JPH09104656A - Liquid crystal composition and optically anisotropic material comprising the same and compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a discotic liquid crystal composition low in a liquid crystal phase transfer temperature, capable of fixing the molecular arrangement in the liquid crystal phase and useful as a liquid crystal material. SOLUTION: This liquid crystal composition comprises a discotic liquid crystalline compound of formula I (R is a group of formula II; R<21> , R<22> are each H, methyl; R<23> is an alkoxy containing P2 which is the substituent of a compound of formula III; R<24> , R<25> , R<26> are each H, an alkyl) and a non-discotic liquid crystalline compound having at least one kind of the same substituent. The liquid crystal composition can easily be coated in a wet state and subsequently heated at a relatively low a temperature to form an oriented thin film having an optical anisotropicity of monodomain on a general oriented liquid crystal film. The optical anisotropicity of the thin film can be fixed by the application of light or heat energy. The employment of the thin film with a liquid crystal display element enables to improve the angle of visibility as a phase difference film. The mixing ratio of the discotic liquid crystal compound to the non-discotic liquid crystal compound is 50-100wt.% as the content of the discotic liquid crystal compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a liquid crystal composition useful as a liquid crystal material, an optically anisotropic material comprising the same, and a retardation film for a liquid crystal display device.

[0002]

2. Description of the Related Art In recent years, liquid crystal display devices have been widely used in word processors, personal computers, televisions, etc., and industrial activities related to materials, devices and the like have been actively carried out. Liquid crystal compounds, which are the basis of liquid crystal display materials, have been actively researched and developed, and many compounds have been developed. It is considered that these compounds are used not only for display devices but also for development of various applications. In addition to the rod-shaped liquid crystal compounds that are well known and widely used in the past, disk-shaped liquid crystal compounds, so-called discotic liquid crystal compounds, have recently been drawing attention.

A typical discotic liquid crystal compound is C.I. Destrade et al., Mol.Cryst.Liq.
Cryst. 71, 111 (1981), edited by The Chemical Society of Japan, Quarterly Chemistry Review No. 22, Liquid Crystal Chemistry, Chapter 5,
Chapter 10 verse 2 (published in 1994) B. Report of Kohne et al., Angew. Chem. 96, 70, 1984.
J. M. Lehn et al., J. Chem.Soc.Chem.Commu
n., p. 1794 (1985) and J. Zhang, J .; S. M
Oore et al., J. Am. Chem.Soc., Vol 116,
Various derivatives described on page 2655 (1994) can be mentioned. To further explain, from a central portion having a disk-like shape, for example, a benzene ring, a cyclohexane ring, a triphenylene ring, a truxene ring, a coronene ring, a phthalocyanine ring, an azacrown ring, an acetylene macrocycle ring, a β-diketone metal complex. It is a compound having a structure in which a plurality of mutually identical or different side chain portions are radially extended.

Examples of the side chain portion include alkanoyloxy groups (eg, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy), alkylsulfonyl groups (eg, hexylsulfonyl, heptyl). Sulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl), alkylthio group (eg, hexylthio, heptylthio, octylthio, nonylthio, decylthio, undecylthio, dodecylthio), alkoxy group (eg, butoxy, pentyloxy, hexyloxy, heptyl) Oxy, octyloxy, nonyloxy, decyloxy, undecyloxy), 2- (4-alkylphenyl) ethynyl group (for example, as an alkyl group Tyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl), terminal vinylalkoxy group (for example, 4-vinylbutoxy, 5-vinylpentyloxy, 6-vinylhexyloxy, 7-vinylheptyloxy, 8- Vinyloctyloxy, 9-vinylnonyloxy), 4-alkoxyphenyl group (for example, the alkoxy group mentioned above in the alkoxy group), alkoxymethyl group (for example, the alkoxy group mentioned above in the alkoxy group). An alkylthiomethyl group (for example, the alkylthio group mentioned above in the alkylthio group), a 2-alkylthioethoxymethyl group (for example, an alkylthio group mentioned above in the alkylthio group), a 2-alkoxyethoxymethyl group (for example With an alkoxy group And the above-mentioned alkoxy groups), 2-alkoxycarbonylethyl groups (for example, the alkoxy groups mentioned above as the alkoxy groups), cholesteryloxycarbonyl, β-sitosteryloxycarbonyl, 4-alkoxyphenoxycarbonyl. Group (for example, an alkoxy group mentioned above as an alkoxy group), 4-alkoxybenzoyloxy group (for example an alkoxy group mentioned above as an alkoxy group), 4-alkylbenzoyloxy group (for example as an alkyl group) , The above 2-
(4-alkylphenyl) ethynyl group),
4-alkoxybenzoyl groups (for example, the alkoxy groups mentioned above as the alkoxy groups), and those in which the above-mentioned benzoyl group is replaced with a cinnamoyl group can be mentioned.

Of the above, the phenyl group is another aryl group (for example, naphthyl group, phenanthryl group,
Anthracenyl group), or may be further substituted in addition to the above-mentioned substituents. Further, the phenyl group is a heteroaromatic 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, thiadiazolyl group, oxadiazolyl group. Group, quinolyl group, isoquinolyl group).

The discotic liquid crystal phase is a columnar phase (colu) in which the central cores of discotic molecules are stacked in columnar form by intermolecular force.
It is known that it can be roughly divided into a mnar phase), a discotic nematic phase in which discotic molecules are randomly aggregated, and a chiral discotic nematic phase. However, W. H. Physical properties of liqui by de jeu
d crystalline materials (1980 by Gordon and
As described in Breach, Science Publishers), columnar phases are often found, but discotic nematic phases are rarely found.

Although the discotic liquid crystal has been attracting attention as a conductive material, it has some interesting optical characteristics. The fact that the triphenylene-based discotic liquid crystal of the present invention has a negative birefringence means that B. Report of Mourey et al. [Mol. Cryst. Liq. Cryst., 84, 193 (1982)
)], In order to apply this property as an optical compensation sheet, it is necessary to statistically arrange all the molecules constituting the thin film in one direction at room temperature. Moreover, the discotic liquid crystal is composed of an alignment region (domain) having a specific directionality microscopically, and does not show optical anisotropy macroscopically, like the liquid crystal composed of conventional rod-shaped molecules. Due to the property of forming a so-called multi-domain, the thin film often does not exhibit favorable optical properties that can be used for an optical compensation sheet.

By the way, as is known in a rod-shaped compound, which is a typical structure of liquid crystal, the formed liquid crystal phase and the transition temperature between the phases often remarkably change due to the subtle difference in the structure. This is not limited to the rod-shaped liquid crystal compound, and the same applies to the discotic liquid crystal compound. It is known that such a change in the phase transition temperature is caused also by mixing of compounds, and therefore the discovery of an excellent mixture is as important as the discovery of a new compound. The required liquid crystal phase and the transition temperature between each phase differ depending on the intended device, and therefore the range of selection can be expanded only by preparing a wide variety of compounds, and it becomes possible to meet various purposes. Become. Further, it is very important from a practical point of view to provide a compound obtained by introducing a polymerizable functional group into the molecule in order to fix the necessary molecular alignment obtained in the liquid crystal phase. .

However, many discotic liquid crystal compounds have not yet been known, and little is known about excellent mixtures. This is the same for the triphenylene derivative which is a particularly attractive compound. Destrade et al.,
J. Phsique, Vol. 40, No. 4, C3-17 (1979) and C.I. Vauchier et al., Mol. Cryst. Liq. Cryst. 66
Vol. 103, p. 103 (1981), only a few examples are mentioned, and the discovery of more useful mixtures is desired.

[0010]

Therefore, the object of the present invention is to exhibit a discotic liquid crystallinity useful as a liquid crystal material, to have a low transition temperature of the liquid crystal phase, and to fix a desired molecular arrangement obtained in the liquid crystal phase. Another object of the present invention is to provide a novel liquid crystal composition that can be used, and further to provide an optically anisotropic material comprising them and a retardation film for a liquid crystal display device using them.

