CN101870651B - Compound, composition containing same, membrane, color filter and flat display device - Google Patents

Abstract

The present invention relates to a compound, a composition containing the compound, a film, a color filter and a flat panel display device. The present invention provides a compound represented by formula (1), wherein X represents an alkyl group with 2 to 20 carbon atoms, a cyclic alkyl group with 3 to 20 carbon atoms, or a substituted or substituted group with 6 to 20 carbon atoms. An unsubstituted aromatic hydrocarbon group, the aromatic hydrocarbon group may have a substituent, E ¹ and E ² each independently represent a linking group or a single bond, A ¹ and A ² each independently represent a divalent substituted or unsubstituted aromatic hydrocarbon group , the divalent aromatic hydrocarbon group may have a substituent, B ¹ , B ² , B ³ and B ⁴ each independently represent a linking group or a single bond, F ¹ and F ² each independently represent a carbon number of 1 to 12 A substituted or unsubstituted alkanediyl group, one or more methylene groups constituting the alkanediyl group may be replaced by an oxygen atom, and ^P1 and ^P2 each independently represent a hydrogen atom or a polymerizable group.

Description

Compound, composition containing same, film, color filter and flat panel display device

technical field

The present invention relates to novel compounds. the

Background technique

The flat panel display (FPD) includes components using films such as polarizers and retardation plates. the

Japanese Patent Laid-Open Publication No. 2003-287623 discloses a retardation film in which a polymerizable compound represented by formula (III-1-1) is dissolved in a solvent, and the resulting solution is applied to a support base. It is obtained by polymerizing the polymerizable compound after the material. the

Contents of the invention

The present invention provides following scheme etc.:

[1] The compound represented by formula (1),

In the formula, X represents an alkyl group with 2 to 20 carbon atoms, a cyclic alkyl group with 3 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 20 carbon atoms,

E ¹ and E ² each independently represent a linking group or a single bond,

A ¹ and A ² each independently represent a divalent substituted or unsubstituted aromatic hydrocarbon group,

B ¹ , B ² , B ³ and B ⁴ each independently represent a linking group or a single bond,

F ¹ and F ² each independently represent a substituted or unsubstituted alkanediyl group with 1 to 12 carbon atoms, and one or more methylene groups constituting the alkanediyl group can be replaced with oxygen atoms,

^P1 and ^P2 each independently represent a hydrogen atom or a polymerizable group;

[2] The compound as described in [1], in formula (1), P ¹ and P ² each independently represent a group represented by formula (P-1),

In the formula, R ¹ , R ² and R ³ each independently represent an alkyl group with 1 to 6 carbon atoms or a hydrogen atom;

[3] A composition containing the compound described in [1] or [2] and a photopolymerization initiator;

[4] A film obtained by polymerizing the compound described in [1] or [2];

[5] A color filter comprising the film described in [4];

[6] A flat panel display device comprising the film described in [4];

[7] A method for producing a film, comprising the step of applying the compound described in [1] or [2] on a substrate, or on an alignment film formed on a substrate. the

Description of drawings

FIG. 1 : is a schematic cross-sectional view of an example of a polarizing film containing the film of the present invention. the

Fig. 2: is a schematic cross-sectional view of an example of a liquid crystal display device including the film of the present invention. the

Fig. 3: is a schematic cross-sectional view of an example of an organic EL display device including the film of the present invention. the

Fig. 4: is a schematic cross-sectional view of an example of a color filter including the film of the present invention. the

Symbol Description

1. 1' film

2. 2' Polarizing film layer

3. 3'adhesive layer

4. 4' Parts containing the membrane of the present invention

5. 5' adhesive layer

6 LCD panels

7 luminescent layer

11 color filters

12 films

13 color filter layer

Detailed ways

Novel compound of the present invention is the compound (hereinafter abbreviated as compound (1)) represented by formula (1),

In the formula, X represents an alkyl group with 2 to 20 carbon atoms, a cyclic alkyl group with 3 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group with 6 to 20 carbon atoms,

E ¹ and E ² each independently represent a linking group or a single bond,

A ¹ and A ² each independently represent a divalent substituted or unsubstituted aromatic hydrocarbon group,

B ¹ , B ² , B ³ and B ⁴ each independently represent a linking group or a single bond,

^F1 and ^F2 each independently represent a substituted or unsubstituted alkanediyl group with 1 to 12 carbon atoms,

One or more methylene groups constituting the alkanediyl group can be replaced by an oxygen atom,

^P1 and ^P2 each independently represent a hydrogen atom or a polymerizable group.

Examples of the alkyl group having 2 to 20 carbon atoms represented by X include ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and 1-methyl Butyl, 3-methylbutyl, hexyl, 1-methylpentyl, 4-methylpentyl, heptyl, 1-methylhexyl, 5-methylhexyl, octyl, 1-methylheptyl , nonyl, 1-methyloctyl, decyl, undecyl and dodecyl, preferably an alkyl group with 3 to 12 carbon atoms. the

Examples of cyclic alkyl groups having 3 to 20 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl, preferably carbon atoms A cyclic alkyl group whose number is 312. the

Examples of unsubstituted aromatic hydrocarbon groups having 6 to 20 carbon atoms include phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl and 3-fluorenyl, preferably An unsubstituted aromatic hydrocarbon group with 6 to 14 carbon atoms. The aromatic hydrocarbon group may have a substituent, and the substituent includes an alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, and a propyl group; a carbon atom group such as a methoxy group, an ethoxy group, or a propoxy group; an alkoxy group having a number of 1 to 5; and a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom. Examples of substituted aromatic hydrocarbon groups include 4-fluorophenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-methylphenyl, 4-ethylphenyl and 3,5-dimethyl phenyl. the

X is preferably an alkyl group having 3 to 12 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms. the

E ¹ and E ² each independently represent a linking group or a single bond, and the linking group includes a divalent organic group. Specific examples thereof include -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-NR ⁶ -, -NR ⁶ -CO-, - O-CH ₂ - and -CH ₂ -O-, R ⁶ represents a hydrogen atom or an alkyl group with 1 to 6 carbon atoms (such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl , hexyl, etc.). Among them, *-CO-O- (* represents a bonding site with 1,4-cyclohexanediyl) is preferable.

The divalent unsubstituted aromatic hydrocarbon group represented by ^A1 and ^A2 is preferably a group formed of a 5-membered or 6-membered aromatic group represented by the following formulas (g-1) to (g-5). group. The hydrogen atom in the divalent aromatic hydrocarbon group can be replaced by a halogen atom, an alkyl group with 1 to 4 carbon atoms (such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc.), carbon Alkoxy with 1 to 4 atoms (such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, etc.), trifluoromethyl, cyano or nitro replace.

Examples of the divalent substituted or unsubstituted aromatic hydrocarbon group include 1,4-phenylene, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 4,4'-biphenylene and fluorene-2,7-diyl, preferably 1,4-phenylene. the

B ¹ , B ² , B ³ and B ⁴ each independently represent a linking group or a single bond, and the linking group includes a divalent organic group. Specific examples thereof include -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-NR ⁶ -, -NR ⁶ -CO-, - CO- and -CS-. Here, R ⁶ represents the same meaning as above. Among them, -O-, -CO-O-, -O-CO-, -O-CO-O-, -CO-, -O-CH ₂ -, -CH ₂ -O- and a single bond are preferable.

B ¹ and B ² are more preferably -O-. B ³ and B ⁴ are more preferably *-O-CO- (* represents a bonding site with F ¹ or F ² ).

