TW200909413A - Compound and optical film - Google Patents

Abstract

The present invention provides a novel compound and a novel optical film capable of reducing the wavelength dependence of phase retardation value. The present invention provides a compound represented by formula (a). [In formula (a), C10 represents a quaternary carbon atom, A10 and A20 represent a divalent cyclic hydrocarbon group or a divalent heterocyclic group. D10 and D20 represent a cyclic hydrocarbon group or a heterocyclic group, and at least one hydrogen contained in these groups being substituted by an electron attracting group. B10 and B20 represent a divalent group. X10 and X20 represent a divalent group such as the group represented by formula (2). (In formula (2), A3 represents -C(=O)-C6H4-, a divalent cyclic hydrocarbon group or a divalent heterocyclic group, B3 has the same meaning as above mentioned B10. n represents an integer of 0 to 4.) E10 and E20 represent an alkylene group etc., P10 and P20 represent a polymeriable group etc.]

Description

[Technical Field] The present invention relates to a compound or the like which is applied to an optical film such as a phase difference film or a polarizing plate, and the optical film can be used for a liquid crystal display device or An electromechanical excitation light display device such as a flat display device. [Prior Art] A flat display device such as a liquid crystal display device (hereinafter also referred to as "LCD") or an organic electroluminescence display device (hereinafter also referred to as "EL") when compared with a cathode discharge device (Braun tube) display device (hereinafter also referred to as "FpD") saves space and consumes less power. Therefore, FpD has been widely used in recent years as a computer, television, mobile phone, car navigator or portable information terminal. In general, a wide variety of optical films such as a polarizing plate and a phase difference plate can be used in the FPD to prevent reflection, enlarge the viewing angle, and the like. It is known that the wavelength dispersion characteristic of the phase difference is one of the optical characteristics of the retardation film. Specifically, the wavelength dispersion of the usual phase difference shows the characteristic of [Re(450)/Re(550)] > 1 > [Re(65〇)/Re(55〇)] (Retentive, Re( ;l) 疋 denotes the phase difference 相位 of the phase difference 测 measured by measuring the wavelength of light and nm. This wavelength dispersion is called positive wavelength dispersion. The retardation film obtained by polymerizing the polymerizable compound can also exhibit positive wavelength dispersion. In the example of Patent Document 1, a retardation film obtained by polymerizing a polymerizable compound having a special structure containing a halogen atom or a sulfur atom shows [Re(45G)/Re(55G)] = l. G65 and [Re(65G)/Re(550)]=〇. The kiss indicates a positive wavelength dispersion, but the positive wavelength dispersion is shifted in the reverse direction when compared with the wavelength dispersion characteristics of the comparative example. k 32〇352 200909413 For optical films, there is a requirement to reduce the wavelength dependence of the phase difference. The degree of wavelength dependence of the phase difference value can be expressed by the value of Re(450)/Re(550). When the value is greater than 1, the wavelength dependence of the phase difference value increases. Here, Re(λ) means a phase difference value of a wavelength λ nm transmitted through the optical film. The optical film of the past, as disclosed in Patent Document 1, is an optical film obtained by coating a compound represented by the formula (20) on an alignment medium, and the optical film provides 1^(450)/1^(550). The value is 1.065, which is not sufficient.

[Patent Document 1] JP-A-2006-58546 ([Patent Application No. 1], [0115], [〇117]) [Disclosure] [Problems to be Solved by the Invention] The object of the present invention is Providing a Dependent Novel Compound and Novel Light [Method for Solving the Problem] A wavelength-dependent film that suppresses the phase difference can be added. The present invention solves the problem, that is, the inventors of the present invention have found that the inventors have found a specific structure and achieved the invention contained in the present invention. [1] A compound represented by the formula (a): 320352 5 200909413

Mmxi^M0-X20-M)-P 20 (In the formula (a), CIO represents a quaternary carbon atom or a quaternary atom; A10 and A20 each independently represent a divalent cyclic hydrocarbon group or a divalent heterocyclic group; A10 and A20 may also be bonded to an alkyl group, an alkoxy group or a halogen atom; D10 and D20 each independently/also represent a hydrocarbon group or a heterocyclic group, and at least one atom system contained in D10 and D20 is substituted with an electron attracting group; D10 • / And D20 may also be linked to each other by a hydrocarbon group, an amine group, an ether group, a thioether group, an aminoalkyl group, a carbonyl group or a single bond; B10 and B20 independently represent -CRR _, -CeC-, _CH-CH_ ' _CH2~CH2- ' -〇- ' ~S_ ' _C(-0)_ n -0(=0)-0- ' -0-C(-0)_ ' -0-0(=0)-0- ' _C(=S)~ ' _C(=S)-0- ' -〇-C(=S)---〇-C(=S)-0-, -CH=N---N=CH- --C(=0)-NR-, -NR-C(=0)---OCH2---NR----CH2O---SCH2---CH2S- '-CH=CH-C(= 0)-0-, -0-C(=0)-CH=CH- or a single bond; here, R and R' each independently represent a hydrogen atom or an alkyl group; when X20 is not a single bond, X10 and X20 Respectively representing a divalent group represented by the formula (2);

[In the formula (2), A3 represents -C(=0)-C6H4-, a divalent cyclic hydrocarbon group or a divalent heterocyclic group; the -C(=0)-C6H4-, a divalent cyclic hydrocarbon group or a divalent group; The heterocyclic group may also bond an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a triple 6 320352 200909413 fluoromethyl group, a trifluoromethyloxy group, a nitrile group, a nitro group or a halogen atom. B3 is the same meaning as B10 and B20, and n is an integer from 1 to 4. When η is 2 to 4, the structural units composed of A3 and Β3 may be the same or different from each other. When Χ20 is a single bond, χιο is a divalent group represented by the formula (3); ·· I. A "1 a hzv-- B: --(3); 丄J Ώ [In the formula (3), A3i represents -C(=〇)-c6H4-, a divalent cyclic hydrocarbon group of 5 to 20 membered rings or a divalent heterocyclic group of 5 to 20 membered ring; the _c(=〇)_d_, a cyclic hydrocarbon group or the heterocyclic ring The group may also be bonded to an alkyl group having a carbon number of 4 to 4, an alkoxy group having 1 to 4 carbon atoms, a trifluoromethyl group, a trifluoromethyloxy group, a nitrile group, a nitro group or a halogen atom; -CH2-CHs -0-, -S-, -C(=0)-, -c(〇)-〇-, -〇-C(=〇)_, _〇_c(=〇)一〇_, -CH- N-, -N=CH-, -C(=〇)-NL' - -NRi, -C(=〇)-, -〇ch2-, -Muscle, -, -CM-, -CiK: HC(=0)-〇-, "(4))_CH=CH- or single bond; here , L, and R1" each independently represent a thio or _ hydrogen atom having a carbon number of i to 4; η represents any integer of 1 to 4; and when 11 is 2 to 4, a structure composed of - and Bn The units may be the same or different from each other.] When X20 is not a single bond, 'E10 and E2〇 respectively represent an alkyl group having a carbon number of 2 to 25; E10 and E2G may also be combined with an alkyl group or an alkoxy group. , trifluoromethyl, trifluoromethyloxy, nitrile, nitro, halogen atom; when X20 is a single bond, E1〇 is a divalent group represented by formula (1}), £2〇表320352 7 200909413 shows a kecioalkylene having 1 to 12 carbon atoms, and a hydrogen atom contained in E20: a halogen group of 4, a silk group having a slave atom number i to 4, or a γ atom atom;

E 3 0>} [In the formula (5), E3 represents the number of carbon atoms! To the extended alkyl group of 12, the atom contained in 1 may also be substituted with an alkoxy group or a halogen atom having a number of diaster numbers of 1 to 4 and a carbon number of i to 4; Bs represents _〇---s___c (=〇) I. -C(=0)-〇-, -〇-c(=〇)_, a c(,NRi_, Qin C")-, -0CH2-, -〇-c('- or single bond; this Wherein, R] represents an alkyl group having a carbon number of 丨 to 4 or a hydrogen atom] When X20 is not a single bond, P10 and P20 each independently represent a hydrogen atom or a chelating group, and at least one of P1 m and m is a polymerizable group; when X20 is a single bond, Pi〇 is an argon atom or a group represented by formula (p-ι) to (p-5), and P20 is a hydrogen atom;

(4) (P-3) (P - 4) [In the formulae (P-1) to (P-5), 匕 to Rs each independently represent an alkyl group having 1 to 4 carbon atoms or a hydrogen atom]). [2] A polymerizable compound represented by the formula (1): 8 320352 200909413

Dl, βΐ ( l ) P2 \ A2 — B2 ～X2—E2~*P2 (in the formula (1), c represents a quaternary carbon atom or a quaternary fluorene atom; and A1 and A2 each independently represent a divalent cyclic hydrocarbon group or a divalent heterocyclic group; A1 and A2 may also be bonded to a top group, an alkoxy group or a _ atom; D1 and D2 each independently represent a hydrocarbon group or a heterocyclic group, and w and d2 may contain at least one hydrogen atom. The electron attracting group is substituted... and D2 may be bonded to each other by a hydrocarbon group, an amine group, a bond group, a sulfur bond group, an amine group, a group or a single bond; B1 and B2 respectively represent -CRR, -, -C^ C-, -CHCH-, -ch2-ch2-, -ο-, -s-, -c(=0)_' _c(=0)_0_, _〇_c(=〇)1, -〇-C (=0)一〇-, -C(=S)-, -C(=S)-0-, -〇一c(=S)_, -〇-C〇S)-〇-, -CH= N-, -N=CH-, -C(=0)-NR-, -_〇〇)_, -0CH2-, -NR-, -CH2〇-, -SCH2-, -CH2S-, -CH= CH--C(=〇)-〇-, -〇-C(=0)-CIH:H- or a single bond; here, R & R' independently represent a hydrogen atom or a burnt group; X1 and X2 Separately, the divalent phors represented by the formula (2) are respectively represented by the formula (2). A.3 B. 3 ^ (2) 1 J η [In the formula (2), A3 represents -C(=0)-C6 H4-, a divalent cyclic hydrocarbon group or a divalent heterocyclic group, the -C(=0)-C6H4_, a divalent cyclic hydrocarbon group or a divalent heterocyclic group may also be bonded to an alkyl group having 1 to 4 carbon atoms, carbon An alkoxy group having 1 to 4 atomic number, a trimethyl group, a difluoromethyloxy group, a nitrile group, a nitro group or a halogen atom; B3 is synonymous with B1 and B2 described in 320352 9 200909413, and η represents 1 to 4 The integers; when ^ is 2 to 4, the structural units composed of A3 and Β3 may be the same or different from each other]. Ε1 and Ε2 each independently represent an alkylene group having 2 to 25 carbon atoms, and Ε1 and Ε2 may also be bonded to an alkyl group, an alkoxy group, a trifluoromethyl group, a trifluoromethyloxy group, a nitrile group, a nitro group, Halogen atom; Ρ1 and Ρ2 each independently represent a hydrogen atom or a polymerizable group, and at least one of ρι and ρ2 is a polymerizable group). [3] The polymerizable compound according to [2], wherein the electron attracting group bonded to the group of di and D2 in the formula (1) is a nitro group, a nitrile group, a trifluoromethyl group, or a formula (4) ) the base represented by or the base represented by the formula (5): -Ό-Ο

(4): C5) [In the formulas (4) and (5), Ra represents a hydrogen atom, a linear alkyl group having 2 to 2 carbon atoms, a fraction of 3 to 18 carbon atoms, and 5 carbon atoms; a cycloalkyl group to 18, a phenyl group, a furanyl group or a thiophenyl group, and Rb represents a linear alkyl group having a carbon number of from j to 18 and a branched form having an inverse atomic number of from 3 to 18. A pyridyl group having a carbon number of 5 to a, a phenyl group, a furyl group or a thienyl group). (4) The polymerizable compound according to [2] or [3], wherein the formula B2 is a single bond, -0 to _s_, _ci) ύ C(=〇)-〇-, -〇_c(=〇)_, Or -0-C (=0) ~ 〇 base. The polymerizable compound according to any one of [2] to [4] wherein the divalent group consisting of C1, D1 and D2 in the formula (1) is selected from the formula oy. ) to the divalent base of the group:

(In the formulae (D-1) to (D-11), the EWG independently represents the electron attracting group; p and q each independently represent 0 to 4, and r represents 〇 to 6. However, when the above group has (EWG) P and (based on EWGX, bp+qss, with stomach (EWG) r and (EWGXi base, lSr + qs1〇). [6] As in any of [2] to [5] The polymerizable group in the formula (1), wherein the polymerizable group in the formula (1) is a propylene group or a methyl propyl group. [7] The polymerizable compound according to [2], wherein the polymerization represented by the formula (1) The compound is a compound selected from the group consisting of compounds represented by the formulae (1-A) to (1-C). 320352 11 200909413

N2 independently represents an integer from 2 to 14; each independently represents an atom or a methyl group. A composition containing a polymerizable compound different from the polymerizable compound according to any one of [2] to [7] and exhibiting liquid crystallinity, and the polymerizability of any one of [2] to [n] Compound. [9] The composition of the item [8], wherein the polymerizable compound which is different from the polymerizable compound of any one of [2] to [7] and which exhibits liquid crystallinity, is a formula (I) , a compound represented by formula (II), formula (ΙΠ) or formula (IV): P110-B110-E110- (B120-A110) S-B130-E120-B140-P120 (I) P110-B110-E110- (A110 -B120) S-E120-B130-P120 (II) P110-B110-E110- (B120-A110) S-F110 (III) P110-B110-E110- (B120-A110) S-B130-F110 (IV) [ In the formulae (I) to (IV), Alio independently represents a divalent cyclic hydrocarbon group, a divalent heterocyclic group, a methylene phenylene group, an oxygen phenyl group or a thiophenylene group; It is also possible to combine an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogen atom; B110, B120, B130 and B140 each independently represent -CRT Ri, J - ' -C = C- ' -CH=CH- ' -CH2-CH2- ' -〇- ' -S- ' -C(=0)- ' -C(=0)-〇- ' -〇-〇(=0)- ' - 〇-C(=0)-〇-' -C(=S)- ' -C(=S)-0---〇-C(=S)-,-0-C(=S)-0- , -CH=N---N=CH-, -N=N-, -N(-0)=N-, -N=N(-0)-, -C(=0)-NRi' -, -NR/ -C(=0)---OCH2---NRiJ ---CH2O- ' -SCH2- > -CH2S- ' -CH=CH-C(=0)-0-,-0-C(=0)-CH=CH- or single bond (and, Rr and Rr each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; E110 and E120 each independently represent an alkylene group having 2 to 25 carbon atoms; and 'E110 and E120 may also be bonded to a carbon number of 1 to An alkyl group of 5, an alkoxy group having 1 to 5 carbon atoms or a halogen atom; P110 and P120 each independently represent a polymerizable group; and F110 represents a hydrogen atom, an alkyl group, a nitrile group, a nitro group, a trifluoromethyl group or a halogen atom. Atomic; 13 320352 200909413 s respectively represent an integer from 1 to 5; when s is 2 to 5, the structural units composed of A110 and B120 may be identical to each other or different from each other]. [10] The composition of the item [8] or [9], wherein the polymerizable compound exhibiting liquid crystallinity with respect to the polymerizable compound of any one of [2] to [7], and [2] The total amount of the polymerizable compound of any one of the items [7] to [7] is from 3 to 50 parts by weight. [11] An optical film comprising the structural unit derived from the polymerizable compound according to any one of [2] to [7]. [12] An optical film, which is obtained by polymerizing the composition of any one of [8] to [9]. [13] The optical film of [11] or [12], which is used for a phase difference (Re (550)) having a wavelength of 55 〇 nm of 113 to 163 nm; 1/4 plate. [H] An optical film according to [11] or [12], which is used for a phase difference (Re(550)) having a wavelength of 55 〇 nm of 250 to 300 nm; an I/2 plate. [15] A polarizing plate comprising the optical film of any one of [11] to [14], and a polarizing film. [16] A flat display device comprising: a polarizing plate of [15] and a liquid crystal panel. [Π] An organic EL display device comprising an organic electroluminescence panel comprising a polarizing plate of [15]. [18] A method for producing an unpolymerized film, which comprises applying the composition of any one of [8] to [1〇] to a support substrate, followed by drying. 320352 14 200909413 [19] A method for producing an unpolymerized film, which comprises applying the composition of any one of [8] to [ι〇] onto an alignment film formed on a support substrate, and then drying it. [20] A method for producing an optical film, which comprises curing the unpolymerized film obtained by the production method of [18] or [19] by polymerization. [21] A compound represented by formula (11) or formula (21):

(EWG in equations (11) to (21) independently represent electron attracting groups, p 1 and ql each independently represent any integer from 〇 to 4; however, 丨w ; — and A1Z are independently represented. i, 4_ stretched phenyl group, the ij-phenylene group may also be bonded to at least one substituent selected from the group consisting of an alkyl group having a carbon number of 4 to 4 and an alkyl group having a carbon number of the stem 4;

Bn, B21 and β31 respectively represent -〇, _s_, -, -c(=0)m〇)...c(=〇)_NRi'...眺, -c(鲁, (〇2 〇c( 〇) 〇- or a single bond, here, [ represents a hospital group or a hydrogen atom having 1 to 4 carbon atoms; X represents a divalent group represented by the formula (3);

[In the formula (3), 'A31 represents a -c (ridge-mono, 5- to (tetra) ring) divalent ring 320352 15 200909413 smog or a divalent heterocyclic group of 5 to 20 membered ring; the -c(tetra)-ci, ring The domain or the heterocyclic group may also bond an alkoxy group having a carbon number i to a 4 (tetra) group, a carbon number of 1 to 4, a dion field, a lanthanum methyl group, a trifluoromethyloxy group, a nitrile group. , nitro or halogen atom; B41 means, 'Rl' -, inverted -, -CH., general CH2_, one 〇 -, I, -C(=0)-, -C(, l' -0-C(4) - CH: [, -N=CH_, -C(=0)~NRi,-, -NR!, -C(=0)-, -〇CH2-, 〇〇NRl ' ~Cm cH=CH-C(= 〇)-〇---0-C(=0)-CH=CH-^ Single bond 'herein' Rl and Rl" each independently represent an alkyl group having 1 to 4 carbon atoms or a hydrogen atom; Π represents 1 to Any-integer of 4; when η is 2 to 4, the structural units composed of a31 and Bum may be the same or different from each other]

En represents an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom contained in Eu may be substituted by a filament having 1 to 4 carbon atoms, a number of carbon atoms of 丨. to 4, or a halogen atom;

Eu represents an alkyl group having a carbon number of 丨 to 12 or a cycloalkyl group, and a hydrogen atom contained in the core may be substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a halogen atom. ;

Pu is a hydrogen atom or a group represented by the formula (P-I) to (Ρ-5);

f moxibustion: today. (P-3) (P-4) (P-5) [In the formulae (P-1) to (P-5), R1 to R5 each independently represent an alkyl group or a hydrogen atom having a carbon number of 1 to 16 320352 200909413; ]). [22] The compound according to [21], wherein the EWG in the formulae (U) and (21) is a nitro group, a nitrile group or a trifluoromethyl group. [23] A compound according to [21] or [22], wherein a31 is any one of the groups represented by formula (4_丨) to (4_5):

