KR20090073006A - Optical film - Google Patents

Abstract

An optical film is provided to make the uniform polarization conversion about the wide wavelength band possible by improving the chemical composition. An optical film(2) is obtained by polymerizing the compound. The compound contains at least one polymerizable group expressed by the following formula(A). -G^a-D^a-Ar-D^b-G^b- (A). D^a and D^b independently show the short-chain-CO-O-, -O-CO-, -C(=S)-O-, -O-C(=S)-, -CR^1R^2-, -CR^1R^2-CR^3R^4-, -OCR^1R^2-, -CR^1R^2-O-, -CR^1R^2-O-CR^3R^4-, -CR^1R^2-O-CO-, -O-CO-CR^1R^2-, -CR^1R^2-O-CO-CR^3R^4-, -CR^1R^2-CO-O-CR^3R^4-, -NR^1-CR^2R^3-, -CR^2R^3-NR^1-, -CO-NR^1- or NR^1-CO-.

Description

Optical film {OPTICAL FILM}

The present invention relates to an optical film.

The flat panel display apparatus (FPD) contains the member using optical films, such as a polarizing plate and retardation plate. As an optical film, the optical film obtained by superposing | polymerizing after apply | coating the solution obtained by melt | dissolving a polymeric compound in a solvent to a support base material is mentioned.

On the other hand, it is known that the retardation (Re (λ)) of the optical film provided by the light having a wavelength of λ nm is determined by the product of the birefringence Δn and the thickness d of the film (Re (λ) = Δn × d). Moreover, the wavelength dispersion characteristic is represented by the value (Re (λ) / Re (550)) obtained by dividing the phase difference value Re (λ) at a wavelength λ nm by the phase difference value Re (550) at 550 nm, and (Re ( λ) / Re (550)) shows a wavelength range close to 1 or reverse wavelength dispersion of [Re (450) / Re (550)] <1 and [Re (650) / Re (550)]> 1. In the wavelength range, it is known that uniform polarization conversion is possible.

SID Symposium Digest of Technical Papers, 2006, 37, p. 1673 discloses a compound (LC242) represented by the following formula as a polymerizable compound.

An object of the present invention is to provide an optical film capable of uniform polarization conversion in a wide wavelength range.

The present invention,

<1> Formula (A)

(Wherein Ar represents a divalent group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, and the total number of π electrons in the aromatic ring contained in the bivalent group) N _π is greater than or _equal to 12. D ^a and D ^b are each independently a single bond, -CO-O-, -O-CO-, -C (= S) -O-, -OC (= S)-,- ^{CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R 2 -O-CR 3 R 4 -, -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ^3- , -CR ² R ³ -NR ^1- , -CO-NR ¹ -or NR ¹ -CO- and R ¹ , R ² , R ³ and R ⁴ Each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ^a and G ^b each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic hetero group; The ring group is a halogen atom, May be substituted with at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, and a nitro group)

Optical film obtained by superposing | polymerizing the compound containing group shown by the and at least 1 polymeric group;

The compound containing group represented by <2> Formula (A) and at least 1 polymeric group is Formula (B)

Wherein Ar, D ^a , D ^b , G ^a and G ^b have the same meanings as defined in <1>, and E ¹ and E ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-,- OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- Or a single bond, R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms) and an optical compound according to <1>, which is a compound containing at least one polymerizable group. film ;

The compound containing group represented by <3> Formula (B) and at least 1 polymeric group is Formula (C)

Wherein Ar, D ^a , D ^b , G ^a , G ^b , E ¹ and E ² have the same meanings as defined in <1> and <2>, and B ¹ and B ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O- , -OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S- CH _2- , -CH ₂ -S- or a single bond, R ⁵ and R ⁶ have the same meaning as described above, A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group; The alicyclic hydrocarbon group and the aromatic hydrocarbon group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a fluoroalkoxy group having 1 to 4 carbon atoms, May be substituted with at least one selected from the group consisting of a cyano group and a nitro group, k and l each independently represent an integer of 0 to 3)

The optical film as described in <2> which is a compound containing group represented by the following and at least 1 polymeric group;

The compound containing group represented by <4> Formula (C) and at least 1 polymeric group is Formula (D)

(Wherein Ar, D ^a , D ^b , G ^a , G ^b , E ¹ , E ² , B ¹ and B ² represent the same meanings as defined in <1>, <2> and <3>, and F Each of ¹ and F ² independently represents an alkylene group having 1 to 12 carbon atoms, and the alkylene group may be substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom. and, also, at least one group of the methylene groups constituting the alkylene may be substituted with -O- or -CO-. P ¹ and P ² of which one represents a polymerizable group, the other is a hydrogen atom or a polymerizable group Indicates)

Optical film as described in <3> which is a compound represented by;

<5> Optical film in any one of <1>-<4> which satisfy | fills Formula (2) and Formula (3);

The compound represented by <6> Formula (D) is Formula (1)

Wherein Ar, E ¹ , E ² , B ¹ , B ² , F ¹ , F ² , P ¹ , P ² , k and l are <1>, <2>, <3> and <4> Have the same meaning as defined, D ¹ and D ² are each independently -CR ¹ R ^2- , -CR ¹ R ² -CR ³ R ^4- , -O-CR ¹ R ^2- , -CR ¹ R ^2- O-, -CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ^1- , and R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above, G ¹ and G ² each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, and the aromatic hydrocarbon group and the aromatic heterocyclic group represent a halogen atom and carbon number. May be substituted with at least one selected from the group consisting of an alkyl group of 1 to 4, a fluoroalkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a cyano group, and a nitro group)

Optical film as described in <4> which is a compound shown by;

<7> Ar is an optical film as described in any one of <1>-<6> which is any of group represented by Formula (Ar-1)-a formula (Ar-13);

(In formula, Z <^1> is a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a carboxyl group, C1-C6 fluorine. A roalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 N-alkylamino group, a C2-C12 N, N- dialkylamino group, a C1-C6 N- An alkylsulfamoyl group or an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, Q ¹ and Q ³ are each independently -CR ⁷ R ^8- , -S-, -NR ^7- , -CO- Or -O-, and R ⁷ and R ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to ^4. Y ¹ , Y ² and Y ³ are each independently an aromatic hydrocarbon group which may be substituted or substituted The aromatic heterocyclic group which may be present W ¹ and W ² independently represent a hydrogen atom, a cyano group, a methyl group or a halogen atom M represents an integer of 0 to 6, and n represents an integer of 0 to 2).

<8> D ^a is -O-CR ¹ R ² - a, D ^b is -CR ¹ R ² -O- in <1> to the optical film described in any of <5>;

<9> G ^a and G ^b is the optical film according to any one of the 1,4-phenylene group <1> to <5>;

<10> D ¹ is -O-CR ¹ R ² -, and, D ² is the optical film according to -CR ¹ R ² -O- in <6>;

<11> G ¹ and G ² The optical film as described in <6> whose is a 1, 4- phenylene group;

The optical film in any one of <1>-<11> whose phase difference value (Re (550)) in <12> wavelength 550nm is 113-163 nm;

Optical film in any one of <1>-<11> whose phase difference value (Re (550)) in <13> wavelength 550nm is 250-300 nm;

<14> Formula (A)

(Wherein, Ar represents a divalent group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocyclic ring, the divalent group the total number of π electrons of the aromatic ring contained in the N _π 12 D ^a and D ^b are each independently a single bond, -CO-O-, -O-CO-, -C (= S) -O-, -OC (= S)-, -CR ¹ R ^{2 -, -CR 1 R 2 -CR 3} R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R 2 -O-CR 3 R 4 -, -CR 1 R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ^3- , -CR ² R ³ -NR ^1- , -CO-NR ¹ -or NR ¹ -CO-, and R ¹ , R ² , R ³ and R ⁴ are each independently A hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ^a and G ^b each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic heterocyclic group each being a halogen atom; Carbon 1-4 alkyl group, a fluoroalkyl group having 1 to 4 carbon atoms in the alkyl group, may be substituted by at least one selected from an alkoxy group, a cyano group and a nitro group consisting of 1 to 4 carbon atoms)

A compound containing a group represented by and at least one polymerizable group and formula (4)

(In formula, A <^11> represents an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a heterocyclic group, The aromatic hydrocarbon group, an alicyclic hydrocarbon group, and a heterocyclic group are a halogen atom, a C1-C6 alkyl group, C1-C6 May be substituted with at least one selected from the group consisting of an alkoxy group, an N-alkylamino group having 1 to 6 carbon atoms, a nitro group, a cyano group, and a mercapto group, B ¹¹ and B ¹² are each independently -CR ¹⁴ R ¹⁵ -, -C≡C-, -CH = CH-, -CH ₂ -CH _2- , -O-, -S-, -C (= O)-, -C (= O) -O-, -OC (= O)-, -OC (= O) -O-, -C (= S)-, -C (= S) -O-, -OC (= S)-, -CH = N-, -N = CH-, -N = N-, -C (= O) -NR 14 -, -NR 14 -C (= O) -, -OCH 2 -, -OCF 2 -, -NR 14 -, -CH 2 O-, —CF ₂ O—, —CH═CH—C (═O) —O—, —OC (═O) —CH═CH— or a single bond, and R ¹⁴ and R ¹⁵ are each independently hydrogen atom, a fluorine atom or an alkyl group having a carbon number of 1~4, R ¹⁴ and R ¹⁵ are combined to form a group having a carbon number of 4-7 alkylene Is Fig. ¹¹ E represents an alkylene group having 1 to 12 carbon atoms, the alkylene group is optionally substituted by at least one selected from alkyl groups, alkoxy groups and halogen atoms, the group consisting of 1 to 6 carbon atoms having 1 to 6 carbon atoms. P ¹¹ represents a polymerizable group, G represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 13 carbon atoms, an alkoxy group of 1 to 13 carbon atoms, a fluoroalkyl group of 1 to 13 carbon atoms, an N-alkylamino group of 1 to 13 carbon atoms, It is a cyano group or a nitro group, or the polymeric group couple | bonded via a C1-C12 alkylene group, The alkylene group is a group which consists of a C1-C6 alkyl group, a C1-C6 alkoxy group, and a halogen atom. May be substituted with at least one selected. T represents an integer of 1 to 5)

A composition containing a compound represented by;

The compound containing group represented by <15> Formula (A) and at least 1 polymeric group is Formula (1)

Wherein Ar represents the same meaning as defined in <14>. D ¹ and D ² each independently represent -CR ¹ R ^2- , -CR ¹ R ² -CR ³ R ^4- , -O-CR ¹ R ^2- , -CR ¹ R ² -O-, -CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ² -,- CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ^1- R <^1> , R <^2> , R <^3> and R <^4> represent the same meaning as the above, G <^1> and G <^2> represent a bivalent aromatic hydrocarbon group or a bivalent aromatic heterocyclic group each independently, The aromatic hydrocarbon group and The aromatic heterocyclic group may be substituted with at least one selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group. E ¹ and E ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O -, -C (= S) -O-,- OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH ₂ -, -CH ₂ -S- or a single bond, R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms B ¹ and B ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH ₂ -., -CH ₂ -S- or a single bond represents the a ¹ and a ² are each independently a divalent represents an alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group is the alicyclic hydrocarbon group and the aromatic hydrocarbon group, halogen Substituted with at least one selected from the group consisting of an atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a fluoroalkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group You may be. k and l respectively independently represent the integer of 0-3. F ¹ and F ² each independently represent an alkylene group having 1 to 12 carbon atoms, and the alkylene group is substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom; At least one methylene group constituting the alkylene group may be substituted with -O- or -CO-. Either one of P ¹ and P ² represents a polymerizable group, and the other represents a hydrogen atom or a polymerizable group)

The composition as described in <14> which is a compound shown by;

<16> The composition as described in <14> or <15> which further contains a photoinitiator;

<17> Polarizing plate containing the optical film and polarizing film in any one of <1>-<11>;

A color filter in which the <18> color filter layer, the alignment film, and the optical film according to any one of <1> to <11> are laminated in this order;

<19> Liquid crystal display device containing the color filter as described in <18>;

<20> Flat panel display apparatus which comprises the polarizing plate and liquid crystal panel as described in <17>;

<21> Organic electroluminescent display provided with the organic electroluminescent panel containing the polarizing plate of <17>;

<22> Formula (1)