Combinations of B ¹ , B ² , B ³ and B ⁴ include combinations shown in Table 1 below. In Table 1, * in columns ^B1 and ^B2 indicates the bonding site with ^F1 or ^F2 , and * in column ^B3 and ^B4 indicates the bonding site with ^P1 or ^P2 .

[Table 1]

^B1 B ² B ³ B ⁴ *-O- -O-* *-CO-O- -O-CO-* *-O- -O-* single key single key *-O- -O-* *-O- -O-* *-O- -O-* single key -O-CO-* *-O- -O-* *-O-CO- single key *-O- -O-* * _-CH2 -O- -O-CH ₂ -* *-CO-O- -O-CO-* *-CO-O- -O-CO-* *-CO-O- -O-CO-* single key single key *-CO-O- -CO-O-* * _-CH2 -O- -O-CH ₂ -* *-O-CO- -CO-O-* *-CO-O- -O-CO-* *-O-CO- -CO-O-* single key single key *-O-CO- -CO-O-* * _-CH2 -O- -O-CH ₂ -* *-O-CO-O- -O-CO-O-* *-CO-O- -O-CO-*

The substituted or unsubstituted alkanediyl groups with 1 to 12 carbon atoms represented by ^F1 and ^F2 are preferably methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene and other straight-chain or unsubstituted alkanediyl groups with 1 to 12 carbon atoms in a branched chain, and more An unsubstituted alkanediyl group having 4 to 8 carbon atoms is preferred, and an alkanediyl group having 4 to 6 carbon atoms is particularly preferred. This alkanediyl group may have a substituent. In addition, one or more methylene groups constituting the alkanediyl group can be replaced with oxygen atoms. Examples of groups in which one or more methylene groups constituting an alkanediyl group are replaced by oxygen atoms include -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -O- _CH2 - _CH2 -O- _CH2 - _CH2- and _-CH2 - _CH2 -O-CH2- _CH2 -O- _{CH2- CH2 -} O- _CH2 - _CH2- .

At least one of ^P1 and ^P2 is preferably a polymerizable group, more preferably both ^P1 and ^P2 are polymerizable groups. The "polymerizable group" refers to a group capable of participating in the polymerization reaction of compound (1).

As the polymerizable group, groups represented by the following formulas (P-1) to (P-5) can be cited,

(In the formula, R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent an alkyl group with 1 to 6 carbon atoms or a hydrogen atom), preferably formula (P-1) and formula (P-2 ), more preferably a group represented by formula (P-1). Examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl.

Specifically, 1-methyl vinyl group, vinyl group, p-stilbene group, epoxy group, methyl epoxy group, groups represented by formula (P-6), and maleic imide group. the

Examples of the compound (1) include compounds represented by formula (1-a1) to formula (1-a50). the

Compound (1) can be prepared according to its structure by the known organic synthesis reactions (such as condensation reaction, esterification reaction, Williamson reaction, Uhlmann reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sotou reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction , Friedel-Crafts reaction, Heck reaction, aldol condensation reaction, etc.) are appropriately combined to manufacture. the

For example, the compound represented by the formula (1-1) is reacted with the compound represented by the formula (1-2) to obtain the compound represented by the formula (1-3), and the compound represented by the obtained formula (1-3) is reacted with the compound represented by the formula ( Compound (1) can be obtained by reacting the compound represented by 1-4). the

(In the formula, E ¹ , E ² , A ¹ , A 2 , B ¹ , B ² , B ³ , ^{B 4 ,} F ¹ , F ² , P ¹ , P ² and X have the same meanings as above.)

The reaction of the compound represented by formula (1-1) and the compound represented by formula (1-2) and the reaction of the compound represented by formula (1-3) and the compound represented by formula (1-4) are preferably in the condition that condensing agent exists next implementation. As the condensing agent, known condensing agents can be used. the

The composition of the present invention contains compound (1). The composition of the present invention may contain one compound (1) or two or more compounds (1). The composition of the present invention may contain a liquid crystal compound other than compound (1). the

As a specific example of the liquid crystal compound, there can be cited Liquid Crystal Handbook (edited by the Liquid Crystal Handbook Editing Committee, Maruzen Co., Ltd., published on October 30, 2012), Chapter 3, "Molecular Structure and Liquid Crystallinity," Section 3.2 "Non-manual Compounds" Compounds with polymerizable groups among the compounds described in Section 3.3 "Chiral Rod Liquid Crystal Molecules". The composition of the present invention may contain two or more types of liquid crystal compounds. the

Examples of liquid crystal compounds include compounds containing a group represented by formula (4) (hereinafter abbreviated as compound (4)). the

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ - (4)

(wherein, P ¹¹ represents a polymerizable group,

A ¹¹ represents a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group. The divalent alicyclic hydrocarbon group and the divalent aromatic hydrocarbon group may have a halogen atom, an alkyl group with 1 to 6 carbon atoms, a carbon number One or more substituents selected from fluoroalkyl groups with 1 to 6 carbon atoms, alkoxy groups with 1 to 6 carbon atoms, fluoroalkoxy groups with 1 to 6 carbon atoms, cyano groups and nitro groups,

B ¹¹ represents -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-NR ¹⁶ -, -NR ¹⁶ -CO-, -CO-, - CS- or a single bond, R ¹⁶ represents a hydrogen atom or an alkyl group with 1 to 6 carbon atoms,

B ¹² and B ¹³ each independently represent -C≡C-, -CH=CH-, -CH ₂ -CH ₂ -, -O-, -S-, -C(=O)-, -C(=O )-O-, -OC(=O)-, -OC(=O)-O-, -CH=N-, -N=CH-, -N=N-, -C(=O)-NR ¹⁶ , -NR ¹⁶ -C(=O)-, -OCH ₂ -, -OCF _{2 -, -CH 2 O-} , -CF ₂ O-, -CH=CH-C(=O)-O-, -OC (=O)-CH=CH- or a single bond,

^E11 represents an alkanediyl group with 1 to 12 carbon atoms, and the alkanediyl group may have a halogenated alkyl group with 1 to 5 carbon atoms, an alkoxy group with 1 to 5 carbon atoms, and a carbon atom As one or more substituents in the haloalkoxy group having 1 to 5, the methylene group contained in the alkanediyl group may be substituted with -O- or -CO-. )

The polymerizable group represented by ^P11 is preferably a radically polymerizable group or a cationically polymerizable group from the viewpoint of high photopolymerization reactivity, and is preferably Groups represented by the following formulas (P-11) to (P-15).

(In the formula, R ¹⁷ to R ²¹ each independently represent an alkyl group having 1 to 6 carbon atoms or a hydrogen atom.)

Specifically, groups represented by the following formulas (P-16) to (P-20) are exemplified. the

The polymerizable group is preferably a group represented by (P-14) to (P-20), and examples thereof include a vinyl group, a p-stilberyl group, an epoxy group, and an oxetanyl group. the

P ¹¹ -B ¹¹ - is particularly preferably acryloyloxy or methacryloyloxy.

The number of carbon atoms in the aromatic hydrocarbon group and alicyclic hydrocarbon group of A ¹¹ is usually 3-18, preferably 5-12, particularly preferably 5 or 6. A ¹¹ is preferably 1,4-cyclohexylene or 1,4-phenylene.

E ¹¹ is preferably a linear alkanediyl group having 1 to 12 carbon atoms. The methylene group contained in the alkanediyl group may be replaced by -O-.

Specifically, methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, Dodecyl, -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ - and -CH ₂ -CH ₂ -O- _CH2 - _CH2 -O- _CH2 - _CH2 -O- _CH2 - _CH2- .

