JP2001166147A - Optical compensation sheet and liquid crystal display device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an optical compensation sheet with high anisotropy of refractive index. SOLUTION: A discotic liquid crystalline molecule with a cinnamoyl side chain and a triphenylene nucleus is used as an optically anisotropic layer of the optical compensation sheet.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an optical compensatory sheet having an optically anisotropic layer formed from discotic liquid crystalline molecules on a transparent support, and a liquid crystal display device.

[0002]

2. Description of the Related Art An STN type liquid crystal display device comprises an STN type liquid crystal cell, two polarizing plates, and one or two optical compensation sheets (retardation plates) provided between the STN type liquid crystal cell and the polarizing plate. Consists of The liquid crystal cell is composed of rod-like liquid crystal molecules, two substrates for enclosing the same, and an electrode layer for applying a voltage to the rod-like liquid crystal molecules. In the STN type liquid crystal cell, an alignment film for aligning rod-like liquid crystal molecules is provided on two substrates. Further, using a chiral agent, the rod-like liquid crystalline molecules are twisted at 180 to 360 degrees. The STN-type liquid crystal display device has a feature that even in a simple matrix electrode structure having no active element (thin film transistor or diode), a large capacity clear display is possible by time division driving. In an STN type liquid crystal display device without an optical compensation sheet, the display image is colored blue or yellow due to the birefringence of the rod-like liquid crystal molecules. Coloring of the displayed image is inconvenient in both monochrome display and color display. The optical compensation sheet is used to eliminate such coloring and obtain a bright and clear image. In some cases, the optical compensation sheet may be provided with a function of expanding the viewing angle of the liquid crystal cell. As the optical compensation sheet, a stretched birefringent film has been conventionally used. Optical compensatory sheets for STN type liquid crystal display devices using stretched birefringent films are described in JP-A-7-104284 and JP-A-7-13021.
There is a description in each gazette of the issue.

It has been proposed to use an optical compensatory sheet having an optically anisotropic layer containing discotic liquid crystal molecules on a transparent support instead of an optical compensatory sheet comprising a stretched birefringent film. The optically anisotropic layer is formed by aligning discotic liquid crystal molecules and fixing the alignment state. Discotic liquid crystalline molecules generally have a large birefringence. The discotic liquid crystal molecules have various alignment forms. The use of discotic liquid crystal molecules makes it possible to produce an optical compensatory sheet having optical properties that cannot be obtained with a conventional stretched birefringent film. B.Mour
Ey et al., Mol. Cryst. Liq. Cryst., Vol. 84, p. 193 (1982) discloses a triphenylene-based discotic liquid crystalline molecule having negative birefringence. In order to use the liquid crystal molecules for the optical compensation sheet, it is necessary to uniformly align all the molecules constituting the optically anisotropic layer. That is, it is desirable that the discotic liquid crystal molecules be monodomain aligned. However, since conventional discotic liquid crystal molecules are aligned in dual domains, alignment defects occur at domain boundaries. Therefore, in many cases, conventional discotic liquid crystal molecules cannot obtain optical properties that can be used for an optical compensation sheet. The optical properties depend on the chemical structure of the discotic liquid crystalline molecules. Many types of discotic liquid crystalline molecules have been studied and developed to obtain the required optical properties.

JP-A-7-306317 and JP-A-9-104
No. 866 discloses discotic liquid crystal molecules suitable for forming an optically anisotropic layer of an optical compensation sheet.
2,3,6,7,10,11-Hexa {4- (4-acryloyloxyhexyloxy) benzoyloxy} triphenylene is disclosed. Incidentally, the retardation (シ ョ ン nd) of the optical compensation sheet is determined according to the optical properties of the liquid crystal cell to be compensated. The retardation (Δnd) is the product of the refractive index anisotropy (Δn) of the optically anisotropic layer and the thickness (d) of the optically anisotropic layer.
If the refractive index anisotropy (△ n) of the optically anisotropic layer is large,
Even if the layer thickness (d) is small, the liquid crystal cell can be compensated. However, in the discotic liquid crystal compounds described in JP-A-7-306317 and JP-A-9-104866,
It was very difficult to form an optically anisotropic layer having a sufficiently large refractive index anisotropy (Δn).

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to provide an optical compensatory sheet having a high refractive index anisotropy.

[0006]

An object of the present invention is to provide an optical compensatory sheet of the following (1) to (7) and the following (8):
This was achieved by the liquid crystal display device of (9). (1) A transparent support, an alignment film, and an optically anisotropic layer formed from discotic liquid crystalline molecules represented by the following formula (I) in this order. .06
An optical compensation sheet having a refractive index anisotropy in the range of 5 to 0.16:

[0007]

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Wherein A ¹ and A ² each independently represent a hydrogen atom, a halogen atom or a carbon atom having 1 to 12 carbon atoms.
Y is a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms;
An alkoxy group, an acyl group having 2 to 13 carbon atoms,
An alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms; or A ² and Y combine to form a 5- or 6-membered ring; A halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or carbon atom 2 to 13 atoms
L is -O-, -CO-,-
A divalent linking group selected from the group consisting of S-, -NH-, an alkylene group, an alkenylene group, an alkynylene group, an arylene group and a combination thereof; Q is a polymerizable group; 2, 3 or 4; and b is an integer from 0 to (4-a)]. (2) The optical compensation sheet according to claim 1, wherein the optically anisotropic layer has a refractive index anisotropy in the range of 0.090 to 0.16. (3) The optical compensation sheet according to (1), wherein the alignment film is made of a modified polyvinyl alcohol, an acrylic acid copolymer, or a methacrylic acid copolymer containing 1 to 90 mol% of a repeating unit represented by the following formula (II):

[0009]

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[0010] [wherein, R ² represents a hydrogen atom, a halogen atom or a carbon atoms is an alkyl group of 1 to 6; L ⁰
Is a divalent linking group selected from the group consisting of —O—, —CO—, —NH—, —SO ₂ —, an alkylene group, an alkenylene group, an arylene group and a combination thereof; and R ⁰ is And a hydrocarbon group having 10 to 100 carbon atoms which may be substituted by a fluorine atom]. (4) The discotic liquid crystal molecules are twisted in the optically anisotropic layer, and the twist angle is 90 to 36.
The optical compensatory sheet according to (1), which has a range of 0 degrees. (5) The optical compensation sheet according to (4), wherein the optically anisotropic layer contains a compound having optical rotation. (6) The optical compensation sheet according to (1), wherein the discotic liquid crystal molecules are oriented at an average inclination angle of 50 to 90 degrees with respect to the plane of the transparent support. (7) The optical compensation sheet according to (1), wherein the discotic liquid crystalline molecules are oriented such that the tilt angle changes with the distance between the discotic liquid crystalline molecules and the plane of the transparent support.

(8) STN liquid crystal cell, two polarizing plates disposed on both sides thereof, and one or two optical compensation sheets disposed between the STN liquid crystal cell and one or both polarizing plates An STN type liquid crystal display device comprising:
The optical compensation sheet has, in this order, a transparent support, an alignment film, and an optically anisotropic layer formed from the discotic liquid crystalline molecules represented by the formula (I). Having a refractive index anisotropy in the range of 0.065 to 0.16, the discotic liquid crystalline molecules are oriented at an average tilt angle in the range of 50 to 90 degrees, and further twisted,
An STN liquid crystal display device having a twist angle in the range of 90 to 360 degrees. (9) TN liquid crystal cell, TN comprising two polarizing plates disposed on both sides thereof and one or two optical compensation sheets disposed between the TN liquid crystal cell and one or both polarizing plates -Type liquid crystal display device, wherein the optical compensation sheet has a transparent support, an alignment film, and an optically anisotropic layer formed from the discotic liquid crystal molecules represented by the formula (I) in this order, The optically anisotropic layer has a refractive index anisotropy in the range of 0.065 to 0.16, and the discotic liquid crystalline molecules are changed according to the distance between the discotic liquid crystalline molecules and the plane of the transparent support. A TN-type liquid crystal display device, wherein the liquid crystal display device is oriented so that the tilt angle changes. In the present specification, the tilt angle of the discotic liquid crystal molecules is:
It means the angle between the disk surface of discotic liquid crystalline molecules and the surface of the support. A state in which the liquid crystal molecules are oriented at an average inclination angle in the range of 50 to 90 degrees is referred to as a state in which the liquid crystal molecules are substantially vertically oriented.

[0012]

As a result of the research by the present inventors, when an optically anisotropic layer is formed from the discotic liquid crystalline molecules represented by the above formula (I), a high refractive index difference of 0.065 to 0.16 can be obtained. It has been found that anisotropy can be achieved. Since an optically anisotropic layer having a high refractive index anisotropy was obtained, it was possible to sufficiently compensate the liquid crystal cell even with a relatively thin optical compensatory sheet. Further, when the optically anisotropic layer is thin, it is easy to control the alignment of the discotic liquid crystalline molecules, and an optimum alignment state can be obtained. The optical compensatory sheet of the present invention can easily control the orientation of the discotic liquid crystal molecules. Therefore, not only the optical compensatory sheet for STN-type liquid crystal display devices assumed at the beginning of the research but also other liquid crystal display devices (for example, TN type liquid crystal display device) can be effectively used by appropriately controlling the alignment state.

[0013]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS FIG. 1 shows an alignment state of rod-like liquid crystal molecules in a liquid crystal cell and a discotic liquid crystal in an optically anisotropic layer in a pixel portion of an STN type liquid crystal display device when no voltage is applied (off). FIG. 3 is a cross-sectional view schematically illustrating an orientation state of a hydrophilic molecule. As shown in FIG. 1, the liquid crystal cell includes an upper substrate (1
1) Between the lower alignment film (12) and the upper alignment film (14) of the lower substrate (15), rod-like liquid crystal molecules (13a-1)
3e) has a liquid crystal layer formed therein. Alignment film (1
Due to the functions of the chiral agent added to the liquid crystal layer and the chiral agent added to the liquid crystal layer, the rod-like liquid crystal molecules (13a to 13e) are twisted as shown in FIG. Although omitted in FIG. 1, the upper substrate (11) and the lower substrate (15) of the liquid crystal cell each have an electrode layer. The electrode layer has a function of applying a voltage to the rod-like liquid crystal molecules (13a to 13e). S
When the applied voltage of the TN type liquid crystal cell is 0 (when no voltage is applied), as shown in FIG.
3e) is oriented substantially parallel (in the horizontal direction) to the plane of the alignment films (12, 14). Then, rod-like liquid crystalline molecules (1
3a to 13e) are oriented so as to form a spiral in a horizontal plane while being twisted along the thickness direction (in FIG. 1, approximately 240 ° counterclockwise from 13a to 13e). When a voltage is applied (on) to the STN-type liquid crystal cell, the rod-like liquid crystal molecules (13b to 13b) at the central portion in the liquid crystal cell are applied.
13d) is oriented more vertically (rearranged in parallel to the direction of the electric field) as compared to when no voltage is applied (off). Rod-like liquid crystal molecules (13a, 13a) near the alignment films (12, 14)
The orientation state of e) does not substantially change even when a voltage is applied.

An optical compensation sheet is disposed below the liquid crystal cell. The optical compensation sheet shown in FIG. 1 has an alignment film (22) and an optically anisotropic layer on a transparent support (23) in this order. The optically anisotropic layer is a layer obtained by aligning discotic liquid crystal molecules (21a to 21e) and fixing the molecules in the aligned state. In the present invention, as shown in FIG. 1, discotic liquid crystal molecules (21a
21e) is oriented substantially perpendicular to the plane of the alignment film (22). And, as shown in FIG.
The discotic liquid crystal molecules (21a to 21e) spiral in a horizontal plane while being twisted along the thickness direction (in FIG. 1, approximately 24 clockwise from 21a to 21e).
It is preferable to orient in such a direction as 0 °). In FIG. 1, rod-like liquid crystal molecules and discotic liquid crystal molecules are 13a and 21e, 13b and 21d, and 13c and 21c.
c, 13d and 21b, and 13e and 21a have a corresponding relationship. That is, the discotic liquid crystal molecules 21e optically compensate the rod-like liquid crystal molecules 13a, and similarly, the discotic liquid crystal molecules 21a optically compensate the rod-like liquid crystal molecules 13e. Each correspondence will be described with reference to FIG.

FIG. 2 is a schematic diagram showing the refractive index ellipsoids of the rod-like liquid crystal molecules of the liquid crystal cell and the discotic liquid crystal molecules of the optical compensatory sheet which has a relationship of optically compensating the rod-like liquid crystal molecules. The refractive index ellipsoid (13) of the rod-like liquid crystal molecules of the liquid crystal cell has a refractive index (1) in a plane parallel to the alignment film.
3x, 13y) and the refractive index (13) in the thickness direction of the liquid crystal cell.
z). In the STN type liquid crystal cell, the refractive index (13x) in one direction in a plane parallel to the alignment film has a large value, and the refractive index (13y) in the plane perpendicular to the direction and the refractive index (13x) in the thickness direction of the liquid crystal cell (13x). 13z) is a small value. Therefore, the refractive index ellipsoid (13) has a shape in which a rugby ball is laid horizontally as shown in FIG. In such a liquid crystal cell having a non-spherical refractive index ellipsoid,
Angle dependence of birefringence occurs. This angle dependency is eliminated by using an optical compensation sheet.

The refractive index ellipsoid (21) of the discotic liquid crystal molecules of the optical compensatory sheet which has a relationship of optically compensating the rod-like liquid crystal molecules also has a refractive index (21x, 21y) in a plane parallel to the alignment film. The optically anisotropic layer is formed by the refractive index (21z) in the thickness direction. In the present invention, by aligning the discotic liquid crystal molecules substantially vertically, the refractive index (21x) in one direction in a plane parallel to the alignment film becomes a small value, and the in-plane refraction in the direction perpendicular to that direction is reduced. Rate (2
1y) and the refractive index (21z) in the thickness direction of the optically anisotropic layer
Is a large value. Therefore, the refractive index ellipsoid (21)
Has an upright disk shape as shown in FIG. From the above relationship, the retardation generated in the liquid crystal cell (1) can be offset by the optical compensation sheet (2). That is, the refractive index (13x, 13
y, 13z), the refractive index of discotic liquid crystal molecules (21x, 21y, 21z), the thickness of a rod-shaped liquid crystal molecule layer having the same director direction (13t), and the thickness of the discotic liquid crystal molecule layer (21t) If the liquid crystal display device is designed so as to satisfy the following expression, the angle dependence of the liquid crystal cell can be eliminated. │ (13x-13y) × 13t│ = │ (21x-21
y) × 21t││ (13x-13z) × 13t│ = │ (21x-21
z) × 21t│

FIG. 3 is a schematic diagram showing the layer structure of an STN type liquid crystal display device. The liquid crystal display device shown in FIG. 3A includes a lower polarizing plate (3) in order from the backlight (BL) side.
a), a lower optical compensation sheet (2a), an STN type liquid crystal cell (1), and an upper polarizing plate (3b) in this order. The liquid crystal display device shown in FIG. 3B includes, in order from the backlight (BL) side, a lower polarizing plate (3a), a lower optical compensation sheet (2a), an upper optical compensation sheet (2b), and an STN-type liquid crystal cell ( 1) and an upper polarizing plate (3b). The liquid crystal display device shown in FIG. 3C includes, in order from the backlight (BL) side, a lower polarizing plate (3a), an STN-type liquid crystal cell (1), an upper optical compensation sheet (2b), and an upper polarizing plate ( 3b). The liquid crystal display device shown in FIG. 3D includes, in order from the backlight (BL) side, a lower polarizing plate (3a), an STN-type liquid crystal cell (1), a lower optical compensation sheet (2a), and an upper optical compensation sheet ( 2b), and an upper polarizing plate (3b). The liquid crystal display device shown in FIG. 3E includes, in order from the backlight (BL) side, a lower polarizing plate (3a) and a lower optical compensation sheet (2).
a), STN type liquid crystal cell (1), upper optical compensation sheet (2)
b) and the upper polarizing plate (3b).

FIG. 3 shows the lower polarizing plate (3a) as an arrow.
, The normal (director) direction (DDa) of the discotic liquid crystal molecules near the alignment film of the lower optical compensation sheet (2a) (DDa), and the vicinity of the liquid crystal cell of the lower optical compensation sheet (2a). The direction of the normal (director) of the discotic liquid crystalline molecule (director) (DDb), the rubbing direction of the lower alignment film of the liquid crystal cell (1) (RDa), and the rubbing direction of the upper alignment film of the liquid crystal cell (1) (RDb) , The normal (director) direction (D) of the discotic liquid crystal molecules near the liquid crystal cell of the upper optical compensation sheet (2b).
Dc), the normal (director) direction (DDd) of the disk surface of the discotic liquid crystalline molecules near the alignment film of the upper optical compensation sheet (2b), and the transmission axis (TAb) of the upper polarizing plate (3b). . The exact angles are described in FIGS. 4 and 5.