[0011]

As a result of intensive studies, the present inventors have found that the object of the present invention can be achieved by the following liquid crystal composition. (1) A discotic liquid crystal compound having a substituent capable of forming a new bond between at least one kind of molecule or intramolecularly, and a substitution capable of forming a new bond between at least one kind of molecule or intramolecularly A liquid crystal composition comprising a monocyclic or fused-ring aromatic compound having a non-discotic liquid crystal group. (2) The substituent capable of forming a new bond intermolecularly or intramolecularly is a polymerizable substituent
The liquid crystal composition according to item (1). (3) The discotic liquid crystalline compound is represented by the following general formula (1), wherein (1) or
The liquid crystal composition according to item (2). General formula (1)

[0012]

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In the formula, R ²¹ and R ²² each independently represent a hydrogen atom or a methyl group, and R ²³ represents an alkoxy group containing the substituent P2. R ²⁴ , R ²⁵ and R ²⁶ of the substituent P2 each independently represent a hydrogen atom or an alkyl group. (4) The liquid crystal composition according to item (1) or (2), wherein the compound having no discotic liquid crystallinity is represented by the following general formula (2). General formula (2)

[0014]

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In the formula, D1 represents a benzene ring or a naphthalene ring, and a total of n substituents A and substituents [(L1) _s-
P4]-is arranged. The k L1 and P4 are each independently, and the (n−k) A is independently a hydrogen atom, an alkyl group or an alkoxy group. n is 6 when D1 is a benzene ring and 8 when it is a naphthalene ring, and k represents an integer of 1 to 3. s and t represent 0 or 1. X1 represents an alkyleneoxy group. R ⁴¹ and R ⁴² each independently represent a hydrogen atom or a methyl group, and R ⁴⁴ , R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom or an alkyl group. R ⁴³ has the same meaning as P 4. (5) The compound not having discotic liquid crystallinity is a compound represented by the general formula (2),
The liquid crystal composition according to item (3). Compounds represented by the general formulas (3) and (4) are particularly useful as the non-discotic liquid crystal compound. General formula (3)

[0016]

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In the formula, D4 represents a benzene ring or a naphthalene ring, and has a total of n substituents Q and substituents (L4-P7).
Represents a group in which-is arranged. The k L4s and P7s are each independently, and the (nk) Qs each independently represent a hydrogen atom, an alkyl group or an alkoxy group. n is 6 when D4 is a benzene ring and 8 when it is a naphthalene ring, and k is 3 when D4 is a benzene ring and 2 when D4 is a naphthalene ring. However, the 2,6-di-substituted form of naphthalene is excluded. X4 represents an alkyleneoxy group. R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R
⁷⁵ and R ⁷⁶ are R ⁴¹ , R ⁴² , R ⁴³ of the general formula (2),
It is synonymous with R ⁴⁴ , R ⁴⁵ and R ⁴⁶ . General formula (4)

[0018]

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In the formula, L5 represents an alkylene group. R
⁸⁴ , R ⁸⁵ and R ⁸⁶ each independently represent a hydrogen atom or an alkyl group.

Further, the liquid crystal composition according to (1), the liquid crystal composition according to (2), the liquid crystal composition according to (3), the liquid crystal composition according to (4) or the above.
By using the liquid crystal composition according to (5), the layer necessary for forming a new bond according to (1) above is further added to the layer formed of the liquid crystal composition on the support. This makes it possible to obtain a novel optically anisotropic material, preferably by polymerization, and this optically anisotropic material has made it possible to realize a retardation film for a liquid crystal display device. It should be noted that the compound used in the present invention does not matter even if the hydrogen atom in the compound is a deuterium atom.

[0021]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail. The substituent capable of forming a new bond intermolecularly or intramolecularly of the present invention may be either a group capable of forming a bond between the same kind of functional groups or a group capable of forming a bond between different kinds of functional groups, preferably polymerized. The resulting substituent. For example, R. Sandler and W. Kalaw (SR Sandle
r, W. Karo), Organic Functional Group Preparations (Oragnic Functional Group)
Preparations) and the substituents described in Volumes 1 and 2 (Academic Press, New York, London, 1968). Among them, a multiple bond (the constituent atom may be a carbon atom or a non-carbon atom) and a hetero-membered ring such as oxirane or aziridine, more preferably R.I. A. M. Hikm
et al.'s research report [Macromolecules, 25, 4194 (1992)] and [Polymer, 34, No. 8, 173].
6 (1993)], D.I. J. Broer et al. [Macromolecules, 26, 1244 (1993)
)], Double bonds, ie acryloyl groups, vinyloxy groups and epoxy groups.

The discotic liquid crystal compound of the present invention has been described in the section of the prior art, but will be described again. The discotic liquid crystal compound is characterized by having a discotic molecular portion in its mother nucleus. The disk-shaped morphological characteristics of the mother nucleus portion excluding the side chain portion can be expressed as follows for the hydrogen-substituted compound which is the original compound thereof. First, the size of the molecule is determined as follows. 1) Construct a nearly planar, preferably planar, molecular structure for the molecule. In this case, it is preferable to use standard values for the bond distance and bond angle according to the mixture of the orbitals.
Reference can be made to Chapter 15 of Part II Volume II (Maruzen, 1993). 2) Using the structure obtained in 1) as an initial value, the structure is optimized by the molecular orbital method or the molecular force field method. As the method, for example, Gaussian92, MOPAC93, CHAR
Mm / QUANTA, MM3, and preferably G
aussian92. 3) Give each structure-optimized atom a sphere defined by the van der Waals radius, and describe the shape of the molecule. 4) Let a, b, and c be the three edges of the rectangular parallelepiped that can accommodate the molecular portion having the shape obtained in 3) above. In order to reduce the arbitrariness further, it is preferable to perform the above 3) and the following as follows. 3 ′) The center of gravity of the structure obtained by the structure optimization is moved to the origin, and the coordinate axes are set to the principal axes of inertia (inertia tensor ellipse). The main axis of the body). 4 ') Give each atom a sphere defined by the van der Waals radius, and describe the shape of the molecule. 5 ') The lengths in the respective coordinate axis directions are measured on the van der Waals surface, and these are designated as a, b, and c, respectively. If a disk-shaped form is defined using a, b, and c obtained by the above procedure, a ≧ b> c and a ≧ b ≧ a /
2, preferably a ≧ b> c and a ≧ b ≧ 0.7a. Further, it is preferable that b / 2> c. Specific examples of the compound include derivatives of the mother nucleus compound described in the above-mentioned document. For example,
Benzene derivatives, triphenylene derivatives, truxene derivatives, phthalocyanine derivatives, porphyrin derivatives, anthracene derivatives, azacrown derivatives, cyclohexane derivatives, β-diketone metal complex derivatives, and phenylacetylene macrocycles. Review No.15 New Aromatic Chemistry ”
(The University of Tokyo Press, 1977) and cyclic compounds and their heteroatom-substituted electronic structures. Further, as in the case of the above-described metal complex, an assembly of a plurality of molecules may be formed by hydrogen bonding, coordination bond, or the like to form a disk-shaped molecule. A discotic liquid crystal compound is formed by a structure in which a linear alkyl group, an alkoxy group, a substituted benzoyloxy group or the like is radially substituted as a side chain with these as the central nucleus of the molecule.
The mother nucleus compound preferably forms a discotic nematic (N _D ) phase, and particularly preferably triphenylene and truxene. Examples of the side chain include an alkyl group, an alkoxy group, an alkylthio group and an acyloxy group, and the side chain may contain an aryl group or a heterocyclic group. In addition, C.I. Hans
ch, A. Leo, R.A. W. Taft, Chemical Review Magazine (Chem. Rev.), 1991, 91, 1
It may be substituted with the substituents described on pages 65-195 (American Chemical Society), and representative 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 portion include an alkanoyloxy group (eg, hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy), an alkylsulfonyl group (eg, hexylsulfonyl, heptyl). Sulfonyl, octylsulfonyl, nonylsulfonyl, decylsulfonyl, undecylsulfonyl), alkylthio groups (eg, hexylthio, heptylthio, dodecylthio), alkoxy groups (eg, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy) , Undecyloxy), 2- (4-alkylphenyl) ethynyl group (for example, methyl, ethyl, propyl, butyl, pentyl, hexyl as an alkyl group, Butyl, octyl, nonyl), a terminal vinylalkoxy group (for example, 4-vinylbutoxy, 5-vinylpentyloxy, 6-vinylhexyloxy, 7-vinylheptyloxy, 8-vinyloctyloxy, 9-vinylnonyloxy), 4-alkoxyphenyl group (for example, the alkoxy group mentioned above in the alkoxy group), alkoxymethyl group (for example, the alkoxy group mentioned above in the alkoxy group), alkylthiomethyl group (for example, the alkylthio group mentioned above) Of the above-mentioned alkylthio group), 2-alkylthiomethyl (for example, the alkylthio group mentioned above for the alkylthio group), 2-alkylthioethyloxymethyl (for example, the alkylthio group mentioned above for the alkylthio group) , 2-alkoxyeth Cimethyl group (for example, the alkoxy group mentioned above as the alkoxy group), 2-alkoxycarbonylethyl group (for example, the alkoxy group mentioned above as the alkoxy group), cholesteryloxycarbonyl, β-sitosteryloxycarbonyl , 4-alkoxyphenoxycarbonyl group (for example, the alkoxy group mentioned above in the alkoxy group), 4-alkoxybenzoyloxy group (for example, the alkoxy group mentioned above in the alkoxy group), 4-alkylbenzoyloxy Examples thereof include a group (for example, the alkyl group mentioned above in the 2- (4-alkylphenyl) ethynyl group) and a 4-alkoxybenzoyl group (for example, an alkoxy group mentioned above in the alkoxy group).