Compound (4) includes compounds represented by formula (I), formula (II), formula (III), formula (IV), formula (V) and formula (VI). the

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -B ¹⁵ -A ¹⁴ -B ¹⁶ -E ¹² -B ¹⁷ -P ¹² (I)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -B ¹⁵ -A ¹⁴ -F ¹¹ (II)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -B ¹⁵ -E ¹² -B ¹⁷ -P ¹² (III)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -A ¹³ -F ¹¹ (IV)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -B ¹⁴ -E ¹² -B ¹⁷ -P ¹² (V)

P ¹¹ -B ¹¹ -E ¹¹ -B ¹² -A ¹¹ -B ¹³ -A ¹² -F ¹¹ (VI)

(In the formula, A ¹² to A ¹⁴ have the same meaning as A ¹¹ , B ¹⁴ to B ¹⁶ have the same meaning as B ¹² , B ¹⁷ has the same meaning as B ¹¹ , and E ¹² has the same meaning as E ¹¹ .

In the formula, ^F11 represents a hydrogen atom, an alkyl group with 1 to 13 carbon atoms, an alkoxy group with 1 to 13 carbon atoms, a cyano group, a nitro group, a trifluoromethyl group, a dimethylamino group, a hydroxyl group, Methylol, formyl, sulfonic acid group (-SO ₃ H), carboxyl, alkoxycarbonyl group with 2 to 11 carbon atoms or a halogen atom, the methylene group contained in the above-mentioned alkyl group and the above-mentioned alkoxy group can be Replace with -O-. )

Specific examples of compound (4) include formula (I-1) to (I-4), formula (II-1) to formula (II-4), formula (III-1) to formula (III-26 ), the compounds represented by formula (IV-1) to formula (IV-19), formula (V-1) to formula (V-2), formula (VI-1) to formula (VI-6). In the following formulae, k1 and k2 represent an integer of 2-12. These liquid crystal compounds are easy to synthesize or are commercially available, so they are easy to obtain and are preferred. the

The content of the liquid crystal compound in the composition of the present invention is 90 parts by weight or less with respect to 100 parts by weight of the total of the liquid crystal compound and compound (1). the

The composition of the present invention may also contain additives such as polymerization initiators, polymerization inhibitors, photosensitizers, leveling agents, solvents, and chiral agents. In particular, it is preferable to contain an organic solvent from the viewpoint of easiness of film-forming the compound of the present invention, and furthermore, it is preferable to contain a polymerization initiator. the

[polymerization initiator]

The polymerization initiator preferably contains a photopolymerization initiator, and the photopolymerization initiator is preferably a photopolymerization initiator that generates radicals by light irradiation. the

Examples of the photopolymerization initiator include benzoin compounds, benzophenone compounds, benzil ketal compounds, α-hydroxyketone compounds, α-aminoketone compounds, triazine compounds, iodonium salts, and sulfonium salts. the

Specifically, IRGACURE 907 (manufactured by Ciba), IRGACURE 184 (manufactured by Ciba), IRGACURE 651 (manufactured by Ciba), IRGACURE 819 (manufactured by Ciba), IRGACURE 250 (manufactured by Ciba), IRGACURE 369 (manufactured by Ciba Corporation), SEIKUOL BZ (manufactured by Seiko Chemical Co., Ltd.), SEIKUOL Z (manufactured by Seiko Chemical Co., Ltd.), SEIKUOL BEE (manufactured by Seiko Chemical Co., Ltd.), KAYACURE BP100 (manufactured by Nippon Kayaku Co., Ltd.), KAYACURE UVI-6992 (manufactured by DOW Corporation), ADEKA OPTOMER SP-152 (manufactured by ADEKA Co., Ltd.), ADEKA OPTOMER SP-170 (manufactured by ADEKA Co., Ltd.), TAZ-A (manufactured by SiberHegner Corporation of Japan), TAZ-PP (manufactured by SiberHegner Corporation of Japan ), TAZ-104 (manufactured by Sanwa Chemical Co., Ltd.), etc. the

The content of the polymerization initiator in the composition of the present invention is usually 0.1 to 30 parts by weight, preferably 0.5 to 10 parts by weight based on 100 parts by weight of the compound (1) and the liquid crystal compound in total. Within the above range, the compound (1) and the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) and the liquid crystal compound. the

[polymerization inhibitor]

Examples of polymerization inhibitors include hydroquinone, hydroquinone compounds having substituents such as alkoxy groups, catechol compounds having substituents such as alkyl groups such as butyl catechol, pyrogallol compounds, Radical scavengers such as 2,2,6,6-tetramethylpiperidine-1-oxyl radicals, thiophenol compounds, β-naphthylamine compounds, β-naphthol compounds, and the like. the

By using a polymerization inhibitor, the control of the polymerization reaction of compound (1) and a liquid crystal compound becomes easy, and the stability of the obtained film can be improved. The content of the polymerization inhibitor in the composition of the present invention is usually 0.1 to 30 parts by weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the compound (1) and the liquid crystal compound in total. Within the above range, the compound (1) and the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) and the liquid crystal compound. the

[Photosensitizer]

Examples of the photosensitizer include xanthone compounds such as xanthone and thioxanthone (for example, 2,4-diethylthioxanthone, 2-isopropylthioxanthone, etc.), anthracene, and substituted compounds having an alkoxy group. Based anthracene compounds (such as dibutoxyanthracene, etc.), phenothiazine and rubrene. the

By using a photosensitizer, the polymerization reaction of the compound (1) can be advanced with high sensitivity, and the temporal stability of the resulting film can be improved. The content of the photosensitizer in the composition of the present invention is usually 0.1 to 30 parts by weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the compound (1) and the liquid crystal compound in total. Within the above range, the compound (1) and the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) and the liquid crystal compound. the

[leveling agent]

Examples of leveling agents include additives for radiation-curable coatings (manufactured by BYK-Chemie Japan: BYK-352, BYK-353, BYK-361N), coating additives (manufactured by Toray Dow Corning: SH28PA, DC11PA, ST80PA), paint Additives (Shin-Etsu Chemical Co., Ltd.: KP321, KP323, X22-161A, KF6001), fluorine-based additives (DIC Corporation: F-445, F-470, F-479), etc. the

By using a leveling agent, a smoother film can be obtained. In addition, in the film production process, the fluidity of the composition of the present invention can also be controlled to adjust the crosslink density in the obtained film. Content of the leveling agent in the composition of this invention is 0.01-30 weight part normally with respect to a total of 100 weight part of compound (1) and a liquid crystal compound, Preferably it is 0.05-10 weight part. Within the above range, the compound (1) and the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) and the liquid crystal compound. the

[solvent]

As the solvent, as long as it is an organic solvent capable of dissolving the compound (1) and the liquid crystal compound, and is inert to the polymerization reaction, specifically, water; methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, Alcohol solvents such as methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether; ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate , ethyl lactate and other ester solvents; acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, methyl isobutyl ketone and other ketone solvents; pentane, hexane, heptane and other non- Chlorinated aliphatic hydrocarbon solvents; non-chlorinated aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; ether solvents such as tetrahydrofuran and dimethoxyethane; and chlorinated hydrocarbon solvents such as chloroform and chlorobenzene. These organic solvents may be used alone or in combination. the

In order to facilitate coating, it is desirable to adjust the viscosity of the composition of the present invention to, for example, 10 mPa·s or less, preferably about 0.1 to 7 mPa·s. the

The fluidity of the composition of the present invention can be controlled by changing the amount of the solvent, but the composition of the present invention preferably contains a solvent from the viewpoint of easy film formation. Content of a solvent is 10-10000 weight part normally with respect to 100 weight part of compound (1), Preferably it is 100-5000 weight part. the

