JP2013147607A - Composition and optical film - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition for producing an optical film, which expresses excellent adhesiveness between a base or a polarizing film and an optical film; and to provide an optical film produced from the composition.SOLUTION: There are provided a composition comprising the following (A), (B), and (C); and an optical film formed of the composition: (A) a polymerizable liquid crystal compound; (B) a compound comprising a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule; and (C) a photopolymerization initiator, wherein the compound (B) preferably comprises an isocyanato group as the active hydrogen reactive group.

Description

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

  In a flat panel display (FPD), members including optical films such as a polarizing plate and a retardation plate are used. As such an optical film, what was manufactured by apply | coating the composition containing a polymeric liquid crystal compound, a photoinitiator, and a solvent on a base material is known. For example, in Patent Document 1, after aligning a polymerizable liquid crystal compound contained in a coating film formed by applying the composition on a substrate subjected to an alignment treatment, the polymerizable liquid crystal compound is polymerized. The formed optical film is described.

JP 2007-148098 A

  When an optical film is produced by applying a composition on a substrate that has been subjected to an orientation treatment, if the adhesion between the substrate and the resulting optical film is higher, peeling during processing occurs. Since it is easy to obtain a high quality optical film, it is preferable. However, since there is a limit to improving the adhesion by the optical film production process, it is preferable in that the production process can be simplified if the composition itself can form a highly adhesive optical film. Realization of a composition comprising

［式（X）中、
ｎは１〜１０までの整数を表わし、Ｒ^１’は、炭素数２〜２０の２価の脂肪族又は脂環式炭化水素基、或いは炭素数５〜２０の２価の芳香族炭化水素基を表わす。各繰り返し単位にある２つのＲ^２’は、一方が−ＮＨ−であり、他方がＮ−Ｃ（＝Ｏ）−Ｒ^３’で示される基である。Ｒ^３’は、水酸基又は炭素−炭素不飽和結合を有する基を表す。
式（Ｘ）中のＲ^３’のうち、少なくとも１つのＲ^３’は炭素−炭素不飽和結合を有する基である。］
〔４〕前記（Ａ）が、式（Ａ）で表される化合物である、〔１〕〜〔３〕のいずれか記載の組成物。

［式（Ａ）中、
Ｘ^１は、酸素原子、硫黄原子又は−ＮＲ^１−を表す。Ｒ^１は、水素原子又は炭素数１〜４のアルキル基を表す。
Ｙ^１は、置換基を有していてもよい炭素数６〜１２の１価の芳香族炭化水素基、又は置換基を有していてもよい炭素数３〜１２の１価の芳香族複素環式基を表す。
Ｑ^３及びＱ^４は、それぞれ独立に、水素原子、置換基を有していてもよい炭素数１〜２０の１価の脂肪族炭化水素基、炭素数３〜２０の脂環式炭化水素基、置換基を有していてもよい炭素数６〜２０の１価の芳香族炭化水素基、ハロゲン原子、シアノ基、ニトロ基、−ＮＲ^２Ｒ^３又は−ＳＲ^２を表すか、Ｑ^３及びＱ^４が互いに結合して、これらがそれぞれ結合する炭素原子とともに芳香環又は芳香族複素環を形成している。Ｒ^２及びＲ^３は、それぞれ独立に、水素原子又は炭素数１〜６のアルキル基を表す。
Ｄ^１及びＤ^２は、それぞれ独立に、単結合、−Ｃ（＝Ｏ）−Ｏ−、−Ｃ（＝Ｓ）−Ｏ−、−ＣＲ^４Ｒ^５−、−ＣＲ^４Ｒ^５−ＣＲ^６Ｒ^７−、−Ｏ−ＣＲ^４Ｒ^５−、−ＣＲ^４Ｒ^５−Ｏ−ＣＲ^６Ｒ^７−、−ＣＯ−Ｏ−ＣＲ^４Ｒ^５−、−Ｏ−ＣＯ−ＣＲ^４Ｒ^５−、−ＣＲ^４Ｒ^５−Ｏ−ＣＯ−ＣＲ^６Ｒ^７−、−ＣＲ^４Ｒ^５−ＣＯ−Ｏ−ＣＲ^６Ｒ^７−又は−ＮＲ^４−ＣＲ^５Ｒ^６−又は−ＣＯ−ＮＲ^４−を表す。
Ｒ^４、Ｒ^５、Ｒ^６及びＲ^７は、それぞれ独立に、水素原子、フッ素原子又は炭素数１〜４のアルキル基を表す。
Ｇ^１及びＧ^２は、それぞれ独立に、炭素数５〜８の２価の脂環式炭化水素基を表し、該脂環式炭化水素基を構成するメチレン基は、酸素原子、硫黄原子又は−ＮＨ−に置き換っていてもよく、該脂環式炭化水素基を構成するメチン基は、第三級窒素原子に置き換っていてもよい。
Ｌ^１及びＬ^２は、それぞれ独立に、１価の有機基を表し、Ｌ^１及びＬ^２のうち少なくとも一方が、重合性基を有する有機基である。］
〔５〕前記（Ａ）は、
前記式（Ａ）のＬ^１が式（Ａ１）で表される基であり、かつＬ^２が式（Ａ２）で表される基の化合物である、〔４〕記載の組成物。
Ｐ^１−Ｆ^１−（Ｂ^１−Ａ^１）_ｋ−Ｅ^１− （Ａ１）
Ｐ^２−Ｆ^２−（Ｂ^２−Ａ^２）_ｌ−Ｅ^２− （Ａ２）

［式（Ａ１）及び式（Ａ２）中、
Ｂ^１、Ｂ^２、Ｅ^１及びＥ^２は、それぞれ独立に、−ＣＲ^４Ｒ^５−、−ＣＨ_２−ＣＨ_２−、−Ｏ−、−Ｓ−、−ＣＯ−Ｏ−、−Ｏ−ＣＯ−Ｏ−、−ＣＳ−Ｏ−、−Ｏ−ＣＳ−Ｏ−、−ＣＯ−ＮＲ¹−、−Ｏ−ＣＨ_２−、−Ｓ−ＣＨ_２−又は単結合を表す。
Ａ^１及びＡ^２は、それぞれ独立に、炭素数５〜８の２価の脂環式炭化水素基又は炭素数６〜１８の２価の芳香族炭化水素基を表し、該脂環式炭化水素基を構成するメチレン基は、酸素原子、硫黄原子又は−ＮＨ−に置き換っていてもよく、該脂環式炭化水素基を構成するメチン基は、第三級窒素原子に置き換っていてもよい。
ｋ及びｌは、それぞれ独立に、０〜３の整数を表す。ｋが２以上の整数である場合、複数のＢ^１は互いに同一であっても異なっていてもよく、複数のＡ^１は互いに同一であっても異なっていてもよい。ｌが２以上の整数である場合、複数のＢ^２は互いに同一であっても異なっていてもよく、複数のＡ^２は互いに同一であっても異なっていてもよい。
Ｆ^１及びＦ^２は、炭素数１〜１２の２価の脂肪族炭化水素基を表す。
Ｐ^１は、重合性基を表す。
Ｐ^２は、水素原子又は重合性基を表す。
Ｒ^１、Ｒ^４及びＲ^５は、前記と同じ意味を表す。］
〔６〕〔１〕〜〔５〕のいずれか記載の組成物に含まれる重合性成分を重合して形成される光学フィルム。
〔７〕以下の（１）及び（２）を含む光学フィルムの製造方法。
（１）〔１〕〜〔５〕のいずれか記載の組成物を、基材上に塗布する工程；
（２）（１）により基材上に塗布された塗布膜中に含まれる重合性成分を重合することにより光学フィルムを形成する工程。
〔８〕前記基材が、水酸基を有する材料からなる、〔７〕記載の光学フィルムの製造方法。
〔９〕前記水酸基を有する材料が、トリアセチルセルロースをケン化して得られる材料である、〔８〕記載の光学フィルムの製造方法。
〔１０〕前記基材が、その表面に光配向性ポリマーから形成された配向膜が設けられたものである、〔７〕〜〔９〕のいずれか記載の光学フィルムの製造方法。
〔１１〕前記配向膜は、前記光配向性ポリマーが光照射により架橋構造を形成して設けられたものである、〔１０〕記載の光学フィルムの製造方法。
〔１２〕〔７〕〜〔１１〕のいずれか記載の製造方法により得られる光学フィルム。
〔１３〕位相差性を有する、〔６〕又は〔１２〕記載の光学フィルム。
〔１４〕〔１３〕記載の光学フィルムを含む偏光板。
〔１５〕〔６〕、〔１２〕又は〔１３〕記載の光学フィルムを備えたフラットパネル表示装置。 Under such circumstances, as a result of intensive studies, the present inventor has reached the present invention. That is, the present invention includes the following inventions.
[1] A composition comprising the following (A), (B) and (C).
(A) Polymerizable liquid crystal compound (B) Compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule (C) Photopolymerization initiator [2] The (B) is an active hydrogen reactive group The composition according to [1], which is a compound having an isocyanato group.
[3] The composition according to [1], wherein (B) is a compound represented by the following formula (X).

[In the formula (X),
n represents an integer of 1 to 10, and R ^{1 ′} is a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms, or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. Represents. Two R ^{2 ′ in} each repeating unit is a group represented by one —NH— and the other is N—C (═O) —R ^{3 ′} . R ^{3 ′} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
Of R ^{3 ′} in formula (X), at least one R ^{3 ′} is a group having a carbon-carbon unsaturated bond. ]
[4] The composition according to any one of [1] to [3], wherein (A) is a compound represented by formula (A).

[In the formula (A),
X ¹ represents an oxygen atom, a sulfur atom, or —NR ¹ —. R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Y ¹ is a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a monovalent aromatic complex having 3 to 12 carbon atoms which may have a substituent. Represents a cyclic group.
Q ³ and Q ⁴ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 3 to 20 carbon atoms. Represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a halogen atom, a cyano group, a nitro group, —NR ² R ³ or —SR ² , or Q ³ and Q ⁴ are bonded to each other to form an aromatic ring or an aromatic heterocyclic ring together with the carbon atoms to which they are bonded. R ² and R ³ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, —C (═O) —O—, —C (═S) —O—, —CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —CR ⁶ R. ^{7 -, - O-CR 4} R 5 -, - CR 4 R 5 -O-CR 6 R 7 -, - CO-O-CR 4 R 5 -, - O-CO-CR 4 R 5 -, - CR ^{4 R 5 -O-CO-CR} 6 R 7 -, - CR 4 R 5 -CO-O-CR 6 R 7 - or ^-NR 4 ^-CR 5 ^{R 6} - or -CO-NR ⁴ - represents a.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the methylene group constituting the alicyclic hydrocarbon group is an oxygen atom, a sulfur atom or — NH- may be substituted, and the methine group constituting the alicyclic hydrocarbon group may be substituted with a tertiary nitrogen atom.
L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group. ]
[5] (A)
The composition according to [4], wherein L ^{1 in the} formula (A) is a group represented by the formula (A1), and L ² is a compound having a group represented by the formula (A2).
P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) ₁ -E ^2- (A2)

[In Formula (A1) and Formula (A2),
^{B 1,} B 2, ^{E 1} and ^{E 2,} each _{^{independently, -CR 4 R 5 -, -}} CH 2 -CH 2 -, - O -, - S -, - CO-O -, - O-CO It represents —O—, —CS—O—, —O—CS—O—, —CO—NR ¹ —, —O—CH ₂ —, —S—CH ₂ — or a single bond.
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, and the alicyclic hydrocarbon The methylene group constituting the group may be replaced by an oxygen atom, a sulfur atom or -NH-, and the methine group constituting the alicyclic hydrocarbon group is replaced by a tertiary nitrogen atom. May be.
k and l each independently represents an integer of 0 to 3. When k is an integer of 2 or more, the plurality of B ¹ may be the same or different from each other, and the plurality of A ¹ may be the same or different from each other. When l is an integer of 2 or more, the plurality of B ² may be the same or different from each other, and the plurality of A ² may be the same or different from each other.
F ¹ and ^{F 2} represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ represents a polymerizable group.
P ² represents a hydrogen atom or a polymerizable group.
R ¹ , R ⁴ and R ⁵ represent the same meaning as described above. ]
[6] An optical film formed by polymerizing a polymerizable component contained in the composition according to any one of [1] to [5].
[7] A method for producing an optical film comprising the following (1) and (2):
(1) The process of apply | coating the composition in any one of [1]-[5] on a base material;
(2) The process of forming an optical film by superposing | polymerizing the polymeric component contained in the coating film apply | coated on the base material by (1).
[8] The method for producing an optical film according to [7], wherein the substrate is made of a material having a hydroxyl group.
[9] The method for producing an optical film according to [8], wherein the material having a hydroxyl group is a material obtained by saponifying triacetylcellulose.
[10] The method for producing an optical film according to any one of [7] to [9], wherein the substrate is provided with an alignment film formed of a photoalignable polymer on the surface thereof.
[11] The method for producing an optical film as described in [10], wherein the alignment film is provided by forming a crosslinked structure of the photoalignable polymer by light irradiation.
[12] An optical film obtained by the production method according to any one of [7] to [11].
[13] The optical film according to [6] or [12], which has retardation.
[14] A polarizing plate comprising the optical film according to [13].
[15] A flat panel display device comprising the optical film according to [6], [12] or [13].

