JP2001139950A - Optically anisotropic material, optical compensating film and liquid crystal display element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a novel optically anisotropic material capable of using for optical compensating films for enlarging the angle of visibility of a liquid crystal display and further obtain a liquid crystal display element assembled with the optically anisotropic material. SOLUTION: This optically anisotropic material is characterized in that it contains at least one kind of compound having at least two aromatic groups or aromatic heterocyclic groups in arbitrary sites in the molecule and a part capable of forming an intramolecular hydrogen bond.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel optically anisotropic material used as an optical compensation film capable of compensating a viewing angle of a liquid crystal display, and a wide field of view incorporating the optically anisotropic material. The present invention relates to a corner liquid crystal display element.

[0002]

2. Description of the Related Art CRTs have been mainly used as display devices for OA equipment such as desktop personal computers and word processors.
A liquid crystal display element (hereinafter, also referred to as a liquid crystal display)
It is widely used instead of CRTs because it is thin and lightweight, and has low power consumption. Liquid crystal displays use anisotropic liquid crystal materials and polarizers, so even if a good display is obtained when viewed from the front, the display performance deteriorates when viewed from an oblique angle. Therefore, a viewing angle compensator is required to improve the performance. As the compensating plate, first, a compensating plate capable of canceling this anisotropy, that is, a compensating plate having so-called optical anisotropy is effective.

[0003] From such a viewpoint, as a compensating plate capable of performing viewing angle compensation, a biaxial film having a retardation in the plane and a refractive index in the thickness direction smaller than the in-plane refractive index. The use of stretched films is proposed. However, since the director of the liquid crystal in the cell changes continuously in the film thickness direction, optical rotation dispersion occurs, and when viewing from one azimuth, good viewing angle compensation is performed, but viewing from another azimuth is performed. Sometimes sufficient compensation was not achieved. In addition, since the biaxially stretched film has no change in the refractive index in the thickness direction, there is a problem that the influence of optical rotation dispersion cannot be completely eliminated by the biaxially stretched film.

Therefore, in order to sufficiently compensate the viewing angle of the liquid crystal display, in addition to the condition that the liquid crystal display has in-plane retardation and the condition that the refractive index in the thickness direction is smaller than the in-plane refractive index, It is considered that the requirement that the refractive index continuously changes in the thickness direction must be satisfied. It has been proposed to use an optically anisotropic element obtained by fixing the orientation of a liquid crystalline compound as an optical compensation sheet satisfying these conditions. Liquid crystal compounds include
Since there are various orientation modes, by fixing the orientation mode, an optically anisotropic element having optical performance that cannot be obtained with a biaxially stretched film can be obtained.

In recent optical compensatory sheets, it has been proposed to use a discotic liquid crystal compound in place of the rod-like liquid crystal compound. It has been proposed to introduce a polymerizable group and stably fix the alignment state by a polymerization reaction, and has actually shown a remarkable effect on the expansion of the viewing angle of a liquid crystal display.

[0006] However, as for compounds exhibiting discotic liquid crystallinity, many compounds have not yet been known, and even excellent mixtures have not been known. Further, improvement of these compounds is desired also from the viewpoint of manufacturing cost, and new materials capable of achieving a wider viewing angle of a liquid crystal display are required, and research is being continued.

[0007]

SUMMARY OF THE INVENTION The present invention solves the above-mentioned problems, and provides a new optically anisotropic material which can be used for an optical compensation film capable of expanding a viewing angle of a liquid crystal display. Is what you do. Further, the present invention provides a liquid crystal display device incorporating the optically anisotropic material.

[0008]

The object of the present invention is achieved by the following method.

(1) At least 2 at any position in the molecule
An optically anisotropic material comprising at least one compound having two aromatic groups or aromatic heterocyclic groups and having a moiety capable of hydrogen bonding in a molecule.

(2) An optically anisotropic material comprising at least one compound represented by the general formula (I).

In the general formula (I), A ₀ -B ₀ , wherein A ₀ and B ₀ each represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and at least one hydrogen bond-donating moiety in the molecule. And at least one hydrogen bond-accepting moiety.

(3) An optically anisotropic material comprising at least one compound represented by the general formula (II).

Formula (II) A ₁ -B _{1 wherein} A ₁ and B ₁ each represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and A ₁ represents at least one hydrogen bond-donating moiety. And B ₁ has at least one hydrogen bond-accepting moiety.

(4) An optically anisotropic material comprising at least one compound represented by the general formula (III).

[0015]

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In the formula, A ₂ and B ₂ represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and X represents a chalcogen atom or N
It represents R _101, R ₁₀₁ represents a hydrogen atom or a substituent. A ₂
Having a hydrogen bond donor moiety in the position adjacent A ₂ and> C = X above are attached. However, when X is NR ₁₀₁ and R ₁₀₁ is a hydrogen atom, it may be a hydrogen bond-accepting moiety, and when X is NR ₁₀₁ , R ₁₀₁ and either one of A ₂ or B ₂ It may be condensed to form a ring.

(5) An optically anisotropic material containing at least one compound represented by the general formula (IV).

General formula (IV) A ₃ -Y = Z-B _{3 In the} formula, A ₃ and B ₃ represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and Y and Z represent a carbon atom or Represents a nitrogen atom. When Y and Z are both carbon atoms, Y or either of Z has an intramolecular hydrogen bond possible substituents, A ₃ and B ₃ on the -Y = position adjacent Z- is bonded Has a moiety capable of intramolecular hydrogen bonding with a substituent on Y or Z. When Y and Z are both nitrogen atoms have a hydrogen bond donor moiety to the position adjacent -Y = Z- on A ₃ and B ₃ are bonded.
When either Y or Z is a nitrogen atom, it has a hydrogen bond donating moiety at the adjacent position where -Y = Z- on A ₃ and B ₃ is bonded, or A substituent on a carbon atom of Y or Z and a hydrogen atom on the carbon atom having a substituent capable of intramolecular hydrogen bond on the carbon atom, and a substituent on the carbon atom of Y or Z adjacent to -Y = Z- on A ₃ and B ₃ It has a bondable part.

(6) An optically anisotropic material containing at least one compound represented by the general formula (V).

Formula (V) A ₄ -B ₄ -C _{4 wherein} A ₄ , B ₄ and C ₄ each represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, wherein A ₄ is at least 1 When one of B ₄ and C ₄ has at least one hydrogen bond-accepting moiety, and when A ₄ has at least one hydrogen-bond accepting moiety, B ₄ , C ₄
Has at least one hydrogen bond donating moiety.

(7) An optical compensation film comprising at least one compound represented by the general formula (I).

(8) An optical compensation film comprising at least one compound represented by the general formula (II).

(9) An optical compensation film comprising at least one compound represented by the general formula (III).

(10) An optical compensation film comprising at least one compound represented by the general formula (IV).

(11) An optical compensation film comprising at least one compound represented by the general formula (V).