The concentration of the solid content in the composition of the present invention is usually 2 to 50% by weight, preferably 5 to 50% by weight. If the concentration of solid content is 2% by weight or more, the obtained film will not become too thin, and it is generally easy to obtain a film having birefringence required for optical compensation of a liquid crystal panel. In addition, if the concentration of the solid content is 50% by weight or less, the viscosity of the composition of the present invention will not become too low, and the obtained film is generally less likely to have uneven film thickness. Here, "solid content" refers to a component obtained by removing a solvent from the composition of the present invention. the

[chiral agent]

As the chiral agent, known chiral agents can be used (for example, described in Liquid Crystal Device Handbook Chapter 3 Item 4-3 "Chiral Agents for TN and STN", page 199, edited by the 142nd Committee of the Japan Society for the Promotion of Science, 1989 ). Chiral agents generally contain chiral carbon atoms, and chiral axis compounds or chiral surface compounds without chiral carbon atoms can also be used as chiral agents. Specific examples of the chiral axis compound or the chiral face compound include binaphthalene, helicalne, p-arylene and derivatives thereof. the

Examples of the chiral agent include JP-A-2007-269640, JP-A-2007-269639, JP-A-2007-176870, JP-A-2003-137887, and JP-A-2000-515496. The chiral agent disclosed in the gazette, Japanese Patent Application Laid-Open No. 2007-169178 and Japanese Patent Application Publication No. Hei 9-506088 is preferably Paliocolor LC756 manufactured by BASF Corporation. the

The content of the chiral agent is usually 0.1 to 30 parts by weight, preferably 1 to 25 parts by weight, based on 100 parts by weight of the compound (1) and the liquid crystal compound in total. Within the above range, the compound (1) and the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) and the liquid crystal compound. the

The film of the present invention transmits light and is a film having an optical function. The optical function refers to refraction, birefringence, and the like. The retardation film which is a kind of film of the present invention is used for converting linearly polarized light into circularly polarized light or elliptically polarized light, or conversely converting circularly polarized light or elliptically polarized light into linearly polarized light, or converting linearly polarized light direction of polarization. the

This film is obtained by polymerizing compound (1). One compound (1) may be polymerized, or two or more compounds (1) may be polymerized. In addition, the film of the present invention can also be produced by polymerizing the composition of the present invention. the

From the viewpoint of easiness of film formation, it is preferable to use a solution obtained by dissolving compound (1) in an organic solvent, and to obtain an optical film by applying the solution on a support substrate, drying, and polymerizing. The concentration of the solid content in the solution is usually 2 to 50% by weight, preferably 5 to 50% by weight. the

Examples of the coating method on the support substrate include extrusion coating, direct gravure coating, reverse gravure coating, CAP coating, and die coating. A method of coating using a coating machine such as a dip coater, a bar coater, or a spin coater is also mentioned. the

As the supporting base material, a supporting base material capable of forming an alignment film on the supporting base material is preferable. Specifically, glass, a plastic sheet, a plastic film, and a translucent film are mentioned. Examples of the light-transmitting film include polyolefin films such as polyethylene, polypropylene, and norbornene-based polymers; polyvinyl alcohol films; polyethylene terephthalate films; polymethacrylate films; Ester films; cellulose ester films; polyethylene naphthalate films; polycarbonate films; polysulfone films; polyethersulfone films; polyetherketone films; polyphenylene sulfide films; and polyphenylene ether films. the

In a process requiring film strength, such as a film bonding process, a transport process, and a storage process, the use of a supporting base material enables easy handling without causing film damage or the like. the

It is preferable to apply a solution of the compound (1) on the alignment film after forming the alignment film on the support substrate. The alignment film preferably has solvent resistance that does not dissolve in the solution of the compound (1) when the solution is applied. Moreover, it is preferable that an alignment film has heat resistance in heat processing for removing a solvent and aligning a liquid crystal. Furthermore, it is preferable that peeling or the like does not occur due to friction or the like during rubbing. The alignment film is preferably formed of an alignment polymer or a composition containing an alignment polymer. the

Examples of the alignment polymer include polyamides having an amide bond in the molecule, gelatin compounds, polyimides having an imide bond in the molecule, and polyamic acid, polyvinyl alcohol, alkyl Modified polyvinyl alcohol, polyacrylamide, polyoxazole, polyethyleneimine, polystyrene, polyvinylpyrrolidone, polyacrylic acid and polyacrylate. These alignment polymers may be used alone or in combination of two or more. In addition, copolymers of these alignment polymers may also be used. These oriented polymers can be easily obtained by polycondensation such as dehydration polycondensation and deamination polycondensation, chain polymerization such as radical polymerization, anionic polymerization, and cationic polymerization, coordination polymerization, ring-opening polymerization, and the like. the

These alignment polymers are usually dissolved in a solvent and used in the form of a solution. The solvent is not limited. Specifically, water; alcohol solvents such as methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, methyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether; ethyl acetate, butyl acetate, ethylene glycol Methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate, ethyl lactate and other ester solvents; acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, Ketone solvents such as methyl isobutyl ketone; non-chlorinated aliphatic hydrocarbon solvents such as pentane, hexane, and heptane; non-chlorinated aromatic hydrocarbon solvents such as toluene and xylene; nitrile solvents such as acetonitrile; tetrahydrofuran, dimethoxy Ether solvents such as ethyl ethane; and chlorinated hydrocarbon solvents such as chloroform and chlorobenzene. These organic solvents may be used alone or in combination of two or more. the

The alignment film can be formed using a commercially available alignment film material as it is. Examples of commercially available alignment film materials include SUNEVER (registered trademark, manufactured by Nissan Chemical Industries, Ltd.) and OPTOMER (registered trademark, manufactured by JSR Corporation). the

If such an alignment film is used, it is unnecessary to control the refractive index by stretching, so the in-plane unevenness of birefringence is reduced, and a film that can cope with the enlargement of flat panel display (FPD) can be formed on the support base material. the

As a method of forming an alignment film on a support substrate, a method in which a commercially available alignment film material or a compound as an alignment film material is prepared as a solution, coated on a support substrate, and then annealed is mentioned. the

The thickness of the alignment film is usually 10 to 10000 nm, preferably 10 to 1000 nm. If it is within the above range, the compound (1) can be oriented at a desired angle on the alignment film. According to needs, the alignment film can be subjected to rubbing treatment, or polarized UV irradiation can be performed on the alignment film. Through the treatment, the compound (1) can be oriented at a desired angle and direction, and can express the produced film. The shape and slope of the refractive index ellipsoid in the birefringent state are adjusted. In addition, when performing a rubbing treatment, or when irradiating an alignment film with polarized UV, if masking is performed, an alignment pattern can be formed on the film. the

As a method of rubbing the alignment film, there may be mentioned a method of bringing a rotating rubbing roll wound with a rubbing cloth into contact with the alignment film being transported on a table. the

[Preparation steps of unpolymerized film]

A solution of the compound (1) is coated on a supporting substrate or on an alignment film formed on a supporting substrate, and dried to obtain a non-polymerized film. When the unpolymerized film exhibits a nematic liquid crystal phase, it has birefringence due to monodomain orientation. Unpolymerized films are generally monodomain oriented by drying at 0 to 250°C. Compound (1) exhibits a liquid crystal phase at a low temperature, and thus obtains monodomain alignment at a relatively low temperature, and maintains monodomain alignment even when cooled to about 0 to 100° C. after alignment. the

[Unpolymerized film polymerization process] 

The obtained unpolymerized film is polymerized and cured to obtain a polymerized film. Since this polymer film is a film in which the orientation of the compound (1) is fixed, it is less susceptible to changes in birefringence due to heat. the