  ADVANTAGE OF THE INVENTION According to this invention, the composition for optical film manufacture excellent in adhesiveness and the optical film formed by apply | coating this composition can be provided.

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

1. Composition (hereinafter, the composition of the present invention is sometimes referred to as “the present composition”, and an optical film produced from the present composition is sometimes referred to as “the present optical film”).
This composition comprises (A) a polymerizable liquid crystal compound, (B) a compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule (hereinafter, sometimes referred to as “compound (B)”). And (C) a photopolymerization initiator. The present invention provides the present composition, the present optical film, and the like. Hereinafter, the present invention will be described in detail with reference to the drawings as necessary. It should be noted that the dimensions and the like in the drawings are arbitrary for ease of viewing.

1-1. Compound (B)
As described above, the compound (B) has a carbon-carbon unsaturated bond and an active hydrogen reactive group in its molecule. The “active hydrogen reactive group” as used herein is a group reactive to a group having active hydrogen such as a carboxyl group (—COOH), a hydroxyl group (—OH), an amino group (—NH ₂ ), and the like. Typical examples include glycidyl group, oxazoline group, carbodiimide group, aziridine group, imide group, isocyanato group, thioisocyanato group, maleic anhydride group and the like. The number of carbon-carbon unsaturated bonds and active hydrogen reactive groups in the compound (B) is 1 to 20, preferably 1 to 10, respectively.

  In the compound (B), it is preferable that at least two active hydrogen reactive groups are present. In this case, a plurality of active hydrogen reactive groups may be the same or different.

  The carbon-carbon unsaturated bond that the compound (B) has may be a carbon-carbon double bond, a carbon-carbon triple bond, or a combination thereof, but is preferably a carbon-carbon double bond. Among them, the compound (B) preferably contains a carbon-carbon unsaturated bond as a vinyl group and / or a (meth) acryl group. Further, the active hydrogen reactive group is preferably at least one selected from the group consisting of an epoxy group, a glycidyl group and an isocyanato group, and a compound (B) having an acrylic group and an isocyanato group is particularly preferable.

  Specific examples of the compound (B) include compounds having a (meth) acryl group and an epoxy group, such as methacryloxyglycidyl ether and acryloxyglycidyl ether; (meth) acryl groups and oxetane, such as oxetane acrylate and oxetane methacrylate. A compound having a group; a compound having a (meth) acryl group and a lactone group, such as lactone acrylate and lactone methacrylate; a compound having a vinyl group and an oxazoline group, such as vinyl oxazoline and isopropenyl oxazoline; isocyanatomethyl acrylate Oligomers of compounds having a (meth) acryl group and an isocyanato group, such as isocyanatomethyl methacrylate, 2-isocyanatoethyl acrylate and 20 isocyanatoethyl methacrylate It is below. Moreover, the compound etc. which have vinyl groups, vinylene groups, and acid anhydrides, such as methacrylic anhydride, acrylic anhydride, maleic anhydride, and vinyl maleic anhydride, are mentioned. Among them, methacryloxyglycidyl ether, acryloxyglycidyl ether, isocyanatomethyl acrylate, isocyanatomethyl methacrylate, vinyl oxazoline, 2-isocyanatoethyl acrylate, 2-isocyanatoethyl methacrylate and the above oligomers are preferred, isocyanatomethyl acrylate, 2-isocyanatoethyl acrylate and the aforementioned oligomers are particularly preferred.

［式（Ｘ）中、
ｎは１〜１０までの整数を表わし、Ｒ^１’は、炭素数２〜２０の２価の脂肪族又は脂環式炭化水素基、或いは炭素数５〜２０の２価の芳香族炭化水素基を表わす。各繰り返し単位にある２つのＲ^２’は、一方が−ＮＨ−であり、他方がＮ−Ｃ（＝Ｏ）−Ｒ^３’で示される基である。Ｒ^３’は、水酸基又は炭素−炭素不飽和結合を有する基を表す。
式（Ｘ）中のＲ^３’のうち、少なくとも１つのＲ^３’は炭素−炭素不飽和結合を有する基である。］ Here, a compound having an isocyanato group as the active hydrogen reactive group and more preferable as the compound (B) is specifically shown. This preferable compound (B) is represented by the following formula (X), for example.

[In the formula (X),
n represents an integer of 1 to 10, and R ^{1 ′} is a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms, or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. Represents. Two R ^{2 ′ in} each repeating unit is a group represented by one —NH— and the other is N—C (═O) —R ^{3 ′} . R ^{3 ′} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
Of R ^{3 ′} in formula (X), at least one R ^{3 ′} is a group having a carbon-carbon unsaturated bond. ]

化合物（ＸＸ）は市場から容易に入手できる市販品をそのまま又は必要に応じて精製して用いることもできる。該市販品としては、例えば、Ｌａｒｏｍｅｒ（登録商標）ＬＲ−９０００（ＢＡＳＦ社製）等が挙げられる。 Among the compounds (B) represented by the formula (X), a compound represented by the following formula (XX) (hereinafter sometimes referred to as “compound (XX)”) is particularly preferable (n Is as defined above.

Compound (XX) may be a commercially available product that can be easily obtained from the market, or may be used after purification, if necessary. Examples of the commercially available product include Laromer (registered trademark) LR-9000 (manufactured by BASF).

  The content of the compound (B) in the present composition is expressed as a content ratio with respect to the total mass of the present composition, preferably in the range of 0.01 to 10% by mass, and more preferably in the range of 0.1 to 5% by mass. . If it is in the said range, the reactivity of the photo-alignment polymer in this composition will not be reduced.

1-2. Polymerizable liquid crystal compound The (A) polymerizable liquid crystal compound contained in the composition is a compound having a polymerizable group and exhibiting a liquid crystal state. The polymerizable group means a group involved in the polymerization reaction of the polymerizable liquid crystal compound.

［式（Ａ）中、
Ｘ^１は、酸素原子、硫黄原子又は−ＮＲ^１−を表す。Ｒ^１は、水素原子又は炭素数１〜４のアルキル基を表す。
Ｙ^１は、置換基を有していてもよい炭素数６〜１２の１価の芳香族炭化水素基、又は置換基を有していてもよい炭素数３〜１２の１価の芳香族複素環式基を表す。
Ｑ^３及びＱ^４は、それぞれ独立に、水素原子、置換基を有していてもよい炭素数１〜２０の１価の脂肪族炭化水素基、炭素数３〜２０の脂環式炭化水素基、置換基を有していてもよい炭素数６〜２０の１価の芳香族炭化水素基、ハロゲン原子、シアノ基、ニトロ基、−ＮＲ^２Ｒ^３又は−ＳＲ^２を表すか、Ｑ^３及びＱ^４が互いに結合して、これらがそれぞれ結合する炭素原子とともに芳香環又は芳香族複素環を形成している。Ｒ^２及びＲ^３は、それぞれ独立に、水素原子又は炭素数１〜６のアルキル基を表す。
Ｄ^１及びＤ^２は、それぞれ独立に、単結合、−Ｃ（＝Ｏ）−Ｏ−、−Ｃ（＝Ｓ）−Ｏ−、−ＣＲ^４Ｒ^５−、−ＣＲ^４Ｒ^５−ＣＲ^６Ｒ^７−、−Ｏ−ＣＲ^４Ｒ^５−、−ＣＲ^４Ｒ^５−Ｏ−ＣＲ^６Ｒ^７−、−ＣＯ−Ｏ−ＣＲ^４Ｒ^５−、−Ｏ−ＣＯ−ＣＲ^４Ｒ^５−、−ＣＲ^４Ｒ^５−Ｏ−ＣＯ−ＣＲ^６Ｒ^７−、−ＣＲ^４Ｒ^５−ＣＯ−Ｏ−ＣＲ^６Ｒ^７−又は−ＮＲ^４−ＣＲ^５Ｒ^６−又は−ＣＯ−ＮＲ^４−を表す。
Ｒ^４、Ｒ^５、Ｒ^６及びＲ^７は、それぞれ独立に、水素原子、フッ素原子又は炭素数１〜４のアルキル基を表す。
Ｇ^１及びＧ^２は、それぞれ独立に、炭素数５〜８の２価の脂環式炭化水素基を表し、該脂環式炭化水素基を構成するメチレン基は、酸素原子、硫黄原子又は−ＮＨ−に置き換っていてもよく、該脂環式炭化水素基を構成するメチン基は、第三級窒素原子に置き換っていてもよい。
Ｌ^１及びＬ^２は、それぞれ独立に、１価の有機基を表し、Ｌ^１及びＬ^２のうち少なくとも一方が、重合性基を有する有機基である。］ One suitable example of the polymerizable liquid crystal compound is, for example, one represented by the formula (A) (hereinafter sometimes referred to as “compound (A)”).

[In the formula (A),
X ¹ represents an oxygen atom, a sulfur atom, or —NR ¹ —. R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Y ¹ is a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a monovalent aromatic complex having 3 to 12 carbon atoms which may have a substituent. Represents a cyclic group.
Q ³ and Q ⁴ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 3 to 20 carbon atoms. Represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a halogen atom, a cyano group, a nitro group, —NR ² R ³ or —SR ² , or Q ³ and Q ⁴ are bonded to each other to form an aromatic ring or an aromatic heterocyclic ring together with the carbon atoms to which they are bonded. R ² and R ³ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, —C (═O) —O—, —C (═S) —O—, —CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —CR ⁶ R. ^{7 -, - O-CR 4} R 5 -, - CR 4 R 5 -O-CR 6 R 7 -, - CO-O-CR 4 R 5 -, - O-CO-CR 4 R 5 -, - CR ^{4 R 5 -O-CO-CR} 6 R 7 -, - CR 4 R 5 -CO-O-CR 6 R 7 - or ^-NR 4 ^-CR 5 ^{R 6} - or -CO-NR ⁴ - represents a.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the methylene group constituting the alicyclic hydrocarbon group is an oxygen atom, a sulfur atom or — NH- may be substituted, and the methine group constituting the alicyclic hydrocarbon group may be substituted with a tertiary nitrogen atom.
L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group. ]

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and a sec-butyl group. Among these, a C1-C3 alkyl group is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is especially preferable.

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

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

Of the substituent Z ¹ , the halogen atom may be any of a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, but is preferably a fluorine atom, a chlorine atom and a bromine atom.
Among the substituents Z ¹ , specific examples of the alkyl group include the same as those exemplified as the alkyl group for R ¹ . Among these, a methyl group and an ethyl group are more preferable, and a methyl group is particularly preferable.

Among the substituents Z ^1, the alkylsulfinyl group includes methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, Examples thereof include a pentylsulfinyl group and a hexylsulfinyl group. Among these, an alkylsulfinyl group having 1 to 4 carbon atoms is preferable, an alkylsulfinyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfinyl group is particularly preferable.

Among the substituents Z ¹ , the alkylsulfonyl group includes a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, Examples thereof include a pentylsulfonyl group and a hexylsulfonyl group. Among these, an alkylsulfonyl group having 1 to 4 carbon atoms is preferable, an alkylsulfonyl group having 1 to 2 carbon atoms is more preferable, and a methylsulfonyl group is particularly preferable.

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

Among the substituents Z ¹ , the alkoxy group includes a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. Is mentioned. Among these, an alkoxy group having 1 to 4 carbon atoms is preferable, an alkoxy group having 1 to 2 carbon atoms is more preferable, and a methoxy group is particularly preferable.

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

Of the substituents Z ¹ , the N-alkylamino group includes N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group. Group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, N-hexylamino group and the like. Among these, an N-alkylamino group having 1 to 4 carbon atoms is preferable, an N-alkylamino group having 1 to 2 carbon atoms is more preferable, and an N-methylamino group is particularly preferable.

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

Among the substituents Z ¹ , the N-alkylsulfamoyl group includes N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group and N-hexylsulfamoyl group Groups and the like. Among these, an N-alkylsulfamoyl group having 1 to 4 carbon atoms is preferable, an N-alkylsulfamoyl group having 1 to 2 carbon atoms is more preferable, and an N-methylsulfamoyl group is particularly preferable.