(Wherein, Ar represents a divalent group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocyclic ring, the divalent group the total number of π electrons of the aromatic ring contained in the N _π 12 . more than the D ¹ and D ² are each independently in each ^{-CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ⁴ -, -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ¹ -and represents R ¹ , R ² , R ³ and R ⁴ each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ¹ and G ² each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic group The heterocyclic group is a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, It may be substituted with at least one selected from the group consisting of an alkoxy group, a cyano group and a nitro group having 1 to 4. E ¹ and E ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH ₂ -,- O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC (= S ) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- or a single bond And R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to ^4. C ¹ and B ² are each independently —CR ⁵ R ⁶ —, —CH ₂ —CH ₂ —, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- or single bond Indicates. A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a C1-4 carbon atom. It may be substituted by at least one selected from the group consisting of a fluoroalkyl group, an alkoxy group having 1 to 4 carbon atoms, a fluoroalkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group. k and l respectively independently represent the integer of 0-3. F ¹ and F ² each independently represent an alkylene group having 1 to 12 carbon atoms, and the alkylene group is substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom; At least one methylene group constituting the alkylene group may be substituted with -O- or -CO-. Either one of P ¹ and P ² represents a polymerizable group, and the other represents a hydrogen atom or a polymerizable group)

Compound represented by;

The compound as described in <22> which satisfy | fills <23> Formula (2) and Formula (3);

<24> Ar is a compound according to <22> or <23>, which is any of groups represented by formulas (Ar-1) to (Ar-13);

(In formula, Z <^1> is a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a carboxyl group, C1-C6 fluorine. A roalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 N-alkylamino group, a C2-C12 N, N- dialkylamino group, a C1-C6 N- An alkylsulfamoyl group or an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, Q ¹ and Q ³ are each independently -CR ⁷ R ^8- , -S-, -NR ^7- , -CO- Or -O-, and R ⁷ and R ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to ^4. Y ¹ , Y ² and Y ³ are each independently an aromatic hydrocarbon group which may be substituted or substituted It represents an aromatic heterocyclic ring which may. W ¹ and W ² each independently represent a hydrogen atom, a cyano group, a methyl group or a halogen Represent characters. M represents an integer of 0~6, n represents an integer of 0 to 2)

<25> The compound according to any one of <22> to <24>, wherein D ¹ is -O-CR ¹ R ² -and D ² is -CR ¹ R ² -O-;

<26> The compound according to any one of <22> to <25>, in which G ¹ and G ² are 1,4-phenylene groups;

<27> A method for producing an unpolymerized film, wherein the solution containing the compound according to any one of <22> to <26> is applied onto a support substrate or an alignment film formed on the support substrate, and dried.

<28> It provides the manufacturing method etc. of the optical film which superpose | polymerize the unpolymerized film obtained by the manufacturing method as described in <27>.

The optical film of this invention is possible for uniform polarization conversion in a wide wavelength range.

The optical film of this invention is a following formula (A)

(Wherein, Ar represents a divalent group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocyclic ring, the divalent group the total number of π electrons of the aromatic ring contained in the N _π 12 D ^a and D ^b are each independently a single bond, -CO-O-, -O-CO-, -C (= S) -O-, -OC (= S)-, -CR ¹ R ^{2 -, -CR 1 R 2 -CR 3} R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R 2 -O-CR 3 R 4 -, -CR 1 R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ^3- , -CR ² R ³ -NR ^1- , -CO-NR ¹ -or NR ¹ -CO-, and R ¹ , R ² , R ³ and R ⁴ are each independently A hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ^a and G ^b each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic heterocyclic group each being a halogen atom; Carbon 1-4 alkyl group, a fluoroalkyl group having 1 to 4 carbon atoms in the alkyl group, may be substituted by at least one selected from an alkoxy group, a cyano group and a nitro group consisting of 1 to 4 carbon atoms)

It is obtained by superposing | polymerizing the compound (henceforth abbreviated as a compound (A)) containing the group shown by this and at least 1 polymeric group.

In the present invention, the term "optical film" refers to a film having optical function as a film that can transmit light. Optical function means refraction, birefringence, etc. A retardation film, which is a kind of optical film, is used to convert linearly polarized light into circularly polarized light or elliptically polarized light, or conversely convert circularly or elliptically polarized light into linearly polarized light.

By having the group represented by said formula (A), the optical film of this invention becomes uniform polarization conversion in a wide wavelength range. Moreover, the wavelength dispersion characteristic of an optical film can be adjusted by adjusting content of group represented by Formula (A) in an optical film.

Ar is a divalent group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, and the total number N _π of the π electrons in the aromatic ring contained in the divalent group is 12 or more, preferably Preferably it is 12 or more and 22 or less, More preferably, it is 13 or more and 22 or less.

Ar is preferably a divalent group having at least two aromatic rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.

Examples of the aromatic hydrocarbon ring include benzene ring, naphthalene ring, anthracene ring, and phenanthroline ring, and the like, and the aromatic hetero ring include furan ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, Benzothiazole ring; and the like. Especially, a benzene ring, a thiazole ring, and a benzo thiazole ring are preferable.

Ar is preferably any group among the groups represented by the following formulas (Ar-1) to (Ar-13).

(In formula, Z <^1> is a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a carboxyl group, C1-C6 fluorine. A roalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 N-alkylamino group, a C2-C12 N, N- dialkylamino group, a C1-C6 N- An alkylsulfamoyl group or an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, Q ¹ and Q ³ are each independently -CR ⁷ R ^8- , -S-, -NR ^7- , -CO- Or -O-, and R ⁷ and R ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to ^4. Y ¹ , Y ² and Y ³ are each independently an aromatic hydrocarbon group which may be substituted or substituted It represents an aromatic heterocyclic ring which may. W ¹ and W ² each independently represent a hydrogen atom, a cyano group, a methyl group or a halogen Represent characters. M represents an integer of 0~6, n represents an integer of 0 to 2)

As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, A fluorine atom, a chlorine atom, and a bromine atom are preferable.

Examples of the alkyl group having 1 to 6 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group. The alkyl group of -4 is preferable, a C1-C2 alkyl group is more preferable, and a methyl group is especially preferable.

Examples of the alkylsulfinyl group having 1 to 6 carbon atoms include methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and pentyl A sulfinyl group, hexyl technical finyl, etc. are mentioned, A C1-C4 alkylsulfinyl group is preferable, A C1-C2 alkylsulfinyl group is more preferable, A methylsulfinyl group is especially preferable.

Examples of the alkylsulfonyl group having 1 to 6 carbon atoms include methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group and pentyl A sulfonyl group, a hexyl sulfonyl group, etc. are mentioned, A C1-C4 alkylsulfonyl group is preferable, A C1-C2 alkylsulfonyl group is more preferable, A methylsulfonyl group is especially preferable.

Examples of the fluoroalkyl group having 1 to 6 carbon atoms include fluoromethyl group, trifluoromethyl group, fluoroethyl group, pentafluoroethyl group, heptafluoropropyl group and nonafluorobutyl group, and the like. Fluoroalkyl group is preferable, a C1-C2 fluoroalkyl group is more preferable, and trifluoromethyl group is especially preferable.

Examples of the alkoxy group having 1 to 6 carbon atoms include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group and hexyloxy group. A C1-C4 alkoxy group is preferable, A C1-C2 alkoxy group is more preferable, A methoxy group is especially preferable.

Examples of the alkylthio group having 1 to 6 carbon atoms include methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group and pentyl tea. A group, a hexylthio group, etc. are mentioned, A C1-C4 alkylthio group is preferable, A C1-C2 alkylthio group is more preferable, A methylthio group is especially preferable.

Examples of the N-alkylamino group having 1 to 6 carbon atoms include N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, and N-sec-butylamino group , N-tert-butylamino group, N-pentylamino group, N-hexylamino group, etc. are mentioned, A C1-C4 N-alkylamino group is preferable, A C1-C2 N-alkylamino group is more preferable, N-methylamino group is particularly preferred.

Examples of the N, N-dialkylamino group having 2 to 12 carbon atoms include N, N-dimethylamino group, N-methyl-N-ethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N -Diisopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group, N, N-dihexylamino group, etc. are mentioned, N of C2-C8 is mentioned. , N-dialkylamino group is preferable, N, N-dialkylamino group having 2 to 4 carbon atoms is more preferable, and N, N-dimethylamino group is particularly preferable.

As a C1-C6 N-alkyl sulfamoyl group, N-methyl sulfamoyl group, N-ethyl sulfamoyl group, N-propyl sulfamoyl group, N-isopropyl sulfamoyl group, N-butyl sulfamoyl group, N Isobutyl sulfamoyl group, N-sec-butyl sulfamoyl group, N-tert-butyl sulfamoyl group, N-pentyl sulfamoyl group, N-hexyl sulfamoyl group and the like. An alkyl sulfamoyl group is preferable, a C1-C2 N-alkyl sulfamoyl group is more preferable, and an N-methyl sulfamoyl group is especially preferable.

As a C2-C12 N, N- dialkyl sulfamoyl group, N, N- dimethyl sulfamoyl group, N-methyl-N-ethyl sulfamoyl group, N, N- diethyl sulfamoyl group, N, N- Dipropylsulfamoyl group, N, N-diisopropylsulfamoyl group, N, N-dibutylsulfamoyl group, N, N-diisobutylsulfamoyl group, N, N-dipentylsulfamoyl group, N, N -Dihexyl sulfamoyl group etc. are mentioned, A C2-C8 N, N- dialkyl sulfamoyl group is preferable, A C2-C4 N, N- dialkyl sulfamoyl group is more preferable, N, N-dimethylsulfamoyl group is particularly preferred.

Z ¹ is a halogen atom, methyl group, cyano group, nitro group, carboxyl group, methylsulfonyl group, trifluoromethyl group, methoxy group, methylthio group, N-methylamino group, N, N-dimethylamino group, N-methylsulfamo It is preferable that it is a diary or N, N- dimethyl sulfamoyl group.

Examples of the alkyl group having 1 to 4 carbon atoms in R ⁷ and R ⁸ include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group and the like. An alkyl group is preferable and a methyl group is more preferable.

Q ¹ is, -S-, -CO-, -NH-, -N (CH 3) - and should preferably, Q ³ is preferably, -S-, -CO-.

As an aromatic hydrocarbon group in Y <^1> , Y <^2> and Y <^3> , C6-C20 aromatic hydrocarbon groups, such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, and a biphenyl group, are mentioned, A phenyl group and a naphthyl group It is preferable and a phenyl group is more preferable. The aromatic heterocyclic group contains at least one hetero atom such as nitrogen atom, oxygen atom or sulfur atom such as furyl group, pyrrolyl group, thienyl group, pyridinyl group, thiazolyl group and benzothiazolyl group, and contains 4 to 4 carbon atoms. 20 aromatic heterocyclic groups are mentioned, and a furyl group, a pyrrolyl group, thienyl group, a pyridinyl group, and a thiazolyl group are preferable.

Such an aromatic hydrocarbon group and an aromatic heterocyclic group may have at least one substituent, and as a substituent, a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, C1-C1 C6-C6 alkylsulfonyl group, carboxyl group, C1-C6 fluoroalkyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, C1-C6 N-alkylamino group, C2-C12 N, N-dialkylamino group, C1-C6 N-alkylsulfamoyl group, C2-C12 N, N- dialkylsulfamoyl group, etc. are mentioned, A halogen atom, a C1-C2 alkyl group, Cyano group, nitro group, alkylsulfonyl group of 1 to 2 carbon atoms, fluoroalkyl group of 1 to 2 carbon atoms, alkoxy group of 1 to 2 carbon atoms, alkylthio group of 1 to 2 carbon atoms, N-alkylamino group of 1 to 2 carbon atoms C2-C4 N, N-dialkylamino group, C1-C2 alkyl sulfamoyl It is preferred.

Halogen atom, C1-C6 alkyl group, cyano group, nitro group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, carboxyl group, C1-C6 fluoroalkyl group, C1-C6 Alkoxy group, C1-C6 alkylthio group, C1-C6 N-alkylamino group, C2-C12 N, N-dialkylamino group, C1-C6 N-alkylsulfamoyl group, and C2-C6 Examples of the N, N-dialkylsulfamoyl group for 12 include the same ones described above.

As Y <^1> , Y <^2> and Y <^3> , it is preferable to independently represent group represented by following formula (Y-1)-(Y-6).

(In formula, Z <^2> is a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a carboxyl group, a C1-C6 fluorine. C1-C6 alkoxy group, C1-C6 thioalkyl group, C1-C6 N-alkylamino group, C2-C12 N, N-dialkylamino group, C1-C6 N-alkyl A sulfamoyl group or an N, N-dialkyl sulfamoyl group having 2 to 12 carbon atoms, R represents a hydrogen atom or a methyl group, a ₁ represents an integer of 0 to 5, and a ₂ Represents an integer of 0 to 4, b ₁ Represents an integer of 0 to 3, b ₂ represents an integer of 0 to ₂ )

It is more preferable that Y <^1> , Y <^2> and Y <^3> are group represented by Formula (Y-1) or Formula (Y-3) each independently from the point which manufacture of a compound (A) is easy.