(4) The compound according to any one of [21] to [23], wherein Pi in the formulae (U) and (21) is a group represented by the formula (p_1). [25] A composition comprising the compound according to any one of [21] to [24], and a polymerizable compound exhibiting liquid crystallinity. [26] An optical film obtained by polymerizing a composition of the item [25]. [27] An optical film comprising the structural unit derived from the compound of any one of [21] to [.24]. [28] A λ/4 plate which is an optical film of [26] or [27], and a phase difference (Re(550)) of light having a wavelength of 550 nm transmitted through the optical film is 113 to 163 nm. . [29] A type of/2 plate, which is an optical film of [26] or [27], and a phase difference (Re(550)) of light having a wavelength of 550 nm transmitted through the optical film of the sea is 250 to 300 nm. By. [30] A polarizing plate comprising the optical film according to any one of [26] to [29], and a polarizing film. [31] A flat display device comprising the polarizing plate of [30] and the liquid crystal 17 320352 200909413 panel. [32] An organic electroluminescence display device comprising the polarizing plate of [30] and an organic electroluminescence panel. [33] A method for producing an unpolymerized film, which comprises applying a solution containing the composition of [25] to a support substrate, followed by drying. [34] A method for producing an unpolymerized film, which comprises applying a solution containing the composition of [25] onto an alignment film formed on a support substrate, and drying the solution. [35] A method for producing an optical film, which is obtained by curing the unpolymerized film obtained by the method of any one of [33] or [34]. [Effect of the Invention] The present invention can provide a novel compound and a novel optical film which can further suppress the wavelength dependency of the retardation value. The optical film of the present invention can have a wide range and a desired phase difference. Therefore, the optical film can be used as a λ/4 plate or a λ /2 plate even if it is only one optical film. An optical film containing a structural unit derived from the polymerizable compound represented by the formula (1) is an optical film exhibiting wavelength dispersion characteristics in which positive wavelength dispersion is suppressed, and a structural unit capable of supplying such a characteristic (from the formula (1) The structural unit of the polymerizable compound has a small content and can be provided at low cost. Further, since the polymerizable compound represented by the formula (1) is excellent in compatibility and can be dissolved in a general-purpose organic solvent, it is possible to easily adjust the optical properties of the optical film when a monomer as a polymer for an optical film is used. By adding the polymerizable compound represented by the formula (1) in a small amount, the optical film can be moved in the opposite direction to the positive wavelength dispersion. 18 320352 200909413 [Embodiment] The compound of the present invention is a compound represented by the formula (a): a foot, /fine-BlOHaO-E10, M (a) D20 ^i\20^2Q-^^E20-f20 (formula (a) In the above, CIO represents a four-stage complex atom or a fourth-order stone atom; A10 and A20 independently represent a divalent cyclic hydrocarbon group or a divalent heterocyclic group; and A10 and A20 may also be bonded to an alkyl group, an alkoxy group or a dentate. Atom; D10 and D20 are each independently a hydrocarbon group or a heterocyclic group, and at least one hydrogen atom contained in D10 and D20 is substituted with an electron attracting group; D10 and D20 may also be a fe group, an amine group, a bond group, or a sulfur bond group. , an amine group, a thiol or a single bond to each other; B10 and B20 independently represent -CRR' -, -CeC-, -CIKH-, -CH2-CH2-, -0-, _S-, -C (=0)-, -C(=0)-0_, -0-C(=0)---0-C(=0)-0---C(=S)-c(=s)- O-, -0-C(=S)---0-C(=S)-0-, -CH=N---N=CH---C(=0)-NR-, _NR_C(= 0) -, -OCH2-, -NR-, -CH2O-, -SCH2-, -CH2S-, -CH=CH-C(=0)-0-,-0-C(=0)-CH=CH - or a single bond; here, R and R' each independently represent a ruthenium atom or a ruthenium; when X20 is not a single bond, X10 and X20 are independently represented by (2) a divalent group represented; ---A3--B 3 ---(2) J η [In the formula (2), A3 represents -C(=0)-C6H4-, a divalent cyclic hydrocarbon group or Divalent 19 320352 200909413 soil base; the -C (=0) -C6H4-, monovalent cyclic fe group or divalent heterocyclic group may also be a carbon number of 1 to 4, carbon number 1 to Alkoxy, tri-l-decyl, tri-IL-decyloxy, nitrile, schlossyl or halogen atom; B3 is the same meaning as mo and B20 described above; η represents an integer from 1 to 4; 2 to 4 o', the structural units composed of A3 and B3 may be the same or different from each other. When X20 is a single bond, X10 represents a divalent group represented by formula (3);

[In the formula (3), A31 represents a -C(=0)-C6H4-, a divalent cyclic hydrocarbon group of 5 to 20 membered rings or a divalent heterocyclic group of 5 to 20 membered ring; a cyclic hydrocarbon group or the same The cyclic group may also be bonded to an alkyl group having a carbon number of i to 4, an alkoxy group having a carbon atom to 4, a trifluoromethyl group, a trifluoromethyloxy group, a nitrile group or a nitro halogen atom; the earth 〜 represents -CR/R /' -, -C three C_, _CH=CH_, _CH2—CH2—, 0~, ~S_, -c(=0)-, -C(=0)-0-,-0-CO0)-,- 〇-c(=〇)—〇_—CH=N-, -N=CH-, -C(=〇)-NRi,-, —NRl,-c(=0)_, _〇CH2—〇〇 NRl ~ ' ~CH2° CH=CH-C(=0)-0- ' -〇-C(=0)-CH=CH~^ Early key; here 'R!, and Rl, are independently represented Carbon number U. A group or a hydrogen atom; the alkene η represents any integer from 1 to 4; when #11 is 2 to 4, the structural units composed of i and 41 kg may be the same or different from each other] When Χ20 is not a single bond, Ε1〇 and Ε2〇 respectively represent the alkyl groups of carbons 2 to 25, and Ε10 and Ε20 may also be combined with alkyl, alkoxy 20 320352 200909413, trifluoromethyl, Fluoromethyloxy, nitrile, nitro, halogen atom; when X20 is a single bond, E10 represents (b) represents a divalent group, E20 represents an alkylene group or a cycloalkyl group having 1 to 12 carbon atoms, and the hydrogen atom contained in E2〇 may also pass through an alkyl group having 1 to 4 carbon atoms.丨 to 4 is substituted by an oxy group or a halogen atom; f 4umm Μ 5 (b) [In the formula (b), E3 represents an alkyl group having a carbon number of 丨 to 12, and a hydrogen atom contained in Es may also pass through a carbon atom. a number of 1 to 4 alkyl groups, an alkoxy group having a carbon number of 4 to 4 or a halogen atom; b5 represents -0---S-, -c(=o)-, -C(=0)-0- , -〇-c(=〇)---C(=0)-NRi- > -NRi-C(=〇)~ > OCH2 0 C(-0)- or single bond, ·here, a group having a carbon number of i to 4 or a hydrogen atom] When X20 is not a single bond, 'P1〇 and P2〇 each independently represent a hydrogen atom or a polymerizable group, and at least one of P10 and P20 is a polymerizable group; When X20 is a single bond, pi is a hydrogen atom or (ρ_ι) to the base 'P20 is a hydrogen atom; 乂^r2

—Q R4 R5 (P-1) (P-2) (P-3)

(P'5) [In the formulae (Ρ-l) to (P-5), 匕 to Rs each independently represent an alkyl group having a carbon number of 4 or a hydrogen atom]). The embodiment of the compound of the present invention is a polymerizable compound (hereinafter referred to as "polymerizable compound (1)") represented by the following formula (1): 320352 21 200909413.

Dl\ /A1—B1 ～XI—E1—P1 /V (η D2 Α2 — Β2~Χ2 — Ε2—Ρ2 Ο), where ci represents a quaternary carbon atom or a quaternary atom. Since C1 is a quaternary substituent, the faces constituting A1 and B1 form a face with the faces constituting A2 and B2. To 14 baht. And to form 11 〇. To 13 baht. ,good. Therefore, the polymerizable compound (1) of the present embodiment is in an organic solvent; in the case of the solution, the compatibility of the oxime with the liquid crystal compound described later, and the tendency of the phase difference of the photonic film obtained by the force is increased. Preferably. Among them, in terms of the easiness of the production of the compound (1), it is preferred that C1 is a quaternary carbon atom. In the formula (1), A1 and A2 each independently represent a divalent cyclic hydrocarbon group or a dioxime group, and represent a divalent cyclic hydrocarbon group having a carbon number of about 5 to 2 Å or a carbon number of about 5 to A divalent heterocyclic group of 20 is preferred. In the case of the divalent cyclic hydrocarbon group as A1 and A2, a cycloalkyl group having a carbon number of about 5 to 10 such as a pentyl group or a % hexyl group, and a carbon number represented by the following formula of about 6 to 20 may be used. Aromatic group,

An alicyclic base consisting of a 5-member ring and a 6-member ring, or 320352 22 200909413

A heterocyclic group composed of a 5-membered ring and a 6-membered ring represented by the following formula. ◎, mouth, $, 旮, 〇,, public A1 and A2 can also be combined with a base, a hospitaloxy or a halogen atom. For example, a part of the hydrogen atom of the above divalent cyclic hydrocarbon group or divalent heterocyclic group may also be an alkyl group having a carbon number of about i to 4 such as a methyl group, an ethyl group, an isopropyl group or a third butyl group; Alkoxy groups having a carbon number of about 4 to methoxy, ethoxy, etc.; monofluoromethyl, difluorodecyloxy; nitrile; nitro; fluorine atom, gas atom, > Atomic substitution. Among them, when A1 and A2 are the same type of base, it is preferable because it is easy to manufacture. Further, when 1,4-phenylene group, 1,4-cyclohexylene group, and 3 fluorenyl group 1> 4-phenylene group are used as A1 and A2, it is preferable because it is easy to produce. _ D1 and D2 are each independently a hydrocarbon group or a heterocyclic group, and at least one hydrogen atom contained in ruthenium and osmium is substituted with an electron attracting group. In the case where the electron-attracting group is contained in any one of D1 and D2, even if the content of the structural unit derived from the polymerizable compound (1) is such that the positive wavelength dispersion is shifted in the reverse direction, it is easy to It is preferable to control D to the wavelength dispersion characteristics of the optical film. In particular, when both D1 and D2 contain an electron attracting group, the polymerizable compound (1) can be easily formed into a combination of D32 and D2. The hydrocarbon group is a cyclic, linear or branched hydrocarbon group having 1 to 20 carbon atoms. Specifically, when a group which is not substituted with an electron attracting group is used as a cyclic hydrocarbon group, for example, cyclopentane is exemplified. A cycloalkyl group having a carbon number of from about 5 to about 12, such as a cyclohexyl group, and the like, and an aromatic group substituted with an electron attracting group having a carbon number of about 6 to 20 represented by the following formula.

(ΒΛΛ3) γ (EWG)^ (EWG),

Here, the EWG independently represents an electron attracting group. p and Q respectively represent 0 to 4, and r represents 0 to 6. However, when the above group has (EWG)p and (EWGX, l$p+q$8, and has (EWG)r and (EWG)q2 groups, 1 S r + q S 10 . Generally, the electron-attracting group is substituted with a ruthenium atom bonded to a carbon atom at the carbon atom of the carbon atom bonded to C1. The heterocyclic group which can be substituted at D1 and D2 and which can be substituted by an electron attracting group can be used. For example, the following formula, etc. 24 320352 200909413 >^-(EWG)t ^(EWG)t Q(EWG)t (EWG)t

R ^T^(EWGX ^(EWG), _^^Nr- (pG)» NR'

(EWG)rV

In the formula, the EWG independently represents an electron attracting group. t represents an integer from 1 to 5, and preferably from 1 to 2. Usually, the electron attracting group replaces the hydrogen atom bonded to the carbon atom of the alpha position of the hetero atom. Here, examples of the electron attracting group include a nitro group, a nitrile group, a trifluoromethyl group, a group represented by the formula (4), a group represented by the formula (5), and the like. Among them, the polymerizable compound (1) can be easily produced by using a schlossyl group, a nitrile group or a trifluoromethyl group.

(4) (5) (In the formulae (4) and (5), Ra represents a hydrogen atom, a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, and carbon. a cycloalkyl group having 5 to 18 atoms, a phenyl group, a furyl group or a thienyl group; Rb represents a linear alkyl group having 1 to 18 carbon atoms, a branched alkyl group having 3 to 18 carbon atoms, and a carbon number 5 to 18 cycloalkyl, phenyl, furyl or thienyl). D1 and D2 may also be bonded to each other by a hydrocarbon group, an amine group, an ether group, a thioether group, an amine group 25 320352 200909413 alkyl group, a carbonyl group or a single bond. The above hydrocarbon group is preferably a hydrocarbon group having a carbon number of about 1 to 5, and more preferably a methylene group, an ethyl group, a propyl group or the like, or a single bond of an alkyl group via a double bond or a triple bond. Replaced by the connection, the base, and so on. The divalent group (-C1D1D2-) composed of Cl, D1 and D2 is preferably a group in which D1 and D2 are bonded to each other, and as a specific example thereof, it is represented by the formula (D-1) to (D-11). Divalent base, etc.

In the formulae (D-1) to (D-11), the EWG independently represents an electron attracting group. p and q represent independent 0 to 4, respectively, and r represents 0 to 6. However, when the above base has (EWG)P and (EWGX base, l$p + q$8, with (EWG)r and (EWGX basis, l$r + qS10. Preferably p= q=r=l ° Further, the EWG is preferably substituted for a hydrogen atom bonded to a carbon atom having an r position with respect to the carbon atom corresponding to Cl. (D-1) is more preferable from the viewpoint of ease of manufacture, especially (D-1-1) represented by the following formula is preferred. 26 320352 200909413

(wherein EWG represents an electron attracting group such as --, -CN_, -CF3_). Further, the partial hydrogen atom contained in the above-exemplified structure as D1 and D2 may be a group having a carbon number of about 1 to 4 Å through a methyl group, an ethyl group, an isopropyl group or a third butyl group; An alkoxy group having an oxygen group or an ethoxy group having a carbon number of about 1 to 4; a fluorine atom, a gas atom, and a halogen atom; B1 and B2 respectively represent -CRR, ... - Csc_,, «-, one-to-one, -s-, _c(=0)1, _c(=〇)_〇_, one 〇_c (Lu, - 〇-C(=0)_〇_, _c(=s)_, -c(=s)_〇_,, -〇-c(=s)_o-, -CH=N~N, _c( =〇)_NR...(4)(4)_, -0CH2-, -NR-, -CH2〇-, -SCH2_, Confucian_, Pu ah (=〇)_〇_, -〇-C(=G)-aH:H- or Here, R & R, the subunit clearly represents a ruthenium atom or a thio group, and the alkyl group is preferably an alkyl group having a carbon number of from a methyl group or an ethyl group of from 4 to 4. Further, B1 and β2 are In the case of the same type of divalent group, it is preferable to be easy to manufacture. From the viewpoint of easiness of producing the polymerizable compound (1), β1 and Β2 of the formula (1)_ are -C (♦). , -(:(♦〇_, -OC(O)-, _〇-c(=〇)_〇_, -〇_, _s_ or single bond is preferred. 320352 27 200909413 § B1 and B2 are the above combinations The base time 'is improved in liquid crystallinity, and it is easy to form molecular alignment. XI and X2 each independently represent a divalent group represented by the formula (2). ^ _ --A3- B3 — —^ (2) ή 2) Medium 'A3 represents -C(=0)-C6H4-, divalent cyclic hydrocarbon group or divalent impurity In the case of the divalent cyclic hydrocarbon group or the divalent heterocyclic group, specifically, the divalent cyclic hydrocarbon group or the divalent heterocyclic group exemplified by A1 and A2 can be exemplified, and in terms of ease of manufacture, Is a 1,4-phenylene, 1,4-cyclohexylene, 3-methyl-1,4-phenylene, 3-decyloxy-1,4-phenylene, benzene ring carbon atom It is preferably substituted with a divalent group of 1 to 3 nitrogen atoms, especially fluorene, 4-phenylene, 1,4-cyclohexylene, 3-mercapto-1,4-phenylene, 3-methoxy The base-:ι,4_ is preferably a phenylene group. The above -C(=0)-C6H4_, a divalent cyclic hydrocarbon group or a divalent heterocyclic group may also be bonded to an alkyl group having 1 to 4 carbon atoms or a carbon atom. An alkoxy group, a fluoromethyl group, a difluorodecyloxy group, a nitrile group, a canister or a sulfonium atom of from 丨 to 4. Further, when XI and X2 are the same type of divalent group, they are easily produced.士. B3 means the same meaning as B2, in which the ease of manufacture and S 'by -COO)-, -C(four))-0_, -0_c(=0), , , -s~ or single bond Preferably, η represents an integer of 1 to 4. When n is 2 or more, structural units composed of A3 & B2 may be different from each other. 52 28 200909413 The viewpoint that the obtained polymerizable compound is easy to handle at the time of casting is preferably 1 or 2, especially when it is 1, it is easy to manufacture. E1 and E2 are respectively The alkyl group having 2 to 25 carbon atoms is independently represented, and the alkyl group having 4 to 12 carbon atoms is preferred. Although the hydrogen atom of E1 and E2 may be substituted by an alkyl group, an alkoxy group, a trifluoromethyl group, a difluoromethyloxy group, a nitrile group, a nitro group or a halogen atom, it is preferably an unsubstituted one. When E1 and E2 are the same type of alkylene group, they are easy to manufacture. P1 and P2 each independently represent a hydrogen atom or a polymerizable group. Here, the term "polymerizable group" means a substituent capable of polymerizing the polymerizable compound of the present embodiment, and specific examples thereof include a vinyl group, a p-stilbene group, an acryl group, and a methyl group. Acrylsulfonyl, carboxyl, methylcarbonyl, hydroxy, decylamino, alkylamino having 1 to 4 carbon atoms, amine group, epoxy group, oxetanyl group, aldehyde group, isocyanate group, In addition, in order to allow the above-exemplified groups to be bonded to E1 and E2, the polymerizable group may contain a group represented by B1 and B2, and in addition, it is easy to handle the photopolymerization. In order to make it easy to make ', it is preferred to use acrylonitrile or fluorenyl fluorenyl, especially for propylene. ^ At least one of P1 and P2 is a polymerizable group, and both P1 and P2 are polymerized. In the case of a base, the enthalpy hardness of the obtained optical film tends to be different. 320352 29 200909413 Specific examples of the polymerizable compound (1) include, for example, 式_幻, (1_B) and (j-C). And etc., wherein, in the formula, nl is 2, n2 is 2 to 8, R, is a compound of a hydrogen atom It is made by Rong Li, and it can suppress the wavelength dispersion of the optical film.

(In the formulae (1 A) to (i__c), nl each independently represents an integer of 1 to 3 to independently represent an integer of 2 to 14, respectively; R" independently represents a gas atom or a methyl group). Specific examples of the compound (a polymerizable compound represented by the following formula (1-2) (1 3 )) 320352 30 200909413

The method for producing the polymerizable compound (1) may, for example, be a carbonyl compound having a structure of Cl, D1 and D2 and a carbonyl group, and the carbonyl compound may contain A1 (A2), B1 (B2), X1 (X2). a method in which a compound of E1 (E2) and P1 (P2) acts and is condensed, and the like. A compound containing A1 (A2), B1 (B2), X1 (X2), E1 (E2), and P1 (P2) can be made to contain A1 (=A2), B1 (=B2), and X1 (=X2). ), E1 (=E2), Ρ1〇Ρ2) compounds of various structural units are condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction, benzylation reaction, fungus head (sonogashira) Reaction, Suzuki-Miyaura reaction, root-bank reaction, Kudama reaction, Lushan reaction, Buchwald-Hartwig reaction, Wittig reaction, Friedel-Crafts reaction, Heck reaction, 31 320352 200909413 Aldol ( Aldol) is prepared by combining a reaction or the like. An embodiment of the optical film of the present invention is an optical film containing a structural unit derived from the polymerizable compound (1). In the optical film of the present embodiment, a plurality of different polymerizable compounds (1) may be used as the polymerizable compound (1). The optical film of the present embodiment may be an optical film containing only a structural unit derived from the polymerizable compound (1), or may contain a polymerizable compound having a liquid crystal property different from the polymerizable compound (1) (hereinafter also referred to as " The structural unit of the liquid crystal compound "). When a structural unit derived from a liquid crystal compound is contained, it tends to increase the alignment factor and further increase the phase difference. In this case, when the polymerizable compound (1) is copolymerized with the liquid crystal compound, the polymerizable group of P1 and/or P2 contained in the polymerizable compound (1) and the polymerizable group of the liquid crystal compound can react with each other. The polymerizable group is particularly preferred because it is easily photopolymerized when it is an acrylonitrile group. Further, the wavelength dependence of the refractive index of the obtained optical film can be controlled by changing the content of the structural unit derived from the polymerizable compound (1) contained in the optical film and the content of the structural unit derived from the liquid crystal compound (wavelength) dispersion). Specific examples of the liquid crystal compound include, for example, a liquid crystal handbook (Limited by the Liquid Crystal Handbook Compilation Committee, Maruzen (issued), issued on October 30, 2009). Chapter 3 Molecular Structure and Liquid Crystallinity 3. 2 Non-chiral (nonchira 1) A compound having a polymerizable group among the compounds described in the rod-like liquid crystal molecules and the chiral rod-like liquid crystal molecules. In the case of a liquid crystal compound, several different liquid crystal compounds may be used in combination. 32 320352 200909413 The liquid crystal compound may, for example, be a compound represented by the following formula (i), formula (π), formula (m) or formula Ον). P110-B110-E110- (B120-A110) S-B130-E120-B140-P120 (I) P110-B110-E110- (A110-B120) S-E120-B130-P120 (II) ΡΠ0-Β110-Ε110- (B120-A110) S-F110 (III) P110-B110-E110- (B120-A110) S-B130-F110 (IV) Further, in the above formula (I), formula (II), formula (melon) or In (IV), A110 each independently represents a divalent cyclic hydrocarbon group, a divalent heterocyclic group, a fluorenylene group, an oxyphenylene group or a sulfur-extended phenyl group. In A110, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or a halogen atom may be bonded. B110, B120, B130, and B140 represent independent -CRi Ri ' -, -C = C-, -CH=CH-, -CH2-CH2-, -〇-, -S-, -C(=0)-, respectively. , -C(=0)-0---0-C(=0)-, -〇-C(=〇)-〇_, _c(=s)_, -C(=S)-〇-, -〇-C(=S)-, -0-C(=S)-〇-, -CH=N-, -N=CH-, -N=N_, -N(4〇)=N-,- N=N(—〇)-, -COCOn,-, -NRi -C(=0)-^-OCH2-'-NR^ - '-CH2O---SCH2->-CH2S-' -CH=CH -C(=0)-0-, -〇-C(=0)-CH=CH- or a single bond (still, Ri, and Ri each independently represent a hydrogen atom or a burnt number of 1 to 4 carbon atoms) . E110 and E120 each independently represent an alkylene group having 2 to 25 carbon atoms. Further, E110 and E120 may also bond an alkyl group having a carbon number of 丨 to 5, an alkoxy group having 1 to 5 carbon atoms or a halogen atom. The difluoromethyl group or the fluorines P110 and P120 each independently represent a polymerizable group. F110 represents a halogen atom such as a hydrogen atom, an alkyl group, a nitrile group, a nitro group or an atom. 320352 33 200909413 s respectively represent an integer '1 to 5' and preferably 1 to 3. When s is 2 to 5, the structural units composed of A110 and B120 may be the same or different from each other. The liquid crystal compound may, for example, be a compound represented by the following formulas (1_1) to (1-15), -(CH2V~〇.H2〇5S〇H-^00-(ΟΗ^4·~〇' H2〇=CH^- COO^(CH2)e"0 HjOCH-COOKCH^-aCDO^