(12) A liquid crystal display device incorporating at least one optically anisotropic material as described in 2 to 6 above.

Hereinafter, the present invention will be described in more detail.
The optically anisotropic material according to the present invention will be described.

The characteristics of the optically anisotropic material used in the present invention, the refractive indices n _x in a certain plane, and n _y, an optical axis perpendicular to the plane (hereinafter, referred to as director) the refractive index of n
_{When z} is set, the refractive index in an extremely small area in the liquid crystal layer (optically anisotropic material) is _nx ≧ _ny > _nz . As described above, the optically anisotropic material of the present invention refers to a material having a different refractive index in one direction and another direction, and the material may be a compound alone or a composition containing at least one kind of the compound. In the present invention, the orientation order of these molecules is not particularly limited, but those having only N phase as the only liquid crystal layer are preferable.

In order to fix the optically anisotropic material according to the present invention without impairing the alignment form in the liquid crystal state, it is preferable that the material does not undergo a transition from the liquid crystal layer to the crystal phase at the time of fixing. Further, when a film is formed, it is desirable that the orientation form is maintained under the use conditions and that the film can be handled like a solid. Further, in the present invention, the state of immobilization is the most typical and preferable mode in which the orientation is maintained by polymerizing in a liquid crystal state or the like, but is not limited thereto. When the optically anisotropic material is used as the optical compensation film,
Under the use conditions of the optical compensation film, specifically, usually 0 ° C
In a temperature range of -30 ° C to 70 ° C under severer conditions, the film has no fluidity and does not cause a change in the orientation form due to an external field or an external force. It refers to a state in which the form can be kept stable. For example, in a temperature range of usually from 0 ° C. to 50 ° C., there is no particular problem as long as shearing is forcibly applied and there is no disturbance in the orientation form.

The compounds represented by the general formulas (I) to (V) used in the present invention have any of the above-mentioned properties, and at the same time, have good domain cohesion due to uniform defect-free orientation. Is desirable. When the integration of the domains is poor, the resulting structure becomes a polydomain, an alignment defect occurs at the boundary between the domains, and light is scattered. In addition, the transmittance of the film is undesirably reduced.

The specific structure of the compound is at least 2
It is composed of a mother nucleus having two aromatic groups or aromatic heterocyclic groups, and substituents and side chains around it. As the side chain, a monofunctional one is preferably used, but a compound obtained by partially linking the compounds using a bifunctional one and oligomerizing or polymerizing the compound is also used as the material of the present invention. It can be preferably used.

Hereinafter, the compounds represented by formulas (I) to (V) will be described in detail. A ₀ and B ₀ in the general formula (I) are 5
Represents a 6-membered aromatic group or aromatic heterocyclic group, for example, benzene ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, tetrazine ring, pyrrole ring, pyrazole ring, triazole ring, furan ring, Examples include a thiophene ring, a thiazole ring, an oxazole ring, an imidazole ring, a thiadiazole ring, an oxadiazole ring, a quinoline ring, and an isoquinoline ring. Of these, a benzene ring and a pyridine ring are preferred.

These aromatic groups and aromatic heterocyclic groups are
It may be substituted by a halogen atom or another substituent, and examples of the substituent include an alkyl group (for example, a methyl group, an ethyl group, an isopropyl group, a hydroxyethyl group, a methoxymethyl group, a trifluoromethyl group, a t-butyl group, etc. ),
Cycloalkyl groups (eg, cyclopentyl group, cyclohexyl group, etc.), aralkyl groups (eg, benzyl group, 2-
Phenethyl group, etc.), aryl group (for example, phenyl group, naphthyl group, p-tolyl group, p-chlorophenyl group, etc.),
Alkoxy group (for example, methoxy group, ethoxy group, isopropoxy group, n-butoxy group, etc.), aryloxy group (for example, phenoxy group, etc.), cyano group, acylamino group (for example, acetylamino group, propionylamino group, etc.), alkylthio Group (eg, methylthio group, ethylthio group, n-butylthio group, etc.), arylthio group (eg, phenylthio group, etc.), sulfonylamino group (eg, methanesulfonylamino group, benzenesulfonylamino group, etc.), ureido group (eg, 3-methylureido) Group, 3,
3-dimethylureido group, 1,3-dimethylureido group, etc.), sulfamoylamino group (eg, dimethylsulfamoylamino group), carbamoyl group (eg, methylcarbamoyl group, ethylcarbamoyl group, dimethylcarbamoyl group, etc.), Sulfamoyl group (eg, ethylsulfamoyl group, dimethylsulfamoyl group, etc.), alkoxycarbonyl group (eg, methoxycarbonyl group, ethoxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenoxycarbonyl group, etc.), sulfonyl group (eg, methane Sulfonyl group, butanesulfonyl group, benzenesulfonyl group, etc.), acyl group (eg, acetyl group, propanoyl group, butanoyl group, etc.), amino group (eg, methylamino group, ethylamino group, dimethylamino group, etc.), hydroxyl group Nitro group, although an imido group (e.g. phthalimido group), preferably a halogen atom, a hydroxyl group, an amino group, an acyl group, a carbamoyl group, an alkoxy group, a cyano group.

The aromatic ring and the aromatic hetero ring may have a side chain, and examples of the side chain include an alkyl group, an alkoxy group, an alkylthio group and an acyloxy group. An aromatic group or a heterocyclic group may be contained therein. Further, when the side chain is C.I. Hansch, A .; Le
o, R. W. Taft, Chemical Review Magazine (Che
m. Rev .. ), 1991, Vol. 91, pp. 165-195 (American Chemical Society), and examples thereof include an alkoxy group, an alkyl group, an alkoxycarbonyl group, and a halogen atom. Further, the side chain may have a functional group such as an ether group, an ester group, a carbonyl group, a thioether group, a sulfoxide group, a sulfonyl group, and an amide group.
Hereinafter, the side chain will be described in detail.

Examples of the side chain include an alkanoyloxy group (eg, a hexanoyloxy group, a heptanoyloxy group, an octanoyloxy group, a nonanoyloxy group,
Decanoyloxy group, undecanoyloxy group, etc.), alkylsulfonyl group (eg, hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, etc.), alkylthio group (eg, Hexylthio group, heptylthio group, dodecylthio group, etc.), alkoxy group (for example, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc.), 2-
(4-alkylphenyl) ethynyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group,
Pentyl group, hexyl group, heptyl group, octyl group, nonyl group, etc., terminal vinyl alkoxy group (for example, 4-vinylbutoxy group, 5-vinylpentyloxy group, 6-vinylhexyloxy group, 7-vinylheptyloxy group) , 8
-Vinyloctyloxy group, 9-vinylnonyloxy group, etc.), 4-alkoxyphenyl group (for example, the above-mentioned alkoxy group as the alkoxy group), and alkoxymethyl group (for example, the above-mentioned alkoxy group as the alkoxy group) Alkylthiomethyl group (for example, the above-described alkylthio group as the alkylthio group), 2-alkylthioethyl (for example, the above-mentioned alkylthio group as the alkylthio group),
Alkylthioethoxymethyl group (for example, the above-mentioned alkylthio group as the alkylthio group), 2-alkoxyethoxymethyl group (for example, the above-mentioned alkoxy group as the alkoxy group), 2-alkoxycarbonylethyl group (for example, As the alkoxy group, those described above for the alkoxy group), a cholesteryloxycarbonyl group, a β-sitosteryloxycarbonyl group,
4-alkoxyphenoxycarbonyl groups (for example, those mentioned above in the alkoxy group as the alkoxy group),
A 4-alkoxybenzoyloxy group (for example, those described above as the alkoxy group as the alkoxy group), a 4-alkylbenzoyloxy group (for example, as the alkyl group,
Examples thereof include the above-mentioned 2- (4-alkylphenyl) ethynyl groups) and 4-alkoxybenzoyl groups (for example, those described above for the alkoxy groups as the alkoxy groups).

