TW200914539A - Compound for anisotropic film - Google Patents

Abstract

The present invention relates to a compound for anisotropic film represented by the following formula (1) in the form of free acid, which is useful for anisotropic films such as polarizing films and has high dichroism in the short wavelength region (380 nm-500 nm) and excellent durability. (L1 is -(CH=CH)r- or -(C ≡ C)s -. R and s are an integer of 1-5. Ar1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted heterocyclic group. M is an integer of 0-3. p and k are 0 or 1. p and k are not 0 at the same time. X1 is a hydrogen atom or an organic group. X2 is a hydrogen atom, a nitro group, a substituted or unsubstituted amino group, or a group represented by the following formula (1-a). When X2 is a hydrogen atom, a nitro group, or a substituted or unsubstituted amino group, m is not 0).

Description

200914539 VI. Description of the Invention: [Technical Field] The present invention relates to a light-emitting display element such as a photochromic element or a liquid crystal element (LCD), an organic electroluminescence element (〇LED), a touch type, A useful anisotropic film such as a polarizing film provided in an output/input element such as a panel. [Prior Art] D In recent years, a television using a prior art CRT has been replaced because it is widely used in a flat display or a television receiver such as an LCD. Further, the color reproducibility of the NTSC belonging to the current television system depends on the phosphor characteristics of the CRT, and there is a problem that only about half of the actual object color can be expressed. On the other hand, a photographing apparatus such as a digital camera or a camcorder has been expected to produce a more accurate reproduction of information in a wide range of color representations (color reproduction) in a range larger than the range defined by NTSC in recent years. The display of the ship's color space. S such a background T' LCD or the like replaces the CRT's flat-panel display in principle, and performs a display with a higher chroma color than the CRT, and develops into a new dynamic expansion color space with high functionality of the flat display. Normalization. As a result, the "Extended-gamut YCC color space f〇r vide〇 application-xy YCC" was issued as an international standard 1966_2_4. The xyYCC color space system can almost express the specifications of the actual object color, and thus 97125650 200914539 can also express the material sense or three-dimensional sense of the colorful object. However, the color of the turtle that has been used in the past is a modification of the display used for the various components of the "corresponding to the display of the xyYCC color space. For example: (1) The use of backlights with good purity of RGB three primary colors (2) The use of micro-filters for applying complementary colors to RGB three primary colors} (1) The representative means is (4) _ money used in cold cathode tubes In the case of (2), the use of a micro-filter for adding yellow and nitrogen is mentioned (see Patent Documents 1 and 2). Thus, the factor that governs the color reproducibility of the LCD is a member related to light emission or a member having absorption in the visible light wavelength region, and a polarizing light having absorption in the visible light wavelength region as in the case of the microcalender _ (polarizing film) On the other hand, there is still a situation in which there is no full review. In view of the correspondence between the xyYCC expansion color space and the improvement of the backlight or the micro-lighter, it is necessary to improve the characteristics of the short-wavelength region and the long-wavelength region at both ends of the visible light. However, since the optical properties of the polarizing film of the prior art in the visible light wavelength region are not constant, such as the optical characteristics such as dichroism, there is a problem that the contrast at a specific wavelength or color is lowered. In particular, the short-wavelength region belonging to the blue light complementary color has low dichroism, so the color purity of the blue light is lowered, and color reproducibility cannot be sufficiently obtained. In addition, in the case of the liquid crystal panel 97125550 200914539 for a video camera or an automotive liquid crystal panel, the non-iodine has a two-color color in the visible light wavelength region as a whole due to the durability problem at a high temperature. Organic compounds. However, the molecular structure of a compound having absorption at a short wavelength is generally characterized in that the breadth of the π-common vehicle is smaller than that of the compound having absorption at a long wavelength, that is, the molecular length tends to be short. In general, in order to obtain a sufficient aspect ratio in the case of a dichroic compound, it is necessary to have a long molecular length. Therefore, when a compound having absorption at a short wavelength is used as a dichroic compound, it is difficult to balance the two, so that it has been used so far. The polarizing film is a compound having a low dichroism in a short-wavelength region and is expected to have high dichroism in a short-wavelength region. In addition, 'the use of such a purpose' is a problem caused by the edge of the edge or the edge of the edge of the change in temperature, and the durability of the high temperature is also solved. The combination of a polymer material such as a modified polyethylene (polyvinyl alcohol derivative) and a dichromatic substance f becomes important, and thus development of a novel dichroic compound is desired. [Patent Document 1] Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. 2-25285. SUMMARY OF THE INVENTION The object of the present invention is to provide a polarizing film. Useful as a color-comprising compound. The object of the present invention is to provide an anisotropic composition for use in the skin length (four). The object of the present invention is to provide an anisotropic compound which is excellent in durability. 97125550 200914539 The inventors have carefully examined and found that the free acid form is as follows. (i) The compound for anisotropic film shown can solve the above problems, and the present invention is also a compound for anisotropic film (Application No. 1) which is characterized in that the free acid form is as follows Formula (1): [Chemical 1]

(S〇3H)p <S°3H)k [In the formula (1), the L1 system is a (CH=CH)r- group or a - (Ce〇s-group, and r and s are each independently an integer of 1 to 5;

Ar1 is a phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; m is an integer of 0 to 3; P and k are each independently 〇 or b, p, k is not simultaneously 〇; χ1 is a hydrogen atom or an organic group; X2 is a hydrogen atom, a nitro group, an amine group which may have a substituent or a group of the following formula (la) wherein Χ2 is a hydrogen atom, a nitro group When an amine group which may have a substituent, m is not 0; [Chemical 2]

(In the formula (1 a), the Ar2 group may have a substituent phenyl group, a substituent which may have a substituent of 97,172,550, 200914539, a naphthyl group or a heterocyclic group which may have a substituent; and B1 may be a phenyl group which may have a substituent. a naphthyl group having a substituent or a heterocyclic group which may have a substituent; an integer of η series 0 to 3)]. Further, the present invention is a compound (Application No. 9), which is characterized in that the free acid form is as shown in the following formula (9): [Chemical 3]

[In the formula (9), Ar21 is a phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; h is an integer of 1 to 5; t is 0 to 3 R21 is an alkyl group which may have a substituent, an alkyl group which may have a substituent, a carboxyl group or a hydrogen atom; an X22 hydrogen atom, a nitro group, an amine group which may have a substituent or a formula (9-a) a group in which, when X22 is a hydrogen atom, a nitro group, or an amine group which may have a substituent, t is not 0; [Chemical 4], /7 (9-a) 97125650 〇200914539 (Formula (9-a) In the above, Ar22 may be a phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; B may be a phenyl group which may have a substituent, a naphthyl group which may have a substituent or a heterocyclic group having a substituent; an integer of lanthanum 0 to 3)]. According to the present invention, it is possible to provide a compound which is useful for an anisotropic film such as a polarizing film, and which has high dichroism and excellent durability in a short-wavelength region. [Embodiment] Hereinafter, embodiments of the compound for an anisotropic film of the present invention will be described in detail. The following description of the components of the present invention is an example (present example) of the embodiment of the present invention, and the present invention is not limited to the contents. The anisotropic film which is applicable to the anisotropic compound of the present invention is any one selected from the total direction of the three-dimensional coordinate system towel in the direction of the film thickness direction of the compound containing the dye and the _ 2 direction. The direction has an anisotropic film on the electromagnetic properties. Examples of the electromagnetic properties include absorption, refraction, and the like: electrical properties such as electrical properties, electrical resistance, and electrical capacitance. The film having optical anisotropy such as absorption and refraction is, for example, a linear polarizing film, a circularly polarizing film, a retardation film, an anisotropic film, or the like. The case of this 5 brothers book towel is purely written as an anisotropic film, and the system contains the layer 1 of the invention, and the layer f contains the ageing material and (5). The compound for anisotropic film of the present invention has a function as a function of a dye, and the anisotropic film system containing the compound for anisotropic film of the present invention also functions as a dye film. Further, the term "pigment" as used herein refers to a compound which has absorption in a visible long region. The anisotropic film produced by using the compound for anisotropic film of the present invention is preferably a functional film having an absorption anisotropy as a main effect. Hereinafter, the anisotropic compound of the present invention will be described in detail. In addition, the so-called "substitutable" can also have a substituent. Eight other 12 =:= replaces all carbon numbers of one carbon number, and the compound of formula (1) is represented by (1) in the position of the anisotropic compound of the present invention: the eagle form is as follows [Chemical 5] - Ar1-N々

Ο) ¢) m (S〇3H)p (S〇州I X1—L1-

[In the formula (1), the L1 system-(C!H:H)r- group or the -(CE C)s-group r and the s system are respectively 97125650 200914539 and represent an integer of 1 to 5;

Ar is a phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; m is an integer of 0 to 3; P and k are each independently represented by 0 or 1, but p , k is not at the same time; X is a hydrogen atom or an organic group; X 2 is a hydrogen atom, a nitro group, an amine group which may have a substituent or a group represented by the following formula (I-a) wherein 'the hydrogen is at χ 2 When an atom, a nitro group or an amine group which may have a substituent, m is not 0; (1-) (In the formula (1-a), the Ar2 series may have a substituent, and may have a substituent. a naphthyl group or a heterocyclic group which may have a substituent; U β1 is a phenyl group which may have a substituent, a naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; an integer of η series 0 to 3 )]. ► The compound for anisotropic film of the present invention is an azo compound having a distethyl moiety and a dilute decylamine or a decylamine moiety. The structure in which the diphenylethylene moiety and the dilute group are linearly high with respect to the amine or the blocky guanamine moiety, and the azo compound has a small contribution to the extension of the 7-inch electron carotid system, so the anisotropic film of the present invention In the state where the compound has absorption in the short-wavelength region, a larger aspect ratio of 97,116,050 and 200914539 can be obtained and high dichroism is exhibited. The anisotropic compound of the present invention can also exhibit high dichroism as a compound having not only a short-wavelength region but also a region other than the absorption region. <Ar1 and Ar2> The ArH(1-a) in the formula (1) "is a phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent, or a heterocyclic group which may have a substituent. Examples of the phenylene group include an anthracene, a 4-phenylene group, a fluorene group, and a 3-phenylene group. From the viewpoint of linearity of the knife, a 1,4-phenylene group is preferred. Examples of the stretching naphthyl group include i,4_anthranyl group, 2,6-extension group, &amp; 7-naphthyl group, etc., and from the viewpoint of molecular linearity, I 4 - extension is preferred. Tetaki, 2,6-anthracenyl, more preferably 1, anthranyl. The heterocyclic group is a divalent heterocyclic group, and the group derived from a monocyclic or bicyclic heterocyclic ring is preferred. Examples of the atom other than the carbon of the heterocyclic group include a nitrogen atom, a sulfur atom and an oxygen atom, and a nitrogen atom is particularly preferred. When the heterocyclic group has a structure other than carbon, the lining is _, may also be different. When the heterocyclic group is a _(tetra) group derived from a monocyclic ring, it is preferably in the form of a molecular weight, which is preferably the following formula (1-a0) at the 2, 5 position or 3, 6-position bonding 2 compensation nitrogen-containing aromatic 6-member ring 'Specially good is 2, 5_ than pyridinediyl. Soil [Chem. 7] 97125650 12 200914539

) + ' Q ~ Q are each independently represent a carbon atom or a nitrogen atom, and ^ or Q of Q1 to Q4 are nitrogen materials, and the rest are carbon families, and carbon atoms of qi to q4 may have a substituent. When the heterocyclic group is a base of a heterocyclic ring derived from a bicyclic ring, the molecular linearity

As shown by the following formula (ab a), the linking position is preferably a divalent heterocyclic group in which the benzene ring portions are aligned with each other. [化8]

