addition, since the glass substrate used for the base material has no birefringence, the front retardation value of the optical film produced on the glass substrate can be obtained by measuring the film with the glass substrate with a measuring machine. . The obtained optically measured front phase difference values were measured at wavelengths of 451 nm, 549 nm, and 628 nm, respectively, and [Re (451) / Re (549)] (referred to as α) and [Re (628) / Re (549). ]] (Β) was calculated.

3-2. Measurement of chromaticity The transmittance of the obtained optical film was measured using an ultraviolet-visible-infrared spectrophotometer (UV-3150; manufactured by Shimadzu Corporation). From the measured transmittance and the color matching function of the C light source, the chromaticities a ^* and b ^* in the L ^* a ^* b ^* (CIE) color system and their absolute values | a ^* | and | b ^* | Was calculated.

3-3. Wet and heat resistance test of optical film The obtained optical film was stored in an oven at a temperature of 60 ° C. and a humidity of 90% for 1000 hours. The phase difference value and chromaticity before and after storage were measured. The difference △ α of α after the test with respect to before storage α, before storage of | a ^* | after storage for | a ^* | difference of Δ | a ^* |, before storage of | b ^* | after storage for | was calculated as | b ^* | difference of Δ | b ^*. If Δα is −0.2 or more and +0.2 or less and Δ | a ^* | and Δ | b ^* | are −3.0 or more and +3.0 or less, it is judged that the heat and humidity resistance of the optical film is good. it can. Table 2 shows the measurement result of the phase difference value, and Table 3 shows the measurement result of the chromaticity.

It was shown that the optical films of the examples had small Δα, Δ | a ^* | and Δ | b ^* |, and were excellent in heat and moisture resistance. In addition, among the examples, the optical films of Examples 1 to 6 containing a phenolic antioxidant as an antioxidant were particularly small in Δ | b ^* |, and were shown to be superior in wet heat resistance.

  According to the present invention, an optical film having excellent moisture and heat resistance can be obtained.

1, 1 ′, 12: the optical film of the present invention,
2: Polarizing film layer,
3, 3 ′: adhesive layer,
4a, 4b, 4c, 4d, 4e, 4, 4 ′: polarizing plate of the present invention,
5, 5 ′: adhesive layer,
6: Liquid crystal panel,
7: Organic EL panel,
10a, 10b: liquid crystal display device,
11: Organic EL display device,
13: Color filter layer,
14: Color filter.

Claims (9)

A composition comprising a compound represented by formula (A), an antioxidant and a photopolymerization initiator.

Wherein (A), X ¹ is, -S -, - O- or -NR ¹ - represents a. R ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms.
Q ¹ and Q ² are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic having 6 to 20 carbon atoms. Represents a hydrocarbon group, a halogen atom, a cyano group, a nitro group, —NR ² R ³ or —SR ² , and Q ¹ and Q ² may be bonded to each other to form an aromatic ring or an aromatic heterocyclic ring. . R ² and R ³ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, —CO—O—, —CS—O—, —CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —CR ⁶ R ⁷ —, —O—CR ^4. R ⁵ —, —CR ⁴ R ⁵ —O—CR ⁶ R ⁷ —, —CO—O—CR ⁴ R ⁵ —, —O—CO—CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —O—CO— CR ⁶ R ⁷ —, —CR ⁴ R ⁵ —CO—O—CR ⁶ R ⁷ —, —NR ⁴ —CR ⁵ R ⁶ — or —CO—NR ⁴ — is represented.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and —CH ₂ — contained in the alicyclic hydrocarbon group is —O—, — S— or —NH— may be substituted, and —CH (—) — contained in the alicyclic hydrocarbon group may be substituted with —N (—) —.
L ¹ and L ² each independently represent a monovalent organic group, and at least one selected from the group consisting of L ¹ and L ² represents a group having a polymerizable group. ]   The composition according to claim 1, wherein the photopolymerization initiator is an alkylphenone compound. The composition according to claim 1 or 2, wherein L ¹ in formula (A) is a group represented by formula (A1), and L ² in formula (A) is a group represented by formula (A2). object.
P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) _l -E ^2- (A2)
Wherein (A1) and formula ^{(A2), B 1, B} 2, E 1 and E ^2, each ^{independently, -CR 11 R 12 -, -} CH 2 -CH 2 -, - O -, - S —, —CO—O—, —O—CO—O—, —CS—O—, —O—CS—O—, —CO—NR ¹¹ —, —O—CH ₂ —, —S—CH ₂ —. Or it represents a single bond.
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, and the alicyclic hydrocarbon —CH ₂ — contained in the group may be replaced by —O—, —S— or —NH—, and —CH (—) — contained in the alicyclic hydrocarbon group represents —N (-)-May be replaced.
k and l each independently represents an integer of 0 to 3. When k is an integer of 2 or more, the plurality of B ¹ and A ¹ may be the same as or different from each other. If l is an integer of 2 or more, a plurality of B ² and A ² may be the same or different from each other.
F ¹ and F ² represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ and P ² represent a hydrogen atom or a polymerizable group, and at least one is a polymerizable group.
R ¹¹ and R ¹² represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ] The composition according to claim 2 or 3, wherein the alkylphenone compound is a compound represented by the formula (C-1).

[In Formula (C-1), Q ³ represents a hydrogen atom or a methyl group. ]   The composition according to any one of claims 1 to 4, wherein the antioxidant is a phenol-based antioxidant.   The optical film formed by superposing | polymerizing the polymeric component contained in the composition as described in any one of Claims 1-5.   A retardation film obtained by polymerizing a polymerizable component contained in the composition according to claim 1.   A polarizing plate having at least one selected from the group consisting of the optical film according to claim 6 and the retardation film according to claim 7.   A flat panel display device having at least one selected from the group consisting of the optical film according to claim 6 and the retardation film according to claim 7.