WO2015046826A1

WO2015046826A1 - Inverse-wavelength dispersible compound, and inverse-wavelength dispersible composition and optically anisotropic body comprising same

Info

Publication number: WO2015046826A1
Application number: PCT/KR2014/008751
Authority: WO
Inventors: 이민형; 전성호; 서경창; 김정현; 홍미라; 장형빈; 문정욱
Original assignee: 주식회사 엘지화학
Priority date: 2013-09-30
Filing date: 2014-09-19
Publication date: 2015-04-02

Abstract

The present invention relates to an inverse-wavelength dispersible compound, and an inverse-wavelength dispersible composition and an optically anisotropic body comprising the same. The inverse-wavelength dispersible compound according to the present invention is capable of providing stronger and more stable inverse-wavelength dispersion, thereby being capable of providing an optically anisotropic body having superior optical properties.

Description

【Specification】

[Name of invention]

Reverse wavelength dispersible compound, reverse wavelength dispersible composition and optically anisotropic body comprising same

Technical Field

The present invention relates to a reverse wavelength dispersible compound, a reverse wavelength dispersible composition and an optically anisotropic body comprising the same.

Background Art

As the share of liquid crystal displays (LCDs) in the display field rises, interest in organic light emitting diodes (LEDs), which are considered as next-generation displays, is gradually increasing.

OLED displays are gaining attention as the displays of the future because they are superior to LCDs in various fields such as thickness, power consumption, speed of response, viewing angle, and can be used for various purposes such as transparent and flexible products.

However, OLEDs have a short lifespan and a low luminous efficiency, and thus are still limited in size. In particular, OLEDs are difficult to realize perfect black due to interference of external light.

In order to achieve more perfect black color, a method of minimizing interference by external light using two polarizing films in an OLED display has been proposed. Method using two sheets of polarizer film is relatively simple, and can affect the sharpness of the display, there is a problem in the production ^cost, which increases.

Accordingly, various methods for minimizing interference by external light, such as a method of using a reverse wavelength dispersion film instead of the polarizing film, have been proposed, but the effect is still insufficient.

[Contents of invention] ᅳ

[Problem to solve]

It is an object of the present invention to provide a reverse wavelength dispersible compound which makes it possible to provide a stronger and more stable reverse wavelength dispersion.

In addition, the present invention and the reverse wavelength dispersion composition comprising the compound It is for providing an optically anisotropic body.

[Measures of problem]

According to the present invention, there is provided a reverse wavelength dispersible compound represented by the following general formula (1):

[Formula 1]

In Chemical Formula 1,

A is a carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms;

E ¹ , E ² , D ¹ , and D ² are each independently a single bond or a divalent linking group;

L ¹ and L ² are each independently —H, —F, —CI, —Br, —I, —CN, —NC, —NCO, —OCN, —SCN, —C (= 0) NR ¹ R ² , -C (= 0) R, -OC (= 0) R 1, -NH 2, -SH, -SR 1, -SO 3 H, -S0 2 R 1, - OH, -NO 2, -CF 3l - SF ₃ , substituted or unsubstituted silyl, substituted or unsubstituted carbon number

1 to 40 carbyls or hydrocarbyls, or -S _p -P, wherein at least one of L ¹ and L ² is -Sp-P, P is a polymerizable group, and s _p is a spacer group or a single bond R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms;

m and π each independently represent an integer of 1 to 5; M or n is

If two or more, each repeating unit of two or more repeating-(D ¹ -G ¹ )-or-(G ² -D ² )-may be the same or different from each other;

G ¹ and G ² are each independently a non-aromatic carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms, wherein at least one of G ¹ and G ² increases A carbocyclic or heterocyclic group, and any one of the hydrogens contained in the carbocyclic or heterocyclic group is substituted with a group represented by the following Chemical Formula 2:

[Formula 2]

In Chemical Formula 2,

ρ is an integer of 1 to 10, and if ρ is 2 or more, each repeating unit of-(Q ¹ )-repeated two or more times may be the same or different from each other,

Q ¹ is each independently a divalent group selected from the group consisting of -C≡C-, -CY ¹ = CY ^2- , and a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 20 carbon atoms, wherein Y ¹ And Y ² are each independently —H, —F, —CI —CN, or —R ¹ ,

B ¹ is -H, -F, -CI, -Br, -I, -CN, -NC, -NCO, -OCN, -SCN, -C (= O) NR ¹ R ² ,-C (= O) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -SO ₂ R ¹ , -OH, -NO ₂ , -CF ₃ , -SF ₃ , a polymerizable group (as defined in Formula 1 above) P), a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C2-C4 acyl group, the C2-C6 alkynylene group which the C2-C4 acyl group couple | bonded with the terminal, C1-C6 An alcohol group of 5 or an alkoxy group having 1 to 12 carbon atoms, and R ¹ and R ² are each independently -H or alkyl having 1 to 12 carbon atoms.

Furthermore, according to the present invention, it is obtained from a composition comprising the reverse wavelength dispersion compound, and the following formula | And an optically anisotropic body satisfying the formula

(I)

A ri (450nm) An (550nm ) (1 .0

(Equation II)

An (650nm / An (550nrn) > 1 .0

In the above formulas (I) and (I), Δη (λ) means specific birefringence at wavelength λ. Hereinafter, an optically anisotropic body obtained from a reverse wavelength dispersible compound and a composition including the same according to embodiments of the present invention will be described. Prior to this, the terminology is for the purpose of referring only to particular embodiments, and unless it is stated to the contrary in the specification, it is intended to limit the invention. Not intended As used herein, the singular forms “a,” “an” and “the” include plural forms as well, unless the phrases clearly indicate the opposite.

Also, as used herein, the meaning of “comprising” embodies a particular characteristic, region, integer step, operation, element, or component, and excludes the addition of other specific characteristics, region, integer, step, operation, element, or component. It is not.

On the other hand, the "reverse wavelength dispersible compound" itself shows liquid crystallinity and reverse wavelength dispersibility, or does not itself show liquid crystallinity, but is polymerized or crosslinked with any liquid crystal compound so that the liquid crystal compound is reverse wavelength. It means a compound that can exhibit dispersibility. Specifically, after orienting a composition containing the reverse wavelength dispersible compound or the reverse wavelength dispersible compound and a liquid crystal compound (for example, a semi-ungsogenic mesogenic compound having liquid crystallinity) in a liquid crystal state, the state When irradiating active energy rays, such as an ultraviolet-ray, can obtain the superposition | polymerization which fixed the orientation structure of liquid crystal molecule. The polymer obtained in this way has anisotropy of physical properties such as refractive index, dielectric constant, magnetization rate, elastic modulus, thermal expansion rate, and the like, so that it can be applied as an optical anisotropic body such as a retardation plate, a polarizing plate polarizing prism, a brightness enhancing film, and an optical fiber coating material. .

In addition, "specific birefringent index" means a phase difference value in the wavelength λ of transmitted light passing through the optical film, and may be represented by Δη (λ).

In addition, "mesogenic group" means a group having the ability to induce liquid crystal phase behavior. And "spacer groups" are known to those of ordinary skill in the art, for example in C. Tschierske, G. Pelzl, S. Diele, Angew. Chem. 2004, 116, 6340-6368. The spacer group refers to a flexible organic group connecting the mesogenic group and the polymerizable group.

And “carbyl groups” comprise one or more carbon atoms (eg, —C≡C—) free of any non-carbon atoms, or optionally one or more non-carbon atoms (eg, N, O, S, P At least one carbon atom in combination with Si Carbonyl), meaning any monovalent or polyvalent organic radical moiety. "Hydrocarbyl group" means a carbyl group that additionally contains one or more H atoms and optionally one or more heteroatoms (eg, N, 0, S, P, Si).

