阅读说明：本技术 化合物和组合物 (Compounds and compositions ) 是由 飞田宪之 大川春树 于 2015-10-14 设计创作，主要内容包括：本发明提供一种包含聚合性液晶化合物和式(1)所示化合物的组合物,所述(1)所示化合物是在波长350nm～550nm的范围具有最大吸收的发挥作为二向色性色素的功能的化合物。提供式(1)所示的化合物,式(1)中,R～(1)表示氢原子等,R～(2)表示氢原子等,R～(3)表示氢原子等,Z表示-CO-等,Y表示式(Y1)所示的基团或式(Y2)所示的基团。式(Y1)中,*表示与N的键合部位。式(Y2)中,*表示与N的键合部位,P～(1)和P～(2)各自独立地表示-S-等,Q～(1)和Q～(2)各自独立地表示＝N-等。(The present invention provides a composition comprising a polymerizable liquid crystal compound and a compound represented by formula (1), wherein the compound represented by formula (1) has a maximum absorption in a wavelength range of 350nm to 550nm and functions as a dichroic dye. Provided is a compound represented by the formula (1), wherein R in the formula (1) 1 Represents a hydrogen atom or the like, R 2 Represents a hydrogen atom or the like, R 3 Represents a hydrogen atom or the like, Z represents-CO-or the like, and Y represents a group represented by the formula (Y1) or a group represented by the formula (Y2). In formula (Y1), a symbol represents a bonding site to N. In the formula (Y2), a represents a bonding site with N, P 1 And P 2 Each independently represents-S-, etc. -, Q 1 And Q 2 Each independently represents ═ N-or the like.)

1. A composition comprising a polymerizable liquid crystal compound and a compound represented by the formula (1),

in the formula (1), R¹Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms or-N (R)¹⁰)(R¹¹)，R¹⁰Represents an acyl group having 1 to 20 carbon atoms, R¹¹R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms¹⁰And R¹¹May be bonded to each other and together with the nitrogen atom to which they are bonded form a compound containing-N-CO-or-N-SO₂-a ring of (a) and (b),

one or more hydrogen atoms constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group and the arylsulfonyl group may be substituted with a halogen atom, a hydroxyl group, an amino group or a substituted amino group,

an-O-or-NR group may be inserted between carbon atoms constituting the alkyl group and the alkoxy group²⁰-，R²⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

R²represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

R³represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms or-N (R)¹²)(R¹³)，

R¹²An acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms or an arylsulfonyl group having 6 to 20 carbon atoms,

R¹³r represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms¹²And R¹³May be bonded to each other and together with the nitrogen atom to which they are bonded form a compound containing-N-CO-or-N-SO₂-a ring of (a) and (b),

one or more hydrogen atoms constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group and the arylsulfonyl group may be substituted with a halogen atom, a hydroxyl group, an amino group or a substituted amino group,

an-O-or-NR group may be inserted between carbon atoms constituting the alkyl group and the alkoxy group³⁰-，R³⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,

z represents-CO-or-SO₂-，

Y represents a group represented by the formula (Y1) or a group represented by the formula (Y2),

in the formula (Y1), a bond site to N is represented,

in the formula (Y2), a represents a bonding site with N, P¹And P²Each independently represents-S-, -O-or-N (R)¹⁴)-，R¹⁴Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Q¹And Q²Each independently represents ═ N-or ═ CH-.

2. The composition of claim 1, wherein the polymerizable liquid crystal compound exhibits a smectic liquid crystal phase.

3. The composition of claim 1 or 2, further comprising a polymerization initiator.

4. A polarizing film formed from the composition of any one of claims 1 to 3.

5. The polarizing film of claim 4, having a maximum absorption wavelength λ_max1The maximum absorption wavelength lambda of the compound represented by the formula (1)_max2And is larger.

6. The polarizing film of claim 5, having a λ_max1And λ_max2The difference is 10nm or more.

7. The polarizing film according to any one of claims 4 to 6, which shows a Bragg peak in an X-ray diffraction measurement.

8. A liquid crystal display device comprising the polarizing film according to any one of claims 4 to 7.

9. A liquid crystal cell comprising the polarizing film according to any one of claims 4 to 7, a liquid crystal layer, and a substrate.

10. The liquid crystal cell of claim 9, wherein the polarizing film is disposed between the substrate and the liquid crystal layer.

11. A liquid crystal cell as claimed in claim 10 wherein a color filter is further disposed between the substrate and the liquid crystal layer.

12. A circularly polarizing plate having the polarizing film of any one of claims 4 to 7 and 1/4 wave plates.

13. An organic EL display device comprising the polarizing film according to any one of claims 4 to 7 and an organic EL element.

14. An organic EL display device comprising the circularly polarizing plate according to claim 12 and an organic EL element.

Technical Field

The present invention relates to compounds and compositions.

Background

Patent document 1 describes a polarizing film containing a dichroic light-absorbing compound (dichroic dye) dispersed in a polymerizable liquid crystal compound that is aligned. However, there is no description of a dichroic dye having an absorption maximum at a wavelength of 350 to 550 nm.

Patent document 2 describes a disazo dye having a 1, 4-naphthyl structure as a dichroic dye having a maximum absorption at a wavelength of 350 to 550 nm. However, the dichroic ratio of the polarizing film including the disazo-based pigment is low.

Documents of the prior art

Patent document

Patent document 1: japanese Kohyo publication 2007-510946

Patent document 2: japanese patent No. 1454637

Disclosure of Invention

Problems to be solved by the invention

There is a demand for a compound that exhibits a function as a dichroic dye having a maximum absorption in the wavelength range of 350nm to 550 nm.

Means for solving the problems

The present invention includes the following inventions.

[1] A compound represented by the formula (1).

[ in the formula, R¹Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms or-N (R)¹⁰)(R¹¹)，R¹⁰Represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms or an arylsulfonyl group having 6 to 20 carbon atoms, R¹¹R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms¹⁰And R¹¹May be bonded to each other and together with the nitrogen atom to which they are bonded form a compound containing-N-CO-or-N-SO₂-a ring of (a). One or more hydrogen atoms constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group and the arylsulfonyl group may be substituted with a halogen atom, a hydroxyl group, an amino group or a substituted amino group. an-O-or-NR group may be inserted between carbon atoms constituting the above alkyl group and the above alkoxy group²⁰-，R²⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

R²Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

R³Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms or-N (R)¹²)(R¹³)。R¹²Represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms or an arylsulfonyl group having 6 to 20 carbon atoms, R¹³To representHydrogen atom or C1-20 alkyl group, R¹²And R¹³May be bonded to each other and together with the nitrogen atom to which they are bonded form a compound containing-N-CO-or-N-SO₂-a ring of (a). One or more hydrogen atoms constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group and the arylsulfonyl group may be substituted with a halogen atom, a hydroxyl group, an amino group or a substituted amino group. an-O-or-NR group may be inserted between carbon atoms constituting the above alkyl group and the above alkoxy group³⁰-，R³⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

Z represents-CO-or-SO₂-。

Y represents a group represented by the formula (Y1) or a group represented by the formula (Y2). ]

(wherein denotes a bonding site to N.)

(wherein, represents a bonding site with N, P¹And P²Each independently represents-S-, -O-or-N (R)¹⁴)-，R¹⁴Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Q¹And Q²Each independently represents ═ N-or ═ CH-. )

[2] A composition comprising a polymerizable liquid crystal compound and the compound of [1 ].

[3] The composition according to [2], wherein the polymerizable liquid crystal compound exhibits a smectic liquid crystal phase.

[4] The composition as described in [2] or [3], which further comprises a polymerization initiator.

[5] A polarizing film comprising the compound according to [1 ].

[6] A polarizing film comprising the composition according to any one of [2] to [4 ].

[7]Such as [5]]Or [6]]The polarizing film, the maximum absorption wavelength λ of the polarizing film_max1The maximum absorption wavelength lambda of the compound represented by the formula (1)_max2And is larger.

[8]Such as [7 ]]The polarizing film of lambda_max1And λ_max2The difference is 10nm or more.

[9] The polarizing film according to any one of [5] to [8], which shows a Bragg peak in X-ray diffraction measurement.

[10] A liquid crystal display device comprising the polarizing film according to any one of [5] to [9 ].

[11] A liquid crystal cell comprising the polarizing film according to any one of [5] to [9], a liquid crystal layer, and a substrate.

[12] The liquid crystal cell according to [11], wherein the polarizing film is disposed between the substrate and the liquid crystal layer.

[13] The liquid crystal cell according to [12], wherein a color filter is further disposed between the substrate and the liquid crystal layer.

[14] A circularly polarizing plate comprising the polarizing film according to any one of [5] to [9] and an 1/4 wave plate.

[15] An organic EL display device comprising the polarizing film according to any one of [5] to [9] and an organic EL element.

[16] An organic EL display device comprising the circularly polarizing plate according to [14] and an organic EL element.

ADVANTAGEOUS EFFECTS OF INVENTION

The compound of the present invention is a novel compound having a maximum absorption in a wavelength range of 350nm to 550nm and functioning as a dichroic dye, and a polarizing film having a high dichroic ratio can be formed from a composition containing the compound.

Drawings

Fig. 1 is a schematic view showing a continuous production method of a polarizing film of the present invention.

Fig. 2 is a schematic view of a continuous manufacturing method of a circularly polarizing plate having a polarizing film of the present invention.

Fig. 3 is a schematic view of a liquid crystal cell provided with the polarizing film of the present invention.

Fig. 4 is a schematic view of a liquid crystal cell provided with the polarizing film of the present invention.

Fig. 5 is a schematic view of a liquid crystal cell provided with the polarizing film of the present invention.

Detailed Description

< Compound represented by formula (1) >

The azo group of the compound represented by formula (1) of the present invention (hereinafter sometimes referred to as compound (1)) is preferably a trans-azo group.

In the formula (1), R¹Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms or-N (R)¹⁰)(R¹¹)。

Examples of the alkyl group having 1 to 20 carbon atoms include: an unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, and an n-decyl group.

One or more hydrogen atoms constituting the alkyl group having 1 to 20 carbon atoms may be substituted with a halogen atom (e.g., fluorine atom), a hydroxyl group, an amino group or a substituted amino group. Examples of the substituted amino group include: and amino groups substituted with one or two alkyl groups having 1 to 20 carbon atoms, such as an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, and an N, N-diethylamino group. Examples of the alkyl group in which one or more hydrogen atoms are substituted with a halogen atom or the like include: a C1-20 haloalkyl group such as a fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, nonafluorobutyl group, etc., a C1-20 hydroxyalkyl group such as a hydroxymethyl group, 2-hydroxyethyl group, etc., an aminomethyl group, a C1-20 alkyl group having an unsubstituted or substituted amino group such as a 2- (N, N-dimethylamino) ethyl group, etc.

The carbon atoms constituting the above alkyl group may be interrupted by-O-or-NR²⁰-，R²⁰The alkyl group having 1 to 20 carbon atoms is the same as the above group. having-O-or-NR-inserted between carbon atoms²⁰Examples of the alkyl group of (A) include: methoxymethyl, 2-ethoxyethyl, 2- (2-ethoxyethoxy) ethyl, 2- [2- (ethylamino) ethyl) amino]Ethyl, and the like.

Examples of the alkoxy group having 1 to 20 carbon atoms include: an unsubstituted straight-chain or branched alkoxy group having 1 to 20 carbon atoms such as a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a n-pentoxy group, an isopentoxy group, a neopentoxy group, a n-hexoxy group, a n-heptoxy group, a n-octoxy group, a n-nonoxy group, and a n-decyloxy group.