FIG. 4 is a plan view showing preferred optical directions for each element of the STN type liquid crystal display device. FIG.
Is an arrangement that emphasizes front contrast. FIG. 4 (a) shows the lower polarizing plate and ST as shown in FIG. 3 (a).
This is a case where one optical compensation sheet is provided between the liquid crystal cell and the N-type liquid crystal cell. (B) of FIG. 4, as shown in (b) of FIG.
This is a case where two optical compensation sheets are provided between the lower polarizing plate and the STN type liquid crystal cell. FIG. 4 (c) is the same as FIG. 3 (c).
As shown in (1), there is a case where one optical compensation sheet is provided between the STN type liquid crystal cell and the upper polarizing plate. FIG. 4D
FIG. 3D shows a case where two optical compensation sheets are provided between the STN type liquid crystal cell and the upper polarizing plate as shown in FIG. FIG. 4E shows one optical compensation sheet between the lower polarizing plate and the STN liquid crystal cell and between the STN type liquid crystal cell and the upper polarizing plate as shown in FIG. This is a case where one optical compensation sheet is provided in total. X is the standard (0
゜), and the meaning of each arrow is shown in FIG.
As described in the above. The transmission axis of the lower polarizing plate (TA
The arrangement may be such that a) and the transmission axis (TAb) of the upper polarizing plate are interchanged.

FIG. 5 is a plan view showing another preferred optical direction for each element of the STN type liquid crystal display device.
FIG. 5 shows an arrangement in which color is emphasized. (A) of FIG.
As shown in FIG. 3A, this is a case where one optical compensation sheet is provided between the lower polarizing plate and the STN type liquid crystal cell. FIG. 5B shows a case where two optical compensation sheets are provided between the lower polarizing plate and the STN liquid crystal cell, as shown in FIG. 3B. FIG. 5C shows a case where one optical compensation sheet is provided between the STN type liquid crystal cell and the upper polarizing plate as shown in FIG. 3C. FIG. 5D shows a case where two optical compensation sheets are provided between the STN liquid crystal cell and the upper polarizing plate, as shown in FIG. 3D. FIG. 5 (e) shows the lower polarizing plate and ST as shown in FIG. 3 (e).
One optical compensation sheet and ST between the N-type liquid crystal cell
This is the case where two optical compensation sheets are provided between the N-type liquid crystal cell and the upper polarizing plate. X is a reference direction (0 °), and the meaning of each arrow is as described with reference to FIG. The transmission axis (TAa) of the lower polarizing plate and the transmission axis (TAb) of the upper polarizing plate may be interchanged.

[Transparent Support] As the support, it is preferable to use a polymer film which is transparent and has small optical anisotropy. Transparent support means that the light transmittance is 80% or more. Small optical anisotropy means
Specifically, the in-plane retardation (Re) is 20 nm.
Or less, more preferably 10 nm or less. Further, the retardation (Rth) in the thickness direction is preferably 100 nm or less, and is preferably 5 nm or less.
More preferably, it is 0 nm or less. The in-plane retardation (Re) and the thickness direction retardation (Rth) of the transparent support are defined by the following formulas. Re = (nx ¹ −ny ¹ ) × d ¹ Rth = [{(nx ¹ + ny ¹ ) / 2} −nz ¹ ] × d ¹ where nx ¹ and ny ¹ are in-plane refractive indices of the transparent support. Where nz ¹ is the refractive index in the thickness direction of the transparent support, and d ¹ is the thickness of the transparent support.

Examples of polymers include cellulose esters,
Includes polycarbonate, polysulfone, polyethersulfone, polyacrylate and polymethacrylate. Cellulose esters are preferred, acetyl cellulose is more preferred, and triacetyl cellulose is most preferred. The polymer film is preferably formed by a solvent casting method. The thickness of the transparent support is
It is preferably 20 to 500 μm, and 50 to 2 μm.
More preferably, it is 00 μm. In order to improve the adhesion between the transparent support and the layer provided thereon (adhesive layer, alignment film or optically anisotropic layer), the transparent support is subjected to a surface treatment (eg, glow discharge treatment, corona discharge treatment, ultraviolet light). (U
V) treatment, flame treatment). An adhesive layer (undercoat layer) may be provided on the transparent support.

[Alignment Film] The alignment film is formed by rubbing an organic compound (preferably a polymer), obliquely depositing an inorganic compound, forming a layer having microgrooves, or by using a Langmuir-Blodgett method (LB film). (Eg, ω-tricosanoic acid, dioctadecylmethylammonium chloride, methyl stearylate). In addition, the application of an electric field,
There is also known an alignment film in which an alignment function is generated by applying a magnetic field or irradiating light. An alignment film formed by rubbing a polymer is particularly preferable. The rubbing treatment is performed by rubbing the surface of the polymer layer several times with paper or cloth in a certain direction. The thickness of the alignment film is 0.01 to 10 μm
Is preferably, and more preferably, 0.05 to 1 μm. In the optical compensation sheet for a TN type liquid crystal cell, it is preferable that the discotic liquid crystal molecules are oriented so that the tilt angle changes with the distance between the discotic liquid crystal molecules and the plane of the transparent support. For this purpose, it is preferable to use a polymer that does not reduce the surface energy of the alignment film (a normal polymer for an alignment film) as a polymer constituting the alignment film. Ordinary polymers for alignment films are described in many documents and many commercially available products are available.

In the optical compensatory sheet for the STN type liquid crystal cell, it is preferable to use, as the polymer constituting the alignment film, a polymer which lowers the surface energy of the alignment film. As the functional group for lowering the surface energy to be introduced into the polymer, a hydrocarbon group having 10 to 100 carbon atoms which may be substituted by a fluorine atom is effective. The hydrocarbon group is preferably present on the surface of the alignment film.
For that purpose, a hydrocarbon group is introduced into the side chain terminal of the polymer. The main chain of the polymer is preferably polyvinyl alcohol, polyacrylic acid or polymethacrylic acid. In the optical compensation sheet for an STN type liquid crystal cell, the alignment film has a repeating unit represented by the following formula (II) of 1 to 90.
It is particularly preferred that it consists of a modified polyvinyl alcohol, acrylic acid copolymer or methacrylic acid copolymer containing mol%.

[0025]

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In the formula (II), R ² is a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms. R ² is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom, methyl or ethyl, and most preferably a hydrogen atom or methyl. In the formula (II), L ⁰ represents —O—, —CO—, —NH—, —SO
_2- , a divalent linking group selected from the group consisting of alkylene, alkenylene, arylene and combinations thereof. In the case of modified polyvinyl alcohol, L ⁰
Is -O-L ⁰⁰ -(-O- is bonded to the main chain and L ^{00 is}
Is, -O -, - CO -, - NH -, - SO 2 -, an alkylene group, an alkenylene group, a divalent linking group selected from the group consisting of arylene groups and combinations thereof) is particularly preferred. In the case of an acrylic acid copolymer or a methacrylic acid copolymer, L ⁰ is -CO-L ⁰⁰
(-CO- is bonded to the main chain, and L ⁰⁰ is -O-,
-CO -, - NH -, - SO 2 -, an alkylene group, an alkenylene group, a divalent linking group selected from the group consisting of arylene groups and combinations thereof) is particularly preferred.

In the case of modified polyvinyl alcohol, L
⁰ is -O-, -O-alkylene group-, -O-alkylene group-alkenylene group-, -O-alkylene group-arylene group-, -O-alkylene group -O-, -O-alkylene group -O -CO -, - O-alkylene group -NH-SO ₂
-Arylene group -O-, -O-alkylene group -O-CO
-Alkylene group -O-, -O-alkylene group -CO-N
H -, - O-alkylene group -NH-SO ₂ -, - O- alkylene group -O-CO- arylene group -, - O-arylene group -O-CO- alkylene group -O- arylene group -, - O -Arylene group-, -O-alkylene group-CO
-O-, -O-alkylene group -CO- or -O-arylene group -CO-O-, preferably -O-,
-O- alkylene group -NH-SO ₂ - arylene group -O
-, -O-alkylene group- or -O-alkylene group-
More preferably, it is an arylene group. In these linking groups, the left side is bonded to the main chain, and the right side is bonded to R ⁰ .

In the case of an acrylic acid copolymer or a methacrylic acid copolymer, L ⁰ is —CO—O—, —CO—O
-Alkylene group-, -CO-O-alkylene group-alkenylene group-, -CO-O-alkylene group-arylene group-, -CO-O-alkylene group -O-, -CO-O-alkylene group -O- CO-, -CO-O-alkylene group-
NH-SO ₂ - arylene group -O -, - CO-O- alkylene group -O-CO- alkylene group -O -, - CO-O
- an alkylene group -CO-NH -, - CO- O- alkylene group _{-NH-SO 2 -, - CO} -O- alkylene group -O
-CO-arylene group-, -CO-NH-, -CO-N
H-arylene group-, -CO-NH-arylene group-C
O-O-, -CO-O-arylene group -O-CO-alkylene group -O-arylene group-, -CO-O-arylene group-, -CO-NH-arylene group -NH-CO-,
-CO-NH-arylene group -O-, -CO-O-alkylene group -CO-O-, -CO-O-alkylene group -C
O-, -CO-O-arylene group -CO-O- or-
CO-NH- is preferably an alkylene group -NH-CO-O- in which, -CO-O -, - CO -O- alkylene group -NH-SO ₂ - arylene group -O -, - CO-NH
-, -CO-NH-arylene group -O-, -CO-O-
More preferably, it is an alkylene group-, -CO-O-alkylene group -arylene group- or -CO-O-alkylene group -O-CO-arylene group-, -CO-O
-Or -CO-NH- is most preferred. In these linking groups, the left side is bonded to the main chain, and the right side is R
^Bind to ⁰ .

The alkylene group may have a branched or cyclic structure. The number of carbon atoms in the alkylene group is 1
It is preferably from 30 to 30, more preferably from 1 to 15, and most preferably from 1 to 12. The alkenylene group may have a branched or cyclic structure. The alkenylene group preferably has 2 to 30 carbon atoms, more preferably 2 to 16 carbon atoms, and most preferably 2 to 4 carbon atoms. The arylene group is preferably phenylene or naphthylene, more preferably phenylene, and most preferably p-phenylene. The arylene group may have a substituent. Examples of the substituent of the arylene group include a halogen atom, carboxyl, cyano, nitro, carbamoyl, sulfamoyl, an alkyl group, a cycloalkyl group, an alkoxy group, an alkylthio group, an acyl group, an acyloxy group, an alkyl-substituted carbamoyl group, and an alkyl-substituted sulfamoyl. Groups, amide groups, sulfonamide groups and alkylsulfonyl groups.

In the formula (II), R ⁰ is a hydrocarbon group having 10 to 100 carbon atoms which may be substituted by a fluorine atom. The hydrocarbon group is an aliphatic group, an aromatic group, or a combination thereof. The aliphatic group may be cyclic, branched, or linear. The aliphatic group is preferably an alkyl group (may be a cycloalkyl group) or an alkenyl group (may be a cycloalkenyl group). The hydrocarbon group may have a substituent that does not show strong hydrophilicity, such as a halogen atom. The number of carbon atoms in the hydrocarbon group is preferably from 10 to 80, more preferably from 10 to 60, and
Most preferably, it is 0 to 40.

The hydrocarbon group preferably has a steroid structure. The steroid structure has an exclusion volume effect in addition to the function of lowering the surface energy of the alignment film. When an exclusion volume effect is imparted to the alignment film, the liquid crystal molecules are brought upright in synergy with the effect of lowering the surface energy. In the present specification, the steroid group means a cyclopentanohydrophenanthrene ring group or a ring group in which a part of the bond of the ring is a double bond. The number of carbon atoms of the hydrocarbon group having a steroid group is preferably 18 to 100, more preferably 19 to 60, and most preferably 20 to 40. Further, the hydrocarbon group also preferably contains at least two aromatic rings or aromatic heterocycles. More preferably, the hydrocarbon group contains at least two aromatic rings.
The two aromatic rings are directly connected by a single bond (the two aromatic rings form a biphenyl structure) or an ethynylene bond (-C≡
It is particularly preferred that C-) is linked (two aromatic rings form a tolan structure).

The hydrocarbon group may have a substituent that does not show strong hydrophilicity, such as another halogen atom, in addition to the fluorine atom. The modified polyvinyl alcohol, acrylic acid copolymer or methacrylic acid copolymer preferably contains the repeating unit represented by the formula (II) in an amount of 2 to 80 mol%, more preferably 3 to 70 mol%.

The modified polyvinyl alcohol contains a repeating unit represented by the following formula (III) (a repeating unit corresponding to vinyl alcohol) in addition to the repeating unit represented by the formula (II). Further, the modified polyvinyl alcohol generally contains a repeating unit represented by the following formula (IV) (a repeating unit corresponding to vinyl acetate) in addition to the repeating units represented by the formulas (II) and (III).

[0034]

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[0035] Polyvinyl alcohol is generally prepared by saponification of polyvinyl acetate. Therefore, polyvinyl alcohol usually contains some repeating units corresponding to vinyl acetate represented by the above formula (IV). The modified polyvinyl alcohol containing a repeating unit represented by the formula (II) usually contains a small amount of the repeating unit represented by the formula (IV).

The acrylic acid copolymer or methacrylic acid copolymer has a repeating unit represented by the following formula (V) (a repeating unit corresponding to acrylic acid or methacrylic acid) in addition to the repeating unit represented by the formula (II). Including.

[0037]

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In the formula (V), R ¹ is a hydrogen atom (acrylic acid copolymer) or methyl (methacrylic acid copolymer). In the formula (V), M is a proton,
It is an alkali metal (eg, Na, K) ion or an ammonium ion. The ammonium ion is an organic group (eg,
Methyl) to be substituted (primary to quaternary).
Examples of ammonium ions include NH ₄ , NH ₃ CH ₃ ,
NH ₂ (CH ₃ ) ₂ , NH (CH ₃ ) ₃ and N (CH
₃ ) Includes ₄ .

In the case of the modified polyvinyl alcohol, a group different from the repeating unit may be bonded to the terminal of the polymer. Examples of the terminal group include an alkylthio group.

Polymerizable groups may be introduced into the modified polyvinyl alcohol or (meth) acrylic acid copolymer. When a modified polyvinyl alcohol or a (meth) acrylic acid copolymer having a polymerizable group is used in combination with a discotic liquid crystal molecule having a polymerizable group, the modified polyvinyl alcohol or the (meth) acrylic acid copolymer and the liquid crystal molecule can be optically combined. Chemical bonding can be achieved through the interface between the anisotropic layer and the alignment film. Thereby, the durability of the optical compensation sheet can be improved. The type of the polymerizable group is determined according to the type of the polymerizable group (Q) of the discotic liquid crystal molecule described below. The polymerizable group (Q) of the liquid crystal molecule is preferably an unsaturated polymerizable group (Q1 to Q7 described below), an epoxy group (Q8) or an aziridinyl group (Q9), as described later. It is more preferably a saturated polymerizable group, and most preferably an ethylenically unsaturated polymerizable group (Q1 to Q6). Similarly, the polymerizable group of the modified polyvinyl alcohol or (meth) acrylic acid copolymer is preferably an unsaturated polymerizable group, an epoxy group or an aziridinyl group, more preferably an unsaturated polymerizable group, and more preferably an ethylenically unsaturated group. Most preferably, it is a saturated polymerizable group.

It is preferable that the main chain and the polymerizable group are not directly linked but are linked via a linking group. In the case of the modified polyvinyl alcohol, examples of the linking group include -O-, -O-alkylene group-, -O-alkylene group-alkenylene group-,-
O- alkylene group - arylene group -, - O- alkylene group -O -, - O- alkylene group -O-CO -, - O- alkylene group -NH-SO ₂ - arylene group -O -, - O
-Alkylene group -O-CO-alkylene group -O-, -O
-Alkylene group -CO-NH-, -O-alkylene group-
NH-SO ₂ -, - O-alkylene group -O-CO- arylene group -, - O-arylene group -O-CO- alkylene group -O- arylene group -, - O-arylene group -, -
O-alkylene group -CO-O-, -O-alkylene group-
CO- and -O-arylene groups -CO-O- are included (the left side is bonded to the main chain, and the right side is bonded to the polymerizable group).

In the case of an acrylic acid copolymer or a methacrylic acid copolymer, examples of the linking group include -CO- and -CO
-O-, -CO-NH-, -CO-NH-alkylene group-, -CO-NH-alkylene group -O-, -CO-NH
-Alkylene group -CO-O-, -CO-NH-alkylene group -O-CO-, -CO-NH-alkylene group -CO
-NH-, -CO-alkylene group -O-CO-, -CO
-Arylene group -O-alkylene group -O-CO-, -C
O-arylene group -O-alkylene group -O-, -CO-
And an arylene group -O-alkylene group- and -CO-alkylene group -O-CO- (the left side is bonded to the main chain, and the right side is bonded to the polymerizable group).

The above alkylene group may have a branched or cyclic structure. The number of carbon atoms in the alkylene group is 1
It is preferably from 30 to 30, more preferably from 1 to 20, still more preferably from 1 to 15, and most preferably from 1 to 12. The arylene group is preferably phenylene or naphthylene, more preferably phenylene, and p-
Most preferably, it is phenylene. The arylene group may have a substituent. Examples of the substituent of the arylene group include a halogen atom (F, Cl, Br), carboxyl, cyano, nitro, carbamoyl, sulfamoyl, alkyl group, cycloalkyl group, alkoxy group, alkylthio group, acyl group, acyloxy group, alkyl Includes substituted carbamoyl, alkyl-substituted sulfamoyl, amide, sulfonamide and alkylsulfonyl groups.

