TW201100410A - Compound, optical film and method for making an optical film - Google Patents

Abstract

The invention provides a compound having a divalent group and represented by the following formula (1-1) or (1-2), wherein Z1 and Z2 respectively independently represent a hydrogen atom etc., Q1 and Q2 respectively independently represent -S- etc. Y1 represents a substituted or unsubstituted polycyclinc aromatic hydrocarbon group, or a substituted or unsubstituted poly cyclic aromatic heterocyclic group; D1 and D2 respectively independently represent a single bond or a divalent bonded group, G1 and G2 respectively independently represent a divalent aliphacyclic hydrocarbon group. This invention also provides an optical film by polymerizing the above compound.

Description

201100410 VI. Description of the Invention: [Technical Field] The present invention relates to a compound, an optical film, and an optical film. [Prior Art] The flat panel display device (FPD) includes a polarizing plate or a phase difference plate. A member of an optical film. The optical film may be, for example, an optical film obtained by dissolving a polymerizable compound in a solvent. Such a polymeric compound in SID Symposiura

Digest of Technical Papers, 2006, Vol. 37, p. 1673, has been disclosed as a compound of the formula (LC242). SUMMARY OF THE INVENTION The present invention provides the following. [1] A compound having a 2-base represented by the formula (1_υ or formula (1_2): '

(wherein Ζ1 and Ζ2 each independently represent a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 丨6, a cyano group, a nitro group, an alkyl group having a carbon number of 丨6, and a carbon number of 1; Alkylsulfonyl group to 6, fluorine 1 to 6 321867 201100410 Burning base, therefore 1 to 6 entertainment 4 [〇 〇, λ.,, (SUHanyl) Ί〗 1 to 6 alkane sulfur Ν Ν 至 Ν Ν Ν 烧 烧 Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν Ν 'dialkylamine thiol or -C00H; Q and Q are independently represented - CRlR2_, _s, _nr2, , ^ and R2 independently represent a hydrogen atom or a carbon number of 1 to 4 / Ο L Table It Generation: an unsubstituted polycyclic aromatic hydrocarbon group or a substituted or unsubstituted oxime cyclic aromatic heterocyclic group; D and D each independently represent a single bond or a divalent linking group; G1 and G2 represent the two-valent An alicyclic hydrocarbon group which may have 4 atomic groups, a carbon number of 1 to 4, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a cyano group or The nitro group, the _CH2_ of the alicyclic hydrocarbon group may also be substituted by -0---S- or -NH-). [2] The compound according to [1], which has a divalent group represented by the formula or the formula (2-2): ο ~^-A1^-E1-G^D1

D2_G2_E2+A2_B2 Bu (2-1)

Bi-Ai^_Ei_Gi_Di

D2-G2-E2{-A2-B2)y~- (2*2) 5 321867 201100410 (Formula A, z, ^", (^, ^, ^, ^, and ^ respectively represent and ^] Defining the same meaning; E and E respectively represent a single bond or a divalent linking group; B and B respectively represent a single bond or a divalent linking group; A and A respectively represent a divalent alicyclic hydrocarbon group or a divalent aromatic group a hydrocarbon group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having a carbon number of 4 to 4, an alkoxy group having a carbon number of 4 to 4, and a carbon number of 1. a fluoroalkoxy group, a cyano group or a nitro group to 4; k and 1 each independently represent an integer of 〇 to 3) [3] A compound of the item [1], which is a formula (3 - 丨) or a formula ( 3_2) shown: P1_F1

E^G^D1

D2_G2_E2_^A2_B2l ρ2_ρ2 (3-χ)(Ζ, P^F^B^A^E^G^D1

D2__G2_E2^.A2_B2^__F2_p2 (3-2) (where Ζ1, Ζ2, Q1, Q2, Υ1, D1, D2, G1, G2, Ε1, Ε2, Β1, Β2, A1, A2, k, and 1 respectively represent The same meaning as defined in [1] and [2]; F1 and F2 each independently represent an alkyldiyl group having 1 to 12 carbon atoms; the alkanediyl group may also have an alkyl group having 1 to 5 carbon atoms, carbon The alkoxy group or the halogen atom of 1 to 5, the -CH2- of the pyridyl group may be substituted by -〇-, -C0-; 321867 6 201100410 p1 and p2 each independently represent a hydrogen atom or a polymerizable group). [4] The compound according to any one of [1] to [3], wherein γ1 is a group represented by formula or formula (^-4):

(In the formula, 'z3 independently represents a halogen atom, a carbon number of 丄 to 6, a sulphur group, a nitrogen group, a succinyl nitrite' group, a carbon number of 1 to 6, a calcined base, and a carbon number of 1 to 6 Two bases, a carbaryl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a sulfur-burning group having 1 to 6 carbon atoms, a N-N-diamine group having 2 to 8 carbon atoms, and a carbon number of 1 N-alkylamino group to 4, material county, Weizhi to 6 N_ carbyl amine gamma, carbon number 2 to 12 N, H-aminoamine or -C00H; 〇V1 represents -CO-, -S-, -NR3-, -〇-, _Seu are independently represented by ^N=, 'R3 are respectively independent" and represent an atom or an alkyl group having 1 to 4 carbon atoms; however, vl, wl, W2, r And at least one of W5's claims contains s, N, 〇 or Se; a respectively represents 〇 to an integer of 3). [5 [4] The compound of the formula [4], wherein the base of the formula (γ1)) is the base of the formula 321867 7 1 , and the base represented by the formula (Υ-4) is the formula (Υ3-3). ) shown 201100410

(Ζ\ (Υ3·3) (wherein Z3, a, V1, and w2 represent the same meanings as defined in [4], respectively.) [6] A compound such as [4] or [5], where , Shanghai is -S_, _NR3_, or _〇_. [7] The compound of any one of [1] to [6] wherein g1 and g2 are trans, 4-cyclohexyldiyl. The compound according to any one of [2] to [7], wherein, VIII, and human 2 are each independently represented by a 1,4-phenylene group or an ι,4-cyclohexanediyl group, the 1> The 4-phenylene group and the 1'4-1⁄4 hexanediyl group may also have an _ atom, an alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group, a cyano group or a nitro group. [9] a compound of any one of [8], wherein only the compound is bonded to Al

[11] A composition comprising the compound of any one of [1] to [IG] and a liquid crystal compound (only, 'different from the aforementioned compound). 321867 8 201100410 [12] The composition of [11], wherein the liquid crystal compound is represented by the formula (2: liquid crystal compound: pu-扒11吟Bl2-G (10), (wherein, A" is independent And a divalent aromatic hydrocarbon group, a divalent alicyclic hydrocarbon group or a divalent heterocyclic group, and the aromatic hydrocarbon group, the alicyclic hydrocarbon group, and the heterocyclic group may have a halogen atom, an alkyl group having a carbon number of 66, or Alkoxy group having a carbon number of 丨6, an N-alkylamino group having 1 to 6 carbon atoms, N,N-dialkylalkylamino group having a carbon number of 2 to 12, a nitro group, a cyano group or a thio group; And B12 are independently represented - CRlY5_, _c Ξ c-, κΗ_, -CH2-CH2-, -〇-, -s-, -c(=〇)-, _c(=0)-0-, -〇-c (=〇)-, -0-C(=0)-0- ^ -C(=S)- ' -C(=S)-0---0-COS)---CH=N-, . _N=CH—, —N=N—, —C〇0)-NR16-, -NR16-C(=0)-, -〇CH2-, -OCF2- > -NR16- s -CH2O- ^ -CF2O - > -CH=CH-C(=0)-〇-. -(HX=0)-CH=CH- or a single bond, and R14 and R15 independently represent a hydrogen atom, a fluorinated fluorine atom or a carbon number of 1 to 4 The alkyl group, or the combination of Ru and R15, represents an alkanediyl group having a carbon number of 4 to 7; and R16 represents a hydrogen atom or a carbon number of 1 to 4; 11; E represents an alkanediyl group having 1 to 12 carbon atoms; the alkanediyl group may also have an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a halogen atom; * G represents a hydrogen atom, a self atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a fluoroalkyl group having 1 to 13 carbon atoms, and an N-alkyl group having 1 to 13 carbon atoms. Amino group, N,N-dialkylamino group having 2 to 26 carbon atoms, cyano group or nitro group, also 9 321867 201100410 or an alkyl group having a carbon number of 1 to 18 having a polymerizable group, and the alkyl group may also be used. An alkoxy group having 1 to 6 carbon atoms or an i atom; t represents an integer of 1 to 5). [13] The composition of [11] or [12], which further comprises a polymerization initiator. [14] The composition of [13], wherein the polymerization initiator contains an acetophenone compound. [15] An optical film obtained by polymerizing a compound of any one of [mouth to oxime]. [16] An optical film obtained by polymerizing a composition according to any one of the items. [Π] An optical film such as [15] or [16] whose phase difference (Re(550)) in the wavelength of 55 〇 nm is used for /4 plates of 113 to 163 nm. [18] The optical film of [15] or [16], which has a phase difference (Re(550)) of 55 〇 nm, is 250 to 300 nro; [19] A polarizing plate comprising the optical film and the polarizing film according to any one of [15] to [18]. [20] A color filter which is formed on an alignment film coated on a color filter substrate to form an optical film according to any one of [15] to [18]. [21] A liquid crystal display device comprising a color filter of [2〇]. [22] A flat panel display device is provided with a liquid crystal panel including the polarizing plate of [19]. The inter-organic rainbow display (four) is an organic electroluminescence panel having a polarizing plate containing the old item. 321867 10 201100410 [24] A method for producing an unpolymerized film, which comprises applying a solution containing the compound of any one of [1] to [10] on a support substrate or on a support substrate. The oriented film is dried again. [25] A method of producing an optical film, characterized in that the unpolymerized film obtained by the method of [24]* is cured. [Embodiment] The compound of the present invention contains a divalent group represented by the following formula (1-1) or formula (1-2).

O Y1 VI In the formula (1-1) and the formula (1-2), Z1 and Z2 each independently represent a ruthenium atom, a halogen atom, a ruthenium group having a number of turns of 1 to 6, a cyano group, a terminal group, and a carbon number of 1 to 6. An alkylsulfinyl group, an alkylsulfonyl group having 1 to 6 carbon atoms, a fluoroalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, N-alkylamino group having 1 to 6 carbon atoms, N,N-dialkylamino group having 2 to 12 carbon atoms, N-alkylamine sulfonyl group having 1 to 6 carbon atoms, and carbon number 2 to 12 N,N-dialkylamine sulfonyl or -C00H. The halogen atom may, for example, be a gas atom, a gas atom, a desert atom or a halogen atom, and is preferably a fluorine atom, a chlorine atom or a desert atom. The alkyl group having 1 to 6 carbon atoms may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group or a hexyl group, preferably a carbon number. The alkyl group of 1 to 4 is more preferably an alkyl group having 1 to 2 carbon atoms, and particularly preferably 11 321867 201100410 is a methyl group. The alkylsulfinyl group having 1 to 6 carbon atoms may, for example, be a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group or a butylsulfinylene group. Base, isobutylsulfinyl, t-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl and hexylsulfinyl, preferably a carbon number of 1 to 4 The sulfinyl group is more preferably an alkylsulfinyl group having 1 to 2 carbon atoms, particularly preferably a methylsulfinyl group. The alkylsulfonyl group having 1 to 6 carbon atoms may, for example, be methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl or isobutylsulfonate. An anthracenyl group, a second butyl sulfonyl group, a tert-butylsulfonyl group, a pentylsulfonyl group and a hexylsulfonyl group, preferably an alkylsulfonyl group having 1 to 4 carbon atoms, more preferably a carbon number of 1 The alkylsulfonyl group to 2 is particularly preferably a methylsulfonyl group. The fluoroalkyl group having 1 to 6 carbon atoms may, for example, be a fluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group or a nonafluorobutyl group, and preferably a fluorine having a carbon number of 1 to 4. The alkyl group is more preferably a fluoroalkyl group having 1 to 2 carbon atoms, particularly preferably a trifluoromethyl group. Examples of the alkoxy group having 1 to 6 carbon atoms include a decyloxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, and a third butoxy group. The pentyloxy group and the hexyloxy group are preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 2 carbon atoms, and particularly preferably an anthracenyloxy group. Examples of the alkylthio group having 1 to 6 carbon atoms include an anthracenylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a second butylthio group, and a third butylthio group. The pentylthio group and the hexylthio group are preferably an alkylthio group having 1 to 4 carbon atoms, more preferably an alkylthio group having 1 to 2 carbon atoms, and particularly preferably an anthracenethio group. 12 321867 201100410 The N-alkylamine group having 1 to 6 carbon atoms may, for example, be N-decylamino, N-ethylamino, N-propylamino, N-isopropylamino, N- Butylamino group, N-1 isobutylamino group, N-second butylamino group, N-tert-butylamino group, N-pentylamino group and N-hexylamino group, preferably carbon number 1 The N-alkylamino group to 4, more preferably the N-alkylamino group which is a hindered number of 1 to 2 is particularly preferably an N-methylamino group. The carbon number is 2 to 12, and the fluorene-dialkylamine group may, for example, be anthracene, fluorenyl-dimethylamino group, fluorenyl-methyl-hydrazine-ethylamino group, hydrazine, fluorene-diethylamino group. ,Ν,Ν_dipropylamino, hydrazine, hydrazine-diisopropylamino, hydrazine, hydrazine-dibutylamino, hydrazine, hydrazine-diisobutyl butylamino, hydrazine, hydrazine-dipentane The amino group, hydrazine, hydrazine-dihexylamino group, preferably a carbon number of 2 to 8, a fluorenyl-dialkylamino group, more preferably a carbon number of 2 to 4, a fluorenyl-dialkylamino group, It is especially suitable for hydrazine, hydrazine-dimethylamino. The hydrazine-alkylamine sulfonyl group having 1 to 6 carbon atoms may, for example, be hydrazine-methylamine sulfonate, fluorenyl group, fluorenyl-ethylamine sulfonyl group, fluorenyl-propylamine sulfonyl group, hydrazine-isopropyl group. Amine sulfonic acid group, Ν-butylamine continuation base, Ν-isobutylamine acid group, hydrazine-t-butylamine sulfonyl group, hydrazine-tert-butylamine sulfonyl group, fluorenyl-pentyl group Aminesulfonyl and hydrazine-hexylamine sulfonyl, preferably a hydrazine-alkylamine sulfonyl group having 1 to 4 carbon atoms, more preferably a fluorene-alkylamine sulfonyl group having 1 to 2 carbon atoms. It is especially suitable for the indole-hydrazinylsulfonyl group. The carbon number is from 2 to 12, and the fluorene-dialkylamine sulfonyl group may, for example, be anthracene, fluorenyl-didecylamine sulfonyl group, fluorenyl-fluorenyl-fluorenyl-ethylamine sulfonyl group, hydrazine, hydrazine. -diethylamine sulfonyl, hydrazine, hydrazine-dipropylamine sulfonyl, hydrazine, hydrazine-diisopropylamine sulfonyl, hydrazine, hydrazine-dibutylamine sulfonyl, hydrazine, hydrazine Diisobutylamine sulfonyl, hydrazine, hydrazine-dipentyl sulfonyl hydrazide and hydrazine, hydrazine-dihexylamine sulfonyl hydrazide, preferably having a carbon number of 2 to 8, hydrazine-dialkylamine sulfonate The sulfhydryl group is more preferably a carbon number of 2 to 4, a fluorenyl-dialkylamine sulfonyl group, and particularly preferably an anthracene, fluorene-dimethylamine sulfonyl group. 13 321867 201100410 Z1 and Z2 are divided into two groups: hydrogen atom, _ atom, methyl group, aryl group, nitro group, methylsulfonyl group, trifluoromethyl group, methoxy group, sulfonium group, N_decylamine Base, N,N-dimethylamino, sulfamidino, N,N, dimethylaminesulfonyl or -C00H. In the formulae (1-1) and (b), Q1 and Q2 each independently represent -CRY S NR2---C0- or 0-, and R1 and R2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. base. The alkyl group having 1 to 4 carbon atoms in R1 and R2 may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group or a tert-butyl group, and preferably has a carbon number of 1 to 2. Alkyl, more preferably methyl. Q1 and Q2 should each independently represent -S---CO-, -NH---N(CH3)- » more preferably ~S- or -C0-. The group represented by the formula (1-1-A) in the divalent group represented by the formula (1-1) may, for example, be represented by the following formula (1-1-1) to formula (1-1-18). The base shown. Y1

Q person N

(1-1-A) 321867 14 201100410

(1-1-1) (1-1-2) (1-1-3) (1-1-4)

(1-1-9) (1-1-11) (1-1Ί0) Y1

(1-1-14)

NC CN (1-1-18) 15 321867 201100410 The group represented by the formula (1 to 2-A) in the divalent group represented by the formula (1-2) can be exemplified by the following formula (1). -2-1) to the meaning of formula (1-2-5). Earth ’,

(1-2-5) N(CH3)2 " Br ch3 (1.2.1) (1-2-2) (1-2-3) In the formula (Μ) and formula (1-2), γ1 represents a substitution Or non-...the aromatic hydrocarbon group or the substituted or unsubstituted polyhydrocarbyl group, for example, two or more #, Fangxiangzhi group, and two condensed aromatic groups formed by two: ?#_ Aromatic 47! = the aromatic hydrocarbon group formed. And there is a condensed aromatic heterocyclic ring having at least a "heterocyclic heterocyclic ring and a ring", and at least one of the aromatic ring and the aromatic ring and aromatic ring.形 群 群 】 】 】 】 】 】 】 】 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 个 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少 至少1 321867 16 201100410 ^ 6 alkyl, cyano, exact, nitroso, carbon number i to 6 alkyl sulfonyl group, alkyl sulfonyl group having 1 to 6 moles, carbon number 丨 to 6 a fluoroalkyl group, an alkoxy group having an inverse number of 1 to 6, an alkylthio group having a carbon number of 丨6, an N-hospital base having a carbon number of 丨6, a N having a carbon number of 2 to 8, and a ruthenium Amine, amine continuation, N-alkylamine sulfonyl group having 1 to 6 carbon atoms, N,N-dialkylamine sulfonyl group having 2 to 12 carbon atoms, or -C〇〇H. The group represented by the formula (Ytl) to the formula (γΐ- is more preferably a group represented by the formula (Υ1-:!) to the formula (Υ1·^).

(Υ1^) (γΐ.5) (Yl6) (Yh7) (wherein Z represents independently a halogen atom, an alkyl group having a carbon number of i to 6, a cyano group, a nitro group, a nitroso group, and a carbon number of 丨6 Alkyl sulfonyl group, a carbaryl group having a carbon number of 丨6, a carbaryl group having a carbon number of 丨6, an alkoxy group having a carbon number of 丨6, an alkylthio group having an ammonium number of 1 to 6, and a carbon number 2 to 8 dialkylamino group, alkylamino group having 1 to 4 carbon atoms, amine sulfonyl group, carbon number 丨 to 6 N_ 17 321867 201100410 alkylamine sulfonyl group 'carbon number 2 to 12 n,N-dialkylamine sulfonyl or -C00H; V1 and V2 independently represent -c〇---S-, -NR2-, -0---Se- or -S〇2-; W , W, W3, W4, and W5 respectively represent _ cr3 = or, R3 independently represents a cesium atom or a carbon number of 1 to 4; however, among v1, v2, w1, W2, W3, W4, and W5 At least one of the lines contains s, n, 〇 or Se; a respectively represents an integer from 〇 to 3, and b independently represents an integer from 0 to 2). The formula represented by the formula (Y1-:!) is any one of the formulas represented by the formula (YLD to the formula (γ2_6). The formula represented by the formula (Y1·^) is the formula (γ2_7) Or a group represented by the formula (γ2-9), wherein the group represented by the formula (^-3) is a group represented by the formula (γ2_8) or the formula (γ2-ΐ〇). It is represented by the formula (Yq) The basis is any one of the formulas represented by the formula (Yq丨) to the formula (Υ2_13). The formula represented by the formula (Yi-5) is a formula (γ2-Η) to a formula (γ2_16). Any one of the groups shown. It is more preferably any one of the groups represented by the formula (Y3-l) to the formula (Υ3-6). 321867 18 201100410

CY2-5) (Y2-6) (Y2-7) (Y2-8) n^v(z3)b

(Y2-9)

(Y2-10) (Z3), (Z3)a

0 (Z3)a

(Y2-15)

19 321867 201100410

(Υ3·3) m

(Υ3-6) (wherein, Z3, V1, V2, W1, W2, W3, W4, W5, a, and b have the same meanings as described above), a halogen atom in Z3, an alkyl group having 1 to 6 carbon atoms, Alkylsulfonyl group having 1 to 6 carbon atoms, alkylsulfinyl group having 1 to 6 carbon atoms, fluoroalkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, and carbon number 1 to 6 Alkylthio group, N,N-dialkylamino group having 2 to 8 carbon atoms, N-alkylamine sulfonyl group having 1 to 4 carbon atoms and 1 to 6 carbon atoms to 2 The N,N-dialkylsulfinyl group of 12 may be the same as described above, for example. Wherein 'Z3 is preferably a halogen atom, a fluorenyl group, an ethyl group, an isopropyl group, a second _:, a fluorenyl group, a phenyl group, a cis group, a methyl group, a nitroso group, an i fluoromethyl group, a decyloxy group, a beta-decyl fluorenyl group, an N,N-didecylamino group, an N-amino group or a -C00H, more preferably an anthracene e ^ ' a prison atom, a fluorenyl group, an ethyl group, an isopropyl group, a second 321867 20 201100410 Butyl, pentyl, hexyl, cyano, nitro, trifluoromethyl, especially methyl, ethyl, isopropyl, t-butyl, pentyl or hexyl. V1 and V2 should be independent of _S_, _NR3_ or -0-, respectively. The w1 to r systems should be independently -cr3= or. * At least one of V1, V2 and W1 to W5 preferably contains S, N or 0. a should be 0 or 1, and b should be 0. Specific examples of Y1 include, for example, a group represented by the formula (ar-Ι) to the formula (ar-840). Further, in the following groups, Me represents a methyl group, Et represents an ethyl group, and * represents a binding site. ❹ 21 321867 201100410

(ar-001) (ar-003) (ar-004) (ar-005) (ar-006) (ar-007)

(ar-008) (ar-010) (ar-011) (ar-012) (ar-013) (ar-014)

(ar-016) (ar-016) (ar-018) (ar-019) (ar-020) (ar-021)

(ar-022) (ar-025) (ar-025) (ar-026) (ar-027) (ar-028)

(ar-029) (ar-030) (ar-031) (ar-032) (ar-033) (ar-034) (ar-035) 22 321867 201100410

(ar-036) (ar-037) (ar-038) (ar-039) (ar-040) (ar-041) (ar-042)

(ar-043) (ar-044) (ar-045) (ar-046) (ar-047) (ar-048) (ar-049)

(ar-050) (ar-053) (ar-053) (ar-053) (ar-054) (ar-055) (ar-056)

(ar-057) (ar-058) (ar-059) (ar-060) (ar-061) (ar-062) (ar-063)

(ar-064) (ar-065) (ar-066) (ar-067) (ar-068) (ar-069) (ar-070) 23 321867 201100410

(ar-072) (ar-074) (ar-074) (ar-075) (ar-076) (ar-077)

(ar-078) (ar-081) (ar-081) (ar-082) (ar-083) (ar-084)

(ar-085) (ar-086) (ar-087) (ar-088) (ar-089) (ar-090) (ar-091)

(ar-092) (ar-095) (ar-095) (ar-096) (ar-097) (ar-098)

(ar-099) (ar-100) (ar-101) (ar-102) (ar-103) (ar-104) (ar-105) 24 321867

2〇ll〇〇410 • · C . o2n' ... s Secret BVa 八 u wn S MeHN〇2S, Secret SW Η, h i

〇* * * ♦ * * (ar-106) (ar-107> (ar-108) (ar-109) (ar^llO) (ar-111) (ar-112) x> b -~b -d D- -o- ^ ^ ^ ♦ ♦ 丰* * * * (ar-113) (ar-114) (ar-115) (ar-116) (ar-117) (ar-118) (ar-119) / w ^ 7λ-

G 0> Factory ♦ ♦ ♦ ♦ 参 (ar-120) (ar-121) (ar-122) (ar-123) (ar-124) (ar-125) (ar-126)

Me Me F Me Me Me — F

v _F K F. >-\ F_ W /Λ-ρ ρ-^Λ-Μβ Q~F ppp 广广 / (ar-127) (ar-128) (ar-129) (ar.130) (ar -131) (ar-X32) (ar-133)

Me corpse, ~v_, fortunately

G ψ r i \38) One (-) l 1 t 13^ (ar.137) (^38> ^ (a,l34) (-135> 201100410

(ar-141) (ar-142) (ar-143) (ar-144) (ar-14S) (ar-146) (ar-147)

(ar-148) (ar-149) (ar-150) (ar-151) (ar-152) (ar-153) (ar-154)

(ar-155) (ar-158) (ar-158) (ar-158) (ar-160) (ar-161)

CN (ar-162) (ar-163) (ar_164) (ar-165) (ar-166) (ar-167) (ar-168)

26 321867 201100410

(ar-177) (ar-177) (ar-178) (ar-179) (ar-180) (ar-181) (ar-182)

(ar-183) (ar-184) (ar-185) (ar-187) (ar-188) (ar-189)

Me02S.

Φ Yu Xiao

(ar-190) (ar-193) (ar-193) (ar-194) (ar-195) (ar-196)

(ar-197) (ar-198) (ar-199) (ar-200)

(ar-205) (ar-205) (ar-206) (ar-207) (ar-208) (ar-209) (ar-210) 27 321867 201100410

Me take

♦

Me F

(ar-213) (ar-214)

(ar-215) (ar-216) (ar-217) (ar-212) (ar-211)

Me F

(ar-222) (ar-223) (ar-224)

(ar-229) (ar-230) (ar-225) (ar-226) (ar-227) (ar-228)

(ar-236) (ar-232) (ar-232) (ar-232) (ar-234) (ar-235)

★ ♦ Fortunately * (ar-239) (ar-240) (ar-241) (ar-242)

(ar-243) (ar-244) (ar-245) 28 321867 201100410

(ar-246) (ar-247) (ar-248) (ar-249) (ar-250) (ar-251) (ar-252)

(ar-253) (ar-254) (ar-255) (ar-256) (ar-257) (ar-258) (ar-259)

(ar-260) (ar-261) (ar-262) (ar-263) (ar-264) (ar-265) (ar>266)

(ar-267) (ar-270) (ar-270) (ar-270) (ar-271) (ar-272) (ar-273)

* * * * * * * (ar-274) (ar-275) (ar-276) (ar-277) (ar-278) (ar-279) (ar-280) 29 321867 201100410

(ar-288) (ar-289) (ar-290) (ar-291) (ar-292) (ar-293) (ar-294)

(ar-303) (ar-305) (ar-305) (ar-305) (ar-306) (ar-307) (ar-308)

30 321867 201100410 ❹ ❹

F Fv f -Me FTM( )—Me F—f J—F (ar-316) (ar-317) (ar-318) (ar-319) (ar-320) (ar-321) (ar- 322) Me NC-

(ar-323) (ar-326) (ar-325) (ar-326) (ar-327) (ar-328) (ar-329)

N

Me CN Me

Me, N02 ( y-N02

(ar-330) (ar-331) (ar-332) (ar-333) (ar-334) (ar-335) (ar-336) Me. Et.