[In the formula (Ι-al), the ring α is a 5- or 6-membered ring heterocyclic ring. The ring α is bonded to the benzene ring in the formula (1_al) to form a condensed ring. The base system represented by the formula (1-al) may have a substituent]. As a binding ring group represented by the formula (Ι-al), there are a quin〇linediyl group, an extended isoindolyl group, a naphthyridinediyl group, a qUinoxaiinediyi group, a benzothiadiazolediyl group, a phthalimidediyl group, etc., particularly preferably 5 , 8-extended porphyrin group, 5, 8-extended isoindolyl, 5, 8-naphthyridinediyl, 5, 8-quinoxalinediyl. As Ar1 and Ar2, each is independently a substituent which may have a substituent, a 4-phenylene group, a 1,4-naphthyl group which may have a substituent, or a group represented by the above formula (Ι-al). 97125650 13 200914539 {Substituent of Ar1 and Ar2} Examples of the substituent of Ar1 and Ar2 include an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an amine group which may have a substituent, a carboxyl group, and Atom, a reductive acid group, a transbasic group. Specific examples of good substituents of Ar1 and Ar2 are listed below. The number of carbon atoms which may have a substituent is usually 1 or more and 6 or less, preferably 4 or less, more preferably 3 or less. Examples of the group which may be substituted for the alkyl group include an alkoxy group, a hydroxyl group, a halogen atom, a sulfonic acid group, a carboxyl group and the like. Specific examples of the alkyl group may be a methyl group or an ethyl group, and particularly preferably a lower alkyl group which may have a substituent. The alkoxy group carbon number which may have a substituent is usually 1 or more and 6 or less, preferably 4 or less, more preferably 3 or less. Examples of the group which may be substituted for the alkoxy group include a decyloxy group, a thiol group, a halogen atom, a repeating acid group, and a thiol group. Specific examples of the oxyoxy group include an alkyl group which may have a substituent such as a decyloxy group, an ethoxy group, a n-propoxy group, a n-butoxy group, a ethoxy group, a 2' 3-dihydroxypropoxy group or the like. The oxy group is particularly preferably a lower alkoxy group which may have a substituent. The amine group which may have a substituent is usually represented by -NH2, -NHRa, -NR〃Rr, and is independently an alkyl group which may have a substituent, a phenyl group which may have a substituent, or a fluorenyl group which may have a substituent . The alkyl group carbon number is usually 1 or more and 4 or less' is preferably 2 or less. The phenyl group carbon number is usually 6 or more and 10 or less, preferably 8 or less. Examples of the group which may be substituted for the alkyl group and the phenyl group include an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a hydroxyl group, a sulfonic acid group, a carboxyl group, and a functional atom. 97125650 14 200914539 The fluorenyl group is represented by -COR&quot;, and R5 represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent or a phenyl group which may have a substituent. The alkyl group and the alkoxy group have a carbon number of usually 1 or more and 4 or less, preferably 2 or less. The phenyl group carbon number is usually 6 or more and 1 or less, preferably 8 or less. Examples of the alkyl group, the alkoxy group, and the phenyl group may include a carbon number of ruthenium group, a stone alkoxy group having an inverse number of 1 to 4, a hydroxyl group, a sulfonic acid group, and a carboxyl group. Halogen atoms and the like. Specific amino groups which may have a substituent (IV) are an amine group, a methylamino group, an ethylamine group, a propylamino group, a dimethylamino group, a phenylamino group, an ethyl aryl group, a benzamidine group. Amino group and the like. Examples of the tooth atom system include a fluorine atom, a chlorine atom, an atom, and an atom. As the substituent of Ar and Ar2, the dyeing property of the riding polymer substrate, such as molecular linearity, solubility in water, and ruthenium bonding, is preferred, and it is preferred that the substituent has no substituent substituent. , foxyl n via propyloxy, county, two base, fluorine atom, recorded, amine or ethoxylated amine =

Preferably, the non-filament has a substituent as a substituent, a 4-group, and a methoxy group. ', soil T is not only one of these special substituents, the substitution is fine 3 towns, and the face is 2 _ loading to read the nails, take the squat. It is better to pick up the atoms. The neighboring of Gobi [better Ar1 and Ar2} for water solubility, hydrogen bonding, etc.

The Ar and Ar systems are each independently represented by the viewpoint of the dyeability of the polymer substrate, and particularly preferably a stretched phenyl group which may have a substituent or a stretchable naphthyl group which may have a substituent, particularly It is an unsubstituted phenyl group, a silky one, and has a carboxyl group, a sulphate group, a methyl group, a methoxy group, a benzyl group, a 2,3 bis propyl propyloxy group as a substituent. a phenyl group having an amine group or an ethylamino group, or a sulfhydryl group having a substituent, a rhein group, a 1,4-naphthyl group having a thiol group, or a thiol group having a substituent, a rhein group, The base 2, 6_ is a naphthyl group. '&lt;L*&gt; L-(CH=CH)r- group or -(c^c)s- group. ^ and s are separated into integers of 5. From the viewpoint of the stability of the compound, it is preferable that r is preferable to 卜3, and s is preferably 1 to 3 and more preferably 1 in terms of stability of the compound. Further, in terms of molecular linearity, L1 is preferably a &lt;β1&gt; H W)1*- group, and particularly preferably a -(CH=CH)- group. The oxime system of the formula (1-a) represents a phenyl group having a substituent, a group which may have a substituent or a heterocyclic group which may have a substituent. In the case where B is a heterocyclic group, the carbon number is usually 3 or more and 15 cores are monovalent heterocyclic groups per group, preferably, more preferably 12 or less heterocyclic groups. for. The X heterocyclic group, specifically, a ketone ring, a ketone ring, and a pyridine group derived from a pyridine ring, a pyrazole ring, a pyridine group, or the like, is preferably a ring derived from a ring, a substituent ring of (8) or a ring. 97125650 200914539 Examples of the substituent which may have oxime include a sulfonic acid group, a carboxyl group, a hydroxyl group, a nitro group, a cyano group, a halogen atom, an alkyl group which may have a substituent, an alkoxy group which may have a substituent, and the like. An amine group having a substituent, an amine carbenyl group which may have a substituent, an amine sulfonyl group which may have a substituent, a phenyl group which may have a substituent, an aryloxy group which may have a substituent - may have a substituent A carbonyloxy group or the like. * The number of carbon atoms of the base which may have a substituent is usually 1 or more and 6 or less, preferably 4 or less. Examples of the group which may be substituted for the alkyl group include an alkoxy group, a phenoxy group, a hydrazine group, a hydroxyl group, a halogen atom, a sulfonic acid group, and a carboxyl group. Specific examples of the alkyl group include a mercapto group, an ethyl group and the like, and particularly preferably a lower alkyl group which may have a substituent. The number of carbon atoms of the alkoxy group which may have a substituent is usually 1 or more and 15 or less, preferably 13 or less, more preferably 9 or less. Examples of the group which may be substituted with the alkoxy group include an alkoxy group, a phenoxy group, a phenyl group, a hydroxyl group, a tooth atom, a sulfonic acid group, a carboxyl group and the like. Specific examples of the decyloxy group include a methoxy group, an ethoxy group, a n-propoxy group, a n-butoxy group, a hydroxyethoxy group, a 2,3-dihydroxypropoxy group, a carboxymethoxy group, and the like. The alkoxy group having a substituent is particularly preferably a lower alkoxy group which may have a substituent. The amine group which may have a substituent is usually represented by -xian 2, -NHR85, _NR86R87. R to R are each independently an alkyl group which may have a substituent, a phenyl group which may have a substituent, or a fluorenyl group which may have a substituent. The sleek base carbon number is usually! The above is 1 or less, preferably 6 or less, more preferably 4 or less. The phenyl group carbon number is usually 6 or more and 12 or less, preferably 8 or less. Examples of the alkyl group which may be substituted for R85 to R87 and the phenyl group of 97125650 17 200914539 include a phenyl group which may have a substituent, a carbon group of carbon number 4, a hydroxyl group of carbon number 4, a thiol group, and a continuation. Acid base, rebel and tooth atom. Examples of the group which may be substituted for the phenyl group include an alkyl group having a carbon number of 丨4, an alkoxy group having a carbon number of 丨4, a carboxylic acid group, a thiol group, and a thiol group. The fluorenyl group is represented by -COR88, and R88 represents an alkyl group which may have a substituent, an alkoxy group having a substituent or an alkenyl group which may have a substituent, a block group which may have a substituent, and a substituent group A phenyl group or an aromatic heterocyclic group which may have a substituent. 〇 The alkyl group and the alkoxy group each have a carbon number of usually 1 or more and 8 or less, preferably 5 or less. The alkenyl group and the alkynyl group have a carbon number of usually 2 or more and 18 or less, preferably 12 or less, more preferably 8 or less. The phenyl group carbon number is usually 6 or more and 18 or less, preferably 15 or less, and more preferably 9 or less. The number of the aromatic heterocyclic ring is usually 3 or more and 1 or less, preferably 6 or less. Specific examples thereof include a pyridyl group which may have a substituent. The group which may be substituted with the alkyl group, the alkoxy group, the alkenyl group, the alkynyl group, the strepyl group and the aromatic heterocyclic group may, for example, be a hydroxyl group, a sulfonic acid group, a carboxyl group or a halogen atom. A nitro group, an alkyl group which may be substituted, an alkoxy group which may be substituted, an amine group which may be substituted, and a phenyl group which may be substituted. Specific examples of the amine group which may have a substituent are an amine group, a methylamino group, an ethylamino group, a benzylamino group, a 4-carboxybenzylamino group, a phenylamino group, a 4-sulfonic acid phenyl group. Amine, etidylamino, benzoguanylamino, acrylamidoamine, crotonamide, 3-reradyl-propylamine, laurylamine, and the like. The number of carbon atoms of the amine oxime group which may have a substituent is usually 丨 or more and 6 or less, which is preferably 4 or less compared with 97125650 18 200914539. The group which may be substituted with the amine mercapto group may, for example, be an alkyl group having 1 to 4 carbon atoms which may be substituted. Specific examples of the amine sulfhydryl group which may have a substituent include an amine fluorenyl group and an N-decylamine fluorenyl group. The amine having a substituent may have a carbon number of usually 1 or more and 6 or less, more preferably 4 or less. The group which may be substituted for the aminesulfonyl group may, for example, be an alkyl group having 1 to 4 carbon atoms which may be substituted. Specific examples of D as the aminesulfonyl group which may have a substituent include an aminesulfonyl group and an N-decylaminesulfonyl group. The phenyl group carbon number which may have a substituent is usually β or more and 1 Å or less, preferably 8 or less. Examples of the group which may be substituted for the phenyl group include an alkoxy group, a hydroxyl group, a sulfonic acid group, a carboxyl group and the like. Specific examples of the phenyl group which may have a substituent include a phenyl group, a sulfonic acid phenyl group, and a 4-sulfonic acid phenyl group. (1) The base which is a pure base which may have a substituent is preferably a phenyl group or a phenyl group, and examples of the group which may be substituted with an aryl group include a burnt group, a methoxy group, a thiol group, and a sulfonic acid group. , hydroxyl, etc. Specific examples of the aryloxy group which may have a substituent include a phenoxy group, a 2-naphthyloxy group, a p-nonylphenoxy group, and a p-nonyloxyphenoxy group. Alkylphenoxy and the like. The oxy group which may have a substituent is represented by 〇«, and the same is the same as the above R88 ′. As a specific example of a substituent-reading oxy group, the exemplified ethyl ethoxy group, 97125650 19 200914539 stupidyloxy valence oxime, 3 retino-propenylamine, rhein benzoyloxy Base. ~ The number and position of the substituent of {B] The phenyl group of B may have one or more substituents, and may have two or more substituents, and preferably three or less substituents. The substitution position of the substituent is in the case of a substituent, and is 4 positions with respect to the azo group, and in the case of 2 or more substituents, the base of the towel is preferably the base. Replaced by 4 digits. The naphthyl group of β1 may have one or more substituents, and may have two or more substituents, and the substituent 3 may be as light as possible. Wherein the substitution position of the substituent (IV) in the case of a 1-naphthyl group, the position of the substituted azo group is taken as the i position, and the substitution is preferably the -4 position, and in the case of the 2-naphthyl group. When the substituent is one, the position of the substituted azo group is taken as the 2 position, and the substitution is preferably the 6 position. When the substituent is on the oxime, the base having the highest stack is substituted with the azo. The position of the base is taken as 2 digits, and it is preferable to replace it with 6 digits. The β1 aromatic heterocyclic group may have two or more substituents, and preferably three or less substituents. (Preferred Β1) Preferred is a phenyl group which may have a substituent or a naphthyl group which may have a substituent, especially in view of molecular characterization, _, a fine methyl group, ? The oxy group, the thiol group, the benzyl group, the amide group, the amine group, the hydroxy group, the phenyl group and the naphthyl group are preferably used as the substituent. &lt;Ρ&gt; 97125650 20 200914539 X represents a hydrogen atom or an organic group. The organic group referred to in the present invention is a group containing a carbon atom, and specifically, an alkyl group which may have a substituent, a carboxyl group, an alkoxycarbonyl group which may have a substituent, and a benzene which may have a substituent A naphthyl group which may have a substituent, and a heterocyclic group which may have a substituent. The alkyl group which may have a substituent is usually 1 or more and 8 or less, and preferably X 5 or less. Examples of the substituent to substitute the substituent include an alkoxy group and a carboxyl group. Specific examples of the alkyl group which may have a substituent include a methyl group, an ethyl group and the like, and particularly preferably a lower alkyl group which may have a substituent. The alkoxy group having a substituent may have a carbon number of 2 or more and 1 or less, preferably 8 or less. The group which may substitute the alkoxycarbonyl group may, for example, be an alkoxy group or a phenyl group. Specific examples of the silk group which may have a substituent include a methoxycarbonyl group, an ethoxycarbonyl group and the like. The phenyl group which may have a substituent is usually 6 or more and 15 or less, and preferably 12 or less. The base which can replace the fresh base is exemplified by silk, alkoxy group, zoic, county, and may have a substituted red county #. Specific examples of the amine group having a substituent may be the same as those described above as the substituent of B1. Specific examples of the phenyl group which may have a substituent include a phenyl group which may have a substituent such as a phenyl group or a 4-stone group. The naphthyl group which may have a substituent usually has a carbon number of 1 Å or more and 15 or less, preferably 12 or less. As a group which can substitute the naphthyl group, a batch, a siloxane group, a carboxyl group and the like are emitted. A naphthyl group having a substituent such as a naphthyl group having a substituent, such as a caffeine 2-cacoyl group, a methyl-2-naphthyl group or the like. 97125650 21 200914539 A heterocyclic group-containing i-valent heterocyclic group which may have a substituent, and usually an aromatic heterocyclic group is generally an aromatic group having a carbon number of 3 or more and 10 or less (preferably 6 or less): a cyclic group. Examples of the group which may be substituted for the heterocyclic group include an alkyl group, an alkoxy group, an acyl group, a phenyl group, and a thiol group. Specific examples of the heterocyclic group which may have a substituent include a ring derived from a (tetra) ring, a bell ring, a ring, and the like, and are preferably a group derived from a bite. {Preferred X1} X1 is preferably a phenyl group which may have a substituent, a filament which may have a substituent, a thiol group and a fluorene nitrogen atom. From the viewpoint of water solubility of the compound, a slow group is preferred. From the viewpoints of dichroism and stability of the compound, an unsubstituted phenyl group or a nitro group, an amine group, a county, a ruthenium, a fluorenylamino group or a benzoylamino group as a substituent is preferred. One of the phenyl groups. A preferred combination of CL1 and X1&gt; In the above preferred combination of L1 and X1, from the viewpoint of dichroism and stability of the compound, an L1 system-(CIK:H)- group, a lanthanoid system is preferred. The phenyl group which may have the substituent I is more preferably a phenyl group. Further, from the viewpoint of water solubility, it is preferred that L1 is a -(CH=CH)- group and X1 is a fluorenyl group. Among them, a specific example of a better compound is further described in detail in Items 2 to 4. &lt;X2&gt; X2 is a hydrogen atom, a schlossyl group, an amine group which may have a substituent or a group represented by the following formula (i-a). 97125650 22 200914539, N-Ar2-]-n VIII (1_a) \ /η N-B1 The amine group which may have a substituent is usually represented by -NH2, -NHR95, -NI^R97. R95 to R97 are each independently an alkyl group which may have a substituent, a phenyl group which may have a substituent or a fluorenyl group which may have a substituent. The carbon number of the base is usually 1 or more and 6 or less, preferably 4 or less. The phenyl group carbon number is usually 6 or more and 18 or less, preferably 15 or less, and more preferably 9 or less. Examples of the alkyl group or the phenyl group which may be substituted for R95 to R97 include a phenyl group which may have a substituent, an alkoxy group, a thiol group, a acid group, a thiol group, and a tooth atom. Examples of the base which may be substituted for the phenyl group include a carbon group having 1 to 4 carbon atoms, an alkoxy group having a carbon number of 4, a sulfonic acid group, a carboxyl group, and a hydroxyl group. The fluorenyl group is represented by -C0R98. 'R98 means an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, and may have a substituent A phenyl group or an aromatic heterocyclic group which may have a substituent. Each of the alkyl group and the alkoxy group has a carbon number of usually 1 or more and 8 or less, preferably 4 or less. The number of carbon atoms and the sigma block are usually 2 or more and a or less, preferably 12 or less, and more preferably 8 or less. The phenyl group carbon number is usually 6 or more and 18 or less, preferably 15 or less, and more preferably 9 or less. The aromatic heterocyclic group has a carbon number of usually 3 or more and 1 or less, preferably 6 or less. Specific examples thereof include a counter group which may have a substituent. As a substitutable hetero group, the alkoxy group, the alkenyl group, the silk, the silk, and the base of the noodle county, the formula can be listed as 97125550 23 200914539, which is a rhodium group, a rhein group, a aryl group, a halogen atom, A succinyl group, an alkyl group which may be substituted, an alkoxy group which may be substituted, an amine group which may be substituted, and a phenyl group which may be substituted. Specific examples of the amine group which X2 may have a substituent are an amine group, a mercaptoamine group, an ethylamine group, a benzylamino group, a 4-decylbenzylamino group, a phenylamino group, a 4-lithus Acid phenyl. Amino, ethinylamino, benzoguanylamino, acrylamidoamine, crotonamide, 3-mercapto-acrylyiylamino, lauric acid amine, and the like. From the viewpoint of dichroism, X2 is preferably a group having a molecular length longer than the formula (Ι-a). &lt;m&gt; The m system represents an integer of 〇3. Here, when the above oxime 2 is a hydrogen atom, a nitro group or an amine group which may have a substituent, m is not ruthenium. The preferred m値 for the purpose of making the color tone better is different, but as the compound having absorption mainly in the short wavelength region, m is preferably 〇 〜 2, and more preferably 1 is 〇 〜1. Although the above X2 is a hydrogen atom, an amine group which may be substituted or may have a substituent, m is not 0, but the free acid form is a compound represented by the formula (1) having a Wei in the visible light wavelength region, and it is necessary to be a molecule. It has an azo group on 1 _. &lt;n&gt; η represents an integer of 0 to 3. The preferred η 以 for the purpose of making the color tone better is not a compound having absorption mainly in the short-wavelength region, and preferably 97125650 24 200914539 n is 〇 〜1. &lt;P, k&gt; When P and k are independent of 〇 or 卜, respectively, they are G. From the viewpoint of the resolution of water, it is preferred that P and k are both &lt;molecular weight&gt; (

