JP5266801B2 - Optical film and optical film manufacturing method - Google Patents

Abstract

The invention relates to an optical film and its manufacture method. The optical film is formed by filming and stretching a composition, wherein the composition comprises compound with more than two at least one kind group selected from acryloyl and methyl acryloyl and group shown in formula A. In formula A, B1 and B2 independently show hydroxyl, alkyl of C1-6, alkoxy or epoxypropoxy of C1-6; X shows bivalent alkyl, thioether group, sulfonyl group, ether bond or single bond, the alkyl can comprise -CO-O-, a1 and a2 independently show integers of 0-4.

Description

  The present invention relates to an optical film and a method for producing the optical film.

  Patent Document 1 discloses a retardation plate obtained by stretching a thermoplastic resin containing a monomer having a positive refractive index anisotropy and a monomer having a negative refractive index anisotropy. However, specifically, as such a thermoplastic resin, only a polycarbonate composed of phosgene and bisphenol is disclosed, and since phosgene is used, industrial production of the polycarbonate is not always easy. Furthermore, as the monomer having negative refractive index anisotropy used for the polycarbonate, only the following [F] and [G] which are dehydration condensates of 9-fluorene and phenol are disclosed.

WO99 / 06057 pamphlet

  As a result of intensive studies on the above-mentioned problems, the present inventors have found an optical film that can be produced without using phosgene and that can perform uniform polarization conversion in a wide wavelength region, and has led to the present invention.

（式（Ａ）中、Ｂ_１及びＢ_２は、それぞれ独立に、水酸基、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基又はグリシドキシ基を表す。Ｘは、２価の炭化水素基、スルフィド基、スルホニル基、エーテル結合又は単結合を表し、該炭化水素基は、−ＣＯ−Ｏ−を含んでいてもよい。ａ_１及びａ_２は、それぞれ独立に、０〜４の整数を表す。） The present invention provides a composition comprising a compound having two or more groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A). And an optical film obtained by further stretching.

(In formula (A), B ₁ and B ₂ each independently represent a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a glycidoxy group. X is a divalent carbonization. Represents a hydrogen group, a sulfide group, a sulfonyl group, an ether bond or a single bond, and the hydrocarbon group may contain —CO—O—, each of a ₁ and a ₂ independently represents 0 to 4; Represents an integer.)

  The present invention also provides a composition comprising a compound having at least two groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A). The optical film is a film formed by photopolymerization and then stretched.

（式（Ａ−１）〜式（Ａ−３）中、Ｂ_１、Ｂ_２、ａ_１及びａ_２は、上記と同じ意味を表す。） In the present invention, the compound having at least one group selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A) is an acryloyl group in the molecule. And a compound having two or more groups selected from the group consisting of methacryloyl groups and having a group represented by formula (A-1), formula (A-2) or formula (A-3). It is a certain optical film.

(In formula (A-1) to formula (A-3), B ₁ , B ₂ , a ₁ and a ₂ represent the same meaning as described above.)

（式（Ａ−４）中、Ｒ_１５及びＲ_１６は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_７及びＸ_８は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。ｖ_４及びｗ_４は、それぞれ独立に、０〜６の整数を表す。Ｘは、上記と同じ意味を表す。） In the present invention, the compound having at least two groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A) is represented by the formula (A-4 It is the said optical film which is a compound represented by this.

(In formula (A-4), R ₁₅ and R ₁₆ each independently represent a hydrogen atom or a methyl group, and X ₇ and X ₈ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, v ₄ and w ₄ each independently represents an integer of 0 to 6. X is the same as above. Represents meaning.)

（式（Ｉ）中、Ｒ_１は、水素原子又はメチル基を表し、Ｒ_２は、５〜２０員環の芳香族炭化水素基又は芳香族複素環基を表す。該芳香族炭化水素基又は芳香族複素環基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基又はハロゲン原子を含んでいてもよい。）

（式（ＩＩ）中、Ｒ_３は水素原子又はメチル基を表し、Ｒ_４及びＲ_５は、それぞれ独立に、水素原子、炭素数１〜６のアルキル基、又はＲ_４及びＲ_５が連結して形成される炭素数４〜６のアルキレン基を表す。該アルキル基及び該アルキレン基は、水酸基、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。Ｒ_６は単結合又は炭素数２〜６のオキシアルキレン基を表す。）

（式（ＩＩＩ）中、Ｒ_７は水素原子又はメチル基を表し、Ｒ_８は、水素原子、メチル基又は５〜２０員環の環状炭化水素基を表す。該環状炭化水素基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基、ハロゲン原子、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。該アルキル基、該アルコキシ基、該アリール基及び該アラルキル基は、水酸基又はハロゲン原子を含んでいてもよい。） Moreover, this invention is the said optical film whose composition is a composition containing the at least 1 sort (s) of monomer (1) further chosen from the group which consists of a monomer represented by Formula (I)-Formula (III).

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.)

（式（Ｉ）中、Ｒ_１は、水素原子又はメチル基を表し、Ｒ_２は、５〜２０員環の芳香族炭化水素基又は芳香族複素環基を表す。該芳香族炭化水素基又は芳香族複素環基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基又はハロゲン原子を含んでいてもよい。）

（式（ＩＩ）中、Ｒ_３は水素原子又はメチル基を表し、Ｒ_４及びＲ_５は、それぞれ独立に、水素原子、炭素数１〜６のアルキル基、又はＲ_４及びＲ_５が連結して形成される炭素数４〜６のアルキレン基を表す。該アルキル基及び該アルキレン基は、水酸基、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。Ｒ_６は単結合又は炭素数２〜６のオキシアルキレン基を表す。）

（式（ＩＩＩ）中、Ｒ_７は水素原子又はメチル基を表し、Ｒ_８は、水素原子、メチル基又は５〜２０員環の環状炭化水素基を表す。該環状炭化水素基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基、ハロゲン原子、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。該アルキル基、該アルコキシ基、該アリール基及び該アラルキル基は、水酸基又はハロゲン原子を含んでいてもよい。） The present invention is also a composition comprising a polymer obtained by polymerizing at least one monomer (1) selected from the group consisting of monomers represented by formulas (I) to (III). It is a certain optical film.

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.)

  Moreover, this invention is the said optical film whose monomer represented by Formula (I) is at least 1 sort (s) of monomer chosen from the group which consists of N-vinyl carbazole, vinyl naphthalene, and vinyl anthracene.

  In the present invention, the monomer represented by the formula (II) is N, N-dimethylacrylamide, N, N-diethylacrylamide, N- (2-hydroxyethyl) acrylamide, N-isopropylacrylamide, acryloylmorpholine, dimethyl. The optical film is at least one monomer selected from the group consisting of aminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate.

  In the present invention, the monomer represented by the formula (III) is methyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-tetrahydropyranyl (meth) acrylate, The optical film as described above, which is at least one monomer selected from the group consisting of isobornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, adamantyl (meth) acrylate and 1-acryloyl-4-methoxynaphthalene.

（式（ＩＶ）中、Ｒ_９及びＲ_１０は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_１及びＸ_２は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。Ｚ_１及びＺ_２は、それぞれ独立に、単結合又はメチレン基を表す。ｓは１又は２の整数、ｔは０又は１の整数を表す。ｖ_１及びｗ_１は、それぞれ独立に、０〜６の整数を表す。）

（式（Ｖ）中、Ｒ_１１及びＲ_１２は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_３及びＸ_４は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。Ｚ_３及びＺ_４は、それぞれ独立に、単結合又はメチレン基を表す。ｖ_２及びｗ_２は、それぞれ独立に、０〜６の整数を表す。） Moreover, this invention is the said optical film whose composition is a composition containing at least 1 sort (s) of monomer further selected from the group which consists of a monomer represented by Formula (IV) and Formula (V).

(In formula (IV), R ₉ and R ₁₀ each independently represent a hydrogen atom or a methyl group, and X ₁ and X ₂ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₁ and Z ₂ each independently represents a single bond or a methylene group, s is an integer of 1 or 2, t represents an integer of 0 or 1. v ₁ and w ₁ each independently represent an integer of 0 to 6.)

(In formula (V), R ₁₁ and R ₁₂ each independently represent a hydrogen atom or a methyl group, and X ₃ and X ₄ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₃ and Z ₄ each independently represents a single bond or a methylene group, and v ₂ and w ₂ are respectively Independently represents an integer of 0 to 6.)

（式（ＶＩ）中、Ｒ_１３及びＲ_１４は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_５及びＸ_６は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。Ｒは、それぞれ独立に、水酸基、ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基、グリシドキシ基、ニトロ基又はシアノ基を表す。ｖ_３及びｗ_３は、それぞれ独立に、０〜６の整数を表し、ｗは、それぞれ独立に、０〜４の整数を表す。ｗが２以上整数である場合、複数のＲは、それぞれ異なる種類の基であってもよい。） Moreover, this invention is the said optical film whose composition is a composition containing the monomer further represented by Formula (VI).

(In Formula (VI), R ₁₃ and R ₁₄ each independently represent a hydrogen atom or a methyl group, and X ₅ and X ₆ each independently represent an alkylene group having 2 to 6 carbon atoms.) The group may include an alkyl group having 1 to 6 carbon atoms, a hydroxyl group, or a carbonyl group, and each R is independently a hydroxyl group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, or a 1 to 6 carbon atoms. Represents an alkoxy group, a glycidoxy group, a nitro group, or a cyano group, v ₃ and w ₃ each independently represent an integer of 0 to 6, and w independently represents an integer of 0 to 4. When it is an integer of 2 or more, the plurality of R may be different types of groups.

（式（ＶＩ−１）中、Ｒ_１３、Ｒ_１４、Ｘ_５、Ｘ_６、ｖ_３及びｗ_３は、上記と同じ意味を表す。） Moreover, this invention is the said optical film whose monomer represented by Formula (VI) is a monomer represented by Formula (VI-1).