* Fortunately (ar-340) (ar-341) (ar-337) (ar-338) (ar-339)

(ar-344) (ar-345) (ar-346)

♦ ♦ (ar-342) (ar-343) F -Br

* ♦ ♦ ** (ar-347) (ar-348) (ar-349) (ar-350) 31 321867 201100410

(ar-351) (ar-354) (ar-354) (ar-355) (ar-356) (ar-357)

(ar-365) (ar-366) (ar-367) (ar-368)

(ar-372) (ar-373) (ar-374) (ar-375) (ar-369) (ar-370) (ar-371)

(ar-376) (ar-377) (ar-378)

(ar-379) (ar-380) (ar-381) (ar-382)

(ar-385) (ar-383) (ar-384) 32 321867 201100410

Me

this

(ar-394) (ar-395) (ar-395) (ar-397) (ar-398) (ar-399)

(ar-400) (ar-403) (ar-403) (ar-404) (ar-405) (ar-406)

(ar-407) (ar-408) (ar-409) (ar-410) (ar-411) (ar-412) (ar-413)

(ar-414) (ar-415) (ar-416) (ar-417) (ar-418) (ar-419) (ar-420) 33 321867 201100410

(ar-421) (ar-422) (ar-423) (ar-424) (ar-425) (ar-426) (ar-427)

(ar-428) (ar-429) (ar-430) (ar-431) (ar-432) (ar-433) (ar-434)

(ar-435) (ar-436) (ar-437) (ar-438) (ar-439) (ar_440) (ar-441)

(ar-442) (ar-443) (ar-444) (ar-445) (ar-446) (ar-447) (ar-448)

(ar-449) (ar-450) (ar-451) (ar-452) (ar-453) (ar-454) (ar-455)

(ar-456) (ar-457) (ar-458) (ar-459) (ar-460) (ar-461) (ar-462) 34 321867 201100410

(ar-463) (ar-465) (ar-465) (ar-466) (ar-467) (ar-468) (ar-469)

(ar-471) (ar-473) (ar-474) (ar-475) (ar-476)

(ar-470)

*

(ar-478) *

(ar-479) (ar-480) (ar-481) (ar-482) (ar-483) (ar-485)

(ar-491) (ar-492)

(ar-498) (ar-499) (ar-500) (ar-501) (ar-502) (ar-503) (ar-504) 35 321867 201100410

(ar-505) (ar-506) (ar-508) (ar-509) (ar-510) (ar-511)

(ar-512) (ar-513) (ar-514) (ar-515) (ar-516) (ar-517) (ar-518)

(ar-533) (ar-536) (ar-536) (ar-536) (ar-537) (ar-538) (ar-539)

(ar-540) (ar-541) (ar-542) (ar-543) (ar-544) (ar-545) (ar-546) 36 321867 201100410

(ar-547) (ar-548) (ar-549) (ar-550) (ar-551) (ar-552) (ar-553)

(ar-554) (ar-555) (ar-556) (ar-557) (ar-558) (ar-559) (ar-560)

(ar-561) (ar-562) (ar-563) (ar-564) (ar-565) (ar-566) (ar-567)

(ar-568) (ar-571) (ar-571) (ar-571) (ar-572) (ar-573) (ar-574)

(ar-575) (ar-576) (ar-577) (ar-578) (ar-579) (ar-580) (ar-581)

37 321867 201100410

(ar-596) (ar-597) (ar-599) (ar-599) (ar-600) (ar-601) (ar-602)

(ar-603) (ar-605) (ar-606) (ar-607) (ar-608) (ar-609)

(ar-610) (ar-611) (ar-613) (ar-613) (ar-614) (ar-615) (ar-616)

(ar-617) (ar-618) (ar-619) (ar-620) (ar-621) (ar-622) (ar-623)

(ar-624) (ar-625) (ar-626) (ar-627) (ar-628) (ar-629) (ar-630) 38 321867 201100410

(ar-631) (ar-632) (ar-633) (ar-634) (ar-635) (ar-636) (ar-637)

(ar-638) (ar-639) (ar-640) (ar-641) (ar-642) (ar-643) (ar-644)

(ar-645) (ar-648) (ar-648) (ar-649) (ar-650) (ar-651)

(ar-659) (ar-662) (ar-662) (ar-663) (ar-664) (ar-665)

(ar-666) (ar-667) (ar-668)

39 321867 201100410

* (ar-680)

(ar-674) (ar-675) (ar-676)

* * ψ (ar-677) (ar-678) (ar-679)

φ φ # (ar-681) (ar-682) (ar-683)

(ar-684) (ar-685) (ar-686)

Kiosk ¥ . Umbrella Umbrella Umbrella — (ar-687) (ar-688) (ar-689) (ar-690) (ar-691) (ar-692) (ar-693)

(ar-694) (ar-695) (ar-696) (ar-697) (ar-698) (ar-699) (ar-700)

(ar-702) (ar-702) (ar-703) (ar-704) (ar-705) (ar-706) (ar-707) 40 321867 201100410

^ ♦ ♦本幸孝 ♦ (ar-708) (ar-709) (ar-710) (ar-711) (ar-712) (ar-713) (ar-714) c6h13

(ar-715) (ar-716) (ar-717)

(ar-718)

*

(ar-722) (ar-724) (ar-725) (ar-726) (ar-727)

Ben (ar-728)

(ar-736) (ar-737) (ar-738) (ar-739) (ar-740) (ar-741) (ar-742) 41 321867 201100410

(ar-743) (ar-744) (ar-745) (ar-746) (ar-747) (ar-748) (ar-749)

(ar-750) (ar-753) (ar-753) (ar-753) (ar-755) (ar-756)

(ar-757) (ar-760) (ar-760) (ar-760) (ar-761) (ar-762) (ar-763)

(ar-764) (ar-767) (ar-767) (ar-768) (ar-769) (ar-770)

(ar-772) (ar-772) (ar-773) (ar-774) (ar-775) (ar-776) (ar-777) 42 321867 201100410

(ar-778) (ar-779) (ar-780) (ar-781) (ar-782) (ar-783) (ar-784)

(ar-785) (ar-788) (ar-788) (ar-788) (ar-790) (ar-791)

(ar-792) (ar-795) (ar-795) (ar-796) (ar-797) (ar-798)

(ar-799) (ar-802) (ar-802) (ar-802) (ar-803) (ar-804) (ar-805)

(ar-806) (ar-807) (ar-808) (ar-809) (ar-810) (ar-811) (ar-812) 43 321867 201100410

聿 幸* (ar-813) (ar-814) (ar-815)

(ar-816) (ar-817)

(ar-820)

(ar-821) (ar-822)

(ar-823) (ar-824) (ar-825) (ar-826)

(ar-827)

* · * (ar-828) (ar-829)

(ar-834)

* * (ar-835) (ar-836)

(ar-837) (ar-838) (ar-839) (ar, 84〇) In the formulas u-l) and (1-2), 'D1 and D2' each independently represent a single bond or a divalent linking group. The divalent linking group may, for example, be -C〇-0-, -〇-c〇~, -C(=S)~〇-, -〇-C(=S)-, -CR4R5-, -CR4R5-CR6R7- , -〇-CR4R5-, -CR4R5-〇-, -CR4R5-〇-CR6R7---CR4R5-0-C0-,-0-C0-CR4R5 _CR4R5-0-C0-CR6R7-, -CR4R5-C0-0 -CR6R7-, -NR8-CR4R5-, -CR4R5-NR8-, -CO-NR8-, -NR8-CO-, -0-, -S-, -NR8-, and -CR4=CR5-. R4, R5, R6 and R7 each independently represent a hydrogen atom, a gas atom, or a carbon number of 1 to 4 (e.g., anthracenyl, ethyl, propyl, isopropyl 321867 44 201100410 to 4 alkyl groups (for example, A) Base, butyl, etc.), R8 represents a hydrogen atom or a carbon number i group, an ethyl group, a propyl group, an isopropyl group, a butyl group or the like.

D1 and D2 should be *-0-C0-, *-〇_c(=s), ~, *-NR8-CR4R5- or *-NR8-C0, more preferably *_〇一C0__, *_〇 _c (= 幻口*-NR8-CG. Here is the base or material shown by the formula (dipole) (the binding site of the base shown by R. R4, R5, R1 r7 should be divided into positions to represent the gas atom Or a filament having a carbon number of 1 to 4, more preferably a hydrogen atom or a methyl red group. R8 is preferably a hydrogen atom, a methyl group or an ethyl group. In the formula (1-1) and the formula (1-2), G1 and G2 The divalent alicyclic hydrocarbon group is independently represented, and the hydrogen atom of the alicyclic hydrocarbon group may also be a south atom, an alkyl group having a carbon number of 4 to 4, a fluoroalkyl group having a carbon number of 4 to 4, and a carbon number of 4 to 4. Substituted by alkoxy, cyano or nitro, the -CIL of the alicyclic hydrocarbon group may also be substituted by -〇_, -s- or -NH-. The divalent alicyclic hydrocarbon group constitutes a carbon atom of the ring and The number of atoms may be, for example, 3 to 10 and 2 to 2 alicyclic alicyclic hydrocarbon groups, preferably a group represented by the formula g(g 1) to the formula (gl〇), more preferably a 5-membered ring or 6 Member ring.

The hydrogen atom of the group represented by the above formula (g-Ι) to the formula (g-1〇) may be an alkyl group having a carbon number of 4 to 4 such as a methyl group, an ethyl group, an isopropyl group or a tributyl group;曱45 321867 201100410 Alkoxy groups having 1 to 4 carbon atoms such as an oxy group and an ethoxy group; a fluorine-based group having a carbon number of 1 to 4 such as a trifluoromethyl group; and a fluoroalkane having 1 to 4 carbon atoms such as a trifluoromethoxy group. An oxy group; a cyano group; a nitro group; a halogen atom such as a fluorine atom, a gas atom or a bromine atom. G1 and G2 are preferably a group represented by the formula (g-i), and more preferably iota, 4-cyclohexanediyl is particularly preferably a trans-1,4-cyclohexanediyl group. The compound of the present invention is preferably a compound containing a divalent group represented by formula (2-1) or formula (2-2):

(2-1) Y1

(2-2) (wherein g2 represents the same meaning as the above; E and E2 each independently represent a single bond or a divalent linkage; B and B each independently represent a single bond or a divalent linkage; A1 and A2 respectively Independently representing a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a functional atom, an alkyl group having a carbon number of 4 to 4, a fluoroalkyl group having 1 to 4 carbon atoms, Alkoxy groups having a carbon number of 4 to 4, a fluoroalkoxy group having 1 to 4 carbon atoms, a cyano group or a nitro group; and 321867 46 201100410 k and \ each independently represent an integer of 3 to 3). The divalent linking group in E and E may be, for example, _CR9R1. ---Ch2-CH2- ' 〇-, -s-, -co-o-, -0一c〇_, _〇_c〇_〇_, _c(=s)_〇一, 〇C(S ), -〇-c(=s)-〇---CO-NR11-, -NR^-CO-, -O-CH2-, CIL·0, -S-CH2-, -CH2-S-,- NR11-, and -CR9=CR1G_. R9 and

R1° independently represents a hydrogen atom, a fluorine atom or a carbon atom of i to 4, and Ru represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

E and E should be independent of _c〇_〇_, _〇c〇_, _〇_c〇_〇一, CO NR , -CO-, _CH2-〇-, _CH2-S- or single bond, respectively. It should be a CO-〇-. The divalent linking group in B and B2 may, for example, be _CR9RlD---CH2-CH2-, -〇- > -s- > -C0-0- . -o-co- > -0-C0- 0- . -C(=S)-〇- ' 0-C(-S)-, -〇-C(=S)-〇-, one CO-NR11-, -«〇-, -O-CH2- -CH2-0-, -S-CH2-, -CH2-S---NR11-, and -CR9=CR1(>-. In terms of the ease of manufacture of the compound of the present invention, it is preferred to combine only 〇 and β2 bound only to A2 independently represent -CH2-CH2-, -C0-0-, -0-C0-, -C0-NH-, -NH-C0-, -0-CH2-, -CH2- 0- or a single bond, in the case where the compound of the present invention exhibits high liquid crystallinity, it is preferably _C〇_〇一 or -0-C0-. In the case of the compound of the present invention, it is preferred to use B2. The divalent alicyclic hydrocarbon group or the divalent aromatic hydrocarbon group in A and A may, for example, be a group represented by the above formula (g-1) to formula (g-10), and have the following formula (&_υ to formula) a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms as shown in (a-8). 321867 47 201100410

The hydrogen atom of the group represented by the above formula (al) to the formula (a-8) may also be a carbon number (tetra) group such as a mercapto group, an ethyl group or an isopropyl group 't-butyl group; a methoxy group or an ethoxy group; An alkoxy group having 1 to 4 carbon atoms; a fluoroalkyl group having a carbon number of i to 4 such as a trifluoromethyl group; a fluorine alkoxy group having a carbon number of 1 to 4 such as a trifluoromethoxy group; a gas group; a nitro group; A halogen atom such as an atom, a gas atom or a bromine atom is substituted. Among them, A1 and A2 should each independently be fluorene, 4-phenylene or fluorene, and 4_cyclohexanediyl can be more easily produced by the compound of the present invention, and more preferably 1,4-extended. Insofar as it is easier to manufacture the compound of the present invention, it is preferred that A1 and A2 are the same. From the viewpoint of the liquid crystallinity of the compound of the present invention, k and 1 are 〇 to 2. Preferably, the sum of k and 1 is 5 or less, and more preferably 4 or less. The compound of the present invention is more preferably a compound represented by formula (3-oxime) or formula (3-2): Y1

P1-F1^B1-A1^El-Gl_DlV〇)^D2_G2_E2/A2_B2^rF2_p2 (3-l) 48 321867 201100410

Di

pl_Fl_LBl.Al •D2—G2-E2+A2 - B2)pF2-P2 (3*2) (in the formula, % 2, Y1, D1, D2, G1, G2, E1, E2, B1, ^ AA, k and 1 point g 丨丨 main - h D, r2 x knives ^ table does not have the same meaning as the above; F and F2 respectively represent a burning two base which can have a carbon number of 1 to 5 ^ f 12; The base of the calcined base may also be a methoxy group or a tooth atom of 1 to 5, j is substituted by a hydrazine-co-; P and F respectively represent a hydrogen atom or a polymerizable group.

• The -2 of the stone readings from 1 to 12 in -rr// F is -(H -(CH2)4-, -(CH2)5-, -Ύ Γϋ, . (CH2)6-, -(CH2 ) 7-, -(CH2)8-, -(CH2 V, • -(CH2)i〇-, -(CF2)4~, -frp, (CF2)6-, &_(CF2)8_, It should be _(CH2)4_, and ~(CH2)6-. It should be combined with β1 and B2 combined with F2, respectively, as -〇_,

C〇_〇-, "〇_? 〇H, -CO, -, -NH-C0- or a single bond. And at least one of P is a polymerizable group, and the silk obtained from the compound of the present invention is The film hardness is excellent (10), and pl and P2 are polymerizable groups. The polymerizable group may be a soil p which can participate in the polymerization reaction of the compound of the present invention, and specific examples thereof include an ethyl group and a vinyloxy group. Phenylethyl, p-phenylvinyl)phenyl, propylene fluorenyl, methacryl fluorenyl, propylene methoxy, methyl propyl methoxy, sulfhydryl, acetyl, benzyl, amine Mercapto group, N-alkylamino group having 1 to 4 carbon atoms, amine group, epoxy group, oxo ring 321867 49 201100410 Butanyl group, formamyl group, isocyanate group and isothiocyanate group. It is suitable for photopolymerization, and is preferably a radical polymerizable group or a cationic polymerizable group, which is easy to handle and the compound of the present invention is also easy to manufacture, and is more preferably an acryloxy group or a methacrylium group. The oxy group is particularly preferably an acryloxy group. The polymerizable group may also be directly bonded to F1 and F2, but preferably via one or more divalent linking groups (for example, in the above B) Specific examples of the combination of -D1-GLELU^Bi-F1-P1 and -D2-G2-E2-(A2-B2)-wide F2-P2 can be exemplified by the formula ( R-1) to a group represented by the formula (R-134). Further, in the following formula, * represents a binding site to a group represented by the formula (1-1-A) or the formula U-2-A), η represents an integer of 2 to 12.

201100410 Ο

(R-I3) (R-14) (R-15) (R-16) (R-17) (R-25) (R-26) (R-27) (R-28) (R-29) (R-30) * One Ο * One ο * One 〇 - °x / One, - 〇 / = (R-19) /CnHjir-o~~%, .Ή (R-20) f-CnH2iT-〇~ i. }—CnH2fr (R-21) \ (R-22) (R-23) (R-18)

(R-32) -q i; (R-33)

*——Q 51 〇CpHafr-O—^ b~CnH2f^O—¢, ·», b (R-34) (R-35) Π (R-36) 321867 201100410

(R-43)

(R-44)

(R-39) (IMO) (R-41) (R42)

(R-45) (R-46) (R-47) (R-48)

(R-49) *

>—0—CnHjn-

*—0, (R-50) (R-51)

(R-53) (R-54) (R-55) )—CnHaT-O-^ (R-52)

(R-56) o 52 321867 201100410 * —ο

(R-57) (R-58) (R-59) (R-60) (R-61) (R-62) (R_63) (R-64) (R-65)

(R-66) (R-67)

53 (R-68) 321867 201100410

(R-79) (R*80) 54 (R-69) (R-70) (R-71) (R-72) (R-73) (R-74) (R-75) (R-76 ) (R-77) (R-78)

321867 (R-81) (R-82) (R-83) (R-84) (R-85) (R-86) (R-87) (R-88) (R-89) (R-90 ) (R-9I) (R-92) 201100410

56 (R-93) (R-94) (R-95) (R-96) (R-97) (R-98) (R.99) (R-100) (R-101) (R-102 ) (R-103) (R-104)

321867 201100410

57 (R-105) (R-106) (R-107) (R-108) (R-I09) (R-110) (R-112) (R-113) (R-114) (R-115 ) (R-H6) 321867 201100410

(R-117) (R-118) (R-119) (R-120) (R-121)

(R-122)

(R-123) (R-124) (R-125) (R-126) (R-127) (R-128) c 58 321867 201100410

(R-129)

(R-130) (R-131) (R-132) (R-133) '^CnH2n+1 (R-134) 本—Q

The compound of the present invention may, for example, be a compound represented by the formula (Al-1) to the formula (A73-8). Further, in the following formula, * represents a binding site, and for example, the compound represented by the formula (A1 -1) is a compound described below.

ο P

59 321867 201100410 >OCeHirO__,; (A1_1)

- cK

-Q-C^Hg-O

Uac price cp (Al-2) *-〇-<一厂1>. 6(^2-〇一6" 〇'C4h12-9 f; (Al-4)

3-/^V〇CeH12-〇^ (A2_1) -O-C4H1 (A2-2) *-〇- (A2-3) 〇-c4h1: (A2-4) (A3-1) CK^He—Q 〆ό~' Ό-*\__)~CeHi2—Ο / Ο *^3^〇·°βΗ12-Ρ _/.-Oic *-〇-〇^c Bu C4H8—O^y -〇-〇4Ηβ~

jr-〇-c4He-q / (A3-2) 〇-CeH, Ύ (A3-3)

b-C4H8-Q D-C4Ht

2-〇V (A3-4) *-o~\ yc6Hr

l2T

3-ζ^-Ο CeH12-^_/ (A4-1)

Vo-c^He-q ~〇-C4H| 丨8-(A4-2) *-〇-(, __/~〇_CeHi2~Q / Jv *-〇^H-C6h12-...(A4-3> 〇-c4h12-o (A4-4) 〇-C4He-C^y -0", _)~〇6Ηΐ2~(^.^ (Al-5) (Al-6) (Al-7) (Al- 8) (A2_5) (Α2·6) (A2-7) (Α2·8) (A3-5) (A3-6) (A3-7) (A3-8) (A4-5) (A4-6) (A4-7) (A4-8) 60 321867 201100410 >-a〇eHirQ / (Α5-1)

Vo -〇C4H8 ρ 〆

*-〇^\>oc4h8-q / (A5-2) '' ·4' d *-0-〇-f (A5-3) '=^ O-CeH^-Q / i5 b-C4H12-Q / (A5-4) *-0-< ,^-O-CeH^-Q / (T*.〇_Γ>_Ρ—^ 0-C'He-Q 〆cT *-〇·/~/- 〇eHi2~p /

*-〇)-\^^〇CeH12"9 / iQoc^e-^/ (A6_2) d ^ ° (A6-3> b-CeHu-〇, / 0-C4H1: (Α6·1) .^ry〇 ^4Hr, (A6-4)

’-〇-(,_)-0-〇6Η12-〇^ί P b-c4Ha-o^l2T

O^C-HgrC^ Ο *_〇_0"oCeHir〇)_/ (A7-1) *_〇~O^0'c<,He'c]_/ (A7_2)

R-<)--/^-〇-C6H12-C^_y (class (A7-4) one •-©-(^/-ΟβΗΐί—

(A8_1) (A8_2) (A8-3) (A8-4)

(A5-5) (A5-6) (A5-7) (A5-8) (A6-5) (A6-6) (A6-7) (A6-8) (A7-5) (A7-6) (A7-7) (A7-8) (A8-5) (A8-6) (A8-7) (A8-8) 61 321867 201100410

*—〇Hh〇C6HirCU (A9-1) *_〇_Q— o ~ •-Ο-^νο-ο,,Ηβ-Ο ,; (A9-2)^ cT(A9_3) (A9-4) - O'CqH^Q / o-c4h8~qo (A9-5) (A9-6) (A9-7) (A9-8)

〇~c4h12-q / K^>〇CeHirp (AHM) -〇-( %rocAHrC( β (A10-2) *-ο-ζ\-ο-〇4\η-ο , (A10-6) ( A10-5) O-Cel (A10-3) *-ch; Bu c4h (A10-7) (A10-8)

-OCeHt (AIM) such as 2-^_y -o-^^o-CaHs-^j (All-2)--OLh卞,-3) Wide OCeH, 〇'〇4Hi2-q b-C4H| (All- 4) *-o~('广c6h12—丨(Α11·5) (All-6) (All-7) (All-8)

*-cK V〇c$h12h (A12-1) V〇-c4h, -〇-/eVo-c4HB--o^* (A12-2) *-〇-(^3"0*〇βΗΐ2'^_ ^ (A12-3)

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Well-known organic synthesis reactions described in Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, New Experimental Chemistry Lectures, etc. (eg, condensation reaction, acetification reaction, Wi 11 iamson reaction, U1 lmann reaction, Wittig reaction, Schiff test generation) Reaction, benzoylation reaction, bacterial head reaction, Suzuki-Miyaura reaction, root bank reaction, bear field reaction, Laoshan reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, Aldol reaction, etc. And the right combination to make. For example, a compound represented by formula (3-1) or formula (3-2) in which D1 and D2 are *-0-C0- can be obtained by formulating a compound represented by formula (11-1) with 11) The compound shown is reacted to obtain a compound represented by the formula (11-3), and the compound represented by the formula (11-3) is obtained by the compound represented by the formula (1b). The compound is reacted to produce: H0-Ar-0H (11-1) (wherein Ar represents a divalent group represented by the above formula (1-1) or the above formula (1-2)) P1—F^bi_ai^_ei__gi__c 〇2H (112) (wherein, G1, E1, A1, B1, F1, P1, and k are the same meanings as above) PA^E1—G1—CO-Ar-OH (u.3) Ο 'Ar, G1, Ε1, A1, Β1, F1, Ρ1 and k are the same meanings as above.) H〇2〇—G2—E2-(-A2—B2^-HP2—Ρ2 (11 -4) 321867 201100410 (In the formula, 'G2, E2, A2 U, & ! means the same meaning as above.) Also, G1 and G2, E1 and E2, A1 and A2, B1 and B2, F1 and F, P1 and P and k When all of the same as 1 are respectively, the compound represented by the formula (n - i) can be reacted with 2 equivalents or more of the compound of the formula (1b 2) to form a phase-by-stage system. A compound of the formula (11-1) and a compound represented by the formula (11-2) and a compound represented by the formula (II-3) and a formula (11-4) The reaction of the ruthenium compound is preferably carried out in the presence of a condensing agent. The condensing agent may, for example, be 1-cyclohexyl_3_(2-morpholinoethyl)carbonyldiazide imine p-toluenesulfonate or dicyclohexyl. Carbonyl quinone imine, ethyl ethyl _3_(3_ • dimethylaminopropyl) carbonyl diimide, 1-ethyl-3-(3-didecylaminopropyl carbonyl) ruthenium diimide Hydrochloride, bis(2,6-diisopropylphenyl)carbonyldiimide, bis(dithiocarbazide) bis quinone imine, N, Ν'-diisopropyl a carbodiimide compound such as an imine; 2-mercapto-6-nitrobenzoic anhydride, Q 2, 2 -carbonyl bis-1 fluorene-imidazole, 1, hydrazine-oxalyldiimidazole, azide-based acid The purpose of this is, 1 (4-nitro stupid)-1 Η-1,2,4-triterpene, hexa-sodium sulphate 111- and one-spot-l-oxyl-l 11 pirate Dish iron salt, hexafluoride acid 1||-Benyl sulphate bis(monodecylamino) disc drilling salt, four-sided side acid N, N, Ν', N - Tetramethyl-anthracene-(N-Boprene-imino)urea salt,](1,2,2,2-tetrachloroethoxyl-yloxy), permethylide, benzoic acid Oxygen charcoal 'N-carbobenzoxysuccinimide, 0-(6-chlorobenzotriazol-1-yl)-N,N,Ν',Ν'-tetramethylurea rust salt of tetrafluoroborate, Hexafluoroacid 0-(6-chlorobenzotriazol-1-yl)-indole, anthracene, Ν', Ν'-tetradecylurea rust salt, 321867 79 201100410 Tetrafluoropic acid 2-bromo-1 - Ethyl ° ratio ° iron salt, 2- gas-1,3-dimethylisoxazoline rust salt, hexafluorophosphate 2-gas-1,3-dimethylimidazolinium salt, iodide 2 -Chloro-1-indenyl acridine rust salt, p-toluenesulfonic acid 2-ox-1-indolyl acridine salt, p-toluenesulfonic acid 2-fluoro-1-indolyl acridine rust salt, three gas Pentachloroacetate and the like. From the viewpoints of reactivity, cost, and selectivity of a solvent which can be used, it is preferably dicyclohexylcarbonyldiimide, and ethyl-3-(3-dimethylaminopropyl)carbonyldiimide, 1 -ethyl-3-(3-didecylaminopropyl)carbonyldiimide hydrochloride, bis(2,6-diisopropylphenyl)carbonyldiimide, bis(trimethyl)矽alkyl)carbonyldiimide, N, Ν'-diisopropylcarbonyldiimide and 2,2'-carbonylbis-1Η-mipropene. Next, the composition relating to the present invention will be explained. The composition of the present invention comprises a compound of the present invention and a liquid crystal compound which is different from the compound of the present invention. Specific examples of the liquid crystal compound are, for example, "Liquid Crystal Handbook (Edited by Liquid Crystal Manuals, Maruzen Co., Ltd., October 30, 2004), Chapter 3, Molecular Structure and Liquid Crystallinity, 3.2 Non-Planar Rod Liquid Crystals A molecule having a polymerizable group among the molecules described in "3.3 palmar rod-like liquid crystal molecules". One type of liquid crystal compound can be used, and two or more kinds of liquid crystal compounds can also be used. By using the composition containing the compound of the present invention and the liquid crystal compound, the optical characteristics such as the wavelength dispersion value or the retardation value of the optical film obtained by polymerizing the composition can be adjusted to a desired value. The liquid crystal compound may, for example, be a liquid crystal compound represented by the formula (20) (hereinafter sometimes referred to as a compound (20)) or the like: 80 321867 201100410 pll - Ε11 - απ^β12.

G (20) It or 2 fresh fragrant base, 2 alicyclic alicyclic hydrocarbon fresh money, (10) Cyclohexyl and the heterocyclic group: can: have a south atom, carbon number ... the base, carbon number (1) : N-alkylamino group of carbonaceous rabbits 1 to 6, carbon number 21, amphoteric amine group m or old; 'N — c Ξ c-, -CH=CH- Ο Ο respectively represent -CR14R15- CH2 CH2 〇', -s-, -C(=〇)-, -c〇〇)-〇__, _〇_&〇)—, 〇—C(-0)-0-, -C(=S )-, a C(=S)-〇-, -〇-c(=s)_, _CH=N-, -N=CH-, -N=N-, -C(=〇)_NRl6_, 智6_c (=〇)_, n, -〇cf2-, n, _CM_, _CF2〇_, _ch=ch_c(4))—〇_, :〇-C(=0)-CH=CH- or single bond, and γ are independent And a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, or ... and ρ are bonded to an alkanediyl group having a carbon number of 4 to 7; to represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; Ε denotes a calcined base having a slave number of 1 to 12; the calcined base may also have an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a halogen atom; Ρ11 represents a polymerizable group; a hydrogen atom, a halogen atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a fluoroalkyl group having 1 to 13 carbon atoms, Between 1 and 13 - an alkylamino group, a carbon number of 2 to 26, a fluorenyl-dialkylamino group, a cyano group or a nitro group, or an alkyl group having a polymerizable group having 1 to 18 carbon atoms, The alkyl group may also have a decyloxy group or a halogen atom having 1 to 6 carbon atoms; 81 321 S67 201100410 t represents an integer of 1 to 5). The polymerizable base of the P& G towel can be used as long as it can be used in the present invention. For example, ethyl, vinyloxy, phenethyl, and p-(2-phenylethylene) can be used. Phenyl, acrylonitrile, propyloxy, methyl propylene, ketone propyl oxy, county, ethyl hydrazine, hydroxy, aminomethyl decyl, amine, carbon number Ni to amine group of i to 4, epoxy group, lactulose, methyl sulfonyl group, 100% or -N=〇S, and the like. Among them, in the case of light A, the reaction is agglomerated, and 3' is preferably a radical polymerizable group or a cationic polymerizable group, the liquid crystal compound is also easy to handle, and is acryloxy, Methyl propylene methoxy or vinyloxy. Further, the carbon number of the aromatic hydrocarbon group, the alicyclic hydrocarbon group and the heterocyclic group of A11 is preferably from 3 to 18, more preferably from 5 to 12, particularly preferably 5 or 6. The compound (10) may, for example, be a compound represented by the formula (2〇-n and the formula (10)_2): P11-E11-(B11-A11)tl-Bi2_El2_pl2 (2〇_. P, 1-E11-(Bu-AI1)t2 -B12-F11 (20-2) (^, Ε, Ε, β11, Αη, Β12 represent the same meaning as above; F!1 represents a hydrogen atom, a self atom, a carbon number of 1 S 13 , a carbon number! a oxy group of 13, a fluoroalkyl group having 1 to 13 carbon atoms, a N-alkylamine gas having a carbon number of 1 to 13, an N,N-dialkylamino group having a carbon number of 2 to 26, a cyano group or a schlossyl group; E represents a dimer of the inverse of 1 to 12, and the dialkyl group may have a C 1 to 6 alkyl group, an alkoxy group having 1 to 6 or a halogen atom; P 12 represents a polymerizable group; t1 and t2 An integer of 1 to 5 is shown. 321867 82 201100410 The compounds represented by the formulas (20-1) and (20-2) are, for example, the formula (I), the formula (II), the formula (III), and the formula (III). IV) and the compound of formula (V):

Ρ1,-ΕΠ-ΒΙ1-Α11-Β1-A1-B1-A13-BI4-EI2-P P11-Eu-B11-A11-B12-A12-B13-A13-B14-F11 (II) (III) (IV) (V) (wherein A12 to A15 have the same meaning as A11, and B13 to B16 have the same meaning as 〇). In the compounds represented by the formulae (20-1), (20-2), (I), (π), (in), (IV) and (V), the bonds of p11 and e11 are preferred. The knot is a sputum bond or a vinegar bond, and the bond between P12 and E12 is preferably _ bond or vinegar bond. Specific examples of the liquid crystal compound include, for example, a formula (丨-丨) to a formula (?_5), a formula (B1-1) to a formula (B20-8), and a formula (C1-1) to a formula (C4-8). a compound represented by the formula (I), a compound represented by the formula (II), a compound represented by the formula (Π-1) to the formula (Π-6), and the like, and a compound represented by the formula (II); 1) a compound represented by the formula (III-19) and a compound represented by the formula (ΠΙ); a compound represented by the formula (IV-1) to the formula (IV-14), etc., represented by the formula (IV) The compound represented by the formula (V-1) to the formula (V-5) is a compound represented by the formula (ν). Further, in the following formula, 'k represents an integer of 1 to 11, and * represents a binding site. These liquid crystal compounds are preferred liquid crystal compounds because they are easily synthesized or commercially available. 83 321867 201100410

3^-(叫~〇〇^〇_^〇^^^〇°-(叫乂__gt;〇-(叫-〇〇^〇_^5^〇_}-〇·0-,·^ 201100410

>ceHi2<y (BM) >-o-c4He-q *-〇- -o-c4He-q > (Bl-2) -c4h12-〇. -OCeH1; -〇-c4Hi

*~°~{3~0'CsH«'0^_y C®3-1) o 2:〆 -〇C6Ht 〇-c6h12-o 〇

Q V〇-C4He·

VV le-^_y (B2-2) *-〇-{^)-〇^»n-〇>_j (B2-3) *-〇-〇-ξ 3-C4h*-〇o ic^-y (B2-4) *·<η^〇6Η12-^ ^ _〇〆(B3_2) -o-c4h8-c (B3-3) *-〇- 〇-C4H12-〇^ o (B3-4) D -(3-〇.C6Hl2<^yo (B4-1)

0-C4H1 -〇-CeH OC, :4Ηβ-Oy β -6Hi2-q/ <5 -d ^Hg-o / (B4-2) 0 -< (B4-3) *-〇- 〇-C6H12 -〇^y V (B4-4) *〇- o-c4h12 r )-〇H>CeH12-〇o*c4hb-o 0' ^Hi2—〇v / (Bl-5) (Bl-6) (Bl -7) (Bl-8) (B2-S) (B2-6) (B2-7) (B2-8) (B3-S) (B3-6) (B3-7) (B3-8) (B4 -5) (B4-6) (B4-7) (B4-8) 85 321867 201100410