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

Although the substituents Z ^1, has been given the specific examples and preferred examples among these, substituents Z ¹ is a halogen atom, an alkyl group having 1 to 2 carbon atoms, cyano group, nitro group, C 1 -C ˜2 alkylsulfonyl group, C 1-2 fluoroalkyl group, C 1-2 alkoxy group, C 1-2 alkylsulfanyl group, C 1-2 N-alkylamino group, carbon number Preferred are an N, N-dialkylamino group having 2 to 4 carbon atoms and an alkylsulfamoyl group having 1 to 2 carbon atoms. A halogen atom, methyl group, cyano group, nitro group, sulfo group, carboxy group, trifluoromethyl group, methoxy group Particularly preferred are groups, methylsulfanyl groups, N, N-dimethylamino groups and N-methylamino groups.

［式（Ｙ−１）〜式（Ｙ−６）中、
＊は結合手を表し、Ｚ¹は前記置換基Ｚ¹を表す。
ａ１は０〜５の整数、ａ２は０〜４の整数、ｂ１は０〜３の整数、ｂ２は０〜２の整数をそれぞれ表す。Ｒ⁸は水素原子又はメチル基を表す。
なお、ａ１、ａ２、ｂ１及びｂ２が２以上の整数である場合、同一基に存在する複数のＺ¹は互いに同一であっても異なっていてもよい。］ When Y ¹ is a monocyclic aromatic hydrocarbon group which may have a substituent or a monocyclic aromatic heterocyclic group which may have a substituent, a preferred example thereof is represented by the formula ( Y-1) to groups represented by formula (Y-6), respectively.

[In Formula (Y-1)-Formula (Y-6),
* Represents a bond, and Z ¹ represents the substituent Z ¹ .
a1 represents an integer of 0 to 5, a2 represents an integer of 0 to 4, b1 represents an integer of 0 to 3, and b2 represents an integer of 0 to 2, respectively. R ⁸ represents a hydrogen atom or a methyl group.
When a1, a2, b1 and b2 are integers of 2 or more, a plurality of Z ¹ present in the same group may be the same or different from each other. ]

Among these, Y ¹ is particularly preferably a group represented by the formula (Y-1) or the formula (Y-3) in terms of easy production of the compound (A) and cost.

When Y ¹ is a polycyclic aromatic hydrocarbon group which may have a substituent or a polycyclic aromatic heterocyclic group which may have a substituent, a preferred example thereof is represented by the formula ( Groups represented by Y ¹ -1) to formula (Y ¹ -7), respectively.

［式（Ｙ¹−１）〜式（Ｙ¹−７）中、
＊は結合手を表し、Ｚ¹は前記置換基Ｚ¹を表す。
Ｖ¹及びＶ²は、それぞれ独立に、−ＣＯ−、−Ｓ−、−ＮＲ⁹−、−Ｏ−、−Ｓｅ−又は−ＳＯ₂−を表す。Ｒ⁹は、水素原子又は炭素数１〜４のアルキル基を表す。
Ｗ¹〜Ｗ⁵は、それぞれ独立に、−ＣＨ＝又は−Ｎ＝を表す。
ただし、Ｖ¹、Ｖ²及びＷ¹〜Ｗ⁵のうち少なくとも１つは、Ｓ、Ｎ、Ｏ又はＳｅといったヘテロ原子又は該へテロ原子を含む基を表す。
ａは、０〜３の整数を表す。
ｂは、０〜２の整数を表す。
なお、ａ、ｂが２以上の整数である場合、同一基に存在する複数のＺ¹は互いに同一であっても異なっていてもよい。］

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

V ¹ and V ² are each independently preferably —S—, —NR ⁹ — or —O—, and W ^{1 to} W ⁵ are each independently preferably —CH═ or —N═.
a is preferably 0 or 1, and b is preferably 0.

Furthermore, in the case where Y ¹ is a polycyclic aromatic hydrocarbon group which may have a substituent or a polycyclic aromatic heterocyclic group which may have a substituent, the formula ( Y ² -1) to a group represented by formula (Y ² -6) are more preferable.

［式（Ｙ²−１）〜式（Ｙ²−６）中、
＊、Ｚ¹、ａ、ｂ、Ｖ¹、Ｖ²及びＷ¹は、前記と同じ意味を表す。］

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

In the groups represented by the formulas (Y ² -1) to (Y ² -6), Z ¹ is a halogen atom, a methyl group, an ethyl group, an isopropyl group, a sec-butyl group, a cyano group, or a nitro group. Group, sulfo group, nitroso group, carboxy group, trifluoromethyl group, methoxy group, methylsulfanyl group, N, N-dimethylamino group and N-methylamino group are preferred, halogen atom, methyl group, ethyl group, isopropyl group , Sec-butyl group, cyano group, nitro group and trifluoromethyl group are more preferable, and methyl group, ethyl group, isopropyl group, sec-butyl group, pentyl group and hexyl group are particularly preferable.

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

Examples of the alicyclic hydrocarbon group represented by Q ³ and Q ⁴ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group. A cyclic alkyl group having a number of 3 to 12 is preferred.

Examples of the aromatic hydrocarbon group represented by Q ³ and Q ⁴ include a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-fluorenyl group, a 2-fluorenyl group, and a 3-fluorenyl group. And an aromatic hydrocarbon group having 6 to 14 carbon atoms is preferred.

The aliphatic hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group represented by Q ³ and Q ⁴ may each have a substituent. Examples of the substituent include those exemplified as Z ¹ .

R ² and R ³ are each an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group and an ethyl group, and particularly preferably a methyl group.

で示される部分構造が、式（Ｑ）で示される構造であるとより好ましい。

［式（Ｑ）中、
Ｘ²は、式（Ａ）中のＸ¹として例示した原子又は基と同じであり、Ｙ^２は、式（Ａ）中のＹ^１として例示した基と同じである。］ Here, Q ³ and Q ⁴ may be bonded to each other to form an aromatic ring or an aromatic heterocyclic ring. The ring formed by Q ³ and Q ⁴ is preferably an aromatic heterocyclic ring. For example, the compound represented by the formula (Q ′) in the compound (A)

The partial structure represented by is more preferably a structure represented by the formula (Q).

[In the formula (Q),
X ² is the same as the atom or group exemplified as X ¹ in formula (A), and Y ² is the same as the group exemplified as Y ¹ in formula (A). ]

As described above, each of X ¹ , Y ¹ , Q ³ and Q ⁴ has been described with specific examples. Specific examples of these combinations are represented by the formula (ar) in the compound (A).

で示される部分構造で表すと、以下の式（ａｒ−１）〜式（ａｒ−１３５）からなる群より選ばれるものを挙げることができる。

When represented by a partial structure represented by the formula, those selected from the group consisting of the following formulas (ar-1) to (ar-135) can be given.

  Among the partial structures represented by the above formula (ar), the compound (A) containing the structure represented by the formula (ar-86) is easier to produce the compound (A) itself, and the compound Since it is easy to control the wavelength dispersion of the retardation of the optical film formed from this composition containing (A), it is preferable.

D ¹ and D ² in the formula (A) are each independently —O—C (═O) —, —O—C (═S) —, —O—CR ⁴ R ⁵ —, —NR ⁴ —. CR ⁵ R ⁶ — or —NR ⁴ —CO— is preferred, more preferably * —O—C (═O) —, * —O—C (═S) —, * —O—CR ⁴ R ⁵ —, * —NR ⁴ —CR ⁵ R ⁶ — or * —NR ⁴ —CO—, more preferably * —O—C (═O) —, * —O—C (═S) — or * —NR ⁴ —CO -(Wherein * represents a bond to the benzene ring to which Q ¹ and Q ² are bonded in the partial structure represented by the formula (ar)).

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

The divalent alicyclic hydrocarbon group represented by G ¹ and G ² includes a monocyclic hydrocarbon group and a bridged cyclic hydrocarbon group, and is a 5-membered ring or a 6-membered ring. Is preferred. The alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a saturated alicyclic hydrocarbon group. In addition, the alicyclic hydrocarbon group represented by G ¹ and G ^{2 is the case} where —CH ₂ — constituting it is replaced by —O—, —S— or —NH—, or the methine constituting it. In some cases, the group may be replaced by a tertiary nitrogen atom. That is, G ¹ and G ² may be a group containing a hetero atom. Here, a specific example of G ¹ and G ^2, is represented respectively by the formulas (g-1) ~ formula (g-10).

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

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

L ¹ and L ² in the formula (A) are each independently a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group.
More preferably, L ¹ is a group represented by formula (A1) (hereinafter, sometimes referred to as “group (A1)”), and L ² is a group represented by formula (A2) (hereinafter, optionally). "Group (A2)").

P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) _l -E ^2- (A2)
[In Formula (A1) and Formula (A2),
^{B 1,} B 2, ^{E 1} and ^{E 2,} each _{^{independently, -CR 4 R 5 -, -}} CH 2 -CH 2 -, - O -, - S -, - CO-O -, - O-CO It represents —O—, —CS—O—, —O—CS—O—, —CO—NR ¹ —, —O—CH ₂ —, —S—CH ₂ — or a single bond.
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, and the alicyclic hydrocarbon The methylene group constituting the group may be replaced by an oxygen atom, a sulfur atom or -NH-, and the methine group constituting the alicyclic hydrocarbon group is replaced by a tertiary nitrogen atom. May be.
k and l each independently represents an integer of 0 to 3. When k is an integer of 2 or more, the plurality of B ¹ may be the same or different from each other, and the plurality of A ¹ may be the same or different from each other. When l is an integer of 2 or more, the plurality of B ² may be the same or different from each other, and the plurality of A ² may be the same or different from each other.
F ¹ and ^{F 2} represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ represents a polymerizable group.
P ² represents a hydrogen atom or a polymerizable group.
R ⁴ and R ⁵ represent the same meaning as described above. ]

In the groups (A1) and (A2), specific examples of the divalent alicyclic hydrocarbon group represented by A ¹ and A ² are the divalent alicyclic hydrocarbon groups of G ¹ and G ^2. The preferred examples are the same as the preferred examples of G ¹ and G ² . The divalent aromatic hydrocarbon group represented by A ¹ and A ² may be monocyclic or polycyclic (polycyclic or condensed with a plurality of aromatic rings linked by a single bond). Including polycyclic). Examples of the divalent aromatic hydrocarbon group represented by A ¹ and A ² include those represented by formula (a-1) to formula (a-8), respectively. In addition, the aromatic hydrocarbon group represented by A ¹ and A ² is preferably a group having a symmetry axis or a symmetry plane.

The hydrogen atom contained in the alicyclic hydrocarbon group and aromatic hydrocarbon group represented by A ¹ and A ² may be substituted with a substituent. Examples of the substituent include the same ones as those exemplified as the substituent Z ² which the alicyclic hydrocarbon group represented by G ¹ and G ² may optionally have.

A ¹ and A ² are each independently preferably a 1,4-phenylene group or cyclohexane-1,4-diyl. From the viewpoint of easier production of the compound (A), 1,4-phenylene is preferred. A phenylene group is preferred.

B ¹ and B ² are preferably the same type of group since the production of the compound (A) tends to be easy. Further, k, when l is an integer of 2 or more, B ^2, which is between B ^1, two A ² located between the two A ¹ _{are, -CH 2 -CH 2 -, -} C (= O ) —O—, —CO—NH—, —O—CH ₂ — or a single bond is preferred because the production of the compound (A) tends to be easier. From the viewpoint of easily forming the present optical film exhibiting high liquid crystallinity, B ^2, which is between B ^1, two A ² located between the two A ¹ are both, -C (= O) -O- in Preferably there is.
B ¹ bonded to F ¹ and B ² bonded to F ² are each independently —O—, —C (═O) —O—, —O—C (═O) —, It is more preferably —O—C (═O) —O—, —CO—NH—, —NH—CO— or a single bond.

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

F ¹ and F ² are each independently preferably an alkanediyl group having 1 to 12 carbon atoms, and more preferably a linear alkanediyl group. In particular, an unsubstituted alkanediyl group is preferred. The hydrogen atom contained in the alkanediyl group may be substituted with an alkoxy group having 1 to 5 carbon atoms or a halogen atom. In addition, —CH ₂ — constituting the alkanediyl group may be replaced with —O— or —C (═O) —.

P ¹ and P ² are a hydrogen atom or a polymerizable group, and at least one is a polymerizable group. In order to obtain the present optical film having more excellent hardness, the compound (A) in which P ¹ and P ² are both polymerizable groups is preferable.

Here, the polymerizable group means a characteristic group capable of polymerizing the compound (A), specifically, vinyl group, vinyloxy group, styryl group, p- (2-phenylethenyl) phenyl group, Polymerizable group having an ethylenically unsaturated group such as acryloyl group, methacryloyl group, acryloyloxy group, methacryloyloxy group; carboxy group; acetyl group; hydroxy group; carbamoyl group; alkylamino group having 1 to 4 carbon atoms; amino group Oxiranyl group; oxetanyl group, formyl group, isocyanato group, isothiocyanato group and the like.
As the polymerizable group, a radical polymerizable group and a cationic polymerizable group suitable for photopolymerizing the compound (A) are preferable, and an acryloyl group, a methacryloyl group, an acryloyloxy group, and a methacryloyloxy group are particularly preferable. Among them, the polymerizable group is preferably each independently an acryloyloxy group or a methacryloyloxy group, and particularly preferably an acryloyloxy group.