I. Reverse wavelength dispersion compound

According to an embodiment of the invention, the formula

Dispersible compounds are pore:

[

In Chemical Formula 1,

And L ² are each independently -H, -F, -CI, -Br, -I, -CN, -NC, -NCO, -OCN ᅳ -SCN, -C (= O) NR ¹ R ² , -C (= O) R ¹ , -OC (= O) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -S0 ₂ R ¹ ,-OH, -NO ₂ , -CF ₃ ,- SF ₃ , substituted or unsubstituted silyl, substituted or unsubstituted carbon number

1 to 40 carbyls or hydrocarbyls, or -Sp-P, wherein at least one of L ¹ and L ² is -S _p -P, P is a polymerizable group, and s _p is a spacer group or a single bond R ¹ and R ² are each independently -H or alkyl having 1 to 12 carbon atoms;

m and n are each independently an integer from 1 to 5; M or n is

G ¹ and G ² are each independently a non-aromatic carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms, wherein at least one of G ¹ and G ² is A carbocyclic or heterocyclic group, and any one of the hydrogens contained in the carbocyclic or heterocyclic group is substituted with a group represented by the following Chemical Formula 2:

[

In Chemical Formula 2,

p is an integer of 1 to 10, and if p is 2 or more, each repeating unit of-(Q ¹ )-which is repeated two or more times may be the same or different from each other,

Q ¹ is independently a divalent group selected from the group consisting of -C≡C-, -CY ¹ = CY ^2- , and a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 20 carbon atoms, wherein Y ¹ And Y ² are each independently -H, -F, -CI -CN, or -R ¹ ,

B ¹ is -H, -F, -Gl, -Br, -I, -CN, -NC, -NCO, -OCN, -SCN, -C (= O) NR ¹ R ² ,-C (= 0) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -SO ₂ R ¹ , -OH, -NO ₂ , -CF ₃ , -SF ₃ , a polymerizable group (as defined in Formula 1 above) P), a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C2-C4 acyl group, the C2-C6 alkynylene group which the C2-C4 acyl group couple | bonded with the terminal, C1-C6 An alcohol group of 5 or an alkoxy group having 1 to 12 carbon atoms, and R ¹ and R ² are each independently -H or alkyl having 1 to 12 carbon atoms.

As a result of the continuous experiments of the present inventors, the compounds having the structure represented by the formula (1) surprisingly exhibits liquid crystallinity and reverse wavelength dispersion, or do not show liquid crystallinity by themselves but are polymerized with arbitrary liquid crystal compounds or It was confirmed that crosslinking can exhibit reverse wavelength dispersion, thereby providing an optically anisotropic body having a thin thickness and excellent optical properties.

In particular, the compound represented by the formula (1) is a mesogenic group (particularly, L ^1-

The bridging group HQ ¹ ] _P -B ¹ ) of the conjugated structure having high polarization at any one of (D ¹ -G ¹ ) _m -group and-(G ² -D ² ) _n -L ² group) is in the vertical direction. It has a T-shaped structure connected in (axial direction). In other words, unlike the H-shaped symmetric compound in which two rod-shaped mesogenic compounds are symmetrically connected by a bridging group, The reverse wavelength dispersible compound has an asymmetric structure in the form of τ. Accordingly, the compound of Formula 1 may exhibit stable reverse wavelength dispersion by the bridging group having a high polarization vertically and excellent orientation by the asymmetric mesogenic group in the T-shape.

In Formula 1, A is a carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms.

The carbocyclic or heterocyclic group in A is a 5-membered ring (e.g. cyclopentane, tetrahydrofuran, tetrahydrothiofuran, pyridine; 6-membered ring (e.g. cyclonucleic acid, silinane, cyclonuxene, Tetrahydropyran, tetrahydrothiopyran, 1,3-dioxane, 1,3-dithiane, piperidine); 7-membered ring (e.g. cycloheptane); or fused group (e.g. tetrahydronaphthalene, decahydro Naphthalene, indane, bicyclo [1 .1.1] pentane-1,3-diyl, bicyclo [2.2.2] octane-1,4-diyl, spiro [3.3] heptane-2,6-diyl, octa Hydro-4,7-methano-indane-2,5-diyl) and the like.

The aromatic group in A is benzene, biphenylene, triphenylene, naphthalene, anthracene, binaphthylene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzpyrene Fluorene, indene, indenofluorene, spirobifluorene, and the like. In addition, the heteroaromatic groups in A, G ¹ and G ² are 5-membered rings (e.g., blood, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole). , Furan, thiophene, selenophene, oxazole, isoxazole, ^ thiazole, ^ thiazole, ^ oxadiazole, 2,4-oxadiazole,

1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1 ′ 3,4-thiadiazole); 6-membered rings (e.g. pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5 -Tetrazine, 1,2,3,4-tetrazin, 1,2,3,5-tetrajeon); Or fused groups (e.g. carbazole, indole, isoindole, indolizine, indazole, vanzimidazole, benzotriazole, purine, naftimidazole, phenanthrimidazole, pyridimidazole, pyrazineimidazole Quinoxalineimidazole, benzoxazole, _2,2,22 , ₂₂₂₂ _,, _2,2 J 308HCH9SHCHSCCHCC08FCSSCHFFF-----------

(CH ₂ ) ₃ -,-(CH ₂ ) _4- , -CF ₂ CH _2- , -CF2CH2-, -CH = CH-, -CY ^ CY-, -CH = N-, -N = CH-, -N = N-, -CH = CR ^1- , -C≡C-, -CH = CH-COO-, -OCO-CH = CH-, or -CR ¹ R ^2- . Wherein Y ¹ and Y ² are each independently —H, —F, —CI, —CN, or —R ¹ , and R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms. . In Formula 1, L ¹ and L ² are each end of a mesogenic group, each independently -H, -F, -CI, -Br, -I, -CN, -NC, -NCO, -OCN,- SCN,-C (= 0) NR R ² , -C (= O) R ¹ , -OC (= O) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -S0 ₂ R , -OH, -NO _2l -CF ₃ , -SF ₃ , substituted or unsubstituted silyl, substituted or unsubstituted Caviar or hydrocarbyl having 1 to 40 carbon atoms, or -S _p -P, wherein L ¹ and L At least one of ^two is -Sp-P. Wherein P is a polymerizable group, S _p is a spacer group or a single bond, and R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms.

By way of non-limiting example, L ¹ and L ² may be selected from linear, branched or cyclic alkyl groups having 1 to 25 carbon atoms which are mono- or polysubstituted or unsubstituted with F, CI, Br, I, or CN; Wherein at least one non-adjacent CH ₂ group is each independently-ᄋ-, -S-, -NH-, -NR ^1- , SiR ¹ R ^2- , -CO-, -COO-, -OCO-,-OCO -Ο-, -S-CO-, -CO-S-, -SO _2- , -CO-NR ^1- , -NR ¹ -CO-, -NR ¹ -CO-NR ¹ -,-CY ¹ = CY ^2- , or -C≡C-can be replaced. Wherein Y ¹ and Y ² are each independently —H, —F, —CI, —CN, or —R ¹ , and R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms. . '

Further, L ¹ and L ² are alkyl having 1 to 20 carbon atoms, oxaalkyl having 1 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, and having 1 to C carbon atoms. 20 silyl, ester having 1 to 20 carbon atoms, amino having 1 to 20 carbon atoms, and fluoroalkyl having 1 to 20 carbon atoms.