It is preferable that each of W ¹ and W ² is independently a hydrogen atom, a cyano group or a methyl group, and more preferably a hydrogen atom.

It is preferable that m is 0 or 1. n is preferably 0.

Ar is more preferably a group represented by the following formula (Ar-6a), formula (Ar-6b), formula (Ar-6c), formula (Ar-10a) or (Ar-10b), and formula (Ar-6a) , Group represented by formula (Ar-6b) or formula (Ar-6c) is particularly preferable.

(Wherein Z ¹ , n, Q ¹ , Z ² , a ₁ and b ₁ represent the same meanings as above)

Specific examples of the group represented by formulas (Ar-1) to (Ar-4) include groups represented by formulas (ar-1) to (ar-29).

Specific examples of the group represented by the formula (Ar-5) include groups represented by the formulas (ar-30) to (ar-39).

As a specific example of group represented by Formula (Ar-6) and Formula (Ar-7), group represented by Formula (ar-40)-Formula (ar-119) is mentioned.

As a specific example of group represented by Formula (Ar-8) and Formula (Ar-9), group represented by Formula (ar-120)-a formula (ar-129) is mentioned.

As a specific example of group represented by Formula (Ar-10), group represented by Formula (ar-130)-a formula (ar-149) is mentioned.

Specific examples of the group represented by the formula (Ar-11) include groups represented by the formulas (ar-150) to (ar-159).

As a specific example of group represented by Formula (Ar-12), group represented by Formula (ar-160)-a formula (ar-179) is mentioned.

Specific examples of the group represented by the formula (Ar-13) include groups represented by formulas (ar-180) to (ar-189).

D ^a and D ^b are each independently a single bond, -CO-O-, -O-CO-, -C (= S) -O-, -OC (= S)-, -CR ¹ R ² -,- CR ¹ R ² -CR ³ R ^4- , -O-CR ¹ R ^2- , -CR ¹ R ² -O-, -CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O -CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ^3- , -CR ² R ³ -NR ^1- , -CO-NR ¹ -or NR ¹ -CO-, R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, A fluorine atom or an alkyl group having 1 to 4 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group and the like).

D ^a and D ^b are each independently selected from ^{-CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ^{1 R 2 -CO-O-CR} 3 R 4 -, -NR 1 -CR 2 R 3 - , or -CR ² R ³ - is preferable, ^{and, -CR 1 R 2 -CR 1 R} 2 -, -O- CR ¹ R ² - or -CR ¹ R ² -O- is more preferable that the. It is particularly preferable that D ^a is —O—CR ¹ R ² —, and it is particularly preferable that D ^b is —CR ¹ R ² —O—. It is preferable that R <^1> , R <^2> , R <^3> and R <^4> are a hydrogen atom or a C1-C4 alkyl group each independently, and it is more preferable that they are a hydrogen atom, a methyl group, or an ethyl group.

G ^a and G ^b each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, and the aromatic hydrocarbon group and the aromatic heterocyclic group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a fluoro carbon having 1 to 4 carbon atoms. It may be substituted by at least one selected from the group consisting of an alkyl group, a C1-4 alkoxy group, a cyano group and a nitro group. It is preferable that G ^a and G ^b are each independently a divalent aromatic hydrocarbon group.

As a bivalent aromatic hydrocarbon group, group represented by following formula (a-1)-(a-8) is mentioned, The group represented by a formula (a-1) is preferable, and a 1, 4- phenylene group is more preferable.

As a divalent aromatic heterocyclic group, a furandidi group, a pyrrolediyl group, a thiophendiyl group, a pyridine diyl group, a thiazole diyl group, etc. are mentioned.

In addition to the group represented by said formula (A), a compound (A) has at least 1 polymeric group. It is preferable that a compound (A) has 1-4 polymerizable groups, and it is preferable to have two polymerizable groups from the point of the film hardness of the optical film obtained.

The polymerizable group may be any group that can participate in the polymerization reaction of the compound (A), and specifically, a vinyl group, p-stilbene group, acryloyl group, methacroyl group, acryloyloxy group, methacroyloxy group , Carboxyl group, acetyl group, hydroxyl group, carbamoyl group, N-alkylamino group having 1 to 4 carbon atoms, amino group, epoxy group, oxetanyl group, formyl group, -N = C = O, -N = C = S and the like. have. Especially, since it is suitable for photopolymerization, a radically polymerizable group or a cationic polymerizable group is preferable, Acryloyl group or a methacroyl group is more preferable at the point which is easy to handle and manufacture of a compound (A) is more preferable, And acryloyl group are particularly preferable.

Although a polymeric group may couple | bond directly with the terminal of the group represented by Formula (A), it is preferable to couple | bond via one or more bivalent coupling groups.

As such a compound (A), following formula (B)

(Wherein Ar, D ^a , D ^b , G ^a and G ^b represent the same meaning as described above, and E ¹ and E ² are each independently —CR ⁵ R ⁶ —, —CH ₂ —CH ₂ —, — O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC (= S ) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- or a single bond R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms)

It is preferable that it is a compound containing group represented by following formula (C)

(Wherein Ar, D ^a , D ^b , G ^a , G ^b , E ¹ and E ² have the same meanings as above, and B ¹ and B ² are each independently —CR ⁵ R ⁶ —, —CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)- , -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH _2- S- or a single bond, R ⁵ and R ⁶ have the same meaning as described above, A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group, and the alicyclic hydrocarbon group and The aromatic hydrocarbon group is selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a fluoroalkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group May be substituted with at least one selected. K and l each independently represent an integer of 0 to 3)

It is more preferable that it is a compound containing group represented by following formula (D)

(Wherein Ar, D ^a , D ^b , G ^a , G ^b , E ¹ , E ² , B ¹ and B ² have the same meanings as above, and F ¹ and F ² are each independently 1 to 12 carbon atoms). An alkylene group, wherein the alkylene group may be substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom, and at least one constituting the alkylene group Methylene group may be substituted with -O- or -CO- One of P ¹ and P ² represents a polymerizable group, and the other represents a hydrogen atom or a polymerizable group)

It is especially preferable that it is a compound represented by.

It is preferable that E <^1> and E <^2> are respectively independently -O-, -S-, -CO-O-, or -O-CO-. It is more preferable that E <^1> is -CO-O- and E <^2> is -O-CO-.

As a bivalent alicyclic hydrocarbon group or bivalent aromatic hydrocarbon group represented by A <^1> and A <^2> , group represented by said formula (a-1)-formula (a-8), following formula (g-1)-formula (g Alicyclic hydrocarbon group which may contain the hetero atom represented by -10) is mentioned.

The group represented by said formula (a-1)-formula (a-8) and formula (g-1)-(g-10) is C1-C4, such as a methyl group, an ethyl group, an isopropyl group, and a tert- butyl group. Alkyl group; C1-C4 alkoxy groups, such as a methoxy group and an ethoxy group; C1-C4 fluoroalkyl groups, such as a trifluoromethyl group; Fluoroalkoxy groups having 1 to 4 carbon atoms such as trifluoromethoxy group; Cyano group; Nitro group; It may be substituted by halogen atoms, such as a fluorine atom, a chlorine atom, and a bromine atom.

It is preferable that A <^1> and A <^2> are the same group from the point which is easy to manufacture the compound containing group represented by Formula (C), or the compound represented by Formula (D), and is a ¹ , 4- phenylene group or 1, 4- cyclo It is more preferable that it is a hexylene group, and it is especially preferable that it is a 1, 4- phenylene group.

Type in that they are easy to manufacture of a compound represented by the formula or a compound (D) containing a group represented by (C), it is preferably the same group are B ¹ and B ^2. B ¹ and B ^{2, which} are only bonded to A ¹ or A ² , are each independently —CH ₂ —CH ₂ —, —CO—O—, —O—CO—, —CO—NH—, —NH—CO— , -O-CH _2- , -CH ₂ -O- or a single bond, preferably -CO-O in terms of liquid crystallinity of the compound containing a group represented by the formula (D) and the compound represented by the formula (D) Or -O-CO-. B ¹ and B ² combined with E ¹ or E ² are each independently —O—, —CO—O—, —O—CO—, —O—CO—O—, —CO—NH—, —NH. It is preferable that it is -CO- or a single bond.

It is preferable that k is an integer of 0-2. It is preferable that l is an integer of 0-2. It is preferable that the sum of k and l is an integer of 5 or less, It is more preferable that it is an integer of 4 or less, It is especially preferable to satisfy following formula (2) and (3).

As a compound represented by Formula (D), it is following formula (1).

(Wherein Ar, E ¹ , E ² , B ¹ , B ² , F ¹ , F ² , P ¹ , P ² , k and l have the same meanings as above, and D ¹ and D ² are each independently ^{-CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R 2 -O-CR 3 R 4 - , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ^1- , and R ¹ , R ² , R ³ and R ⁴ have the same meaning as described above, and G ¹ and G ² each independently represents a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, and the aromatic hydrocarbon group and the aromatic heterocyclic group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, and carbon atoms May be substituted with at least one selected from the group consisting of 1 to 4 alkoxy groups, cyano groups, and nitro groups)

The compound represented by is preferable.

D ¹ and D ² are each independently selected from ^{-CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ^{1 R 2 -CO-O-CR} 3 R 4 -, -NR 1 -CR 2 R 3 - , or -CR ² R ³ - is preferable, ^{and, -CR 1 R 2 -CR 1 R} 2 -, -O- CR ¹ R ² - or -CR ¹ R ² -O- is more preferable that the. It is particularly preferable that D ¹ is -O-CR ¹ R ² -and D ² is -CR ¹ R ² -O-. It is preferable that R <^1> , R <^2> , R <^3> and R <^4> are a hydrogen atom or a C1-C4 alkyl group each independently, and it is more preferable that they are a hydrogen atom, a methyl group, or an ethyl group.

As a specific example of G <^1> and G <^2> , group represented by said Formula (a-1)-(a-8) is mentioned, The group represented by Formula (a-1) is preferable, A 1, 4- phenylene group More preferred.

Formula (1-A) and Formula (1-B)

As a specific example of group represented by, the group represented by following formula (R-1)-a formula (R-78) is mentioned. In addition, n in formula (R-1)-a formula (R-78) represents the integer of 2-12.

As a specific example of a compound (1), the compound of the following Table 1 is mentioned.

In the said Table 1, the compound (xvi) is a group represented by the compound represented by the group represented by Ar (120), the group represented by Ar, the group represented by Ar (121), or the group represented by Ar (120) Any of the mixture of the group compound represented by) and the group compound represented by Formula (ar-121) is meant. The compound (xvii) is a compound represented by the group represented by the formula (ar-122) in which the group represented by Ar, a group represented by the group represented by the formula (ar-123) in the group represented by Ar, or a compound represented by the group represented by the formula (ar-122) represented by Ar Any of the mixture of the compound represented by the formula (ar-123) is meant.

Representative examples of compound (i) and compound (vi) described in Table 1 are shown below.

The manufacturing method of a compound (A) is demonstrated below using a compound (1) as an example.

Compound (1) is a known organic synthesis reaction described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, New Experimental Chemistry Lectures (e.g., condensation reaction, esterification reaction, Williamson reaction, Ulman) Reaction, Wittich reaction, sif base reaction, benzylation reaction, sonogashira reaction, suzuki-miyaura reaction, negishi reaction, kumata reaction, hiyama reaction, bukwald-heartwig reaction, Friedel craft reaction, heck reaction, aldol Reaction, etc.) can be manufactured by combining suitably according to the structure.

For example, in the case of compound (1) in which D ¹ is -O-CR ¹ R ² -and D ² is -CR ¹ R ² -O-, the formula (1-1)

(Wherein Ar represents the same meaning as above)

Compound represented by formula and formula (1-2)

(Wherein R ¹ , R ² , G ¹ , E ¹ , A ¹ , B ¹ , F ¹ , P ¹ and k have the same meanings as above, and X ¹ represents a halogen atom)

By reacting the compound represented by the presence of a base, Formula (1-3)

(Wherein Ar, R ¹ , R ² , G ¹ , E ¹ , A ¹ , B ¹ , F ¹ , P ¹ and k represent the same meaning as above)

The compound represented by Formula (1-3) obtained by obtaining the compound represented by

(Wherein R ¹ , R ² , G ² , E ² , A ² , B ² , F ² , P ² and l have the same meaning as above, and X ² represents a halogen atom)

It can manufacture by making the compound shown by reacting in presence of a base.