^-Q-O'C^He-o^/ (B5-2) (B5-6) *-〇-/~~V-OCgH^'O. / *-q *-〇 *-〇-

〇-CeH 12y 〇-C4H, 2-〇 o (BS-3) (B5-4)

(B5-7) (B5-8) •-o-OoCeH,^ (B6-1) *.〇^3_〇>-〇^H8-^y (B6-5) *-oO-〇-C4H8 -c^_y (B6-2) *-〇-(3~0'C6Hir^_/ (B6-6) *-〇« .V_____ . (B6-4) <6H12 >-〇4Ηΐ2'0 - OCeH, (B7-1)

(B6-7) (B6-8) _〇^_^-〇K:4H,-^V (B7.5) r~y~〇-c^2~^j *-〇·

》<6...r〇yo 〇τ〇4Η-|2**〇. 0 (B7-3) (B7-4) (B8-1) 0~C4He—0 0 -C6H12—Q / (B7-6 ) (B7-7) (B7-8)

*-〇- *-〇- 〇-C4H8-〇^_y (B8-5) 0-C4K8-0^y 0 (B8-2) *-〇〇-〇ΑΗ12·〇〆(Β8·6) < ° 〇-CeH12-C^y (B8-3) w 〇-〇4HB-〇^_y (B8-7) <° 〇*C4H12-〇^y (B8-4) o corpse (B8-8) 86 321867 201100410 *-0-< V〇*C6H12· (Β94)

Γ〇μ (Β9-2)

D-C6H

KV o-c6i (B9-3) *-〇- OO4He-0 0〆 *-〇- *-〇-

0-C4H

'T ^βΗΐ2'^ /

-〇-C4Hb~C 〇-C6H12-〇 o -OC6H12

>CeH (B9-4) *-〇-( )-〇6Η1; ^-〇-C, H8-C^y (B10-2) (B10-3) *-c (B10^4) (Bll- 1)

〇-C4He-〇 O ><KUHe-0 0

'V o

QV〇-C4He-〇(B12-1) :6H,2-〇^y (B12,2) p (B12-3) 〇-CeH12-〇^y ^ b-C4HB-^y ^〇-c4h12- ( B12^») .-〇^>〇6H12- (B9.5) (B9-6) (B9-7) (B9-8) (B10-5) (B10-6) (B10-7) (B10 -8) (Bll-5) (B11-6) (Bll-7) (Bll-8) (B12-5) (B12-6) (Β12·7) (B12-8) 0 87 321867 201100410 (B13- 1)

(B13-2) *Ό- V 0-C4H8-^y D-C6Hy

CeHt2~^_y

-〇-^~^-〇·〇βΗΐ2"^ / ^^°yj (B1'2) )-〇-〇4^6' >CeHi2"<°0"〇4Ηή2~ (B14-3) * -〇-(B14-4) >c4h -eH12—q

O^3""°CeHl2<^/ (财^"')* 〇-〇Η·ο-ο4Ηβ-^_/ (B15-2) — Ο-ΓνΡ (B15-3) / OCeH12-Q_/ ^ 〇3-TVP (B15-4) w ο^4Ηι2-〇^7

O-CeH 〇-C4HB-C^yi2y

(Β16-υ ..0^y}〇-c^-<y *-〇-Q-〇-c4He-〇^y (B16-2) *-〇-<^y〇'ceH«·^ o o-TV-f (B16-3) w 〇-CeH12-^7 C4H12-〇^y (B13-5) (B13-6) (B13-7) (BI3-8) (B14-5) ( B14-<) (B14-7) (B14*8> (B15-S) (B15-6) (B15-7) (BI5-8) (B16-5) (B16-6) (B16-7) (B16-8)

88 321867 201100410

(B17-2) (B17-3) (B17-4) * Order C~CeH12-^_y >-〇-〇4«8'

3-CeH >C4He-0ct

>O~〇*c4He-o

(B18-1) (B18-2) (B18-3) (B18-4) (B19-1) (B19-2) (B19-3) (B19-4) (B20-1) eHi2~^ /

aV •c disease Hr

(B20-2) *-〇^)KK:eHl2'V/

(B17-5) (Β17·6) (B17-7) (B17-8) (B18-5) (B18-6) (B18-7) (B18-8) (B19-5) (B19-6) (Bli^T) (B19-8) (B20-5) (B20-6) (B20-7) (B20-8) 89 321867 201100410

kV (Ci-2) (Cl-3) * (CM)

(CM) (Cl-5) (Cl-6) (Cl-7) (Cl-8) 0

〇〆 *-〇-^y〇-C«Hg-^_/ (C2-2)

-OC»H (C3-1) (C2-5) (C2-6) (C2-7) (C2-8)

''c<He~^_/ (C3-5)

JC, He-qy (C3-2) *-O-{y〇-C^2<y (C3-6) b-CeH,2-〇^y (C3-3) *-〇- i.. ( C3-7) 〇- •y (C3-4) (C3-8) D*CeH1; (C4-1) (C4-5)

*-〇. -Q-ck:4H8-〇^/ (C4-2) (C4-6) *« ~ "·〇, '(C4-3) *—0 (C4-7) 〇-c4h 〇- C4He»C^_y (C4-4) *K)H〇-c6H12-0^y (C4-8) 90 321867 201100410 (II- 1)

91 (II-2) (II-3) (II-4) (II-5) (II-6) 321867 201100410 μ{〇Η2)ίΓ·1

(III-1) -CHCHzJk-O-^3'0-<CH2)ir0_O~§_^_5~O_0-<CH2>k~0(b(ch2)t

-〇-(CH7)r〇 卜 <CH2)rH

(CH2)k- 0-(CH2)k-〇' .( >>(CH2W〇i<^K>^CH2)k-0^ _3^〇-((4) >(CH2)r Bu (CH2 )r

) one (CW)

Br -〇-(CH2)r

Br

〇-(CH2)k-〇 (CH2)k-0- 3-a (called 3~°~{ (CH2)r-<

〇-(CH2)ir°·¢111-2)(III-3) (ΠΪ-4) (II卜5) (III- 6) (III- 7) (III-8) (III- 9) (III - 1 0) (III-1 1) (III-1 2) (III- 1 3) (III- 1 4) (III- 1 5) (III- 1 6) (in-1 7) (III-1 8) (III- 1 9) 92 321867 201100410 . «3~°~(CH2)k—0-^^-^^-〇-(CH2)k—CH3 o

Ό—(CH2)fCH3 〇-(CH2)|T~CH3 O— )-(CH2)k-

;N o

^-o-iCHA-oO^-Q-^-o7 3~〇(CH2)"0^^~^-〇~Q~CN ^W2)k-cH^CKH〇cK ^3~°~(CH2) Ir0 3-°-(ch2)k-〇-〇-〇^

OH >-CN "〇〇,

(ch2>"ch3 (IV-1) (iv-2)(IV-3) (IV-4) (IV-5) (IV-6) (IV-7) (IV-8) (IV-9) (IV- 1 〇) (IV-1 1) (IV-1 2) (IV-1 2) (iv-1 4) 321867 93 201100410 3~〇~(CH2)k

〇--\ }^CN (V- 1) (V-2)

3^(CH2)k-3~〇iCH2)"o^C>^〇q (V- 3) (V-4) 3^^(CH2)k-〇^~^-^NQ-CN (V_5) When a composition containing a liquid crystal compound is used for the purpose of controlling the thermal properties of the obtained optical film, it is preferable to use the formula (1-1) to the formula G in terms of excellent reliability of the obtained optical film. 5), formula (then-丨) to formula (B20-8), (C1-1) to formula (C4-8), formula (Π-1) to formula (II-6) and formula (III 1) to The liquid crystal compound represented by the formula (III-19) is preferably of the formula (1_5), the formula (B1-1) to the formula (B20-8), and is excellent in compatibility with the compound of the present invention. C1-1) to the liquid crystal compound of the formula (C4-8) and the formula (in-ι) to the formula (ΠΙ-19), in which an optical film exhibiting reverse wavelength dispersion can be obtained, preferably B1-1) to a liquid crystal compound represented by the formula (β2〇_8) and (c1) to the formula (C4-8). The amount of the liquid crystal compound used is 100 parts by weight relative to the total of the liquid crystal compound and the compound of the present invention. It is generally 90 parts by weight or less. The composition of the present invention preferably further comprises a polymerization initiator. The polymerization initiator preferably contains a photopolymerization initiator. The photopolymerization initiator is preferably a photopolymerization initiator which generates a radical by light irradiation. 321867 94 201100410 The photopolymerization initiator may, for example, be a benzoin compound, a benzophenone compound, an acetophenone compound or a sulfhydryl group. a phosphine compound, a three-till compound, an iodine' sulfonium salt, and a sulphur salt. Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzene. Oxidized isobutyl ether. The benzophenone compound may, for example, be benzophenone, methyl ortho-benzoyl benzoate, 4-phenylbenzophenone, 4-phenylidene- 4'-A Diphenyl sulfide, 3,3',4,4,-tetrakis(t-butylperoxycarbonyl)benzophenone and U 2,4,6-trimethylbenzophenone. The compound may, for example, be α,α-diethoxyethyl benzene, 2-methylmorpholinyl-l-(4-nonylthiophenyl)propan-1-one, 2-benzyl-2-ene Methylamino-1-(4-morpholinylphenyl)butane-indole-ketone, 2-hydroxy-2-methyl-1-phenylpropane-I-ketone, 1,2-diphenyl a 2,2-dimethoxy^-ethanone, 2-fluorenyl-2-methyl-b[4-(2-carbylethoxy) An oligomer of propylidene acetonyl sulfonylcyclohexylphenyl fluorene and 2-transyl-2-yl fluorenyl-[4-monoethylidene] Q phenyl]propanone-I-ketone. The brewing-based phosphine oxide compound may, for example, be 2,4,6-trimethylbenzoyldiphenylphosphine oxide or bis(2,4,6-trimethylbenzylidene)phenylphosphine oxide. The compound may, for example, be 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-trimethyl, 2,4'bis(trichloromethyl)-6-( 4-methoxynaphthyl)--^-tris-indole-bisindole chloromethyl^(4)methoxystyryl)-1,3,5-trianthene, 2,4-bis(trichloro Methyl)|[2-(5-methylaminopyran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)_6_[2_(furan-2- Vinyl]_1'3'5-triazine, 2,4-bis(trichloromethyl)_6_[2_(4_ 321867 95 201100410 diethylamino-2-methylphenyl)vinyl]- 1,3,5-trianthene and 2,4-bis(trichloroindenyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3, 5-trin . For the photopolymerization initiator, Irgacure 907 (manufactured by Ciba Japan Co., Ltd.), Irgacurel 84 (manufactured by Ciba Japan Co., Ltd.), Irgacure 651 (manufactured by Ciba Japan Co., Ltd.), and Irgacure 819 (manufactured by Ciba Japan Co., Ltd.) can be used. , Irgacure 250 (manufactured by Ciba Japan Co., Ltd.), irgacure 369 (manufactured by Ciba Japan Co., Ltd.), SEIKUOL BZ (made by Seiko Co., Ltd.), SEIKUOL Z (made by Seiko Chemical Co., Ltd.), SEIKU〇L BEE ( Seiko Chemical Co., Ltd., KAYACURE BP100 (manufactured by Nippon Chemical Co., Ltd.), KAYACURE UVI-6992 (manufactured by DOW Co., Ltd.), ADEKA 0PT0MER SP~i.52 (manufactured by ADEKA Co., Ltd.), ADEKA 〇pT〇MER SP -170 (manufactured by ADEKA Co., Ltd.), TAZ_A (manufactured by Japan A), TAZ-PP (manufactured by Siber Hegner, Japan), and TAZ-104 (manufactured by Sanwa Chemical Co., Ltd.). The heat resistance and the heat and humidity resistance of the optical film to which it is applied tend to become high. The photopolymerization initiator is preferably acetophenone, more preferably 2-benzylmethyl-mercaptoamine. Phenyl phenyl)_ι_ butanone. The content of the polymerization initiator in the composition of the present invention is generally from 〇1 to 30 parts by weight, based on the total amount of the liquid crystal compound and the compound of the present invention, preferably from 〇5 to 1 part by weight. . If it is within the above range, the compound of the present invention can be polymerized without disturbing the orientation of the liquid crystal compound. 321867 96 201100410 The composition of the invention may also comprise a photosensitizer. The photosensitizer may, for example, be an xanthone, thioxaniihone or the like. An anthrone compound (for example, '2,4-diethylthiazinone, 2-isopropylthio Anthracene or the like, an anthracene, an anthracene compound having a substituent such as an alkoxy group (for example, dibutoxyanthracene, etc.), phenothiazine, and rubrene. By using a photosensitizing agent, the polymerization reaction of the compound of the present invention can be carried out with high sensitivity, and the temporal stability of the obtained optical film can be improved. The content of the photosensitizer is usually from 0.1 to 30 parts by weight, preferably from 0.5 to 10 parts by weight, based on 100 parts by weight of the total of the liquid crystal compound and the compound of the present invention. When it is within the above range, the compound of the present invention can be polymerized without disturbing the orientation of the liquid crystal compound. The composition of the present invention may also comprise a polymerization inhibitor. The polymerization inhibitor is, for example, a hydroquinone compound having a substituent such as a hydroquinone or an alkoxy group, a catechol compound having a substituent such as an alkyl group such as a butyl catechol, or a pyrogallol compound, 2, 2, A radical scavenging agent such as 6, 6-tetramethyl-1-piperidinyloxy radical, a thiophenol compound, a cold-naphthylamine compound, a 5-naphthol compound or the like. By using a polymerization inhibitor, the polymerization reaction of the liquid crystal compound or the compound of the present invention can be easily controlled, and the stability of the obtained optical film can be improved. The content of the polymerization inhibitor is from 0.1 to 30 parts by weight, preferably from 0.5 to 10 parts by weight, based on 100 parts by weight of the total of the liquid crystal compound and the compound of the present invention. If it is within the above range, the compound of the present invention can be polymerized without disturbing the orientation of the liquid crystal compound. The composition of the present invention may also contain a ping agent. The coating agent may, for example, be an additive for a radiation hardening coating (BYK-97 321867 201100410 352, ΒΥΚ-353, BYK-361N), and a coating additive (Toray Dow Corning Co., Ltd., SH28PA, DC11PA, ST80PA) ), coating additives (manufactured by Shin-Etsu Chemical Co., Ltd.: KP32; l, KP323, X22-161A, KF6001), fluorine-based additives (made by DIC Corporation: F-445, F-470, F-479). By using a leveling agent, a smoother optical film can be obtained. Further, the flowability of the composition of the present invention can be controlled during the production of the optical film or the crosslinking density in the obtained optical film can be adjusted. The content of the leveling agent is preferably 〇· 01 to 30 parts by weight, based on the total weight of the liquid crystal compound and the compound of the present invention, 〇 5 to 1 part by weight. If it is within the above range, the compound of the present invention can be polymerized without disturbing the orientation of the liquid crystal compound. The composition of the present invention preferably contains an organic solvent in terms of its fluidity. The organic solvent may be a solvent which can dissolve the organic solvent such as the compound of the present invention or a liquid crystal compound and is inert to the polymerization reaction, and specific examples thereof include decyl alcohol, ethanol, ethylene glycol, and isopropyl alcohol. Propylene glycol is an alcohol solvent such as ethylene glycol methyl ether or ethylene glycol butyl ether; ethyl acetate, butyl acetate, ethylene glycol decyl ether acetate, butyrolactone, propylene glycol methyl ether acetate, Ethyl acetate solvent; ketone solvent such as copper, methyl ethyl, cyclohexane, cyclohexanyl, 2-heptane, methyl isobutyl ketone; pentyl alcohol, hexazepine, gargane, etc. Non-chlorinated aliphatic smoke solvent; non-chlorinated aromatic hydrocarbon solvent such as toluene, xylene, and stupid; nitrile solvent such as acetonitrile; propylene glycol monomethyl ether, tetrahydrofuran, methoxyacetone, etc. Solvent; gas imitation, chlorine stupid and other chlorinated smog solvents; benzene and so on. These organic solvents may be used singly or in combination of two types of 321867 98 201100410 or more. In particular, the compound of the present invention and the composition of the present invention are excellent in compatibility, and are soluble in an alcohol solvent, a solvent, a ketone solvent, a non-chlorinated aliphatic hydrocarbon solvent, and a non-vaporized aromatic hydrocarbon solvent. Therefore, it is possible to form a film without using a gasification hydrocarbon solvent such as chloroform. The content of the organic solvent is usually 10 to 10,000 parts by weight, preferably 100 to 5,000 parts by weight, based on 100 parts by weight of the compound of the present invention. When the composition of the present invention contains an organic solvent, the viscosity thereof tends to be less likely to cause uneven film thickness of the optical film, and is generally 0.1 to 10 Pa · s, and preferably 0.1 to 7 Pa · s. The solid content in the composition of the present invention is usually from 2 to 50% by weight, preferably from 5 to 50% by weight. If the concentration of the solid content is 2% by weight or more, • the optical film is not too thin, and there is a tendency to easily obtain an optical film having a birefringence required for optical compensation of the liquid crystal panel. Further, when the concentration of the solid content is 50% by weight or less, the viscosity of the composition is not too small, and the film thickness unevenness of the optical film tends to be less likely to occur. Here, the "solid content" means a component which remains after the organic solvent is removed from the composition of the present invention. Next, an optical film relating to the present invention will be described. In the present invention, the term "optical film" means a film which can penetrate light through a film and has an optical function. Optical function means refraction, birefringence, and the like. A retardation film of one type of optical film is used to convert linearly polarized light into circularly polarized or elliptically polarized light, or conversely to convert circularly polarized or elliptically polarized light into a linearly polarized 'light. The optical film of the present invention has a structural unit derived from the compound of the present invention, but the wavelength dispersion characteristics of the optical film 99 321867 201100410 can be adjusted by adjusting the content of the structural unit. When the content of the monoterpene of the compound derived from the present invention in the optical film is increased, it exhibits flatter wavelength dispersion characteristics and further inverse wavelength dispersion characteristics. Specifically, the composition of the present invention containing an optical film having a content of a structural unit derived from the compound of the present invention, which is determined by the following operations (a) to (e), is prepared and The composition may be polymerized: (a) The composition of the present invention is prepared to have a different content of the composition of the present invention from about 2 to 5; (b) The same film thickness is produced for each of the prepared compositions and is derived from An optical film having a different structural unit content of the compound of the present invention; (c) determining a phase difference value of the optical film obtained in (b); (d) a phase difference value obtained according to (c), And determining the correlation between the content of the structural unit derived from the compound of the present invention and the phase difference of the optical film; (e) determining the optical film of the film thickness from the correlation obtained by (d) The desired phase difference value is required to be derived from the content of the building blocks of the compounds of the invention. Generally, the phase difference Re(λ) in a certain wavelength; I is divided by the value of the phase difference Re(550) in 550mn (Re(λ)/Re(550)) is close to 1 in the wide-band region, or in Display [Re(450)/Re(550)]<l and [Re(650)/

In the wide-band region of the reverse wavelength dispersion of Re(550)]&gt;i, the same polarization conversion can be performed. The optical film of the present invention can be obtained by polymerizing the compound of the present invention. It is also possible to polymerize one type of the compound of the present invention or to polymerize two types of the compound of the present invention. Further, the optical disk of the present invention can be produced by combining the compound of the present invention with 100 321867 201100410. In the case of easy-to-eat, it is preferred to use a solution in which the compound of the present invention is dissolved in an organic solvent, and the solution is applied to a support substrate, dried, and entangled to obtain an optical film. The solid content concentration in such a solution is generally from 2 to 50% by weight, preferably from 5 to 50% by weight. The unpolymerized film sheet can be obtained by drying a solution of the compound of the present invention on a support substrate and drying. When the unpolymerized film shows a nematic liquid crystal phase, the resulting optical film system exhibits birefringence due to monodomain orientation. The film thickness of the optical film can be adjusted by appropriately adjusting the compound content of the present invention in the compound solution of the present invention or the coating amount of the solution on the support substrate. When the amount of the compound of the present invention is constant, the retardation value (retardation value and Re(in)) of the optical film of the second film is determined according to the formula (7), so that in order to obtain the desired Re (A) is only required to adjust the film thickness d and Δη (λ). ° Q Re( λ )=άχΔη( λ ) (7) (wherein, Re(1) represents a wavelength; a phase difference value 'd' in the film represents a film thickness, and Δη(λ) represents a birefringence in a wavelength ^1111). The coating method of the solution of the compound of the present invention on the support substrate can be exemplified by extrusion coating, direct gravure coating, reverse gravure coating, CAP coating, and die coating. For example, a method of applying an applicator such as a dipping applicator or a bar coating machine may be employed. Examples of the support substrate include glass, plastic sheets, and plastic film sheets. The translucent film may, for example, be a polyolefin film such as polyethylene, polyacryl, or ice-reducing = 321867 101 201100410 polymer; a polyvinyl alcohol film; a polyethylene terephthalate film; Methacrylate film; polyacrylate film; cellulose ester film; polyethylene naphthalate film; polycarbonate film; polysulfone film; polyether film; Poly-1 嗣 film; polyphenylene sulfide film; polyphenylene oxide film. In the step of requiring the strength of the optical film, such as the bonding step, the transporting step, and the storage step of the optical film, the support substrate can be easily handled without damage or the like of the optical film. After forming an oriented film on the support substrate, a solution of the compound of the present invention is applied to the oriented film. The oriented film system preferably has a solvent resistance which is insoluble in the solution when the solution of the compound of the present invention is applied. Further, the orientation film preferably has heat resistance in a heat treatment for removing a solvent or aligning liquid crystal molecules. Further, it is preferable that an oriented film such as peeling due to friction or the like does not occur during rubbing. Such an oriented film is preferably composed of a directional polymer or a composition containing a directional polymer. The above-mentioned directional polymer may, for example, be a polyamine or a gelatin compound having a stilbene bond in a molecule, a polyamidimide having a ruthenium bond in a molecule, and a polyglycolic acid or a polyethylene glycol having a hydrolyzate thereof. , calcined modified polyethyl decyl alcohol, polypropylene decylamine, polyoxazole, polyethyleneimine, polystyrene, polyvinyl ketone, polyacrylic acid and polyacrylic acid ester. These oriented polymers may be used singly or in combination of two or more kinds. It is also possible to use a copolymer of a directional polymer for this purpose. These oriented polymers can be easily obtained by polycondensation such as dehydration polycondensation, deamination polycondensation, radical polymerization, anionic polymerization, cationic polymerization, etc., 102, 321,867, 201100410, lock polymerization, coordination polymerization, ring-opening polymerization, and the like. . These oriented polymers are generally dissolved in a solvent and used as a solution. Solvents are not limited. Specifically, for example, water. _ β 扒, sterol, ethanol, ethylene glycol, isopropanol, propylene glycol, ethylene glycol, cup, ethylene glycol, etc., an alcohol solvent; ethyl acetate, butyl acetate, B Alcoholic solvent such as diol methyl-acetic acid vinegar, propylene glycol methyl ether acetate vinegar, lactic acid ethyl acetate; acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, methyl Non-chlorinated aliphatic ketone solvents such as butyl ketone, such as bismuth pentoxide, hexazone, and hexanol; non-chlorinated aromatic smog solvents such as acetaminophen and diphenylbenzene; nitrile solvents such as acetonitrile; An ether solvent such as a fine powder, a tetrahydrofuran or a dimethoxyethane; a chlorinated hydrocarbon solvent such as a milk imitation or a chlorobenzene. These organic solvents can be used singly or in combination of two or more types. .—The village directly uses the commercially available directional kneaded mosquito-forming film. The commercially available oriented film material may, for example, be Sunever (registered trademark; manufactured by Nissan Chemical Industries Co., Ltd.), 〇ptiner (registered trademark; JSR Co., Ltd., G荨. Right-handed oriented film, due to disability The Folding System can provide the optical film of the large dimension of the birefringence in the surface of the birefringence, which can also correspond to the flat (10). The method of forming the formula (4) on the support button can be exemplified by supporting the following: or the commercially available oriented film material or the material used as the oriented film as a method of making money (four), pure, and carrying out the method. The thickness of the gas oriented film, generally iG to l_nm, preferably from 1 G to 10 Å to the right, allows the compound of the present invention to be oriented at a desired angle to the oriented film 321867 103 201100410. The alignment film may be rubbed as needed, or the alignment film may be subjected to polarized UV irradiation, by which the compound of the present invention or the like may be oriented in a desired direction. That is, the shape or inclination of the refractive index ellipsoid showing the birefringence state of the manufactured optical film can be adjusted. The method of rubbing the oriented film may be, for example, a method of winding the rubbing cloth so that the rubbing roller in rotation contacts the oriented film carried on the stage. The method of laminating an unpolymerized film on an oriented film laminated on such a supporting substrate can reduce the production cost as compared with the method of producing a liquid crystal cell and injecting a liquid crystal compound into the liquid crystal cell, and Film production diaphragm. The removal of the solvent may be carried out in parallel with the polymerization reaction, but in terms of film formability, it is preferred to remove almost all of the solvent before the polymerization reaction. The method for removing the solvent may, for example, be a method such as natural drying, air drying, and pressure reduction drying. The temperature at which the solvent is removed by heating is generally from 0 to 250 ° C, preferably from 50 to 220 ° C, more preferably from 80 to 170 ° C. The heating time is preferably from 10 seconds to 60 minutes, more preferably 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 sufficiently heat-resistant can be used as the supporting substrate. By polymerizing the obtained unpolymerized film to be cured, a film having a direct orientation of the compound of the present invention, that is, a polymer film can be obtained. A diaphragm that is less susceptible to the effects of heat on birefringence can be obtained. The method of polymerizing the unpolymerized film may be appropriately determined depending on the type of the liquid crystal compound and the compound of the present invention. When the polymerizable group in the compound 104 321867 201100410 and the liquid crystal compound of the present invention is a photopolymerizable group, photopolymerization 4 can be used, and if the polymerizable group is thermopolymerizable I, a thermal polymerization method can be used. • By photopolymerization, the unpolymerized film can be polymerized at a low temperature to support the substrate. The range of heat resistance of the substrate is widened, and the point at which it can be easily manufactured industrially is suitable for photopolymerization. A polymerizable group of the compound of the present invention and a liquid crystal compound. Further, from the viewpoint of film formability, photopolymerization is also preferred. The photopolymerization reaction can be carried out by irradiating the unpolymerized film with visible light, ultraviolet light or laser light. In terms of handling, it is particularly suitable for ultraviolet light. The light irradiation can also be carried out by using the compound of the present invention at a temperature of the liquid crystal phase. At this time, the polymeric film may be patterned by masking or the like. The birefringence Δη (λ) can be prepared by appropriately adjusting the exposure enthalpy, the heating temperature, and the heating time during the polymerization to the desired phase difference. The optical film of the present invention has a thinner film thickness than the stretched film which imparts a phase difference by the extension of the polymer. 0 By peeling off the support substrate, a film in which an oriented film and an optical film are laminated can be obtained. Further, the oriented film can be peeled off to obtain an optical film. The optical film thus obtained is excellent in transparency and can be used as a film for various displays. The thickness of the optical film is as described above, and varies depending on the phase difference of the optical film, but the thickness is preferably 01 to 10/zm, and more preferably 0.2 to 5 #m, in terms of reduction in photoelasticity, particularly preferably 0.5 to 3 #m. The retardation of the optical film exhibiting birefringence is generally 5 Å to 5 Å nm', preferably 100 to 300 nm. Such a film can be subjected to the same polarized light in a wider wide-band region. 321867 105 201100410 The converted optical film can be used as an optical compensation film in all liquid crystal panels or FPDs such as organic EL. The optical film of the present invention can be used as a wide band and/4 or λ/2 plate. When it is used as a wide-band λ /4 plate or a λ /2 plate, the content of the structural unit derived from the compound of the present invention and the film thickness of the optical film in the optical film can be appropriately selected. When the film is used as the λ/4 plate, the film is adjusted so that it is 135 to 1634〇ηηη, and the film is adjusted to be about 137. 5 nm. Thick enough. When the λ/2 plate is used, it is preferable to adjust the film thickness so that the Re (550) of the obtained optical film is 250 to 300 nm, preferably 273 to 277 nm, and particularly about 275 nm. The optical film of the invention can also be used as an optical film for the VACVertical Α * igmnent ''vertical orientation' mode. When it is used as the optical film for the va mode, the content of the structural unit derived from the compound of the present invention in the optical film may be appropriately selected. The film thickness may be adjusted so that the obtained light or sheet Re (55 Å) is generally 4 Å to i 〇〇 nm, and preferably 60 to 80 nm. By using only a small amount of the compound of the present invention, the wavelength dispersion characteristic of the optical film can be shifted by a value close to 1, and the desired wavelength dispersion characteristics can be modulated in a simple manner. The optical film of the present invention can also be used for anti-reflection film such as anti-reflection (AR) film, offset, _ 1 A film, retardation film, ellipsoidal film, viewing angle expansion film or through-liquid crystal display. Optically compensated for diaphragms and the like. The optical film of the present invention can exhibit excellent optical characteristics even if one sheet is used, and a plurality of sheets can be laminated. Alternatively, it can be used in combination with other diaphragms. Specific examples of the combination with other films include, for example, an elliptically polarizing plate in which an optical film of the present invention is bonded to a polarizing film, and the optical film of the present invention is further bonded to the ellipsic polarizing plate as a wide band; The wide-band circular polarizer of the board •etc. The optical film of the present invention can be formed by being applied to a support substrate or an alignment film and polymerizing it. Therefore, as shown in Fig. 1, a wide band is formed on the color filter more simply than in the past. Domain, for example; 1/4, λ/2 optical film sepals. Fig. 1 is a schematic view showing a color filter 1 of the present invention. The color filter 1 sequentially laminates the color filter layer 4, the alignment film 3, and the optical film 2 of the present invention. An example of a method of manufacturing such a color filter 1 will be described below. First, a directional polymer is laminated on the color filter layer 4, and rubbing treatment is performed to form the alignment film 3. The oriented polymer can also be laminated by an inkjet method. Then, on the obtained oriented film 3, a solution of the compound of the present invention in which the content of the compound of the present invention is adjusted is prepared in such a manner that the obtained optical film has a desired wavelength dispersion property, and the solution is applied. The optical film 2 is formed by the thickness of the desired phase difference. By using such a color filter 1, a thinner liquid crystal display device can be manufactured. As an example, a schematic view of a liquid crystal display device 5 of the present invention is shown in Fig. 2 . The liquid crystal display device 5 shown in Fig. 2 is attached to the polarizing plate 6 via a bonding agent of 107 321867 201100410 to fix the substrate 7 opposed to the back surface by a glass substrate or the like. The optical film 2' is formed on the color filter '4" formed on the substrate 7, with the alignment film 3 interposed therebetween. Further, on the optical film 2, a counter electrode 8 is formed, and a liquid crystal phase 9 is formed on the counter electrode 8. On the f-light side, the substrate n such as a glass substrate is fixed via the adhesive. Further, a thin film transistor (?{;7) and an insulating layer 主动 for actively driving the liquid crystal layer are formed on the substrate U. Further, a transparent electrode 13 and/or a reflective electrode 13 composed of Ag, A1 or IT〇 (indium addition) is formed on the TFT. The liquid crystal display cleavage 5 shown in Fig. 2 has a configuration in which the number of optical films is smaller than that of the conventional liquid crystal display device, and a thinner liquid crystal display can be manufactured. An example of a method of manufacturing the liquid crystal display device 5 on the liquid crystal layer side of the substrate on which one of the η-loaded color filters 1' is formed will be described below. On the substrate on the backlight side, it can be made on the acid glass. The open electrode gate insulating film composed of &amp; _ and the amorphous layer are deposited and patterned, and then the amorphous X-ray knife is annealed to form a crystallized semiconductor film, and thereafter ' The regions on both sides of the gate electrode are doped with p, B, etc. to form an n-channel, p-pass, and TFT. Further, by forming an insulating layer composed of Si〇2, it is possible to form a substrate on the backlight side. Further, the transparent electrode 13 for the all-transmissive display device is laminated on the backlight side substrate n on the backlight side substrate n. Further, in the same manner, by using Ag, A1 or the like instead of ΙΤ0, the reflective electrode 13 for a fully reflective display device can be obtained. Further, by appropriately combining the reflective electrode and the transparent electrode, the electrode on the backlight side of the transflective liquid crystal display device can also be obtained. 108 321867 201100410 Ο ❹ In addition, the color filter Zhan 4 is formed on the opposite substrate 7 '. By using R, G, and 彩色 color; * light film, you can also get full color LCD display device. Next, a directional polymer is coated on the color light-passing sheet layer 4, and the alignment film 3 is formed by rubbing. The alignment film 3 is coated with a solution of the compound of the present invention, heated to a temperature range of the (iv) phase, and polymerized by ultraviolet irradiation to form an optical film 2. After the optical film is formed, the counter electrode 8 can be formed by the weir 0. Further, an alignment film is formed on the counter electrode to form a liquid crystal, and finally, the liquid crystal display device 5 can be fabricated by being combined with the substrate on the backlight side. The optical film of the present invention can also be used for a reflective liquid crystal display, an organic EL display II or an FPD film of the above optical film, and a FPD system having the phase difference plate is not particularly limited. For example, a liquid crystal display device (10) may be used. The function of the membrane film) = this is obtained with a polarizer and a polarizing film. And on the body two # layer &amp; optical film of the invention ^, body, on the single side or double-sided axe of the polarizing film or use the next 四 (4) combined cut % / book, "connect (four),, 咅 came In the present specification, the splicer "refers to both the adhesive and the adhesive, with reference to Figs. 3 to 5", explains the polarizing plate of the present invention. Figure 3 (a) to Figure 3 (e). The circular structure is not the polarizing plate of the present invention. FIG. 3( a ) is not a polarizing plate 3 〇 &amp; the laminate 15 is directly bonded to the laminate, and the laminate is supported by the substrate 16 . The alignment film 17 and the light 321867 109 201100410 are formed by the film 18. The polarizing plate 30a is laminated with a supporting base material 16, an orientation film 17, an optical film 18, and a polarizing film 15 in this order. The polarizing plate 30b shown in Fig. 3(b) is bonded to the polarizing film 15 via the adhesive layer 19. The polarizing plate 30c shown in Fig. 3(c) directly bonds the laminate 14 to the laminate 14', and further laminates the laminate 14' and the polarizing film 15 directly. The polarizing plate 30d shown in Fig. 3(d) is bonded to the polarizing film 14' via the adhesive layer 19, and the laminate 14' and the polarizing film 15 are directly bonded to each other. The polarizing plate 30e shown in Fig. 3(e) has the laminate 14 bonded to the polarizing film 14' via the adhesive layer 19, and further, the laminate 14' and the polarizing film are interposed via the adhesive layer 19'. The film 15 is laminated. An optical film 18 from which the support substrate 16 and the alignment film 17 are peeled off from the laminate 14 or a film composed of the alignment film 17 and the optical film 18 from which the support substrate 16 is peeled off from the laminate 14 may be used. Sheet to replace laminate 14. An optical film 18' from which the support substrate 16' and the alignment film 17' are peeled off from the laminate 14' may be used, or an alignment film 17' and an optical film from which the support substrate 16' is peeled off from the laminate 14' may be used. A diaphragm composed of a diaphragm 18' is substituted for the laminate 14'. The polarizing plate of the present invention may also laminate a plurality of laminates, and the plurality of laminates may all be the same or different. The polarizing film 15 may be a film having a polarizing function, and specifically, for example, a film in which a polyvinyl alcohol film is immersed in iodine or a dichroic dye after 110 321 867 201100410, and a polyvinyl alcohol is used. A membrane for adsorbing iodine or a dichroic dye after the membrane is extended. The adhesive used for the adhesive layer 19 and the adhesive layer 19' is preferably an adhesive having high transparency and excellent heat retention. Examples of such an adhesive include an acrylic adhesive, an epoxy adhesive, an urethane-based adhesive, and the like. The flat panel display device of the present invention includes the optical film of the present invention, and specifically includes a liquid crystal display device having a laminate of the polarizing plate of the present invention and a liquid crystal panel, or a bonded film. An organic EL display device of an organic EL panel of a polarizing plate and a light-emitting layer of the invention. The liquid crystal display device and the organic EL display device are taken as an example, and an embodiment of the flat panel display device of the present invention will be described below. Fig. 4 is a schematic view showing a bonding product 21 of a liquid crystal panel 20 and a polarizing plate 30 of a liquid crystal display device of the present invention. The laminate 21 is obtained by laminating the polarizing plate 30 of the present invention and the liquid crystal panel 20 via the adhesive layer 22. Using an electrode (not shown), a voltage is applied to the liquid crystal panel 20, and the liquid crystal molecules are driven to display black and white. Fig. 5 is a schematic view showing an organic EL panel 23 of an organic EL display device of the organic EL display device of the present invention. The organic EL panel 23 is formed by bonding the polarizing film 30 of the present invention and the light-emitting layer 24 via the adhesive layer 25. In the above organic EL panel, the polarizing film 30 functions as a wide-band circular polarizing plate. Further, the light-emitting layer 24 is a layer of at least one layer composed of a conductive organic compound. 111 321867 201100410 (Embodiment) Hereinafter, the present invention will be described in more detail by way of examples, but the invention is not limited thereto. (Example 1) <Synthesis Example of Compound (A1-1)>

