JP7192933B2 - Polymer, method for producing the same, and optical film using the same - Google Patents

Description

TECHNICAL FIELD The present invention relates to a novel polymer, a method for producing the same, and an optical film using the same. The present invention relates to a novel polymer suitable for an optical compensation film for EL, a method for producing the same, and an optical film using the same.

Liquid crystal displays are widely used in mobile phones, computer monitors, notebook computers, and televisions as the most important display devices in the multimedia society.

Many optical films are used in liquid crystal displays to improve display characteristics. In particular, retardation films play a major role in improving contrast when viewed from the front or obliquely and in compensating for color tone. As conventional retardation films, polycarbonate and cyclic polyolefin are used, and both of these polymers are polymers having positive birefringence. Here, the positive and negative of birefringence are defined as follows.

The optical anisotropy of a polymer film molecularly oriented by stretching or the like is defined by nx as the refractive index in the fast axis direction in the plane of the film when the film is stretched, ny as the refractive index in the in-plane direction of the film perpendicular to it, and can be represented by a refractive index ellipsoid where nz is the refractive index in the thickness direction. Note that the fast axis refers to an axial direction in which the refractive index is low in the plane of the film.

Negative birefringence means that the stretching direction is the fast axis direction, and positive birefringence means the fast axis direction is the direction perpendicular to the stretching direction.

That is, in uniaxial stretching of a polymer having negative birefringence, the refractive index in the stretching axis direction is small (fast axis: stretching direction), and in uniaxial stretching of a polymer having positive birefringence, the axial direction perpendicular to the stretching axis has a small refractive index (fast axis: direction perpendicular to the stretching direction).

Many polymers have positive birefringence. Polymers having negative birefringence include acrylic resin and polystyrene, but acrylic resin has a small retardation and does not have sufficient properties as a retardation film. Polystyrene has a large photoelastic coefficient in the low-temperature region, so it is not used at present due to the stability of the phase difference, such as a change in the phase difference with a small amount of stress, and the practical problem of low heat resistance. .

A stretched polymer film that exhibits negative birefringence has a high refractive index in the thickness direction of the film, making it an unprecedented retardation film. Useful as a retardation film for compensating the viewing angle characteristics of displays such as displays (VA-LCD), in-plane alignment liquid crystal displays (IPS-LCD), reflective liquid crystal displays (reflective LCD), and viewing angle compensation films for polarizing plates. , and there is a strong market demand for retardation films having negative birefringence.

A method for producing a film in which the refractive index in the thickness direction of the film is increased by using a polymer having positive birefringence has been proposed. One is a treatment method in which a heat-shrinkable film is adhered to one or both sides of a polymer film, the laminate is heated and stretched, and a shrinkage force is applied in the film thickness direction of the polymer film (for example, Patent Documents 1 to 3). ). A method of uniaxially stretching a polymer film in-plane while applying an electric field has also been proposed (see, for example, Patent Document 4).

In addition, a retardation film composed of fine particles having negative optical anisotropy and a transparent polymer such as a maleimide copolymer has been proposed (see, for example, Patent Document 5).

However, the methods proposed in Patent Documents 1 to 4 have a problem of poor productivity due to the extremely complicated manufacturing process. Also, the control of the uniformity of the retardation is much more difficult than the conventional control by stretching.

The retardation film obtained in Patent Document 5 is a retardation film exhibiting negative birefringence by adding fine particles having negative optical anisotropy. There is a demand for a retardation film that does not require the addition of Further, with the expansion of display applications, there is a demand for a retardation film with higher heat resistance.

In addition, fumaric acid diester copolymers and retardation films made thereof have been proposed (see, for example, Patent Documents 6 to 12).

Although the fumaric acid diester-based copolymers proposed in Patent Documents 6 to 12 and films made thereof have a high retardation, there is currently a demand for a film having a high retardation even in a thinner film. there is

Furthermore, a single film type retardation film material has been proposed by combining a positive birefringent material and a negative birefringent material (see, for example, Patent Documents 13 and 14), and achieves higher optical properties. Therefore, there is a need for polymer materials exhibiting negative birefringence that can be composited.

Japanese Patent No. 2818983 JP-A-05-297223 JP-A-05-323120 JP-A-06-88909 JP 2005-156862 A JP 2008-112141 A JP 2012-032784 A WO2012/005120 JP 2008-129465 A JP 2006-193616 A WO2014/013982 WO2014/084178 WO2014/196552 WO2016/060115

The present invention has been made in view of the above problems, and an object of the present invention is to provide a polymer exhibiting negative birefringence by using a monomer unit having a specific structure, and a polymer obtained by using the same. An object of the present invention is to provide a polymer which is excellent in retardation properties and compatibility with different types of polymers and which can be easily combined, and an optical film comprising the same.

The present inventors have made intensive studies to solve the above problems, and as a result, have found that a specific copolymer can solve the above problems, and have completed the present invention.

That is, the present invention provides a polymer which does not contain an organic acid containing a bismethide group or a bismethidate and contains a monomer residue unit represented by the general formula (1), a method for producing the polymer, and It relates to an optical film using it.

(Here, R ₁ is a cyano group, R ₂ is a cyano group, an ester group (-C(=O)OX ₁ or an amide group (-C(=O)N(X ₄ )(X ₅ ) (here X ₁ represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 1 to 12 carbon atoms, and X ₄ to X ₅ each represent a linear alkyl group having 1 to 12 carbon atoms. , a branched alkyl group having 1 to 12 carbon atoms), R ₃ represents hydrogen, R ₄ to R ₈ each independently represent hydrogen, a hydroxy group, a carboxy group, or a sulfoxy group, and R ₄ to R ₈ shows a hydroxy group.)
Polymers suitable for the optical compensation film of the present invention are described in detail below.

The polymer of the present invention is a polymer containing a monomer residue unit represented by general formula (1). The polymer of the present invention exhibits negative birefringence and compatibility with different polymers by containing the monomer residue unit represented by the general formula (1).

R ₁ in the general formula (1) of the present invention is a cyano group, R ₂ is a cyano group, an ester group (-C(=O)OX ₁ or an amide group (-C(=O)N(X ₄ ) ( X ₅ ) (here, X ₁ represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 1 to 12 carbon atoms, and X ₄ to X ₅ each represent a a linear alkyl group, a branched alkyl group having 1 to 12 carbon atoms), R ₃ represents hydrogen, R ₄ to R ₈ each independently represent hydrogen, a hydroxy group, a carboxy group, or a sulfoxy group, At least one of R ₄ to R ₈ represents a hydroxy group.

Examples of linear alkyl groups having 1 to 12 carbon atoms in X _{1 ,} X ₄ and X ₅ include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group. Examples of branched alkyl groups having 1 to 12 carbon atoms include isopropyl group, sec-butyl group, tert-butyl group, and isobutyl group. Examples of cyclic groups having 3 to 14 carbon atoms include , for example, a cyclopropyl group, a cyclobutyl group, a cyclohexyl group, a phenyl group, a naphthyl group and the like.

R ₃ in the general formula (1) of the present invention represents hydrogen.

R ₄ to R ₈ in general formula (1) of the present invention each independently represent hydrogen, a hydroxy group, a carboxy group or a sulfoxy group, and at least one of R ₄ to R ₈ represents a hydroxy group.