The L-acid form is the knives 1 of the compound for an anisotropic film of the present invention represented by the formula (1), and is preferably in the form of a free acid, and is preferably 1,500 or less, more preferably 5% or less. for! the following. Soil &lt;Water Soluble&gt; The compound of the present invention is a compound of "water compound". &lt;About salt type&gt; 2 The compound for anisotropic film is in the form of free acid (swim type) The existence of the village. ^ ztr and 'M compound and the free acid 檨 can be obtained by using the mountain salt type, the original 'can be converted into the desired salt type. As a salt type exchange method, can be arbitrarily known. Na. The following method.) In the aqueous solution of the compound obtained by lone 3L, a strong acid such as hydrochloric acid is added, and the oral substance is acid-deposited in the form of free hydrazine to obtain the desired alkali solution of the ion (for example, 'A Wei Cailu And the salt exchange method for neutralizing the acidic group of the compound. 2) Adding an excessive excess of the acid salt having the desired counter ion to the aqueous solution of the compound obtained by the salt type (for example, chlorination) Na, gas stealing, salt exchange method in the form of salting out 97125650 25 200914539 cake. The (four) sex Yangxuan exchange resin of the material 3 - the continuous liquid W, the compound is acidified after the acid form With a solution (for example , sodium hydroxide aqueous solution, aqueous solution of hydrazine hydroxide) to salt the acid exchange method of the neutralization of the α substance. 4) For the county material, read the dissolved ribs Γ method. Hydrogen oxyhydration aqueous solution) a cation exchange resin for the water gorge riding side of the salt type lysate, and (4) salt exchange of the heterogeneous conjugate of the present invention is a sulphuric acid type or a salt type, which is based on a compound pKa and ρΗ of the compound solution. Therefore, the anisotropy of the present invention is based on the torographic base of the compound _ various forms · free acid type; any salt type: when there are two or more acidic groups, the free acid type and the salt type Mixing, mixing of two or more kinds of salt forms, etc. In particular, the acidic group of the azo compound in the anisotropic film is preferably agglomerated by an anisotropic compound described later or has an anisotropic film. The effect of the treatment in the solution of the dissociable salt of the substrate of the compound may be a salt type different from that of the user in the step of producing the anisotropic film. An alkali metal salt such as Na, Li or κ, which may be substituted with a thiol group or a hydroxyalkyl group Salt or organic amine salt. Examples of organic amines include low-grade alkylamines of carbon number β, low-level amines of carbon number substituted by base group, and lower alkane 97125550 of Weib 6 substituted by silk. 26 200914539 Alkamine, etc. In the case of the salt-transformed τ, its face is limited to the genus, and it can also be mixed with a plurality of species. It can also be mixed with a plurality of compounds in the molecule, and can also be mixed with the new species in the composition. .

The preferred form of the acidic group of the compound for an anisotropic film of the present invention differs depending on the production step of the compound, the content of the anisotropic compound described later, or the like, and the high solubility in water. If necessary (for example, because the migration energy of the compound to the substrate is increased, and the composition for the anisotropic film must be a high compound concentration), it is preferred to have a lithium salt, a triethylamine salt, An organic amine salt substituted with a water-soluble group or one or more of these salts. On the other hand, in the case where low solubility to water is necessary (for example, in the case where the compound is not desired to be precipitated from the compound solution, etc.), it is preferred to have a free acid form, a sodium salt, a potassium salt. An alkaline earth metal salt such as a calcium salt or more than one of these salts. Specific examples of the compound for an anisotropic film represented by the above formula (1) as a free acid form include specific examples of the compound for an anisotropic film which are contained in the following formulas (2) to (8). For example, there are other compounds for anisotropic films such as the following. &lt; 97125650 27 200914539 [Chemical]

97125650 28 200914539 1-2. The compound represented by the formula (2) and the formula (3) is a free acid form of the compound of the above formula (1), and the free acid form is represented by the following formula (2). Anisotropic film used for characters [化11] ^

[In the formula (2), Ar2, B1, Hi, k, and the carrier are the same. ] (2)

The n- and P-forms are preferably an anisotropy compound which is an anisotropy of a free acid form such as H(2), and a compound for the film of the above formula (1).