In the above, the phenyl group may be another aromatic group (for example, a naphthyl group, a phenanthryl group or an anthracenyl group), or may be further substituted in addition to the above substituents. Further, the phenyl group is an aromatic hetero ring (for example, pyridyl group, pyrimidyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, thiazolyl group,
Oxazolyl group, thiazolyl group, thiadiazolyl group, oxadiazolyl group, quinolyl group, isoquinolyl group). The compounds of the present invention are formed by the appropriate combination of the structure and number of the above-mentioned mother nucleus, substituents and side chains.

The term "hydrogen bond donating moiety" refers to a substituent or an atom capable of donating a hydrogen bond, and specifically includes an acylamino group (eg, acetylamino group, propionylamino group, etc.) and a sulfonylamino group (eg, methane group). Sulfonylamino group, benzenesulfonylamino group, etc.), sulfamoylamino group (eg, dimethylsulfamoylamino group), carbamoyl group (eg, methylcarbamoyl group, ethylcarbamoyl group, dimethylcarbamoyl group, etc.), sulfamoyl group (eg, ethyl) Dissociative protons such as sulfamoyl group, dimethylsulfamoyl group, etc., amino groups (eg, methylamino group, ethylamino group, dimethylamino group, etc.), hydroxyl group, sulfonic acid group, carboxylic acid group, mercapto group And a position adjacent to the bonding position A heterocyclic group having a dissociable proton (for example, 1H-2-pyrrolyl group, 1H-2-imidazolyl group, 1H-2-pyrazolyl group, 1H-2-indolyl group, 1H-2-purinyl group, etc.) and the like; On the other hand, the hydrogen bond-accepting moiety represents a substituent and an atom capable of accepting a hydrogen bond, specifically, an alkoxy group (for example, a methoxy group, an ethoxy group, an isopropoxy group, an n-butoxy group, etc.), an aryloxy group and the like. Group (eg, phenoxy group), acylamino group (eg, acetylamino group, propionylamino group, etc.), alkylthio group (eg, methylthio group, ethylthio group, n-butylthio group, etc.), arylthio group (eg, phenylthio group, etc.), sulfonylamino Group (eg, methanesulfonylamino group, benzenesulfonylamino group, etc.), sulfamoylamino group (eg, Dimethylsulfamoylamino group), carbamoyl group (eg, methylcarbamoyl group, ethylcarbamoyl group, dimethylcarbamoyl group, etc.), sulfamoyl group (eg, ethylsulfamoyl group, dimethylsulfamoyl group, etc.), alkoxycarbonyl group (eg, Methoxycarbonyl group, ethoxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenoxycarbonyl group, etc.), sulfonyl group (eg, methanesulfonyl group, butanesulfonyl group, benzenesulfonyl group, etc.), acyl group (eg, acetyl group, propanoyl group, A substituent such as a butanoyl group), an amino group (eg, a methylamino group, an ethylamino group, a dimethylamino group), an oxo group, a thioxo group, a hydroxyl group or a nitro group; Chalcogen A heterocyclic group having a non-atom atom (for example, a 2-pyridyl group, a 2-thienyl group, a 2-furyl group, a 2-pyrrolyl group, a 2-pyrazolyl group, a 2-imidazolyl group, a 2-thiazolyl group, a 2-quinolyl group, -Isoquinolyl group), a halogen atom and the like.

A ₁ and B ₁ in the general formula (II) have the same meanings as A ₀ and B ₀ in the general formula (I), respectively. It has the same meaning as the definition in (I).

A ₂ and B ₂ in the general formula (III) have the same meanings as A ₀ and B ₀ in the general formula (III).
Represents a chalcogen atom or NR ₁₀₁ , and R ₁₀₁ represents a hydrogen atom or a substituent. Examples of the chalcogen atom include oxygen, sulfur, selenium, and tellurium, and preferably oxygen and sulfur. As the substituents represented by R _101, an alkyl group (e.g. methyl, ethyl,
Isopropyl group, hydroxyethyl group, methoxymethyl group, trifluoromethyl group, t-butyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), aralkyl group (eg, benzyl group, 2-phenethyl group, etc.), Aryl group (eg, phenyl group, naphthyl group, p-tolyl group, p-chlorophenyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, isopropoxy group, n-butoxy group, etc.), aryloxy group (eg, phenoxy group) Etc.), a hydroxyl group and the like,
Preferred are an alkyl group and an aryl group.

Further, there is a hydrogen bond donating moiety at the adjacent position where A ₂ on A ₂ and> C = X are bonded, and X is NR
_{When 101} and R ₁₀₁ are a hydrogen atom, they may be hydrogen bond-accepting moieties. The hydrogen bond accepting moiety and the hydrogen bond donating moiety have the same meaning as defined in the general formula (I). or,
When X is NR ₁₀₁ , R ₁₀₁ and either one of A ₂ or B ₂ may be condensed with each other to form a ring, but the ring formed is a pyridine ring, a pyrimidine ring, a pyridazine ring, Examples include a pyrazine ring, a triazine ring, a tetrazine ring, a pyrrole ring, a pyrazole ring, a triazole ring, an imidazole ring, a thiadiazole ring, an oxadiazole ring, a quinoline ring, and an isoquinoline ring.

A ₃ and B ₃ in the general formula (IV) have the same meanings as A ₀ and B ₀ in the general formula (I).
Y and Z in the above represent a carbon atom or a nitrogen atom, which may be the same or different, and when both Y and Z are carbon atoms, one of Y or Z is a substituent capable of forming an intramolecular hydrogen bond. Having a group capable of forming an intramolecular hydrogen bond with a substituent on Y or Z at the adjacent position where -Y = Z- on A ₃ and B ₃ is bonded, The part is
Represents a hydrogen bond-accepting moiety and a hydrogen bond-donating moiety, and the hydrogen bond-accepting moiety and the hydrogen bond-donating moiety have the same meanings as defined in formula (I).

