TW201100377A - Chemical compound - Google Patents

Abstract

This invention provides a chemical compound represented by the following general formula (1): Wherein X represents an alkyl group having a number of carbon atoms of 2 to 20, a cyclic alkyl group having a number of carbon atoms of 3 to 20 or an aromatic hydrocarbon group having a number of carbon atoms of 6 to 20, which aromatic hydrocarbon group may or may not be substituted; E1 and E2 each independently represents a bonding group or a single bond; A1 and A2 each represents a divalent aromatic hydrocarbon group which may or may not be substituted; B1, B2, B3 and B4 each independently represents a bonding group or a single bond; F1 and F2 each independently represents an alkanediyl group having a number of earbon atoms of 1 to 12 which is substituted or unsubstitute, and one or more than one of the methylene group constituting the alkanediyl group may be substituted with an oxgen atom; and P1 and P2 each independently represents a hydrogen atom or polymeric group.

Description

201100377 VI. Description of the Invention: TECHNICAL FIELD OF THE INVENTION The present invention relates to a novel compound. [Prior Art] A flat panel display device (FPD) includes a member using a film such as a polarizing plate or a phase difference plate. Japanese Laid-Open Patent Publication No. 2003-287623 discloses a retardation film which is applied to a support by a solution obtained by dissolving a polymerizable compound represented by the formula (III-1-1) in a solvent. After the base material, the polymerizable compound is obtained by polymerization.

(111-1-1) SUMMARY OF THE INVENTION The present invention provides the following. [1] A compound represented by formula (1) P1, W1

2, A2 I γ Β 4, ρ2 (1) (wherein 'X represents an alkyl group having 2 to 20 carbon atoms, a ring-shaped group having a carbon number of 3 to 20, or a substituted or unsubstituted aromatic having a carbon number of 6 to 20 a hydrocarbon group; Ε1 and Ε2 each independently represent a linking group or a single bond; 4 321987 201100377 . A and A forces independently represent a substituted or unsubstituted divalent aromatic hydrocarbon group; β B, B and B points a group or a single bond; _F!AF2 independently represents a substituted or unsubstituted carbon number of 1 to 12, and a methylene group constituting one or more of the calcined bases may be substituted An oxygen atom; P and P each independently represent a hydrogen atom or a polymerizable group). [2] The compound of [1], wherein, in the formula (1), the group represented by the formula (P-1) is independently represented by a broad: R{ R2 "r3 (P_1) (wherein R!, R2 and R3 each independently represent a carbon number! to an alkyl group or a ruthenium atom of 6) [3] A composition comprising a compound of [丨] or [2] and a photopolymerization initiator G [4] A film obtained by polymerizing a compound of [. or !^]. [5] A color filter comprising a film of [4]. [6] A flat panel display device comprising [4; [7] A method for producing a film comprising the steps of applying a compound of [丨] or [2] onto a substrate or forming an oriented film on a substrate. The novel compound of the present invention is a compound represented by the formula (1) (hereinafter abbreviated as the compound (1))·· 5 321987 201100377

X (wherein X represents an alkyl group having 2 C 20 carbon atoms, a cyclic alkyl group having 3 to 2 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms; and E and E are each independently The ground represents a linking group or a single bond; and the division represents the unsubstituted divalent aromatic smoky group; B, B2, B3, and B4 each independently represent a linking group or a single bond; and F1 and F2 independently represent carbon The substituted or unsubstituted alkanediyl group of '12' may constitute one or more sub-f groups of the alkanediyl group which may be substituted with an oxygen atom; and P and P2 each independently represent a hydrogen atom or a polymerizable group). The alkyl group having 2 to 20 carbon atoms represented by X may, for example, be an ethyl group, a propyl group, an isopropyl group, a butyl 'isobutyl group, a secondary butyl group, a tertiary butyl group, a pentyl group or a methyl butyl group. 3-methylbutyl, hexyl, 1-decylpentyl, 4-methylpentyl, heptyl, 1-decylhexyl, 5-decylhexyl, octyl, benzylheptyl, decyl, 1- The mercaptooctyl group, the decyl group, the undecyl group, and the dodecyl group are preferably those having a carbon number of 3 to 12. The cyclic alkyl group having 3 to 20 carbon atoms may, for example, be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, and a cyclodecyl group, and has a carbon number of 3 A cycloalkyl group of 12 is preferred. Examples of the unsubstituted aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-yl group, a 2-position group, and a 3-fluorenyl group. An unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms is preferred. Such an aromatic hydrocarbon group may have a substituent, and the substituent may, for example, be a methyl group, an ethyl group, a propyl group 321987 6 201100377, a ruthenium wire, a methoxy group, an ethoxy group, a propoxy group or the like having a carbon number of 1 to 5 oxy groups, and fluorine atoms, chlorine atoms, desert atoms and other dentate atoms. The substituted aromatic hydrocarbon group may, for example, be 4-fluorophenyl, 4-methoxyphenyl, ethoxyphenyl, nonylphenyl, 4-ethylphenyl, and 3,5-dimethyl stupid 6 The aromatic hydrocarbon group X to 12 is preferably an alkyl group having 3 to 12 carbon atoms or a carbon number. Ο The surface base or single bond, the linking system contains 21⁄2 organic groups. Specific examples thereof include: anthracene, -o-co-, -0-C0♦, a C0_NR6_, a nourishment (3)-, a side 2, and a H 6 represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. (Example: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hexyl, etc.). In the basin, it is preferable that *P (* indicates a bonding portion with the U-ring-burning diyl group). The unsubstituted 2 fresh aromatic hydrocarbon group represented by A and A is preferably a fluorenyl group consisting of the following formula r, to the aryl group of the 5-membered ring or the 6-membered ring aromatic group. The hydrogen atom in the aromatic hydrocarbon group may be a (iv) atom, a carbon number to 4 (for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc.), carbon number i to Alkoxy groups of 4 (e.g., methoxy, ethoxy, 3-yl: isopropoxy, butoxy, tert-butoxy, etc.), trifluoromethyl, cyano, or nitro substituted.

(4) (9-5) Such a substituted or filamentous divalent (four) _ group can be, for example, 321987 7 201100377 1,4-phenylene, naphthalene-2,6 and ―2,7·; The phenylene group is preferably a "base group", a phenylene group, and a phenyl group, and each independently represents a linking group or a single bond, and the cascading group contains a divalent organic group. Specific examples thereof include, for example, t-〇, 卿, , -s:, r, rc. 八κ-CO-, -CO-, 0-, -0, -, _〇-c〇-〇_, _C0... and single button are preferred. Ui2-0-, B and B2 are preferably _〇. It is preferable that β3 and a bonding site of * _〇 c〇 or F2 are used. (Tables are not combined with F-.2, Γβ3 and β4, for example, the group shown in Table 1 below. Table Ή骇Β, * Table reading F, F2 bonding part blocking and B blocking * Indicates the bonding site with it. [Table 1] Factory. Here, R6 means the same meaning as above. And -C0-0- . . _ - r ^LU-〇~ χ

And a substituted or unsubstituted alkanediyl group having a carbon number of 1 to 12 as shown by F2, 321987 8 201100377 by an anthracene group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a heptyl group. Preferably, the unsubstituted alkanediyl group having a linear number of 1 to 12 carbon atoms, such as a decyl group, a hydrazine group, a hydrazine group, an undecyl group, a dodecyl group, or a branched group, is preferred. The unsubstituted alkanediyl group having 4 to 8 carbon atoms is preferred, and the alkanediyl group having 4 to 6 carbon atoms is particularly preferred. The alkanediyl group may have a substituent. Further, one or more methylene groups constituting the alkanediyl group may be substituted with an oxygen atom. The group in which one or more methylene groups constituting the alkanediyl group may be substituted with an oxygen atom may, for example, be -CH2-CH2-O-CH2-CH2-, 〇-CH2-CH2-0-CH2-CH2-0 -CH2-CH2-, and -CH2-CH2-0-CH2-CH2-0-CH2-CH2-0-CH2-CH2-. At least one of P1 and P2 is preferably a polymerizable group, and P1 and P2 are preferably a polymerizable group. The term "polymerizable group" means a group which can participate in the polymerization reaction of the compound (1). The polymerizable group may, for example, be a group represented by the following formulas (P-1) to (P-5). The group represented by (P-1) and (P-2) is preferred, and the group represented by (P-1) is preferred. The alkyl group having 1 to 6 carbon atoms may, for example, be an anthracenyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, a pentyl group or a hexyl group.