N I (9) [In the formula (3), Αγ'Β1, !^, ^ are the same as those in the above formula (2) in the form of the free acid as described above and in the 11th system. The middle portion is preferably a compound for an anisotropic film represented by a free acid form such as &lt;(2) or (3). The compound for anisotropic film represented by the following formula (3-1) is [Chem. 13] 97125650 29 200914539

[In the formula (3-1), the XU〆 and η systems are the same as those described in the above formula (3). Further, the free acid form is preferably a compound for an anisotropic film represented by the following formula ((4)) [Chemical Formula 14]

[In the formula (3-ΙΙ), it is a hydrogen atom or an organic group; β32 is a heterocyclic group which may have a substituent and may have a substituent, and a heterocyclic group which may have a substituent; X1, Ar and η It is the same as that described in the above formula (3-1). &lt;Χ32&gt; X32 is a hydrogen atom or an organic group, and specific examples and preferred examples thereof are the same as those of the specific examples and preferred examples of X above. \32 and χι can be the same or different, and the same is preferable in terms of ease of synthesis. &lt;β32&gt; Β32 represents a phenyl group which may have a substituent, a stretched naphthyl group which may have a substituent or a heterocyclic group which may have a substituent, and specific examples and preferred examples thereof are a phenyl group and a naphthene group Specific examples and preferred examples of the substituents of the hetero group and the heterocyclic group are as described above with 9712256 30 200914539

The same as those described in Ar1 and Ar2. The specific examples of the compound for an anisotropic film represented by the above formula (2) or (3) in the form of a free acid are as follows. However, the present invention is not limited thereto. Further, the following specific examples are described in the form of a free acid. [化15]

(2-4) θ''

SO^H HOUS C^-COI

(2-5} h3c-c=o-comh

Μ=Ν—^^-NHC0-C=C-CI^ (2-6) ^C-Ci :QNH*

NHC〇-r^ 97125650 31 200914539 [Chem. 16] (2-7)

Γ (2-10)

jSCjaH SO^H 雠H off

(2-11)

97125650 32 200914539[化π] (2-14)

(2-15)

(2-17}

97125650 33 200914539 [Chem. 18] (2-20)

H,c &lt;2-21)

(2-24)〇^rrco

97125650 34 200914539[化19] (2-25)

So3h

ο so3h h〇3s (Cj&gt; so3h (2-27) Γ ho3s 〇 ί 97125650 (2-28}

rs-pM=NH〇4^-rSH〇)

COOH

HOaS S03H (2-30) HOOC-C= Γ . (2-31)

So3h

sL so3h

HO3S HOOC 35 200914539 [Chem. 20] (2-32)

Factory (S〇3H

H03S

$OaH =n_〇-c (2-33)

O^^C-|^-&lt;y^C=C^p)-N-N-〇-N=N-(P&gt;-C H03S Factory 〇) ί (2-34) ο

So3h (2-35)

HO3S

C=c-^-N=N HOaS

SO3H

OH

-C=C-^*N

rSD3H

Η H HO3S

POOH OH (2-36)

S03H

So3h (2-37)

I

SOaH (2-38)

O3H

&lt;〇^c=c-9-n-(Qhc=c*-^)-n=n-〇-n=n 〇 ho3s S〇3H

97125650 36 200914539 [Chem. 21]

(2-44)

97125650 37 200914539 [Chem. 22]

(2-51)

s~0 97125650 38 200914539 [Chem. 23] (2-52)

0^rr°cH HQ^S HOafi Γ (2-53) (2-54)

NHCQ—C iHCO—C-H H so3h (2-55) -OOJ sq^H HC 2—OCHM-

* HQsS HD^ Q&gt;-^-ocHnhQ-c=c^Q-n=n (2—56) (2-57)

L

J 97125650 39 200914539 [Chem. 24]

Ο fS〇3H ---- /r^ h3c

HO^S (2-62) so3h

&lt;〇^g=g-rNH〇^c=cp^N=N^Q^Np=cHQ&gt; ho3s 〇ch3 (2-63) ϋ h3c so3h HOaS 〇CHa 1-3. Equation (4), Formula ( 5) and a compound represented by the formula (6) in the compound of the anisotropic film represented by the above formula (1) in a free acid form, and an anisotropic film compound represented by the following formula (4) in a free acid form. It is better. [Chem. 25] X1—L1-^

N-Αγ^-Vn π_Β1 97125650 40 (4) 0 200914539 [In the formula (4), Ar1, Ar2, R1, T1, Y1 1 Β L χ, k, n, and ρ are respectively associated with the above formula (1) the same. In the form of a free-formed compound of the anisotropic film represented by the above formula (4),

The acid form is as follows (the anisotropy _ compound represented by 4-n is preferred. [Chem. 26]

In the formula (6), X1, AlJ2, β1 and η are the same as those described in the above formula (4). In the compound for an anisotropic film represented by the above formula (4), it is preferred to use an anisotropic coffee compound represented by the following formula (5) in a free oxime form. [化27]

[In the formula (5), the f-cluster has a phenyl group which has a silk taken off, a thiol group which may have a substituent or a heterocyclic group which may have a substituent; and the L system represents -(CH=CH)r, -yl or ~(c = n, 苴 * _ , 乂 - L) s - the base 'r and s, each independently 'is an integer from 1 to 5; X3 is a hydrogen atom or an organic group;

Ar, L1, X1, ρ and k are the same as those described in the above formula (4). &lt;L2&gt; 97125650 200914539 In the formula (5), L2 represents -(CH=CH)r~ group or _(c=c)-, and is independently an integer of 5th. Specific examples and preferred examples of the above-mentioned L1 are the same as the specific examples and preferred examples of the above L1. &lt;Β12&gt; In the formula (5), W represents a stretched phenyl group which may have a substituent, a stretched naphthyl group which may have a substituent, or a heterocyclic group which may have a substituent. Specific examples and preferred examples of the above are the same as the specific examples and preferred examples of the above-mentioned ·ι·1 and Ar2. 〇 &lt;X3&gt; / 'X3 is a hydrogen atom or an organic group in the formula (5). Specific examples and preferred examples are the same as the specific examples and preferred examples of the above X1. In the compound of the anisotropic film represented by the above formula (5), the free acid form is preferably an anisotropy compound represented by the following formula (6) in the form of a free acid. [化 28]

[In the formula (6), a 1,4-phenylene group which may have a substituent, or a 1,4-phenylene group which may have a substituent; a 1,4-phenylene group having a substituent or may have 1,4_strandyl group of the substituent; 'X and X are the same as those described in the above formula (5), respectively). &lt;Arn&gt; 97125650 42 200914539 In the formula (6), Ar11 represents a 1,4-phenylene group which may have a substituent or a 1,4-naphthyl group which may have a substituent. The preferred substituent of Ar11 is the same as the case of the 1,4-phenylene group which may have a substituent of Ar1 or the 1,4-naphthyl group which may have a substituent. &lt;B13&gt; In the formula (6), B13 is a 1,4-phenylene group which may have a substituent or a 1,4-naphthyl group which may have a substituent. A preferred substituent of B13 is the same as the case where Ar2 may have a 1,4-phenylene group which may be substituted for a certain f 1,4-phenylene group or may have a substituent. Specific examples of the compound for an anisotropic film represented by the above formula (4), (5) or (6) in the form of a free acid are as follows. However, the present invention is not limited thereto. In addition, the following specific examples are described in the form of a free acid.

C 97125650 43 200914539 [Chem. 29]

97125650 44 200914539 [Chem. 30]

97125650 45 200914539[化31] (4-13)

Γ

97125650 46 200914539 [Chem. 32]

97125650 47 200914539 [Chem. 33]

97125650 48 200914539[化 34]

(4-3 0)

97125650 49 200914539 [化35] (4-3 5)

(4-37)

Ho3s

97125650 50 200914539 [Chem. 36] (4-3 9)

1-4. The compound represented by the formula (7) and the formula (8) is an isotropic property as shown in the following formula (7) in the free acid form of the compound for an anisotropic film represented by the above formula (1). The compound for the film is preferred.

Ut 37] ^

[In the formula (7), 2, X12 is a hydrogen atom, a hetero group, an amine group which may have a substituent; and A and A are each independently a phenyl group which may have a substituent, a naphthyl group which may have a substituent or may have a substituent a heterocyclic group; j is an integer of 0 to 2; L1, X1 'k and p are the same as those described in the above formula (1). &lt;X12&gt; In the formula (7), X12 represents a hydrogen atom, a nitro group, and an amine group which may have a substituent. The amine group which may have a substituent is usually represented by -NH2, -NHR51, -NR52R53, and the RR groups are each independently, which may be an alkyl group which may have a substituent, and may have a substituent of 97,162,550, 51, 2009, 539, phenyl or may have a substituent. The base. The number of carbon atoms in the base is usually 1 or more and 4 or less, preferably 2 or less. The phenyl group carbon number is usually 6 or more and 18 or less, preferably 15 or less, and more preferably 9 or less. The fluorenyl group is represented by -C0R54. R54 represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or a phenyl group which may have a substituent. The alkyl group and the alkoxy group of R54 each have a carbon number of usually 1 or more and 4 or less, preferably 2 Å or less. The alkyl group which may be substituted with R54, the alkoxy group and the phenyl group may, for example, be an alkoxy group (generally a carbon number, a hydroxyl group, a sulfonic acid group, a carboxyl group or an amine group (specifically The amine group represented by the above-mentioned - ship, -NHR51, -NR52R53, a halogen atom, etc. The base of the substitutable alkyl group, a phenyl group or a fluorenyl group of the above R51 to R53 is a sucrose base and a Specific examples of the amine group which may have a substituent include an amine group, a methylamino group, an ethylamino group, a propylamino group, a didecylamino group, and a benzene group. An amino group, an ethenylamino group, a benzhydrylamino group, etc. As X12, particularly a hydrogen atom, a nitro group, an amine group, an ethyl fluorenyl group, and a benzamidine which may have a substituent on a benzene ring Alkyl groups are preferred. &lt;A丨 and A2&gt; In the formula (7), A1 and A2 are each independently a phenyl group which may have a substituent, a naphthyl group which may have a substituent or a substituent which may have a substituent Specific examples and preferred examples of the A1 and A2 are the same as the specific examples of the above Arl and Red 2 and the preferred examples of 97125650 52 200914539. &lt;j&gt; In the formula (7), j An integer of 0 to 2. In the sense of: = a Q,

(8) The same as those in the above formula (7) [in the formula (8), x, xi2, Al, A2, Ll &amp; In the compound for an anisotropic film represented by the above formula (8), the compound of the anisotropic film represented by the following formula is preferably used in the form of a free oxime.

[In the formula (8), ^ and j are the same as those described in the above formula (8)]. The formula of the compound for an anisotropic film represented by the above formula (7) or (8) is as follows. However, the present invention is not limited thereto. Further, the following specific examples are described in the form of a free acid. [40]

HC〇-g=g—COOH

97125650 54 200914539[化 41]

(7-9)

NHC〇-C=C-CO〇H Η Η

(7-11)

97125650 55 200914539[化42]

/Ρ^ΗΗΟ,ε

0-〇ΟΗΝ-〇^=〇Η〇^Ι (7-16)

(7-17)

(7-18)

97125650 56 200914539 [Chem. 43]

(7-20)

(7-21) ^cx&gt;-o«^-co〇h (7-22)

2. Compound represented by the formula (9) The compound of the present invention is a novel compound represented by the following formula (9), and is suitable for use as an anisotropic compound. [化44]

97125650 57 200914539 [In the formula (9), 'Ar21 means a phenyl group which may have a substituent, a heterocyclic group which may have a substituent, and a substituent; h is an integer of 1 to 5; t is 〇~3 An integer: ^ represents a phenyl group which may have a substituent, a thiol group which may have a substituent, a few groups or a hydrogen atom; X represents a hydrogen atom, a nitro group, an amine group which may have a substituent or the following formula (9-a) a group in which, when X22 is a hydrogen atom, a nitro group, or an amine group which may have a substituent, 't is not ruthenium;

(In the formula (9-a), Ar22 represents a phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; and B represents a phenyl group which may have a substituent, A naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; u is an integer of 0 to 3)]. &lt;Ar21 and Ar22〉