The above alkyl group may have a branch. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and preferably 1 to 15 carbon atoms.
It is more preferably from 10 to 10, and most preferably from 1 to 6. The cycloalkyl group is preferably cyclohexyl. The alkoxy group is
It may have a branch. The alkoxy group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 6. The alkylthio group may have a branch. The number of carbon atoms of the alkylthio group is preferably 1 to 20, more preferably 1 to 15, and more preferably 1 to 10
Is more preferable, and 1 to 6 is most preferable. The acyl group has 2 to 20 carbon atoms.
Is preferably 2 to 15, more preferably 2 to 10, and most preferably 2 to 6. The acyloxy group preferably has 2 to 20 carbon atoms, more preferably 2 to 15 carbon atoms, further preferably 2 to 10 carbon atoms, and most preferably 2 to 6 carbon atoms.

The alkyl-substituted carbamoyl group preferably has 2 to 20 carbon atoms, and preferably has 2 to 15 carbon atoms.
Is more preferable, 2 to 10 is more preferable, and 2 to 6 is most preferable. The alkyl part of the alkyl-substituted carbamoyl group may further have a substituent (eg, an alkoxy group). The alkyl-substituted sulfamoyl group has 2 to 2 carbon atoms.
It is preferably 0, more preferably 2 to 15, further preferably 2 to 10, and 2
It is most preferably from 6 to 6. The alkyl part of the alkyl-substituted sulfamoyl group may further have a substituent (eg, an alkoxy group). The amide group preferably has 2 to 20 carbon atoms, and preferably has 2 to 15 carbon atoms.
Is more preferable, 2 to 10 is more preferable, and 2 to 6 is most preferable. The number of carbon atoms of the sulfonamide group is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, and more preferably 1 to 6.
Is most preferred. The alkylsulfonyl group preferably has 1 to 20 carbon atoms,
It is more preferably from 15 to 15, further preferably from 1 to 10, and most preferably from 1 to 6. The alkyl part of the alkylsulfonyl group may further have a substituent (eg, an alkoxy group).

The above polymerizable group can be introduced into the repeating unit represented by the formula (II) having a hydrocarbon group. The polymerizable group is preferably a substituent of a hydrocarbon group, more preferably a substituent of the most terminal hydrocarbon group or a fluorine atom-substituted hydrocarbon group. It is preferable that the hydrocarbon group and the polymerizable group are not directly linked but are linked via a linking group. Examples of the linking group include -O-, -C
O-, -O-CO-, -CO-O-, -O-CO-O
-, - CO-NH -, - SO 2 -NH -, - NH-CO
-, - NH-CO-O -, - NH-SO 2 -, - alkylene group -, - alkenylene group -, - alkynylene group -,
-O-alkylene group- and -alkylene group -O- are included (the left side is bonded to the hydrocarbon group, and the right side is bonded to the polymerizable group). The alkylene group may have a branched or cyclic structure. The number of carbon atoms in the alkylene group is 1
It is preferably from 30 to 30, more preferably from 1 to 20, still more preferably from 1 to 15, and most preferably from 1 to 12. The alkenylene group and the alkynylene group may have a branched or cyclic structure. The alkenylene group and the alkynylene group preferably have 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and more preferably 2 to 15 carbon atoms.
Is more preferably, and most preferably 2 to 12. The hydrocarbon group may have two or more polymerizable groups as substituents.

In the case of modified polyvinyl alcohol, a strong hydrophilic group may be introduced into the polymer. By introducing a strong hydrophilic group into the modified polyvinyl alcohol, an alignment film can be formed using an aqueous solvent. (Meta)
In the case of an acrylic acid copolymer, a carboxyl group (—CO
Since OM) functions as a strong hydrophilic group, an alignment film can be formed using an aqueous solvent without separately introducing a hydrophilic group. The strong hydrophilic group is introduced into the modified polyvinyl alcohol as a repeating unit having a hydrophilic group, or a hydrophilic group is introduced into the repeating unit having a hydrocarbon group. A strong hydrophilic group means that it shows stronger hydrophilicity than a hydroxyl group of polyvinyl alcohol. The repeating unit having a group showing a stronger hydrophilicity than the hydroxyl group of polyvinyl alcohol is a modified polyvinyl using the repeating unit, instead of a modified polyvinyl alcohol using a repeating unit derived from vinyl alcohol instead of the repeating unit. Alcohol means a repeating unit having higher solubility in water. Such hydrophilic groups include anionic groups (eg, carboxyl, sulfo), cationic groups (eg, ammonium, amino, amide, sulfonamide, hydrazide, hydrazino, carbamoyl, sulfamoyl) and nonionic groups Groups (eg, a group composed of polyethylene glycol).

Modified polyvinyl alcohol or (meth)
The polymerization degree of the acrylic acid copolymer is 200 to 5000
, And particularly preferably 300 to 3000. The molecular weight of the modified polyvinyl alcohol or (meth) acrylic acid copolymer is from 9000 to 2
00000, preferably 13,000 to 13
0000 is particularly preferred. Two or more kinds of modified polyvinyl alcohol or (meth) acrylic acid copolymer may be used in combination. A modified polyvinyl alcohol or (meth) acrylic acid copolymer may be used after crosslinking. The cross-linking reaction is preferably carried out using a cross-linking agent at the same time as or after the application of the coating solution for the alignment film. Examples of the crosslinking agent include a methylol phenol resin, an amino resin (for example, a resin obtained by addition polymerization of melamine, benzoquanamine or urea with formaldehyde or alcohol), an amine compound, a triazine compound, an isocyanate compound, an epoxy compound, and a metal oxide. Compounds, metal halides, organic metal halides, metal salts of organic acids, metal alkoxides and compounds containing oxazoline groups. The amount of the cross-linking agent used is preferably 0.1 to 20% by weight, more preferably 0.5 to 15% by weight of the coating amount of the alignment film. The amount of the cross-linking agent remaining in the alignment film unreacted is preferably 1.0% by weight or less, more preferably 0.5% by weight or less of the coating amount of the alignment film.

[Optical Anisotropic Layer] The optically anisotropic layer
It has a refractive index anisotropy in the range of 0.065 to 0.16. More preferably, the refractive index anisotropy is in the range of 0.090 to 0.16. The refractive index anisotropy (Δn) is
It is defined by the following equation. Δn = nx−ny wherein Δn is the refractive index anisotropy of the optically anisotropic layer;
nx is the maximum refractive index of the optically anisotropic layer; and ny is the minimum refractive index of the optically anisotropic layer. In the present invention, an optically anisotropic layer is formed from discotic liquid crystalline molecules represented by the following formula (I).

[0050]

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In the formula (I), A ¹ and A ² each independently represent a hydrogen atom, a halogen atom (F, Cl, B
r) an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. A ¹ and A ² are each independently preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and preferably have 1 hydrogen atom or 1 carbon atom.
It is more preferably an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and most preferably a hydrogen atom, methyl, ethyl or methoxy.
In the formula (I), Y represents a hydrogen atom, a halogen atom (F, Cl, Br), an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and 2 to 2 carbon atoms. 13 acyl groups, having 1 to 12 carbon atoms
Is an alkylamino group or an acyloxy group having 2 to 13 carbon atoms. Y is a hydrogen atom, a halogen atom,
An alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms is preferable, and a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms is preferable. More preferably a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and more preferably a hydrogen atom, methyl, ethyl or methoxy. Is most preferred.

In the formula (I), A ² and Y may combine to form a 5- or 6-membered ring. Form 5
The membered ring or the six-membered ring includes a cycloheptadiene ring and a cyclohexadiene ring. As shown in the formula (I), the carbon-carbon double bond is of a trans type.

In the formula (I), Z is a halogen atom (F, Cl, Br), an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and 2 to 2 carbon atoms. 13 acyl groups, having 1 to 12 carbon atoms
Is an alkylamino group or an acyloxy group having 2 to 13 carbon atoms. The number of carbon atoms in the alkyl group is
It is preferably 1 to 8. Examples of alkyl groups include:
Methyl, ethyl, n-propyl, n-pentyl and n
-Heptyl is included. Examples of the above alkoxy groups include methoxy and 2-methoxyethoxy. Examples of the above acyl groups include acetyl. Examples of the above-mentioned alkylamino group include methylamino, ethylamino and dimethylamino. The acyloxy group includes acetyloxy and acryloyloxy. Z is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, and preferably an alkyl group having 1 to 4 carbon atoms. More preferably, it is most preferably methyl.

In the formula (I), L represents —O—, —CO
And a divalent linking group selected from the group consisting of-, -S-, -NH-, an alkylene group, an alkenylene group, an alkynylene group, an arylene group, and combinations thereof. L
Is a group obtained by combining at least two divalent groups selected from the group consisting of -O-, -CO-, -S-, -NH-, an alkylene group, an alkenylene group, an alkynylene group and an arylene group. Preferably, -O-, -CO
-, An alkylene group, an alkenylene group, an alkynylene group and an arylene group, more preferably a group obtained by combining at least two divalent groups selected from the group consisting of -O-, -CO-, an alkylene group and an alkenylene group. And a group obtained by combining at least two divalent groups selected from the group consisting of alkynylene groups, and at least two divalent groups selected from the group consisting of -O-, -CO- and an alkylene group. It is most preferred that these groups are combined. The alkylene group preferably has 1 to 12 carbon atoms. The alkenylene group and the alkynylene group preferably have 2 to 12 carbon atoms. The arylene group preferably has 6 to 10 carbon atoms. The alkylene group, alkenylene group, alkynylene group and arylene group may have a substituent (eg, an alkyl group, a halogen atom, a cyano, an alkoxy group, an acyloxy group).

Examples of L are shown below. The left side is bonded to any carbon atom as a substituent of the benzene ring of the formula (II), and the right side is bonded to a polymerizable group (Q) described later. AL represents an alkylene group, alkenylene group or alkynylene group, and AR represents an arylene group. The following n is
It is an integer of 2 to 15.

L1: -AL-CO-O-AL- L2: -AL-CO-O-AL-O- L3: -AL-CO-O-AL-O-AL- L4: -AL-CO-O -AL-O-CO-L5: -CO-AR-O-AL-L6: -CO-AR-O-AL-O-L7: -CO-AR-O-AL-O-CO-L8: -CO -NH-AL-L9: -NH-AL-O-L10: -NH-AL-O-CO-L11: -O-AL-L12: -O-AL-O-L13: -O-AL-O- CO-

L14: -O-AL-O-CO-NH-AL-L15: -O-AL-S-AL-L16: -O-CO-AL-AR-O-AL-O-CO-L17: -O-CO-AR-O-AL-CO-L18: -O-CO-AR-O-AL-O-CO-L19: -O-CO-AR-O-AL-O-AL-OC
O-L20: -O-CO-AR-O-AL-O-AL-OA
L-O-CO-L21: -S-AL-L22: -S-AL-O-L23: -S-AL-O-CO-L24: -S-AL-S-AL-L25: -S-AR -AL- L26: -O-

L27:-(O-AL) n-L28:-(O-AL) n-O-L29:-(O-AL) n-O-CO-L30: -AL-L31: -AL-O -L32: -AL-O-CO- L33: -O-AL-CO-O-AL- L34: -O-AL-CO-O-AL-O- L35: -O-AL-CO-O-AL -O-CO-L36: -O-AL-CO-AL-L37: -O-AL-CO-AL-O-L38: -O-AL-CO-AL-O-CO-

When an asymmetric carbon atom is introduced into AL (alkylene group, alkenylene group or alkynylene group),
The discotic liquid crystal molecules can be twisted and aligned in a spiral shape. Examples of AL * containing an asymmetric carbon atom are given below. The left side is the triphenylene ring side, and the right side is the polymerizable group (Q) side. The carbon atoms marked with * are asymmetric carbon atoms. The optical activity may be either S or R.

AL * 1: -CH ₂ CH ₂ -C * HCH _{3
-CH 2 CH 2 CH 2 - AL} * 2: -CH 2 CH 2 CH 2 -C * HCH 3 -CH
_{2 CH 2 - AL * 3:} -CH 2 -C * HCH 3 -CH 2 CH 2 CH
_{2 CH 2 - AL * 4:} -C * HCH 3 -CH 2 CH 2 CH 2 CH 2
_{CH 2 - AL * 5: -CH} 2 CH 2 CH 2 CH 2 -C * HCH 3
_{-CH 2 - AL * 6: -CH} 2 CH 2 CH 2 CH 2 CH 2 -C * H
_{CH 3 - AL * 7: -C} * HCH 3 -CH 2 CH 2 CH 2 CH 2
_{- AL * 8: -CH 2 -C} * HCH 3 -CH 2 CH 2 CH
_{2 - AL * 9: -CH 2} CH 2 -C * HCH 3 -CH 2 CH
_{2 - AL * 10: -CH 2} CH 2 CH 2 -C * HCH 3 -CH
_{2 - AL * 11: -CH 2} CH 2 CH 2 CH 2 -C * HCH 3
−

[0061] _{AL * 12: -C * HCH 3} -CH 2 CH 2 CH 2 - AL * 13: -CH 2 -C * HCH 3 -CH 2 CH 2 - AL * 14: -CH 2 CH 2 -C * _{HCH 3 -CH 2 - AL * 15} : -CH 2 CH 2 CH 2 -C * HCH 3 - AL * 16: -CH 2 -C * HCH 3 - AL * 17: -C * HCH 3 -CH 2 - AL _{* 18: -C * HCH 3 -CH} 2 CH 2 CH 2 CH 2
_{CH 2 CH 2 - AL * 19} : -CH 2 -C * HCH 3 -CH 2 CH 2 CH
_{2 CH 2 CH 2 - AL *} 20: -CH 2 CH 2 -C * HCH 3 -CH 2 CH
_{2 CH 2 CH 2 - AL *} 21: -CH 2 CH 2 CH 2 -C * HCH 3 -CH
_{2 CH 2 CH 2 - AL *} 22: -C * HCH 3 -CH 2 CH 2 CH 2 CH 2
CH ₂ CH ₂ CH ₂ −

AL * 23: -CH ₂ -C * HCH ₃ -CH
_{2 CH 2 CH 2 CH 2 CH} 2 CH 2 - AL * 24: -CH 2 CH 2 -C * HCH 3 -CH 2 CH
_{2 CH 2 CH 2 CH 2 -} AL * 25: -CH 2 CH 2 CH 2 -C * HCH 3 -CH
_{2 CH 2 CH 2 CH 2 -} AL * 26: -C * HCH 3 - (CH 2) 8 - AL * 27: -CH 2 -C * HCH 3 - (CH 2) 8 - AL * 28: -CH 2 _{-C * HCH 2 CH 3 - AL} * 29: -CH 2 -C * HCH 2 CH 3 -CH 2 - AL * 30: -CH 2 -C * HCH 2 CH 3 -CH 2 CH
_{2 - AL * 31: -CH 2} -C * HCH 2 CH 3 -CH 2 CH
_{2 CH 2 CH 2 - AL *} 32: -CH 2 -C * H (n-C 3 H 7) -CH 2
_{CH 2 - AL * 33: -CH} 2 -C * H (n-C 3 H 7) -CH 2
CH ₂ CH ₂ CH ₂ −

AL * 34: -CH ₂ -C * H (OCOCH
_{3) -CH 2 CH 2 - AL} * 35: -CH 2 -C * H (OCOCH 3) -CH 2
_{CH 2 CH 2 CH 2 - AL} * 36: -CH 2 -C * HF-CH 2 CH 2 - AL * 37: -CH 2 -C * HF-CH 2 CH 2 CH 2 C
_{H 2 - AL * 38: -CH} 2 -C * HCl-CH 2 CH 2 - AL * 39: -CH 2 -C * HCl-CH 2 CH 2 CH 2
_{CH 2 - AL * 40: -CH} 2 -C * HOCH 3 -CH 2 CH 2 - AL * 41: -CH 2 -C * HOCH 3 -CH 2 CH 2 C
_{H 2 CH 2 - AL * 42} : -CH 2 -C * HCN-CH 2 CH 2 - AL * 43: -CH 2 -C * HCN-CH 2 CH 2 CH 2
_{CH 2 - AL * 44: -CH} 2 -C * HCF 3 -CH 2 CH 2 - AL * 45: -CH 2 -C * HCF 3 -CH 2 CH 2 CH
₂ CH ₂ −

In the formula (I), Q is a polymerizable group. Examples of Q are shown below.

[0065]

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Q is preferably an unsaturated polymerizable group (Q1 to Q7), an epoxy group (Q8) or an aziridinyl group (Q9), more preferably an unsaturated polymerizable group, and an ethylenically unsaturated group. Most preferably, it is a polymerizable group (Q1 to Q6). In the formula (I), a is 1,
2, 3 or 4. a is preferably 1, 2 or 3, more preferably 1 or 2, and most preferably 1. When a is 2 or more,
The combination of a plurality of L and Q is preferably the same. In the formula (I), b is an integer from 0 to (4-a). It is particularly preferable that b is 0. Discotic liquid crystalline molecules represented by the following formula (Ia) are particularly preferred.

[0067]

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In the formula (Ia), A ¹ and A ² are
Independently of one another, a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms or a 1 to 12 carbon atom.
Is an alkoxy group. The definition and examples of each group are the same as those of A ¹ and A ^{2 in} the formula (I). In the formula (Ia), Y represents a hydrogen atom, a halogen atom,
An alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, or an acyloxy group having 2 to 13 carbon atoms It is. The definition and examples of each group are the same as those of Y in the formula (I). In the formula (Ia), or A ² and Y combine to form a 5- or 6-membered ring. Examples of the five-membered or six-membered ring are those represented by the formula (I)
Is the same as In the formula (Ia), Z ¹ , Z ² and Z ³ each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a carbon atom An acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, or an acyloxy group having 2 to 13 carbon atoms. The definition and examples of each group are the same as those of Z in the formula (I). In the formula (Ia), L represents —O—, —CO—, —S—,
—NH—, a divalent linking group selected from the group consisting of an alkylene group, an alkenylene group, an alkynylene group, an arylene group, and a combination thereof. The definition and examples of each group are the same as those of L in the formula (I). In the formula (Ia), Q is a polymerizable group. The definition and examples of each group are the same as those of Q in formula (I).