Specific monomer residue units represented by general formula (1) include, for example, 2-hydroxy-α,β,β-trifluorostyrene residue units, 3-hydroxy-α,β, β-trifluorostyrene residue unit, 4-hydroxy-α,β,β-trifluorostyrene residue unit, 2-carboxy-α,β,β-trifluorostyrene residue unit, 3-carboxy-α,β , β-trifluorostyrene residue unit, 4-carboxy-α,β,β-trifluorostyrene residue unit, 4-sulfoxy-α,β,β-trifluorostyrene residue unit, 2,3-dihydroxy- α,β,β-trifluorostyrene residue unit, 2,4-dihydroxy-α,β,β-trifluorostyrene residue unit, 3,4-dihydroxy-α,β,β-trifluorostyrene residue unit , 2-hydroxycinnamonitrile residue unit, 3-hydroxycinnamonitrile residue unit, 4-hydroxycinnamonitrile residue unit, 2-carboxycinnamonitrile residue unit, 3-hydroxycinnamonitrile residue unit , 4-hydroxycinnamonitrile residue unit, 2-carboxycinnamonitrile residue unit, 3-carboxycinnamonitrile residue unit, 4-carboxycinnamonitrile residue unit, 4-sulfoxycinnamonitrile residue unit, 2-hydroxycinnamic acid residue unit, 3-hydroxycinnamic acid residue unit, 4-hydroxycinnamic acid residue unit, 2-carboxycinnamic acid residue unit, 3-carboxycinnamic acid residue unit, 4-carboxycinnamic acid residue unit, 4-sulfoxycinnamic acid residue unit, methyl 2-hydroxycinnamate residue unit, methyl 3-hydroxycinnamate residue unit, methyl 4-hydroxycinnamate residue unit, methyl 2-carboxycinnamate residue unit, methyl 3-carboxycinnamate residue unit, methyl 4-carboxycinnamate residue unit, methyl 4-sulfoxycinnamate residue unit, 2-hydroxy ethyl cinnamate residue unit, ethyl 3-hydroxycinnamate residue unit, ethyl 4-hydroxycinnamate residue unit, ethyl 2-carboxycinnamate residue unit, ethyl 3-carboxycinnamate residue unit, ethyl 4-carboxycinnamate residue unit, ethyl 4-sulfoxycinnamate residue unit, propyl 2-hydroxycinnamate residue unit, propyl 3-hydroxycinnamate residue unit, 4-hydroxycinnamate propyl acid residue unit, 2-propyl carboxycinnamate residue unit, 3-carboxy propyl residue unit propyl imilate residue unit, propyl 4-carboxycinnamate residue unit, propyl 4-sulfoxycinnamate residue unit, 4-sulfoxy-α,β,β-trifluoro-1-vinylnaphthalene residue unit, 2,3-dihydroxy-α,β,β-trifluoro-1-vinylnaphthalene residue unit, 2,4-dihydroxy-α,β,β-trifluoro-1-vinylnaphthalene residue unit, 3,4- Dihydroxy-α,β,β-trifluoro-1-vinylnaphthalene residue unit, 2-hydroxy-β-cyano-1-vinylnaphthalene residue unit, 3-hydroxy-β-cyano-1-vinylnaphthalene residue unit , 4-hydroxy-β-cyano-1-vinylnaphthalene residue unit, 2-carboxy-β-cyano-1-vinylnaphthalene residue unit, 3-hydroxy-β-cyano-1-vinylnaphthalene residue unit, 4 -hydroxy-β-cyano-1-vinylnaphthalene residue unit, 2-carboxy-β-cyano-1-vinylnaphthalene residue unit, 3-carboxy-β-cyano-1-vinylnaphthalene residue unit, 4-carboxy -β-cyano-1-vinylnaphthalene residue unit, 4-sulfoxy-β-cyano-1-vinylnaphthalene residue unit, β-(2-hydroxy-1-naphthyl)acrylic acid residue unit, β-(3 -hydroxy-1-naphthyl) acrylic acid residue unit, β-(4-hydroxy-1-naphthyl) acrylic acid residue unit, β-(2-carboxy-1-naphthyl) acrylic acid residue unit, β-( 3-carboxy-1-naphthyl) acrylic acid residue unit, β-(4-carboxy-1-naphthyl) acrylic acid residue unit, β-(4-sulfoxy-1-naphthyl) acrylic acid residue unit, β- (2-hydroxy-1-naphthyl)methyl acrylate residue unit, β-(3-hydroxy-1-naphthyl)methyl acrylate residue unit, β-(4-hydroxy-1-naphthyl)methyl acrylate residue unit, β-(2-carboxy-1-naphthyl) methyl acrylate residue unit, β-(3-carboxy-1-naphthyl) methyl acrylate residue unit, β-(4-carboxy-1-naphthyl) acrylic methyl acid residue unit, β-(4-sulfoxy-1-naphthyl)methyl acrylate residue unit, β-(2-hydroxy-1-naphthyl)ethyl acrylate residue unit, β-(3-hydroxy-1 -naphthyl)ethyl acrylate residue unit, β-(4-hydroxy-1-naphthyl)ethyl acrylate residue unit , β-(2-carboxy-1-naphthyl) ethyl acrylate residue unit, β-(3-carboxy-1-naphthyl) ethyl acrylate residue unit, β-(4-carboxy-1-naphthyl) acrylic acid ethyl residue unit, β-(4-sulfoxy-1-naphthyl)ethyl acrylate residue unit, β-(2-hydroxy-1-naphthyl)propyl acrylate residue unit, β-(3-hydroxy-1- naphthyl)propyl acrylate residue unit, β-(4-hydroxy-1-naphthyl)propyl acrylate residue unit, β-(2-carboxy-1-naphthyl)propyl acrylate residue unit, β-(3- Carboxy-1-naphthyl)propyl acrylate residue unit, β-(4-carboxy-1-naphthyl)propyl acrylate residue unit, β-(4-sulfoxy-1-naphthyl)propyl acrylate residue unit, 2 - hydroxycinnamamide residue unit, 3-hydroxycinnamamide residue unit, 4-hydroxycinnamamide residue unit, 2-carboxycinnamamide residue unit, 3-carboxycinnamamide residue unit, 4 -Carboxycinnamamide residue unit, 4-sulfoxycinnamamide residue unit, N,N-dimethyl-2-hydroxycinnamamide residue unit, N,N-dimethyl-3-hydroxycinnamamide residue unit , N,N-dimethyl-4-hydroxycinnamamide residue unit, N,N-dimethyl-2-carboxycinnamamide residue unit, N,N-dimethyl-3-carboxycinnamamide residue unit, N , N-dimethyl-4-carboxycinnamamide residue unit, N,N-dimethyl-4-sulfoxycinnamamide residue unit, N,N-diethyl 2-hydroxycinnamamide residue unit, N,N- diethyl 3-hydroxycinnamamide residue unit, N,N-diethyl 4-hydroxycinnamamide residue unit, N,N-diethyl 2-carboxycinnamamide residue unit, N,N-diethyl 3-carboxycinnamamide namamide residue unit, N,N-diethyl 4-carboxycinnamamide residue unit, N,N-diethyl 4-sulfoxycinnamamide residue unit, 2-hydroxy-β-methylstyrene residue unit, 3- Hydroxy-β-methylstyrene residue unit, 4-hydroxy-β-methylstyrene residue unit, 2-carboxy-β-methylstyrene residue unit, 3-carboxy-β-methylstyrene residue unit, 4-carboxy- β-methylstyrene residue unit, 4 - sulfoxy-β-methylstyrene residue unit, 2-hydroxybenzylidenemalononitrile residue unit, 3-hydroxybenzylidenemalononitrile residue unit, 4-hydroxybenzylidenemalononitrile residue unit, 2,3-dihydroxybenzylidenemalononitrile residue group unit, 2,4-dihydroxybenzylidenemalononitrile residue unit, 3,4-dihydroxybenzylidenemalononitrile residue unit, 2-carboxybenzylidenemalononitrile residue unit, 3-carboxybenzylidenemalononitrile residue unit, 4-carboxy benzylidenemalononitrile residue unit, 2,3-dicarboxybenzylidenemalononitrile residue unit, 2,4-dicarboxybenzylidenemalononitrile residue unit, 3,4-dicarboxybenzylidenemalononitrile residue unit, 4-sulfoxy benzylidenemalononitrile residue unit, dimethyl 2-hydroxybenzylidenemalonate residue unit, dimethyl 3-hydroxybenzylidenemalonate residue unit, dimethyl 4-hydroxybenzylidenemalonate residue unit, dimethyl 2,3-dihydroxybenzylidenemalonate residue Group unit, dimethyl 2,4-dihydroxybenzylidenemalonate residue unit, dimethyl 3,4-dihydroxybenzylidenemalonate residue unit, dimethyl 2-carboxybenzylidenemalonate residue unit, dimethyl 3-carboxybenzylidenemalonate residue unit , dimethyl 4-carboxybenzylidenemalonate residue unit, dimethyl 2,3-dicarboxybenzylidenemalonate residue unit, dimethyl 2,4-dicarboxybenzylidenemalonate residue unit, dimethyl 3,4-dicarboxybenzylidenemalonate residue unit, dimethyl 4-sulfoxybenzylidenemalonate residue unit, diethyl 2-hydroxybenzylidenemalonate residue unit, diethyl 3-hydroxybenzylidenemalonate residue unit, diethyl 4-hydroxybenzylidenemalonate residue unit, 2 , 3-dihydroxybenzylidenemalonate diethyl residue unit, 2,4-dihydroxybenzylidenemalonate diethyl residue unit, 3,4-dihydroxybenzylidenemalonate diethyl residue unit, 2-carboxybenzylidenemalonate diethyl residue unit, 3 -Carboxybenzylidenemalonate diethyl residue unit, 4-carboxybenzylidenemalonate diethyl residue unit, 2,3-dicarboxybenzylidenemalonate diethyl residue unit, 2,4-dicarbo Diethyl xybenzylidene malonate residue unit, 3,4-dicarboxybenzylidene diethyl malonate residue unit, 4-sulfoxybenzylidene diethyl malonate residue unit, 2-hydroxybenzylidene dipropyl malonate residue unit, 3-hydroxybenzylidene dipropyl malonate residue unit, 4-hydroxybenzylidene dipropyl malonate residue unit, 2,3-dihydroxybenzylidene dipropyl malonate residue unit, 2,4-dihydroxybenzylidene dipropyl malonate residue unit, 3,4-dihydroxybenzylidene dipropyl malonate residue unit, dipropyl 2-carboxybenzylidenemalonate residue unit, dipropyl 3-carboxybenzylidenemalonate residue unit, dipropyl 4-carboxybenzylidenemalonate residue unit, dipropyl 2,3-dicarboxybenzylidenemalonate residue unit, dipropyl 2,4-dicarboxybenzylidenemalonate residue unit, dipropyl 3,4-dicarboxybenzylidenemalonate residue unit, dipropyl 4-sulfoxybenzylidenemalonate residue unit, 2-hydroxybenzylidenemalonic acid Diisopropyl residue unit, diisopropyl 3-hydroxybenzylidenemalonate residue unit, diisopropyl 4-hydroxybenzylidenemalonate residue unit, diisopropyl 2,3-dihydroxybenzylidenemalonate residue unit, diisopropyl 2,4-dihydroxybenzylidenemalonate residue group unit, diisopropyl 3,4-dihydroxybenzylidenemalonate residue unit, diisopropyl 2-carboxybenzylidenemalonate residue unit, diisopropyl 3-carboxybenzylidenemalonate residue unit, diisopropyl 4-carboxybenzylidenemalonate residue unit, 2 ,3-dicarboxybenzylidenemalonate diisopropyl residue unit, 2,4-dicarboxybenzylidenemalonate diisopropyl residue unit, 3,4-dicarboxybenzylidenemalonate diisopropyl residue unit, 4-sulfoxybenzylidenemalonate diisopropyl residue group unit, dibutyl 2-hydroxybenzylidenemalonate residue unit, dibutyl 3-hydroxybenzylidenemalonate residue unit, dibutyl 4-hydroxybenzylidenemalonate residue unit, dibutyl 2,3-dihydroxybenzylidenemalonate residue unit, 2 ,4-dihydroxybenzylidenemalonate dibutyl residue unit, 3,4-dihydroxybenzylidenemalonate dibutyl residue unit, dibutyl 2-carboxybenzylidenemalonate residue unit, dibutyl 3-carboxybenzylidenemalonate residue unit, dibutyl 4-carboxybenzylidenemalonate residue unit, dibutyl 2,3-dicarboxybenzylidenemalonate residue unit , dibutyl 2,4-dicarboxybenzylidenemalonate residue unit, dibutyl 3,4-dicarboxybenzylidenemalonate residue unit, dibutyl 4-sulfoxybenzylidenemalonate residue unit, diisobutyl 2-hydroxybenzylidenemalonate residue unit, diisobutyl 3-hydroxybenzylidenemalonate residue unit, diisobutyl 4-hydroxybenzylidenemalonate residue unit, diisobutyl 2,3-dihydroxybenzylidenemalonate residue unit, diisobutyl 2,4-dihydroxybenzylidenemalonate residue unit, 3,4-dihydroxybenzylidenemalonate diisobutyl residue unit, 2-carboxybenzylidenemalonate diisobutyl residue unit, 3-carboxybenzylidenemalonate diisobutyl residue unit, 4-carboxybenzylidenemalonate diisobutyl residue unit, 2,3- diisobutyl dicarboxybenzylidenemalonate residue unit, diisobutyl 2,4-dicarboxybenzylidenemalonate residue unit, diisobutyl 3,4-dicarboxybenzylidenemalonate residue unit, diisobutyl 4-sulfoxybenzylidenemalonate residue unit, Di-sec-butyl 2-hydroxybenzylidenemalonate residue unit, di-sec-butyl 3-hydroxybenzylidenemalonate residue unit, di-sec-butyl 4-hydroxybenzylidenemalonate residue unit, 2,3-dihydroxybenzylidenemalonic acid disec-butyl residue unit, disec-butyl 2,4-dihydroxybenzylidenemalonate residue unit, disec-butyl 3,4-dihydroxybenzylidenemalonate residue unit, disec-butyl 2-carboxybenzylidenemalonate residue unit, di-sec-butyl 3-carboxybenzylidenemalonate residue unit, di-sec-butyl 4-carboxybenzylidenemalonate residue unit, di-sec-butyl 2,3-dicarboxybenzylidenemalonate residue unit, 2 ,4-dicarboxybenzylidenemalonate disec-butyl residue unit, 3,4-dicarboxybenzylidenemalonate disec-butyl residue unit, 4-sulfoxybenzylidenemalonate disec-butyl residue unit, 2- hydroxybenzylidemma di-tert-butyl ronate residue unit, di-tert-butyl 3-hydroxybenzylidenemalonate residue unit, di-tert-butyl 4-hydroxybenzylidenemalonate residue unit, di-tert-butyl 2,3-dihydroxybenzylidenemalonate residue unit, di-tert-butyl 2,4-dihydroxybenzylidenemalonate residue unit, di-tert-butyl 3,4-dihydroxybenzylidenemalonate residue unit, di-tert-butyl 2-carboxybenzylidenemalonate residue unit, 3-carboxybenzylidenemalonate di-tert-butyl residue unit, 4-carboxybenzylidenemalonate di-tert-butyl residue unit, 2,3-dicarboxybenzylidenemalonate di-tert-butyl residue unit, 2,4-di Carboxybenzylidenemalonate di-tert-butyl residue unit, 3,4-dicarboxybenzylidenemalonate di-tert-butyl residue unit, 4-sulfoxybenzylidenemalonate di-tert-butyl residue unit, α-cyano-2- hydroxycinnamic acid residue unit, α-cyano-3-hydroxycinnamic acid residue unit, α-cyano-4-hydroxycinnamic acid residue unit, α-cyano-2-carboxycinnamic acid residue unit, α-Cyano-3-carboxycinnamic acid residue unit, α-cyano-4-carboxycinnamic acid residue unit, α-cyano-4-sulfoxycinnamic acid residue unit, α-cyano-2-hydroxycinnamic acid methyl acid residue unit, methyl α-cyano-3-hydroxycinnamate residue unit, methyl α-cyano-4-hydroxycinnamate residue unit, methyl α-cyano-2-carboxycinnamate residue unit , α-cyano-3-carboxycinnamate methyl residue unit, α-cyano-4-carboxymethyl cinnamate residue unit, α-cyano-4-sulfoxymethyl cinnamate residue unit, α-cyano-2 -ethyl hydroxycinnamate residue unit, ethyl α-cyano-3-hydroxycinnamate residue unit, ethyl α-cyano-4-hydroxycinnamate residue unit, α-cyano-2-carboxycinnamic acid ethyl residue unit, ethyl α-cyano-3-carboxycinnamate residue unit, ethyl α-cyano-4-carboxycinnamate residue unit, ethyl α-cyano-4-sulfoxycinnamate residue unit, α -propyl cyano-2-hydroxycinnamate residue unit, propyl α-cyano-3-hydroxycinnamate residue unit, propyl α-cyano-4-hydroxycinnamate residue unit, α-cyano-2- Carbo propyl xycinnamate residue unit, propyl alpha-cyano-3-carboxycinnamate residue unit, propyl cyano-4-carboxycinnamate residue unit, propyl alpha-cyano-4-sulfoxycinnamate residue unit, α-cyano-2-hydroxycinnamate isopropyl residue unit, α-cyano-3-hydroxycinnamate isopropyl residue unit, α-cyano-4-hydroxycinnamate isopropyl residue unit, α-cyano -2-carboxycinnamate isopropyl residue unit, α-cyano-3-carboxycinnamate isopropyl residue unit, α-cyano-4-carboxycinnamate isopropyl residue unit, α-cyano-4-sulfoxycinnamic isopropyl acid residue unit, butyl α-cyano-2-hydroxycinnamate residue unit, butyl α-cyano-3-hydroxycinnamate residue unit, butyl α-cyano-4-hydroxycinnamate residue unit , α-cyano-2-butyl carboxycinnamate residue unit, α-cyano-3-butyl carboxycinnamate residue unit, α-cyano-4-butyl carboxycinnamate residue unit, α-cyano- Butyl 4-sulfoxycinnamate residue unit, isobutyl α-cyano-2-hydroxycinnamate residue unit, isobutyl α-cyano-3-hydroxycinnamate residue unit, α-cyano-4-hydroxycinnamic acid isobutyl residue unit, α-cyano-2-carboxycinnamate isobutyl residue unit, α-cyano-3-carboxycinnamate isobutyl residue unit, α-cyano-4-carboxycinnamate isobutyl residue unit, α-cyano-4-sulfoxycinnamate isobutyl residue unit, α-cyano-2-hydroxycinnamate sec-butyl residue unit, α-cyano-3-hydroxycinnamate sec-butyl residue unit, α- Cyano-4-hydroxycinnamate sec-butyl residue unit, α-cyano-2-carboxycinnamate sec-butyl residue unit, α-cyano-3-carboxycinnamate sec-butyl residue unit, α -cyano-4-carboxycinnamate sec-butyl residue unit, α-cyano-4-sulfoxycinnamate sec-butyl residue unit, α-cyano-2-hydroxycinnamate tert-butyl residue unit, α - tert-butyl cyano-3-hydroxycinnamate residue unit, tert-butyl α-cyano-4-hydroxycinnamate residue unit, tert-butyl α-cyano-2-carboxycinnamate residue unit, α-cyano-3-carboxycinnamic acid tert-butyl alpha-cyano-4-carboxycinnamic acid tert-butyl residue unit, α-cyano-4-sulfoxycinnamic acid tert-butyl residue unit, α-cyano-2-hydroxycinnamic acid (2 -methoxyethyl) residue unit, α-cyano-3-hydroxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-4-hydroxycinnamic acid (2-methoxyethyl) residue unit, α- Cyano-2-carboxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-3-carboxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-4-carboxycinnamic acid (2 -methoxyethyl) residue unit, α-cyano-4-sulfoxycinnamic acid (2-methoxyethyl) residue unit, and the like.