(1) Synthesis of compound (Ι-a) 2,5 g of 2,5-dimethoxyaniline, 25 g of benzothiophene-2-carboxylic acid and 125. 3 g of dehydrated chloroform were mixed and reacted. To the obtained mixture was added 1.71 g of N,N-dimethylaminopyridine. The resulting mixture was cooled in an ice bath, and 3,8 g of N, Ν'-dicyclohexylcarbonyldiimide was added and allowed to react for 1 hour. Thereafter, the mixture was returned to room temperature, and the resulting mixture was filtered through a silica gel to remove a precipitate, followed by concentration under reduced pressure. The residue was added to a l/2 (v/v) solution of ethyl acetate-heptane to crystallize. The crystals of the precipitated (1-a) 33. 4 g were obtained by filtration. The yield was 76% based on 2,5-dimethoxyaniline. (2) Synthesis of compound (Ι-b) Mixed compound (1-&amp;) 33.352, 2,4-bis(4-decyloxyphenyl) 112 321867 201100410 -1,3-dithia-2, 4-diphosphetane-2,4-disulfide (2, 4-bis (4-methoxyphenyl)-l,3~dithia-2, 4-diphosphetane-2,4 . -disulfide)(Lawesson' s reagent) 22.4 g and 200 g of toluene, and the mixture was heated to 80 ° C to react the obtained mixture. After cooling, it was concentrated to obtain a red viscous solid having a compound (Ι-b) and a decomposition product of Lawesson's reagent as a main component. (3) Synthesis Example of Compound (1-c) A mixture containing the compound (Ι-b) obtained in the above paragraph, 25 5 g of sodium ruthenium oxide and 580 g of water were mixed, and the obtained mixture was allowed to react under ice cooling. Then, an aqueous solution containing 95.6 g of potassium ferricyanide was added to the mixture under ice cooling to react at room temperature for 12 hours. Filter and take the precipitated yellow precipitate. The collected temple was washed with water and then washed with ethanol, washed with ethanol, and vacuum dried to obtain a pale yellow solid (5 g) containing compound (b) as a main component. The yield is based on the compound (la). (4) Synthesis of compound (Ι-d) Ο Mixed compound (1-C〇19.5g and 97.5g of chlorinated rust, heated to 180°C for 2 hours) After cooling the obtained mixture, water was added thereto, and the obtained precipitate was extracted and washed with water, followed by calcination to obtain a solid A and a saponin 8 g containing the compound (b d) as a main component. The compound (ic) is 95%. (5) Synthesis of compound (A1-1) Mixed compound (ld) 5. 00 g, intervening (1) m廿g compound (A) 14. 68 g, dimercaptoamine group ratio唉0·20g and gas imitation 60ml. In the mixture of Lu, A w , .,., add 1-ethyl-3-(3-dioxyl 复 τ makeup propyl) under ice cooling. Carbonyl quinone imine hydrochloride 321867 113 201100410 7· 68g' The obtained reaction solution is mixed, and the alcohol is added to the residue to be crystallized. After the hydrazine, the pressure is reduced. The solution was dissolved in a white air, dried in a vacuum to give a white color, and the obtained product was obtained by filtration, and the yield was _d. Compound (4)-1) 2Η) ' 7. 40~7· 46 (m, 2Η), 7 8 3 to 7〇829 (m, 7.22 (s, confirmed by grain observation by a polarizing microscope) The phase transition temperature of the compound (Al 1). The compound (Α1_ι) exhibits a smectic phase from Μα to 155C at a temperature rise, from 155. (: to 18 〇. The 向 is above the nematic phase, when cooling, Crystallization was carried out until the nematic phase was exhibited at 93 t. (Example 2) Synthesis Example of <Compound as Diffusion>

(1) Synthesis Example of Compound (5-a) 18.9 g of 2,5-dimethoxyaniline, benzofuran- 2 - oxoic acid 114 321867 201100410 20. Og and dehydrated gas imitation 125. Og, which is allowed to react. N,N-dimethylaminopyridine i.5 ig was added to the obtained mixture ‘. The resulting mixture was cooled in an ice bath. 'N, Ν'-dicyclohexylcarbodiimide 28. 〇g was added and allowed to react for 1 hour. Thereafter, it was returned to room temperature and reacted overnight. The resulting mixture was filtered through a silica gel to remove a white precipitate and a brown component, and then concentrated under reduced pressure. The mixture was crystallized by adding an ethyl acetate/graft solution (v/v = 1 / 2) to the residue. 4克。 The precipitated crystals were filtered and dried in vacuo to give a pale yellow powder of compound (5-a) 14.4g. The yield is based on 2,5_ ® dimethoxyaniline benchmark of 39%. (2) Synthesis of Compound (5-b) Mixed Compound (5-a) 13. Og, 2, 4-bis(4-methoxyphenyl)-1,3-'monothia 2, 4- A dish of kiwi was burned with 2-, 4-monosulfide (Lawesson's test drug) 9. 2g and benzene 〇〇 l〇〇g, and the temperature was raised to 8 (TC was used to react the resulting mixture for 5 hours. After cooling) It is a red viscous solid which is a main component of the decomposition product of the chemical compound (5-b) and Lawesson's. 〇 (3) The synthesis example of the compound (5-c) is mixed with the compound obtained in the preceding paragraph ( a mixture of 5-b), sodium hydroxide 10.5 g and water 250 g, the resulting mixture is allowed to react under ice cooling. Then, an aqueous solution containing 39.3 g of potassium ferricyanide is added under ice cooling to cause a reaction. The reaction was carried out for 12 hours at room temperature, and the precipitated yellow sag was collected by filtration, and the precipitated chamber was washed with water, then washed with hexane, washed with ethanol, and vacuum dried to obtain a compound (5- c) The pale yellow solid as a main component is 0.3 g. The yield is 69% based on the compound (5-a). (4) Synthesis of the compound (5-d) 321867 115 201100410 Mixed compound (5-c) 7. 〇 g and 35.0 g of vaporized pyridine rust, and the mixture was heated to 180 ° C for 2 hours. After cooling the obtained mixture, water was added thereto, and the obtained precipitate was collected by filtration, washed with water and then hexane to obtain a compound ( 5-d) solid as a main component of 6.5 g. The yield is 100% based on the compound (5-c). (5) Synthesis of compound (A5-1) Mixed compound (5-d) 1. 60 g, Compound (A) 4. 96 g, dimethylaminopyridine 0.07 g and gas imitation 30 ml. In the obtained mixture, N, Ν'-diisopropylcarbonyldiimide 171 g was added under ice cooling. The reaction solution was reacted overnight at room temperature, filtered with hydrazine, and concentrated under reduced pressure. The residue was crystallized by adding decyl alcohol. The crystals were collected by filtration and dissolved in chloroform. The phenol was filtered, and the resulting white precipitate was filtered, washed with ethanol, and dried in vacuo to give a white powder (yield: 5-1): 4.73 g. The yield was 77% based on the compound (5-d). 1 H-NMR (CDC13) of A5-1): δ (ppm) 1. 45~1· 91 (m, 2 4H), 2. 3 5~2. 8 3 (m, 1 2H), 3. 9 2~3· 9 7 (t, 4H), 4. 15 to 4. 20 (t, 4H), 5·79~5. 84 (dd, 2H), 6·07~6. 17 (m, 2 H), 6.37~ 6.44 (xn, 2H), 6.87~7.01 (m, 8H), 7.25 (s, 2H), 7. 31 to 7. 34 (t, 1H), 7. 40~7. 42 (t, 1H), 7 · 55~7: 6 0 (m, 2H), 7. 6 8~7. 7 1 (d, 1H) · Confirmation of phase transfer of the obtained compound (A5-1) by grain observation by a polarizing microscope temperature. The compound (A5-1) exhibits a nematic phase from 180 ° C or higher at the time of temperature rise, and exhibits a nematic phase at 9 yc upon cooling, and is crystallized. (Example 3) <Synthesis Example of Compound (Eight Bud)> 321867 116 201100410

,ΟΗ,CHO COOEt

COOH

MeO—(\ OMe. nh2

(")MeO

COOH

OMe (6-b)

OMe ?H (4) ΪΜβ «-) 〇H OH^ΟΗ:φ («) -γ{η

C6H12-〇-^~^-〇 (A)

-COOH

^0-CeH120-Q-0^-M Contains 0^〇Η〇Ό·〇°*Η, 2·ν (A6-1)

(1) 5-Methylbenzene bite ° South-2 tickic acid synthesis example mixed 5-mercapto salicylaldehyde 50g, potassium carbonate 101.51g, tetrabutylammonium bromide 11.84g, potassium iodide 30. 48g and toluene , warm to 80 ° C. To the obtained dispersion, diethyl bromomalonate 114. lg was added dropwise thereto, and the mixture was reacted at 110 ° C (returning at the boiling point of toluene) for 24 hours. To the obtained brown solution, 3 ml of 3 g of potassium hydroxide was added and further reacted for 24 hours. After the obtained reaction liquid was cooled to room temperature, it was concentrated under reduced pressure with an evaporator. 40 g of potassium hydroxide and 400 ml of ethanol were added to the residue, and the mixture was stirred at 80 ° C for 1 hour. After cooling to room temperature, the ethanol was distilled off in a distiller. The residue was dissolved in 500 ml of pure water and 500 g of ice, and the pH was adjusted to 3 with 2N sulfuric acid. The leaching of the precipitated yellow precipitate was carried out, and the mixture was washed with EtOAc (3 mL). The yield was 68% based on 4-methyl salicylaldehyde. (2) Synthesis Example of Compound (6-a) 30.4 g of 2,5-dimethoxyaniline, 35.0 g of 5-mercaptobenzofuran-2-carboxylic acid, 20.1 g of triethylamine, N, N' - 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. After the obtained solution was cooled in an ice bath, hexafluorodisic acid 1H-benzotris-yt-1-yloxytris(dimethylamino)phosphonium salt (hereinafter referred to as Β0Ρ reagent) 92.28 g was added. It was reacted at room temperature for 24 hours. A mixed solution of water and methanol (2 parts by volume of water and 1 part by volume of decyl alcohol) was added to the obtained mixture to cause crystallization. The obtained precipitate was collected by filtration, washed with a mixed solution of water and decyl alcohol (1 part by volume of water, 1 part by volume of decyl alcohol), and dried in vacuo to give the compound (6-a) 23.8 g of pale yellow powder. The yield was about 39 ° / 〇 on the basis of 2, 5-dimethoxyaniline. (3) Synthesis of compound (6-b) f Mixed compound (6-a) 23. 8g, 2, 4-bis(4-decyloxyphenyl)-1,3-dithia-2, 4 - Di-heterocyclic butyl ketone-2,4-disulfide (Lawesson's reagent) 16. lg and toluene 80 g, and the mixture was heated to 80 ° C and the resulting mixture was reacted for 8 hours. After cooling, it was concentrated to obtain a red viscous solid having a compound (6-b) and a decomposition product of Lawesson's reagent as a main component. (4) Synthesis Example of Compound (6-c) A mixture containing the compound (6-b) obtained in the above paragraph, oxidized

I sodium 18.4 g and water 400 g, and the resulting mixture was stirred under ice cooling. Then, an aqueous solution containing 68. 7 g of potassium ferricyanide was added under ice cooling to cause a reaction. The reaction was allowed to proceed at room temperature for 24 hours, and the precipitated yellow precipitate was filtered. The precipitate thus obtained was washed with water and then washed with hexane, washed with ethanol, and dried in vacuo to obtain 14.8 g of a pale yellow solid compound (6-c) as a main component. The yield was 59% based on the compound (6-a). (5) Synthesis of compound (6-d): Compound (6-c) 14.8 g and gasified pyridinium 74. 0 g (5 times mass 118 · 321867 201100410), and heated to 180 C for 2 hours. . After the obtained mixture was cooled, water was added thereto, and the obtained sinking chamber was taken, and washed with water and then burned to obtain a solid ίο. 4 g which had a compound (6-d) as a main component. The yield was 77% based on the compound (6-c). (6.) Synthesis of compound (A6-1) The compound (6-d), 70 g, compound (A), 5.02 g, dimethylaminopyridine, 0.07 g, and gas, 30 ml. To the resulting mixture was added N, Ν'-diisopropyl succinimide 1.73 g under ice cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered over silica gel, and concentrated under reduced pressure. The sterol was added to the residue to crystallize it. The crystals were collected by filtration and redissolved in chloroform. While stirring the obtained solution, sterol was added, and the resulting white precipitate was collected by filtration, washed with heptane, and dried in vacuo to give a white powdery compound (A6-1) 4·72 g. The yield was 75% based on the compound (6-d). 1 H-NMR (CDC13) of the compound (A6-1): δ (ppm) 1. 45 〜1. 85 (m, 24H), 2. 34~2· 83 (m, 1 2H), 2.84 ( s, 3H), 3. 92~3. 9 7 (t, 4 Η), 4. 15 〜4. 20 (t, 4 Η), 5. 79 〜5· 84 (dd, 2 Η) 6 Ο 7 ~6. 1 7 (m, 2Η), 6. 3 7~6, 4 4 (m, 2Η), 6. 8 7~7. 〇1 (m, 〇8 Η), 7. 2 2 (m, 3 Η) ' 7. 4 4 to 7. 4 7 (m, 3 H) ' The phase transition temperature of the obtained compound (Α6-1) was confirmed by pattern observation with a polarizing microscope. The compound (Α6_ι) was from 146 at elevated temperature.呈现 The nematic phase is present above 190 ° C, and is 1 于 when cooling. (: The nematic-phase is crystallized. • (Example 4) <Synthesis of Compound (A1 〇-1)> 321867 319 201100410

(1) Synthesis of 5-isobutylbenzofuran 40 g of 4-isobutylphenol was dissolved in N,N'-dimercaptoacetamide 240. Og. After the solution was cooled in an ice bath, 10.9 g of sodium hydroxide was added in 10 portions to be added. After stirring at room temperature for 1 hour, after the end of the hydrogen generation, 33.17 g of a gas acetaldehyde dimercaptoacetal was added dropwise. After stirring at 80 ° C for 5 hours, it was confirmed that the reaction mixture was completed, and the reaction liquid was added to 1000 ml of water and 400 ml of decyl isobutyl ketone to carry out liquid separation. The organic layer was recovered, and further, the organic layer was washed twice with 800 ml of pure water. After the organic layer was recovered, it was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a red viscous liquid. Separately, 400 g of toluene and 2.61 g of orthophosphoric acid were mixed and heated to 110 °C. A solution of a red viscous liquid dissolved in 100 ml of toluene was added dropwise to the solution. After stirring at 110 ° C for 3 hours, it was cooled to room temperature. The reaction solution was washed twice with a 1N aqueous sodium hydrogencarbonate solution, and finally washed with 500 ml of purified water. The organic layer was taken up, and dried over anhydrous sodium sulfate. The yield is 90% based on the 4-isopropylphenol benchmark 120 321867 201100410. 4克。 (2) 2-Methyl hydrazide i-butyl bromo bromo compound. The solution #皮^, methyl methacrylate solution was mixed at room temperature for 2 hours, and the reaction mixture was allowed to cool to room temperature with 100 t of the solution, and the pure hydrazine was added to the sodium hydride. with. Adjust Qiu to 8^ and A stupid liquid. 6克后后过渡。 The recovery, the machine layer, the addition of activated carbon 2. 6g after the transition. The evaporator is decompressed and decompressed, and the product is dissolved in (10) towel, and the person is said to be a tube (four) analyzer (transfer: gas imitation / heptane = l / l (v / v) - gas imitation 1 〇〇 ν 〇 %%) . The original ingredients were taken out, concentrated in an evaporator, and dried in vacuo to give a pale red viscous liquid of 2-carbazyl-5-isobutylbenzofuran 8·5 g. The yield was 28% on the basis of 5-isobutylbenzofuran. (3) 5-Isobutylbenzone. Synthetic example of flu-2-pyruic acid 16.40 g of 2-mercapto-5-isobutylbenzofuran and 9.43 g of sulfonic acid of an amine were mixed with 60 ml of pure water. After cooling in an ice bath, a solution of sodium chlorite &amp; 78 g of water in 50 ml was added dropwise. The reaction was carried out in a water bath for 36 hours. To the reaction solution, 100 ml of toluene was dropped, and 5 g of hydrogen hydroxide was discharged to adjust the pH to 12. After the liquid separation, the water layer was recovered, and the water layer was further washed with 300 ml of a stupid. The aqueous layer was recovered, and the pH was made 2 with 2N-hydrochloric acid, and then 300 ml of toluene was added to carry out liquid separation. The organic layer was taken up, dried over anhydrous sodium sulfate, and evaporated, evaporated, evaporated, evaporated, evaporated, evaporated. The yield is based on the 2-methylindolyl-5-isobutylbenzofuran standard of 38% 〇121 321867. 201100410 (4) The synthesis of the compound (10-a) is mixed with 2, 5-dimethoxyaniline 4. 71g, 5-isobutylbenzofuran-2-carboxylic acid 8. 71g, triethylamine 3. llg, hydrazine, Ν'-didecylaminopyridine 0. 75g and dehydrated N, Ν'-dimethyl乙含胺35. Og. After the obtained solution was cooled in an ice bath, 14.28 g of a reagent was added and reacted at room temperature for 24 hours. A mixed solution of water and decyl alcohol (2 parts by volume of water and 1 part by volume of decyl alcohol) was added to the obtained mixture to cause crystallization. The obtained precipitate was collected by filtration, washed with a mixed solution of water and methanol (1 part by volume of water, 1 part by volume of decyl alcohol), and dried under vacuum to give 5.7 g of a pale yellow powder compound (1 〇-a). Yield The benchmark for 2,5-dimethoxyaniline was 53%. (5) Synthesis Example of Compound (10-b) Mixed Compound (10-8) 4.7 Å, 2,4-Bis(4-decyloxyphenyl)-1,3-dithia-2, 4-di 9.2 g of a heterocyclic butadiene-2,4-disulfide (Lawesson's reagent) and 100 g of toluene were placed, and the mixture was heated to 80 ° C to react the resulting mixture for 5 hours. After cooling, it was concentrated to obtain a red viscous solid having a compound (10-b) and a decomposition product of Lawesson's reagent as a main component. (6) Synthesis of compound (10-c) A mixture containing the compound (10-b) obtained in the above item, sodium hydroxide 3. lg and water 50 g were mixed, and the obtained mixture was stirred under ice cooling. Then, an aqueous solution containing 11.94 g of potassium ferricyanide was added under ice cooling to cause a reaction. The reaction was allowed to proceed at room temperature for 24 hours, and the precipitated yellow precipitate was filtered. The precipitate which was collected by filtration was washed with water and then with hexane, and washed with methanol. The yellow powder was added to a solvent of heptane-ethyl acetate 1:1 (volume ratio), stirred at room temperature for 1 hour, and then allowed to stand overnight in an ice bath. The pale yellow powder of 122 321 867 201100410 was collected by filtration, and dried in vacuo to give 2.5 g of pale yellow solid compound (10-c). The yield was 51% based on the compound (10_a). (7) Synthesis Example of Compound (10-c) • Mixed Compound (10-c) 2. 5 g and pyridinium chloride 12·5 g 'The temperature was raised to 1801: The reaction was allowed to proceed for 2 hours. After cooling the obtained mixture, the obtained precipitate was collected by adding water, and washed with water, benzene and then hexane to obtain 1.8 g of a solid having a compound (ΙΟ-d) as a main component. The yield is 77% based on the compound ® (l〇-c) basis. (8) Synthesis example of the compound (A10-1) The compound (10-d): 80 g, the compound (A) 4.92 g, a dimercaptoamine, a base. 0.07g of pyridine and 30ml of gas. To the obtained mixture, under ice cooling, Ν, Ν'-diisopropylcarbodiimide 1.70 g was added. The obtained reaction solution was allowed to react at room temperature overnight, and then concentrated under reduced pressure. The sterol was added to the residue to be crystallized. The crystals were collected by filtration and redissolved in the gas. While stirring, the obtained solution was added with decyl alcohol, and the resulting white precipitate was collected by filtration, washed with ethanol, and recovered by hydrazine column chromatography with chloroform 8 〇v〇1〇/〇_acetone 20 vol%. The first component of winter was concentrated under reduced pressure with an evaporator and then crystallized with cold methanol. The resulting pale yellow powder was collected by filtration and dried to give a white powdery compound (10)-1) 46 () g. The yield was 72% based on the compound (ΙΟ-d). 123 321867 201100410 Compound (A 10 — 1)】—— KTVA-D (Ή 1 \ 义 f

3H). 1. 2 9^1. 3 1 (d 3H T 2 4 7 S^n Q d, 3H, 48 to I 79 (m, 26H), 2. 35 to 4 t 3 2, t: ~2 · 83 扯 5H), 3· 93~3. 9 7 h 4H), 7. 0 2 (m' 8H), 7· 2 (m 2H) 6ΊΓ), 5/ 79~5. 84 (stick 2H), 6. 7~6. 17

Un, 2H), 6.37 to 6.44 (m, 2H), 6.87 3 (m, 3H), 7. 48 to 7.50 (m, 3H) The obtained compound was confirmed by grain observation by a polarizing microscope (A10) -1) Phase transfer temperature. The compound (A1(M) shows a phase with high viscosity from (4) C at the time of temperature rise, at 169. (: shows a clear point. When cooling, it has a clear rib from 167 ° C, and a nematic phase appears at 1Q5t. Crystallization. (Example 5) <Synthesis Example of Compound (Aii_1)>

(A) (1) Synthesis example of 4,6-dimercaptobenzofuran 25 g of 3'5-dimethylphenol was dissolved in N,N,-dimethylacetamide - the solution was cooled by an ice bath Add 9 82g of sodium hydroxide. In. The mixture was mixed with chloroacetaldehyde dimethyl acetal 25.49 g. After 15 hours at 100 C, the reaction solution was added to 1000 ml of water and 400 ml of decyl isobutyl 124 321867 201100410 ketone for liquid separation. The organic layer was recovered, and the organic layer was washed twice with 5 liters of 1N aqueous sodium hydroxide solution, and the organic layer was further washed twice with pure water of 8 〇〇mi. After recovering the organic layer, it was dehydrated with anhydrous sodium sulfate, and the mixture was reduced under reduced pressure with an evaporator to obtain a pale red viscous liquid. Further, 400 g of toluene and orthophosphoric acid 3. 〇ig were mixed and heated. A solution of a pale red viscous liquid dissolved in 100 ml of a solution was dropped into the solution. Take 丨1〇. Stir for 3 hours and then cool to room temperature. The reaction solution was washed twice with a 1 N aqueous sodium hydrogencarbonate solution, and finally washed with 500 ml of purified water. The organic layer was recovered, dried over anhydrous sodium sulfate, concentrated under reduced pressure using an evaporator, and dried in vacuo to give 4,6-dimethylbenzene as a pale red viscous liquid. The yield is 55% based on 3,5-dimethylbenzene. (2) The combination of 2-mercapto- 4,6-dimethyl benzoate • The order of 6-methylbenzopyrene 21. 62g dissolved in N,N,-dimethyl decylamine = 8. 4g. After the solution was cooled by a water bath, it was dripped into a dish to brew a chlorine coffee. Put the powder and the color of the work solution to the temperature of H, and then to ^. (10) Mix 1 () hours. 〇 The anti-remaining was cooled to room temperature, fresh water was added to the ml and allowed to be neutralized for 1 hour, and neutralized with ... acid reflux. After adjusting the pH to 8, dilute with toluene. 6克后过滤。 After the organic layer was added, activated carbon 2. 6g and filtered. The mixture was concentrated under reduced pressure with an evaporator, and the residue was dissolved in chloroform and crystallised from heptane. 5克。 The crystals were collected by filtration, and dried under vacuum to give a pale yellow powder of 2-methylmercaptobenzene and squid 19.5 g. The yield was 4% based on the 4,6-dimercaptobenzofuran standard. (3) 4,6-Dimercaptobenzofuran-2-carboxylic acid, an example of 2-methylmercapto-4,6-dimethylbenzofuran 19.5 g, amine sulfonic acid 13.04 g and 1_ pure water is mixed. Cool in an ice bath and add sodium chlorite 321867 125 201100410 12. 15 g of water in 100 ml of solution. The reaction was carried out in a water bath for 36 hours. To the reaction solution, 100 ml of toluene and 25 g of potassium hydroxide were added to adjust the pH to 12. After liquid separation, the aqueous layer was recovered, and the aqueous layer was further washed with 20 mM of benzene. The aqueous layer was recovered, and the pH was made 2 with 2N-hydrochloric acid, and then toluene was added to 40 mM. The organic layer was collected, dried over anhydrous sodium sulfate, and then evaporated to dryness. The yield was 67% based on 2-carbamimido-4,6-dimercaptobenzofuran. (4) Synthesis of 4,6-dimercaptobenzofuran-2-carboxylic acid

