| 5583679 | Liquid crystal display with optical compensatory sheet having discotic molecules varyingly inclined | December, 1996 | Ito et al. | |
| 5646703 | Liquid crystal display | July, 1997 | Kamada et al. | |
| 5805253 | Liquid crystal display with compensators having minimum retardations in the inclined direction | September, 1998 | Mori et al. | |
| 20060170851 | Method for producing film with twisted tilted alignment, film with twisted tilted alignment, and image display using same | August, 2006 | Kawamoto | 349/123 |
| 20070091228 | Liquid crystal display device | April, 2007 | Itadani et al. | 349/96 |
| DE3911620 | October, 1990 | |||
| JP6214116 | August, 1994 | |||
| JP0926572 | January, 1997 | |||
| JP9292522 | November, 1997 | |||
| JP1054982 | February, 1998 | |||
| JP2866372 | December, 1998 | |||
| WO/1996/037804 | November, 1996 | COMPENSATION FILM FOR LIQUID CRYSTAL DISPLAY DEVICE AND OCB MODE LIQUID DISPLAY DEVICE HAVING THE COMPENSATION FILM |
1. A retardation plate comprising: a transparent support; and an optically anisotropic layer formed from a discotic liquid crystalline compound, wherein the discotic liquid crystalline compound has a molecule oriented and fixed with an angle between a discotic plane of the molecule and a plane of the transparent plane substantially being a right angle, and the discotic liquid crystalline compound has a wavelength dispersion value smaller than that of compound (A):
2. The retardation plate according to claim 1, wherein the discotic liquid crystalline compound is represented by formula (IV):
3. The retardation plate according to claim 1, wherein the discotic liquid crystalline compound is represented by formula (DI):
*-(-L21-divalent cyclic group )n1-L22-L23-Q1 Formula (DI-R): wherein * represents the bonding site with the 5-membered ring in the formula (DI); L21 represents a single bond or a divalent linking group; the divalent cyclic group represents a divalent linking group having at least one cyclic structure; n1 represents an integer of 0 to 4; L22 represents *—O—, *—O—CO—, *—CO—O—, *—O—CO—O—, *—S—, *—N(R)H—, *—SO2—, *—CH2—, *—CH═CH—, or *C≡C— (where * represents the bonding site with the benzene ring in the formula (DI-R)); L23 represents a divalent linking group selected from the group consisting of —O—, —S—, —C(═O)—, —SO2—, —NH—, —CH2—, —CH═CH—, and —C≡C—, and combinations thereof, when the group is a group containing a hydrogen atom, the hydrogen atom may be substituted with a substituent; and Q1 each independently represents a polymerizable group or a hydrogen atom.
4. The retardation plate according to claim 1, wherein the compound (A) has a wavelength dispersion value, which is a ratio of a retardation at a wavelength of 480 mn to a retardation at a wavelength of 750 nm, of 1.18.
FIELD OF THE INVENTION
The invention relates to a retardation plate which uses a discotic liquid crystalline compound with a small wavelength dispersion value, and in which the discotic plane of the liquid crystalline compound is oriented generally perpendicular to the transparent support plane.
BACKGROUND OF THE INVENTION
A liquid crystal display generally includes a liquid crystal cell, polarizing elements, and retardation plates. In a transmission type liquid crystal display, generally, two sheets of polarizing elements are disposed on the opposite sides of the liquid crystal cell, and one sheet or two sheets of the retardation plates are disposed between the liquid crystal cell and the respective polarizing elements. In a reflection type liquid crystal display, generally, a reflection plate, a liquid crystal cell, a sheet of a retardation plate, and a sheet of a polarizing element are disposed in this order. The liquid crystal cell generally includes a rod-like liquid crystalline molecule layer, two sheets of substrates for sealing it, an electrode layer for applying a voltage to the rod-like liquid crystalline molecules, and alignment film layers for controlling the orientation of the rod-like liquid crystalline molecules. For the liquid crystal cell, there are proposed various display modes according to the difference in the orientation state of the rod-like liquid crystalline molecules, such as TN (Twisted Nematic), IPS (In-Plane Switching), FLC (Ferroelectric Liquid Crystal), OCB (Optically Compensatory Bend), STN (Super Twisted Nematic), VA (Vertically Aligned), and ECB (Electrically Controlled Birefringence) modes, for the transmission type, and TN, HAN (Hybrid Aligned Nematic), and GH (Guest-Host) modes for the reflection type.
The retardation plates are used in various liquid crystal displayes in order to eliminate image coloration or enlarge the viewing angle. As the retardation plate, a drawn birefringent polymer film has been used in the background art. There has been proposed the use of a retardation plate having an optically anisotropic layer formed of liquid crystalline molecules on a transparent support in place of a retardation plate formed of a drawn birefringent film. The liquid crystalline molecules have various orientation forms. For this reason, the use of the liquid crystalline molecules enables realization of the optical properties not obtainable with a drawn birefringent polymer film.
The optical properties of the retardation plate are determined according to the optical properties of the liquid crystal cell, specifically, the difference in display mode as described above. The used of the liquid crystalline molecules enables manufacturing of retardation plates having various optical properties adaptable to various display modes of the liquid crystal cell. As the liquid crystalline molecules, generally, rod-like liquid crystalline molecules or discotic liquid crystalline molecules are used. As the retardation plates using liquid crystalline molecules, the ones adaptable to various display modes have already been proposed. For example, retardation plates for the TN mode liquid crystal cell are described in each specification of JP-A-6-214116, U.S. Pat. No. 5,583,679, U.S. Pat. No. 5,646,703 and GP-A No. 3911620A1. Whereas, retardation plates for the IPS mode or FLC mode liquid crystal cell are described in JP-A-9-292522 and JP-A-10-54982. Further, retardation plates for the OCB mode or HAN mode liquid crystal cell are described in each specification of U.S. Pat. No. 5,805,253 and WO96/37804. Still further, retardation plates for the STN mode liquid crystal cell are described in JP-A-9-26572. Then, retardation plates for the VA mode liquid crystal cell are described in Japanese Patent No. 2866372.
Most of the discotic liquid crystalline molecules heretofore used for retardation plates are 2,3,6,7,10,11-hexa{4-(4-acryloyloxybutyloxy)benzoyloxy}triph enylene and derivatives thereof Further, examples using other discotic liquid crystalline molecules have been also reported. However, in any case, the wavelength dispersion value is higher than that of the compound represented by the compound (A).