Moreover, in the case of the compound (1) whose E <^1> is -O-CO- and E <^2> is -CO-O-, for example, Formula (1-5)

(Wherein Ar, D ¹ , D ² , G ¹ and G ² represent the same meaning as above)

Compound represented by formula and formula (1-6)

(Wherein A ¹ , B ¹ , F ¹ , P ¹ and k represent the same meaning as above)

The esterification reaction of the compound represented by is performed in the presence of an esterification agent, and formula (1-7)

(Wherein Ar, D ¹ , D ² , G ¹ , G ² , A ¹ , B ¹ , F ¹ , P ¹ and k represent the same meanings as above)

Compound obtained by obtaining and represented by Formula (1-7) obtained

(Wherein A ² , B ² , F ² , P ² and l have the same meaning as above)

It can manufacture by esterifying the compound represented by the presence of an esterification agent.

Specific examples of the esterifying agent include 1-cyclohexyl-3- (2-morpholinoethyl) carbodiimide meto-p-toluenesulfonate, dicyclohexylcarbodiimide, 1-ethyl-3- (3- Dimethylaminopropyl) carbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, bis (trimethylsilyl) carbodiimide, Carbodiimide compounds such as bisisopropylcarbodiimide, 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazole, 1,1'-oxalyldiimidazole, diphenyl Phosphoryl azide, 1 (4-nitrobenzenesulfonyl) -1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1H-benzotria Zol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N, N ', N'-tetramethyl-O- (N-succinimidyl) uronium tetrafluoro Late, N- (1,2,2,2-tetrachloroethoxycarbonyloxy) succinimide, N-carbobenzoxysuccinimide, O- (6-chlorobenzotriazol-1-yl)- N, N, N ', N'-tetramethyluronium tetrafluoroborate, O- (6-chlorobenzotriazol-1-yl) -N, N, N', N'-tetramethyluronium hexafluoro Lophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate , 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium p-toluenesulfonate, 2-fluoro-1-methylpyridinium p-toluenesulfonate, trichloroacetatepentachloro Phenyl ester etc. are mentioned.

The optical film of this invention is obtained by superposing | polymerizing a compound (A). One type of compound (A) may be polymerized and two or more types of compound (A) may be polymerized. Moreover, you may superpose | polymerize the liquid crystal compound (it abbreviates as a liquid crystal compound hereafter) which has a polymeric group other than a compound (A) and a compound (A).

As the liquid crystal compound, three "molecular structure and liquid crystal" of the liquid crystal handbook (Liquid Crystal Handbook Editing Committee edition, issued March 30, 2000), 3.2 "non-chiral rod-shaped liquid crystal molecules" and 3.3 "chiral" The compound which has a polymeric group is mentioned in the compound of "rod-shaped liquid crystal molecule."

One type of liquid crystal compound may be used and two or more types of liquid crystal compounds may be used.

As a specific example of such a liquid crystal compound, Formula (4)

(In formula, A <^11> represents an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a heterocyclic group, The aromatic hydrocarbon group, an alicyclic hydrocarbon group, and a heterocyclic group are a halogen atom, a C1-C6 alkyl group, C1-C6 May be substituted with at least one selected from the group consisting of an alkoxy group, an N-alkylamino group having 1 to 6 carbon atoms, a nitro group, a cyano group, and a mercapto group, B ¹¹ and B ¹² are each independently -CR ¹⁴ R ¹⁵ -, -C≡C-, -CH = CH-, -CH ₂ -CH _2- , -O-, -S-, -C (= O)-, -C (= O) -O-, -OC (= O)-, -OC (= O) -O-, -C (= S)-, -C (= S) -O-, -OC (= S)-, -CH = N-, -N = CH-, -N = N-, -C (= O) -NR 14 -, -NR 14 -C (= O) -, -OCH 2 -, -OCF 2 -, -NR 14 -, -CH 2 O-, —CF ₂ O—, —CH═CH—C (═O) —O—, —OC (═O) —CH═CH— or a single bond, and R ¹⁴ and R ¹⁵ are each independently hydrogen atom, a fluorine atom or an alkyl group having a carbon number of 1~4, R ¹⁴ and R ¹⁵ are combined to form a group having a carbon number of 4-7 alkylene Is Fig. ¹¹ E represents an alkylene group having 1 to 12 carbon atoms, the alkylene group is optionally substituted by at least one selected from alkyl groups, alkoxy groups and halogen atoms, the group consisting of 1 to 6 carbon atoms having 1 to 6 carbon atoms. P ¹¹ represents a polymerizable group, G represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 13 carbon atoms, an alkoxy group of 1 to 13 carbon atoms, a fluoroalkyl group of 1 to 13 carbon atoms, an N-alkylamino group of 1 to 13 carbon atoms, It is a cyano group or a nitro group, or the polymeric group couple | bonded via a C1-C12 alkylene group, The alkylene group is a group which consists of a C1-C6 alkyl group, a C1-C6 alkoxy group, and a halogen atom. May be substituted with at least one selected. T represents an integer of 1 to 5)

The compound represented by the following (it abbreviates as a compound (4) hereafter) etc. are mentioned.

It is preferable that carbon number of the aromatic hydrocarbon group, alicyclic hydrocarbon group, and heterocyclic group of A <^11> is 3-18, It is more preferable that it is 5-12, It is especially preferable that it is 5 or 6.

Such aromatic hydrocarbon groups, alicyclic hydrocarbon groups and heterocyclic groups include a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an N-alkylamino group having 1 to 6 carbon atoms, a nitro group, a cyano group and a mercap It may be substituted by at least one selected from the group consisting of earthenware, and the same as those mentioned above as a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a C1-C6 N-alkylamino group are mentioned. Can be.

Examples of the alkyl group having 1 to 4 carbon atoms represented by R ¹⁴ and R ¹⁵ include the same ones as described above. Examples of the alkylene group having 4 to 7 carbon atoms formed by bonding of R ¹⁴ and R ¹⁵ include tetramethylene group, pentamethylene group, hexamethylene group and the like.

Alkylene group having 1 to 12 carbon atoms represented by E ^11, there may be mentioned the same as described above. The alkylene group may be substituted with at least one selected from the group consisting of an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, and a halogen atom, and an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, and a halogen As an atom, the same thing as mentioned above is mentioned.

As a polymeric group in Formula (4), what is necessary is just a group which can superpose | polymerize with a compound (A), A vinyl group, a vinyloxy group, p-stilbene group, acryloyl group, acryloyloxy group, a methacroyl group, Methacroyloxy group, carboxyl group, acetyl group, hydroxyl group, carbamoyl group, amino group, C1-C4 alkylamino group, epoxy group, oxetanyl group, formyl group, -N = C = O or -N = C = S and the like Can be mentioned. Especially, since it is suitable for photopolymerization, a radically polymerizable group or a cation polymerizable group is preferable, and since it is easy to handle and manufacture of a liquid crystal compound, an acryloyloxy group, a methacroyloxy group, or a vinyloxy group is also preferable. desirable.

Examples of the halogen atom represented by G include those mentioned above. Examples of the alkyl group having 1 to 13 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group and decyl group. Examples of the alkoxy group having 1 to 13 carbon atoms include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group and hexyloxy group, Decyloxy group etc. are mentioned. Examples of the fluoroalkyl group having 1 to 13 carbon atoms include fluoromethyl group, trifluoromethyl group, fluoroethyl group, pentafluoroethyl group, heptafluoropropyl group, and nonafluorobutyl group. Examples of the N-alkylamino group having 1 to 13 carbon atoms include N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group and N-sec-butylamino group , N-tert-butylamino group, N-pentylamino group, N-hexylamino group and the like.

Examples of the alkylene group having 1 to 12 carbon atoms when G represents a polymerizable group which is bonded via an alkylene group having 1 to 12 carbon atoms include the same as those described above. Such alkylene groups include those having 1 to 1 carbon atoms. It may be substituted by at least one selected from the group consisting of an alkyl group of 6, an alkoxy group having 1 to 6 carbon atoms and a halogen atom.

As compound (4), the compound represented by Formula (4-1) and Formula (4-2) is mentioned.

^{(Wherein, P 11, E 11, B} 11, A 11, B 12 , and t have the same meanings as defined above, E ¹² is an alkylene group having 1 to 12 carbon atoms, the group alkylene, having a carbon number of 1 to It may be substituted with at least one selected from the group consisting of an alkyl group of 6, an alkoxy group having 1 to 6 carbon atoms and a halogen atom, P ¹² represents a polymerizable group, and F ¹¹ is a hydrogen atom, a halogen atom, or a C 1 -13 Alkyl group, alkoxy group having 1 to 13 carbon atoms, fluoroalkyl group having 1 to 13 carbon atoms, N-alkylamino group having 1 to 13 carbon atoms, cyano group or nitro group)

As a compound represented by Formula (4-1) and Formula (4-2), the compound represented by following formula (I), formula (II), formula (III), formula (IV), or formula (V) is mentioned. have.

(In formula, A <^12> -A <^15> represents an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a heterocyclic group independently, The aromatic hydrocarbon group, an alicyclic hydrocarbon group, and a heterocyclic group are a halogen atom, a C1-C6 alkyl group, . 1 to 6 carbon atoms is optionally an alkoxy group, is substituted with at least one selected from the group consisting of N- alkyl amino group, a nitro group, a cyano group and a mercapto group of a carbon number of 1 to 6, B ¹³ ~B ¹⁶ are each independently - CR ¹⁴ R ^15- , -C≡C-, -CH = CH-, -CH ₂ -CH _2- , -O-, -S-, -C (= O)-, -C (= O) -O -, -OC (= O)-, -OC (= O) -O-, -C (= S)-, -C (= S) -O-, -OC (= S)-, -CH = N -, -N = CH-, -N = N-, -C (= O) -NR 14 -, -NR 14 -C (= O) -, -OCH 2 -, -OCF 2 -, -NR 14 - , -CH ₂ O-, -CF ₂ O-, -CH = CH-C (= O) -O-, -OC (= O) -CH = CH- or a single bond, R ¹⁴ and R ¹⁵ are Same meaning as above)

Examples of the compound represented by the formula (4-1), formula (4-2), formula (I), formula (II), formula (III), formula (IV) and formula (V) include P ¹¹ and E ^11. P ¹¹ , E ¹¹ , P ¹² and E ¹² are preferably selected such that the bond between and the bond between P ¹² and E ¹² is an ether bond or an ester bond.

Specific examples of the compound (4) include the following formulas (I-1) to (I-5), formulas (II-1) to (II-6), and formulas (III-1) to (III-). 19), compounds represented by formulas (IV-1) to (IV-14), and formulas (V-1) to (V-5). In the following formula, k represents the integer of 1-11. The following liquid crystal compound is easy to synthesize | combines, and is preferable at the point of acquisition such as being commercially available.

When superposing | polymerizing a compound (A) and a liquid crystal compound, the usage-amount of a liquid crystal compound is 90 weight part or less normally when the sum total of a compound (A) and a liquid crystal compound is 100 weight part.

The polymerization reaction is usually carried out in the presence of a polymerization initiator.

As a polymerization initiator, a photoinitiator is preferable. As a photoinitiator, a benzoin compound, a benzophenone compound, a benzyl ketal compound, the (alpha)-hydroxy ketone compound, the (alpha)-amino ketone compound, an iodonium salt, a sulfonium salt, etc. are mentioned. As a specific example of such a photoinitiator, Irgacure 907 (IRGACURE907; Chiba Japan Corporation), Irgacure 184 (IRGACURE184; Chiba Japan Corporation), Irgacure 651 (IRGACURE651; Chiba Japan Corporation) , Irgacure 819 (IRGACURE819; manufactured by Chiba Japan Co., Ltd.), Irgacure 250 (IRGACURE250; manufactured by Chiba Japan Co., Ltd.), Irgacure 369 (IRGACURE369; manufactured by Chiba Japan Co., Ltd.), Sakekuol BZ (SEIKUOL BZ; Seiko Chemical Co., Ltd.), Seikool Z (SEIKUOL Z; Seiko Chemical Co., Ltd.), Seikool BEE (Seiko Chemical Co., Ltd.), Kayakure BP100 (KAYACURE BP100; Nippon Gunpowder Co., Ltd.), Kayakure UVI-6992 (KAYACURE UVI-6992; manufactured by Dow Corporation), Adeka OPTOMER SP-152 (ADEKA OPTOMER SP-152; manufactured by ADEKA Corporation), Adeka OPTOMER SP-170 (ADEKA OPTOMER SP-170; manufactured by ADEKA Corporation), etc. Liftable .