(In formula (VI-1), R ₁₃ , R ₁₄ , X ₅ , X ₆ , v ₃ and w ₃ represent the same meaning as described above.)

Moreover, this invention is the said optical film with which phase difference value Re ((nu)) in wavelength (nu) nm of the transmitted light which permeate | transmits an optical film satisfies the following formula.
Re (450) <Re (550) <Re (650)

  Moreover, this invention is a phase difference plate which consists of said optical film.

（式（Ａ）中、Ｂ_１及びＢ_２は、それぞれ独立に、水酸基、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基又はグリシドキシ基を表す。Ｘは、２価の炭化水素基、スルフィド基、スルホニル基、エーテル結合又は単結合を表し、該炭化水素基は、−ＣＯ−Ｏ−を含んでいてもよい。ａ_１及びａ_２は、それぞれ独立に、０〜４の整数を表す。） The present invention also provides an optical film composition comprising a compound having at least two groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A). It is.

(In formula (A), B ₁ and B ₂ each independently represent a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a glycidoxy group. X is a divalent carbonization. Represents a hydrogen group, a sulfide group, a sulfonyl group, an ether bond or a single bond, and the hydrocarbon group may contain —CO—O—, each of a ₁ and a ₂ independently represents 0 to 4; Represents an integer.)

（式（Ｉ）中、Ｒ_１は、水素原子又はメチル基を表し、Ｒ_２は、５〜２０員環の芳香族炭化水素基又は芳香族複素環基を表す。該芳香族炭化水素基又は芳香族複素環基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基又はハロゲン原子を含んでいてもよい。）

（式（ＩＩ）中、Ｒ_３は水素原子又はメチル基を表し、Ｒ_４及びＲ_５は、それぞれ独立に、水素原子、炭素数１〜６のアルキル基、又はＲ_４及びＲ_５が連結して形成される炭素数４〜６のアルキレン基を表す。該アルキル基及び該アルキレン基は、水酸基、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。Ｒ_６は単結合又は炭素数２〜６のオキシアルキレン基を表す。）

（式（ＩＩＩ）中、Ｒ_７は水素原子又はメチル基を表し、Ｒ_８は、水素原子、メチル基又は５〜２０員環の環状炭化水素基を表す。該環状炭化水素基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基、ハロゲン原子、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。該アルキル基、該アルコキシ基、該アリール基及び該アラルキル基は、水酸基又はハロゲン原子を含んでいてもよい。） Moreover, this invention is the said composition for optical films containing the at least 1 sort (s) of monomer (1) chosen from the group which consists of a monomer further represented by Formula (I)-Formula (III).

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.)

（式（Ｉ）中、Ｒ_１は、水素原子又はメチル基を表し、Ｒ_２は、５〜２０員環の芳香族炭化水素基又は芳香族複素環基を表す。該芳香族炭化水素基又は芳香族複素環基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基又はハロゲン原子を含んでいてもよい。）

（式（ＩＩ）中、Ｒ_３は水素原子又はメチル基を表し、Ｒ_４及びＲ_５は、それぞれ独立に、水素原子、炭素数１〜６のアルキル基、又はＲ_４及びＲ_５が連結して形成される炭素数４〜６のアルキレン基を表す。該アルキル基及び該アルキレン基は、水酸基、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。Ｒ_６は単結合又は炭素数２〜６のオキシアルキレン基を表す。）

（式（ＩＩＩ）中、Ｒ_７は水素原子又はメチル基を表し、Ｒ_８は、水素原子、メチル基又は５〜２０員環の環状炭化水素基を表す。該環状炭化水素基は、水酸基、炭素数１〜１２のアルキル基、炭素数１〜１２のアルコキシ基、炭素数６〜１２のアリール基、炭素数７〜１２のアラルキル基、グリシドキシ基、炭素数２〜４のアシル基、カルボキシル基、ハロゲン原子、酸素原子、硫黄原子又は窒素原子を含んでいてもよい。該アルキル基、該アルコキシ基、該アリール基及び該アラルキル基は、水酸基又はハロゲン原子を含んでいてもよい。） Moreover, this invention is the said composition for optical films containing the polymer formed by superposing | polymerizing the at least 1 sort (s) of monomer (1) further selected from the group which consists of a monomer represented by Formula (I)-Formula (III). is there.

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.)

（式（ＩＶ）中、Ｒ_９及びＲ_１０は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_１及びＸ_２は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。Ｚ_１及びＺ_２は、それぞれ独立に、単結合又はメチレン基を表す。ｓは１又は２の整数、ｔは０又は１の整数を表す。ｖ_１及びｗ_１は、それぞれ独立に、０〜６の整数を表す。）

（式（Ｖ）中、Ｒ_１１及びＲ_１２は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_３及びＸ_４は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。Ｚ_３及びＺ_４は、それぞれ独立に、単結合又はメチレン基を表す。ｖ_２及びｗ_２は、それぞれ独立に、０〜６の整数を表す。） Moreover, this invention is the said composition for optical films containing the at least 1 sort (s) of monomer further selected from the group which consists of a monomer represented by Formula (IV) and Formula (V).

(In formula (IV), R ₉ and R ₁₀ each independently represent a hydrogen atom or a methyl group, and X ₁ and X ₂ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₁ and Z ₂ each independently represents a single bond or a methylene group, s is an integer of 1 or 2, t represents an integer of 0 or 1. v ₁ and w ₁ each independently represent an integer of 0 to 6.)

(In formula (V), R ₁₁ and R ₁₂ each independently represent a hydrogen atom or a methyl group, and X ₃ and X ₄ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₃ and Z ₄ each independently represents a single bond or a methylene group, and v ₂ and w ₂ are respectively Independently represents an integer of 0 to 6.)

（式（ＶＩ）中、Ｒ_１３及びＲ_１４は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_５及びＸ_６は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。Ｒは、それぞれ独立に、水酸基、ハロゲン原子、炭素数１〜６のアルキル基、炭素数１〜６のアルコキシ基、グリシドキシ基、ニトロ基又はシアノ基を表す。ｖ_３及びｗ_３は、それぞれ独立に、０〜６の整数を表し、ｗは、それぞれ独立に、０〜４の整数を表す。ｗが２以上整数である場合、複数のＲは、それぞれ異なる種類の基であってもよい。） Moreover, this invention is the said composition for optical films containing the monomer further represented by Formula (VI).

(In Formula (VI), R ₁₃ and R ₁₄ each independently represent a hydrogen atom or a methyl group, and X ₅ and X ₆ each independently represent an alkylene group having 2 to 6 carbon atoms.) The group may include an alkyl group having 1 to 6 carbon atoms, a hydroxyl group, or a carbonyl group, and each R is independently a hydroxyl group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, or a 1 to 6 carbon atoms. Represents an alkoxy group, a glycidoxy group, a nitro group, or a cyano group, v ₃ and w ₃ each independently represent an integer of 0 to 6, and w independently represents an integer of 0 to 4. When it is an integer of 2 or more, the plurality of R may be different types of groups.

  Moreover, this invention is the said composition for optical films which contains a photoinitiator (3) further.

  Moreover, this invention is a manufacturing method of the optical film which film-forms the said composition for optical films, and also extends | stretches.

  Moreover, this invention is a manufacturing method of the said optical film which extends | stretches, after forming into a film and photopolymerizing the composition for optical films.

  Moreover, this invention is a manufacturing method of the said optical film formed into a film by casting the solution containing the composition for optical films on a smooth surface, and distilling a solvent off.

  The optical film of the present invention can be produced without using phosgene, and enables uniform polarization conversion in a wide wavelength range.

Hereinafter, the present invention will be described in detail. The “optical film” refers to 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 has at least two groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule, and a compound having a group represented by the formula (A) (hereinafter “compound ( A) ”may be formed into a film and further stretched.

B ₁ and B ₂ each independently represent a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a glycidoxy group. X represents a divalent hydrocarbon group, sulfide group, sulfonyl group, ether bond or single bond, and the hydrocarbon group may contain —CO—O—. a ₁ and a ₂ each independently represents an integer of 0 to 4;

X is particularly preferably an alkylene group having 0 to 6 carbon atoms.
Examples of X include groups represented by formula (X-1) to formula (X-9).

（式（Ｘ−４）中、Ｒ’は、炭素数１〜６のアルキレン基を表す。）

(In formula (X-4), R ′ represents an alkylene group having 1 to 6 carbon atoms.)

  The group represented by the formula (A) is particularly preferably a group represented by the formula (A-1), the formula (A-2) or the formula (A-3).

式（Ａ−１）〜式（Ａ−３）中、Ｂ_１、Ｂ_２、ａ_１及びａ_２は、上記と同じ意味を表す。

In formula (A-1) to formula (A-3), B ₁ , B ₂ , a ₁ and a ₂ represent the same meaning as described above.

The (meth) acryloyl group (referred to as a generic name for acryloyl group and methacryloyl group) contained in the compound (A) is obtained by esterifying (meth) acrylic acid directly to the hydroxyl group of an aromatic hydrocarbon group. It may be obtained by esterifying (meth) acrylic acid to a terminal hydroxyl group obtained by reacting ethylene oxide with a hydroxyl group of an aromatic hydrocarbon group. It may be obtained by esterifying benzoic acid with the hydroxyl group of the aliphatic hydrocarbon group and then esterifying (meth) acrylic acid with the terminal hydroxyl group of benzoic acid.
As the compound (A), a compound having an aromatic hydrocarbon group and two (meth) acryloyl groups is preferable because it is easy to prepare. For example, a compound represented by the formula (A-4) is preferable.