One or more hydrogen atoms constituting the alkoxy group having 1 to 20 carbon atoms may be substituted with a halogen atom (e.g., fluorine atom), a hydroxyl group, an amino group or an amino group having a substituent. Examples of the substituted amino group include: and amino groups substituted with one or two alkyl groups having 1 to 20 carbon atoms, such as an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, and an N, N-diethylamino group. Examples of the alkoxy group in which one or more hydrogen atoms are substituted with a halogen atom or the like include: a C1-20 haloalkoxy group such as fluoromethoxy, trifluoromethoxy, pentafluoroethoxy and nonafluorobutoxy, a C1-20 hydroxyalkoxy group such as hydroxymethoxy and 2-hydroxyethoxy, an aminomethoxy group, a C1-20 alkoxy group having an unsubstituted or substituted amino group such as 2- (N, N-dimethylamino) ethoxy group, and the like.

The carbon atoms constituting the above alkoxy group may be interrupted by-O-or-NR²⁰-, between carbon atoms interrupted by-O-or-NR²⁰Examples of the alkoxy group of (A) include: methoxymethoxy, 2-ethoxyethoxy, 2- (2-ethoxyethoxy) ethoxy, 2- [2- (ethylamino) ethyl) amino]Ethoxy and the like.

Examples of the acyl group having 1 to 20 carbon atoms include: an unsubstituted acyl group having 1 to 20 carbon atoms such as a formyl group, an acetyl group, an ethylcarbonyl group, a n-propylcarbonyl group, an isopropylcarbonyl group, a n-butylcarbonyl group, an isobutylcarbonyl group, a tert-butylcarbonyl group, a n-pentylcarbonyl group, an isopentylcarbonyl group, a neopentylcarbonyl group, a n-hexylcarbonyl group, a n-heptylcarbonyl group, a n-octylcarbonyl group, a n-nonylcarbonyl group, a n-decylcarbonyl group and the like. One or more hydrogen atoms constituting the acyl group may be substituted with a halogen atom (e.g., fluorine atom), a hydroxyl group, an amino group, or a substituted amino group. Examples of the substituted amino group include: and amino groups substituted with one or two alkyl groups having 1 to 20 carbon atoms, such as an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, and an N, N-diethylamino group. Examples of the acyl group in which one or more hydrogen atoms are substituted with a halogen atom or the like include: c1-20 haloacyl groups such as trifluoroacetyl group, pentafluoroethylcarbonyl group, nonafluorobutylcarbonyl group and the like.

Examples of the alkoxycarbonyl group having 2 to 20 carbon atoms include: an unsubstituted alkoxycarbonyl group having 2 to 20 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an isopropoxycarbonyl group, a n-butoxycarbonyl group, an isobutoxycarbonyl group, a t-butoxycarbonyl group, a n-pentyloxycarbonyl group, an isopentyloxycarbonyl group, a neopentyloxycarbonyl group, a n-hexyloxycarbonyl group, a n-heptyloxycarbonyl group, a n-octyloxycarbonyl group, a n-nonyloxycarbonyl group, a n-decyloxycarbonyl group and the like. One or more hydrogen atoms constituting the alkoxycarbonyl group may be substituted with a halogen atom (e.g., a fluorine atom), a hydroxyl group, an amino group, or a substituted amino group. Examples of the substituted amino group include: and amino groups substituted with one or two alkyl groups having 1 to 20 carbon atoms, such as an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, and an N, N-diethylamino group. Examples of the alkoxycarbonyl group in which one or more hydrogen atoms are substituted with a halogen atom or the like include: a haloalkoxycarbonyl group having 2 to 20 carbon atoms such as fluoromethoxycarbonyl group, trifluoromethoxycarbonyl group, pentafluoroethoxycarbonyl group, nonafluoro-n-butoxycarbonyl group and the like.

Examples of the acyloxy group having 1 to 20 carbon atoms include: an unsubstituted acyloxy group having 1 to 20 carbon atoms such as an acetoxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an isopropylcarbonyloxy group, an n-butylcarbonyloxy group, an isobutylcarbonyloxy group, a tert-butylcarbonyloxy group, an n-pentylcarbonyloxy group, an isopentylcarbonyloxy group, a neopentylcarbonyloxy group, an n-hexylcarbonyloxy group, an n-heptylcarbonyloxy group, an n-octylcarbonyloxy group, an n-nonylcarbonyloxy group, an n-decylcarbonyloxy group and the like. One or more hydrogen atoms constituting the acyloxy group may be substituted with a halogen atom (e.g., a fluorine atom), a hydroxyl group, an amino group, or a substituted amino group. Examples of the substituted amino group include: and amino groups substituted with one or two alkyl groups having 1 to 20 carbon atoms, such as an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, and an N, N-diethylamino group. Examples of the acyloxy group in which one or more hydrogen atoms are substituted with a halogen atom or the like include: a C1-20 haloacyloxy group such as a fluoroacetoxy group, a trifluoroacetyloxy group, a pentafluoroethylcarbonyloxy group, or a nonafluorobutylcarbonyloxy group.

-N(R¹⁰)(R¹¹) R in (1)¹⁰Represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms or an arylsulfonyl group having 6 to 20 carbon atoms, R¹¹R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms¹⁰And R¹¹May be bonded to each other and together with the nitrogen atom to which they are bonded form a compound containing-N-CO-or-N-SO₂-a ring of (a). Form R¹⁰One or more hydrogen atoms of the acyl group, the alkylsulfonyl group and the arylsulfonyl group in (a) may be substituted with a halogen atom (e.g., fluorine atom), a hydroxyl group, an amino group or an amino group having a substituent. Examples of the substituted amino group include: and amino groups substituted with one or two alkyl groups having 1 to 20 carbon atoms, such as an N-methylamino group, an N-ethylamino group, an N, N-dimethylamino group, and an N, N-diethylamino group. Form R¹¹In which an-O-or-NR group may be inserted between carbon atoms of the alkyl group²⁰-。R¹⁰In (1) to (20) acyl groups and the above-mentioned R¹Wherein the same group as the acyl group having 1 to 20 carbon atoms, and the acyl group in which one or more hydrogen atoms constituting the acyl group are substituted with a halogen atom or the like may be mentioned¹The same groups as in (1).

Examples of the C1-20 alkylsulfonyl group include: examples of the unsubstituted alkylsulfonyl group having 1 to 20 carbon atoms such as a methylsulfonyl group, an ethylsulfonyl group and an n-propylsulfonyl group, and a group in which one or more hydrogen atoms constituting the alkylsulfonyl group are substituted with a halogen atom or the like include: haloalkanesulfonyl group having 1 to 20 carbon atoms such as trifluoromethanesulfonyl group, pentafluoroethanesulfonyl group, heptafluoro-n-propanesulfonyl group and the like.

Examples of the arylsulfonyl group having 6 to 20 carbon atoms include a benzenesulfonyl group and a p-toluenesulfonyl group, and examples of the group in which one or more hydrogen atoms constituting the arylsulfonyl group are substituted with a halogen atom or the like include a p-trifluoromethylbenzenesulfonyl group.

R¹¹In the above formula (I), the alkyl group having 1 to 20 carbon atoms is the same as R¹The same group as the C1-20 alkyl group, and the alkyl group in which one or more hydrogen atoms constituting the alkyl group are substituted with a halogen atom or the like may be mentioned¹The same groups as in (1).

-N(R¹⁰)(R¹¹) Tool (A)Examples of the body include: acylamino, ethylcarbonylamino, n-propylcarbonylamino, isopropylcarbonylamino, n-butylcarbonylamino, isobutylcarbonylamino, tert-butylcarbonylamino, n-pentylcarbonylamino, isopentylcarbonylamino, neopentylcarbonylamino, n-hexylcarbonylamino, n-heptylcarbonylamino, n-octylcarbonylamino, n-nonylcarbonylamino, n-decylcarbonylamino, trifluoroacetylamino.

R¹⁰And R¹¹containing-N-CO-or-N-SO-which may be bound to each other and formed together with the nitrogen atom to which they are bound₂Examples of the "ring" may include 2-pyrrolidone-1-yl group and the like.

R¹Preferably an alkyl group having 1 to 10 carbon atoms which may have a halogen atom (preferably a fluorine atom), an alkyl group having 1 to 20 carbon atoms in which-O-is inserted between constituent carbon atoms, an alkoxy group having 1 to 10 carbon atoms which may have a halogen atom (preferably a fluorine atom), an alkoxy group having 1 to 20 carbon atoms in which-O-is inserted between constituent carbon atoms, an acyl group having 1 to 10 carbon atoms which may have a halogen atom (preferably a fluorine atom), an alkoxycarbonyl group having 2 to 10 carbon atoms which may have a halogen atom (preferably a fluorine atom), an acyloxy group having 1 to 10 carbon atoms which may have a halogen atom (preferably a fluorine atom), or-N (R)¹⁰)(R¹¹)，R¹⁰Preferably an acyl group having 1 to 20 carbon atoms which may have a halogen atom (preferably a fluorine atom), R¹¹Preferably a hydrogen atom.

R¹More preferably a linear alkyl group having 1 to 10 carbon atoms which may have a fluorine atom or-N (R)¹⁰)(R¹¹)，R¹⁰More preferably an acyl group having 1 to 10 carbon atoms which may have a fluorine atom, R¹¹Preferably a hydrogen atom.

R¹Particularly preferred is a linear alkyl group having 1 to 10 carbon atoms which may have a fluorine atom.

In the formula (1), R²Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

R²Examples of the alkyl group having 1 to 20 carbon atoms include: and R as defined above¹Wherein the same groups are used for unsubstituted alkyl groups having 1 to 20 carbon atoms.

R²Preferably a hydrogen atom.

In the formula (1), R³Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an acyl group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an acyloxy group having 1 to 20 carbon atoms or-N (R)¹²)(R¹³)。R¹²Represents an acyl group having 1 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms or an arylsulfonyl group having 6 to 20 carbon atoms, R¹³R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms¹²And R¹³May be bonded to each other and together with the nitrogen atom to which they are bonded form a compound containing-N-CO-or-N-SO₂-a ring of (a). One or more hydrogen atoms constituting the alkyl group, the alkoxy group, the acyl group, the alkoxycarbonyl group, the acyloxy group, the alkylsulfonyl group and the arylsulfonyl group may be substituted with a halogen atom, a hydroxyl group, an amino group or a substituted amino group. an-O-or-NR group may be inserted between carbon atoms constituting the above alkyl group and the above alkoxy group³⁰-，R³⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

R³In the above formula, the alkyl group having 1 to 20 carbon atoms, the alkoxy group having 1 to 20 carbon atoms, the acyl group having 1 to 20 carbon atoms, the alkoxycarbonyl group having 2 to 20 carbon atoms and the acyloxy group having 1 to 20 carbon atoms are respectively the same as those mentioned above for R¹Wherein the alkyl group having 1 to 20 carbon atoms, the alkoxy group having 1 to 20 carbon atoms, the acyl group having 1 to 20 carbon atoms, the alkoxycarbonyl group having 2 to 20 carbon atoms and the acyloxy group having 1 to 20 carbon atoms are the same.

R¹²In the above formula, the C1-20 acyl group, C1-20 alkylsulfonyl group and C6-20 arylsulfonyl group are respectively the same as those mentioned above for R¹⁰Wherein the acyl group having 1 to 20 carbon atoms, the alkylsulfonyl group having 1 to 20 carbon atoms and the arylsulfonyl group having 6 to 20 carbon atoms are the same group.

R¹³In the above formula (I), the alkyl group having 1 to 20 carbon atoms is the same as R¹¹The same group as the C1-20 alkyl group in (A).

-N(R¹²)(R¹³) Specific examples of (A) include the compounds mentioned above under-N (R)¹⁰)(R¹¹) The same applies to the specific examples of (1).