The group (A1) and the group (A2) have been described with reference to specific examples. However, in consideration of the ease of production of the compound (A), the group (A1) and the group (a2) are the same. That is, L ¹ and L ² are preferably the same.
Similarly, in compound (A), D ¹ and D ² are the same, and G ¹ and G ² are the same, that is, in compound (A), -D ¹ -G ¹ -L ¹ a group represented, if a group represented by -D ² -G ² -L ² are identical preferred. If it does in this way, a compound (A) can be manufactured more easily.

Specific examples of -D ¹ -G ¹ -L ¹ when L ¹ is a group represented by formula (A1), and -D ² when L ² is a group represented by formula (A2) examples of -G ² -L ^2, include groups represented by the following formulas (R-1) ~ formula (R-134).
In the formulas (R-1) to (R-134), n represents an integer of 2 to 12, preferably 3 to 10, and more preferably 4 to 8.

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

Examples of the compound (A) include the following compounds (i) to (xxvii). In Table 1, L ¹ represents -D ¹ -G ¹ -L ¹ , and L ² represents -D ² -G ² -L ² .

In Table 1, for example, the compound (A) represented by (i) (hereinafter, this compound (A) is referred to as “compound (xvi)” according to the numbers in Table 1) is represented by the formula (ar) partial structure represented in formula (ar-39) is a structure represented by ^the group mentioned above represented by ^{-D 1 -G 1 -L 1 (R} -1) ~ (R-48) , (R-56) ~ ( R-120) and (R-129) ~ a group selected from the group consisting of ^(R-131), a group represented by -D ^{2 -G} 2 -L 2 above The compounds which are groups selected from the group consisting of (R-1) to (R-48) and (R-56) to (R-131).
For example, in the compound (xvi), the partial structure represented by the formula (ar) is a structure represented by the formula (ar-39), and the group represented by -D ¹ -G ¹ -L ¹ is the above-described group. of (R-1) ~ (R -48), a group selected from the group consisting of (R-56) ~ (R -120) and (R-129) ~ (R -131), -D 2 - A compound in which the group represented by G ² -L ² is a group selected from the group consisting of the above (R-1) to (R-48) and (R-56) to (R-131); a structure represented by ^{ar-40), -D 1 -G} 1 group represented by -L ¹ are described above (R-1) ~ (R -48), (R-56) ~ (R- 120) and (R-129) ~ (a group selected from the group consisting of ^{R-131), -D 2 -G} 2 -L groups represented by ² described above (R-1) ~ (R- 48) and R-56) ~ (a mixture of a compound which is a group selected from the group consisting of R-131), i.e., Compound (xvi) means a mixture of two compounds (A).

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

  Further, examples of the compound (A) include those represented by formulas (A1) to (A61).

（式（Ａ１）中の２つの＊は、（Ａ１−１）〜（Ａ１−８）のいずれかの＊と結合している。）

(Two * in the formula (A1) are bonded to any one of (A1-1) to (A1-8).)

（式（Ａ２）中の２つの＊は、（Ａ２−１）〜（Ａ２−８）のいずれかの＊と結合している。）

(Two * s in the formula (A2) are bonded to any one of (A2-1) to (A2-8).)

（式（Ａ３）中の２つの＊は、（Ａ３−１）〜（Ａ３−８）のいずれかの＊と結合している。）

(Two * in the formula (A3) are bonded to any one of (A3-1) to (A3-8).)

（式（Ａ４）中の２つの＊は、（Ａ４−１）〜（Ａ４−８）のいずれかの＊と結合している。）

(Two * in the formula (A4) are bonded to any one of (A4-1) to (A4-8).)

（式（Ａ５）中の２つの＊は、（Ａ５−１）〜（Ａ５−８）のいずれかの＊と結合している。）

(Two * in the formula (A5) are bonded to any one of (A5-1) to (A5-8).)

（式（Ａ６）中の２つの＊は、（Ａ６−１）〜（Ａ６−８）のいずれかの＊と結合している。）

(Two * s in formula (A6) are bonded to any one of (A6-1) to (A6-8).)

（式（Ａ７）中の２つの＊は、（Ａ７−１）〜（Ａ７−８）のいずれかの＊と結合している。）

(Two * in the formula (A7) are bonded to any one of (A7-1) to (A7-8).)

（式（Ａ８）中の２つの＊は、（Ａ８−１）〜（Ａ８−８）のいずれかの＊と結合している。）

(Two * in the formula (A8) are bonded to any one of (A8-1) to (A8-8).)

（式（Ａ９）中の２つの＊は、（Ａ９−１）〜（Ａ９−８）のいずれかの＊と結合している。）

(Two * in the formula (A9) are bonded to any one of (A9-1) to (A9-8).)

（式（Ａ１０）中の２つの＊は、（Ａ１０−１）〜（Ａ１０−８）のいずれかの＊と結合している。）

(Two * in the formula (A10) are bonded to any one of (A10-1) to (A10-8).)

（式（Ａ１１）中の２つの＊は、（Ａ１１−１）〜（Ａ１１−８）のいずれかの＊と結合している。）

(Two * in the formula (A11) are bonded to any one of (A11-1) to (A11-8).)

（式（Ａ１２）中の２つの＊は、（Ａ１２−１）〜（Ａ１２−８）のいずれかの＊と結合している。）

(Two * s in formula (A12) are bonded to any one of (A12-1) to (A12-8).)

（式（Ａ１３）中の２つの＊は、（Ａ１３−１）〜（Ａ１３−８）のいずれかの＊と結合している。）

(Two * in the formula (A13) are bonded to any one of (A13-1) to (A13-8).)

（式（Ａ１４）中の２つの＊は、（Ａ１４−１）〜（Ａ１４−８）のいずれかの＊と結合している。）

(Two * in the formula (A14) are bonded to any one of (A14-1) to (A14-8).)

（式（Ａ１５）中の２つの＊は、（Ａ１５−１）〜（Ａ１５−８）のいずれかの＊と結合している。）

(Two * in the formula (A15) are bonded to any one of (A15-1) to (A15-8).)

（式（Ａ１６）中の２つの＊は、（Ａ１６−１）〜（Ａ１６−８）のいずれかの＊と結合している。）

(Two * in the formula (A16) are bonded to any one of (A16-1) to (A16-8).)

（式（Ａ１７）中の２つの＊は、（Ａ１７−１）〜（Ａ１７−８）のいずれかの＊と結合している。）

(Two * in the formula (A17) are bonded to any one of (A17-1) to (A17-8).)

（式（Ａ１８）中の２つの＊は、（Ａ１８−１）〜（Ａ１８−８）のいずれかの＊と結合している。）

(Two * in the formula (A18) are bonded to any one of (A18-1) to (A18-8).)

（式（Ａ１９）中の２つの＊は、（Ａ１９−１）〜（Ａ１９−８）のいずれかの＊と結合している。）

(Two * s in formula (A19) are bonded to any one of (A19-1) to (A19-8).)

（式（Ａ２０）中の２つの＊は、（Ａ２０−１）〜（Ａ２０−８）のいずれかの＊と結合している。）

(Two * in the formula (A20) are bonded to any one of (A20-1) to (A20-8).)

（式（Ａ２１）中の２つの＊は、（Ａ２１−１）〜（Ａ２１−８）のいずれかの＊と結合している。）

(Two * s in formula (A21) are bonded to any one of (A21-1) to (A21-8).)

（式（Ａ２２）中の２つの＊は、（Ａ２２−１）〜（Ａ２２−８）のいずれかの＊と結合している。）

(Two * in the formula (A22) are bonded to any one of (A22-1) to (A22-8).)

（式（Ａ２３）中の２つの＊は、（Ａ２３−１）〜（Ａ２３−８）のいずれかの＊と結合している。）

(Two * s in the formula (A23) are bonded to any one of (A23-1) to (A23-8).)

（式（Ａ２４）中の２つの＊は、（Ａ２４−１）〜（Ａ２４−８）のいずれかの＊と結合している。）

(Two * s in the formula (A24) are bonded to any one of (A24-1) to (A24-8).)

（式（Ａ２５）中の２つの＊は、（Ａ２５−１）〜（Ａ２５−８）のいずれかの＊と結合している。）

(Two * in the formula (A25) are bonded to any one of (A25-1) to (A25-8).)

（式（Ａ２６）中の２つの＊は、（Ａ２６−１）〜（Ａ２６−８）のいずれかの＊と結合している。）

(Two * in the formula (A26) are bonded to any one of (A26-1) to (A26-8).)

（式（Ａ２７）中の２つの＊は、（Ａ２７−１）〜（Ａ２７−８）のいずれかの＊と結合している。）

(Two * in the formula (A27) are bonded to any one of (A27-1) to (A27-8).)

（式（Ａ２８）中の２つの＊は、（Ａ２８−１）〜（Ａ２８−８）のいずれかの＊と結合している。）

(Two * s in formula (A28) are bonded to any one of (A28-1) to (A28-8).)

（式（Ａ２９）中の２つの＊は、（Ａ２９−１）〜（Ａ２９−８）のいずれかの＊と結合している。）

(Two * s in the formula (A29) are bonded to any one of (A29-1) to (A29-8).)

（式（Ａ３０）中の２つの＊は、（Ａ３０−１）〜（Ａ３０−８）のいずれかの＊と結合している。）

(Two * in the formula (A30) are bonded to any one of (A30-1) to (A30-8).)

（式（Ａ３１）中の２つの＊は、（Ａ３１−１）〜（Ａ３１−８）のいずれかの＊と結合している。）

(Two * in the formula (A31) are bonded to any one of (A31-1) to (A31-8).)

（式（Ａ３２）中の２つの＊は、（Ａ３２−１）〜（Ａ３２−８）のいずれかの＊と結合している。）

(Two * s in formula (A32) are bonded to any one of (A32-1) to (A32-8).)

（式（Ａ３３）中の２つの＊は、（Ａ３３−１）〜（Ａ３３−８）のいずれかの＊と結合している。）

(Two * in the formula (A33) are bonded to any one of (A33-1) to (A33-8).)

（式（Ａ３４）中の２つの＊は、（Ａ３４−１）〜（Ａ３４−８）のいずれかの＊と結合している。）

(Two * in the formula (A34) are bonded to any one of (A34-1) to (A34-8).)

（式（Ａ３５）中の２つの＊は、（Ａ３５−１）〜（Ａ３５−８）のいずれかの＊と結合している。）

(Two * in the formula (A35) are bonded to any one of (A35-1) to (A35-8).)

（式（Ａ３６）中の２つの＊は、（Ａ３６−１）〜（Ａ３６−８）のいずれかの＊と結合している。）

(Two * in the formula (A36) are bonded to any one of (A36-1) to (A36-8).)

（式（Ａ３７）中の２つの＊は、（Ａ３７−１）〜（Ａ３７−８）のいずれかの＊と結合している。）

(Two * s in formula (A37) are bonded to any one of (A37-1) to (A37-8).)

（式（Ａ３８）中の２つの＊は、（Ａ３８−１）〜（Ａ３８−８）のいずれかの＊と結合している。）

(Two * s in the formula (A38) are bonded to any one of (A38-1) to (A38-8).)

（式（Ａ３９）中の２つの＊は、（Ａ３９−１）〜（Ａ３９−８）のいずれかの＊と結合している。）

(Two * s in formula (A39) are bonded to any one of (A39-1) to (A39-8).)

（式（Ａ４０）中の２つの＊は、（Ａ４０−１）〜（Ａ４０−８）のいずれかの＊と結合している。）

(Two * s in formula (A40) are bonded to any one of (A40-1) to (A40-8).)

（式（Ａ４１）中の２つの＊は、（Ａ４１−１）〜（Ａ４１−８）のいずれかの＊と結合している。）

(Two * in the formula (A41) are bonded to any one of (A41-1) to (A41-8).)

（式（Ａ４２）中の２つの＊は、（Ａ４２−１）〜（Ａ４２−８）のいずれかの＊と結合している。）

(Two * in the formula (A42) are bonded to any one of (A42-1) to (A42-8).)

（式（Ａ４３）中の２つの＊は、（Ａ４３−１）〜（Ａ４３−８）のいずれかの＊と結合している。）

(Two * in the formula (A43) are bonded to any one of (A43-1) to (A43-8).)

（式（Ａ４４）中の２つの＊は、（Ａ４４−１）〜（Ａ４４−８）のいずれかの＊と結合している。）

(Two * in the formula (A44) are bonded to any one of (A44-1) to (A44-8).)