4克。 Distribute 3, 5-dimethylbenzene 15Og, polyformic acid (paraformaldehyde) 230. lg, anhydrous gasification town 175. 4g dispersed in 900ml of acetonitrile. After stirring for 30 minutes in an ice bath, 474 g of triethylamine was added dropwise over two hours. The mixture was allowed to react in a water bath for 8 hours and at room temperature for 14 hours. After adding 1500 ml of cold 5N-hydrochloric acid to the reaction mixture to adjust the acidity, the mixture was partitioned between 400 ml of ethyl acetate to recover an organic layer. The aqueous layer was further partitioned with 400 ml of ethyl acetate. The organic layer was taken up, mixed with the previous organic layer, and then evaporated, and evaporated. The residue was dissolved in 400 ml of toluene, and 3 g of activated carbon and 20 g of silica gel were added thereto, and the mixture was stirred at room temperature for 30 minutes, and filtered. The filtrate was recovered, concentrated under reduced pressure on an evaporator, and dried in vacuo to give &lt;RTIgt;&lt;/RTI&gt; The yield is about 92 ° / for the 3,5-dimethylphenol. . 4, 6-dimethyl salicylaldehyde 45.0 g, potassium carbonate 101. 0 g was dispersed in 126 321867 201100410 Ν, Ν'-dimercaptoacetamide 360 ml. Og。 After adding to ethyl bromoacetate 50. Og. The mixture was allowed to react at 80 ° C for 4 hours. After cooling the reaction mixture to room temperature, 400 ml of decyl isobutyl ketone was added thereto, and the mixture was adjusted to be acidic with 1000 ml of cold 1N-hydrochloric acid, followed by liquid separation. The organic layer was washed 3 times with 1000 ml of pure water, and the organic layer was recovered. After dehydration with anhydrous sodium sulfate, the solvent was distilled off in a distiller. 40 g of potassium hydroxide and 400 ml of ethanol were added to the residue, and the mixture was stirred at 80 ° C for 1 hour. After cooling to room temperature, the solvent was distilled off in a distiller, and 100 mL of pure water was added thereto. After confirming that the pH was 12 or more, the aqueous layer was washed twice with toluene and washed once with gem. The aqueous layer was recovered and neutralized with 4N-sulfuric acid to adjust pH to 3. The precipitated yellow precipitate was filtered, washed with purified water and dried in vacuo to give 4,6-dimethylbenzofuran-2-carboxylic acid as a yellow powder. The yield was 83% based on the 4,6-dimercaptosyl aldehyde. (5) Synthesis of compound (11-a): 2, 5-dimethoxyaniline 11.1 g, 4,6-dimercaptobenzofuran-2-carboxylic acid 14.27 g, triethylamine 7.59义,^'-Dimercaptopyridine pyridine q 1.83g and dehydrated N,N'-dimercaptoacetamide 100.Og. After the obtained solution was cooled in an ice bath, 34.85 g of a BOP reagent was added and reacted at room temperature for 24 hours. A mixed solution of water and decyl alcohol (2 parts by volume of water and 1 part by volume of decyl alcohol) was added to the obtained mixture to cause crystallization. The leaching of the compound (ll-a) 16.2 g was obtained by washing with a mixture of water and decyl alcohol (3 parts by volume of water, 2 parts by volume of methanol). The yield was 66% based on 2,5-dimethoxyaniline. (6) Synthesis Example of Compound (11-b) Mixed Compound (ll-a) 16. 2,4-Bis(4-methoxyphenyl)-127 321867 201100410 1,3-Dithia-2, 4-Di-filled heterocyclic butadiene-butadiene-butadiene (Lawesson, s reagent) 9. 2g and acetaminophen, heated to 8 〇t, and the resulting mixture was reacted for 12 hours. After cooling, it was concentrated to obtain a red viscous solid having a compound (u_b) and a decomposition product of Lawesson, s as a main component. (7) Synthesis Example of Compound (11-c) A mixture containing the compound (11-b) obtained in the above item, 11.8 g of sodium hydroxide and 250 g of water were mixed, and the obtained mixture was reacted under ice cooling. Then, an aqueous solution containing 44.17 g of ferricyanide was added and added under ice cooling to cause a reaction. The reaction was carried out at 6 CTC for 12 hours, and the precipitated yellow precipitate was collected by filtration. The money was taken and then washed in a row and crystallized with toluene. The obtained yellow color was dried under vacuum to give a pale yellow solid (4 g) of compound (1)-c as a main component. The yield is (10) based on the compound (1) (4). (8) Synthesis Example of Compound (11-d) After mixing the compound (1)-chlorinated core, the temperature was raised to reflux for 3 hours. The resulting compound was added to ice, and the resulting precipitate was taken into consideration. After rinsing with water, it was washed with a 4 Λ 本 , , , , , 真空 真空 真空 真空 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 化合物 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率 收率The compound (Hc) is 93 〇 / (9) The synthesis of the compound (All-1) is a mixed compound (ll-d) 3. 00 g, which is incorporated into your product. (A) 8.47 g, dimethylamino group Pyridine 0·12g and gas imitation 40ml.

Add Ν, Ν '_ diisopropylcarbodiimide 2 QA „ .92g to the mixture of π parts, so that the reaction solution is allowed to react to the night after being filtered. Add methanol to crystallize it. Filter and take a &amp; ° in the residue> Check the next day, redissolve in the gas, add 321867 128 201100410 into the 〇.3g of activated carbon, stir at room temperature for 丨 hours After filtering the solution and concentrating the filtrate to 1/3 under reduced pressure in an evaporator, methanol was added while stirring, and the resulting white precipitate was filtered, washed with heptane, and dried in vacuo to give a white powder (A11-1 7. 60g. The yield is 71% of the compound (n_d)*. Compound (A1 1-1)] H-NMR (CDC13) : δ (ρρχη) 1. 45 〜1. 85 (m 24H), 2· 36~2. 87 (m, 18H), 3·93~3· 97 (t, 4H), 4.15 to 4·20 (t, 4Η), 5. 79 to 5. 8 4 (dd, 2H), 6. Ο 7~6. 1, 7 (m, 2 H), 6.37~6.45 (m, 2H), 6.87~7.01 (m, 9H), 7.20 (, s, 1H), 7. 2 3 (s, 2H), 7· 5 3 (s, 1H) ' Obtained by grain observation with a polarizing microscope The phase transition temperature of the compound (A11-1). The compound (A11-1) exhibits a highly viscous intermediate phase from 1 〇 5 to 137 ° C at elevated temperatures. The discrimination of the liquid crystal phase is difficult, but at 137 ° C. The nematic phase is shown in the above. The nematic liquid crystal phase is up to i8 〇 ° c or more, and when it is cooled, the nematic phase is present at 61 ° C to carry out crystallization. (Example 6) <Compound (A15-1) Synthesis Example

(A) (1) Synthesis of 5-fluorobenzofuran-2carboxylic acid 1? 9 321867 201100410 Mixing 5-fluorosalicylide 25g, potassium carbonate 49.32g, and 2-butanone 200g, heating to 80 °C. 5 g of diethyl bromomalonate was added dropwise to the obtained dispersion, and the reaction was carried out at 100 ° C for 24 hours. The obtained red-brown solution was allowed to cool to room temperature, and then washed with pure water and 1 mol/L aqueous potassium carbonate solution. The organic layer was recovered, dried over anhydrous sodium sulfate, and concentrated under reduced pressure using an evaporator. 25 g of potassium hydroxide and 250 ml of ethanol were added to the residue, and the mixture was stirred at 80 ° C for 2 hours. After cooling to room temperature, the ethanol was distilled off in a distiller. The residue was dissolved in 500 ml of pure water and 500 g of ice, and the pH was adjusted to 3 with 2N sulfuric acid. The lavender precipitates were collected by filtration, and further washed with 1000 ml of pure water, and dried in vacuo to give a pale yellow powder of 5-bromobenzidine. The yield was 73% for the 4-fluorosalicylaldehyde benchmark. (g) Ν 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 24 0克。 0- 0. 0g. After the obtained solution was cooled in an ice bath, 51.57 g of a BOP reagent was added and reacted at room temperature for 24 hours. A mixed solution of water and decyl alcohol (2 parts by volume of water and 1 part by volume of decyl alcohol) was added to the obtained mixture to cause crystallization. The resulting precipitate was washed with a mixture of water and decyl alcohol (1 part by volume of water, 1 part by volume of decyl alcohol), and dried in vacuo to give a pale yellow powder of compound (15-a) 32. lg. Yield The basis for 2,5-dimethoxyaniline was 92%. (3) Synthesis of compound (15-b) Compound (15-a) 32. 0g, 2, 4-bis(4-methoxyphenyl)-1,3-dithia-2, 4- Diphosphetane-2,4-disulfide 130 321867 201100410 (Lawesson's reagent) 24. 6g and toluene 320g' were heated to 8{rc and the resulting mixture was allowed to react for 24 hours. After cooling, it was concentrated to obtain a yellow solid which had a compound (15-b) and a decomposition product of Lawesson's reagent as a main component. (4) Synthesis Example of Compound (15-c) A mixture containing the compound (15-b) obtained in the above item, 21.7 g of sodium oxynitride and 500 g of water were mixed, and the obtained mixture was poured under ice cooling. Then, add iron sulphate 81 · 3g to make it react. The reaction was carried out for 2 hours at room temperature. The precipitated yellow precipitate was collected by filtration. The leached precipitate was washed with water and then washed with hexanes (washed with toluene) and dried in vacuo to give a solid yellow solid. The yield was 91% based on the compound (15-a). (5) Synthesis Example of Compound (15-d) • The compound (15-c) was mixed with 〇g and pyridinium chloride 50. Og, and the mixture was heated to 1800 C for 2 hours. After cooling the obtained mixture, water was added thereto, and the obtained precipitate was collected by filtration, washed with water, hexane, and toluene to give a solid &amp; s g as a main component of the hydrazine compound (15-d). The yield was 66% based on the compound (15-c). (6) Synthesis Example of Compound (A15-1) ～ Mixed Compound (15-d) 3.00 g, Compound (A) 8 75 g, dimethylamino group D 唆 0.12 g and chloroform 50 ml. To the obtained mixture, hydrazine, Ν'-diisopropylcarbodiimide 3. 〇 2 g was added under ice cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered over silica gel, and concentrated under reduced pressure. Methanol was added to the residue to cause crystallization. The crystals were collected by filtration and redissolved in chloroform. After adding 0.3 g of activated carbon and stirring for 1 hour, it was filtered. The filtrate was condensed with an evaporator concentration of 131 321867 201100410, and methanol was added to the side of the mixture, and the resulting white sink was collected by filtration. The product was washed with a heptane and dried under vacuum to give a white powdery compound (A15-1) 8.20 g. The yield is Y5% based on the compound (i5 to d). Compound, (A15-1)] H-NMR (CDC13): δ (ppm) 1. 46 〜1. (m 24H) ' 2· 36~2. 84 (m' 12H), 3. 93~3 9 8 (t' 4H), 4〇 (Τ' ~ 4· 20 (t,, 5·80~5. ·84 (dd, 2Η), 6·07~6· 17 (m 2 Η) 6. 37~6· 44 (m, 2Η), 6·87~7· 〇2 (m, 8Η), 7 ΐ4^ , 72 19 (dt, 1Η), 7. 28 (s, 2Η), 7. 33 to 7. 37 (dd, 1Η) 7 50 to 7. 5 5 (in' 2Η) &quot;, /· 5 0 Borrow The phase transition temperature of the obtained compound (A15-1) was confirmed by the grain observation by a polarizing microscope. The discrimination of the phase (liquid crystal phase) of the compound (A15-1) showing a high viscosity from 143 C to 178 C at the time of temperature rise It is very difficult, but it shows a clear nematic phase above 178 ° C, to 2 〇〇. The nematic phase appears above 〇. When the temperature is lowered, it is 'to 11 〇. (: The nematic phase is present and crystallized.) 7) <Synthesis Example of Compound (A57-1)>

(1) Synthesis of 5-propylbenzofuran-2carboxylic acid: 4-propyl salicylate 27·8 g, carbonic acid bell 46. 81 g, tetrabutyl bromide 11.84 g, potassium telluride 30 · 48g and toluene, warmed to 80 ° C. 2,5 g, 18-crown-6 (18-crown-6) 2·8 g of diethyl bromomalonate was added dropwise to the dispersion obtained in 132 321867 201100410, at 110 ° C (at the boiling point of toluene) The reaction was refluxed for 24 hours. The obtained red-brown reaction solution was cooled to room temperature, and then concentrated under reduced pressure using an evaporator. Potassium hydroxide (27. 8 g, ethanol 278 ml) was added to the residue and stirred at 80 ° C for 1 hour. After cooling to room temperature, ethanol was distilled off in a distiller. The residue was dissolved in 500 ml of pure water and 500 g of ice, and the pH was adjusted to 3 with 2N sulfuric acid. The leaching of the yellow precipitate was carried out by filtration, and the mixture was washed with aq. The yield was 17% based on 4-propyl salicylaldehyde. (2) Synthesis of compound (57-a): 2,5-dimethoxyaniline 4. 3 g, 5-propylbenzopyrene-2-slow acid 5.7 §, triethylamine 2.82 bogey ^' - dimethylaminopyridine 0.682 and dehydrated hydrazine, Ν'-dimercaptoacetamide 30. Og. After the obtained solution was cooled in an ice bath, 12.96 g of a BOP reagent was added and reacted at room temperature for 24 hours. A mixed solution of water and methanol (2 parts by volume of water and 1 part by volume of decyl alcohol) was added to the resulting mixture to cause crystallization. The obtained precipitate was collected by filtration, washed with a mixed solution of water and methanol (1 part by volume of water, 1 part by volume of methanol), and vacuum-dried to obtain a compound (57-3) of 6.33 y. The 2,5-dimethoxyaniline standard was 67%. (3) Synthesis of Compound (57-b) Mixed Compound (57-a) 6. 0g, 2, 4-bis(4-methoxyphenyl)-1,3-dithia-2, 4- Two kinds of heterocyclic butadiene-butane-2,4-disulfide (Lawesson's reagent) 9.2 g and toluene 100 g were heated to 80 ° C, and the resulting mixture was reacted for 5 hours. After cooling, it was concentrated to obtain a red viscous solid which had a compound (57-b) and a decomposition product of Lawesson's 133 321867 201100410 as a main component. (4) Synthesis of Compound (57-c) A mixture containing the compound (57-b) obtained in the above item, sodium hydroxide, 4.5 g, and water 5 〇S was mixed, and the obtained mixture was stirred under ice cooling. Then, potassium ferricyanide I6. 8 § was added under ice cooling to cause a reaction. The reaction was carried out for 48 hours at room temperature, and the precipitated yellow precipitate was collected by filtration. The precipitate obtained by filtration was washed with water, then washed with hexane, washed with ethanol, and dried under vacuum to give compound (Μ-e). 28 g of a pale yellow solid as a main component. The yield was 42% based on the compound (57-a). (5) Synthesis Example of Compound (5 [d) 2.7 g of a compound (57-c) and 13.5 g of pyridinium chloride were mixed, and the mixture was heated to 180 ° C to carry out a reaction for 2 hours. After the obtained mixture was cooled, water was added thereto, and the obtained sink was collected by filtration, and washed with water and hexane to obtain 2.4 g of a solid having compound (57-d) as a main component. The yield is 97% based on the compound (57-c). (6) Synthesis of the compound (A57-1) Mixed compound (57-d) 1. 85 g, compound (A) 5. 〇〇g, dimethyl Aminopyridine 0. 07g and gas imitation 20ml. To the obtained mixture, hydrazine, Ν'-diisopropylcarbonyldiimide 1·72 g was added under ice cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered over silica gel, and concentrated under reduced pressure. Methanol was added to the residue to cause crystallization. The crystals were filtered off and redissolved in chloroform. While stirring the obtained solution, methanol was added thereto, and the resulting white precipitate was filtered, washed with hexane, and dried in vacuo to give white powdery compound (A57-1) 3.85 g. The yield was 77% based on the compound (57-d). 321867 134 201100410 1 H-NMR (CDC 1 3 ) of compound (A5 7 - 1): δ (p pm) 0. 9 4~Ο. 9 9 (t, 3H), 1. 4 5~1. 86 ( m, 26H), 2. 3 5~2. 4 7 (m, 8H), 2. 6 7~ 2. 8 3 (m, 6H), 3. 9 2~3. 9 7 (m, 4H), 4. 1 5~4. 2 0 (t, 4H), 5, 79~5. 84 (dd, 2H), 6. 07~6. 17 (xn, 2H), 6. 37~6. 44 (m , 2H), 6. 8 7~7· 0 1 (m, 8H), 7· 2 5 (s, 2H), 7. 4 6-7. 4 9 (m, 4H) by texture with a polarizing microscope The phase transition temperature of the obtained compound (A57-1) was confirmed by observation. Compound (A57-1) exhibits a highly viscous phase from 131 ° C to 143 ° C at elevated temperatures, a clear nematic phase from 143 ° C, and a further nematic phase from compound (A57-1) to above 180 ° C. phase. When the temperature is lowered, a nematic phase is exhibited at 100 ° C to carry out crystallization. (Example 8) <Synthesis Example of Compound (A25-1)>

(1) Synthesis of compound (25-a): 2,5-monodecyloxyaniline 15.8 g, porphin [3, 2-b] porphin-2-carboxylic acid 19·〇g, triethyl 4g, N,N,-dimethylaminopyridine 4.85g and dehydrated N,N-dimethylacetamide 95. 〇g. After the obtained solution was cooled in an ice bath, 47. 9 g of a reagent was added and reacted at room temperature for 24 hours. To the resulting mixture, a mixed solution of water and decyl alcohol (2 parts by volume of water, 1 part by volume of 321321867 135 201100410 alcohol) was added to crystallize. The obtained precipitate was collected by filtration, washed with a mixed solution of water and methanol (1 part by volume of water, 1 part by volume of methanol), and dried under vacuum to give a compound (25-a) 21.0 g of a yellow powder. The yield was 64% based on 2,5-dimethoxyaniline. (2) Synthesis of Compound (25-b) Mixed Compound (25-&amp;) 27. (^, 2,4-bis(4-decyloxyphenyl)-1,3-dithia-2, 4-diphosphetane-2,4-disulfide (Lawesson's reagent) 17.8g and toluene 122g, the temperature was raised to 80 ° C, and the obtained mixture was reacted for 5 hours. Filtration, precipitation after cooling In the hall, a brown solid having a compound (25-b) and a decomposition product of Lawesson's reagent as a main component is obtained. (3) A synthesis example of the compound (25-c) is mixed with the compound (25-b) obtained in the foregoing paragraph. The mixture of the aqueous solution of the aqueous solution of the aqueous solution of the potassium ferrocyanide 70. 7g was added to the reaction under ice cooling to allow the reaction. The reaction was carried out for 12 hours, and the precipitated yellow precipitate was collected by filtration. The precipitate obtained by filtration was washed with water and then washed with hexane, washed with ethanol and vacuum dried to give compound (25-c) as a main component. The yellow solid is 15 g. The yield is 58% based on the compound (25-a). (4) Synthesis of the compound (25-d) Mixed compound (25-c) 15. Og and gasified pyridyl镔75. Og, the temperature was raised to 180 ° C for 3 hours. After the obtained mixture was cooled, water was added, and the obtained sink was taken, washed with water, hot benzene, and hexane to obtain The compound (25-d) as a main component of the solid 6. 6 g. The yield is 136 321867 201100410 (25-c) basis is 45%. (5) Synthesis of compound (A25-1) mixed compound (25- d) 2. Og, compound (A) 5. 76g, dimethylaminopyridine 0. 08g and chloroform 30ml. In the obtained mixture, under ice cooling, add Ν,Ν'-diisopropylcarbonyldiazine The imine was 1.98 g. The reaction solution was allowed to react at room temperature overnight, 0.8 g of activated carbon was added, and after standing overnight, it was filtered with silica gel and concentrated under reduced pressure. Methanol was added to the residue. The crystals were crystallized, and the crystals were collected by filtration and dissolved in chloroform. The obtained lyophile was stirred while adding the decyl alcohol, and the resulting brown precipitate was collected by filtration, washed with ethanol, and dried in vacuo to give a pale brown powder. A25-l) 4. 30g. The yield is 60% based on the compound (25-d). • 1 H-NMR of the compound (A2 5-1) (C DC 1 3 ) : δ (p pm) 1. 2 6~1. 8 7 (m, 2 4H), 2. 33~2. 81 (m, 12H), 3. 92~3. 96 (t, 4H ), 4. 15 • ~ 4. 20 (t, 4H), 5. 79~5. 84 (dd, 2H), 6. 07~6. 17 (m, 2 Η), 6·3 7~6. 4 4 (m, 2 Η), 6. 8 7~7. 0 1 (m, 8 Η), 7. 1 8 (s, 2H), 7. 23 〜 7. 31 (d, 1 Η), 7. 5 2 to 7· 54 (d, 1 Η), 7.82 (s, 1H) The phase transition temperature of the obtained compound (A25-1) was confirmed by pattern observation with a polarizing microscope. The compound (A25-1) exhibited a nematic phase from 175 ° C to 180 ° C at a temperature rise, a nematic phase from 180 ° C to 238 ° C or more, and a clear point at 238 ° C. At the time of cooling, a nematic phase is exhibited at 168 ° C to carry out crystallization. (Example 9) <Synthesis Example of Compound (A41-1)>

(7-b) (41-c) 137 321867 201100410 (1) Synthesis of the compound (4b a) Dimethoxyaniline 35. 4g, triethylamine 46. 7g

6克。 Solid 76. 6g. The yield is 2. 5-. In a container, 2, 5-dimethoxy^ and dehydrated chloroform are mixed, and the reaction is carried out while 50. 〇g. The mixed solution was allowed to warm to 6 Torr.揭 Reveal: layer thickness 'to obtain compound (4i-a) dimethoxy phenamine is 98%. (2) Synthesis Example of Compound (41-b) A solid having a compound (4bb) and a decomposition product of Lawesson,s reagent as a main component was obtained in the same manner as in the synthesis example of the compound U-b). (3) Synthesis example of the compound (41-c) A solid having the compound (41-c) as a main component is obtained in the same manner as in the synthesis of the compound (1-c). (4) Synthesis Example of Compound (41-d) A solid having the compound (41-d) as a main component was obtained in the same manner as in the synthesis of the compound (?-d). (5) Synthesis Example of Compound (A41-1) The compound (A41-1) was obtained in the same manner as in the synthesis of the compound (A1 -1). The yield was 68% based on the compound (41-d). 1 H-NMR (CDC13) of the compound (A4 1-1): δ (ppm) i 44~ 24 Η)' 2. 32 〜2. 64 (m, 12 Η), 3·91 〜3. 97 4 η 4. ι 4 〜4, 20 (t, 4H), 5·79~5. 84 (m, 2H), 6. 07~6. (m 2H) ^ 3 6~6.44 (m, 2H), 6.8 5~7.0 1 (m, 8H), 7.3 7~7 q'n r , 〇u, 8. 13~8· 17 (m, 2H) · 90 (m, 9H), by grain observation with a polarizing microscope The phase transition temperature of the obtained compound 321867 138 201100410 (A41-1) was confirmed. If the temperature is raised, turn around 214 °C to move to the smectic phase. If the temperature is further increased, it changes to the 'nematic phase' near 234 °C. If the temperature is further raised, it changes to an isotropic phase at around 275 °C. When the temperature is lowered from this, it becomes a nematic phase at around 269 ° C, becomes a smectic phase at around 227 ° C, and returns to crystallization near 204 ° C. That is, the compound (A41-1) exhibits a smectic phase from 214 ° C to 234 ° C at a temperature rise, and a nematic phase from 234 ° C to 275 ° C. Further, at the time of temperature lowering, a nematic phase is exhibited from 269 ° C to 227 ° C, and a stratified phase is present from 227 ° C to 204 ° C. (Example 10) <Synthesis Example of Compound (A43-1)> (1) Synthesis Example of Compound (43-d)

In the synthesis example of the compound (41-d), the same is carried out except that the 4-phenylbenzoquinone gas of the starting material is replaced with 4-(4-n-propylphenyl)benzoquinone gas. In the same manner, the compound (43-d) is synthesized in accordance with the above reaction mechanism. (2) Synthesis Example of Compound (A43-1) In the synthesis example of the compound (1-1), the same method is used except that the compound (1-d) of the starting material is changed to the compound (43-d). The compound (A43-1) was obtained. The yield was 65% based on the compound (43-d). 139 321867 201100410 Compound (A4 3- 1) 1 H-Nmr (CDC ΐ3): δ (ppm) 〇. ^~工· 〇l (t, 3H) 1. 44 〜1. 87 (m, 26H)' 2 34 〜2 8 3 (m, 14H), 3 92 〜3 98 (t, 4H), 4. 14~4. 21 (t, 4H), 5. 79~5. 84 (m, 2H), 6 〇7~6.18(m'2H), 6.3 6~6.4 4(m, 2H), 6.8 6~7.〇2(m, 8H)' 7_ 20~7. 31 (m, 4H), 7. 56 ~? 6〇(d, 2H>, 7 6 9~7 7 3 (d, 2H), 8. 07~8. 11 (d, 2H) The obtained compound was confirmed by grain observation by a polarizing microscope (A43- 1) The phase transition temperature of the crystal. If the temperature is raised, it will change to the homogeneous phase near i43 °c. If the temperature is lowered from here, it will return to crystal near U8〇c. It can also be known that the compound (A43-D is not The liquid crystal phase is shown. (Example 11) <Compound Synthesis Example

&lt;A) (1) A synthesis example of the compound (66-a) is mixed with 2,3-dicyanohydroquinone 1 〇. (^, potassium hydroxide 35 〇 2 and water 70. Og while stirring the mixture The mixture was cooled to room temperature, 40.0 g of sulfuric acid was added, and stirring was continued. Ethyl acetate was added to the obtained mixture and stirred, and the organic layer was taken out. The layer was concentrated under reduced pressure, and the solvent was evaporated, and then dried in vacuo to give </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; b) Synthesis Example 321867 140 201100410 Mixed compound (66-a) 10. Og, 2-amino-6-methoxybenzo[3]e 19.1 g and tetrahydromethane 200.0 g, while giving the mixture The mixture was heated to room temperature, and the ruthenium, Ν'-dicyclohexylcarbodiimide 12. 5 g was dissolved in tetrahydrofuran (37 g, and added dropwise at room temperature, ' while stirring The mixture was heated and stirred at 80 ° C for 36 hours. The obtained mixture was allowed to cool to room temperature, and the white precipitate was removed by filtration, and the obtained filtrate was concentrated under reduced pressure to remove solvent. The residue was crystallized, and the resulting pale green powder was filtered and washed with chloroform, and the obtained pale green powder was dissolved in tetrahydrofuran, and methanol was added thereto for crystallization. After filtering the resulting green sink, the reaction was carried out. The compound (66-b) was 2.8 g in vacuo, and the yield was 16% based on the compound (66-a). ' (3) Synthesis of Compound (A66-1) • Mixed Compound (66-b) 2. Lg, 4-dimethylaminopyridine 0. 18g, compound (A) 6.16g, chloroform 123g. Then, in the obtained mixture, it is added dropwise at room temperature to make Ν, Ν'-dicyclohexylcarbonyl 4.56 g of imipenem dissolved in q chloroform 10.7 g of the solution was stirred. After filtering the obtained mixture, 62 g of 2N hydrochloric acid was placed and stirred to separate the liquid, and the organic layer was taken out. After that, the organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated to give the solvent, and the mixture was stirred and evaporated. The resulting precipitate was filtered and dried in vacuo to give compound (A66-l) 4. lg. The rate is 59% based on the compound (66-b). 141 321867 201100410 Compound (A66 1) 1 H-NMR (CDC13): δ (ppm) 丄 12Η), 2. 2 9~2· 5 6 (m, 8Η), 2· 56~2 7 5 (· 4~1. 85 ( m, 3H) '3. 92~3. 97(t, 4H), 4.16~4 丄, 4H), 3.89 (s, 4 (dd, 2H), 6. 07~6· 17 (m, 2H), 6 3 7 , =), 5· 79~5. 8 6~7. 01 (xn, 8H), 7. 08~7· 13 (dd, 1H) 7· ^ 2H)' 6. 8 0~7. 5 2 (m, 2H)' 8· 〇〇 (d, 1H), 'Cd' 1H), 7. 5 The phase transition temperature of the obtained compound (A66-1) was confirmed by grain observation by a polarizing microscope. . The compound (A66-丨) has a γ ratio of 125 Χ from 14 Χ: from 14 (TC shows a highly viscous phase, the liquid crystal phase is difficult to judge, but shows a clear liquid crystal phase above 140 ° C. (Examples 12 to 24) And Comparative Example 1) <Example of the production of the optical film> A 2% by mass aqueous solution of a polyvinyl alcohol (polyethyl hexanhydroxide total %, manufactured by Wako Pure Chemical Industries, Ltd.) was applied to the glass substrate to form a film having a dry thickness of 1 Then, the composition of the surface of the obtained film was subjected to a rubbing treatment, and the composition of the film which had been subjected to the rubbing treatment was dried at the drying temperature shown in Table 2 for 1 minute. '- Warming to the temperature at the time of light irradiation shown in Table 2, the ultraviolet light of the cumulative light amount of _, and =, and forming the light of the film thickness shown in Table 3 321867 142 201100410 [Table 1] The compound of the present invention (%) Liquid crystal compound (%) Polymerization initiator (%) Coating agent (%) Solvent (%) Example 1 2 A1-1 (14.55) Irgacure 8 19 (0.44) BYK3 6 IN (0.01) 85.00 Example 1 3 A5—1 (14.55) — Irgacure 819 (0.44) BYK3 61N (0.01) 85.00 Example 1 4 A6 — 1 (14.55) — Irgacure 8 19 (0. 44) BYK3 6 IN (0.01) 85.00 Example 1 5 A10-1 (14.55) An Irgacure 8 1 9 (0.44) BYK3 61N (0.01) 85.00 Example 1 6 A11-1 (29.10) — Irgacure 819 (0.87) BYK3 6 IN (0.03) 70.00 Example 1 7 A15-1 (14.55) — Irgacure 8 19 (0.44) BYK3 6 IN (0.01) 85.00 Example 1 8 A57-1 (14.55) An Irgacure 8l9 (0.44) BYK3 6 IN ( 0.01) 85.00 Example 1 9 A25-1 (14.55). An Irgacure 8l9 (0.44) BYK3 6 IN (0.01) 85.00 Example 2 0 A11-1 (9.70) LC242 (9.70) Irgacure 819 (0.58) BYK3 61N (0.02 80.00 Example 2 1 A11-1 (11.64) LC242 (7.76) Irgacure 8l9 (0.58) BYK3 6 IN (0.02) 80.00 Example 2 2 A11-1 (13.58) LC242 (5.82) Irgacure 819 (0.58) BYK3 6 IN (0.02) 80.00 Example 2 3 A11-1 (15.52) LC242 (3.88) Irgacure 819 (0.58) BYK3 6 IN (0.02) 80.00 Example 2 4 A11-1 (17.46) LC242 (1.94) Irgacure 8l9 (0.58) BYK3 6 IN (0.02) 80.00 Comparative Example 1 - LC242 (29.04) Irgacure 819 (0.89) BYK3 6 IN (0.09) 69.15 LC242: Liquid crystal compound of the following formula sold by BASF Corporation Q 〇-\ }—{ /=( &gt;—( )-〇,0 LC242 one &gt;~〇-(CH2)4—〇卞^ c^°~(ch2)4_〇h(= Polymerization initiator: Irgacure 819 (manufactured by Ciba Japan Co., Ltd.: acid phosphine oxide compound) 143 321867 201100410 Coating agent · BYK361N (manufactured by BYK Japan) Solvent: cyclopentanone [Table 2] Drying temperature after coating Light accumulated by issu (mJ/cm2) Example 1 2 150eC ----- 140° 〇-— 2400 Example 1 3 1453⁄4 UO^ 2400 Example 1 4 22〇°C ------___ 2l〇°〇........ 2400 Example 1 5 22〇°C —— 15〇°〇2400 Example 1 6 140°C 80°〇2400 Example 1 7 220°C X65°C 2400 Example 1 8 175°C 110°C 2400 Example 1 9 2203⁄4 135°C 2400 Example 2 0 110 ° C 80 ° C 2400 Example 2 1 115 ° C 80 ° C 2400 Example 2 2 U5 ° C 80 ° C 2400 Example 2 31 120 ° C 80 ° C 2400 Example 2 4 120 ° C 80 ° C 2400 Comparative Example 1 45 ° C Room temperature 1200 <Measurement of optical characteristics> The front retardation value of the optical film was measured using a measuring machine (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.). Further, the glass substrate used for the substrate has no birefringence. Therefore, the film of the glass substrate is measured by a measuring machine, and the front surface difference value of the optical film produced on the glass substrate can be obtained. The optical phase difference obtained by the measurement was measured at wavelengths of 447.3 nm, 546.9 nm, and 627.8 nm, and [Re(447. 3;)/Re (546. 9)] was calculated as α. And [Re(627. 8)/Re(546. 9)] (as ^. Also, using a laser microscope (LEXT, manufactured by Olympus), the film thickness d (β iq) of the optical film must be determined. Not shown in Table 3. The Δ π system calculates the value of 9) 321867 144 201100410 by the film thickness (^11=1^(546. 9)/d). [table 3]