式（Ａ−４）中、Ｒ_１５及びＲ_１６は、それぞれ独立に、水素原子又はメチル基を表し、Ｘ_７及びＸ_８は、それぞれ独立に、炭素数２〜６のアルキレン基を表す。該アルキレン基は、炭素数１〜６のアルキル基、水酸基又はカルボニル基を含んでいてもよい。ｖ_４及びｗ_４は、それぞれ独立に、０〜６の整数を表す。Ｘは、上記と同じ意味を表す。

In formula (A-4), R ₁₅ and R ₁₆ each independently represent a hydrogen atom or a methyl group, and X ₇ and X ₈ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group. v ₄ and _{w 4} represent each independently an integer of 0 to 6. X represents the same meaning as described above.

  Specific examples of the compound (A) include compounds represented by the formula (A-5) and the formula (A-6).

式（Ａ−５）及び式（Ａ−６）中、ｖ_４及びｗ_４は、上記と同じ意味を表す。

In formula (A-5) and formula (A-6), v ₄ and w ₄ represent the same meaning as described above.

  More specifically, examples of the compound (A) include monomers represented by formula (A-7) to formula (A-9). The monomer represented by the formula (A-7) is A-BPE-4 (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.), and the monomer represented by the formula (A-8) is A-BP- As 2E (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.), the monomer represented by the formula (A-9) is commercially available as LC242 (trade name, manufactured by BASF).

Two or more types of compounds (A) may be used in combination.
The content of the compound (A) is, for example, 10 to 95% by weight, preferably 20 to 90% by weight, when the total amount of all monomers and the compound (A) contained in the optical film of the present invention is 100% by weight. Particularly preferred is 30 to 80% by weight. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  In the optical film of the present invention, the composition is further selected from the group consisting of monomers represented by formulas (I) to (III) (hereinafter sometimes referred to as “monomer (I) to monomer (III)”). It is preferable that the composition contains at least one monomer (1).

R ₁ represents a hydrogen atom or a methyl group, preferably a hydrogen atom.

R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an aralkyl having 7 to 12 carbon atoms. A group, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, a carboxyl group, or a halogen atom.

  Specific examples of the aromatic hydrocarbon group or the aromatic heterocyclic group include an aromatic hydrocarbon group such as phenyl group, benzyl group, naphthyl group or anthracenyl group, pyrrole group, furanyl group, pyrazinyl group, pyrazole group, pyridinyl group. Or aromatic heterocyclic groups, such as a thiazole group, etc. are mentioned.

  Examples of the aromatic hydrocarbon group or aromatic heterocyclic group include alkyl groups having 1 to 12 carbon atoms such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group, and an octyl group, such as a methoxy group or an ethoxy group. An alkoxy group having 1 to 12 carbon atoms, for example, a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom, for example, an acyl group having 2 to 4 carbon atoms such as an acetyl group, a hydroxyl group, a glycidoxy group or a carboxyl group; May be.

The aromatic hydrocarbon group or aromatic heterocyclic group may be a monovalent group in which a plurality of aromatic hydrocarbon groups or aromatic heterocyclic groups are bonded via a linking group. Examples of the linking group include a hydrocarbon group having about 1 to 6 carbon atoms such as a methylene group, an ethylidene group, a propylidene group, an isopropylidene group, a cyclohexylidene group, an ethylene group or a propylene group, an oxygen atom, a sulfur atom, and a carbonyl group. or -CO ₂ - and the like. A plurality of aromatic hydrocarbon groups or aromatic heterocyclic groups may be bonded by a single bond.

  A plurality of different monomers may be used in combination as the monomer (I).

  Specifically, examples of a plurality of aromatic hydrocarbon groups bonded by a single bond include a biphenyl group, and a group represented by the following formula in which a plurality of aromatic hydrocarbon groups are bonded by an isopropylidene group. Can be mentioned.

  Examples of the monomer (I) include alkyl styrene such as o-methyl styrene, m-methyl styrene, p-methyl styrene, 2,4-dimethyl styrene, o-ethyl styrene or p-ethyl styrene, such as hydroxy styrene, t- Substituted styrenes such as butoxystyrene, vinyl benzoic acid, vinyl benzyl acetate, o-chlorostyrene or p-chlorostyrene, in which a hydroxyl group, alkoxy group, carboxyl group, acyloxy group or halogen is bonded to the benzene ring, such as 4-vinylbiphenyl Or a vinyl biphenyl compound such as 4-hydroxy-4'-vinylbiphenyl, a compound having a condensed ring and a vinyl group such as vinylnaphthalene or vinylanthracene, an aromatic hydrocarbon group such as N-vinylphthalimide, a heterocyclic group and a biphenyl group. Compounds having a Le group.

  Examples of the monomer (I) having an aromatic heterocyclic group include N-vinylcarbazole and N-vinylindole.

  As the monomer (I), when the optical film is at least one monomer selected from the group consisting of N-vinylcarbazole, vinylnaphthalene and vinylanthracene, the optical film can perform more uniform polarization conversion in a wide wavelength range. This is preferable because it becomes possible.

  The content of the monomer (I) may not be included when the total amount of all monomers and the compound (A) contained in the optical film of the present invention is 100% by weight. , Preferably 2 to 15 mol%, particularly preferably 3 to 10 mol%. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

R ₃ represents a hydrogen atom or a methyl group, preferably a hydrogen atom.

R ₄ and R ₅ each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkylene group having 4 to 6 carbon atoms formed by connecting R ₄ and R ₅ . The alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom, or a nitrogen atom. R ₆ represents a single bond or an oxyalkylene group having 2 to 6 carbon atoms.

  A plurality of different monomers may be used in combination as the monomer (II).

  Specific examples of the monomer (II) include, for example, (meth) acrylamide (which is a generic name for acrylamide and methacrylamide), N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-isopropyl ( N-substituted (meth) acrylamides such as meth) acrylamide, N-butyl (meth) acrylamide or N- (2-hydroxyethyl) acrylamide, such as N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) Examples include N, N-substituted (meth) acrylamides such as acrylamide, N, N-dipropyl (meth) acrylamide, (meth) acryloylmorpholine, 2-dimethylaminoethyl (meth) acrylate, or 2-diethylaminoethyl (meth) acrylate. It is done.

  As the monomer (II), N, N-dimethylacrylamide, N, N-diethylacrylamide, N- (2-hydroxyethyl) acrylamide, N-isopropylacrylamide, acryloylmorpholine, 2-dimethylaminoethyl (meth) acrylate and It is preferable that it is at least one monomer selected from the group consisting of 2-diethylaminoethyl (meth) acrylate because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  Monomer (II) is commercially available from Wako Pure Chemical Industries, Ltd., Tokyo Chemical Industry Co., Ltd., Sigma-Aldrich Japan Co., Ltd., and the like. What is necessary is just to use what is marketed as monomer (II) as it is.

  The content of the monomer (II) may not be included when the total amount of all the monomers and the compound (A) contained in the optical film of the present invention is 100% by weight. , Preferably 10 to 70 mol%, particularly preferably 15 to 60 mol%. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

R ₇ represents a hydrogen atom or a methyl group, preferably a hydrogen atom.

R ₈ represents a hydrogen atom, a methyl group, or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. It may contain 2 to 4 acyl groups, carboxyl groups, halogen atoms, oxygen atoms, sulfur atoms or nitrogen atoms. The alkyl group, the alkoxy group, the aryl group and the aralkyl group may contain a hydroxyl group or a halogen atom.

  Examples of the cyclic hydrocarbon group include aromatic hydrocarbon groups such as phenyl group, naphthyl group and anthranyl group, for example, cycloalkyl groups such as cyclopentyl group, cyclohexyl group, isobornyl group, tricyclodecanyl group and adamantyl group. It is done.

The cyclic hydrocarbon group includes an alkyl group having 1 to 12 carbon atoms such as a methyl group, an ethyl group, an isopropyl group, a t-butyl group or an octyl group, for example, an alkoxy group having 1 to 12 carbon atoms such as a methoxy group or an ethoxy group. A group, for example, a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom, an acyl group having 2 to 4 carbon atoms such as an acetyl group, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, A hydroxyl group, glycidoxy group or carboxyl group may be bonded.
The carbon atom contained in the cyclic hydrocarbon group may be substituted with a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom.

  A plurality of different monomers may be used in combination as the monomer (III).

  Specific examples of the monomer (III) include (meth) acrylic acid, methyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, anthracenyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-tetrahydropyrani Examples include ru (meth) acrylate, isobornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, adamantyl (meth) acrylate, and 1-acryloyl-4-methoxynaphthalene.

  As the monomer (III), methyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-tetrahydropyranyl (meth) acrylate, isobornyl (meth) acrylate, tricyclo When the optical film is at least one monomer selected from the group consisting of decanyl (meth) acrylate, adamantyl (meth) acrylate and 1-acryloyl-4-methoxynaphthalene, the optical film can perform more uniform polarization conversion in a wide wavelength range. This is preferable because it can be performed.

  The content of the monomer (III) may not be included when the total amount of all the monomers and the compound (A) contained in the optical film of the present invention is 100% by weight. , Preferably 5 to 90 mol%, particularly preferably 10 to 80 mol%. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  Two or more different monomers may be combined among the monomers (I) to (III) constituting the monomer (1). In particular, a combination of monomer (I) and monomer (II) or a combination of monomer (I) and monomer (III) is preferred.

  The content of the monomer (1) may not be included when the total amount of all the monomers and the compound (A) contained in the optical film of the present invention is 100% by weight, for example, 5 to 90% by weight. , Preferably 10 to 80% by weight, particularly preferably 20 to 70% by weight. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  The optical film of the present invention is a composition containing a polymer obtained by polymerizing at least one monomer (1) selected from the group consisting of monomer (I) to monomer (III). Is preferred.