（式（Ａ４５）中の２つの＊は、（Ａ４５−１）〜（Ａ４５−８）のいずれかの＊と結合している。）

(Two * in the formula (A45) are bonded to any one of (A45-1) to (A45-8).)

（式（Ａ４６）中の２つの＊は、（Ａ４６−１）〜（Ａ４６−８）のいずれかの＊と結合している。）

(Two * in the formula (A46) are bonded to any one of (A46-1) to (A46-8).)

（式（Ａ４７）中の２つの＊は、（Ａ４７−１）〜（Ａ４７−８）のいずれかの＊と結合している。）

(Two * in the formula (A47) are bonded to any one of (A47-1) to (A47-8).)

（式（Ａ４８）中の２つの＊は、（Ａ４８−１）〜（Ａ４８−８）のいずれかの＊と結合している。）

(Two * s in the formula (A48) are bonded to any one of (A48-1) to (A48-8).)

（式（Ａ４９）中の２つの＊は、（Ａ４９−１）〜（Ａ４９−８）のいずれかの＊と結合している。）

(Two * in the formula (A49) are bonded to any one of (A49-1) to (A49-8).)

（式（Ａ５０）中の２つの＊は、（Ａ５０−１）〜（Ａ５０−８）のいずれかの＊と結合している。）

(Two * s in the formula (A50) are bonded to any one of (A50-1) to (A50-8).)

（式（Ａ５１）中の２つの＊は、（Ａ５１−１）〜（Ａ５１−８）のいずれかの＊と結合している。）

(Two * in the formula (A51) are bonded to any one of (A51-1) to (A51-8).)

（式（Ａ５２）中の２つの＊は、（Ａ５２−１）〜（Ａ５２−８）のいずれかの＊と結合している。）

(Two * s in formula (A52) are bonded to any one of (A52-1) to (A52-8).)

（式（Ａ５３）中の２つの＊は、（Ａ５３−１）〜（Ａ５３−８）のいずれかの＊と結合している。）

(Two * in the formula (A53) are bonded to any one of (A53-1) to (A53-8).)

（式（Ａ５４）中の２つの＊は、（Ａ５４−１）〜（Ａ５４−８）のいずれかの＊と結合している。）

(Two * in the formula (A54) are bonded to any one of (A54-1) to (A54-8).)

（式（Ａ５５）中の２つの＊は、（Ａ５５−１）〜（Ａ５５−８）のいずれかの＊と結合している。）

(Two * s in formula (A55) are bonded to any one of (A55-1) to (A55-8).)

（式（Ａ５６）中の２つの＊は、（Ａ５６−１）〜（Ａ５６−８）のいずれかの＊と結合している。）

(Two * s in formula (A56) are bonded to any one of (A56-1) to (A56-8).)

（式（Ａ５７）中の２つの＊は、（Ａ５７−１）〜（Ａ５７−８）のいずれかの＊と結合している。）

(Two * in the formula (A57) are bonded to any one of (A57-1) to (A57-8).)

（式（Ａ５８）中の２つの＊は、（Ａ５８−１）〜（Ａ５８−８）のいずれかの＊と結合している。）

(Two * in the formula (A58) are bonded to any one of (A58-1) to (A58-8).)

（式（Ａ５９）中の２つの＊は、（Ａ５９−１）〜（Ａ５９−８）のいずれかの＊と結合している。）

(Two * in the formula (A59) are bonded to any one of (A59-1) to (A59-8).)

（式（Ａ６０）中の２つの＊は、（Ａ６０−１）〜（Ａ６０−８）のいずれかの＊と結合している。）

(Two * s in formula (A60) are bonded to any one of (A60-1) to (A60-8).)

（式（Ａ６１）中の２つの＊は、（Ａ６１−１）〜（Ａ６１−８）のいずれかの＊と結合している。）

(Two * in the formula (A61) are bonded to any one of (A61-1) to (A61-8).)

  Moreover, the following can also be used as a compound (A).

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

The method for producing the compound (A) in the case where D ¹ and D ² are * —O—CO— will be briefly described. First, a compound represented by formula (1-1) (compound (1-1)) and a compound represented by formula (1-2) (compound (1-2)) were respectively prepared, and this compound (1 -1) and compound (1-2) are reacted to obtain the compound represented by formula (1-3) (compound (1-3)).

［式中、Ｘ¹、Ｙ¹、Ｑ¹、及びＱ²は、式（Ａ）中と同一の意味を表わす。］

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

［式中、Ｇ^１、Ｅ^１、Ａ^１、Ｂ^１、Ｆ^１、Ｐ^１及びｋは前記と同じ意味を表わす。］

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

［式中、Ｘ¹、Ｙ¹、Ｑ¹、Ｑ²、Ｇ^１、Ｅ^１、Ａ^１、Ｂ^１、Ｆ^１、Ｐ^１及びｋは前記と同じ意味を表わす。］

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

  Subsequently, a compound (A) can be manufactured by making the obtained compound (1-3) and the compound (compound (1-4)) represented by Formula (1-4) react.

［式中、Ｇ^２、Ｅ^２、Ａ^２、Ｂ^２、Ｆ^２、Ｐ^２及びｌは前記と同じ意味を表わす。］

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

  The reaction between the compound (1-1) and the compound (1-2) and the reaction between the compound (1-3) and the compound (1-4) can be carried out in the presence of an esterifying agent. preferable.

  Examples of the esterifying agent (condensing agent) include 1-cyclohexyl-3- (2-morpholinoethyl) carbodiimide met-para-toluenesulfonate, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1- Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (partially marketed as Water Soluble Carbodiimide), bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, bisisopropyl Carbodiimides such as carbodiimide; 2-methyl-6-nitrobenzoic anhydride, 2,2′-carbonylbis-1H-imidazole, 1,1′-oxalyldiimidazole, diphenylphosphoryl azide, 1 (4-nitro Enesulfonyl) -1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N, N ′, N′-tetramethyl-O— (N-succinimidyl) uronium tetrafluoroborate, N- (1,2,2,2-tetrachloroethoxycarbonyloxy) succinimide, N-carbobenzoxy Succinimide, O- (6-chlorobenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium tetrafluoroborate, O- (6-chlorobenzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium Xafluorophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate, 2-chloro- Examples thereof include 1-methylpyridinium iodide, 2-chloro-1-methylpyridinium paratoluene sulfonate, 2-fluoro-1-methylpyridinium paratoluene sulfonate, and trichloroacetic acid pentachlorophenyl ester. Among them, as a condensing agent, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, 1-ethyl-3- (3-dimethyl) are used because of their reactivity, cost, and a wide range of solvents. Aminopropyl) carbodiimide hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, bisisopropylcarbodiimide, and 2,2′-carbonylbis-1H-imidazole are preferred.

  When this composition contains a compound (A) as (A), the content represents the content rate with respect to solid content of this composition, and the range of 10-99.9 mass% is preferable, and 20-99. The range of mass% is more preferable, the range of 50 to 97 mass% is more preferable, and the range of 80 to 95 mass% is particularly preferable. When the content of the compound (A) is in the above range, the obtained optical film can perform uniform polarization conversion in a wide wavelength range. Here, solid content means the quantity remove | excluding the solvent mentioned later from this composition. In the present composition, compound (A) may be used alone, or two or more compounds (A) may be used in combination as represented by compound (xvi) in Table 1.

  As described above, the compound (A) preferable as the polymerizable liquid crystal compound (A) contained in the composition has been described with reference to specific examples, but the composition is a liquid crystal compound different from the compound (A) (hereinafter, In some cases, “compound (A ′)” may be contained. Specific examples of the compound (A ′) include “3.8.6 Network (fully crosslinked type)” of Liquid Crystal Handbook (Edited by Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd., October 30, 2000), Among the compounds described in "6.5. 1 Liquid crystal material b. Polymerizable nematic liquid crystal material", compounds having a polymerizable group, JP2010-31223A, JP2010-270108A, and JP2011. And polymerizable liquid crystal compounds described in JP-A-6360 and JP-A-2011-207765.

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

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

Examples of the aromatic hydrocarbon ring represented by A ¹¹ include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrolin ring, and examples of the aromatic heterocyclic ring include a furan ring, a pyrrole ring, a thiophene ring, and a pyridine ring. , Thiazole ring and benzothiazole ring. Among these, a benzene ring, a thiazole ring and a benzothiazole ring are preferable. Examples of the aromatic hydrocarbon ring or aromatic heterocyclic ring represented by A ¹¹ include divalent groups represented by formula (Ara-1) to formula (Ara-11), respectively.

［式（Ａｒａ−１）〜式（Ａｒａ−１１）中、
Ｘ³は、式（Ａ）中のＸ^３と同じ意味を表す。同一基中に存在する複数のＸ¹は互いに同一であっても異なっていてもよい。
Ｙ³は、式（Ａ）中のＹ¹として例示した基と同じものを表す。
Ｚ³は、式（Ａ）中のＺ¹として例示した基と同じものを表す。
Ｗ^ａ及びＷ^ｂは、それぞれ独立に、水素原子、シアノ基、メチル基又はハロゲン原子を表す。
ｍは、０〜６の整数を表す。
ｎは、０〜４の整数を表す。
ｏは、０〜２の整数を表す。
ｍ、ｎ及びｏが２以上の整数である場合、同一基中に存在する複数のＺ³は互いに同一であっても異なっていてもよい。］

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

As the aromatic hydrocarbon ring or aromatic heterocycle represented by A ¹¹ , groups represented by the formula (Ara-1) and the formula (Ara-7) are preferable, and specific examples thereof include the following groups. Is done.

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

Examples of the polymerizable group represented by P ¹¹ and P ¹² include the same groups as those exemplified as the polymerizable group represented by P ¹ and P ² of the compound (A). A photopolymerizable group is preferable because it can be polymerized (cured) at a lower temperature, and a radical polymerizable group or a cationic polymerizable group is more preferable. In particular, the handling is easy, and the production of the compound (3) is also easy. , P ¹¹ and P ¹² are preferably groups represented by formulas (P-1) to (P-5), respectively.

［式（Ｐ−１）〜（Ｐ−５）中、
Ｒ¹⁷〜Ｒ²¹はそれぞれ独立に、炭素数１〜６のアルキル基又は水素原子を表す。＊は、Ｂ¹¹との結合手を表す。］

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

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

  Examples of the compound (3) include the following.

  When this composition contains the compound (3) as (A), the content thereof is, for example, 90% of the compound (3) with respect to 100 parts by mass of the total amount of the compound (A) and the compound (3). It is not more than part by mass, preferably not more than 70 parts by mass, more preferably not more than 40 parts by mass. In addition, the wavelength dispersion characteristic of the optical film formed with this composition is controllable when this composition contains a compound (3) with a compound (A). Specifically, in the polymer (polymer of compound (A) or (co) polymer of compound (A) and compound (3)) contained in the optical film, a structure derived from compound (A). The present optical film having desired wavelength dispersion characteristics can be formed by the content of the unit and the content of the structural unit derived from the compound (3). When the content of the structural unit derived from the polymer compound (A) in the optical film is increased, the reverse wavelength dispersion characteristic tends to be exhibited. In order to form the present optical film having desired wavelength dispersion characteristics, about 2 to 5 kinds of the present compositions having different contents of structural units derived from the compound (A) are prepared. An optical film having the same film thickness is manufactured and the retardation value is obtained. Then, from the result, the correlation between the content of the structural unit derived from the compound (A) and the retardation value of the optical film is obtained, and from the obtained correlation, the desired retardation value is given to the optical film at the above film thickness. What is necessary is just to determine content of the structural unit derived from the compound (A) required in order to give.

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

  Examples of the alkylphenone compound include α-aminoalkylphenone compounds, α-hydroxyalkylphenone compounds, and α-alkoxyalkylphenone compounds.

  Examples of the α-aminoalkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2-benzyl. Examples include butan-1-one and 2-dimethylamino-1- (4-morpholinophenyl) -2- (4-methylphenylmethyl) butan-1-one, preferably 2-methyl-2-morpholino-1. -(4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, and the like. As the α-aminoalkylphenone compound, commercially available products such as Irgacure (registered trademark) 369, 379EG, 907 (above, manufactured by BASF Japan Ltd.), and Sequol (registered trademark) BEE (produced by Seiko Chemical Co., Ltd.) Also good.

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

  Examples of the α-alkoxyalkylphenone compound include diethoxyacetophenone and benzyldimethyl ketal. Commercially available products such as Irgacure 651 (above, manufactured by BASF Japan Ltd.) may be used as the α-alkoxyalkylphenone compound.

  The alkylphenone compound is preferably an α-aminoalkylphenone compound, and more preferably a compound represented by formula (C-1). If the photopolymerization initiator contained in the present composition is any of these compounds, the resulting optical film tends to be excellent in heat resistance and moist heat resistance.