;〇-<CH2)s-OCO-CH-CH2 -(1-3) ^0^)2^-000-^===(3⁄4 (bu f) COO^CH2)4-〇C0-CH- CH2 (1-5) 000-^^-0-(^2^--000 CH==CH2 (1-1) -0C0-CH=CH2 (Bu 25 (1-65 H2£>=PH-CQO -(QH2)4~^( CH2)*— 0C0 -CH=CH2

©Q-iCH^e-O. H2p=CH—COO-(CH2)4· H2〇=CH—C0Q-(CH^ri H2p=CH-.COO^CH^4~-〇.

h^h^oo^ch.hs-O-cod (1-7) -(Cti2)4-PC〇; -ch=ch2 (1-8) :CH2>e-〇C〇^H-CH2 (4)) HCH^e-ocO (1-10) (1-11) ~^^^-0-<CH2)6-〇CX>-CH=pH2 34 320352 200909413 H2C=CH—Ό.~(Cfl2)6: ~〇~ H2C—OH—Ο—(^82)4;~Q-

Br

^—^一Ο-t(GH2)4-^〇'r^CH=CH2 QA/fe (Η3> ^-~Ο-(QH^g·-〇—CH=CH2

OMe (1-14) 0 (1-15) or a compound (CH2)e-CH3 H2 <>>CH-COO-(CH2)8-Ο represented by the formula (Dish-1) to (nr-6) H2G=CH-COO-(CH2)4-(

(III-1) απ-2)

Or a compound represented by the formula (IV-1) to (IV-6), etc., is preferable because it is easy to obtain. 35 320352 200909413 (IV,1) (IV-2) (IV-3) H2C=CH-Cbp-(CH2)5-0C00-^^~C00-^J)—och3 H20=CH*CQ0-(CH2 )0-^)~~^^-C00-(CH2)7-CH3 H2〇=CH—COO-(CH2)4~〇—~OCQ~^°^~OCflHi7

(IV-4) (IV-6) The wavelength dispersion characteristics of the optical film of the present embodiment can be arbitrarily determined depending on the content of the structural unit derived from the polymerizable compound (1) in the optical film. When only the liquid crystal compound is used without using the polymerizable compound (1), the obtained optical film is a film which exhibits a positive wavelength dispersion. Further, by increasing the content of the structural unit derived from the polymerizable compound (1) in the structural unit in the optical film, the wavelength dispersion can be arbitrarily moved in the reverse direction by the positive wavelength dispersion. Specifically, the composition containing the liquid crystal compound and the polymerizable compound (1) is prepared by preparing about 2 to 5 kinds of compositions having different amounts of structural units derived from the polymerizable compound (1), and then forming the respective compositions. An optical film of the same thickness was obtained in the manner described later, and the phase difference of the obtained optical film was determined. From the results, the correlation between the content of the structural unit derived from the polymerizable compound (1) and the phase difference of the optical film was determined. Further, the content of the structural unit derived from the polymerizable compound (1) required for 36 320352 200909413 may be determined by the correlation relationship obtained in order to obtain the phase difference required for the optical film in the film thickness. An example of the method for producing an optical film of the present invention is as follows. The structural unit derived from the polymerizable compound (1) and the optical film of the liquid crystal compound of the present embodiment can be described as follows. ''In the case of a human compound (1), a liquid crystal compound, and an organic solvent, 1 is added to a polymerization initiator, a polymerization inhibitor, a photo-sensitizing 曰1 乂 ear^, a leveling agent, and the like, and then prepared into mixture. In particular, it is preferable that the organic solvent is not contained in the film formation because the film formation is easy, and the poly σ ε 〜1 system has a function of hardening the optical film. The total amount of the polymerizable compound (1) and the liquid crystal compound in the mixed solution is equal to the total amount of the polymerizable compound (1) and the liquid crystal compound, and the polymerizable compound (1) is 1 to 50 parts by weight, or 3 is severely damaged. 'It is preferably from 1 to 30 parts by weight. When it is 1 part by weight, 1 = it is preferable that the positive wavelength is dispersed in the reverse direction by the stomach, and when the dO f is less than 1 part, it is preferable because it can be made into an inexpensive optical film. L polymerization initiator] In the case of the optical film of the present embodiment, a polymerization initiator is usually used in order to polymerize the liquid crystal compound and the chemical substance (1). In the preferred embodiment of the present invention, a liquid crystal compound or a polymerization initiator is preferably used. The method of combining DM 'this' polymerization initiator is carried out by photopolymerization*, a starter, a benzyl ketal, a salt, etc., and more specifically, for example, a benzoin or a diphenyl ketone ~ ketones, amino ketones, sulfonium salts, strontium. 'For example, Irgacure 907, Irgacure 320352 37 200909413 819, Irgacure 184, Irgacure 651, Irgacure 250, and Irgacure 369 (all of which are manufactured by Ciba Specialties Chemical Co., Ltd.), Seikuol BZ, Seikuol Z, and Seikuol BEE (above, All are manufactured by Seiko Chemical Co., Ltd.), Kayacure BP100 (manufactured by Sakamoto Chemical Co., Ltd.),

Kayacure UVI-6992 (manufactured by Dow Co., Ltd.), Adekaoptomer-SP-152, and Adekaoptomer-SP-170 (all of which are manufactured by Asahi Kasei Co., Ltd.). In addition, when the amount of the polymerization initiator is 100 parts by weight based on the total of the liquid crystal compound and the polymerizable compound (1), it is usually from 0.1 part by weight to 30 parts by weight, and from 0.5 part by weight to 10 parts by weight. It is better. As long as it is within the above range, the alignment property of the liquid crystal compound is not disturbed, and the polymerizable compound (1) can be polymerized. [Polymerization inhibiting agent] When preparing the optical film of the present embodiment, a polymerization inhibiting agent can also be used. Examples of the polymerization inhibitor include hydroquinones such as hydroquinone, hydroquinones having a substituent such as alkyl ether, and catechols having a substituent such as an alkyl ether such as butyl catechol, and pyrodal 1〇1. Free radical scavengers such as 2, 2, 6, 6-tetramethyl-hydrazine-a-cyloxy radical, sulfur, /3 -naphthylamine and naphthol. By using a polymerization inhibiting agent, the polymerization of the liquid crystal compound or the polymerizable compound (1) can be controlled, and the stability of the obtained optical film can be improved. In addition, the amount of the polymerization inhibitor is usually from 0.1 part by weight to 3 parts by weight 'and from 0.5 part by weight to 1 part by weight based on 100 parts by weight based on the total of the liquid crystal compound and the polymerizable compound (1). The parts by weight are preferred. As long as the alignment property of the liquid crystal compound is not disturbed within the above range, the polymerizable compound 38 1 320352 200909413 (1) can be polymerized. [Photosensitizer] When the optical film of the present embodiment is prepared, a photosensitizer can also be used. The photosensitizer may, for example, be x _ (xanthone), thiopurine or the like, or a hydrazine having a substituent such as an alkyl ether; a porphyrin n well or a ruthenium (Rubrene) ° The polymerization of the liquid crystal compound or the polymerizable compound 〇) can be made highly sensitive by using a photosensitizer. The amount of the photosensitive sensitizer is usually from 0.1 part by weight to 30 parts by weight, based on 100 parts by weight, based on the total of the liquid crystal compound and the polymerizable compound (1), and is 0.5 parts by weight to 10 weights are better. As long as it is within the above range, the alignment of the liquid crystal compound is not disturbed, and the polymerizable compound can be polymerized. [Leveling Agent] Further, when the optical film of the present embodiment is prepared, a leveling agent can also be used. The leveling agent may, for example, be an additive for a radiation hardening coating (by BYK, manufactured by Chemie: BYK-352, BYK-353, BYK-36), a coating additive (manufactured by Toray Dow Corning: SH28PA, DC11PA, ST80PA), And coating additives (manufactured by Shin-Etsu Lee Co., Ltd.: KP321, KP323, X22-161A, KF6001). The optical film can be made smooth by using a leveling agent. Further, in the production process of the optical film, the fluidity of the mixed solution containing the polymerizable compound (1) or the crosslinking density of the optical film obtained by polymerizing the liquid crystal compound or the polymerizable compound (1) can be controlled. At the same time, the specific value of the amount of the leveling agent used is 'in comparison with the liquid crystal compound and the polymerizable compound (1). 39 320352 200909413 Lu 10 is 10 sold ' 晷 / 8 π 士 ^ 77 τ ' is usually 〇 · 1 The parts by weight are preferably 30 parts by weight, and more preferably the weight of the person is from h summer to 1 g. As long as it is within the above range, the alignment of the liquid crystal openings is not disturbed, and the polymerizable properties can be combined. [Organic solvent], the organic solvent of the mixed solution of the polymerizable compound (1) and the liquid crystal compound, and the organic solvent which can dissolve the polymerizable compound (1) and the liquid crystal 2 σ substance, specifically, for example, Such as methanol, ethanol, ethylene glycol, ',, propanol, methyl cellosolve, butyl race, 3⁄4 and other alcohol solvents; acetic acid B, acetate acetate, ethylene glycol Ester ester solvents such as phthalic acid esters, T - ~r rin • 7 butane phthalate, propylene glycol methyl ether acetate; acetamidine, methyl ethyl ketone, cyclopentanyl, cyclohexanone, methyl amyl Ketone, methyl isobutyl, network, etc., solvent, n-hexane, heptane and other aliphatic hydrocarbon solvents; toluene-toluene, benzene and other aromatic hydrocarbon solvents; acetonitrile, propylene glycol monomethyl is| , dimethoxyethane, lactic acid, chloroform, and the like. These organic solvents may be used singly or in combination of several kinds. Among them, the composition of the present embodiment is excellent in compatibility, and can be dissolved in an alcohol, an ether A agent, a ketone solvent, a non-chlorinated aliphatic hydrocarbon solvent, and a non-gas aromatic hydrocarbon solvent. Even if a halogenated hydrocarbon such as chloroform is not used, it can be dissolved and applied. The viscosity of the mixed solution containing the polymerizable compound (1) and the liquid crystal compound can be adjusted to such an extent that it is easy to apply, and is usually at least 1 ÅPa · S and preferably from about 0.1 to 7 Pa · S. Further, the solid content concentration in the above mixed solution is usually from 5 to 5 % by weight. When the concentration of the solid portion is 5% or more, the optical film is not made too thin, and the optical compensation for the liquid crystal panel tends to provide the necessary optical anisotropy. In addition, when it is less than 5% by mole, since the viscosity of the above mixed solution is low, there is a problem that it is difficult to make the film thickness of the optical film - the τ - - 佳 τ - Next, the mixed solution is coated After the substrate is supported, dried and polymerized, the desired optical film can be obtained on the support substrate. When P1 and/or P2 contained in the polymerizable compound (1) and the polymerizable group contained in the liquid crystal compound are photopolymerizable, light such as visible light, ultraviolet light, or laser light can be irradiated and cured; The polymerizable group is thermally polymerizable', and it can be polymerized by heating. From the viewpoint of film formation, photopolymerizers are preferred, and from the viewpoint of handling properties, those which are polymerized by ultraviolet light are particularly preferred. When the solvent is dried, in order to improve the film formability in the case of photopolymerization, it is preferred to dry the solvent almost before the photopolymerization to obtain an unpolymerized film. Further, in the case of thermal polymerization, drying and polymerization are usually carried out at the same time. However, a method of obtaining an unpolymerized film by almost drying the solvent before the polymerization is preferred because it has excellent film formability. The method of drying the solvent may, for example, be natural drying, ventilating drying, or reduced pressure. The specific heating temperature is preferably from 1 Torr to 12 〇 ° C, and more preferably from 25 to 801 °. At the same time, the heating time is preferably from 1 second to 60 minutes, and from 30 seconds to 30 minutes. When the heating temperature and the heating time are within the above range, a supporting substrate which is not necessarily sufficiently heat resistant may be used as the supporting substrate. The coating method of the support substrate may, for example, be an extrusion coating method, direct 41 320352 200909413 direct gravia coating, reverse gravure coating method, cap coating method (CAP coating), die coating method, or the like. Meanwhile, for example, a method of using, for example, a dip coater, a bar coater, a spin coater, a "coating machine", a squeegee-coating method, a method, and the like can be cited. It is sufficient that an alignment film can be formed on the support substrate. Examples thereof include glass, plastic sheets, plastic films, and translucent films. Further, the light transmissive film may, for example, be a polyolefin film such as polyethylene, polypropylene or a norbornene polymer; a polyvinyl alcohol film, a polyethylene terephthalate film, a polydecyl acrylate film, or a poly Acrylate film, cellulose ester film, polyethylene naphthalate (PEN) film, polycarbonate film, polyfluorene film, polyether film, polyether ketone film, polyphenylene sulfide (p〇lyphenylenesulfide) , PPS) film, polyphenylene oxide film, and the like. In the optical film-based film which is usually obtained by the liquid crystal compound and the polymerizable compound, for example, in the step of using the film bonding step of the embodiment, the step of transporting or storing the film, and the like, the strength of the film is required. It is also possible to use a supporting substrate so that it can be prevented from being damaged or the like and can be handled easily. In the film of the present embodiment, it is preferred to apply a mixed solution after forming an alignment film on the support material. The alignment film must have heat resistance which is not dissolved by application of the mixed solution containing the polymerizable compound (1), heat treatment by solvent removal or liquid crystal alignment, and is not rubbed. The resulting friction or the like causes peeling or the like; and it is a polymer or a composition containing a polymer. The above polymer may, for example, be a polyamine or a gelatin having a guanamine bond in the molecule, a polyimine having a quinone bond in the molecule, and a hydrolyzate thereof. Poly 320 352 42 200909413 Amino acid (polyamic arirn ^ aCld) ), polyvinyl alcohol, alkyl modified polyvinyl alcohol, polypropylene decylamine, polycarbazole, flat 7 __ μ ^ * & 'Pingyi E-amine, polyacrylic acid, polyacrylic acid bismuth polymer. These polymers may be used singly or in combination of two or after forming a copolymer. The polymer can be easily obtained by polycondensation such as deamination or radical polymerization, anionic polymerization, cationic polymerization or the like, riding, coordination polymerization or riding polymerization. Further, these alignment film materials can be dissolved after being dissolved in a solvent. Although the solvent is not particularly limited, specific examples thereof include water, an alcohol solvent such as alcohol, ethanol, ethylene glycol, isopropanol, propylene glycol, methyl ceramide, and butyl thioacetate; Vinegar, ethylene glycol methyl ether acetate, r-butane vinegar, propylene glycol methyl ether acetate vinegar and other vinegars are dissolved! Ketones such as propyl, decyl ethyl hydrazine, cyclopentanone, cyclohexanone, methyl amyl ketone, methyl isobutyl ketone, etc.; tetraburn, hexanyl, heptyl aliphatic hydrocarbon solvent; toluene, An aromatic hydrocarbon solvent such as xylene or benzene; acetonitrile, propylene glycol monomethyl ether, tetrahydrofuran, dimethoxyethane, ethyl lactate, chloroform, and the like. These organic solvents may be used singly or in combination of several kinds. A commercially available alignment film can also be used as it is for the alignment film. As for the commercially available aligning film, there are SUNEVER (registered trademark, manufactured by Nissan Chemical Co., Ltd.) and 〇.pTMER (registered trademark, JSR system), etc., for the application of the polarizing uv to the photosensitive polyimide. For the modified polyvinyl alcohol, there are p〇VAL (registered by Zen, Kuraray). As long as such an alignment film is used, since the refractive index is not controlled by stretching, the in-plane dispersion of birefringence can be made small. Therefore, it is possible to provide an effect of a large optical film of 43 320352 200909413 which can also correspond to the enlargement of the FPD on the support substrate. The method of forming an alignment film on the support substrate may be, for example, an application of an alignment film on the support substrate after the material of the alignment film is applied onto the support substrate. The thickness of the alignment film of the tooth decay is usually 10 nm to 10, OOO nm, and preferably 100 nm to 1, 〇〇0 nm. In the optical anisotropic layer forming step to be described later, the polymerizable compound (1), the liquid crystal compound, and the like are aligned on the alignment film to a desired angle.

In addition, such an alignment film can be rubbed or polarized with UV light for necessity. Thus, the polymerizable compound (1), the liquid crystal compound, and the like can be aligned to a desired direction. As for the nibbing method of the alignment film, for example, a method in which a rubbing roller that has been wound with a rubbing cloth and is rotating is carried on a stage and brought close to the alignment film being transported can be used. [Preparation Step of Unpolymerized Film] When an alignment film is formed on a support substrate, a mixed solution containing the polymerizable compound (1) and a liquid crystal compound can be applied onto an alignment film and dried to obtain an unpolymerized film. . When the unpolymerized film exhibits a liquid crystal phase such as a nematic phase, it may have birefringence due to monodomain alignment. Since the unpolymerized film is at about 〇 to 12 〇. In the crucible alignment (and preferably 25 to 8 (the low temperature of TC), when used as an alignment film, a support substrate having heat resistance as exemplified above may not be used sufficiently, and even after cooling to about 30 to 10. 〇, it does not crystallize. [Polymerization step of unpolymerized film] 44 320352 200909413 The polymerization step of the unpolymerized film is obtained by polymerizing the unpolymerized film obtained in the above step of preparing the unpolymerized film and then curing it. Thereby, the liquid crystal compound and the polymerizable compound (1) can be made into an optically fixed film, that is, a polymer film. Therefore, the refractive index change in the plane direction of the film can be made small, and the normal direction of the film can be obtained. A polymer film having a large refractive index change. The method of polymerizing the unpolymerized film is determined by the type of the liquid crystal compound and the polymerizable compound (1). For example, the unpolymerized film can be polymerized by photopolymerization or thermal polymerization. In the present embodiment, in particular, it is preferred to polymerize the unpolymerized film by photopolymerization. According to this method, the heat resistance of the support substrate can be selected because the unpolymerized film can be polymerized at a low temperature. In addition, it is also easy to industrially manufacture. The method of photopolymerizing an unpolymerized film is, for example, a method of polymerizing an unpolymerized film by irradiating ultraviolet rays onto an unpolymerized film, etc. The optical film thus obtained That is, the liquid crystal polymer can be obtained without using a liquid crystal polymer. In the polymerization step of the unpolymerized film, the polymerizable compound (1) and the liquid crystal compound can be crosslinked by photopolymerization. The effect of the change in birefringence is affected. Further, it is not necessary to use a surface treatment agent such as a surfactant on the obtained optical film. In other words, the alignment film used in the optical film of the present embodiment is supported by the substrate. The adhesion to the alignment film and the adhesion between the alignment film and the optical film are good, and the optical film can be easily obtained. The optical film of the present embodiment has the same phase as the stretched film. In the case of film comparison of the difference, it is usually a film. 45 320352 200909413 In the method for producing an optical film of the present embodiment, the step of peeling off the base material may be included after the above steps. The film obtained by the above-described configuration is a film composed of an alignment film and an optical film. Further, in addition to the step of peeling off the support substrate, a step of peeling off the alignment film may be further included. The optical film formed by the optical film is a film composed only of an optical anisotropic layer. Further, after appropriately adjusting the amount of the coating liquid of the mixed solution or the concentration of the coating liquid, it is possible to prepare the desired phase. When the polymerizable compound (1) in the mixed solution is constant, the retardation value (Re) of the obtained optical film can be determined by the formula (6), and therefore When the desired Re (re) is obtained, it is only necessary to adjust the film thickness d.