(P-1) (P-2) (P-3) / (P-4) (P-5) (wherein R1, R2, R3, R4 and R5 independently represent a carbon number of 1 to 6 Base or hydrogen atom). Specific examples thereof include 1-methylvinyl group, vinyl group, and p-diphenyl 9 321987 201100377 ethylene group, epoxy group, decyl epoxy group, group of formula (P_6), and mala Imino group. The plant (1) (P-6) ch3 compound (1) may, for example, be a compound represented by the formula (1-al) to (l-a50). 10 321987 201100377 〇—〇4^~~〇~^

Ο Ο

t)-C5H1Q-〇H0>-C

ο ο (1-a1) (1-a2)

^~l5-C6H12-〇-^-C

)^Q)-o-c6h12- 0 ο Υ (1-a3)

Vc7h14-〇 ο

(1-a4) .0 ^O-CeH^-OnQ-O^^ _ O-Q-O-CeH^-O^ (1-a5) 1/P_c6h12-〇-<^^-c

0.0, 尸"O^O'CsH12_0\= (1-a6)

2 fly ο ο (1-a7) ^-c6h12-o-^^-c

(1-a8) (1-a9) Ann \ OOgH-ij

ο ο o'c6h12-彳 Υ (1-a10) 11 321987 201100377 Ο ^~1d-C6H12-〇4 )Ό-〇ν..„

o 0 0 p

0-C4H8-〇hQ-C

pHQ-〇-c4H8-' 0 o (1-a12) ^>-c5h10-〇hQ-c

P^J^OCS^〇~ (1-a13) , 0 ^~Ίκ:6η12-ο-^κ^

0 0 ^Q..,{O-〇C6H12-〇〆 (1-a14) p

)-C7H14-〇H0^C

K>{分 0C7H1T , 0 0 )-CeH16-〇-^-' JD-CsH12-〇^h

Jh>c8h16-

Y h〇-C6H12- 0, tC6H12-〇-^H My, 〇-C6H12-〇^^-i

,〇^-〇-c6Hi2^ P-O_0C6H12_l p-〇-0'C6H12-0v (1-a19), 0 (1-a20) 12 321987 201100377

(1-a21) (1-a22) Ρ 〇-〇4Η8-ο

Ο

(1-a24) (1-a25) /τΛ o-c7h14-o- (1-a26) Ο 々〇-C8H16-〇-Qh

~O^〇C8H16-〇〆 (1-a27)

(1-a28) (1-a29) "If 2-α

0 0 )^o-c6H12-o>_/ (1.a3〇) 13 321987 201100377 .c6h12-o-^ ^1>C6H12-.

hQk>C6H12-〇(i-a31)

一〆(1_a32) C6H12-〇^K^ H^G^〇c6H12-p (1_a33) c6h12-o

Kh

/r〇^-o-<z^2-o^ (1a35) 〇-c6h12-oh:

(1-a37) 14 321987 201100377

(1-a38) f\-, C6Hi2' (1-a39)

<° O-CgH^^O

O

Heart { points. C6h12-:〆(1__ 卢〇-C6H12-〇^^

^0_O_0C6Hl2-〇^_/ (1-a41) C6H12-〇

(1_a42) ❹ ^〇-〇6Η12-〇^〇>,..〇η〇^°^Η°^°·°6Ηι2~^ d-a43) 15 321987 201100377

(1-a44) Heart points. .C6H12'

K>" points. (1-a45) 〇C6H12 - 〇 ^〇-C6H12-〇-^

-<Q>"0'C6H12-| \Jk>c6h12—〇〆(1a46) (1-a47) b p

O-^O^q ^o-<Q-〇.c6h12-〇^ (1-a48) p

^〇-C6H12-〇-〇-C

O

Y (1-a49) 0 ^o-c6h12-〇-〇-°),

o (1-350) The compound (1) can be appropriately combined with the conventional organic synthesis reaction described in Methoden der Organischen Chemie, Organic Reactions 'Organic Syntheses' Comprehensive Organic Synthesis, New Experiment 16 321987 201100377 Chemical Lecture, etc. (eg condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction, Wittig reaction, Schiff test reaction, benzylation reaction, simple reaction, eucalyptus-gongpu reaction, root bank reaction, Xiongtian reaction, Laoshan reaction,

Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, aldol reaction, etc.). For example, by reacting a compound represented by the formula (M) with a compound represented by the formula (1-2) to obtain a compound represented by the formula (1-3), the obtained compound represented by the formula (1-3) and The compound represented by the formula (ι_4) is reacted to obtain the compound (1). H,

(1-1) Ο

(wherein 'E1, E, A1, A2, B1, B2, B3, B4, F1, F2, P1, P2 and X have the same meanings as described above). Reaction of a compound represented by the formula (1-1) with a compound represented by the formula (1-2), and a reaction of a compound represented by the formula (1-3) with a compound represented by the formula (1-4), 17 321987 201100377 It is preferably carried out in the presence of a condensing agent. A condensing agent can be used by a person skilled in the art. The composition of the present invention contains the compound (1). The composition of the present invention may contain one kind of compound (1)' or may contain two or more kinds of compounds (υ. The composition of the present invention may contain a liquid crystal compound different from the compound (such as ruthenium). Specific examples of such a liquid crystal compound may be used. For example, in the LCD Handbook (Edited by the Liquid Crystal Manual Editorial Board, Maruzen (share), issued on January 3, 2013), "3rd ♦ Molecular Structure and Liquid Crystallinity" The compound described in the "3.3 棒 rod-shaped liquid crystal molecule" is a compound having a polymerizable group. The composition of the present invention may contain two or more kinds of liquid crystal compounds. The liquid crystal compound may, for example, include a group represented by the formula (4). The compound (hereinafter abbreviated as the compound (4)): Ρ11-ΒΙ1-Ε11-Β12-ΑΙ1-β13- (4) (wherein Ρ11 represents a polymerizable group; represents a divalent alicyclic hydrocarbon group or a divalent aromatic hydrocarbon group) The divalent halo-type light-based group and the divalent aromatic hydrocarbon group may have an alkoxy group derived from a (iv) atom, a carbon number to a 6= group, a carbon number i to 6, a carbon number i to 6, carbon

a number of substituents of the group i to 6 of the neooxy group, the cyano group and the determinant group; the mountain core 1U b11 represents -〇-, -s-, _C0_0_, -0_C0~0, m6, to T: base: B: 2 and? Do not stand independently - CEC_, _CH^^ S-, -C('-, ~c(=〇)-〇_, _〇-c(·, Na(4)—, 321987 18 201100377 -CH=N-,- N=CH-, -N=N-, -C(=0)-NR16-, -NR16-C(=0)-, -0CH2-, -OCF2-, -CH2〇-, -CF2〇-, - CH=CH-C(=0)-0-, -0-C(=0)-CH=CH-, or a single bond; E11 represents an alkanediyl group having 1 to 12 carbon atoms, and the alkanediyl group may have a substituent selected from the group consisting of a carbon number of 1 to 5, an alkoxy group having 1 to 5 carbon atoms, and a haloalkoxy group having 1 to 5 carbon atoms, which is selected from the group consisting of The mercapto group may be substituted by -0- or -C0-. The polymerizable group represented by P11 is preferably a radical polymerizable group or a cationic polymerizable group, from the viewpoint of high reactivity of photopolymerization. From the viewpoint of easy handling and easy production of a liquid crystal compound, the polymerizable group represented by P11 is preferably a group represented by the following formulas (P-11) to (P-15):