Among the residue units represented by the general formula (1), 2-hydroxybenzylidenemalononitrile residue units and 3-hydroxybenzylidene are used to exhibit higher negative retardation and higher compatibility with different polymers. malononitrile residue unit, 4-hydroxybenzylidenemalononitrile residue unit, 2,3-dihydroxybenzylidenemalononitrile residue unit, 2,4-dihydroxybenzylidenemalononitrile residue unit, 3,4-dihydroxybenzylidenemalononitrile residue unit, 2-carboxybenzylidenemalononitrile residue unit, 3-carboxybenzylidenemalononitrile residue unit, 4-carboxybenzylidenemalononitrile residue unit, 2,3-dicarboxybenzylidenemalononitrile residue unit, 2,4-di Carboxybenzylidene malononitrile residue unit, 3,4-dicarboxybenzylidene malononitrile residue unit, 4-sulfoxybenzylidene malononitrile residue unit, 2,3-disulfoxybenzylidene malononitrile residue unit, 2-hydroxybenzylidene dimethyl malonate residue unit, dimethyl 3-hydroxybenzylidene malonate residue unit, dimethyl 4-hydroxybenzylidene malonate residue unit, dimethyl 2,3-dihydroxybenzylidene malonate residue unit, 2,4-dihydroxybenzylidene malonate dimethyl residue unit, dimethyl 3,4-dihydroxybenzylidenemalonate residue unit, dimethyl 2-carboxybenzylidenemalonate residue unit, dimethyl 3-carboxybenzylidenemalonate residue unit, dimethyl 4-carboxybenzylidenemalonate residue unit , dimethyl 2,3-dicarboxybenzylidenemalonate residue unit, dimethyl 2,4-dicarboxybenzylidenemalonate residue unit, dimethyl 3,4-dicarboxybenzylidenemalonate residue unit, 4-sulfoxybenzylidenemalonic acid dimethyl residue unit, diethyl 2-hydroxybenzylidenemalonate residue unit, diethyl 3-hydroxybenzylidenemalonate residue unit, diethyl 4-hydroxybenzylidenemalonate residue unit, diethyl 2,3-dihydroxybenzylidenemalonate residue unit , 2,4-dihydroxybenzylidenemalonate diethyl residue unit, 3,4-dihydroxybenzylidenemalonate diethyl residue unit, 2-carboxybenzylidenemalonate diethyl residue unit, 3-carboxybenzylidenemalonate diethyl residue unit, 4 - Diethyl carboxybenzylidenemalonate residue unit, diethyl 2,3-dicarboxybenzylidenemalonate residue unit, diethyl 2,4-dicarboxybenzylidenemalonate residue unit, diethyl 3,4-dicarboxybenzylidenemalonate residue unit , 4-sulfoxybenzylidenemalonate diethyl residue unit, 2-hydroxybenzylidenemalonate dipropyl residue unit, 3-hydroxybenzylidenemalonate dipropyl residue unit, 4-hydroxybenzylidenemalonate dipropyl residue unit, 2,3- dipropyl dihydroxybenzylidene malonate residue unit, dipropyl 2,4-dihydroxybenzylidene malonate residue unit, dipropyl 3,4-dihydroxybenzylidene malonate residue unit, dipropyl 2-carboxybenzylidene malonate residue unit, 3-carboxybenzylidene dipropyl malonate residue unit, 4-carboxybenzylidene dipropyl malonate residue unit, 2,3-dicarboxybenzylidene malonate dipropyl residue unit, 2,4-dicarboxybenzylidene dipropyl malonate residue unit, 3,4- Dipropyl dicarboxybenzylidenemalonate residue unit, dipropyl 4-sulfoxybenzylidenemalonate residue unit, diisopropyl 2-hydroxybenzylidenemalonate residue unit, diisopropyl 3-hydroxybenzylidenemalonate residue unit, 4-hydroxybenzylidenemalonic acid diisopropyl residue unit, diisopropyl 2,3-dihydroxybenzylidenemalonate residue unit, diisopropyl 2,4-dihydroxybenzylidenemalonate residue unit, diisopropyl 3,4-dihydroxybenzylidenemalonate residue unit, 2-carboxybenzylidenemalonic acid diisopropyl residue unit, diisopropyl 3-carboxybenzylidene malonate residue unit, diisopropyl 4-carboxybenzylidene malonate residue unit, diisopropyl 2,3-dicarboxybenzylidene malonate residue unit, 2,4-dicarboxybenzylidene malonate diisopropyl residue unit, diisopropyl 3,4-dicarboxybenzylidenemalonate residue unit, diisopropyl 4-sulfoxybenzylidenemalonate residue unit, dibutyl 2-hydroxybenzylidenemalonate residue unit, dibutyl 3-hydroxybenzylidenemalonate residue group unit, 4-hydroxybenzylidenemalonate dibutyl residue unit, 2,3-dihydroxybenzylidenemalonate dibutyl Butyl residue unit, dibutyl 2,4-dihydroxybenzylidenemalonate residue unit, dibutyl 3,4-dihydroxybenzylidenemalonate residue unit, dibutyl 2-carboxybenzylidenemalonate residue unit, dibutyl 3-carboxybenzylidenemalonate residue Group unit, dibutyl 4-carboxybenzylidene malonate residue unit, dibutyl 2,3-dicarboxybenzylidene malonate residue unit, dibutyl 2,4-dicarboxybenzylidene malonate residue unit, 3,4-dicarboxybenzylidene malonate dibutyl acid residue unit, dibutyl 4-sulfoxybenzylidenemalonate residue unit, diisobutyl 2-hydroxybenzylidenemalonate residue unit, diisobutyl 3-hydroxybenzylidenemalonate residue unit, diisobutyl 4-hydroxybenzylidenemalonate residue unit , diisobutyl 2,3-dihydroxybenzylidenemalonate residue unit, diisobutyl 2,4-dihydroxybenzylidenemalonate residue unit, diisobutyl 3,4-dihydroxybenzylidenemalonate residue unit, diisobutyl 2-carboxybenzylidenemalonate residue unit , diisobutyl 3-carboxybenzylidenemalonate residue unit, diisobutyl 4-carboxybenzylidenemalonate residue unit, diisobutyl 2,3-dicarboxybenzylidenemalonate residue unit, diisobutyl 2,4-dicarboxybenzylidenemalonate residue unit , 3,4-dicarboxybenzylidenemalonate diisobutyl residue unit, 4-sulfoxybenzylidenemalonate diisobutyl residue unit, 2-hydroxybenzylidenemalonate disec-butyl residue unit, 3-hydroxybenzylidenemalonate disec- Butyl residue unit, di-sec-butyl 4-hydroxybenzylidenemalonate residue unit, di-sec-butyl 2,3-dihydroxybenzylidenemalonate residue unit, di-sec-butyl 2,4-dihydroxybenzylidenemalonate residue unit , 3,4-dihydroxybenzylidenemalonate disec-butyl residue unit, 2-carboxybenzylidenemalonate disec-butyl residue unit, 3-carboxybenzylidenemalonate disec-butyl residue unit, 4-carboxybenzylidenemalonate di-sec-butyl acid residue unit, 2,3-dicarboxybenzylidene di-sec-butyl malonate residue unit, 2,4-dicarboxybenzylidene di-sec-butyl malonate residue unit, 3,4-dicarboxybenzylidene di-sec-butyl malonate residue unit, 4-sulfoxybenzylidene di-sec-butyl malonate residue unit, di-tert-butyl 2-hydroxybenzylidene malonate residue unit, di-tert-butyl 3-hydroxybenzylidene malonate residue group unit, di-tert-butyl 4-hydroxybenzylidenemalonate residue unit, di-tert-butyl 2,3-dihydroxybenzylidenemalonate residue unit, di-tert-butyl 2,4-dihydroxybenzylidenemalonate residue unit, 3 , 4-dihydroxybenzylidene malonate di-tert-butyl residue unit, 2-carboxybenzylidene malonate di-tert-butyl residue unit, 3-carboxybenzylidene malonate di-tert-butyl residue unit, 4-carboxybenzylidene malonate di-tert-butyl residue unit tert-butyl residue unit, di-tert-butyl 2,3-dicarboxybenzylidenemalonate residue unit, di-tert-butyl 2,4-dicarboxybenzylidenemalonate residue unit, 3,4-dicarboxybenzylidenemalonic acid Di-tert-butyl residue unit, di-tert-butyl 4-sulfoxybenzylidenemalonate residue unit, α-cyano-2-hydroxycinnamic acid residue unit, α-cyano-3-hydroxycinnamic acid residue unit , α-cyano-4-hydroxycinnamic acid residue unit, α-cyano-2-carboxycinnamic acid residue unit, α-cyano-3-carboxycinnamic acid residue unit, α-cyano-4-carboxy cinnamic acid residue unit, α-cyano-2-sulfoxycinnamic acid residue unit, α-cyano-3-sulfoxycinnamic acid residue unit, α-cyano-4-sulfoxycinnamic acid residue unit, α-cyano- methyl 2-hydroxycinnamate residue unit, methyl α-cyano-3-hydroxycinnamate residue unit, methyl α-cyano-4-hydroxycinnamate residue unit, α-cyano-2-carboxycinnamic methyl acid residue unit, methyl α-cyano-3-carboxycinnamate residue unit, methyl α-cyano-4-carboxycinnamate residue unit, methyl α-cyano-4-sulfoxycinnamate residue residue unit, α-Cyano-2-hydroxycinnamate ethyl residue unit, α-cyano-3-hydroxycinnamate ethyl residue unit, α-cyano-4-hydroxycinnamate ethyl residue unit, α-cyano-2 -ethyl carboxycinnamate residue unit, α-cyano-3-ethyl carboxycinnamate residue unit, α-cyano-4-ethyl carboxycinnamate residue unit, α-cyano-2-su ethyl sulphoxycinnamate residue unit, α-cyano-3-ethyl sulfoxycinnamate residue unit, α-cyano-4-ethyl sulfoxycinnamate residue unit, propyl α-cyano-2-hydroxycinnamate residue unit , α-cyano-3-hydroxycinnamate propyl residue unit, α-cyano-4-hydroxycinnamate propyl residue unit, α-cyano-2-carboxycinnamate propyl residue unit, α-cyano- propyl 3-carboxycinnamate residue unit, propyl α-cyano-4-carboxycinnamate residue unit, propyl α-cyano-4-sulfoxycinnamate residue unit, α-cyano-2-hydroxycinnamic acid isopropyl residue unit, α-cyano-3-hydroxycinnamate isopropyl residue unit, α-cyano-4-hydroxycinnamate isopropyl residue unit, α-cyano-2-carboxycinnamate isopropyl residue unit, α-Cyano-3-carboxycinnamate isopropyl residue unit, α-cyano-4-carboxycinnamate isopropyl residue unit, α-cyano-4-sulfoxycinnamate isopropyl residue unit, α-cyano-2- Butyl hydroxycinnamate residue unit, butyl α-cyano-3-hydroxycinnamate residue unit, butyl α-cyano-4-hydroxycinnamate residue unit, butyl α-cyano-2-carboxycinnamate residue unit, butyl α-cyano-3-carboxycinnamate residue unit, butyl α-cyano-4-carboxycinnamate residue unit, butyl α-cyano-4-sulfoxycinnamate residue unit, α- cyano-2-hydroxycinnamate isobutyl residue unit, α-cyano-3-hydroxycinnamate isobutyl residue unit, α-cyano-4-hydroxycinnamate isobutyl residue unit, α-cyano-2-carboxy isobutyl cinnamate residue unit, isobutyl α-cyano-3-carboxycinnamate residue unit, isobutyl α-cyano-4-carboxycinnamate residue unit, isobutyl α-cyano-4-sulfoxycinnamate residue unit, sec-butyl α-cyano-2-hydroxycinnamate residue unit, sec-butyl α-cyano-3-hydroxycinnamate residue unit, sec-butyl α-cyano-4-hydroxycinnamate residue Group unit, sec-butyl α-cyano-2-carboxycinnamate residue unit, sec-butyl α-cyano-3-carboxycinnamate residue unit, sec-butyl α-cyano-4-carboxycinnamate residue unit, α-cyano-4-sulfoxycinnamic acid s ec-butyl residue unit, α-cyano-2-hydroxycinnamate tert-butyl residue unit, α-cyano-3-hydroxycinnamate tert-butyl residue unit, α-cyano-4-hydroxycinnamic acid tert-butyl residue unit, α-cyano-2-carboxycinnamic acid te
rt-butyl residue unit, tert-butyl α-cyano-3-carboxycinnamate residue unit, tert-butyl α-cyano-4-carboxycinnamate residue unit, α-cyano-4-sulfoxycinnamic acid tert-butyl residue unit, α-cyano-2-hydroxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-3-hydroxycinnamic acid (2-methoxyethyl) residue unit, α-cyano -4-hydroxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-2-carboxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-3-carboxycinnamic acid (2- methoxyethyl) residue units, α-cyano-4-carboxycinnamic acid (2-methoxyethyl) residue units, α-cyano-4-sulfoxycinnamic acid (2-methoxyethyl) residue units are preferred, and 2- Hydroxybenzylidenemalononitrile residue unit, 3-hydroxybenzylidenemalononitrile residue unit, 4-hydroxybenzylidenemalononitrile residue unit, 2,3-dihydroxybenzylidenemalononitrile residue unit, 2,4-dihydroxybenzylidenemalononitrile residue unit, 3,4-dihydroxybenzylidenemalononitrile residue unit, dimethyl 2-hydroxybenzylidenemalonate residue unit, dimethyl 3-hydroxybenzylidenemalonate residue unit, dimethyl 4-hydroxybenzylidenemalonate residue unit, 2,3 -dihydroxybenzylidenemalonate dimethyl residue unit, 2,4-dihydroxybenzylidenemalonate dimethyl residue unit, 3,4-dihydroxybenzylidenemalonate dimethyl residue unit, 2-hydroxybenzylidenemalonate diethyl residue unit, 3-hydroxy diethyl benzylidenemalonate residue unit, diethyl 4-hydroxybenzylidenemalonate residue unit, diethyl 2,3-dihydroxybenzylidenemalonate residue unit, diethyl 2,4-dihydroxybenzylidenemalonate residue unit, 3,4-dihydroxy diethyl benzylidenemalonate residue unit, dipropyl 2-hydroxybenzylidenemalonate residue unit, dipropyl 3-hydroxybenzylidenemalonate residue unit, dipropyl 4-hydroxybenzylidenemalonate residue unit, dipropyl 2,3-dihydroxybenzylidenemalonate residue unit, dipropyl 2,4-dihydroxybenzylidenemalonate residue unit, dipropyl 3,4-dihydroxybenzylidenemalonate residue unit, 2-hydroxy diisopropyl droxybenzylidenemalonate residue unit, diisopropyl 3-hydroxybenzylidenemalonate residue unit, diisopropyl 4-hydroxybenzylidenemalonate residue unit, diisopropyl 2,3-dihydroxybenzylidenemalonate residue unit, 2,4-dihydroxy diisopropyl benzylidenemalonate residue unit, diisopropyl 3,4-dihydroxybenzylidenemalonate residue unit, dibutyl 2-hydroxybenzylidenemalonate residue unit, dibutyl 3-hydroxybenzylidenemalonate residue unit, dibutyl 4-hydroxybenzylidenemalonate residue unit, dibutyl 2,3-dihydroxybenzylidenemalonate residue unit, dibutyl 2,4-dihydroxybenzylidenemalonate residue unit, dibutyl 3,4-dihydroxybenzylidenemalonate residue unit, diisobutyl 2-hydroxybenzylidenemalonate residue unit, diisobutyl 3-hydroxybenzylidenemalonate residue unit, diisobutyl 4-hydroxybenzylidenemalonate residue unit, diisobutyl 2,3-dihydroxybenzylidenemalonate residue unit, diisobutyl 2,4-dihydroxybenzylidenemalonate residue unit, diisobutyl 3,4-dihydroxybenzylidenemalonate residue unit, disec-butyl 2-hydroxybenzylidenemalonate residue unit, disec-butyl 3-hydroxybenzylidenemalonate residue unit, di-4-hydroxybenzylidenemalonate residue unit sec-butyl residue unit, di-sec-butyl 2,3-dihydroxybenzylidenemalonate residue unit, di-sec-butyl 2,4-dihydroxybenzylidenemalonate residue unit, di-sec-3,4-dihydroxybenzylidenemalonate butyl residue unit, di-tert-butyl 2-hydroxybenzylidenemalonate residue unit, di-tert-butyl 3-hydroxybenzylidenemalonate residue unit, di-tert-butyl 4-hydroxybenzylidenemalonate residue unit, 2,3 -di-tert-butyl dihydroxybenzylidenemalonate residue unit, di-tert-butyl 2,4-dihydroxybenzylidenemalonate residue unit, di-tert-butyl 3,4-dihydroxybenzylidenemalonate residue unit, α-cyano-2 -Hydroxycinnamic acid residue unit, α-cyano-3-hydroxycinnamic acid residue unit, α-cyano-4-hydroxycinnamic acid residue unit, α-cyano-2-carboxycinnamic acid residue unit , α-cyano- 3-carboxycinnamic acid residue unit, α-cyano-4-carboxycinnamic acid residue unit, α-cyano-2-sulfoxycinnamic acid residue unit, α-cyano-3-sulfoxycinnamic acid residue unit, α-cyano-4-sulfoxycinnamic acid residue unit, methyl α-cyano-2-hydroxycinnamate residue unit, methyl α-cyano-3-hydroxycinnamate residue unit, α-cyano-4-hydroxy methyl cinnamate residue unit, ethyl α-cyano-2-hydroxycinnamate residue unit, ethyl α-cyano-3-hydroxycinnamate residue unit, ethyl α-cyano-4-hydroxycinnamate residue group unit, α-cyano-2-hydroxycinnamate propyl residue unit, α-cyano-3-hydroxycinnamate propyl residue unit, α-cyano-4-hydroxycinnamate propyl residue unit, α- Cyano-2-hydroxycinnamate isopropyl residue unit, α-cyano-3-hydroxycinnamate isopropyl residue unit, α-cyano-4-hydroxycinnamate isopropyl residue unit, α-cyano-2-hydroxy Butyl cinnamate residue unit, butyl α-cyano-3-hydroxycinnamate residue unit, butyl α-cyano-4-hydroxycinnamate residue unit, isobutyl α-cyano-2-hydroxycinnamate residue group unit, α-cyano-3-hydroxycinnamate isobutyl residue unit, α-cyano-4-hydroxycinnamate isobutyl residue unit, α-cyano-2-hydroxycinnamate sec-butyl residue unit, α-Cyano-3-hydroxycinnamate sec-butyl residue unit, α-cyano-4-hydroxycinnamate sec-butyl residue unit, α-cyano-2-hydroxycinnamate tert-butyl residue unit , α-cyano-3-hydroxycinnamate tert-butyl residue unit, α-cyano-4-hydroxycinnamate tert-butyl residue unit, α-cyano-2-hydroxycinnamate (2-methoxyethyl ) residue unit, α-cyano-3-hydroxycinnamic acid (2-methoxyethyl) residue unit, and α-cyano-4-hydroxycinnamic acid (2-methoxyethyl) residue unit are more preferable. One or more of these residue units may be included.