Ar and the Ar of the formula (9-a) are each independently represented by a stretching phenyl group which may have a substituent, a stretching naphthyl group which may have a substituent or a heterocyclic group which may have a substituent, and specific examples and preferred examples thereof Specific examples and preferred examples of the substituents which may be possessed by the stearyl group, the extended naphthyl group or the heterocyclic group of Ar21 and Ar22 are independently the same as those described in the above A ri and A r 2 97125650 58 200914539 . &lt;b22&gt;&lt;R21&gt; is a phenyl group which may have a substituent, a terpene 3 which may have a substituent, a heterocyclic group which may have a substituent, and a specific example and a preferred example of a phenyl group The specific substituents, the number of substituents or the substituents of the substituents possessed by Cai Ji and Shijisuke are the same as those described in the above (1). The 〇β filaments may have a phenyl group which may have a substituent, and may have a filament, a carboxyl group or a ruthenium atom of a substituent, wherein a phenyl group which may have a substituent, a compound which may have a substituent, a secret example, a stupid base, and a specific example of a substituent which the silk may have The preferred embodiment is the same as those described in the above g. <x22> X22 represents a hydrogen atom, a nitro group, an amine group which may have a substituent or a group represented by the following formula (9-a). ~(NVAr«)-N々* u N-B22 (9-a) X Specific examples and preferred examples, specific examples of the amine group which may have a substituent, and a good example of a car and an amine group Specific examples and preferred examples of the substituent are the same as those described for the amine group having a substituent of X. <t> is an integer of 0 to 3. When the above Χ22 is a hydrogen atom, a nitro group, and an amine group having a substituent of 97125650 59 200914539, t is not ruthenium. The purpose of making the color tone better is different, but it is resident in a short wavelength region. The compound having an absorption, preferably t is 〇 〜 2, and more preferably 七 (Μ. When X22 is a hydrogen atom, an exact group or an amine group which may have a substituent, t is not 〇, Because the compound of formula (9)_ has absorption in the visible wavelength region, and the molecule needs to have an azo group above 丨. &lt;u&gt; U represents an integer of 0 to 3 to make the color tone better. Although it is different for the purpose, although it is different, it is a compound that corrects the long-range shot, and is more than 0~1. 疋&lt;h&gt; h is an integer of 丨~5. h is 1~3. Preferably, it is better to use Bu. 2 &lt;Better combination of Bu and &&gt; In the above h and the combination towel 'in terms of the double button and the compound mosquito, it is preferable that h is W and the phenyl group which may have a substituent is preferable. More preferably, from the viewpoint of water solubility, h~R and base are preferred. &lt;Preferred combination of XM t> in the form of free acid (9) The compound shown is a compound of the following combination: 疋X and t are °, and &quot;2 is a phenyl group which is the above formula (9, . , , 1 s. R or which may have a substituent is good 97125650 #世 60 200914539 is that R21 is a county or an unsubstituted phenyl group. The second plant is preferably a compound represented by the above formula (9-a). In this case, h is preferably 1. The hydrazine is a carboxyl group. Or the best is the phenyl of the Q county or the silk phenyl silk, preferably the filament of the special substituent ± = fh $ 1 _. From the standpoint of age, it is preferred that X22 is a nitro group, an amine group, a mercaptoamine group, an acetamino group or a 4-phenyl group. &lt;Molecular weight&gt; The molecular weight of the compound of the present invention represented by the above formula (9) as the free acid form is preferably 5 Å or more in terms of the free acid form, more preferably 5% or less, still more preferably 1300 or less. Good for 1200 or less. &lt;Water-soluble&gt; _ Acid form The compound of the above formula (9) is usually a water-soluble hydrazine compound. &lt;Regarding the salt type&gt; The acid form of the present invention which is the above formula (9) may be used in the form of a lyophilic acid form (free acid form), and a part of the acid group may be a salt type. Further, the salt compound may be mixed with the free acid form. Further, in the case of obtaining a salt type at the time of production, it may be used as it is, or may be converted into a desired salt type. The salt type, the preferred examples thereof and the like are as described above in relation to the salt form of the compound for anisotropic film of the present invention. 97125650 61 200914539 &lt;Specific Example&gt; A specific example of the compound of the present invention represented by the above formula (9) as a free acid form can be derived from the above-described formula (1) to (8) as the free acid form. Among the specific examples of the compound for a film, those satisfying the condition of the formula (9) are listed, but are not limited thereto. 3. Method for synthesizing a compound The compound of the anisotropic film represented by the above formula (1M8) and the free citric acid form of the hair-form compound represented by the above formula (8) can be produced according to a known method. 3-1. Method for synthesizing a compound represented by the formula (2) and the formula (3) For example, a compound having a free acid form as shown in the above formula (2-oxime) can be subjected to the following steps of <1> to <3>. And manufacturing. <1> 4-Amino-4-stone-succinyl stilbene 2,2'-sodium citrate was incubated at room temperature on Ν-methyl-2- gamma, and cinnamic acid chloride and sodium carbonate were added. I's thiolated at room temperature for 2 hours. After the completion of the reaction, it was discharged from water, and the thiol compound was taken out by salting out. <2> The obtained thiol compound was dissolved in water and heated to 6 〇~ publication. c. Add sodium hydrosulfide to carry out the reduction reaction. After completion of the reaction, the mixture was cooled to room temperature, and the reduced compound was taken out by salting out. <3> According to the general method {for example, refer to Hiroshi's "New Dye Chemistry" (Zhaopu, December 21, 2008, "Technology Newspaper Issue", pp. 396~409)} The compound is obtained by coupling in a phenol to obtain a compound of the formula (2-1) as a free acid form of the sodium salt form 97125650 62 200914539. Further, the compound of the present invention represented by the above formula (9) in the form of a free acid can also be synthesized in the same manner. 3-2. Method for synthesizing a compound represented by the formula (4), the formula (5), and the formula (6) For example, the compound represented by the following formula (4-4a) can be subjected to the following steps (B). Made for manufacturing. [化47]

(A) According to the general method {for example, refer to Hiroshi's "New Dye Chemistry" (December 21, 2011, Technical Newspapers, Issued on pages 396 to 409)} 4,4,-diaminostilbene -2, 2,-disulfonic acid is tetrazotized, and is coupled with 8-aminonaphthalene-2-a(1,7-gluconic acid) under acidic conditions, and then neutralized with an aqueous solution of nitrogen oxide. The compound represented by the following formula (4_4b) is obtained. [化48]

(B) in the presence of sodium carbonate,

97125650 63 200914539 (4-4a) The compound shown. 3-3. A method for synthesizing a compound represented by the formula (7) and the formula (8), for example, a compound represented by the above formula (7-丨) in a free acid form can be subjected to the following steps (i) to (iv). And manufacturing. (i) According to the general method (for example, refer to Hiroshi, "New Dye Chemistry" (December 21, 2011, Technology News Hall issue), page 3% ~ page 4, page 9} 4-Amino-4' - The nitrostilbene 2, 2, and oxalic acid are diazotized and coupled with a stearamine acid. (i. Next, the caustic alkali is added to carry out a hydrolysis reaction at 6 (four). c. Thereafter, the reaction liquid is salted out to obtain a monoazo compound. (111) The obtained monoazo compound is dispersed in N-A In the base, the sodium carbonate is added as a deacidifying agent, and the temperature is raised to 7 M (rc, and cinnamic acid chloride is added for thiolation. After the p (IV) reaction is completed, it is discharged by water. The compound represented by the above formula (7-1) is obtained as a sodium salt in the form of a free acid. 4. The composition for an anisotropic film can be used for the production of an anisotropic film. The composition for an anisotropic film contains the compound for an anisotropic film of the present invention and a solvent further containing a compound of the present invention dissolved or dispersed in a solvent. Further, the article describes an anisotropic composition or a detailed description below. In the case of the anisotropic film, the compound for anisotropic film of the present invention may be used alone, or two or more kinds of the compounds for anisotropic film of the present invention may be used in combination, or a group of 97,162,650, 2009, 14,539 Å or Knowing other dichroic substances such as dichroic compounds In addition, in order to impart desired properties to the produced anisotropic film or to form a composition suitable for production, various solvents, additives, and the like may be used in combination, even in order to maintain the degree of reduction of alignment. Other compounds such as an ultraviolet absorbing compound or an external absorbing compound such as a ray absorbing compound can be used in combination, whereby the durability of the anisotropic film can be improved, the hue can be corrected, and the polarizing performance can be improved, and various hues can be produced. The solvent used in the composition for an anisotropic film is preferably water, an organic solvent having water miscibility, or a mixture thereof. Specific examples of the organic solvent include methyl alcohol. Alcohols such as ethyl alcohol and isopropyl alcohol; multi-axises such as ethylene glycol, diethylene glycol, and glycerin; cyanobacteria, ethyl sulphon, etc.; Ν-methyl 吼 铜 copper, Ν A single or a mixture of two or more kinds of aprotic solvents such as dimethyl dimethyl carbamide.