However, a retardation plate has been required to have various wavelength dispersion values according to the intended use. Particulary, in recent years, the one with a low wavelength dispersion value has become in demand. For example, taking a λ/4 plate as an example of the retardation plate, a retardation plate using liquid crystalline molecules having a small wavelength dispersion value is higher in performances than the plate using liquid crystalline molecules having a large wavelength dispersion value when comparisons are made for all the wavelengths in the visible region.
SUMMARY OF THE INVENTION
An object of an illustrative, non-limiting embodiment of the invention is to provide a retardation plate, in which the discotic plane of the liquid crystalline compound is oriented substantially perpendicular to the transparent support plane, and which as a small wavelength dispersion value.
The foregoing object is achieved by the following aspects of the invention.
1. A retardation plate comprising:
a transparent support; and
an optically anisotropic layer formed from a discotic liquid crystalline compound, wherein the discotic liquid crystalline compound has a molecule oriented and fixed with an angle between a discotic plane of the molecule and a plane of the transparent plane substantially being a right angle, and the discotic liquid crystalline compound has a wavelength dispersion value smaller than that of compound (A):
2. The retardation plate according to the item 1, wherein the discotic liquid crystalline compound is represented by formula (IV):
wherein D represents triphenylene, n1 represents an integer of 3 to 6; and R 1 , R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyloxy group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, or a substituted or unsubstituted alkoxycarbonyl group having 1 to 20 carbon atoms.
3. The retardation plate according to the item 1, wherein the discotic liquid crystalline compound is represented by formula (DI):
wherein Y 11 , Y 12 , and Y 13 each independently represent methine or a nitrogen atom; L 1 , L 2 , and L 3 each independently represent a single bond or a divalent linking group; H 1 , H 2 , and H 3 each independently represent formula (DI-A) or formula (DI-B); and R 1 , R 2 , and R 3 each independently represent formula (DI-R):
Formula (DI-A):
wherein YA 1 and YA 2 each independently represent methine or a nitrogen atom; XA represents an oxygen atom, a sulfur atom, methylene, or imino; * represents the bonding site with L 1 to L 3 ; and ** represents the bonding site with R 1 to R 3 ,
Formula (DI-B):
wherein YB 1 and YB 2 each independently represent methine or a nitrogen atom; XB represents an oxygen atom, a sulfur atom, methylene, or imino; * represents the bonding site with L 1 to L 3 ; and ** represents the bonding site with R 1 to R 3 , and
*-(-L 21 -divalent cyclic group)n1-L 22 -L 23 -Q 1 Formula (DI-R):
wherein * represents the bonding site with the 5-membered ring in the formula (DI); L 21 represents a single bond or a divalent linking group; the divalent cyclic group represents a divalent linking group having at least one cyclic structure; n1 represents an integer of 0 to 4; L 22 represents *—O—, *—O—CO—, *—CO—O—, *—O—CO—O—, *—S—, *—N(R)H—, *—SO 2 —, *—CH 2 —, *—CH═CH—, or *—C≡C— (where * represents the bonding site with the benzene ring in the formula (DI-R)); L 23 represents a divalent linking group selected from the group consisting of —O—, —S—, —C(═O)—, —SO 2 —, —NH—, —CH 2 —, —CH═CH—, and —C≡C—, and combinations thereof, when the group is a group containing a hydrogen atom, the hydrogen atom may be substituted with a substituent; and Q 1 each independently represents a polymerizable group or a hydrogen atom.
Incidentally, in this specification, the wordings “substantially (or generally) right angle” and “substantially (or generally) pependicular” means that it includes not only the embodiment of precisely 90° but also the embodiment of 90±5° or 90±10°. However, 90±5° is preferred.
Whereas, the wavelength dispersion value is the value obtained by dividing the retardation value at a short wavelength (a given wavelength in 400 nm to 550 nm) by the retardation value at a long wavelength (a given wavelength in 600 nm to 800 nm), revealed by the orientation of liquid crystal molecules. Namely, Wavelength dispersion value=(Retardation value at a short wavelength)/(Retardation value at a long wavelength).
In accordance with the invention, it is possible to provide a retardation plate in which the discotic plane of the liquid crystalline compound and the transparent support plane are oriented generally perpendicular to each other, and which has a small wavelength dispersion value.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is a schematic cross sectional view of an exemplary embodiment of a retardation plate of the invention.
FIG. 2 is a perspective view of an exemplary embodiment of a retardation plate of the invention.
FIG. 3A is a schematic side view 3 A of an exemplary embodiment of the invention, and FIG. 3B is a schematic front view 3 B of one embodiment thereof.
DETAILED DESCRIPTION OF THE INVENTION
Below, exemplary embodiments of the invention will be described in details.
(Wavelength Dispersion Value)
The wavelength dispersion value is the value represented by Wavelength dispersion value={Retardation value at a short wavelength (a given wavelength in 400 run to 550 nm)}/{Retardation value at a long wavelength (a given wavelength in 600 nm to 800 nm)}. Herein, the retardation value is the value measured with discotic liquid crystalline molecules oriented generally perpendicular to the alignment film plane. The measurement of retardation is possible by means of various devices. For example, as the device capable of such a measurement, mention may be made of KOBRA (manufactured by Oji Scientific Instruments Co., Ltd.) as an example. For example, by carrying out the measurement with KOBRA-31 PR, it is possible to measure the retardation at 480 nm (±5 nm) and 750 nm (±5 nm).
The following compound (A) is oriented generally perpendicular to the alignment film plane, and the measurement is carried out by means of KOBRA-31PR, thereby to obtain a wavelength dispersion value (480 nm/750 nm)=1.18.
A discotic liquid crystalline compound for use in the invention is characterized by having a smaller wavelength dispersion value than that of the compound (A).
The discotic liquid crystalline compound for use in the invention has a wavelength dispersion value of preferably 1.03 to 1.17, and particularly preferably 1.05 to 1.14 in terms of the wavelength dispersion value (480 nm/750 nm) measured by KOBRA-31PR.
(Discotic Liquid Crystalline Compound)
The discotic liquid crystalline compound in accordance with the invention is preferably a compound represented by the following formula (I) or the following formula (DI).