(P-11) (P-12) (P-13) (P-14) (P-15) 〇 (wherein, R17 to R21 each independently represent an alkyl group having 1 to 6 carbon atoms or a hydrogen atom). Specifically, for example, the groups represented by the following formulae (P-16) to (P-20) can be mentioned. H3C /= \= /〇\ 〇! \ /,ch3 "? CH3 (P-16) (P-17) (P-18) (P-19) (P-20) Polymeric basis (P- 14) to (P-20) is preferably a group, for example, vinyl, stilbene, epoxy, propylene oxide group 19 321987 201100377 (oxetanyl) ° 丨广—B! - particularly preferred for propylene oxy or methacryloxy. The carbon number of the aromatic hydrocarbon group and the aliphatic hydrocarbon group of Α11 is usually from 3 to 18, preferably from 5 to 12, and preferably from 5 or 6. Α11 is preferably 1,4-cyclohexylene or 1,4~, and Ε11 is preferably a linear carbon number of 12 to alkanediyl. The fluorenyl group contained in the alkanediyl group. It may be substituted with -0-. Specifically, for example, methylene, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, thiol, and Sulfhydryl, decyldecyl, dodecyl, -CH2_CH2_〇_CH2-CH2_, -CH2-CH2-O-CH2-CH2-O-CH2-CH2-, and -CH2-CH2-O- The CH2-CH2-O-CH2-CH2-O-CH2-CH2-indole compound (4) may, for example, be a formula (I), a formula (I), a formula (in), a formula (IV) or a formula (V). And the formula (VI) Was:? Ρπ_Βπ_Επ_Βΐ2_Απ_Βΐ3_Αΐ2_Βΐ4_Αΐ3_Βΐ5_Αΐ4_Βΐ6_Εΐ2_Βΐ7_ρ] 2 ^ ι ^ ρΠ_ΒΠ_ΕΠ_Βΐ2_ΑΠ_Βΐ3_Αΐ2_Βΐ4_Αΐ3_Βΐ5_Αΐ4_ρ11 (π) ρΠ_Β "_ΕΠ_Β12_ΑΠ_Βΐ3_Αΐ2_Βΐ4_Αΐ3_Βΐ5_Εΐ2_Βΐ7_ρ12 ρΠ_ΒΠ_ΕΠ_Β12_ΑΠ_Βΐ3_Αΐ2_Βΐ4_Αΐ3_ρ11 〇ν) ρΠ_ΒΠ_ΕΠ_ΒΙ2_ΑΠ_Βΐ3_Αΐ2_Βΐ4_Εΐ2_Βΐ7_ρ12 (γ) u-Bu-En-Bl2-ku-Bu ~ kn- ¥ n (VI) (in the formula, Α12 to Α14 Synonymous with Α11, Β14 to Β16 are synonymous with Β12, Β17 is synonymous with Β11, Ε12 is synonymous with Ε11; where 'F11 denotes a hydrogen atom, an alkyl group of carbon number ι to η, an alkoxy group having a carbon number of 1 to 13, a cyano group , nitro, trifluoromethyl, dimethylamino, hydroxy, 20 321987 201100377 hydroxy fluorenyl, carbhydryl, sulfo (-S 〇 3H), carboxyl, alkoxycarbonyl having 2 to 11 carbons, or The halogen atom, the aforementioned alkyl group and the methylene group contained in the aforementioned alkoxy group may be substituted by -0-). Specific examples of the compound (4) include, for example, the formula (〖- υ to the formula (丨_4), the formula (II-1) to the formula (II-4), the formula (III-1) to the formula (111_26), Formula (Ιν_υ to formula (IV-19), formula (V-1) to formula (V-2), formula (νι_υ to formula (νι__6)). However, in the following formula, kl and k2 represent 2 The number of such liquid crystal compounds is better because it is easy to synthesize or is commercially available.

321987 21 201100377 jO-(CHdid·. 'O^_Q_^_^~O"<^CH2)k2'0~^_ (Μ) servant __(four) seven (four) ^〇-(CH2)kf〇-Q^ _^^^Q-〇~(CH2)k2-〇^ (μ3)

(X〇H2)k2-H 3- 0-(CH2)k<

^ (M) (11-1) 50-(0^.00^0^0^0^^ (II-2) ^Q-(CH2)k<C>(^°_^^^(^〇' (〇H2)k2^ (II-3)

=3-〇~(CH2)k1,0 •O^Q^OfO^HCH as-Η M 321987 22 201100377 ^〇«Q_〇:^0"〇~(CH2)k2_〇'JL= 3-° -' (CH2)ki-〇- (m-1)

❹

〇-(CH2)k-〇 -0 especially >

〇-(CH2)k2' 3-〇-(CH2)k1-〇(丨丨丨-2)(III-3) (IIW) (m-5) (in-6) (III-7) (III- 8) 23 321987 201100377

(111-9) (111-10) _J^-〇-(CH2)k1—(CH2)k2-〇-^__ ("M 1) (111-12)

(111-14) Br } N〇2 -0—(CH2)k2—〇' (111-15) (111-16) N02,·〇卜O—(CH2)k2——3^°~(CH2) Ki_0 =3k)_(ch汍"〇-〇-(CH2)k2-〇- (111-17) C- (111-18) (111-19) 24 321987 201100377

〇-(CH2)k1—Ο

O—(CH2)k2—〇

-Ο—(CH2)k—〇 ο—(CH2)k—0’

Ο—(CH2)k2 Ο—(CH2)k2—Ο Λ. ο

(ΙΙΙ-20) (111-21) (ΙΙΙ-22) (ΙΙΙ-23) (ΙΙΙ-24) (ΙΙΙ-25) (ill-26) ❹ 25 321987

201100377

> -(CH2)k1 -o^'HG)_^-QQ-cn Q-〇n )〇-(cha"〇{)~hQ^^_cn (IV-1) (IV-2) (IV- 3) (IV-4) (IV-5) (IV-6) (IV-7) (IV-8) (IV-9) (IV-10) (IV-11) (IV-12) (IV- 13) (IV-14)

26 321987 201100377 ❹

=J"0_(CH2)k1~°~O_0N > -}

(CH2X2_H :>

-(CH2)k2-H-(CH2)k1-0

〇~^~^~〇~(CH2)k2-H )·°-(叫广〇·^^,ν〇-(〇Η2〉κ-Κ(0Η2)Κ2-Η (V-1) (IV- 15) (IV-16) (IV-17) (IV-18) (IV-19) _^-0—(ΘΗ2)κ —— ^^-〇-(CH2)k2-〇^ (V-2) -ο—(CH2>k“0·c 〇< (VI-1) -〇~(CH2)k1- (VI-2) Ο 3"' CHCH2>k1—丨

(VI-3) (VM) -Ο—(0Η2)κ —0 m <y -ο—(0Η2χ1-

0-Λ\ /)-COOH (VI-5) (VI-6) The content of the liquid crystal compound in the composition of the present invention is 90 parts by weight or less based on 100 parts by weight of the total of the liquid crystal compound and the compound (1). 27 321987 201100377 The composition of the present invention may further comprise: a polymerization initiator, a polymerization inhibitor, a photosensitizer, a flattening UeVeling agent, _, a palmitic fresh additive. In particular, it is preferred to include an organic solvent from the viewpoint of easily forming the composition of the present invention, and it is preferred to include a polymerization initiator. [Polymerization initiator] The polymerization initiator is preferably a photopolymerization initiator, and the photopolymerization initiator is preferably a photopolymerization initiator which generates a radical due to irradiation. The photopolymerization initiator may, for example, be a benzoin compound, a benzophenone compound, a sulfhydryl compound, an α-carbyl compound, an α-amino ruthenium compound, a triterpene compound, an onium salt or a phosphonium salt. Specifically, for example, IRGACURE 907 (manufactured by Ciba Japan Co., Ltd.), IRGACURE 184 (manufactured by Ciba Japan Co., Ltd.), IRGACURE 651 (manufactured by Ciba Japan Co., Ltd.), IRGACURE 819 (manufactured by Ciba Japan Co., Ltd.), and IRGACURE 250 (Ciba) Japan, Inc., IRGACURE 369 (manufactured by Ciba Japan Co., Ltd.), SEIKUOL BZ (made by Seiko Chemical Co., Ltd.), SEIKU0L Z (made by Seiko Chemical Co., Ltd.), SEIKUOL BEE (made by Seiko Chemical Co., Ltd.), KAYACURE BP100 (manufactured by Nippon Kayaku Co., Ltd.), KAYACURE UVI-6992 (manufactured by DOW Co., Ltd.), ADEKA 0PT0MER SP-152 (manufactured by ADEKA Co., Ltd.), ADEKA 0PT0MER SP-170 (manufactured by ADEKA Co., Ltd.), TAZ- A (made by Japan SiberHenger Co., Ltd.), TAZ-PP (made by Japan Siber Hegner Co., Ltd.), TAZ-104 (made by Sanwa Chemical Co., Ltd.), and the like. 100 psi of the total of the compound (1) and the liquid crystal compound, this 32 1987 28 201100377

1. 1 part by weight to within range ', the compound (1) or [parts may be preferred without disturbing the compound (1) or the liquid crystal form. In the case of the orientation of the above-mentioned crystalline compound [polymerization inhibitor] hydrogenation, a polymerization inhibitor having a substituent such as an alkoxy group may, for example, be a compound, a gallic phenol, a 2, 2, 6, a base-trapping agent, or a stupid The thiophenol compound wind brewing compound, the butyl catechin material has a substituent such as a silk, the tea is tetradecyl-1-piperidinyloxy radical, etc., from the ^,/5-nylamine compound, no-cai Compounds, etc. By using a polymerization inhibitor, it is easy to control the polymerization reaction of the compound (1) and the liquid crystal compound, and the stability of the obtained film can be improved. 5重量份至1. 1重量重量至至1重量重量至至1重量重量至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至至〇 The weight is preferred. If it is within the above range, the compound (1) or the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) or the liquid crystal compound. [Photosensitizer] The photosensitizer may, for example, be a ketone ketone compound such as xanthone or scorpion scorpion (Zhuang Yuyi &111; 11 〇 116) (for example, 2,4-diethyl) An anthraquinone compound (for example: dibutoxyanthracene, etc.), phenoseiazine, and red fluorescein (purine ketone, 2-isopropylthioxanthene, etc.), anthracene, an alkoxy group or the like. Rubrene). By the use of a photosensitizer, the polymerization of the compound (1) can be carried out with high sensitivity. 29 321987 201100377 The reaction can be improved, and the stability of the obtained film can be improved. The amount of the photosensitizer in the composition of the present invention is usually from 0.1 part by weight to 30 parts by weight, and from 0.5 part by weight to 10 parts by weight, based on the total amount of the compound (1) and the liquid crystal compound. It is better. If it is within the above range, the compound (1) or the liquid crystal compound can be polymerized without disturbing the orientation of the compound (1) or the liquid crystal compound. [coating agent]