Re(546.9) a β d (um) Δη Example 1 2 142.5 0.923 1.016 2.431 0.059 Example 1 3 117.2 0.857 1.030 1.588 0.074 Example 1 4 106.5 0.844 1.036 1.519 0.070 Example 1 5 102.9 0.887 1.024 1.741 0.059 Example 1 6 155.5 0.805 1.043 2.635 0.059 Example 1 7 121.2 0.903 1.023 1.581 0.077 Example 1 8 84.1 0.914 1.017 1.707 0.049 Example 1 9 111.8 0.800 1.037 1.670 0.067 Example 2 0 105.4 1.007 0.989 1.086 0.097 Example 2 1 99.4 0.988 0.989 1.113 0.089 Example 2 2 97.3 0.963 1.000 1.150 0.085 Example 2 3 90.3 0.930 1.008 1.187 0.076 Example 2 4 80.1 0.887 1.018 1.189 0.067 Comparative Example 1 141.0 1.075 0.978 1.001 0.141

(Example 25) <Synthesis Example-2 of Compound (A11-1)>

(a) (1) 4,6-dimercaptobenzophenone sigma-2-carboxylic acid synthesis Example 4,6-dimercapto-salt 146. 6g, potassium carbonate 330. 7g dispersed in 145 321867 201100410 1\1,? ^'-Dimethylacetamide 70 () 1111. After heating to 80 ° (:, 30 ml of butyl bromoacetate was added dropwise for 30 minutes. The mixture was reacted at 130 ° C for 2 hours. After cooling the reaction solution to room temperature, thiol isobutyl ketone was added. 600 ml, and the organic layer was washed twice with pure water of 100 Om1, and the organic layer was further washed twice with 100 ml of pure water. After dehydration with anhydrous sodium sulfate, the solvent was removed by an evaporator to dissolve the residue in acetic acid 240 g. 72 g of an aqueous solution of hydrogen desert acid was added, and the mixture was stirred at 40 ° C for 1 hour. After cooling to room temperature, 150 g of IN-hydrochloric acid was added, and the precipitated white powder was collected by filtration. The obtained white powder was further washed with 1 N hydrochloric acid. After drying, it was dried by vacuum to give a yellow powder of 4,6-dimethylbenzofuran-2-carboxylic acid (81. 7 g). The yield was 44% based on 4,6-dimethyl salicylaldehyde. 2克。 Og and chloroform 400. Og. With ice, the synthesis of the compound (11-a) is mixed with 2, 5-dimethoxyaniline 96. 6g, 4,6-dimercaptobenzofuran-2-carboxylic acid 80. Og and chloroform 400. Og. After cooling the obtained suspension in a bath, a mixture of 1-ethyl-3-(3-dimethylaminodiyl) dimethylimine hydrochloride 88.7 g and 300 g of chloroform was added to the chamber for 4 hours. Warm response 48 small The obtained mixture was concentrated, and a mixed solution of 1 N-hydrochloric acid and decyl alcohol (2 parts by volume of water and 1 part by volume of methanol) was added thereto to cause crystallization. The obtained precipitate was collected by filtration, and a mixed solution of water and decyl alcohol was added ( 2 parts by volume of water and 1 part by volume of decyl alcohol. The precipitated pale yellow precipitate was collected by filtration, washed with a water-methanol mixture (2 parts by volume of water, 1 part by volume of methanol), and dried in vacuo to give a pale yellow powder. Compound (11-a) 124. 2 g. The yield is 91% based on 4,6-dimethylbenzofuran-2-carboxylic acid. (3) Synthesis of compound (11-b) 146 321867 201100410 Mixed compound (11-8) 123.0 bogey, 2,4-bis(4-methoxyphenyl)-'1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent) 9. 2g and 1200g of toluene, heated to 110 ° C, the resulting mixture was reacted for 8 hours. After cooling to room temperature, it was separated from 1N-aqueous sodium hydroxide solution. The organic layer was recovered and added. 2克。 The yield of the fresh yellow powder with the compound (Ub) as a main component 109. 2g. The yield is obtained by the filtration of the yellow precipitate. The compound (11-a) has a basis of 85%. ^ (4) Synthesis of compound (11-c) The compound (11-b) 60.0, sodium hydroxide 53.8 g and water 100 g are mixed, and the obtained mixture is ice-cooled. After stirring, potassium ferricyanide, 133. Og, and methanol 51 g were added to make a reaction. The reaction was carried out for 36 hours at room temperature, and the precipitated yellow precipitate was collected by filtration. The precipitate obtained by filtration was washed with a mixed solution of heptane and toluene (3 parts by volume of heptane, 1 part by volume of toluene), and the obtained yellow powder was dried in vacuo to give compound (11-c) as a main component. Yellow q solid 51.3g. The yield was 86% based on the compound (11-b). (5) Synthesis of compound (11-d) The compound (ll-c) 40. Og and pyridinium chloride 400. Og were heated to 180 ° C for 3 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. After rinsing with water, the mixture was washed with toluene and dried in vacuo to give 36.6 g of a yellow solid compound (U-d) as a main component. The yield was 99% based on the compound (11-c). (6) Synthesis of compound (A11-1) Mixed compound (U-d) 35. Og, compound (A) 98. 8 g, dimercaptoamine 147 321867 201100410 Pyridine 1.37 g and toluene 700 ml. To the resulting mixture was added N, Ν'-dicyclohexylcarbonyldiimide 55 6 g under ice cooling. The resulting reaction solution was allowed to react at room temperature overnight, filtered over silica gel, and concentrated under reduced pressure. Methanol was added to the residue/inspection for crystallization. The crystals were collected by filtration, redissolved in chloroform, and 2. 3 g of activated carbon was added thereto, and stirred at room temperature for several hours. The solution was filtered, and the filtrate was concentrated to 1/3 under reduced pressure in an evaporator, and then the mixture was stirred and filtered, and the white precipitate formed was filtered, washed with heptane, and dried in vacuo to give a white powder (All-1) ) 74. 5g. The yield was 60% based on the compound (ΙΙ-d). (Example 26) <Synthesis Example-3 of the compound (A11-1)> The same procedure as in the synthesis example-2 of the compound (A11-1) except that the ethyl bromoacetate was used instead of the butyl bromoacetate. Compound (A-11) was synthesized. (Example 27) <Synthesis Example of Compound (A61-1)>

321867 148 201100410 (1) Synthesis of 3,6-dimethyl salicylaldehyde 50 g of 2,5-dimethylphenol, 30. 7 g of polyoxymethylene, and anhydrous magnesium chloride 58. 4 g were dispersed in 500 ml of tetrahydrofuran. After stirring for 30 minutes in an ice bath, 82.83 g of triethylamine was added dropwise over two hours. When the mixture was reacted in a water bath for 8 hours, it was reacted at room temperature for 120 hours. After adding 1500 ml of cold 5N-hydrochloric acid to the reaction mixture to make it acidic, it was extracted twice with 400 ml of ethyl acetate to collect an organic layer. After the organic layer was dried over anhydrous sodium sulfate, it was filtered over Celite, and the filtrate was concentrated under reduced pressure at 40 ° C under an evaporator. The residue was dissolved in 100 ml of hydrazine, and 600 ml of heptane was added to the solution. 30 g of tannin was added to the solution and stirred for 1 hour, followed by filtration. 5克。 The filtrate was concentrated under reduced pressure, and the heptane was added to the residue, and the heptane was evaporated to give a yellow liquid. The yield is 2,5-didecylphenol group. The standard is 17%. (2) Synthesis of 4,7-dimercaptobenzopyrene-2-carboic acid 10.8 g of 3,6-dimethylhydrazine, 23.63 g of carbonic acid dispersed in q N,Ν' - Dimercaptoacetamide in 70 ml. After heating to 80 ° C, 13.61 g of tributyl bromoacetate was added dropwise over 10 minutes. The mixture was reacted at 130 ° C for 3 hours. After cooling the reaction mixture to room temperature, 200 ml of decyl isobutyl ketone was added, and the mixture was separated into 1000 ml of pure water. Further, the organic layer was washed twice with 300 ml of pure water, and the organic layer was recovered. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 40 g of acetic acid, and 8 g of an aqueous solution of hydrogen desert acid was added thereto, followed by stirring at 40 ° C for 1 hour. After cooling to room temperature, 10 g of IN-hydrochloric acid was added, and the precipitated white powder was collected by filtration. The obtained white powder was further washed with 1N-hydrochloric acid water, then washed with heptane, and dried in vacuo to give white 149 321 867 201100410 color powder of 4,7-dimethylbenzo-fol-2- Rebel acid 7. 31 g. The yield was 55% based on 3,6-dimercapto salicylaldehyde. (3) Synthesis of compound (61-a): 2, 5-dimethoxyaniline 8. 82 g, 4,7-dimercaptobenzofuran-2-carboxylic acid 7. 30 g and 38 g of gas. After the ice bath was cooled in an ice bath, 4-ethyl-3-(3-didecylaminopropyl) succinic acid imide hydrochloride was added over a period of 4 hours. The mixture was reacted at room temperature for 24 hours. Further, 1.18 g of 2,5-dimethoxyaniline was added to the reaction solution and allowed to react for 48 hours. The obtained mixture was concentrated, and a mixed solution of 1N-hydrochloric acid and methanol (2 parts by volume of hydrochloric acid and 1 part by volume of methanol) was added to the residue, and 400 g of heptane was added and crystallized. The obtained sink was collected by filtration, and a mixed solution of hydrochloric acid-sterol (2 parts by volume of hydrochloric acid and 1 part by volume of methanol) was added. The precipitated pale yellow-green precipitate was collected by filtration, and further washed with a water-sterol mixed solution (2 parts by volume of water and 1 part by volume of decyl alcohol). The obtained pale yellow-green precipitate was washed with a mixed solution of 1N-K0H aqueous solution-decyl alcohol (1 part by volume of a potassium hydroxide aqueous solution and 2 parts by volume of methanol), and then washed with 150 g of water and then filtered. The compound (61-a) 8.82 g was obtained as a pale yellow powder. The yield was 71% based on 4,7-dimethylbenzofuran-2-carboxylic acid. (4) Synthesis of Compound (61-b) Mixed Compound (61-8) 8.822, 2,4-bis(4-methoxyphenyl)-1,3-dithia-2, 4-diplex Heterocyclic Dingxuan-2,4-disulfide (Lawesson's reagent) 6.58 g and toluene 88 g, and the mixture was heated to 110 ° C to react the resulting mixture for 12 hours. After cooling, the precipitated orange solid was removed by filtration, and heptane was added to the filtrate to be crystallized. Filtration of the precipitated yellow 150 321867 201100410 color precipitate, dried by vacuum to obtain a bright yellow powder of the compound (61-b) ‘ 4. 7 g. The yield was 51% based on the compound (61-a). (5) Synthesis Example of Compound (61-c) Compound (61-b) 4.27, potassium hydroxide 3.83 g and water 73 g were mixed, and the obtained mixture was allowed to react under ice cooling. Then, 11.23 g of potassium ferricyanide was added under ice cooling, and then 15 g of decyl alcohol was added to cause a reaction. After reacting for 12 hours at room temperature, the precipitated yellow precipitate was collected by filtration. The precipitate thus obtained was washed with water, methanol and ethanol, and a pale yellow precipitate was collected by filtration. The light yellow solid 3. 0g of the compound (61-c) as a main component was obtained. The yield was 73% based on the compound (61-a). (6) Synthesis example of the compound (61-d): The compound (61-c) was mixed with 0.8 g and the chlorinated β 唆镔 15.4 g, and the mixture was heated to 190 ° C for 7 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. After rinsing with water, the mixture was washed with benzene, and dried in vacuo to give 2.41 g of yel. Yield q The compound (61-c) was 85% based on the standard. (7) Synthesis of compound (A61-1): Compound (61-d): 2.41 g, compound (A): 6.80 g, dimethylamino group, 0. 09 g, and chloroform (38 ml). To the resulting mixture was added hydrazine, Ν'-diisopropylcarbodiimide 2.34 g under ice cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered over silica gel, and concentrated under reduced pressure. In the residue, sterol is added to crystallize it. The crystals were collected by filtration, redissolved in chloroform, and activated carbon of 0. After filtering the solution and concentrating the filtrate to 1/3 under reduced pressure in an evaporator, a 151 321867 201100410 alcohol was added while stirring vigorously, and the resulting white precipitate was collected by filtration, washed with heptane, and dried in vacuo to give an off-white powder. Compound (A61_1) 4 52 g. The yield was 53% based on the compound (61-d). 2^Γ(26 (Tl3) :8(ppm) Χ· 82(- ～4 2 0 “ Λ: 18Η), 3· 92~3. 97 (t' 4Η)' 15 • j.u, 4Η), 5. 80~5. 84 (dd, 2Η), 6. 07~6 18 im 2 13、二·2Γ6 74 = 4(Π;' 2H); 6. 87 ～7. 〇2 (m' 8H) ' 7·2~7. (m, 2 Η), 7. 2 4 (s, 2 Η), 7. 5 7 (s, 1 Η) The obtained compound was confirmed by grain observation by a polarizing microscope (相61-1) Phase transition temperature. Compound (aw-d shows a high viscosity phase from 136 ° at 138 °C, from 138. (: Get a clear nematic phase. Further compound (A61 - 1) A nematic phase is present at a temperature of 150 ° C or higher. When the temperature is lowered, a nematic phase is present at 90 ° C to carry out crystallization. (Example 28) <Synthesis Example of Compound (A69-1)>

(a) 152 321867 201100410 (1) Synthesis of 3-cyclohexyl-6-methyl salicylaldehyde. 2~ cyclohexyl-5-nonylphenol i〇〇g, polyacetal 39.5 g, anhydrous • chlorine Huazhen 75. 〇g is dispersed in 900 ml of tetrahydrofuran. 4克。 After stirring in an ice bath for 30 minutes. The mixture was allowed to react in a water bath for 8 hours at a temperature of 96 hours. After adding cold 5N-hydrochloric acid 150 〇mi to the reaction mixture to make it acidic, it was extracted twice with ethyl acetate of 4 〇〇mi to collect the organic layer. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40 C. The residue was dissolved in 1 〇〇mi, and 600 ml of heptane was added to the solution. After 38 g of tannin was added to the solution, the solvent was removed by an evaporator. After heptane was added to the residue for extraction, heptane was distilled off, and yttrium was slowly crystallized to obtain a yellow crystal of 4,6-dimethyl salicylaldehyde 35-2 g. The yield was 31% based on 2-cyclohexyl-5-methylphenol. (2) 4_Mercapto-7-cyclohexylbenzofuran-2-carboxylic acid, 3-cyclohexyl-6-methyl salicylaldehyde 35. 〇g, potassium carbonate 72. 2g dispersed in N' N, dimethyl dimethyl acetamide in 300 ml. After the temperature was increased to 80 ° C, the third butyl bromoacetate was added dropwise 41.6 g. The mixture was reacted for 3 hours at 13 (TC). After cooling the reaction mixture to room temperature, 2 ml of methyl isobutyl ketone was added, and the mixture was separated by 1000 ml of pure water. Further washed with 5 ffll of pure water. The organic layer was collected twice, and the organic layer was collected, dried over anhydrous sodium sulfate, and then evaporated to the solvent. The residue was dissolved in 240 g of acetic acid, and 72 g of aqueous hydrobromic acid solution was added thereto, and stirred at 4 ° C for 1 hour. After cooling to room temperature, the precipitated white powder was collected by adding 1N-hydrazine hydrochloride 5〇2, and the obtained white powder was further washed with 1N hydrochloric acid, then washed with g-hexane and dried by vacuum. White powder of 4-mercapto-7-cyclohexylbenzofuran-2-carboxylic acid 25. 8 g. Yield 153 321867 201100410 3-cyclohexyl-6-methyl salicylaldehyde benchmark is 59%. (3) The singularity of the compound (69-a) is 2,5-didecyloxyaniline 22. 2 g, 4-mercapto-7-cyclohexylbenzofuran-2-carboxylic acid 25. 00 g, triethylamine 9.79 g 4克与。 After the suspension was stirred in an ice bath, the addition of 1-ethyl-3-(3-dimethylaminopropyl) carbonyl diimine hydrochloride hydrochloride 20. 4g and Mix of chloroform 100g The mixture was reacted at room temperature for 72 hours. The obtained mixture was concentrated, and a mixture of 1N-hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol) was added to the residue, and 400 g of heptane was added thereto to crystallize it. The precipitate obtained was collected by filtration, and a mixed solution of hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of methanol) was added, and the precipitated pale yellow-green precipitate was collected by filtration to obtain a mixed solution of water and methanol. 2 parts by volume, 1 part by volume of methanol, and further washed. The obtained pale yellow-green precipitate was washed with a mixed solution of 1N-K0H aqueous solution-sterol (1 part by volume of potassium hydroxide aqueous solution, 2 parts by volume of decyl alcohol). Then, it was washed with 150 g of decyl alcohol, and then filtered, and dried under vacuum to give 12.3 g of compound (69-a) as a pale yellow powder. The yield was based on 4-mercapto-7-cyclohexylbenzofuran-2-carboxylic acid. 32%. (4) Synthesis of compound (69-b) Mixed compound (69-a) 12. 3g, 2, 4-bis(4-decyloxyphenyl)-1,3-dithia- 2, 4-diphosphetane-2,4-disulfide (Lawesson's reagent) 7. 6g and terpene 120g, heated to 110 ° C, the resulting mixture was reacted for 6 hours After cooling, the benzene solution was washed three times with a 2N-aqueous sodium hydroxide solution of 50 mM, and then the organic layer was recovered and concentrated, then heptane was added and the solvent was further distilled off with an evaporator. sterol 50 g 154 321 867 was added to the residue. 5 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The yield was 90% based on the compound (69-a). (5) Synthesis Example of Compound (69-c) The compound (69-b) obtained by the above-mentioned compound was mixed with 5 g, potassium hydroxide (yield: 58) and 182 g of water, and the obtained mixture was allowed to react under ice cooling. Then, 28.09 g of potassium ferricyanide was added to prepare a dispersion containing the compound (69-b). 40 g of methanol was added to the dispersion and reacted at 40 ° C for 2 hours, and the mixture was reacted at room temperature for 24 hours, and the precipitated yellow precipitate was collected by filtration. The precipitate which was collected by filtration was washed with water and then with hexane. Further, it was dispersed in 400 ml of a mixed solution of toluene-heptane (1 part by volume of toluene and 2 parts by weight of heptane) to recover a pale yellow insoluble component. 5克。 Light yellow solid as a main component of the compound (69-c) 4. 5g. The yield was 36% based on the compound (69-a). (6) Synthesis Example of Compound (69-d) q The compound (69-c) was mixed with 54.54 g of a chlorination ratio of 45.4 g, and the mixture was heated to 180 ° C for 3 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. 4克。 After washing with water, the benzene was washed with benzene, and dried in vacuo to give a compound (69-d) as a main component of the gram yellow solid 3. 4g. The yield was 80% based on the compound (69-c). (7) Synthesis of compound (A69_1) 3.40 g of a compound (69-d), 7.87 g of a compound (A), and a dimethylamine group σ are 0.1 ml and 40 ml of a gas. To the resulting mixture was added Ν, Ν'-diisopropylcarbodiimide 2.71 g under ice cooling. The resulting reaction solution was obtained. 155 321867 201100410 The reaction was carried out at room temperature - overnight, after the transition to qing, concentrated under reduced pressure. The sterol is added to the residue and hydrazine to be crystallized. The crystals were collected by filtration and redissolved in chloroform.: 3 g of activated carbon was added at room temperature (hours. The transition solution and (iv) liquid were concentrated to 1/3 under reduced pressure in an evaporator, and then methanol was added while stirring. The white precipitate formed was collected by filtration, washed with heptane, and dried in vacuo to give 4.48 g of compound (A69-1) as an off-white powder. The yield was 45% based on the compound. (A69-l)t η-匪R (CDci3): s (ppm) 丄ay 34H), 2. 34~2. 54 (m, 11H), 2. 65~2. 85 (m' 4H). i (T, n 20 (t, 4 6. 3 7~6. 7· 56 (s, ~3· Μ (tt, 1H), 3.92~3. 97 (t, 4H), 4 15"H), 3. 1〇H), 5.79 ~5.84(dd, 2H), 6.07~6.17(m'2H) 2H) 4 4 (m, 2H), 6.86 to 7.14 (m, 1 Ο H), 7. 2 5 ( s 1H) The phase transition temperature of the obtained compound (A69-1) was confirmed by the grain observation by a polarizing microscope. The compound (A69-1) showed a highly viscous phase at 2 〇 7 ° C at a temperature rise, and was carried out at 220 ° C. Thermal polymerization. (Example 29) <Synthesis Example of Compound (A70-1)>

(A) (1) Synthesis example of 3-propyl water emulsion 156 321867 201100410 75 g of 2-propylphenol, 71.3 g of polyfluorene, and 78.7 g of anhydrous magnesium chloride were dispersed in 900 ml of tetrahydrocyanate. 5克。 After the ice bath was stirred for a few minutes, the amount of triethylamine was added dropwise. The mixture was allowed to react in hydrazine for 8 hours and at room temperature for 96 hours. After adding 5 N-hydrochloric acid 15 〇〇mi' to the reaction mixture to adjust the acidity, the mixture was extracted twice with 40 ml of ethyl acetate, and the organic layer was collected. After the organic layer was dehydrated with anhydrous sodium sulfate, the evaporator was at 40. (The following concentration is concentrated under reduced pressure. The residue is dissolved in 100 ml of hydrazine.) 600 ml of heptane is added to the solution. 90 g of yttrium gum is added to the solution, and the solvent is removed by an evaporator. Gengxuan is added to the residue for extraction. The yield of 2-propyl salicylic acid was 28. 8 g. The yield of 2-propylbenzene was 32%. (2) Synthesis of 7-propyl benzofuran-2-carboxylic acid For example, a 3-propyl water emulsion chain 28·8 g and a potassium carbonate 59.3 g were dispersed in 200 ml of n N,~dimethylacetamide. After heating to 8 (TC, the bromoacetic acid was added dropwise for 3 minutes. Tributyl ester 34. The mixture was reacted for 2 hours at 13 (rc). After cooling the reaction solution to room temperature, decyl isobutyl _ 2 〇〇 ml was added, and the mixture was partitioned with pure water 0 1000 ml to further 500 ml. The organic layer was washed twice with pure water, and the organic layer was collected. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 150 g of acetic acid, and 45 g of aqueous hydrobromic acid solution was added thereto, and the mixture was stirred at 4 Torr for 1 hour. After cooling to room temperature, 15 g of shame hydrochloric acid was added, and the precipitated white powder was collected by filtration. The obtained white powder was washed with acid water, and then washed. After washing with heptane, it was dried in vacuo to give a white powder of 7-propylbenzofuran-2-carboxylic acid 28. lg. The yield was 78% based on the 3 propyl water. (3) Compound ( Synthetic example of 7〇-a) 321867 157 201100410 2,5-dimethoxyaniline 20, 25 g, 7-propyl benzophenone ° Nan-2-remediation 18. Og, triethylamine 8. 92g dispersion 6克与chloroform。 After adding the suspension of the resulting solution in an ice bath, the reaction was carried out for 4 hours, adding 1-ethyl-3-(3-didecylaminopropyl) carbonyl diimide hydrochloride 18.6 g and chloroform 100 g of the mixture was reacted at room temperature for 72 hours. The obtained mixture was concentrated, and a mixture of 1N-hydrochloric acid and methanol (2 parts by volume of hydrochloric acid, 1 part by volume of methanol) 400 g and 150 g of heptane were added to the residue to be crystallized. The precipitate obtained was collected by filtration, and a mixed solution of hydrochloric acid and methanol was added (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol). A pale yellow-green precipitate was collected by filtration, and a mixed solution of 1N-K0H aqueous solution-sterol was used. 8克份。 7-volume of potassium hydroxide aqueous solution, 1 part by volume of methanol, and the filtrate was filtered, and dried in vacuo to give a pale yellow powder of the compound (70-a) 19. 8g. The furan-2-carboxylic acid standard is 66%. (4) Synthesis of compound (70-b) Mixed compound (70-&amp;) 19.82, 2,4-bis(4-methoxyphenyl)-1 3-dithia-2,4-di-filled butylene 2,4-disulfide (Lawesson's reagent) 14.2g and phenylbenzene 198g, heated to 110 ° C, the resulting mixture was reacted for 6 hours After cooling, the toluene solution was washed three times with 500 ml of a 2N-aqueous sodium hydroxide solution, and then the organic layer was collected, concentrated, and then heptane was added to crystallize. 6克。 The fresh yellow crystals were obtained by filtration. The yield was 90 ° / 〇 based on the compound (70-a). (5) Synthesis example of the compound (70-c) 18.6 g of a compound (7〇-b), 17.86 g of water and 33 g of water were mixed, and the obtained mixture was allowed to react under ice cooling. Then, 52.41 g of potassium nitrate was added to the ferric cyanide 158 321867 201100410 to prepare a dispersion containing the compound (70-b). 70 g of methanol was added to the dispersion and reacted at 40 ° C for 2 hours, and reacted at room temperature for 24 hours, and the precipitated yellow precipitate was collected by filtration. The precipitate which was collected by filtration was washed with water and then with methanol. The yellow powder was further washed with hot ethanol and filtered. The obtained yellow powder was dried in vacuo to give 15.8 g of pale yellow solid compound (70-c). The yield was 76% based on the compound (70-a). (6) Synthesis example of the compound (70-d) 15.8 g of the compound (70-c) and 158 g of a π chlorination ratio were mixed, and the mixture was heated to 180 ° C for 3 hours. The obtained mixture was added to ice, and the obtained precipitate was filtered, washed with water, washed with toluene, and dried in vacuo to give 13.6 g of a solid yellow solid compound (70-d). The yield ' is 94% based on the compound (70-c). (7) Synthesis of compound (A70-1) Mixed compound (70-d) 5. 00 g, compound (A) 13. 5 g, dimethylamino group β is determined by β = 0.19 g and chloroform 60 ml. To the obtained mixture was added Ν, Ν'-diisopropylcarbodiimide 4.65 g under ice cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered over silica gel, and concentrated under reduced pressure. The sterol was added to the residue to be crystallized. The crystals were collected by filtration, redissolved in chloroform, and 0.3 g of activated carbon was added and stirred at room temperature for 1 hour. After filtering the solution and concentrating the filtrate to 1/3 under reduced pressure in an evaporator, methanol was added to the mixture, and the resulting white precipitate was filtered, washed with heptane, and dried in vacuo to give a white powder (A70-l) ) 8. 38g. The yield was 48% based on the compound (70-d). 159 321867 201100410 3H) 1 45^1. 84 (m. 26H) , 2. 34^2. 48 (m. 8H) ; 2 6^: 2. 71 (m, 4H), 2. 94 to 3. 00 (t, 2H), 3.92 to 3.97 (t 4H) 17 7. 2 (I:, 4"0, 4H), 5. 79~5· 84 (仏2H), 6. 〇7 2 6 (m, 2H), 6' 36~6. 44 (m, 2H), 6. 87~6. 98 (m. 2~7. 2 4 (m, 4H), 7·52~7. 53 (m, 2H) 8H) The phase transition temperature of the obtained compound (A70-1) was confirmed by pattern observation by a polarizing microscope. The compound (Moq) showed a highly viscous phase from 137 C to 142 C at a temperature rise, and a clear nematic phase was obtained from 142 °C. Further, the compound (A70-1) is in the form of 22 (TC or more exhibits a nematic phase, and when it reaches a nematic phase, it undergoes crystallization. ^ (Examples 30 to 33 and Comparative Example 1) <Manufacture of optical film Example: A 2% by mass aqueous solution of polyvinyl alcohol (polyethylene glycol 1 〇〇〇 〇〇〇 Γ Γ Γ Γ Γ 制 制 制 ) ) ) ) ) , , , , , , , , , , , , 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The surface of the obtained film: = After the surface of the rubbing treatment was applied by spin coating, Table 4 was dried, and the resultant 'dryed at the drying temperature shown in Table 5 for 1 minute. The temperature at the time of light irradiation described in Table 5, the side surface of the film, the film of the film, the amount of the outer line, and (4) the film thickness of the film shown in Table 6 321867 160 201100410 [Table 4] The compound of the present invention (%) Liquid crystal compound (%) Polymerization initiator (%) Coating agent (%) Solvent (%) Example 3 0 A61-1 (19.40) - Irgacure 819 (0.58) BYK3 6 IN (0.02) 80.00 Example 3 1 A70-1 (19.40) — Irgacure 8 19 (0.58) BYK3 61N (0.02) 80.00 Example 3 2 A69-1 (4.85) B1-1 (14.55) Irgacure 819 (0.58) BYK3 6 IN (0.02) 80.00 Example 3 3 A69-1 (9.70) Bl-1 (9.70) Irgacure 8 19 (0.58) BYK3 6 IN (0.02) 80.00 Comparative Example 1 One LC242 (29.04) Irgacure 819 (0.89) BYK3 6 IN (0.09) 69.15