Re( λ )=dxAn( λ ) (6) (wherein Re represents the phase difference at a wavelength of nm, d represents the film thickness, and η ( λ ) represents the refractive index anisotropy at another nm) . The optical film thus obtained is excellent in transparency and can be used as a film for various displays. The thickness of the layer formed is as described above because of the difference in phase difference of the obtained film. In the present embodiment, the thickness is preferably from 0.1 to 10/zm, and more preferably from 0.5 to 3 /z m from the viewpoint of reducing photoelasticity. As described above, in the step of preparing the unpolymerized film, an unpolymerized film (liquid crystal layer) is laminated on the alignment film laminated on any of the support groups #. Therefore, when compared with the method of producing a liquid crystal cell (cel 1) and injecting a liquid crystal compound into the liquid crystal cell, the production cost can be reduced. Also, a film of a roll film can be produced. 46 320352 200909413 When the alignment film is used to have birefringence, the usual retardation value is about 50 to 500 nm, and preferably 1 to 300 nm. By using a film having such optical characteristics, all liquid crystal panels or flat displays (FPDs) such as organic ELs can be optically compensated for a reverse wavelength dispersion by a film. / In order to use the optical film of the present embodiment as the /4 plate or λ/2 plate of the wide cheek band, the content of the structural unit derived from the polymerizable compound (1) can be appropriately selected according to the formula (6). σ, in the case of /4 plates, the phase: the value is as long as the film thickness is adjusted so that the obtained optical film can be used as a coffee, and preferably 135 to i40 nm, and preferably λ/2 plate, as long as the film thickness is adjusted so that the resulting optical film

Re (55 Å) is preferably 250 to 300 nm, and preferably 273 to 277 faces, preferably about 275 nm. When the optical film of the present invention is used as the optical film for the vertical alignment (VA, :r:3liinTent) mode, the structure can be selected by appropriately selecting the structural unit derived from the t-complex compound (1).相位 and 尬", , (6), ιηη p The phase difference Re (550) of the chamber is 40 to 0.1, and is preferably about 6 to 8 brilliant. The optical film of the photo-dissipation property of the embodiment is used as an anti-reflection film having an excellent wavelength, and an optical film having an excellent wavelength, for example, an anti-reflection (10) film or the like, and a penetrating liquid crystal 亍1 臈, The circular polarizing film and the wide viewing angle film are used, and the optical compensation film for three-view compensation of the present embodiment n is used. However, even if only one film is used, an excellent optical alpha laminate can be displayed. 47 320352 200909413 In addition, it may be combined with another film. Specifically, for example, a circularly polarizing plate in which the optical film of the embodiment is bonded to a polarizing film may be used, and this embodiment may be further applied to the circularly polarizing plate. The optical film of the form is a wide frequency band λ /4 plate A zoned circular polarizing plate, etc. Further, the film of the present embodiment may be used in a phase difference plate of a reflective liquid crystal display or an organic electroluminescence (EL) display, and the phase difference plate or the optical film may be provided. The flat display device is not particularly limited, and examples thereof include a liquid crystal display device (LCD) or organic electroluminescence (EL). The film of the present embodiment can be used in a wide range of applications. For example, a polarizing plate in which the optical film and the polarizing film of the present embodiment are laminated, and a flat display device including the polarizing plate are described below. The polarizing plate of the present embodiment is a film having a polarizing function, that is, The optical film may be bonded to one surface or both surfaces of the polarizing plate directly or by using an adhesive or an adhesive. However, in the following descriptions of the first and second drawings, the following may be followed. The agent or the adhesive is collectively referred to as an adhesive. In the first embodiment (a) to the first embodiment (e), (1) an embodiment in which the optical film 1 and the polarizing film layer 2 are directly bonded together (first) Figure (a)); (2) make An embodiment in which the film 1 and the polarizing film layer 2 are bonded together via the adhesive layer 3 (Fig. 1 (b)); (3) The optical film 1 and the optical film are directly bonded together, and then the optical film is bonded An embodiment in which the polarizing film layer 2 is directly bonded (Fig. 1 (c)); (4) the optical film 1 and the optical film are bonded together via the adhesive layer 3, and the optical film and the polarizing film layer are bonded together. 2 embodiment of direct bonding (Fig. 1 (d)); and (5) bonding the optical film 1 and the optical film Γ via the adhesive layer 3 to 48 320352 200909413, and then optically bonding the polarizing film layer 2 The embodiment in which the adhesive layer 3 is bonded to each other (Fig. 1(e)), etc. The polarizing plate of the present embodiment is obtained by bonding a polarizing film and an optical film of the present embodiment. As the optical film (hereinafter sometimes referred to as a liquid crystal layer), a film containing only a structural unit derived from the polymerizable compound (1) may be used, or a laminated film composed of a supporting substrate, an alignment film, and a liquid crystal layer may be used, and A laminated film composed of an alignment film and a liquid crystal layer. In the polarizing plate of the present embodiment, a plurality of optical films may be laminated, and the optical films of the plurality of layers may be all made of (4), or may be used in combination. More specifically, the polarizing plate of the present embodiment can be exemplified as shown in Figs. 2(a) to (k). In Figs. 2(a) to (e), a film composed of a liquid crystal layer u or a liquid crystal layer 11 (optical anisotropic layer) and an alignment film layer 12 or an alignment film layer 12 is used as an optical film. 1 and optical film 1, Fig. 2 (a) to (e) are compositions in which the optical film 1 and the polarizing film layer 2 are directly bonded together (Fig. 2 (a)), and the film 1 and the polarizing film layer 2 are interposed via the adhesive layer 3 And the composite, Wei Cheng (Fig. 2 (b)); optical film! a composition in which the optical film i' is directly bonded to each other and the optical film Γ and the polarizing film layer 2 are directly bonded together (Fig. 2(c)); the film 1 and the optical film [adhered to the adhesive layer 3] a composition in which the polarizing film layer 2 is directly bonded to the optical film i (Fig. 2(d)); and a light film, the film 1 and the optical film are bonded together via the adhesive layer 3, and then the optical film 1 is bonded. A composition which is bonded to the polarizing film layer 2 via the adhesive layer 3 (Fig. 2(e)). Further, in FIGS. 2(f) and (g), a film composed of a liquid crystal layer 11 or a liquid layer 49 320352 200909413 crystal layer 11' is used as the optical film 1 and the optical film 丨 in the optical film 1. The alignment film layer 12 or the alignment film layer 12 is not contained. Further, in Fig. 2(f), the optical film 1 and the polarizing film layer 2 are bonded together via a pair of adhesive layers 3. On the other hand, in Fig. 2(g), the optical film j and the optical film are bonded together via the adhesive layer 3, and the polarizing film layer 2 is bonded to the outside via the adhesive layer 3'. . Fig. 2 (h) shows the same structure as Fig. 2 (f). However, unlike the second figure (1), the alignment substrate layer 12 formed on the surface of the support substrate 13 and the liquid crystal layer 11 formed on the surface of the alignment film layer 12 are used. The layered body (film) is used as the film j. - Figure 2 (i) shows the same structure as Fig. 2 (g). However, the difference from the second figure (g) is that the film layer is formed on the surface of the support substrate 13 or the support substrate 13 using the support substrate 13 or the support substrate 13'. 12 or an alignment film layer 12', and a laminate (film) of a liquid crystal layer u formed on the surface of the alignment film layer 12 or the alignment layer 12 as the optical film 1 or the optical film 1. Fig. 2 (j) and (1) show the same configuration as Fig. 2 (g). However, the second film (1) is used as an optical film, and the material selected from w, the alignment film layer 2, and the # substrate 13 is used as an optical medium. (1) The ruthenium film is formed as an optical frame, and the ray Z and the support substrate 13 are white. The film formed of the liquid crystal layer 11 as the other polarizing film layer may be a film having a polarizing function, and may be exemplified. For example, 320352 50 200909413 A film in which a polyethylene film is adsorbed by a hard or dichroic dye, or a film in which a polyvinyl alcohol film is stretched or a dichroic dye is used. γ is used in an adhesive layer. 3 and the adhesive of the adhesive layer 3' are preferably an adhesive which is excellent in heat and excellent in heat and good in heat. For such an adhesive, for example, an acrylonitrile-based, epoxy-based or polycarbamic acid can be used. Cool (10)) is an adhesive or the like. Further, in the polarizing film, as shown in Fig. 1 (c) to Fig. 1 (e), the photoprecipitated film may be bonded to one to three layers in accordance with necessity. In the case of the light-receiving film of the embodiment, the light-receiving film of the embodiment includes, for example, a partial lens that has been bonded to the embodiment. A liquid crystal display device of a liquid crystal panel of a film and a liquid plate; or an organic electroluminescence light (hereinafter also referred to as "el", an organic EL display device of a panel) having a polarizing film and a light-emitting layer bonded to the present embodiment. The liquid crystal display device and the organic EL display device will be described in detail below with reference to the liquid crystal display device and the organic EL display device. The liquid crystal display device may include, for example, a liquid crystal panel of the liquid crystal panel shown in FIG. The liquid crystal panel is bonded by the polarizing film 4 of the present embodiment and the liquid crystal panel 6 via the adhesive layer 5. According to the above-described embodiment, after the voltage is applied to the liquid crystal panel, an electrode (not shown) is used. In the liquid crystal molecule, the effect of the light shutter can be exhibited. [Organic EL display device] The organic EL display device includes, for example, an organic EL display device including an EL panel shown in Fig. 4. The organic anal panel is applied. The polarizing film 4 and the light-emitting layer 7 of the form are bonded to each other via the adhesive layer 320352 51 200909413 The polarizing film 4 in the above-described organic EL panel has a wide-band circular polarizing plate. At the same time, the light-emitting layer 7 is a layer of at least one layer composed of a conductive organic compound. In another embodiment of the compound of the present invention, the & compound represented by the formula (n) is sometimes referred to as " The compound (1)))) or a compound represented by the formula (9) (hereinafter sometimes referred to as "compound (21)").

(21) Here, the EWG independently represents an electron attracting group. The electron attracting group may, for example, be a nitro group, a nitrile group 'trifluoromethyl group or a fluorine group. Pl and ql each independently represent any integer from 〇 to 4. However, ^ Spl + ql$8, especially pi=qi = i is preferred. Field pl-ql-l%, in the case of the compound (U), the bonding position of EWg in the benzene ring is preferably a position in which a carbon atom represented by "^" in the following formula is bonded; In the case of (2)), it is preferred to combine the position of any carbon atom represented by 1j to "lllj" in the following right formula.

320352 52 200909413 八 "and Au respectively represent 丨, 4_ phenyl, on the 丨, 4 phenyl" can also be combined with thiol, ethyl, isopropyl, tert-butyl, etc. a secret of a carbon atom number of 丨纟4; at least one substituent group of a group of alkoxy groups having an alkyloxy group and an oxy group having from 1 to 4 carbon atoms.

Bn, B21 and B 31 respectively represent _〇_, _s_, _c(=〇)_, -0CH2-, -0-C(=0)-0- or a single bond to an alkyl group or a hydrogen atom of 4 . XI represents a divalent group represented by the formula (3) -C(=〇)-〇-.-〇-c(=〇)-._c(=〇)_NRi, __NRi, _c(=〇)_ here' h, indicating the number of carbon atoms

A 31

B 41 quinone of η (3) In the formula (3), A31 represents a -C(=〇)-C6H4-, a 5- to 20-membered hydrocarbon group or a 5- to 20-membered ring divalent heterocyclic group. Its =(=〇)-d, a cyclic hydrocarbon group or the heterocyclic group may also be bonded: a number of carbon atoms such as I, methyl, ethyl, isopropyl, 筮_ 浐, n, (d) second butyl 1 to 4# ^"^, ethoxylated squaring carbon number... methyl, trifluoromethyloxy; nitrile; nitro = halogen atom such as desert atom. (4) Sub (four) children,

Plant-α, a The so-called divalent heterocyclic group refers to a divalent cyclic disulfide atom having a specific hetero atom and a carbon atom. "With or without an aromatic 320352 53 200909413, for example, a group having an aromatic divalent heterocyclic group is represented by the following formula.

For example, a group represented by the following formula which does not have an aromatic divalent heterocyclic group.

~0~, L is especially based on the formula (4-υ to formula (4-5)), and is based on the formula (4-2) and formula (4-5). For the piece.

Ν- (4) (4-2) (4) (4-4) (4-5) b41 means -CRl, Rl" -, - (four) ―, _cH=gh...id, -0- ' -S- > -C( =〇)- > -C(=0)-0-. -〇-C(.〇)- , -〇-C(=〇)_〇_

-CH=N->-N=CH^-C(=0)-NR/ - >-NR/ -C(=〇)- _〇CH ,i,-, -chi, -CH=CH- C(tetra))+, Ic(=〇)_ch=ch^ Single bond Here, R! and 仏 each independently represent an alkyl group having 1 to 4 carbon atoms or a hydrogen atom. η represents any integer from 1 to 4. When n is 2 to 4, the structural units composed of "and" may be identical to each other or may be different from each other. 1 As described later, n is an integer of 2 to 4 from the viewpoint of easy handling of the compound (1)) or the compound (21), and the viewpoint of improving the alignment of the compound. .

En represents an alkylene group having 1 to 12 carbon atoms. a hydrogen atom in a " may also be a methyl group, an ethyl group, an isopropyl group, a third butyl group, etc., having a number of atoms of 1 to 4; a oxy group such as a oxy group or an ethoxy group having a carbon number of up to 4 Oxyloxy; trifluoroindolyl, trifluoromethyloxy; guess base; exact base; or fluorine atom, chlorine atom, bromine atom and other dentate atom substitution. However, it is preferably not substituted. E21 represents an alkyl group or a cycloalkyl group having 1 to 12 carbon atoms. The group containing a methyl group, an ethyl group, an isopropyl group, a third butyl group and the like having a carbon number of 1 to 4; a methoxy group such as a methoxy group or an ethoxy group; a group; a trifluoromethyloxy group; a nitrile group; a soil, or a fluorine atom, a chlorine atom, a bromine atom or the like. Ρ π is a group represented by (P-1) to (P_5) or a hydrogen atom.

In the formula (P-l) SS (P-5), & to! ^ independently represents an alkyl group having 2 to 4 carbon atoms such as a methyl group, a group, an isopropyl group, and a t-butyl group. In the case of PlI, it is preferable that the structure of the right danma is ρ_υ to the formula (p_5) because the structure of the obtained fresh film from the compound (1) or (2) is easily fixed, especially (The base of ρ-υ is preferably. 320352 55 200909413 The method of producing the compound (11) and the compound (21) of the present embodiment, the carbonyl compound represented by the formula (11-B) and the formula (21-C) When the sulfhydryl compound is reacted with a phenol containing oxime such as phenol, o-nonyl phenol or 2-decyloxyphenol, the ketone compound is obtained by reacting the phenol compound with a phenol such as phenol, o-nonyl phenol or 2-decyloxyphenol, and then obtaining the formula (11_B_1) and formula (1). Bu B-2), a formula of (21-C-1) and a formula (21-C-2).

Next, by, for example, methyl iodide, ethyl iodide, n-propyl iodide, moth isopropyl, broken n-butyl, money second base, orbital cyclohexane, desertified isopropyl , brominated cyclopropyl, evolved isobutyl, brominated cyclobutyl, desertified n-pentyl, evolved second pentyl, evolved n-hexyl, brominated cyclohexyl, 淳320352 56 200909413 Cycloheptyl, brominated a compound capable of supplying Ez, such as n-heptyl, n-octyl bromide, n-decyl bromide, n-dodecyl bromide, n-tetradecyl bromide, n-hexyl chloride, n-octyl chloride, etc. A monophenol intermediate is obtained. The monophenol intermediate can also be re-refined by a Shixi rubber column chromatography or the like. Specific examples of the mono-introgress intermediate of the compound (11) of the present embodiment can be exemplified by the formula (1-A-1) to the formula (1-A-45). 57 320352 200909413

58 320352 200909413

\

(1-A-29)

59 320352 200909413

Specific examples of the monophenol intermediate to which the compound (21) of the present embodiment is supplied include, for example, the formula (2-A-1) to the formula (2-A-45). 60 320352 200909413

61 320352 200909413

(2-A-28) (2-A-29) (2-A-30) 62 320352 200909413

The compound (11) and the compound (21) of the present embodiment can be produced by reacting a single-aged intermediate with a compound having a structure in which Bu-X-En-B31-Pu is supplied. When Βιι is -〇C(=0)-, as long as the corresponding toluene, carboxylic chloride or carboxylic acid trimethylate compound is used as the supply 320352 63 200909413

The compound of the structure of Bn-X-L-B"-?11 can be used together with monophenol. When & is ♦, it is only necessary to use the corresponding substance.

The compound of the structure of Bn-X-Eu-Bsi-Pii can be esterified: "The compound which should be supplied with the structure of Bu-X-Eu-Bu-Pn can be mentioned, for example, by the formula (3-A-1) The carboxylic acid represented by the formula (3-A-124), the chloride of the carboxylic acid, and the like: wherein k in the formula represents each independently an integer of 1 to 12.

Jk> One (CH2)r〇^^H (4) -('〇~(CH2>»^<>〇-^h (3-A-2) (3-A-3) M^-〇-( CH2)jPj0^>^H (3_a_4) ==Λ0~(°Η2)κ0^〇--ξΗ(3-A-5) ^〇-(ΟΗ2)ίΡγ~ζ]}-^Η (3-α -6) 64 320352 200909413. Wide CH2)r〇~〇g OH (3-A-7)

-0—(CH2)jfO八 (3-A-8) Ο

〇-<CH2)r〇^ , Μ (3-A-9) OH ^0-{0Η2\-〇-〇-ζΗ (3—A-10)

Ό

PH Ο

. -{CH2)r〇~\ -〇-(CH2)f〇 (3-A-ll) (3Ά-12) (3-A-13) (3-A-14)

O

—(CH2)jt〇

0-

0

OH, 0,

-0 a (CH2)r〇H〇^Q^O~^H

〇-陶Γ<Η卜. H o—(CH2)ir〇Οζ^ζ〇-ζΗ (3-A-15) (3"A,16> (3-A-17) (3-Α*~18) 65 320352 200909413 _3~〇- (CH2)it〇

-(CHzk

QH (3-A-20) b Q. (3 十扣 ^〇-(C Mizhou 2)

b OH (3-A-24) O yo^cm-o-O^Q^ <3~A_23) 峨(3士25) Q .〇-(CH2)iP name. (3:26) 3-°-<CH2)ir

^-0-(03⁄4 OH 0 o "〇~(CH2)k

3·〇~_『〇·〇^

OH o (3-A-27) (3-A-28) (3-A-29) (3-A-30) (3-A-31) (3-A-32) (3Ά-33) ( 3-A-34) 66 320352 200909413

3^~(CH2)r〇-〇^-Q^^〇H (3*A~35) Q. -(CHzJtr

(3-A**36) -(CH々.〇^〇^〇i _3~〇-(叫-〇-〇~^〇_^〇~〇-<〇" (3-A-39 )々ο~(α3〇—(4)(3+42) jh2>t〇

^h〇-(CH2)r〇-(3_0v/=\vW~\ 0K><.3-^(CH2)r〇-〇^_^^-C^i^-(CH2)k-〇- Q^_Q^>-〇-( o

^-(CH2)rO-〇-〇)_^^0~0^〇H (3 士37) (3~A_38) (3-A-40) (3_A~4l) (3-A-43) ( 3-A-44) (3-A~45) (3~A~46) (3Ά~47) (3Ά~48) (3-A-49) (3-A-50> 320352 67 200909413 J-〇 -(CH2)Ir〇〇^H (3:51) -(CH2)r〇^Q^H (3士52) (3-A-53)

€Η2)Γ

Η (3- A-55) (3-A-56>

Η (3-A_58) pH (3-A-57)

pH (3~A~60) ^O-iCH^irO-O-^./~\ PH (3-A-61)

PH (3-A-€2)

68 320352 200909413 (3+65) 3-〇-(CH2)r〇^}-<° ο 七-<CH2)k-〇^^Q_^^Q^H3^^ι<^〇^ζΟ~ ζ (3~A~66)

(3-A-67) (3-A-68) 3^°~<CH2)ir〇〇-t o (3_Α·69) o

Q o (3-A-70) o

-O-iCH^-C 乂OH

(3-A-71) (3+72)

H-(CH2)kH3-(^-(〇H (3-A-74) (3-A-76) (3-A-73)

H~(CH2)r<〇^PH(3-A-75) H-(CH2)k-0-〇-(°_^^H Η_(〇Η^_ (3-A-77) (3- A-78) H-(〇H2)k-〇-^^^OH H-(CH2)k-CH° (3-A-80) (3-A-79) 200909413 Η—(CH2)k*

(3 -Α_83) Η—(ΟΗ2)τ〇-(3-ζ pH (3-Α-81)

(CH2)kH^3_^〇_.^^_^:>H (3-Α-84)Η - (CH2)r0_O~^Q_^O~^H Η-ι (3-A-85) H —(CH2)ri

(3~A - 86)

H-(CH2)r〇^〇^H〇^H (3 -A-87)