［式（Ｃ−１）中、Ｑ³は、水素原子又はメチル基を表す。］

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

  Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

  Examples of the benzophenone compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and 3,3 ′, 4,4′-tetra (tert-butylperoxy). Carbonyl) benzophenone, 2,4,6-trimethylbenzophenone and the like.

  Examples of the oxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one- 2-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine and N-acetoxy-1- [9-ethyl-6 -{2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine and the like. As said oxime compound, you may use commercial items, such as Irgacure OXE-01, OXE-02 (above, the BASF Japan company make), N-1919 (made by ADEKA company).

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

  The content of the photopolymerization initiator in the present composition is represented by the content ratio with respect to the solid content of the present composition, and is preferably in the range of 0.1% by mass to 30% by mass, more preferably 0.5% by mass. It is the range of -10 mass%. If it is in the said range, when superposing | polymerizing the polymeric component contained in this composition, it can suppress more disturbing the orientation of a compound (A). In addition, solid content means the total remove | excluding low volatile components, such as an organic solvent, from this composition containing the solvent (organic solvent) etc. which are mentioned later.

1-4. Organic Solvent The composition preferably contains a solvent, particularly an organic solvent, in order to improve the operability of optical film production. As the organic solvent, (A) [polymerizable liquid crystal compound], compound (B), a photopolymerization initiator, and other organic solvents that can dissolve the constituent components of the present composition are preferable. Furthermore, polymerization of compound (A) and the like is preferable. A solvent inert to the polymerization reaction of the conductive liquid crystal compound is more preferable. Specifically, alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether and phenol; ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone , Ester solvents such as propylene glycol methyl ether acetate and ethyl lactate; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone and methyl isobutyl ketone; non-chlorine aliphatic such as pentane, hexane and heptane Hydrocarbon solvents; Non-chlorine aromatic hydrocarbon solvents such as toluene and xylene; Nitrile solvents such as acetonitrile; Tetrahydro Chlorinated solvents chloroform and chlorobenzene; run and ether solvents such as dimethoxyethane and the like. These organic solvents may be used alone or in combination of two or more. Among these organic solvents, alcohol solvents, ester solvents, ketone solvents, non-chlorine aliphatic hydrocarbon solvents and non-chlorine aromatic hydrocarbon solvents are preferable. In particular, the components constituting the composition are excellent in compatibility, and can be dissolved in alcohol solvents, ester solvents, ketone solvents, non-chlorine aliphatic hydrocarbon solvents, chlorine aromatic hydrocarbon solvents, and the like. Therefore, the present composition can be obtained which can be coated on a suitable base material and produced the present optical film without using a chlorinated solvent such as chloroform.

  In addition, when this composition contains the organic solvent, 10 mass parts-10000 mass parts are preferable with respect to 100 mass parts of solid content, More preferably, they are 100 mass parts-5000 mass parts. Moreover, the solid content concentration in this composition becomes like this. Preferably it is 2-50 mass%, More preferably, it is 5-50 mass%. The definition of this solid content is as above-mentioned.

  Moreover, this composition may contain additives, such as a photosensitizer, a leveling agent, and a chiral agent, as needed. Hereinafter, these additives that the composition may optionally contain will be described.

1-5. Photosensitizer Examples of the photosensitizer include xanthones such as xanthone and thioxanthone; anthracene having a substituent such as anthracene and alkyl ether; phenothiazine; and rubrene.
By using a photosensitizer, polymerization of the compound (A) or the like can be made highly sensitive. Moreover, as the usage-amount of a photosensitizer, it is 0.1 mass part-30 mass parts with respect to 100 mass parts of polymerizable liquid crystal compounds, especially a compound (A), Preferably 0.5 mass part- 10 parts by mass.

1-6. Leveling agent Examples of the leveling agent include organic modified silicone oil-based, polyacrylate-based and perfluoroalkyl-based leveling agents. Specifically, for example, DC3PA, SH7PA, DC11PA, SH28PA, SH29PA, SH30PA, ST80PA, ST86PA, SH8400, SH8700, FZ2123 (all are manufactured by Toray Dow Corning Co., Ltd.), KP321, KP323, KP324, KP326, KP340, KP341, X22-161A, KF6001 (all manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (all, Momentive Performance Materials Japan) Made by a limited liability company), Fluorinert (registered trademark) FC-72, FC-40, FC-43, FC-3283 (all above) (Manufactured by Tomo 3M Co., Ltd.), MegaFac (registered trademark) R-08, R-30, R-90, F-410, F-411, F-443, F-445, F -470, F-477, F-479, F-482, F-482 (all of which are manufactured by DIC Corporation), Ftop (trade name) EF301, EF303, EF351, EF352 (All from Mitsubishi Materials Electronics Chemical Co., Ltd.), Surflon (registered trademark) S-381, S-382, S-383, S-393, SC-101, SC-105, KH- 40, SA-100 (all are manufactured by AGC Seimi Chemical Co., Ltd.), trade names E1830, E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.), BM-1000, BM-1100, BYK-352, BYK-3 3, BYK-361N (both trade name: BM Chemie Co., Ltd.), and the like. These leveling agents may be used alone or in combination of two or more.

  By using a leveling agent, the obtained optical film can be further smoothed. Furthermore, in the production process of the optical film, the fluidity of the composition (A) can be controlled, or the crosslinking density of the optical film obtained by polymerizing the compound (A) or the like can be adjusted. Moreover, the usage-amount of a leveling agent is 0.1-30 mass parts with respect to 100 mass parts of polymerizable liquid crystal compounds, especially a compound (A), Preferably it is 0.1-10 mass parts. is there.

1-7. Chiral agent As the chiral agent, a known chiral agent (for example, described in Liquid Crystal Device Handbook, Chapter 3-4-3, TN, chiral agent for STN, 199 pages, edited by Japan Society for the Promotion of Science, 142nd Committee, 1989) Can be used.
The chiral agent generally contains an asymmetric carbon atom, but an axially asymmetric compound or a planar asymmetric compound containing no asymmetric carbon atom can also be used as the chiral agent. Examples of the axial asymmetric compound or the planar asymmetric compound include binaphthyl, helicene, paracyclophane, and derivatives thereof.
For example, JP 2007-269640 A, JP 2007-269639 A, JP 2007-176870 A, JP 2003-137879 A, JP 2000-51596 A, JP 2007-169178 A, A compound as described in JP-T-9-506088 is exemplified, and preferably, paliocolor (registered trademark) LC756 manufactured by BASF Japan Ltd. is used.
The usage-amount of a chiral agent is 0.1 mass part-30 mass parts, for example with respect to 100 mass parts of compounds (A), for example, Preferably they are 1.0 mass part-25 mass parts. If it is in the said range, when superposing | polymerizing the polymeric component contained in this composition, it can suppress more disturbing the orientation of a compound (A).

2. Optical Film Subsequently, an optical film (present optical film) formed from the present composition will be described.
This optical film is obtained by polymerizing the polymerizable component (polymerizable liquid crystal compound) contained in the above-described composition. The present optical film is a film that can transmit light and has an optical function. The optical function means refraction, birefringence and the like.

  Among the present optical films, those excellent in transparency in the visible light region are preferable because they can be used as various display device members. The thickness of the optical film can be appropriately adjusted depending on the use of the optical film. For example, the thickness of the optical film may be appropriately adjusted depending on the retardation value, but is preferably 0.1 μm to 10 μm, and reduces the photoelasticity. More preferably, it is 0.2 μm to 5 μm.

  When using this optical film for a display device, this optical film can be used as a single layer, or a plurality of the optical films may be laminated to form a laminate, or may be combined with other films. By using in combination with other films, it can be used for retardation films, viewing angle compensation films, viewing angle widening films, antireflection films, polarizing films, circularly polarizing films, elliptically polarizing films, brightness enhancement films, and the like.

  In particular, the present optical film uses the compound (A) and the compound (3) as (A) of the present composition, and changes the optical properties depending on the orientation state of both, thereby obtaining a VA (vertical alignment) mode, It can be adjusted as a retardation film for various liquid crystal display devices such as an IPS (in-plane switching) mode, an OCB (optically compensated bend) mode, a TN (twisted nematic) mode, and an STN (super twisted nematic) mode.

2-1. Retardation film A retardation film which is a kind of optical film is one of the preferred embodiments of the present optical film. The retardation film is used for converting linearly polarized light into circularly polarized light or elliptically polarized light, or conversely converting circularly polarized light or elliptically polarized light into linearly polarized light, or changing the polarization direction of linearly polarized light.

As the retardation film, the refractive index in a slow axis direction in a plane n _x, the refractive index n _y in the direction (fast axis direction) perpendicular to the slow axis in the plane, the refractive index in the thickness direction It is known that _nz can be classified as follows. That is,
positive A plate of _{n x> n y ≒ n z} ,
negative C plate of _{n x ≒ n y> n z} ,
positive C plate of _{n x ≒ n y <n z} ,
A positive O plate and a negative O plate where n _x ≠ _ny ≠ _nz are listed.

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

In addition, a film thickness can be prepared so that a desired phase difference may be given by adjusting suitably content of the compound (A) and compound (3) which are contained in this composition. Since the retardation value (retardation value, Re (λ)) of the obtained retardation film is determined as shown in Equation (4), Δn (λ) is obtained in order to obtain a desired Re (λ). The film thickness d may be adjusted as appropriate.
Re (λ) = d × Δn (λ) (4)
(In the formula, Re (λ) represents a retardation value at a wavelength λnm, d represents a film thickness, and Δn (λ) represents a birefringence at a wavelength λnm.)

2-2. Production method of the present optical film The present optical film is produced by preparing an appropriate base material, applying the present composition on the base material, drying it, and polymerizing a polymerizable component contained in the present composition. be able to. Hereinafter, an example of the manufacturing method of this optical film is demonstrated. As described above, the polymerizable component is preferably the compound (A) or a mixture of the compound (A) and the compound (3).

2-2-0. Preparation of base material As a base material which can be used for manufacture of this optical film, glass, a plastic sheet, a plastic film, and a translucent film are preferable, for example. Examples of the translucent film include polyolefin films such as polyethylene, polypropylene and norbornene polymers; polyvinyl alcohol films; polyethylene terephthalate films; polymethacrylate films; polyacrylate films; cellulose ester films; Polycarbonate film; polysulfone film; polyethersulfone film; polyetherketone film; polyphenylene sulfide film and polyphenylene oxide film.

  As a base material used for manufacture of this optical film, what consists of a material which has a hydroxyl group is preferable, and it is more preferable that it is a film consisting of the material which has a hydroxyl group. The film made of a material having a hydroxyl group may be a film obtained by forming a material having a hydroxyl group, and after forming a material having a hydroxyl group precursor into a film (precursor film), The precursor group contained may be modified to a hydroxyl group. Such reforming includes, for example, plasma treatment under vacuum or atmospheric pressure, laser treatment, ozone treatment, saponification treatment, or flame treatment. In addition, a film made of a material having no hydroxyl group or precursor group thereof is prepared, a primer treatment for applying a coupling agent to the film surface, a monomer having a hydroxyl group or a polymer having a hydroxyl group is attached to the surface, radiation, It may be obtained by a method of graft polymerization in which plasma and ultraviolet rays are irradiated and reacted. In this case, a material having a hydroxyl group is arranged on the film surface, but even such a film is referred to as a film made of a material having a hydroxyl group in this specification. As described above, when a film (base material) made of a material having a hydroxyl group is used, the adhesion between the base material and the present optical film tends to be higher.

  Among films (base materials) made of a material having a hydroxyl group, a film obtained by subjecting a triacetyl cellulose film to a saponification treatment is preferable. By saponifying the triacetyl cellulose film, the triacetyl cellulose in the film is saponified, and a film made of a material having a hydroxyl group can be easily obtained, particularly in terms of cost and handling during production. preferable.

  Moreover, it is preferable that an alignment film is provided on the surface of the base material used for manufacturing the optical film on which the optical film is formed. Thus, the polymerizable liquid crystal compound can be polymerized after the (A) polymerizable liquid crystal compound in the optical film is aligned in a desired direction depending on the alignment direction of the alignment film. In the case of using a base material made of a material having a hydroxyl group, an alignment film may be provided on the base material. Details of the alignment film will be described later.

2-2-1. Preparation of an unpolymerized film By apply | coating this composition on a base material, an unpolymerized film is obtained on this base material. When the unpolymerized film exhibits a liquid crystal phase such as a nematic phase, it has birefringence due to monodomain alignment.

  Examples of the method for applying the composition onto a substrate include extrusion coating, direct gravure coating, reverse gravure coating, CAP (cap) coating, die coating, ink jet, dip coating, and slit coating. Method, spin coating method, and application by a bar coater. Among these, application by a CAP coating method, an inkjet method, a dip coating method, a slit coating method, a die coating method, and a bar coater is preferable in that the present composition can be continuously applied on a substrate in a RolltoRoll format.