Hereinafter, specific examples of the discotic liquid crystal molecules represented by the formula (I) will be shown. Specific examples (1) to (42)
6) will be exemplified with reference to formula (Ia). The asymmetric carbon atom (C *) in the specific examples (379) to (382) is a (R) -form, and the specific examples (383) to (382)
The asymmetric carbon atom (C *) in (386) is a (S) -form, and the asymmetric carbon atom (C *) in specific examples (387) to (390) is a racemic body.

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (1) H H H H H H O Q8 (2) H H H H H H OCH 2 Q8 (3) H H H H H H O (CH 2) 2 Q8 (4) H H H H H H O (CH 2) 3 Q8 (5) H H H H H H O (CH ₂ ) ₄ Q 8 (6) H H H H H H O (CH ₂ ) ₅ Q 8 (7) H H H H H H O (CH ₂ ) ₆ Q 8 (8) H H H H H H O (CH ₂ ) ₇ Q 8 (9) H H H H H H O (CH ₂ ) ₈ Q ₈ (10) H H H H H H O (CH ₂ ) ₉ Q 8 ───────── ───────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (11) H H H H H H O (CH ₂ ) ₁₀ Q8 (12) H H H H H H O (CH ₂ ) ₁₁ Q8 (13) H H H H H H O (CH ₂ ) ₁₂ Q8 (14) H H H H H H O O (CH ₂ ) ₁₃ Q8 (15) H H H H H H O (CH ₂ ) ₁₄ Q8 (16) H H H H H H O (CH ₂ ) ₁₅ Q8 (17) H H H H H H OCH ₂ OCO Q1 (18) H H H H H H O (CH ₂ ) ₂ OCO Q 1 (19) H H H H H H O (CH ₂ ) ₃ OCO Q 1 (20) H H H H H H O (CH ₂ ) ₄ OCO Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (21) H H H H H H O (CH ₂ ) ₅ OCO Q1 (22) H H H H H H O (CH ₂ ) ₆ OCO Q1 (23) H H H H H H O (CH ₂ ) ₇ OCO Q1 (24) H H H H H H O (CH ₂ ) ₈ OCO Q1 (25) H H H H H H O (CH ₂ ) ₉ OCO Q1 (26) H H H H H H O O (CH ₂ ) ₁₀ OCO Q1 (27) H H H H H H O (CH ₂ ) ₁₁ OCO Q1 (28) H H H H H H O (CH ₂ ) ₁₂ OCO Q1 (29) H H H H H H H O (CH ₂ ) ₁₃ OCO Q1 (30) H H H H H H O (CH ₂ ) ₁₄ OCO Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (31) H H H H H H O (CH ₂ ) ₁₅ OCO Q1 (32) H H H H H H OCH ₂ OCO Q5 (33) H H H H H H O (CH 2) 2 OCO Q5 (34) H H H H H H O (CH 2) 3 OCO Q5 (35) H H H H H H O (CH 2) 4 OCO Q5 (36) H H H H H H O (CH ₂ ) ₅ OCO Q5 (37) H H H H H H O (CH ₂ ) ₆ OCO Q 5 (38) H H H H H H O (CH ₂ ) ₇ OCO Q5 (39) H H H H H H O (CH ₂ ) ₈ OCO Q5 (40) H H H H H H O (CH ₂ ) ₉ OCO Q5 ───────────── ───────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² ( ³ ) H H H H H H O (CH ₂ ) ₁₀ OCO Q5 (42) H H H H H H O (CH ₂ ) ₁₁ OCO Q5 (43) H H H H H H O (CH ₂ ) ₁₂ OCO Q5 (44) H H H H H H O (CH ₂ ) ₁₃ OCO Q5 (45) H H H H H H O (CH ₂ ) ₁₄ OCO Q5 (46) H H H H H H O O (CH ₂ ) ₁₅ OCO Q5 (47) H H H H H H OCH ₂ O Q1 (48) H H H H H H O (CH 2) 2 O Q1 (49) H H H H H H O (CH 2) 3 O Q1 (50) H H H H H H O (CH 2) 4 O Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (51) H H H H H H O (CH ₂ ) ₅ O Q1 (52) H H H H H H O (CH ₂ ) ₆ O Q1 (53) H H H H H H O (CH ₂ ) ₇ O Q1 (54) H H H H H H O (CH ₂ ) ₈ O Q1 (55) H H H H H H O (CH ₂ ) ₉ O Q1 (56) H H H H H H O (CH ₂ ) ₁₀ O Q1 (57) H H H H H H O (CH ₂ ) ₁₁ O Q1 (58) H H H H H H O (CH ₂ ) ₁₂ O Q1 (59) H H H H H H O (CH ₂ ) ₁₃ O Q1 (60) H H H H H H O (CH ₂ ) ₁₄ O Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (61) H H H H H H O _{(CH 2) 15 O Q1 (} 62) H CH 3 H H H H O Q8 (63) H CH 3 H H H H OCH 2 Q8 (64) H CH 3 H H H H O (CH 2) 2 Q8 ( 65) H CH ₃ H H H H O (CH ₂ ) ₃ Q 8 (66) H CH ₃ H H H H O (CH ₂ ) ₄ Q 8 (67) H CH ₃ H H H H O (CH ₂ ) ₅ Q 8 (68) H CH ₃ H H H H O (CH ₂ ) ₆ Q 8 (69) H CH ₃ H H H H O (CH ₂ ) ₇ Q 8 (70) H CH ₃ H H H H O (CH ₂ ) ₈ Q8 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (71) H CH ₃ H H H H O (CH ₂ ) ₉ Q 8 (72) H CH ₃ H H H H O (CH ₂ ) ₁₀ Q 8 (73) H CH ₃ HH H H O (CH ₂ ) ₁₁ Q8 (74) H CH ₃ HH H H O (CH ₂ ) ₁₂ Q8 (75) H CH ₃ H H H H OCH ₂ OCO _{Q1 (76) H CH 3 H} H H H O (CH 2) 2 OCO Q1 (77) H CH 3 H H H H O (CH 2) 3 OCO Q1 (78) H CH 3 H H H H O (CH ₂ ) ₄ OCO Q1 (79) H CH ₃ H H H H O (CH ₂ ) ₅ OCO Q1 (80) H CH ₃ H H H H O (CH ₂ ) ₆ OCO Q1 ───────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (81)} H CH 3 H H H H O (CH ₂ ) ₇ OCO Q 1 (82) H CH ₃ H H H H O (CH ₂ ) ₈ OCO Q 1 (83) H CH ₃ H H H H O (CH ₂ ) ₉ OCO Q 1 (84) H CH ₃ H H H H O (CH ₂ ) ₁₀ OCO Q1 (85) H CH ₃ HH H H O (CH ₂ ) ₁₁ OCO Q1 (86) H CH ₃ HH H H H O (CH ₂ ) ₁₂ OCO Q1 (87 ) H CH ₃ H H H H OCH ₂ OCO _{Q5 (88) H CH 3 H} H H H O (CH 2) 2 OCO Q5 (89) H CH 3 H H H H O (CH 2) 3 OCO Q5 (90) H CH 3 H H H H O (CH ₂ ) ₄ OCO Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (91) H CH ₃ H H H H O (CH ₂ ) ₅ OCO Q5 (92) H CH ₃ H H H H O (CH ₂ ) ₆ OCO Q5 (93) H CH ₃ HH H H O (CH ₂ ) ₇ OCO Q5 (94) H CH ₃ H H H H O (CH ₂ ) ₈ OCO Q5 (95) H CH ₃ HH H H O (CH ₂ ) ₉ OCO Q5 (96) H CH ₃ HH H H H O O (CH ₂ ) ₁₀ OCO Q5 (97 ) H CH ₃ H H H H O (CH ₂ ) ₁₁ OCO Q5 (98) H CH ₃ H H H H O (CH ₂ ) ₁₂ OCO Q5 (99) H CH ₃ HH H H OCH ₂ O Q1 (100) H CH ₃ H H H H O (CH ₂ ) ₂ O Q1 ─────────────────────────────── ─────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (101) H CH ₃ H H H H _{O (CH 2) 3 O Q1} (102) H CH 3 H H H H O (CH 2) 4 O Q1 (103) H CH 3 H H H H O (CH 2) 5 O Q1 (104) H CH 3 _{H H H H O (CH 2} ) 6 O Q1 (105) H CH 3 H H H H O (CH 2) 7 O Q1 (106) H CH 3 H H H H O (CH 2) 8 O Q1 (107 ) H CH ₃ H H H H O (CH ₂ ) ₉ O Q1 (108) H CH ₃ H H H H O (CH ₂ ) ₁₀ O Q 1 (109) H CH ₃ H H H H O (CH ₂ ) ₁₁ O Q1 (110) H CH ₃ H H H H O (CH ₂ ) ₁₂ O Q1 ────────────────────────────── ── ───

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (111) CH ₃ H H H H H O Q8 (112) CH ₃ H H H H H O CH ₂ Q8 (113) CH ₃ H H H H H O (CH ₂ ) ₂ Q 8 (114) CH ₃ H H H H H O (CH ₂ ) ₃ Q 8 ( _{115) CH 3 H H H H} H O (CH 2) 4 Q8 (116) CH 3 H H H H H O (CH 2) 5 Q8 (117) CH 3 H H H H H O (CH 2) 6 Q8 _{(118) CH 3 H H H} H H O (CH 2) 7 Q8 (119) CH 3 H H H H H O (CH 2) 8 Q8 (120) CH 3 H H H H H O (CH 2) 9 Q8 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (121) CH ₃ H H H H H O (CH ₂ ) ₁₀ Q 8 (122) CH ₃ H H H H H O (CH ₂ ) ₁₁ Q 8 (123) CH ₃ H H H H H O (CH ₂ ) ₁₂ Q 8 (124) CH ₃ H H H H H OCH ₂ OCO _{Q1 (125) CH 3 H H} H H H O (CH 2) 2 OCO Q1 (126) CH 3 H H H H H O (CH 2) 3 OCO Q1 (127) CH 3 H H H H H O (CH ₂ ) ₄ OCO Q1 (128) CH ₃ H H H H H O (CH ₂ ) ₅ OCO Q 1 (129) CH ₃ H H H H H O O (CH ₂ ) ₆ OCO Q 1 (130) CH ₃ H H H H H O (CH ₂ ) ₇ OCO Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (131) CH ₃ H H H H H O (CH ₂ ) ₈ OCO Q1 (132) CH ₃ HHHHHO (CH ₂ ) ₉ OCO Q1 (133) CH ₃ HHHHHO (CH ₂ ) ₁₀ OCO Q1 (134) CH ₃ H H H H H O (CH ₂ ) ₁₁ OCO Q1 (135) CH ₃ H H H H H O (CH ₂ ) ₁₂ OCO Q1 (136) CH ₃ H H H H H O O CH ₂ OCO _{Q5 (137) CH 3 H H} H H H O (CH 2) 2 OCO Q5 (138) CH 3 H H H H H O (CH 2) 3 OCO Q5 (139) CH 3 H H H H H O (CH ₂ ) ₄ OCO Q5 (140) CH ₃ H H H H H O (CH ₂ ) ₅ OCO Q5 ─────────────────────────── ─────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (141)} CH 3 H H H H H O (CH ₂ ) ₆ OCO Q5 (142) CH ₃ HHHHHO (CH ₂ ) ₇ OCO Q5 (143) CH ₃ HHHHHO (CH ₂ ) ₈ OCO Q5 (144) CH ₃ H H H H H O (CH ₂ ) ₉ OCO Q5 (145) CH ₃ H H H H H O (CH ₂ ) ₁₀ OCO Q5 (146) CH ₃ H H H H H H O (CH ₂ ) ₁₁ OCO Q5 (147 ) CH ₃ H H H H H O (CH ₂ ) ₁₂ OCO Q5 (148) CH ₃ H H H H H O CH ₂ O _{Q1 (149) CH 3 H H} H H H O (CH 2) 2 O Q1 (150) CH 3 H H H H H O (CH 2) 3 O Q1 ───────────── ───────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (151)} CH 3 H H H H H _{O (CH 2) 4 O Q1} (152) CH 3 H H H H H O (CH 2) 5 O Q1 (153) CH 3 H H H H H O (CH 2) 6 O Q1 (154) CH 3 H H H H H O (CH ₂ ) ₇ O Q1 (155) CH ₃ H H H H H O (CH ₂ ) ₈ O Q1 (156) CH ₃ H H H H H H O (CH ₂ ) ₉ O Q1 (157 ) CH ₃ H H H H H O (CH ₂ ) ₁₀ O Q1 (158) CH ₃ H H H H H H O (CH ₂ ) ₁₁ O Q 1 (159) CH ₃ H H H H H O (CH ₂ ) _{12 O Q1 (160) CH 3 CH} 3 H H H H O Q8 ───────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (161)} CH 3 CH 3 H H H H OCH ₂ Q8 (162) CH ₃ CH ₃ H H H H O (CH ₂ ) ₂ Q8 (163) CH ₃ CH ₃ H H H H O (CH ₂ ) ₃ Q8 (164) CH ₃ CH ₃ H H H H O (CH ₂ ) ₄ Q 8 (165) CH ₃ CH ₃ H H H H O (CH ₂ ) ₅ Q 8 (166) CH ₃ CH ₃ H H H H O (CH ₂ ) ₆ Q 8 (167) CH ₃ CH _{3 H H H H O (CH} 2) 7 Q8 (168) CH 3 CH 3 H H H H O (CH 2) 8 Q8 (169) CH 3 CH 3 H H H H O (CH 2) 9 Q8 (170 ) CH ₃ CH ₃ H H H H O (CH ₂ ) ₁₀ Q8 ────────────────────────────────── ──

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (171)} CH 3 CH 3 H H H H O (CH ₂ ) ₁₁ Q8 (172) CH ₃ CH ₃ H H H H O (CH ₂ ) ₁₂ Q8 (173) CH ₃ CH ₃ HH H H OCH ₂ OCO _{Q1 (174) CH 3 CH 3} H H H H O (CH 2) 2 OCO Q1 (175) CH 3 CH 3 H H H H O (CH 2) 3 OCO Q1 (176) CH 3 CH 3 H H H H O (CH ₂ ) ₄ OCO Q1 (177) CH ₃ CH ₃ HHHHO (CH ₂ ) ₅ OCO Q1 (178) CH ₃ CH ₃ HHHHO (CH ₂ ) ₆ OCO Q1 (179) CH ₃ CH ₃ H H H H O (CH ₂ ) ₇ OCO Q1 (180) CH ₃ CH ₃ H H H H O (CH ₂ ) ₈ OCO Q1 ──────────────── ────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (181)} CH 3 CH 3 H H H H O (CH ₂ ) ₉ OCO Q1 (182) CH ₃ CH ₃ HHHHO (CH ₂ ) ₁₀ OCO Q1 (183) CH ₃ CH ₃ HHHHO (CH ₂ ) ₁₁ OCO Q1 (184) _{CH 3 CH 3 H H H H} O (CH 2) 12 OCO Q1 (185) CH 3 CH 3 H H H H OCH 2 OCO _{Q5 (186) CH 3 CH 3} H H H H O (CH 2) 2 OCO Q5 (187) CH 3 CH 3 H H H H O (CH 2) 3 OCO Q5 (188) CH 3 CH 3 H H H H O (CH ₂ ) ₄ OCO Q5 (189) CH ₃ CH ₃ HHHHO (CH ₂ ) ₅ OCO Q5 (190) CH ₃ CH ₃ HHHHO (CH ₂ ) ₆ OCO Q5 ────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (191)} CH 3 CH 3 H H H H O (CH ₂ ) ₇ OCO Q5 (192) CH ₃ CH ₃ HHHHO (CH ₂ ) ₈ OCO Q5 (193) CH ₃ CH ₃ HHHHO (CH ₂ ) ₉ OCO Q5 (194) _{CH 3 CH 3 H H H H} O (CH 2) 10 OCO Q5 (195) CH 3 CH 3 H H H H O (CH 2) 11 OCO Q5 (196) CH 3 CH 3 H H H H O (CH 2 ) ₁₂ OCO Q5 (197) CH ₃ CH ₃ H H H H OCH ₂ O _{Q1 (198) CH 3 CH 3} H H H H O (CH 2) 2 O Q1 (199) CH 3 CH 3 H H H H O (CH 2) 3 O Q1 (200) CH 3 CH 3 H H H H O (CH ₂ ) ₄ O Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (201)} CH 3 CH 3 H H H H O (CH ₂ ) ₅ O Q1 (202) CH ₃ CH ₃ HHHHO (CH ₂ ) ₆ O Q1 (203) CH ₃ CH ₃ HHHHO (CH ₂ ) ₇ O Q1 (204) CH ₃ CH ₃ H H H H O (CH ₂ ) ₈ O Q 1 (205) CH ₃ CH ₃ H H H H O (CH ₂ ) ₉ O Q 1 (206) CH ₃ CH ₃ H H H H O (CH ₂ ) ₁₀ O Q1 (207) CH ₃ CH ₃ HH HHO (CH ₂ ) ₁₁ O Q1 (208) CH ₃ CH ₃ HH HHO (CH ₂ ) ₁₂ O Q1 (209) H H H CH ₃ H H O Q8 (210) H H H CH 3 H H OCH 2 Q8 ───────────────────────────────── ──