Of the above-mentioned groups, the phenyl group may be another aryl group (for example, naphthyl group, phenanthryl group, anthracenyl group), or may be further substituted in addition to the above-mentioned substituents. Further, the phenyl group is a heteroaromatic ring (for example, pyridyl group, pyrimidyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, thiazolyl group, imidazolyl group, oxazolyl group, thiadiazolyl group. , Oxadiazolyl group, quinolyl group, isoquinolyl group). Examples of the monocyclic or condensed ring aromatic compound of the present invention include a benzene ring, a naphthalene ring,
The thing which has an anthracene ring, a phenanthrene ring, and a pyrene ring is mentioned. Of these, those having a benzene ring and a naphthalene ring are preferable.

Therefore, the discotic liquid crystalline compound in the present invention is preferably the compounds represented by the following general formulas (5) and (6) in addition to the compounds represented by the general formula (1). The six R's in these general formulas may be the same or different.
Further, as the compound not having discotic liquid crystallinity, a compound having a group capable of forming a new bond, preferably one having two or more polymerizable substituents, is preferable, and more preferably,
In addition to the compound represented by the general formula (2), there are compounds represented by the following general formulas (7) and (8).
A particularly preferred compound in the former is a compound represented by the general formula (1), and a particularly preferred compound in the latter is a compound represented by the general formula (2). General formula (5)

[0026]

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In the formula, R ¹¹ and R ¹² each independently represent a hydrogen atom or a methyl group, and R ¹³ represents an alkoxy group containing the above substituent P1. R ¹⁴ , R ¹⁵ , and R ¹⁶ of the substituent P1 each independently represent a hydrogen atom or an alkyl group. n represents 0 or 1. General formula (6)

[0028]

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In the formula, R ³¹ and R ³² each independently represent a hydrogen atom or a methyl group, and R ³³ represents an alkoxy group containing the substituent P3. R ³⁴ , R ³⁵ and R ³⁶ of the substituent P3 each independently represent a hydrogen atom or an alkyl group. General formula (7)

[0030]

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In the formula, D2 represents a benzene ring or a naphthalene ring, and a total of n substituents B and substituents [(L2) _s-
P5]-is arranged. The k L2 and P5 are each independently, and the (nk) B's each independently represent a hydrogen atom, an alkyl group or an alkoxy group. n is 6 when D2 is a benzene ring, is 8 when it is a naphthalene ring, and l is 0 or 1. k represents an integer of 1 to 3. s and t represent 0 or 1. X2 represents an alkyleneoxy group.
R ⁵¹ and R ⁵² each independently represent a hydrogen atom or a methyl group, and R ⁵⁴ , R ⁵⁵ and R ⁵⁶ each independently represent a hydrogen atom or an alkyl group. ^R53 has the same meaning as P5. General formula (8)

[0032]

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In the formula, D3 represents a benzene ring or a naphthalene ring, and a total of n substituents C and substituents [(L3) _s-
P6] -represents a group. The k L3 and P6 are each independently, and the (nk) C's each independently represent a hydrogen atom, an alkyl group or an alkoxy group. n is 6 when D3 is a benzene ring, is 8 when it is a naphthalene ring, and k is an integer of 1 to 3. s and t represent 0 or 1. X3 represents an alkyleneoxy group. R ⁶¹ and R ⁶² each independently represent a hydrogen atom or a methyl group, and R ⁶⁴ , R ⁶⁵ and R ⁶⁶ each independently represent a hydrogen atom or an alkyl group. R ⁶³ is P6
Is synonymous with

The general formula of the present invention will be described in detail below.
explain. In the general formula (5), R¹¹, R¹²Are each
It independently represents a hydrogen atom or a methyl group. When n is 0,
Substituent P1 represents an unsaturated double bond group. The substituent R
¹⁴, R ^FifteenAre each independently a hydrogen atom, an alkyl group (for example,
Methyl, ethyl, n-propyl, isopropyl, n-butyl
Chill, pentyl, hexyl, heptyl, octyl, noni
And lower alkyl groups such as methyl and ethyl are
Methyl is more preferable. ) And R¹⁴But
R at the methyl group^FifteenIs a hydrogen atom or R¹⁴, R^FifteenBut water together
A combination of elementary atoms is preferred.

The substituent R ¹⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. Methyl is preferred. ), A hydrogen atom and a lower alkyl group are preferred, and a hydrogen atom is more preferred.

The alkoxy residue formed by substituting the terminal substituent P1 is an alkyleneoxy group (for example, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy, etc. It represents a substituted alkyleneoxy group containing an ether bond such as ethyleneoxyethoxy). However, the terminal substituent P1 may be directly bonded to the aromatic ring.

When n is 1, the terminal substituent P1 of R ¹³ represents a so-called vinyl ether group. The substituents R ¹⁴ and R ¹⁵ of the substituent P1 are each independently a hydrogen atom or an alkyl group (eg methyl group). , Ethyl, n-propyl, isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, lower alkyl groups such as methyl and ethyl are preferred, and methyl is more preferred), and R ¹⁴ is methyl. R ¹⁵ is a hydrogen atom, or R ¹⁴ , R
A combination of ¹⁵ is preferably a hydrogen atom.

The substituent R ¹⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. Methyl is preferred. ), A hydrogen atom and a lower alkyl group are preferred, and a hydrogen atom is more preferred.
Therefore, as the substituent P1, an unsubstituted vinyloxy group which is a functional group having a high polymerization activity is generally preferably used.

The alkoxy residue formed by substituting the terminal substituent P1 is an alkyleneoxy group (eg ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy), an alkyleneoxy-substituted alkoxy group (eg 2-ethyleneoxyethoxy).

Specific examples TP-1 to TP-50 of the compound of the present invention represented by the general formula (5) are shown below (the general formula and the substituents thereof are shown in the table). There is no limitation.

[0041]

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[0042]

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In the general formula (1), R ²¹ and R ²² each independently represent a hydrogen atom or a methyl group. The terminal substituent P2 of R ²³ represents a so-called acryloyloxy group. The substituents R ²⁴ and R ²⁵ of the substituent P2 are each independently a hydrogen atom, an alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, pentyl, hexyl,
Examples include heptyl, octyl and nonyl, lower alkyl groups such as methyl and ethyl are preferred, and methyl is more preferred. ) Wherein R ²⁴ is methyl and R ²⁵ is a hydrogen atom, or a combination of both R ²⁴ and R ²⁵ is a hydrogen atom. More preferably, both R ²⁴ and R ²⁵ are hydrogen atoms.

The substituent R ²⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. Methyl is preferred. And a hydrogen atom is preferable. Therefore, as the substituent P2, generally, a functional group having a high polymerization activity such as an unsubstituted acryloyloxy group, a methacryloyloxy group, and crotonoyloxy is preferably used.

The alkoxy residue formed by substituting the terminal substituent P2 is an alkyleneoxy group (for example, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy, etc. It represents a substituted alkyleneoxy group containing an ether bond such as ethyleneoxyethoxy).

Specific examples TP-51 to TP80 of the compounds of the present invention represented by the general formula (1) (general formulas and their substituents are shown in the table) are shown below, but the present invention is limited thereto. There is no such thing.

[0047]

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In the general formula (6), R ³¹ and R ³² each independently represent a hydrogen atom or a methyl group. The terminal substituent P3 of R ³³ represents a so-called oxirane group. The substituent P3
The substituents R ³⁴ and R ³⁵ each independently represent a hydrogen atom, an alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, methyl, ethyl). Preferred is a lower alkyl group, and more preferred is methyl). R ³⁴ and R ³⁵ are both preferably a hydrogen atom.

The substituent R ³⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. Methyl is preferred. Represents a hydrogen atom or a lower alkyl group such as methyl, ethyl or n-propyl.

The alkoxy residue formed by substituting the terminal substituent P3 is an alkyleneoxy group (eg ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy), an alkyleneoxy-substituted alkoxy group (eg 2-ethyleneoxyethoxy).

Specific examples TP-81 to TP105 of the compound of the present invention represented by the general formula (6) (general formulas and their substituents are shown in the table) are shown below, but the present invention is limited thereto. There is no such thing.

[0052]

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Other than the above, the following specific examples can be given as the discotic liquid crystalline compound of the present invention.

[0054]

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[0055]

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[0056]

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[0057]

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In the general formula (2), A is independently a hydrogen atom or an alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl), preferably a lower alkyl group such as methyl or ethyl. , And further preferably a methyl group) and an alkoxy group (for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group and an n-butoxy group are mentioned, and a methoxy group and an ethoxy group are more preferable). Most preferably, A is a hydrogen atom.

R ⁴¹ and R ⁴² each independently represent a hydrogen atom or a methyl group. The terminal substituent P4 of R ⁴³ represents a group containing a so-called acryloyl group. The substituents R ⁴⁴ and R ⁴⁵ of the substituent P4 are each independently a hydrogen atom or an alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-).
Examples thereof include butyl, pentyl, hexyl, heptyl, octyl and nonyl, lower alkyl groups such as methyl and ethyl are preferable, and methyl group is more preferable. ), R
Preferred is a combination in which ⁴⁴ is methyl and R ⁴⁵ is a hydrogen atom, or R ⁴⁴ and R ⁴⁵ are hydrogen atoms. Particularly preferably R ⁴⁴ and R
^This is the case where both ⁴⁵ are hydrogen atoms.