When either Y or Z is a nitrogen atom, it has a hydrogen bond-donating moiety at the adjacent position of -Y = Z- on A ₃ and B ₃ , or Y or have an intramolecular hydrogen bond possible substituents on Z carbon atoms, a ₃
And has a -Y = Z- and substituents and intramolecular hydrogen bond moiety on the carbon atom of Y or Z at the adjacent position bound on B _3, and intramolecular hydrogen-bondable moieties Has the same meaning as defined above.

When both Y and Z are nitrogen atoms, A ₃ or B ₃ has a hydrogen bond-donating moiety at the adjacent position where -Y = Z- is bonded.

When Y and Z are carbon atoms, they may be substituted with a halogen atom or another substituent, and the substituent may be an alkyl group (eg, a methyl group, an ethyl group,
Isopropyl group, hydroxyethyl group, methoxymethyl group, trifluoromethyl group, t-butyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), aralkyl group (eg, benzyl group, 2-phenethyl group, etc.), Aryl group (eg, phenyl group, naphthyl group, p-tolyl group, p-chlorophenyl group, etc.), alkoxy group (eg, methoxy group, ethoxy group, isopropoxy group, n-butoxy group, etc.), aryloxy group (eg, phenoxy group) ), A cyano group, an acylamino group (eg, an acetylamino group, a propionylamino group, etc.), an alkylthio group (eg, a methylthio group, an ethylthio group, n-
Butylthio group, etc.), arylthio group (for example, phenylthio group), sulfonylamino group (for example, methanesulfonylamino group, benzenesulfonylamino group, etc.), ureido group (for example, 3-methylureido group, 3,3-dimethylureido group, 1 , 3-dimethylureido group, etc.), sulfamoylamino group (eg, dimethylsulfamoylamino group), carbamoyl group (eg, methylcarbamoyl group, ethylcarbamoyl group, dimethylcarbamoyl group, etc.), sulfamoyl group (eg, ethylsulfa Moyl group, dimethylsulfamoyl group, etc.), alkoxycarbonyl group (eg, methoxycarbonyl group, ethoxycarbonyl group, etc.), aryloxycarbonyl group (eg, phenoxycarbonyl group, etc.), sulfonyl group (eg, methanesulfonyl group, pig Sulfonyl group, benzenesulfonyl group, etc.), acyl group (eg, acetyl group, propanoyl group, butanoyl group, etc.), amino group (eg, methylamino group, ethylamino group, dimethylamino group, etc.), hydroxyl group, nitro group, imide group (For example, phthalimide group)
And an alkyl group and an aryl group are preferred.

[0045] A _4, B _4, C ₄ in the general formula (V) have the same meanings as defined in formula (I) A _0, B ₀ in, A ₄ is at least 1
One of B ₄ and C ₄ has at least one hydrogen bond-accepting moiety,
When A ₄ has at least one hydrogen bond-accepting moiety, one of B ₄ and C ₄ has at least one hydrogen bond-donating moiety, and the hydrogen bond-accepting moiety and the hydrogen bond-donating moiety are: It has the same definition as in general formula (I).

The specific structures of the compounds represented by formulas (I) to (V) which can be used in the present invention are shown below.

[0047]

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[0050]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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[0065]

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[0070]

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The structures shown above correspond to the general formulas (I) to (V)
Is a typical example of the compound represented by the formula, and the compound used in the present invention is not limited thereto.

The orientation of these compounds of the present invention is fixed by thermal polymerization by heating after or after orientation after film formation. However, the photopolymerization using a photopolymerization initiator or the like may be used for fixing the orientation by polymerization.

The optically anisotropic material of the present invention can be used as an optical compensation film. The optical compensation film is a film for compensating a viewing angle of a liquid crystal display element, and preferably, a director is provided on the upper surface of the film. And the lower surface. More preferably, a hybrid orientation that is gradually changed in the film thickness direction is formed, and no optical axis exists.

In the present invention, as a condition for greatly improving the viewing angle characteristics of the TN type liquid crystal cell, the optical axis is preferably inclined at 5 ° to 50 ° from the normal direction of the film surface, preferably at 10 ° to 40 °. The degree is more preferable. Further the thickness of the film d, if the refractive index n _z in the director alignment obtained when the director of the liquid crystal is brought oriented uniaxially to face one direction perpendicular thereto the direction of refractive indices n _x, n _y The product Δn × d is defined by a retardation value, and the difference between the product and the optical compensation film is usually 50 nm or more and 3000 nm or less, preferably 10 nm or less.
It is not less than 0 nm and not more than 2000 nm.

For compensating the viewing angle, it is more preferable that the absolute value of the product of the birefringence of the liquid crystal and the film thickness is substantially equal between the liquid crystal cell and the optically anisotropic material.

In order to obtain a compensation film in which the hybrid orientation is uniformly fixed by using the compounds represented by the general formulas (I) to (V) as described above, a substrate described below is used.
In the present invention, it is preferable to perform the following steps.

First, the substrate will be described. In order to obtain the hybrid alignment of the present invention, it is desirable to sandwich the upper and lower portions of the liquid crystalline material at different interfaces, or to use an electric field, a field, and the like. The orientation at the upper and lower interfaces becomes the same, and it is difficult to obtain the hybrid orientation of the present invention. As a specific mode, a single substrate and an air interface are used so that the lower interface of the liquid crystal layer is in contact with the substrate and the upper interface is in contact with air. Although the substrate having different interfaces at the top and bottom can be used, it is preferable to use one substrate and the air interface from the viewpoint of the manufacturing process.

The substrate that can be used in the present invention is desirably an anisotropic alignment substrate so that the tilt direction of the liquid crystal (projection of the director onto the alignment substrate) can be defined. The alignment substrate has a function of defining the alignment direction of the compound of the optically anisotropic layer.

The alignment substrate may be formed by rubbing an organic compound (preferably a polymer), obliquely depositing an inorganic compound, forming a layer having microgrooves, or an organic compound (e.g., ω-tricosanoic acid,
It can be provided by a means such as accumulation (LB film) of dioctadecyldimethylammonium chloride, methyl stearylate).

Further, there is known an alignment substrate having an alignment function when an electric field, a magnetic field, or light is applied.

Preferably, the alignment substrate is formed by rubbing a polymer. As the alignment substrate that can be used in the present invention, specifically, those having the following in-plane anisotropy are desirable, and polyimide, polyamideimide, polyamide, polyetherimide, polyetheretherketone, Polyether ketone, polyketone sulfide, polyether sulfone, polysulfone, polyphenylene sulfide, polyphenylene oxide, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyacetal, polycarbonate, polyarylate, acrylic resin, polyvinyl alcohol, polypropylene, cellulose plastics, Plastic film substrates such as epoxy resin and phenolic resin and uniaxially stretched film substrates, aluminum, iron, copper, etc. with slit-shaped grooves on the surface A metal substrate, an alkali glass etched surface in a slit form, borosilicate glass is a glass substrate such as flint glass.

In the present invention, the above-mentioned various substrates obtained by subjecting the above-mentioned substrate to a surface treatment such as a hydrophilic treatment or a hydrophobic treatment may be used.