Since the polymer containing the monomer residue unit represented by the general formula (1) of the present invention exhibits good optical properties, it further comprises at least It preferably contains one or more monomeric residue units.

(Here, R ₁₇ to R ₁₉ represent hydrogen. Further, R ₂₀ to R ₂₇ each independently represent hydrogen, halogen, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 1 to 12 carbon atoms. Alkyl group, cyclic group having 3 to 14 carbon atoms, cyano group, nitro group, hydroxy group, carboxy group, thiol group, alkoxy group ( _-OX43 ), ester group (-C(=O) _OX44 or -CO( =O)-X ₄₅ ), amide group (-C(=O)N(X ₄₆ )(X ₄₇ ) or -NX ₄₈ C(=O)X ₄₉ ), acyl group (-C(=O)X ₅₀ ) or an amino group (—N(X ₅₁ )(X ₅₂ )) (where X ₄₃ to X ₄₅ are each independently a linear alkyl group having 1 to 12 carbon atoms, a branched chain having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms, and each of X ₄₆ to X ₅₂ is independently hydrogen, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 1 to 12 carbon atoms. or a cyclic group having 3 to 14 carbon atoms.) In addition, adjacent substituents of R ₂₀ to R ₂₇ may form a condensed ring structure, and R ₂₀ and R ₂₆ and R ₂₁ may form a condensed ring structure. and R ₂₇ may form a ring structure with the same atom.)

(Here, R ₂₈ to R ₃₀ represent hydrogen. Further, R ₃₁ to R ₃₄ each independently represent hydrogen, halogen, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 1 to 12 carbon atoms. Alkyl group, cyclic group having 3 to 14 carbon atoms, cyano group, nitro group, hydroxy group, carboxy group, thiol group, alkoxy group (-OX ₆₃ ), ester group (-C(=O)OX ₆₄ or -CO( =O)-X ₆₅ ), amide group (-C(=O)N(X ₆₆ )(X ₆₇ ) or -NX ₆₈ C(=O)X ₆₉ ), acyl group (-C(=O)X ₇₀ ) or an amino group (—N(X ₇₁ )(X ₇₂ )) (where X ₆₃ to X ₆₅ are each independently a linear alkyl group having 1 to 12 carbon atoms, a branched group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms, and each of X ₆₆ to X ₇₂ is independently hydrogen, a linear alkyl group having 1 to 12 carbon atoms, or a branched alkyl group having 1 to 12 carbon atoms. or a cyclic group having 3 to 14 carbon atoms.) In addition, adjacent substituents of R ₃₁ to R ₃₄ may form a condensed ring structure, and R ₃₁ and R ₃₂ and R ₃₃ may form a condensed ring structure. and R ₃₄ may form a ring structure with the same atom.)
R ₁₇ to R ₁₉ in general formula (3) of the present invention represent hydrogen.

Further, R ₂₀ to R ₂₇ in the general formula (3) in the present invention are each independently hydrogen, halogen, linear alkyl group having 1 to 12 carbon atoms, branched alkyl group having 1 to 12 carbon atoms, 3 to 14 cyclic groups, cyano groups, nitro groups, hydroxy groups, carboxy groups, thiol groups, alkoxy groups ( _-OX43 ), ester groups (-C(=O) _OX44 or -CO(=O)-X ₄₅ ), amide group (-C(=O)N(X ₄₆ )(X ₄₇ ) or -NX ₄₈ C(=O)X ₄₉ ), acyl group (-C(=O)X ₅₀ ) or amino group ( —N(X ₅₁ )(X ₅₂ )) (where X ₄₃ to X ₄₅ are each independently a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or represents a cyclic group having 3 to 14 carbon atoms, and each of X ₄₆ to X ₅₂ is independently hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a 3 to 14 cyclic groups). Adjacent substituents of R ₂₀ to R ₂₇ may form a condensed ring structure, and R ₂₀ and R ₂₆ and R ₂₁ and R ₂₇ may form a ring structure with the same atom.

Halogen in R ₂₀ to R ₂₇ includes, for example, fluorine, chlorine, bromine, etc. Examples of linear alkyl groups having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, butyl group, Linear alkyl groups having 1 to 12 carbon atoms such as pentyl group and hexyl group can be mentioned. Examples of branched alkyl groups having 1 to 12 carbon atoms include isopropyl group, isobutyl group, sec-butyl group, tert- Examples include branched alkyl groups having 1 to 12 carbon atoms such as butyl group, and examples of cyclic groups having 3 to 14 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentanyl group, phenyl cyclic groups having 3 to 14 carbon atoms such as groups, naphthyl groups, anthryl groups, furyl groups, pyranyl groups, pyrrolyl groups, imidazolyl groups, pyridyl groups, indolyl groups, carbazolyl groups, etc. Specific alkoxy groups include: Examples include a methoxy group, an ethoxy group, and the like. Specific ester groups include, for example, a methyloxycarbonyl group, an ethyloxycarbonyl group, an acetoxy group, a propoxy group, and the like. Specific amide groups include Examples include dimethylamide group, diethylamide group and the like. Specific acyl groups include acetyl group, propionyl group, benzoyl group and the like. Specific amino groups include dimethylamino group and diethylamino group. etc.

Examples of linear alkyl groups having 1 to 12 carbon atoms in X ₃₆ to X ₅₂ include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group. Examples of branched alkyl groups having 1 to 12 carbon atoms include isopropyl group, sec-butyl group, tert-butyl group, and isobutyl group. Examples of cyclic groups having 3 to 14 carbon atoms include Cyclopropyl group, cyclobutyl group, cyclohexyl group, phenyl group, naphthyl group and the like.

Specific monomer residue units represented by general formula (3) include, for example, indole residues such as N-vinylindole residue units and N-methyl-3-vinylindole residue units. units, N-vinylcarbazole residue units, N-vinylcarbazole residue units such as 3-methyl-N-vinylcarbazole, 3-chloro-N-vinylcarbazole, and the like. Among these, N-vinylcarbazole residue units are preferred, and N-vinylcarbazole is more preferred, in order to exhibit higher negative retardation and higher compatibility with different polymers.

R ₂₈ to R ₃₀ in general formula (4) in the present invention represent hydrogen.

Further, R ₃₁ to R ₃₄ in the general formula (4) in the present invention are each independently hydrogen, halogen, linear alkyl group having 1 to 12 carbon atoms, branched alkyl group having 1 to 12 carbon atoms, 3 to 14 cyclic groups, cyano groups, nitro groups, hydroxy groups, carboxy groups, thiol groups, alkoxy groups (-OX ₆₃ ), ester groups (-C(=O)OX ₆₄ or -CO(=O)-X ₆₅ ), amide group (-C(=O)N(X ₆₆ )(X ₆₇ ) or -NX ₆₈ C(=O)X ₆₉ ), acyl group (-C(=O)X ₇₀ ) or amino group ( —N(X ₇₁ )(X ₇₂ )) (where X ₆₃ to X ₆₅ are each independently a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or represents a cyclic group having 3 to 14 carbon atoms, and each of X ₆₆ to X ₇₂ is independently hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a 3 to 14 cyclic groups). Adjacent substituents of R ₃₁ to R ₃₄ may form a condensed ring structure, and R ₃₁ and R ₃₂ and R ₃₃ and R ₃₄ may form a ring structure with the same atom.

Halogen in R ₃₁ to R ₃₄ includes, for example, fluorine, chlorine, bromine and the like, and examples of linear alkyl groups having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, butyl group, Linear alkyl groups having 1 to 12 carbon atoms such as pentyl group and hexyl group can be mentioned. Examples of branched alkyl groups having 1 to 12 carbon atoms include isopropyl group, isobutyl group, sec-butyl group, tert- Examples include branched alkyl groups having 1 to 12 carbon atoms such as butyl group, and examples of cyclic groups having 3 to 14 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentanyl group, phenyl cyclic groups having 3 to 14 carbon atoms such as groups, naphthyl groups, anthryl groups, furyl groups, pyranyl groups, pyrrolyl groups, imidazolyl groups, pyridyl groups, indolyl groups, carbazolyl groups, etc. Specific alkoxy groups include: Examples include a methoxy group, an ethoxy group, and the like. Specific ester groups include, for example, a methyloxycarbonyl group, an ethyloxycarbonyl group, an acetoxy group, a propoxy group, and the like. Specific amide groups include Examples include dimethylamide group, diethylamide group and the like. Specific acyl groups include acetyl group, propionyl group, benzoyl group and the like. Specific amino groups include dimethylamino group and diethylamino group. etc.

Examples of linear alkyl groups having 1 to 12 carbon atoms in X ₅₃ to X ₇₂ include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group. Examples of branched alkyl groups having 1 to 12 carbon atoms include isopropyl group, sec-butyl group, tert-butyl group, and isobutyl group. Examples of cyclic groups having 3 to 14 carbon atoms include Cyclopropyl group, cyclobutyl group, cyclohexyl group, phenyl group, naphthyl group and the like.

Specific monomer residue units represented by general formula (4) include, for example, N-vinylsuccinimide residue units such as N-vinylsuccinimide residue units, and N-vinylphthalimide residue units. , 4-methylphthalimide residue unit, 4-chloromethylphthalimide residue unit, N-vinylphthalimide residue units such as 4-nitrophthalimide residue unit, N-vinyl 2,3-naphthalene dicarboximide residue unit , N-vinyl naphthalenedicarboximides such as N-vinyl 1,8-naphthalenedicarboximide residue units. Among these, N-vinylphthalimide residue units are preferred, and N-vinylphthalimide residue units are more preferred, in order to exhibit higher negative retardation and higher compatibility with different polymers.

The method for producing the polymer of the present invention is not particularly limited, but for example, a production method of polymerizing a monomer represented by general formula (5) can be mentioned.