Below, a detailed description will be given sequentially from the following formula (I):
In the formula (I), D is a discotic core. The discotic core is situated at the center of the discotic compound, and forms the discotic plane. The discotic core is a well known conception in the molecular structure of the discotic liquid crystalline molecules. The discotic liquid crystal is described in various documents (C. Destrade et al., Mol. Crysr. Liq. Cryst. , vol. 71, page 111(1981); Kikann Kagaku No Sousetsu No. 22, Ekisyou No Kagaku , chapter 5, chapter 10, section 2, (1994) edited by the Chemical Society of Japan; B. Kohne et al., Angew. Chem. Soc. Chem. Comm. , page 1794 (1985); J. Zhang et al., J. Am. Chem. Soc. , vol. 116, page 2655 (1994); and the like.
Below, examples of the discotic core will be shown. Y in each compound denotes the following formula (VI). R 1 , R 2 , R 3 , R 4 , and R 5 in the formula (VI) have the same definitions as those of the formula (I), and the preferred ranges thereof are also the same.
The discotic core (D) is particularly preferably triphenylene (Z4).
The discotic core (D) may have a substituent other than Y (the formula (VI)). Examples of the substituent which the discotic core may have include halogen atoms (a fluorine atom, a chlorine a atom, bromine atom, and an iodine atom), a cyano group, a hydroxyl group, an amino group, a carbamoyl group, a sulfamoyl group, a mercapto group, an ureido group, an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, a substituted aryl group, a heterocyclic group, an alkoxy group, a substituted alkoxy group, an aryloxy group, a substituted aryloxy group, an acyl group, an acyloxy group, an alkoxycarbonyl group, a substituted alkoxycarbonyl group, an aryloxycarbonyl group, a substituted aryloxycarbonyl group, a substituted amino group, an amido group, an imido group, an alkoxycarbonylamino group, a substituted alkoxycarbonylamino group, an aryloxycarbonylamino group, a substituted aryloxycarbonylamino group, a substituted carbamoyl group, a sulfonamido group, a substituted sulfamoyl group, an alkylthio group, a substituted alkylthio group, an arylthio group, a substituted arylthio group, an alkyl sulfonyl group, a substituted alkyl sulfonyl group, an aryl sulfonyl group, a substituted aryl sulfonyl group, an alkyl sulfinyl group, a substituted alkyl sulfinyl group, an aryl sulfinyl group, a substituted aryl sulfinyl group, a substituted ureido group, a phosphoric acid amido group, a substituted silyl group, an alkoxycarbonyloxy group, a substituted alkoxycarbonyloxy group, an aryloxycarbonyloxy group, and a substituted aryloxycarbonyloxy group.
The alkyl group may have a cyclic structure or a branched structure. The number of carbon atoms of the alkyl group is preferably 1 to 30. The alkyl moiety of a substituted alkyl group has the same definition as that for an alkyl group, and the preferred range thereof also has the same definition. Examples of the substituent of the substituted alkyl group have the same definition as that for the examples of the substituent of the discotic core except for an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkyl group, and a substituted alkynyl group, and the preferred range thereof also has the same definition.
The alkenyl group may have a cyclic structure or a branched structure. The number of carbon atoms of the alkenyl group is preferably 2 to 30. The alkenyl moiety of a substituted alkenyl group has the same definition as that for an alkenyl group, and the preferred range thereof also has the same definition. Examples of the substituent of the substituted alkenyl group are the same as the examples of the substituent of a substituted alkyl group. The alkynyl group may have a cyclic structure or a branched structure. The number of carbon atoms of the alkynyl group is preferably 2 to 30. The alkynyl moiety of a substituted alkynyl group has the same definition as that for an alkynyl group. Examples of the substituent of the substituted alkynyl group have the same definition as that for the examples of the substituent of a substituted alkyl group, and the preferred range thereof also has the same definition.
The number of carbon atoms of the aryl group is preferably 6 to 30. The aryl moiety of a substituted aryl group has the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of the substituted aryl group have the same definition as that for the examples of the substituent of the discotic core, and the preferred range thereof also has the same definition.
The heterocyclic group preferably has a 5-membered or 6-membered heterocyclic ring. The heterocyclic ring may be condensed with another heterocyclic ring, aliphatic ring, or aromatic ring. The hetero atom of the heterocyclic ring is preferably a nitrogen atom, an oxygen atom, or a sulfur atom. The heterocyclic group may have a substituent. Examples of the substituent of the heterocyclic group have the same definition as that for the examples of the substituent of the discotic core, and the preferred range thereof also has the same definition.
The alkyl moieties of an alkoxy group and a substituted alkoxy group have the same definition as that for an alkyl group, and the preferred ranges thereof also have the same definition. Examples of the substituent of the substituted alkoxy group have the same definition as that for the examples of the substituent of a substituted alkyl group, and the preferred range thereof also has the same definition. The aryl moieties of an aryloxy group and a substituted aryloxy group have the same definitions as those for an aryl group, and the preferred ranges also have the same definitions. Examples of the substituent of the substituted aryloxy group have the same definition as that for the examples of the substituent of the discotic core, and the preferred range thereof also has the same definition.
The acyl group is represented by formyl or —CO—R, where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The acyloxy group is represented by formyloxy or —O—CO—R, where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The alkyl moieties of an alkoxycarbonyl group and a substituted alkoxycarbonyl group are the same as an alkyl group. Examples of the substituent of a substituted alkoxycarbonyl group have the same definition as that for the examples of the substituent of a substituted alkyl group, and the preferred range thereof also has the same definition.
The aryl moieties of an aryloxycarbonyl group and a substituted aryloxycarbonyl group have the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted aryloxycarbonyl group have the same definition as that for the examples of the substituent of the discotic core, and the preferred range thereof also has the same definition.
The substituted amino group is represented by —NH—R or —N(—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The amido group is represented by —NH—CO—R, where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The imido group is represented by —N(—CO—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The alkyl moieties of an alkoxycarbonylamino group and a substituted alkoxycarbonylamino group have the same definition as that for an alkyl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted alkoxycarbonylamino group are the same as the examples of the substituent of a substituted alkyl group.
The aryl moieties of an aryloxycarbonylamino group and a substituted aryloxycarbonylamino group have the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted aryloxycarbonylamino group are the same as the examples of the substituent of the discotic core.