R¹²And R¹³containing-N-C groups which may be bonded to each other and formed together with the nitrogen atom to which they are bondedO-or-N-SO₂Examples of the "ring" may include 2-pyrrolidone-1-yl group and the like.

R³Preferably an alkyl group having 1 to 10 carbon atoms which may have a halogen atom (preferably a fluorine atom) or-N (R)¹²)(R¹³)，R¹²Preferably an acyl group having 1 to 20 carbon atoms which may have a halogen atom (preferably a fluorine atom) or an alkylsulfonyl group having 1 to 20 carbon atoms which may have a halogen atom (preferably a fluorine atom), R¹³Preferably a hydrogen atom.

Z represents-CO-or-SO₂-。

In the formula (1), Y represents a group represented by the formula (Y1) or a group represented by the formula (Y2),

(wherein denotes a bonding site to N.)

(wherein, represents a bonding site with N, P¹And P²Each independently represents-S-, -O-or-N (R)¹⁴)-，R¹⁴Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, Q¹And Q²Each independently represents ═ N-or ═ CH-. ).

P¹preferably-S-.

P²preferably-S-.

R¹⁴Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group and a tert-butyl group.

Q¹Preferably, it is ═ CH-.

Q²Preferably, N-.

Specific examples of the compound (1) include compounds represented by the following formulae (1-1) to (1-18).

Among them, compounds represented by the formulae (1-4), (1-7), (1-12) and (1-14) are more preferable, and compounds represented by the formulae (1-12) and (1-14) are still more preferable.

The compound (1) can be produced by reacting a compound represented by the formula (2) (hereinafter, sometimes referred to as a compound (2)) with a compound represented by the formula (3) (hereinafter, sometimes referred to as a compound (3)).

[ in the formula, R¹、R²And Y represents the same meaning as above.]

[ in the formula, R³And Z represents the same meaning as above, and X represents a hydroxyl group, a chlorine atom, a bromine atom or an iodine atom.]

R may be added as necessary¹、R³The compound (1) is produced by protecting with an appropriate protecting group, then performing a reaction, and then performing a deprotection reaction.

As the compound (2) and the compound (3), compounds produced by a known method can be used, and commercially available compounds can be used.

The reaction of the compound (2) with the compound (3) is usually carried out in a solvent in the presence of a base.

Examples of the solvent include solvents in which both the compound (2) and the compound (3) are soluble, such as chloroform. Examples of the base include N, N-dimethylaminopyridine. The catalyst may be diisopropylcarbodiimide (IPC) or the like.

The reaction temperature is usually-15 to 70 ℃ and preferably 0 to 40 ℃. The reaction time is usually 15 minutes to 48 hours.

After the reaction is completed, the compound (1) is extracted by a common extraction means such as recrystallization, reprecipitation, extraction, various chromatographies, and the like.

The compound (1) is a compound that functions as a dichroic dye, and exhibits higher dichroism particularly by being aligned together with a polymerizable liquid crystal compound. Therefore, the polarizing film in which the compound (1) and the polymerizable liquid crystal compound are aligned together exhibits higher dichroism. The compound (1) has a maximum absorption in a wavelength range of 350 to 510nm, preferably 400 to 500nm, more preferably 410 to 490nm, and still more preferably 420 to 480 nm. In addition, since the compound (1) has light resistance, the polarizing film including the compound of the present invention is excellent in light resistance.

The light resistance of the polarizing film can be determined, for example, by the following method.

A protective film was placed on the surface of the formed polarizing film, and light was irradiated from above under the following conditions. The light resistance was determined from the ratio of the absorbance of the polarizing film having the maximum absorption wavelength of 501nm after the light resistance test to the absorbance of the polarizing film having the maximum absorption wavelength of 501nm before the test.

For example, when a polarizing film is formed using a dichroic dye represented by the formula (1-10) described in Japanese patent application laid-open No. 2013-101328 and a light resistance test is performed, the absorbance of the polarizing film after the light resistance test at the maximum absorption wavelength of 548nm of the polarizing film is 47% before the test.

(light irradiation conditions in light resistance test)

The use equipment comprises the following steps: santest XLS + manufactured by ATLAS company

Using a light source: xenon arc lamp

Exposure conditions: 250mW/m²

Test time: 120 hours

Exposure amount: 108000KJ/m²

Temperature: 60 deg.C

Next, the composition of the present invention comprising the polymerizable liquid crystal compound and the compound (1) will be described.

The composition of the present invention may contain two or more compounds (1).

< polymerizable liquid Crystal Compound >

The polymerizable liquid crystal compound is a compound having a polymerizable group in a molecule and capable of exhibiting a liquid crystal phase by being aligned, and is preferably a compound capable of exhibiting a liquid crystal phase by being aligned alone.

The polymerizable group is a group participating in a polymerization reaction, and is preferably a photopolymerizable group. The polymerizable group here means a group that can participate in a polymerization reaction by an active radical, an acid, or the like generated from a polymerization initiator described later. Examples of the polymerizable group include a vinyl group, a vinyloxy group, a 1-chloroethenyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group, a methacryloyloxy group, an epoxyethyl group and an oxetanyl group. Among them, preferred are acryloyloxy, methacryloyloxy, vinyloxy, epoxyethyl and oxetanyl, and more preferred is acryloyloxy.

The polymerizable liquid crystal compound may be of thermotropic liquid crystal type or of lyotropic liquid crystal type.

The polymerizable liquid crystal compound may be a polymerizable liquid crystal compound exhibiting a nematic liquid crystal phase, a polymerizable liquid crystal compound exhibiting a smectic liquid crystal phase, or a polymerizable liquid crystal compound exhibiting both a nematic liquid crystal phase and a smectic liquid crystal phase. Preferably exhibit smectic liquid crystal phases, more preferably exhibit highly ordered smectic liquid crystal phases. The composition of the present invention comprising the polymerizable liquid crystal compound exhibiting a smectic liquid crystal phase can provide a polarizing film more excellent in polarizing properties. The composition of the present invention may contain two or more kinds of polymerizable liquid crystal compounds.

The compound (1) can exhibit high dichroism even in a state of being dispersed between dense molecular chains, which is formed by a polymerizable liquid crystal compound exhibiting a smectic liquid crystal phase, and a composition containing the compound (1) can provide a polarizing film having a high dichroism ratio.

Examples of highly ordered smectic liquid crystal phases include smectic B phase, smectic D phase, smectic E phase, smectic F phase, smectic G phase, smectic H phase, smectic I phase, smectic J phase, smectic K phase and smectic L phase. Among them, smectic B phase, smectic F phase and smectic I phase are preferable. When the smectic liquid crystal phase exhibited by the polymerizable liquid crystal compound is such a highly ordered smectic phase, a polarizing film having a higher degree of orientational order can be obtained. A polarizing film obtained from a composition comprising a highly ordered smectic liquid crystal compound exhibiting a high degree of orientational order shows bragg peaks derived from a highly ordered structure such as a hexagonal (Hexatic) phase or a crystalline (Cystal) phase in X-ray diffraction measurement. The bragg peak is a peak derived from a plane periodic structure of molecular orientation. The polarizing film obtained from the composition of the present invention preferably has a periodic interval

The type of the liquid crystal phase exhibited by the polymerizable liquid crystal compound can be confirmed, for example, as follows. A suitable substrate is prepared, a solution containing a polymerizable liquid crystal compound and a solvent is applied to the substrate to form a coating film, and then heat treatment or reduced pressure treatment is performed to remove the solvent contained in the coating film. Next, the coating film formed on the substrate is heated to an isotropic phase temperature, and gradually cooled to develop a liquid crystal phase, and the liquid crystal phase is examined by texture observation using a polarization microscope, X-ray diffraction measurement, or differential scanning calorimetry. In this examination, for example, it was confirmed that cooling to the 1 st temperature thereby showing a nematic liquid crystal phase, followed by gradual cooling to the 2 nd temperature thereby showing a smectic liquid crystal phase.

The polymerizable liquid crystal composition is preferably a compound represented by formula (4) (hereinafter, may be referred to as compound (4)).

U¹-V¹-W¹-X¹-Y¹-X²-Y²-X³-W²-V²-U² (4)

[ in the formula (4),

X¹、X²and X³Independently of one another, a 1, 4-phenylene group which may have a substituent or a cyclohexane-1, 4-diyl group which may have a substituent. However, X¹、X²And X³At least one of them is a 1, 4-phenylene group which may have a substituent. -CH constituting cyclohexane-1, 4-diyl₂-may be replaced by-O-, -S-or-NR-. R represents an alkyl group having 1 to 6 carbon atoms or a phenyl group.

Y¹And Y²Independently of one another represent-CH₂CH₂-、-CH₂O-, -COO-, -OCOO-, single bond, -N ═ N-, -CR^a＝CR^b-, -C.ident.C-or-CR^a＝N-。R^aAnd R^bIndependently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

U¹Represents a hydrogen atom or a polymerizable group.

U²Represents a polymerizable group.

W¹And W²Independently of one another, represents a single bond, -O-, -S-, -COO-or-OCOO.

V¹And V²Independently represent optionally substituted alkanediyl having 1 to 20 carbon atoms, -CH₂-may be replaced by-O-, -S-or-NH-.]

In the compound (4), X¹、X²And X³At least one of them is preferably a 1, 4-phenylene group which may have a substituent.

The 1, 4-phenylene group which may have a substituent is preferably unsubstituted. The cyclohexane-1, 4-diyl group which may have a substituent is preferably a trans-cyclohexane-1, 4-diyl group which may have a substituent. The trans-cyclohexane-1, 4-diyl group which may have a substituent is preferably an unsubstituted trans-cyclohexane-1, 4-diyl group.

Examples of the substituent which may be optionally substituted for the 1, 4-phenylene group or the substituted cyclohexane-1, 4-diyl group include: an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, or an n-butyl group, a cyano group, and a halogen atom.

Y¹Is preferably-CH₂CH₂-, -COO-or a single bond, Y²Is preferably-CH₂CH₂-or-CH₂O-。

U²Is a polymerizable group. U shape¹Is a hydrogen atom or a polymerizable group, and is preferably a polymerizable group. U shape¹And U²Preferably, all of them are polymerizable groups, and more preferably all of them are photopolymerizable groups. The polymerizable liquid crystal compound having a photopolymerizable group is advantageous in that polymerization can be performed at a lower temperature.

U¹And U²The polymerizable groups shown may be different from each other, and are preferably the same. Examples of the polymerizable group include a vinyl group, a vinyloxy group, a 1-chloroethenyl group, an isopropenyl group, a 4-vinylphenyl group, an acryloyloxy group, a methacryloyloxy group, an epoxyethyl group and an oxetanyl group. Among them, preferred are acryloyloxy, methacryloyloxy, vinyloxy, epoxyethyl and oxetanyl, and more preferred is acryloyloxy.

V¹And V²Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, a pentane-1, 5-diyl group, a hexane-1, 6-diyl group, a heptane-1, 7-diyl group, an octane-1, 8-diyl group, a decane-1, 10-diyl group, a tetradecane-1, 14-diyl group and an eicosane-1, 20-diyl group. V¹And V²Preferably C2-C12 alkanediyl, more preferably C6-C12 alkanediyl.

The substituent optionally having the C1-20 alkanediyl group which may have a substituent includes a cyano group and a halogen atom. The alkanediyl group is preferably an unsubstituted alkanediyl group, and more preferably an unsubstituted straight-chain alkanediyl group.

W¹And W²Preferably independently of one another, a single bond or-O-.

Specific examples of the compound (4) include compounds represented by the following formulae (4-1) to (4-43). In the case where the compound (4) has a cyclohexane-1, 4-diyl group, the cyclohexane-1, 4-diyl group is preferably a trans group.