On the above-mentioned various alignment substrates, the compounds represented by the general formulas (I) to (V) as in the present invention are applied, followed by a uniform alignment step and a fixing step. Coating on a substrate can be performed using a solution in which the material is dissolved in various solvents, or a material in a molten state,
From the viewpoint of the process, solution coating is preferably performed using a solution in which the compounds represented by formulas (I) to (V) are dissolved in a solvent. Hereinafter, the solution coating will be described.

The compounds represented by the general formulas (I) to (V) are dissolved in a solvent to prepare a solution having a predetermined concentration. The solvent at this time depends on the type of the material, but is usually a halogenated hydrocarbon such as chloroform, dichloromethane, carbon tetrachloride, dichloroethane, tetrachloroethane, trichloroethylene, tetrachloroethylene, chlorobenzene, orthodichlorobenzene, phenol, or parachlorophenol. Phenols, benzene, toluene, xylene, methoxybenzene, aromatic hydrocarbons such as 1,2-dimethoxybenzene, acetone, ethyl acetate, t-butyl alcohol, glycerin, ethylene glycol, triethylene glycol, ethylene glycol monomethyl Ether, diethylene glycol dimethyl ether, ethyl cellosolve, butyl cellosolve, 2-pyrrolidone,
N-methyl-2-pyrrolidone, pyridine, triethylamine, dimethylformamide, dimethylacetamide,
Acetonitrile, butyronitrile, carbon disulfide and the like, and a mixed solvent thereof are used.

The concentration of the solution depends on the solubility of the material and ultimately the thickness of the intended optical compensation film, and cannot be unconditionally determined. However, it is usually used in the range of 1 to 60% by mass. Is in the range of 3 to 40% by mass.

[0086] These solutions are then applied onto the above-mentioned alignment substrate. As a coating method, a spin coating method, a roll coating method, a printing method, an immersion pulling method, a curtain coating method (die coating method) and the like can be adopted. After the application, the solvent is removed, and a layer having a uniform thickness is first formed on the substrate. The solvent removal conditions are not particularly limited, as long as the solvent can be substantially removed and the layer of the material does not flow or run down. Usually, the solvent is removed by air drying at room temperature, drying on a hot plate, drying in a drying furnace, or blowing hot or hot air.

The purpose of this coating / drying step is to first uniformly form a layer of the compound represented by any of formulas (I) to (V) on the substrate. I haven't. In order to perform the orientation, it is preferable in the present invention to perform the following heat treatment.

The heat treatment is performed at a temperature equal to or higher than the liquid crystal transition point of the compounds represented by the general formulas (I) to (V). That is, the alignment is performed in the liquid crystal state of the material, or the material is once brought into an isotropic liquid state higher than the temperature range exhibiting a liquid crystal phase, and then the temperature is lowered to a temperature range exhibiting a liquid crystal phase. Usually, the temperature of the heat treatment is in the range of 50 ° C to 300 ° C, and particularly preferably in the range of 80 ° C to 200 ° C.

Although the time required for the liquid crystal to be sufficiently oriented depends on the compounds represented by the general formulas (I) to (V), it cannot be said unconditionally, but it is usually from 5 seconds to 2 hours. And preferably in the range of 10 seconds to 40 minutes, particularly preferably in the range of 20 seconds to 20 minutes. If the time is shorter than 5 seconds, the temperature of the material layer may not reach the predetermined temperature and the orientation may be insufficient. If the time is longer than 2 hours, the productivity may be reduced, which is not preferable.

In the present invention, in the heat treatment step, a magnetic field or an electric field may be used in order to orient the compounds represented by the general formulas (I) to (V). The orientation state obtained in this way is then cooled or polymerized by light or heat or the like to be fixed without impairing the orientation state, thereby obtaining the optical compensation film of the present invention.

In the present invention, the angle in the film thickness direction of the hybrid orientation film can be adjusted to a desired angle by appropriately selecting the compound to be used, the orientation substrate, and the like. Even after the film is once formed, the angle can be adjusted to a desired angle by using a method such as uniformly shaving the film surface or immersing the film surface in a solvent to uniformly dissolve the film surface. The solvent used at this time was the compound used,
It is appropriately selected according to the type of the alignment substrate.

When the optically anisotropic material of the present invention obtained by the above steps is actually disposed in a liquid crystal cell as an optical compensation film, the above-mentioned oriented substrate is peeled off from the film as a mode of use of the film, and compensation is performed. It is possible to use the film alone or to use it as it is formed on an alignment substrate.

When the film is used alone, a method of mechanically peeling the oriented substrate using a roll or the like at the interface with the optical compensation film, a method of peeling by applying ultrasonic waves in a poor solvent, a method of peeling the oriented substrate, Examples thereof include a method of peeling by giving a temperature change using a difference in thermal expansion coefficient with a film, a method of dissolving and removing an alignment substrate itself, or an alignment film on an alignment substrate. Since the releasability depends on the adhesion between the compound represented by any one of the general formulas (I) to (V) and the alignment substrate, a method most suitable for the system should be adopted.

Next, in the case where the optical compensation film is used in a state formed on the alignment substrate, the alignment substrate is transparent and optically isotropic, or when the alignment substrate is a necessary member for the liquid crystal display device. Can be used as it is as a target liquid crystal display element. Further, the optical compensation film of the present invention obtained by aligning and fixing the compounds represented by the general formulas (I) to (V) on the alignment substrate is peeled off from the substrate to form another film more suitable for optical use. It can be used after being transferred onto a substrate.

For example, if an alignment substrate to be used is necessary for obtaining a hybrid alignment mode, but a substrate that has an unfavorable effect on a liquid crystal display device is used, the alignment substrate is immobilized. It can be used after being removed from the later optical compensation film. Specifically, the following method can be used. A substrate suitable for the liquid crystal display element to be incorporated into the target liquid crystal display device and a compensation film on the alignment substrate are attached with an adhesive, and then peeled at the interface between the alignment substrate and the compensation film of the present invention, It is possible to manufacture a liquid crystal display element by transferring the compensation film to a substrate side suitable for a liquid crystal display element.A substrate suitable for a liquid crystal display element used for transfer is only required to have an appropriate flatness. Although not particularly limited, glass and a transparent plastic film having optical isotropy are preferred.
Examples of such a plastic film include polymethacrylate, polystyrene, polycarbonate, polyether sulfone, polyphenylene sulfide, polyarylate, amorphous polyolefin, triacetyl cellulose, and epoxy resin. Among them, polymethyl methacrylate, polycarbonate, polyarylate, triacetylose, polyether sulfone and the like are preferably used.

Even if it is optically anisotropic, if it is necessary for a liquid crystal display device, it can be used as it is. Examples of such a film include a retardation film and a polarizing film obtained by stretching a plastic film such as polycarbonate or polystyrene.