(Here, R ₁ is a cyano group, R ₂ is a cyano group, an ester group (-C(=O)OX ₁ or an amide group (-C(=O)N(X ₄ )(X ₅ ) (here X ₁ represents a linear alkyl group having 1 to 12 carbon atoms or a branched alkyl group having 1 to 12 carbon atoms, and X ₄ to X ₅ each represent a linear alkyl group having 1 to 12 carbon atoms. , a branched alkyl group having 1 to 12 carbon atoms), R ₃ represents hydrogen, R ₄ to R ₈ each independently represent hydrogen, a hydroxy group, a carboxy group, or a sulfoxy group, and R ₄ to R ₈ shows a hydroxy group.)
Specific monomers in general formula (5) of the present invention include, for example, 2-hydroxy-α,β,β-trifluorostyrene, 3-hydroxy-α,β,β-trifluorostyrene, 4- Hydroxy-α,β,β-trifluorostyrene, 2-carboxy-α,β,β-trifluorostyrene, 3-carboxy-α,β,β-trifluorostyrene, 4-carboxy-α,β,β- trifluorostyrene, 4-sulfoxy-α,β,β-trifluorostyrene, 2,3-dihydroxy-α,β,β-trifluorostyrene, 2,4-dihydroxy-α,β,β-trifluorostyrene, 3,4-dihydroxy-α,β,β-trifluorostyrene, 2-hydroxycinnamonitrile, 3-hydroxycinnamonitrile, 4-hydroxycinnamonitrile, 2-carboxycinnamonitrile, 3-hydroxycinnamonitrile , 4-hydroxycinnamonitrile, 2-carboxycinnamonitrile, 3-carboxycinnamonitrile, 4-carboxycinnamonitrile, 4-sulfoxycinnamonitrile, 2-hydroxycinnamic acid, 3-hydroxycinnamonitrile , 4-hydroxycinnamic acid, 2-carboxycinnamic acid, 3-carboxycinnamic acid, 4-carboxycinnamic acid, 2-sulfoxycinnamic acid, 3-sulfoxycinnamic acid, 4-sulfoxycinnamic acid, 2-hydroxy methyl cinnamate, methyl 3-hydroxycinnamate, methyl 4-hydroxycinnamate, methyl 2-carboxycinnamate, methyl 3-carboxycinnamate, methyl 4-carboxycinnamate, 4-sulfoxycinnamic acid methyl, ethyl 2-hydroxycinnamate, ethyl 3-hydroxycinnamate, ethyl 4-hydroxycinnamate, ethyl 2-carboxycinnamate, ethyl 3-carboxycinnamate, ethyl 4-carboxycinnamate, 4-ethyl sulfoxycinnamate, propyl 2-hydroxycinnamate, propyl 3-hydroxycinnamate, propyl 4-hydroxycinnamate, propyl 2-carboxycinnamate, propyl 3-carboxycinnamate, 4-carboxy Propyl cinnamate, Propyl 4-sulfoxycinnamate, 2-hydroxy-α,β,β-trifluoro-1-vinylnaphthalene, 3-hydroxy-α,β,β-trifluoro-1-vinylnaphthalene, 4- Hydroxy-α,β,β-trifluoro-1-vinylnaphthalene, 2-carboxy-α,β,β-trifluoro-1-vinylnaphthalene Lunaphthalene, 3-carboxy-α,β,β-trifluoro-1-vinylnaphthalene, 4-carboxy-α,β,β-trifluoro-1-vinylnaphthalene, 4-sulfoxy-α,β,β-tri Fluoro-1-vinylnaphthalene, 2,3-dihydroxy-α,β,β-trifluoro-1-vinylnaphthalene, 2,4-dihydroxy-α,β,β-trifluoro-1-vinylnaphthalene, 3,4 -dihydroxy-α,β,β-trifluoro-1-vinylnaphthalene, 2-hydroxy-β-cyano-1-vinylnaphthalene, 3-hydroxy-β-cyano-1-vinylnaphthalene, 4-hydroxy-β-cyano -1-vinylnaphthalene, 2-carboxy-β-cyano-1-vinylnaphthalene, 3-hydroxy-β-cyano-1-vinylnaphthalene, 4-hydroxy-β-cyano-1-vinylnaphthalene, 2-carboxy-β -cyano-1-vinylnaphthalene, 3-carboxy-β-cyano-1-vinylnaphthalene, 4-carboxy-β-cyano-1-vinylnaphthalene, 4-sulfoxy-β-cyano-1-vinylnaphthalene, β-( 2-hydroxy-1-naphthyl) acrylic acid, β-(3-hydroxy-1-naphthyl) acrylic acid, β-(4-hydroxy-1-naphthyl) acrylic acid, β-(2-carboxy-1-naphthyl) Acrylic acid, β-(3-carboxy-1-naphthyl) acrylic acid, β-(4-carboxy-1-naphthyl) acrylic acid, β-(2-sulfoxy-1-naphthyl) acrylic acid, β-(3- Sulfoxy-1-naphthyl) acrylic acid, β-(4-sulfoxy-1-naphthyl) acrylic acid, β-(2-hydroxy-1-naphthyl) methyl acrylate, β-(3-hydroxy-1-naphthyl) acrylic methyl acid, β-(4-hydroxy-1-naphthyl)methyl acrylate, β-(2-carboxy-1-naphthyl)methyl acrylate, β-(3-carboxy-1-naphthyl)methyl acrylate, β- (4-Carboxy-1-naphthyl) methyl acrylate, β-(4-sulfoxy-1-naphthyl) methyl acrylate, β-(2-hydroxy-1-naphthyl) ethyl acrylate, β-(3-hydroxy- 1-naphthyl) ethyl acrylate, β-(4-hydroxy-1-naphthyl) ethyl acrylate, β-(2-carboxy-1-naphthyl) ethyl acrylate, β-(3-carboxy-1-naphthyl) acrylic ethyl acetate, β- (4-carboxy-1-naphthyl) ethyl acrylate, β-(4-sulfoxy-1-naphthyl) ethyl acrylate, β-(2-hydroxy-1-naphthyl) propyl acrylate, β-(3-hydroxy- 1-naphthyl)propyl acrylate, β-(4-hydroxy-1-naphthyl)propyl acrylate, β-(2-carboxy-1-naphthyl)propyl acrylate, β-(3-carboxy-1-naphthyl)acryl propyl acid, β-(4-carboxy-1-naphthyl)propyl acrylate, β-(4-sulfoxy-1-naphthyl)propyl acrylate, 2-hydroxycinnamamide, 3-hydroxycinnamamide, 4-hydroxy Cinnamamide, 2-carboxycinnamamide, 3-carboxycinnamamide, 4-carboxycinnamamide, 2-sulfoxycinnamamide, 3-sulfoxycinnamamide, 4-sulfoxycinnamamide, N,N- dimethyl-2-hydroxycinnamamide, N,N-dimethyl-3-hydroxycinnamamide, N,N-dimethyl-4-hydroxycinnamamide, N,N-dimethyl-2-carboxycinnamamide, N, N-dimethyl-3-carboxycinnamamide, N,N-dimethyl-4-carboxycinnamamide, N,N-dimethyl-4-sulfoxycinnamamide, N,N-diethyl 2-hydroxycinnamamide, N , N-diethyl 3-hydroxycinnamamide, N,N-diethyl 4-hydroxycinnamamide, N,N-diethyl 2-carboxycinnamamide, N,N-diethyl 3-carboxycinnamamide, N,N -diethyl 4-carboxycinnamamide, N,N-diethyl 4-sulfoxycinnamamide, 2-hydroxy-β-methylstyrene, 3-hydroxy-β-methylstyrene, 4-hydroxy-β-methylstyrene, 2- Carboxy-β-methylstyrene, 3-carboxy-β-methylstyrene, 4-carboxy-β-methylstyrene, 2-sulfoxy-β-methylstyrene, 3-sulfoxy-β-methylstyrene, 4-sulfoxy-β-methyl Styrene, 2-hydroxybenzylidenemalononitrile, 3-hydroxybenzylidenemalononitrile, 4-hydroxybenzylidenemalononitrile, 2,3-dihydroxybenzylidenemalononitrile, 2,4-dihydroxybenzylidenemalononitrile, 3,4-dihydroxybenzylide 2-carboxybenzylidenemalononitrile, 2-carboxybenzylidenemalononitrile, 3-carboxybenzylidenemalononitrile, 4-carboxybenzylidenemalononitrile, 2,3-dicarboxybenzylidenemalononitrile, 2,4-dicarboxybenzylidenemalononitrile, 3,4-dicarboxybenzylidenemalononitrile Carboxybenzylidene malononitrile, 4-sulfoxybenzylidene malononitrile, dimethyl 2-hydroxybenzylidene malonate, dimethyl 3-hydroxybenzylidene malonate, dimethyl 4-hydroxybenzylidene malonate, dimethyl 2,3-dihydroxybenzylidene malonate, 2,4 -dimethyl dihydroxybenzylidene malonate, dimethyl 3,4-dihydroxybenzylidene malonate, dimethyl 2-carboxybenzylidene malonate, dimethyl 3-carboxybenzylidene malonate, dimethyl 4-carboxybenzylidene malonate, 2,3-dicarboxybenzylidene malonate Dimethyl, dimethyl 2,4-dicarboxybenzylidenemalonate, dimethyl 3,4-dicarboxybenzylidenemalonate, dimethyl 4-sulfoxybenzylidenemalonate, diethyl 2-hydroxybenzylidenemalonate, diethyl 3-hydroxybenzylidenemalonate, 4 - diethyl hydroxybenzylidene malonate, diethyl 2,3-dihydroxybenzylidene malonate, diethyl 2,4-dihydroxybenzylidene malonate, diethyl 3,4-dihydroxybenzylidene malonate, diethyl 2-carboxybenzylidene malonate, 3-carboxybenzylidene malonate diethyl acid, diethyl 4-carboxybenzylidenemalonate, diethyl 2,3-dicarboxybenzylidenemalonate, diethyl 2,4-dicarboxybenzylidenemalonate, diethyl 3,4-dicarboxybenzylidenemalonate, 4-sulfoxybenzylidenemalonate diethyl acid, dipropyl 2-hydroxybenzylidenemalonate, dipropyl 3-hydroxybenzylidenemalonate, dipropyl 4-hydroxybenzylidenemalonate, dipropyl 2,3-dihydroxybenzylidenemalonate, dipropyl 2,4-dihydroxybenzylidenemalonate, 3,4 -dipropyl dihydroxybenzylidene malonate, dipropyl 2-carboxybenzylidene malonate, dipropyl 3-carboxybenzylidene malonate, dipropyl 4-carboxybenzylidene malonate, 2,3-dicarboxybe dipropyl benzylidenemalonate, dipropyl 2,4-dicarboxybenzylidenemalonate, dipropyl 3,4-dicarboxybenzylidenemalonate, dipropyl 4-sulfoxybenzylidenemalonate, diisopropyl 2-hydroxybenzylidenemalonate, 3-hydroxybenzylidenemalonate diisopropyl acid, diisopropyl 4-hydroxybenzylidenemalonate, diisopropyl 2,3-dihydroxybenzylidenemalonate, diisopropyl 2,4-dihydroxybenzylidenemalonate, diisopropyl 3,4-dihydroxybenzylidenemalonate, diisopropyl 2-carboxybenzylidenemalonate, 3 -diisopropyl carboxybenzylidenemalonate, diisopropyl 4-carboxybenzylidenemalonate, diisopropyl 2,3-dicarboxybenzylidenemalonate, diisopropyl 2,4-dicarboxybenzylidenemalonate, diisopropyl 3,4-dicarboxybenzylidenemalonate, 4- Diisopropyl sulfoxybenzylidenemalonate, dibutyl 2-hydroxybenzylidenemalonate, dibutyl 3-hydroxybenzylidenemalonate, dibutyl 4-hydroxybenzylidenemalonate, dibutyl 2,3-dihydroxybenzylidenemalonate, dibutyl 2,4-dihydroxybenzylidenemalonate , dibutyl 3,4-dihydroxybenzylidenemalonate, dibutyl 2-carboxybenzylidenemalonate, dibutyl 3-carboxybenzylidenemalonate, dibutyl 4-carboxybenzylidenemalonate, dibutyl 2,3-dicarboxybenzylidenemalonate, 2,4- dibutyl dicarboxybenzylidenemalonate, dibutyl 3,4-dicarboxybenzylidenemalonate, dibutyl 4-sulfoxybenzylidenemalonate, diisobutyl 2-hydroxybenzylidenemalonate, diisobutyl 3-hydroxybenzylidenemalonate, diisobutyl 4-hydroxybenzylidenemalonate , diisobutyl 2,3-dihydroxybenzylidenemalonate, diisobutyl 2,4-dihydroxybenzylidenemalonate, diisobutyl 3,4-dihydroxybenzylidenemalonate, diisobutyl 2-carboxybenzylidenemalonate, diisobutyl 3-carboxybenzylidenemalonate, 4-carboxy diisobutyl benzylidenemalonate, diisobutyl 2,3-dicarboxybenzylidenemalonate, 2,4-dicarboxybe diisobutyl benzylidenemalonate, diisobutyl 3,4-dicarboxybenzylidenemalonate, diisobutyl 4-sulfoxybenzylidenemalonate, disec-butyl 2-hydroxybenzylidenemalonate, disec-butyl 3-hydroxybenzylidenemalonate, 4
- di-sec-butyl hydroxybenzylidene malonate, di-sec-butyl 2,3-dihydroxybenzylidene malonate, di-sec-butyl 2,4-dihydroxybenzylidene malonate, di-sec-butyl 3,4-dihydroxybenzylidene malonate, 2 -di-sec-butyl carboxybenzylidenemalonate, di-sec-butyl 3-carboxybenzylidenemalonate, di-sec-butyl 4-carboxybenzylidenemalonate, di-sec-butyl 2,3-dicarboxybenzylidenemalonate, 2,4- di-sec-butyl dicarboxybenzylidenemalonate, di-sec-butyl 3,4-dicarboxybenzylidenemalonate, di-sec-butyl 4-sulfoxybenzylidenemalonate, di-tert-butyl 2-hydroxybenzylidenemalonate, 3-hydroxy Di-tert-butyl benzylidene malonate, di-tert-butyl 4-hydroxybenzylidene malonate, di-tert-butyl 2,3-dihydroxybenzylidene malonate, di-tert-butyl 2,4-dihydroxybenzylidene malonate, 3,4-dihydroxy Di-tert-butyl benzylidene malonate, di-tert-butyl 2-carboxybenzylidene malonate, di-tert-butyl 3-carboxybenzylidene malonate, di-tert-butyl 4-carboxybenzylidene malonate, 2,3-dicarboxybenzylidene malonate Di-tert-butyl, di-tert-butyl 2,4-dicarboxybenzylidenemalonate, di-tert-butyl 3,4-dicarboxybenzylidenemalonate, di-tert-butyl 4-sulfoxybenzylidenemalonate, α-cyano-2 - hydroxycinnamic acid, α-cyano-3-hydroxycinnamic acid, α-cyano-4-hydroxycinnamic acid, α-cyano-2-carboxycinnamic acid, α-cyano-3-carboxycinnamic acid, α-Cyano-4-carboxycinnamic acid, α-cyano-4-sulfoxycinnamic acid, methyl α-cyano-2-hydroxycinnamate, methyl α-cyano-3-hydroxycinnamate, α-cyano-4 - methyl hydroxycinnamate, methyl α-cyano-2-carboxycinnamate, methyl α-cyano-3-carboxycinnamate, methyl α-cyano-4-carboxycinnamate, α-cyano-4-sulfoxycinnamate methyl formate, ethyl α-cyano-2-hydroxycinnamate, ethyl α-cyano-3-hydroxycinnamate, α-cyano-4-hydroxy ethyl cinnamate, ethyl α-cyano-2-carboxycinnamate, ethyl α-cyano-3-carboxycinnamate, ethyl α-cyano-4-carboxycinnamate, α-cyano-4-sulfoxycinnamic acid ethyl, propyl α-cyano-2-hydroxycinnamate, propyl α-cyano-3-hydroxycinnamate, propyl α-cyano-4-hydroxycinnamate, propyl α-cyano-2-carboxycinnamate, propyl α-cyano-3-carboxycinnamate, propyl α-cyano-4-carboxycinnamate, propyl α-cyano-4-sulfoxycinnamate, isopropyl α-cyano-2-hydroxycinnamate, α-cyano Isopropyl-3-hydroxycinnamate, Isopropyl α-cyano-4-hydroxycinnamate, Isopropyl α-cyano-2-carboxycinnamate, Isopropyl α-cyano-3-carboxycinnamate, α-cyano-4 -isopropyl carboxycinnamate, isopropyl α-cyano-4-sulfoxycinnamate, butyl α-cyano-2-hydroxycinnamate, butyl α-cyano-3-hydroxycinnamate, α-cyano-4-hydroxycinnamate Butyl cinnamate, butyl α-cyano-2-carboxycinnamate, butyl α-cyano-3-carboxycinnamate, butyl α-cyano-4-carboxycinnamate, butyl α-cyano-4-sulfoxycinnamate , isobutyl α-cyano-2-hydroxycinnamate, isobutyl α-cyano-3-hydroxycinnamate, isobutyl α-cyano-4-hydroxycinnamate, isobutyl α-cyano-2-carboxycinnamate, α -isobutyl cyano-3-carboxycinnamate, isobutyl α-cyano-4-carboxycinnamate, isobutyl α-cyano-4-sulfoxycinnamate, sec-butyl α-cyano-2-hydroxycinnamate, α- Sec-butyl cyano-3-hydroxycinnamate, sec-butyl α-cyano-4-hydroxycinnamate, sec-butyl α-cyano-2-carboxycinnamate, α-cyano-3-carboxycinnamic acid sec-butyl, sec-butyl α-cyano-4-carboxycinnamate, sec-butyl α-cyano-4-sulfoxycinnamate, tert-butyl α-cyano-2-hydroxycinnamate, α-cyano-3 - tert-butyl hydroxycinnamate, tert-butyl α-cyano-4-hydroxycinnamate, tert-butyl α-cyano-2-carboxycinnamate , tert-butyl α-cyano-3-carboxycinnamate, tert-butyl α-cyano-4-carboxycinnamate, tert-butyl α-cyano-4-sulfoxycinnamate, α-cyano-2-hydroxycinnamate Amic acid (2-methoxyethyl), α-cyano-3-hydroxycinnamic acid (2-methoxyethyl), α-cyano-4-hydroxycinnamic acid (2-methoxyethyl), α-cyano-2-carboxy Cinnamic acid (2-methoxyethyl), α-cyano-3-carboxycinnamic acid (2-methoxyethyl), α-cyano-4-carboxycinnamic acid (2-methoxyethyl), α-cyano-4- sulfoxycinnamic acid (2-methoxyethyl) and the like.