H—(Cl·^- (3 -A- 88) (3-A-89) (3-A-90) (3-A-91) ^<Η^}-ζ<ΗΗ (3-A- 92) 70 320352 200909413

H-iCH^rO

H-(CH2)k·

H—(CH2)i

Q H-陶!Γ<Η〇ξ^_^〇ξΗ

H-Wro-O^Q^O^HH-(CH2)trO〇^^K>^H H-(CH2)k- H-(CH2)k-

(3-A-93) (3-A-94) (3-A-95) (3-A-96) (3-A-97) (3-A-98) (3-A-99) ( 3-A-100) (3-A-101) (3-A-102) (3-A-1CS) (3-A-104) (3-A-105) (3-A-106) (3 -A-107) (3-A-108) 71 320352 200909413 H-(CH2)k-〇~〇·^

(3-A-109)

H one (CH2)

(3-A-11Q) (3-A-lll) (3-A-112) (3-A-113) (3~A~114) (3-A-115) (3-A-116) 72 320352 200909413 (3-A-117) s^〇~(CH2)ir〇-^^-^^-(〇H (3-A-118) (3-A-119) 々〇-(ch々0> 〇^^h (3_A_120) 3~.,2)1<-〇-〇〇~{_〇^〇^-(CH2)r〇-〇-〇^Q^〇: OH (3-A-121) pH (3-A-122) (CH2)k-0

(3-A-123) ^Ο-(0Η2), γ〇-{3^(3-A-124) A method for producing a compound represented by the formula (3-Al) to the formula (3-A-124) By compounding each structural unit containing octa 31, B31, B41, Βδΐ, E11 and Pli, for example, by condensation reaction, esterification reaction, Williamson reaction, Woolmann reaction, benzylation reaction, and bacterial head reaction , eucalyptus-gongpu reaction, root-bank reaction, Xiongtian reaction, Laoshan reaction, Bucherbaard-Hartway reaction, Wittig reaction, Friedel-Craits reaction, Heck reaction or acid-alcohol reaction are combined. Specifically, for example, the method of [0036] to [0040], the method of Japanese Patent Laid-Open Publication No. 2005-289980 ([0185]), Macromolecules, 27, 6722 to 6727 can be applied. (1994) method, Advanced Functional 73 320352 200909413

Materials, 15 volumes, methods from 1961 to 1972, etc. were prepared. The optical film of the present embodiment is an optical film containing a structural unit derived from at least one compound selected from the group consisting of the compound (11) and the compound (21) (hereinafter, also referred to as "the present compound"). The optical film of this embodiment can be obtained by polymerizing the composition containing the present compound. In addition, the compound may also contain a compound which is different from the compound (11) and the compound (21) and exhibits liquid crystallinity (hereinafter sometimes referred to as "liquid crystal compound"). An optical film containing a structural unit derived from a liquid crystal compound is preferred because of an increase in alignment and an increase in phase difference. In order to copolymerize the present compound and the liquid crystal compound, a polymerizable group in which the polymerizable group of Pi 1 contained in the present compound and the polymerizable group of the liquid crystal compound are mutually reactive is preferable, and in particular, a mutual polymerizable group is used. When it is a group represented by the formula (P-1), it is preferable because it is easily photopolymerized. Further, the wavelength dependence of the refractive index of the obtained optical film can be controlled by changing the content of the content of the structural unit derived from the present compound contained in the optical film and the content of the structural unit derived from the liquid crystal compound. Specific examples of the liquid crystal compound include, for example, a liquid crystal handbook (edited by the Liquid Crystal Handbook Compilation Committee, Maruzen Co., Ltd., issued on October 30, 2004). Chapter 3: Molecular Structure and Liquid Crystallinity 3.2 Non-chiral (nonchiral) A compound having a polymerizable group among the compounds described in the rod-like liquid crystal molecules and the 3.8 chiral rod-like liquid crystal molecules. The liquid crystal compound may also be used in combination with a plurality of different liquid crystal compounds. The liquid crystal compound may, for example, be a compound represented by the following formula (V), formula (VI), formula (VE), formula (M) or formula (IX). 74 320352 200909413 P210-E210-B210-A210-B220-A220-B230-A230-B240-A240-B250-A250-B260-E220-P220 (v) P210-E210-B210-A210-B220-A220-B230-A230 -B240-A240-B250-E220-P220 (VI) P210-E210-B210-A210-B220-A220-B230-A230-B240-E220-P220 (VII) P210-B210-B210-A210-B220-A220-B230 -A230-B240-F210 (VIII) P210-E210-B210-A210-B220-A220-B230-F210 (IX) In the above formula (V), formula (VI), formula (W), formula (Μ) and In (IX), hydrazine 210, hydrazine 220, hydrazine 230, hydrazine 240, and hydrazine 250 each independently represent a divalent cyclic hydrocarbon group, a divalent heterocyclic group, an aromatic hydrocarbon group, a mercapto group or a sulfur-extended phenyl group. On Α210, Α220, Α230, Α240 and Α250, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a nitro group, a nitrile group, a phenyl group or a decylamino group may be bonded. Or a halogen atom. Β210, Β220, Β230, Β240, Β250, and Β260 respectively represent independent -CR11R12-, _CeC~, -CH=CH_, -CH2-CH2-, -0-, -S_, _C(=0)_., _C( =0)_0-,-0-0(=0)-, _0_C(=0)-0-, -C(=S)-, -C(=S)-0-,-0_C(=S)_ , -CH=N_, -N=CH-, -N=N~~, -C(=0)-NRii_, _NRii_C(=0)-, -OCH2-, -OCF2-, -NRii-, -CH2O- , -CF2O-' -CH=CH-C(=0)-0---0-C(=0)-CH=CH- or a single bond, and Ru and R12 independently represent an argon atom or a fluorine atom, respectively. Or an alkyl group having 1 to 4 carbon atoms or a stretching group having 5 to 7 carbon atoms after the combination of Ru and R12. E210 and E220 each independently represent an alkylene group having 1 to 12 carbon atoms. E210 and E220 may also be bonded to an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogen atom. 75 320352 200909413 P210 and P220 are each independently shown as a polymerizable group. The alkyl group, the carbon atom difluoromethyl group, and the dimercaptoamine group F21Q of the formula (P-1) to the formula (P-5) are represented by a hydrogen atom and a hydrogen atom having a carbon number of from 1 to 13. A group, a nitrile group, a confirming group, or a halogen atom. Specific examples of the liquid crystal compound include, for example, the following formulas (HI) to (1-25), (II-1) to (11-6), ([(1) to (ΠΙ_29), (7) to (1) to (IV-24)). And a compound represented by (V-1) to (V-5), etc., wherein m in the formula each independently represents an integer of any of 1 to 12. 320352 76 200909413

(1-2»)

«>-(.咏〇-^_

J^>-(CH2k〇〇{_Q_Q_^〇~〇~(CH2)srO·^ 3-〇^CHz)m〇-Q-^-^^_^-Q-〇

'-(CHzte-C

(r-22) (1-23) (1-24) (1-25) (II-1) » (II-2) (11-3) (Π-4) (II-5) (II-6 ) 3203.52 77 200909413

(CH2)s (III-丨3) ==s/h°^CH2)ni~0 (III-(4) 3^〇-(CH2)fr〇~〇-^_^_^O〇~(CH2W〇^ (III-15) 3〇(CH2)rS-〇3~〇~丨(CH2)

:CH2)nr〇- (III-17)' (III-18) 3-°*(CH2) 3-° 丨一 (CH2)sr〇·

"(CH2)FF 'fir〇^= (III-19) 3^CH2>sr~〇^^"^C^0;~"^H^~0^CH2)fir〇^= (III- 20) 3-°

Vx -(CH^

-fCH2)sr〇

I (III-21) _^〇-(CH2)sr (III-22) 78 320352 200909413 Q-iCH^RrO-

(III-23) 3^(〇H^c>〇^q.K>^CH2)^ N〇2 3-chch^-ς^ 〇(III-24) (III-25) (III-26) ( III-27) (III-Z8) (III-29) 79 320352 200909413 -(CH2)firCH3 —^~°·(〇Η2)β~·丨j-OlCHsJsr-O』. -(cHzfer〇O-^Q_^~〇"°~ eJ^-(CH2)jir〇-{3^_^^~0_CN 3^(CH2)fiT°

(CH^srCHs

=>°~

o y〇i{ :CH2)i P^sr 丨

-(CH^fir-CHj (IY-11) (IV-12) (IV- 13) (IY-14) (IV-15) (IV-16) (IV-17) (IV-18) (IV- 19) (IV-20)' (IV- 21) (IV- 22) (IV-23>. ψ (IV- 24) 80 320352 200909413 3-°-(CH2)RT〇-〇-^^_cn (v -1) (V-2) (V-3) (V-4) J〇-(CH2>sr〇{^~^-Q-CN (V-5) As long as it is such a compound, it can be easily manufactured. The optical film obtained by polymerizing the composition containing the present compound and the liquid crystal compound according to the present embodiment will be described below as a manufacturing method. An example of the method of the optical film of the embodiment. First, an organic solvent, a polymerization initiator, a polymerization inhibitor, a photosensitizer, a crosslinking agent, a leveling agent, and the like are mixed in the present compound and the liquid crystal compound. The composition is prepared as a composition (hereinafter, also referred to as the present composition), and the composition is prepared into a solution, especially when the organic solvent is contained in the film formation, because the film formation can be easily formed, and the polymerization initiator is used. It has a function of hardening the obtained optical film. [Polymerization initiator] This composition is usually There is a polymerization initiator for polymerizing a liquid crystal compound or the present compound. A preferred method for producing an optical film is, for example, a method of photopolymerizing a liquid crystal compound or the present compound. Therefore, the polymerization initiator is photopolymerized at 81 320352 200909413 The photopolymerization initiator may, for example, be a benzoin, a diphenyl ketone, a benzyl ketal, an α-hydroxy ketone, an amino ketone, an onium salt, a phosphonium salt or the like, more specifically For example, Irgacure 907, Irgacure 184, Irgacure 651, Irgacure 819, Irgacure 250, and Irgacure 369 (all of which are manufactured by Ciba Specialties Chemical Co., Ltd.), Seikuol BZ, Seikuol Z, and Seikuol BEE (all of which are Seiko) Chemical company), Kayacure BP100 (manufactured by Nippon Kayaku Co., Ltd.), Kayacure UVI-6992 (manufactured by Dow Co., Ltd.), Adekaoptomer-SP-152, Adekaoptomer-SP-170 (all of which are manufactured by Asahi Chemical Co., Ltd.), etc. When the total amount of the liquid crystal compound and the present compound is 1 part by weight, the polymerization initiator is usually used in an amount of from 0.1 part by weight to 30 parts by weight, and in an amount of 0.5 part by weight. It is preferably 1 part by weight. The compounding property of the liquid crystal compound is not disturbed as long as it is within the above range, and the compound can be polymerized to 0 [polymerization inhibiting agent] The composition may also contain a polymerization inhibiting agent. The polymerization inhibiting agent may, for example, be hydroquinone or a hydroquinone having a substituent such as an alkyl ether or a catechol having a substituent such as an alkyl ether such as a butyl catechol, a gallic phenol, or 2, 2, 6. A free radical make-up agent such as 6-tetradecyl-1-piperidinyloxy radical, a thiophenol, a cold-naphthylamine, and a/5-naphthol. By containing a polymerization inhibiting agent, the polymerization of the liquid crystal compound or the present compound can be controlled, and the stability of the obtained optical film and the virginity of the liquid crystal composition before coating can be improved. Further, when the total amount of the liquid crystal compound and the present compound 82 320352 200909413 is 100 parts by weight, the polymerization inhibiting agent is usually used in an amount of from 0.1 part by weight to 30 parts by weight, and preferably from 0.5 part by weight to 10 parts by weight. . As long as it is within the above range, the alignment of the liquid crystal compound is not disturbed, and the present compound can be polymerized. [Photosensitizer] Further, the composition may contain a photosensitizer. The photosensitizer may, for example, be a xanthone such as xanthone or thioxanthone, an anthraquinone or an anthracene having a substituent such as an alkyl ether, phenothimethamine or erythritol. By using a photosensitizer, polymerization of a liquid crystal compound or the present compound can be made highly sensitive. 5重量份至10重量份为。 good. As long as it is within the above range, the alignment of the liquid crystal compound is not disturbed, and the present compound can be polymerized. [Leveling agent] Further, the composition may also contain a leveling agent. The leveling agent may, for example, be an additive for radiation hardening paint (made by BYK Chemie, Japan: BYK-352, BYK-353, BYK-361N), a coating additive (manufactured by Toray Dow Corning Co., Ltd.: SH28PA 'DC11PA, ST80PA), and a coating additive ( Shin-Etsu Chemical Co., Ltd.: KP32, KP323, X22-161A, KF6001) or fluorine-based additives (manufactured by Dainippon Ink Chemical Industry: F-445, F-470, F-479). The optical film can be made smooth by using a leveling agent. Further, the fluidity of the composition solution may be controlled during the production of the optical film, or the cross-linking of the optical film obtained by polymerizing the liquid crystal compound and the present compound may be adjusted 83 320352 200909413. Further, the specific value of the amount of the leveling agent used is from 0.1 part by weight to 30 parts by weight, and preferably from 0.5 part by weight to 10 parts by weight, based on 100 parts by weight of the total of the liquid crystal compound and the present compound. . As long as it is within the above range, the alignment of the liquid crystal compound is not disturbed, and the compound can be polymerized. [Organic solvent] The organic solvent contained in the present composition is an organic solvent which can dissolve the present compound and a liquid crystal compound, and specific examples thereof include decyl alcohol, ethanol, ethylene glycol, isopropyl alcohol, propylene glycol, and methyl group. Alcohol solvent such as bismuth or butyl acesulfame; ester solvent such as ethyl acetate, butyl acetate, ethylene glycol decyl ether acetate, T-butyrolactone or propylene glycol methyl ether acetate; acetone, A Ketone solvents such as ketoethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone or methyl isobutyl ketone; aliphatic hydrocarbon solvents such as pentane, hexane or heptane; An aromatic hydrocarbon solvent such as benzene or chlorobenzene; acetonitrile, propylene glycol monodecyl ether, tetrahydrofuran, dimethoxyethane, ethyl lactate, chloroform or phenol. These organic solvents may be used singly or in combination of several kinds. In addition, since the composition of the present embodiment is excellent in compatibility, it can be dissolved in an alcohol, an ether solvent, a ketone solvent, a non-chlorinated aliphatic hydrocarbon solvent, a non-chlorinated aromatic hydrocarbon solvent, etc., so that it is not The halogenated hydrocarbon such as chloroform may be dissolved and applied. The wavelength dispersion characteristics of the optical film of the present embodiment can be arbitrarily determined depending on the content of the structural unit derived from the present compound in the optical film. When only the liquid crystal compound is used without using the present compound, the obtained optical film is a film which exhibits a positive wavelength dispersion. Moreover, Re(450)/Re(550) and Re(650)/Re(550) can be made smaller by increasing the content of the structural unit derived from the compound in the unit 84 320352 200909413 of the optical film. That is, the wavelength dispersion is shifted in a direction in which the reverse wavelength is being shifted toward the negative. Specifically, a method in which Re(450)/Re(550) or the like is made smaller and the wavelength dispersion is shifted in a direction toward the negative reverse wavelength dispersion is contained, and the composition of the present compound and the liquid crystal compound is contained as long as it is prepared. After about two to five kinds of compositions having different structural units derived from the present compound, an optical film of the same thickness is obtained for each composition described later, and the phase difference of the obtained optical film is determined. As a result, the correlation between the content of the structural unit of the present compound and the phase difference of the optical film is determined, and the required correlation relationship is used to determine the phase difference required for supplying the optical film of the above film thickness. The content of the structural unit derived from the present compound. In the present composition, when the weight ratio of the present compound and the liquid crystal compound is 100 parts by weight based on the total amount of the present compound and the liquid crystal compound, the total weight of the present compound is usually from 1 to 50 parts by weight 'and from 1 to 30% by weight. The time is better. When it is 1 part by weight or more, it is preferable that the wavelength dispersion is significantly shifted from the negative direction to the negative direction, and when it is 50 parts by weight or less, the liquid crystal layer of the mixture can be stably obtained when it is 30. When the amount is less than the weight, it is preferable because it can be inexpensively prepared into an optical film. The viscosity of the composition is adjusted to such an extent that it is easy to apply, usually below 10 Pa·s, and preferably from about 0.1 to 7 Pa·s. Further, the solid content concentration in the composition solution is usually from 5 to 50% by weight. When the concentration of the solid content is 5% by weight or more, the optical film is not made too thin, and the optical compensation of the liquid crystal panel can provide the necessary light 85 320352 200909413. In addition, when it is corrected for the 5Q weight, it is described. Since the viscosity of the liquid is low, it is preferable that the film thickness of the optical film is not easily generated. + The applicant applies the solution of the composition to the substrate to be aggregated. Thereafter, the desired optical film can be obtained on the support substrate. ' As long as the cation group in the P1 and the liquid crystal compound contained in the present compound is photopolymerizable, it can be irradiated with visible light, ultraviolet light, or laser light to be hardened; as long as the polymerizable group is thermally polymerizable = Heat it to polymerize. In addition, from the viewpoint of film formation, photopolymerizers are preferred, and in terms of processing points, it is particularly preferable to be polymerized by ultraviolet light. In the case of hydrazine polymerization, in order to improve the film formability, it is preferable to dry the solvent in the photopolymerization, and it is preferable to obtain a non-polymerized film. In the case of thermal polymerization, it is usually possible to simultaneously dry: It is preferable to dry the solvent almost before the polymerization to obtain an unpolymerized film and then to polymerize the film, which is preferable because it has excellent film formability. 5 The dry method may be, for example, natural drying, ventilating and drying, and drying and drying. The specific heating temperature is preferably 1 〇 ft in ft. In addition, the heating time is 1 sec to;;: 釭 is better, and 卩 30 sec to 3 〇 min is better. When the heating temperature and the heating time are within the above range, a supporting substrate which is not necessarily sufficiently heat resistant may be used as the supporting substrate. The coating method of the support substrate may, for example, be an extrusion coating method, a direct gravia coating method, a reverse gravure coating method, a 320352 86 200909413 cap coating method, a cooker coating method, or the like. Further, a method of applying the coating using a coater such as a >coating machine, a bar coater, or a spin coater can be mentioned. The support substrate may be any one that can form an alignment film on the support substrate. For example, glass, plastic sheets, plastic films, and translucent films can be mentioned. Further, the light-transmitting film may, for example, be a polyvinylidene film such as polyethylene, polypropylene or a norbornene polymer; a polyvinyl alcohol film, a polyethylene terephthalate film, a polymethacrylate film, or the like; Polyacrylate film, cellulose ester film, polyethylene naphthalate (PEN) film, polycarbonate film, polysulfone film, polyether sulfone film, polyether ruthenium film, poly-stranded sulfide (0〇 1叩]16]^161163111£丨如,??8) Membrane, polyphenylene oxide film, etc. In general, an optical film obtained by including a liquid crystal compound and a composition of the present compound is a film. For example, in the step of using the film bonding step of the embodiment, the step of transporting or storing the film, and the like, the strength of the film is required. It is also possible to use a supporting substrate so that it can be prevented from being damaged or the like and can be handled easily. In the optical film of the present embodiment, it is preferable to apply a solution of the composition after forming an alignment film on a support material. The alignment film must have heat resistance which is not dissolved by a solution containing a composition containing the composition or the like, heat treatment due to removal of a solvent or liquid crystal alignment, and is not caused by rubbing. Scraping or the like causes peeling or the like; and it is a polymer or a composition for an alignment film containing a polymer. The polymer may, for example, be a polyamine or a gelatin having a guanamine bond in the molecule, a polyimine having a quinone bond in the molecule, and a polyamic acid or a polyvinyl alcohol having a hydrolyzate thereof. , alkyl modified polyvinyl alcohol, 87 320352 200909413 polypropylene decylamine, polycarbazole, polyethylene diamine, polystyrene, polyethylene heptaidine brewing I, polyacrylic acid or polyacrylic acid vinegar and other polymers. These gatherers h may be used singly or in combination of two or more types, or may be used in combination. These polymers can be easily obtained by dehydration, deamination or the like and polycondensation of the two groups by chain polymerization, anionic polymerization, cationic polymerization or the like, chain polymerization, 酉5 = or ring-opening polymerization. - own place t

Further, these polymers can be applied after being dissolved in a solvent. The solvent is not particularly limited, but specifically, for example, water 'methanol, '^diol, isopropyl alcohol, propylene glycol, methyl cyproterone, butyl racereol, a solvent; ethyl acetate, butyl acetate , Ethylene glycol methyl ether acetate, ester solvent such as butyrolactone, propylene glycol methyl ether acetate; C-, hydrazine is 7-ketone, cyclopentanone, cyclohexanone, decyl amyl ketone, hydrazine a base-isobutyl _= solvent; an aliphatic hydrocarbon solvent such as pentane, hexane or heptane; an aromatic hydrocarbon solvent such as benzene, toluene or chlorobenzene; acetonitrile, propylene glycol monomethyl hydrazine tetrahydrofuran, Dimethoxyethane, ethyl lactate, chloroform, and the like. These include: "The solvent can be used alone" or a combination of several kinds. In addition, in order to form an alignment film, a commercially available material can be used as it is. Commercially available alignment film materials include, for example, SUNEVER (Registry)膜., manufactured by Membrane Chemical Co., Ltd., 0PTMER (registered trademark, manufactured by JSR), etc. As long as these alignment films are used, the in-plane dispersion of birefringence can be made small by not controlling the refractive index by stretching. Therefore, it is possible to provide an effect of a large-sized optical film which can also correspond to an increase in size of the FPD on the support substrate. Regarding a method of forming an alignment film on the above-mentioned support substrate, for example, an alignment film commercially available from 320352 88 200909413 can be used. After the material is applied as a matching @ and coated on the substrate of the support, an alignment film is formed on the substrate. The compound of the film material is used as a solution, and the thickness of the alignment film obtained by annealing is obtained by the annealing* , sa *, 年度 annual, usually from 1 〇 to 10,000 nm, and preferably from (10) mn to UGGmn. As long as it is within the above range, the preparation of the unpolymerized film (4), which will be described later, has the present compound and liquid liquefaction.