When the concentration of the compound for anisotropic film of the present invention is dissolved in the solvent, the concentration is preferably 〇·01% by weight or more based on the solubility of the compound or the concentration at which the compound is formed. Preferably, it is 10 miles. The lower part is more preferably 5% by weight or less, and the other is preferably 41% by weight. The material is tested by the material. The hair is mixed with the compound. If necessary, the surfactant can be added. ==Yin: Subsystem, cation system , non-ionic system of any kind. The addition = is also carried out by o, G1% by weight or more and iG% by weight or less. Further, the composition for anisotropic film of the present invention may be added to the substrate in order to enhance the dyeing of the substrate. Specifically, there is a photo of the original "Three New Dye Processing Lectures, Volume 7 Dyeing 11", Kyoritsu Publishing Co., Ltd., 1972 (I) 15 曰 ' pp. 233-251 or Yamashita Hiroshi, and the work of Kanejiro (5) Knife activity The interface chemistry of the agent and the dyeing aid" Chengwentang Xinguangshe Co., Ltd., which was issued on September 5, 2003, (4) to 173 pages, etc. Or the above interface is active! Inorganic salts such as raw materials, alcohols, glycols, urea, sodium chloride, and s salt. The concentration thereof is usually preferably (four)% by weight or more and more preferably by weight or less. 5. Anisotropic film It is known that an anisotropic film is produced using the compound for anisotropic film of the present invention. The anisotropic property may contain other compounds in addition to the anisotropic coffee compound of the present invention, for example, a known blue dichroic dye, a broken or the like, or the above-mentioned interface active anti-additive. Of course, the compounds represented by the compounds for anisotropic films of the present invention can be combined with each other. Examples of the production method of the anisotropic enthalpy include the following methods (4) to (4). (a) a method of dyeing an extended polyethylene base material substrate by using a solution (an anisotropic film composition) containing the compound for an anisotropic film of the present invention, (6) using an anisotropy containing the present invention A method of stretching a polyethylene polymer base material such as a solution of a compound (an anisotropic film composition), and then extending the polymer substrate such as polystyrene to dissolve the polymer substrate In a solution such as a compounding liquid for an anisotropic film (an anisotropic composition), and a method of stretching after forming a film into a film (4), the compound for anisotropic film of the present invention is dissolved in an appropriate solvent. In the case of preparing a film for forming a film (an anisotropic film), the composition is formed into a film, and the surface of the surface of the scale is used in accordance with the wet type to make the anisotropic film contained in the composition. The method of aligning/layering with a compound may be carried out by using the above-mentioned compounds (4) to (C), but it is particularly preferable to use (4) to (C). The following is a description of a method for producing a retort film using the compound for an anisotropic film of the present invention, and particularly for the above-mentioned (4) to (five) square wire for rutting of the compound for anisotropic film of the present invention. The composition of the anisotropic lining is described in detail. In addition, as for the method of producing an anisotropic film by the method of the above (4) or the composition used in this case, a known method and composition can be suitably used, for example, International No. 2_/1G7() No. 35 (4) The methods and compositions called in etc. In the case of using the compound for anisotropic film of the present invention to form an anisotropic film, in the method of any of the above (4) to (4), the compound for anisotropic film of the present invention is dissolved in a suitable solvent. The solvent contained in the above-mentioned composition for an anisotropic film can be mentioned as a solvent. Further, as the substrate which is dyed by using the solution containing the anisotropic compound of the present invention in the above (4) and (6), or the anisotropic compound of the invention in the above (6) method, Examples of the substrate to be formed include a polyvinyl alcohol resin, a polyvinyl acetate resin, an ethylene/vinyl acetate (heart) resin, a nylon resin, and a polyester. Among them, a polymer material having high affinity with the anisotropic coffee compound of the present invention such as polystyrene is preferred. As the type of polyvinyl alcohol, the optical properties such as the degree of polarization or dichroism are preferable, and the molecular weight and the degree of high-quality are preferably good, and the shrinkage defect or the purpose of suppressing the temperature is determined by the purpose. In terms of both the characteristics of the county and the environmental resistance, it is possible to appropriately adjust the degree of the dichromatic substance f and the degree of chemical conversion of the polyvinyl alcohol or the degree of change (hydrophobic silk synthesis ratio) (4) B-derivative. As a specific method for controlling the interaction between the polymer material and the compound for anisotropic film of the present invention, the combination of the polymer material and the compound for anisotropic film of the present invention is combined with the proton supply property.臓, Ο, Ο NHC0, etc., as a functional group, proton acceptability _N=N_, =, -NH2, old ϋ, -(tetra)-, and phenyl or naphthyl, etc. are effective (R and R , 4 arbitrary substituents). By further adjusting the density of the functional group 1 , the effect of the double color _ property can be improved. The dyeing, film formation and extension in the methods of (a) and (c) can be carried out by the methods generally described below. In the dyeing bath in which the above-mentioned anisotropic composition and (4) the dyeing auxiliary agent such as sodium, Mang, and other inorganic salts, surfactants, etc. are added, usually in the machine, 8 generations of the town, the polymer _ immersion Further, the dyeing is carried out for 10 minutes or less (----- s s s s s s s s s s s s s s s s s s s s s s s s s s s s s s s Alternatively, the organic solution is sprayed, and the present invention is added to a hydrophilic sputum such as a methyl ketone amine, which is formed by a film of the pure sputum, and a film of the sputum liquid. , extrusion method, etc., and the film is reduced into dyed thin enamel. The concentration of the ancient body to be dissolved in the solvent is such that the type of the polymer is not more than 5% by mass of the knives, preferably 10% by weight or more, and usually '5 parts by weight, preferably 20 parts or less. In addition, the concentration of the compound for the anisotropic film which is dissolved in the solvent is about 〇-1_ or more, preferably 〇.8_ or more _== % or less, preferably 2.5% by weight or less. X, hang for 5 weights of dyeing and film formation, and the unstretched film obtained by filming is suitable for stretching in the early axis direction. The invention is characterized in that: the molecules are aligned to exhibit dichroism. As a method of stretching in a single: a method of stretching and stretching by a wet method, a method of stretching by stretching, and a dry type of η 箄The method 4 for stretching and stretching may be carried out by any method. The stretching ratio is carried out under 2 = 聚 is a polymer polymer, and the polyethylene glycol is preferably 3 or more and β or less. = Extension, after the rationale, 'Improve the durability of the extension_ and the degree of polarization (4) acid treatment. By the treatment, the light transmittance of the anisotropic film is increased. As a condition of boric acid treatment, Hydrophilic high score 9712250 69 200914539 sub-polymer and the present invention The concentration of the compound for the film is different, and the concentration of the boric acid is usually 1% by weight or more, preferably 5% by weight or more, usually 15% by weight or less, preferably 1% by weight or less. Further, the temperature is desirably 3 (TC or more, preferably 5 (rc or more, usually the following range. In the case where the boric acid concentration is less than 丨% by weight or the treatment temperature is not full. The treatment effect is small, and in the case where the boric acid concentration exceeds 15% by weight or the treatment temperature exceeds 8 (TC or more, there is a case where the anisotropic 臈 becomes brittle &; 〇 〇 ( ( ( a a a a a The film thickness of the anisotropic film is usually 5 Å or more, particularly preferably 80/zm or more, preferably 200 Å or less, and particularly preferably 5% or less. The compound for anisotropic film of the present invention exhibits a short wavelength. The two-color I·sheng improvement in the region is particularly excellent, and not only the short-wavelength region, but also the high dichroism in all regions having absorption. The so-called short-wavelength region here generally means 380 nm. An area of ~500 nm, the anisotropy of the present invention The characteristic of the compound for J is that it has a high dichroism in the region (b), and the compound can also have absorption on the long wavelength side, and the absorption is extremely large in the short wavelength region. In the short-wavelength region, as long as it has absorption in the above region and exhibits high dichroism, it can be suitably used. The anisotropic film system containing the compound for anisotropic film of the present invention is used in addition to light absorption in the field. The anisotropy can be selected as a polarizing film for obtaining linear polarization, circularly polarized light, or circularly polarized light, and the selection of the composition for permeable membrane formation and the substrate or the composition containing the compound for a directional film of the present invention. It can be functionalized as a refractive index: 97125650 200914539 Various anisotropic films such as conductivity or conduction anisotropy can be used as polarizing elements which can be applied to various versatility. When the anisotropic film is used as a polarizing element, an anisotropic film formed by the method represented by the above (a) to (c) may be used as it is, or a protective layer, an adhesive layer, and a reflection layer may be used. Layers of various functions such as a layer and a retardation layer are laminated and formed as a laminate. In the case where the anisotropic film of the present invention is formed on a substrate as a polarizing element, the anisotropic film formed by direct use is used, and an adhesive layer other than the above protective layer is simply formed by a wet film forming method or the like. Or an antireflection layer, an alignment film, and a layer having various functions described below are formed as a body: as a phase difference; a function of an I film, a function as a brightness enhancement film, a function as a reflective film, and a half-through A layer having an optical function such as a function of a transflective film, a function as a diffusion film, or the like. The layer having the spinning function can be formed, for example, by the following method. The layer which is a function of the retardation film is described in, for example, the extension process described in Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. The layer which is processed to form the function of the 0-lifting film can be formed into a fine hole by a method such as that described in Japanese Laid-Open Patent Publication No. 2002-169025 or the Japanese Patent Publication No. Hei. It is formed by two or more cholesteric liquid crystal layers having different wavelengths. 97125650 71 200914539 A layer having a function as a reflective thin or semi-transmissive reflective film can be formed by a metal thin film obtained by vapor deposition or sputtering. A layer having a function as a diffusion thin layer can be formed by coating a resin solution containing fine particles on the above protective layer. Further, the layer system having a retardation film or an optical compensation can be formed by coating a liquid crystal compound such as a disc-crystalline compound or a ship-crystal compound. The anisotropic film of the compound for anisotropic film of the present invention can be used not only in a liquid crystal display or an organic EL display, but also in that a wide range of color expression can be obtained and a highly heat-resistant polarizing element can be obtained. It is suitably used for applications such as liquid crystal projectors that require high heat resistance, display panels for automobiles, and the like. [Examples] Next, the present invention will be more specifically described by way of examples, and the present invention is not limited to the following examples within the scope of the gist of the invention. In the following embodiments, the two-color ratio is After the rhombohedral polarizer is placed on the spectrophotometer of the incident optical system to measure the transmittance of the anisotropic film, the calculation is performed by the following. s Two-color ratio (D)=Az/Ay Az=-l〇g(Tz)

Ay=-log(Ty)

Tz: transmittance of polarized light with respect to the absorption axis direction of the anisotropic film: transmittance of polarized light with respect to the direction of the polarization axis of the anisotropic film 97125650 72 200914539 [Example 1] 4-amino-4,重量重量。 _ nitrostilbene - 2,2,-disulfonic acid sodium 8.9 parts by weight dissolved in 90 parts by weight of N-methylpyrrolidone, adding sodium carbonate 丨. 6 parts by weight and cinnamic acid chloride 5. 0 weight The reaction was carried out at 6 ° C for 30 minutes. After the reaction was completed, it was discharged from water, and the resulting precipitate was removed by salting out. This material was suspended in 115 parts by weight of water, and 24 parts by weight of sodium hydrosulfide (7% by weight) was added, and the reaction was carried out at 60 C for 30 minutes. After completion of the reaction, a compound represented by the following formula (2-la) which is a sodium salt is obtained by salting out. [化49]

(2-la)

5 parts by weight of the sodium salt of the compound of the above formula (2-la) was dissolved in water (10) by weight. Under the condition of salt g·, add (4) _ G 73 parts by weight to carry out muttonization, freshly expect 0, and the parts by weight are coupled under the test conditions, and the target of the salt-releasing component is used as the nano-salt (H) ) the compound shown. The maximum absorption wavelength (1 cis) in the aqueous solution of this compound is 386 nm. [化 50]

Qt [Embodiment 2]

OH 97125650 73 200914539 In the same manner as in Example 1, a 4-amino- 4,-nitrostilbene-2,2-disulfonic acid sodium was thiolated with cinnamic acid, and the reduction reaction was carried out in the same manner with sodium hydrosulfide. 'And the Qing is paved with a ± (27) Qing compound. Then, the diazonium b-reaction is carried out, and the compound is obtained by the combination of (10) parts by weight under the test conditions, and the compound is obtained as the compound of the formula (2-2). The maximum absorption wavelength (long-term) in the 10_aqueous solution was 389 nm. [化 51]

,so3h j—C—CONH

Ο^ί [Example 3], city 4 - nitrate 'diphenyl (tetra) -2, 2, - dibasic acid sodium 8.9 parts by weight: in 90 parts by weight of water, under acidic conditions of hydrochloric acid, adding nitrous acid steel b The person is subjected to diazotization, and is coupled with the surface enthalpy of 9 parts by weight under the conditions of the test, and is obtained as a compound represented by the formula (2_3a) under the sodium salt by 鴎n [52].

(2 - 3 a) 97125650 200914539 5 parts by weight of the sodium salt of the compound of the above formula (2-3a) was dissolved in a water loo by weight. Next, 4 parts by weight of sodium hydroxide and 2 parts by weight of dimercaptosulfate were added, and the reaction was carried out at 90 C for 6 hours. After the completion of the reaction, the resulting precipitate was filtered by salting out. The material was suspended in 1 part by weight of water, and 1.2 parts by weight of sodium hydrosulfide (70%) was added thereto, and the reaction was carried out at 6 ° C for 30 minutes. After the completion of the reaction, a compound represented by the following formula (2-3b) which is a sodium salt is obtained by salting out. [化53]

5 parts by weight of the sodium salt of the compound of the above formula (2-3b) was dissolved in the N-fluorenyl ratio of "different 50 parts by weight, 0.6 parts by weight of sodium carbonate and cinnamic acid vaporized 2. 5 parts by weight, the reaction was carried out at 60 Torr for 30 minutes. After the completion of the reaction, the precipitate formed by filtration was taken out by salting out, and the compound represented by the formula (2-3) was obtained as a steel salt by obtaining a target hydrazine. The maximum absorption wavelength (λ max) in the aqueous solution of 1 〇 ppm of this compound was 363 nm. [化54]

97125650 75 200914539 [Example 4] 8. 9 parts by weight of sodium 4-amino-4,-nitrostilbene~2,2,-disulfonate was dissolved in 90 parts of water. Under acidic conditions of hydrochloric acid, sodium hexanoate was added to carry out diazotization, and 4.2 parts by weight of aniline methanesulfonic acid was coupled under acidic conditions. After completion of the reaction, sodium hydroxide was added to raise the temperature to 6 (TC, and the hydrolysis reaction was carried out under the reaction of strong base I1. After the reaction was completed, the mixture was neutralized with hydrochloric acid, and then sodium hydrogen sulfide (70%) was added in an amount of 2.4 parts by weight. The reaction was carried out at 6 (rc for 30 minutes). After the completion of the reaction, a compound represented by the following formula (2-6a) as a sodium salt was obtained by salting out.