Among them, preferred is at least 1 selected from the group consisting of the compounds represented by formula (4-5), formula (4-6), formula (4-7), formula (4-8), formula (4-9), formula (4-10), formula (4-11), formula (4-12), formula (4-13), formula (4-14), formula (4-15), formula (4-22), formula (4-24), formula (4-25), formula (4-26), formula (4-27), formula (4-28) and formula (4-29).

The composition of the present invention may contain two or more compounds (4). When two or more polymerizable liquid crystal compounds are combined, at least 1 of them is preferably the compound (4), and more preferably two or more of them are the compound (4). By combining them, the liquid crystal phase may be temporarily maintained even at a temperature not higher than the liquid crystal-crystalline phase transition temperature. The mixing ratio in the case of combining two polymerizable liquid crystal compounds is usually 1: 99 to 50: 50, preferably 5: 95 to 50: 50, and more preferably 10: 90 to 50: 50.

The compound (4) can be produced by a method described in publicly known documents such as Lub et al, Recl, Trav, Chim, Pays-Bas, 115, 321-328(1996) and Japanese patent No. 4719156.

From the viewpoint of improving the alignment properties of the polymerizable liquid crystal compound, the content of the polymerizable liquid crystal compound in the composition of the present invention is preferably 70 to 99.5 parts by mass, more preferably 80 to 99 parts by mass, even more preferably 80 to 94 parts by mass, and particularly preferably 80 to 90 parts by mass, based on 100 parts by mass of the solid content of the composition of the present invention. Here, the solid component means the total amount of components other than the solvent in the composition of the present invention.

The composition of the present invention preferably contains a polymerization initiator and a solvent, and may contain a photosensitizer, a polymerization inhibitor and a leveling agent.

The content of the compound (1) in the composition of the present invention is usually 50 parts by mass or less, preferably 0.1 part by mass or more and 10 parts by mass or less, and more preferably 0.1 part by mass or more and 5 parts by mass or less, per 100 parts by mass of the polymerizable liquid crystal compound. When the content of the compound (1) is 50 parts by mass or less based on 100 parts by mass of the polymerizable liquid crystal compound, a polarizing film with less alignment disorder between the polymerizable liquid crystal compound and the compound (1) tends to be obtained.

< solvent >

The solvent is preferably a solvent which can completely dissolve the polymerizable liquid crystal compound and the compound (1). Further, a solvent inert to the polymerization reaction of the polymerizable liquid crystal compound is preferable.

Examples of the solvent include: alcohol solvents such as methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, ethylene glycol methyl ether, ethylene glycol butyl ether, propylene glycol monomethyl ether, etc.; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ -butyrolactone, propylene glycol methyl ether acetate, ethyl lactate, and the like; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran and dimethoxyethane; and chlorine-containing solvents such as chloroform and chlorobenzene. These solvents may be used alone or in combination of two or more.

When the composition of the present invention contains a solvent, the content of the solvent is preferably 50 to 98% by mass based on the total amount of the composition of the present invention. In other words, the solid content in the composition of the present invention is preferably 2 to 50% by mass. When the solid content is 50% by mass or less, the viscosity of the composition of the present invention is lowered, and the thickness of the polarizing film obtained from the composition of the present invention becomes substantially uniform, and the polarizing film tends to be less likely to be uneven. The solid content may be determined in consideration of the thickness of the polarizing film to be manufactured.

< polymerization initiator >

The polymerization initiator is a compound that can initiate a polymerization reaction of the polymerizable liquid crystal compound. The polymerization initiator is preferably a photopolymerization initiator which generates active radicals by the action of light.

Examples of the polymerization initiator include: benzoin compounds, benzophenone compounds, alkylphenone compounds, acylphosphine oxide compounds, triazine compounds, iodonium salts, and sulfonium salts.

Examples of benzoin compounds include: benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

Examples of the benzophenone compound include: benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3 ', 4, 4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2, 4, 6-trimethylbenzophenone.

Examples of the alkylphenyl ketone compound include: diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, oligomers of 1, 2-diphenyl-2, 2-dimethoxyethane-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] propan-1-one, 1-hydroxycyclohexyl phenyl ketone and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] propan-1-one.

As the acylphosphine oxide compound, 2, 4, 6-trimethylbenzoyldiphenylphosphine oxide and bis (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide can be mentioned.

Examples of the triazine compound include: 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) vinyl ] -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (furan-2-yl) vinyl ] -1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (4-diethylamino- 2-methylphenyl) vinyl ] -1, 3, 5-triazine and 2, 4-bis (trichloromethyl) -6- [2- (3, 4-dimethoxyphenyl) vinyl ] -1, 3, 5-triazine.

As the polymerization initiator, a commercially available polymerization initiator can be used. Examples of commercially available polymerization initiators include: IRGACURE (イルガキユア) (registered trademark) 907, 184, 651, 819, 250, and 369(Ciba japan ltd.); SEIKUOL (registered trademark) BZ, Z and BEE (seiko chemical corporation); KAYACURE (power ヤキユア I) (registered trademark) BP100 and UVI-6992 (manufactured by Dow Corp.); ADEKA OPTMER SP-152 and SP-170 (ADEKA, Inc.); TAZ-A and TAZ-PP (Siber Hegner, Japan); and TAZ-104(Sanwa Chemical Co.).

When the composition of the present invention contains a polymerization initiator, the content of the polymerization initiator in the composition of the present invention is usually 0.1 to 30 parts by mass, preferably 0.5 to 10 parts by mass, and more preferably 0.5 to 8 parts by mass per 100 parts by mass of the polymerizable liquid crystal compound, from the viewpoint of not easily disturbing the orientation of the polymerizable liquid crystal compound.

< photosensitizers >

In the case where the composition of the present invention contains a photopolymerization initiator, the composition of the present invention preferably contains a photosensitizer. The composition of the present invention contains a photopolymerization initiator and a photosensitizer, and thus the polymerization reaction of the polymerizable liquid crystal compound tends to be further accelerated. Examples of the photosensitizer include: xanthone compounds such as xanthone and thioxanthone (e.g., 2, 4-diethylthioxanthone, 2-isopropylthioxanthone); anthracene compounds such as anthracene and alkoxy-containing anthracene (e.g., dibutoxyanthracene); phenothiazine and rubrene.

When the composition of the present invention contains a photosensitizer, the content of the photosensitizer in the composition of the present invention is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 10 parts by mass, and still more preferably 0.5 to 8 parts by mass, per 100 parts by mass of the polymerizable liquid crystal compound.

< polymerization inhibitor >

Examples of the polymerization inhibitor include radical scavengers such as hydroquinone, alkoxy-containing catechol (e.g., butylcatechol), pyrogallol, and 2, 2, 6, 6-tetramethyl-1-piperidinyloxy radical; thiophenols; beta-naphthylamines and beta-naphthols.

The composition of the present invention contains a polymerization inhibitor, whereby the degree of progress of the polymerization reaction of the polymerizable liquid crystal compound can be controlled.

When the composition of the present invention contains a polymerization inhibitor, the content of the polymerization inhibitor in the composition of the present invention is preferably 0.1 to 30 parts by mass, more preferably 0.5 to 10 parts by mass, and still more preferably 0.5 to 8 parts by mass, per 100 parts by mass of the polymerizable liquid crystal compound.

< leveling agent >

The leveling agent refers to a substance having the following functions: the fluidity of the composition of the present invention is adjusted so that the coating film obtained by coating the composition of the present invention is flatter. For example, a surfactant can be cited. Preferred leveling agents are those containing a polyacrylate compound as a main component and those containing a fluorine atom-containing compound as a main component.

Examples of the leveling agent containing a polyacrylate compound as a main component include: BYK-350, BYK-352, BYK-353, BYK-354, BYK-355, BYK-358N, BYK-361N, BYK-380, BYK-381, and BYK-392(BYK Chemie Co.).

Examples of the leveling agent containing a fluorine atom-containing compound as a main component include: megafac (registered trademark) R-08, R-30, R-90, F-410, F-411, F-443, F-445, F-470, F-471, F-477, F-479, F-482, F-483(DIC corporation); surflon (registered trademark) S-381, S-382, S-383, S-393, SC-101, SC-105, KH-40, and SA-100(AGC Seimi Chemical Co.); e1830 and E5844 (Daikin Fine Chemical Laboratory Co., Ltd.); f top EF301, EF303, EF351 and EF352(Mitsubishi Materials Electronic Chemicals).

When the composition of the present invention contains a leveling agent, the content of the leveling agent is preferably 0.3 parts by mass or more and 5 parts by mass or less, and more preferably 0.5 parts by mass or more and 3 parts by mass or less, per 100 parts by mass of the polymerizable liquid crystal compound.

When the content of the leveling agent is within the above range, the polymerizable liquid crystal compound tends to be easily aligned horizontally, and the obtained polarizing film tends to be smoother. When the content of the leveling agent relative to the polymerizable liquid crystal compound exceeds the above range, the polarizing film obtained tends to be easily uneven. The composition of the present invention may comprise more than two leveling agents.

< method for producing polarizing film >

The polarizing film containing the compound (1) can be obtained by, for example, coating the composition of the present invention. The resin composition can be preferably produced by a production method comprising the following steps (a) to (C).

Step (A): coating the composition of the present invention on the surface of a substrate or a substrate having an alignment film formed thereon

A step (B): a step of aligning the polymerizable liquid crystal compound and the compound (1) contained in the formed coating film

Step (C): a step of irradiating the aligned polymerizable liquid crystal compound with active energy ray to polymerize the polymerizable liquid crystal compound

< Process (A) >

< substrate >

The substrate may be a glass substrate or a resin substrate, and is preferably a resin substrate. By using a film base material containing a resin, a thin polarizing plate can be obtained.

The resin substrate is preferably a transparent resin substrate. The transparent resin substrate is a substrate having a light transmittance allowing light to pass therethrough, particularly visible light, and the light transmittance is a characteristic in which the visual sensitivity correction transmittance (the positive water vapor transmission rate in terms of viewing rate) for all light rays having a wavelength of 380nm to 780nm is 80% or more.

The substrate is preferably a retardation film having a function of 1/4 wave plate (hereinafter, sometimes referred to as 1/4 wave plate). The circularly polarizing plate can be obtained by using 1/4 wave plates as the base material.

In this case, the polarizing film is preferably laminated so that the transmission axis and the slow axis (optical axis) of the 1/4 wave plate are substantially 45 °. Substantially 45 ° generally refers to the range of 45 ± 5 °.

Further, by aligning or making the optical axes of the polarizing film and the 1/4 wave plate orthogonal to each other, a polarizing film that functions as an optical compensation film can be obtained.

The 1/4 wave plate generally has the optical characteristics shown by formula (40), and preferably has the optical characteristics shown by formula (40-1).

100＜Re(550)＜160 (40)

130＜Re(550)＜150 (40-1)

Re (550) represents an in-plane phase difference value for light having a wavelength of 550 nm.

Further, the 1/4 wave plate preferably has reverse wavelength dispersion characteristics. The inverse wavelength dispersion characteristic is that the in-plane retardation value at a short wavelength is larger than the in-plane retardation value at a long wavelength, and preferably satisfies optical characteristics expressed by expressions (50) and (51). Re (λ) represents an in-plane phase difference value for light of wavelength λ nm. The circularly polarizing plate including the 1/4 wave plate having the optical characteristics shown in formula (50) and formula (51) tends to have excellent antireflection characteristics because uniform polarization conversion characteristics can be obtained for light having each wavelength in the visible light region.

Re(450)/Re(550)≤1.00 (50)

1.00≤Re(630)/Re(550) (51)

The substrate may be a retardation film having the function of 1/2 wave plate.