The substituent R ⁴⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. A methyl group is preferred. And a hydrogen atom is preferable. Therefore, the substituent P4 is generally an unsubstituted acryloyloxy group, methacryloyloxy group,
Those containing a functional group having a high polymerization activity such as a crotonoyloxy group are preferably used.

In the formula, k benzoyloxy groups bonded to the benzene ring and the naphthalene ring may be the same or different. k is preferably 2 or 3. X1 is an alkyleneoxy group (for example, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy), an alkyleneoxy-substituted alkyleneoxy group (for example, 2-ethyleneoxyethoxy).
Represents However, the terminal substituent P4 may be directly bonded to the aromatic ring represented by D1. Specific examples of the present invention represented by the general formula (2) are shown below, but the present invention is not limited thereto. The group derived from the benzene ring or naphthalene ring of D1 in the general formula (2) is represented by the following formulas I to
Illustrated in XVI.

[0062]

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Next, R in the above formulas I to XVI is represented by the following A-1 to
This is illustrated in A-30. In addition, for example, I
II-A-3 indicates that R in the formula III, which is an example of a group derived from a benzene ring, is A-3 below. In addition, Rs in formulas I to XVI may be different from each other.

[0064]

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In the general formula (7), each B independently represents a hydrogen atom or an alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, preferably a lower alkyl group such as methyl or ethyl). , And further preferably a methyl group) and an alkoxy group (for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group and an n-butoxy group are mentioned, and a methoxy group and an ethoxy group are more preferable). Most preferably, B is a hydrogen atom.

R ⁵¹ and R ⁵² each independently represent a hydrogen atom or a methyl group. The substituents R ⁵⁴ and R ⁵⁵ are each independently a hydrogen atom, an alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, pentyl, hexyl,
Examples include heptyl, octyl and nonyl, lower alkyl groups such as methyl and ethyl are preferred, and methyl is more preferred. ), R ⁵⁴ is a methyl group, R ⁵⁵ is a hydrogen atom,
Alternatively, R ⁵⁴ and R ⁵⁵ are preferably a combination of hydrogen atoms.

The substituent R ⁵⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. A hydrogen atom is preferred.

In the formula, k benzoyloxy groups bonded to the benzene ring and naphthalene ring may be the same or different. k is preferably 2 or 3. X2 represents an alkyleneoxy group (for example, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy) or a substituted alkyleneoxy group (for example, 2-ethyleneoxyethoxy). However,
The terminal substituent P5 may be directly bonded to the aromatic ring represented by D2.

As the substituent P5, those containing an unsubstituted vinyloxy group, which is a functional group having a high polymerization activity, are generally preferably used.

Specific examples of the present invention represented by the general formula (7) are shown below in accordance with the case of the general formula (2), but the present invention is not limited thereto. D2 of the general formula (7)
Examples of the group derived from the benzene ring or naphthalene ring include those of the formulas I to XVI as in the case of the general formula (2). Formula I ~
Examples of R of XVI are shown in B-1 to B-60 below, but R may be different from each other.

[0071]

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[0072]

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In the general formula (8), each C independently represents a hydrogen atom or an alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, n-butyl, preferably a lower alkyl group such as methyl or ethyl). , And further preferably a methyl group) and an alkoxy group (for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group and an n-butoxy group are mentioned, and a methoxy group and an ethoxy group are more preferable). Most preferably, C is a hydrogen atom.

R ⁶¹ and R ⁶² each independently represent a hydrogen atom or a methyl group. The terminal substituent P6 of R ⁶³ represents a group containing a so-called oxirane group. The substituents R ⁶⁴ and R ⁶⁵ of the substituent P6 are each independently a hydrogen atom or an alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, n).
-Butyl, pentyl, hexyl, heptyl, octyl,
Nonyl is preferred, and lower alkyl groups such as methyl and ethyl are preferable, and methyl is more preferable. ), R
Both ⁶⁴ and R ⁶⁵ are preferably hydrogen atoms.

The substituent R ⁶⁶ is a hydrogen atom, a substituted or unsubstituted alkyl group (eg, methyl, ethyl, n-propyl,
Examples include isopropyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, 2-chloroethyl, 3-methoxyethyl, 2- (2-methoxyethoxy) ethyl, and lower alkyl groups such as methyl and ethyl are preferable. Methyl is preferred. Represents a hydrogen atom or a lower alkyl group such as methyl, ethyl or n-propyl.

In the formula, k benzoyloxy groups bonded to the benzene ring and the naphthalene ring may be the same or different. X3 represents an alkyleneoxy group (for example, ethyleneoxy, propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy) or a substituted alkyleneoxy group (for example, 2-ethyleneoxyethoxy). However, the terminal substituent P6 may be directly bonded to the aromatic ring represented by D3. Below, the general formula (8)
Specific examples of the present invention represented by are shown according to the case of the general formula (2), but the present invention is not limited thereto. Examples of the group derived from the benzene ring or naphthalene ring of D3 in the general formula (8) include formulas I to XVI as in the case of the general formula (2). Examples of R in formulas I to XVI are shown below in C-1 to C-30, but R may be different from each other.

[0077]

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For the general formula (3),
Has the same meaning as the symbol at the corresponding position in
The details of this are already clear.
L5 in the general formula (4) has the same meaning as X1 in the general formula (2).
R⁸⁴, R⁸⁵And R ⁸⁶Is R in the general formula (2)⁴⁴, R⁴⁵
And R⁴⁶And are synonymous with each other.

The synthesis method of the compounds represented by the general formulas (1), (5) and (6) is described in Japanese Patent Application No. 6-97.
No. 443, which can be synthesized accordingly. The compounds represented by the general formula (2), the general formula (3), the general formula (7) and the general formula (8) can also be prepared by replacing the triphenylene derivative with a benzene derivative or a naphthalene derivative according to the method described in the above specification. It can be synthesized. These and the compounds represented by the general formula (4) will be described later.

The mixing ratio in the composition comprising the discotic liquid crystalline compound and the compound which is not discotic liquid crystalline in the present invention is preferably 50% or more by weight as the content of the discotic liquid crystalline compound.
It is less than 0%, more preferably 60% or more and 100%
Is less than.

As a method for producing the mixture, for example, both powders are mixed using a mortar, a ball mill, a paint shaker or the like. Alternatively, both are stirred and mixed in a liquid state in which they are heated and melted. Further, a method in which both are made into a solution by using a solvent and then mixed is given. The solvent that can be used in the solution method is selected from a range from polar solvents such as N, N-dimethylformamide (DMF) and dimethylsulfoxide (DMSO) to nonpolar solvents such as benzene and hexane. it can. Non-polar solvents such as benzene and hexane, halogenated solvents such as dichloromethane and chloroform, esters such as methyl acetate and butyl acetate, ketones such as acetone and methyl ethyl ketone,
Ethers such as tetrahydrofuran and 1,2-dimethoxyethane are preferable, and a mixed solvent can also be used. Of these, halogenated solvents and ketones are preferred.

The optically anisotropic material constituted by using the discotic liquid crystal composition of the present invention may be constituted only by the discotic liquid crystal composition, but it is generally desired that it is formed on the support. Of the liquid crystal layer exhibiting the above optical anisotropy or a layer in which light or heat energy is applied to the liquid crystal layer is provided above or below the optical anisotropic layer or according to the application. There may be a protective film or support between the layers.

It is desirable that the support material has a good light transmittance and, in addition, has a near optical isotropy. Therefore,
A support formed of a material having a small intrinsic birefringence value sold under the trade name of glass, ZEONEX (Nippon Zeon), ARTON (Nippon Synthetic Rubber), Fujitac (Fujifilm) or the like is preferable. However, even for materials with a large intrinsic birefringence value such as polycarbonate, polyacrylate, polysulfone, and polyethersulfone, it is possible to form an optically isotropic support by controlling the molecular orientation during film formation. It is possible, and they are preferably used.

As the material for the protective film, for example, polymethylmethacrylate, acrylic acid / methacrylic acid copolymer, styrene / maleimide anhydride copolymer, polyvinyl alcohol, N-methylolacrylamide, styrene.
Vinyl toluene copolymer, chlorosulfonated polyethylene, nitrocellulose, polyvinyl chloride, chlorinated polyolefin, polyester, polyimide, vinyl acetate / vinyl chloride copolymer, ethylene / vinyl acetate copolymer, polyethylene, polypropylene, polycarbonate, etc. And organic substances such as a silane coupling agent. In addition, a Langmuir-Blodgett method (LB) such as ω-tricosanoic acid, dioctadecyldimethylammonium chloride and methyl stearate is used.
) Can also be used.