Further, as an example of the second substrate used,
The liquid crystal display cell itself can be mentioned. The liquid crystal display cell uses a glass substrate with two upper and lower electrodes,
If the optical compensation film of the present invention is transferred onto one of the upper and lower or both surfaces of the glass, the incorporation of the optical compensation film has already been achieved. In addition, it is of course possible to manufacture the optical compensation film of the present invention using the glass substrate itself forming the display cell as an alignment substrate. The binder or pressure-sensitive adhesive for adhering the second substrate used for the transfer and the optically anisotropic material of the present invention is not particularly limited as long as it is of optical grade, but may be acrylic, epoxy, ethylene-acetic acid. Vinyl copolymers, rubbers, urethanes, and mixtures thereof can be used. Further, the optical compensation film of the present invention may be provided with a protective layer such as a transparent plastic film for protecting the surface.

The thus obtained optical compensation film of the present invention is incorporated into a liquid crystal display in an arrangement as described below to exhibit an optical compensation effect, that is, a viewing angle compensation, on the liquid crystal display. it can. The optical compensation film is usually used as one or more sheets, but preferably one or two sheets, especially two sheets, can exert a suitable optical compensation effect.

When a plurality of optical compensation films are used, the value obtained by summing the absolute value of the product of the birefringence and the film thickness of each optical compensation film is preferably within the above range. However, the value obtained by multiplying the birefringence and the film thickness does not necessarily need to be completely the same between the liquid crystal cell and the optical compensation film. As compared with the case where no film is incorporated, a remarkable viewing angle compensation effect can be obtained.

The optical compensation film of the present invention is incorporated into a liquid crystal display device under the above-described arrangement conditions. Liquid crystal display elements other than the optical compensation film incorporated in the device, such as a polarizing plate and a driving liquid crystal cell, are not particularly limited, but the arrangement conditions, materials, and the like of each element will be described below.

A liquid crystal cell is obtained by sandwiching a nematic liquid crystal material between two alignment-treated electrode substrates. The electrode substrate is disposed on a glass substrate having an ITO conductive film, a transistor thin film electrode, a diode thin film electrode, and the like, and a rubbing polyimide film, a rubbing polyvinyl alcohol film, or the like is usually used. As the alignment film, an obliquely deposited silicon oxide film or the like can be preferably used.

The optical compensation film of the present invention, when used as one or a plurality of sheets, exerts a remarkable effect in improving the viewing angle of a liquid crystal display. Also, conventional optical films,
For example, it can be used in combination with an optical film having a negative uniaxial refractive index structure, an optical film having a positive uniaxial refractive index structure, or an optical film having a biaxial refractive index structure. . However, the optical compensatory film of the present invention plays a decisive role in compensation, and excellent compensation such as the optical compensatory film of the present invention is obtained no matter how the conventional optical film alone is used in any combination. It is impossible to achieve the effect.

As described above, the liquid crystal display device incorporating the optical compensation film of the present invention can obtain a wide viewing angle which has not been obtained conventionally.

In the conventional liquid crystal cell, the setting range of the parameters of the liquid crystal cell is limited in order to obtain a viewing angle as wide as possible. However, the optical compensatory film of the present invention can easily control the orientation mode, and can almost completely compensate for the orientation mode of any liquid crystal cell. Therefore, the degree of freedom in setting the parameters of the liquid crystal cell is increased, and the optical compensation film of the present invention is highly valuable from the viewpoint of industrial production of the liquid crystal cell.

[0105]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. (Synthesis of Compound (II-4)) In an eggplant flask, 1.25 g of the following compound (VI), 0.77 ml of triethylamine, D
10 ml of ME (dimethoxyethane) was added, and 0.39 ml of methanesulfonic acid chloride was slowly added dropwise at 0 ° C.
The mixture was stirred for 0.5 hours as it was. After returning to room temperature, 0.12 g of 4-dimethylaminopyridine, 5-hydroxy-2-
(4-hydroxy-2-pyridyl) -phenol 0.3
0 g was added and the mixture was stirred for 5 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and then purified using silica gel column chromatography to obtain compound (II-4). The structure is MS,
Confirmed by NMR.

[0106]

Embedded image

(Synthesis of Compound (III-10)) 1.46 g of the following compound (VII), 0.77 ml of triethylamine and 10 ml of DME were added to an eggplant flask, and 0.39 ml of methanesulfonic acid chloride was slowly added dropwise at 0 ° C. Stirred for 0.5 hour. After returning to room temperature, 0.12 g of 4-dimethylaminopyridine, 2,3,4,3 ', 4'-
0.20 g of pentahydroxybenzophenone was added and stirred for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure.
Purify using silica gel column chromatography,
Compound (III-10) was obtained. The structure was confirmed by MS and NMR.

[0108]

Embedded image

(Synthesis of Compound (IV-18)) 1.17 g of the following compound (VIII), 0.77 ml of triethylamine and 10 ml of DME were added to an eggplant flask, and 0.39 ml of methanesulfonic acid chloride was slowly added dropwise at 0 ° C. Stirred for 0.5 hour. After returning to room temperature, 0.12 g of 4-dimethylaminopyridine and 0.37 g of 4,4'-azo-di-resorcinol were added, followed by stirring for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and purified using silica gel column chromatography to obtain compound (IV-18). The structure was confirmed by MS and NMR.

[0110]

Embedded image

(Synthesis of Compound (V-8)) 1.46 g of the following compound (IX) and 0.1 mL of triethylamine were placed in an eggplant-shaped flask.
77 ml and DME (10 ml) were added, and methanesulfonic acid chloride (0.39 ml) was slowly added dropwise at 0 ° C., followed by stirring for 0.5 hour. After returning to room temperature, 0.12 g of 4-dimethylaminopyridine and 0.44 g of 2,5-bis- (2,4-dihydroxyphenyl) -pyrazine were added, and the mixture was stirred for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and purified using silica gel column chromatography to obtain compound (V-8). The structure was confirmed by MS and NMR.

[0112]

Embedded image

Example 1 Optically Anisotropic Material Containing Liquid Crystalline Compound (Preparation of Film (1)) A method for preparing an optically anisotropic material using the composition containing a liquid crystal compound of the present invention and its physical properties will be described below. . 100 μm of polyether sulfone
Thick film (FS-130 manufactured by Sumitomo Bakelite Co., Ltd.)
0, size 100 mm × 100 mm) as a substrate.
A gelatin undercoat layer of 1 μm was provided, and a polyamic acid (SE-7210 manufactured by Nissan Chemical Industries, Ltd.) was formed thereon as an alignment film.
Was applied to form a polyimide film at 180 ° C. This polyimide film was rubbed with a rubbing machine to give an orientation ability. The compound (II-4) synthesized above was dissolved in methyl ethyl ketone, and a 10% by mass liquid was applied by a spin coater at 1000 rpm to form a non-oriented layer.