Examples of the resin constituting the substrate include: polyolefins such as polyethylene, polypropylene, and norbornene polymers; a cycloolefin resin; polyvinyl alcohol; polyethylene terephthalate; polymethacrylates; a polyacrylate; cellulose esters such as triacetyl cellulose, diacetyl cellulose, and cellulose acetate propionate; polyethylene naphthalate; a polycarbonate; polysulfones; polyether sulfone; a polyether ketone; polyphenylene sulfide; and polyphenylene ethers and the like. Preferably cellulose ester, cycloolefin resin, polycarbonate, polyethersulfone, polyethylene terephthalate, or polymethacrylate.

Cellulose esters are those obtained by esterifying at least a part of the hydroxyl groups contained in cellulose, and are commercially available. In addition, substrates comprising cellulose esters are also commercially available. Examples of commercially available substrates containing cellulose esters include: fujitac (registered trademark) film (Fuji film Co., Ltd.), KC8UX2M (Konica Minolta Opto Co., Ltd.), KC8UY (Konica Minolta Opto Co., Ltd.), KC4UY (Konica Minolta Opto Co., Ltd.), and the like.

The cycloolefin resin is a resin containing a polymer of a cycloolefin such as norbornene or polycyclic norbornene monomer or a copolymer thereof. The cycloolefin resin may have a ring-opened structure, or may be hydrogenated after the cycloolefin resin having a ring-opened structure is hydrogenated. The cyclic olefin resin may contain a structural unit derived from a chain olefin and a vinylated aromatic compound within a range in which transparency is not significantly impaired and hygroscopicity is not significantly increased. The cycloolefin resin may have a polar group introduced into the molecule thereof.

Examples of the chain olefin include ethylene and propylene, and examples of the vinylated aromatic compound include styrene, α -methylstyrene and alkyl-substituted styrene.

When the cyclic olefin resin is a copolymer of a cyclic olefin and a chain olefin or a vinyl aromatic compound, the content of the structural unit derived from the cyclic olefin is usually 50 mol% or less, preferably 15 to 50 mol% based on the total structural units of the copolymer.

When the cyclic olefin resin is a terpolymer of a cyclic olefin, a chain olefin and a vinylated aromatic compound, the content of the structural unit derived from the chain olefin is usually 5 to 80 mol% based on the total structural units of the copolymer, and the content of the structural unit derived from the vinylated aromatic compound is usually 5 to 80 mol% based on the total structural units of the copolymer. Such a terpolymer has an advantage of being able to relatively reduce the amount of the expensive cyclic olefin used.

Cycloolefin resins are commercially available. Examples of commercially available cycloolefin resins include: topas (registered trademark) (Ticona (germany)), Arton (registered trademark) (JSR corporation), ZEONOR (ゼオノア) (registered trademark) (japan regon corporation), ZEONEX (ゼオネツクス) (registered trademark) (japan regon corporation), and APEL (registered trademark) (mitsui corporation), and the like. Such a cycloolefin resin can be formed into a film by a known means such as solvent casting or melt extrusion and used as a substrate. Examples of commercially available substrates containing a cycloolefin resin include: エスシ - ナ (registered trademark) (waterlogging chemical Co., Ltd.), SCA40 (registered trademark) (waterlogging chemical Co., Ltd.), ZEONOR film (registered trademark) (Optes Co., Ltd.), Arton film (registered trademark) (JSR Co., Ltd.), and the like.

The substrate may be subjected to a surface treatment. Examples of the surface treatment method include: a method of treating the surface of a base material with corona or plasma in an atmosphere of vacuum to atmospheric pressure; a method of laser processing a surface of a base material; a method of treating a surface of a base material with ozone; a method of saponifying the surface of a base material; a method of flame treating a surface of a base material; a method of coating a coupling agent on the surface of a substrate; a method of performing a primer treatment on a surface of a substrate; and graft polymerization methods in which a reactive monomer or a reactive polymer is attached to the surface of a substrate and then the substrate is irradiated with radiation, plasma, or ultraviolet rays to react the monomer or polymer. Among them, preferred are: a method of corona or plasma treating a surface of a substrate under an atmosphere of vacuum to atmospheric pressure.

Examples of the method of surface treatment of the substrate by corona or plasma include: a method of treating the surface of a substrate by disposing the substrate between opposing electrodes at a pressure near atmospheric pressure and generating corona or plasma; a method of circulating a gas between the opposing electrodes, converting the gas into plasma between the electrodes, and blowing the converted gas to the substrate; and a method of performing surface treatment of a substrate by generating glow discharge plasma under low pressure conditions.

Among them, preferred are: a method of treating the surface of a substrate by disposing the substrate between opposing electrodes at a pressure near atmospheric pressure and generating corona or plasma; or a method in which a gas is passed between the opposing electrodes, the gas is made into a plasma between the electrodes, and the plasma-made gas is blown onto the substrate. The surface treatment by corona or plasma is generally carried out by a commercially available surface treatment apparatus.

The substrate may have a protective film on the side opposite to the side coated with the composition of the present invention. Examples of the protective film include: films of polyethylene, polyethylene terephthalate, polycarbonate, polyolefin, and the like, and films further having an adhesive layer on the films, and the like. Among them, polyethylene terephthalate is preferable because of small thermal deformation at the time of drying. By providing the protective film on the side opposite to the side on which the present composition is applied, the fluctuation of the film and slight vibration of the applied side during substrate transfer can be suppressed, and the uniformity of the coating film can be improved.

From the viewpoint of weight to such an extent that practical handling is possible, the thickness of the base material is preferably small, and if it is too thin, the strength tends to be reduced, and the workability tends to be deteriorated. The thickness of the substrate is usually 5 to 300 μm, preferably 20 to 200 μm.

The length of the substrate in the longitudinal direction is usually 10 to 3000m, preferably 100 to 2000 m. The length of the substrate in the short side direction is usually 0.1 to 5m, preferably 0.2 to 2 m.

< alignment film >

The alignment film in the present invention is a film having an alignment regulating force for aligning a polymerizable liquid crystal compound in a desired direction.

The alignment film preferably has solvent resistance that does not dissolve due to application of the composition of the present invention, and heat resistance for use in heat treatment for removing the solvent and aligning the polymerizable liquid crystal compound. Examples of such an alignment film include: an alignment film containing an alignment polymer, a photo-alignment film, and a groove alignment film in which a concave-convex pattern and/or a plurality of grooves are formed on a surface to align the grooves.

Examples of the oriented polymer include: polyamides or gelatins having an amide bond in a molecule; polyimide having an imide bond in the molecule, and polyamic acid, polyvinyl alcohol, alkyl-modified polyvinyl alcohol, polyacrylamide, polyoxazoles, polyethyleneimine, polystyrene, polyvinylpyrrolidone, polyacrylic acid, and polyacrylates as their hydrolysates. Among them, polyvinyl alcohol is preferable. More than 2 kinds of alignment polymers may be used in combination.

The alignment film containing an alignment polymer is generally formed as follows: a composition in which an oriented polymer is dissolved in a solvent (hereinafter, sometimes referred to as an oriented polymer composition) is applied to a substrate, and the substrate is formed on the surface thereof by removing the solvent; alternatively, the oriented polymer composition is formed on the surface of the substrate by applying the composition to the substrate, removing the solvent, and rubbing (rubbing method).

Examples of the solvent include: alcohol solvents such as water, methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, etc.; ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ -butyrolactone, propylene glycol methyl ether acetate, ethyl lactate, and the like; ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, and methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran and dimethoxyethane; and chlorinated hydrocarbon solvents such as chloroform and chlorobenzene. These solvents may be used alone, or two or more of them may be used in combination.

The concentration of the orientation polymer in the orientation polymer composition is within a range in which the orientation polymer material is completely soluble in the solvent, and is preferably 0.1 to 20% by mass, and more preferably about 0.1 to 10% by mass in terms of solid content, relative to the solution.

The alignment polymer composition may be a commercially available alignment film material. Commercially available alignment film materials include Sunever (registered trademark, manufactured by Nissan chemical industries, Ltd.), OPTMER (registered trademark, manufactured by JSR corporation), and the like.

Examples of the method for applying the oriented polymer composition to a substrate include: a known method such as a spin coating method, an extrusion method, a gravure coating method, a die coating method, a slit coating method, a bar coating method, a coating method such as an applicator method, a printing method such as a flexographic printing method, and the like. When the polarizing film of the present invention is produced by a Roll-to-Roll (Roll) type continuous production method described later, a printing method such as a gravure coating method, a die coating method, or a flexographic printing method is generally used as the coating method.

Examples of the method for removing the solvent contained in the oriented polymer composition include a natural drying method, a forced air drying method, a heat drying method, a reduced pressure drying method, and the like.

Rubbing (rubbing method) is performed as necessary to impart an alignment regulating force to the alignment film.

By selecting the direction in which rubbing is performed, the direction of the orientation restriction force can be arbitrarily controlled.

Examples of the method for imparting orientation restriction by the rubbing method include: a method of bringing a film of an oriented polymer formed on the surface of a base material by applying an oriented polymer composition to the base material and annealing the same into contact with a rubbing roll around which a rubbing cloth is wound and rotated.

The photo alignment film is generally formed as follows: a composition containing a polymer or monomer having a photoreactive group and a solvent (hereinafter, sometimes referred to as "composition for forming a photoalignment film") is applied to a substrate, and irradiated with light (preferably polarized UV) to form a film on the surface of the substrate. The photo alignment film is more preferable from the viewpoint that the direction of the alignment regulating force can be arbitrarily controlled by selecting the polarization direction of the irradiated light.

The photoreactive group means a group that generates liquid crystal aligning ability by light irradiation. Specifically, there may be mentioned: and a group participating in a photoreaction originating in liquid crystal aligning ability, such as orientation induction or isomerization reaction, dimerization reaction, photocrosslinking reaction, or photolysis reaction of molecules by light irradiation. Among them, a group participating in dimerization reaction or photocrosslinking reaction is preferable from the viewpoint of excellent orientation. The photoreactive group is preferably a group having an unsaturated bond, particularly a double bond, and particularly preferably a group having at least one bond selected from a carbon-carbon double bond (C ═ C bond), a carbon-nitrogen double bond (C ═ N bond), a nitrogen-nitrogen double bond (N ═ N bond), and a carbon-oxygen double bond (C ═ O bond).

Examples of the photoreactive group having a C ═ C bond include: vinyl, polyene, stilbene, stilbazole, chalcone, and cinnamoyl. Examples of the photoreactive group having a C ═ N bond include groups having a structure of an aromatic schiff base, an aromatic hydrazone, or the like. Examples of the photoreactive group having an N ═ N bond include: azophenyl, azonaphthyl, aromatic heterocyclic azo group, bisazo group, formazan (formazan) group, and a group having an azoxybenzene structure. Examples of the photoreactive group having a C ═ O bond include a benzophenone group, a coumarin group, an anthraquinone group, and a maleimide group. These groups may have substituents such as alkyl groups, alkoxy groups, aryl groups, allyloxy groups, cyano groups, alkoxycarbonyl groups, hydroxyl groups, sulfonic acid groups, and halogenated alkyl groups.

Among them, a photoreactive group participating in a photodimerization reaction is preferable, and cinnamoyl group and chalcone group are preferable from the viewpoint of easily obtaining a photo alignment film which requires a small amount of polarized light for photo alignment and is excellent in thermal stability and temporal stability. The polymer having a photoreactive group is particularly preferably: the terminal part of the polymer side chain is provided with a polymer of cinnamoyl capable of forming a cinnamic acid structure.

The solvent contained in the composition for forming a photo-alignment film may be the same solvent as that contained in the above-described alignment polymer composition, and may be appropriately selected according to the solubility of the polymer or monomer having a photoreactive group.

The content of the polymer or monomer having a photoreactive group in the composition for forming a photo alignment film may be appropriately adjusted according to the kind of the polymer or monomer and the thickness of the target photo alignment film, and is preferably at least 0.2 mass%, and more preferably in the range of 0.3 to 10 mass%. The composition for forming a photo-alignment film may contain a polymer material such as polyvinyl alcohol or polyimide, and a photosensitizer within a range that does not significantly impair the characteristics of the photo-alignment film.