It is a well-known fact in the case of rod-shaped liquid crystals that the protective film provided on the support in advance often has a great influence on the molecular alignment at the time of forming the liquid crystal layer as an alignment film. It is almost always used as an inorganic or organic alignment film. This is one of the techniques preferably used in the present invention, and as a metal oblique deposition film, S
The iO orthorhombic vapor-deposited film and a rubbed polyimide film are typical as the organic alignment film, but other rubbed modified Poval, a rubbed silylating agent-treated glass substrate, or a rubbed gelatin film may be used. Used. However, instead of rubbing, a method in which a polyvinyl alcohol thin film is stretched 4 to 5 times, or a glass substrate is directly rubbed without providing the above protective film can be used.

Magnetic field orientation and electric field orientation are available as methods other than the above in which the discotic liquid crystal coated on the substrate is oriented obliquely. In this method, after coating the discotic liquid crystal on the substrate, a zone for applying a magnetic field or an electric field at a desired angle is required, but the zone itself needs to be adjusted to a temperature at which a discotic nematic phase is formed. is there.

The liquid crystal layer constituting the optically anisotropic material of the present invention can be formed as a thin film on the support by a coating method such as a vapor deposition method, spin coating, dip coating or extrusion coating. In particular, in the liquid crystal of the present invention, the tendency that the optical axis is aligned in the direction of application is often observed at the stage of application.

Therefore, the liquid crystal thin film is formed on a suitable support in a state where at least one of the interfaces is in contact with the gas phase, that is, by a general coating method, and after drying, the disc liquid is formed at a temperature within the liquid crystal phase forming temperature range. Tick nematic phase or uniaxial columnar phase is formed and heat-treated for a certain period of time, and then it is directly subjected to thermal polymerization or photocrosslinking polymerization and then cooled to have desired optical characteristics and high thermal durability. An optically anisotropic material can be obtained.

The polymerization process used in the present invention is generally carried out after the liquid crystal exhibits preferable optical anisotropy, that is, after the monodomain is uniaxially aligned by heating on the alignment film. In the case of an epoxy group, cationic type polymerization by ultraviolet rays is also possible, but after orientation in a short time, the temperature can be further raised by several tens of degrees and fixed by thermal polymerization. However, radical polymerization or cationic polymerization using a photopolymerization initiator with ultraviolet rays generally has a very high polymerization rate and is preferable in terms of productivity in the manufacturing process.

Examples of the photopolymerization initiator in the present invention include US Pat. Nos. 2,367,661 and 2,367,67.
No. 0 α-carbonyl compounds described in each specification,
Acyloin ethers described in US Pat. No. 2,448,828, US Pat. No. 2,722,512
.Alpha.-hydrocarbon substituted aromatic acyloin compounds described in U.S. Pat. No. 3,046,127.
No. 2,951,758, a polynuclear quinone compound, a combination of a triarylimidazole dimer / p-aminophenyl ketone described in US Pat. No. 3,549,367, JP-A-6
0-105667, acridine and phenazine compounds described in US Pat. No. 4,239,850, oxadiazole compounds described in US Pat. No. 4,212,970, and the like. . The content concentration of these photopolymerization initiator systems in the composition of the present invention is usually low, and when the content is inappropriately high, undesired results such as blocking of effective rays are produced. The amount of photoinitiator system in the present invention is 0.
The range of 01% to 20% is sufficient, and more preferably 0.5% to 5% to obtain good results. Further, in the present invention, various organic amine compounds can be used in combination, if necessary, thereby enhancing the effect. Examples of these organic amine compounds include triethanolamine, diethanolaniline, p-dimethylaminobenzoic acid ethyl ester, and Michler's ketone. The amount of the organic amine compound added is preferably 50 to 200% of the total amount of the photopolymerization initiator. Further, the photopolymerization initiator used in the present invention may contain N-phenylglycine or 2
The photopolymerization initiation ability can be further enhanced by adding a hydrogen donating compound such as -mercaptobenzothiazole and N, N-dialkylaminobenzoic acid alkyl ester. Further, in order to suppress polymerization inhibition by oxygen,
Adding a small amount of a surfactant is often effective.

[0091] The polymerization of the epoxy group, as the ultraviolet activatable cationic catalyst, allyl diazonium salt (hexafluorophosphate, tetrafluoroborate), diaryliodonium salts, VIa Group Arironiumu salt (PF ₆ ^-,
An allylsulfonium salt having an anion such as AsF ₆ ⁻ or SbF ₆ ⁻ is preferably used.

As the light rays for polymerization, electron rays, ultraviolet rays, visible rays and infrared rays (heat rays) can be used if necessary, but ultraviolet rays are generally used. Low-pressure mercury lamps (sterilization lamps, fluorescent chemical lamps, black lights), high-pressure discharge lamps (high-pressure mercury lamps, metal halide lamps), short arc discharge lamps (ultra-high pressure mercury lamps, xenon lamps, mercury-xenon lamps) are used as the light rays. Can be mentioned.

In the case of the benzoyloxytriphenylene ring compound of the present invention, λma at about 270 nm is generally used.
254 nm because x has a large molecular extinction coefficient
Short wave ultraviolet rays such as may not be used effectively. Therefore, as the photopolymerization initiator, a compound having an absorption band in the near ultraviolet described below is preferably used, and a light source that can strongly emit near ultraviolet light, such as a high pressure mercury lamp or a metal halide lamp is also preferably used.

[0094]

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The action of the optically anisotropic material of the present invention, that is, the retardation film for a liquid crystal display device will be described below with reference to the drawings, taking a TN type liquid crystal display device as an example. 1 and 2 show polarization states of light propagating in a liquid crystal cell when a sufficient voltage equal to or higher than a threshold voltage is applied to the liquid crystal cell. Since the transmittance characteristic of light particularly when a voltage is applied greatly contributes to the viewing angle characteristic of the contrast, a case where a voltage is applied will be described as an example. FIG. 1 is a diagram showing a polarization state when light is vertically incident on a liquid crystal cell. Natural light L0 is polarization axis PA
When the light is perpendicularly incident on the polarizing plate A having, the light transmitted through the polarizing plate PA becomes linearly polarized light L1.

When the arrangement state of the liquid crystal molecules when a sufficient voltage is applied to the TN type liquid crystal cell is schematically shown as a model with one liquid crystal molecule, LC is shown in the schematic diagram. When the molecular long axis of the liquid crystal molecules LC in the liquid crystal cell LCS is parallel to the light path, there is no difference in the refractive index on the incident surface (in the plane perpendicular to the light path), and therefore the light propagates in the liquid crystal cell. There is no phase difference between the ordinary light and the extraordinary light, and the linearly polarized light that has passed through the LC cell propagates as it is even if it passes through the liquid crystal cell. When the polarization axis PB of the polarizing plate B is set to be perpendicular to the polarization axis PA of the polarizing plate A, the linearly polarized light L2 that has passed through the liquid crystal cell cannot pass through the polarizing plate B and is in a dark state.

FIG. 2 is a diagram showing the polarization state of light when the light obliquely enters the liquid crystal cell. Natural light L of incident light
When 0 is obliquely incident, the polarized light L1 transmitted through the polarizing plate A
Is almost linearly polarized (in the actual case, it becomes elliptically polarized due to the characteristics of the polarizing plate). In this case, the refractive index anisotropy of the liquid crystal causes a difference in the refractive index on the incident surface of the liquid crystal cell, and the light L2 transmitted through the liquid crystal cell is elliptically polarized light and is not completely blocked by the polarizing plate B. As described above, in the case of oblique incidence, blocking of light in a dark state becomes insufficient, resulting in a large decrease in contrast, which is not preferable.

The present invention is intended to prevent such a decrease in contrast due to oblique incidence and improve viewing angle characteristics. FIG. 3 shows an example of the configuration according to the present invention. An optically anisotropic material RF having an optical axis inclined from the normal direction of the liquid crystal cell is arranged between the polarizing plate B and the liquid crystal cell. The optically anisotropic material RF is a birefringent body that polarizes more as the angle of incidence of light with respect to the optical axis increases. As in the case of FIG. 2, the elliptically polarized light L2 which is obliquely incident on the liquid crystal display element having such a structure and is transmitted through the liquid crystal cell is elliptically polarized light L2 due to the phase delay action when transmitting the optically anisotropic material RF. It was possible to realize a good liquid crystal display device which is modulated to the original linearly polarized light and has the same transmittance even at various oblique incidences and has no viewing angle dependence.

It is presumed as follows that the viewing angle of the liquid crystal display device was significantly improved by the present invention. Most TN-LCDs adopt a normally white mode. In this mode, the transmittance of light from the black display portion remarkably increases as the viewing angle increases, resulting in a sharp decrease in contrast. Black display is the state when voltage is applied,
At this time, the TN type liquid crystal cell can be regarded as a positive uniaxial optically anisotropic body whose optical axis is slightly inclined from the direction normal to the surface of the cell. Further, in the case of intermediate gradation, it is considered that the optical axis thereof is further inclined from the normal line direction of the LC cell.