Bl-1 : a liquid crystal compound represented by formula (Bl-1)

(B1-1) LC242: the same polymerization initiator as above: Irgacure 819 (manufactured by Ciba Japan Co., Ltd.: Q acid phosphine oxide compound) Coating agent: BYK361N (manufactured by BYK Japan) Solvent: cyclopentanone [Table 5 The temperature cumulative light amount (mJ/cm2) at the time of drying the light after application. Example 3 0 150 ° C 110 ° C 2400 Example 3 1 150 ° C 95 ° C 1200 Example 3 2 180 ° C 150 ° C 2400 Example 3 3 195 ° C 185 ° C 2400 Comparative Example 1 45 ° C Room temperature 1200 161 321867 201100410 <Measurement of optical characteristics> Optical film was measured using a measuring machine (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.) The positive phase difference. Further, since the glass substrate used for the substrate has no birefringence, the film of the glass substrate is measured by a measuring machine, and the front retardation value of the optical film produced on the glass substrate can be obtained. The optical phase difference obtained by the measurement was measured at wavelengths of 447.3 nm, 546.9 nm, and 627.8 nm, and [Re(447. 3)/Re (546·9)] was calculated as α. And [Re(627.8)/Re(546.9)] (as stone). Further, the film thickness d (Mm) of the optical film was measured using a laser microscope (LEXT, manufactured by Olympus Co., Ltd.). The results are shown in Table 6. The value of Δη system Re (546. 9) was calculated by dividing the film thickness (Δη=ί^(546. 9)/d). [Table 6] ------ . - Implementation of the body 丨 q η α β d (//m) Δη Example 3 1 _84.5 0.888 1.017 1.186 0.071 95.0 0.873 1.025 1.279 0.071 Gong Shi Example 3 2 __98. 3 0.956 1.002 1.160 0.086 Polymerization Example 3 3 Comparative Example 1 0.938 1.006 1.087 0.067 141.0 1.075 0.978 1.001 0.141 (Examples 34 to 39 and Comparative Examples 2 to 7) <Thermal physical properties of the composition> <Modulation of the composition> Modulation table Composition of the composition of 7. 162 321867 201100410 [Table 7] Compound (%) of the present invention Liquid crystal compound (%) Polymerization initiator (%) Coating agent (%) Solvent (%) Example 3 4 A11-1 (14.6) B5-1 ( 4.9) Irgacure 819 (0.6) BYK3 6 IN (0.02) 79.88 Example 3 5 A11-1 (14.6) B11-1 (4.9) Irgacure 8ι9 (0.6) BYK3 61N (0.02) 79.88 Example 3 6 A11-1 (14.6 B1-1 (4.9) Irgacure 8 19 (0.6) BYK3 6 IN (0.02) 79.88 Example 3 7 A11-1 (14.6) B2-1 (4.9) Irgacure 8 19 (0.6) BYK3 6 IN (0.02) 79.88 Implementation Example 3 8 A11-1 (14.6) B9-1 (4.9) Irgacure 8l9 (0.6) BYK3 6 IN (0.02) 79.88 Example 3 9 A11-1 (14.6) C1-1 (4.9) Irgacure 8l9 (0.6) BYK3 6 IN (0.02) 79.88 Comparative Example 2 A B5-1 (19.5) Irgacure 819 (0.6) BYK3 61N (0.02) 79.88 Comparative Example 3 - B11-1 (19.5) Irgacure 8l9 (0.6) BYK3 6 IN (0.02) 79.88 Comparative Example 4 — B1-1 (19.5) Irgacure 8l9 (0.6) BYK3 6 IN (0.02) 79.88 Comparative Example 5 A B2-1 (19.5) Irgacure 8l9 (0.6) BYK3 6 IN (0.02) 79.88 Comparative Example 6 - B9-1 ( 19.5) Irgacure 8l9 (0.6) BYK3 6 IN (0.02) 79.88 Comparative Example 7 - C1-1 (19.5) Irgacure 8 19 (0.6 ) BYK3 6 IN (0.02) 79.88 Polymerization initiator: Irgacure 819 (manufactured by Ciba Japan Co., Ltd.: fluorenylphosphine oxide compound) Coating agent: BYK361N (manufactured by BYK Japan) Solvent: cyclopentanone (thermal property observation) The glass substrate was coated with a 2% by mass aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 completely saponified, manufactured by Wako Pure Chemical Industries, Ltd.) ADD 163 321867 201100410 After heat drying, a film having a thickness of 89 nm was formed. The surface of the diaphragm is subjected to rubbing treatment to form an oriented film. The composition of the composition of Table 8 was coated by spin coating on the surface on which the rubbing treatment was carried out. The coated substrate was heated using a polarizing microscope (heating station, LTS 350, manufactured by Linkam, polarized light microscope: BX-51, manufactured by Olympus Co., Ltd.) equipped with a heating stage, and heated at a temperature rising rate of 30 ° C /min. While observing the behavior of the composition. Observe the behavior with natural cooling when cooling down. The results are shown in Table 8. [Table 8] shows the temperature range of the single-domain structure Te~TbCC) or ～(7)) When cooling at the temperature rise T. Tb Tb Tc Example 3 4 74t: 1501 1503⁄4 4QX: Example 3 5 124t: 160*C 160 ^ 36 ° C Example 3 6 ΊΊΧ: 160^160t: 35X: Example 3 7 76*C 160t: 160t: 38t: Example 3 8 ΊΤΟ 160*0 160t: 39*C Example 3 9 Ί2Χ: 150^ 1501 40X: Comparative Example 2 loot: 1S0X: 180t: 80X: Comparative Example 3 180T: 190t: 190^: 165^C Comparative Example 4 120t: 180^: 180^ 100^: Comparative Example 5 160t: 180t: 1801^ 145 ^ Comparative Example 6 125t: 140^140V ΙΟδΧ: Comparative Example 7 120^: 150t: m°c 100X:

Ta: the temperature at which the single-domain structure begins to form from the crystalline phase to the nematic phase; Tb. The temperature of the nematic phase is maintained at a south temperature,

Tc: Temperature of crystallization <Production example of the film sheet> 164 321867 201100410 A 2% by mass aqueous solution of polyvinyl alcohol (polyvinyl alcohol 1000 completely saponified, manufactured by Wako Pure Chemical Industries, Ltd.) was applied to the glass substrate, and * After heat drying, a film having a thickness of 89 nm was formed. The surface of the diaphragm is subjected to rubbing treatment to form an oriented film. The composition described in Table 7 was applied by spin coating on the surface on which the rubbing treatment was carried out, and dried at the temperature (Td) shown in Table 9 for 1 minute. After leaving at a temperature (Te) shown in Table 9, the film was irradiated with ultraviolet rays having an accumulated light amount of 2400 mJ/cm2 to form a film. Here, Te is a temperature required for producing a uniform film in a single domain reproducibility without crystallizing the liquid crystal, and the lower the Te, the more the optical film can be produced at a lower temperature. [Table 9]

Td Te Example 3 4 loot: 70V Example 3 5 130t: 70X: Example 3 6 ιοον 70V Example 3 7 loot: 70X: Example 3 8 loot: 70 ° C Example 3 9 loot: 70 ° C Comparison Example 2 not: 80V Comparative Example 3 180V 165X: Comparative Example 4 not: 80X: Comparative Example 5 120t: 90V Comparative Example 6 1451 120V Comparative Example 7 120t: 100Ϊ: (Example 40) <Synthesis of Compound (A71-1) Example 165 321867 201100410

(A) (1) Synthesis example of 5-chloro-4,6-dimercaptosyl aldehyde: 100 g of 4-chloro-3, 5-dimercaptophenol, 47.94 g of polyfurfural, anhydrous magnesium hydride 91. 19g was dispersed in 800 ml of acetonitrile. After stirring for 30 minutes in an ice bath, 129.23 g of triethylamine was added dropwise over two hours. The mixture was allowed to react in a water bath for 3 hours and at 50 ° C for 18 hours. After adding 5N-hydrochloric acid to the reaction mixture to make it acidic, it was extracted twice with 600 ml of ethyl acetate, and the organic layer was collected. After the organic layer was dehydrated with anhydrous sodium sulfate, 3 g of activated carbon was added and stirred, and then filtered over celite, and the filtrate was concentrated under reduced pressure at 40 ° C or less. After adding 1000 ml of heptane to the residue, the insoluble matter was removed by filtration. The 00 g of 5-chloro-4,6-dimethyl salicylaldehyde (20 g) was obtained as a pale yellow powder. The yield was 17% based on 4-chloro-3,5-dimethylphenol. (2) Dispersion of 5-chloro-4,6-dimethyl salicylaldehyde 20. 00 g, potassium carbonate 36. 68 g dispersion of 5-chloro-4,6-dimethylbenzofuran-2-carboxylic acid In the Ν, Ν '- dimethyl acetamide 150ml. After heating to 80 ° C, the flower was added to the third butyl bromoacetate 21.13 g at 10 166 321 867 201100410 minutes. The mixture was allowed to react at 130 ° C for 3 hours. After cooling the reaction mixture to room temperature, methyl isobutyl ketone 200 m 1 was added, and the mixture was separated by pure water of 10 0 Om 1 . Further, the organic layer was washed twice with pure water of 30 O1, and the organic layer was recovered. After dehydration with anhydrous sodium sulfate, the solvent was removed with an evaporator. The residue was dissolved in 6Og of acetic acid, and 2Og of trifluoroacetic acid was added thereto, followed by stirring at 60 ° C for 1 hour. After cooling to room temperature, 10 g of IN-hydrochloric acid water was added, and the precipitated white powder was collected by filtration. The obtained white powder was further washed with 1N-hydrochloric acid water, then washed with heptane and dried in vacuo to give 5-chloro-4,6-dimethylbenzofuran-2- as a white powder. The acid is 19.37g. The yield is 80% based on 5-chloro-4,6-dimercaptosylamine. (00) 00g dispersed in the synthesis of the compound (71-a) of 2, 5-didecyloxyaniline 19. 43g, 5-chloro-4,6-dimercaptobenzofuran-2-carboxylic acid 19. 00g Chloroform 200g. After cooling the obtained suspension in an ice bath, a mixture of 17.64 g of chloroform and 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbonyldiimide hydrochloride was added over 6 hours. Anti-q at room temperature should be 24 hours. Further, 0.2 g of 2, didecyloxyaniline was added to the reaction solution and allowed to react for 48 hours. The obtained mixture was concentrated, and 400 g of a mixed solution of 1N-hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of methanol) was added to the residue to be crystallized. The obtained pale yellow powder was washed with decyl alcohol, then washed with toluene and then filtered. The compound (71-8) 13.632 was obtained as a pale yellow powder. The yield was 45% based on the 5-chloro-4,6-dimethylbenzofuran-2-carboxylic acid standard. (4) Synthesis of Compound (71-b) Mixed Compound (71-a) 13. 63 g, 2, 4-bis(4-methoxyphenyl)-167 321867 201100410 1,3-Dithia-2 4-diphosphetane-2,4-disulfide (Lawesson's reagent) 9.19 g and toluene 150 g, the temperature was raised to 110 ° C, and the resulting mixture was reacted for 6 hours. After cooling, a 1 N-aqueous sodium hydroxide solution was added. The organic layer was recovered, and 100 ml of heptane was added to crystallize it. The red crystals were taken and dried to give an orange powder compound (71-b) 14.24 g. Although impurities from Lawesson's reagents are mixed in, they are still used directly in the next stage. (5) Synthesis Example of Compound (71-c) Compound (71-b) 14. 24. Potassium hydroxide 11.60 g and water 220 g, and the obtained mixture was reacted under ice cooling. Then, 34.03 g of potassium ferricyanide was added under ice cooling, and then 44 g of methanol was added to cause a reaction. The reaction was carried out at room temperature for 12 hours and at 80 ° C for 8 hours. The precipitated pale yellow precipitate was collected by filtration. The precipitate collected by filtration was washed with water, methanol, and ethanol, and the pale yellow chamber was filtered. The pale yellow powder obtained was dried under vacuum to give 10.3 g of pale yellow solid compound (71-c). The yield was 73% based on the compound (71-a) and the second stage. (6) Synthesis Example of Compound (71-d) 100 g of a compound (71-c) and 100 g of pyridinium chloride were mixed, and the mixture was heated to 190 ° C for 2 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. After rinsing with water, the mixture was washed with benzene and chloroform, and dried in vacuo to give 7.20 g of a yellow solid compound (71-d). The yield was 78% based on the compound (71-c). (7) Synthesis of compound (A71-1) Mixed compound (7 b) l. 00 g, compound (A) 2. 54 g, dimethylamine 168 321867 201100410 pyridine 0.24 g and 40 ml. To the resulting mixture was added N, Ν'-diisopropylcarbodiimide 〇.88 g under ice cooling. The obtained reaction solution was allowed to react at room temperature overnight, filtered over celite, and concentrated under reduced pressure. Ethanol was added to the residue to cause crystallization. The crystals were collected by filtration, redissolved in a gas mixture, and 0.3 g of activated carbon was added thereto, and stirred at room temperature for a few hours. The solution was filtered, and the filtrate was concentrated to 1/3 under reduced pressure in an evaporator. &lt;&quot;&quot;&quot;&quot;&quot;&quot;&quot;&&&&&&&&&&&&&&&&&&&& g. The yield was 78% based on the compound ^ (7 b d). Compound (A7 1-1)] h-NMR (CDCl3): δ(ρριη) [ 4 5^ 8 5 24Η) ' 2· 35~2· 85 (m, 18Η), 3·93~3· 98 ( t,4Η) 4 ], ~4. 20 (t, 4H), 5. 8 0~5. 84 (dd, 2H), 6· Ο 7~6. 18 (m ί&gt; Η), 6 · 3 7 ~6 · 4 4 (χη, 22), 6. 8 7 ~ 7. Ο 1 (m' 8 Η), 7 2 5 (, s 1Η), 7. 32 (s, 1Η), 7· 52 (d, 1Η) 5 The phase transition temperature of the obtained compound (A71-1) was confirmed by pattern observation with a polarizing microscope. Compound (A71-1) was heated from 148. (: to 154 ° C shows a highly viscous phase, a clear nematic phase is obtained from i54 ° C. Ο Further compound (A71-1) is up to 16 〇. (: The above appears nematic phase, when cooling, to The nematic phase was crystallized at 127 ° C. (Example 41) <Synthesis Example of Compound (A21-1)> 321867 169 201100410 〇〇〇H Me.-*"NH2

OMe

OH

a: OMe (21-c) (21-d)

Unακ^ι ^O-CeHu-O-Q-O COOH^ ^ 〇. cc6h12o-Q-o

Q

N^S 〕 only ^η〇^0^&gt;·0 CeHir V (A21-1) (1) Synthesis of compound (21-a) 2.2 g of 2,5-dimethoxyaniline, benzothiazole 00 g of carboxylic acid was dispersed in a gas-like l〇〇g. After cooling the obtained suspension in an ice bath, a mixture of 11.77 g and 70 g of a mixture of 1-ethyl-3-(3-didecylaminopropyl) succinimide hydrochloride was added for 4 hours. , react at room temperature for 24 hours. Further, 0.5 g of 2,5-dimethoxyaniline was added to the reaction solution and allowed to react for 48 hours. The obtained mixture was concentrated, and a mixed solution of 1N-hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol) was added to the residue, and 40 g of a mixture of hexane and 150 g of hexane was added to crystallize. The obtained sink was collected by filtration, and a mixed solution of hydrochloric acid and methanol (2 parts by volume of hydrochloric acid and 1 part by volume of methanol) was added. The precipitated fresh yellow precipitate was collected by filtration, and further washed with a water-methanol mixture (2 parts by volume of water and 1 part by volume of methanol). The fresh yellow precipitate thus obtained was washed with a mixed solution of 1N-K0H aqueous solution/decyl alcohol (1 part by volume of a potassium hydroxide aqueous solution and 2 parts by volume of methanol), and then washed with 150 g of water and then filtered. The compound (21-a) 8.47 g was obtained as a yellow powder. The yield was 48% based on the benzothiazole-2-carboxylic acid standard. 170 321867 201100410 (2) Synthesis of compound (21-b) Mixed compound (21-a) 8. 47g, 2, 4-bis(4-methoxyphenyl)-1,3-dithia-2 4-diphosphetane-2,4-disulfide (Lawesson's reagent) 6.54 g and toluene 85 g, and the mixture was heated to 110 ° C to react the resulting mixture for 6 hours. After cooling, a 1 N-aqueous sodium hydroxide solution was added. The organic layer was recovered, and 10 mmol of heptane was added to crystallize it. The orange crystals were collected by filtration and dried under vacuum to give a compound (21-b) as a pale yellow powder. Although impurities from Lawesson's reagents are mixed in, they are still used directly in the next stage. (3) Synthesis example of the compound (21-c) 8.90 g of the compound (21-b), 8.25 g of hydrogen chloride, and 156 g of water, and the obtained mixture was allowed to react under ice cooling. Then, iron (potassium cyanide) 24.19 g was added under ice cooling, and then methanol (3Og) was added to cause a reaction. The reaction was carried out at room temperature for 12 hours, and at 50 ° C for 12 hours, and the precipitated pale yellow precipitate was collected by filtration. The precipitate which was collected by filtration was washed with water, methanol, and ethanol, and a pale yellow precipitate was collected by filtration. The pale yellow powder obtained was dried under vacuum to give 7.40 g of pale yellow solid compound (21-c). The yield was 84% based on the compound (21-a). (4) Synthesis Example of Compound (21-d) The compound (21-c) was mixed with 00 g of 00 g and chlorinated π to 105 g, and the mixture was heated to 190 ° C for 3 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. After rinsing with water, it was washed with benzene, and dried under vacuum to give 6.00 g of a yellow solid compound (21-d) as a main component. The yield was 94% based on the compound (21-c). 171 321867 201100410 (5) Synthesis of compound (A21 -1) Mixed compound (21-d) 1. 00 g, compound (A) 2. 93 g, dimethylaminopyridine 0.04 g and 50 ml. To the obtained mixture, N,N '-isopropyl-indenyl imine was introduced under ice cooling, and the reaction solution was allowed to react at room temperature overnight, filtered over Celite, and concentrated under reduced pressure. Methanol was added to the residue to cause crystallization. The crystals were collected by filtration, redissolved in a gas mixture, and 0.3 g of activated carbon was added and stirred at room temperature for 1 hour. After filtration and solution, the fish liquid was concentrated to 1 / 3 under reduced pressure in an evaporator, and methanol was added while stirring vigorously, and the resulting white precipitate was collected by filtration, washed with heptane and dried in vacuo to give a white powder (A21). -l) 2.70g. The yield was 74% based on the compound (21-d). ^21^1^1 H~NMR (CDC13): 6 (ppm) 1. 4 5-1 8 3 (m = 4H), 2.32~2.50 (ni, 8H), 2, 62~2.84 (m, 4H) 2 5 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. (t, 4H), 5. 80~5. 8 4 (dd 2H)~ ?76' 1 8 (m, 2H), 6·3 7~6. 4 4 (m, 2H), 6. 8 7~ 7 ί) 3 (m, 8 0 0 uTTh) 3«2 (2d' 2H) ' 7- 5〇^7· 59 (- 2H) 7· 00 (dd, 1H), 8. 14~8. 17 ( Dd, 1H) The phase transition temperature of the obtained compound (A21-1) was confirmed by pattern observation with a polarizing microscope. Compound-1) showed a highly viscous phase from 137 ° 〇 to 155 ° C at elevated temperature, and a clear nematic phase was obtained from 155 ° C. Further, the compound (A21-1) is in the range of Π0Χ: the nematic phase is present above, and is 121 when the temperature is lowered. (: The nematic phase was crystallized. (Examples 42 to 43 and Comparative Example 1) <Production Example of Optical Film Sheet> Polyvinyl alcohol (polyvinyl alcohol 1 〇〇〇 fully saponified bismuth) was applied to a glass substrate. 2% by mass aqueous solution of Wako Pure Chemical Industries Co., Ltd., dry Ί 2 321867 201100410 After drying, a film having a thickness of 89 nm is formed. Then, the surface of the obtained film is subjected to rubbing treatment, and rubbing treatment has been carried out. On the other hand, the composition of the composition of Table 10 was applied by spin coating, and dried at the drying temperature shown in Table 11 for 1 minute. Then, while heating to the temperature at the time of light irradiation shown in Table 11, the table 11 was irradiated. The ultraviolet light having a cumulative amount of light was formed to form an optical film having a film thickness as described in Table 12. [Table 10] 实施 Example 4 2 Example 4 3 Comparative Example 1 Compound of the present invention (%> A71-1 (19.40) A21- 1 (19.40) Liquid crystal compound (%) Polymerization initiator (%)

Irgacure 819 (0.58) Coating agent (%) BYK3 6 IN (0.02) Solvent (%) 80.00 LC242 (29.04)

Irgacure 819 (0.58) Irgacure 8ι9 (0.89) BYK3 6 IN (0.02) BYK3 61N (0.09) 80.00 69.15 LC242 : Same polymerization initiator as above: Irgacure 819 (manufactured by Ciba Japan Co., Ltd.: fluorenylphosphine oxide compound) ❹ Coating agent: BYK361N (manufactured by BYK Japan) Solvent: cyclopentanone [Table 11] Drying temperature after coating j&quot; Example 4 2 Example 4 3 160 ° C 165 ° C Comparative Example 1 45 ° C < Optical characteristics Measurement] 7200 7200 1200 Light measurement measuring machine (K0BRA-WR, front phase difference of Wang Xue film), and measurement of glass substrate system used for substrate 321867 173 201100410 No birefringence Therefore, the film of the glass substrate is measured by a measuring machine, and the front surface difference value of the optical film produced on the glass substrate can be obtained. The optical phase difference obtained by the measurement is measured at wavelengths of 45. 9 nm, 549.4 nra, and 627.8 nm, and [Re(450. 9)/Re (549.4)] (as 0:) and [1^(;627.8)/{^(549.4)] (as cold). Further, the film thickness d (/zm) of the optical film was measured using a laser microscope (LEXT, manufactured by Olympus Co., Ltd.). The results are shown in Table 12. The value of Δη Re (549.4) is calculated by dividing the thickness by Δ n = Re (549. 4) / d). [Table 12]

Re(549.4) a β d (fjtm) Δη Example 4 2 75.0 0.811 1.039 1.150 0.060 Example 4 3 112.0 0.858 1.030 1.546 0.072 Comparative Example 1 141.0 1.075 0.978 1.001 0.141 Examples 12 to 24, Examples 30 to 33, and The optical film systems of Examples 42 to 43 [Re (447.3) / Re (546.9)] (the values in the table are 1 or less. Further, [Re (627.8) / Re (546.9)] (Table /5) The value is 1 or more. That is, the wavelength dependence of the refractive index indicates the so-called inverse wavelength dispersion property, so that the same polarization conversion can be performed in a wide wide-band region. If the diaphragm of the embodiment is used for a liquid crystal panel Further, from the examples 2A to 24 and the examples 32 to 33, it is understood that only the compound of the present invention is mixed with the liquid crystal compound, and the wavelength dispersion property can be freely controlled from the positive wavelength dispersion to the reverse wavelength dispersion. Further, if Examples 34 to 39 and Comparative Examples 2 to 7 were compared, it was found that by mixing the compound of the present invention with a liquid crystal compound, the temperature of the single domain structure 174 321867 201100410 was shifted to the low temperature side, and the optical film could be produced at a lower temperature. Diaphragm. (Examples 44 to 45) <Light Production Example of Membrane> In the same manner as in Examples 42 to 43 and Comparative Example 1, the composition of the composition shown in Table 13 was applied by spin coating, and dried at 140 ° C for 1 minute, and then heated at 80 ° C. An optical film was formed by irradiating ultraviolet rays having an accumulated light amount of 2400 mJ/cm 2 . The results are shown in Table 14. [Table 13] Compound (%) of the present invention Liquid crystal compound (%) Polymerization initiator (%) Coating agent (%) Solvent (%) Example 4 4 ΑΠ-1 (21.79) B1-1 (5.45) Irgacure 3 6 9 (1.90) BYK3 6 IN (0.02) 70.84 Example 4 5 A11-1 (21.79) B1-1 (5.45 Irgacure 819 (0.89) BYK3 6 IN (0.02) 71.85 . Polymerization initiator: Irgacure 369 (manufactured by Ciba Japan Co., Ltd.: acetonitrile compound)

Irgacure 819 (manufactured by Ciba Japan Co., Ltd.: ^ mercapto phosphine oxide compound)

U Coating agent: BYK361N (manufactured by BYK Japan) Solvent: cyclopentanone [Table 14]

Re(549.4) a β d (//m) Δη Example 4 4 147.0 0.891 1.016 2.380 0.062 Example 4 5 143.6 0.876 1.021 2.251 0.064 <Heat resistance test of optical film> The results obtained in Example 44 and Example 45 were obtained. The optical film was kept in an oven at a temperature of 85 ° C and a humidity of 0% for 1 hour, and subjected to a heat resistance test. 175 321867 201100410 The optical characteristics before and after the test were measured, and further, the value of the α value after the test minus the value of the α value of the initial value was taken as the amount of change Δα. When Δα is -0.2 or more and +0.2, the change in optical characteristics can be judged to be small. The results are shown in Table 15. [Table 15]

Re(549.4) α 0 Δ α Example 4 4 Initial value 147.0 0.891 1.016 0.06 After test 144.7 0.885 1.018 Example 4 5 Initial value 149.2 0.876 1.021 -0.001 143.8 after test 0.875 1.021 <Damp heat resistance test of optical film> The optical film obtained in Example 44 and Example 45 was kept in an oven at a temperature of 60 ° C and a humidity of 90% for 1,000 hours, and subjected to a moist heat resistance test. The optical characteristics before and after the test were measured, and the value of the α value after the test minus the α value of the initial value was used as the amount of change Δα. When Δ α is -〇. 2 or more + 0.2 or less, it can be judged that the change in optical characteristics is small. The results are shown in Table 16. [Table 16]

Re(549.4) a β Δ α Example 4 4 Initial value 151.7 0.891 1.016 -0.014 After test 150.0 0.905 1.012 Example 4 5 Initial value 143.6 0.876 1.021 -0.100 After test 103.4 0.976 0.994 As shown in Table 15 and Table 16, It is understood that the optical film of the present invention exhibits good heat and moisture heat resistance in a heat resistance test and a heat and humidity resistance test in which Δα is −0.2 or more and +0.2 or less. Further, as shown in Table 16, it was found that the optical film of Example 44 showed a smaller Δα in the heat and humidity resistance. Therefore, when an acetophenone compound was used as a polymerization initiator, it further showed good heat and humidity resistance. Sex, that is, good fortune. 176 321867 201100410 (Example 46) <Synthesis Example of Compound (A72-1)> j^0H —- y^Z〇 —► ' y^y-c〇°»