  In the optical film of the present invention, the composition further includes a monomer represented by the formula (IV) and the formula (V) (hereinafter sometimes referred to as “monomer (IV)” and “monomer (V)”). A composition containing at least one selected monomer is preferable.

R ₉ and R ₁₀ each independently represent a hydrogen atom or a methyl group, and X ₁ and X ₂ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group. Z ₁ and Z ₂ each independently represents a single bond or a methylene group. s represents an integer of 1 or 2, and t represents an integer of 0 or 1. v ₁ and w ₁ each independently represents an integer of 0 to 6.

R ₁₁ and R ₁₂ each independently represent a hydrogen atom or a methyl group, and X ₃ and X ₄ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group. Z ₃ and Z ₄ each independently represents a single bond or a methylene group. v ₂ and _{w 2} each independently represents an integer of 0 to 6.

  Specific examples of the monomer (IV) and the monomer (V) include monomers represented by the formula (IV-1) and the formula (V-1).

式（ＩＶ−１）及び式（Ｖ−１）中、Ｒ_９〜Ｒ_１２、ｓ、ｔ、ｖ_２及びｗ_２は、上記と同じ意味を表す。

In formula (IV-1) and formula (V-1), R _{9 to} R ₁₂ , s, t, v ₂ and w ₂ represent the same meaning as described above.

  More specifically, examples of the monomer (IV) include monomers represented by formulas (IV-2) to (IV-4). The monomer represented by the formula (IV-4) is commercially available as DCP (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.).

式（ＩＶ−２）及び式（ＩＶ−３）中、ｖ_１及びｗ_１は上記と同じ意味を表す。

In formula (IV-2) and formula (IV-3), v ₁ and w ₁ represent the same meaning as described above.

The (meth) acryloyl group contained in the monomer (IV) may be obtained by esterifying (meth) acrylic acid directly to the hydroxyl group of an atomic group having an alicyclic hydrocarbon group, It may be obtained by esterifying (meth) acrylic acid to a terminal hydroxyl group obtained by reacting ethylene oxide with a hydroxyl group of an atomic group having an alicyclic hydrocarbon.
Specifically, the compound represented by the formula (IV-1) is obtained by reacting caprolactone with acrylic acid and reacting a terminal carboxylic acid with an alicyclic alcohol (tricyclodecanedial alcohol). Moreover, the compound represented by Formula (V-1) is obtained by making glycidyl acrylate react with alicyclic alcohol (tricyclodecanedial alcohol).

  Examples of the monomer (IV) further include a monomer represented by the formula (IV-5).

In formula (IV-5), R ₉ , R ₁₀ , v ₁ and w ₁ represent the same meaning as described above.

  More specifically, for example, monomers represented by formula (IV-6) or formula (IV-7) are exemplified.

In formula (IV-7), v ₁ and w ₁ represent the same meaning as described above.

The acryloyl group contained in the monomer represented by the formula (IV-6) is obtained by esterifying acrylic acid directly to a hydroxyl group bonded to an alicyclic hydrocarbon.
The acryloyl group contained in the monomer represented by the formula (IV-7) is obtained by esterifying acrylic acid to a terminal hydroxyl group obtained by reacting ethylene oxide with a hydroxyl group bonded to an alicyclic hydrocarbon group. It is what was done.

  More specifically, examples of the monomer (V) include a monomer represented by the formula (V-2). The monomer represented by the formula (V-2) is commercially available as A-CHD-4E (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.).

  The content of the monomer (IV) may not be included when the total amount of all the monomers and the compound (A) contained in the optical film of the present invention is 100% by weight, for example, 5 to 90% by weight. , Preferably 10 to 80% by weight, particularly preferably 20 to 70% by weight. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  The content of the monomer (V) may not be included when the total amount of all the monomers and the compound (A) contained in the optical film of the present invention is 100% by weight, for example, 5 to 90% by weight. , Preferably 10 to 80% by weight, particularly preferably 20 to 70% by weight. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  The optical film of the present invention is preferably a composition containing a monomer represented by formula (VI) (hereinafter sometimes referred to as “monomer (VI)”).

R ₁₃ and R ₁₄ each independently represent a hydrogen atom or a methyl group, and X ₅ and X ₆ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group. R each independently represents a hydroxyl group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a glycidoxy group, a nitro group, or a cyano group. v ₃ and _{w 3} are each independently an integer of Less than six, w each independently represent an integer of 0 to 4. When w is an integer of 2 or more, the plurality of R may be different types of groups.

  As the monomer (VI), a compound represented by the formula (VI-1) is particularly preferable.

In formula (VI-1), R ₁₃ , R ₁₄ , X ₅ , X ₆ , v ₃ and w ₃ represent the same meaning as described above.

  More specifically, examples of the monomer (VI) include a monomer represented by the formula (VI-2). The monomer represented by the formula (VI-2) is commercially available as A-BPEF (trade name, manufactured by Shin-Nakamura Chemical Co., Ltd.).

  The (meth) acryloyl group contained in the monomer (VI) may be obtained by esterifying (meth) acrylic acid directly on the hydroxyl group of bisphenolfluorene, ethylene oxide or the like on the hydroxyl group of bisphenolfluorene. It may be obtained by esterifying (meth) acrylic acid to a terminal hydroxyl group obtained by reacting.

  The content of the monomer (VI) may not be included when the total amount of all the monomers and the compound (A) contained in the optical film of the present invention is 100% by weight, for example, 5 to 90% by weight. , Preferably 10 to 80% by weight, particularly preferably 20 to 70% by weight. Within the above range, it is preferable because the optical film can perform more uniform polarization conversion in a wide wavelength range.

  The optical film of the present invention is a composition in which the composition contains a compound (A) and a monomer copolymerizable with monomer (I) to monomer (VI) (hereinafter sometimes referred to as “copolymerizable monomer”). There may be.

  Examples of the copolymerizable monomer include a monomer represented by the following formula (Da) (hereinafter sometimes referred to as “monomer (Da)”), vinyl esters such as vinyl acetate, and (anhydrous) malein. Acids, maleic acid derivatives such as maleic acid (half) esters, maleimides, ethylene, α-olefin compounds having 3 to 20 carbon atoms, cyclic olefins having 5 to 20 carbon atoms, vinyl compounds, trifunctional or more polyfunctional photopolymerization Compound.

(In the formula (Da), R ₁₇ represents a hydrogen atom or a methyl group, R ₁₈ represents an atomic group having at least one group having a 5- to 20-membered aromaticity, and Y represents the number of carbon atoms. Represents an alkylene group having 2 to 6 carbon atoms or an alkyleneoxy group having 2 to 6 carbon atoms, and the alkylene group and the alkyleneoxy group may contain an alkyl group, a hydroxyl group or a carbonyl group having 1 to 6 carbon atoms. Represents an integer of 1 to 6.)

  As the monomer (Da), a monomer represented by the formula (D-2) or the formula (D-3) is preferable.

(In Formula (D-2) and Formula (D-3), Y ₁ each independently represents an alkylene group having 2 to 6 carbon atoms. The alkylene group is an alkyl group having 1 to 6 carbon atoms or a hydroxyl group. R ₁₈ each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a glycidoxy group. Each independently represents an integer of 0 to 5, and q independently represents an integer of 0 to 4. R ₁₇ and m each independently represent the same meaning as described above.

  Specific examples of the monomer (D-2) include a monomer represented by the formula (D-2-1), and specific examples of the monomer (D-3) include those represented by the formula (D-3-1). And monomers represented.

The production method of the monomer (D-a) is, for example, using a phenol compound as a compound that gives the structure of R _18, by reacting an alkylene oxide such as ethylene oxide to the _{compound, R 18 - (Y) m} -OH And further esterifying acrylic acid or methacrylic acid, for example, using a halogenated benzene compound as the compound giving the structure of R ₁₈ , reacting the compound with an alkylene diol, and R _18- (Y) Examples thereof include a method of obtaining _m- OH and further esterifying with acrylic acid or methacrylic acid.

  The compounds represented by formula (D-2-1) and formula (D-3-1) are trade names of NK ester A-LEN-10 and NK ester A-CMP-1E from Shin-Nakamura Chemical Co., Ltd. It is commercially available.

  Examples of the α-olefin compound having 3 to 20 carbon atoms used as the copolymerizable monomer include propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1 A linear α-olefin having 3 to 20 carbon atoms such as tetradecene, 1-hexadecene, 1-octadecene, 1-eicocene, 4-methyl-1-pentene, 3-methyl-1-pentene, 3- Examples thereof include branched α-olefins having 4 to 20 carbon atoms such as methyl-1-butene.

  Among ethylene and α-olefin compounds having 3 to 20 carbon atoms, ethylene, propylene and 1-butene, which are linear α-olefins having 3 or 4 carbon atoms, were formed into a film. In view of excellent flexibility, ethylene is particularly preferable.

  The cyclic olefin used as a copolymerizable monomer is a compound having a polymerizable carbon-carbon double bond in the carbocycle. Specifically, bicyclo [2,2,1] hept-2-ene, 6-alkylbicyclo [2,2,1] hept-2-ene, 5,6-dialkylbicyclo [2,2,1] Methyl group, ethyl group, butyl, such as hept-2-ene, 1-alkylbicyclo [2,2,1] hept-2-ene, 7-alkylbicyclo [2,2,1] hept-2-ene A norbornene derivative having an alkyl group having 1 to 4 carbon atoms such as a group introduced therein, tetracyclo [4,4,0,12,5,17,10] -3-dodecene, also called dimethanooctahydronaphthalene, 8 -Alkyltetracyclo [4,4,0,12,5,17,10] -3-dodecene, 8,9-dialkyltetracyclo [4,4,0,12,5,17,10] -3-dodecene Dimethanooctahydronaphthale A dimethanooctahydronaphthalene derivative in which an alkyl group having 3 or more carbon atoms is introduced into the 8-position and / or 9-position, a norbornene derivative in which one or more halogens are introduced in the molecule, the 8-position and / or And a derivative of dimethanooctahydronaphthalene in which halogen is introduced at the 9-position.