The weight of the sodium salt of the compound of the above formula (2-6a) is 7 parts by weight of the N-methyl hydrazine, and the ketone is added in an amount of 0.5 parts by weight. 1 serving, at 6 〇. The reaction was carried out for 3 minutes. After the completion of the reaction, it was discharged from water, and the precipitate formed by filtration was taken out by salting out, and the compound represented by the formula (2-6) was obtained as a sodium salt. The maximum absorption wavelength (Amax) in the 1 〇 PPm aqueous solution of this compound was 400 nm. [化56] 97125650 76 200914539

重量重量进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行进行。 Coupling with 2 parts by weight of phenylmorphine under acidic conditions. After completion of the reaction, the material was suspended in 1 liter by weight of water, and 2.4 parts by weight of sodium hydrosulfide (70%) was added thereto, and the mixture was subjected to reverse anesthesia for 3 minutes at 6 (after the reaction was completed) by salting out. The compound represented by the following formula (2_6〇a) is obtained as a sodium salt.

(2 6 0 a)

4 parts by weight of the sodium salt of the compound of the above formula (2-60a) is dissolved in 50 parts by weight of the N-methyl group, and 1.6 parts by weight of sodium carbonate and cinnamic acid chloride are added. The parts by weight were reacted for 30 minutes. After the reaction is over, by

ί| ? I ' error is filtered by salting out to remove the precipitate produced, and to obtain the compound of the formula (2-6G) as a nano salt. The maximum absorption wavelength (Amax) in the 1 〇 PPm aqueous solution of this compound is 407 nm 〇 [Chem. 58] 97125650 77 200914539 Ο - [Example 6]

The same as in Example 4, 4-amino-4'-nitrostilbene~2,2'-diacid sodium 8.9 parts by weight of diazotized, and 1-aminonaphthalene-8-supply acid (peri acid) 4.5 parts by weight of the coupling under acidic conditions. After the reaction is completed, it is taken out by salting out.

Compound. This material was suspended in 250 parts by weight of water, and sodium hydrogen sulfide (70%) was added thereto. 4 parts by weight of 'reaction was carried out at 60 ° C for 30 minutes. After completion of the reaction, a compound represented by the following formula (2-25a) which is a sodium salt is obtained by salting out. [化59]

(2-25a) The sodium salt of the compound of the above formula (2-25a) is 6.3 parts by weight dissolved in the N-hydrazine ratio of each 疋 80 parts by weight, 1.6 parts by weight of sodium carbonate and cinnamic acid chloride are added. The compound was reacted with 0.5 parts by weight, and the reaction was carried out for 1 hour at 6 Torr. After the completion of the reaction, the precipitate formed by filtration was taken out by salting out, and the compound represented by the formula (2-25) was obtained as a sodium salt of the target. The maximum absorption wavelength (λ max) in the 1 Oppm aqueous solution of this compound was 42 〇 nm. 97125650 78 200914539 [Chem. 60]

[Example 7] The same as Example 4, 4~-amino-4, stilbene 2,2,2-dilybdate 8.9 parts by weight diazotized, and 8-amino group- 2-naphthyl (1,7-gluconic acid) 4·5 accented coupling under light conditions. After the completion of the reaction, the compound was taken out by salting out. This material was added to 25 g parts by weight of water, and sodium hydride sulfide (7 (U) 2.4 vol. 1 part') was added to react at 6 ° C for 1 hour. After the reaction was completed, salting was carried out (4) as a touch. The compound shown by the following formula da). [化61]

The sodium salt of the compound of the above formula (2 26a) is 6.3 parts by weight dissolved in the N_曱 base σ ratio bite @同8 0会吾 t+&gt;, the wound is added 'carbonate 1.7 weight And 5,000 parts of cinnamic acid gasification were carried out in the next step. After the completion of the reaction, the sputum produced by the extraction was removed by salting out, and the compound represented by the formula (2-26) was obtained as a sodium salt by obtaining a target. 97125650 79 200914539 The maximum absorption wavelength (Umax) of the 10 卯m aqueous solution of this chemistry is 415 nm 〇 [Chem. 62]

SOaH (2 - 2 6) [Example 8] "The same as 4_Amino_4' _nitrodiphenylethylene u _ 2 ~ Cannes 8.9 parts by weight diazotization ' and 5 -Aminonaphthalene-2-supply acid (1,6-Grape i〇4. 5 coupling under heavy surface conditions. After the reaction is completed, the σ substance is taken out by salting out. The substance is suspended in the water lake. The reaction was carried out by adding sodium hydrosulfide emu 4 parts at 6{rc for 1 hour. After the completion of the reaction, salting out (10) to a compound represented by the formula (2 - (10). [Chem. 63]

HaN

NH, HOaS (2 - 6.3 parts by weight of the sodium salt of the compound represented by the above formula (2-27a) is dissolved in 80 parts by weight of 吼 吼 ming, 'addition of sodium carbonate, 6 parts by weight, and cinnamon g 97125650 200914539 · 〇 by weight, the reaction is carried out at 60 ° C for 1 hour. After the end of the reaction, the X-drain is filtered by salting out to remove the resulting sink, and the target is used as the nano-salt (2- 27) The compound has a maximum absorption wavelength (Amax) of 415 nm in a 1 〇 PPm aqueous solution of this compound.

Ν'Γ&quot;

(2-2 7) [Embodiment 9]

To the 1 GG parts by weight of the distilled water, a sodium salt of the compound represented by the following formula (5)) was added, and 0.05 parts by weight of anhydrous sodium sulfate 〇. 2 parts by weight, and stirred and dissolved, as a dyeing liquid. A polyvinyl alcohol film (0PL film, manufactured by Nippon Synthetic Chemical Co., Ltd., film thickness: 75 Am) was subjected to dipping and dyeing in a dyeing solution of 50 ° C for 1 minute, and after washing the residual dye in 5 (TC water bath, at 5 The solution was extended to 6 times in a 4% by weight aqueous solution of boric acid. After the extension, the residual boric acid was washed in a room temperature water bath to obtain an anisotropic film having a thickness of 30/zm by air blowing. The maximum absorption wavelength and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is known that it has high dichroism. [Chem. 65] 97125650 81 200914539 SO3H ho3s (2-1) [Example 10] 2-2) The sodium salt of the compound shown is substituted for the sodium salt of the compound of the above formula (2), and an anisotropic film is obtained by the same method as in Example 9. The maximum absorption wavelength of the anisotropic film The monomer penetration f I ratio and the two-color ratio at the wavelengths are shown in Table 1, and it is known that it has high dichroism.

[Example 11] 2) An anisotropy was obtained by the same method as in Example 9 except that the sodium salt of the compound of the following formula (2-3) was used instead of the sodium salt of the compound of the above formula (2_D). The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the film has high dichroism.

[Example 12] 97125650 82 200914539 An anisotropy was obtained in the same manner as in Example 9 except that the sodium salt of the compound represented by the following formula (2-6) was used instead of the sodium salt of the compound represented by the above formula (2_ι). Sex film. The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the dichroic property is high. [68]

_ Η [Example 13] The same procedure as in Example 9 was carried out except that the sodium salt of the compound of the following formula (2-60) was used instead of the sodium salt of the compound of the above formula (2-1). The white I1 green film has a maximum absorption wavelength at the a-axis anisotropy and a monomer transmittance and a two-color ratio at the wavelength, and it is known that it has high dichroism. [化69]

K H c2-6〇&gt;

HOaS H»C

[Example 14] An anisotropic film was obtained in the same manner as in Example 9 except that the sodium salt of the compound of the formula (2-25) was used instead of the sodium salt of the compound of the above formula (24). The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the dichroic property is high. [化70] 97125650 83 200914539

,S〇3H

H03s

(2-25) [Example 15] The same procedure as in Example 9 was carried out except that the sodium salt of the compound of the following formula (2-26) was used instead of the sodium salt of the compound of the above formula (2_ι). Anisotropic film. The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the dichroic property is high. [化71]

(2-26) SQaH

[Example 16] An intermediate film was obtained by the same method as in Example 9 except that the sodium salt of the compound of the following formula (2-27) was used instead of the above formula (5)); The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the dichroic property is high. [化72]

97125650 84 200914539 [Comparative Example 1] In addition to the sodium salt of the compound represented by the above formula (2-1), "Chrysophenine (CI-24895) (the following structural formula)" manufactured by Tokyo Chemical Industry Co., Ltd., which has been subjected to desalination purification, is used. An anisotropic film was obtained in the same manner as in Example 9. The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the dichroism is insufficient. [化73] chrysophenine (CI-24895)

°C2Hs [Comparative Example 2] The same procedure as in Example 9 was carried out except that the sodium salt of the compound of the following formula (B-1) was used instead of the sodium salt of the compound of the above formula (2_1:). Directional film. The maximum absorption wavelength of the anisotropic film and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 1, and it is understood that the dichroism is insufficient. [化74] so3h Ο^§-Ν-&lt;^-0=ϋ^ρ^Ν=Ν·Η〇Κ0Η (4) ho3s 97125650 85 200914539 [Table l]

4 parts of aminodiphenylethylene 2,2,-disulfonic acid parts by weight is dissolved in 500 parts by weight of water, and under acidic conditions of hydrochloric acid, sodium nitrite is added to the weight of 1 〇 to be diazotized, and 27 parts by weight of 8-aminonaphthoic acid (1,7-gluconic acid) was coupled under acidic conditions. After the reaction, the compound represented by the following formula (4-4,) was obtained as a sodium salt by passing through a sodium hydroxide aqueous solution. q [化75]

9 parts by weight of the sodium salt of the compound of the above formula (4-4,) was dissolved in 200 parts by weight of N-methylpyrazine, and 3 parts by weight of sodium carbonate and cinnamic acid vaporized by weight parts were added to 6 The reaction was carried out for 2 hours to obtain a compound of the formula (4-4) as a sodium salt. The maximum absorption wavelength (Amax) in the aqueous solution of this compound is 97125650 86 200914539 444 nm. [化76]

29 parts by weight of monoaminostilbene- 2,2'-disulfonic acid is dissolved in water 625 to promote work T, and under acidic conditions of hydrochloric acid, sodium nitrite n weight ^, diazotization, and 5- Aminonaphthalene-2-sulfonic acid (1,6-gluconic acid) was used in an amount of 34 parts by weight to obtain a compound represented by the following formula (4-5) as a sodium salt.

Coupling with k pieces. After the reaction, 9 parts by weight of the sodium salt of the compound of the above formula (4-5,) was dissolved in 200 parts by weight of sodium chloropyrrolidone by adding an aqueous solution of sodium hydroxide (North 77), and sodium carbonate 3 weight was added. The mixture was reacted with 5 parts by weight of cinnamic acid chloride at 60 ° C for 2 hours to obtain a compound of the formula (4-5) as a target under sodium hydrazine. This compound is ΙΟρρπι 434nm. The maximum absorption wavelength in aqueous solution (λ_ is [讹 78] 97125650 87 200914539

[Example 19] 33 parts by weight of 4-amino-4'-nitrodiphenylacetin-2,2,-dihydrobine sodium was dissolved in 670 parts by weight of water, and nitrous acid was added under acidic conditions of hydrochloric acid. 7 parts by weight of sodium was used for the carbonization, and 8 parts by weight of the m-methyl exfoliate was coupled under heterogeneous conditions. After the reaction, the mixture was neutralized with an aqueous sodium hydroxide solution to obtain a compound represented by the following formula (4-29a) as a sodium salt. [化79]

3 parts by weight of the sodium salt of the compound of the above formula (4-29a) was suspended in 600 parts by weight of N-methyl ketone. Subsequently, 9 parts by weight of sodium carbonate and 13 parts by weight of cinnamic acid chloride were added and reacted at 6 ° C for 3 minutes. After the reaction, saline was added to the system to remove the precipitate produced by filtration. The cake was suspended in 1250 parts by weight of water and added with 8 parts by weight of sodium hydrosulfide (7% by weight) at 6 Torr. The reaction was carried out under the arm for 1 hour to obtain a compound represented by the following formula (4-29b) as a sodium salt. [化80] 97125650 88 200914539