The substituted carbamoyl group is represented by —CO—NH—R or —CO—N(—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The sulfonamido group is represented by —NH—SO 2 R where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group. The substituted sulfamoyl group is represented by —SO 2 —NH—R or —SO 2 —N(—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The alkyl moieties of an alkylthio group and a substituted alkylthio group are the same as an alkyl group. Examples of the substituent of the substituted alkylthio group are the same as the examples of the substituent of a substituted alkyl group.
The aryl moieties of an arylthio group and a substituted arylthio group have the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of the substituted arylthio group have the same definition as that for the examples of the substituent of the discotic core, and the preferred range thereof also has the same definition.
The alkyl moieties of an alkyl sulfonyl group and a substituted alkyl sulfonyl group have the same definition as that for an alkyl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted alkyl sulfonyl group have the same definition as that for the examples of the substituent of a substituted alkyl group, and the preferred range thereof also has the same definition.
The aryl moieties of an aryl sulfonyl group and a substituted aryl sulfonyl group have the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted aryl sulfonyl group have the same definition as that for the examples of the discotic core, and the preferred range thereof also has the same definition.
The alkyl moieties of an alkyl sulfinyl group and a substituted alkyl sulfinyl group have the same definition as that for an alkyl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted alkyl sulfinyl group have the same definition as that for the examples of the substituent a substituted alkyl group, and the preferred range thereof also has the same definition.
The aryl moieties of an alkyl sulfinyl group and a substituted alkyl sulfinyl group have the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted alkyl sulfinyl group have the same definition as that for the examples of the substituent of the discotic core, and the preferred range thereof also has the same definition.
The substituted ureido group is represented by —NH—CO—NH—R or —NH—CO—N(—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The phosphoric acid amido group is represented by —NH—O—P(═O)(—OH)—O—R or —NH—O—P(═O)(—O—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The substituted silyl group is represented by —SiH 2 —R, —SiH(—R) 2 or —Si(—R) 2 , where R is an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aryl group, or a substituted aryl group.
The alkyl moieties of an alkoxycarbonyloxy group and a substituted alkoxycarbonyloxy group are the same as an alkyl group. Examples of the substituent of a substituted alkoxycarbonyloxy group have the same definition as that for the examples of a substituted alkyl group, and the preferred range thereof also has the same definition.
The aryl moieties of an aryloxycarbonyloxy group and a substituted aryloxycarbonyloxy group have the same definition as that for an aryl group, and the preferred range thereof also has the same definition. Examples of the substituent of a substituted aryloxycarbonyloxy group have the same definition as that for the examples of discotic core, and the preferred range thereof also has the same definition.
In the formula (I), n1 is an integer of 3 to 20, preferably an integer of 3 to 15, more preferably an integer of 3 to 12, further preferably an integer of 3 to 10, still further preferably an integer of 4 to 8, and most preferably 6.
In the formula (I), R 1 , R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or a substituent, and examples thereof may include the same ones as the examples of the substituent of the discotic core. Whereas, any two of R 1 , R 2 , R 3 , R 4 and R 5 may combine with each other to form a ring. Examples thereof may include an aliphatic or aromatic ring. Preferably, R 1 , R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a cyano group, a substituted or unsubstituted alkoxycarbonyl group or a halogen atom.
R 2 and R 3 , and R 4 and R 5 are in a cis-trans positional relationship with respect to a carbonyloxy group. The cis form is the form in which substituents are present along the same direction as the carbonyloxy group with respect to the cyclopropane ring plane. Whereas, the trans form is the form in which substituents are present in the opposite direction from the carbonyloxy group with respect to the cyclopropane ring plane. This positional relationship has no particular restriction unless otherwise specified.
In the formula (I), stereoisomers of enantiomer and diastereoisomer are present according to the combination of the substituents of R 1 , R 2 , R 3 , R 4 and R 5 , but these have no particular restriction unless otherwise specified.
The discotic compound represented by the formula (I) is preferably represented by the following formula (II):
In the formula (II), D is a discotic core; n1 is an integer of 3 to 20; R 1 , R 2 , R 3 and R 5 each represent a hydrogen atom or a substituent, and may combine with each other to form a ring; m represents an integer of 1 to 5; and R 6 represents a substituent, and when a plurality of R 6 's are present, these may be respectively the same or different from each other, and may combine with each other to form a ring.
The D, R 1 , R 2 , R 3 and R 5 are the same as D, n1, R 1 , R 2 , R 3 and R 5 defined in relation to the formula (I), and the preferred range thereof also has the same definition.
In the formula (II), R 6 represents a substituent, and examples thereof may include the same ones as the examples of the substituents of the discotic core. Preferred examples of R 6 may include a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxycarbonyloxy group, a substituted or unsubstituted aryloxycarbonyloxy group, or a substituted or unsubstituted acyloxy group. Further preferably, at least one R 6 is a substituted alkyl group, a substituted alkoxy group, a substituted alkoxycarbonyl group, a substituted aryl group, a substituted aryloxy group, a substituted alkoxycarbonyloxy group, a substituted aryloxycarbonyloxy group, or a substituted acyloxy group, and has a polymerizable group at the end of the substituent.
In the formula (II), the substation site of R 6 has no particular restriction unless otherwise specified. Preferably, at least one R 6 's is present at the para position.
In the formula (II), R 5 is in a cis/trans positional relationship with respect to the carbonyloxy group. This positional relationship has no particular restriction unless otherwise specified. Cis is preferred.
The discotic compound of the invention, for example, the discotic compound represented by the formula (I), can have a polymerizable group. The discotic compound having a polymerizable group (polymerizable discotic compound) can be fixed the state in which the discotic plane of the discotic compound is oriented by the polymerization reaction.
When the compound represented by the formula (I) has a polymerizable group, it is preferable that R 4 is a substituted alkyl group, a substituted alkoxy group, a substituted aryl group, or a substituted aryloxy group, and has a polymerizable group at the end of each substituent.
The polymerizable discotic compound is further preferably represented by the formula (III):
In the formula (III), D is a discotic core; n1 represents an integer of 3 to 20; R 1 , R 2 , R 3 and R 5 each represent a hydrogen atom or a substituent, and may combine with each other to form a ring.
D, n1, R 1 , R 2 , R 3 and R 5 are the same as D, R 1 , R 2 , R 3 and R 5 defined in relation to the formula (I), and the preferred range thereof also has the same definition.
In the formula (III), L is a divalent linking group selected from an oxygen atom, a sulfur atom, a carbonyl group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, and combinations thereof.