The usage-amount of a polymerization initiator is 0.1 weight part-30 weight part normally with respect to a total of 100 weight part of a liquid crystal compound and a compound (A), Preferably they are 0.5 weight part-10 weight part. If it is in the said range, a compound (A) can be polymerized without disturbing the orientation of a liquid crystal compound.

The wavelength dispersion characteristic of the optical film of this invention can be arbitrarily determined by adjusting content of the structural unit derived from the compound (A) in an optical film. When content of the structural unit derived from the compound (A) in an optical film becomes large, the optical film obtained will show a flat wavelength dispersion characteristic and also reverse wavelength dispersion characteristic.

In order to obtain the optical film which shows the wavelength dispersion characteristic calculated | required, what is necessary is just as follows, for example. First, about 2-5 types of compositions containing the liquid crystal compound and compound (A) from which content of the structural unit derived from a compound (A) differ are prepared, and the optical film of the same film thickness is manufactured using each composition. . The phase difference value of the obtained optical film is measured, and the correlation between the content of the structural unit derived from a compound (A) and the phase difference value of an optical film is calculated | required. Based on the obtained correlation, content of the structural unit derived from the compound (A) required for the optical film in the said film thickness to show a desired phase difference value is calculated | required, and a liquid crystal compound and a compound (A) so that it may become said content. A composition containing is prepared to polymerize.

The manufacturing method of the optical film of this invention is demonstrated below.

First, a compound (A), the said liquid crystal compound, and the said polymerization initiator are mixed, and the composition containing a compound (A) is prepared. Since the film can be easily formed when forming the obtained composition, when preparing the composition, it is preferable to prepare the solution containing a compound (A) using an organic solvent. Moreover, you may use additives, such as a polymerization inhibitor, a photosensitizer, and a leveling agent, as needed.

As a polymerization inhibitor, the catechol compound which has substituents, such as a hydroquinone compound which has substituents, such as a hydroquinone or an alkyl ether, alkyl ethers, such as butyl catechol, a pyrogallol compound, 2,2,6,6- tetramethyl- Radical supplements such as 1-piperidinyloxy radicals, thiophenol compounds, β-naphthylamine compounds, β-naphthol compounds and the like.

By using a polymerization inhibitor, control of a polymerization reaction becomes easy and the stability of the optical film obtained can be improved. The usage-amount of a polymerization inhibitor is 0.1 weight part-30 weight part normally with respect to a total of 100 weight part of a liquid crystal compound and a compound (A), Preferably they are 0.5 weight part-10 weight part. If it is in the said range, a compound (A) can be polymerized without disturbing the orientation of a liquid crystal compound.

Examples of the photosensitizer include xanthone compounds such as xanthone and thioxanthone, anthracene compounds having substituents such as anthracene or alkyl ether, phenothiazine, rubrene and the like.

By using a photosensitizer, a polymerization reaction can be performed with high sensitivity. The usage-amount of a photosensitizer is 0.1 weight part-30 weight part normally with respect to a total of 100 weight part of a liquid crystal compound and a compound (A), Preferably they are 0.5 weight part-10 weight part. If it is in the said range, a compound (A) can be polymerized without disturbing the orientation of a liquid crystal compound.

As a leveling agent, additives for radiation-hardening paints (BIC Chemie Japan make: BYK-352, BYK-353, BYK-361N), paint additives (Dore Dow Corning Corporation make: SH28PA, DC11PA, ST80PA), paint additives Tsu Chemical Co., Ltd. make: KP321, KP323, X22-161A, KF6001), and a fluorine additive (Deinippon Ink Chemical Co., Ltd. make: F-445, F-470, F-479), etc. are mentioned.

By using a leveling agent, the optical film can be smoothed. Moreover, the fluidity | liquidity of the composition containing a compound (A) can be controlled in the manufacturing process of an optical film, or the crosslinking density of the optical film obtained can also be adjusted. The usage-amount of a leveling agent is 0.1 weight part-30 weight part normally with respect to a total of 100 weight part of a liquid crystal compound and a compound (A), Preferably they are 0.5 weight part-10 weight part. If it is in the said range, a compound (A) can be polymerized without disturbing the orientation of a liquid crystal compound.

The organic solvent is an organic solvent which can dissolve a compound (A), a liquid crystal compound, or the like, and may be a solvent which is inert to the polymerization reaction, and specifically, methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, and methyl cell. Alcohol solvents such as low solve and butyl cellosolve; Ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate, and ethyl lactate; Ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, and methyl isobutyl ketone; Aliphatic hydrocarbon solvents such as pentane, hexane and heptane; Aromatic hydrocarbon solvents such as toluene, xylene and chlorobenzene; Nitrile solvents such as acetonitrile; Ether solvents such as propylene glycol monomethyl ether, tetrahydrofuran and dimethoxyethane; Halogenated hydrocarbon solvents such as chloroform; Phenol; Etc. can be mentioned. These organic solvents may be used independently and may be used in combination of 2 or more type. In particular, the composition containing the compound (A) and the liquid crystal compound is excellent in compatibility and can be dissolved in an alcohol solvent, an ester solvent, a ketone solvent, a non-chlorinated aliphatic hydrocarbon solvent and a non-chlorinated aromatic hydrocarbon solvent. The film can be formed without using a solvent.

The viscosity of the solution containing the compound (A) is usually adjusted to 10 Pa · s or less, preferably 0.1 to 7 Pa · s, in consideration of the applicability of the composition.

Moreover, the density | concentration of solid content in the solution containing a compound (A) is 5-50 weight% normally. When the concentration of the solid content is 5% or more, the optical film does not become too thin and tends to give a birefringence necessary for optical compensation of the liquid crystal panel. Moreover, when the density | concentration of solid content is 50% or less, since the viscosity of a composition does not become small too much and there exists a tendency for a nonuniformity to arise to the film thickness of an optical film, it is preferable.

An optical film can be obtained by apply | coating the solution containing such a compound (A) on a support base material, and drying and superposing | polymerizing.

The unpolymerized film is obtained when apply | coating the solution containing compound (A) on a support base material, and drying. When an unpolymerized film shows liquid crystal phases, such as a nematic phase, the optical film obtained shows birefringence by monodomain orientation. Since an unpolymerized film is orientated normally at about 0-120 degreeC, Preferably it is 25-80 degreeC, the support base material which heat resistance is not necessarily sufficient can be used. Moreover, since an unpolymerized film does not crystallize even if it cools to about 10-30 degreeC after orientation, handling is easy.

The film thickness can be prepared by suitably adjusting the density | concentration of the compound (A) in the solution containing a compound (A), and the application amount of this solution on a support base material. In the case of the solution where the quantity of a compound (A) is constant, the phase difference value (retardation value, Re ((lambda))) of the optical film obtained is Formula (7)

Re (λ) = d × Δn (λ) (7)

(Wherein Re (λ) represents a phase difference value at a wavelength λnm, d represents a film thickness, and Δn (λ) represents a birefringence at a wavelength λnm)

In order to obtain the desired Re (λ), the film thickness d may be adjusted.

As a coating method to a support base material, an extrusion coating method, the direct gravure coating method, the reverse gravure coating method, the CAP coating method, the die coating method, etc. are mentioned. Moreover, the method of apply | coating using coaters, such as a dip coater, a bar coater, and a spin coater, is also mentioned.

Glass, a plastic sheet, a plastic film, a light transmissive film, etc. are mentioned as a support base material. As a translucent film, Polyolefin films, such as polyethylene, a polypropylene, and norbornene-type polymer; Polyvinyl alcohol film; Polyethylene terephthalate film; Polymethacrylic acid ester film; Polyacrylic acid ester film: cellulose ester film; Polyethylene naphthalate film; Polycarbonate film; Polysulfone film; Polyether sulfone film; Polyether ketone film; Polyphenylene sulfide film; Polyphenylene oxide film; Etc. can be mentioned.

Even in the process where the intensity | strength of the optical film, such as an attachment process of an optical film, a conveyance process, and a storage process is calculated | required, using a support base material, it can handle easily, without rupture of an optical film.

After forming an orientation film on a support base material, it is preferable to apply | coat the solution containing a compound (A) on this orientation film. It is preferable that an oriented film has solvent tolerance which does not melt | dissolve in the solution at the time of application | coating of the solution containing a compound (A). Moreover, it is preferable that an orientation film has heat resistance in heat processing for removal of a solvent and orientation of a liquid crystal molecule. Moreover, it is preferable that it is an oriented film in which peeling etc. by a friction etc. do not arise at the time of rubbing. As such an oriented film, what consists of a polymer or a composition containing a polymer is preferable.

The polymer may be a polyamide or gelatin compound having an amide bond in a molecule, a polyimide having an imide bond in a molecule, and a polyamic acid, polyvinyl alcohol, alkyl-modified polyvinyl alcohol, polyacrylamide, or polyoxa which is a hydrolyzate thereof. And polymers such as sol, polyethyleneimine, polystyrene, polyvinylpyrrolidone, polyacrylic acid or polyacrylic acid ester. These polymers may be used independently, or may mix and use two or more types. Moreover, the copolymer of these polymers may be sufficient. These polymers can be easily obtained by polycondensation such as dehydration polycondensation and deamine polycondensation, radical polymerization, anion polymerization, chain polymerization such as cationic polymerization, coordination polymerization, ring-opening polymerization and the like.

These polymers are normally used as a solution which melt | dissolved in the solvent. Solvents are not limited. Specifically, water; Alcohol solvents such as methanol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, methyl cellosolve and butyl cellosolve; Ester solvents such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, γ-butyrolactone, propylene glycol methyl ether acetate, and ethyl lactate; Ketone solvents such as acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone, and methyl isobutyl ketone; Aliphatic hydrocarbon solvents such as pentane, hexane and heptane; Nitrile solvents, such as aromatic hydrocarbon solvents, such as toluene, xylene, and chlorobenzene, and acetonitrile; Ether solvents such as propylene glycol monomethyl ether, tetrahydrofuran and dimethoxyethane; Halogenated hydrocarbon solvents such as chloroform; Etc. can be mentioned. These organic solvents may be used independently or may be used in combination of 2 or more type.

You may form an oriented film using the commercially available aligning film material as it is. Examples of commercially available alignment film materials include San Eva (registered trademark; manufactured by Nissan Chemical Industries, Ltd.), Optomer (registered trademark; manufactured by JSR Corporation), and the like.

By using such an alignment film, since it is not necessary to control the refractive index by extending | stretching, in-plane deviation of birefringence becomes small and it can provide the large optical film which can respond to the enlargement of a flat panel display device (FPD) on a support base material.

As a method of forming an oriented film on a support base material, the method of apply | coating as a solution the compound used as the oriented film material or material of an oriented film marketed on a support base material, and apply | coats an annealing after that is mentioned.

The thickness of the alignment film is usually 10 nm to 10000 nm, preferably 10 nm to 1000 nm. When it is in the said range, a compound (A) etc. can be orientated at a desired angle on the alignment film. As needed, you may rub the orientation film, and you may irradiate polarization UV to an orientation film.

As a method of rubbing an alignment film, the method of making the rubbing roll wound around the rotating rubbing cloth contact with the alignment film carried on the stage is conveyed.

The method of laminating | stacking an unpolymerized film on the oriented film laminated | stacked on such a support base material can reduce a production cost compared with the method of manufacturing a liquid crystal cell, and inject | pouring a liquid crystal compound into this liquid crystal cell, and also a roll film The production of film in is also possible.

Although removal of a solvent may be performed in parallel with a polymerization reaction, it is preferable from a viewpoint of film formation to remove most solvents before performing a polymerization reaction.

As a removal method of a solvent, methods, such as natural drying, ventilation drying, and vacuum drying, are mentioned. It is preferable that it is 10-120 degreeC, and, as for the temperature at the time of heating and removing a solvent, it is more preferable that it is 25-80 degreeC. It is preferable that they are 10 second-60 minutes, and, as for a heat time, it is more preferable that they are 30 seconds-30 minutes. If heating temperature and a heat time exist in the said range, the support base material in which heat resistance is not necessarily enough as a support base material can be used.

By superposing | polymerizing and hardening the obtained unpolymerized film, the film by which the orientation of the compound (A) was fixed, ie, a polymerized film, is obtained. An optical film with a small refractive index change in the planar direction of the film and a large refractive index change in the normal direction of the film is obtained.