Also, in -Sp-P which is an example of L ¹ and L ² , P is a polymerizable group, and preferably, CH ₂ = CZ ¹ -COO-, CH ₂ = CZ ¹ -CO-, CH ₂ = CZ ^{_{2 - (O) a -,}} CH 3 -CH = CH-O-, (CH 2 = CH) 2 CH-OCO-, (CH 2 = CH-CH 2) 2 CH-OCO-, (CH 2 = CH ) ₂ CH-O-, (CH ₂ = CH- CH ₂ ) ₂ N-, (CH ₂ = CH-CH ₂ ) ₂ N-CO-, HO-CZ ¹ Z ^-, HS-CZ'Z ^-, ΗΖΉ-, HO-C -NH-, CH ₂ = CZ ¹ -CO-NH-, CH ₂ = CH- (COO) _a -Phe- (0) b-, CH ₂ = CH- (CO) _a -Phe- (O) _b- , Phe-

CH = CH-, HOOC-, OCN-, Z ¹ Z ² Z ³ Si-

^'Are each independently -H, -F, -CI, -CN, -CF ₃ , phenyl, or alkyl having 1 to 5 carbon atoms, wherein Phe is -F, -CI, -Br, -I, -CN, -NC, -NCO, -OCN, -SCN, -C (= 0) NR R ² ,-C (= O) R ¹ , -NH ² , -SH, -SR ¹ , -SO ₃ H, -S0 ₂ Or 1,4-phenylene unsubstituted or substituted by R ¹ , -OH, -NO ₂ , -CF ₃ , or -SF ₃ , wherein a and b are each independently 0 or 1. And, in -Sp-P which is an example of the L ¹ and L ² , S _p is -Xp--

It is selected from the formula -X'-S _p 'to be S _p ' -P. S _p 'is alkylene having 1 to 20 carbon atoms mono- or polysubstituted with -F, -CI ᅳ -Br, -I, or -CN, wherein at least one -CH ₂ -group in the alkylene is -0 -, -S-, -NH-, -NR ^1- , SiR ¹ R ² -,-CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S- ^{, -NR 1 -CO-0-, -O} -CO-NR 1 - can be substituted with, -CH = CH-, or ^{-C≡C- -, - NR 1 -CO-} NR 1. And X 'is -O-, -S-, -CO-, -COO-, -OCO-, -Ο-COO-, -CO-NR ^1- , -NR ¹ -CO-, -NR -CO -NR ¹ -,-OCH _2- , -CH ₂ 0-, -SCH _2- , -CH ₂ S-, -OCF _2- , -CF ₂ O-, -SCF _2- , -SF ₂ O-,- CF ₂ CH ₂ -,-CF ₂ CF _2- , -CH = N-, -N = CH-, -N = N-, -CH = CR ^1- , -CY ¹ = CY ^2- , -C≡C -, -CH = CH-COO-, -OCO-CH = CH-, or a single bond. Wherein Y ¹ and Y ² are each independently —H, —F, —CI, —CN, or —R ¹ , and R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms. . In addition, in Formula 1, m and n may have the same or different values, and may each independently be an integer of 1 to 5. Where m Or when n is 2 or more, each repeating unit of-(D ¹ -G ¹ )-or-(G ² -D ² )-that is repeated two or more times may be the same or different from each other. For example, when m is 2, D ¹ or G ¹ included in each repeating unit of-(D ¹ -G ¹ )-(D ¹ -G ¹ )-is the same as or different from each other in the aforementioned range. Can be. Meanwhile, in Formula 1, G ¹ and G ² are each independently a non-aromatic carbocyclic or heterocyclic group having 5 to 8 carbon atoms, or an aromatic or heteroaromatic group having 6 to 20 carbon atoms, wherein the G ¹ and At least one of G ² is the carbocyclic or heterocyclic group.

The carbocyclic group, heterocyclic group, aromatic group, and heteroaromatic group in G ¹ and G ² are replaced with the definitions for A.

In particular, according to an embodiment of the present invention, at least one of the G ¹ and G ² is the carbocyclic or heterocyclic group, any one hydrogen contained in the carbocyclic or heterocyclic group is represented by the formula It is substituted with a group represented by:

[Formula 2]

十 Q

In Chemical Formula 2,

Q ¹ is each independently a divalent group selected from the group consisting of -C≡C-, -CY = CY ^2- , and a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 20 carbon atoms, wherein Y ¹ and Each Y ² is independently —H, —F, —CI, —CN, or —R ¹ ,

B ¹ is -H, -F, -CI, -Br, -I, -CN, -NC, -NCO, -OCN, -SCN, -C (= 0) NR ¹ R ² ,-C (= 0) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -SO ₂ R ¹ , -OH, -N0 _2> -CF _3l -SF ₃ , a polymerizable group (P as defined in Formula 1 above ), An alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an acyl group having 2 to 4 carbon atoms, and having 2 to 4 carbon atoms at the terminal An acyl group bonded to an alkynylene group having 2 to 6 carbon atoms, an alcohol group having 1 to 5 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms, and R ¹ and R ² are each independently -H or alkyl having 1 to 12 carbon atoms. to be.

In Formula 2,-[Q ¹ ] _p -may be composed of at least one subgroup Q ¹ selected from the group consisting of a pi-conjugated linear group, an aromatic group and a heteroaromatic group. For example,-[Q ¹ ] _p -may be composed of one or more subgroups Q ¹ selected from the group having a coupling angle of 120 degrees or more, preferably 180 degrees. Here, p is an integer of 1 to 10, and if p is 2 or more, each repeating unit of-(Q ¹ )-repeated two or more times may be the same or different from each other.

By way of non-limiting example, such subgroup Q ¹ is a divalent aromatic group connected to an adjacent group in the para-position (eg 1,4-phenylene, naphthalene-2,6-diyl, indan-2,6-diyl, Thieno [3,2-b] thiophene-2,5-diyl) or a group comprising sp-splended carbon atoms (eg, -C≡C-). Further, the subgroup Q ¹ may include -CH = CH-, -CY = CY ^2-, and -CH = CR ^1- . Wherein Y ¹ and γ ² are each independently —H, —F, —CI, —CN, or —R ¹ , and R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms. .

In addition,-[Q ¹ ] _P -is selected from the group consisting of -C≡C-, substituted or unsubstituted 1,4-phenylene, and substituted or unsubstituted 9H-fluorene-2,7-diyl. It may include one or more groups. At this time, the H atom in the 9-position in the fluorene group may be replaced with a carbyl or hydrocarbyl group.

Preferably, the above-[Q ¹ ] _p -is ᅳ C≡C——, — C≡≡C— C = C ^'~ ,

It may be selected from the group consisting of.

Where r is 0, 1, 2, 3, or 4 and D is -F, -CI, -Br, -I, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN , -C (= O) NR ¹ R ² , -C (= O) X, -C (= 0) OR ¹ , -NR ¹ R ² , -OH, -SF ₅ , substituted or unsubstituted silyl, carbon number Aryl of 6 to 12, straight or branched chain alkyl of 1 to 12 carbon atoms, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy. In Formula 2, B ¹ is -H, -F, -CI, -Br, -I, -CN, -NIC, -NCO, -OCN, -SCN, -C (= O) NR ¹ R ² , -C (= O) R ¹ , -NH _2> -SH, -SR ¹ , -SO ₃ H, -SO ₂ R ¹ , -OH, -NO ₂ , -CF ₃ , -SF ₃ , a polymerizable group ( P 2 as defined in Formula 1, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an acyl group having 2 to 4 carbon atoms, and an alky having 2 to 6 carbon atoms in which an acyl group having 2 to 4 carbon atoms is bonded to the terminal. It is a nylene group, a C1-C5 alcohol group, or a C1-C12 alkoxy group, and said R <^1> and R <^2> is respectively independently -H or C1-C12 alkyl. In particular, according to an embodiment of the present invention, B ¹ is selected from the group consisting of a pi-conjugated linear group, an aromatic group and a heteroaromatic group such that the bridging group of Formula 2 has a conjugated structure among the above-described exemplary groups. It may be preferable to be the above group (for example, the group referred to above Q ¹ ). As a non-limiting example, as the reverse wavelength dispersible compound of Chemical Formula 1, compounds represented by RD-01 to RD-42 according to embodiments to be described later may be exemplified. However, the reverse wavelength dispersible compound is not limited to the compounds of RD-01 to RD-42, and may be implemented in various combinations in the above-described range.