  This optical film can also be handled in a state of being laminated with the base material. By laminating the base material on the optical film, the optical film is prevented from being damaged when the film is transported or stored, and can be easily handled.

  As described above, when the present optical film is produced, the substrate is used as it is or after the alignment film is formed on the substrate, and then the present composition is applied. It is preferable to apply the present composition on the alignment film after forming the alignment film. By using the base material on which the alignment film is formed in this way, it is not necessary to control the refractive index by stretching with respect to the present optical film, so that in-plane variation in birefringence is reduced. Therefore, it is possible to manufacture a large optical film that can cope with an increase in the size of a flat panel display (FPD).

  As a method for forming an alignment film, a method using an alignment polymer that imparts an alignment regulating force by rubbing (hereinafter referred to as “rubbing method” in some cases), or a light that imparts an alignment regulating force by irradiating polarized light. A method using an orientation polymer (hereinafter, sometimes referred to as “photo-alignment method”), a method of obliquely depositing silicon oxide on the surface of a substrate, and a long-chain alkyl group using a Langmuir-Blodgett method (LB method). Examples thereof include a method for forming a monomolecular film. Among these, the photo-alignment method is more preferable from the viewpoint of the alignment uniformity of the polymerizable liquid crystal compound such as the compound (A) contained in the present composition, the processing time and the processing cost of the present optical film production. The alignment film preferably has a solvent resistance that does not dissolve in components contained in the composition, for example, the solvent contained in the composition, even if the composition is applied thereon. Further, the alignment film has a solvent removal from the undried film and (A) a polymerizable liquid crystal compound (compound (A) or a mixture of compound (A) and compound (3)) during liquid crystal alignment. Heat resistance against heat treatment is also required.

  When the alignment film is formed by a photo-alignment method, examples of the photo-alignment polymer used in the photo-alignment method include a polymer having a photosensitive structure. When a polymer having a photosensitive structure is irradiated with polarized light, the photosensitive structure in the irradiated portion is isomerized or cross-linked so that the photo-alignable polymer is aligned, and an alignment regulating force is imparted to the film made of the photo-alignable polymer. The Examples of the photosensitive structure include an azobenzene structure, a maleimide structure, a chalcone structure, a cinnamic acid structure, a 1,2-vinylene structure, a 1,2-acetylene structure, a spiropyran structure, a spirobenzopyran structure, and a fulgide structure. . These polymers may be used alone or in combination of two or more. These polymers are obtained by using a monomer having a photosensitive structure by polycondensation such as dehydration or deamination, chain polymerization such as radical polymerization, anionic polymerization, or cationic polymerization, coordination polymerization, or ring-opening polymerization. be able to. Further, a plurality of monomers having different photosensitive structures may be used, and their copolymers may be used. Examples of such photo-alignable polymers include Japanese Patent No. 4450261, Japanese Patent No. 4011652, Japanese Patent Application Laid-Open No. 2010-49230, Japanese Patent No. 444090, Japanese Patent Application Laid-Open No. 2007-156439, Japanese Patent Application Laid-Open No. 2007-232934, and the like. Mention may be made of the photoalignable polymers described.

  As the photo-alignment polymer, a film that forms a crosslinked structure by light irradiation is preferable. Any material that forms a crosslinked structure is preferred in that sufficient durability can be secured when the composition is applied.

  In order to form an alignment film on a substrate, the photo-alignment polymer is a solution (orientation film forming composition) dissolved in a solvent, and the alignment film forming composition is applied onto the substrate. The method is simple and preferred. The solvent used in the composition for forming an alignment film can be appropriately selected depending on the type of the alignment polymer and the photo-alignment polymer dissolved in the solvent. Specifically, water, methanol, ethanol, ethylene glycol, isopropyl alcohol, Alcohol solvents such as propylene glycol, ethylene glycol methyl ether, ethylene glycol butyl ether or propylene glycol monomethyl ether; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate or ethyl lactate; Ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone or methyl isobutyl ketone; pentane, hexane or hepta Toluene or an aromatic hydrocarbon solvent such as xylene, nitrile solvents such as acetonitrile; aliphatic hydrocarbon solvents like ether solvents such as tetrahydrofuran or dimethoxyethane; chlorinated solvents chloroform or chlorobenzene; and the like. These organic solvents may be used alone or in combination of two or more.

  In order to form an alignment film from the alignment film forming composition, as described above, first, the alignment film forming composition is applied onto the substrate. As a coating method, the same method as exemplified as a method for coating the above-described composition on a substrate can be employed. Also in this case, a method in which the present composition can be continuously applied onto a substrate in the RolltoRoll format is preferable in terms of commercial production.

  Subsequently, the coating film (alignment film forming coating film) obtained by coating the alignment film forming composition on the substrate is dried, and low-boiling components such as a solvent contained in the alignment film forming composition are aligned. Remove from the film-forming coating film.

  Examples of the drying method include natural drying, ventilation drying, heat drying, reduced pressure drying, and the like, or a combination thereof. The specific drying temperature is preferably 10 to 250 ° C, and more preferably 25 to 200 ° C. The drying time is preferably 5 seconds to 60 minutes, more preferably 10 seconds to 30 minutes, although it depends on the type of solvent contained in the alignment film forming composition used. When the drying temperature and the drying time are within the above ranges, damage to the base material can be suppressed when any of the base materials is used.

  Thus, the alignment film is formed by applying the alignment regulating force to the coating film for forming the alignment film formed on the substrate by the method described above. Here, the photo-alignment method exemplified as a preferable method for imparting the alignment regulating force will be described in detail.

  In order to impart the alignment regulating force by the photo-alignment method, polarized light irradiation (for example, linearly polarized ultraviolet rays) is performed on the alignment film forming coating film. The polarized light irradiation can be performed using, for example, an apparatus described in JP-A-2006-323060. For example, on the alignment film forming coating film, for example, by preparing a photomask corresponding to a desired plurality of regions, and repeatedly performing polarized light irradiation (for example, linearly polarized ultraviolet rays) through the photomask for each region, A patterned alignment film can be formed. As said photomask, what provided the light-shielding pattern on films, such as quartz glass, soda-lime glass, or polyester, is mentioned, for example. The exposed light is blocked in the portion covered with the light shielding pattern, and the exposed light is transmitted in the uncovered portion. Since the influence of thermal expansion is small, quartz glass is preferable as the substrate used for the photomask.

  A patterned alignment film can be formed by a photo-alignment method. Here is an example. First, an alignment film forming coating film (including a photo-alignment polymer) is passed through a first photomask having a void corresponding to the first pattern region (the remaining region is a light-shielding pattern). The first polarized light having the first polarization direction is irradiated (first polarized light irradiation). By this first polarized light irradiation, the direction of the orientation regulating force of the first pattern region is made to correspond to the first polarized light direction. Next, a second polarization direction (which is different from the first polarization direction) is passed through a second photomask having a gap corresponding to the second pattern region (the remaining region is a light-shielding pattern). For example, the second polarized light having a direction perpendicular to the first polarization direction is irradiated (second polarized light irradiation). By this second polarized light irradiation, the direction of the orientation regulating force of the second pattern region is made to correspond to the second polarized light direction. As a result, an alignment film having a plurality of pattern regions with different directions of alignment regulating force can be obtained. Furthermore, a patterned alignment film having three or more pattern regions having different orientation regulating force directions can be formed by repeatedly performing polarized light irradiation through three or more types of photomasks. In view of the reactivity of the photo-alignment polymer, it is preferable that the irradiated light is ultraviolet light for each irradiation with polarized light.

  Thus, the film thickness of the alignment film or the patterned alignment film formed on the substrate is, for example, 10 nm to 10000 nm, preferably 10 nm to 1000 nm. With such a range, the polymerizable liquid crystal compound (A) (compound (A) or a mixture of the compound (A) and the compound (3))) contained in the composition can be oriented at a desired angle. it can.

2-2-2. Polymerization of unpolymerized film Polymerize a polymerizable liquid crystal compound [compound (A) or a mixture of compound (A) and compound (3)] contained in the unpolymerized film formed on a substrate or an alignment film. And this optical film is obtained by making it harden | cure. In this optical film, the orientation of the polymerizable liquid crystal compound is fixed, and the optical film is not easily affected by changes in birefringence due to heat.

  As a method for polymerizing the compound (A) or the compound (A) and the compound (3), a photopolymerization method is preferable. According to the photopolymerization method, since the polymerization can be carried out at a low temperature, the selection range of the heat resistance of the substrate to be used is expanded. The photopolymerization reaction is performed by irradiating an unpolymerized film with visible light, ultraviolet light, or laser light. In view of handling, ultraviolet light is particularly preferable.

The unpolymerized film formed by applying the present composition on the substrate or the alignment film can be irradiated with light as it is to cure the unpolymerized film, but the unpolymerized film is dried. It is preferable to remove the solvent from the unpolymerized film.
The solvent may be removed in parallel with the polymerization reaction, but it is preferable to remove most of the solvent before the polymerization. As the removal method, the same method as exemplified as the drying method in the method of forming the alignment film is employed. Among these, natural drying or heat drying is preferable, and the temperature at the time of natural drying or heat drying is preferably in the range of 0 ° C to 250 ° C, more preferably in the range of 50 ° C to 220 ° C, and in the range of 80 ° C to 170 ° C. Is more preferable. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. As long as the heating temperature and the heating time are within the above ranges, a substrate that does not necessarily have sufficient heat resistance can be used.

  Thus, the optical film formed on the base material, preferably the base material provided with the orientation film (the orientation film-containing base material) is a retardation plate having retardation (hereinafter referred to as “this retardation”. It is called a “board”. The retardation film is one of the preferred embodiments using the optical film. The retardation plate is used for converting linearly polarized light into circularly polarized light or elliptically polarized light, or conversely converting circularly polarized light or elliptically polarized light into linearly polarized light, or converting the polarization direction of linearly polarized light.

  Moreover, after polymerizing the compound (A) and the like to cure the unpolymerized film, the substrate is peeled off to obtain a film (laminated film) in which the alignment film and the present optical film are laminated. Further, the alignment film can be peeled off to obtain a single-layer optical film. Further, after another substrate (film or plate) is bonded to the laminated film, the substrate or the alignment film laminated on the optical film can be peeled off to perform transfer. .

3. Polarizing plate The optical film can be used, for example, for producing a polarizing plate. The polarizing plate preferably has at least one of the above-described retardation plates. Here, the structure of the polarizing plate using the present retardation plate in which the substrate / alignment film / present optical film is laminated will be described.
As this polarizing plate, as shown in FIGS. 1 (a) to 1 (e), (1) a polarizing plate 4a (FIG. 1 (a)) in which the retardation film 1 and the polarizing film layer 2 are directly laminated. )); (2) Polarizing plate 4b (FIG. 1 (b)) in which the retardation film 1 and the polarizing film layer 2 are bonded together through an adhesive layer 3 ′; (3) the retardation film 1 and the main plate A polarizing plate 4c (FIG. 1 (c)) in which the retardation plate 1 ′ is laminated and the retardation plate 1 ′ and the polarizing film layer 2 are laminated; (4) The retardation plate 1 and the retardation plate 1 And a polarizing plate 4d (FIG. 1 (d)) in which a polarizing film layer 2 is laminated on the retardation film 1 ′; and (5) the retardation film 1 And the retardation plate 1 ′ bonded via the adhesive layer 3, and further the polarized light obtained by bonding the retardation plate 1 ′ and the polarizing film layer 2 via the adhesive layer 3 ′. 4e (FIG. 1 (e)), and the like. Here, the adhesive is a generic term for an adhesive and / or an adhesive. In the description of FIG. 1, the substrate provided with the alignment film, that is, the alignment film-containing substrate is described. However, the alignment film-containing substrate can be replaced with a substrate not provided with the alignment film.

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

  Moreover, the polarizing film layer 2 may further include a film serving as a protective film, if necessary. Examples of the protective film include polyolefin films such as polyethylene, polypropylene and norbornene polymers, polyethylene terephthalate films, polymethacrylate films, polyacrylate films, cellulose ester films, polyethylene naphthalate films, polycarbonate films, and polysulfone films. , Polyethersulfone film, polyetherketone film, polyphenylene sulfide film and polyphenylene oxide film.

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

4). Flat panel display device In the flat panel display device of the present invention, the optical film is extremely useful as a member related to a flat panel display device. For example, a liquid crystal display device including a liquid crystal panel in which the present optical film and a liquid crystal panel are bonded together, or an organic electroluminescence (hereinafter also referred to as “EL”) panel in which the optical film of the present invention and a light emitting layer are bonded together. And an organic EL display device. A liquid crystal display device and an organic EL display device will be briefly described as embodiments of the flat panel display device of the present invention.