The film layer of the compound is aligned on the alignment film to a desired angular sound. M Another such alignment film can be used for 搓ς or polarized uv irradiation in accordance with the necessity. In this case, the film layer having the present compound and the liquid crystal compound can be aligned in a desired direction. The wiping method of the alignment film can be carried out, for example, by carrying a rubbing roller which has been wound up with a twisted cloth and being rotated, on a stage and bringing it closer to the alignment film being conveyed. '[Modulation step of unpolymerized film]. The step of preparing the unpolymerized film may be, for example, applying a solution of the composition onto an alignment film on any supporting substrate, and drying the solution to obtain the present compound and liquid crystal. A method of a film of a compound (hereinafter sometimes referred to as an unpolymerized film); a method of injecting a liquid crystal compound into the liquid crystal cell after the liquid crystal cell is formed, and the like. In particular, a method of obtaining an unpolymerized film on an alignment film laminated on a support substrate is because the production cost can be reduced, and a film of the roller film can be produced, and the obtained unpolymerized film exhibits a nematic phase. When the liquid crystal phase is equal, it may have birefringence due to monodomain alignment. Since the unpolymerized film is aligned at about 〇 to 120 ° C (preferably at a low temperature of 25 to 89 320 352 2009094 13 80 ° C), it may be used as an alignment film and may not necessarily have sufficient exemplification as described above. The base of the heat-resistant substrate is not crystallized even after cooling to about 30 to 10 ° C after the alignment. [Polymerization Step of Unpolymerized Film] In the polymerization step of the unpolymerized film, the unpolymerized film obtained in the preparation step of the above unpolymerized film is polymerized and then cured. Thereby, the alignment of the film layer (hereinafter sometimes referred to as a liquid crystal layer) having a structural unit derived from the present compound and a structural unit derived from the liquid crystal compound can be fixed, and the liquid crystal layer, the alignment film, and the support group can be obtained. An optical film made of layers. Therefore, an optical film having a small refractive index change in the planar direction of the liquid crystal layer and a large refractive index change in the normal direction of the liquid crystal layer can be produced. The method of polymerizing the unpolymerized film is determined by the type of the liquid crystal compound and the compound. For example, the above unpolymerized film can be polymerized by photopolymerization or thermal polymerization. In the present embodiment, in particular, it is preferred that the unpolymerized film is polymerized by photopolymerization. According to this method, since the unpolymerized film is polymerized at a low temperature, the heat resistance of the support substrate can be selected to a wider extent. At the same time, industrial manufacturing is also made easy. The method of photopolymerizing the unpolymerized film may, for example, be a method of polymerizing an unpolymerized film by irradiating ultraviolet rays onto an unpolymerized film. In this way, the obtained optical film can be obtained without using a liquid crystal polymer. In the polymerization step of the unpolymerized film, the compound and the liquid crystal compound can be crosslinked by photopolymerization. Therefore, it is possible to exhibit an effect that it is hard to be affected by the change in the birefringence due to heat. 90 320352 200909413 Further, it is not necessary to use a surfactant surface treatment agent on the obtained optical film. In other words, in the w film used in the optical film of the present embodiment, the adhesion between the support substrate and the alignment film and the adhesion between the alignment film and the optical direction are good, and the optical film can be easily obtained. Prefilming The optical film of the present embodiment is usually a film when compared with a film having a phase difference of the same film as the stretched film. After the above steps, the step of peeling off the support substrate may also be included. The film obtained by such a constitution is an optical film composed of an alignment film and a liquid crystal layer g. θ into

Further, in addition to the step of peeling off the above-mentioned supporting substrate, a step of peeling off the alignment film may be contained. The obtained optical film does not contain a supporting substrate or an alignment film, but is a film composed of a structural unit derived from the present compound and a structural unit derived from a liquid crystal compound, that is, an optical film composed only of a liquid crystal layer. Further, after appropriately adjusting the amount of the composition or the concentration of the organic solvent, the film thickness can be adjusted to provide a desired retardation value. The phase difference of the optical film (re1; ardatiQn,

Re(1)) can be determined as in equation (6), so it is only necessary to adjust the film thickness d to obtain the desired Re(1).

Re(A)=dxAn(A) (6) (wherein Re(A) represents the phase difference of the wavelength and the time of the coffee, d represents the film thickness, Δ n(;l) represents; the refractive index anisotropy at Inm ). The film thickness of the liquid crystal layer in the optical film of the present embodiment is preferably (M to 1 Å, and it is more preferable to use Q5 to _ from the viewpoint of reducing photoelasticity. 320352 91 200909413 In the case of birefringence, the phase difference is usually about 50 to 500 nm, and preferably 100 to 300 nm. By using a film having such optical characteristics, all liquid crystal panels or organic EL and other flat display can be made into a film. Optical compensation for reverse wavelength dispersion is required. The optical film thus obtained is excellent in transparency and can be used as a film for various displays. For example, the optical film of the present embodiment is used as a λ /4 plate in a wide-band domain. Or in the case of a λ/2 plate, it is only necessary to appropriately select the content of the structural unit derived from the present compound, and then adjust the film thickness of the liquid crystal layer to increase the film thickness of the liquid crystal layer according to the formula (6). Specifically, _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ For λ/2 plate, just adjust the film thickness of the liquid crystal layer to The Re (550) of the obtained optical film may be 250 to 300 nm, preferably 273 to 277 nm, and more preferably about 275 nm. The optical film of the present embodiment is used as a vertical alignment (VA, vertical alingment). When the optical film for the mode is used, it is only necessary to appropriately select the content of the structural unit derived from the present compound, and the film thickness of the liquid crystal layer may be adjusted according to the formula (6). Specifically, the film thickness should be adjusted so that Re (550) is 40. The optical film of the present embodiment can be widely used as an optical film having excellent wavelength dispersion characteristics. The optical film may, for example, be an antireflection (AR) film or the like. A film, a polarizing film, a retardation film, a circularly polarizing film, an enlarged viewing angle film, and an optical compensation film for viewing angle compensation of a transmissive liquid crystal display, etc. 92 320352 200909413 Although the optical film of the present embodiment has only one sheet Although excellent optical characteristics are shown, a plurality of sheets may be laminated. Alternatively, it may be combined with another film. Specifically, for example, a circular film in which the optical film of the present embodiment is bonded to a polarizing film may be used. In the light-emitting plate, the optical film of the present embodiment is used as a wide-band circular polarizing plate which is bonded to a λ /4 plate in a wide-band domain, and the like, and by adding a small amount of the present compound, In the optical film

The value of Re(450)/Re(550) is lowered, and as a result, a wavelength-dependent optical film having a reduced phase difference can be easily prepared. The film of the present embodiment may be a phase difference plate of a reflective liquid crystal display or an organic electroluminescence (EL) display, and a flat display device including the phase difference plate or the optical film. The above flat display device is also not particularly limited, and may be, for example, a liquid crystal display device (acD) or organic electroluminescence (EL). So, consider it. For example, the film system according to the present embodiment can have such a wide range of uses. 1. A polarizing plate in which the optical film and the polarizing film of the present embodiment are laminated, and a plane including the polarizing plate are described below. The polarizer is a film with a polarizing function, that is, it is biased.

Examples of the above-mentioned first and second figures (6) include (1) an embodiment in which direct bonding is carried out (Fig. 1 320352 93 200909413). (a)), (2) an embodiment in which the optical film 1 and the polarizing film layer are combined (Fig. 1 (8)); (3) the agent layer 3 is attached directly to the film, and then the optical alignment is performed. 2 1 is a direct application form in which the optical film/the polarizing layer 2 is directly bonded (Fig. 1 (c)); (4) the optical film 丨 and the optical film r are bonded together via the adhesive layer 3, and then An embodiment in which the optical film i'-cut polarizing film layer 2 is directly bonded to each other (Fig. i ((1)); and (5) is such that the optical film and the photonic film 1 are bonded together by the carrier layer 3; Further, the optical film 1 and the polarizing film layer 2 are bonded to each other via an adapter layer 3' (Fig. (e)). The polarizing plate of the present embodiment is made of a polarizing film. The optical film of the present embodiment is bonded together. As the optical film, a layer containing only a structural unit derived from the present compound and a structural unit derived from a liquid crystal compound (that is, a liquid crystal layer only) may be used. support An optical film composed of a material, an alignment film, and a liquid crystal layer, and an optical film composed of an alignment film and a liquid crystal layer. The polarizing plate of the present embodiment may have a plurality of optical films laminated thereon, and the optical film of the plurality of layers may be laminated. The same type may be used in combination, or different types may be used in combination. More specifically, the polarizing plate of the present embodiment can be exemplified as shown in Figs. 2(a) to (k). In the drawings (a) to (e), a film composed of the liquid crystal layer 11 or the liquid crystal layer 11' and the alignment film layer 12 or the alignment film layer 12' is used as the optical film 1 and the optical film 。. a) to (e) are respectively a composition in which the optical film 1 and the polarizing film layer 2 are directly bonded together (Fig. 2(a)); the optical film 1 and the polarizing film layer 2 are pasted via the adhesive layer 3 Synthetic composition (Fig. 2(b)); the optical film 1 and the optical film Γ are directly bonded together, and the optical film 1' is directly bonded to the 94 320352 200909413 flat light layer 2 (Fig. 2(c) The optical film 1 and the photo-adhesive film 1 " are bonded together by the adhesive layer 3, and the polarizing film layer 2 is directly bonded to the optical film 1 (Fig. 2 (d)); The film 1 and the optical film 1 are bonded together via the adhesive layer 3, and the optical film 1 and the polarizing film layer 2 are bonded to each other via the adhesive layer 3' (Fig. 2 &). Further, in FIGS. 2(1) and 1(g), a film composed of the liquid crystal layer u or the liquid helium layer 11 is used as the optical film 1 and the optical film, and the optical film 1 does not contain an alignment film. Layer 12 or alignment film layer 12,. In addition, in Figure 2 (1), the optical film! The polarizing film layer 2 is bonded to each other via a pair of adhesive layers 3. On the other hand, in Fig. 2(g), the optical film} and the optical film 1 are bonded via the adhesive layer 3 (four), and the polarizing film layer 2 is bonded to the outside via the adhesive layer 3'. ★ Fig. 2 (6) shows the same configuration as Fig. 2 (1). However, unlike the second figure (1), the film is formed by the cut substrate 13, the alignment film layer 12 formed on the surface of the support substrate 13, and the liquid crystal layer 11 formed on the surface of the alignment film layer a. A laminate (film) formed. Fig. 2 (1) shows the same configuration as Fig. 2 (g). However, the difference = Fig. 2 (8) where the 'optical film 丨 or optical alignment is to use the alignment film layer 12 or alignment containing the support ^ (4) or the branch material 13' formed on the surface of the cut substrate 13 or the support substrate. A layered body (film) of the liquid crystal layer 11' on the surface of the film layer 12, the disk-shaped alignment film layer 12 or the alignment film layer 12. The structure of the day. However, it is represented by the liquid crystal layer (Fig. 2(j) and (k) and the second image (g) in the two films, the optical film 1 in Fig. 2 (j), 320352 95 200909413 1 Γ In the film formed, the optical film 1 is a film composed of the liquid crystal layer 11, the alignment film layer 12, and the support substrate 13. Further, in the optical film 第 in Fig. 2(k), a film composed of the liquid crystal layer 11', the alignment film layer 12, and the support substrate 13 is used, and the optical film 1 is a film composed of the liquid crystal layer 11. The polarizing film layer may be a film having a polarizing function, and may be, for example, a film obtained by adsorbing iodine or a dichroic dye on a polyvinyl alcohol film, or iodine or dichroism after stretching a polyvinyl alcohol film. Film of pigment, etc. The adhesive for the adhesive layer 3 and the adhesive layer 3' can be preferably an adhesive having high transparency and excellent heat resistance. As such an adhesive, for example, an acrylic, epoxy or polyamine phthalate (PU)-based adhesive or the like can be used. Further, in the polarizing film, as shown in Figs. 1(c) to 1(e), the optical film may be bonded to one to three layers in accordance with necessity. The flat display device (FPD) of the present embodiment is provided with the optical film of the present embodiment, and may be, for example, a liquid crystal display device (LCD) including a liquid crystal panel to which the polarizing film of the embodiment and the liquid crystal panel are bonded, or An organic electroluminescence (EL) display device having an organic electroluminescence panel to which the polarizing film and the light-emitting layer of the embodiment are bonded is provided. The embodiment of the FPD according to the present embodiment will be described in detail below with respect to the LCD and the EL. [LCD] The LCD can be, for example, an LCD having a liquid crystal panel shown in FIG. In the LCD, the polarizing film 4 and the liquid crystal panel 6 of the present embodiment are bonded to each other via the adhesive layer 5. According to the above composition, by using an electrode not shown in the figure, after the voltage is applied to the liquid crystal panel, the liquid crystal molecules are driven to express the effect of the light shutter 96 320352 200909413. [EL] ρτ望 It has the special purpose of the organic electroluminescent surface shown in Fig. 4. In the above-described organic electroluminescence panel, the optical film 4 and the light-emitting layer 7 of the present embodiment are bonded to each other via the adhesive layer 5. The optical film 4 in the above organic electroluminescence panel has a function as a wide-frequency circular polarizing plate. Further, the above-mentioned light-emitting layer 7 is a layer of at least one layer composed of a conductive compound. BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in more detail by way of examples. <Production Example of Polymerizable Compound (1-1)> Synthesis Example of Polymerizable Compound (丨_丨)

(Synthesis example of ethyl 4-(6-carbylhexyloxy) benzoate (PG-a)) 150 g (0.90 mol) of ethyl 4-hydroxybenzoate; [.86 g (1. 35 mol) of potassium carbonate, 750 g of N,N-dimercaptoacetamide, and the temperature was raised to 80 C. The receiver was dropped 244 g (1.44 mol) of 6-isohexanol in 2 hours, and then stirred at 80 ° C for 2 hours. After cooling, the reaction solution was poured into ice 320352 97 200909413 in water by extraction with acetic acid. After the solvent was washed with water, the solvent was distilled off under reduced pressure to give 312 g of 4-(6-hydroxyhexyloxy)benzoic acid ethyl ester (PG-a) as a main component. White solid. (Synthesis example of 4-(6-hydroxyhexyloxy) benzoic acid (pG_b)) 312 g of a white solid obtained as a main component of (PG-a) obtained by the life-span was dissolved in decyl alcohol. Next, a methanol solution (328 g (5.85 mol) of potassium pentoxide) containing potassium hydroxide in a saturated state was dropped, and then spoiled at 7 ° C for 8 hours. After cooling, 600 g of 36% hydrochloric acid was slowly added. 195 g (0. 82 mol) of 4-(6-hydroxyhexyloxy)benzoic acid was obtained by washing the white solid precipitated with water and separating it by filtration and drying at 50 ° C under reduced pressure. (PG-b) A white solid based on the main component. The yield based on (PG-a) was 91%. (Synthesis example of (4-(6-acryloyloxyhexyloxy) benzoic acid) (PG-c)) The (PG-b) obtained in the preceding paragraph is 195 g of the main component ((PG-b) is 〇. 82 mol) was dissolved in 1,4-dioxane after being replaced with nitrogen in a container of 208 g of N,N-dimethylaniline. After the reaction solution was warmed to 70 ° C, I48 g (1.44 mol) of acrylonitrile chloride was dropped over 30 minutes and allowed to mix for 2 hours. After cooling, the reaction solution was poured into ice water, and extracted with ethyl citrate. After the ethyl acetate phase was washed with water, the solvent was distilled off under reduced pressure to give 120 g (0.41 mol) of 4-(6-propenyloxyhexyloxy)benzoic acid (PG_c). The white solid of the ingredients. The yield based on (PG-b) was 91%. (Synthesis example of ethoxylated 4-ethoxybenzoic acid ethoxylated ester (pG-d)) 166 g (1.2 mol) of 4-hydroxybenzoic acid, 121 g (1.2 mol) of tri-98 320352 200909413 ethylamine and 1193 g of chloroform was placed in a container and stirred. A mixed solution of 113 g (1.2 mol) of chlorodecylethyl ether and 298 g of chloroform was added dropwise over 30 minutes at room temperature, and stirred for 2 hours. After cooling, the reaction solution was washed with water, an aqueous hydrochloric acid solution and an aqueous sodium carbonate solution, and then the organic layer was taken. After the organic layer was evaporated to dryness under reduced pressure, 251 g (yield) of y. (Synthesis example of 4-(4-(6-propenyloxyhexyloxy)benzyloxy)benzoic acid (PG-e)) The ethoxylated 4-hydroxybenzoic acid ethoxylated ester obtained in the above paragraph ( PG-d) In a 124 g yellow liquid containing as a main component, 147 g (0.50 mol) of a white solid of (PG-c) obtained in the preceding paragraph, and 7. 7 g (63 mmol) of 4-diamine-based hydrazine were determined. 824g of chloroform. Next, 123 g (0.60 mol) of N,N'-dicyclohexylcarbodiimide (DCC) was dissolved in 165 g of chloroform, and the mixture was stirred at room temperature for 24 hours. Thereafter, the organic layer obtained by removing the solid matter after filtration was washed twice with 989 g of 2N hydrochloric acid. The washed organic layer was evaporated to give a 237 g of pale yellow liquid. To the resulting liquid, 474 g of ethanol and 12.7 g (50 mol) of pyridinium sulfonate were added and stirred at 60 ° C for 3 hours. After the reaction solution was cooled to room temperature, white crystals were precipitated, so that the solid matter was taken out after filtration. The obtained solid matter was sufficiently washed with ethanol and dried to obtain 180 g of (4-(4-(6-propenyloxyhexyloxy)benzyloxy)benzoic acid (PG-e). The yield based on PG-c) was 86%. In the vessel, 4.6 g (13 mmol) of 9,9-bis(4-hydroxyphenyl)*, 10.7 g (32 mmol) of (4-( 4-(6-Phenyloxyhexyloxy)benzyloxy)benzoic acid (PG-e), 0.3 g (3 mmol) of 4-dimercaptoamine σ ratio biting and 107 g 99 320352 200909413 chloroform mixture Thereafter, 5.4 g (26 mmol) of hydrazine, Ν'-dicyclohexylcarbodiimide (DCC) was dissolved in 21 g of chloroform, and the mixture was stirred at room temperature for 24 hours. Thereafter, 107 g of 2N was added. After hydrochloric acid, the solid matter was removed by filtration, and the filtrate was separated, and the organic layer was taken out. 107 g of 2N hydrochloric acid was added to the obtained organic layer, and the mixture was washed, the solvent was distilled off, and methanol was added to obtain a solid. After the obtained solid matter was sufficiently washed, 8.6 g of a pale yellow solid polymerizable compound (1-1) was obtained. The yield based on 9,9-bis(4-hydroxyphenyl)indole was 58%. <Production Example of Polymerizable Compound (1-2)> Structure adhesion compound (1-2) as described below. Synthesis Example are shown as follows.

(Synthesis Example of 2,7-Dinitro-9,9-bis(4-hydroxyphenyl)anthracene) In a container, 25.0 g (93 mmol) of 2,7-dishhosyl-9-fluorenone, 87 g (925 mmol) of a mixture of 0.49 g (5 mmol) of 3-cyanopropionic acid and 4.5 g of sulfuric acid were mixed and stirred at 90 ° C for 3 hours. When the reaction solution was added to a vessel in which 35 g of methanol and 70 g of water had been added, crystals were precipitated. After the crystals were separated by filtration, 24. g (55 mmol) of 2,7-dinitro-9,9-bis(4-pyridylphenyl)anthracene yellow crystals as 2,7-dishhosyl- 9-100 320352 200909413 The yield based on ketone is 59%. In addition to the use of the previous item, 2 7~-gu | η η is substituted for 9,9-bis (4-shirt phenyl phantom: recorded -9,9-bis (4-~ylphenyl) into μ彳, "^ The rest of the steps are the same as in the <Production Example of Polymerized E-Form (1-1)>, and 11.