The coating agent may, for example, be an additive for radiation hardening paint ("BYK-352, BYK-353, BYK-361N" by BYK), a coating additive (SH28PA, DC11PA, ST80PA, manufactured by Toray Dow Corning Co., Ltd.), and a coating material. Additives (manufactured by Shin-Etsu Chemical Co., Ltd., KP321, KP323, Χ22-161Α, KF6001), fluorine-based additives (made by DIC Corporation, F-445, F-470, F-479). A smoother film can be obtained by using a leveling agent. Further, the fluidity of the composition of the present invention can be controlled during the manufacture of the film, or the crosslinking density in the obtained film can be adjusted. The content of the leveling agent in the composition of the present invention is usually from 0.01 part by weight to 3 parts by weight, and 〇. 5 parts by weight to 10 parts by weight relative to 100 parts by weight of the total of the compound (1) and the liquid crystal compound. The parts by weight are preferred. If it is within the above range, the compound (1) or the liquid crystal compound can be polymerized without disturbing the orientation of the compound (D or the liquid crystal compound. [Solvent] The solvent is an organic solvent which can dissolve the compound (丨) and the liquid crystal compound. And it is a solvent which is inert to the polymerization reaction, and specifically, for example, 30 321987 201100377 such as: water; methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, thioglycoside, butyl cyanisol, Alcohol solvent such as propylene glycol monodecyl ether; ester solvent such as ethyl acetate, butyl acetate, ethylene glycol methyl ether acetate, 7-butyrolactone, propylene glycol decyl ether acetate, ethyl lactate a ketone solvent such as acetone, mercaptoethyl ketone, cyclopentanone, cyclohexanone, methyl amyl ketone or decyl isobutyl ketone; non-chlorinated aliphatic hydrocarbon such as pentane, hexane or heptane; Solvent; non-vaporized aromatic hydrocarbon solvent such as toluene or xylene; nitrile solvent such as acetonitrile; ether solvent such as tetrahydrofuran or dimethoxyethane; and chlorinated hydrocarbon solvent such as chloroform or chlorobenzene. These organic solvents can be used alone or in combination. For ease of application, the viscosity of the composition of the present invention is preferably adjusted to, for example, 1 OmPa·s or less, so as to be adjusted to about 0.1 to 7 mPa·s. It is preferably controlled by changing the amount of solvent. The solvent of the composition of the present invention is preferably contained in the form of a film, and the solvent is preferably contained in an amount of from 10 to 10,000 by weight based on 100 parts by weight of the compound (1). And preferably from 100 to 5,000 parts by weight. The concentration of the solid portion in the composition of the present invention is usually from 2 to 50% by weight, and preferably from 5 to 50% by weight. If the concentration of the solid portion is When the amount is 2% by weight or more, the obtained film is not too thin, and a film having a birefringence required for optical compensation of the liquid crystal panel is easily obtained. Further, if the concentration of the solid portion is 50% by weight or less, The viscosity of the composition of the invention is not too small, and the film thickness of the obtained film tends to be less likely to be uneven. Here, the "solid portion" means a component remaining after removing the solvent from the composition of the present invention. Palm agent] 31 321987 201100377 The palm-type agent can use a conventional palm-type agent (for example, "Liquid of Liquid Crystal Components, 3rd, 4th, 4th, TN, STN, Palm, 199 pages, 142th Committee of the Society for the Promotion of Science, 1989" The palmitic agent generally contains an asymmetric carbon atom, but an axial asymmetric compound or a planar asymmetric compound containing no asymmetric carbon atom can also be used as a palmitic agent. Asymmetric asymmetric compound or surface Specific examples of the asymmetrical compound include, for example, binaphthyl, helicene, paracyclane phane, and derivatives thereof. Examples of the palmitic agent include: Japanese Patent Laid-Open 2GG7 -26964G, 曰本特开2007-269639, Japanese Patent Laid-Open No. 2-77-1687, Japanese Unexamined-137887, and Japanese Special Report _51549 (Catch Bulletin, Japan Special Open 2007- The palmitic agent disclosed in Japanese Patent Publication No. 169178 and Japanese Patent Publication No. 506088 is preferably a Palioc〇i〇r LC756 manufactured by the company. With respect to the total weight fraction of the yttrium compound (1) and the liquid crystal compound, the palm is usually from Q. 丨 by weight to 3Q parts by weight, and is preferably ns 置 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The film of the compound (1) or the liquid crystal* is made to allow light to penetrate the film and has optical function; the function 'system means refraction, birefringence, etc., without disturbing the compound. The t-position difference of the light or ellipsoid of the present invention is: converting the money into a circularly polarized light, or changing the direction of polarization of the linearly polarized light. The first conversion is a straight line 321987 32 201100377 The film is obtained by polymerizing the compound (1) The compound (1) can be polymerized, and two or more kinds of the compound (1) can be polymerized. Further, the film of the present invention can be produced by polymerizing the composition of the present invention. In view of the above, it is preferred to use a solution obtained by dissolving the compound (1) in an organic solvent, and the solution is applied onto a support substrate, dried, and polymerized to obtain an optical film. The concentration of solids in the liquid is usually 2 to 5 0% by weight, and preferably 5 to 5% by weight. | ° The method of applying to the support substrate may be, for example, extrusion coating, direct gravure coating, reverse gravure coating, CAP coating. The method and the die coating method may be, for example, a method of coating using an applicator such as a dip coater, a bar coater, or a spin coater. ^ ' 支撑 a support substrate to be used for the support substrate For example, a glass, a plastic sheet, a plastic film, and a light transmissive film may be used. The translucent film may, for example, be polyethylene, polypropylene or norbornene/ ( N〇rb〇rnene) is a polyolefin film such as a polymer; a polyvinyl alcohol film; a polyethylene terephthalate film; a polyfluorene-acrylic acid film; a poly-_ film; a cellulose vine film; Ethylene diacetate film; polycarbonate film, polysulfone film; poly-hard film; poly-bond film; polyphenylene sulfide film; and polyphenylene ether film. ',' bonding step in film , transportation steps, storage steps, etc., which require the strength of the film, (4) using a supporting substrate, Roughing, etc. can be treated as follows. 'Unfoiled after forming an oriented film on the support substrate, it is preferred to apply a solution of the compound (1) on the oriented film 321987 33 201100377. The oriented film has a coating The solvent resistance of the solution of the compound (丨) is not soluble in the solvent. Further, the orientation film is preferably heat-resistant in a heat treatment for removing the solvent or directing the liquid crystal. In the case of rubbing, an oriented film which does not cause peeling or the like due to friction or the like is preferable. Such an oriented film is preferably composed of a directional polymer or a composition containing a directional polymer. For example, a polyamine or a gelatin compound having a guanamine bond in the molecule, a polyamidimide having a kinetic imine bond in the molecule, and a polyglycolic acid, a polyvinyl alcohol, an alkyl modified poly Vinyl alcohol, polypropylene decylamine, poly P« polyoxazole, polyethyleneimine, polystyrene, polyethylene than fluorenone, polyacrylic acid and polyacrylate. These oriented polymers may be used singly or in combination of two or more. In addition, copolymers of such a conjugated polymer can also be used. These oriented polymers can be polycondensed via dehydration. It is easily obtained by chain condensation polymerization such as polycondensation, radical polymerization, anionic polymerization, cationic polymerization or the like, depolymerization polymerization, ring-opening polymerization or the like. These oriented polymers are usually dissolved in a solvent towel to make a solution for use. The solvent is not particularly limited. Specific examples thereof include water; alcohol solvents such as methanol, ethanol, ethylene glycol, isopropanol, propylene glycol, methyl ceramide, butyl cyanidin, propylene glycol monodecyl amide; ethyl acetate, acetic acid An ester solvent such as butyl vinegar, ethylene glycol methyl ether acetate g曰, 7-butyrolactone, propylene glycol methyl ether acetate, lactic acid ethyl acetate; etc.; C-, methyl ethyl hydrazine, cyclopentamidine, cyclohexane , ketone solvents such as methyl amyl hydrazine and decyl isobutyl ketone; non-chlorinated aliphatic hydrocarbon solvents such as pentyl, hexane, and heptane; non-vaporized aromatics such as oxime, xylene, etc. 321987 34 201100377 Solvent-like solvents; acetonitrile and other guessing solvents; tetrachlorine agents can be used alone or in combination of two or more. These aligning oriented film materials are used to form the oriented film. The shares sold in the market are ==SUN_ (registered trademark, manufactured by Gifu Chemical Industry Co., Ltd.). ) and 0PT 〇 MER (registered trademark, 股份有限公司 ο = = = = = = 彡 延伸 延伸 延伸 延伸 延伸 延伸 延伸 延伸 延伸 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型 大型The method can orient the film material or as an oriented film. If the film is commercially available on a supporting substrate, the method of annealing is performed to form a solution and the thickness of the oriented film is usually 1Q to 1G, _nm 1, OOOnm. It is better if the helmet is from the 10 to ❹ to the desired angle on the film, then the compound (1) can be rubbed and fixed according to the requirement, and the compound (1) is at the desired angle. And the direction-oriented film shows the refractive index of the birefringent state of the opening and closing of the ellipsoid. In addition, if the white film and the tilting are performed during the rubbing treatment, the masking is performed, and the polarizing direction of the film can be c-polarized. The method of rubbing the film by rubbing can be performed by rubbing in the rotation of the cloth and on the stage, and the method of rubbing the film is carried out. The film of the match 1 is contacted with the film 3219S7 35 201100377 [unpolymerized film Modulation step] by coating on an oriented film on a support substrate or formed on a support substrate The solution of (1) is dried and obtained to obtain an unpolymerized film. When the unpolymerized film exhibits a nematic liquid crystal phase, it has birefringence oriented by a single region. The unpolymerized film is usually passed through 0 to 250°. C is dried for single-area orientation. Compound (1) exhibits a single-region orientation at a lower temperature due to the liquid crystal phase at a low temperature, and maintains single-region orientation even after cooling to a temperature of about 0 to 100 ° C after orientation. Step] A polymer film is obtained by polymerizing and hardening the obtained unpolymerized film. The polymer film is a film which fixes the orientation of the compound (1), and thus is not easily affected by changes in birefringence due to heat. The method of polymerizing the unpolymerized film is appropriately determined depending on the type of the polymerizable group of the compound (1). When the polymerizable group of the compound (1) is a photopolymerizable group, a photopolymerization method is used, and if the polymerizable group is heat In the case of a polymerizable group, a thermal polymerization method is used. When the photopolymerization method is used, the selection of the heat resistance of the substrate can be broadened by polymerizing the unpolymerized film at a low temperature, and From the viewpoint of easy production in the industry, it is preferred to use the compound (1) having a photopolymerizable group. The photopolymerization reaction is carried out by irradiating visible light, ultraviolet light or laser light to the unpolymerized film. The ultraviolet light is particularly preferable. The removal of the solvent can be carried out in parallel with the polymerization reaction, but from the viewpoint of film formability, it is preferred to remove most of the solvent before the polymerization reaction. The removal method may be, for example, natural drying. Drying, drying under reduced pressure, drying by heating, etc. The temperature at which the solvent is removed by heating is usually 10 to 200 36 321987 201100377 C, and preferably 20 to 15 (TC is preferred. The heating time is usually 1 sec to 8 sec. It is preferable that the film of the present invention can be produced by a coating method, for example, if the heating temperature and the heating are as described above, the film of the invention can be used. The film can be fabricated on a support substrate having a flexible substrate and a substrate having a curvature, and the substrate is supported to form a film having an oriented film and a film of the present invention, and the alignment film is peeled off. The film of the present invention is obtained. = outside' may also be formed by attaching another county material to a support substrate or forming a film of the present invention on the film, and then forming a support layer of the film of the present invention, peeling off, or peeling the branch The substrate and the oriented film were peeled off and transferred. The phase difference (delay) of the film obtained by phosphine drought can be prepared by appropriately adjusting the content of the compound (1) and the liquid helium: cerium compound in the composition of the present invention in such a manner that the desired phase difference can be obtained. The retardation value, ❹Re, \)) is determined by the fine formula (7), and (4) in order to obtain the desired Re(λ), only Δη(λ) and the film thickness d may be adjusted.