When the optical axis of the liquid crystal cell is tilted from the direction normal to the surface of the liquid crystal cell, it is expected that the compensation will be insufficient in an optically anisotropic body having the optical axis in the normal direction. If the liquid crystal cell can be regarded as a positive uniaxial optical anisotropic body, a negative uniaxial optical anisotropic body is preferable for compensating for it. For this reason, in the present invention, the optical axis of the negative uniaxial optical anisotropic body in which the optical axis is inclined from the normal direction or the optical axis of the optical anisotropic body having negative uniaxiality in the microscopic direction is continuously normal. It is estimated that the viewing angle characteristics were significantly improved by the optical anisotropic body tilted from the direction.

Negative uniaxiality in the present invention means a relationship of nα <nβ = nγ, where nα, nβ, and nγ are the refractive indices in the triaxial direction of a sheet having optical anisotropy in ascending order. I have. Therefore, it has a characteristic that the refractive index in the optical axis direction is the smallest. However, it is not necessary that the values of nβ and nγ be exactly equal, and it is sufficient if they are almost equal. Specifically, | nβ-nγ | / | nβ-nα
If | <0.2, there is no practical problem. TFT, T
As a condition for greatly improving the viewing angle characteristics of the N-type liquid crystal cell, the optical axis is preferably inclined at 5 to 50 degrees from the normal direction of the sheet surface, more preferably 10 to 40 degrees, and more preferably 10 degrees. ~ 30 degrees is most preferred. Furthermore, when the thickness of the sheet is D, 100 <(nβ−nα) × D <400
It is desirable to satisfy the condition of nm.

The discotic liquid crystal constituting the optically anisotropic material of the present invention may be used alone or in combination.
Particularly, by appropriately mixing the liquid crystals, the phase transition temperature is often controlled, the optical structure of the liquid crystal phase is controlled, and the film-forming property is effectively improved.

[0103]

EXAMPLES The present invention will be described in detail below with reference to examples. The non-discotic liquid crystalline compound represented by the general formula (3) of the present invention is generally synthesized by the following route.
That is, it is a condensation of a benzene derivative or a naphthalene derivative with an acid chloride of a side chain substituent or a mixed acid anhydride. In this example, the synthesis of the present inventions VI-A-3 and XI-A-3 was illustrated. In addition, I-A-3, II-A-3, I
II-A-3, IV-A-3, V-A-3, IX-A-3, X
-A-3 is also synthesized in the same manner, and its identification data is exemplified, but the present invention is not limited thereto. (Note that VI-A-
3, the benzene ring of D4 of the general formula (3) is the formula VI,
It shows that R is A-3. )

(Synthesis of Non-Discotic Liquid Crystalline Compound) Example 1 Synthesis of VI-A-3 In a 100 ml three-necked flask, 5.0 g of 4- (4-acryloyloxybutyloxy) benzoic acid and triethylamine 5.3 ml. , Tetrahydrofuran 50ml, 0 ℃
Then, 1.46 ml of methanesulfonyl chloride was added dropwise, and subsequently 57.8 mg of 4-dimethylaminopyridine was added, and the mixture was stirred for 10 minutes as it was. 0.6 g of pyrogallol was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure and then purified using silica gel column chromatography to obtain 3.93 g (96%) of oily VI-A-3.
Obtained. Identification data of VI-A-3 ¹ H-NMR (CDCl ₃ ) δ: 7.9 (d, 4H),
7.8 (d, 2H), 7.5 (m, 3H), 7.0
(D, 4H), 6.9 (d, 2H), 6.3 (m, 3)
H), 6.1 (m, 3H), 5.9 (m, 3H), 4.
1 (m, 12H), 1.7 (m, 12H)

Example 2 Synthesis of XI-A-3 In a 50 ml three-necked flask 5.0 g 4- (4-acryloyloxybutyloxy) benzoic acid and 25 ml methylene chloride, 4.4 ml thionyl chloride, catalytic amount of Dimethylformamide was added, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, excess thionyl chloride and methylene chloride as a solvent were distilled off under reduced pressure. To this, 1.5 g of 1,7-dihydroxynaphthalene and 10 ml of pyridine were added, and the mixture was stirred overnight at room temperature. After distilling off excess pyridine under reduced pressure, the residue was purified by silica gel column chromatography to obtain an oily XI-
2.4 g (49%) of A-3 was obtained. Identification data of XI-A-3 ¹ H-NMR (CDCl ₃ ) δ: 8.1 (m, 5H),
7.6 (m, 4H), 7.1 (m, 4H), 6.4 (d
d, 2H), 6.2 (dd, 2H), 5.9 (dd, 2)
H), 4.2 (m, 8H), 1.8 (m, 8H)

Identification data of IA-3 ¹ H-NMR (CDCl ₃ ) δ: 7.9 (d, 4H),
7.4 (m, 4H), 7.0 (d, 4H), 6.4
(M, 2H), 6.2 (m, 2H), 6.0 (m, 2)
H), 4.2 (m, 8H), 1.8 (m, 8H) Phase transition temperature measurement by DSC and polarization microscope observation Crystal phase-92 ° C-Liquid crystal phase-107 ° C-Isotropic liquid II-A- Identification data of 3 ¹ H-NMR (CDCl ₃ ) δ: 8.1 (d, 4H),
7.2 (m, 4H), 7.1 (d, 4H), 6.4 (d
d, 2H), 6.2 (dd, 2H), 6.0 ((dd,
2H), 4.2 (m, 8H), 1.9 (m, 8H) Phase transition temperature measurement by DSC and polarization microscope observation Crystal phase-60 ° C-N Liquid crystal phase-64 ° C-Isotropic liquid III-A -3 identification data _{^{1 H-NMR (CDCl 3)}} δ: 8.1 (d, 4H),
7.3 (s, 4H), 7.1 (d, 4H), 6.4 (d
d, 2H), 6.2 (dd, 2H), 6.0 ((dd,
2H), 4.2 (m, 8H), 1.8 (m, 8H) DSC and polarization microscope observation

Crystalline phase-97 ° C.-N liquid crystal phase-155 ° C.-Identification data for isotropic liquid IV-A-3 ¹ H-NMR (CDCl ₃ ) δ: 8.1 (d, 6H),
7.1 (s, 3H), 7.0 (d, 6H), 6.5 (d
d, 3H), 6.1 (dd, 3H), 5.8 ((dd,
3H), 4.3 (m, 6H), 4.1 (m, 6H),
Identification data of 1.9 (m, 12H) VA-3 ¹ H-NMR (CDCl ₃ ) δ: 8.1 (d, 2H),
7.9 (dd, 4H), 7. 5 (m, 2H), 7.3
(Dd, 1H), 7.1 (d, 2H), 7.0 ((d,
4H), 6.3 (m, H), 6.1 (m, 3H), 5.
9 (m, 3H), 4.1 (m, 12H), 1.8 (m,
12H) Identification data of IX-A-3 ¹ H-NMR (CDCl ₃ ) δ: 8.2 (d, 4H),
7.8 (d, 2H), 7.6 (t, 2H), 7.5
(D, 2H), 7.2 (d, 4H), 6.4 (dd, 2)
H), 6.2 (dd, 2H), 6.0 (dd, 2H),
4.2 (m, 8H), 1.8 (m, 8H) Phase transition temperature measurement by DSC and polarization microscope observation Crystal phase -130 ° C-N liquid crystal phase -133 ° C-Isotropic liquid X-A-3 Identification data ¹ H-NMR (CDCl ₃ ) δ: 8.1 (m, 5H),
7.9 (d, 2H), 7.7 (t, 1H), 7.5
(M, 2H), 7.1 (t, 4H), 6.4 (d, 2)
H), 6.2 (m, 2H), 6.0 (dd, 2H),
4.2 (m, 8H), 1.8 (m, 8H)

The non-discotic liquid crystalline compound represented by the general formula (4) of the present invention was generally synthesized by the following route. That is, it is a reaction of reacting resorcinol with an ω-haloalcohol or an ester of ω-haloalcohol, followed by deacylation, if necessary, and then vinylcarbonylation. II-
The synthesis of A-20 and II-A-31 was exemplified. In addition, II-A-25, II-A-32, and II-A-33 were synthesized in the same manner, and the identification data thereof are illustrated, but the present invention is not limited thereto. (In II-A-20, the resorcinol moiety of the general formula (4) has the formula II, and R is A-
It shows that it is 20. )

Example 3 Synthesis of II-A-20 a) Synthesis of 1,3-di- (4-hydroxybutoxy) benzene In a 300 ml three-necked flask, resorcinol 18.0.
g, potassium carbonate 50.0 g and N, N-dimethylacetamide 100 ml were added, and 4-chlorobutylacetate 52.0 g was added dropwise at 120 ° C., and the mixture was stirred for 5 hours as it was. After cooling, the reaction mixture is poured into 150 ml of water, 300 ml
It was extracted with ethyl acetate and washed twice with 100 ml of water. The extract was dried over anhydrous magnesium sulfate and filtered. The solvent was concentrated under reduced pressure, dissolved in 75 ml of methanol, 75 ml of an aqueous solution of 31.4 g of potassium hydroxide was gradually added dropwise, and the mixture was heated under reflux for 2 hours. After cooling, 200 ml of water and 48 ml of concentrated hydrochloric acid were added, and the precipitated crystals were filtered under reduced pressure and washed with water. After drying, recrystallization with a solvent of hexane / ethyl acetate = 1/1,
1,3-di- (4-hydroxybutoxy) benzene 3
2.0 g (90%) was obtained.