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (211) H H H CH ₃ H H _{O (CH 2) 2 Q8 (} 212) H H H CH 3 H H O (CH 2) 3 Q8 (213) H H H CH 3 H H O (CH 2) 4 Q8 (214) H H H CH 3 H H O (CH ₂ ) ₅ Q 8 (215) H H H CH ₃ H H O (CH ₂ ) ₆ Q 8 (216) H H H CH ₃ H H O (CH ₂ ) ₇ Q 8 (217) H H H CH _{3 H H O (CH 2) 8} Q8 (218) H H H CH 3 H H O (CH 2) 9 Q8 (219) H H H CH 3 H H O (CH 2) 10 Q8 (220) H H H CH ₃ H H O (CH ₂ ) ₁₁ Q8 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (221) H H H CH ₃ H H O (CH ₂ ) ₁₂ Q8 (222) H H H CH ₃ H H OCH ₂ OCO Q1 (223) H H H CH 3 H H O (CH 2) 2 OCO Q1 (224) H H H CH 3 H H O (CH 2) 3 OCO Q1 (225) H H H CH 3 H H O (CH _{2) 4 OCO Q1 (226)} H H H CH 3 H H O (CH 2) 5 OCO Q1 (227) H H H CH 3 H H O (CH 2) 6 OCO Q1 (228) H H H CH 3 H H O (CH ₂ ) ₇ OCO Q1 (229) H H H CH ₃ HHO (CH ₂ ) ₈ OCO Q1 (230) H H H CH ₃ HHO (CH ₂ ) ₉ OCO Q1 ───────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (231) H H H CH ₃ H H O (CH ₂ ) ₁₀ OCO Q1 (232) H H H CH ₃ HHO (CH ₂ ) ₁₁ OCO Q1 (233) H H H CH ₃ H H O (CH ₂ ) ₁₂ OCO Q1 (234) H H H CH ₃ H H OCH ₂ OCO Q5 (235) H H H CH 3 H H O (CH 2) 2 OCO Q5 (236) H H H CH 3 H H O (CH 2) 3 OCO Q5 (237) H H H CH 3 H H O (CH _{2) 4 OCO Q5 (238)} H H H CH 3 H H O (CH 2) 5 OCO Q5 (239) H H H CH 3 H H O (CH 2) 6 OCO Q5 (240) H H H CH 3 H H O (CH ₂ ) ₇ OCO Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (241) H H H CH ₃ H H _{O (CH 2) 8 OCO Q5} (242) H H H CH 3 H H O (CH 2) 9 OCO Q5 (243) H H H CH 3 H H O (CH 2) 10 OCO Q5 (244) H H H CH ₃ HHO (CH ₂ ) ₁₁ OCO Q5 (245) HHH CH ₃ HHO (CH ₂ ) ₁₂ OCO Q5 (246) H H H CH ₃ HHOCH ₂ O Q1 (247) H H H CH 3 H H O (CH 2) 2 O Q1 (248) H H H CH 3 H H O (CH 2) 3 O Q1 (249) H H H CH 3 H H O (CH ₂ ) ₄ O Q1 (250) H H H CH ₃ H H O (CH ₂ ) ₅ O Q1 ─────────────────────────── ─────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (251) H H H CH ₃ H H _{O (CH 2) 6 O Q1} (252) H H H CH 3 H H O (CH 2) 7 O Q1 (253) H H H CH 3 H H O (CH 2) 8 O Q1 (254) H H H CH ₃ HHO (CH ₂ ) ₉ O Q1 (255) H H H CH ₃ HHO (CH ₂ ) ₁₀ O Q1 (256) H H H CH ₃ HHO (CH ₂ ) ₁₁ O Q1 (257 _{) H H H CH 3 H H} O (CH 2) 12 O Q1 (258) H H H H CH 3 H O Q8 (259) H H H H CH 3 H OCH 2 Q8 (260) H H H H CH 3 H O (CH ₂ ) ₂ Q8 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (261)} H H H H CH 3 H _{O (CH 2) 3 Q8 (} 262) H H H H CH 3 H O (CH 2) 4 Q8 (263) H H H H CH 3 H O (CH 2) 5 Q8 (264) H H H H CH 3 H O (CH ₂ ) ₆ Q8 (265) H H H H CH ₃ H O (CH ₂ ) ₇ Q8 (266) H H H H CH ₃ H O (CH ₂ ) ₈ Q8 (267) H H H H CH ₃ H O (CH ₂ ) ₉ Q 8 (268) H H H H CH ₃ H O (CH ₂ ) ₁₀ Q 8 (269) H H H H CH ₃ H O (CH ₂ ) ₁₁ Q 8 (270) H H H H CH ₃ H O (CH ₂ ) ₁₂ Q8 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (271) H H H H CH ₃ H OCH ₂ OCO Q1 (272) H H H H CH 3 H O (CH 2) 2 OCO Q1 (273) H H H H CH 3 H O (CH 2) 3 OCO Q1 (274) H H H H CH 3 H O (CH _{2) 4 OCO Q1 (275)} H H H H CH 3 H O (CH 2) 5 OCO Q1 (276) H H H H CH 3 H O (CH 2) 6 OCO Q1 (277) H H H H CH 3 H O (CH ₂ ) ₇ OCO Q1 (278) H H H H CH ₃ H O (CH ₂ ) ₈ OCO Q1 (279) H H H H H CH ₃ H O (CH ₂ ) ₉ OCO Q1 (280) H H H H CH ₃ H O (CH ₂ ) ₁₀ OCO Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (281) H H H H CH ₃ H O (CH ₂ ) ₁₁ OCO Q1 (282) H H H H CH ₃ H O (CH ₂ ) ₁₂ OCO Q1 (283) H H H H CH ₃ H OCH ₂ OCO Q5 (284) H H H H CH 3 H O (CH 2) 2 OCO Q5 (285) H H H H CH 3 H O (CH 2) 3 OCO Q5 (286) H H H H CH 3 H O (CH _{2) 4 OCO Q5 (287)} H H H H CH 3 H O (CH 2) 5 OCO Q5 (288) H H H H CH 3 H O (CH 2) 6 OCO Q5 (289) H H H H CH 3 H O (CH ₂ ) ₇ OCO Q5 (290) H H H H CH ₃ H O (CH ₂ ) ₈ OCO Q5 ─────────────────────── ─────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (291) H H H H CH ₃ H O (CH ₂ ) ₉ OCO Q5 (292) H H H H CH ₃ H O (CH ₂ ) ₁₀ OCO Q5 (293) H H H H H CH ₃ H O (CH ₂ ) ₁₁ OCO Q5 (294) H H H H CH ₃ H O (CH ₂ ) ₁₂ OCO Q5 (295) H H H H CH ₃ H OCH ₂ O Q1 (296) H H H H CH 3 H O (CH 2) 2 O Q1 (297) H H H H CH 3 H O (CH 2) 3 O Q1 (298) H H H H CH 3 H O (CH ₂ ) ₄ O Q1 (299) H H H H CH ₃ H O (CH ₂ ) ₅ O Q1 (300) H H H H CH ₃ H O (CH ₂ ) ₆ O Q1 ───────── ───────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (301) H H H H CH ₃ H O (CH ₂ ) ₇ O Q 1 (302) H H H H CH ₃ H O (CH ₂ ) ₈ O Q 1 (303) H H H H CH ₃ H O (CH ₂ ) ₉ O Q 1 (304) H H H _{H CH 3 H O (CH 2} ) 10 O Q1 (305) H H H H CH 3 H O (CH 2) 11 O Q1 (306) H H H H CH 3 H O (CH 2) 12 O Q1 (307 _{) H CH 3 H CH 3 H} H O Q8 (308) H CH 3 H CH 3 H H OCH 2 Q8 (309) H CH 3 H CH 3 H H O (CH 2) 2 Q8 (310) H CH 3 H _{CH 3 H H O (CH 2} ) 3 Q8 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ L Q CH (311) H CH ₃ H CH ₃ H H O (CH ₂ ) ₄ Q 8 (312) H CH ₃ H CH ₃ H H O (CH ₂ ) ₅ Q 8 (313) H CH ₃ H CH ₃ H H O (CH ₂ ) ₆ Q 8 (314) H CH _{3 H CH 3 H H O (CH} 2) 7 Q8 (315) H CH 3 H CH 3 H H O (CH 2) 8 Q8 (316) H CH 3 H CH 3 H H O (CH 2) 9 Q8 (317 _{) H CH 3 H CH 3 H} H O (CH 2) 10 Q8 (318) H CH 3 H CH 3 H H O (CH 2) 11 Q8 (319) H CH 3 H CH 3 H H O (CH 2) ₁₂ Q8 (320) H CH ₃ H CH ₃ H H O OCH ₂ OCO Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQＱ (321) H CH ₃ H CH ₃ H _{H O (CH 2) 2 OCO} Q1 (322) H CH 3 H CH 3 H H O (CH 2) 3 OCO Q1 (323) H CH 3 H CH 3 H H O (CH 2) 4 OCO Q1 (324) _{H CH 3 H CH 3 H H} O (CH 2) 5 OCO Q1 (325) H CH 3 H CH 3 H H O (CH 2) 6 OCO Q1 (326) H CH 3 H CH 3 H H O (CH 2 ) ₇ OCO Q1 (327) H CH ₃ H CH ₃ H H O (CH ₂ ) ₈ OCO Q1 (328) H CH ₃ H CH ₃ H H O (CH ₂ ) ₉ OCO Q1 (329) H CH ₃ H CH _{3 H H O (CH 2)} 10 OCO Q1 (330) H CH 3 H CH 3 H H O (CH 2) 11 OCO Q1 ──────────────────── ─── ─────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (331)} H CH 3 H CH 3 H H O (CH ₂ ) ₁₂ OCO Q1 (332) H CH ₃ H CH ₃ H H OCH ₂ OCO _{Q5 (333) H CH 3 H} CH 3 H H O (CH 2) 2 OCO Q5 (334) H CH 3 H CH 3 H H O (CH 2) 3 OCO Q5 (335) H CH 3 H CH 3 H H O (CH ₂ ) ₄ OCO Q5 (336) H CH ₃ H CH ₃ HHO (CH ₂ ) ₅ OCO Q5 (337) H CH ₃ H CH ₃ HHO (CH ₂ ) ₆ OCO Q5 (338) H CH ₃ H CH ₃ HHO (CH ₂ ) ₇ OCO Q5 (339) H CH ₃ H CH ₃ HHO (CH ₂ ) ₈ OCO Q5 (340) H CH ₃ H CH ₃ HHO (CH ₂ ) ₉ OCO Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (341)} H CH 3 H CH 3 H H O (CH ₂ ) ₁₀ OCO Q5 (342) H CH ₃ H CH ₃ H H O (CH ₂ ) ₁₁ OCO Q5 (343) H CH ₃ H CH ₃ HHO (CH ₂ ) ₁₂ OCO Q5 (344) H CH ₃ H CH ₃ H H OCH ₂ O _{Q1 (345) H CH 3 H} CH 3 H H O (CH 2) 2 O Q1 (346) H CH 3 H CH 3 H H O (CH 2) 3 O Q1 (347) H CH 3 H CH 3 H H _{O (CH 2) 4 O Q1} (348) H CH 3 H CH 3 H H O (CH 2) 5 O Q1 (349) H CH 3 H CH 3 H H O (CH 2) 6 O Q1 (350) H CH ₃ H CH ₃ H H O (CH ₂ ) ₇ O Q1 ─────────────────────────────────── ─

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ^{2 Z 3 L Q ──────────────────────────────────── (351)} H CH 3 H CH 3 H H O (CH ₂ ) ₈ O Q1 (352) H CH ₃ H CH ₃ H H O (CH ₂ ) ₉ O Q1 (353) H CH ₃ H CH ₃ H H O (CH ₂ ) ₁₀ O Q1 (354) _{H CH 3 H CH 3 H H} O (CH 2) 11 O Q1 (355) H CH 3 H CH 3 H H O (CH 2) 12 O Q1 (356) H H H H H H (OCH 2 CH 2) ₂ Q8 (357) H H H H H H (OCH ₂ CH ₂ ) ₃ Q8 (358) H H H H H H (OCH ₂ CH ₂ ) ₄ Q8 (359) H H H H H H (OCH ₂ CH ₂ ) ₂ OCO Q1 (360) H H H H H H (OCH ₂ CH ₂ ) ₃ OCO Q1 ───────────────────────── ───────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (361) H H H H H H ( OCH ₂ CH ₂ ) ₄ OCO Q1 (362) H H H H H H (OCH ₂ CH ₂ ) ₂ OCO Q5 (363) H H H H H H (OCH ₂ CH ₂ ) ₃ OCO Q5 (364) H H H _{H H H (OCH 2 CH 2} ) 4 OCO Q5 (365) H H H H H H (OCH 2 CH 2) 2 O Q1 (366) H H H H H H (OCH 2 CH 2) 3 O Q1 (367 ) H H H H H H ( OCH 2 CH 2) 4 O Q1 (368) H H H H H H O (CH 2) 2 OCO Q2 (369) H H H H H H O (CH 2) 3 OCO Q2 (370) H H H H H H O (CH 2) 4 OCO Q2 ──────────────────── ───────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (371) H H H H H H O (CH ₂ ) ₅ OCO Q 2 (372) H H H H H H O (CH ₂ ) ₆ OCO Q 2 (373) H H H H H H O (CH ₂ ) ₇ OCO Q 2 (374) H H H H H H O (CH ₂ ) ₈ OCO Q 2 (375) H H H H H H O O (CH ₂ ) ₉ OCO Q 2 (376) H H H H H H H O (CH ₂ ) ₁₀ OCO Q 2 (377) H H H H H H O (CH ₂ ) ₁₁ OCO Q2 (378) H H H H H H O (CH ₂ ) ₁₂ OCO Q2 (379) H H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ Q8 (380) H H H H H H O (CH 2) 2 C * HCH 3 (CH 2) 3 OCO Q1 ────────────────── ─────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (381) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ OCO Q5 (382) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ O Q 1 (383) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ Q8 (384) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ OCO Q 1 (385) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ OCO Q5 (386) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ O Q1 (387) H H _{H H H H O (CH 2} ) 2 C * HCH 3 (CH 2) 3 Q8 (388) H H H H H H O (CH 2) 2 C * HCH 3 (CH 2) 3 OCO Q1 (389) H H H H H H O (CH 2) 2 C * HCH 3 (CH 2) 3 OCO Q5 ( 390) H H H H H H O (CH ₂ ) ₂ C * HCH ₃ (CH ₂ ) ₃ O Q1 ───────────────────────── ───────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (391) H H H H H H ( _{CH 2) 4 Q8 (392)} H H H H H H (CH 2) 5 Q8 (393) H H H H H H (CH 2) 6 Q8 (394) H H H H H H (CH 2) 7 Q8 (395) H H H H H H (CH 2) 8 Q8 (396) H H H H H H (CH 2) 4 OCO Q1 (397) H H H H H H (CH 2) 5 OCO Q1 (398) H H H H H H (CH 2) 6 OCO Q1 (399) H H H H H H (CH 2) 7 OCO Q1 (400) H H H H H H (CH 2) 8 OCO Q1 ───── ───────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (401) H H H H H H ( CH ₂ ) ₄ OCO Q5 (402) H H H H H H (CH ₂ ) ₅ OCO Q5 (403) H H H H H H (CH ₂ ) ₆ OCO Q5 (404) H H H H H H (CH ₂ ) ₇ OCO Q5 (405) H H H H H H (CH ₂ ) ₈ OCO Q5 (406) H H H H H H (CH ₂ ) ₄ O Q1 (407) H H H H H H (CH ₂ ) ₅ O Q1 (408) H H H H H H (CH ₂ ) ₆ O Q1 (409) H H H H H H (CH ₂ ) ₇ O Q 1 (410) H H H H H H (CH ₂ ) ₈ O Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ──────────────────────────────────── (411) H H H H H H O _{(CH 2) 2 COO (CH} 2) 2 Q8 (412) H H H H H H O (CH 2) 2 COO (CH 2) 2 OCO Q1 (413) H H H H H H O (CH 2) 2 COO (CH ₂ ) ₂ OCO Q5 (414) H H H H H H O (CH ₂ ) ₂ COO (CH ₂ ) ₂ O Q 1 (415) H H H H H H O (CH ₂ ) ₂ CO (CH _{2 ) 3 Q8 (416) H H} H H H H O (CH 2) 2 CO (CH 2) 3 OCO Q1 (417) H H H H H H O (CH 2) 2 CO (CH 2) 3 OCO Q5 ( 418) H H H H H H O (CH 2) 2 CO (CH 2) 3 O Q1 (419) H H H H H H O (CH 2) 2 CH = CH (CH 2) 2 Q8 (420) H H H H H H O (CH ₂ ) ₂ CH = CH (CH ₂ ) ₂ OCO Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples A ¹ A ² YZ ¹ Z ² Z ³ LQ ──────────────────────────────────── (421) H H H H H H O (CH ₂ ) ₂ CH = CH (CH ₂ ) ₂ OCO Q5 (422) H H H H H H O (CH ₂ ) ₂ CH = CH (CH ₂ ) ₂ O Q 1 (423) H H H H H H OCH ₂ C≡C (CH ₂ ) ₃ Q8 (424) H H H H H H O OCH ₂ C≡C (CH ₂ ) ₃ OCO Q1 (425) H H H H H H O OCH ₂ C≡C (CH ₂ ) ₃ OCO Q5 (426) H H H H H H OCH 2 C≡C (CH 2) 3 O Q1 ─────────────────────────── ─────────