What is necessary is just to determine suitably the method of superposing | polymerizing an unpolymerized film according to the kind of liquid crystal compound and a compound (A). The photopolymerization method is used if the polymerizable group in the compound (A) and the liquid crystal compound is a photopolymerizable group, and the thermal polymerization method is used if the polymerizable group is a thermopolymerizable group. According to the photopolymerization method, a compound (A) having a photopolymerizable polymerizable group and a liquid crystal can be polymerized at a low temperature, and the selection of heat resistance of the supporting substrate becomes wider and industrially easy to manufacture. Preference is given to using compounds. Moreover, the photopolymerization method is preferable also from a film formation viewpoint. The photopolymerization reaction is carried out by irradiating the unpolymerized film with visible light, ultraviolet light or laser light. Ultraviolet light is particularly preferable in terms of handling. You may perform light irradiation at the temperature at which a compound (A) takes a liquid crystal phase. At this time, a polymeric film can also be patterned by masking etc.

The optical film of this invention has favorable adhesiveness of a support base material and an optical film, and adhesiveness of an oriented film and an optical film, and its manufacture is easy.

The optical film of this invention is a thin film compared with the stretched film which gives retardation by extending a polymer.

By peeling a support base material, the film in which the oriented film and the optical film were laminated is obtained. Moreover, an optical film can be obtained by peeling an orientation film.

The optical film obtained in this way is excellent in transparency, and is used as various display films. Although the thickness of an optical film differs with the phase difference value of an optical film as mentioned above, it is preferable that it is 0.1-10 micrometers, and it is more preferable that it is 0.5-3 micrometers in the point which makes photoelasticity small.

The phase difference value of the optical film which shows birefringence is about 50-500 nm normally, Preferably it is 100-300 nm.

The optical film which is such a thin film and which can perform uniform polarization conversion in a wider wavelength range can be used as an optical compensation film in FPDs, such as all liquid crystal panels and organic EL.

The optical film of the present invention can be used as a wideband [lambda] / 4 plate or [lambda] / 2 plate. When using as a broadband (lambda) / 4 plate or (lambda) / 2 plate, what is necessary is just to select suitably content of the structural unit derived from the compound (A) in an optical film, and the film thickness of an optical film. When using as a (lambda) / 4 plate, what is necessary is just to adjust a film thickness so that Re (550) of the optical film obtained may be 113-163 nm normally, Preferably it is 135-140 nm, Especially preferably, it is about 137.5 nm. When using as a (lambda) / 2 plate, what is necessary is just to adjust a film thickness so that Re (550) of the optical film obtained may be 250-300 nm normally, Preferably it is 273-277 nm, Especially preferably, it is about 275 nm.

The optical film of the present invention can also be used as an optical film for VA (Vertical Alingment) mode. When using as an optical film for VA modes, what is necessary is just to select content of the structural unit derived from the compound (A) in an optical film suitably. What is necessary is just to adjust film thickness so that Re (550) of the optical film obtained may become 40-100 nm, More preferably, it is about 60-80 nm.

The optical film of this invention can also be used for antireflection films, such as an anti-reflection (AR) film, a polarizing film, retardation film, an elliptical polarizing film, a viewing angle expansion film, or the optical compensation film for viewing angle compensation of a transmissive liquid crystal display.

Although the optical film of this invention shows the outstanding optical characteristic also in one sheet | seat, you may laminate and use multiple sheets. Moreover, you may use in combination with another film. As a specific example combined with another film, the elliptical polarizing plate which adhered the optical film of this invention to the polarizing film, the broadband circular polarizing plate etc. which attached the optical film of this invention as a broadband (lambda) / 4 plate further to the elliptically polarizing plate are mentioned. Can be.

Since the optical film of this invention can be formed by apply | coating on a support base material or an oriented film, and superposing | polymerizing, as shown in FIG. The optical film of can be formed.

1 is a schematic view showing a color filter 1 according to the present invention.

As for the color filter 1, the color filter layer 4, the oriented film 3, and the optical film 2 of this invention are laminated | stacked in this order.

An example of the manufacturing method of such a color filter 1 is described below. First, the alignment polymer is laminated on the color filter layer 4, and a rubbing treatment is performed to form the alignment film 3. The oriented polymer may be laminated using the inkjet method.

Next, on the obtained orientation film 3, the solution containing the compound (A) whose content of the compound (A) was adjusted so that the optical film obtained may have desired wavelength-dispersion characteristic is prepared so that it may become thickness which becomes a desired phase difference value. The solution is applied to form the optical film 2.

By using such a color filter 1, it becomes possible to manufacture a thinner liquid crystal display device. As an example, the schematic diagram which shows the liquid crystal display device 5 which concerns on this invention was shown in FIG.

In the liquid crystal display device 5 shown in FIG. 2, the board | substrate 7 which opposes backlights, such as a glass substrate, is fixed on the polarizing plate 6 via an adhesive agent. The optical film 2 'is formed on the color filter layer 4' manufactured on the board | substrate 7 through the alignment film 3 '. In addition, the counter electrode 8 is formed on the optical film 2 ', and the liquid crystal phase 9 is formed on the counter electrode 8. As for the backlight side, the board | substrate 11, such as a glass substrate, is being fixed to the polarizing plate 10 via an adhesive agent. In addition, a thin film transistor (TFT) and an insulating layer 12 are formed on the substrate 11 for active driving of the liquid crystal layer, and the transparent electrode 13 made of Ag, Al, or ITO (Indium Tin Oxide) is formed on the TFT. And / or a reflective electrode 13 'is formed. The structure of the liquid crystal display device 5 shown in FIG. 2 is a structure with few sheets of an optical film compared with the conventional liquid crystal display device, and manufacture of a thinner liquid crystal display device becomes possible.

An example of the manufacturing method of the liquid crystal display device 5 in which the color filter 1 'was formed in the liquid crystal layer side of one board | substrate is described below. On the substrate on the backlight side, a semiconductor thin film is formed on borosilicate glass by depositing and patterning a gate electrode made of Mo, MoW, or the like, and amorphous silicon, and annealing the amorphous silicon with an excimer laser. P, B and the like can be doped in both regions of the gate electrode to form n-channel and p-channel TFTs. Further, the backlight side substrate is obtained by forming the insulating layer 12 made of SiO ₂ . Further, by sputtering ITO on the backlight side substrate 11, the transparent electrode 13 for a full transmissive display device can be laminated on the backlight side substrate. Similarly, by using Ag, Al, or the like instead of ITO, the reflective electrode 13 'for all reflective display devices is obtained. Moreover, the backlight side electrode for semi-transmissive liquid crystal display devices is also obtained by combining suitably a reflection electrode and a transparent electrode.

On the other hand, the color filter layer 4 'is formed in the board | substrate 7 which opposes. By using together the color filter of R, G, and B, the full color liquid crystal display device is also obtained. Next, the alignment film 3 'is formed by apply | coating and rubbing an oriented polymer on the color filter layer 4'. Polymerization and the optical film 2 'are formed by ultraviolet irradiation, apply | coating the composition containing the compound (A) which concerns on this invention on this alignment film 3', and heating to the temperature range which takes a liquid crystal phase. After formation of the optical film, the counter electrode 8 can be formed by sputtering ITO. Further, the liquid crystal display device 5 can be manufactured by forming an alignment film on the counter electrode, forming the liquid crystal phase 9, and finally assembling together with the backlight side substrate.

Moreover, the optical film of this invention can be used also for the retardation plate of a reflective liquid crystal display and an organic electroluminescent display, and the FPD provided with the retardation plate and the said optical film. The said FPD is not specifically limited, For example, a liquid crystal display device (LCD) and organic EL are mentioned.

Next, the FPD provided with the polarizing plate of this invention and this polarizing plate is demonstrated.

The polarizing plate of this invention contains the optical film and polarizing film of this invention, and is usually obtained by laminating | stacking the optical film and polarizing film of this invention. Specifically, it is obtained by adhering the optical film of the present invention directly to one or both surfaces of a film having a polarizing function, that is, a polarizing film, or using an adhesive. In this specification, "adhesive" means both an adhesive agent and an adhesive. Hereinafter, the polarizing plate of this invention is demonstrated using FIGS.

3 (a) to 3 (e) are schematic diagrams showing the polarizing plate 1 of the present invention.

As for the polarizing plate 30a shown to FIG. 3 (a), the laminated body 14 and the polarizing film 15 are directly affixed, and the laminated body 14 is the support base material 16, the oriented film 17, and the optics. Film 18. The polarizing plate 30a is laminated | stacked in the order of the support base material 16, the orientation film 17, the optical film 18, and the polarizing film 15. As shown in FIG.

The laminated body 14 and the polarizing film 15 are affixed through the adhesive bond layer 19 in the polarizing plate 30b shown to FIG. 3 (b).

As for the polarizing plate 30c shown to FIG. 3 (c), the laminated body 14 and the laminated body 14 'are directly attached, and the laminated body 14' and the polarizing film 15 are directly attached.

In the polarizing plate 30d shown in FIG. 3 (d), the laminate 14 and the laminate 14 ′ are attached to each other via the adhesive layer 19, and the polarizing film 15 is stacked on the laminate 14 ′. ) Is directly attached.

The polarizing plate 30e shown in FIG. 3E attaches the laminate 14 and the laminate 14 'via the adhesive layer 19, and further, the laminate 14' and the polarizing film 15. This structure has the structure which affixed this through the adhesive bond layer 19 '.

Instead of the laminated body 14, you may use the optical film 18 which peeled the support base material 16 and the orientation film 17 from the laminated body 14, and peels off the support base material 16 from the laminated body 14. You may use the film which consists of the oriented film 17 and the optical film 18 as long. Instead of the laminated body 14 ', you may use the optical film 18' which peeled the support base material 16 'and the orientation film 17' from the laminated body 14 ', and supports it from the laminated body 14'. You may use the film which consists of the orientation film 17 'and the optical film 18' which peeled the base material 16 '.

The polarizing plate of this invention may laminate | stack a plurality of laminated bodies, and all of these some laminated bodies may be the same, and may differ.

The polarizing film 15 may be a film having a polarizing function, specifically, a film drawn by adsorbing an iodine or a dichroic dye to a polyvinyl alcohol-based film and a polyvinyl alcohol-based film drawn to adsorb iodine or a dichroic dye. The film etc. which were made are mentioned.

It is preferable that the adhesive agents used for the adhesive bond layer 19 and the adhesive bond layer 19 'are adhesives with high transparency and excellent heat resistance. As such an adhesive, an acrylic adhesive, an epoxy adhesive, a urethane adhesive, etc. are mentioned.

The flat panel display device of this invention is equipped with the optical film of this invention, Specifically, the liquid crystal display device provided with the attachment with the polarizing plate of this invention and a liquid crystal panel, The polarizing plate of this invention, and a light emitting layer adhere The organic electroluminescence display provided with the organic electroluminescent panel mentioned is mentioned.

As an embodiment of the flat panel display device of the present invention, a liquid crystal display device and an organic EL display device will be described below as an example.

4 is a schematic view showing the attachment 21 of the liquid crystal panel 20 and the polarizing plate 30 of the liquid crystal display device of the present invention. The adhesive 21 is obtained by attaching the polarizing plate 30 and the liquid crystal panel 20 of the present invention through the adhesive layer 22. By applying a voltage to the liquid crystal panel 20 using an electrode (not shown), the liquid crystal molecules can be driven to perform monochrome display.

5 is a schematic view showing the organic EL panel 23 of the organic EL display device of the present invention. The organic EL panel 23 is made by attaching the polarizing film 30 and the light emitting layer 24 of the present invention through the adhesive layer 25.

In the organic EL panel, the polarizing film 30 functions as a broadband circular polarizing plate. The light emitting layer 24 is at least one layer made of a conductive organic compound.

Example

Hereinafter, although an Example demonstrates this invention still in detail, this invention is not limited to these Examples.

Example 1

(1) According to the method of Unexamined-Japanese-Patent No. 2004-262884, hydroquinone and dihydropyran were made to react and the compound represented by said Formula (VII-1-1) was obtained.

(2) 100.1 g of the compound represented by the obtained Formula (VII-1-1), 97.1 g of potassium carbonate, 64 g of 6-bromohexanol and 200 ml of N, N-dimethylacetamide were mixed. The obtained mixture was reacted at 90 ° C under nitrogen atmosphere, and then reacted at 100 ° C. The reaction mixture obtained was left to cool to room temperature. Methyl isobutyl ketone was added to the reaction mixture, the mixture was stirred, and the solution was separated into an organic layer and an aqueous layer. The obtained organic layer was washed with pure water, aqueous sodium hydroxide solution and further pure water. Anhydrous sodium sulfate was added to the organic layer after washing | cleaning, and it dehydrated. After sodium sulfate was removed by filtration, the filtrate obtained was concentrated under reduced pressure. Methanol was added to the obtained residue, and the precipitate which precipitated was extracted by filtration. The extracted precipitate was dried in vacuo to give 126 g of the compound represented by the formula (VII-1-2). Yield 91% (based on 6-chlorohexanol).