In addition, the reverse wavelength dispersion compound represented by Chemical Formula 1 may be synthesized by applying known reactions, and a more detailed synthesis method will be described through examples. II. Reverse wavelength dispersion composition

On the other hand, according to another embodiment of the invention, there is provided a reverse wavelength dispersion composition comprising the compound represented by the formula (1).

The reverse wavelength dispersible composition may be a composition in which the compound represented by Chemical Formula 1 is dissolved in a solvent together with a polymerization initiator. The composition represented by Formula 1 may be included alone or in combination of two or more kinds.

Here, as the polymerization initiator, radical polymerization initiators conventional in the art to which the present invention pertains may be used. The content of the polymerization initiator may be determined in a conventional range capable of efficiently eliciting the polymerization reaction of the reverse wavelength dispersible compound. According to embodiments of the invention, the polymerization initiator may comprise from 10 parts by weight ^_0/0, preferably 0.5 to 8 parts by weight ⁰ /, based on the total weight of the composition.

The solvent is benzene, toluene, xylene, mesitylene, n-butylbenzene, diethylbenzene, tetralin, methoxybenzene, 1,2-dimethoxybenzene, ethylene glycol dimethyl Ether, diethylene glycol dimethyl ether, acetone, Methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclonucleanone, ethyl acetate, methyl lactate, ethyl lactate,. Ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate,

Propylene glycol monoethyl ether acetate, Y-butyrolactone, 2-pyridone, N-methyl- 2-pyridone, dimethylformamide, chloroform, dichloromethane, carbon tetrachloride, dichloroethane, trichloroethylene, tetrachloroethylene , chlorobenzene, t- butyl alcohol, diacetone alcohol, glyceryl ^'lean, mono-O paroxetine, ethylene glycol, triethylene glycol, nuclear xylene glycol, ethylene glycol monomethyl ether, ethyl cellosolve, butyl cellosolve to, or their It may be a complex of. Among these solvents, a boiling point of 60 to 250 ^° C. is advantageous for forming a uniform film thickness at the time of application of the composition, and is advantageous for minimizing the residual of the solvent and the deterioration of the orientation.

The reverse wavelength dispersion composition may optionally further include a sensitizer such as xanthone, thioxanthone, chlorothioxanthone, phenothiazine, anthracene, diphenylanthracene, and the like.

Further, the reverse wavelength dispersion composition may optionally contain quaternary ammonium salts, alkylamine oxides, polyamine derivatives, polyoxyethylene-polyoxypropylene condensates, sodium lauryl sulfate, ammonium lauryl sulfate, and alkyl-substituted aromatic sulfonic acids. Surfactants such as salts, alkyl phosphates and perfluoroalkyl sulfonates; Storage stabilizers such as hydroquinone, hydroquinone monoalkyl ethers, pyrogalls, thiophenols, 2-naphthylamines, and 2-hydroxynaphthalenes; Antioxidants such as 2,6-di-t-butyl-P-cresol and triphenylphosphite; UV absorbers such as salicylic acid ester compounds, benzophenol compounds, benzotriazole compounds, cyanoacrylate compounds, and nickel complex salt compounds may be further included.

In addition, the reverse wavelength dispersion composition may further include particulate matter for selectively adjusting optical anisotropy or improving the strength of the polymerized film as necessary. The particulate matter is hacklite, montmorillonite, kallinite, ZnO, TiO ₂ , Ce0 ₂ , Al ₂ 0 ₃ , Fe ₂ O ₃ , Zr0 ₂ , MgF ₂ , SiO ₂ , SrCO ₃ , Ba (OH) ₂ , Ca Inorganic particulate matters such as (OH) ₂ , Ga (OH) ₃ , AI (OH) ₃ , Mg (OH) ₂ , Zr (OH) ₄ ; Organic particulate matter such as carbon nanotubes, fullerenes, dendrimers, polyvinyl alcohols, polymethacrylates, and polyimides. In addition to the compound represented by Chemical Formula 1, the reverse wavelength dispersion composition may further include any liquid crystal compound. The arbitrary liquid crystal compound may be polymerized or not. Here, as said arbitrary liquid crystal compound, the liquid crystal compound which has an ethylenically unsaturated bond, the compound which has an optical active group, a rod-like liquid crystal compound, etc. are mentioned. Then, there the liquid crystal compound of any will be heunhap in appropriate amounts depending on their structure, the preferably the compound is the total compound weight of the 20 parts by weight ^_0/0 or more of the formula (1), or 50 parts by weight ^_0/0 or more It may be advantageous to be included in terms of achieving the above object.

■

III. Optically anisotropic

On the other hand, according to another embodiment of the invention, there is provided an optically anisotropic body formed using the reverse wavelength dispersion composition.

In particular, as the optically anisotropic body is formed using the above-mentioned reverse wavelength dispersing compound, the optically anisotropic substance may exhibit reverse wavelength dispersibility satisfying the following Formulas I and II.

(I)

ᅀ n (450 nm / ᅀ n (550 nm) 1 -0

(Equation II)

ᅀ η (650ηπι) / ᅀ n (550nm)〉 1 · 0

(Wherein Δη (λ) means non-birefringence at wavelength λ), the optically anisotropic body applies the above-mentioned reverse wavelength dispersible composition to a support substrate, and the reverse wavelength dispersible composition It is possible to obtain by desolventing the liquid crystal compound in the oriented state, and then irradiating and polymerizing the energy ray.

Here, the support substrate is not particularly limited, but a preferred example is a glass plate, polyethylene terephthalate film, polyimide film, polyamide film, polymethyl methacrylate film, polystyrene film, polyvinyl chloride film, polytetrafluoroethylene film , Cellulose-based film, silicon film and the like can be used. And, a polyimide alignment film or on the support substrate What gave polyvinyl alcohol the alignment film can be used preferably.

As a method of applying the composition to the support substrate, a known method may be used. For example, a coating method, a spin coating method, a bar coating method, a dip coating method, a spray coating method, or the like may be applied. And, the thickness of the film formed by the composition may vary depending on the use, preferably may be selected in the range of 0.01 to 100.

In addition, as a method of orienting the said liquid crystal compound, the method of performing a pre-orientation process on a support substrate is mentioned as a non-limiting example. As a method of performing an orientation process, the method of forming the liquid crystal aligning side containing various polyimide oriented films or polyvinyl alcohol-type oriented films on a support substrate, and performing a process, such as rubbing, is mentioned. Moreover, the method of applying a magnetic field, an electric field, etc. to the composition on a support substrate is mentioned.

In addition, the method of polymerizing the reverse wavelength dispersion composition may be a known method using light, heat, or electromagnetic waves.

The optically anisotropic body may be used in a retardation film, a polarizing element, an antireflection film, a selective emission film, a viewing angle compensation film, or the like of a liquid crystal display or an OLED display. In particular, when the optically anisotropic body formed using the composition is applied to an OLED display, interference by external light can be minimized, thereby enabling a more perfect black.

【Effects of the Invention】

The reverse wavelength dispersion compound according to the present invention can provide a stronger and more stable reverse wavelength dispersion, thereby providing an optically anisotropic body having excellent optical properties.

[Brief Description of Drawings]

1 a to. 10 illustrates a scheme for synthesizing a reverse wavelength dispersion compound according to one embodiment of the present invention, respectively.

[Specific contents to carry out invention]

Hereinafter, the operation and effect of the invention will be described in more detail with reference to specific examples. However, these embodiments are only presented as an example of the invention, whereby the scope of the invention is not determined.

Compound RD-01 was synthesized according to the scheme shown in FIGS. 1a to 1c.

(Synthesis of Compound 2)

About 100 g of Compound 1 ((rs, 4'r) -4'-pentyl- [1, r-bi (cydohexan)]-4-one) and about 60 g of tetramethylenediamine are tetrahydrofuran ), And about 300 ml of n-butyl lithium was slowly added dropwise at about -78 ^° C. After stirring for about 2 hours, ethynyltrimethylsilane was added thereto and further stirred for about 1 hour. The reaction product was extracted with dichloromethane and water, and the organic layer was chemically dried and purified by column chromatography to obtain about 120 g of Compound 2.