[0113]

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──────────────────────────────────── Specific examples (427) (428) (429) (430) (431) L O (CH 2) 2 O (CH 2) 3 O (CH 2) 4 O (CH 2) 5 O (CH 2) 6 Q Q8 Q8 Q8 Q8 Q8 ─────── ─────────────────────────────

──────────────────────────────────── Specific examples (432) (433) (434) (435) (436) L O (CH 2) 7 O (CH 2) 8 O (CH 2) 9 O (CH 2) 10 O (CH 2) 11 Q Q8 Q8 Q8 Q8 Q8 ─────── ─────────────────────────────

──────────────────────────────────── Specific examples (437) (438) (439) (440) (441) L O (CH ₂ ) ₁₂ O (CH ₂ ) ₂ OCO O (CH ₂ ) ₃ OCO O (CH ₂ ) ₄ OCO O (CH ₂ ) ₅ OCO Q Q8 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (442) (443) (444) (445) (446) L O (CH ₂ ) ₆ OCO O (CH ₂ ) ₇ OCO O (CH ₂ ) ₈ OCO O (CH ₂ ) ₉ OCO O (CH ₂ ) ₁₀ OCO Q Q1 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (447) (448) (449) (450) (451) L O (CH ₂ ) ₁₁ OCO O (CH ₂ ) ₁₂ OCO O (CH ₂ ) ₂ OCO O (CH ₂ ) ₃ OCO O (CH ₂ ) ₄ OCO Q Q1 Q1 Q5 Q5 Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples (452) (453) (454) (455) (456) L O (CH ₂ ) ₅ OCO O (CH ₂ ) ₆ OCO O (CH ₂ ) ₇ OCO O (CH ₂ ) ₈ OCO O (CH ₂ ) ₉ OCO Q Q5 Q5 Q5 Q5 Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples (457) (458) (459) (460) (461) L O (CH ₂ ) ₁₀ OCO O (CH ₂ ) ₁₁ OCO O (CH ₂ ) ₁₂ OCO O (CH ₂ ) ₂ O O (CH ₂ ) ₃ O Q Q5 Q5 Q5 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (462) (463) (464) (465) (466) L O (CH ₂ ) ₄ O O (CH ₂ ) ₅ O O (CH ₂ ) ₆ O O (CH ₂ ) ₇ O O (CH ₂ ) ₈ O Q Q1 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (467) (468) (469) (470) L O (CH ₂ ) ₉ O O (CH ₂ ) ₁₀ O O (CH ₂ ) ₁₁ O O (CH ₂ ) ₁₂ O Q Q1 Q1 Q1 Q1 ────────────────────────────────────

[0123]

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──────────────────────────────────── Specific examples (471) (472) (473) (474) (475) L O (CH 2) 2 O (CH 2) 3 O (CH 2) 4 O (CH 2) 5 O (CH 2) 6 Q Q8 Q8 Q8 Q8 Q8 ─────── ─────────────────────────────

──────────────────────────────────── Specific examples (476) (477) (478) (479) (480) L O (CH 2) 7 O (CH 2) 8 O (CH 2) 9 O (CH 2) 10 O (CH 2) 11 Q Q8 Q8 Q8 Q8 Q8 ─────── ─────────────────────────────

──────────────────────────────────── Specific examples (481) (482) (483) (484) (485) L O (CH ₂ ) ₁₂ O (CH ₂ ) ₂ OCO O (CH ₂ ) ₃ OCO O (CH ₂ ) ₄ OCO O (CH ₂ ) ₅ OCO Q Q8 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (486) (487) (488) (489) (490) L O (CH ₂ ) ₆ OCO O (CH ₂ ) ₇ OCO O (CH ₂ ) ₈ OCO O (CH ₂ ) ₉ OCO O (CH ₂ ) ₁₀ OCO Q Q1 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (491) (492) (493) (494) (495) L O (CH ₂ ) ₁₁ OCO O (CH ₂ ) ₁₂ OCO O (CH ₂ ) ₂ OCO O (CH ₂ ) ₃ OCO O (CH ₂ ) ₄ OCO Q Q1 Q1 Q5 Q5 Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples (496) (497) (498) (499) (500) L O (CH ₂ ) ₅ OCO O (CH ₂ ) ₆ OCO O (CH ₂ ) ₇ OCO O (CH ₂ ) ₈ OCO O (CH ₂ ) ₉ OCO Q Q5 Q5 Q5 Q5 Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples (501) (502) (503) (504) (505) L O (CH ₂ ) ₁₀ OCO O (CH ₂ ) ₁₁ OCO O (CH ₂ ) ₁₂ OCO O (CH ₂ ) ₂ O O (CH ₂ ) ₃ O Q Q5 Q5 Q5 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (506) (507) (508) (509) (510) L O (CH ₂ ) ₄ O O (CH ₂ ) ₅ O O (CH ₂ ) ₆ O O (CH ₂ ) ₇ O O (CH ₂ ) ₈ O Q Q1 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (511) (512) (513) (514) L O (CH ₂ ) ₉ O O (CH ₂ ) ₁₀ O O (CH ₂ ) ₁₁ O O (CH ₂ ) ₁₂ O Q Q1 Q1 Q1 Q1 ────────────────────────────────────

[0133]

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──────────────────────────────────── Specific examples (515) (516) (517) (518) (519) L O (CH 2) 2 O (CH 2) 3 O (CH 2) 4 O (CH 2) 5 O (CH 2) 6 Q Q8 Q8 Q8 Q8 Q8 ─────── ─────────────────────────────

──────────────────────────────────── Specific examples (520) (521) (522) (523) (524) L O (CH ₂ ) ₇ O (CH ₂ ) ₈ O (CH ₂ ) ₉ O (CH ₂ ) ₁₀ O (CH ₂ ) ₁₁ Q Q8 Q8 Q8 Q8 Q8 ─────────────────────────────

──────────────────────────────────── Specific examples (525) (526) (527) (528) (529) L O (CH ₂ ) ₁₂ O (CH ₂ ) ₂ OCO O (CH ₂ ) ₃ OCO O (CH ₂ ) ₄ OCO O (CH ₂ ) ₅ OCO Q Q8 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (530) (531) (532) (533) (534) L O (CH ₂ ) ₆ OCO O (CH ₂ ) ₇ OCO O (CH ₂ ) ₈ OCO O (CH ₂ ) ₉ OCO O (CH ₂ ) ₁₀ OCO Q Q1 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (535) (536) (537) (538) (539) L O (CH ₂ ) ₁₁ OCO O (CH ₂ ) ₁₂ OCO O (CH ₂ ) ₂ OCO O (CH ₂ ) ₃ OCO O (CH ₂ ) ₄ OCO Q Q1 Q1 Q5 Q5 Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples (540) (541) (542) (543) (544) L O (CH ₂ ) ₅ OCO O (CH ₂ ) ₆ OCO O (CH ₂ ) ₇ OCO O (CH ₂ ) ₈ OCO O (CH ₂ ) ₉ OCO Q Q5 Q5 Q5 Q5 Q5 ────────────────────────────────────

──────────────────────────────────── Specific examples (545) (546) (547) (548) (549) L O (CH ₂ ) ₁₀ OCO O (CH ₂ ) ₁₁ OCO O (CH ₂ ) ₁₂ OCO O (CH ₂ ) ₂ O O (CH ₂ ) ₃ O Q Q5 Q5 Q5 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (550) (551) (552) (553) (554) L O (CH ₂ ) ₄ O O (CH ₂ ) ₅ O O (CH ₂ ) ₆ O O (CH ₂ ) ₇ O O (CH ₂ ) ₈ O Q Q1 Q1 Q1 Q1 Q1 ────────────────────────────────────

──────────────────────────────────── Specific examples (555) (556) (557) (558) L O (CH ₂ ) ₉ O O (CH ₂ ) ₁₀ O O (CH ₂ ) ₁₁ O O (CH ₂ ) ₁₂ O Q Q1 Q1 Q1 Q1 ────────────────────────────────────

Instead of introducing an asymmetric carbon atom into the divalent linking group (L) of the discotic liquid crystalline molecule, a compound (chiral agent) having an asymmetric carbon atom and exhibiting optical activity is used as an optically anisotropic layer. , The discotic liquid crystalline molecules can be helically twisted and aligned. As the compound containing an asymmetric carbon atom, various natural or synthetic compounds can be used. The same or similar polymerizable group as the discotic liquid crystalline molecule may be introduced into the compound containing an asymmetric carbon atom. When a polymerizable group is introduced, the discotic liquid crystal molecules are aligned substantially vertically (homogeneously) and then fixed, and at the same time, the compound containing an asymmetric carbon atom is also optically anisotropic by the same or similar polymerization reaction. Can be fixed in the functional layer.

In order to uniformly align the discotic liquid crystal molecules even on the air interface side, a fluorine-containing surfactant or a cellulose ester can be added to the optically anisotropic layer. The fluorinated surfactant is composed of a hydrophobic group containing a fluorine atom, a nonionic, anionic, cationic or amphoteric hydrophilic group and an optionally provided linking group. The fluorine-containing surfactant comprising one hydrophobic group and one hydrophilic group is represented by the following formula. Rf-L5-Hy wherein Rf is a monovalent hydrocarbon group substituted with a fluorine atom, L5 is a single bond or a divalent linking group,
Hy is a hydrophilic group. The above Rf functions as a hydrophobic group. The hydrocarbon group is preferably an alkyl group or an aryl group. The alkyl group preferably has 3 to 30 carbon atoms, and the aryl group preferably has 6 to 30 carbon atoms. Some or all of the hydrogen atoms contained in the hydrocarbon group are substituted with fluorine atoms. It is preferable to replace 50% or more of the hydrogen atoms contained in the hydrocarbon group with a fluorine atom.
More preferably, 0% or more is substituted, more preferably 70% or more is substituted, and most preferably 80% or more is substituted. The remaining hydrogen atoms may be further substituted with another halogen atom (eg, chlorine atom, bromine atom). Examples of Rf are shown below.

[0145] _{Rf1: n-C 8 F 17} - Rf2: n-C 6 F 13 - Rf3: Cl- (CF 2 -CFCl) 3 -CF 2 - Rf4: H- (CF 2) 8 - Rf5: H- _{(CF 2) 10 - Rf6:} n-C 9 F 19 - Rf7: pentafluorophenyl _{Rf8: n-C 7 F 15} - Rf9: Cl- (CF 2 -CFCl) 2 -CF 2 - Rf10: H- (CF _{2) 4 - Rf11: H- (} CF 2) 6 - Rf12: Cl- (CF 2) 6 - Rf13: C 3 F 7 -

In the above formula, the divalent linking group is an alkylene group, an arylene group, a divalent heterocyclic residue, -CO
—, —NR— (R is an alkyl group having 1 to 5 carbon atoms or a hydrogen atom), —O—, —SO ₂ — and a divalent linking group selected from the combination thereof. preferable. An example of L5 in the above formula is shown below. The left side is bonded to a hydrophobic group (Rf), and the right side is a hydrophilic group (Hy).
To join. AL represents an alkylene group, AR represents an arylene group, and Hc represents a divalent heterocyclic residue. Incidentally, an alkylene group, an arylene group and a divalent heterocyclic residue are
It may have a substituent (eg, an alkyl group).

[0147] L0: single bond _{L51: -SO 2 -NR- L52: -AL} -O- L53: -CO-NR- L54: -AR-O- L55: -SO 2 -NR-AL-CO-O- L56: -CO-O- L57: -SO 2 -NR-AL-O- L58: -SO 2 -NR-AL- L59: -CO-NR-AL- L60: -AL-O-AL- L61: - _{hc-AL- L62: -SO 2 -NR} -AL-O-AL- L63: -AR- L64: -O-AR-SO 2 -NR-AL- L65: -O-AR-SO 2 -NR- L66 : -O-AR-O-

Hy in the above formula is any one of a nonionic hydrophilic group, an anionic hydrophilic group, a cationic hydrophilic group and an amphoteric hydrophilic group. Nonionic hydrophilic groups are particularly preferred. An example of Hy in the above formula is shown below.

Hy1:-(CH ₂ CH ₂ O) n -H (n
Is an integer of 5 to _{30) Hy2 :-( CH 2 CH 2} O) n -R1 (n is 5 to 3
0 integer, R1 is an alkyl group having 1 to 6 carbon _{atoms) Hy3 :-( CH 2 CHOHCH 2)} n -H (n is 5 to 30 integer) Hy4: -COOM (M represents a hydrogen atom, an alkali metal atom or dissociated state) Hy5: -SO ₃ M (M is a hydrogen atom, an alkali metal atom or dissociated _{state) Hy6 :-( CH 2 CH 3 O} ) n -CH 2 CH 2 CH 2
—SO ₃ M (n is an integer of 5 to 30, M is a hydrogen atom or an alkali metal atom) Hy7: —OPO (OH) ₃ Hy8: —N ⁺ (CH ₃ ) ₃ .X ⁻ (X is a halogen atom) Hy9 : -COONH ₄

Nonionic hydrophilic groups (Hy1, Hy2, H
y3) is preferable, and a hydrophilic group (Hy1) composed of polyethylene oxide is most preferable. A fluorine-containing surfactant having two or more hydrophobic or hydrophilic groups containing a fluorine atom may be used. Two or more fluorine-containing surfactants may be used in combination. For fluorinated surfactants, see various references (eg, Hiroshi Horiguchi, “New Surfactants”, Sankyo Publishing (197
5), MJ Schick, Nonionic Surfactants, Marcell Dek
ker Inc., New York, (1967), JP-A-7-13293). The amount of the fluorinated surfactant is preferably in the range of 0.01 to 30% by weight, more preferably 0.05 to 10% by weight, and more preferably 0.1 to 5% by weight of the amount of the discotic liquid crystal molecules. % Is more preferable.

As the cellulose ester, a lower fatty acid ester of cellulose is preferably used. The “lower fatty acid” in the lower fatty acid ester of cellulose means a fatty acid having 6 or less carbon atoms. The number of carbon atoms is preferably 2 to 5, more preferably 2 to 4. A substituent (eg, hydroxy) may be bonded to the fatty acid. Two or more fatty acids may form an ester with cellulose. Examples of lower fatty acid esters of cellulose include cellulose acetate, cellulose propionate, cellulose butyrate, cellulose hydroxypropionate, cellulose acetate propionate, and cellulose acetate butyrate. Cellulose acetate butyrate is particularly preferred. The butyrylation degree of cellulose acetate butyrate is preferably 30% or more, and preferably 3% or more.
More preferably, it is 0 to 80%. The acetylation degree of cellulose acetate butyrate is preferably 30% or less, more preferably 1 to 30%. Cellulose ester is used in an amount of 0.005 to 0.5.
Preferably, it is used in an amount in the range of 5 g / m ² ,
The range is more preferably from 0.01 to 0.45 g / m ² , still more preferably from 0.02 to 0.4 / m ² , and more preferably from 0.03 to 0.35 / m ^2. Is most preferred. It is also preferable to use 0.1 to 5% by weight of the discotic liquid crystal molecules.

The optically anisotropic layer is composed of a discotic liquid crystalline molecule, and if necessary, a compound containing an asymmetric carbon atom (a compound having optical rotation), a fluorinated surfactant, a cellulose ester, or the following polymerizable compound. It is formed by applying a coating solution containing an initiator and other additives on the alignment film. As a solvent used for preparing the coating solution, an organic solvent is preferably used. Examples of organic solvents include amides (eg,
N, N-dimethylformamide), sulfoxide (eg,
Dimethyl sulfoxide), heterocyclic compound (eg, pyridine), hydrocarbon (eg, benzene, hexane), alkyl halide (eg, chloroform, dichloromethane), ester (eg, methyl acetate, butyl acetate), ketone (eg, acetone, Methyl ethyl ketone) and ethers (eg, tetrahydrofuran, 1,2-dimethoxyethane). Alkyl halides and ketones are preferred. Two or more organic solvents may be used in combination.

The coating solution can be applied by a known method (eg, extrusion coating, direct gravure coating, reverse gravure coating, die coating, bar coating). The aligned discotic liquid crystalline molecules are fixed while maintaining the aligned state. The immobilization is preferably performed by a polymerization reaction of the polymerizable group (Q) introduced into the discotic liquid crystalline molecule. The polymerization reaction includes a thermal polymerization reaction using a thermal polymerization initiator and a photopolymerization reaction using a photopolymerization initiator. Photopolymerization reactions are preferred. Examples of photopolymerization initiators include α
-Carbonyl compounds (U.S. Pat.
369670), acyloin ethers (described in US Pat. No. 2,448,828), α-hydrocarbon-substituted aromatic acyloin compounds (described in US Pat. No. 272251)
No. 2), polynuclear quinone compounds (US Pat. No. 304)
Nos. 6127 and 2951758), a combination of a triarylimidazole dimer and p-aminophenyl ketone (described in US Pat. No. 3,549,367), an acridine and phenazine compound (JP-A-60-105667, U.S. Pat. No. 4,239,850) and oxadiazole compounds (U.S. Pat. No. 4,221,970).