  Examples of vinyl compounds used as copolymerizable monomers include vinyl acetate, (anhydrous) maleic acid and maleimide. Furthermore, the vinyl compound which has a C5-C20 alicyclic structure is mentioned.

  Examples of the vinyl compound having an alicyclic structure used as a copolymerizable monomer include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecanyl group, a norbornenyl group, and an adamantyl group. It is a compound consisting of an alicyclic hydrocarbon group having about 3 to 12 carbon atoms and a vinyl group.

  Examples of the trifunctional or higher polyfunctional photopolymerizable compound used as a copolymerizable monomer include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, Examples include dipentaerythritol hexamethacrylate. The copolymerizable monomers may be used alone or in combination of two or more. The trifunctional or higher polyfunctional photopolymerizable compound may be one type or two or more types of trifunctional or higher polyfunctional photopolymerizable compounds.

  The optical film of the present invention is obtained by forming a film of a composition for optical film containing the compound (A) (hereinafter sometimes referred to as “composition”) and further stretching. The step of forming a film and further stretching includes a photopolymerization step. The photopolymerization may be performed after film formation and before stretching, may be performed while film formation is performed while stretching, or may be performed after film formation and further stretching. In particular, the optical film of the present invention is preferably obtained by further stretching the composition after it is formed into a film and photopolymerized.

  The composition comprises compound (A) and, if necessary, at least one monomer (1) selected from the group consisting of photopolymerization initiator (3), monomer (I) to monomer (III), monomer (I ) To at least one monomer selected from the group consisting of monomer (VI) and monomer (V), and a monomer obtained by polymerizing at least one monomer (1) selected from the group consisting of monomer (III) It is prepared by mixing (VI), a copolymerizable monomer, a polymerization inhibitor, a photosensitizer, an organic solvent, a leveling agent or a plasticizer.

  Examples of the photopolymerization initiator (3) include benzoins, benzophenones, benzyl ketals, α-hydroxy ketones, α-amino ketones, iodonium salts, sulfonium salts, and the like. More specifically, Irgacure ( Irgacure) 907, Irgacure 184, Irgacure 651, Irgacure 250, Irgacure 369 (all are manufactured by Ciba Japan Co., Ltd.), Seiko All BZ, Seiko All Z, Seiko All BEE (all are manufactured by Seiko Chemical Co., Ltd.), Kaya Cure ( kayacure) BP100 (manufactured by Nippon Kayaku Co., Ltd.), Kayacure UVI-6992 (manufactured by Dow), Adekaoptomer SP-152 or Adekaoptomer SP-170 (all above, ADEKA Corporation) it can.

  Moreover, the usage-amount of a photoinitiator (3) is 0.1 weight part-30 weight part with respect to 100 weight part of total amounts, for example of a compound (A) and monomer (I)-monomer (VI), Preferably they are 0.5 weight part-10 weight part. If it is in the said range, a monomer can be polymerized, without reducing the transmittance | permeability.

The composition may contain a polymerization inhibitor in order to control the polymerization of monomer (I) to monomer (VI) and compound (A) and to improve the stability of the resulting optical film. Examples of the polymerization inhibitor include hydroquinones having a substituent such as hydroquinone or alkyl ether, catechols having a substituent such as alkyl ether such as butylcatechol, pyrogallols, 2,2,6,6-tetramethyl-1 -Radical scavengers such as piperidinyloxy radical, thiophenols, β-naphthylamines, β-naphthols and the like.
The amount of the polymerization inhibitor used is, for example, 0.1 to 30 parts by weight, preferably 0.5 to 100 parts by weight of the total amount of compound (A) and monomer (I) to monomer (VI). Parts by weight to 10 parts by weight. If it is in the said range, a compound (A) and monomer (I)-monomer (VI) can be polymerized, without reducing the transmittance | permeability.

The composition may contain a photosensitizer in order to increase the sensitivity of the reaction of the photopolymerization initiator. Examples of the photosensitizer include xanthones such as xanthone or thioxanthone, anthracene having a substituent such as anthracene or alkyl ether, phenothiazine, or rubrene.
The amount of the photosensitizer used is, for example, 0.1 to 30 parts by weight, preferably 0 with respect to 100 parts by weight of the total amount of the compound (A) and the monomer (I) to the monomer (VI). .5 to 10 parts by weight. Within the above range, the compound (A) and the monomer (I) to the monomer (VI) can be polymerized with high sensitivity without decreasing the transmittance.

The composition may contain a leveling agent. Examples of leveling agents include Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, 29SHPA, SH30PA, polyether-modified silicone oil SH8400 (manufactured by Torresilicone), KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Silicone), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufactured by GE Toshiba Silicone), Florinato (trade name) FC430, FC431 (Manufactured by Sumitomo 3M Co., Ltd.), MegaFuck (trade name) F142D, F171, F172, F173, F177, F18 , R30 (manufactured by Dainippon Ink & Chemicals, Inc.), Ftop (trade name) EF301, EF303, EF351, EF352 (manufactured by Shin-Akita Kasei Co., Ltd.), Surflon (tradename) S381, S382 SC101, SC105 (Asahi Glass Co., Ltd.), E5844 (Daikin Fine Chemical Laboratory Co., Ltd.), BM-1000, BM-1100 (Brand name: BM Chemie Co., Ltd.), Mega Fuck (trade name) ) R08, BL20, F475, F477 or F443 (Dainippon Ink Chemical Co., Ltd.).
By using a leveling agent, the obtained film (membrane) can be smoothed. Furthermore, in the production process of film formation, the fluidity of the composition can be controlled, and the crosslinking density of the film obtained by polymerizing the monomer can be adjusted.
The content of the leveling agent is, for example, relative to 100 parts by weight of the total of the compound (A), the monomer (I) to the monomer (VI) contained as necessary, the photopolymerization initiator (3) and the copolymerizable monomer. And 0.001 to 2.0 parts by weight, preferably 0.005 to 1.5 parts by weight. If it is in the said range, a monomer can be polymerized, without reducing the transmittance | permeability.

The composition may contain a plasticizer. As the plasticizer, phosphoric acid ester, carboxylic acid ester or glycolic acid ester is used. Examples of phosphate esters include triphenyl phosphate (TPP), tricresyl phosphate (TCP), cresyl diphenyl phosphate, octyl diphenyl phosphate, diphenyl biphenyl phosphate, trioctyl phosphate or tributyl phosphate.
The carboxylic acid ester is typically a phthalic acid ester or a citric acid ester. Examples of the phthalic acid ester include dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), dioctyl phthalate (DOP), diphenyl phthalate (DPP) or diethyl hexyl phthalate (DEHP). Examples of the citric acid ester include O-acetyl triethyl citrate (OACTE), O-acetyl tributyl citrate (OACTB), acetyl triethyl citrate or acetyl tributyl citrate.
Examples of other carboxylic acid esters include butyl oleate, methylacetyl ricinoleate, dibutyl sebacate, and various trimellitic acid esters.

  Examples of glycolic acid esters include triacetin, tributyrin, butyl phthalyl butyl glycolate, ethyl phthalyl ethyl glycolate, methyl phthalyl ethyl glycolate or butyl phthalyl butyl glycolate. Also trimethylolpropane tribenzoate, pentaerythritol tetrabenzoate, ditrimethylolpropane tetraacetate, ditrimethylolpropane tetrapropionate, pentaerythritol tetraacetate, sorbitol hexaacetate, sorbitol hexapropionate, sorbitol triacetate tripropionate, inositol pentaacetate Or sorbitan tetrabutyrate is also a good example.

  Among the plasticizers, triphenyl phosphate, tricresyl phosphate, cresyl diphenyl phosphate, tributyl phosphate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dioctyl phthalate, diethyl hexyl phthalate, triacetin, ethyl phthalyl ethyl glycolate, trimethylol Propane tribenzoate, pentaerythritol tetrabenzoate, ditrimethylolpropane tetraacetate, pentaerythritol tetraacetate, sorbitol hexaacetate, sorbitol hexapropionate, sorbitol triacetate tripropionate, etc. are preferred, especially triphenyl phosphate, diethyl phthalate, ethyl phthalyl Ethyl glycolate, trimethylo Le propane tribenzoate, pentaerythritol tetrabenzoate, ditrimethylolpropane tetra acetate, sorbitol hexaacetate, sorbitol hexapropionate or sorbitol triacetate tripropionate are preferred.

One or more plasticizers may be used in combination. The addition amount of the plasticizer may be appropriately selected within a range that does not significantly impair the film properties of the present invention, and is, for example, about 0.1 to 30% by weight with respect to the total solid content of the composition in the present invention. .
Specific examples of the plasticizer include (di) pentaerythritol esters described in JP-A No. 11-124445, glycerol esters described in JP-A No. 11-246704, and diglycerol esters described in JP-A No. 2000-63560. And citric acid esters described in JP-A-11-92574 and substituted phenyl phosphates described in JP-A-11-90946.

Examples of the organic solvent include ethers, aromatic hydrocarbons, ketones, alcohols, esters or amides.
Examples of ethers include tetrahydrofuran, tetrahydropyran, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono Butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate Methyl cellosolve acetate, ethyl cellosolve acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether acetate, methoxybutyl acetate, methoxy pentyl acetate, anisole, and the like phenetole or methyl anisole.

Examples of aromatic hydrocarbons include benzene, toluene, xylene, mesitylene and the like.
Examples of ketones include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, and cyclohexanone.
Examples of alcohols include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.