(Synthesis of Compound 3)

About 120 g of Compound 2 and about 100 g of K ₂ CO ₃ (potassium carbonate) were dissolved in methane, and then stirred at room temperature for about 24 hours. This was filtered to remove excess K ₂ CO ₃ and extracted with dichloromethane and water. After the extracted organic layer was chemically dried, the solvent was removed, and purified by column chromatography to obtain about 110g of Compound 3.

(Synthesis of Compound 5)

About 100 g of Compound 4 (1,4-diethynylbenzene) was dissolved in tetrahydrofuran, and then stirred for about 20 minutes at about -78 ^° C. About 500ml n- Butyl lithium in 2.5M hexane was slowly added dropwise over about 2 hours. After stirring for about 4 hours, about 100ml of chlorotrimethylsilane was added thereto and stirred for about 24 hours. The reaction product was extracted with ethyl acetate and water, and the organic layer was chemically dried and purified by column chromatography to obtain about 60 g of compound 5.

(Synthesis of Compound 6)

About 200 g of 1,4-diiodobenzene, about 3 g of Pd (PPh ₃ ) ₂ CI ₂ (Bis (triphenylphosphine) palladium (ll) dichloride), about 5 g of Cul (copper iodide), and about 200 ml of 1 \ 1, [ \ 1-Diisopropylethylamine (1 \ 1-01 0 | 31 "0 11 3 116) was dissolved in tetrahydrofuran, and then tetrahydrofuran in which about 50 g of Compound 5 was dissolved was slowly added dropwise. After stirring under reflux for about 24 hours, the resulting salt was filtered off, extracted with dichloromethane and water, and the extracted organic layer was chemically dried and purified by column chromatography to obtain about 70 g of Compound 6.

(Synthesis of Compound 8)

After about 100g compound 7 (4-hydroxy-3- iodobenzoic acid) and approximately 400g Ν, Ν- DI isopropyl ethyl amine (N, N-diisopropylethylamine) in dissolved in dichloromethane, of about 200g under about 0 ^° C Methyl chloromethyl ether was slowly added dropwise. After stirring for about 24 hours, it was washed with about 500ml of ammonium chloride, extracted with dichloromethane and water. Then, the extracted organic layer was chemically dried, and then the solvent was removed. The obtained material and potassium hydroxide aqueous solution were added to methanol and stirred under reflux for about 3 hours. 6N hydrochloric acid was added thereto, precipitated, and filtered to remove the solvent. And, after removing the extra foreign matter using a nucleic acid, and dried for about 48 hours to obtain about 110g of compound 8.

Synthesis of Compound 9

About 100 g of Compound 8, about 100 g of Compound 3, and about 70 g of 4- (dimethylamino) pyridine) in dichloromethane After melting, the mixture was stirred for about 30 minutes. About 80 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added thereto and stirred for about 24 hours, followed by dichloromethane and water. Extracted. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 150 g of compound 9.

(Synthesis of Compound 10)

About 100 g of Compound 9 and about 300 ml of 6N hydrochloric acid were dissolved in tetrahydrofuran, and then stirred at about 40 ^° C. for about 24 hours. After extraction with dichloromethane and water, the extracted organic layer was chemically dried and purified by column chromatography to obtain about 80 g of Compound 10.

(Synthesis of Compound 12-1)

About 80 g of the compound 10, about 50 g of the compound 11-1 ((1 r, 4r) -4-((4- (acryloyloxy) butoxy) carbonyl) cyclohexanecarboxylic acid), about 5 g of 4- (dimethylamino) pyridine ( 4- (dimethylamino) pyridine)), and about 50 g of Ν, Ν- diisopropylethylamine (N, N-diisoprapylethylamine) were dissolved in dichloromethane and stirred for about 30 minutes. About 80 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide and about 50 g of ethynyltrimethylsilane are added thereto. After stirring for 24 hours, the mixture was extracted with dichloromethane and water. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 100 g of Compound 12-1.

(Synthesis of Compound 13-1)

About 80 g of the compound 12-1, about 20 g of ethynyltrimethylsilane, about 3 g of Pd (PPh ₃ ) ₂ CI ₂ (Bis (triphenylphosphine) palladium (ll) dichloride), and about 5 g of Cul (copper iodide) was dissolved in tetrahydrofuran and stirred at reflux for about 24 hours. The resulting salt was filtered off and extracted with dichloromethane and water. The extracted organic layer was chemically dried and purified by column chromatography. _// : ols _/ -800 ₁ s2Ml _> dAV ₇

this

ιυαο ⁾ 02 ε ᅳ

^{^{^{) (Ρ Ή) XPPH))}}} (Η2ε ι寸ί 69 I 909Η30寸ρΪ9 Ζ9Ζ / .73 -. Eu - - - - -

⁽ H ^{) () (} Η ^{) (} 8 寸 sr09¾ε ^h u ⁾ Γ ^ζ 6ε ⁹⁰寸 .ωss-. -. --·

Compound RD-02 was synthesized according to the scheme shown in FIGS. 1 a to 1 c.

(Synthesis of Compound 12-2)

Example 55 except that about 55 g of Compound 11-2 ((1 r, 4r) -4-(((6- (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid) was used instead of Compound 11-1. About 100 g of Compound 12-2 was obtained by the same method as the synthesis of Compound 12-1.

(Synthesis of Compound 13-2)

About 70 g of Compound 13-2 was obtained by the same method as the synthesis of Compound 13-1 of Example 1, except that Compound 12-2 was used instead of Compound 12-1.

(Synthesis of Compound 14-2)

About 70 g of Compound 14-2 was obtained by the same method as the synthesis of Compound 14-1 of Example 1, except that Compound 13-2 was used instead of Compound 13-1. ^'

(Synthesis of Compound 15-2)

About 70 g of Compound 15-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 14-2 was used instead of Compound 14-1.

(Synthesis of Compound RD-02)

Except for using the compound 15-2 instead of the compound 15-1, About 50 g of Compound RD-02 was obtained by the same method as the synthesis of Compound RD-1 of Example 1.

The NMR spectrum of the obtained Compound RD-2 is as follows.

1H NMR (CDCI _3, standard ^{TMS) δ (ρρι η):} 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1 H, d ), 6.05 (1 H, dd), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H, s), 1.60- 1.12 (52H, m) Example 3: Synthesis of Compound RD-03

Compound RD-03 was prepared according to the scheme shown in FIGS. 1a to 1c.

^• Synthesized.

(Synthesis of Compound 12-3)

Example 1, except that about 60 g of Compound 11-3 ((1 r, 4r) -4-(((8- (acr loyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid) was used instead of Compound 11-1. About 100 g of Compound 12-3 was obtained by the same method as the synthesis of Compound 12-1.

(Synthesis of Compound 13-3)

About 70 g of Compound 13-3 was obtained by the same method as the synthesis of Compound 13-1 of Example 1, except that Compound 12-3 was used instead of Compound 12-1.

(Synthesis of Compound 14-3)

Except for using the compound 13-3 instead of the compound 13-1, About 70 g of Compound 14-3 was obtained by the same method as the synthesis of Compound 14-1 of Example 1.

(Synthesis of Compound 15-3)

About 70 g of Compound 15-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 14-3 was used instead of Compound 14-1.

Synthesis of Compound RD-03

About 50 g of Compound RD-03 was obtained by the same method as the synthesis of Compound RD-1 of Example 1, except that Compound 15-3 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-3 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) δ (ρριη): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1 H, d ), 6,05 (1 H, dd), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H, s), 1.60-1.12 (56H, m) Example 4: Synthesis of Compound RD-04

Compound RD-04 was synthesized according to the scheme shown in FIGS. 2a and 2b.