1,3-di- (4-hydroxybutoxy)
Identification data of benzene ¹ H-NMR (CDCl ₃ , ppm): 1.6 to 2.0 (m, 8H), 3.7 (t, 4H), 4.
0 (t, 4H), 6.4 ~ 6.6 (m, 3H), 7.15 (t, 1H)

B) Synthesis of II-A-20 In a 100 ml three-necked flask, 18.0 g of 1,3-di- (4-hydroxybutoxy) benzene and 2 of triethylamine were added.
4 ml and 50 ml of acetonitrile were added, and 15.4 g of acrylic acid chloride was slowly added dropwise under ice cooling, and the mixture was stirred for 1 hour as it was, then returned to room temperature and further stirred for 2 hours. The reaction mixture was poured into 150 ml of water, extracted with 300 ml of ethyl acetate and washed twice with 100 ml of water. The extract was dried over anhydrous magnesium sulfate and filtered. After the solvent was concentrated under reduced pressure, it was purified using silica gel column chromatography and 1,3-
Di- (4-acryloyloxybutoxy) benzene 21
g (85%) was obtained.

Identification data of 1,3-di- (4-acryloyloxybutoxy) benzene ¹ H-NMR (CDCl ₃ , ppm): 1.7 to 2.0 (m, 8H), 3.95 (t, 4H),
4.25 (t, 4H), 5.7 ~ 6.4 (6H), 6.4 ~ 6.6 (m, 3H), 7.
15 (t, 1H)

Example 4 Synthesis of II-A-31 a) Synthesis of 1,3-di- (6-hydroxyhexyloxy) benzene In a 300 ml three-necked flask, 5.5 g of resorcinol,
21.0 g of potassium carbonate and 50 ml of N, N-dimethylacetamide were added, 19.0 g of 6-chloro-1-hexanol was added dropwise at 120 ° C., and the mixture was stirred for 6 hours as it was. After cooling, the reaction mixture was poured into 100 ml of water, extracted with 200 ml of ethyl acetate and washed twice with 100 ml of water. The extract was dried over anhydrous magnesium sulfate and filtered. The solvent was concentrated under reduced pressure, the crystals were washed with hexane and dried, and 1,3-di- (6
-Hydroxyhexyloxy) benzene 11.5 g (7
4%).

Identification data of 1,3-di- (6-hydroxyhexyloxy) benzene ¹ H-NMR (CDCl ₃ , ppm): 1.3 to 1.9 (m, 8H), 3.65 (t, 4H),
3.95 (t, 4H), 6.4 ~ 6.6 (m, 3H), 7.15 (t, 1H)

B) Synthesis of II-A-31 Into a 100 ml three-necked flask, 9.3 g of 1,3-di- (6-hydroxyhexyloxy) benzene, 10 ml of triethylamine and 30 ml of acetonitrile were placed, and acrylic acid chloride was cooled under ice cooling. 6.5 g was slowly added dropwise, and the mixture was stirred as it was for 1 hour, returned to room temperature and further stirred for 2 hours. The reaction mixture was poured into 100 ml of water, extracted with 200 ml of ethyl acetate and washed twice with 100 ml of water. Dry filtration was performed with anhydrous magnesium sulfate. After the solvent was concentrated under reduced pressure, it was purified using silica gel column chromatography and 1,3-
10.4 g (80%) of di- (6-acryloyloxyhexyloxy) benzene was obtained.

Identification data of 1,3-di- (6-acryloyloxyhexyloxy) benzene ¹ H-NMR (CDCl ₃ , ppm): 1.3 to 1.9 (m, 8H), 3.9 (t, 4H), 4.
15 (t, 4H), 5.8 ~ 6.4 (6H), 6.4 ~ 6.6 (m, 3H), 7.15
(t, 1H)

Identification data of II-A-32 ¹ H-NMR (CDCl ₃ , ppm): 3.8 (m, 8H), 4.1 (t, 4H), 4.3 (t, 4H)
4H), 5.8 ~ 6.4 (6H), 6.4 ~ 6.6 (m, 3H), 7.15 (t, 1H)

Identification data of II-A-25 ¹ H-NMR (CDCl ₃ , ppm): 3.6 to 3.9 (m, 16H), 4.1 (t, 4H),
4.3 (t, 4H), 5.8 ~ 6.4 (6H), 6.4 ~ 6.6 (m, 3H), 7.15
(t, 1H)

Identification data of II-A-33 ¹ H-NMR (CDCl ₃ , ppm): 1.4 to 2.0 (m, 16H), 3.5 (m, 8H),
3.95 (t, 4H), 4.2 (t, 4H), 5.9 ~ 6.4 (6H), 6.4 ~ 6.
6 (m, 3H), 7.15 (t, 1H)

Example 5 (Liquid Crystal Composition) A predetermined amount of a triphenylene derivative and a compound not having discotic liquid crystallinity were weighed to prepare a solution of 2-butanone or dichloromethane, and then the solvent was evaporated to obtain a composition. With respect to this composition, a change in liquid crystal phase was observed with a DSC and a polarization microscope. The results are shown in Tables 1 and 2.

[0121]

[Table 1]

[0122]

[Table 2]

From Table 1 and Table 2, the composition of the present invention is obviously useful for controlling the phase transition temperature.

Example 6 (Optically Anisotropic Material Made of Liquid Crystal Composition) A method for producing an optically anisotropic material made of the liquid crystal composition of the present invention and its physical properties will be described below. 100 μm thick film of polyether sulfone (FS-1300 manufactured by Sumitomo Bakelite Co., Ltd.,
A substrate having a size of 100 mm × 100 mm) is provided with a 0.1 μm gelatin undercoat layer, polyamic acid (SE-7210 manufactured by Nissan Chemical Industries, Ltd.) is applied as an alignment film on the gelatin undercoat layer, and the polyimide film is baked at 180 ° C. And This polyimide film was rubbed by a rubbing machine to give orientation ability. The liquid crystal compositions 1, 3, 4, and 11 described in Table 1 and Table 2 of Example 3 were dissolved in methyl ethyl ketone,
Liquid crystal composition 10 wt%, cellulose acetate butyrate (CAB551-0.2 Eastman Chemical) 2.2 wt%,
Irgacure 907 (manufactured by Ciba Geigy) is 3.3 wt.
%, Sensitizer (Kayacure DETX Nippon Kayaku) was added to 1 wt% to prepare a liquid with a spin coater.
The liquid crystal composition was applied at 0 rpm to form a non-aligned layer of the liquid crystal composition, and four kinds of film-like materials were prepared. These were designated as film-like materials A, B, C, and D. Each of them was heated to a predetermined temperature and oriented, then rapidly cooled and, if necessary, irradiated with light, and their apparent optical axis inclination angles β and Δn · d were measured by ellipsometry. For the measurement, an Shimadzu ellipsometer (AEP-100) was used as a transmission mode to determine the angle dependence of the retardation, and the optimum triaxial refractive index and optical axis direction were calculated from the values. However, at this time, the retardation value was not always 0, so the apparent optical axis tilt angle β was obtained based on the angle having the minimum value.

Film A The liquid crystal composition 1 was about 120 to 1 when observed by a polarization microscope.
Form a discotic nematic phase at 57 ° C.
Therefore, the film-shaped material A is brought into contact with the metal roller heated to a surface temperature of 155 ° C. for 10 seconds from the support side, and immediately thereafter, the film-shaped material A is brought into contact with the metal roller heated to a surface temperature of 140 ° C. for 30 seconds from the support side. Then, the optically anisotropic material of the present invention was obtained by bringing it into contact with a metal roller whose surface temperature was adjusted to 0 ° C. for 10 seconds. When this sheet was observed with a polarizing microscope, it was observed that the optical anisotropy existed in the monodomain (it is considered that the optical anisotropy of the discotic nematic phase was fixed in the glass state). Further, according to the measurement by ellipsometry, the apparent optical axis tilt angle β was 35 ° and Δn · d = 125 nm.

Film-like material B The liquid crystal composition 3 was about 130 to 1 as observed by a polarizing microscope.
A discotic nematic phase is formed at 62 ° C.
Therefore, the film-like material B was brought into contact with the metal roller heated to a surface temperature of 150 ° C. for 30 seconds from the support side, and then continuously irradiated with a xenon lamp for 20 seconds at the same temperature, and immediately thereafter, the surface temperature was adjusted to 20 ° C. The optically anisotropic material of the present invention was obtained by contacting the above-mentioned metal roller for 10 seconds. When this sheet was observed with a polarizing microscope,
It was observed that the optical anisotropy exists in the monodomain. This optically anisotropic material no longer exhibited liquid crystallinity, and the optical anisotropy did not change even when heated again to 200 ° C. Further, according to the measurement by ellipsometry, the apparent optical axis tilt angle β was 32 ° and Δn · d = 155 nm.