  Examples of the esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, Methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, ethyl 3-oxypropionate, 3-methoxypropionate Acid methyl, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, 2-metho Methyl cypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, 2-oxy-2- Ethyl methyl propionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, 2-oxobutane Examples include methyl acid, ethyl 2-oxobutanoate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, and γ-butyrolactone.

Examples of amides include N, N-dimethylformamide and N, N-dimethylacetamide.
Examples of other solvents include N-methylpyrrolidone and dimethyl sulfoxide.
A solvent can be used individually or in combination of 2 types or more, respectively.
The amount of the organic solvent in producing the composition is such that the total concentration of compound (A) and monomer (I) to monomer (VI) is adjusted to 10% by weight or more, preferably 20 to 50% by weight. is there.

  Monomer (I) to monomer (III) may be contained in the composition as a polymer polymerized in advance (hereinafter sometimes referred to as “polymer (1)”). Examples of the copolymerization format of the polymer (1) include a random format and a block format. When the block format is so small that the structural units constituting the polymer (1) do not form domains, the copolymer (1) can be obtained. This is preferable because the transparency of the obtained optical film is improved.

  As a method for preparing the polymer (1), for example, the monomer (I) to the monomer (III) are prepared in an organic solvent so as to have a concentration of 10% by weight or more, preferably 20 to 40% by weight. And a method of obtaining a solution containing the polymer (1) by stirring for about 1 to 24 hours while heating to about 20 to 100 ° C., preferably about 40 to 90 ° C., particularly preferably about 60 to 80 ° C. Is mentioned. In order to control the reaction, a monomer or a polymerization initiator to be used may be added during the polymerization, or may be added after being dissolved in an organic solvent.

  Further, when a gas copolymerizable monomer such as ethylene or propylene is used, it may be produced under such a copolymerizable monomer atmosphere, preferably under pressure, instead of nitrogen.

  Examples of the polymerization initiator include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane-1-carbonitrile), 2 , 2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (2,4-dimethyl-4-methoxyvaleronitrile), dimethyl-2,2′-azobis (2-methylpropionate) ) Or 2,2′-azobis (2-hydroxymethylpropionitrile); an azo compound; lauryl peroxide, tert-butyl hydroperoxide, benzoyl peroxide, tert-butyl peroxybenzoate, cumene hydroperoxide, Diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, t organic peroxides such as rt-butylperoxyneodecanoate, tert-butylperoxypivalate or (3,5,5-trimethylhexanoyl) peroxide; inorganic peroxides such as potassium persulfate, ammonium persulfate or hydrogen peroxide An oxide etc. are mentioned. A redox initiator using a thermal polymerization initiator and a reducing agent in combination can also be used as the polymerization initiator.

  Examples of the organic solvent include aromatic hydrocarbons such as toluene and xylene; ethyl acetate, butyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and the like. Examples include esters; aliphatic alcohols such as n-propyl alcohol or isopropyl alcohol; ketones such as methyl ethyl ketone or methyl isobutyl ketone.

  The optical film of the present invention is usually produced by forming the composition into a film (filming) and further stretching the obtained film. Photopolymerization is preferably performed between the film forming step and the stretching step. As a method of forming a film of the composition, for example, a solvent casting method in which a solution containing the composition is cast on a smooth surface and the solvent is distilled off, and the composition is extruded into a film with a melt extruder or the like. And melt extrusion method. In particular, the solvent casting method is preferable because a solution containing the composition can be directly formed into a film.

  As a photopolymerization method, the composition is cured by photopolymerization with ultraviolet light (UV). Examples of ultraviolet light generation sources include fluorescent chemical lamps, black light, low pressure, high pressure, ultrahigh pressure mercury lamps, metal halide lamps, and sunlight. The irradiation intensity of the ultraviolet light may be constant throughout, or the physical properties after curing can be finely adjusted by changing the intensity during the curing.

Examples of the stretching method include a stretching method by a tenter method and a stretching method by stretching between rolls.
Stretching may be either uniaxial stretching or biaxial stretching, and may be either longitudinal stretching or lateral stretching. In particular, from the viewpoint of productivity, uniaxial stretching is preferable, and uniaxial longitudinal stretching is particularly preferable.

The ratio ([Re (450)] / [Re (550)]) of the retardation [Re (450)] having a wavelength of 450 nm and the retardation [Re (550)] having a wavelength of 550 nm of the light transmitted through the optical film is a wavelength. It is defined as a dispersion coefficient α, and in order for the optical film to perform uniform polarization conversion in a wide wavelength range, it is preferable that the optical film has a wavelength dispersion characteristic that the wavelength dispersion coefficient α is less than 1.00. The optical film of the present invention thus obtained usually has a wavelength dispersion coefficient α of less than 1.00.
The retardation value Re (ν) at the wavelength νnm of light transmitted through the optical film is generally increased to the right in the visible range of 300 to 700 nm, such as satisfying the relationship of Re (450) <Re (550) <Re (650). Therefore, uniform polarization conversion can be performed in a wide wavelength range.

Since the optical film of the present invention can perform uniform polarization conversion in a wide wavelength range, it is used as a retardation plate such as a λ / 2 plate or a λ / 4 plate, a viewing angle improving film, or the like. If the optical film is a λ / 4 plate, it can be combined with a linear polarizing plate to make a circular polarizing plate in a wide wavelength range, and if it is a λ / 2 plate, it can be combined with a linear polarizing plate. A polarization rotation element having a wide wavelength range can be obtained. Therefore, it can be used for various liquid crystal display devices, cathode ray tubes (CRT), touch panels, anti-reflection filters in electroluminescence (EL) lamps, and liquid crystal projectors.
The retardation plate of the present invention is thus composed of the above optical film, and can perform uniform polarization conversion in a wide wavelength range.

  Hereinafter, the present invention will be described in more detail with reference to examples. In the examples, “%” and “parts” are by weight and parts by weight unless otherwise specified.

(Chromatic dispersion characteristics)
A film-like material was produced from the synthesized resin by a solvent casting method. The film-like material was stretched by an autograph with temperature control (Strograph T, manufactured by Toyo Seiki Seisakusho Co., Ltd.) to produce the optical film of the present invention. The film thickness of the optical film is measured with a thickness meter (Sendai Nikon Co., Ltd.), and an automatic birefringence meter (KOBRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.) is used for wavelength dispersion characteristics in the wavelength range of 450 nm to 750 nm. And measured.

(Optical anisotropy)
When the polymer main chain is uniaxially oriented by stretching, it has negative birefringence when it has optical anisotropy in which the orientation direction and the direction in which the refractive index is maximized are different (for example, perpendicular to each other). ing. On the other hand, when the orientation direction and the direction in which the refractive index is maximum match or nearly match (for example, when the difference between the orientation direction and the direction in which the refractive index is maximum is within 10 degrees), positive birefringence have. The direction in which the refractive index is maximized can be obtained from an automatic birefringence meter.

Example 1
In a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 400 parts of methyl methacrylate, 193 parts of N-vinylcarbazole and 1103 parts of propylene glycol monomethyl ether acetate were mixed and dissolved, and then the temperature was raised to 70 ° C. Thereafter, 2.46 parts of a polymerization initiator (azobisisobutyronitrile) was added and stirred at 70 ° C. to obtain a solution containing a polymer. To 100 g of the obtained solution, 12 g of a compound (A) represented by the formula (A-7) (A-BPE-4, manufactured by Shin-Nakamura Chemical Co., Ltd.), a photopolymerization initiator (3) (2-Methyl) -1-4- (methylthio) pheny-2-morpholino-propan-1-one, Irgacure 907, manufactured by Ciba Japan Co., Ltd.) was mixed and dissolved, and then the release film made of polyethylene terephthalate was 300 μm. Coated with an applicator of the gap, dried at 100 ° C. for 30 minutes, UV irradiation (high pressure mercury lamp: 200 mJ / cm ² per pass: 365 nm), and further stretched 1.8 times using a temperature-controlled autograph stretching machine. A film was obtained. The optical film was measured for wavelength dispersion characteristics using an automatic birefringence meter (KOBRA-WR, manufactured by Oji Scientific Instruments) in the wavelength range of 450 nm to 750 nm. The optical film has a film thickness of 80 μm, positive birefringence, Re (550) = 180 nm, Re (450) / Re (550) = 0.88, Re (500) / Re (550) = 0. The optical characteristics were 93, Re (600) / Re (550) = 1.03, Re (650) / Re (550) = 1.05, and Re (750) / Re (550) = 1.07.

(Example 2)
Film thickness: 75 μm in the same manner as in Example 1 except that the compound (A-BP-2E, manufactured by Shin-Nakamura Chemical Co., Ltd.) represented by the formula (A-8) is used as the compound (A). Positive birefringence, Re (550) = 220 nm, Re (450) / Re (550) = 0.81, Re (500) / Re (550) = 0.92, Re (600) / Re ( 550) = 1.08, Re (650) / Re (550) = 1.15, and Re (750) / Re (550) = 1.28.

(Example 3)
As in Example 1, except that the compound (LC242, manufactured by BASF) represented by the formula (A-9) is used as the compound (A), the film thickness: 85 μm, positive birefringence, Re (550) = 140 nm, Re (450) / Re (550) = 0.85, Re (500) / Re (550) = 0.93, Re (600) / Re (550) = 1.07, Re ( 650) / Re (550) = 1.13 and Re (750) / Re (550) = 1.22.

Example 4
200 parts of methyl methacrylate [monomer (III)], 200 parts of N-vinylcarbazole [monomer (I)], 193 parts of N, N-diethylacrylamide [monomer (II)], 1103 parts of propylene glycol monomethyl ether acetate Except for changing to 1080 parts, the film thickness: 75 μm, positive birefringence, Re (550) = 152 nm, Re (450) / Re (550) = 0.88, Re as in Example 1. (500) / Re (550) = 0.94, Re (600) / Re (550) = 1.03, Re (650) / Re (550) = 1.06, Re (750) / Re (550) = 1.08 optical film was obtained.