The method of polymerizing the unpolymerized film is appropriately determined depending on the type of polymerizable group of the compound (1). If the polymerizable group of the compound (1) is a photopolymerizable group, a photopolymerization method is used, and if the polymerizable group is a thermal polymerizable group, a thermal polymerization method is used. By the photopolymerization method, it is possible to polymerize the unpolymerized film at low temperature, and it is preferable to use a compound (1) having a photopolymerizable group from the viewpoint of a wide range of options for the heat resistance of the supporting substrate and the ease of industrial production. . The photopolymerization reaction can be performed by irradiating the unpolymerized film with visible light, ultraviolet rays or laser light. From the viewpoint of handling, ultraviolet rays are particularly preferred. the

Removal of the solvent may be performed in parallel with the polymerization reaction, but it is preferable to substantially remove the solvent before the polymerization reaction from the viewpoint of film-forming properties. Methods such as natural drying, ventilation drying, reduced-pressure drying, and heating drying are mentioned as the removal method. The temperature at the time of heating to remove the solvent is usually 10 to 200°C, preferably 20 to 150°C. The heating time is usually 10 seconds to 60 minutes, preferably 30 seconds to 30 minutes. As long as the heating temperature and heating time are within the above-mentioned ranges, a supporting base material whose heat resistance is not necessarily sufficient can be used as the above-mentioned supporting base material. the

The film of the present invention can be produced by a coating method. A thin film can be produced on a support base material having flexibility or curvature represented by a flexible substrate. the

By peeling off the supporting substrate, a laminated film in which an alignment film and the film of the present invention are laminated can be obtained, and further, the film of the present invention can be obtained by peeling off the alignment film. In addition, it is also possible to bond another support substrate to the film of the present invention formed on the support substrate or the orientation film, and peel off the support substrate on which the film of the present invention is formed, or peel the support substrate and the orientation film. film, from which the transfer is performed. the

By appropriately adjusting the contents of the compound (1) and the liquid crystal compound in the composition of the present invention, the film thickness can be adjusted so that a desired phase difference can be obtained. The retardation value (retardation value, Re(λ)) of the obtained film is determined as in Equation (7), so in order to obtain a desired Re(λ), Δn(λ) and thickness d may be appropriately adjusted. the

Re(λ)＝d×Δn(λ) (7)

(In the formula, Re(λ) represents the retardation value at the wavelength λnm, d represents the film thickness, and Δn(λ) represents the birefringence at the wavelength λnm.)

The film thus obtained is excellent in transparency and can be used as a film for various displays. The thickness of the formed layer varies depending on the retardation value of the obtained film as described above, but the thickness is preferably 0.1 to 10 μm, and preferably 0.2 to 5 μm from the viewpoint of reducing photoelasticity. the

The film of the present invention can change the optical properties in various ways by changing the orientation state of the compound (1). As a result, when used as a retardation film for liquid crystal panels, the optical characteristics can be changed so that it can be used in VA mode, IPS mode, OCB mode, TN mode, and STN mode. the

More specifically, the refractive index of the in-plane slow axis of the film of the present invention is defined as n _x , the refractive index in the direction (direction of the slow axis) perpendicular to the in-plane slow axis is defined as _ny , and the refractive index in the thickness direction When the refractive index is defined as _nz , it is possible to manufacture film with no retardation, positive A plate, negative C plate, The positive C plate of n _x ≠ _ny ≠ n _z positive O plate and negative O plate.

In addition, it is known that selective reflection occurs in a thin film in which the orientation of the chiral nematic phase is fixed, and it was confirmed that the film of the present invention also exhibits selective reflection. Its selective reflection wavelength band can be selected according to the purpose of use of the film. The central wavelength of the selective reflection wavelength band λ (nm) is represented by λ=n·P, where n represents the average refractive index of the composition, and P represents the helical pitch (μm) of the chiral nematic phase. Generally, if the content of the chiral agent increases, P decreases, so the selective reflection wavelength band can be controlled by controlling the content of the chiral agent. In these cases, it is preferable to orientate so that the chiral helical axis is substantially perpendicular to the plane direction of the transparent support. the

By using a chiral agent in this way, twist alignment films, selective reflection films, brightness enhancement films, negative C plates, and the like can be produced. In addition, when used as a film of a negative C plate, it is preferable to have a selective reflection wavelength band in the ultraviolet region. the

Even a single film of the present invention exhibits excellent optical properties, but a plurality of films having the same function may be laminated, or may be used in combination with other films. Therefore, the film of the present invention can be used as a retardation film, a viewing angle compensation film, a viewing angle expanding film, an antireflection film, a polarizing film, a circular polarizing film, an elliptically polarizing film, a brightness enhancement film, and the like. the

In addition, since the film of the present invention can be formed by polymerization by coating and ultraviolet irradiation, the film can also be formed in a liquid crystal cell or on a color filter without going through steps such as bonding. In addition, optical functions can also be patterned, and it is most suitable as a retardation plate for so-called in-cell use. the

1 is a schematic cross-sectional view showing an example of a polarizing film containing the film of the present invention, FIG. 2 is a schematic cross-sectional view showing an example of a liquid crystal display device containing the film of the present invention, and FIG. 3 shows an organic EL display containing the film of the present invention. A schematic cross-sectional view of an example of a device, and FIG. 4 is a schematic cross-sectional view showing an example of a color filter including the film of the present invention. In these figures, the film may be only the film of the present invention, may be a film in which an orientation film is laminated on the film of the present invention, or may be a film in which an orientation film and a supporting substrate are laminated on the film of the present invention. In addition, adhesives and adhesives are sometimes collectively referred to as adhesives. the

An embodiment of a polarizing film including the film of the present invention is shown in FIG. 1 . Fig. 1 (a) is the embodiment that film 1 of the present invention is directly bonded with polarizing film layer 2, and Fig. 1 (b) is that film 1 of the present invention and polarizing film layer 2 are bonded via adhesive layer 3 implementation. Fig. 1 (c) is the embodiment that the film 1 of the present invention is directly bonded to the film 1 ' of the present invention, and the film 1 ' of the present invention is directly bonded to the polarizing film layer 2, and Fig. 1 (d) is the embodiment of bonding An embodiment in which the film 1 of the present invention and the film 1' of the present invention are bonded via the adhesive layer 3, and the polarizing film layer 2 is bonded directly on the film 1' of the present invention. Fig. 1 (e) is that film 1 of the present invention and film 1 ' of the present invention are bonded through adhesive layer 3, then film 1 ' of the present invention and polarizing film layer 2 are interposed between adhesive layer 3 ' Fitting implementation. the

The polarizing film layer may be a film as long as it has a polarizing function. Specifically, a film obtained by absorbing iodine or a dichroic dye on a polyvinyl alcohol-based film and stretching it, and a film obtained by stretching a polyvinyl alcohol-based film and absorbing iodine , Films obtained from dichroic pigments, etc. Moreover, a polarizing film may have the film which becomes a protective film as needed. Examples of protective films include polyolefin films such as polyethylene, polypropylene, and norbornene-based polymers; polyethylene terephthalate films; polymethacrylate films; polyacrylate films; film; polyethylene naphthalate film; polycarbonate film; polysulfone film; polyethersulfone film; polyetherketone film; polyphenylene sulfide film; and polyphenylene ether film, etc. the

The adhesive used for the adhesive layer 3 and the adhesive layer 3' is preferably an adhesive with high transparency and excellent heat resistance. As an adhesive, an acrylic adhesive, an epoxy adhesive, a polyurethane adhesive, etc. are mentioned. the