(72-*) MeO

^η12-ο-〇,Κ&gt;{ (A72-1) (1) Synthesis of 4, 5, 6-trimethylsaponin 1 to 3, 4, 5-trimethylbenzene, 10.0Og, 5. 51 g of polyfluorene and 10.49 g of anhydrous magnesium 'magnesium were dispersed in 60 ml of acetonitrile. After stirring in an ice bath for 30 minutes, 14.86 g of triethylamine was added dropwise over two hours. The mixture was reacted at 50 ° C for 8 hours and allowed to react at room temperature for 24 hours. After 400 ml of ethyl acetate and 100 ml of pure water were added to the reaction mixture, 1N-hydrochloric acid was added to adjust the acidity, and the organic layer was collected. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure at 40 °C using an evaporator. The residue was purified by a column chromatography using ethyl acetate and heptane (1:3 by volume) as a solvent to give a yellow powder of 4,5,6-trimethyl salicylaldehyde 8.10 g. The yield was 67% based on 3,4,5-trimethylphenol. (2) 4,5,6-trimethylbenzopyrene-2 - a combination of oxo-acids, 4,5,6-trimethylhydrazine aldehyde 8.10 g, potassium carbonate 16.36 g dispersed in hydrazine, Ν '- Dimercaptoacetamide 50ml. After heating to 80 ° C, 30 minutes 177 321867 201100410 dropwise addition of butyl bromoacetate 9.62g. The mixture was reacted at 135 ° C for 2 hours. After cooling the reaction mixture to room temperature, 200 ml of decyl isobutyl ketone was added, followed by filtration. The filtrate was recovered and separated from 1000 ml of pure water. Further, the organic layer was washed twice with 500 ml of pure water, and the organic layer was recovered. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 150 g of acetic acid, and 45 g of an aqueous hydrobromic acid solution was added thereto, followed by stirring at 40 ° C for 1 hour. After cooling to room temperature, 150 g of 1N-hydrochloric acid water was added, and the precipitated pale red powder was collected by filtration. The obtained pale red powder was further washed with 1N-hydrochloric acid water, then washed with benzene, and dried by vacuum to give a pale red powder of 4,5,6-trimercaptobenzofuran-2-carboxylic acid. 6. 34g. The yield was 63% on the basis of 4,5,6-trimethyl salicylaldehyde. (3) Synthesis of compound (72-a): 2, 5-dimethoxyaniline 7.13g, 4, 5, 6-trimethylbenzofuran-2-carboxylic acid 6. 34g dispersed in gas 30g. After cooling the obtained suspension in an ice bath, a mixture of 1.55 g and 100 g of chloroform was added to the mixture of 1-ethyl-3-(3-didecylaminopropyl) carbodiimide hydrochloride for 4 hours. , reacted at room temperature for 48 hours. The obtained mixture was concentrated under reduced pressure, and a mixture of 1N-hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol) was added to the residue to crystallize it. The obtained precipitate was collected by filtration, and a mixed solution of hydrochloric acid and methanol (2 parts by volume of hydrochloric acid and 1 part by volume of methanol) was added. The pale orange precipitate was collected by filtration, washed with a mixed solution of 1N-K0H aqueous solution and decyl alcohol (1 part by volume of aqueous potassium hydroxide solution, 2 parts by volume of decyl alcohol), and then filtered. The compound (72-a) was obtained as a pale yellow powder (yield: 9.39 g). The yield was 89% based on 4,5,6-trimercaptobenzofuran-2-carboxylic acid. (4) Synthesis Example of Compound (72-b) 178 321867 201100410 Mixed Compound (72-a) 9. 39g, 2, 4-bis(4-methoxyphenyl)-'1,3-dithia- 2,4-Diphosphetane-2,4-disulfide (Lawesson's reagent) 6.71 g and 95 g of toluene, and the mixture was heated to 1 i ° ° C to react the resulting mixture for 4 hours. After cooling, 500 ml of a 2N-aqueous sodium hydroxide solution and 1 g of heptane were added to the toluene solution, and the precipitated yellow crystals were collected by filtration. The obtained precipitate was further washed with a heptane and a 2N-aqueous sodium hydroxide solution, and dried in vacuo to give a pale yellow powder compound (72-b) 9.83 g. Although compound (72-b) contains 3% of the Lewiss's drug, it is still used directly in the next stage. (5) Synthesis Example of Compound (72-c) 9.83 g of compound (72-b), 8.47 g of potassium hydroxide and 400 g of water were mixed, and the obtained mixture was allowed to react under ice cooling. Then, 24.84 g of iron potassium cyanide was added under ice cooling to prepare a dispersion containing the compound (72-b). 70 g of decyl alcohol was added to the dispersion, and the mixture was reacted at 60 ° C for 48 hours, and the precipitated yellow precipitate was collected by filtration. The precipitate which was collected by filtration was washed with water and then washed with methanol. Q The yellow powder was further recrystallized from hot toluene. The resulting pale yellow crystals were collected by filtration and dried in vacuo to give a pale yellow solid (4, 60 g). The yield was 47% based on the compound (72-a). (6) Synthesis Example of Compound (72-d) The compound (72-c) was mixed with 60 g of 4 g of 60 g of chloropyridinium chloride, and the mixture was heated to 180 ° C for 3 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. l 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。. The yield was 97% based on the compound (72-c). 179 321867 201100410 (7) Synthesis of compound (A 7 2 _ 1) Mixed compound (72-d) l·10 g, compound (A) 2.97 g, dimercaptoaminopyridine 0.04 g and gas imitation 20 ml, hydrazine Benzene 20ml. To the obtained mixture, N, Ν'-diisopropylcarbodiimide 1. 〇 2 g was added under ice cooling. The resulting reaction solution was allowed to react at room temperature overnight. 4 g of chopped rubber and 200 mg of activated carbon were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour, and then filtered over Celite, and the filtrate was concentrated under reduced pressure. After the gas imitation was removed, decyl alcohol was added to the solution to cause crystallization. The off-white powder was filtered, washed with ethanol twice, then washed with heptane and dried in vacuo to give the compound (A72-1) 2. 95 g. The yield was 78% based on the compound (72-d). Compound (A72-1)] H-NMR (CDC13): δ (ppm) 1. 45 〜1. 84 (m, 24 Η), 2. 27~2. 50 (m, 17 Η), 2. 62~2 · 84 (m, 4Η), 3. 9 3~3. 97 (t, 4H), 4, 16~4· 20 (t, 4H), 5. 79~5. 84 (dd, 2H) '6.07~ 6.17 (m, 2H), 6.37~6.45 (m, 2H), 6.87~7 • 02 (m, 8H), 7. 22~7. 23 (2s, 3H) ' 7·. 54 (s' 1H) The phase transition temperature of the obtained compound (A72-1) was confirmed by grain observation by a polarizing microscope. The compound (A72_1;) exhibits a highly viscous phase from 136 ° (: to 148 ° C) from 148. (: a clear nematic phase is obtained. Further compound (A72-1) is 170 to 170. A nematic phase is present, and a nematic phase is present at a temperature of 120 ° C to carry out crystallization. (Example 47) <Synthesis Example of Compound (A73-1)> 180 321867 201100410

(1) Synthesis of 6-methylbenzoxan-2-pyreic acid. 4-methyl salicylaldehyde 20. Og, potassium carbonate 48. 73g dispersed in hydrazine, Ν'-dimethylacetamide In 100ml. After heating to 70 ° C, 28. 65 g of tributyl bromoacetate was added dropwise over 30 minutes. The mixture was reacted at 135 ° C for 2 hours. After cooling the reaction mixture to room temperature, 200 ml of methyl isobutyl ketone was added, and the mixture was separated into 1000 ml of pure water. Further, the organic layer was washed twice with 500 ml of pure water, and the organic layer was recovered. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 150 g of acetic acid, and 45 g of a hydrobromic acid aqueous solution was added thereto, followed by stirring at 40 ° C for 1 hour. After cooling to room temperature, 150 g of 1N-hydrochloric acid was added, and the precipitated white powder was filtered. The white powder obtained was further washed with 1 N-hydrochloric acid, and then washed with hexanes and toluene, and then dried in vacuo to give a white powder of 6-methylbenzofuran-2-carboxylic acid 20.58 g. The yield is based on the 4-mercapto-water salicylaldehyde standard of 80 ° / 〇. (2) Synthesis of compound (73-a): 2, 5-dimethoxyaniline 26.9 g, 6-methylbenzofuran-2-181 321867 201100410 Carboxylic acid 20.00 g and chloroform 100 g. After cooling the obtained suspension in an ice bath, a mixture of 23.94 g of pethylethyl-3-(3-didecylaminopropyl)carbonyldiamine imide hydrochloride and 120 g of a gas mixture was added for 4 hours at room temperature. Reaction for 48 hours. The obtained mixture was concentrated, and 400 g of a mixed solution of 1N-hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol) was added to the residue to be crystallized. The obtained precipitate was collected by filtration, and a mixed solution of hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid water and 1 part by volume of decyl alcohol) was added. The pale yellow-green precipitate was collected by filtration, washed with a mixed solution of 1N-K0H aqueous solution and decyl alcohol (2 parts by volume of potassium hydroxide aqueous solution, 1 part by volume of decyl alcohol) and filtered. The compound (73-a) was obtained as a pale yellow powder (yield: 31.26 g). The yield was 89% based on 6-methylbenzofuran-2-carboxylic acid. (3) Synthesis of compound (73~b) Mixed compound (73-a) 31. 26g, 2, 4-bis(4-decyloxyphenyl)-1,3-dithia-2, 4- Di-phosphetane-2,4-disulfide (Lawesson's reagent) 24.73 g and 300 g of hydrazine were heated to 110 ° C and the resulting mixture was reacted for 6 hours. After cooling, the toluene solution was washed three times with 500 ml of a 2N aqueous sodium hydroxide solution, and then the organic layer was collected, and n-heptane was added to crystallize. The obtained fresh yellow crystals were collected by filtration, and dried to give a bright yellow powder compound (73-b). The obtained compound (73-b) was used in its entirety directly in the following stages. (4) Synthesis Example of Compound (73-c) Compound (73-b) 35.69, potassium hydroxide 33.37 g and water 630 g were mixed. Then, 97.91 g of potassium ferricyanide was added to prepare a dispersion containing the compound (73-b). To the dispersion, 126 g of decyl alcohol was added, and the mixture was reacted at 40 ° C for 2 hours, and 182 321 867 201100410 was reacted at room temperature for 24 hours, and the precipitated pale yellow precipitate was collected by filtration. The precipitate thus obtained was washed with water and then washed with methanol. Further, it was filtered with hot methanol = net yellow powder. The obtained pale yellow color was dried under vacuum to give 23.31 g of a pale yellow solid which had compound (73-c) as a main component. The yield was 66% based on the compound (73-a). (5) Synthesis of compound (73-d) Compound (73-c) 23. 31 g, and pyridinium chloride 233. lg, and the mixture was heated to 18 Torr to carry out a reaction for 3 hours. The resulting mixture was added to ice, and the resulting precipitate was collected by filtration. After washing with water, it was washed with toluene, dispersed in a saturated aqueous solution of sodium dithionite, chloroform, and mixed for 2 hours under the crucible. After the dispersion was passed through, the precipitate was washed with pure water, and dried under vacuum to obtain a yellow solid 21·2 g containing compound (73-d) as a main component. The yield was 1% by mole based on the compound (73-c). (6) Synthesis Example of Compound (A73-i) Mixed Compound (73-d) 1.0 g, Compound (A) 2. 96 g, Dimethylamine Q Group D 唆〇. 4 g and chloroform 20 ml, toluene 20 ml . To the resulting mixture was added N, Ν'-diisopropyl succinimide 1. 〇2 g under ice cooling. The resulting reaction solution was allowed to react at room temperature overnight. 4 g of Shiqi gum and 200 mg of activated carbon were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour, and then filtered under a vacuum of 'Shidazu soil' to remove the chloroform. Then, methanol was added to the solution to cause crystallization. The off-white powder was collected by filtration, washed with ethanol twice, and then washed with g. The yield was 57% based on the compound (73-d). 183 321867 201100410 2 4H)(A23 H~NMR (CDC13): δ (ppm) 1. 45~i. 85 (m, 49, fw36~2.87 (m, 15H), 3-93~3.97 (t, 4H) 41 二6 3(;L:H)4,5.79~5· 84 (枝(四) ' &quot;7~6 &quot;I,1 16 (d 1ΜΊ 5 (m, 2H), 6. 87~6· 99 (m, 8H), 7. 13~7 57'U 1H) (S'2HK7-38(S'1H)'7 51 (-1H) The obtained compound was confirmed by grain observation by a polarizing microscope ( Phase transition temperature of A73—丨). Compound (A73-1) shows a highly viscous phase from 82 ° C to 141 C at elevated temperature, and a clear nematic phase from 141. 进步. Progressive compound (A73-1) The nematic phase is exhibited at 18 〇t or more, and the nematic phase is exhibited at 84 ° C when the temperature is lowered, and crystallization is slowly progressed. (Example 48) <Synthesis Example of Compound (A63-1)>

(A6M) 184 1 3, 4, 6-trimethyl salicylaldehyde synthesis of 2, 3, 5-tridecylphenol 2 〇. 〇〇g, polyfurfural 11. 03g, anhydrous magnesium hydride 20.97 g was dispersed in acetonitrile 12 〇g. After the mixture was stirred for 30 minutes at room temperature, triethylamine 29.72 g was added dropwise over two hours. The mixture was reacted in a water bath for 321867 201100410 for 8 hours, and reacted at room temperature for 96 hours. The reaction solution was added to a mixed solvent of 200 ml of ethyl acetate and 400 ml of heptane, and 400 ml of pure water was added. After adding cold 2N-hydrochloric acid, the organic layer was recovered after the sharpness of the μ. After the organic layer was dehydrated with anhydrous sodium sulfate, 20 g of yttrium gum and 2 g of activated carbon were added, and the mixture was stirred stably for 30 minutes, and the dispersion liquid was filtered. The filtrate was concentrated under reduced pressure at 40 ° C or less with an evaporator.楫 #到3,4,6-trimethylsalicylide of pale yellow viscous liquid 24.69g. The yield is ancient t. The standard of 2, 3, 5-trimethylphenol is 102%.

(2) 4, 6, trimethylbenzopyrene: two synthetic examples of citric acid make 3, 4, 6-dimethyl-salt junjun 24...., carbonic acid unloaded 48. and dispersed in N, N' - dimethyl acetamide in l3 〇 ml. After heating to (4), the second butyl bromoacetate 28.64 g was added dropwise over 3 minutes. The mixture was reacted 2 μ% under μΟΌ. After cooling the reaction mixture to room temperature, 2 〇〇 ml of decyl isobutyl ketone was added, and the mixture was separated into 1000 ml of pure water. Further, the organic layer was washed twice with 5 N of 1N aqueous hydrochloric acid, and the organic layer was collected. After dehydration with anhydrous sodium sulfate, the solvent was distilled off with an evaporator. The residue was dissolved in 15 g of acetic acid, and 45 g of an aqueous hydrobromic acid solution was added thereto, followed by stirring at 40 c for 1 hour. After cooling to room temperature, 1 N hydrochloric acid 15 〇g was added to take the precipitated white powder. The obtained white powder was further washed with 1N-hydrochloric acid, then washed with heptane and benzene, and dried in vacuo to give white powder of 4,6,3-trimethylbenzofuran-2-carboxylic acid. H.89g. The yield is 3〇% based on 3,4,6-trimethyl salicylaldehyde. (3) Synthesis example of the compound (63-a) 2,5-dimethoxyaniline i6. 75 g, 4,6,7-tridecyl benzofuran decanoic acid l4 89 g was dispersed in chloroform 75mi. After the 185 321867 201100410 suspension was obtained by cooling in an ice bath, '1-ethyl-3-(3-didecylaminopropyl) carbonyldiamine imide hydrochloride was added in an amount of 14.37 g and gas imitation. A 100 g mixture was reacted at room temperature for 72 hours. The obtained mixture was concentrated under reduced pressure, and a mixture of 1N-hydrochloric acid and decyl alcohol (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol) was added to the residue, and 40 g of a mixture of 15 g of heptane was added and crystallized. The obtained sink was filtered, and a mixed solution of hydrochloric acid and methanol (2 parts by volume of hydrochloric acid and 1 part by volume of decyl alcohol) was added. The pale yellow precipitate was collected by filtration, washed with a 1N-K0H aqueous solution-methanol mixture (1 part by volume of potassium hydroxide aqueous solution, 2 parts by volume of methanol) and filtered. The compound (63-a) 22.71 g was obtained as a pale yellow powder. The yield was 92 ° / 〇 on the basis of 6-methylbenzofuran-2-carboxylic acid. (4) Synthesis of Compound (63-b) Mixed Compound (63-a) 22. 71 g, 2, 4-bis(4-decyloxyphenyl)-1,3-dithia-2, 4- Dihexahydrocyclobutane-2,4-disulfide (Lawesson's reagent) 16.24 g and 228 g of chloroform, heated to 110 ° C, and the resulting mixture was reacted for 6 hours. After cooling, it was washed three times with 500 ml of a 2-N sodium hydroxide aqueous solution in a toluene solution, and then the organic layer was collected, concentrated, and then granulated by crystallization. And the compound (63-b) 23.78 g was obtained by filtration. Although the compound (63-b) contains a decomposition product of Lawesson's reagent, it is still used in its entirety in the next stage. (5) Synthesis Example of Compound (63-c) 23.78 g of a compound (63-b), 20.48 g of potassium hydroxide and 389 g of water were mixed. Then, 60.09 g of potassium ferricyanide was added to prepare a dispersion containing the compound (63-b). 77.83g of sterol was added to the dispersion, and reacted at 50 ° C for 4 186 321 867 201100410 hours, and reacted at room temperature for 24 hours. The precipitate obtained by filtering the precipitated scutellariae was washed with water and then washed with methanol. net. Into two, children,. The mixture was washed with hot ethanol and filtered. The yellow color obtained by vacuum drying = page powder The light yellow solid with compound (63-c) as a main component 2 〇 = to 86% of the compound (63-a). g yield (6) Synthesis of compound (63-d) Compound (63-c) 20. 14 g and pyridinium chloride 2 〇〇 · lg were allowed to react at 18 ° C for 3 hours. The resulting mixture was added to ice/dish and the resulting precipitate was filtered. After washing with water, it was washed with benzene, dispersed in a saturated aqueous solution of sodium dithionite, chloroform and spoiled at room temperature for 2 hours. The dispersion was filtered, and the precipitate was washed with pure water, and dried under vacuum to give 18 9 g of an orange solid compound (s). The yield was 1 〇 2% based on the compound (63-c). (7) Synthesis Example of Compound (A63-1) The compound (63-d) 1.0 g, the compound (a) 2.97 g, the dimercaptoamine decylpyridine 0.04 g, chloroform 2 〇 ml, and toluene 20 ml were mixed. To the resulting mixture was added hydrazine, Ν'-diisopropylcarbodiimide i 〇 2 g under ice cooling. The resulting reaction solution was allowed to react at room temperature overnight. 4 g of tannin extract and 200 mg of activated carbon were added to the reaction solution, and the mixture was stirred at room temperature for 1 hour, and then passed through Shixiazao soil. After removing the chloroform by the reduction of the enthalpy/cylinder filtration liquid, the solution was added with T alcohol. The crystallization y was taken up in an off-white powder, and further washed with ethanol twice, and then washed with Geng Hyun and vacuum-dried to give an off-white powder (yield-1) 2. 65 g. The yield was 7 (10) based on the compound (63-d). 321867 187 201100410 Compound (A6 3 -1)]H-NMR (CDC I3): S (ppm) 1. 47~ι· 82 (m ' 2 4H) ' 2. 3 6~2. 5 2 (m, 1 7H), 2. 5 2~2. 8 5 (m, 4H), 3. 9 3 to 3. 9 7 (t, 4 Η), 4. 16 to 4. 20 (t, 4Η), 5· 79 to 5.84 (dd, 2Η), 6.07~6·17 (χη, 2Η), 6.37~6.45 (χη, 2Η), 6.87~7 .Ο 5 (m, 9 Η), 7 · 2 3 (s, 2 Η), 7. 5 3 (s, 1 H). The phase transition temperature of the obtained compound (Α63-1) was confirmed by grain observation with a polarizing microscope. The compound (Α63-1) was heated from 136. (: to 139t shows a highly viscous phase, and a clear nematic phase is obtained from 139 °c. Further compound (A63-1) to l8 (rected as a nematic phase above rc, at 125 ° C when cooling) (Examples 49 to 51, Comparative Example 1) <Example of Production of Optical Film> Polyvinyl Alcohol (Polyvinyl Alcohol 1000 Complete Saponification = Wako Pure Chemical Industries Co., Ltd.) The 2% by mass aqueous solution of the system is formed into a thickness of 89 nra after drying. The composition of the surface of the obtained W is applied to the surface of the obtained W. Then, the main cloth table was heated to the temperature shown in Table 18, and the ultraviolet light of the cumulative light amount shown in Table 18, and/or the optical film irradiated while the dish was formed. The film thickness shown in Table 19 was formed. 321867 188 201100410 [Table 17] Compound (%) of the present invention Liquid crystal compound (%) Polymerization initiator (%) Coating agent (%) Solvent (%) Example 4 9 A72-1 (28.04) An Irgacure 3 6 9 (1.97) BYK3 6 IN (0.03) 69.97 Example 5 0 A73-1 (28.03) An Irgacure 819 (1.96) BYK3 6 IN (0.03) 69.97 Example 5 0 A63-1 (2 8.03) Irgacure 819 (1.96) BYK3 6 IN (0.03) 69.98 Comparative Example 1 LC242 (29.04) Irgacure 819 (0.89) 1 BYK3 6 IN (0.02) 69.15 LC242 : Same polymerization initiator as above: Irgacure 819 (Ciba Japan Co., Ltd.: sulfhydryl phosphine oxide compound) Coating agent: BYK361N (manufactured by BYK Japan) Solvent: cyclopentanone [Table 18] Drying temperature after coating Temperature cumulative light amount (mJ/cm2) at the time of light irradiation Example 4 9 155 ° C 120 ° C 2400 Example 5 0 1103⁄4 90 ° C 2400 Example 5 1 155 ° C 120 ° C 2400 1 Comparative Example 1 Γ 45 ° C ------- - room temperature -1 ~--- 1200 <Measurement of optical characteristics> The front surface difference of the optical film was measured using a measuring machine (K0BRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.). χ 'The glass substrate used for the substrate has no birefringence. Therefore, the diaphragm of the glass substrate is measured by a measuring machine, and the front surface difference of the optical enthalpy of (4) on the glass substrate can be obtained. The difference of the optical 敎 (4) position difference is at the wavelength 447. 546·9(10) and 627. 8nm were respectively measured. 'Calculating coffee (4) 7.3)/Re (546. 9)] 321867 189 201100410 ( Is α〇 and [Re (627. 8) / Re (546. 9)] (as the phantom. Further, the film thickness dUm of the optical film was measured using a laser microscope (LEXT, manufactured by Glyrapus Co., Ltd.). The results are shown in Table 19. The value of Re (546.9) was calculated by dividing the film thickness (^11 = 1^(546. 9)/d). [Table 19] 丨__ 1 III Example 4 9 Re(546.9) '' _ 126.4 α ~0791 ~ 1.039 d (&quot;m) 2.573 Zki 0.049 Λ ίδΙτΊ 5 0 Example 5 1 142.4 126.8 0.898 0.853 1.016 -- --. 2.091 0.068 1.026 2.528 1.001 0.050 0.141 Comparative Example 1 141.0 1.075 -------- 0.978 (Industrial Applicability) The optical film of the present invention can perform the same polarization conversion in a wide frequency band region. . BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a schematic view showing a color filter 本 of the present invention. Fig. 2 is a schematic view showing a liquid crystal display device 5 of the present invention. Fig. 3 (a) to (e) are schematic views showing a polarizing plate 3 of the present invention. Fig. 4 is a schematic view showing a bonding product 21 of a liquid crystal panel 2A and a polarizing plate 30 of a liquid crystal display device of the present invention. Fig. 5 is a schematic view showing an organic El panel 23 of the organic EL display device of the present invention. [Main component symbol description] 2, 2' optical diaphragm 4, 4' color filter layer 6, 10 polarizing plate 1 1 color filter 3 ' 3' orientation film 5 liquid crystal display farm 190 321867 201100410 7, 11 substrate 9 liquid crystal layer 13 transparent electrode 30, 30a, 30b, 30c, 30d '14, 14' laminate 16, 16' support substrate 18, 18' optical film 20 liquid crystal panel ^ 23 organic EL panel 8 counter electrode 12 TFT, insulating layer 13, reflective electrode e polarizing plate 15 polarizing film 17, 17' alignment film 19, 19', 22, 25 adhesive layer 21 bonding product 24 luminescent layer 191 321867

Claims (1)

201100410 VII 1. Patent application scope: -2) (In the formula, 'Z1 and Z2 are in contact with each other to represent a hydrogen atom, a (four) sub, a carbon number of ^ to 6, a cyano group, a succinyl group, a carbon number, a calcined base of 6 to 6 carbon atoms, and a carbon number of 1 to 6.眺(d) fluorenyl group, carbon number 丨 to 6 fluorowire, carbon number 1 to 6 alkoxy group, carbon number 丨 to 6 alkylthio group, carbon number 1 to 6 N-alkylamino group, carbon number 2 N,N-dialkylamino group to 12, N-alkylamine sulfonyl group having a carbon number of 6 to N,N-dialkylamine sulfonyl group of 2 to 12 or -C00H; A compound having the formula G—丨) or a formula (1 valent group: Q and Qj are each independently represented by —CRf —, _s_, _nr2_, _c〇— or 〇_, and R and R each independently represent a hydrogen atom or a carbon number. An alkyl group of 丨 to 4; a polycyclic aromatic hydrocarbon group which is unsubstituted or unsubstituted, or a substituted or unsubstituted polycyclic aromatic heterocyclic group; &lt; D and 0 each independently represent a single bond or a divalent Linkage base Y and G each independently represent a divalent alicyclic hydrocarbon group, and the alicyclic hydrocarbon group may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, and an alkyl group having 1 to 4 carbon atoms. Oxyl, cyano or nitro, CH2~ of the alicyclic hydrocarbon group may also be substituted by _〇---S- or -NH-). A compound of the first aspect of the patent, wherein the compound has a divalent group represented by the formula (2-1) 192 321867 201100410 〇 G or the formula (2-2) (2-1) —~~E1-丨 G^D1 D2-G2-E2-(-A2-B2^—(2-2) Z1 Z2 (wherein Z1, Z2, Q1, Q2, γ1, Dl, D2, and G2 are respectively indicated in the first item of the patent application scope The definitions have the same meaning; E and E are independent representations of single bonds or divalent linkages; B1 and B2 each independently represent a single bond or a divalent linkage; A1 and A2 independently represent a divalent alicyclic hydrocarbon group or a divalent The aromatic hydrocarbon group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, an alkoxy group having a carbon number of 4 to 4, and carbon. a fluoroalkoxy group, a cyano group or a nitro group of 1 to 4; k and 1 each independently represent an integer of 〇 to 3). The compound of the first aspect of the patent application is of the formula (34) (3-2) )): ^ P1—F1&gt;|b1_A1^_E1—g1_d1h^^^_d2_g2_e2+a2__b2^__f2 ~P2 (3-1) 321867 193 201100410 p1—pi l_AlX_El_Gl_Dl (3-2) (wherein, Z1, Z2, Q1, Q2, Y1, d1, D2, G1, G2, E1, E2, B1, B, A, A2, k, and 1 respectively represent the scope of the patent application And the definitions of the two items have the same meaning; F1 and F2 each independently represent an alkanediyl group having a carbon number of 12 to 12; the alkanediyl group may also have an alkyl group having 1 to 5 carbon atoms and an alkyl group having a carbon number of 5 to 5 An oxy group or a halogen atom, the -CH2- group of the alkanediyl group may be substituted by _〇_, _c〇-; and pl and P2 each independently represent a hydrogen atom or a polymerizable group). 4. The compound of claim 1, wherein γ1 is a group represented by the formula (Yl_D or (YL4): (&gt; wherein Z3 independently represents a halogen atom, an alkyl group having a carbon number of j to 6, a cyano group, a nitro group, a nitroso group, an alkylsulfonyl group having 1 to 6 carbon atoms, and a carbon number of 1 to 6; Alkyl sulfinyl group, a fluoroalkyl group having a carbon number of 丨6, an alkoxy group having a carbon number of i to 6, a carbon number! to an alkylthio group of 6 or a N,N-dialkyl group having 2 to 8 carbon atoms Amine group, N-alkylamino group having 1 to 4 carbon atoms, amine sulfonyl group, N-alkylamine sulfonyl group having 1 to 6 carbon atoms, carbon number 2 to 12 194 321867 201100410 N, N-II Alkylamine sulfonyl or -C00H; V1 represents -CO-, -S-, -NRl, -〇-, -Seu〇2_; w1, W2, W3, W4, and W5 independently represent -dN=, and R3 independently represents a hydrogen atom or a carbon number of 1 to 4 The alkyl group; however, at least one of W1, w2, w, w4, and w5 contains s, N, 〇, or Se; a each independently represents 〇 to an integer of 3). 5. The compound according to claim 4, wherein the group represented by the formula (γΐ~ι) is a group represented by the formula (Y3-1), and the group represented by the formula (γ1_4) is a formula (Υ3-3) shows the base: (Υ3-3) (In the formula, 'Z3, a, V1, and W2 respectively have the same meanings as defined in the fourth item of the patent application scope). The compound of claim 4, wherein yl is -(10)3~, or -〇-. 7. The compound of claim 1, wherein g^g2 is trans 4-cyclohexanediyl. The compound of claim 2, wherein A1 and A2 are independently represented by 1,4-phenylene or 1,4-cyclohexanediyl, the anthracene, 4-phenylene and 1, The 4-cyclohexanediyl group may also have a halogen atom, a alkyl group having a carbon number of i to 4, a trifluoromethyl group, a cyano group or a nitro group. 321867 195 201100410 9. The compound of claim 3, wherein only B bound to a1 and B2 bound only to A2 independently represent -CH2-CH2~, C〇〇- &gt; -〇~c〇 - n ~c〇-NH_ ' -NH-C0- ' -O-CH2- ' ~CH2~〇- or single bond, B1 combined with F1 and B2 combined with F2 are independent of -〇~, ~CO- 〇-&gt; -o-co-, _〇-C0-0-, -C0-NH-, -NH-C0- or a single bond. 10. The compound of claim 3, wherein p1 and p2 each independently represent a hydrogen atom, an acryloxy group or a mercaptopropenyloxy group, and pl and P2 are not hydrogen atoms at the same time. A composition comprising a compound of the ninth aspect of the patent application and a liquid crystal compound (except that is different from the compound of the scope of the patent application). 12. The composition of claim U, wherein the liquid crystal compound is a liquid crystal compound represented by formula (20): pll_Ell__^Bll__All^_Bl2___G (2〇) (wherein A system/7 independently indicates 2 price An aromatic hydrocarbon group, a divalent alicyclic hydrocarbon group or a divalent heterocyclic group, the aromatic hydrocarbon group, the alicyclic hydrocarbon group and the heterocyclic group may have an atomic number, a carbon number of 丨 to 6, and a carbon number ( 6 to alkoxy, carbon number! to 6 N-homoylamine, carbon 2 to 12 N,N-dialkylamine, nitro, cyano or thio; B11 and B12 are independent Representation—CRuRl5_, seven c_, _ch=ch_, -ch2-ch2-, -ο-, -s-, one c(=0)...c(=〇)_〇_, —〇_c(=〇)_ -oc(=o)-o- , -c(=s)- , -c(=s)-〇_ , _〇_c(=s)_ , -CH=N-, H, -N= N-, ~&lt;:(=〇)-服16_,_NR"-c(=〇)-, 321867 196 201100410 -0CH2---OCFr, -NR16-, -cm---CF2O-, -CH= CH-C(=0) -0-, -O-Ci^OyCIKH- or a single bond, R14 and R15 independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms, or a combination of R14 and R15 Together, it represents an alkyldiyl group having 4 to 7 carbon atoms; R16 represents hydrogen Or an alkyl group having 1 to 4 carbon atoms; E11 represents an alkanediyl group having 1 to 12 carbon atoms; the alkanediyl group may also have an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a halogen atom; P11 represents a polymerizable group; and G represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 13 carbon atoms, an alkoxy group having 1 to 13 carbon atoms, a fluoroalkyl group having 1 to 13 carbon atoms, and a carbon number of 1 to N-detergent amino group of 13, N, N-dialkylamino group, an aryl group or a nitro group having 2 to 26 carbon atoms, or an alkyl group having 1 to 18 carbon atoms having a polymerizable group, the alkane The group may also have an alkoxy group having a carbon number of 1 to 6 or a halogen atom; t represents an integer of 1 to 5. The composition of claim 11 further comprising a polymerization initiator. The composition of claim 13 wherein the polymerization initiator comprises an acetophenone compound. 15. An optical film obtained by polymerizing a compound of claim 1 of the patent application. An optical film obtained by polymerizing the composition of any one of claims 11 to 14. 17. An optical film according to claim 15 or 16, The retardation value of the long 55〇11111 in (1 ^ (550)) of from 113 to 16,311,111 and is / 4,197,321,867,201,100,410 plate. 18. The optical film of claim 15 or 16, which is a λ/2 plate having a phase difference (Re(550)) at a wavelength of 550 nm of 250 to 300 nm. A polarizing plate comprising the optical film and the polarizing film of any one of claims 15 to 18. 20. A color filter formed on a directional film coated on a color filter substrate, wherein the optical film of any one of claims 15 to 18 is formed. A liquid crystal display device comprising the color filter of claim 20 of the patent application. 22. A flat panel display device comprising a liquid crystal panel comprising a polarizing plate of claim 19 of the patent application. An organic EL display device comprising an organic electroluminescence panel comprising the polarizing plate of claim 19 of the patent application. A method for producing an unpolymerized film, which comprises applying a solution containing the compound of claim 1 to a support substrate or an oriented film formed on a substrate to be dried. A method of producing an optical film, characterized in that the unpolymerized film obtained by the production method of claim 24 of the patent application is cured. 198 321867