ReU)=dxAn(A) (7) (wherein, Re( ;^车_ +丄) is not in the wavelength (10) phase difference, d is the film thickness, and in) is the birefringence at the wavelength λ nm). The resulting film is excellent in transparency and is used as a display for various displays. As described above, the thickness of the layer formed varies depending on the mesh difference of the obtained film, but the thickness is preferably 〇1 to 1〇#m, and from the viewpoint of reducing photoelasticity, from 〇.2 to 5 Preferably. 37 321987 201100377 The film of the present invention can change various optical properties by changing the orientation state of the compound (1). As a result, when used as a retardation film for a liquid crystal panel, the optical characteristics can be changed to allow for VA (Vert i ca 1 Alignment) mode, iPSUn-Plane Switching 'plane conversion mode', 〇CB (Optical Compensated) Bend, optically compensated bend mode, TM (Twisted Nematic) mode, and STN (super twisted nematic) mode. More specifically, when the refractive index in the slow axis direction in the plane of the film of the present invention is defined as nx, the refractive index in the direction perpendicular to the slow axis in the plane (fast axis direction) is defined as ny, and the thickness direction is When the refractive index is defined as nz, a film having no phase difference of nx~ny%nz, a positive a plate of nx>ny-nz, a negative c plate of ru 1 ny&gt;nz, a positive C plate of nx and ny&lt;nz can be manufactured. , nx_ny: ^nz's positive and negative 0 board. In addition, films oriented to the orientation of the palmitic nematic phase are known to selectively reflect, and selective reflection is also confirmed in the films of the present invention. The selective reflection wavelength band can be selected depending on the purpose of use of the film. Selectively Reflected Wavelength The center wavelength of the band (nm) is as shown by ι = η.ρ, where n is the average refractive index of the composition and P is the helical pitch of the palmitic nematic phase (from m). In general, if the content of the palmitic agent is increased, P will become smaller, so controlling the content of the palmitic agent can also control the selective reflection wavelength band. At this time, the orientation is made such that the palm axis is almost perpendicular to the direction of the surface of the transparent support. By using a palm-like agent in this way, a twisted oriented film, a selective reflection film, a brightness enhancement film, and a negative C plate can be produced. In addition, when used as a 321987 38 201100377 .I plate phase % ' to have a selective reflection wavelength band in the ultraviolet region. 1. Produce your film. Even if it is only one film, it still shows excellent optical special effects. The film layer of the same function can also be used with other films. The film of the invention can be used for retardation film and viewing angle film. After the angle of view is enlarged, the polarizing film, the brightness is raised, the film is high, and the film is polarized, and the polarizing film or the polarizing film is er. </ </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> A thin crucible is formed directly on the liquid crystal 5~ sheet. In addition, it is also possible to carry out the patterning of optical functions, and it is also the most pleasing to enter the 仃子子 machine! Figure!^ is used as a phase difference plate for the so-called unit.略略面®, 帛/the schematic d-side view of the film containing the partiality of the film of the present invention, and the second figure shows the outline cross-section of the case-example, the third == organic liquid of the liquid crystal display The EL shows the second aspect of the farm, and the table does not include the schematic view of the film of the present invention, and the fourth figure shows a schematic cross-sectional view of the yttrium of the package. The film of the present invention may be only the film of the present invention, or may be the film of the present invention or may be an oriented film of the film of the present invention. Tooth soil. Further, the adhesive and the adhesive are collectively referred to as a bonding center f, and the first embodiment indicates an embodiment in which the polarizing film of the film of the present invention is included. Fig. 1 (4) is an embodiment in which the film of the present invention is bonded to the film of the polarizing film layer by a layer. Fig. 1(C) shows an embodiment in which the film of the present invention 321987 39 201100377 1 is directly bonded to the film crucible of the present invention, and then the film crucible of the present invention and the polarizing film layer 2 are directly bonded together, Fig. 1 (d) An embodiment in which the film 1 of the present invention is bonded to the film of the present invention via the adhesive layer 3, and then the polarizing film layer 2 is directly bonded to the film of the present invention. Fig. 1(e) shows that the film 1 of the present invention is bonded to the film of the present invention via the adhesive layer 3, and then the film of the present invention and the polarizing film layer 2 are bonded to each other via the adhesive layer 3'. Implementation form. The polarizing film layer may be a film having a polarizing function, and specifically, for example, a film obtained by adsorbing iodine or a dichroic dye to a polyvinyl alcohol film and extending the film, and stretching the polyvinyl alcohol film A film obtained by adsorbing iodine or a dichroic dye. Further, the polarizing film layer can be provided as a film of a protective film as needed. The protective film may, for example, be a polyolefin film such as polyethylene, polypropylene or a norbornene-based polymer; a polyethylene terephthalate film; a polydecyl acrylate film; a polyacrylate film; a cellulose ester film; Ethylene naphthalate film; polycarbonate film; polysulfone film; polyether ruthenium film; polyether ketone film; polyphenylene sulfide film; and polyphenylene ether film. The adhesive used in the adhesive layer 3 and the adhesive layer 3' is preferably an adhesive having high transparency and excellent heat resistance. The subsequent agent may, for example, be an acrylic adhesive, an epoxy adhesive, an urethane adhesive or the like. Further, as shown in Figs. 1(c) to 1(e), two or more films of the present invention may be bonded directly or via an adhesive layer. In the flat panel display device of the present invention, the liquid crystal display device including the liquid crystal panel in which the polarizing film of the film of the present invention is bonded to the liquid crystal panel is provided, and the present invention is provided. 40 321987 201100377 An organic EL display device of an organic electroluminescence (hereinafter referred to as "EL") panel in which a polarizing film of a film of the invention and a light-emitting layer are bonded together. Hereinafter, a liquid crystal display device and an organic EL display device which are embodiments of the flat panel display device of the present invention will be described in detail. [Liquid Crystal Display Device] Specific examples of the liquid crystal display device include a liquid crystal display device including a liquid crystal panel as shown in Figs. 2(a) and 2(b). In the above liquid crystal panel, as shown in Fig. 2(a), the member 4 including the film of the present invention and the liquid crystal panel 6 are bonded together via the adhesive layer 5, or the film of the present invention is included in Fig. 2(b). The member 4 and the member 4' including the film of the present invention are bonded to both surfaces of the liquid crystal panel 6 via the adhesive layer 5 and the adhesive layer 5'. According to the above configuration, by applying a voltage to the liquid crystal panel by using an electrode (not shown), liquid crystal molecules can be driven to display a black-and-white surface. [Organic EL display device] Specific examples of the organic EL display device include an organic EL display device including an organic EL panel shown in Fig. 3. In the above organic EL panel, the member 4 including the film of the present invention and the light-emitting layer 7 are bonded together via the adhesive layer 5. The light-emitting layer 7 is a layer of at least one layer composed of a conductive organic compound. Further, in the above-described organic EL panel, when the member 4 including the film of the present invention is a polarizing film, the function of the wide-band circular polarizing plate is exhibited. Therefore, the anti-reflection function can be imparted to the organic EL panel. [Filter, color sheet] Fig. 4 is a schematic cross-sectional view showing an example of a color filter 11 containing the film of the present invention, 41 321987 201100377. The color filter 11 is a color filter in which the color filter layer 13 is formed on the polarizing film 12 of the present invention. An example of a method of manufacturing the color filter 11 will be described. First, after the alignment film material is coated on the support substrate, rubbing treatment is performed to form an alignment film. The human is adjusted on the oriented film to adjust the thickness in such a manner that the resulting film exhibits a desired retardation value, and is coated in such a manner as to adjust the compound in such a manner that the resulting film exhibits desired wavelength dispersion characteristics. (1) A solution of the compound (1) in a concentration or the like to form a film. Next, a color filter layer 13 is formed on the obtained film 12 of the present invention. (Embodiment) Hereinafter, the present invention will be described in more detail by way of examples. In the examples, the "parts" are % by weight and parts by weight unless otherwise specified. (Example 1) [Synthesis Example of Compound (l-a14)]