Moreover, as shown in FIG.1(c) - FIG.1(e), the film of this invention of 2 or more sheets can be bonded directly or via an adhesive layer. the

The flat panel display device of the present invention has the film of the present invention, specifically, a liquid crystal display device having a liquid crystal panel formed by laminating a polarizing film containing the film of the present invention and a liquid crystal panel, and having a film containing the film of the present invention An organic EL device of an organic electroluminescent (hereinafter referred to as "EL") panel in which a polarizing film and a light-emitting layer are bonded together. the

As embodiments of the flat panel display device of the present invention, a liquid crystal display device and an organic EL display device will be described in detail below. the

[Liquid crystal display device]

As a specific example of a liquid crystal display device, the liquid crystal display device etc. which have the liquid crystal panel shown in FIG. (2) and FIG. 2(b) are mentioned. As shown in FIG. 2( a), the above-mentioned liquid crystal panel is formed by bonding the member 4 containing the film of the present invention and the liquid crystal panel 6 through the adhesive layer 5, or as shown in FIG. 2( b), will contain The member 4 of the film of this invention and the member 4' containing the film of this invention are bonded to both surfaces of the liquid crystal panel 6 via the adhesive layer 5 and the adhesive layer 5', respectively. According to the above configuration, by applying a voltage to the liquid crystal panel using electrodes not shown, the liquid crystal molecules are driven to perform monochrome display. the

[Organic EL display device]

Specific examples of the organic EL display device include an organic EL display device having the organic EL panel shown in FIG. 3 , and the like. The aforementioned organic EL panel is formed by bonding a member 4 including the film of the present invention and a light-emitting layer 7 via an adhesive layer 5 . The light-emitting layer 7 is at least one layer formed of a conductive organic compound. the

In the above-mentioned organic EL panel, when the member 4 including the film of the present invention is a polarizing film, it functions as a broadband circularly polarizing plate. Therefore, an antireflection function can be imparted to the organic EL panel. the

[color filter]

FIG. 4 is a schematic cross-sectional view showing an example of a color filter 11 including the film of the present invention. the

The color filter 11 is a color filter formed by forming a color filter layer 13 on the film 12 of the present invention. the

An example of a method of manufacturing the color filter 11 will be described. First, an alignment film material is coated on a support base material, and rubbing treatment is performed to form an alignment film. Next, on the obtained alignment film, a solution containing compound (1) is applied while adjusting the thickness in such a manner that the obtained film exhibits a desired retardation value, to form a film, wherein the applied solution is a compound (1) A solution in which the concentration and the like are adjusted so that the resulting film exhibits desired wavelength dispersion characteristics. Next, the color filter layer 13 is formed on the obtained film 12 of the present invention. the

Example

Hereinafter, the present invention will be described in more detail by way of examples. "%" and "part" in an example are % by weight and a part by weight, unless otherwise specified. the

Embodiment 1 [synthetic example of compound (1-a14)]

(1) Synthesis of compound (e)

Compound (e) is obtained by reacting compound (d) and compound (h) as shown in the following synthetic scheme. the

(Synthesis example of compound (d))

Compound (a) was synthesized according to the method described in JP-A-2004-262884. the

100 g of the compound (a), 97 g of potassium carbonate, and 64 g of 6-chlorohexanol were heated in N,N-dimethylacetamide at 90° C. under a nitrogen atmosphere to perform a reaction. Furthermore, it heated to 100 degreeC, and reacted. The resulting reaction mixture was cooled to room temperature, pure water and methyl isobutyl ketone were added, and the organic layer was separated. The organic layer was washed with an aqueous sodium hydroxide solution and pure water, and then dehydrated. The dehydrating agent was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. Methanol was added to the obtained residue, and the formed precipitate was taken out by filtration and vacuum-dried to obtain 126 g of compound (b). Yield: 91% (based on 6-chlorohexanol). the

Mix 126g of compound (b), 1.4g of 3,5-di-tert-butyl-4-hydroxytoluene, 117g of N,N-dimethylaniline, 1g of 1,3-dimethyl-2-imidazolidinone and chloroform . In a nitrogen atmosphere, 58 g of acryloyl chloride was dropped to the obtained mixture under ice-cooling, and pure water was further added and reacted. The organic layer was separated from the resulting reaction mixture. The organic layer was washed with hydrochloric acid water, saturated sodium carbonate aqueous solution and pure water. A dehydrating agent was added to the organic layer, followed by drying. After removing the dehydrating agent, 1 g of 3,5-di-tert-butyl-4-hydroxytoluene was added to the obtained filtrate, followed by concentration under reduced pressure to obtain compound (c). the

Compound (c) and 200 ml of tetrahydrofuran were mixed. After further adding 200 ml of tetrahydrofuran to the obtained mixture, hydrochloric acid water and concentrated hydrochloric acid water were added, and the reaction was carried out at 60° C. under a nitrogen atmosphere. The reaction mixture was washed with 500 ml of saturated brine, and dehydrated with a dehydrating agent. The dehydrating agent was filtered, and the obtained filtrate was concentrated under reduced pressure. Hexane was added to the obtained concentrate, followed by stirring under ice cooling. The precipitated solid was taken out by filtration and vacuum-dried to obtain 90 g of compound (d). The yield was 79% (based on compound (c)). the

(Synthesis example of compound (h))

200 g of trans-1,4-cyclohexanedicarboxylic acid and 1000 ml of N,N-dimethylacetamide were mixed. After heating up the obtained mixture to 80 degreeC, stirring under nitrogen atmosphere, 96 g of potassium carbonate and 10 g of potassium iodide were added. Furthermore, 140 g of benzyl chloride was added, and the obtained solution was reacted at 120 degreeC for 6 hours. After standing to cool the obtained reaction solution to room temperature, it poured into 1500 g of ice, and stirred. The obtained crystals were taken out by filtration, washed with water/methanol 3:2 (v/v) and water successively. The washed crystals were vacuum-dried to obtain 251 g of a powder containing compound (f). the

251 g of powder containing compound (f) and 600 ml of chloroform were mixed. The obtained solution was ice-cooled, and 93.53 g of chloromethyl ether and 146.83 g of triethylamine were added dropwise under a nitrogen atmosphere. The resulting solution was reacted at room temperature for 3 hours under a nitrogen atmosphere. To the obtained reaction solution was added 600 ml of toluene, and the precipitated triethylamine hydrochloride was removed by filtration. The obtained filtrate was washed with water and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration and the solvent was removed from the resulting filtrate. The obtained concentrated residue was vacuum-dried to obtain 242 g of a liquid containing compound (g). the

242 g of the liquid containing the compound (g) and 250 ml of tetrahydrofuran were mixed. After adding 10 g of 10% palladium-carbon (50% water content) to the obtained solution under a nitrogen atmosphere, the resulting mixture was reacted under a hydrogen atmosphere at room temperature and normal pressure for 6 hours. The resulting reaction mixture was filtered, and after removing the catalyst, the solvent was removed. The residue was dissolved in chloroform, and the resulting solution was filtered through silica gel. The insoluble matter on the silica gel was extracted with chloroform, and the resulting chloroform solution was concentrated under reduced pressure. Heptane was added to the obtained residue to crystallize it. The obtained crystals were taken out by filtration and dried in vacuo to obtain 106 g of compound (h). Yield: 39% (based on trans-1,4-cyclohexanedicarboxylic acid). the

(Synthesis example of compound (e))