The amount of the photopolymerization initiator used is preferably 0.01 to 20% by weight of the solid content of the coating solution.
More preferably, it is 5 to 5% by weight. Light irradiation for the polymerization of discotic liquid crystalline molecules preferably uses ultraviolet light. The irradiation energy is 20 mJ /
cm ^{2 to} 50 J / cm ² , preferably 10
More preferably, it is 0 to 2000 mJ / cm ² . Light irradiation may be performed under heating conditions to promote the photopolymerization reaction. The thickness of the optically anisotropic layer is preferably 0.1 to 50 μm, more preferably 1 to 30 μm, and most preferably 5 to 20 μm. When two optical compensatory sheets are used in the liquid crystal display device, the thickness may be half the thickness of the optically anisotropic layer (the above-mentioned preferred range) required when using one optical compensatory sheet. The average tilt angle of the discotic liquid crystalline molecules in the optically anisotropic layer is 50 to 90 degrees. The angle of inclination is preferably as uniform as possible. However, if the tilt angle changes continuously along the thickness direction of the optically anisotropic layer, there is no problem even if there is a slight change.

In the case of an optical compensatory sheet for an STN type liquid crystal cell, the twist angle (twist angle) of the discotic liquid crystal molecules is equal to the twist angle of the STN type liquid crystal cell (generally, 1).
80 to 360 degrees, preferably more than 180 degrees to 270
It is preferable that the angle is adjusted to be similar (within ± 10 degrees as much as possible) depending on the angle. When one optical compensation sheet is used for a liquid crystal display device, the twist angle of the discotic liquid crystal molecules is preferably in the range of 180 to 360 degrees. When two optical compensation sheets are used in a liquid crystal display device, the twist angle of the discotic liquid crystal molecules is preferably in the range of 90 to 180 degrees. When the optical compensation sheet is used for an STN-type liquid crystal display device, the wavelength dependence of the birefringence of the optically anisotropic layer (Δn
(Λ) is preferably a value close to the wavelength dependence of the birefringence of the liquid crystal of the STN type liquid crystal cell.

[Liquid crystal display device] The optical compensation sheet of the present invention can be used for various liquid crystal display devices. TN
(Twisted Nematic), IPS (In-Plane Switchin)
g), FLC (Ferroelectric Liquid Crystal), OCB
(Optically Compensatory Bend), STN (SupperTwi
sted Nematic), VA (Vertically Aligned), GH
(Guest-Host) and HAN (Hybrid Aligned Nemati)
Liquid crystal display devices of various display modes such as c) have been proposed. When the optical compensatory sheet of the present invention is used for a TN liquid crystal display device or an STN liquid crystal display device, particularly a STN liquid crystal display device, a remarkable effect can be obtained. The STN type liquid crystal display device includes an STN type liquid crystal cell, one or two optical compensatory sheets disposed on one or both sides of the liquid crystal cell, and a pair of polarizing plates disposed on both sides thereof. S
In the TN type liquid crystal display device, the relationship between the alignment direction of the rod-shaped liquid crystal molecules of the liquid crystal cell and the alignment direction of the discotic liquid crystal molecules is determined by the director of the rod-shaped liquid crystal molecules of the liquid crystal cell closest to the optical compensation sheet. The long axis direction) and the director of the discotic liquid crystalline molecules of the optical compensation sheet closest to the liquid crystal cell (the normal direction of the disk-shaped core plane) are substantially in the same direction when viewed from the normal direction of the liquid crystal cell. (Less than ± 10 degrees). The transparent support of the optical compensation sheet can also function as a protective film on the liquid crystal cell side of the polarizing film. In this case, the transparent support should be arranged so that the slow axis (the direction in which the refractive index is maximized) and the transmission axis of the polarizing film are substantially perpendicular or substantially parallel (less than ± 10 degrees). Is preferred.

[0157]

EXAMPLES [Synthesis Example 1]

[0158]

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(1a) Synthesis of 4- (4-hydroxybutyloxy) cinnamic acid In a 1-liter three-necked flask, p-hydroxybenzaldehyde (40.0 g, 328 mmol) and 4-chlorobutyl acetate (54.3 g, 360 mmol),
Charge potassium carbonate (45.3 g, 32.8 mmol) and dimethylformamide (150 ml),
Stirred at C for 3 hours. After cooling, add water to the reaction mixture,
Extracted with ethyl acetate. After the solvent was distilled off, malonic acid (40.8 g, 392 mmol), pyrrolidine (10 ml) and pyridine (200 ml) were added to the obtained oil solution, and the mixture was stirred at 120 ° C. for 2 hours. After cooling to 60 ° C., methanol (200 ml) and a 40% by weight aqueous potassium hydroxide solution (200 ml) were added, and the mixture was further stirred at 60 ° C. for 2 hours. Then, after cooling, the reaction mixture was washed with water (4 liters).
Into a hydrochloric acid aqueous solution in which concentrated hydrochloric acid (330 ml) is dissolved,
The precipitated crystals were separated by filtration. The obtained crystals were recrystallized from acetonitrile to obtain the title compound (65.6).
g, yield: 85%).

(1b) Synthesis of 4- (4-acryloyloxybutyloxy) cinnamic acid In a 500 ml three-necked flask, the compound obtained in the above (1a) (20.0 g, 84.6 mmol), N, N −
Dimethylaniline (14.3 g, 118 mmol), acrylic acid chloride (9.6 ml, 118 mmol), nitrobenzene (0.1 g) and tetrahydrofuran (140 ml) were charged and stirred at 60 ° C. for 3 hours. After cooling, the reaction mixture was poured into a dilute aqueous hydrochloric acid solution, and the precipitated crystals were separated by filtration. Dimethylacetamide (30 ml), triethylamine (12 ml) and nitrobenzene (0.1 g) were added to the obtained crude crystals, and the mixture was stirred at 60 ° C. for 30 minutes. After cooling, pour the reaction mixture into dilute aqueous hydrochloric acid,
The precipitated crystals were separated by filtration. The obtained crystals were recrystallized from a mixed solvent of acetonitrile and water to give the title compound (20.0 g, yield: 81%).

(1c) Synthesis of 2,3,6,7,10,11-hexakis [4- (4-acryloyloxybutyloxy) cinnamoyloxy] triphenylene (20) In a 500 ml three-necked flask, methanesulfonyl chloride ( 31.6 g, 276 mmol), nitrobenzene (0.24 g) and tetrahydrofuran (180 m
1) and cooled to 0 ° C. This solution was added to the above (1)
Compound obtained in b) (80.0 g, 276 mmol)
And diisopropylethylamine (39.2 g, 30
(4 mmol) in tetrahydrofuran (180 ml) was added dropwise. After stirring at 0 ° C. for 1 hour, the reaction mixture was added to diisopropylethylamine (35.7 g, 276 mmol) and 4-dimethylaminopyridine (3.4 g, 2 g).
8 mmol) and then 2,3,6,7,1
0,11-hexahydroxytriphenylene (8.1
g, 25 mmol) of tetrahydrofuran (80 ml)
The suspension was added. After stirring at room temperature for 12 hours, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent,
The oil was purified by column chromatography to give the title compound (42.4 g, 87%).

[0162] ^{1 H-NMR (CDCl3) δ} ; 1.85 (24H, brs) 3.95 (12H, brs) 4.25 (12H, brs) 5.80 (6H, d) 6.10 (6H, dd) 6.40 (6H, d) 6.50 (6H, d) 6.70 (12H, d) 7.30 (12H, d) 7.85 (6H, d) 8.25 (6H, s)

[Synthesis Example 2]

[0164]

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(2a) Synthesis of 4- (2-hydroxyethyloxy) cinnamic acid In the same manner as in (1a) of Synthesis Example 1, except that 4-chloroethyl acetate was used instead of 4-chlorobutyl acetate. The title compound was obtained.

(2b) Synthesis of 4- (2-acryloyloxyethyloxy) cinnamic acid The title compound was obtained in the same manner as in (1b) of Synthesis Example 1, except that the compound obtained in (2a) was used. Was.

(2c) Synthesis of 2,3,6,7,10,11-hexakis [4- (2-acryloyloxyethyloxy) cinnamoyloxy] triphenylene (18) The compound obtained in the above (2b) was obtained. Except for using, the title compound was obtained in the same manner as in Synthesis Example 1 (1c).

[0168] ^{1 H-NMR (CDCl3) δ} ; 4.05 (12H, t) 4.30 (12H, t) 5.80 (6H, d) 6.10 (6H, dd) 6.40 (6H, d) 6.50 (6H, d) 6.75 (12H, d) 7.30 (12H, d) 7.85 (6H, d) 8.25 (6H, s)

[Synthesis Example 3]

[0170]

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(3a) Synthesis of 4- (6-hydroxyhexyloxy) cinnamic acid In the same manner as in (1a) of Synthesis Example 1, except that 6-chlorohexyl acetate was used instead of 4-chlorobutyl acetate. The title compound was obtained.

(3b) Synthesis of 4- (6-acryloyloxyhexyloxy) cinnamic acid The title compound was obtained in the same manner as in (1b) of Synthesis Example 1, except that the compound obtained in the above (3a) was used. Was.

(3c) Synthesis of 2,3,6,7,10,11-hexakis [4- (6-acryloyloxyhexyloxy) cinnamoyloxy] triphenylene (22) The compound obtained in the above (3b) was synthesized. Except for using, the title compound was obtained in the same manner as in Synthesis Example 1 (1c).

^1. 40-1.60 (24H, m) 1.60-1.90 (24H, m) 3.95 (12H, t) 4.20 (12H, 1H-NMR (CDCl 3) δ) t) 5.80 (6H, d) 6.10 (6H, dd) 6.40 (6H, d) 6.75 (12H, d) 7.30 (12H, d) 7.85 (6H, d) 8.25 (6H, s)

[Synthesis Example 4]

[0176]

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(4a) Synthesis of 4- (8-hydroxyoctyloxy) cinnamic acid In the same manner as in (1a) of Synthesis Example 1, except that 8-chlorooctyl acetate was used instead of 4-chlorobutyl acetate. The title compound was obtained.

(4b) Synthesis of 4- (8-acryloyloxyoctyloxy) cinnamic acid The title compound was obtained in the same manner as in (1b) of Synthesis Example 1, except that the compound obtained in the above (4a) was used. Was.

(4c) Synthesis of 2,3,6,7,10,11-hexakis [4- (8-acryloyloxyoctyloxy) cinnamoyloxy] triphenylene (24) The compound obtained in the above (4b) was synthesized. Except for using, the title compound was obtained in the same manner as in Synthesis Example 1 (1c).

^1. 40-1.60 (48H, m) 1.60-1.90 (24H, m) 3.95 (12H, t) 4.20 (12H, 1H-NMR (CDCl3) δ; t) 5.80 (6H, d) 6.10 (6H, dd) 6.40 (6H, d) 6.50 (6H, d) 6.75 (12H, d) 7.30 (12H, d) 7.85 (6H, d) 8.25 (6H, s)

[Synthesis Example 5]

[0182]

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(5a) Synthesis of 4- (10-hydroxydodecyloxy) cinnamic acid (1a) of Synthesis Example 1 except that 10-chlorododecyl acetate was used instead of 4-chlorobutyl acetate.
The title compound was obtained in the same manner as described above.

(5b) Synthesis of 4- (10-acryloyloxidedecyloxy) cinnamic acid The title compound was obtained in the same manner as in (1b) of Synthesis Example 1, except that the compound obtained in the above (5a) was used. Was.

(5c) Synthesis of 2,3,6,7,10,11-hexakis [4- (10-acryloyloxidedecyloxy) cinnamoyloxy] triphenylene (28) The compound obtained in the above (5b) was obtained. Except for using, the title compound was obtained in the same manner as in Synthesis Example 1 (1c).

¹ H-NMR (CDCl 3) δ; 1.40 to 1.60 (96H, m) 1.60 to 1.90 (24H, m) 3.95 (12H, t) 4.20 (12H, m) t) 5.80 (6H, d) 6.10 (6H, dd) 6.40 (6H, d) 6.50 (6H, d) 6.75 (12H, d) 7.30 (12H, d) 7.85 (6H, d) 8.25 (6H, s)

[Synthesis Example 6]

[0188]

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(6a) Synthesis of 4- (4-hydroxybutyloxy) benzaldehyde In a 1-liter three-necked flask, p-hydroxybenzaldehyde (24.4 g, 20 mmol) and 4-chlorobutyl acetate (36.1 g, 240 mmol) ), Potassium carbonate (33.2 g, 240 mmol) and dimethylformamide (150 ml) were charged and stirred at 120 ° C. for 3 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent, the oil was dissolved in methanol (100 ml) and potassium hydroxide (22.4) was added.
g, 0.4 mmol) of water (50 ml) was slowly added dropwise and refluxed for 2 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent, the oil was purified by column chromatography to obtain the title compound (35.3 g, yield: 91%).

(6b) Synthesis of methyl 3- [4- (4-hydroxybutyloxy) phenyl] -2-butenoic acid In a 300 ml three-necked flask, the compound obtained in the above (6a) (20 g, 103 mmol) was added. , Triethyl-2
-Charge phosphonopropionate (25.7 g, 108 mmol) and tetrahydrofuran (50 ml)
A methanol solution (21.8 g) of 28% by volume sodium ethoxide was added dropwise thereto. After stirring for 2 hours, dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent, the residue was purified by column chromatography to obtain the title compound (20.6 g, 76%).

(6c) Synthesis of 3- [4- (4-hydroxybutyloxy) phenyl] -2-butenoic acid In a 300 ml three-necked flask, the compound obtained in the above (6b) (20.4 g, 77.2) was added. Mmol) and methanol (50 ml), into which an aqueous solution (30 ml) of potassium hydroxide (8.66 g, 154 mmol) was added.
Was gradually added dropwise. After refluxing for 2 hours, dilute hydrochloric acid (500
ml), and the precipitated crystals were separated by filtration. The obtained crystals were recrystallized from acetonitrile to give the title compound (16.8 g, 87%).

(6d) Synthesis of 2,3,6,7,10,11-hexakis [4- (4-acryloyloxyoctyloxy) cinnamoyloxy] triphenylene (78) The compound obtained in the above (6c) was obtained. Synthesis Example 1 except for using
The title compound was obtained in the same manner as in (1c).

[0193] ^{1 H-NMR (CDCl3) δ} ; 1.90 (24H, brs) 2.20 (18H, s) 4.00 (12H, brs) 4.25 (12H, brs) 5.80 (6H, d) 6.10 (6H, dd) 6.40 (6H, d) 6.80 (12H, d) 7.25 (12H, d) 7.90 (6H, s) 8.35 (6H, s)

[Synthesis Example 7]

[0195]

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(7a) Synthesis of 4- (4-hydroxybutyloxy) acetophenone In a 1-liter three-necked flask, p-hydroxyacetophenone (27.2 g, 20 mmol) and 4-chlorobutyl acetate (36.1 g, 240 mmol) were added. ), Potassium carbonate (33.2 g, 240 mmol) and dimethylformamide (150 ml).
Stirred for hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent, the oil was dissolved in methanol (100 ml) and potassium hydroxide (22.4) was added.
g, 0.4 mmol) of water (50 ml) was slowly added dropwise and refluxed for 2 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent, the oil was purified by column chromatography to obtain the title compound (35.3 g, yield: 85%).

(7b) Synthesis of methyl 3- [4- (4-hydroxybutyloxy) phenyl] -2-methylacrylic acid In a 300 ml three-necked flask, the compound obtained in the above (7a) (15 g, 72. 0 mmol), triethylphosphonoacetate (17.0 g, 75.6 mmol) and tetrahydrofuran (50 ml), and a 28% by volume methanol solution of sodium ethoxide (15.3 g) was added dropwise. After refluxing for 3 hours, dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporating the solvent, the residue was purified by column chromatography to obtain the title compound (13.6 g, 68%).

(7c) Synthesis of 3- [4- (4-hydroxybutyloxy) phenyl] -2-methylacrylic acid In a 300 ml three-necked flask, the compound obtained in the above (7b) (13.6 g; 9 mmol) and methanol (50 ml), and an aqueous solution (30 ml) of potassium hydroxide (5.5 g, 98 mmol) was gradually added dropwise thereto. After refluxing for 2 hours, dilute hydrochloric acid (500m
The reaction mixture was poured into 1), and the precipitated crystals were separated by filtration.
The obtained crystals were recrystallized from acetonitrile to give the title compound (7.0 g, 57%).

(7d) Synthesis of 2,3,6,7,10,11-hexakis [4- (4-acryloyloxyoctyloxy) cinnamoyloxy] triphenylene (127) The compound obtained in the above (7c) was obtained. Synthesis Example 1 except for using
The title compound was obtained in the same manner as in (1c).

¹ H-NMR (CDCl 3) δ; 1.90 (24H, brs) 2.60 (18H, s) 4.00 (12H, brs) 4.25 (12H, brs) 5.80 (6H, br) d) 6.10 (6H, dd) 6.35 (6H, d) 6.80 (12H, d) 7.45 (12H, d) 8.35 (6H, s)

(Physical Properties of Discotic Liquid Crystalline Molecules) The discotic liquid crystal molecules (2
0), (18), (22), (24), (28), (7)
Regarding 8) and (127), changes in the liquid crystal phase were observed with a DSC (differential scanning calorimeter) and a deflection microscope. The results are shown in Table 1 below. For example, a discotic liquid crystalline molecule (20) is converted from a crystalline phase at 124 ° C. to N
Transferred to the _D phase was transferred from the N _D phase to an isotropic liquid at 222 ° C..