(Synthesis of Compound 17)

About 100 g of Compound 16 (4- (4-hydroxyphenyl) cyclohexanone) Approximately 120 g of Ν, Ν-diisopropylethylamine (Ν, Ν-diisopropylethylamine) is dissolved in dichloromethane, and then about 50 g of methylchloromethyl ether at room temperature. (methyl chloromethyl ether) was slowly added dropwise. This After stirring for about 2 hours, the mixture was extracted with dichloromethane and water. Then, the extracted organic layer was chemically dried, the solvent was removed, and purified by column chromatography to obtain about 120 g of Compound 17.

(Synthesis of Compound 18)

About 120 g of compound 17 and about 100 g of N ᅳ Ν, Ν ', Ν'-tetramethylethylenediamine (^ 46 3 ^ ᅣ 6116 (^ 116)

After dissolving in tetrahydrofuran, the mixture was stirred at about -78 ° C for 20 minutes. About 500 ml of n-butyl lithium in 2.5M hexane was slowly added dropwise over 2 hours. After stirring for about 4 hours, ethynyltrimethylsilane was added thereto and further stirred for about 24 hours. After the reaction product was extracted with ethyl acetate and water, the organic layer was chemically dried and purified by column chromatography to obtain about 100 g of Compound 18.

(Synthesis of Compound 19)

About 100 g of Compound 18 and about 10 g of tetrabutylammonium fluoride hydrate were dissolved in tetrahydrofuran and stirred for about 2 hours. After the reaction was extracted with ethyl acetate and water, the organic layer was chemically dried and purified by column chromatography to obtain about 80 g of compound 19.

(Synthesis of Compound 21)

About 70 g of compound 19, about 70 g of compound 20 [4- (methoxymethoxy) benzoic acid], and about 50 g of 4- (dimethylamino) pyridine] were dissolved in dichloromethane for about 30 minutes. Stirred. About 80 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added thereto, followed by stirring for about 24 hours, followed by dichloromethane and water. Extracted. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 80 g of Compound 21.

Synthesis of Compound 22

About 80 g of Compound 21 and about 300 ml of 6N hydrochloric acid were dissolved in tetrahydrofuran, and then stirred at about 40 ^° C. for about 24 hours. And, _// : ols _/ -800 ₁ s2Ml> dAV ₇

o

^{^{^{) Η (ρ Ή) Ή)}}} ({Ή) (ρρ Ή3卜39 (ρ237 0寸(ρ3寸ρ工ρρ 2 909 / ζ Ζ寸9Ζ.. - -. - - - - - -.

) ⁽ Ή ⁽ Ή ^{) ()}寸 ζ6ε 寸 ε ^ι寸 ρρΗ ⁾ Ηε3η09ζ6 ^ 92 ../ ss-. ^" ᅳ ^"" -·- Example 5: Synthesis of Compound RD-05

Compound RD-05 was synthesized according to the scheme shown in FIGS. 2a and 2b.

(Synthesis of Compound 23-2)

Compound 23-1 of Example 4, except for using compound 11-2 ((1 r, 4r) -4-(((6- (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid) instead of compound 11-1 In the same manner as in the synthesis of about 100 g of Compound 23-2 was obtained.

(Synthesis of Compound 24-2)

About 70 g of Compound 24-2 was obtained by the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 23-2 was used instead of Compound 23-1.

(Synthesis of Compound RD-05)

About 50 g of Compound RD-05 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 24-2 was used instead of Compound 24-1.

The NMR spectrum of the obtained Compound RD-05 is as follows.

¹ H NMR (CDCI ₃ , TMS) δ (ρρη): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d) , 7.21 (2H, d), 6.27 (2H, dd), 6.05 (2H, dd), 5.59 (2H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (4H, t) , 2.50 (1 H, s), 1.60-1 .12 (31 H, m)

Compound RD-06 was synthesized according to the scheme shown in FIGS. 2a and 2b.

(Synthesis of Compound 23-3)

Compound 23 of Example 4, except that Compound 11-3 7-3 ((lr, 4r) -4-(((8- (acryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid) was used instead of Compound 11-1 About 100 g of Compound 23-3 was obtained by the same method as the synthesis of -1.

(Synthesis of Compound 24-3)

About 70 g of Compound 24-3 was obtained by the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 23-3 was used instead of Compound 23-1.

Synthesis of Compound RD-06

About 50 g of Compound RD-06 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 24-3 was used instead of Compound 24-1.

The NMR spectrum of the obtained Compound RD-06 is as follows.

1 H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d),

7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (2H, dd), 6.05 (2H, dd), 5.59 (2H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (4H, t), 2.50 (1 H, s), 1.60-1.12 (39H, m) Example 7: Synthesis of Compound RD-07

Compound RD-07 was synthesized according to the scheme shown in FIGS. 3a and 3b.

Synthesis of Compound 26

About 100 g of Compound 25 (4-hydroxybenzoic acid), about 100 g of Ν, Ν'- dicyclonucleosilcarbodiimide (N, N'-dicyclohexylcarbodiimide), about 10 g of 4- (dimethylamino) pyridine (4- (dimethylamino pyridine)), and about 20 g of tert-butanol (tert-butan) were dissolved in tetrahydrofuran and stirred for about 24 hours. After extraction with dichloromethane and water, the extracted organic layer was chemically dried and purified by column chromatography to obtain about 80 g of Compound 26.

(Synthesis of Compound 28-1)

About 60 g of Compound 26, about 50 g of Compound 27-1 [(1 r, 4r) -4- (butoxycarbonyl) cyclohexanecarboxylic acid], about 5 g of 4- (dimethylamino) pyridine), And about 50 g of N, N-diisopropylethylamine (N, N-diisoprapylethylamine) was dissolved in dichloromethane and stirred for about 30 minutes. Here, about 80 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1 -ethyl-3- (3-dimethylaminopropyl) carbodiimide) and about ^' . 50 g of ethynyltrimethylsilane was added and stirred for about 24 hours, followed by extraction with dichloromethane and water. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 80 g of Compound 28-1. Got it.

(Synthesis of Compound 29-1)

About 80 g of Compound 28-1 and about 50 g of tetrafluoraacetic acid were dissolved in dichloromethane and stirred for about 24 hours. After extraction with dichloromethane and water, the extracted organic layer was chemically dried and purified by column chromatography to obtain about 60 g of Compound 29-1.

(Synthesis of Compound 30-1)

About 60 g of Compound 29-1, about 50 g of Compound 19 according to Example 4, and about 50 g of 4- (dimethylamino) pyridine were dissolved in dichloromethane and stirred for about 30 minutes. . About 80 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added thereto and stirred for about 24 hours, followed by dichloromethane and water. Extracted. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 80 g of Compound 30-1.

(Synthesis of Compound 31-1)

About 80 g of Compound 30-1 and about 300 ml of 6N hydrochloric acid were dissolved in tetrahydrofuran, and then stirred for about 24 hours under about 4C C. After extraction with dichloromethane and water, the extracted organic worms were chemically dried and purified by column chromatography to obtain about 60 g of compound 31-1 (m = 3).

(Synthesis of Compound 32-1)

About 80 g of Compound 32-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that Compound 31-1 (m = 3) was used instead of Compound 10.

(Synthesis of Compound 33-1)

About 70 g of Compound 33-1 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-1 was used instead of Compound 14-1.

Synthesis of Compound RD-07 About 30 g of Compound RD-07 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-1 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-07 is as follows.

¹ H NMR (CDCI _3l Standard TMS) 5 (ppm): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (25H, m) Example 8 Synthesis of Compound RD-08

Compound RD-08 was synthesized according to the scheme shown in FIGS. 3a and 3b.

(Synthesis of Compound 28-2)

Compound 27-2 instead of compound 27-1 [(i r, 4r) -4-

About 100 g of Compound 28-2 was obtained by the same method as the synthesis of Compound 28-1 of Example 7, except that ((hexyloxy) carbonyl) cyclohexanecarboxylic acid] was used. .

(Synthesis of Compound 29-2)

Example, except that compound 28-2 was used instead of compound 28-1

About 70 g of Compound 29-2 was obtained by the same method as the synthesis of Compound 29-1 of 7.