56.8 g of compound (d), 2.65 g of N,N-dimethylaminopyridine, 50 g of compound (h) and 300 ml of chloroform were mixed. The obtained mixed solution was stirred under ice-cooling under a nitrogen atmosphere, and a solution obtained by dissolving 48.79 g of dicyclohexylcarbodiimide in 50 ml of chloroform was added dropwise. After the dropwise addition was complete, the resulting mixture was stirred at room temperature. To the obtained reaction mixture were added 200 ml of chloroform and 200 ml of heptane, and the precipitate was removed by filtration. After the filtrate was washed with 2N hydrochloric acid, insoluble components were removed by filtration. After the obtained filtrate was dried over anhydrous sodium sulfate, sodium sulfate was removed by filtration. The solvent was removed from the obtained filtrate, and the obtained solid was vacuum-dried to obtain 100 g of compound (e'). the

100 g of compound (e'), 3.7 g of pure water, 3.8 g of p-toluenesulfonic acid monohydrate, and 200 ml of tetrahydrofuran were mixed and reacted at 50°C under a nitrogen atmosphere. After the obtained reaction solution was left to cool to room temperature, tetrahydrofuran was removed under reduced pressure. To the obtained residue was added 200 ml of heptane. The deposited precipitate was taken out by filtration, washed with pure water, and vacuum-dried. The obtained powder was dissolved in chloroform, and filtered through silica gel. The filtrate was mixed with 400 ml of chloroform, and the resulting solution was concentrated. Toluene was added to the concentrated residue, and the resulting solution was concentrated under reduced pressure. Heptane was added to the concentrated residue to crystallize, and the resulting crystals were taken out by filtration. The taken-out crystals were vacuum-dried to obtain 64 g of compound (e). Yield: 76% (based on compound (d)). the

Synthesis example of compound (1-a14)

3.4 g of phenylhydroquinone, 16 g of compound (e), 0.5 g of 4-dimethylaminopyridine, and 237 g of chloroform were mixed. A solution obtained by dissolving 9.4 g of N,N'-dicyclohexylcarbodiimide in 9 g of chloroform was added dropwise to the obtained mixture at room temperature, and reacted for 36 hours. To the obtained reaction mixture was added 140 g of 2N hydrochloric acid, and the obtained mixture was filtered. After washing by adding 140 g of 2N hydrochloric acid to the obtained filtrate, it was concentrated to obtain about 50 g of a concentrate. 0.4 g of activated charcoal was added to the concentrate, and it was filtered through celite. After the obtained filtrate was concentrated, methanol was added to the concentrated residue to obtain a solid. The obtained solid was washed with methanol to obtain 8.4 g of compound (1-a14) as a white solid. Yield: 47% (based on phenylhydroquinone). the

¹ H-NMR (CDCl ₃ ) of compound (1-a14): δ (ppm) 1.35-1.91 (m, 24H), 2.35-2.58 (m, 12H), 3.93 (t, 4H), 4.17 (t, 4H ), 5.81(dd, 2H), 6.12(m, 2H), 6.40(dd, 2H), 6.84～6.99(m, 8H), 7.11(m, 3H), 7.38(m, 5H)

The phase transition temperature of the obtained compound (1-a14) was confirmed by structural observation with a polarizing microscope. Compound (1-a14) exhibits a nematic phase from 84°C to 198°C when the temperature rises, and turns into an isotropic phase at 198°C. When the temperature is lowered from 200°C, it will be in nematic phase from 198°C to 36°C, and will crystallize at 36°C. Thus, the compound (1-a14) exhibits nematic liquid crystallinity not only in a wide temperature range but also in the vicinity of 40°C. the

Embodiment 2 [synthetic example of compound (1-a3)]

1.0 g of t-butylhydroquinone, 6.0 g of compound (e), 0.2 g of 4-dimethylaminopyridine and 121 g of chloroform were mixed. A solution obtained by dissolving 4.5 g of N,N'-dicyclohexylcarbodiimide in 24 g of chloroform was added dropwise to the obtained mixture at room temperature, and reacted for 3 hours. After adding 60 g of 2N hydrochloric acid to the obtained reaction solution, the obtained mixture was filtered. The obtained filtrate was washed with 60 g of 2N hydrochloric acid, and then concentrated to obtain about 40 g of a concentrate. 0.3 g of activated charcoal was added to the concentrate, and it was filtered through celite. The solvent was distilled off from the obtained filtrate. Methanol was added to the obtained concentrated residue to obtain a solid. The obtained solid was washed with methanol to obtain 4.1 g of compound (1-a3) as a white solid. Yield: 71% (based on tert-butylhydroquinone). the

¹ H-NMR (CDCl ₃ ) of compound (1-a3): δ (ppm) 1.34 (s, 9H), 1.35-1.91 (m, 24H), 2.35-2.58 (m, 12H), 3.94 (t, 4H) , 4.17(t, 4H), 5.81(dd, 2H), 6.12(m, 2H), 6.40(dd, 2H), 6.84～7.06(m, 11H)

The phase transition temperature of the obtained compound (1-a3) was confirmed by structural observation with a polarizing microscope. It was confirmed that compound (1-a3) exhibited a smectic phase from 66°C to 96°C and a nematic phase from 96°C to at least 180°C when the temperature was raised. When the temperature is lowered from 180°C, it is confirmed that the nematic phase is formed from 180°C to at least 29°C, and no crystallization occurs. Compound (1-a3) not only exhibits nematic liquid crystallinity over a wide temperature range, but also exhibits nematic liquid crystallinity at around 30°C. the

Comparative Example 1 [Synthesis Example of Compound (III-1-1)]

(Synthesis example of compound (i))

84.5 g of ethyl 4-hydroxybenzoate, 84.2 g of 4-chlorobutyl acetate, 105 g of potassium carbonate, and 254 g of N,N-dimethylacetamide were mixed, and the obtained mixture was heated to 100° C. and stirred. After cooling, methyl isobutyl ketone was added to the reaction mixture, and after washing with water, the solvent was removed to obtain 126 g of an oily substance mainly composed of compound (i). Yield: 88% (based on ethyl 4-hydroxybenzoate). the

(Synthesis example of compound (j))

126 g of an oily substance mainly composed of compound (i), 378 g of methanol, 252 g of water, and 54 g of sodium hydroxide were mixed and reacted at 65°C. After cooling the reaction mixture, it was poured into 756 g of ice, and hydrochloric acid was further added. The precipitated solid was taken out, washed with water and heptane, and dried to obtain 91 g of a solid mainly composed of compound (j). Yield: 97% (based on compound (i)). the

(Synthesis example of compound (k))

Under a nitrogen atmosphere, 90.0 g of a solid mainly composed of compound (j) and 77.8 g of N,N-dimethylaniline were dissolved in 720 g of N,N-dimethylacetamide. After cooling the obtained solution to 0 degreeC, 58.1 g of acryloyl chlorides were dripped and it was made to react at room temperature. After adding 1N hydrochloric acid to the obtained reaction mixture, the precipitated solid was taken out. The solid removed was dissolved in ethyl acetate. After the obtained solution was washed with water, the solvent was removed to obtain 102 g of a solid mainly composed of compound (k). Yield: 90% (based on compound (j)). the

(Synthesis example of compound (III-1-1))

3 g of hydroquinone, 16 g of a solid mainly composed of compound (k), 0.7 g of 4-dimethylaminopyridine, and 127 g of chloroform were mixed. A solution obtained by dissolving 12 g of N,N'-dicyclohexylcarbodiimide in 32 g of chloroform was added dropwise to the obtained mixture at room temperature, and reacted for 3 hours. After adding 159 g of 2N hydrochloric acid to the reaction mixture, it was filtered. After washing by adding 159 g of 2N hydrochloric acid to the obtained filtrate, the solvent was distilled off, and methanol was added to obtain a solid. The obtained solid was washed with methanol to obtain 12.0 g of compound (III-1-1) as a white solid. Yield: 66% (based on hydroquinone). the