(Example 5)
In a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 500 parts of methyl methacrylate and 1430 parts of propylene glycol monomethyl ether acetate were mixed and dissolved, and then heated to 70 ° C. Thereafter, 2.23 parts of a polymerization initiator (azobisisobutyronitrile) was added and stirred at 70 ° C. to obtain a solution containing a polymer. To 10.0 g of the obtained solution, 0.7 part of N-vinylcarbazole [monomer (I)], 9.3 g of A-BPE-4 [compound (A)], photopolymerization initiator (3) (Irgacure 184, Ciba Japan Co., Ltd.) 0.1 g and polyether-modified silicone oil SH8400 (Toray Silicone Co., Ltd.) 0.05 g were mixed and dissolved, and then released onto a polyethylene terephthalate release film with a 300 μm gap applicator. Coating, drying at 100 ° C. for 30 minutes, UV irradiation (high pressure mercury lamp: 200 mJ / cm ² per pass: 365 nm), and stretching 1.8 times using a temperature-controlled autograph stretching machine, an optical film was obtained. The optical film was measured for wavelength dispersion characteristics using an automatic birefringence meter (KOBRA-WR, manufactured by Oji Scientific Instruments) in the wavelength range of 450 nm to 750 nm. The optical film has a film thickness of 52 μm, positive birefringence, Re (550) = 71 nm, Re (450) / Re (550) = 0.90, Re (500) / Re (550) = 0. The optical characteristics were 95, Re (600) / Re (550) = 1.04, Re (650) / Re (550) = 1.06, Re (750) / Re (550) = 1.07.

(Example 6)
As in Example 5, except that A-BP-2E is used as the compound (A), the film thickness is 62 μm, the positive birefringence, Re (550) = 84 nm, Re (450) / Re ( 550) = 0.81, Re (500) / Re (550) = 0.92, Re (600) / Re (550) = 1.08, Re (650) / Re (550) = 1.14, Re An optical film of (750) / Re (550) = 1.20 was obtained.

(Example 7)
N-vinylcarbazole [monomer (I)] 1.5 parts, A-BPE-4 [compound (A)] 18.5 g, photopolymerization initiator (3) (Irgacure 184, manufactured by Ciba Japan Co., Ltd.) 0 .2 g, 10 parts of propylene glycol monomethyl ether acetate and 0.5 g of MegaFac (trade name) F475 (manufactured by Dainippon Ink & Chemicals, Inc.) are mixed and dissolved, and then a 300 μm thick film is formed on a polyethylene terephthalate release film. An optical film was obtained in the same manner as in Example 5 except that coating was performed using a gap applicator and UV irradiation was performed (high pressure mercury lamp: 200 mJ / cm ² per pass: 365 nm). The optical film has a film thickness of 28 μm, positive birefringence, Re (550) = 71 nm, Re (450) / Re (550) = 0.86, Re (500) / Re (550) = 0. The optical characteristics were 93, Re (600) / Re (550) = 1.05, Re (650) / Re (550) = 1.09, Re (750) / Re (550) = 1.13.

(Example 8)
Other than changing 1.5 parts of N-vinylcarbazole [monomer (I)] to 0.3 parts of N-vinylcarbazole [monomer (I)] and 4.7 parts of N, N-diethylacrylamide [monomer (II)] In the same manner as in Example 7, film thickness: 38 μm, positive birefringence, Re (550) = 72 nm, Re (450) / Re (550) = 0.88, Re (500) / Re ( 550) = 0.94, Re (600) / Re (550) = 1.04, Re (650) / Re (550) = 1.07, Re (750) / Re (550) = 1.09 A film was obtained.

Example 9
Example 1 except that 1.5 parts of N-vinylcarbazole [monomer (I)] is changed to 0.5 parts of N-vinylcarbazole [monomer (I)] and 9.5 parts of methyl methacrylate [monomer (III)] 7 and film thickness: 33 μm, positive birefringence, Re (550) = 79 nm, Re (450) / Re (550) = 0.85, Re (500) / Re (550) = 0 .93, Re (600) / Re (550) = 1.05, Re (650) / Re (550) = 1.08, Re (750) / Re (550) = 1.10. .

(Example 10)
In a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 500 parts of methyl methacrylate and 1430 parts of propylene glycol monomethyl ether acetate were mixed and dissolved, and then heated to 70 ° C. Thereafter, 2.23 parts of a polymerization initiator (azobisisobutyronitrile) was added and stirred at 70 ° C. to obtain a solution containing a polymer. To 70 g of the obtained solution, 35 g of a monomer represented by the formula (IV-4) (DCP, manufactured by Shin-Nakamura Chemical Co., Ltd.) [monomer (IV)] and 45 g of A-BPE-4 [compound (A)] , Photopolymerization initiator (3) (2-Methyl-1-4- (methylthio) pheny-2-morpholino-propan-1-one, Irgacure 907, manufactured by Ciba Japan Co., Ltd.) 1.0 g, polyether-modified After mixing and dissolving 0.85 g of silicon oil SH8400 (Toray Silicone Co., Ltd.), it was applied on a polyethylene terephthalate release film with a 300 μm gap applicator, dried at 100 ° C. for 30 minutes, and irradiated with UV (high pressure Mercury lamp: 200 mJ / cm ² per pass: 365 nm), and further stretched 1.8 times using a temperature-controlled autograph stretching machine to obtain an optical film. The obtained optical film was measured for wavelength dispersion characteristics using an automatic birefringence meter (KOBRA-WR, manufactured by Oji Scientific Instruments) in the wavelength range of 450 nm to 750 nm. The optical film has a film thickness of 98 μm, positive birefringence, Re (550) = 240 nm, Re (450) / Re (550) = 0.94, Re (500) / Re (550) = 0. 97, Re (600) / Re (550) = 1.02, Re (650) / Re (550) = 1.05, Re (750) / Re (550) = 1.07.

(Example 11)
Except for changing 35 g of DCP [monomer (IV)] to 29 g of a monomer represented by formula (V-2) (A-CHD-4E, manufactured by Shin-Nakamura Chemical Co., Ltd.) [monomer (V)] In the same manner as in Example 10, an optical film was obtained. The optical film has a film thickness of 92 μm, positive birefringence, Re (550) = 0252 nm, Re (450) / Re (550) = 0.89, Re (500) / Re (550) = 0. 94, Re (600) / Re (550) = 1.05, Re (650) / Re (550) = 1.08, Re (750) / Re (550) = 1.13.

(Example 12)
33 g of A-CHD-4E [monomer (V)], 42 g of A-BPE-4 [compound (A)], photopolymerization initiator (3) (2-Methyl-1-4- (methylthio) pheny-2-morpholino -propan-1-one, Irgacure 907, manufactured by Ciba Japan Co., Ltd.) 0.8 g, 55 parts of propylene glycol monomethyl ether acetate, MegaFac (trade name) F475 (manufactured by Dainippon Ink & Chemicals, Inc.) 3 g was mixed and dissolved, and then applied to a release film made of polyethylene terephthalate with a 300 μm gap applicator and UV irradiation (high pressure mercury lamp: 200 mJ / cm ² per pass: 365 nm) as in Example 10. In the same manner, an optical film was obtained. The optical film has a film thickness: 42 μm, positive birefringence, Re (550) = 142 nm, Re (450) / Re (550) = 0.88, Re (500) / Re (550) = 0. 94, Re (600) / Re (550) = 1.06, Re (650) / Re (550) = 1.11, Re (750) / Re (550) = 1.16.

(Example 13)
In a reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 500 parts of methyl methacrylate and 1430 parts of propylene glycol monomethyl ether acetate were mixed and dissolved, and then heated to 70 ° C. Thereafter, 2.23 parts of a polymerization initiator (azobisisobutyronitrile) was added and stirred at 70 ° C. to obtain a solution containing a binder polymer. To 70 g of the obtained solution (binder polymer), monomer (A-BPEF, manufactured by Shin-Nakamura Chemical Co., Ltd.) [monomer (VI)] 11 g, A-BPE-4 [ Compound (A)] 69 g, photopolymerization initiator (3) (2-Methyl-1-4- (methylthio) pheny-2-morpholino-propan-1-one, Irgacure 907, manufactured by Ciba Japan Co., Ltd.) 1 0.08 g, 0.85 g of polyether-modified silicone oil SH8400 (Toray Silicone Co., Ltd.) was mixed and dissolved, and then applied onto a polyethylene terephthalate release film with a 300 μm gap applicator and dried at 100 ° C. for 30 minutes. And UV irradiation (high pressure mercury lamp: 200 mJ / cm ² per pass: 365 nm), and further stretched 1.8 times using a temperature-controlled autograph stretching machine to obtain an optical film. The obtained optical film was measured for wavelength dispersion characteristics using an automatic birefringence meter (KOBRA-WR, manufactured by Oji Scientific Instruments) in the wavelength range of 450 nm to 750 nm. The optical film has a film thickness of 89 μm, positive birefringence, Re (550) = 262 nm, Re (450) / Re (550) = 0.86, Re (500) / Re (550) = 0. The optical characteristics were 93, Re (600) / Re (550) = 1.06, Re (650) / Re (550) = 1.12, and Re (750) / Re (550) = 1.20.