(1-a14) (1) Synthesis of Compound (e) The compound (e) is obtained by reacting the compound (d) and the compound (h) as shown in the following scheme. 321987 42 201100377 Η' C6H12-〇hQ^〇H (d) &gt; DCC.DMAP CHCI3 HOOO&lt; fn % 0—C6H12-〇-\^_3&quot;〇(e,&gt; (h) p η % 0—06Η12 -〇-^3^° (e)

-C00H H+

THF (synthesis of compound (d)) o h〇_(3~oh DHP, PPTs THF~' H0- K2C03l H0-C6HiyCI DMAc HOCeH12-〇-Q^O' , (b) propylene gas

CHCI 3

Yp-CeH12-〇-{^-d~^ \P-C6Hi2~〇~^3_OH 〇 (6) Fly (d) The compound (a) is synthesized by the method described in JP-A-2004-262884. The N,N-dimercaptoacetamide was heated at 90 ° C under a nitrogen atmosphere to react 100 g of the compound (a), 97 g of potassium carbonate and 64 g of 6-chlorohexanol. It was further heated to 100 ° C to cause a reaction. The resulting reaction mixture was cooled to room temperature, and after adding pure water and methyl isobutyl ketone, the organic layer was separated. The organic layer was washed with an aqueous sodium hydroxide solution and pure water, and then subjected to dehydration treatment. After the dehydrating agent was removed by filtration, the resulting filtrate was concentrated under reduced pressure. After methanol was added to the obtained residue, the resulting precipitate was taken by filtration and dried in vacuo to give 126 g of Compound (b). Yield: 91% (based on 6-chlorohexane). Compound (b) 126g, 3, 5-di-tert-butyl-4-hydroxyindole benzene 1. 4g, N, N-dimethylaniline 117g, 1,3-dimercapto-2- sigma Lin Kezheng lg 43 321987 201100377 and gas-like mixing. Under a nitrogen atmosphere, 58 g of propylene helium gas was added dropwise to a person under ice cooling, and then pure water was added thereto to cause a reaction. From the reaction mixture of two, the organic layer was separated. The organic layer was washed with hydrochloric acid water, a saturated aqueous solution of sodium carbonate and purified water. A dehydrating agent is added to the organic layer to dry it. After removing the dehydrating agent, 3,5-di-tertiary butyl 4-hydroxytoluene lg ' was added to the obtained mash and concentrated under reduced pressure to give the compound (c). Compound (c) was mixed with 200 mL of tetrahydrofuran. Further, 200 mL of tetrahydrofuran was added to the obtained mixture, and then hydrochloric acid water and concentrated hydrochloric acid water were added, and the reaction was carried out at 60 ° C in a nitrogen atmosphere. The reaction mixture was washed with 500 mL of a saturated saline solution, and then subjected to dehydration treatment with a dehydrating agent. After filtering the dehydrating agent, the resulting filtrate was concentrated under reduced pressure. Hexane was added to the obtained concentrate and stirred under ice cooling. The precipitated solid was taken out by filtration and dried in vacuo to give compound (d) (90 g). Yield: 79% (based on compound (c)). (Synthesis Example of Compound (h))