The method of applying the composition for forming a photo-alignment film to a substrate may be the same as the method of applying the alignment polymer composition to a substrate. The method for removing the solvent from the applied composition for forming a photo-alignment film includes, for example, the same method as the method for removing the solvent from the alignment polymer composition.

For the irradiation of polarized light, after removing the solvent from the composition for forming a photo-alignment film applied on the substrate, polarized UV may be directly irradiated, or polarized light may be irradiated from the base material side to transmit the polarized light. In addition, the polarized light is particularly preferably substantially parallel light. The wavelength of the polarized light to be irradiated is preferably a wavelength in a wavelength region where the photoreactive group of the polymer or monomer having a photoreactive group can absorb light energy. Specifically, UV (ultraviolet) light having a wavelength of 250 to 400nm is particularly preferable. Examples of the light source used for the polarized light irradiation include a xenon lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, a metal halide lamp, and ultraviolet lasers such as KrF and ArF, and the high-pressure mercury lamp, the ultra-high-pressure mercury lamp, and the metal halide lamp are more preferable. These lamps are preferable because the emission intensity of ultraviolet rays having a wavelength of 313nm is large. Polarized UV can be irradiated by irradiating light from the above light source through an appropriate polarizing plate. As the polarizing plate, a polarizing filter, a polarizing prism such as Glan-thompson (Glan-thompson) and Glan-Taylor (Glan-Taylor), or a wire grid type polarizing plate may be used.

Note that, if masking is performed when rubbing or polarized light irradiation is performed, a plurality of regions (patterns) in which the liquid crystal alignment direction is different may be formed.

The groove alignment film is a film in which liquid crystal alignment can be obtained by using a concave-convex pattern or a plurality of grooves on the film surface. The following facts are reported by h.v. kennel et al: when liquid crystal molecules are placed on a substrate having a plurality of linear grooves (grooves) arranged at equal intervals, the liquid crystal molecules are aligned in a direction along the grooves (Physical Review a24(5), p 2713, 1981).

Specific methods for forming the groove alignment film on the surface of the substrate include: a method of forming a concave-convex pattern by exposing the surface of a photosensitive polyimide through an exposure mask having a slit with a periodic pattern shape, and then performing development and rinsing treatments to remove an unnecessary polyimide film; a method of forming a UV-curable resin layer on a plate-like master having grooves on the surface thereof, transferring the resin layer to a substrate film, and curing the resin layer; a method of transferring a substrate film on which a UV curable resin layer is formed, pressing a roll-shaped master having a plurality of grooves against the surface of the UV curable resin layer to form irregularities, and then curing the substrate film may be a method described in japanese patent application laid-open nos. 6-34976 and 2011-242743.

Among the above methods, preferred are: and a method of forming unevenness by pressing a roll-shaped master having a plurality of grooves against the surface of the UV-curable resin layer and then curing the formed unevenness. Stainless steel (SUS) can be used for the roll master from the viewpoint of durability.

The UV curable resin may use a polymer of monofunctional acrylate, a polymer of polyfunctional acrylate, or a polymer of a mixture thereof.

The monofunctional acrylate is a compound having 1 group (hereinafter, sometimes referred to as (meth) acryloyloxy group) selected from acryloyloxy group (CH2 ═ CH-COO-) and methacryloyloxy group (CH2 ═ C (CH3) — COO in the molecule.

Examples of the monofunctional acrylate having 1 (meth) acryloyloxy group include: alkyl (meth) acrylates having 4 to 16 carbon atoms, β carboxyalkyl (meth) acrylates having 2 to 14 carbon atoms, alkylated phenyl (meth) acrylates having 2 to 14 carbon atoms, methoxypolyethylene glycol (meth) acrylates, phenoxypolyethylene glycol (meth) acrylates, isobornyl (meth) acrylates, and the like.

The multifunctional acrylate generally refers to a compound having 2 to 6 (meth) acryloyloxy groups in the molecule.

Difunctional acrylates having 2 (meth) acryloyloxy groups may be exemplified by: 1, 3-butanediol di (meth) acrylate; 1, 3-butanediol (meth) acrylate; 1, 6-hexanediol di (meth) acrylate; ethylene glycol di (meth) acrylate; diethylene glycol di (meth) acrylate; neopentyl glycol di (meth) acrylate; triethylene glycol di (meth) acrylate; tetraethylene glycol di (meth) acrylate; polyethylene glycol diacrylate (PEG-diacrylate); bis (acryloyloxyethyl) ether of bisphenol a; ethoxylated bisphenol a di (meth) acrylate; propoxylated neopentyl glycol di (meth) acrylate; ethoxylated neopentyl glycol di (meth) acrylate and 3-methylpentanediol di (meth) acrylate, and the like.

Examples of the polyfunctional acrylate having 3 to 6 (meth) acryloyloxy groups include:

trimethylolpropane tri (meth) acrylate; pentaerythritol tri (meth) acrylate; tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate; ethoxylated trimethylolpropane tri (meth) acrylate; propoxylated trimethylolpropane tri (meth) acrylate; pentaerythritol tetra (meth) acrylate; dipentaerythritol penta (meth) acrylate; dipentaerythritol hexa (meth) acrylate; tripentaerythritol tetra (meth) acrylate; tripentaerythritol penta (meth) acrylate; tripentaerythritol hexa (meth) acrylate; tripentaerythritol hepta (meth) acrylate; tripentaerythritol octa (meth) acrylate;

a reaction product of pentaerythritol tri (meth) acrylate and an anhydride; a reaction product of dipentaerythritol penta (meth) acrylate and an anhydride;

a reaction product of tripentaerythritol hepta (meth) acrylate and an anhydride;

caprolactone-modified trimethylolpropane tri (meth) acrylate; caprolactone-modified pentaerythritol tri (meth) acrylate; caprolactone-modified tris (2-hydroxyethyl) isocyanurate tri (meth) acrylate; caprolactone-modified pentaerythritol tetra (meth) acrylate; caprolactone-modified dipentaerythritol penta (meth) acrylate; caprolactone-modified dipentaerythritol hexa (meth) acrylate; caprolactone-modified tripentaerythritol tetra (meth) acrylate; caprolactone-modified tripentaerythritol penta (meth) acrylate; caprolactone-modified tripentaerythritol hexa (meth) acrylate; caprolactone-modified tripentaerythritol hepta (meth) acrylate; caprolactone-modified tripentaerythritol octa (meth) acrylate; a reaction product of caprolactone-modified pentaerythritol tri (meth) acrylate and an anhydride; a reaction product of caprolactone-modified dipentaerythritol penta (meth) acrylate and an anhydride; and a reaction product of caprolactone-modified tripentaerythritol hepta (meth) acrylate and an acid anhydride. In the specific examples of the polyfunctional acrylate shown here, the (meth) acrylate means an acrylate or a methacrylate. The caprolactone modification is an open ring body or an open ring polymer in which caprolactone is introduced between a site derived from an alcohol of a (meth) acrylate compound and a (meth) acryloyloxy group.

Commercially available products of the multifunctional acrylate may also be used.

Examples of commercially available products include: A-DOD-N, A-HD-N, A-NOD-N, APG-100, APG-200, APG-400, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMPT, AD-TMP, ATM-35E, A-TMMT, A-9550, A-DPH, HD-N, NOD-N, NPG, TMPT (manufactured by NONGZHUN CHEMICAL CO., LTD.), "ARONIX M-220" "," ARONIX M-325 "," ARONIX M-240 "," ARONIX M-270 "," ARONIX M-309 "," ARONIX M-310 "," ARONIX M-321 "," ARONIX-350 "," ARONIX M-360 "," ARONM-305 "," ARONIX M-306 "," ARONIX M-450 ", (A-D, A-G-400, A-GLY-9-GLY-20-TMM-220, a-M-P, a-M-450, a-A-P, a-B, a-P, a, "ARONIX M-451", "ARONIX M-408", "ARONIX M-400", "ARONIX M-402", "ARONIX M-403", "ARONIX M-404", "ARONIX M [ -405", "ARONIX M-406" (manufactured by Toyo Kagaku Co., Ltd.), "EBECRYL 11", "EBECRYL 145", "EBECRYL 150", "EBECRYL 40", "EBECRYL 140", "EBECRYL 180", DPGDA, HDDA, TPGDA, HPNDA, PETIA, PETRA, TMPTA, TMPEOTA, DPHA, EBECRYL series (manufactured by Daicel-Cytec Co., Ltd.), and the like.

The width of the convex portion is preferably 0.05 to 5 μm, the width of the concave portion is preferably 0.1 to 5 μm, and the depth of the step of the concave portion is 2 μm or less, preferably 0.01 to 1 μm or less. If the amount is within this range, the alignment of the liquid crystal is small.

The thickness of the alignment film is usually 10nm to 10000nm, preferably 10nm to 1000nm, and more preferably 10nm to 500 nm.

Examples of the method for applying the composition of the present invention include: the method is the same as the method exemplified as the method of applying the alignment polymer composition to the substrate.

< Process (B) >

In the case where the composition of the present invention contains a solvent, the solvent is usually removed from the formed coating film.

Examples of the method for removing the solvent include: natural drying, air drying, heat drying, reduced pressure drying, etc.

The polymerizable liquid crystal compound contained in the formed coating film is usually heated to a temperature at which the polymerizable liquid crystal compound is converted into a solution state or higher, and then cooled to a temperature at which liquid crystal alignment occurs, whereby alignment occurs to form a liquid crystal phase.

The temperature at which the polymerizable liquid crystal compound contained in the formed coating film is aligned can be determined in advance by texture observation or the like using a composition containing the polymerizable liquid crystal compound. In addition, the removal of the solvent and the alignment of the liquid crystal may be performed simultaneously. The temperature at this time is preferably 50 to 200 ℃ depending on the kind of the solvent or polymerizable liquid crystal compound to be removed, and more preferably 80 to 130 ℃ when the substrate is a resin substrate.

In the case of obtaining a circularly polarizing plate having the polarizing film of the present invention and the 1/4 wave plate using a substrate which is an 1/4 wave plate, the orientation direction of the polymerizable liquid crystal compound may be set so that the transmission axis of the obtained polarizing film and the slow axis (optical axis) of the substrate are substantially 45 °.

< Process (C) >

The polymerizable liquid crystal compound is polymerized by irradiating the polymerizable liquid crystal compound having been aligned with an active energy ray.

The polymerizable liquid crystal compound having been aligned is polymerized, whereby a polarizing film comprising the polymerizable liquid crystal compound polymerized in an aligned state and the compound (1) aligned together with the polymerizable liquid crystal compound can be obtained.

The polarizing film containing a polymerizable liquid crystal compound polymerized in a state of maintaining a smectic liquid crystal phase has higher polarizing performance than a conventional host-guest polarizing film, that is, a polarizing film obtained by polymerizing a polymerizable liquid crystal compound or the like in a state of maintaining a nematic liquid crystal phase, and has excellent polarizing performance and strength compared to a polarizing film coated with only a dichroic dye or a lyotropic liquid crystal compound.

The light source of the active energy ray may be any light source that generates ultraviolet rays, electron rays, X-rays, or the like. Preferred are light sources having a light emission distribution at a wavelength of 400nm or less, such as a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, an ultrahigh-pressure mercury lamp, a chemical lamp, a black light lamp, a microwave-excited mercury lamp, and a metal halide lamp.

The irradiation energy of the active energy ray is preferably set so that the irradiation intensity in a wavelength region effective for activating the polymerization initiator is 10 to 5000mJ/cm²More preferably 100 to 2000mJ/cm². If the irradiation energy is less than 10mJ/cm²The curing of the polymerizable liquid crystal compound tends to be insufficient.