The alkylene group may have a cyclic structure or a branched structure. The number of carbon atoms of the alkylene group is preferably 1 to 30.
The alkylene moiety of a substituted alkylene group has the same definition as that for an alkylene group. Examples of the substituent of the substituted alkylene group are the same as the examples of the substituent of the discotic core described in relation to the formula (I), except for an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group and a substituted alkynyl group.
The number of carbon atoms of the arylene group is preferably 1 to 30. The arylene group is preferably phenylene or naphthylene, further preferably phenylene, and most preferably p-phenylene.
The arylene moiety of a substituted arylene group is the same as the arylene group. Examples of the substituent of the substituted arylene group are the same as the examples of the substituent of the discotic core described in relation to the formula (I).
In the formula (III), Q is a polymerizable group. The polymerizable group is further preferably an epoxy group or an ethylenic unsaturated group, and most preferably an ethylenic unsaturated group (e.g., vinyl, 1-propenyl, or isopropenyl).
The particularly preferred discotic compound as the discotic compound of the invention is a triphenylene compound represented by the following formula (IV):
In the formula (IV), D1 represents triphenylene, n1 represents an integer of 3 to 6, R 1 , R 2 , R 3 , R 4 and R 5 are each a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyloxy group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, or a substituted or unsubstituted alkoxycarbonyl group having 1 to 20 carbon atoms. The definition and examples of each group are the same as those for the formula (I), and the preferred range thereof also has the same definition.
In the formula (IV), R 1 , R 2 , R 3 , R 4 and R 5 are each preferably a hydrogen atom, a methyl group, an ethyl group, a methyloxy group, an ethyloxy group, a cyano group, a halogen atom, or a substituted or unsubstituted alkoxycarbonyl group.
In the formula (IV), preferably, R 4 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. Further, preferably, R 4 is in trans relation with respect to the carbonyloxy group.
The triphenylene compound represented by the formula (IV) can have a polymerizable group. The triphenylene compound having a polymerizable group (polymerizable triphenylene compound) can be fixed in the state in which the discotic plane including triphenylene is oriented by the polymerization reaction.
When the triphenylene compound represented by the formula (IV) has a polymerizable group, it is preferable that R 4 is a substituted alkyl group having 2 to 20 carbon atoms, a substituted alkoxy group having 2 to 20 carbon atoms, a substituted aryl group having 6 to 20 carbon atoms, or a substituted aryloxy group having 6 to 20 carbon atoms, and has a polymerizable group at the end of the substituent.
In the formula (IV), an asymmetric carbon atom is present, and hence a diastereomer or an enantiomer is present. However, in the invention, no distinction is made between these, and all are assumed to be included. In other words, it is assumed that no distinction is made between the stereoisomers according to the method of describing the structure.
Below, examples of the discotic compound represented by the formula (I) will be shown. Incidentally, when each exemplified compound is shown, it is shown as the exemplified compound (x), where x is the numerical value (x) described beside the exemplified compound.
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| R = | | (19) | |
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| R = | | (36) | |
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| R = | | (53) | |
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| R = | | (64) | |
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| | (75) | ||
| | (76) | ||
Next, the formula (DI) will be described in details.
In the formula (DI), Y 11 , Y 12 , and Y 13 each independently represent methine or a nitrogen atom.
When Y 11 , Y 12 , and Y 13 are each methine, methine may have a substituent. Examples of the substituent of methine may include an alkyl group, an alkoxy group, an aryloxy group, an acyl group, an alkoxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an alkylthio group, an arylthio group, a halogen atom, and a cyano group. Out of these, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an acyloxy group, a halogen atom, and a cyano group are further preferred, and an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 12 carbon atoms, an acyloxy group having 2 to 12 carbon atoms, a halogen atom, and a cyano group are most preferred.
It is most preferable that Y 11 , Y 12 , and Y 13 are all methines. Whereas, it is most preferable that methine is unsubstituted.
In the formula (DI), L 1 , L 2 , and L 3 are each independently a single bond or a divalent linking group. When L 1 , L 2 , and L 3 are each a divalent linking group, they are each independently preferably a divalent linking group selected from the group consisting of —O—, —S—, —C(═O)—, —NH—, —SO 2 —, —CH═CH—, and —C≡C—, and combinations thereof. When the foregoing group is a group containing a hydrogen atom, the hydrogen atom may be substituted with a substituent. Preferred examples of such a substituent may include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a halogen-substituted alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an acyloxy group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 6 carbon atoms, and an acylamino group having 2 to 6 carbon atoms. A halogen atom, and an alkyl group having 1 to 6 carbon atoms are more preferred.
The divalent cyclic group represented by L 1 , L 2 , or L 3 is a divalent linking group having at least one cyclic structure. The divalent cyclic group is preferably a 5-membered ring, a 6-membered ring, or a 7-membered ring, further preferably a 5-membered ring or a 6-membered ring, and most preferably a 6-membered ring. The ring contained in the cyclic group may be a condensed ring. However, it is more preferably a single ring than a condensed ring. Further, the ring contained in the cyclic group may be any of an aromatic ring, an aliphatic ring, and a heterocyclic ring. Examples of the aromatic ring may include a benzene ring and a naphthalene ring. Examples of the aliphatic ring may include a cyclohexane ring. Examples of the heterocyclic ring may include a pyridine ring and a pyrimidine ring. The cyclic groups are preferably an aromatic ring, and a heterocyclic ring.
The cyclic group having a benzene ring out of the divalent cyclic groups represented by L 1 , L 2 , and L 3 is preferably 1,4-phenylene. The cyclic groups having a naphthalene ring are preferably naphthalene-1,5-diyl and naphthalene-2,6-diyl. The cyclic group having a cyclohexane ring is preferably 1,4-cyclohexylene. The cyclic group having a pyridine ring is preferably pyridine-2,5-diyl. The cyclic group having a pyrimidine ring is preferably pyrimidine-2,5-diyl.
The divalent cyclic groups represented by L 1 , L 2 , and L 3 may each have a substituent. Examples of the substituent may include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 16 carbon atoms, an alkenyl group having 1 to 16 carbon atoms, an alkynyl group having 1 to 16 carbon atoms, a halogen-substituted alkyl group having 1 to 16 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, an acyl group having 2 to 16 carbon atoms, an alkylthio group having 1 to 16 carbon atoms, an acyloxy group having 2 to 16 carbon atoms, an alkoxycarbonyl group having 2 to 16 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 16 carbon atoms, and an acylamino group having 2 to 16 carbon atoms.