(3) 126 g of the compound represented by the obtained formula (VII-1-2), 1.40 g of 3,5-di-tert-butyl-4-hydroxytoluene, 116.7 g of N, N-dimethylaniline and 1,3-dimethyl- 1.00 g of 2-imidazolidinone was dissolved in chloroform. The obtained solution was water-cooled, 58.1 g of acryloyl chloride was dripped under nitrogen atmosphere, and it reacted at room temperature. Pure water was added and stirred to the obtained reaction mixture. The organic layer and the aqueous layer were separated, and the obtained organic layer was washed with aqueous hydrochloric acid, saturated aqueous sodium carbonate solution and further pure water. Anhydrous sodium sulfate was added to the organic layer after washing | cleaning, and it dried. After sodium sulfate was removed by filtration, 3,5-di-tert-butyl-4-hydroxytoluene was added to the obtained filtrate, and it concentrated under reduced pressure, and obtained the compound represented by said formula (VII-1-3).

(4) After adding 200 ml of tetrahydrofuran to the compound represented by obtained formula (VII-1-3), 200 ml of tetrahydrofuran was further added. After adding hydrochloric acid to the obtained solution, it was made to react at 60 degreeC by nitrogen atmosphere. Saturated brine was added and stirred to the obtained reaction mixture, and it separated into an organic layer and an aqueous layer. Anhydrous sodium sulfate was added to the obtained organic layer, and it dehydrated. After sodium sulfate was removed by filtration, the filtrate obtained was concentrated under reduced pressure. Hexane was added to the obtained concentrate and stirred under ice cooling. The precipitated solid was extracted by filtration. The extracted solid was vacuum-dried to obtain 90 g of the compound represented by the formula (VII-1-4). Yield: 79% (based on the compound represented by the formula (VII-1-1)).

(5) 5.0 g of 1,4-dihydroxyanthraquinone, 8.6 g of potassium carbonate, 10.1 g of 4- (bromomethyl) benzoate and 60 g of N, N'-dimethylacetamide were added to the vessel. The obtained mixture was stirred at 60 ° C and reacted. The obtained reaction mixture was poured into ice water, and the precipitated solid was extracted by filtration. The extracted solid was wash | cleaned with pure water, and the powder 9.5g containing the compound represented by said formula (VII-1-6) was obtained. After pulverizing the obtained powder, it wash | cleaned with methanol and obtained 7.8 g of the powder of the compound represented by the formula (VII-1-6) whose purity is 96% or more. Yield 66% (based on 1,4-dihydroxyanthraquinone).

To the container, 5.0 g of the compound represented by the obtained formula (VII-1-6), 12 g of ethanol, 40 g of tetrahydrofuran, and 7 g of saturated potassium hydroxide aqueous solution were added. The obtained mixture was stirred at 60 ° C under a nitrogen atmosphere and allowed to react. The obtained reaction mixture was left to cool and then poured into ice water. Hydrochloric acid was added dropwise to the obtained solution until the pH became 2, and the resulting precipitate was separated by filtration. The separated precipitate was washed with water and hexane to obtain 4.7 g of a powder containing the compound represented by the formula (VII-1-7). After pulverizing the obtained powder, it washed with tetrahydrofuran and obtained 3.2 g of the powder of the compound represented by Formula (VII-1-7) whose purity is 96% or more. Yield: 68% (based on the compound represented by the formula (VII-1-6)).

(7) In the container, 2.00 g of the compound represented by the obtained Formula (VII-1-7), 2.3 g of the compound represented by the formula (VII-1-4) obtained in the above (4), and 1.74 g of ethyldimethylaminopropylcarbodiimide hydrochloride. g, 0.18 g of 4-dimethylaminopyridine and 55 g of chloroform were added. To the obtained mixture, 10 g of N, N-dimethylacetamide was added and stirred. After 10 mg of 3,5-di-tert-butyl-4-hydroxytoluene was added to the obtained mixture, 30 g of N, N-dimethylacetamide was further added, and the obtained mixture was reacted for 48 hours. The resulting precipitate was separated by filtration. The powder obtained by vacuum drying the separated precipitate was extracted with ethyl acetate. The obtained organic layer was concentrated to an amount of 1/3 with an evaporator, and then methanol was added. The precipitated solid was washed with methanol to obtain 3.0 g of the compound represented by the formula (VII-1-8). Yield: 74% (based on the compound represented by the formula (VII-1-7)).

Example 2

(1) Example 1 In (2), it carried out similarly to Example 1 (1)-(4) except having used 10-bromodecanol instead of 6-bromohexanol, and the said Formula ( (1-1-5) was obtained. Yield: 60% (based on the compound represented by the formula (VII-1-1)).

(2) In Example 1 (7), it carries out except using the compound represented by the formula (VII-1-5) obtained by said (1) instead of the compound represented by Formula (VII-1-4). By carrying out similarly to Example 1 (5)-(7), the compound represented by said Formula (VII-1-9) can be obtained.

Example 3

(1) J. Chem. Soc., Perkin Trans. In accordance with the method described in 1, 205-210 (2000), a compound represented by the formula (VII-1-1) was obtained from 2,5-dimethoxyaniline.

(2) 10.8 g of the compound represented by the obtained Formula (VII-1-1) and 54.0 g of pyridinium chloride were placed in a container. The resulting mixture was stirred at 220 ° C. After cooling the obtained mixture, 216 g of water was added. The precipitate precipitate was separated by filtration. The separated precipitate was washed with water and hexane to obtain 8.7 g of a solid containing the compound represented by the formula (VII-1-2). Yield: 89% (based on the compound represented by the formula (VII-1-1)).

(3) 7.0 g of the compound represented by the obtained formula (VII-1-2), 11.9 g of potassium carbonate, 13.8 g of 4- (bromomethyl) benzoate and 69 g of N, N-dimethylacetamide were added to the vessel. The obtained mixture was stirred at 60 ° C and reacted. The obtained reaction mixture was poured into ice water, and the obtained solid was separated by filtration. The solid separated by filtration was wash | cleaned with water and hexane, and the solid 14.5g containing the compound represented by a formula (VII-1-3) was obtained. Yield: 91% (based on the compound represented by the formula (VII-1-2)).

(4) 14.0 g of the compound represented by the obtained formula (VII-1-3), 56 g of methanol, 56 g of tetrahydrofuran, 2.6 g of sodium hydroxide, and 28 g of water were added to the vessel. The obtained mixture was stirred at 65 ° C and reacted. The obtained reaction mixture was cooled and then poured into ice water. Hydrochloric acid was added dropwise to the obtained mixture until the pH became 3. The precipitate precipitate was separated by filtration. The separated solid was washed with water and hexane to obtain 13.2 g of a solid containing a compound represented by the formula (VII-1-4). Yield: 99% (based on the compound represented by the formula (VII-1-3)).

(5) Into a container, 3.58 g of the compound represented by the formula (VII-1-4) obtained in the above (4), 3.79 g of the compound (VII-1-4) obtained in Example 1 (4), 4-dimethylamino 0.18 g of pyridine and 243 g of chloroform were added to obtain a mixture. The solution obtained by dissolving 2.96 g of N, N'- dicyclohexylcarbodiimide in 61 g of chloroform was dripped under the ice cooling in the obtained mixture. The obtained mixture was stirred and reacted. The precipitated solid was separated by filtration. The obtained filtrate was concentrated under reduced pressure to an amount of 1/2. Methanol was added to the obtained concentrate. After the obtained mixture was stirred, the precipitated solid was separated by filtration. Methanol wash | cleaned the separated solid, and 5.50g of compounds represented by a formula (VII-1-5) were obtained. Yield: 78% (based on the compound represented by the formula (VII-1-4)).

Example 4

After apply | coating 2% aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 perfect saponification type, Wako Pure Chemical Industries, Ltd.) on the glass substrate, it heat-dried and obtained the film of 89 nm in thickness. After the rubbing treatment was performed on the surface of the obtained film, a solution having the following composition was applied onto the surface on which the rubbing treatment was performed by the spin coat method. After drying for 1 minute on a 130 degreeC hotplate, the ultraviolet-ray of 2400mJ / cm <2> was irradiated, heating at 100 degreeC, and the optical film was obtained.

<Composition>

Compound (A): Compound 13.8% represented by the following Formula (vi-1-5)

Liquid Crystal Compound: LC242 (commercially available from BASF) 16.2%

Photoinitiator: Irgacure 819 (made by Chiba Japan Co., Ltd.) 0.9%

Leveling Agent: BYK361N (Bick Chemie Japan) 0.1%

Solvent: Cyclopentenone

Comparative Example 1

In Example 4, it carried out similarly to Example 4 except not having set the content of LC242 to 29.0%, without using the compound represented by Formula (VII-1-5), and obtained the optical film.

Measurement of Optical Properties

In the wavelength range of 450 nm to 700 nm, the retardation value of the manufactured optical film is measured using a measuring instrument (KOBRA-WR, Oji Measurement Instruments Co., Ltd.), and the retardation value Re (450) having a wavelength of 450 nm in the apparatus accessory program. ), A retardation value Re (550) having a wavelength of 550 nm, and a retardation value Re (650) having a wavelength of 650 nm. The results are shown in Table 2.

Example 5

In Example 4, an optical film can be manufactured by carrying out similarly to Example 4 except using the compound represented by Formula (VII-1-8) instead of the compound represented by Formula (VII-1-5). Can be.

Example 6

In Example 4, an optical film can be manufactured by carrying out similarly to Example 4 except using the compound represented by Formula (VII-1-9) instead of the compound represented by Formula (VII-1-5). Can be.

The optical film of this invention is possible for uniform polarization conversion in a wide wavelength range.

1 is a schematic view showing a color filter 1 of the present invention.

2 is a schematic view showing a liquid crystal display device 5 of the present invention.

3 is a schematic view showing the polarizing plate 30 of the present invention.

4 is a schematic view showing the attachment 21 of the liquid crystal panel 20 and the polarizing plate 30 of the liquid crystal display device of the present invention.

5 is a schematic view showing an organic EL panel 23 of the organic EL display device of the present invention.

* Description of the symbols for the main parts of the drawings *

1, 1 ': color filter

2, 2 ': optical film

3, 3 ': alignment film

4, 4 ': color filter layer

5: liquid crystal display

6, 10: polarizer

7, 11: substrate

8: counter electrode

9: liquid crystal layer

12: TFT, insulation layer

13: transparent electrode

13 ': reflective electrode

30, 30a, 30b, 30c, 30d, 30e: polarizer

14, 14 ': laminate

15: polarizing film

16, 16 ': support substrate

17, 17 ': alignment film

18, 18 ': optical film

19, 19 ', 22, 25: adhesive layer

20: liquid crystal panel

21: Attachment

23: organic EL panel

24: light emitting layer

Claims (28)

Formula (A)

(Wherein Ar represents a divalent group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, and the total number of π electrons in the aromatic ring contained in the bivalent group) N _π is greater than or _equal to 12. D ^a and D ^b are each independently a single bond, -CO-O-, -O-CO-, -C (= S) -O-, -OC (= S)-,- ^{CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R 2 -O-CR 3 R 4 -, -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ^3- , -CR ² R ³ -NR ^1- , -CO-NR ¹ -or NR ¹ -CO- and R ¹ , R ² , R ³ and R ⁴ Each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ^a and G ^b each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic heterocycle A halogen atom, May be substituted with at least one selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group, and a nitro group) The optical film obtained by superposing | polymerizing the compound containing group shown by the and at least 1 polymeric group. The method of claim 1, Compound containing group represented by Formula (A) and at least 1 polymeric group is Formula (B)

Wherein Ar, D ^a , D ^b , G ^a and G ^b have the same meanings as defined in claim ^1, and E ¹ and E ² are each independently —CR ⁵ R ⁶ —, —CH ₂ —CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-,- OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- Or a single bond, R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms) and an optical film which is a compound containing at least one polymerizable group. The method of claim 2, Compound containing group represented by Formula (B) and at least 1 polymeric group is Formula (C)

Wherein Ar, D ^a , D ^b , G ^a , G ^b , E ¹ and E ² have the same meanings as defined in claims ¹ and ² , and B ¹ and B ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O- , -OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S- CH _2- , -CH ₂ -S- or a single bond, R ⁵ and R ⁶ have the same meaning as defined in claim 2. A ¹ and A ² are each independently a divalent alicyclic hydrocarbon group or 2 The aliphatic hydrocarbon group and the alicyclic hydrocarbon group thereof represent a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a fluorine having 1 to 4 carbon atoms. The substituent may be substituted with at least one selected from the group consisting of a rhoalkoxy group, a cyano group, and a nitro group. Represents a) An optical film, which is a compound containing a group represented by the formula and at least one polymerizable group. The method of claim 3, wherein Compound containing group represented by Formula (C) and at least 1 polymeric group is Formula (D)

(Wherein Ar, D ^a , D ^b , G ^a , G ^b , E ¹ , E ² , B ¹ and B ² have the same meanings as defined in claim 1, 2 and 3, and F Each of ¹ and F ² independently represents an alkylene group having 1 to 12 carbon atoms, and the alkylene group may be substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom. and, also, at least one group of the methylene groups constituting the alkylene may be substituted with -O- or -CO-. P ¹ and P ² of which one represents a polymerizable group, the other is a hydrogen atom or a polymerizable group Indicates) The optical film which is a compound represented by. The method of claim 4, wherein Optical film which satisfy | fills Formula (2) and Formula (3).