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

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

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

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

Synthesis of 1-1.4,6-dimethylbenzofuran-2-carboxylic acid 146.6 g of 4,6-dimethylsalicylaldehyde and 330.7 g of potassium carbonate were dispersed in 700 mL of N, N′-dimethylacetamide. The obtained dispersion was heated to 80 ° C., and then 190.5 g of tert-butyl bromoacetate was added dropwise over 30 minutes. The mixed solution after dropping was reacted at 130 ° C. for 2 hours. After cooling the reaction solution to room temperature, 600 mL of methyl isobutyl ketone was added and washed with 1200 mL of pure water. Further, the organic layer was washed twice with 1000 mL of pure water to recover the organic layer. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 240 g of acetic acid, 72 g of an aqueous hydrobromic acid solution was added, and the mixture was stirred at 40 ° C. for 1 hour. After cooling to room temperature, 150 g of 1N (1 mol / L) -hydrochloric acid was added, and the precipitated white powder was collected by filtration. The obtained white powder was further washed with 1N-hydrochloric acid and then vacuum-dried to obtain 81.7 g of 4,6-dimethylbenzofuran-2-carboxylic acid as a yellow powder. The yield was 44% based on 4,6-dimethylsalicylaldehyde.

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

1-3. Synthesis of Compound (11-b) 123 g of Compound (11-a), 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide (Lawson reagent) 9 .2 g and 1200 g of toluene were mixed. The obtained mixture was heated to 110 ° C. and reacted at the same temperature for 8 hours. After cooling to room temperature, it was washed with a 1N aqueous sodium hydroxide solution. The organic layer was collected and 800 mL of n-heptane was added. The deposited yellow precipitate was collected by filtration, washed with n-heptane, and vacuum dried to obtain 109.2 g of compound (11-b) as a bright yellow powder. The yield was 85% based on the compound (11-a).

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

1-5. Synthesis of Compound (11-d) 40 g of Compound (11-c) and 400 g (10 times mass) of pyridinium chloride were mixed, and the resulting mixture was heated to 180 ° C. and reacted at the same temperature for 3 hours. The obtained mixed solution was added to ice, and the deposited precipitate was collected by filtration. The suspension was washed with water, washed with toluene, and vacuum-dried to obtain 36.6 g of a yellow solid mainly composed of compound (11-d). The yield was 99% based on the compound (11-c).

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

1-7. Synthesis of Compound (A11-1) 35 g of Compound (11-d), 98.8 g of Compound (R-1a), 1.37 g of dimethylaminopyridine and 700 mL of toluene were mixed. 55.6 g of N, N′-dicyclohexylcarbodiimide was added to the resulting mixture under ice cooling. The resulting reaction solution was reacted at room temperature overnight, filtered using a filter medium precoated with silica gel, and then concentrated under reduced pressure. Methanol was added to the residue for crystallization. The crystals were collected by filtration, redissolved in chloroform, added with 2.3 g of activated carbon, and stirred at room temperature for 1 hour. The solution was filtered, and the filtrate was concentrated under reduced pressure with an evaporator until the volume was reduced to 1/3. Methanol was added with stirring, the precipitated white precipitate was collected by filtration, washed with heptane, and dried in vacuo. 74.5 g of A11-1) was obtained as a white powder. The yield was 60% based on the compound (11-d).

1-8. Synthesis of Compound (ix-1) Compound (ix-1) was synthesized by the method described in JP2010-31223A.

1-9. Synthesis of photoalignable polymer (Z) The photoalignable polymer (Z) was produced by the method described in Macromol. Chem. Phys. 197, 1919-1935 (1996).
A monomer represented by the formula (Za) is dissolved in 1.5 parts of the obtained monomer (Za) and 0.1 part of methyl methacrylate in 16 parts of tetrahydrofuran and reacted at 60 ° C. for 24 hours. It was. Next, the reaction solution was allowed to cool to room temperature and then dropped into a mixed solution of toluene and methanol to obtain a photoalignable polymer (Z). The number-average molecular weight of the photoalignable polymer (Z) was 33,000. In the photoalignable polymer (Z), the content of the structure derived from the monomer (Za) was 75 mol%.

The number average molecular weight (Mn) in terms of polystyrene of the obtained photo-alignable polymer (Z) was measured using the GPC method under the following conditions.
Device: HLC-8220GPC (manufactured by Tosoh Corporation)
Column; TOSOH TSKgel MultiporeH _XL- M
Column temperature: 40 ° C
Solvent; THF (tetrahydrofuran)
Flow rate: 1.0 mL / min
Detector; RI
Standard material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-5000, A-500

2. Composition Preparation Examples 1-3, Comparative Example 1
Each component shown in Table 2 was mixed, and the resulting solution was stirred at 80 ° C. for 1 hour, and then cooled to room temperature to prepare a composition.

表２中、光重合開始剤は、Ｉｒｇ３６９（イルガキュア３６９（ＢＡＳＦジャパン社製））、レベリング剤には、ＢＹＫ３６１Ｎ（ビックケミージャパン製）、溶剤はトルエン及びシクロペンタノンを用いた。また、化合物（１）における、重合性液晶化合物（ＬＣ２４２）はＢＡＳＦ社製で、下記式の化合物である。

In Table 2, Irg369 (Irgacure 369 (manufactured by BASF Japan)) was used as a photopolymerization initiator, BYK361N (manufactured by BYK Japan) was used as a leveling agent, and toluene and cyclopentanone were used as solvents. Moreover, the polymerizable liquid crystal compound (LC242) in the compound (1) is a compound of the following formula, manufactured by BASF.

[Example of optical film production]
A 5% by mass toluene solution of a photoalignable polymer represented by the formula (Z) was applied on a saponified triacetyl cellulose film, and after drying, a film having a thickness of 300 nm was formed. Subsequently, using a spot cure (SP-7, manufactured by Ushio Electric Co., Ltd.) with a polarized UV irradiation jig, irradiated with linearly polarized light for 5 minutes at an illuminance of 15 mW / cm ² (polarized UV irradiation). )did. The composition shown in Table 1 was applied to the surface subjected to polarized UV irradiation using a bar coater and heated to 130 ° C. to obtain a film oriented in a liquid crystal phase. Then, the optical film was produced by irradiating for 1 minute with the illumination intensity of 40 mW / cm < ² > in wavelength 365nm using Unicure (VB-15201BY-A, Ushio Denki Co., Ltd. product) in the state cooled to room temperature.

[Adhesion evaluation]
In accordance with JIS-K5600, peeling resistance was evaluated using a cross-cut guide I series (CCI-1, 1 mm interval, for 25 squares) manufactured by Cortec Corporation. Table 3 shows the results of counting the number of remaining optical films after the peel test.

[Measurement of optical properties]
The retardation value of the films prepared in Examples 1 to 3 and Comparative Example 1 was measured with a measuring machine (KOBRA-WR, manufactured by Oji Scientific Instruments). The phase difference value Re (λ) was measured at a wavelength (λ) of 549 nm. The results are shown in Table 3.

  It was confirmed that the present optical films of Examples 1 to 3 using the present composition (Compositions 1 to 3) were excellent in adhesion.

1, 1 ', 12: This phase difference plate,
2, 2 ': Polarizing film layer,
3, 3 ′: adhesive layer,
4a, 4b, 4c, 4d, 4e, 4, 4 ': Polarizing plate of the present invention (polarizing plate having the present optical film),
5, 5 ′: adhesive layer,
6: Liquid crystal panel,
7: Organic EL panel,
10a, 10b: liquid crystal display device,
11: Organic EL display device,

Claims (15)

The composition containing the following (A), (B) and (C).
(A) Polymerizable liquid crystal compound (B) Compound having a carbon-carbon unsaturated bond and an active hydrogen reactive group in the molecule (C) Photopolymerization initiator   The composition according to claim 1, wherein (B) is a compound having an isocyanato group as an active hydrogen reactive group. The composition according to claim 1, wherein (B) is a compound represented by the following formula (X).

[In the formula (X),
n represents an integer of 1 to 10, and R ^{1 ′} is a divalent aliphatic or alicyclic hydrocarbon group having 2 to 20 carbon atoms, or a divalent aromatic hydrocarbon group having 5 to 20 carbon atoms. Represents. Two R ^{2 ′ in} each repeating unit is a group represented by one —NH— and the other is N—C (═O) —R ^{3 ′} . R ^{3 ′} represents a group having a hydroxyl group or a carbon-carbon unsaturated bond.
Of R ^{3 ′} in formula (X), at least one R ^{3 ′} is a group having a carbon-carbon unsaturated bond. ] The composition according to any one of claims 1 to 3, wherein (A) is a compound represented by formula (A).

[In the formula (A),
X ¹ represents an oxygen atom, a sulfur atom, or —NR ¹ —. R ¹ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Y ¹ is a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a monovalent aromatic complex having 3 to 12 carbon atoms which may have a substituent. Represents a cyclic group.
Q ³ and Q ⁴ are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 3 to 20 carbon atoms. Represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, a halogen atom, a cyano group, a nitro group, —NR ² R ³ or —SR ² , or Q ³ and Q ⁴ are bonded to each other to form an aromatic ring or an aromatic heterocyclic ring together with the carbon atoms to which they are bonded. R ² and R ³ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
D ¹ and D ² are each independently a single bond, —C (═O) —O—, —C (═S) —O—, —CR ⁴ R ⁵ —, —CR ⁴ R ⁵ —CR ⁶ R. ^{7 -, - O-CR 4} R 5 -, - CR 4 R 5 -O-CR 6 R 7 -, - CO-O-CR 4 R 5 -, - O-CO-CR 4 R 5 -, - CR ^{4 R 5 -O-CO-CR} 6 R 7 -, - CR 4 R 5 -CO-O-CR 6 R 7 - or ^-NR 4 ^-CR 5 ^{R 6} - or -CO-NR ⁴ - represents a.
R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
G ¹ and G ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the methylene group constituting the alicyclic hydrocarbon group is an oxygen atom, a sulfur atom or — NH- may be substituted, and the methine group constituting the alicyclic hydrocarbon group may be substituted with a tertiary nitrogen atom.
L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² is an organic group having a polymerizable group. ] Said (A) is
The composition according to claim 4, wherein L ^{1 in the} formula (A) is a group represented by the formula (A1), and L ² is a compound of the group represented by the formula (A2).
P ¹ -F ^1- (B ¹ -A ¹ ) _k -E ^1- (A1)
P ² -F ^2- (B ² -A ² ) ₁ -E ^2- (A2)

[In Formula (A1) and Formula (A2),
^{B 1,} B 2, ^{E 1} and ^{E 2,} each _{^{independently, -CR 4 R 5 -, -}} CH 2 -CH 2 -, - O -, - S -, - CO-O -, - O-CO It represents —O—, —CS—O—, —O—CS—O—, —CO—NR ¹ —, —O—CH ₂ —, —S—CH ₂ — or a single bond.
A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms or a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms, and the alicyclic hydrocarbon The methylene group constituting the group may be replaced by an oxygen atom, a sulfur atom or -NH-, and the methine group constituting the alicyclic hydrocarbon group is replaced by a tertiary nitrogen atom. May be.
k and l each independently represents an integer of 0 to 3. When k is an integer of 2 or more, the plurality of B ¹ may be the same or different from each other, and the plurality of A ¹ may be the same or different from each other. When l is an integer of 2 or more, the plurality of B ² may be the same or different from each other, and the plurality of A ² may be the same or different from each other.
F ¹ and ^{F 2} represents a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms.
P ¹ represents a polymerizable group.
P ² represents a hydrogen atom or a polymerizable group.
R ¹ , R ⁴ and R ⁵ represent the same meaning as described above. ]   The optical film formed by superposing | polymerizing the polymeric component contained in the composition in any one of Claims 1-5. The manufacturing method of the optical film containing the following (1) and (2).
(1) The process of apply | coating the composition in any one of Claims 1-5 on a base material;
(2) The process of forming an optical film by superposing | polymerizing the polymeric component contained in the coating film apply | coated on the base material by (1).   The method for producing an optical film according to claim 7, wherein the substrate is made of a material having a hydroxyl group.   The method for producing an optical film according to claim 8, wherein the material having a hydroxyl group is a material obtained by saponifying triacetylcellulose.   The method for producing an optical film according to any one of claims 7 to 9, wherein the substrate is provided with an alignment film formed of a photoalignable polymer on the surface thereof.   The method for producing an optical film according to claim 10, wherein the alignment film is provided by forming a crosslinked structure of the photoalignable polymer by light irradiation.   The optical film obtained by the manufacturing method in any one of Claims 7-11.   The optical film according to claim 6 or 12, which has retardation.   A polarizing plate comprising the optical film according to claim 13.   A flat panel display device comprising the optical film according to claim 6, 12 or 13.

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