Among the monomers represented by general formula (5), 2-hydroxybenzylidenemalononitrile, 3-hydroxybenzylidenemalononitrile, 3-hydroxybenzylidenemalononitrile, and 4-hydroxybenzylidenemalononitrile, 2,3-dihydroxybenzylidenemalononitrile, 2,4-dihydroxybenzylidenemalononitrile, 3,4-dihydroxybenzylidenemalononitrile, 2-carboxybenzylidenemalononitrile, 3-carboxybenzylidenemalononitrile, 4- Carboxybenzylidene malononitrile, 4-sulfoxybenzylidene malononitrile, dimethyl 2-hydroxybenzylidene malonate, dimethyl 3-hydroxybenzylidene malonate, dimethyl 4-hydroxybenzylidene malonate, dimethyl 2,3-dihydroxybenzylidene malonate, 2,4 -dimethyl dihydroxybenzylidene malonate, dimethyl 3,4-dihydroxybenzylidene malonate, dimethyl 2-carboxybenzylidene malonate, dimethyl 3-carboxybenzylidene malonate, dimethyl 4-carboxybenzylidene malonate, 2,3-dicarboxybenzylidene malonate Dimethyl, dimethyl 4-sulfoxybenzylidenemalonate, diethyl 2-hydroxybenzylidenemalonate, diethyl 3-hydroxybenzylidenemalonate, diethyl 4-hydroxybenzylidenemalonate, diethyl 2,3-dihydroxybenzylidenemalonate, 2,4-dihydroxy Diethyl benzylidenemalonate, diethyl 3,4-dihydroxybenzylidenemalonate, diethyl 2-carboxybenzylidenemalonate, diethyl 3-carboxybenzylidenemalonate, diethyl 4-carboxybenzylidenemalonate, diethyl 4-sulfoxybenzylidenemalonate, 2- dipropyl hydroxybenzylidenemalonate, dipropyl 3-hydroxybenzylidenemalonate, dipropyl 4-hydroxybenzylidenemalonate, dipropyl 2,3-dihydroxybenzylidenemalonate, dipropyl 2,4-dihydroxybenzylidenemalonate, 3,4-dihydroxybenzylidenemalonate Dipropyl, 2-carboxybenzylidenemalonate dipropyl, 3-carboxybenzylidenemalonate dipropyl, 4-carboxybenzylidenemalonate dipropyl, 4-sulfoxybenzylidenemalonate dipropyl, 2-hydroxy Diisopropyl cybenzylidenemalonate, diisopropyl 3-hydroxybenzylidenemalonate, diisopropyl 4-hydroxybenzylidenemalonate, diisopropyl 2,3-dihydroxybenzylidenemalonate, diisopropyl 2,4-dihydroxybenzylidenemalonate, 3,4-dihydroxybenzylidenemalonate Diisopropyl, diisopropyl 2-carboxybenzylidenemalonate, diisopropyl 3-carboxybenzylidenemalonate, diisopropyl 4-carboxybenzylidenemalonate, diisopropyl 4-sulfoxybenzylidenemalonate, dibutyl 2-hydroxybenzylidenemalonate, dibutyl 3-hydroxybenzylidenemalonate , dibutyl 4-hydroxybenzylidene malonate, dibutyl 2,3-dihydroxybenzylidene malonate, dibutyl 2,4-dihydroxybenzylidene malonate, dibutyl 3,4-dihydroxybenzylidene malonate, dibutyl 2-carboxybenzylidene malonate, 3-carboxy Dibutyl benzylidenemalonate, dibutyl 4-carboxybenzylidenemalonate, dibutyl 4-sulfoxybenzylidenemalonate, diisobutyl 2-hydroxybenzylidenemalonate, diisobutyl 3-hydroxybenzylidenemalonate, diisobutyl 4-hydroxybenzylidenemalonate, 2,3- diisobutyl dihydroxybenzylidenemalonate, diisobutyl 2,4-dihydroxybenzylidenemalonate, diisobutyl 3,4-dihydroxybenzylidenemalonate, diisobutyl 2-carboxybenzylidenemalonate, diisobutyl 3-carboxybenzylidenemalonate, diisobutyl 4-carboxybenzylidenemalonate, diisobutyl 4-sulfoxybenzylidenemalonate, disec-butyl 2-hydroxybenzylidenemalonate, disec-butyl 3-hydroxybenzylidenemalonate, disec-butyl 4-hydroxybenzylidenemalonate, 2,3-dihydroxybenzylidenemalonic acid di-sec-butyl, di-sec-butyl 2,4-dihydroxybenzylidenemalonate, di-sec-butyl 3,4-dihydroxybenzylidenemalonate, di-sec-butyl 2-carboxybenzylidenemalonate, di-3-carboxybenzylidenemalonate sec-butyl, di-sec-butyl 4-carboxybenzylidenemalonate, di-sec-butyl 4-sulfoxybenzylidenemalonate, 2 - di-tert-butyl hydroxybenzylidene malonate, di-tert-butyl 3-hydroxybenzylidene malonate, di-tert-butyl 4-hydroxybenzylidene malonate, di-tert-butyl 2,3-dihydroxybenzylidene malonate, 2,4-dihydroxy Di-tert-butyl benzylidenemalonate, di-tert-butyl 3,4-dihydroxybenzylidenemalonate, di-tert-butyl 2-carboxybenzylidenemalonate, di-tert-butyl 3-carboxybenzylidenemalonate, di-tert-butyl 4-carboxybenzylidenemalonate tert-butyl, di-tert-butyl 4-sulfoxybenzylidenemalonate, α-cyano-2-hydroxycinnamic acid, α-cyano-3-hydroxycinnamic acid, α-cyano-4-hydroxycinnamic acid, α - cyano-2-carboxycinnamic acid, α-cyano-3-carboxycinnamic acid, α-cyano-4-carboxycinnamic acid, α-cyano-2-sulfoxycinnamic acid, α-cyano-3-sulfoxycinnamic acid, α-cyano-4-sulfoxycinnamic acid, methyl α-cyano-2-hydroxycinnamate, methyl α-cyano-3-hydroxycinnamate, methyl α-cyano-4-hydroxycinnamate, α- methyl cyano-2-carboxycinnamate, methyl α-cyano-3-carboxycinnamate, methyl α-cyano-4-carboxycinnamate, methyl α-cyano-4-sulfoxycinnamate, α-cyano-2 -ethyl hydroxycinnamate, ethyl α-cyano-3-hydroxycinnamate, ethyl α-cyano-4-hydroxycinnamate, ethyl α-cyano-2-carboxycinnamate, α-cyano-3-carboxy ethyl cinnamate, ethyl α-cyano-4-carboxycinnamate, ethyl α-cyano-4-sulfoxycinnamate, propyl α-cyano-2-hydroxycinnamate, α-cyano-3-hydroxycinnamic acid propyl, propyl α-cyano-4-hydroxycinnamate, propyl α-cyano-2-carboxycinnamate, propyl α-cyano-3-carboxycinnamate, propyl α-cyano-4-carboxycinnamate, Propyl α-cyano-4-sulfoxycinnamate, Isopropyl α-cyano-2-hydroxycinnamate, Isopropyl α-cyano-3-hydroxycinnamate, Isopropyl α-cyano-4-hydroxycinnamate, α-cyano -2-carboxycinnamate isopropyl, α-cyano-3-carboxycinnamic isopropyl acid, isopropyl α-cyano-4-carboxycinnamate, isopropyl α-cyano-4-sulfoxycinnamate, butyl α-cyano-2-hydroxycinnamate, butyl α-cyano-3-hydroxycinnamate, Butyl α-cyano-4-hydroxycinnamate, Butyl α-cyano-2-carboxycinnamate, Butyl α-cyano-3-carboxycinnamate, Butyl α-cyano-4-carboxycinnamate, α- Butyl cyano-4-sulfoxycinnamate, isobutyl α-cyano-2-hydroxycinnamate, isobutyl α-cyano-3-hydroxycinnamate, isobutyl α-cyano-4-hydroxycinnamate, α-cyano-2 -isobutyl carboxycinnamate, isobutyl α-cyano-3-carboxycinnamate, isobutyl α-cyano-4-carboxycinnamate, isobutyl α-cyano-4-sulfoxycinnamate, α-cyano-2-hydroxycinnamate sec-butyl cinnamate, sec-butyl α-cyano-3-hydroxycinnamate, sec-butyl α-cyano-4-hydroxycinnamate, sec-butyl α-cyano-2-carboxycinnamate, α- sec-butyl cyano-3-carboxycinnamate, sec-butyl α-cyano-4-carboxycinnamate, sec-butyl α-cyano-4-sulfoxycinnamate, tert α-cyano-2-hydroxycinnamate -butyl, tert-butyl α-cyano-3-hydroxycinnamate, tert-butyl α-cyano-4-hydroxycinnamate, tert-butyl α-cyano-2-carboxycinnamate, α-cyano-3 - tert-butyl carboxycinnamate, tert-butyl α-cyano-4-carboxycinnamate, tert-butyl α-cyano-4-sulfoxycinnamate, α-cyano-2-hydroxycinnamate (2-methoxy ethyl), α-cyano-3-hydroxycinnamic acid (2-methoxyethyl), α-cyano-4-hydroxycinnamic acid (2-methoxyethyl), α-cyano-2-carboxycinnamic acid (2- methoxyethyl), α-cyano-3-carboxycinnamic acid (2-methoxyethyl), α-cyano-4-carboxycinnamic acid (2-methoxyethyl), α-cyano-4-sulfoxycinnamic acid (2- methoxyethyl) is preferred, 2-hydroxybenzylidenemalononitrile, 3-hydroxybenzylidenemalononitrile, 4-hydroxybenzylidenemalononitrile, 2,3-dihydro Xybenzylidene malononitrile, 2,4-dihydroxybenzylidene malononitrile, 3,4-dihydroxybenzylidene malononitrile, dimethyl 2-hydroxybenzylidene malonate, dimethyl 3-hydroxybenzylidene malonate, dimethyl 4-hydroxybenzylidene malonate, 2,3 dimethyl-dihydroxybenzylidenemalonate, dimethyl 2,4-dihydroxybenzylidenemalonate, dimethyl 3,4-dihydroxybenzylidenemalonate, diethyl 2-hydroxybenzylidenemalonate, diethyl 3-hydroxybenzylidenemalonate, diethyl 4-hydroxybenzylidenemalonate , diethyl 2,3-dihydroxybenzylidenemalonate, diethyl 2,4-dihydroxybenzylidenemalonate, diethyl 3,4-dihydroxybenzylidenemalonate, dipropyl 2-hydroxybenzylidenemalonate, dipropyl 3-hydroxybenzylidenemalonate, 4-hydroxy Dipropyl benzylidenemalonate, dipropyl 2,3-dihydroxybenzylidenemalonate, dipropyl 2,4-dihydroxybenzylidenemalonate, dipropyl 3,4-dihydroxybenzylidenemalonate, diisopropyl 2-hydroxybenzylidenemalonate, diisopropyl 3-hydroxybenzylidenemalonate , diisopropyl 4-hydroxybenzylidenemalonate, diisopropyl 2,3-dihydroxybenzylidenemalonate, diisopropyl 2,4-dihydroxybenzylidenemalonate, diisopropyl 3,4-dihydroxybenzylidenemalonate, dibutyl 2-hydroxybenzylidenemalonate, 3-hydroxy Dibutyl benzylidenemalonate, dibutyl 4-hydroxybenzylidenemalonate, dibutyl 2,3-dihydroxybenzylidenemalonate, dibutyl 2,4-dihydroxybenzylidenemalonate, dibutyl 3,4-dihydroxybenzylidenemalonate, diisobutyl 2-hydroxybenzylidenemalonate , diisobutyl 3-hydroxybenzylidenemalonate, diisobutyl 4-hydroxybenzylidenemalonate, diisobutyl 2,3-dihydroxybenzylidenemalonate, diisobutyl 2,4-dihydroxybenzylidenemalonate, diisobutyl 3,4-dihydroxybenzylidenemalonate, 2-hydroxy di-sec-butyl benzylidenemalonate, di-sec-butyl 3-hydroxybenzylidenemalonate, 4- di-sec-butyl hydroxybenzylidene malonate, di-sec-butyl 2,3-dihydroxybenzylidene malonate, di-sec-butyl 2,4-dihydroxybenzylidene malonate, di-sec-butyl 3,4-dihydroxybenzylidene malonate, 2- Di-tert-butyl hydroxybenzylidene malonate, di-tert-butyl 3-hydroxybenzylidene malonate, di-tert-butyl 4-hydroxybenzylidene malonate, di-tert-butyl 2,3-dihydroxybenzylidene malonate, 2,4-dihydroxybenzylidene Di-tert-butyl malonate, 3,4-dihydroxybenzylidene Di-tert-butyl malonate, α-cyano-2-hydroxycinnamic acid, α-cyano-3-hydroxycinnamic acid, α-cyano-4-hydroxysilicone Amic acid, α-cyano-2-carboxycinnamic acid, α-cyano-3-carboxycinnamic acid, α-cyano-4-carboxycinnamic acid, α-cyano-2-sulfoxycinnamic acid, α-cyano- 3-sulfoxycinnamic acid, α-cyano-4-sulfoxycinnamic acid, methyl α-cyano-2-hydroxycinnamate, methyl α-cyano-3-hydroxycinnamate, α-cyano-4-hydroxycinnamic acid methyl, ethyl α-cyano-2-hydroxycinnamate, ethyl α-cyano-3-hydroxycinnamate, ethyl α-cyano-4-hydroxycinnamate, propyl α-cyano-2-hydroxycinnamate, Propyl α-cyano-3-hydroxycinnamate, Propyl α-cyano-4-hydroxycinnamate, Isopropyl α-cyano-2-hydroxycinnamate, Isopropyl α-cyano-3-hydroxycinnamate, α- isopropyl cyano-4-hydroxycinnamate, butyl α-cyano-2-hydroxycinnamate, butyl α-cyano-3-hydroxycinnamate, butyl α-cyano-4-hydroxycinnamate, α-cyano- isobutyl 2-hydroxycinnamate, isobutyl α-cyano-3-hydroxycinnamate, isobutyl α-cyano-4-hydroxycinnamate, sec-butyl α-cyano-2-hydroxycinnamate, α-cyano- sec-butyl 3-hydroxycinnamate, sec-butyl α-cyano-4-hydroxycinnamate, tert-butyl α-cyano-2-hydroxycinnamate, tert- α-cyano-3-hydroxycinnamate Butyl, tert-butyl α-cyano-4-hydroxycinnamate, α-cyano-2 -hydroxycinnamic acid (2-methoxyethyl), α-cyano-3-hydroxycinnamic acid (2-methoxyethyl), α-cyano-4-hydroxycinnamic acid (2-methoxyethyl) are more preferable. By polymerizing these monomers, a polymer can be obtained without post-reaction such as deprotection.