This was designated as film (1). Next, the film (1) was brought into contact with the metal roller heated to a surface temperature of 120 ° C. for 30 seconds from the support side to orient the film (1), and immediately thereafter, the film (1) was rapidly cooled by contacting the metal roller adjusted to a surface temperature of 20 ° C. for 10 seconds. Thus, an optically anisotropic material of the present invention was obtained. Observation of the sheet under a polarizing microscope revealed that the sheet had a monodomain orientation state. Further, by ellipsometry, the optical axis tilt angle β was 25 degrees and Δn × d = 131 nm. In the measurement, an ellipsometer (AEP-100, manufactured by Shimadzu Corporation) was used in a transmission mode to determine the angle dependence of the retardation, and the optimum refractive index in the three-axis direction and the direction of the optical axis were calculated from the values. (Preparation of film (2)) Film (2) was prepared in the same manner as in preparation of film (1) except that compound (II-4) used in preparation of film (1) was changed to compound (III-10). I got

Next, the film (2) was brought into contact with the metal roller heated to a surface temperature of 120 ° C. from the support side for 30 seconds, and immediately thereafter, the film (2) was brought into contact with the metal roller adjusted to a surface temperature of 20 ° C. for 10 seconds, whereby An optically anisotropic material of the invention was obtained. When observing this sheet with a polarizing microscope,
It was observed that the monodomain was in the orientation state. Further, by ellipsometry, the optical axis tilt angle β was 30 degrees and Δn × d = 127 nm. (Preparation of Film (3)) Film (3) was prepared in the same manner as in preparation of film (1) except that compound (II-4) used in preparation of film (1) was changed to compound (IV-18).
I got

Next, the film (3) was brought into contact with the metal roller heated to a surface temperature of 100 ° C. from the support side for 30 seconds, and immediately thereafter, brought into contact with the metal roller adjusted to a surface temperature of 20 ° C. for 10 seconds, whereby An optically anisotropic material of the invention was obtained. When observing this sheet with a polarizing microscope,
It was observed that the monodomain was in the orientation state. Further, by ellipsometry, the optical axis tilt angle β was 20 degrees and Δn × d = 137 nm. (Preparation of film (4)) Except that the compound (II-4) used in the preparation of the film (1) was changed to the compound (V-8), the same operation as in the preparation of the film (1) was carried out. I got

Next, the film (4) was brought into contact with the metal roller heated to the surface temperature of 110 ° C. from the support side for 30 seconds, and immediately thereafter, the film (4) was brought into contact with the metal roller adjusted to the surface temperature of 20 ° C. for 10 seconds. An optically anisotropic material of the invention was obtained. When observing this sheet with a polarizing microscope,
It was observed that the monodomain was in the orientation state. Further, by ellipsometry, the optical axis tilt angle β was 15 degrees and Δn × d = 145 nm.

Example 2 Evaluation of Performance of TN-Type Liquid Crystal Display for Enlarging Viewing Angle (Production of Liquid Crystal Display Provided with Film (A)) TAC
127μm thick film (size 100mm × 100m
m) was used as a substrate, a 0.1 μm gelatin undercoat layer was provided thereon, a modified Poval was applied thereon as an alignment film, and this film was rubbed with a rubbing machine to give alignment ability.
Compound (II-4) is dissolved in methyl ethyl ketone,
A mass% liquid was applied at 1000 rpm by a spin coater. Next, the film was brought into contact with the metal roller heated to a surface temperature of 120 ° C. from the support side for 30 seconds.
By contacting for 2 seconds, an optically anisotropic material film (A) of the present invention was obtained. Next, the above film (A) is applied to a TN type liquid crystal cell having a product of the difference between the refractive indexes of the extraordinary light and the normal light and the gap size of the liquid crystal cell of 440 nm and a twist angle of 90 degrees.
And the angle dependence of the contrast in a 0.5 V, 30 MHz rectangular wave with respect to the liquid crystal cell was measured by Otsuka Electronics LC
It was measured by D-5000. The position of the contrast 10 was defined as the viewing angle, and the up, down, left, and right viewing angles were determined.

Further, a liquid crystal display device was manufactured by changing the compounds as shown below. (Preparation of liquid crystal display device provided with film (B)) Compound (II-20) was used in place of compound (II-4) used in preparing a liquid crystal display device provided with film (A), and the surface temperature of a metal roller was changed. Was changed to 90 ° C., a film (B) was prepared in the same manner, and a liquid crystal display device was similarly prepared using the film (B). Otsuka Electronics LCD-
The measurement was performed according to 5000, and the vertical, horizontal, and horizontal viewing angles were obtained. (Preparation of liquid crystal display device provided with film (C)) The same operation was performed except that compound (II-4) used in preparation of the liquid crystal display device provided with film (A) was changed to compound (II-31). To prepare a liquid crystal display device in the same manner as above.
The angle dependence of the contrast in the square wave of Hz was measured by LCD-5000 manufactured by Otsuka Electronics Co., Ltd., and the vertical, horizontal, and vertical viewing angles were obtained. (Preparation of Liquid Crystal Display Device Provided with Film (D)) The compound (II-4) used in preparation of the liquid crystal display device provided with the film (A) was replaced with the compound (II-44), and the surface temperature of the metal roller was changed. Was changed to 110 ° C., a film (D) was prepared in the same manner, and a liquid crystal display device was similarly prepared using the film (D). Dependency on Otsuka Electronics LC
It measured by D-5000, and calculated | required the up-down and right-and-left viewing angles. (Preparation of Liquid Crystal Display Element Provided with Film (E)) The same procedure was repeated except that the compound (II-4) used in the preparation of the liquid crystal display element provided with the film (A) was replaced with the compound (III-10). A film (E) was prepared by the operation, and a liquid crystal display device was similarly prepared using the film (E).
The angle dependence of the contrast in a 30 Hz rectangular wave was measured by LCD-5000 manufactured by Otsuka Electronics Co., Ltd., and the vertical, horizontal, and horizontal viewing angles were obtained. (Preparation of Liquid Crystal Display Device Provided with Film (F)) The compound (II-4) used in preparation of the liquid crystal display device provided with the film (A) was replaced with the compound (III-17), and the surface temperature of the metal roller was changed. Was changed to 100 ° C., a film (F) was produced in the same manner, and a liquid crystal display device was produced in the same manner using the film (F). Dependency on Otsuka Electronics L
The measurement was performed using CD-5000, and the vertical, horizontal, and vertical viewing angles were obtained. (Preparation of Liquid Crystal Display Device Provided with Film (G)) The same procedure was repeated except that the compound (II-4) used in preparing the liquid crystal display device provided with the film (A) was replaced with the compound (IV-7). A film (G) was prepared by the operation, and a liquid crystal display element was similarly prepared using the film (G).
The angle dependence of the contrast in the square wave of Hz was measured by LCD-5000 manufactured by Otsuka Electronics Co., Ltd., and the vertical, horizontal, and vertical viewing angles were obtained. (Preparation of liquid crystal display device provided with film (H)) Compound (II-4) used in preparation of the liquid crystal display device provided with film (A) was changed to compound (IV-19), and the surface temperature of the metal roller was changed. Was changed to 100 ° C., a film (H) was produced in the same manner, and a liquid crystal display device was produced in the same manner using the film (H). Dependency on Otsuka Electronics LC
It measured by D-5000, and calculated | required the up-down and right-and-left viewing angles. (Preparation of Liquid Crystal Display Device Provided with Film (I)) The compound (II-4) used in preparation of the liquid crystal display device provided with the film (A) was replaced with the compound (V-8), and the surface temperature was changed to 1
A film (I) was prepared by the same operation except that the temperature was changed to 10 ° C., and a liquid crystal display device was similarly prepared using the film (I). The properties were measured by LCD-5000 manufactured by Otsuka Electronics Co., Ltd., and the vertical, horizontal, and horizontal viewing angles were determined. (Preparation of Liquid Crystal Display Device Provided with Film (J)) The compound (II-4) used in preparation of the liquid crystal display device provided with the film (A) was changed to the compound (V-23), and the surface temperature was changed to 105. Film (J) by the same operation except that the temperature was changed to ° C.
And a liquid crystal display element is similarly manufactured using the
The angle dependence of the contrast at a rectangular wave of 0.5 V and 30 Hz with respect to the liquid crystal cell was measured by Otsuka Electronics LCD-5000.
And the vertical and horizontal viewing angles were determined.