A solid polymerizable compound (1_2). The yield based on H, B, (yield-9,9-bis(4-diphenyl)) was 64%. <Production Example of Compound I(1 -3)&gt; Polymerizable Compound The structure of (Bu 3) is as follows. The synthesis example is shown below.

(Synthesis example of 2' 7-dibromo-9,9-bis(4-hydroxyphenyl)anthracene) 2,7-dibromo-9-fluorenone, 76 g (732 mmol) containing 20.5 g (73 mmol) The vessel of phenol, 〇. 7 g (7 mmol) of 3-mercaptopropionic acid and 3.4 g of sulfuric acid was heated to 90 ° C and then aged for 3 hours. When the reaction solution was added to a vessel in which 78 ml of sterol and 306 g of water had been added, crystallization was precipitated. The crystals were separated by filtration and washed with toluene to obtain 31. White crystals of 2,7-dibromo-9,9-bis(4-hydroxyphenyl). The yield based on 2,7-dibromo-9-burophilone was 84%. (Synthesis Example of 2,7-Dicyano-9,9-bis(4-pyridylphenyl)anthracene) In a container, 33.1 (23111111〇1) of 2,7-dibromo-9,9 - Bis(4-101 320352 200909413 phenyl) ruthenium, 14.2 g (142 mmol) of copper cyanide and 171 ml of N,N-dimethylformamide were mixed and stirred at 153 ° C for 6 hours. The reaction solution was added to a vessel to which 171 ml of ethylenediamine and 1709 g of water had been added, and then extracted twice with 1,282 ml of ethyl acetate to obtain an ethyl acetate phase. After the obtained ethyl acetate phase was washed with water, the solvent was distilled off and recrystallized from ethanol to obtain crystals. After the obtained crystals were purified by column chromatography, 6.2 g of pale yellow crystals of 2,7-dicyano-9,9-bis(4-hydroxyphenyl)indole were obtained. The yield based on 2,7-dibromo-9,9-bis(4-pyridylphenyl)indole was 24%. In addition to the 2,7-dicyano-9,9-bis(4-hydroxyphenyl)fluorene obtained in the preceding paragraph, in addition to 9,9-bis(4-hydroxyphenyl)fluorene, the &lt;polymerizability Production Example of Compound (1-1)&gt; The same procedure was carried out to obtain 7.9 g of a pale yellow solid polymerizable compound (1-3), which was 2,7-dicyano-9, 9-bis (4). The yield based on -hydroxyphenyl)» was 83%. (Example 1) &lt;Production Example of Optical Film&gt; A 2% by weight aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 completely saponified, manufactured by Wako Pure Chemical Industries, Ltd.) was applied to a glass substrate, and then heated. After drying, a film having a thickness of 89 nm was obtained. Next, after applying a rubbing treatment to the surface, the coating liquid of the composition of Table 1 was applied onto the wiped surface by a spin coating method, and dried at 45 ° C for 1 minute. Then, it was allowed to stand at room temperature for 1 minute, and then irradiated with ultraviolet rays of 1200 mJ/cm 2 to form an optical film having a film thickness of 0.98 / m. In Table 1, LC242 is a liquid crystal compound available from BASF Corporation, polymerization 102 320352 200909413 The initiator is Irgacure 907 (manufactured by Ciba Specialty Chemicals Co., Ltd.), the leveling agent is BYK361N (manufactured by BY本BYK), and the solvent system is used. Pentanone. Further, the weight % in the table other than the solvent means the weight % of the solid content when the coating liquid is 100% by weight. [Table 1] Polymerizable compound (1) Liquid crystal compound --- Photopolymerization initiator leveling agent - Solvent compound number (% by weight) Compound number (% by weight) (% by weight) (% by weight) ----- (% by weight) Example 1 1-2 2.6 LC242 26.4 0.9 0.1 70 Example 2 1-3 1.8 LC242 26.7 1.4 0.1 70 Comparative Example 1 I - LC242 29.0 0.9 0.1 70 Comparative Example 2 1-1 4.0 LC242 25.0. 0.9 0.1 70 Photopolymerizable starter: Irgacure 907 (Ciba Specialty Chemicals) Solvent: cyclopentanone &lt;Measurement of wavelength dispersion characteristics&gt; In the wavelength range of 450 nm to 700 nm, using a measuring instrument (K0BRA) -WR, manufactured by Oji Scientific Instruments Co., Ltd.) After measuring the phase difference of the obtained optical film, the phase difference Re (450) of the wave |45 〇 nm and the phase difference Re of the wavelength of 550 nm were calculated by the device attachment program (55 〇 When the phase difference value Re (650) of the wavelength is 65 〇 nm, it is known that [Re(45〇)/Re(550)]=l. 059, [Re(650)/Re(550)]=0.966. The results are shown in Table 2. 103 320352 200909413 [Table 2]

Re(550)[nm] Re(450)/Re(550) Re(650)/Re(550) d[ //m] Example 1 124 1.059 0. 966 0. 98 Example 2 120 1.063 0.964 1.00 Compare Example 139 1.070 0.960 1.09 Comparative Example 2 112 1.069 0. 960 1.04 (Example 2) An optical film was produced in the same manner as in Example 1 except that the coating liquid of Table 1 was used to prepare a film thickness of 1.00# Optical film of m. After measuring the phase difference of the obtained optical film using a measuring instrument (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.), it was found that [Re(450)/Re(550)] = l. 063, [Re(650)/Re( 550) H). 964. The results are shown in Table 2. (Comparative Example 1) An optical film was produced in the same manner as in Example 1 except that the coating liquid of Table 1 was used, and an optical film having a film thickness of 1.09/zm was formed. After measuring the phase difference of the obtained optical film using a measuring instrument (KOBRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.), it was found that [Re(450)/Re(550)] = l. 070, [Re(650)/Re( 550)]=0. 960. The results are shown in Table 2. (Comparative Example 2) An optical film was produced by the same procedure as in Example 1 except that the coating liquid of Table 1 was used, and an optical film having a film thickness L was formed. After measuring the phase difference of the obtained optical film using a measuring instrument (KOBRA-WR 'Men's Instruments Co., Ltd.), it is known that [Re(450)/Re(550)] = 1. 069, 104 320352 200909413 [Re(650) /Re(550)&gt;0. 960. The results are shown in Table 2. &lt;Production Example of Present Compound (J-3)&gt; The present compound (J-3) has the following structure.

(J-3) The acrylate derivative (PG-e) which can be used in (J-3) or the like is synthesized in accordance with the following route.

HO

COOEt PG-a HO_(CH2)6-0

COOEt PG-a

NaOH

COOH PG-b PG-b

H〇-(CH2)6—〇

〇-(CH2&gt;6-〇

OOH PG-c

HO

COOH CI^O^

PG-d H+ PG-c ---

DCC (Synthesis example of ethyl 4-(6-hydroxyhexyloxy)benzoate (PG-a)) 105 320352 200909413 169 g (l. 〇 2 mol) of ethyl 4-hydroxybenzoate, 211 g (1. 53 mol) The carbonic acid was desorbed, 847 g of N,N-dimercaptoacetamide, and the temperature was raised to 80 T:. Next, 277 g (1.53 mol) of 6-brominated hexane was dropped over 2 hours, followed by scrambled at 80 C for 2 hours. After cooling, the reaction solution was poured into ice water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water, the solvent was distilled off to obtain 377 g of a colorless transparent liquid containing 4-(6-hydroxyhexyloxy)benzoic acid ethyl ester (PG_a) as a main component. (Synthesis Example of 4-(6-Pyridylhexyloxy)benzoic Acid (PG-b)) In 377 g of a colorless transparent liquid containing (PG-a) as a main component obtained in the above paragraph, 905 g of methanol and 181 g were added. Stir the water afterwards. Next, 2,092 g of a methanol solution (containing 397 g (7.08 mol) of potassium hydroxide in a solution) in a saturated state was dropped, and then stirred at about 7 (TC for 5 hours. After cooling), 718 g of 35 was slowly added. % hydrochloric acid. The white solid precipitated by washing with water was separated by filtration and dried under reduced pressure at 50 ° C to give 4-(6-hydroxyhexyloxy)benzoic acid (PG-). b) 228 g of a white solid as a main component. The yield based on ethyl 4-hydroxybenzoate was 94%. (4-(6-Acetyloxyhexyloxy)benzoic acid (PG-c) Synthesis Example) After replacing 228 g (0.99 mol) of (PG-b) white solid obtained in the preceding paragraph with 244 g (2.01 mol) of N,N-dimethylaniline in a container, it was replaced with nitrogen by 2282 g. 1, 4-dioxane was dissolved. After the reaction solution was heated to 70 ° C, '173 g (1.92 mol) of acrylonitrile chloride was dropped over 30 minutes and stirred for 2 hours. After cooling, the reaction solution was poured into ice. In the water, ethyl acetate was added for liquid separation extraction, and the organic layer was taken out. The obtained organic layer was washed with water at 106 320352 200909413, and then the solvent was distilled off under reduced pressure. l 〇 9g (〇.37mol) of 4-(6-propenyloxyhexyloxy)benzoic acid (PG_C) as a white solid. The yield based on (PG-b) is 39%. Synthesis example of ethoxymethyl benzoate (PG_d)) 166 g (1.2 mol) of 4-hydroxybenzoic acid, 121 g (1.2 mol) of triethylamine and 1193 g of chloroform were placed in a container, and After stirring, a mixed solution of 113 g (1.2 mol) of chloromethylethyl ether and 298 g of chloroform was added dropwise over 30 minutes, and stirred for 2 hours. After cooling, the reaction solution was made up of water and aqueous hydrochloric acid. After the aqueous sodium carbonate solution is separated and washed, the organic layer is taken out. After the organic layer is distilled off under reduced pressure, 251 g of yellow hydroxybenzoate (PG-d) as a main component can be obtained. (Synthesis of 4-(4-(6-propenyloxyhexyloxy)benzyloxy)benzoic acid (pG_e)) The ethoxylated 4-hydroxybenzoate (pG-I) obtained in the above paragraph d) In a yellow liquid of 124 g of the main component, 147 g (〇. 5〇111〇1) of the white solid of (PG-c) obtained in the preceding paragraph, and 7. 7 g (63 mmol) of 4-dimethylamine-based absorption were added. (Dian, 824g of gas imitation. Receiver I23 g (0.60 mol) of hydrazine, Ν'-dicyclohexyl sulphate anti-imine (DCC) was dissolved in I65 g of chloroform, and after dropping at room temperature, it was stirred for 24 hours. After that, the solid matter was removed after filtration. The organic layer was washed twice with 989 g of 2N hydrochloric acid. The washed organic layer was evaporated to give a 237 g of pale yellow liquid. To the resulting liquid, 47 勉 of ethanol and 12. 7 g (5 Omol of) of p-toluene ruthenium sulphate were added, and the mixture was stirred for 6 hours in 6 Torr. After the reaction solution was cooled to room temperature, white crystals were precipitated, so that the solid matter was taken out after filtration. The obtained solid matter was sufficiently washed with ethanol at 320352 107 200909413, and then dried to obtain 18 g of (4-(4-(6-propenyloxyhexyloxy)benzyloxy)benzoic acid (PG-). e) The yield based on (PG-c) is %. The structure of the anthracene derivative (J-3A) used in (J-3) or the like can be as follows.

(Synthesis Example of 2,7-Dinitro-9,9-bis(4-hydroxyphenyl)anthracene) In a container, 25.0 g (93 mmol) of 2,7-dishhosyl-9-- 87 g (925_ol) of phenol, 49.49 g (5 mmol) of 3-mercaptopropionic acid and 4.5 g of sulfuric acid were mixed, and stirred at 90 ° C for 3 hours. When the reaction solution was added to a vessel to which 35 g of decyl alcohol and 70 g of water had been added, crystals were precipitated. After the crystals were separated by filtration, 24. g (55 mmol) of 2,7-dinitro-9,9-bis(4-hydroxyphenyl)indole as a yellow crystal was obtained as 2,7-dinitro-9. The yield based on the -g ketone was 59%. (Synthesis Example of (J-3A)) 1 0 g (34 mmol) of 2,7-dinitro-9,9-bis(4-hydroxyphenyl)fluorene, 75 g of N,Ν'-dimethyl A vessel of acetamide, 7. lg (51 mmol) of potassium carbonate, and 5. 3 g (34 mmol) of ethyl iodide was heated to 7 ° C and then allowed to mature for 3 hours. After cooling, 75 g of methyl isobutyl ketone and 105 g of 1N hydrochloric acid were added to the reaction solution, and the mixture was stirred and separated. The obtained organic layer was liquid-washed twice with i 5 g of 1N hydrochloric acid, and then the organic layer was taken out. The crystallization of 15. 7 g of yellow crystals was obtained by concentrating the organic layer of 108 320352 200909413, and then adding n-heptane and crystallization. Further, the obtained crystal was purified by a ruthenium column chromatography to obtain 6.5 g of a yellow crystal (J-3A). The yield based on 2,7-dinitro-9,9-bis(4-hydroxyphenyl)indole was 41%. (Synthesis Example of (J-3)) In a vessel, 5.6 g (12 mmol) of (J-3A), 5.9 g (14 mmol) of (4-(4-(6-acryloxy hexyloxy)) After mixing benzyloxy)benzoic acid (PG-e), 0.2 g (1 mmol) of 4-didecylaminopyridine and 48 g of chloroform, 3.3 g (16 mmol) of N,N'-di The cyclohexylcarbodiimide (DCC) was dissolved in 12 g of chloroform, and the mixture was stirred at room temperature for 24 hours. Thereafter, after adding 59 g of 2N hydrochloric acid, the solid matter was removed by filtration, and the filtrate was separated and the organic layer was taken. After adding 59 g of 2N hydrochloric acid to the obtained organic layer and washing with a liquid separation, the solvent was distilled off, and decyl alcohol was added to obtain a solid matter. After the solid matter was sufficiently washed with methanol, the compound was obtained as a pale yellow solid. (J-3) The yield based on (J-3A) is 44%. <Production Example of Present Compound (J-4)&gt; The structure of the present compound (J-4) is as follows.

109 320352 200909413 The structure of the anthracene derivative (J_4A) which can be used in (J-4) or the like is as follows

The synthesis example of 0 (2,7-dinitro-9,9-bis(4,yl-methyl-phenyl)g) is carried out in addition to the use of the adjacent age to replace the (2, 7 _Shuangshi Xiaoji 9,9-bis(4-p-phenylene)g synthesis example) The same procedure can be used to obtain the present compound 2,7-dinitro-9,9-bis (4_ Base_3_methyl_phenyl)g. The yield based on 2,7-dinitro-9-ketone was 67%. (Synthesis Example of (J-4A)) + In addition to making S 2,7-di-decyl-9, 9-bis(4-transyl-3-yl-phenyl) substituted 2,7-di In the same procedure as in the (Synthesis Example of (J-3A)), the same procedure as in the case of the synthesis of (J-3A) can be obtained (J 4A) ). The yield based on 2,7-dinitro-9,9-bis(4-carbyl-3-indolyl-phenyl) was 49%. &lt;. -4) Synthesis Example&gt; The same procedure as in ((J_3) synthesis example) was carried out except that (J-4A) was used instead of (J-3A). 〇g pale yellow solid (:_ 4). The yield based on (J-4A) was . &lt;Production Example of Present Compound (J-5)> The structure of the present compound (J-5) is as follows. The synthesis example is shown below. 320352 110 200909413

The acrylate derivative (PG-h) which can be used in (J-5) or the like is synthesized in accordance with the following route.

PG-f

Synthesis example of PG-h ((PG-f)) 80 g (0.37 mol) of 4-(4-light phenyl) benzoic acid, 206 g (1.49 mol) of potassium carbonate, 400 g of N, N- The mercaptoacetamide was allowed to warm to 90 °C. Next, 153 g (1.12 mol) of 6-chlorohexanol was added dropwise over 2 hours, followed by stirring at 9 (TC for 8 hours. The reaction solution was cooled, filtered, and the solid matter was removed, and then poured into water to cause crystallization. After filtration, 111 320352 200909413 was taken out. After washing the solid with IN hydrochloric acid, 434 g of undried (PG-f) white solid was obtained. (Synthesis of (PG-g)) 434 g of undried white solid (PG-f), 600 g of tetrahydrofuran, 30 Og of ethylene glycol was added, and the temperature was raised to 65 ° C. Then, 394 g of 10% sodium hydroxide (sodium hydroxide was 0.87 mol) was added dropwise. Then, the mixture was stirred for 3 hours at 65 ° C. After cooling the reaction solution, it was poured into water, and hydrochloric acid was added until it became acidic, and crystals were precipitated. After filtration, the solid matter was taken out, and after drying, 103 g (PG-) was obtained. g) White solid. (Synthesis example of (PG-h)) In 100 g (0.45 mol) of (PG-g) white solid, add 100 g of N,N-dimercaptoacetamide, 123 g ( 1.02 mol) of N,N-dimethylaniline, and allowed to cool to 〇 ° C. Then, 60.5 g (0.67 mol) of acrylonitrile chloride was dropped, followed by room temperature After mixing for 3 hours, the reaction solution was cooled, and 1N hydrochloric acid was added until it became acidic, and crystals were precipitated. After filtration, the solid matter was taken out, and after drying, 80 g of (PG-h) white solid was obtained. g) The yield based on the reference is 64%. &lt;Synthesis Example of (J-5)> The synthesis of ((J-3) is carried out except that (PG-g) is used instead of (PG-e) In the same procedure, a yield of 7. Og of a pale yellow solid (J-5) was obtained. The yield based on (J-3A) was 79%. &lt;Production Example of the present compound (J-6)&gt; The structure of the present compound (J-6) is as follows. The synthesis examples thereof are shown below. 112 320352 200909413

(J-6) The acrylic vinegar derivative (PG-i) which can be used in (J~6) or the like is synthesized in accordance with the following route. PG-e PG-d H+

DCC PG-i 〇·〇-

5克(75丽), 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。白色1) The white solid of (PG-e) obtained in the preceding paragraph, 1.2 g (10 mmol) of 4-didecylaminopyridinium, and 245 g of gas. Next, 2 〇·6 g (1〇〇_〇1) of N,N,dicyclohexylcarbodiimide (DCC) was dissolved in 49 g of chloroform, and the mixture was stirred at room temperature, followed by stirring for 24 hours. Thereafter, the organic layer obtained by removing the solid matter after filtration was washed twice with 989 g of 2N hydrochloric acid. The solvent was removed from the washed organic layer to obtain 88 g of a pale yellow liquid. To the resulting liquid, 88 g of tetrahydrofuran, 1.9 g (8 mm01) of p-toluenesulfonic acid pyridine salt and 88 g of ethanol were added, and the mixture was stirred at 60 ° C for 3 hours. After cooling the reaction solution to 320352 113 200909413, the white solid crystals were precipitated, and the solid matter was taken out after filtration. The PG (i) was obtained in an amount of 19.2 g (PG-i). The yield based on (PG-e) was 48%. &lt;Synthesis Example of (J-6)&gt; Except that 甩(PG-i) is substituted (PG-e), the same procedure as in (combination example of (J-3)) is performed, and 7 is obtained. .3g of pale yellow solid (J-6). The yield based on (J-3A) was 83%. (Example 3) &lt;Production Example of Optical Film&gt; A 2% by weight aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 completely saponified, manufactured by Wako Pure Chemical Industries, Ltd.) was applied to a glass substrate and dried by heating. Thereafter, a film having a thickness of 89 nm was obtained. Next, after applying a rubbing treatment to the surface, the coating liquid (mixed solution) of the composition of Example 3 of Table 3 was applied onto the rubbed surface by a spin coating method, and dried at 45 ° C for 1 minute. . Next, after leaving it for 1 minute at room temperature, it irradiated the ultraviolet-ray of 1200 mJ/cm2, and it was set as the optical film. In Table 3, LC242 was purchased from a liquid crystal compound of BASF Corporation, a polymerization initiator was Irgacure 907 (manufactured by Ciba Specialty Chemicals Co., Ltd.), a leveling agent was BYK361N (manufactured by BY本BYK), and a solvent was a cyclopentanone. Further, the weight % in the table other than the solvent means the weight % of the solid content when the coating liquid is 100% by weight. 114 320352 200909413 [Table 3] Liquid crystal compound photopolymerization initiator, leveling agent Solvent compound number (% by weight) Compound number (% by weight) (% by weight) (% by weight) (% by weight) Example 3 J- 3 3.7 LC242 25.3 0. 9 0. 1 70 Example 4 J-4 3.0 LC242 26.0 0.9 0.1 70 Example 5 J-5 2.4 LC242 26.6 0. 9 0.1 70 Example 6 J-6 5.8 LC242 23.2 0. 9 0.1 70 Comparative Example 3 _ - LC242 29.0 0.9 0.1 70 &lt;Measurement of Wavelength Dispersion Characteristics&gt; The optical film was measured by a measuring instrument (K0BRA-WA, manufactured by Oji Scientific Instruments Co., Ltd.) in a wavelength range of 450 nm to 700 nm. The phase difference value is calculated by the device attachment program, and the phase difference Re (450) at a wavelength of 450 nm, the phase difference Re (550) at a wavelength of 550 nm, and the phase difference Re (650) at a wavelength of 650 nm are calculated. The results are shown in Table 4. In the table, d indicates the film thickness of the liquid crystal layer, and /3 indicates the tilt angle as an index of birefringence, and the smaller the stone value, the more horizontal alignment. It can be seen that the closer the value of Re(450)/Re(550) is to 1, the more the wavelength dependence of the phase difference is lowered. 115 320352 200909413 [Table 4]