The polymer may contain other monomeric residue units as long as they do not exceed the scope of the present invention. Other monomeric residue units include, for example, α-methylstyrene residue units α-substituted styrene residue units such as; (meth) acrylic acid residue units; methyl (meth) acrylate residue units, ethyl (meth) acrylate residue units, butyl (meth) acrylate residue units, etc. Acrylonitrile residue unit; methacrylonitrile residue unit; ethylene residue unit, olefin residue unit such as propylene residue unit; di-n-butyl fumarate residue unit, One or more selected from fumaric acid diester residue units such as bis(2-ethylhexyl) fumarate residue units can be used.

Since the composition of the polymer of the present invention has better retardation characteristics when it is made into an optical compensation film, the monomer residue units represented by the general formula (1) are 5 to 55 mol% and 45 to 95 mol% of the monomer residue units represented by any of the general formulas (3) to (4) are preferable, and 20 to 50 mol% of the monomer residue units represented by the general formula (1) And more preferably 50 to 80 mol% of the monomer residue units represented by any of the general formulas (3) to (4), and 30 to 45 monomer residue units represented by the general formula (1) mol % and 55 to 70 mol % of the monomer residue units represented by any of the general formulas (3) to (4) are particularly preferred.

Since the polymer of the present invention has better heat resistance when made into a film, the glass transition point is preferably 100° C. or higher, more preferably 120° C. or higher, and 150° C. or higher. is particularly preferred.

The polymer of the present invention has excellent mechanical properties, strength when formed into a film, and toughness. The number average molecular weight is preferably 5,000 to 500,000, more preferably 8,000 to 400,000, and particularly preferably 10,000 to 300,000.

As a specific method for producing the polymer of the present invention, any method may be used as long as the copolymer can be obtained, for example, production by radical polymerization of the monomer represented by the general formula (5) can do.

Any of known polymerization methods such as bulk polymerization, solution polymerization, suspension polymerization, precipitation polymerization, and emulsion polymerization can be employed for the radical polymerization.

Examples of polymerization initiators for radical polymerization include benzoyl peroxide, lauryl peroxide, octanoyl peroxide, acetyl peroxide, di-t-butyl peroxide, t-butylcumyl peroxide and dicumyl peroxide. , t-butyl peroxyacetate, t-butyl peroxybenzoate and other organic peroxides; 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(2-butyronitrile), 2 , 2′-azobisisobutyronitrile, dimethyl-2,2′-azobisisobutyrate, 1,1′-azobis(cyclohexane-1-carbonitrile) and other azo initiators.

Solvents that can be used in the solution polymerization method, suspension polymerization method, precipitation polymerization method, and emulsion polymerization method are not particularly limited, and examples include aromatic solvents such as benzene, toluene, and xylene; cyclohexane; dioxane; tetrahydrofuran; acetone; methyl ethyl ketone; dimethylformamide;

The polymerization temperature for radical polymerization can be appropriately set according to the decomposition temperature of the polymerization initiator, and is generally preferably in the range of 30 to 150°C.

The polymer of the invention can be used as an optical film.

When the polymer of the present invention is used as an optical film, the haze is preferably 2% or less, more preferably 1% or less, in order to improve image quality.

When the polymer of the present invention is used as an optical film, it preferably has a total light transmittance of 85% or more in order to improve image quality characteristics.

When the polymer of the present invention is used as an optical film, it is preferably used as an optical compensation film (retardation film) because it has excellent retardation properties.

Since the optical compensation film using the polymer of the present invention exhibits retardation even when not stretched, the refractive index in the fast axis direction in the film plane is nx, and the refractive index in the film in-plane direction perpendicular to it is ny , as an optical compensation film having a relationship of nx≈ny<nz, where nz is the refractive index in the thickness direction of the film.

As an optical compensation film using the polymer of the present invention, it is possible to use the polymer alone, and it is suitable to prepare a composition in which it is mixed with other polymers. At this time, the other polymer to be mixed may be a polymer having negative birefringence or a polymer having positive birefringence.

When the polymer of the present invention is used as an optical compensation film having negative birefringence, the film thickness can be reduced. The absolute value of Rth/film thickness) is preferably 6 or more (nm/μm), more preferably 8 or more, and particularly preferably 9 or more.

Rth=[(nx+ny)/2−nz]×d (A)
(Wherein, nx represents the refractive index in the fast axis direction in the film plane, ny represents the refractive index in the slow axis direction in the film plane, nz represents the out-of-plane refractive index of the film, and d represents the film thickness.)
In the present invention, when a polymer is used as an optical compensation film having negative birefringence, it is preferable that at least one of nx<nz or ny<nz is satisfied because the three-dimensional refractive index can be controlled independently.

The method for producing the optical film using the copolymer of the present invention is not particularly limited, and for example, it can be produced by a solution casting method, a melt casting method, or the like.

The solution casting method is a method in which a solution of the polymer dissolved in a solvent (hereinafter referred to as dope) is cast on a support substrate, and then the solvent is removed by heating or the like to obtain a film. As a method for casting the dope onto the support substrate, for example, a T-die method, a doctor blade method, a bar coater method, a roll coater method, a lip coater method, or the like is used. In particular, industrially, it is common to continuously extrude the dope from a die onto a belt-shaped or drum-shaped support substrate. Examples of supporting substrates that can be used include glass substrates, metal substrates such as stainless steel and ferrotype, and films such as polyethylene terephthalate. In the solution casting method, the solution viscosity of the dope is an extremely important factor when forming a film having high transparency and excellent thickness accuracy and surface smoothness. More preferably ~10000 cPs.

At this time, the coating thickness of the film using the polymer is preferably 1 to 200 μm after drying, more preferably 5 to 100 μm, particularly preferably 10 μm, because excellent surface smoothness and optical properties can be obtained. ~50 μm.

The melt casting method is a molding method in which the polymer is melted in an extruder, extruded into a film form through a slit of a T-die, and then taken off while being cooled by rolls or air.

The optical compensation film using the polymer of the present invention can be used by peeling from the base glass substrate or other optical film, and can also be used as a laminate with the base glass substrate or other optical film. can be used.

The optical compensation film using the polymer of the present invention can also be used after being stretched.

The optical compensation film using the polymer of the present invention can be laminated with a polarizing plate and used as a circular or elliptical polarizing plate, and can be laminated with a polarizer containing polyvinyl alcohol/iodine or the like to form a polarizing plate. is also possible. Further, the optical compensation films can be laminated together or with another optical compensation film.

An optical compensation film using the polymer of the present invention is preferably blended with an antioxidant during film formation or for enhancing the thermal stability of the retardation film itself. Examples of the antioxidant include hindered phenol-based antioxidants, phosphorus-based antioxidants, and other antioxidants, and these antioxidants may be used alone or in combination. Then, since the antioxidant action is synergistically improved, it is preferable to use a combination of a hindered antioxidant and a phosphorus antioxidant. , and a phosphorus-based antioxidant in an amount of 100 to 500 parts by weight. Further, the amount of the antioxidant added is preferably 0.01 to 10 parts by weight with respect to 100 parts by weight of the polymer constituting the retardation film, since a high antioxidant effect can be obtained, and 0.5 ~1 part by weight is more preferred.

Moreover, as an ultraviolet absorber, for example, benzotriazole, benzophenone, triazine, benzoate, etc. may be blended as needed.

The optical film using the polymer of the present invention may contain other polymers, surfactants, polymer electrolytes, conductive complexes, inorganic fillers, pigments, antistatic agents, antiblocking agents, lubricants, and the like. .

According to the present invention, the refractive index in the thickness direction of the film, which is useful as a compensation film or antireflection film for contrast and viewing angle characteristics of liquid crystal displays, is large, in-plane retardation is large, and optical properties such as small wavelength dependence It is possible to provide a polymer suitable for an optical compensation film excellent in

The polymer of the present invention is a polymer suitable for optical compensation films excellent in retardation properties and compatibility, and particularly suitable for optical compensation films for liquid crystal display devices and organic EL devices.

EXAMPLES The present invention will be described below with reference to Examples, but the present invention is not limited to these Examples.

Various physical properties shown in the examples were measured by the following methods.

<Polymer composition>
It was determined by proton nuclear magnetic resonance spectroscopy ( ¹ H-NMR) using a nuclear magnetic resonance spectrometer (manufactured by JEOL, trade name JNM-ECZ400S). Those that were difficult to determine by ¹ H-NMR spectrum analysis were determined by CHN elemental analysis.

<Measurement of number average molecular weight>
Using a gel permeation chromatography (GPC) device (manufactured by Tosoh, trade name HLC-8320GPC (equipped with column GMH _HR -H)), tetrahydrofuran or N,N-dimethylformamide was used as a solvent, and measurement was performed at 40°C. and converted to standard polystyrene or pullulan.

<Measurement of three-dimensional refractive index of film>
It was measured using a fully automatic birefringence meter (manufactured by Oji Scientific Instruments, trade name KOBRA-WPR).

Example 1
5.0 g of ethyl α-cyano-4-hydroxycinnamate, 4.4 g of N-vinylcarbazole, 8.5 g of tetrahydrofuran as a polymerization solvent, and 2,5-dimethyl-2, which is a polymerization initiator, are placed in a 50 ml glass ampoule. 0.17 g of 5-di(2-ethylhexanoylperoxy)hexane was added, and after purging with nitrogen, the reactor was sealed under reduced pressure. This glass ampoule was placed in a constant temperature bath at 62° C. and held for 48 hours to carry out radical polymerization. After completion of the polymerization reaction, the polymer was taken out from the container, dropped into 500 ml of methanol to precipitate, and then vacuum-dried at 80° C. for 10 hours to obtain ethyl-N α-cyano-4-hydroxycinnamate. - 7.7 g of a vinylcarbazole copolymer were obtained. (Yield 82%)
The resulting α-cyano-4-hydroxycinnamate-ethyl-N-vinylcarbazole copolymer had a number-average molecular weight of 22,000 and a copolymer composition of α-cyano-4-hydroxycinnamate-ethyl residue units. /N-vinylcarbazole residue unit = 42/58 (mol%).

The obtained ethyl α-cyano-4-hydroxycinnamate-N-vinylcarbazole copolymer was dissolved in tetrahydrofuran, the solution was coated on a glass substrate with a spin coater, and vacuum-dried at 60° C. for 10 hours. A good film (thickness: 15.2 µm) having a haze of 0.4% and a total light transmittance of 87% was obtained. When the three-dimensional refractive index of the obtained film was measured, it was nx = 1.681, ny = 1.681, nz = 1.704, and Rth/film thickness = -23.0 (nm/μm). and expressed a high negative phase difference.

0.5 g of the obtained ethyl α-cyano-4-hydroxycinnamate-N-vinylcarbazole copolymer and 0.5 g of polymethyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd., number average molecular weight: 270000) were dissolved in 10 g of tetrahydrofuran, The solution was coated on a glass substrate with a spin coater and vacuum-dried at 60° C. for 10 hours to form a good film with a haze of 0.7%. The vinylcarbazole copolymer was a polymer with excellent compatibility.