[0202]

[Table 1] Table 1 液晶 Liquid crystalline molecule phase transition temperature ─ ─────────────────────────────────── (20) Crystal → 124 ° C → N _D → 222 ° C → etc. isotropic liquid (18) crystal → 97 ° C. → columnar _{→ 105 ℃ → N D → 195} ℃ → isotropic liquid (22) crystal → 97 ° C. → columnar _{→ 105 ℃ → N D → 195} ℃ → isotropic liquid ( 24) Crystal → 124 ° C. → N _D → 180 ° C. → Isotropic liquid (28) Crystal → 117 ° C. → N _D → 162 ° C. → Isotropic liquid (78) Crystal → 60 ° C. → Columnar → 78 ° C. → N _D → 219 ° C. → isotropic liquid (127) crystal → 85 ° C. → columnar _{→ 90 ℃ → N D → 165} ℃ → isotropic liquid ─────────────────── ─────── ──────────

Example 1 The following acrylic acid copolymer and triethylamine (20 parts of acrylic acid copolymer)
Wt.) In a mixed solvent of methanol / water (volume ratio = 30).
/ 70) to prepare a 5% by weight solution.

[0204]

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The above solution was applied to a glass plate having a thickness of 1.1 mm using a bar coater. The coating layer was dried with hot air at 100 ° C. for 5 minutes, and the surface was rubbed to form a vertical alignment film. Compound (20) 1.0 obtained in Synthesis Example 1
g of cellulose acetate butyrate having a degree of acetylation of 20% and a degree of butyrylation of 52.0% (CAB-551-).
0.2, Eastman Chemical Co., Ltd.) 10 mg, the following chiral agent 25 mg, and a photopolymerization initiator (Irgacure 369, Nippon Ciba Geigy Co., Ltd.) 30 mg were added.
This is dissolved in methyl ethyl ketone and the solid content is 30% by weight.
Of an optically anisotropic layer was prepared.

[0206]

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An optically anisotropic layer coating solution was applied on the alignment film using a bar coater to form a coating layer of a discotic liquid crystalline compound. Then, the surface temperature was increased to 16
After the coating layer was brought into contact with the metal roller heated to 0 ° C. for 1 minute on the support (glass plate) side, the surface temperature was reduced to 30 ° C.
For 1 minute. Next, an ultraviolet irradiation device (URUTORA-VIOLETP)
Using UVL-58 (16W) manufactured by RODUCTS Co., Ltd., exposure was performed for 10 seconds to produce an optical compensation sheet. Polarized light enters the optical compensation sheet from the support at an angle of 45 degrees with respect to the rubbing axis of the alignment film, and is polarized using an optical device (Multi Chanel Photo Analyzer, manufactured by Otsuka Electronics Co., Ltd.). Analysis was performed to determine the twist angle, which was 230 to 250 degrees. Further, the retardation at the wavelength of 550 nm (Δn
When d) was obtained, it was 820 nm. Δn was determined from the measured retardation (Δnd) and the separately measured film thickness (d). As a result of the measurement, Δn was 0.155.

Example 2 The following modified polyvinyl alcohol was dissolved in a mixed solvent of N-methylpyrrolidone / methylethylketone (volume ratio = 20/80) to prepare a 5% by weight solution.

[0209]

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The above solution was applied to a 1.1 mm thick glass plate using a bar coater. The coating layer was dried with hot air at 80 ° C. for 10 minutes, and the surface was rubbed to form a vertical alignment film. An optically anisotropic layer was formed on the alignment film in the same manner as in Example 1 to produce an optical compensation sheet. Also, at an angle of 45 degrees with respect to the rubbing axis of the alignment film, polarized light is incident on the optical compensation sheet from the support side, and the optical device (Multi Ch.
Anel Photo Analyzer (manufactured by Otsuka Electronics Co., Ltd.) was used to analyze the polarization of the emitted light to determine the twist angle.
230 to 250 degrees. When the retardation (シ ョ ン nd) at a wavelength of 550 nm was determined,
20 nm. The measured retardation (△ n
d) and the thickness (d) (5.4 μm) measured separately, and Δ
n was determined. As a result of the measurement, Δn was 0.152.

Comparative Example 1 An optical compensatory sheet was produced in the same manner as in Example 1 except that the following discotic liquid crystalline compound (x) for comparison was used. The same operation as in Example 1 was performed to determine Δn, and Δn was 0.075. An optical compensatory sheet having the same Δnd value as the retardation (Δnd) described in Example 1 was attempted using the discotic liquid crystalline compound (x) for comparison. Was thicker than the optical compensatory sheet of Example 1, and the comparative discotic liquid crystalline compound (x) was not monodomain oriented.

[0212]

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Comparative Example 2 An optical compensatory sheet was produced in the same manner as in Example 2 except that the discotic liquid crystalline compound (x) for comparison was used. When Δn was determined by performing the same operation as in Example 2, Δn was 0.075. The discotic liquid crystal compound for comparison (x)
And the retardation described in Example 2 (Δn
An attempt was made to produce an optical compensatory sheet having the same Δnd value as in d). The optical compensatory sheet was thicker than the optical compensatory sheet of Example 23, and the comparative discotic liquid crystalline compound (x) was , And the monodomain was not oriented.

Example 3 An STN-type liquid crystal display device having the structure shown in FIG. 3E was manufactured using the optical compensation sheet manufactured in Example 1. On the surface where the liquid crystal cell and the optical compensation sheet were in contact, the alignment direction of the rod-like liquid crystal molecules of the liquid crystal cell was aligned with the alignment direction of the discotic liquid crystal molecules of the optical compensation sheet. The angle between the absorption axis of the exit-side polarizing plate and the orientation direction of the rod-like liquid crystal molecules on the exit side of the liquid crystal cell was adjusted to 45 degrees. The absorption axis of the incident side polarizing plate and the absorption axis of the emission side polarizing plate were arranged so as to be orthogonal to each other. When a voltage was applied to the obtained STN liquid crystal display device, a normally black mode was set. When the viewing angle characteristics were measured, an angle range having a contrast ratio of 5 or more was obtained at 120 degrees or more in the left and right directions and 150 degrees or more in the vertical direction.

Example 4 Polyvinyl alcohol (PV
A-203, manufactured by Kuraray Co., Ltd.) was dissolved in a mixed solvent of methanol / water (volume ratio = 20/80) to prepare a 5% by weight solution. This solution was applied to a 1.1 mm-thick glass plate using a bar coater. The coating layer was dried with hot air at 80 ° C. for 10 minutes, and the surface was rubbed to form an alignment film. 9.0 g of the compound (20) obtained in Synthesis Example 1,
Ethylene glycol-modified trimethylolpropane triacrylate (V # 360, manufactured by Osaka Organic Chemical Industry Co., Ltd.)
1.0 g, the following polymerization initiator 0.3 g and the following fluorine-containing polymer 0.05 g were dissolved in methyl ethyl ketone to prepare an optically anisotropic layer coating solution having a solid content of 25% by weight.

[0216]

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[0219]

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A coating liquid for an optically anisotropic layer was applied on the alignment film using a bar coater to form a coating layer.
The transparent support (glass plate) was brought into contact with a metal roller heated to a surface temperature of 130 ° C. for 1 minute.
It was brought into contact with a metal roller at 0 ° C. for 1 minute. Next, an ultraviolet irradiation device (URUTORA-VIOLETPRODUC)
Using UVL-58 (16W) manufactured by TS Co., Ltd.
Exposure was performed for 0 second to produce an optical compensation sheet. About the produced optical compensation sheet, ellipsometry (M-15)
0, manufactured by JASCO Corporation, and the retardation (Δnd) and the optical axis tilt angle (β) were determined. Note that Δnd
Does not become 0 even at the minimum point (no optical axis),
The angle of the minimum point was defined as the apparent inclination angle (β). Measured retardation (Δnd) and separately measured film thickness (d)
Then, Δn was determined. As a result of the measurement, Δn was 0.075. The apparent inclination angle (β) was 38 °.

Example 5 The following modified polyvinyl alcohol and glutaraldehyde (5% by weight of the modified polyvinyl alcohol) were dissolved in a mixed solvent of methanol / water (volume ratio = 20/80) to give 5% by weight. % Solution was prepared.

[0220]

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This solution was applied to a 100 μm cellulose triacetate film provided with a 0.1 μm gelatin thin film using a bar coater. The coating layer was dried with hot air at 80 ° C. for 10 minutes, and the surface was rubbed to form an alignment film. The coating liquid for the optically anisotropic layer used in Example 4 was applied on the alignment film using a bar coater to form a coating layer. The transparent support was brought into contact with a metal roller heated to a surface temperature of 130 ° C. for 1 minute, and further, a surface temperature of 30 ° C.
For 1 minute. Next, an ultraviolet irradiation device (URUTORA-VIOLET PRODUCTS)
Exposure was performed for 10 seconds using UVL-58 (16W) manufactured by K.K. to produce an optical compensation sheet. About the produced optical compensation sheet, ellipsometry (M-150,
Retardation (Δn) using JASCO Corporation
d) and the optical axis tilt angle (β) were determined. Since Δnd does not become 0 even at the minimum point (there is no optical axis), the angle of the minimum point was defined as an apparent inclination angle (β). The measured retardation (Δnd) was 160 nm, and the apparent inclination angle (β) was 22 °. Further, when Δn was calculated from the measured retardation (Δnd) and thickness (d), it was 0.070.

Example 6 A polarizing plate of a TFT type liquid crystal color television 6E-C3 manufactured by Sharp Corporation was peeled off, and TN
Two optical compensation sheets obtained in Example 5 were mounted so as to sandwich the liquid crystal cell. Thereafter, two polarizing plates were adhered so that the polarizing axes were orthogonal to each other, with the whole being sandwiched on the outermost side, thereby producing a liquid crystal display device. With respect to the obtained liquid crystal display device, white display and black display were performed, and the viewing angle at which the contrast ratio in the upper, lower, left, and right directions was 10: 1 was measured. That is, a rectangular wave voltage is applied to the obtained liquid crystal display device, and the contrast from the front direction and the direction inclined in the vertical and horizontal directions is measured using a spectrometer (LCD-5000, manufactured by Otsuka Electronics Co., Ltd.). And the contrast is 10
Vertical and horizontal viewing angles were obtained. As a result, the vertical viewing angle was 123 degrees, and the horizontal viewing angle was 115 degrees.

[Brief description of the drawings]

FIG. 1 shows the alignment state of rod-like liquid crystal molecules in a liquid crystal cell and the alignment state of discotic liquid crystal molecules in an optically anisotropic layer in a pixel portion of a STN type liquid crystal display device where no voltage is applied (off). It is sectional drawing which shows typically.

FIG. 2 is a schematic diagram showing respective refractive index ellipsoids of rod-like liquid crystal molecules of a liquid crystal cell and discotic liquid crystal molecules of an optical compensation sheet which has a relation of optically compensating the rod-like liquid crystal molecules.

FIG. 3 is a schematic view illustrating a layer configuration of an STN liquid crystal display device.

FIG. 4 is a plan view showing preferred optical directions for each element of the STN liquid crystal display device.

FIG. 5 is a plan view showing another preferred optical direction for each element of the STN type liquid crystal display device.

[Explanation of symbols]

DESCRIPTION OF SYMBOLS 1 Liquid crystal cell 2, 2a, 2b Optical compensation sheet 3, 3a, 3b Polarizer 11 Upper substrate of a liquid crystal cell 12, 14 Alignment film of a liquid crystal cell 13 Refractive index ellipsoid of a rod-like liquid crystal molecule 13a-13e Rod-like liquid crystal molecule 13t Thickness of rod-like liquid crystalline molecule layer 13x, 13y Refractive index of rod-like liquid crystalline molecule in plane parallel to alignment film 13z Refractive index of rod-like liquid crystalline molecule in thickness direction 15 Lower substrate of liquid crystal cell 21 Refraction of discotic liquid crystalline molecule Index ellipsoids 21a to 21e Discotic liquid crystal molecules 21t Thickness of discotic liquid crystal molecule layer 21x, 21y Refractive index in a plane parallel to the alignment film of discotic liquid crystal molecules 21z Refraction in the thickness direction of discotic liquid crystal molecules Ratio 22 Alignment film 23 Transparent support BL Backlight DDa, DDb, DDc, DDd Discotic liquid crystal Normal direction RDa of the disc face of the child, the direction the rubbing direction TAa, the transmission axis X criteria TAb polarizing plate alignment film RDb liquid crystal cell

Claims (9)

[Claims] 1. An optically anisotropic layer comprising a transparent support, an alignment film, and a discotic liquid crystalline molecule represented by the following formula (I) in this order: And an optical compensatory sheet having a refractive index anisotropy in the range of 0.065 to 0.16: Wherein A ¹ and A ² are independently a hydrogen atom,
Y is a halogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms;
Represents a hydrogen atom, a halogen atom, a carbon atom number of 1 to 12
An alkyl group, an alkoxy group having 1 to 12 carbon atoms, an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms. Or A ² and Y are combined to form a 5- or 6-membered ring; Z is a halogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. L is an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms; L is -O-, -CO-,- S-, -NH
-, An alkylene group, an alkenylene group, an alkynylene group,
Q is a divalent linking group selected from the group consisting of an arylene group and a combination thereof; Q is a polymerizable group;
a is 1, 2, 3, or 4; and b is an integer from 0 to (4-a). 2. An optically anisotropic layer having a thickness of 0.090 to 0.5.
The optical compensatory sheet according to claim 1, which has a refractive index anisotropy in a range of 16. 3. The optical compensatory sheet according to claim 1, wherein the orientation film comprises a modified polyvinyl alcohol, acrylic acid copolymer or methacrylic acid copolymer containing 1 to 90 mol% of a repeating unit represented by the following formula (II): Embedded image Wherein R ² is a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms; L ⁰ is —O—,
A divalent linking group selected from the group consisting of —CO—, —NH—, —SO ₂ —, an alkylene group, an alkenylene group, an arylene group and a combination thereof;
⁰ is a hydrocarbon group having 10 to 100 carbon atoms which may be substituted by a fluorine atom]. 4. A discotic liquid crystal molecule is twist-oriented in the optically anisotropic layer, and has a twist angle of 90.
The optical compensatory sheet according to claim 1, wherein the angle is in a range of about to 360 °. 5. The optical compensation sheet according to claim 4, wherein the optically anisotropic layer contains a compound having optical rotation. 6. The optical compensation sheet according to claim 1, wherein the discotic liquid crystalline molecules are oriented at an average inclination angle of 50 to 90 degrees with respect to the plane of the transparent support. 7. The optical compensatory sheet according to claim 1, wherein the discotic liquid crystalline molecules are oriented such that the tilt angle changes with the distance between the discotic liquid crystalline molecules and the plane of the transparent support. 8. An STN liquid crystal cell, two polarizing plates disposed on both sides thereof, and one or two optical compensation sheets disposed between the STN liquid crystal cell and one or both polarizing plates. Wherein the optical compensation sheet comprises a transparent support, an alignment film, and the following formula (I):
Having an optically anisotropic layer formed from discotic liquid crystalline molecules represented in this order, the optically anisotropic layer,
Having a refractive index anisotropy in the range of 0.065 to 0.16,
The discotic liquid crystal molecules are oriented at an average tilt angle in the range of 50 to 90 degrees, are further twisted, and have a twist angle in the range of 90 to 360 degrees. Chemical formula 3] Wherein A ¹ and A ² are independently a hydrogen atom,
Y is a halogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms;
Represents a hydrogen atom, a halogen atom, a carbon atom number of 1 to 12
An alkyl group, an alkoxy group having 1 to 12 carbon atoms, an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms. Or A ² and Y are combined to form a 5- or 6-membered ring; Z is a halogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. L is an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms; L is -O-, -CO-,- S-, -NH
-, An alkylene group, an alkenylene group, an alkynylene group,
Q is a divalent linking group selected from the group consisting of an arylene group and a combination thereof; Q is a polymerizable group;
a is 1, 2, 3, or 4; and b is an integer from 0 to (4-a). 9. A TN liquid crystal cell, two polarizing plates disposed on both sides thereof, and one or two optical compensation sheets disposed between the TN liquid crystal cell and one or both polarizing plates. The optical compensation sheet comprises a transparent support, an alignment film, and an optically anisotropic layer formed from discotic liquid crystalline molecules represented by the following formula (I) in this order. And the optically anisotropic layer is 0.06
It has a refractive index anisotropy in the range of 5 to 0.16, and the discotic liquid crystal molecules are oriented so that the tilt angle changes with the distance between the discotic liquid crystal molecules and the plane of the transparent support. TN-type liquid crystal display device: Wherein A ¹ and A ² are independently a hydrogen atom,
Y is a halogen atom, an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms;
Represents a hydrogen atom, a halogen atom, a carbon atom number of 1 to 12
An alkyl group, an alkoxy group having 1 to 12 carbon atoms, an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms. Or A ² and Y are combined to form a 5- or 6-membered ring; Z is a halogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. L is an acyl group having 2 to 13 carbon atoms, an alkylamino group having 1 to 12 carbon atoms or an acyloxy group having 2 to 13 carbon atoms; L is -O-, -CO-,- S-, -NH
-, An alkylene group, an alkenylene group, an alkynylene group,
Q is a divalent linking group selected from the group consisting of an arylene group and a combination thereof; Q is a polymerizable group;
a is 1, 2, 3, or 4; and b is an integer from 0 to (4-a).