(Example 14)
A-BPEF [monomer (VI)] 13 g, A-BPE-4 [compound (A)] 72 g, photopolymerization initiator (3) (2-Methyl-1-4- (methylthio) pheny-2-morpholino-propan -1-one, Irgacure 907, Ciba Japan Co., Ltd.) 0.8 g, Propylene glycol monomethyl ether acetate 55 parts, MegaFac (trade name) F475 (Dainippon Ink Chemical Co., Ltd.) 1.3 g After mixing and dissolving, it was applied to a release film made of polyethylene terephthalate with an applicator having a gap of 300 μm, and UV irradiation (200 mJ / cm ² : 365 nm per high pressure mercury lamp: 1 Pass) was carried out in the same manner as in Example 13. Thus, an optical film was obtained. The optical film has a film thickness of 42 μm, positive birefringence, Re (550) = 192 nm, Re (450) / Re (550) = 0.85, Re (500) / Re (550) = 0. The optical characteristics were 93, Re (600) / Re (550) = 1.07, Re (650) / Re (550) = 1.13, and Re (750) / Re (550) = 1.21.

  The optical film of the present invention can be produced without using phosgene, and enables uniform polarization conversion in a wide wavelength range.

Claims (22)

A composition comprising a compound having at least two groups selected from the group consisting of acryloyl groups and methacryloyl groups in the molecule and having a group represented by the formula (A) is formed into a film and further stretched. An optical film.

(In formula (A), B ₁ and B ₂ each independently represent a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a glycidoxy group. X is a divalent carbonization. Represents a hydrogen group, a sulfide group, a sulfonyl group, an ether bond or a single bond, and the hydrocarbon group may contain —CO—O—, each of a ₁ and a ₂ independently represents 0 to 4; Represents an integer.)   A composition containing two or more groups having at least one group selected from the group consisting of acryloyl groups and methacryloyl groups in the molecule and containing a group represented by the formula (A) was formed into a film and photopolymerized. 2. The optical film according to claim 1, which is further stretched. The compound having two or more groups selected from the group consisting of acryloyl group and methacryloyl group in the molecule and having the group represented by formula (A) consists of acryloyl group and methacryloyl group in the molecule. A compound having at least two groups selected from the group and having a group represented by the formula (A-1), the formula (A-2) or the formula (A-3). 2. The optical film according to 2.

(In formula (A-1) to formula (A-3), B ₁ , B ₂ , a ₁ and a ₂ represent the same meaning as described above.) A compound having two or more groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A) is represented by the formula (A-4). The optical film according to claim 1, which is a compound.

(In formula (A-4), R ₁₅ and R ₁₆ each independently represent a hydrogen atom or a methyl group, and X ₇ and X ₈ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, v ₄ and w ₄ each independently represents an integer of 0 to 6. X is the same as above. Represents meaning.) The optical composition according to any one of claims 1 to 4, wherein the composition further comprises at least one monomer (1) selected from the group consisting of monomers represented by formulas (I) to (III). the film.

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.) The composition further comprises a polymer obtained by polymerizing at least one monomer (1) selected from the group consisting of monomers represented by formulas (I) to (III). 5. The optical film as described in any one of 5 above.

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.)   The optical film according to claim 5 or 6, wherein the monomer represented by the formula (I) is at least one monomer selected from the group consisting of N-vinylcarbazole, vinylnaphthalene and vinylanthracene.   The monomer represented by the formula (II) is N, N-dimethylacrylamide, N, N-diethylacrylamide, N- (2-hydroxyethyl) acrylamide, N-isopropylacrylamide, acryloylmorpholine, dimethylaminoethyl (meth). The optical film according to any one of claims 5 to 7, which is at least one monomer selected from the group consisting of acrylate and diethylaminoethyl (meth) acrylate.   The monomer represented by the formula (III) is methyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-tetrahydropyranyl (meth) acrylate, isobornyl (meth) acrylate The optical film according to claim 5, wherein the optical film is at least one monomer selected from the group consisting of tricyclodecanyl (meth) acrylate, adamantyl (meth) acrylate, and 1-acryloyl-4-methoxynaphthalene. The optical film according to claim 1, wherein the composition further comprises at least one monomer selected from the group consisting of monomers represented by formula (IV) and formula (V).

(In formula (IV), R ₉ and R ₁₀ each independently represent a hydrogen atom or a methyl group, and X ₁ and X ₂ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₁ and Z ₂ each independently represents a single bond or a methylene group, s is an integer of 1 or 2, t represents an integer of 0 or 1. v ₁ and w ₁ each independently represent an integer of 0 to 6.)

(In formula (V), R ₁₁ and R ₁₂ each independently represent a hydrogen atom or a methyl group, and X ₃ and X ₄ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₃ and Z ₄ each independently represents a single bond or a methylene group, and v ₂ and w ₂ are respectively Independently represents an integer of 0 to 6.) The optical film according to any one of claims 1 to 10, wherein the composition further comprises a monomer represented by the formula (VI).

(In formula (VI), R ₁₃ and R ₁₄ each independently represents a hydrogen atom or a methyl group,
X ₅ and X ₆ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group, an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group may be contained. R each independently represents a hydroxyl group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a glycidoxy group, a nitro group, or a cyano group. v ₃ and _{w 3} are each independently an integer of Less than six, w each independently represent an integer of 0 to 4. When w is an integer of 2 or more, the plurality of R may be different types of groups. ) The optical film according to claim 11, wherein the monomer represented by the formula (VI) is a monomer represented by the formula (VI-1).

(In formula (VI-1), R ₁₃ , R ₁₄ , X ₅ , X ₆ , v ₃ and w ₃ represent the same meaning as described above.) The optical film according to claim 1, wherein a retardation value Re (ν) at a wavelength νnm of transmitted light that passes through the optical film satisfies the following formula.
Re (450) <Re (550) <Re (650)   The phase difference plate which consists of an optical film in any one of Claims 1-13. An optical film composition comprising a compound having two or more groups selected from the group consisting of an acryloyl group and a methacryloyl group in the molecule and having a group represented by the formula (A) is formed into a film. A method for producing an optical film that is further stretched .

(In formula (A), B ₁ and B ₂ each independently represent a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a glycidoxy group. X is a divalent carbonization. Represents a hydrogen group, a sulfide group, a sulfonyl group, an ether bond or a single bond, and the hydrocarbon group may contain —CO—O—, each of a ₁ and a ₂ independently represents 0 to 4; Represents an integer.) The method for producing an optical film according to claim 15 , wherein the composition for an optical film further comprises at least one monomer (1) selected from the group consisting of monomers represented by formulas (I) to (III).

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.) The composition for optical films further contains a polymer obtained by polymerizing at least one monomer (1) selected from the group consisting of monomers represented by formulas (I) to (III). Manufacturing method of the optical film .

(In the formula (I), R ₁ represents a hydrogen atom or a methyl group, and R ₂ represents a 5- to 20-membered aromatic hydrocarbon group or aromatic heterocyclic group. The aromatic hydrocarbon group or The aromatic heterocyclic group includes a hydroxyl group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, and a carbon number. 2-4 acyl groups, carboxyl groups or halogen atoms may be included.)

(In Formula (II), R ₃ represents a hydrogen atom or a methyl group, and R ₄ and R ₅ are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or R ₄ and R ₅ are linked. Represents an alkylene group having 4 to 6 carbon atoms, and the alkyl group and the alkylene group may contain a hydroxyl group, an oxygen atom, a sulfur atom or a nitrogen atom, and R ₆ is a single bond or 2 carbon atoms. Represents an oxyalkylene group of ˜6.)

(In formula (III), R ₇ represents a hydrogen atom or a methyl group, and R ₈ represents a hydrogen atom, a methyl group or a 5- to 20-membered cyclic hydrocarbon group. The cyclic hydrocarbon group is a hydroxyl group, An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidoxy group, an acyl group having 2 to 4 carbon atoms, and a carboxyl group , A halogen atom, an oxygen atom, a sulfur atom, or a nitrogen atom may be contained.The alkyl group, the alkoxy group, the aryl group, and the aralkyl group may contain a hydroxyl group or a halogen atom.) The method for producing an optical film according to any one of claims 15 to 17, wherein the composition for an optical film further comprises at least one monomer selected from the group consisting of monomers represented by formula (IV) and formula (V).

(In formula (IV), R ₉ and R ₁₀ each independently represent a hydrogen atom or a methyl group, and X ₁ and X ₂ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₁ and Z ₂ each independently represents a single bond or a methylene group, s is an integer of 1 or 2, t represents an integer of 0 or 1. v ₁ and w ₁ each independently represent an integer of 0 to 6.)

(In formula (V), R ₁₁ and R ₁₂ each independently represent a hydrogen atom or a methyl group, and X ₃ and X ₄ each independently represent an alkylene group having 2 to 6 carbon atoms. The group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group, Z ₃ and Z ₄ each independently represents a single bond or a methylene group, and v ₂ and w ₂ are respectively Independently represents an integer of 0 to 6.) The manufacturing method of the optical film in any one of Claims 15-18 in which the composition for optical films contains the monomer further represented by Formula (VI).

(In formula (VI), R ₁₃ and R ₁₄ each independently represents a hydrogen atom or a methyl group,
X ₅ and X ₆ each independently represent an alkylene group having 2 to 6 carbon atoms. The alkylene group may contain an alkyl group having 1 to 6 carbon atoms, a hydroxyl group or a carbonyl group. R each independently represents a hydroxyl group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a glycidoxy group, a nitro group, or a cyano group. v ₃ and _{w 3} are each independently an integer of Less than six, w each independently represent an integer of 0 to 4. When w is an integer of 2 or more, the plurality of R may be different types of groups. ) The method for producing an optical film according to any one of claims 15 to 19, wherein the composition for an optical film further comprises a photopolymerization initiator (3). The method for producing an optical film according to any one of claims 15 to 20, wherein the composition for optical film is formed into a film, photopolymerized, and further stretched. The manufacturing method of the optical film in any one of Claims 15-21 formed into a film by casting the solution containing the composition for optical films on a smooth surface, and distilling a solvent off.