Example 2
5.0 g of 4-hydroxybenzalmalononitrile, 4.5 g of 2-vinylnaphthalene, 10 g of tetrahydrofuran as a polymerization solvent and 2,5-dimethyl-2,5-di(2- 0.21 g of ethylhexanoylperoxy)hexane was put into the reactor, and after purging with nitrogen, the reactor was sealed under reduced pressure. This glass ampoule was placed in a constant temperature bath at 62° C. and held for 48 hours to carry out radical polymerization. After the completion of the polymerization reaction, the polymer was taken out from the container, dropped into 500 ml of methanol to precipitate, and then vacuum-dried at 80° C. for 10 hours to give 4-hydroxybenzalmalononitrile-2-vinylnaphthalene copolymer. 6.2 g of polymer were obtained. (Yield 65%)
The obtained 4-hydroxybenzalmalononitrile-2-vinylnaphthalene copolymer had a number average molecular weight of 12,000, and the composition of the copolymer was 4-hydroxybenzalononitrile residue units/2-vinylnaphthalene residue units. = 43/57 (mol%).

0.5 g of the resulting 4-hydroxybenzalmalononitrile-2-vinylnaphthalene copolymer and 0.5 g of polyethylene glycol (manufactured by Tokyo Chemical Industry Co., Ltd., number average molecular weight: 3000) were dissolved in 4 g of tetrahydrofuran, and the solution was spread on a glass substrate. A good film (thickness: 12.4 µm) having a haze of 0.4% and a total light transmittance of 86% was obtained by spin coating and vacuum drying at 60°C for 10 hours. When the three-dimensional refractive index of the obtained film was measured, it was nx = 1.634, ny = 1.633, nz = 1.668, and Rth/film thickness = -34.3 (nm/μm). and expressed a high negative phase difference.

0.8 g of the resulting 4-hydroxybenzalmalononitrile-2-vinylnaphthalene copolymer and 0.2 g of polymethyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd., number average molecular weight: 270000) were dissolved in 9 g of cyclohexanone, and the solution was applied to a glass substrate. A good film with a haze of 0.8% was obtained by coating with a spin coater on top and vacuum drying at 100 ° C. for 10 hours. It was a polymer excellent in

Example 3
5.3 g of 4-carboxybenzalmalononitrile, 4.7 g of N-vinylphthalimide, 12.5 g of N,N-dimethylformamide as a polymerization solvent and 2,5-dimethyl-2 as a polymerization initiator were placed in a 50 ml glass ampoule. , 5-di(2-ethylhexanoylperoxy)hexane (0.19 g) was added, and after purging with nitrogen, the inside was sealed under reduced pressure. Radical polymerization was performed by placing the glass ampoule in a constant temperature bath at 62° C. and holding it for 48 hours. After the completion of the polymerization reaction, the polymer was taken out from the container, dropped into 200 ml of methanol to precipitate, and then vacuum-dried at 80° C. for 10 hours to obtain 4-carboxybenzalmalononitrile-N-vinylphthalimide copolymer. 4.5 g of polymer were obtained. (Yield 45%)
The resulting 4-carboxybenzalmalononitrile-N-vinylphthalimide copolymer had a number average molecular weight of 13,000 and a copolymer composition of 4-carboxybenzalmalononitrile residue units/N-vinylphthalimide copolymer. It was confirmed that the residue unit = 35/65 (mol%).

The resulting 4-carboxybenzalmalononitrile-N-vinylphthalimide copolymer was dissolved in N,N-dimethylformamide, the solution was spin-coated on a glass substrate, and the haze was removed by vacuum drying at 60°C for 180 minutes. A good film (thickness: 13.0 μm) with a total light transmittance of 87% was obtained. When the three-dimensional refractive index of the obtained film was measured, it was nx = 1.626, ny = 1.626, nz = 1.647, and Rth/film thickness = -21.1 (nm/μm). and expressed a high negative phase difference.

0.7 g of the resulting 4-carboxybenzalmalononitrile-N-vinylphthalimide copolymer and 0.3 g of polyvinyl acetate (manufactured by Aldrich, number average molecular weight 53000) were dissolved in 4 g of N,N-dimethylformamide to form a solution. was coated on a glass substrate with a spin coater and vacuum dried at 60 ° C. for 10 hours to form a good film with a haze of 0.8%. was a polymer with excellent compatibility.

Example 4
6.1 g of N,N-dimethyl-4-sulfoxy-α-cyanocinnamicamide, 8.9 g of 2-vinylnaphthalene, 10.0 g of N,N-dimethylformamide as a polymerization solvent, and a polymerization initiator were added to a 50-ml glass ampoule. 0.28 g of a certain 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane was put thereinto, purged with nitrogen, and then sealed under reduced pressure. This glass ampoule was placed in a constant temperature bath at 62° C. and held for 48 hours to carry out radical polymerization. After the completion of the polymerization reaction, the polymer was taken out from the container, dropped into 200 ml of methanol to precipitate, and then vacuum-dried at 80° C. for 10 hours to obtain N,N-dimethyl-4-sulfoxy-α-cyanosilicate. 3.3 g of a amide-2-vinyl naphthalene copolymer was obtained. (Yield 33%)
The resulting N,N-dimethyl-4-sulfoxy-α-cyanocinamide-2-vinylnaphthalene copolymer had a number average molecular weight of 10,000 and a copolymer composition of N,N-dimethyl-4-sulfoxy- It was confirmed that α-cyanocinamide residue units/2-vinylnaphthalene copolymer residue units=29/71 (mol %).

The resulting N,N-dimethyl-4-sulfoxy-α-cyanocinamide-2-vinylnaphthalene copolymer was dissolved in N,N-dimethylformamide, and the solution was spin-coated on a glass substrate and heated at 60°C. A good film (thickness: 9.7 µm) having a haze of 0.5% and a total light transmittance of 86% was obtained by vacuum drying for 10 hours. When the three-dimensional refractive index of the obtained film was measured, it was nx = 1.633, ny = 1.634, nz = 1.652, and Rth/film thickness = -18.5 (nm/μm). and expressed a high negative phase difference.

0.8 g of the resulting N,N-dimethyl-4-sulfoxy-α-cyanocinamide-2-vinylnaphthalene copolymer and 0.3 g of ethyl cellulose (Ethocel Standard 100 manufactured by Dow Chemical Co., number average molecular weight 55000) were combined. Dissolve in 9 g of tetrahydrofuran, apply the solution on a glass substrate with a spin coater, and vacuum dry at 60° C. for 10 hours to obtain a good film with a haze of 0.9%. The sulfoxy-α-cyanocinamide-2-vinylnaphthalene copolymer was a polymer with excellent compatibility.

Comparative example 1
Poly(N-vinylcarbazole) (manufactured by Aldrich, number average molecular weight 35,000) 0.5 g and polymethyl methacrylate (manufactured by Tokyo Kasei, number average molecular weight 270,000) 0.5 g were dissolved in 10 g of tetrahydrofuran, and the solution was placed on a glass substrate. Poly(N-vinylcarbazole) was a poorly compatible polymer, since coating with a spin coater and vacuum drying at 60° C. for 10 hours resulted in a poor film with a haze of 86.6%.

Comparative example 2
Poly(2-vinylnaphthalene) (manufactured by Aldrich, number average molecular weight 50,000) 0.8 g and polymethyl methacrylate (manufactured by Tokyo Kasei, number average molecular weight 270,000) 0.2 g were dissolved in cyclohexanone 9 g, and the solution was placed on a glass substrate. Poly(2-vinylnaphthalene) was a poorly compatible polymer, since coating with a spin coater and vacuum drying at 100° C. for 10 hours resulted in a poor film with a haze of 90.3%.

Comparative example 3
2.8 g of methacrylonitrile, 7.2 g of N-vinylphthalimide, 12.5 g of N,N-dimethylformamide as a polymerization solvent and 2,5-dimethyl-2,5-dimethylformamide as a polymerization initiator were placed in a 50 ml glass ampoule. 0.30 g of (2-ethylhexanoylperoxy)hexane was added, and after purging with nitrogen, the flask was sealed under reduced pressure. The glass ampoule was placed in a constant temperature bath at 62° C. and held for 18 hours to carry out radical polymerization. After completion of the polymerization reaction, the polymer was taken out from the container, dropped into 200 ml of methanol to precipitate, and then vacuum-dried at 80° C. for 10 hours to obtain a methacrylonitrile-N-vinylphthalimide copolymer7. 8 g was obtained. (Yield 78%)
The obtained methacrylonitrile-N-vinylphthalimide copolymer was confirmed to have a number average molecular weight of 21,000.

0.7 g of the obtained methacrylonitrile-N-vinylphthalimide copolymer and 0.3 g of polyvinyl acetate (manufactured by Aldrich, number average molecular weight 53000) were dissolved in 4 g of N,N-dimethylformamide, and the solution was spread on a glass substrate. was coated with a spin coater and vacuum-dried at 60°C for 10 hours to form a poor film with a haze of 92.1%. rice field.

The present invention provides a novel polymer, which is expected to be used as a film, especially an optical compensation film.

Claims (4)

does not contain organic groups containing bismethide acid groups or bismethide salts;
2-hydroxybenzylidenemalononitrile residue unit, 3-hydroxybenzylidenemalononitrile residue unit, 4-hydroxybenzylidenemalononitrile residue unit, 2,3-dihydroxybenzylidenemalononitrile residue unit, 2,4-dihydroxybenzylidenemalononitrile residue unit, 3,4-dihydroxybenzylidenemalononitrile residue unit, α-cyano-2-hydroxycinnamic acid residue unit, α-cyano-3-hydroxycinnamic acid residue unit, α-cyano-4- hydroxycinnamic acid residue unit, α-cyano-2-carboxycinnamic acid residue unit, α-cyano-3-carboxycinnamic acid residue unit, α-cyano-4-carboxycinnamic acid residue unit, α-cyano-2-sulfoxycinnamic acid residue unit, α-cyano-3-sulfoxycinnamic acid residue unit, α-cyano-4-sulfoxycinnamic acid residue unit, methyl α-cyano-2-hydroxycinnamate residue unit, methyl α-cyano-3-hydroxycinnamate residue unit, methyl α-cyano-4-hydroxycinnamate residue unit, ethyl α-cyano-2-hydroxycinnamate residue unit, α -ethyl cyano-3-hydroxycinnamate residue unit, ethyl α-cyano-4-hydroxycinnamate residue unit, propyl α-cyano-2-hydroxycinnamate residue unit, α-cyano-3- propyl hydroxycinnamate residue unit, propyl α-cyano-4-hydroxycinnamate residue unit, isopropyl α-cyano-2-hydroxycinnamate residue unit, isopropyl α-cyano-3-hydroxycinnamate residue unit, isopropyl α-cyano-4-hydroxycinnamate residue unit, butyl α-cyano-2-hydroxycinnamate residue unit, butyl α-cyano-3-hydroxycinnamate residue unit, α -butyl cyano-4-hydroxycinnamate residue unit, isobutyl α-cyano-2-hydroxycinnamate residue unit, isobutyl α-cyano-3-hydroxycinnamate residue unit, α-cyano-4- isobutyl hydroxycinnamate residue unit, sec-butyl α-cyano-2-hydroxycinnamate residue unit, sec-butyl α-cyano-3-hydroxycinnamate residue unit, α-cyano-4-hydroxy sec-butyl cinnamate residue unit, tert-butyl α-cyano-2-hydroxycinnamate residue unit, tert-butyl α-cyano-3-hydroxycinnamate residue unit, α-cyano-4- tert-butyl hydroxycinnamate residue position, α-cyano-2-hydroxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-3-hydroxycinnamic acid (2-methoxyethyl) residue unit, α-cyano-4-hydroxycinnamic acid one or more residue units selected from the group consisting of mic acid (2-methoxyethyl) residue units and 4-carboxybenzalmalononitrile residue units (hereinafter referred to as "(1) residue units") and
N-vinylcarbazole residue unit, 3-methyl-N-vinylcarbazole residue unit, 3-chloro-N-vinylcarbazole residue unit, N-vinylphthalimide residue unit, 4-methylphthalimide residue unit, 4- A polymer comprising only one or more residue units selected from the group consisting of chloromethylphthalimide residue units and 4-nitrophthalimide residue units (hereinafter referred to as "(2) residue units"). . The polymer of claim 1 comprising (1) 5 to 55 mol % of residue units and (2) 95 to 45 mol % of residue units. 2-hydroxybenzylidenemalononitrile, 3-hydroxybenzylidenemalononitrile, 4-hydroxybenzylidenemalononitrile, 2,3-dihydroxybenzylidenemalononitrile, 2,4-dihydroxybenzylidenemalononitrile, 3,4-dihydroxybenzylidenemalononitrile, α- Cyano-2-hydroxycinnamic acid, α-cyano-3-hydroxycinnamic acid, α-cyano-4-hydroxycinnamic acid, methyl α-cyano-2-hydroxycinnamate, α-cyano-3-hydroxy Methyl cinnamate, methyl α-cyano-4-hydroxycinnamate, ethyl α-cyano-2-hydroxycinnamate, ethyl α-cyano-3-hydroxycinnamate, α-cyano-4-hydroxycinnamate ethyl acetate, propyl α-cyano-2-hydroxycinnamate, propyl α-cyano-3-hydroxycinnamate, propyl α-cyano-4-hydroxycinnamate, isopropyl α-cyano-2-hydroxycinnamate , isopropyl α-cyano-3-hydroxycinnamate, isopropyl α-cyano-4-hydroxycinnamate, butyl α-cyano-2-hydroxycinnamate, butyl α-cyano-3-hydroxycinnamate, α -butyl cyano-4-hydroxycinnamate, isobutyl α-cyano-2-hydroxycinnamate, isobutyl α-cyano-3-hydroxycinnamate, isobutyl α-cyano-4-hydroxycinnamate, α-cyano -sec-butyl 2-hydroxycinnamate, sec-butyl α-cyano-3-hydroxycinnamate, sec-butyl α-cyano-4-hydroxycinnamate, tert α-cyano-2-hydroxycinnamate -butyl, tert-butyl α-cyano-3-hydroxycinnamate, tert-butyl α-cyano-4-hydroxycinnamate, α-cyano-2-hydroxycinnamate (2-methoxyethyl), α- One or more selected from the group consisting of cyano-3-hydroxycinnamic acid (2-methoxyethyl), α-cyano-4-hydroxycinnamic acid (2-methoxyethyl) and 4-carboxybenzalmalononitrile 3. The method for producing a polymer according to claim 1, wherein the polymer is obtained by polymerizing a monomer. 3. An optical film comprising the polymer according to claim 1 or 2.