The trans-1,4-cyclohexyl succinic acid hydrazone g was mixed with 100,000 N,N-monodecylamine. The obtained mixture was heated to 8 (one TC) while stirring under a nitrogen atmosphere, and then 96 g of potassium bromate and potassium molybdate were added. Further, after adding 140 g of chlorobenzene to 140 321987 201100377, the resulting solution was reacted at 12 CTC for 6 hours. After the obtained reaction solution was allowed to cool to room temperature, it was poured into 15 〇〇g of ice and stirred. The obtained crystal was taken out by filtration and washed with water: decyl alcohol: 2 (v/v) - followed by water. The washed crystals were vacuum-dried to obtain 25 g of a powder containing the compound (f). 251 g of the powder containing the compound (f) was mixed with 6 〇〇mL of chloroform. The resulting solution was ice-cooled, and then under a nitrogen atmosphere. The ethoxy oxane oxime 93.53 g and diethylamine 146.83 g were added dropwise. The resulting solution was reacted at room temperature for 3 hours under a nitrogen atmosphere. After adding 6 toluene to the obtained reaction solution, borrowed The precipitated triethylamine hydrochloride was removed by filtration, and the obtained filtrate was washed with water and then dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the solvent was removed from the obtained sputum. Drying in a vacuum to obtain a compound g) 242 g of liquid. 242 g of liquid containing compound (g) was mixed with 25 〇mL of tetrahydrofuran. After adding 1% palladium carbon (5 % by weight) O l〇g to the obtained solution in a nitrogen atmosphere, The resulting mixture was reacted in a hydrogen atmosphere at room temperature under normal pressure for 6 hours. The resulting reaction mixture was filtered, and after removal of the catalyst, the solvent was removed. After the residue was dissolved in the gas, the solution was filtered using a silica gel. The chloroform solution was concentrated under reduced pressure, and the resulting residue was crystallized. 1〇6g. Yield: 39% (based on anti-i,4-cyclohexanedicarboxylic acid). (Synthesis of compound (e)) Compound (d) 56.8 g, N, N-dimethyl 2-aminopyridine pyridine 2.65 g, crystallization 32 1987 45 201100377 Compound (h) 50 g and gas imitation 300 niL were mixed. The resulting mixture was ice-cooled and stirred under a nitrogen atmosphere, and then added dropwise to make dicyclohexylcarbodiimide (dicycl) 〇hexyiCarb〇diimide) 48. 79g dissolved in 5仿mL After the completion of the dropwise addition, the resulting mixture was stirred at room temperature, and 2 mL of chloroform and 2 mL of heptane were added to the obtained reaction mixture, and then removed; After the filtrate was washed, the insoluble matter was removed by subtraction. After the obtained filtrate was dried over anhydrous sodium sulfate, sodium sulfate was removed by filtration. The solvent was removed from the obtained filtrate, and the obtained solid was dried in vacuo to give a compound ( e,) 100 g. 100 g of the compound (e'), 3.7 g of pure water, 3.8 g of p-toluenesulfonic acid monohydrate and 200 mL of tetrahydrofuran were mixed, and the mixture was reacted at 5 Torr in a nitrogen atmosphere. After the resulting reaction solution was allowed to stand to room temperature, tetrahydrofuran was removed under reduced pressure. 200 mL of heptane was added to the resulting residue. The precipitated chamber was taken out by filtration, washed with pure water, and vacuum dried. The resulting powder was dissolved in a gas and filtered through a silica gel. After the filtrate was mixed with 4 mL of chloroform, the resulting solution was concentrated. After adding toluene to the concentrated residue, the resulting solution was concentrated under reduced pressure. After heptane was added to the concentrated residue for crystallization, the obtained crystals were taken out by filtration. The crystals taken out were vacuum dried to give Compound (e) 64 g. Yield: 76% (based on compound (d)). (2) Synthesis example of the compound (1 - ai 4) phenylhydroquinone 3. 4 g, the compound (e) i6 g, and 4-dimethylamino ιι were mixed with 5 g of a bite and 237 g of a gas. A solution obtained by dissolving 9.4 g of N,N,-dicyclohexylcarbodiimide in 9 g of chloroform was added dropwise to the resulting mixture, and allowed to react for 36 hours. After adding 140 1987 46 201100377 2N hydrochloric acid to the obtained reaction mixture, the resulting mixture was passed through. To the obtained mash, 14 〇g of 2N hydrochloric acid was added, washed, and concentrated to obtain a concentrate of about 5 〇g. Activated carbon 〇.4g was added to the concentrate and filtered through diatomaceous earth. After the obtained - filtrate was concentrated, methanol was added to the concentrated residue to obtain a solid matter. 4克。 The solid matter obtained by the methanol was washed to give a white solid compound (l-al4) 8.4 g. Yield: 47% (based on phenylhydroquinone). Compound (i-al4)] h-NMR (CDCl3): a (ppm) 1 35~work 91 (m, 24H), 2.35~2.58 (m, 12H), 3.93 (t, 4H), 4.17 (t, 4H), 5. 81 (dd, 2H), 6. 12 (m, 2H), 6. 40 (dd, 2H) 6 8 4 to 6. 99 (m, 8H)' 7. 1 1 (m, 3H ), 7. 3 8 (m, 5H) ' The phase transition temperature of the obtained compound (1-al4) was confirmed by texture observation by a polarizing microscope. When the compound (i-ai4) was heated, it exhibited a nematic phase between gyc and 198C, and became an isotropic phase at 198C. If the temperature is gradually lowered from 2 ° ° C, a nematic phase is present between 198 t and 36 ° C and crystallized at 36 ° C. Thus, the compound (l-al4) exhibits nematic liquid crystallinity not only in a relatively wide temperature range but also nematic liquid crystal in the vicinity of 40 °C. (Example 2) [Synthesis Example of Compound (l-a3)]

(A-2) + Ο Q O—CgH-i (e)

COOH -QC〇x&gt;map. chci3 -C6H12-〇hQ-i

(1-a3)

The tertiary butyl was brewed 1. 〇g, compound (e) 6. Og, 4-dimethylamine 47 321987 201100377 The base pyridine 0·2g and chloroform 121g were mixed. A solution obtained by dissolving 4.5 g of N'N-cyclohexylcarbodiimide in 24 g of chloroform was added dropwise to the resulting mixture at room temperature, and allowed to react for 3 hours. After 60 g of 2N hydrochloric acid was added to the obtained reaction solution, the resulting mixture was filtered. The obtained filtrate was washed with 6 μg of 2N hydrochloric acid and concentrated to give a concentrated liquid about 4 g. 0.3 g of activated carbon was added to the concentrate, and it was filtered with diatomaceous earth. The solvent was distilled off from the obtained filtrate. Methanol was added to the resulting concentrated residue to obtain a solid. The solid matter obtained was washed with methanol to give a compound (l-a3) 4· lg as a white solid. Yield: 71% (based on tributyl hydrazine). Compound U-a3) H-NMR (CDCl3): δ (ppm) 丄 · 34 (s, 9h) 1· 35 〜1. 91 (m, 24H), 2. 35 〜 2. 58 (m, 12H ), 3·94 (t 4Η), 4. 17 (t&gt; 4H), 5. 81 (dd, 2H), 6. 12 (m, 2H), 6. 40 (dd, 2H), 6.84 ~ 7. 0 6 (m, 1 1H) The phase transition temperature of the obtained compound (l-a3) was confirmed by texture observation by a polarizing microscope. It was confirmed that the compound (i_a3) exhibited a smectic phase between μ C and 96 ° C at a temperature rise, and was at 96. (: to at least 18 (the nematic phase appears between TCs. After gradually decreasing the temperature from 180 ° C, it is confirmed that a nematic phase is present between 18 Å and at least 29 ° C, and is not crystallized. Compound (1_a3) is not only The nematic liquid crystallinity was exhibited in a wide temperature range, and the nematic liquid crystallinity was also exhibited in the vicinity of 30 ° C. (Comparative Example 1) [Synthesis Example of Compound (III - Di)] 48 321987 201100377 H Ο /f~\ 3 O-CjHb-CI H3C-^ /=\ NaOH H0-C=/ C〇〇E1 —— 匕0-〇4H8-〇^&gt;-〇〇〇Et K2C03 甲酵,H20 (0 H〇-C4H8— O-^^-COOH 0)

Propylene helium y^〇-C4H"OH^^COOH 〇 (k)

(Synthesis Example of Compound (i)) 4-ethoxybenzoic acid ethyl ester 84. 5 g, 4-butyl butyl acetate 84.2 g, potassium ruthenium carbonate 105 g and N,N-dimercaptoacetamide 254 g The resulting mixture was warmed to 100 ° C and stirred. After cooling, methyl isobutyl ketone was added to the reaction mixture, and after washing with water, the solvent was removed to obtain 126 g of an oily substance containing compound (i) as a main component. Yield: 88% (based on ethyl 4-hydroxybenzoate). (Synthesis Example of Compound (j)) 126 g of an oily substance containing the compound (i) as a main component, 378 g of decyl alcohol, 252 g of hydrazine hydrate and 54 g of sodium hydroxide were mixed and reacted at 65 °C. After the reaction mixture was cooled, it was poured into 756 g of ice, and hydrochloric acid was further added. The precipitated solid was taken out, washed with water and heptane, and dried to obtain 91 g of a solid as a compound (j). Yield: 97% (based on compound (i)). (Synthesis Example of Compound (k)) 90. Og of the compound (j) as a main component in a nitrogen atmosphere, 77.8 g of N,N-dimethylaniline was dissolved in hydrazine, hydrazine-dimercaptoacetamide 720g. After the solution was cooled to 0 ° C, 58. lg of propylene chloride was added dropwise, and the mixture was allowed to react at room temperature. After adding 1 N hydrochloric acid to the obtained reaction mixture, the solid which precipitated was taken out at 49 321987 201100377. The removed solid was dissolved in ethyl acetate. After washing the obtained solution with water, the solvent was removed to obtain 102 g of a solid having the compound (k) as a main component. Yield: 90% (based on compound (j)). (Synthesis Example of Compound (II1-1-1)) 3 g of hydroquinone, solid i6 g of compound (k) as a main component, 0.7 g of 4-dimethylaminopyridine, and 127 g of chloroform were mixed. A solution obtained by dissolving 12 g of N,N,-dicyclohexylcarbodiimide in 32 g of a gas-like mixture was added dropwise to the obtained mixture at room temperature, and allowed to react for 3 hours. After adding 159 g of 2N hydrochloric acid to the reaction mixture, it was filtered. After 159 g of 2N hydrochloric acid was added to the obtained filtrate and washed, the solvent was distilled off, and methanol was added to obtain a solid matter. The obtained solid matter was washed with methanol to give Compound (II1-1-1) 12. 〇g as a white solid. Yield: 66% (based on hydroquinone). The phase transition temperature of the obtained compound (III-1-1) was confirmed by texture observation with a polarizing microscope. If the temperature is gradually increased, it is 1〇7. The 〇 is converted from a crystalline phase to a nematic phase, and is converted to an isotropic liquid phase at 167 ° Cb. If the temperature is gradually lowered, the isotropic liquid phase is converted into a nematic phase at 167 ° Cm, and if the temperature is lowered to near 74 π, it is converted back to the crystal phase. In other words, it is known that the compound (when the temperature is raised, between 107C and 167C, and when the temperature is lowered, between 167. 〇 to 1〇7. 〇, both exhibit a nematic phase. (Example 3 6 to 6 and Comparative Example 2) <Adjustment of Composition> The composition of the composition of Table 2 was prepared. The % in Table 2 is intended to indicate the weight % when the total weight of the composition is 100% by weight. 50 321987 201100377 [Table 2] sputum (l) I liquid crystal compound——--r—— ---- gl&quot; I % 丨% ^ combined starter (%) coating solvent (%) Example 3| l-aH_ Female Example 4丨13⁄4- 30 [30 Example 5 l-al4 10 III-1-1 10 Greedy Example 6 l~a3 10 III-1-1 10 Comparative Example 2 - II - III-1-1 20