Film-like material C The liquid crystal composition 4 was about 135 to 1 as observed by a polarizing microscope.
Form a discotic nematic phase at 46 ° C.
Therefore, the film-like material C was brought into contact with the metal roller heated to a surface temperature of 140 ° C. for 30 seconds from the support side, and further continuously irradiated with a high pressure mercury lamp for 20 seconds at the same temperature. Immediately thereafter, the surface temperature was increased to 20 ° C. The optically anisotropic material of the present invention was obtained by contacting the adjusted metal roller for 10 seconds. When this sheet was observed with a polarizing microscope,
It was observed that the optical anisotropy exists in the monodomain. This optically anisotropic material no longer exhibited liquid crystallinity, and the optical anisotropy did not change even when heated again to 200 ° C. Further, according to the measurement by ellipsometry, the apparent optical axis tilt angle β was 33 ° and Δn · d = 120 nm.

Film-like product D The liquid crystal composition 11 was observed to have a polarization microscope of about 91-1.
It forms a discotic nematic phase at 55 ° C. Therefore, the film-shaped material D was brought into contact with the metal roller heated to a surface temperature of 130 ° C. for 30 seconds from the support side, and the halogen lamp was continuously irradiated for 20 seconds at the same temperature, and immediately after that, the metal was adjusted to a surface temperature of 20 ° C. The optically anisotropic material of the present invention was obtained by contacting with a roller for 10 seconds. When the sheet was observed with a polarizing microscope, it was observed that the optical anisotropy existed in the monodomain. This optically anisotropic material no longer exhibits liquid crystallinity,
The optical anisotropy did not change even when heated to ° C.
Further, according to the measurement by ellipsometry, the apparent optical axis tilt angle β was 31 ° and Δn · d = 122 nm.

Example 7 (Performance evaluation as retardation film for expanding viewing angle of TN type liquid crystal display element) A support was prepared as follows. T
AC 100 μm thick film (Fuji Tuck, size 10
(0 mm x 100 mm) as a substrate, a 0.1 μm gelatin undercoat layer is provided, and modified Poval is applied as an alignment film on it. After drying at 90 ° C, this film is rubbed with a rubbing machine to provide alignment ability. did. The principal refractive index in the plane is n
x ′, ny ′, the refractive index in the thickness direction is nz ′, and the thickness is d ′.
, The TAC film is | nx'-ny '| x
d ′ = 6 nm, {(nx ′ + ny ′) / 2−nz ′} ×
d '= 40 nm, which was almost uniaxial, and the optical axis was almost in the film normal direction. This support is used in Example 6
A film-like product was prepared in the same manner by using the film-like product D in place of the support. This sheet was also observed by polarization microscope to have optical anisotropy in the monodomain. Next, the product of the difference in refractive index between the extraordinary ray and the ordinary ray of the liquid crystal and the gap size of the liquid crystal cell is 480 nm, and the above film-like material is attached to the TN type liquid crystal cell having a twist angle of 90 degrees, and the liquid crystal cell is attached. On the other hand, the angle dependence of the contrast in a 0 to 5 V 30 Hz rectangular wave was confirmed by Otsuka Electronics LCD-5.
000. The position of contrast 10 was defined as the viewing angle, and the viewing angles in the vertical and horizontal directions were obtained. In addition, the contrast ratio when viewed from the front was measured. Here, the measured values of only the TN liquid crystal in which the above film is not attached are also shown. The results are shown in Table 3 below. In FIG. 4, arrows indicate the rubbing direction in the retardation film and the rubbing direction in the liquid crystal cell.

[0130]

[Table 3]

As is apparent from the above table, in the LCD provided with the optical compensation sheet of the present invention, the viewing angle characteristics are remarkably improved. When the discotic liquid crystal compounds used in the above examples are compared with the above-mentioned disc-shaped morphological characteristics, b and c are 0.89 and 0.29, respectively, when a = 1.

[0132]

INDUSTRIAL APPLICABILITY The liquid crystal composition of the present invention easily forms a thin film in an alignment state having a monodomain optical anisotropy on a general liquid crystal alignment film by wet coating and heating at a relatively low temperature. The optical anisotropy of this thin film can be fixed by applying light or heat energy. By using this thin film together with a liquid crystal display element, it became possible to improve its viewing angle as a retardation film.

[Brief description of the drawings]

FIG. 1 is a diagram showing a polarization state of light when light is vertically incident on a liquid crystal cell.

FIG. 2 is a diagram showing a polarization state of light when light obliquely enters a liquid crystal cell.

FIG. 3 is a diagram showing an example of using an optically anisotropic material in a retardation film for a liquid crystal display device.

FIG. 4 is a diagram showing a relationship among a polarization axis of a polarizing plate, a rubbing direction of a liquid crystal cell, and a rubbing direction of an optically anisotropic sheet alignment film when measuring a viewing angle characteristic in an example.

[Explanation of symbols]

TNC: TN type liquid crystal cell A, B: Polarizing plate PA, PB: Polarization axis L0: Natural light L1, L5: Linearly polarized light L2: Modulated light after passing through the liquid crystal cell L3, L4: Elliptical polarization LC: TN type liquid crystal cell State of liquid crystal molecules when a sufficient voltage is applied to the electrodes RF1, RF2: retardation film for liquid crystal display element BL: backlight

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location G02F 1/13 500 G02F 1/13 500 (31) Priority claim number Japanese Patent Application No. 7-222785 (32) ) Priority Day Hei 7 (1995) August 9 (33) Priority claiming country Japan (JP) (72) Inventor Masayuki Negoro 210 Nakanuma, Minamiashigara City, Kanagawa Prefecture Fuji Photo Film Co., Ltd.

Claims (10)

[Claims] 1. A discotic liquid crystalline compound having a substituent capable of forming a new bond between at least one kind of molecule and an intramolecular molecule, and a new bond forming at least one kind of intermolecular or intramolecular form. A liquid crystal composition comprising a monocyclic or condensed ring aromatic compound having a substituent which is not discotic liquid crystallinity. 2. The liquid crystal composition according to claim 1, wherein the substituent capable of forming a new bond intermolecularly or intramolecularly is a polymerizable substituent. 3. The liquid crystal composition according to claim 1, wherein the discotic liquid crystal compound is represented by the following general formula (1). General formula (1) In the formula, R ²¹ and R ²² each independently represent a hydrogen atom or a methyl group, and R ²³ represents an alkoxy group containing the substituent P2. R ²⁴ , R ²⁵ and R ²⁶ of the substituent P2 each independently represent a hydrogen atom or an alkyl group. 4. The liquid crystal composition according to claim 1, wherein the compound having no discotic liquid crystallinity is represented by the following general formula (2). General formula (2) In the formula, D1 represents a benzene ring or a naphthalene ring, and represents a group in which a total of n substituents A and substituents [(L1) _s -P4]-are arranged. The k L1 and P4 are each independently, and the (n−k) A is independently a hydrogen atom, an alkyl group or an alkoxy group. n is 6 when D1 is a benzene ring and 8 when it is a naphthalene ring, and k represents an integer of 1 to 3. s and t represent 0 or 1. X1 represents an alkyleneoxy group. R ⁴¹ and R ⁴² each independently represent a hydrogen atom or a methyl group, and R ⁴⁴ , R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom or an alkyl group. R ⁴³ has the same meaning as P 4. 5. The liquid crystal composition according to claim 3, wherein the compound having no discotic liquid crystallinity is the compound represented by the general formula (2) according to claim 4. 6. An optical anisotropy obtained by forming a new bond between or within molecules of a liquid crystal compound after forming a layer made of the liquid crystal composition according to claim 1 on a support. Isotropic material. 7. Optically anisotropic material according to claim 6, characterized in that the formation of new bonds is by polymerization. 8. The method according to claim 6, wherein at least one of the interfaces is formed in contact with the gas phase.
The optically anisotropic material described in. 9. A compound represented by the following general formula (3). General formula (3) In the formula, D4 represents a benzene ring or a naphthalene ring, and represents a group in which a total of n substituents Q and substituents (L4-P7)-are arranged. k L4 and P7 are independent of each other, and (n
-K) Q's each independently represent a hydrogen atom, an alkyl group or an alkoxy group. n is 6 when D4 is a benzene ring and 8 when it is a naphthalene ring, and k is when D4 is a benzene ring,
3 when D4 is a naphthalene ring; However, the 2,6-di-substituted form of naphthalene is excluded. X4 represents an alkyleneoxy group. R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁷⁵ and R
⁷⁶ has the same meaning as R ⁴¹ , R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁵ and R ⁴⁶ of the general formula (2), respectively. 10. A compound represented by the following general formula (4). General formula (4) In the formula, L5 represents an alkylene group. R ⁸⁴ , R ⁸⁵ and R ⁸⁶ each independently represent a hydrogen atom or an alkyl group.