The method of claim 4, wherein The compound represented by Formula (D) is Formula (1)

(Wherein Ar, E ¹ , E ² , B ¹ , B ² , F ¹ , F ² , P ¹ , P ² , k and l are in claims 1, 2, 3 and 4). Have the same meaning as defined, D ¹ and D ² are each independently -CR ¹ R ^2- , -CR ¹ R ² -CR ³ R ^4- , -O-CR ¹ R ^2- , -CR ¹ R ^2- O-, -CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ^1- , and R ¹ , R ² , R ³ and R ⁴ represent the same meaning as described above, G ¹ and G ² each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, and the aromatic hydrocarbon group and the aromatic heterocyclic group represent a halogen atom and carbon number. May be substituted with at least one selected from the group consisting of an alkyl group of 1 to 4, a fluoroalkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, a cyano group, and a nitro group) The optical film which is a compound represented by. The method according to any one of claims 1 to 6, Ar is an optical film in any one of group represented by Formula (Ar-1)-a formula (Ar-13).

(In formula, Z <^1> is a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a carboxyl group, C1-C6 fluorine. A roalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 N-alkylamino group, a C2-C12 N, N- dialkylamino group, a C1-C6 N- An alkylsulfamoyl group or an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, Q ¹ and Q ³ are each independently -CR ⁷ R ^8- , -S-, -NR ^7- , -CO- Or -O-, and R ⁷ and R ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to ^4. Y ¹ , Y ² and Y ³ are each independently an aromatic hydrocarbon group which may be substituted or substituted It represents an aromatic heterocyclic ring which may. W ¹ and W ² are each independently a hydrogen atom, a methyl group or a halogen Represent characters. M represents an integer of 0~6, n represents an integer of 0 to 2) The method of claim 1, An optical film wherein D ^a is -O-CR ¹ R ² -and D ^b is -CR ¹ R ² -O-. The method of claim 1, An optical film in which G ^a and G ^b are 1,4-phenylene groups. The method of claim 6, An optical film wherein D ¹ is -O-CR ¹ R ² -and D ² is -CR ¹ R ² -O-. The method of claim 6, G ¹ and G ² The optical film whose is a 1, 4- phenylene group. The method of claim 1, The optical film whose retardation value (Re (550)) in wavelength 550nm is 113-163 nm. The method of claim 1, The optical film whose retardation value (Re (550)) in wavelength 550nm is 250-300 nm. Formula (A)

(Wherein, Ar represents a divalent group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocyclic ring, the divalent group the total number of π electrons of the aromatic ring contained in the N _π 12 D ^a and D ^b are each independently a single bond, -CO-O-, -O-CO-, -C (= S) -O-, -OC (= S)-, -CR ¹ R ^{2 -, -CR 1 R 2 -CR 3} R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, -CR 1 R 2 -O-CR 3 R 4 -, -CR 1 R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ^3- , -CR ² R ³ -NR ^1- , -CO-NR ¹ -or NR ¹ -CO-, and R ¹ , R ² , R ³ and R ⁴ are each independently A hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ^a and G ^b each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic heterocyclic group each being a halogen atom; Carbon 1-4 alkyl group, a fluoroalkyl group having 1 to 4 carbon atoms in the alkyl group, may be substituted by at least one selected from an alkoxy group, a cyano group and a nitro group consisting of 1 to 4 carbon atoms) A compound containing a group represented by and at least one polymerizable group and formula (4)

(In formula, A <^11> represents an aromatic hydrocarbon group, an alicyclic hydrocarbon group, or a heterocyclic group, The aromatic hydrocarbon group, an alicyclic hydrocarbon group, and a heterocyclic group are a halogen atom, a C1-C6 alkyl group, C1-C6 May be substituted with at least one selected from the group consisting of an alkoxy group, an N-alkylamino group having 1 to 6 carbon atoms, a nitro group, a cyano group, and a mercapto group, B ¹¹ and B ¹² are each independently -CR ¹⁴ R ¹⁵ -, -C≡C-, -CH = CH-, -CH ₂ -CH _2- , -O-, -S-, -C (= O)-, -C (= O) -O-, -OC (= O)-, -OC (= O) -O-, -C (= S)-, -C (= S) -O-, -OC (= S)-, -CH = N-, -N = CH-, -N = N-, -C (= O) -NR 14 -, -NR 14 -C (= O) -, -OCH 2 -, -OCF 2 -, -NR 14 -, -CH 2 O-, —CF ₂ O—, —CH═CH—C (═O) —O—, —OC (═O) —CH═CH— or a single bond, and R ¹⁴ and R ¹⁵ are each independently hydrogen atom, a fluorine atom or an alkyl group having a carbon number of 1~4, R ¹⁴ and R ¹⁵ are combined to form a group having a carbon number of 4-7 alkylene Is Fig. ¹¹ E represents an alkylene group having 1 to 12 carbon atoms, the alkylene group is optionally substituted by at least one selected from alkyl groups, alkoxy groups and halogen atoms, the group consisting of 1 to 6 carbon atoms having 1 to 6 carbon atoms. P ¹¹ represents a polymerizable group, G represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 13 carbon atoms, an alkoxy group of 1 to 13 carbon atoms, a fluoroalkyl group of 1 to 13 carbon atoms, an N-alkylamino group of 1 to 13 carbon atoms, It is a cyano group or a nitro group, or the polymeric group couple | bonded via a C1-C12 alkylene group, The alkylene group is a group which consists of a C1-C6 alkyl group, a C1-C6 alkoxy group, and a halogen atom. May be substituted with at least one selected. T represents an integer of 1 to 5) The composition containing the compound shown by. The method of claim 14, Compound containing group represented by Formula (A) and at least 1 polymeric group is Formula (1)

Wherein Ar represents the same meaning as defined in claim 14. D ¹ and D ² each independently represent -CR ¹ R ^2- , -CR ¹ R ² -CR ³ R ^4- , -O-CR ¹ R ^2- , -CR ¹ R ² -O-, -CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ² -,- CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ^1- R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, G ¹ and G ² are each independently a divalent aromatic hydrocarbon group or 2 The aromatic aromatic heterocyclic group is represented, and the aromatic hydrocarbon group and the aromatic heterocyclic group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group. It may be substituted with at least one selected from the group consisting of E ¹ and E ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-,- OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH ₂ -, -CH ₂ -S- or a single bond, R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms B ¹ and B ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- or a single bond is represented. A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a fluorine having 1 to 4 carbon atoms. It may be substituted by at least one selected from the group consisting of a roalkyl group, an alkoxy group having 1 to 4 carbon atoms, a fluoroalkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group. k and l respectively independently represent the integer of 0-3. F ¹ and F ² each independently represent an alkylene group having 1 to 12 carbon atoms, and the alkylene group is substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom; At least one methylene group constituting the alkylene group may be substituted with -O- or -CO-. Either one of P ¹ and P ² represents a polymerizable group, and the other represents a hydrogen atom or a polymerizable group) The composition which is a compound represented by. The method according to claim 14 or 15, Furthermore, the composition containing a photoinitiator. The polarizing plate containing the optical film and polarizing film of Claim 1. The color filter in which a color filter layer, an oriented film, and the optical film of Claim 1 are laminated | stacked in this order. A liquid crystal display device comprising the color filter according to claim 18. A flat panel display device comprising the polarizing plate and liquid crystal panel according to claim 17. The organic electroluminescence display provided with the organic electroluminescent panel containing the polarizing plate of Claim 17. Formula (1)

(Wherein, Ar represents a divalent group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon ring and aromatic heterocyclic ring, the divalent group the total number of π electrons of the aromatic ring contained in the N _π 12 . more than D ¹ and D ² are each independently selected from ^{-CR 1 R 2 -, -CR 1} R 2 -CR 3 R 4 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-, - CR ¹ R ² -O-CR ³ R ^4- , -CR ¹ R ² -O-CO-, -O-CO-CR ¹ R ^2- , -CR ¹ R ² -O-CO-CR ³ R ^4- , -CR ¹ R ² -CO-O-CR ³ R ^4- , -NR ¹ -CR ² R ³ -or -CR ² R ³ -NR ^1- , and R ¹ , R ² , R ³ and R ⁴ Each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms, G ¹ and G ² each independently represent a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group, the aromatic hydrocarbon group and the aromatic hetero group; The ring group is a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, It may be substituted with at least one selected from the group consisting of an alkoxy group, a cyano group and a nitro group having 1 to 4 carbon atoms, E ¹ and E ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2- , -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC ( = S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- or Represents a bond, and R ⁵ and R ⁶ each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, B ¹ and B ² are each independently -CR ⁵ R ^6- , -CH ₂ -CH _2; -, -O-, -S-, -CO-O-, -O-CO-, -O-CO-O-, -C (= S) -O-, -OC (= S)-, -OC (= S) -O-, -CO-NR ^5- , -NR ⁵ -CO-, -O-CH _2- , -CH ₂ -O-, -S-CH _2- , -CH ₂ -S- or A single bond is shown. A ¹ and A ² each independently represent a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group include a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a fluorine having 1 to 4 carbon atoms. It may be substituted by at least one selected from the group consisting of a roalkyl group, an alkoxy group having 1 to 4 carbon atoms, a fluoroalkoxy group having 1 to 4 carbon atoms, a cyano group and a nitro group. k and l respectively independently represent the integer of 0-3. F ¹ and F ² each independently represent an alkylene group having 1 to 12 carbon atoms, and the alkylene group is substituted with at least one selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a halogen atom; At least one methylene group constituting the alkylene group may be substituted with -O- or -CO-. Either one of P ¹ and P ² represents a polymerizable group, and the other represents a hydrogen atom or a polymerizable group) Compound represented by. The method of claim 22, The compound which satisfy | fills Formula (2) and Formula (3).

The method of claim 22, Ar is any of groups represented by Formula (Ar-1)-a formula (Ar-13).

(In formula, Z <^1> is a halogen atom, a C1-C6 alkyl group, a cyano group, a nitro group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a carboxyl group, C1-C6 fluorine. A roalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 N-alkylamino group, a C2-C12 N, N- dialkylamino group, a C1-C6 N- An alkylsulfamoyl group or an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, Q ¹ and Q ³ are each independently -CR ⁷ R ^8- , -S-, -NR ^7- , -CO- Or -O-, and R ⁷ and R ⁸ each independently represent a hydrogen atom or an alkyl group having 1 to ^4. Y ¹ , Y ² and Y ³ are each independently an aromatic hydrocarbon group which may be substituted or substituted It represents an aromatic heterocyclic ring which may. W ¹ and W ² each independently represent a hydrogen atom, a cyano group, a methyl group or a halogen Represent characters. M represents an integer of 0~6, n represents an integer of 0 to 2) The method of claim 22, A compound wherein D ¹ is -O-CR ¹ R ² -and D ² is -CR ¹ R ² -O-. The method of claim 22, G ¹ and G ² are 1,4-phenylene groups. A method for producing an unpolymerized film, which is applied to a solution containing the compound according to any one of claims 22 to 26 on a support substrate or an alignment film formed on a support substrate and dried. The unpolymerized film obtained by the manufacturing method of Claim 27 is polymerized, The manufacturing method of the optical film characterized by the above-mentioned.

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