The phase transition temperature of compound (III-1-1) was confirmed by structural observation using a polarizing microscope. Raising the temperature, the crystalline phase changes to the nematic phase around 107°C, and then turns into the isotropic liquid phase around 167°C. When the temperature is lowered, the isotropic liquid phase changes from an isotropic liquid phase to a nematic phase at around 167 °C, and then it returns to a crystalline phase when the temperature is lowered to around 74 °C. That is, it was found that compound (III-1-1) was in a nematic phase from 107°C to 167°C when the temperature was raised, and from 167°C to 107°C when the temperature was lowered. the

Embodiment 3～6 and comparative example 2

<Preparation of composition>

Compositions having the compositions shown in Table 2 were prepared. The % in Table 2 means the weight% when the total weight of a composition is 100 weight%. the

[Table 2]

Photopolymerization initiator: IRGACURE 819 (manufactured by Ciba Corporation; acylphosphine oxide compound)

Leveling agent: BYK 361N (manufactured by BYK-Chemie Japan)

Solvent: Cyclopentanone

<Observation of Thermal Behavior>

A 2% by weight aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 complete saponification type, manufactured by Wako Pure Chemical Industries, Ltd.) was applied on a glass substrate, followed by heating and drying to form a film with a thickness of 89 nm. A rubbing treatment is performed on the surface of the film to form an alignment film. The composition described in Table 2 was coated on the surface subjected to the rubbing treatment by the spin coating method. Using a polarizing microscope equipped with a hot stage (hot stage: LTS350, manufactured by Linkam; polarizing microscope: BX-51, manufactured by Olympus Corporation), the obtained substrate was heated at a heating rate of 30° C./min. Observe the behavior of the composition. Behavior was observed by natural cooling while cooling down. The results are shown in Table 3. the

[table 3]

the Observation results Example 3 It is confirmed that when the temperature is raised, the phase transitions to a nematic phase at 78°C, and a single domain structure begins to form, and the single domain structure is maintained at least up to 150°C. When the temperature is lowered from 150°C, it becomes a nematic phase at 38°C, forming a single domain structure, and crystallizes at 38°C. Example 4 It is confirmed that when the temperature is raised, the phase transitions to a nematic phase at 20°C, and a single-domain structure begins to form, and the single-domain structure is maintained at least up to 150°C. When the temperature is lowered from 150°C, it becomes a nematic phase at 40°C, forming a single domain structure, and crystallizes at 40°C. Example 5 It is confirmed that when the temperature is raised, the phase transitions to the nematic phase at 84°C, and the monodomain structure begins to form, and the monodomain structure is maintained at least up to 150°C. When the temperature is lowered from 150°C, it becomes a nematic phase at 40°C, forming a single domain structure, and crystallizes at 40°C. Example 6 It is confirmed that when the temperature is raised, the phase transitions to a nematic phase at 100°C, and a single domain structure begins to form, and the single domain structure is maintained at least up to 150°C. When the temperature is lowered from 150°C, it becomes a nematic phase at 36°C, forming a single domain structure, and crystallizes at 36°C. Comparative example 2 It is confirmed that when the temperature is raised, the phase transitions to a nematic phase at 143°C, and a single-domain structure begins to form, and the single-domain structure is maintained at least until 158°C. It was also confirmed that when the temperature was lowered from 160°C, the nematic phase was formed at 80°C, forming a monodomain structure.

<Example of film production>

A 2% by weight aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 complete saponification type, manufactured by Wako Pure Chemical Industries, Ltd.) was applied on a glass substrate, followed by heating and drying to form a film with a thickness of 89 nm. A rubbing treatment is performed on the surface of the film to form an alignment film. The composition described in Table 2 was applied by spin coating on the surface subjected to rubbing treatment, and dried at the temperature (T _c ) described in Table 4 for 1 minute. After being left to stand at the temperature (T _d ) described in Table 4 for 1 minute, it was irradiated with ultraviolet light having a cumulative light intensity of 2400 mJ/cm ² to form a film.

<Observation of surface state>

The surface state of the film was observed with a polarizing microscope at a magnification of 400 times. It was marked as ◯ if it was a single domain, and was marked as × if a defect occurred. The results are shown in Table 4. the

<Stability over time> 

After the film was left at room temperature in the atmosphere for 2 weeks, the surface state of the film was observed with a polarizing microscope. It was marked as ◯ if no alignment defect was found, and was marked as × if an alignment defect occurred. The results are shown in Table 4. the

[Table 4]

the T _c (°C) T _d (℃) surface condition Stability over time Example 3 90 30 ○ ○ Example 4 60 30 ○ ○ Example 5 100 50 ○ ○ Example 6 100 50 ○ ○ Comparative example 2 150 140 × ×

<Measurement of Optical Properties>

The retardation value of the film was measured with a measuring instrument (KOBRA-WR, manufactured by Oji Scientific Instruments). The measurement of the retardation value (nm) was performed on a laminate including a glass substrate, an alignment film, and a film. Since the glass substrate and the alignment film have no birefringence (for the glass substrate and the alignment film, Re(447)=Re(547)=Re(628)=0), therefore, the phase difference value measured can be used as the phase of the film difference. The retardation value Re(λ) was measured at wavelengths (λ) of 447nm, 547nm and 628nm. The thickness d (µm) of the film was measured with a laser microscope (LEXT3000, manufactured by Olympus Corporation). The results are shown in Table 5. the

[table 5]

the Re(447) Re(547) Re(628) Re(447)/Re(547) Re(628)/Re(547) d Example 3 109 106 104 1.034 0.981 1.10 Example 4 115 110 108 1.045 0.985 1.10 Example 5 126 116 114 1.083 0.979 0.81 Example 6 130 120 120 1.083 0.977 0.81 Comparative example 3 99 91 86 1.093 0.944 0.54

In Examples, films were produced at low temperatures such as 30°C or 50°C. the

By polymerizing the compound of the present invention, a film having excellent surface state and temporal stability and optical properties can be produced at low temperature. the

Claims (7)

1. A compound represented by formula (1), In the formula, X represents an alkyl group with 2 to 20 carbon atoms or an unsubstituted aromatic hydrocarbon group with 6 to 20 carbon atoms, E ¹ =E ² , and represents -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-NR ⁶ -, -NR ⁶ -CO-, -O-CH ₂ -or -CH ₂ -O-, R ⁶ represents a hydrogen atom or an alkyl group with 1 to 6 carbon atoms, A ¹ = A ² , and represents a group formed of a 5-membered or 6-membered aromatic group represented by the following formulas (g-1) to (g-5), B ¹ =B ² , B ³ =B ⁴ , and represent -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -CO-NR ⁶ -, - NR ⁶ -CO-, -CO- or -CS-, R ⁶ represents a hydrogen atom or an alkyl group with 1 to 6 carbon atoms, F ¹ =F ² , and represents an unsubstituted alkanediyl group with 1 to 12 carbon atoms, P ¹ =P ² , and represents a group represented by formula (P-1), In the formula, R ¹ , R ² and R ³ each independently represent an alkyl group having 1 to 6 carbon atoms or a hydrogen atom. 2. The compound according to claim 1, which is a compound represented by formula (1-a14) or formula (1-a3) 3. A composition comprising the compound according to claim 1 or 2 and a photopolymerization initiator. 4. A film obtained by polymerizing the compound according to claim 1 or 2. 5. A color filter comprising the film according to claim 4. 6. A flat panel display device comprising the film according to claim 4. 7. A method for producing a film comprising the step of applying the compound according to claim 1 or 2 to a substrate or to an alignment film formed on a substrate.