L 1 , L 2 , and L 3 are each preferably a single bond, *—O—CO—, *—CO—O—, *—CH═CH—, *—C≡C—, *-divalent cyclic group-, *—O—CO-divalent cyclic group-, *—CO—O-divalent cyclic group-, *—CH═CH-divalent cyclic group, *—C≡C-divalent cyclic group-, *-divalent cyclic group-O—CO—, *-divalent cyclic group-CO—O—, *-divalent cyclic group-CH═CH—, or *-divalent cyclic group-C≡C—. They are each in particular preferably a single bond, *—CH═CH—, *—C≡C—, *—CH═CH-divalent cyclic group, or *—C≡C-divalent cyclic group, and most preferably a single bond (where * represents the bonding site with the 6-membered ring containing Y 11 , Y 12 , and Y 13 , in the formula (DI)).
H 1 , H 2 , and H 3 each independently represent the following formula (DI-A) or the following formula (DI-B).
In the formula (DI-A), YA 1 and YA 2 each independently represent methine or a nitrogen atom. It is preferable that at least one of YA 1 and YA 2 is a nitrogen atom, and it is most preferable that both are nitrogen atoms. XA represents an oxygen atom, a sulfur atom, methylene, or imino. XA is most preferably an oxygen atom. * represents the bonding site with L 1 to L 3 , and ** represents the bonding site with R 1 to R 3 .
In the formula (DI-B), YB 1 and YB 2 each independently represent methine or a nitrogen atom. It is preferable that at least one of YB 1 and YB 2 is a nitrogen atom, and it is most preferable that both are nitrogen atoms. XB represents an oxygen atom, a sulfur atom, methylene, or imino. XB is most preferably an oxygen atom. * represents the bonding site with L 1 to L 3 , and ** represents the bonding site with R 1 to R 3 .
In the formula (DI), R 1 , R 2 , and R 3 each independently represent the following formula (DI-R).
*-(-L 21 -divalent cyclic group ) n1 -L 22 -L 23 -Q 1 Formula (DI-R):
In the formula (DI-R), * represents the bonding site with the 5-membered ring in the formula (DI).
L 21 is a single bond or a divalent linking group. When L 21 is a divalent linking group, it is preferably a divalent linking group selected from the group consisting of —O—, —S—, —C(═O)—, —NH—, —SO 2 —, —CH═CH— and, C≡C—, and combinations thereof. When the foregoing group is a group containing a hydrogen atom, the hydrogen atom may be substituted with a substituent. Preferred examples of such a substituent may include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a halogen-substituted alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an acyloxy group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group 2 to 6 carbon atoms, and an acylamino group having 2 to 6 carbon atoms. A halogen atom and an alkyl group having 1 to 6 carbon atoms are more preferred.
L 21 is preferably a single bond, and, **—O—CO—, **—CO—O—, **—CH═CH—, or **—C≡C— (where ** represents the left-hand side of L 21 in the formula (DI-R)). Particularly, a single bond is preferred.
The divalent cyclic group in the formula (DI-R) is a divalent linking group having at least one cyclic structure. The divalent cyclic group is preferably a 5-membered ring, a 6-membered ring, or a 7-membered ring, further preferably a 5-membered ring or a 6-membered ring, and most preferably a 6-membered ring. The ring contained in the cyclic group may be a condensed ring. However, it is more preferably a single ring than a condensed ring. Further, the ring contained in the cyclic group may be any of an aromatic ring, an aliphatic ring, and a heterocyclic ring. Examples of the aromatic ring may include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring. Examples of the aliphatic ring may include a cyclohexane ring. Examples of the heterocyclic ring may include a pyridine ring and a pyrimidine ring.
The cyclic groups having a benzene ring out of the divalent cyclic groups are preferably 1,4-phenylene and 1,3-phenylene. The cyclic groups having a naphthalene ring are preferably naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-2,5-diyl, naphthalene-2,6-diyl,and naphthalene-2,7-diyl. The cyclic group having a cyclohexane ring is preferably 1,4-cyclohexylene. The cyclic group having a pyridine ring is preferably pyridine-2,5-diyl. The cyclic group having a pyrimidine ring is preferably pyrimidine-2,5-diyl. The divalent cyclic groups are in particular preferably 1,4-phenylene, 1,3-phenylene, and naphthalene-2,6-diyl.
The divalent cyclic group may have a substituent. Examples of the substituent may include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom), a cyano group, a nitro group, an alkyl group having 1 to 16 carbon atoms, an alkenyl group having 1 to 16 carbon atoms, an alkynyl group having 1 to 16 carbon atoms, a halogen-substituted alkyl group having 1 to 16 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, an acyl group having 2 to 16 carbon atoms, an alkylthio group having 1 to 16 carbon atoms, an acyloxy group having 2 to 16 carbon atoms, an alkoxycarbonyl group having 2 to 16 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 16 carbon atoms, and an acylamino group having 2 to 16 carbon atoms. The substituent of the divalent cyclic group is preferably a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, or a halogen-substituted alkyl group having 1 to 6 carbon atoms. It is further preferably a halogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen-substituted alkyl group having 1 to 4 carbon atoms. It is in particular preferably a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a trifluoromethyl group.
n1 represents an integer of 0 to 4. n1 is preferably an integer of 1 to 3, and in particular preferably 1 or 2.
L 22 represents *—O—, *—O—CO—, *—CO—O—, *—O—CO—O—, *—S—, *—N(R)H—, *—SO 2 —, *—CH 2 —, *—CH═CH—, or *—C≡C— (where * represents the bonding site with the benzene ring in the formula (DI-R)). It is preferably *—O—, *—O—CO—, *—CO—O—, *—O—CO—O—, *—CH 2 —, *—CH═CH—, or *—C═C—, and in particular preferably *—O—, *—O—CO—, *—O—CO—O—, or *—CH 2 —. When the foregoing group is a group containing a hydrogen atom, the hydrogen atom may be substituted with a substituent. Preferred examples of such a substituent may include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a halogen-substituted alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an acyloxy group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 6 carbon atoms, and an acylamino group having 2 to 6 carbon atoms. A halogen atom and an alkyl group having 1 to 6 carbon atoms are more preferred.