0.02 0. 03 Γ 69 卜 0.03 1 69 1 0.02 79 0. 02 79 79 醯 '醯 膦 膦 氧化物 氧化物 ) ) BY : BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY BY The substrate was coated with a 2% by weight aqueous solution of polyvinyl alcohol (polyvinyl alcohol, fully saponified, and Wako Pure Chemical Industries, Ltd.), and dried by heating to form a film having a thickness of 89 nm. An oriented film is formed by subjecting the surface of the film to rubbing treatment. The composition described in Table 2 was applied by a spin coating method on the surface subjected to the rubbing treatment. When the temperature of the substrate was raised, the substrate was heated at a temperature increase rate of 3 〇t/min, and a polarizing microscope with a hot stage was used (hot stage: LTS350, manufactured by Linkam Corporation: polarizing microscope: BX-51, manufactured by OLYMPUS) Observe the behavior of the composition. When cooling down, observe the behavior with natural cooling. The results are shown in Table 3. 51 321987 201100377 [Table 3] Example 3 Example 4 Example 5 Example Comparative Example 2 Observation Results ~ '~~—Confirm the degree, then form a single-area structure at 78 °C, and at least 15 Maintain a single order between the two. The regional structure "after decreasing the temperature from 15 °C, the result shows a nematic phase between 38p and a single-domain structure, and crystallizes at 3 8 C. Indeed, if the degree is 2, rc phase-turns, forming a single-region structure, and to at least 15 (maintaining a single cell between TCs. The region structure. After reducing the temperature from 15 ° ° c, the result is 40 ° between the results The phases are formed and formed into a single-region structure and crystallized at 40 C. Each recognizes 'at 84. (: phase turns #&quot; is oriented, forms a single-region configuration, and maintains a single between at least 150 °C. The regional structure. From 15 (Tc began to lower the temperature, the result shows a nematic phase between 40 C and formed a single-domain structure, 40 C crystallization. ^?J ί 1 〇〇^ ^ ^^ forms an early regional structure, And maintain a single-area structure between at least 15{rc. After the temperature is lowered from 15 °C, the nephew is between the ${t and a single-region structure is formed and crystallized at 36 C. j The structure of the region, and the structure of the V ΐ ΐ ΐ domain is at least 158 ° C. After the temperature is lowered from 16 ° C, the result is a nematic phase and a single-region structure is formed. <Production Example of Film>, coated on a glass substrate 2 polyvinyl alcohol (polyvinyl alcohol 1000 completely saponified in the company and manufactured by Wako Pure Chemical Industries Co., Ltd.) 2 After the weight % aqueous solution, it is dried by heating, and (4) a film having a thickness of 89 nm. The surface of the film is rubbed at 321987 52 201100377 to form an oriented film. The surface of the surface subjected to the rubbing treatment is coated by a spin coating method. The composition described in 2 was dried for 1 minute at the temperature (T.) shown in Table 4. The temperature shown in Table 4 (after 1 minute of standing, the ultraviolet light having an accumulated light amount of 2400 mJ/cm 2 was irradiated, Film was formed. <Observation of surface state> The surface state of the film was observed at a magnification of 400 times with a polarizing microscope. If a single region was present, it was marked as 〇, and if a defect was produced, it was marked as X. The results are shown in Table 4. Stability over time> After placing the film in the atmosphere at room temperature for 2 weeks, observe the surface state of the film with a polarizing microscope. If no orientation defect is found, it is marked as 〇, and if it is determined that directional defect is produced, it is marked as X. Table 4 shows. [Table 4]

TcfC) Td (°C) Surface State Temporal Stability Example 3 90 30 〇〇 Example 4 60 30 〇〇 Example 5 100 50 〇〇 Example 6 100 50 〇〇 Comparative Example 2 150 140 XX < Optical Properties Measurement> The phase difference value of the film was measured by a measuring machine (KOBRA-WR, manufactured by Oji Scientific Instruments Co., Ltd.). The measurement of the phase difference (nm) is performed on a laminate including a glass substrate, an alignment film, and a film, but since the glass substrate and the alignment film do not have birefringence (glass substrate and oriented film system 53 321987 201100377

Re(447)=Re(547)=Re(628)=0), so that the measured phase difference is the phase difference of the film. The phase difference Re(λ) was measured at wavelengths (again) of 447 nm, 547 nm, and 628 nm. The film thickness d (/z m) of the film was measured using a laser microscope (LEXT3000, manufactured by OLYMPUS). The results are shown in Table 5. [table 5]

Re(447) Re(547) Re(628) Re(447)/ Re(547) Re(628)/ Re(547) d Example 3 109 106 104 1034 0.981 1.10 Example 4 115 110 108 1.045 0.985 1.10 Implementation Example 5 126 116 114 1.083 0.979 0.81 Example 6 130 120 120 1.083 0. 977 0.81 ΓComparative Example 3 卜 99 h 91 86 1.093 0.944 0.54 In the examples, it can be made at 3 (TC or 50 ° C low temperature) (Industrial Applicability) By polymerizing the compound of the present invention, a film having excellent surface state and stability over time and having optical characteristics can be produced at a low temperature. [Simplified Schematic] Fig. 1(a) And (e) is a schematic cross-sectional view showing an example of a polarizing film of the film of the present invention. Fig. 2 (a) and (b) are schematic cross-sectional views showing an example of a liquid crystal display device of the film of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 4 is a schematic cross-sectional view showing an example of an organic germanium display device of a film of the present invention. Fig. 4 is a schematic cross-sectional view showing an example of a color filter of a film of the present invention. Fig. 321987 54 201100377. , 1, 12, film 2, 2, polarizing film layer 3, 3, adhesive layer 4, 4 The present invention comprises a thin film member 5, 5, filter 13, adhesive layer 11 a liquid crystal panel filter layer ❹ 6 7 55 321 987 luminescent layer

Claims (1)

201100377 VII. Patent application scope: 1. A compound represented by formula (1): (wherein, X represents an alkyl group having 2 to 20 carbon atoms, an alkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms; , 'E and E respectively Independently represents a linking group or a single bond; A1 and A2 each independently represent a substituted or unsubstituted divalent aromatic group; and two F and F each independently represent a carbon number of 1 to 12 and a base-constituting the second base of the hospital One or more atoms; B, B, B, and B each independently represent a linking group or a single bond; or a substituted or unsubstituted methylene group may be substituted into oxygen P and P respectively independently represent a hydrogen atom or a polymerization Sex base). 2. If you apply for a patent scope! a compound of the formula wherein, in the formula (1), P and P each independently represent a group represented by the formula (P4): R1 R2 soil (wherein R1 (wherein R', R2 and R3 each independently represent a carbon number or a hydrogen atom). A composition of the alkyl group of 6 includes the fifth compound of the patent application and photopolymerization initiation. - A film is obtained by polymerizing a film of the patent application, a compound of item 1 or item 2 or a compound of item 321987 56 201100377. A film comprising the fourth item of the patent application scope. 6. A flat panel display device comprising the film of claim 4 of the patent application. 7. A method for manufacturing a film comprising: claiming the scope of claim 1 Or the step of coating the compound of item 2 on a substrate or on an oriented film on a substrate. ❹ 57 321987