31 parts by weight of the sodium salt of the compound represented by the above formula (4-29b) is dissolved in a water-based weight fraction and a NL amaranth (10) weighting material, and under the conditions of Wei heterogeneous, 2 parts by weight of the diazotization is added. Coupling was carried out under acidic conditions with 6 parts by weight of 8-amino-2-carboxylate α,7-gluconic acid. After the reaction, it was subjected to neutralization by an aqueous solution of sodium hydroxide, and (d) to a compound of the following formula *(d). [化81]

(4-29c) One part by weight of the sodium salt of the compound represented by the above formula (4 length) was dissolved in a water content portion and N-methylxanthone (10) parts by weight. Under acidic conditions of hydrochloric acid, nitroxyl _ 1 part by weight is added and linearized, and 2 parts by weight of the stretching material are coupled under the test conditions, thereby obtaining a compound represented by the following formula (4)) . The maximum absorption wavelength (also max) in the 1 〇 aqueous solution of this compound was 461 nm. [化82] 97125650 89 200914539

Η

ΌΗ (4-29)

The sodium salt of the compound of the above formula (6)) is added to 1 GG parts by weight of hydrazine water. 重量. 05 parts by weight and 2 parts by weight of anhydrous sulphur sulphate, and (4) dissolved, as a dyeing liquid. The polyvinyl alcohol film (binding film) manufactured by Nippon Synthetic Chemical Co., Ltd. was impregnated and dyed in the dyeing solution of the order in the time shown in Table 2, and after washing the residual dye in a 5 〇C water bath, After the extension of the 重 仃 extension m of the 4th heavy side acid water, the residual rotten acid was washed at room temperature with a water bath to obtain an anisotropic film having a thickness of 3 Mm by air blowing. The maximum absorption wavelength of the anisotropy enthalpy in 38 Å to .nm and the monomer transmittance and the two-color ratio at the wavelength are shown in Table 2, and it is understood that the product has high dichroism. [Example 21] An anisotropic film was obtained in the same manner as in Example 2 except that the sodium salt of the compound of the above formula (4-5) was used instead of the sodium salt of the compound of the above formula (4-4). . The maximum absorption wavelength of the anisotropic film at 380 to 780 nm and the monomer transmittance and the two color ratio at the wavelength are shown in Table 2, and it is understood that the product has high dichroism. [Example 22] In addition to the sodium salt of the compound of the above formula (4-29), the sodium salt of the compound of the above formula (4-4) 97125650 90 200914539 was used, and the time was other than the dyeing time shown in Table 2, An anisotropic film was obtained in the same manner as in Example 20. The maximum absorption wavelength of the anisotropic film at 380 to 780 nm and the monomer transmittance and the two color ratio at the wavelength are shown in Table 2, and it is understood that the product has high dichroism. [Comparative Example 3] In place of the compound represented by the above formula (4-4), "Chrysophenine (CI-24895)" manufactured by Tokyo Chemical Industry Co., Ltd., which has been subjected to desalination purification, was used.

An anisotropic film was obtained in the same manner as in Example 20 except for the sodium salt. The maximum absorption wavelength of the anisotropic film at 380~780nm and its wavelength

The monomer transmittance &amp; two-color ratio is described in 纟2, and it is known that bismuth has high dichroism. [Table 2]

4 parts of 4-amino- 4,-nitrodiphenylethylene-2,2'-didendronate was dissolved in 9 parts by weight of water. In an acidic condition of hydrochloric acid, a weight fraction of sodium nitrite is added to carry out diazotization, and an aniline is sb. After completion of the reaction, sodium hydroxide was added and the temperature was raised to 6 Torr. 〇, in the strong recording of the hydrazine reaction. After completion of the reaction, the di(tetra) acid is neutralized, and the salt is subjected to salting out to obtain a compound represented by the following formula (7-la) as a sodium salt. 97125650 91 200914539 [化83] so3h HOsS,

(7-la) f The sodium salt of the compound of the above formula (7__la) is 5.2 parts by weight dissolved in N-mercapto quinone and 50 parts by weight, and 0.6 parts by weight of sodium carbonate and cinnamic acid chloride are added. 2·5 parts by weight, at 6〇. The reaction was carried out for 30 minutes under the armpits. After the reaction, 'discharged from water', the precipitate produced by filtration was taken out by salting out, and the compound of the formula (7-1) below the sodium salt was obtained by obtaining the target. The maximum absorption wavelength (Amax) in the 10 ppm aqueous solution of this compound was 397 nm. [化84] 〇2n

H〇3:

(7-1) [Example 24] 8.9 parts by weight of sodium 4-amino-4,-nitrodiphenylethylene-2,2,disulfonate / glutamic solution was dissolved in 9 parts by weight of water. 2 parts by weight of aniline _ω_methanesulfonic acid was coupled with aniline _ω_methanesulfonic acid under acidic conditions. After the completion of the reaction, sodium hydroxide was added, and the temperature was raised to 6 (TC, and the hydrolysis reaction was carried out under a strong test. After the completion of the reaction, 'after neutralization with hydrochloric acid', salting-out was carried out to obtain the following formula as a sodium salt (7- Compound shown in 2a). 97125650 92 200914539 [Chem. 85]

(7 - 2a) The sodium salt of the compound of the above formula (7-2a) is 5.2 parts by weight dissolved in 50 parts by weight of N-decylpyrrolidone, 0.6 parts by weight of sodium carbonate and cinnamic acid chloride 2 are added. 5 parts by weight, the reaction was carried out at 60 ° C for 30 minutes. After the reaction, the mixture was drained from the water, and the resulting precipitate was removed by salting out. The material was suspended in 100 parts by weight of water, and 1.2 parts by weight of sodium sulphide sulfide (70%) was added, and the reaction was carried out for 6 minutes at 6 (TC). After the reaction was completed, it was discharged from water and filtered by salting out. The resulting precipitate was taken out to obtain a compound of the following formula (7-2) as a target sodium salt. The maximum absorption wavelength (Amax) in the aqueous solution of this compound was 403 nm.

(7-2) [Example 25] To a solution of 1 part by weight of distilled water, a sodium salt of the compound of the following formula (7-丨) was added. 0.05 parts by weight with anhydrous sodium sulfate 〇. 〇 2 parts by weight, and Stir and dissolve as a staining solution. The polyvinyl alcohol film (0PL film) was subjected to dipping and dyeing for 5 minutes in 5, rc of this dyeing solution, 97125550 93 200914539, after washing the residual dye in a 50 〇C water bath, and then 4% by weight of the boric acid aqueous solution at 5 〇 The extension was extended to 6 times. After the extension, the residual boric acid was washed in a room temperature water bath, and dried by air blowing to obtain an anisotropic film having a thickness of 30/zm. The maximum absorption wavelength of the anisotropic film was 420 nm, and its wavelength was The monomer has a transmittance of 40.9% and a two-color ratio of 49.1, which has high dichroism.

SQaH HCbS (7-1) [Example 26] The same method as in Example 25 except that the sodium salt of the compound of the following formula (7-2) was used instead of the sodium salt of the compound of the above formula (7) The anisotropic film has a maximum absorption wavelength of 415 nm, and a monomer transmittance at a wavelength of 44. 2% 'the two-color ratio is 37.1. It has high dichroism. Main 97125650

(7-2) 94 200914539 In addition, this application is based on a Japanese patent application filed on Jul. 9, 2007 (Japanese Patent Application No. 2007-179638), and Japanese Patent Application filed on Sep. 7, 2007. May 2007-232958), Japanese patent application filed on September 14, 2007 (Japanese Patent Application No. 2007-239812), Japanese Patent Application filed on November 15, 2007 (Japanese Patent Application No. 2007-296231) and 2007 The Japanese patent application filed on Dec. 21 (Japanese Patent Application No. 2007-330489) is incorporated herein by reference. 97125650 95

Claims (1)

200914539 VII. Patent application scope: ι_ An anisotropic compound, characterized in that the free acid form is as shown in the following formula (1): Ar1-N々 (1) (S〇3H)p (S03H)k [In the formula (1), the L1 system - (CH = CH) r_ group or a (CsC) s_ group, r &amp; s respectively represent 1 to 5 An integer of Ar which may have a substituent, a phenyl group which may have a substituent, a heptyl group which may have a substituent or a heterocyclic group which has a substituent; m is an integer of 0 to 3; and p and k each independently represent Q or i, However, it is not simultaneously (8) a hydrogen atom or an organic group of X1; a X-ray atom, a nitro group, an amine group which may have a substituent or a group of the following formula (Ι-a) wherein χ2 is a hydrogen atom, When the oxime group and the amine group which may have a substituent, m is not 0; [Chem. 90] (1-a) (In the formula (1-a), the Ar2 group may have a substituent phenyl group, may have a substituent of 97,256,650 96, 200914539 anthranyl group or a heterocyclic group which may have a substituent; a phenyl group of a substituent, a naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; an integer of η series 0 to 3)]. 2. The compound for an anisotropic film according to the first aspect of the invention, wherein the above formula (1) is represented by the following formula (2): In the formula (2), Ar2, Β1, L1, X1, k, η, and ρ are the same meanings as in the above formula (1), respectively. 3. The compound for an anisotropic film according to item 2 of the patent application, wherein the above formula (2) is as shown in the following formula (3): [化92] [In the formula (3), 'Αι^'Β^ΐΛΧ1 and η are the same meanings as in the above formula (2), respectively. 4. The compound for an anisotropic film according to the first aspect of the invention, wherein the above formula (1) is represented by the following formula (4): [Chem. 93] 97125650 97 200914539 Ν ,Ν—A (4) In the formula (4), Ar1, Ar2, Β1, L1, X1, k, η, and ρ are the same meanings as in the above formula (i), respectively. 5. The compound for an anisotropic film according to item 4 of the patent application, wherein the above formula (4) is represented by the following formula (5): [Chem. 94] (5) [In the formula (5), a phenyl group which may have a substituent, a phenyl group which may have a substituent, or a heterocyclic group which may have a substituent; L2 is -(CH=CH)r, - Base or ·~("= threshold, fly a - C) s'-base 'r and s, each independently represents an integer from 1 to 5; X3 is a hydrogen atom or an organic group; Am, (4) are respectively related to the above formula (4) Same meaning in the middle.] 6. If applying for a full-time ninth compound, the above formula (5) is as shown in the following formula (6): [Chem. 95] 97125650 98 200914539 [Formula (6) towel 11 may have a substituent of 1,4-phenylene or may have a substituent of 1,4-naphthyl; B13 may have a substituent, 4-extension or The naphthyl group which may have a substituent; the X1 and X3 systems have the same meanings as in the above formula (5). 7. The anisotropic compound according to the scope of the patent application, wherein the above formula (1) is as shown in the following formula (7): [Chem. 96] -X1 (7) [Ό] A money atom, a nitro group or an amine group which may have a substituent; Α and Α 卿 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立 立a heterocyclic group having a substituent; j is an integer of 0 to 2; k^P is the same as in the above formula (1). An anisotropic film compound according to item 7 of the patent application of the present invention, wherein the above-mentioned 97125650 99 200914539 formula (7) is represented by the following formula (8): So3h [In the formula (8), X, X, A, a2, L1, and j are the same meanings as in the above formula (7). 9. A compound characterized in that the free acid form is as shown in the following formula (9): [In the formula (9), Ar21 may have a substituent of a substituent, a stretching naphthyl group or a heterocyclic group which may have a substituent; h is an integer of 1 to 5; t is 0 to 3 Integer; F is a phenyl group which may have a substituent, may have a residue, a county or a gas atom; is a hydrogen liver, Wei, may have a collision, and the base is shown in (9-a) When X is a hydrogen atom, a nitro group or an amine group which may have a substituent, t is not 0; 97125650 100 200914539 (9-a) (In the formula (9-a), the 'Ar22 system may have a substituent a phenyl group, a naphthyl group which may have a substituent or a heterocyclic group which may have a substituent; B22 is a phenyl group which may have a substituent, and a naphthyl group which may have a substituent _ a heterocyclic group which may have a substituent; u is an integer of 0 to 3)]. 97125650 101 200914539 IV. Designation of representative drawings: (1) The representative representative of the case is: None (2) Simple description of the symbol of the representative figure: None 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: (1) (1-a) 97125650 3