The following table shows the upper, lower, left and right viewing angles of a liquid crystal display device using the films (A) to (J) as viewing angle compensation films and, for comparison, a liquid crystal display device not using an optical compensation film. (Unit is degree)

[0121]

[Table 1]

From the table, the films (A), (B),
(C), (D), (E), (F), (G), (H),
It is clear that the liquid crystal display devices provided with (I) and (J) show excellent viewing angle compensation as compared with the comparative example in which no optical compensation film was used.

[0123]

According to the present invention, a material having optical anisotropy can be provided, whereby an optical compensation film capable of increasing the viewing angle of a liquid crystal display can be obtained. A liquid crystal display element having a wide viewing angle can be obtained.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme court ゛ (Reference) C07D 213/64 C07D 213/64 4C063 213/65 213/65 4C069 213/68 213/68 4H006 213/69 213 / 69 4H027 213/70 213/70 233/70 233/70 237/08 237/08 241/12 241/12 303/24 303/24 487/04 137 487/04 137 C09K 19/38 C09K 19/38 G02B 5/30 G02B 5/30 G02F 1/13363 G02F 1/13363 // C07D 207/333 C07D 207/333 401/04 401/04 401/06 401/06 405/12 405/12 405/14 405/14 F Terms (Reference) 2H049 BA06 BA42 BB43 BB44 BB45 BB48 BB49 BC04 BC05 BC06 BC22 2H091 FA11X FA11Z FB02 LA19 4C048 AA01 BB08 BB09 CC02 CC03 UU10 XX01 4C050 AA01 BB04 CA04 BA04 CA03 BA03CA03 BA02CA03 DA01 DA06 DA43 DB 04 DB08 EA01 4C063 AA01 AA03 BB01 BB08 CC71 DD04 DD11 DD25 DD28 DD34 EE10 4C069 AC07 4H006 AA03 AB64 BJ50 BN30 BP10 BP30 BR60 BS10 KD10 4H027 BA11 BD21 BE04 BE06 CB03 CH03 DA03 DB03 DC03 DD03 DE03

Claims (12)

[Claims] 1. A compound having at least two aromatic groups or aromatic heterocyclic groups at arbitrary positions in a molecule and containing at least one compound having a moiety capable of hydrogen bonding in the molecule. Optically anisotropic material. 2. An optically anisotropic material comprising at least one compound represented by the general formula (I). Formula (I) A ₀ -B ₀ (where A ₀ and B ₀ represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and at least one hydrogen bond-donating moiety and at least one Has one hydrogen bond-accepting moiety.) 3. An optically anisotropic material comprising at least one compound represented by the general formula (II). General formula (II) A ₁ -B ₁ (wherein A ₁ and B ₁ represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and A ₁ has at least one hydrogen bond-donating moiety. And B ₁ has at least one hydrogen bond-accepting moiety.) 4. An optically anisotropic material comprising at least one compound represented by the general formula (III). Embedded image (Wherein, A ₂ and B ₂ represents an aromatic group or an aromatic heterocyclic group 5-6 membered, X represents a chalcogen atom or NR _101, R ₁₀₁ is .A ₂ represents a hydrogen atom or a substituent having a hydrogen bond donor moiety in the position adjacent a ₂ and> C = X is attached above. However, X is at NR _101, and when R ₁₀₁ is a hydrogen atom may be a hydrogen bond acceptor moiety , And X is NR
_In the case of ₁₀₁ , R ₁₀₁ and either one of A ₂ or B ₂ may be fused to each other to form a ring. ) 5. An optically anisotropic material containing at least one compound represented by the general formula (IV). General formula (IV) A ₃ —Y = Z—B ₃ (wherein A ₃ and B ₃ represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and Y and Z represent a carbon atom or a nitrogen atom. When both Y and Z are carbon atoms, one of Y and Z has a substituent capable of hydrogen bonding in the molecule, and -Y = Z- on A ₃ and B ₃ is bonded. Has a moiety capable of intramolecular hydrogen bonding with the substituent on Y or Z. When both Y and Z are nitrogen atoms, -Y = Z- on A ₃ and B ₃ is bonded It has a hydrogen bond donating moiety at an adjacent position.
Further, when either Y or Z is a nitrogen atom, it has a hydrogen bond-donating moiety at the adjacent position where -Y = Z- on A ₃ and B ₃ is bonded, or A substituent on the carbon atom of Y or Z and a hydrogen atom on the carbon atom having a substituent capable of forming an intramolecular hydrogen bond on the carbon atom, and a substituent on the carbon atom of Y or Z adjacent to -Y = Z- on A ₃ and B ₃ It has a bondable part. ) 6. An optically anisotropic material containing at least one compound represented by the general formula (V). General formula (V) A ₄ -B ₄ -C ₄ (where A ₄ , B ₄ and C ₄ represent a 5- to 6-membered aromatic group or an aromatic heterocyclic group, and A ₄ is at least one hydrogen atom When having a bond donating moiety, one of B ₄ and C ₄ has at least one hydrogen bond accepting moiety, and when A ₄ has at least one hydrogen bond accepting moiety, B ₄ ,
Either a C ₄ has at least one hydrogen bond donor moiety. ) 7. An optical compensation film comprising at least one compound represented by the general formula (I). 8. An optical compensation film comprising at least one compound represented by the general formula (II). 9. An optical compensation film comprising at least one compound represented by the general formula (III). 10. An optical compensation film comprising at least one compound represented by the general formula (IV). 11. An optical compensation film comprising at least one compound represented by the general formula (V). 12. A liquid crystal display device incorporating at least one optically anisotropic material according to claim 2.