Re(550)[nm] Re(450)/Re(550) Re(650)/Re(550) d[ μπι] stone [. Example 3 122 1.049 0. 971 1.02 3.8 Example 4 130 1.060 0. 965 1.02 3.1 Example 5 134 1.058 0. 967 1.04 2.0 Example 6 137 1.045 0.974 1.05 4.3 Comparative Example 3 156 1.070 0.960 1.09 1.7 (Example) 4) An optical film was produced in the same manner as in Example 3 except that the coating liquid of Table 3 was used. The phase difference of the obtained optical film was measured using a measuring instrument (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.). The results are shown in Table 4. It can be seen that the closer the value of Re(450)/Re(550) is to 1, the more the wavelength dependence of the phase difference is lowered. (Example 5) An optical film was produced in the same manner as in Example 3 except that the coating liquid of Table 3 was used. The phase difference of the obtained optical film was measured using a measuring instrument (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.). The results are shown in Table 4. It can be seen that the closer the value of Re(450)/Re(550) is to 1, the more the wavelength dependence of the phase difference is lowered. (Example 6) An optical film was produced in the same manner as in Example 3 except that the coating liquid of Table 3 was used. The phase difference of the obtained optical film was measured using a measuring instrument (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.). The results are shown in Table 4, 116 320352 200909413. It can be seen that the closer the value of Re(450)/Re(550) is to 1, the more the wavelength dependence of the phase difference is lowered. (Comparative Example 3) An optical film was produced in the same manner as in Example 3 except that the coating liquid of Table 3 was used. The initial difference of the obtained optical film was measured using a measuring instrument (K〇BRA_WR, manufactured by Oji Scientific Instruments Co., Ltd.). The results are shown in Table 4. [Industrial Applicability] The present invention can provide a novel compound and cage light which can further suppress the wavelength dependence of the retardation value. The present invention (LCD) or organic electroluminescence (EL_^Ba, M is a polymerizable compound represented by the formula (a), and an antireflection film such as an antireflection (AR) film or a method of providing a film between polarizers is provided. An angle-enhancing film, such as an optical fiber film, which has an excellent wavelength and a strong film, and a circularly polarized light, can be added as long as a small amount of this compound is added. Further, the long dispersion property moves in a negative direction, and the method can be used to make the optical film have dispersion characteristics. Wavelength Dispersion Characteristics [Brief Description] Fig. 1 (a) to (e) are cross-sectional views of a polarizing plate according to the present invention. Figs. 2(a) to (k) are polarization polarities related to the present invention. 3 is a cross-sectional view of a cross-sectional illustration of an organic to an embodiment of the present invention. A cross-sectional view of a main component is illustrated by a cross-sectional view of an example of the present invention. 320352 117 200909413 l' r Optical film 2 ' 2, polarizing film Layer 3 ' 3, '3,, then layer 4 polarizing plate 5 Next layer 6 Liquid crystal panel 7 Light-emitting layer 11 'IV Liquid crystal layer 12, 12, alignment film layer 13, 13' Support substrate 118 320352

Claims (1)

200909413 VII. Scope of application: 1. A polymerizable compound represented by formula (a): Di〇/A10-B10—ΧΙΟ—E10-P10 bo ( D20 N A20-B20-X20-E20-P20 ( In the formula (a), CIO represents a quaternary carbon atom or a quaternary austenite atom; A10 and A20 each independently represent a divalent cyclic hydrocarbon group or a divalent heterocyclic group; and A10 and A20 may also be bonded to an alkyl group or an alkoxy group. Or a halogen atom; D10 and D20 are each independently a hydrocarbon group or a heterocyclic group, and at least one of the fluorene atoms contained in D10 and D20 is substituted with an electron attracting group; D10 and D20 may also be substituted by a hydrocarbon group, an amine group, an ether group, a thioether group, an amine alkyl group, a carbonyl group or a single bond to each other; B10 and B20 independently represent -CRR -, _C, three C_, -CH=CH---CH2-CH2---0---S- --C(=0)---C〇0)-0-, -oc(=o)-, -oc(=o)-o-, -c(=s)-, -c(=s) -o-, -〇-C(=S)-, -0-C(=S)-0-, -CH=N-, -N=CH-, -C(=0)_NR-, _NR-C (=0)_, -OCH2-, -NR-, -CH2O-, -SCHr, -CH2S-, -CH=CH-C(=0)-0---0-C(=0)-CH= CH- or a single bond; here, R and R' each independently represent a hydrogen atom or an alkyl group; when X20 is not a single When X10 and X20 respectively represent a divalent group represented by the formula (2); --A3-B 3--(2) J η [In the formula (2), A3 represents -C(=0)-C6H4 - a divalent cyclic hydrocarbon group or a divalent 119 320352 200909413 heterocyclic group, the -C(=〇)-C6H4-, a divalent cyclic hydrocarbon group or a divalent heterocyclic group may also be bonded to an alkyl group having 1 to 4 carbon atoms. Alkoxy group having a carbon number of 丨 to 4, a difluoromethyl group, a trifluoromethyloxy group, a nitrile group, a nitro group or a halogen atom; B3 is synonymous with the above-mentioned B10 and B20; and n is a group of 1 to 4. An integer, when η is 2 to 4, the structural units composed of A3 and Β3 may be the same or different from each other. When Χ20 is a single bond, χιο represents a divalent group represented by the formula (3); f : one A31-B41--(3) 1 J η [In the formula (3), A31 represents -C(=〇)-C6H4-, a divalent cyclic hydrocarbon group of 5 to 20 membered rings or 5 to 20 members a divalent heterocyclic group of the ring; the gas (1) oxime, a hydroxy group or the heterobasic group may also be bonded to a carbon atom having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or the like. Fluoromethyl, trifluoromethyloxy, nitrile, schlossyl or dentate atom; B41 represents -CRr R〆, -, -c C-, _CH=CH-, -CH2-CH2-, i-〇_, _s-., a c(=0)_, -C(=0)-0-,-0-C(=0)_ , -0-C(=0)-〇-, -CH=N-, _N=CH_, -coo)-·/ -, -NR!' -C(=0)-, -0CH2—, _NRl, one , _CH2〇_, -CH=CH-C(=0)-0-, -〇-C(=0)-CH=CH_ or a single bond; here, Ri, and IV' independently represent carbon atoms Number 丨 to 4 alkyl or hydrogen atom; η represents any integer from 1 to 4; when η is 2 to 4, the structural units composed of A3i and may be the same or different from each other] When X20 When not a single bond, E10 and E2 are independently represented by carbon 320352 120 200909413 alkyl having 2 to 25 atoms, and E10 and E20 may be combined with alkyl, alkoxy, trifluoromethyl, trifluoromethyl. a base group, a nitrile group, a nitro group, a halogen atom; when X20 is a single bond, E10 represents a divalent group represented by the formula (b), and E20 represents an alkylene group or a cycloalkyl group having 1 to 12 carbon atoms. The ruthenium atom contained in E2 也 can also pass through an alkyl group having 1 to 4 carbon atoms and a carbon number! Alkoxy or tetra-substituted to 4; .I Eg ............. B 5 - (b) [In the formula (b), E3 represents a carbon number of 1 to 12 The ruthenium atom contained in the alkyl group may also be substituted with an alkyl group having a carbon number of 4 to 4, an alkoxy group having 1 to 4 carbon atoms or a | | element; Bs represents -C(=0)-0- ^ -〇-C(=〇)_ . -C(=0)-NRi- ^ -NR,-C(-〇)-, -OCHr, -〇-C(=0)-〇- or single bond, Here, 'R represents a group or a hydrogen atom having a carbon number of i to 4. When X20 is not a single bond, P1〇 and P2〇 each independently represent an atom or a polymerizable group, and at least the polymerization of (10) is at least polymerization. When the X20 is a single bond, P1 is a hydrogen atom or a group represented by the formula (p-丨) to ^, and P20 is a hydrogen atom; [In the formula (P-1) to (P-5) RdR5 is divided into the surface of the ground (4) atomic number 320352 121 200909413 1 to 4 of the alkyl or hydrogen atom]). 2. A polymerizable compound represented by the formula (1): Dl\ /Al-Bl~XI-E1-P1 D2 A2 - B2 to X2 - E2 - P2 (in the formula (1), C represents four a carbon atom or a quaternary halogen atom; A1 and A2 each independently represent a divalent cyclic hydrocarbon group or a divalent heterocyclic group; A1 and A2 may also be bonded to an alkyl group, an alkoxy group or a halogen atom; D1 and D2 are independently independently a hydrocarbon group or a heterocyclic group; and at least one hydrogen atom contained in D1 and D2 is substituted with an electron attracting group; D1 and D2 may also be substituted by a base group, an amine group, a thiol group, a thiol group or an amine group. Bases, bases or single bonds are linked to each other; B1 and B2 independently represent _CRR, -, -c three c_, -CH=CH-, -CH2-CH2-, -〇-, _s_, _c(=〇 )_, -c(=〇)_〇_, -oc〇o)-, -〇-c(=〇)-〇-, __c(=s)_, _c(=s)_〇_, -〇 -C(=S)_ , _〇_c(=s)_〇_ , _CH=N_ , _n=ch—, C(-0)-NR- ' -NR-C(=〇)~ . -OCH2 - ' -NR- ' -CH2O- ' -SCH2- &gt; -CH2S- &gt; -CH=CH-C(=0)-〇- &gt; -0-C(=0)-CH=CH- or single a bond; here, R and R each independently represent a hydrogen atom or an alkyl group; XI and X2 are independently represented a divalent group represented by the formula (2); A3 B 3 (2) η [In the formula (2), A3 represents a -C(=0)-, a divalent cyclic hydrocarbon group or a divalent heterofluorenyl group; (=o)-aH4-, a divalent cyclic hydrocarbon group or a divalent heterocyclic group, 122 320352 200909413 may also be bonded to a carbon atom having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a difluoromethyl group. a base, a trifluoromethyloxy group, a nitrile group, a nitro group or a dentate atom; B3 is synonymous with the aforementioned B1 and B2; η represents an integer of 1 to 4; and when η is 2 to 4, 'by A3 and Β3 The structural units may be the same or different from each other. Ε1 and Ε2 each independently represent an alkylene group having 2 to 25 carbon atoms, and Ε1 and Ε2 may also be combined with an alkyl group, an alkoxy group, or a trifluoromethyl group. The group, the trifluoromethyloxy group, the tribasic group, the aryl group, and the halogen atom each independently represent a hydrogen atom or a polymerizable group, and at least one of ρ and P2 is a polymerizable group). 3. The polymerizable compound of the first aspect of the patent application, wherein the electron attracting group bonded to the group of D1 and D2 in the formula (1) is an exact group, a nitrile group or a difluoromethyl group, represented by the formula (4) The base or the group represented by the formula (5): - C - 0 II , 〇 (4) - ~ c - Rb ό (5) (Formula (4) and (5) H represent a hydrogen atom, a linear number of carbon atoms 1 to 8 a cylindrical, branched ordinal group having 3 to 18 carbon atoms, a ring having 5 to 18 carbon atoms, a phenyl group, a fluorenyl group or a thienyl group; a linear form having a reverse atomic number of 1 to 18 The number of filaments, the number of condensed atoms is 3 to (4), the branched alkyl group, the cycloalkyl group having 5 to 18 carbon atoms, the phenyl group, the butyl group or the porphin group. 4. The polymerizable compound of claim 2 or 3, wherein B1 and B2 in the formula 320352 123 200909413 (1) are single bonds, -〇-, -S-, -C(=0)-, ~ C〇〇)-〇---0-C(=0)- or -0-C(=0)-0 base. 5. The polymerizable compound according to any one of claims 2 to 4, wherein the divalent group consisting of C1, D1 and D2 in the formula (1) is selected from the formula (D-1). To the divalent group of the group (D-11): (Dl 1) (In the formulae (D-1) to (D-11), the EWG independently represents the electron attracting group; P and q respectively represent the independent 〇 4 4, and r represents 〇 to 6; however, when the above base It is (EWGW(EWG)&lt;base time, Bp + qy, when it has (EWG)r and (EWG)c^ base; [$Γ+(^1〇). 6. As claimed in claim 2纟5, any of the 35 combinations, wherein the polymerizable group in the formula (1) is acrylonitrile or T-based propyl S&amp; based on the polymerized compound as claimed in claim 2 Wherein the polymerizable compound represented by the formula (1) is selected from the group consisting of compounds represented by the formulae (Η) to (1-C): 320352 124 200909413 1-A 1-B 1-C (in the formula (1-A) to UC), nl independently represents that the integers from i to 3 each independently represent an integer of 2 to 14; R, respectively, independently represent a gas atom; Or methyl). A composition comprising: a polymerizable compound different from the polymerizable compound according to any one of claims 2 to 7 and exhibiting liquid crystallinity, and the items of the second and seventh items of the patent application The polymerizable compound of the invention of claim 8, wherein the polymerizable compound which is different from the polymerizable compound of any one of claims 2 to 7 and exhibits liquid crystallinity. , a compound represented by formula (I), formula (II), formula (ΠΙ) or formula (IV): P110-B110-E110- (B120-A110) s-B130-E120-B140-P120 (I) ( II) (III) (IV) P110-B110-E110- (A110-B120) S-E120-B130-P120 P110-B110-E110- (B120-A110) -F110 P110-B110-E110- (B120-A110) S-B130-F110 [In the formulae (I) to (IV), A110 each independently represents a divalent cyclic hydrocarbon group, a divalent heterocyclic group, a methylene extended phenyl group, an oxygen extended phenyl group or a sulfur extended phenyl group ( Thiophenylene); A110 may also be bonded to a carbon atom having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or a halogen atom; B110, B120, B130 and B140 independently represent _CRi Ri-, -C, respectively. C._, -CH =CH-, -CH2_CH2-, -0-, -S--, _C(-0)- ' ^0(=0)-0- ' -0-C(=0)_ N _0_C(=0)_0 - ' ~C(-S)- ' _C(-S)_0_ ^ _0_C(=S)_ N -0~0(-8)-0·· ' -0-C(=0)-CH=CH- or a single bond (and, Ri' and Ri" each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; E110 and E120 each independently represent carbon a number of 2 to 25 alkyl groups; and, E110 and E120 may also be bonded to an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an atom of an atom; 126 320352 200909413 Pi 10 and P120 Respectively, the polymerizable group is independently represented; Fn 〇 represents a hydrogen atom, an alkyl group, a nitrile group, a stone succinyl group, a tris or a γ atom, and S represents an integer of 丨 to 5, respectively; when s is 2 to 5, by Alio And the structural units formed by B120 may be the same or different from each other.] 10. The composition of claim 8 or 9 of the patent application, wherein 'relative to the application is different from items 2 to 7 A total of 1 part by weight of the polymerizable compound of the polymerizable compound of any of the above, and the polymerizable compound of any one of the second to seventh aspects of the patent application, claim 2 to 7 The content of the polymerizable compound according to any one of the items is 3 to 50 parts by weight. 11. An optical film containing: from the application The structural unit of the polymerizable compound according to any one of items 2 to 7. The optical film of the invention is polymerized by the composition of any one of claims 8 to 1. 13. The optical film as claimed in claim u or 12 is used for a /4 plate having a phase difference (Re (550)) of wavelength 550 nm of 113 to 163 nm. U. 12-item optical film used for phase difference (Re(550)) at a wavelength of 550 nm of 250 to 300 nm; 1/2 plate. 15··· kinds of polarizing plates' containing: Patent application range U to An optical film and a polarizing film according to any one of the items of the item of the above-mentioned item of the present invention, which is a polarizing plate of the fifteenth item of the patent application, and a liquid crystal panel. An organic electroluminescent panel comprising a polarizing plate of claim 15 of the patent application. 18. A method for producing an unpolymerized film, which is a composition of any one of claims 8 to 10. After coating on the support substrate, it is dried. 19· - Preparation of unpolymerized film The method of manufacturing the composition of any one of claims 8 to 1 after drying on the alignment film formed on the substrate of the support, and drying the composition. A method of curing an unpolymerized film obtained by the production method of claim No. 19 or 19 by polymerization. 21. A compound which is expressed by the formula (11) or (21) · 'A / &lt;EW% E21-B21 (EWG)w./C\ (EWG)qi P At,x q1 E21-B21 Bfl-X-ErBarP^ (21) (EWGhP (u) (Formula (11) to (21) Wherein, EWG independently represents an electron attracting group; pi and ql each independently represent any integer from 0 to 4; however, i Spl + ql ^ 8 ; Απ and Al2 independently represent 1,4-phenylene The 1,4-phenylene group may also be bonded to at least one substituent selected from the group consisting of a subunit of 1 to 4 and an alkoxy group of (4) subunits i to 4; Bn, B21 and B31 Respectively represent _〇_, _s_, -c(=〇)_, 320352 128 200909413 -C(:〇)-0—— -〇-c(=〇)-, -c(:o)-NRl, —, _NRl —C(=〇)...0CH2~, —〇-c(=o)-o- or single key; here, Ri knife is unique The standing indicates a courtyard or a gas atom having a carbon number of 1 to 4; x represents a divalent group represented by the formula (3); A31 represents ~C(=〇)-C6H4_, a divalent cyclic hydrocarbon group of 5 to 20 membered rings or a divalent heterocyclic group of 5 to 20 membered rings; the _c (gamma h: _, ring-shaped smoke) Or a heterocyclic group may also be bonded to a carbonyl group having a carbon number of 丨 to 4, an alkoxy group having an anatomical number of 1 to 4, a trifluoromethyl group, a trifluoromethyloxy group, a nitro group or a halogen atom. ; heart means "Rl" _, _CeC-, _ch=ch...n, 〇一, -S~, -.-C(=0)~, -C〇0)-〇-, -〇-C(=〇 )-, -〇-c(=〇)-〇-, CH N N-CH-&gt;-0(=0)-^^^ -Ν-NRr -C(=0)~--0CH2-^ - NRi - &gt; -CH2O- ^ -CH=CH-C(=0)-0- ^ -0-C(=〇)-CH=CH- or single bond; here, Rl, and Ri, are independent The ground represents a hospital atom or a hydrogen atom having a carbon number of 1 to 4; η represents an integer of 1 to 4; when η is 2 to 4, the structural units composed of a31 and B41 may be the same as each other.互π denotes an alkylene group having 1 to 12 carbon atoms, and the hydrogen atom contained in En may also pass through an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a halogen atom. Substituted; E21 represents an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group, and the hydrogen atom contained in En is also Substituted by an alkyl group having 1 to 4 carbon atoms, an alkoxy group having a carbon number of J 129 320352 200909413 to 4 or a halogen atom; Pn is a hydrogen atom or a group represented by the formula (P-1) to (p-5) ; [In the formulae (P-1) to (P-5), R1 to R5 each independently represent a carbon atom or a chlorine atom of 1 to 4]. 22. The compound according to claim 21, wherein the EWG in the formulae (11) and (21) is a nitro group, a nitrile group or a trifluoromethyl group. 23. The compound of claim 21, wherein the Asi is any one of the formulas (4-1) to (4-5). 24. The compound of any one of claims 21 to 23, wherein p! in the formulae (11) and (21) is a group represented by the formula (ρ_ι). 25. A composition comprising: the scope of the patent application. A compound of any one of the above items, and a polymerizable compound exhibiting liquid crystallinity. 26. An optical film obtained by polymerizing a composition of claim 25 of the patent application. An optical film comprising the structural unit of the compound of any one of claims 21 to 24 of the patent application. - a 1/4 plate, which is an optical 320352 130 200909413 film of claim 26 or 27, and a phase difference (Re(550)) of light having a wavelength of 55 Onm transmitted through the optical film is 113 to 163 nm . 29. A 1/2 plate which is an optical film of claim 26 or 27, and a phase difference (Re(550)) of light having a wavelength of 550 nm transmitted through the optical film is 250 to 300 nm. A polarizing plate comprising: an optical film according to any one of claims 26 to 29, and a polarizing film. A flat display device comprising: a polarizing plate of claim 30 and a liquid crystal panel. An organic EL display device comprising: a polarizing plate of the 30th patent application; and an organic electroluminescent panel. A method for producing an unpolymerized film, which comprises applying a solution containing the composition of claim 25 to a support substrate, followed by drying. A method for producing an unpolymerized film, which comprises applying a solution containing the composition of the second aspect of the patent application to an alignment film formed on a support substrate, and drying the solution. A method of producing an optical film which is obtained by curing by polymerization by the unpolymerized film obtained by the production method according to any one of claims 33 or 34. 131 320352