The thickness of the polarizing film of the present invention thus formed is preferably in the range of 0.5 μm to 10 μm, and more preferably 1 μm to 5 μm. The thickness of the polarizing film of the present invention can be determined by measurement using an interferometric film thickness meter, a laser microscope, or a stylus film thickness meter.

The polarizing film of the present invention is particularly preferably one that can obtain bragg peaks in X-ray diffraction measurement. Examples of the polarizing film of the present invention from which the bragg peak is obtained include a polarizing film showing a diffraction peak derived from a hexagonal phase or a crystalline phase.

Maximum absorption (. lamda.) of the polarizing film of the present invention_max1) Preferably, the concentration is in the range of 350 to 550nm, more preferably in the range of 410 to 540nm, and still more preferably in the range of 430 to 530 nm. In addition, the maximum absorption (. lamda.) measured by dissolving the compound (1) contained in the polarizing film of the present invention in an appropriate solvent was compared with_max2)，λ_max1Preferably long wavelength shifts occur. This long wavelength shift is exhibited when the compound (1) is dispersed between molecular chains formed by the polymerizable liquid crystal compound that is polymerized, and shows that the compound (1) strongly interacts with the molecular chains. Long wavelength shift refers to the difference in maximum absorption (λ)_max1-λ_max2) The difference is preferably 10nm or more, more preferably 30nm or more, as a positive value.

The polarizing film of the present invention preferably exhibits a dichroic ratio of 15 or more, more preferably 25 or more.

When the substrate used is not an 1/4 wave plate, the circularly polarizing plate can be obtained by laminating the polarizing film of the present invention obtained with a 1/4 wave plate. At this time, it is preferable to stack the polarizing film of the present invention so that the transmission axis is substantially 45 ° to the slow axis (optical axis) of the 1/4 wave plate. Further, a polarizing plate that functions as an optical compensation film can also be obtained by aligning or intersecting the transmission axis of the polarizing film of the present invention with or perpendicular to the optical axis of a retardation film such as an 1/4 wave plate.

The lamination of the polarizing film of the present invention and the 1/4 wave plate may be performed together with the substrate on which the polarizing film of the present invention is formed or the substrate on which the alignment film is formed, or may be performed by removing the substrate, or the substrate and the alignment film. The lamination of the polarizing film of the present invention and 1/4 wave plate formed on the surface of the substrate or the substrate having the alignment film formed thereon can be performed, for example, as follows: the polarizing film of the present invention is formed by bonding the surface thereof to an 1/4 wave plate using an adhesive, and then removing the substrate or the substrate on which the alignment film is formed. In this case, the adhesive may be applied to the polarizing film of the present invention, or may be applied to the 1/4 wave plate.

< method for continuously producing polarizing film of the present invention >

The polarizing film of the present invention is preferably continuously manufactured in a roll-to-roll form. An example of a main part of a method for continuously producing a polarizing film of the present invention in a roll-to-roll manner will be described with reference to fig. 1.

The 1 st roll 210 having the base material wound around the 1 st winding core 210A is, for example, easily available from the market. Among the exemplified substrates, the substrates commercially available in the form of such rolls include: films comprising cellulose esters, cycloolefin resins, polycarbonates, polyethylene terephthalate, and polymethacrylates, and the like.

Next, the substrate is wound out from the 1 st roll 210. The method of rolling out the substrate is performed as follows: the winding core 210A of the 1 st roller 210 is provided with an appropriate rotating means, and the 1 st roller 210 is rotated by the rotating means. Further, an appropriate auxiliary roller 300 may be provided in the direction in which the substrate is conveyed from the 1 st roller 210, and the substrate may be wound out by the rotating means of the auxiliary roller 300. Further, the substrate may be unwound while applying an appropriate tension to the substrate by providing a rotating means to both the 1 st winding core 210A and the auxiliary roller 300.

When the substrate wound off the 1 st roll 210 passes through the coating device 211A, the coating device 211A coats the surface with the composition for forming a photo-alignment film. The coating apparatus 211A for continuously coating the photo-alignment film-forming composition in this manner is preferably a gravure coating method, a die coating method, or a flexographic printing method.

The substrate passed through the coating device 211A is conveyed to a drying furnace 212A, and dried by the drying furnace 212A, thereby continuously forming a first coating film on the surface of the substrate. The drying furnace 212A may be a hot air type drying furnace combining a forced air drying method and a heat drying method, for example. The set temperature of the drying furnace 212A is determined according to the kind of the solvent included in the photo-alignment film forming composition. The drying furnace 212A may include a plurality of regions having different set temperatures, or may be a plurality of drying furnaces having different set temperatures, which are provided in series.

The obtained first coating film is irradiated with polarized light by the polarized UV irradiation device 213A, whereby a photo alignment film can be obtained.

Next, the substrate on which the photo-alignment film is formed passes through the coating apparatus 211B. After the composition of the present invention containing a solvent is coated on the photo-alignment film by the coating apparatus 211B, a second coating film in which the polymerizable liquid crystal compound contained in the composition of the present invention is aligned can be obtained by passing the composition through the drying furnace 212B. The drying furnace 212B plays a role as follows: the present invention relates to a method for producing a photo-alignment film, and more particularly, to a method for producing a photo-alignment film, which comprises the steps of removing a solvent from a composition of the present invention containing the solvent coated on a photo-alignment film, and aligning a polymerizable liquid crystal compound contained in the composition by applying thermal energy. Similarly to the drying furnace 212A, the drying furnace 212B may include a plurality of regions having different set temperatures, or may include a plurality of drying furnaces having different set temperatures, which are provided in series.

The polymerizable liquid crystal compound contained in the second coating film is transferred to the active energy ray irradiation device 213B in an aligned state. The active energy ray irradiation device 213B further performs active energy ray irradiation. The polarizing film is obtained by polymerizing the polymerizable liquid crystal compound in an aligned state by irradiation with an active energy ray from the active energy ray irradiation device 213B.

The polarizing plate continuously manufactured in this manner is wound around the 2 nd winding core 220A, and the 2 nd roll 220 can be obtained. In the winding, co-winding using an appropriate spacer may be performed.

In this manner, the polarizing plate can be continuously manufactured in a Roll-to-Roll (Roll) manner by sequentially passing the substrate from the 1 st Roll 210 through the coating device 211A, the drying furnace 212A, the polarized UV irradiation device 213A, the coating device 211B, the drying furnace 212B, and the active energy ray irradiation device 213B.

In the manufacturing method shown in fig. 1, the method of continuously manufacturing the polarizing film of the present invention is shown, and for example, the polarizing film of the present invention may be continuously manufactured by winding a roll-shaped laminate of the base material and the photo-alignment film around a core by passing the base material from the 1 st roll through the coating apparatus 211A, the drying furnace 212A, and the polarized UV irradiation apparatus 213A in this order, further winding out the roll-shaped laminate, and passing the roll-shaped laminate through the coating apparatus 211B, the drying furnace 212B, and the active energy ray irradiation apparatus 213B in this order.

When the polarizing film of the present invention is manufactured in the form of the 2 nd roll 220, a long polarizing film of the present invention is wound from the 2 nd roll 220, cut into a predetermined size, and then an 1/4 wave plate is attached to the cut polarizing film, whereby a circularly polarizing plate can be manufactured. Further, a 3 rd roll in which a long 1/4 wave plate is wound around a winding core may be prepared, and a long circularly polarizing plate may be continuously manufactured.

A method for continuously manufacturing a long circularly polarizing plate will be described with reference to fig. 2. The manufacturing method comprises the following steps:

a step of continuously winding the polarizing film of the present invention from the 2 nd roll 220 and continuously winding the long 1/4 wave plate from the 3 rd roll 230 on which the long 1/4 wave plate is wound;

a step of obtaining a long circularly polarizing plate by continuously laminating the polarizing film of the present invention and the long 1/4 wave plate; and

and a step of winding the obtained long circularly polarizing plate around the 4 th winding core 240A to obtain a4 th roll 240. This method is so-called roll-to-roll bonding. An adhesive may be used for bonding.

< uses of polarizing film of the present invention >

The polarizing film of the present invention and the circularly polarizing plate having the polarizing film of the present invention and the 1/4 wave plate can be used for various display devices.

The display device is a device having a display element, and includes a light-emitting element or a light-emitting device as a light-emitting source. Examples of the display device provided with the polarizing plate include a liquid crystal display device, an organic Electroluminescence (EL) display device, an inorganic Electroluminescence (EL) display device, an electron emission display device (e.g., a field emission display device (FED), a surface field emission display device (SED)), electronic paper (a display device using electronic ink or an electrophoretic element, the liquid crystal display device includes any one of a transmission type liquid crystal display device, a semi-transmission type liquid crystal display device, a reflection type liquid crystal display device, a direct-view type liquid crystal display device, a projection type liquid crystal display device, and the like.

The polarizing film of the present invention can be effectively used particularly for liquid crystal display devices, organic Electroluminescent (EL) display devices, and inorganic Electroluminescent (EL) display devices.

The circularly polarizing plate having the polarizing film of the present invention and the 1/4 wave plate can be effectively used in particular for organic Electroluminescent (EL) display devices and inorganic Electroluminescent (EL) display devices.

When the polarizing film of the present invention is used in a liquid crystal display device, the polarizing film of the present invention may be disposed outside the liquid crystal cell or may be disposed inside the liquid crystal cell.

In particular, a first configuration in the case of being provided inside a liquid crystal cell of a transmissive active matrix color liquid crystal display device will be described below with reference to fig. 3. The display device 30 is composed of a first substrate 31, a first polarizing film 32 of the present invention, a color filter layer 33, a planarization layer 34, an ITO electrode layer 35, a first alignment film 36, a liquid crystal layer 37, a second alignment film 38, a second polarizing film 39 of the present invention, a TFT layer 40 including a thin film transistor circuit and a pixel electrode, and a second substrate 41.

The color filter layer is a layer that extracts light of a desired wavelength from incident light from the substrate 41 side, and may be a layer that absorbs light of a wavelength other than the desired wavelength from white light and transmits only light of the desired wavelength, or may be a layer that converts the wavelength of incident light to emit light of the desired wavelength.

The above-described first and second polarizing films of the present invention may each comprise an alignment film on the first and second substrate sides. The alignment film may be a rubbing alignment film, or a photo-alignment film may be used.

Also, the first polarizing film of the present invention may include a phase difference layer.

Next, the second configuration will be described below with reference to fig. 4. The display device 60 is composed of a first substrate 61, a first polarizing film 62 of the present invention, a color filter layer 63, a planarization layer 64, an ITO electrode layer 65, a first alignment film 66, a liquid crystal layer 67, a second alignment film 68, a TFT layer 70 including a thin film transistor circuit and a pixel electrode, a second substrate 71, and a second polarizing film 72.

The second polarizing film 72 located on the opposite side of the second substrate 71 from the TFT layer 70 may be the polarizing film of the present invention, or may be a polarizing film obtained by stretching polyvinyl alcohol dyed with iodine.

The third configuration will be described below with reference to fig. 5. The display device 80 is composed of a first substrate 81, a color filter layer 82, a first polarizing film 83 of the present invention, a planarization layer 84, an ITO electrode layer 85, a first alignment film 86, a liquid crystal layer 87, a second alignment film 88, a TFT layer 90 including a thin film transistor circuit and a pixel electrode, a second substrate 91, and a second polarizing film 92.

In the third configuration, the second polarizing film 92 may be the polarizing film of the present invention, or may be a polarizing film obtained by dyeing polyvinyl alcohol with iodine and stretching the same. When the second polarizing film 92 is the polarizing film of the present invention, the second polarizing film may be located between the second substrate 91 and the TFT layer 90, similarly to the first configuration.