L 23 is a divalent linking group selected from the group consisting of —O—, —S—, —C(═O)—, —SO 2 —, —NH—, —CH 2 —, —CH═CH—, and —C≡C—, and combinations thereof. Herein, the hydrogen atoms in —NH—, —CH 2 —, and —CH═CH—, may be substituted other substituents. Examples of other substituents may include a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 6 carbon atoms, a halogen-substituted alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an acyl group having 2 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an acyloxy group having 2 to 6 carbon atoms, an alkoxycarbonyl group having 2 to 6 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 6 carbon atoms, and an acylamino group having 2 to 6 carbon atoms. Particularly, a halogen atom and an alkyl group having 1 to 6 carbon atoms are preferred. Substitution with these groups can improve the solubility in a solvent to be used in preparing a liquid crystalline composition from the liquid crystalline compound of the invention.
L 23 preferably includes a combination of —O—, —C(═O)—, —CH 2 —, —CH═CH—, and —C≡C—. L 23 preferably contains 1 to 20 carbon atoms, and in particular preferably contains 2 to 14 carbon atoms. Further, L 23 preferably contains 1 to 16 units of —CH 2 —, and in particular preferably contains 2 to 12 units of —CH 2 —.
Q 1 is each independently a polymerizable group or a hydrogen atom. When the liquid crystalline compound of the invention is used for an optical film which preferably does not change in magnitude of the phase contrast by heat as an optical compensating film, or the like, Q 1 is preferably a polymerizable group. The polymerization reaction is preferably an addition polymerization (including ring opening polymerization) or condensation polymerization. In other words, The polymerizable group is preferably a functional group capable of an addition polymerization reaction or a condensation polymerization reaction. Below, examples of the polymerizable group will be shown.
Examples of polymerizable group:
Further, the polymerizable group is preferably a functional group capable of the addition polymerization reaction. As such a polymerizable group, an polymerizable ethylenically unsaturated group or a ring opening polymerizable group is preferred.
Examples of the polymerizable ethylenically unsaturated group may include the following formulae (M-1) to (M-6):
In the formulae (M-3) and (M-4), R represents a hydrogen atom or an alkyl group. R is preferably a hydrogen atom or a methyl group.
Out of the foregoing (M-1) to (M-6), (M-1) or (M-2) is preferred, and (M-1) is most preferred.
The ring opening polymerizable groups are preferably cyclic ether groups. Out of these, an epoxy group or an oxetanyl group is more preferred, and an epoxy group is most preferred.
The liquid crystal compound of the invention is preferably a compound represented by the following formula (DII):
In the formula (DII), Y 31 , Y 32 , and Y 33 have the same definitions as those for Y 11 , Y 12 , and Y 13 in the formula (DI), respectively.
In the formula (DII), R 31 , R 32 , and R 33 are each independently represented by the following formula (DII-R):.
In the formula (DII-R), A 31 and A 32 each independently represent methine or a nitrogen atom. It is preferable that at least one of A 31 and A 32 is a nitrogen atom, and it is most preferable that both are nitrogen atoms. X 3 represent an oxygen atom, a sulfur atom, methylene, or imino. X 3 is most preferably an oxygen atom.
The divalent cyclic group in the formula (DII-R) is a divalent linking group having a 6-membered cyclic structure. The ring contained in the cyclic group may be a condensed ring. However, it is more preferably a single ring than a condensed ring. Further, the ring contained in the cyclic group may be any of an aromatic ring, an aliphatic ring, and a heterocyclic ring. Examples of the aromatic ring may include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring. Examples of the aliphatic ring may include a cyclohexane ring. Examples of the heterocyclic ring may include a pyridine ring and a pyrimidine ring.
The cyclic group having a benzene ring out of the divalent cyclic groups are preferably 1,4-phenylene and 1,3-phenylene. The cyclic groups having a naphthalene ring are preferably naphthalene-1,4diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-2,5-diyl, naphthalene-2,6-diyl, and naphthalene-2,7-diyl. The cyclic group having a cyclohexane ring is preferably 1,4-cyclohexylene. The cyclic group having a pyridine ring is preferably pyridine-2,5-diyl. The cyclic group having a pyrimidine ring is preferably pyrimidine-2,5-diyl. The divalent cyclic groups are in particular preferably 1,4-phenylene, 1,3-phenylene, and naphthalene-2,6-diyl.
The divalent cyclic group may have a substituent. Examples of the substituent may include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom), a cyano group, a nitro group, an alkyl group having 1 to 16 carbon atoms, an alkenyl group having 1 to 16 carbon atoms, an alkynyl group having 1 to 16 carbon atoms, a halogen-substituted alkyl group having 1 to 16 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, an acyl group having 2 to 16 carbon atoms, an alkylthio group having 1 to 16 carbon atoms, an acyloxy group having 2 to 16 carbon atoms, an alkoxycarbonyl group having 2 to 16 carbon atoms, a carbamoyl group, an alkyl-substituted carbamoyl group having 2 to 16 carbon atoms, and an acylamino group having 2 to 16 carbon atoms. The substituent of the divalent cyclic group is preferably a halogen atom, a cyano group, an alkyl group having 1 to 6 carbon atoms, or a halogen-substituted alkyl group having 1 to 6 carbon atoms. It is further preferably a halogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen-substituted alkyl group having 1 to 4 carbon atoms. It is in particular preferably a halogen atom, an alkyl group having 1 to 3 carbon atoms, or a trifluoromethyl group.
n3 in the formula (DII-R) represents an integer of 1 to 3. n3 is preferably 1 or 2.
L 31 in the formula (DII-R) has the same definition as that for L 22 in the formula (DI-R).
L 32 in the formula (DII-R) has the same definition as that for L 23 in the formula (DI-R).
Q 3 in the formula (DII-R) has the same definition as that for Q 1 in the formula (DI-R).
Below, specific examples of the compound represented by the formula (I) or the formula (II) will be shown. However, the invention is by no way limited thereto.