(Synthesis of Compound 30-2) About 90 g of Compound 30-2 was obtained by the same method as the synthesis of Compound 30-1 of Example 7, except that Compound 29-2 was used instead of Compound 29-1.

(Synthesis of Compound 31-2)

Example, except that compound 30-2 was used instead of compound 30-1

About 70 g of compound 31-2 (m = 5) was obtained by the same method as the synthesis of compound 31-1 of 7.

(Synthesis of Compound 32-2)

About 80 g of Compound 32-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that Compound 31-2 (m = 5) was used instead of Compound 10.

(Synthesis of Compound 33-2)

About 70 g of Compound 33-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-2 was used instead of Compound 14-1.

(Synthesis of Compound RD-08)

About 30 g of Compound RD-08 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-2 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-08 is as follows.

¹ H NMR (CDCI ₃ , TMS) δ (ρριη): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4Η, d), 7.47 (2Η, d), 7.40 (2Η, d) , 7.21 (2Η, d), 6.27 (1 Η, dd), 6.05 (1 Η, dd), 5.59 (1 Η, dd), 4.13 (4Η, t), 4.05 (1 Η, s), 3.97 (2Η , t), 2.50 (1 mu, t), 1.60-0.90 (29 mu, m) Example 9: Synthesis of Compound RD-09

Compound RD-09 was synthesized according to the scheme shown in FIGS. 3a and 3b.

(Synthesis of Compound 28-3)

Compound 27-3 instead of compound 27-1 [(1 r, 4r) -4-

About 100 g of Compound 28-3 was obtained by the same method as the compound phase of Compound 28-1 of Example 7, except that ((octyloxy) carbonyl) cyclohexanecarboxylic acid] was used.

(Synthesis of Compound 29-3)

About 70 g of Compound 29-3 was obtained by the same method as the synthesis of Compound 29-1 of Example, except that Compound 28-3 was used instead of Compound 28-1.

(Synthesis of Compound 30-3)

About 90 g of Compound 30-3 was obtained by the same method as the synthesis of Compound 30-1 of Example 7, except that Compound 29-3 was used instead of Compound 29-1.

(Synthesis of Compound 31-3)

About 70 g of Compound 31-3 (m = 7) was obtained by the same method as the synthesis of Compound 31-1 of Example 7, except that Compound 30-3 was used instead of Compound 30-1.

(Synthesis of Compound 32-3)

About 80 g of Compound 32- in the same manner as the synthesis of Compound 12-1 of Example 1, except that Compound 31-3 (m = 7) was used instead of Compound 10. Got 3.

(Synthesis of Compound 33-3)

About 70 g of Compound 33-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-3 was used instead of Compound 14-1.

Synthesis of Compound RD-09

About 30 g of Compound RD-09 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-3 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-09 is as follows.

¹ H NMR (CDCI _3> standard TMS) 5 (ppm): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d) , 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H , t), 2.50 (1H, t), 1.60-0.90 (33H, m) Example 10: Synthesis of Compound RD-10

Compound RD-10 was synthesized according to the scheme shown in FIGS. 3a and 3b.

(Synthesis of Compound 32-4)

Compound 31-1 (m = 3) was used instead of Compound 10, and Compound 1 1-2 (n = 6) [(1 r, 4r) -4-(((6-

(acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid] About 80 g of Compound 32-4 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except.

(Synthesis of Compound 33-4)

About 60 g of Compound 33-4 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-4 was used instead of Compound 14-1.

(Synthesis of Compound RD-10)

About 50 g of Compound RD-10 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-4 was used instead of Compound 1 5-1.

The NMR spectrum of the obtained Compound RD-10 is as follows.

¹ H NMR (CDCI _3j Standard TMS) 6 (ppm): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (29H, m) Example 11 Synthesis of Compound RD-11

Compound RD-11 was synthesized according to the scheme shown in FIGS. 3a and 3b.

(Synthesis of Compound 32-5)

Compound 31-2 (m = 5) was used instead of Compound 10, and Compound 1 1-2 (n = 6) [(1 r, 4r) -4-(((6- About 80 g of Compound 32-5 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.

(Synthesis of Compound 33-5)

About 60 g of Compound 33-5 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-5 was used instead of Compound 14-1.

Synthesis of Compound RD-11

About 50 g of Compound RD-11 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-5 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-11 is as follows.

H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m) Example 12: Synthesis of Compound RD-12

Compound RD-12 was synthesized according to the scheme shown in FIGS. 3a and 3b.

(Synthesis of Compound 32-6)

Compound 31-3 (m = 7) was used instead of compound 10, and compound 11-1. Instead of compound 1 1-2 (n = 6) [(i _r , 4r) -4-(((6-

About 80 g of Compound 32-6 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.

(Synthesis of Compound 33-6)

About 60 g of Compound 33-6 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-6 was used instead of Compound 14-1.

(Synthesis of Compound RD-12)

About 50 g of Compound RD-12 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-6 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-12 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d) , 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H , t), 2.50 (1H, t), 1.60-0.90 (37H, m) Example 13: Synthesis of Compound RD-13

Compound RD-13 was synthesized according to the scheme shown in FIGS. 3a and 3b.

(Synthesis of Compound 32-7) Compound 31-1 (m = 3) was used instead of Compound 10, and Compound 11-3 (n = 8) [(ir, 4r) -4-(((8-

(acryloyloxy) octyl) oxy) carbonyl ) ' except for using cyclohexanecarboxylic acid], and in the same manner as in Synthesis of Compound 12-1 in the Example 1 to obtain the compound 32-7 to approximately 80g.

(Synthesis of Compound 33-7)

About 60 g of Compound 33-7 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-7 was used instead of Compound 14-1.

(Synthesis of Compound RD-13)

About 50 g of Compound RD-13 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-7 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-13 is as follows.

1 H NMR (CDCI ₃ , Standard TMS) 6 (ppm): 8.04 (2H, s), 7.56 (4H, d),

7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd ), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H, t), 2.50 (1 H, t), 1.60-0.90 (33H, m) Example 14 Synthesis of Compound RD-14

The compound according to the scheme shown in Figures 3a and 3b

Synthesized. O Jl 5-A 一 3a 3b Se _F S15 £ c _h me

) s ¾ώ 32- Synthesized.

(Synthesis of Compound 32-9)

Compound 31-3 (m = 7) was used instead of Compound 10, and Compound 1 1-3 (n = 8) [(1 r, 4r) -4-(((8- (acryloyloxy)) instead of Compound 11-1. About 80 g of Compound 32-9 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that octyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.

(Synthesis of Compound 33-9)

Synthesis of Compound 15-1 of Example 1, except that Compound 32-9 was used instead of Compound 14-1. In the same manner, about 60 g of compound 33-9 was obtained.

(Synthesis of Compound RD-15)

About 50 g of Compound RD-15 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-9 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-15 is as follows.

H NMR (CDCI3, Standard TMS) 5 (ppm): 8.04 (2H, s), 7.56 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H, t ), 2.50 (1 H, t), 1.60-0.90 (41 H, m) Example 16: Synthesis of Compound RD-16

Compound RD-16 was synthesized according to the scheme shown in FIGS. 4a and 4b.

(Synthesis of Compound 34)

About 200 g of 1,4-diiodobenzene, about 3 g of Pd (PPh ₃ ) ₂ CI ₂

(Bis (triphenylphosphine) palladium (ll) dichloride), about 5 g of Cul (copper iodide), and about 200 ml of Ν, Ν-diaisopropylethylamine (N, N-diisopropylethylamine) were dissolved in tetrahydrofuran, and then To this was slowly added dropwise tetrahydrofuran dissolved about 50 g of compound 4 (1,4- diethynylbenzene). After stirring under reflux for about 24 hours, the resulting salt was filtered off and extracted with dichloromethane and water. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 100 g of Compound 34.