In addition, in the third configuration, the color filter layer 82 may be located on the opposite side of the first substrate 81 from the liquid crystal layer.

Due to the particles contained in the color filter layer, the polarized light is scattered and depolarization may occur. Therefore, among the first to third configurations, more preferred are: the first polarizing film of the present invention has a third configuration on the liquid crystal layer side of the color filter layer.

Examples

The present invention will be described in further detail below with reference to examples. In the examples, "%" and "part(s)" are% by mass and part(s) by mass unless otherwise specified.

Example 1

0.30g of the compound represented by the formula (2A), 0.48g of triethylamine, 0.023g of N, N-dimethylaminopyridine and 3.0g of tetrahydrofuran were mixed. After the resulting mixture was cooled to 0 ℃ 0.39g of the compound represented by the formula (3A) was added dropwise. The resulting mixture was stirred at 25 ℃ for 18 hours. The resulting reaction mixture was concentrated, washed with ethyl acetate and water, and filtered. The obtained solid was washed with acetonitrile and then dried, whereby 0.129g of the compound represented by formula (1A) (hereinafter referred to as compound (IA)) was obtained as an orange solid.

Mw：489(LC-MS)

Maximum absorption wavelength (lambda)_max2) 441nm (chloroform solution)

Example 2

0.30g of the compound represented by the formula (2B), 0.41g of triethylamine, 0.020g of N, N-dimethylaminopyridine and 4.5g of tetrahydrofuran were mixed. After the resulting mixture was cooled to 0 ℃ 0.21g of the compound represented by the formula (3A) was added dropwise. The resulting mixture was stirred at 25 ℃ for 18 hours. The resulting reaction mixture was concentrated, washed with ethyl acetate and water, and filtered. The obtained solid was washed with acetonitrile and then dried, whereby 0.189g of a compound represented by formula (1B) (hereinafter referred to as compound (IB)) was obtained as an orange solid.

Mw：544(LC-MS)

Maximum absorption wavelength (lambda)_max2) 430nm (chloroform solution)

[ polymerizable liquid Crystal Compound ]

As the polymerizable liquid crystal compound, a compound represented by the following formula (4-6) [ hereinafter referred to as compound (4-6) ], a compound represented by the following formula (4-8) [ hereinafter referred to as compound (4-8) ], a compound represented by the following formula (4-14) [ hereinafter referred to as compound (4-14) ], and a compound represented by the following formula (4-17) [ hereinafter referred to as compound (4-17) ].

The compound (4-6) was synthesized by the method described in Lub et al, Recl, Trav, Chim, Pays-Bas, 115, 321-328 (1996). Further, compound (4-8) was produced according to this method.

Compound (4-14) and compound (4-17) were produced according to the method described in Japanese patent No. 4719156.

Compound (4-6):

[ measurement of phase transition temperature ]

The phase transition temperature of the compound (4-6) was determined by determining the phase transition temperature of the film composed of the compound (4-6). This operation is as follows.

The film composed of the compound (4-6) was formed on the glass substrate on which the alignment film was formed, and the phase transition temperature was confirmed by texture observation using a polarization microscope (BX-51, manufactured by olympus) while heating. After the temperature of the compound (4-6) is raised to 120 ℃, the phase is changed into a nematic phase at 112 ℃, a smectic A phase at 110 ℃ and a smectic B phase at 94 ℃ when the temperature is lowered.

Compound (4-8):

[ measurement of phase transition temperature ]

The phase transition temperature of the compound (4-8) was confirmed by the same procedure as that of the compound (4-6). After the temperature of the compound (4-8) is raised to 140 ℃, the phase is changed into a nematic phase at 131 ℃, a smectic A phase at 80 ℃ and a smectic B phase at 68 ℃ when the temperature is lowered.

Compound (4-14):

[ measurement of phase transition temperature ]

The phase transition temperature of the compound (4-14) was confirmed by the same procedure as that of the compound (4-6). After the temperature of the compound (4-14) is raised to 140 ℃, the phase is changed into a nematic phase at 106 ℃, a smectic A phase at 103 ℃ and a smectic B phase at 86 ℃ when the temperature is lowered.

Compound (4-17):

[ measurement of phase transition temperature ]

The phase transition temperature of the compound (4-17) was confirmed by the same procedure as that of the compound (4-6). After the temperature of the compound (4-17) was raised to 140 ℃, the phase was changed to a nematic phase at 119 ℃, a smectic A phase at 100 ℃ and a smectic B phase at 77 ℃ when the temperature was lowered.

Example 3

[ preparation of composition ]

The following ingredients were mixed and stirred at 80 ℃ for 1 hour to obtain composition (1).

Polymerizable liquid crystal compound: 75 parts of compound (4-6)

25 parts of compound (4-8)

Compound (1): compound (1A) 2.5 parts

Polymerization initiator:

6 parts of 2-dimethylamino-2-benzyl-1- (4-morpholinophenyl) butan-1-one (IRGACURE 369; Ciba Speciality Chemicals Co., Ltd.)

Leveling agent:

polyacrylate Compound (BYK-361N; manufactured by BYK-Chemie Co., Ltd.)

1.5 parts of

Solvent: 250 parts of chloroform

[ measurement of phase transition temperature ]

The phase transition temperature of the components contained in the composition (1) was determined in the same manner as in the case of the compound (4-6). The composition is heated to 140 deg.C, and when the temperature is reduced, the phase is changed into nematic phase at 115 deg.C, smectic A phase at 105 deg.C, and smectic B phase at 75 deg.C.

[ production and evaluation of the polarizing film ]

1. Formation of alignment film

A2 mass% aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 completely saponified type, manufactured by Wako pure chemical industries, Ltd.) was applied onto a glass substrate by a spin coating method, and after drying, a film having a thickness of 100nm was formed. Next, the surface of the obtained film was subjected to rubbing treatment to form an alignment film. The rubbing treatment was carried out using a semi-automatic rubbing device (trade name: LQ-008 type, manufactured by Heiyang engineering Co., Ltd.) and a cloth (trade name: YA-20-RW, manufactured by Gikawa chemical Co., Ltd.) under conditions of a pressing amount of 0.15mm, a rotation speed of 500rpm and 16.7 mm/s. By this rubbing treatment, a laminate 1 having an alignment film formed on a glass substrate was obtained.

2. Formation of polarizing films

By passingThe spin coating method applied the composition (1) on the alignment film of the laminate 1, dried by heating on a heating plate at 120 ℃ for 1 minute, and then rapidly cooled to room temperature to form a dried film containing a polymerizable liquid crystal compound aligned on the alignment film. Next, an exposure amount of 2000mJ/cm was measured using a UV irradiation apparatus (SPOT CURE SP-7: manufactured by NIGHT ELECTRIC MACHINE CO., LTD.)²The dried film was irradiated with ultraviolet light (365nm basis), and the polymerizable liquid crystal compound contained in the dried film was polymerized while maintaining the alignment state, thereby forming a polarizing film (1) from the dried film, and obtaining a laminate 2. The thickness of the polarizing film at this time was measured by a laser microscope (OLS 3000, Olympus corporation), and found to be 1.7. mu.m.

X-ray diffraction measurement

The polarizing film (1) was subjected to X-ray diffraction measurement using an X-ray diffraction device X' Pert PRO MPD (manufactured by Spectris corporation). X-rays generated under the conditions of an X-ray tube current of 40mA and an X-ray tube voltage of 45kV using Cu as a target were incident from the rubbing direction (the rubbing direction of the orientation film located under the polarizing film was obtained in advance) through a fixed divergent slit 1/2 °, and were scanned in steps of 2 θ 0.01671 ° in a scan range of 2 θ 4.0 to 40.0 °, and as a result, a sharp diffraction peak (bragg peak) having a full width at half maximum (FWHM) of about 0.31 ° was obtained in the vicinity of 2 θ 20.1 °. In addition, the same results were obtained even with incidence in the perpendicular direction by rubbing. An order period (d) of aboutIt is known that a structure reflecting a highly ordered smectic phase is formed.

4. Determination of dichroic ratio

The absorbance (A) in the transmission axis direction at the maximum absorption wavelength was measured by a two-beam method using a device in which a holder having a laminate 2 was placed in a spectrophotometer (UV-3150, manufactured by Shimadzu corporation)¹) And absorbance (A) in the absorption axis direction²). For this stent, a mesh (mesh) that cuts off 50% of the light is provided on the reference side. According to the determined direction of the transmission axisAbsorbance (A) of (A)¹) And absorbance (A) in the absorption axis direction²) The value of (A) is calculated as the ratio²/A¹) As a dichroic ratio. Maximum absorption wavelength (lambda)_max1) At 452nm, the dichroic ratio at this wavelength shows values up to 38. It can be said that the higher the dichroic ratio, the more useful as a polarizing film. Maximum absorption wavelength (. lamda.) according to Compound (1A)_max2) At 441nm, it was confirmed that long wavelength shift occurred. The results of this long wavelength shift show: in the polarizing film of the present invention, when the compound (1A) is dispersed between the dense molecular chains formed by polymerizing the polymerizable liquid crystal compound, the compound (1A) strongly interacts with the molecular chains.

Further, a protective film (40 μm tac ("KC 4 UY" manufactured by Konica Minolta) was disposed on the surface of the formed polarizing film (1), and light was irradiated therefrom under the following conditions, thereby evaluating the light resistance. The polarizing film formed is excellent in light resistance.

The irradiation conditions of light in the light resistance test are as follows.

The use equipment comprises the following steps: santest XLS + manufactured by ATLAS company

Using a light source: xenon arc lamp

Exposure conditions: 250mW/m²

Test time: 120 hours

Exposure amount: 108000KJ/m²

Temperature: 60 deg.C

Example 4

A composition and a polarizing film each containing the compound (1B) were obtained in the same manner as in example 3, except that the compound (1B) was used instead of the compound (1A) in example 3.

Example 6

A compound represented by the formula (1C) was obtained by the same method as in example 1, except that the compound represented by the formula (2C) was used instead of the compound represented by the formula (2A) in example 1.

Example 7

A compound represented by the formula (1D) can be obtained by the same method as in example 1, except that the compound represented by the formula (2D) is used instead of the compound represented by the formula (2A) in example 1.

Example 8

A compound represented by the formula (1E) was obtained by the same method as in example 1, except that the compound represented by the formula (2E) was used instead of the compound represented by the formula (2A) in example 1.

Example 9

A compound represented by the formula (1F) was obtained by the same method as in example 1, except that the compound represented by the formula (2F) was used instead of the compound represented by the formula (2A) in example 1.

Example 10

A composition and a polarizing film each containing the compound (1C) were obtained in the same manner as in example 3 except that the compound (1C) was used instead of the compound (1A) in example 3.

Example 11

A composition and a polarizing film each containing the compound (1D) were obtained in the same manner as in example 3 except that the compound (1D) was used instead of the compound (1A) in example 3.

Example 12

A composition and a polarizing film each containing the compound (1E) were obtained in the same manner as in example 3 except that the compound (1E) was used instead of the compound (1A) in example 3.

Example 13

A composition and a polarizing film each containing the compound (1F) were obtained in the same manner as in example 3 except that the compound (1F) was used instead of the compound (1A) in example 3.

Industrial applicability

The novel compound of the present invention has a maximum absorption in the wavelength range of 350nm to 550nm and functions as a dichroic dye, and the composition of the present invention containing the compound can provide a polarizing film having a high dichroic ratio.

Description of the symbols

210 st roll

210A roll core

220 nd roller

220A roll core

211A, 211B coating device

212A, 212B drying oven

213A polarized UV irradiation device

213B active energy ray irradiation device

300 auxiliary roller

230 rd roller

230A roll core

240 th roller

240A roll core

300 auxiliary roller