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| X = | —OC 4 H 9 | D-1 | |
| —OC 5 H 11 | D-2 | ||
| —OC 6 H 13 | D-3 | ||
| —OC 7 H 15 | D-4 | ||
| —OC 8 H 17 | D-5 | ||
| —OCH 2 CH(CH 3 )C 4 H 9 | D-6 | ||
| —O(CH 2 ) 2 OCOCH═CH 2 | D-7 | ||
| —O(CH 2 ) 3 OCOCH═CH 2 | D-8 | ||
| —O(CH 2 ) 4 OCOCH═CH 2 | D-9 | ||
| —O(CH 2 ) 5 OCOCH═CH 2 | D-10 | ||
| —O(CH 2 ) 6 OCOCH═CH 2 | D-11 | ||
| —O(CH 2 ) 7 OCOCH═CH 2 | D-12 | ||
| —O(CH 2 ) 8 OCOCH═CH 2 | D-13 | ||
| —O(CH 2 ) 2 CH(CH 3 )OCOCH═CH 2 | D-14 | ||
| —O(CH 2 ) 3 CH(CH 3 )OCOCH═CH 2 | D-15 | ||
| —O(CH 2 CH 2 O) 2 COCH═CH 2 | D-16 | ||
| | D-17 | ||
| —O(CH 2 ) 4 OCOCH═CHCH 3 | D-18 | ||
| —O(CH 2 ) 4 OCH═CH 2 | D-19 | ||
| | D-20 | ||
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| X = | —OCOC 4 H 9 | D-21 | |
| —OCOC 5 H 11 | D-22 | ||
| —OCOC 6 H 13 | D-23 | ||
| —OCO(CH 2 ) 2 OCOCH═CH 2 | D-24 | ||
| —OCO(CH 2 ) 3 OCOCH═CH 2 | D-25 | ||
| —OCO(CH 2 ) 4 OCOCH═CH 2 | D-26 | ||
| —OCO(CH 2 ) 5 OCOCH═CH 2 | D-27 | ||
| —OCO(CH 2 ) 6 OCOCH═CH 2 | D-28 | ||
| —OCO(CH 2 ) 7 OCOCH═CH 2 | D-29 | ||
| —OCO(CH 2 ) 2 CH(CH 3 )OCOCH═CH 2 | D-30 | ||
| | D-31 | ||
| —OCO(CH 2 ) 2 OCOCH═CHCH 3 | D-32 | ||
| —OCO(CH 2 ) 4 OCH═CH 2 | D-33 | ||
| | D-34 | ||
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| X = | —OCOOC 4 H 9 | D-35 | |
| —OCOOC 5 H 11 | D-36 | ||
| —OCOOC 6 H 13 | D-37 | ||
| —OCOO(CH 2 ) 2 OCOCH═CH 2 | D-38 | ||
| —OCOO(CH 2 ) 3 OCOCH═CH 2 | D-39 | ||
| —OCOO(CH 2 ) 4 OCOCH═CH 2 | D-40 | ||
| —OCOO(CH 2 ) 5 OCOCH═CH 2 | D-41 | ||
| —OCOO(CH 2 ) 6 OCOCH═CH 2 | D-42 | ||
| —OCOO(CH 2 ) 7 OCOCH═CH 2 | D-43 | ||
| —OCOOCH(CH 3 )CH 2 CH 2 OCOCH═CH 2 | D-44 | ||
| —OCOOC(CH 2 CH 2 O) 2 COCH═CH 2 | D-45 | ||
| | D-46 | ||
| —OCOO(CH 2 ) 2 OCOCH═CHCH 3 | D-47 | ||
| —OCOO(CH 2 ) 4 OCH═CH 2 | D-48 | ||
| | D-49 | ||
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| X = | —OC 4 H 9 | D-50 | |
| —OC 5 H 11 | D-51 | ||
| —OC 6 H 13 | D-52 | ||
| —OC 7 H 15 | D-53 | ||
| —OC 8 H 17 | D-54 | ||
| —OCH 2 CH(CH 3 )C 4 H 9 | D-55 | ||
| —O(CH 2 ) 2 OCOCH═CH 2 | D-56 | ||
| —O(CH 2 ) 3 OCOCH═CH 2 | D-57 | ||
| —O(CH 2 ) 4 OCOCH═CH 2 | D-58 | ||
| —O(CH 2 ) 5 OCOCH═CH 2 | D-59 | ||
| —O(CH 2 ) 6 OCOCH═CH 2 | D-60 | ||
| —O(CH 2 ) 7 OCOCH═CH 2 | D-61 | ||
| —O(CH 2 ) 8 OCOCH═CH 2 | D-62 | ||
| —O(CH 2 ) 2 CH(CH 3 )OCOCH═CH 2 | D-63 | ||
| —O(CH 2 ) 3 CH(CH 3 )OCOCH═CH 2 | D-64 | ||
| —O(CH 2 CH 2 O) 2 COCH═CH 2 | D-65 | ||
| | D-66 | ||
| —O(CH 2 ) 4 OCOCH═CHCH 3 | D-67 | ||
| —O(CH 2 ) 4 OCH═CH 2 | D-68 | ||
| | D-69 | ||
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| X = | —OCOC 4 H 9 | D-70 | |
| —OCOC 5 H 11 | D-71 | ||
| —OCOC 6 H 13 | D-72 | ||
| —OCO(CH 2 ) 2 OCOCH═CH 2 | D-73 | ||
| —OCO(CH 2 ) 3 OCOCH═CH 2 | D-74 | ||
| —OCO(CH 2 ) 4 OCOCH═CH 2 | D-75 | ||
| —OCO(CH 2 ) 5 OCOCH═CH 2 | D-76 | ||
| —OCO(CH 2 ) 6 OCOCH═CH 2 | D-77 | ||
| —OCO(CH 2 ) 7 OCOCH═CH 2 | D-78 | ||
| —OCO(CH 2 ) 2 CH(CH 3 )OCOCH═CH 2 | D-79 | ||
| | D-80 | ||
| —OCO(CH 2 ) 2 OCOCH═CHCH 3 | D-81 | ||
| —OCO(CH 2 ) 4 OCH═CH 2 | D-82 | ||
| | D-83 | ||
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| X = | —OCOOC 4 H 9 | D-84 | |
| —OCOOC 5 H 11 | D-85 | ||
| —OCOOC 6 H 13 | D-86 | ||
| —OCOO(CH 2 ) 2 OCOCH═CH 2 | D-87 | ||
| —OCOO(CH 2 ) 3 OCOCH═CH 2 | D-88 | ||
| —OCOO(CH 2 ) 4 OCOCH═CH 2 | D-89 | ||
| —OCOO(CH 2 ) 5 OCOCH═CH 2 | D-90 | ||
| —OCOO(CH 2 ) 8 OCOCH═CH 2 | D-91 | ||
| —OCOOCH(CH |