(Synthesis of Compound 35)

About 100 g of Compound 34 was dissolved in tetrahydrofuran and stirred at about -78 ^° C for about 20 minutes. About 500 ml of n-butyl lithium in 2.5M hexane was slowly added dropwise over about 2 hours. After stirring for about 4 hours, about 100ml of chlorotrimethylsilane was added thereto and stirred for about 24 hours. The reaction product was extracted with ethyl acetate and water, and the organic layer was chemically dried and purified by column chromatography to obtain about 60 g of compound 35. (Synthesis of Compound 36)

About 100 g of compound 25 (4-hydroxybenzoic acid) and about 400 g of Ν, Ν-diisopropylethylamine (N, N-diisopropylethylamine) are dissolved in dichloromethane, and then about 200 g of methylchloromethyl ether ^at about 0 ^° C. (methyl chloromethyl ether) was slowly added dropwise. It was stirred for about 24 hours, washed with about 500 ml of ammonium chloride, and extracted with dichloromethane and water. Then, the extracted organic layer was chemically dried, and then the solvent was removed. The obtained material and potassium hydroxide aqueous solution were added to methanol and stirred under reflux for about 3 hours. 6N hydrochloric acid was added thereto, precipitated, and filtered to remove the solvent. Then, the excess foreign material was removed using a nucleic acid, and dried for about 48 hours to obtain about 110 g of Compound 36.

(Synthesis of Compound 37)

About 100 g of Compound 36, about 100 g of Compound 3 according to Example 1, and about 70 g of 4- (dimethylamino) pyridine were dissolved in dichloromethane, followed by stirring for about 30 minutes. About 80 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1-1 교반 -3- (3-dimethylaminopropyl) carbodiimide) was added thereto and stirred for about 24 hours, followed by dichloromethane. Extracted with water. The extracted organic layer was chemically dried and purified by column chromatography to obtain about 150 g of Compound 37.

(Synthesis of Compound 38)

About 100 g of Compound 37 and about 300 ml of 6N hydrochloric acid were dissolved in tetrahydrofuran, and then stirred for about 24 hours at about 40 ^° C. After extraction with dichloromethane and water, the extracted organic layer was chemically dried and purified by column chromatography to obtain about 80 g of Compound 38.

(Synthesis of Compound 39-1)

About 100 g of Compound 39-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that Compound 38 was used instead of Compound 10.

(Synthesis of Compound 40-1) About 30 g of Compound 40-1 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-1 was used instead of Compound 14-1 and Compound 35 was used instead of Compound 6. .

(Synthesis of Compound RD-16)

About 20 g of Compound RD-16 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 40-1 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-16 is as follows.

H NMR (CDCI _3> standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1 H, d), 6.05 (1 H, dd), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H , s), 1.60-1 .12 (48H, m) Example 17 Synthesis of Compound RD-17

Compound RD-17 was synthesized according to the scheme shown in FIGS. 4a and 4b.

(Synthesis of Compound 39-2)

Compound 38 is used instead of compound 10, and compound 1 1 -2 (n = 6) [(1 r, 4r) -4-(((6- (acryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic instead of compound 11-1 acid] About 100 g of Compound 39-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except.

(Synthesis of Compound 40-2)

About 70 g of Compound 40-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-2 was used instead of Compound 14-1 and Compound 35 was used instead of Compound 6. .

(Synthesis of Compound RD-17)

About 50 g of Compound RD-17 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 40-2 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-17 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.40 (2H, d) , 6.27 (1 H, d), 6.05 (1 H, dd), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H, s), 1.60-1 .12 (52H, m) Example 18: Synthesis of Compound RD-18

Compound RD-18 was synthesized according to the scheme shown in FIGS. 4a and 4b.

(Synthesis of Compound 39-3) Compound 38 is used instead of compound 10, and compound 1 1 -3 (n = 8) [(1 r, 4r) -4-(((8-

About 100 g of Compound 39-3 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (acryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid] was used.

(Synthesis of Compound 40-3)

About 70 g of Compound 40-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-3 was used instead of Compound 14-1 and Compound 35 was used instead of Compound 6. .

Synthesis of Compound RD-18

About 50 g of Compound RD-18 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 40-3 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-18 is as follows.

1 H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d),

7.55 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1 H, d), 6.05 (1 H, dd), 5.59 (1 H, d), 4.13 (2H, t ), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1 .12 (56H, m) Example 19: Synthesis of Compound RD-19

Compound RD-19 according to the scheme shown in FIGS. 5a and 5b Synthesized.

(Synthesis of Compound 41-1)

About 70 g of Compound 41-1 was obtained by the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 35 according to Example 16 was used instead of Compound 6.

Synthesis of Compound RD-19

About 30 g of Compound RD-19 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 41-1 was used instead of Compound 24-1.

The NMR spectrum of the obtained Compound RD-19 is as follows.

H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (2H, dd), 6.05 (2H, dd), 5.59 (2H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (4H, t), 2.50 (1 H, t), 1.60-1 .12 (23H, m)

Compound RD-20 was synthesized according to the scheme shown in FIGS. 5a and 5b.

(Synthesis of Compound 41-2)

Use of compound 23-2 according to Example 5 instead of compound 23-1 and compound About 70 g of Compound 41-2 was obtained by the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 35 according to Example 16 was used instead of 6.

Synthesis of Compound RD-20

About 50 g of Compound RD-20 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 41-2 was used instead of Compound 24-1.

The NMR spectrum of the obtained Compound RD-20 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d) , 7.40 (2H, d), 7.21 (2H, d), 6.27 (2H, dd), 6.05 (2H, dd), 5.59 (2H, dd), 4.13 (4H, t), 4.05 (1 H, s) , 3.97 (4H, t), 2.50 (1 H, t), 1.60-1 .12 (31 H, m) Example 21 Synthesis of Compound RD-20

Compound RD-21 was synthesized according to the scheme shown in FIGS. 5a and 5b.

(Synthesis of Compound 41-3)

About the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 23-3 according to Example 6 is used instead of Compound 23-1, and Compound 35 according to Example 16 is used instead of Compound 6. 70 g of compound 41-3 was obtained.

Synthesis of Compound RD-21

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Got it.

The NMR spectrum of the obtained Compound RD-22 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 6 (ppm): 8.04 (2H, d), 7.56 (4H, d) 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd) 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s ), 3.97 (2H, t), 2.50 (1H, t) 1.60-0.90 (25H, m) Example 23: Synthesis of Compound RD-23

Compound RD-23 was synthesized according to the scheme shown in FIGS. 6a and 6b.

(Synthesis of Compound 42-2)

Compound 15- of Example 1, except that Compound 32-2 according to Example 8 (n = 4, m = 5) was used instead of Compound 14-1 and Compound 35 according to Example 16 was used instead of Compound 6. About 60 g of Compound 42-2 was obtained by the same method as the synthesis of 1.

Synthesis of Compound RD-23

About 50 g of Compound RD-23 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-2 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-23 is as follows. _// : O _l s _/ -800 ₁ s2Ml _> dA _V7

Ή ₎ s 寸 99 / Ή ₂₎ 08 _{() Q (l} z 寸 E _dd ᅳ.

_{_{(ρρ (ί ¾ (ρ Ή}} 2 ρ2ρ Ή)卜ζ ^卜寸(ρ (Ζ寸ρ Ή) 9Ζ寸Z 7 - - -. - · - -. -.

^{^{(ϋ (工(pp Ή9pp Ή}} ) 0 (p Ή3) (ρ工ζ2寸Z ζ寸ζ寸(ρ 97.工寸99卜- "-. -. - eu ^-" - eu

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(PP ⁽ p 工⁽ p Ή ^{) (} p Ή ^{) (} p ⁽² 0 ¹ ζ ² ζ 寸 Z ZpHT. ⁷ --.-.-----0 Ή ^{) (H} Ή ⁾ Ή ⁾ Ή ^22ζ 6 εs寸寸 ε ^ι寸^ί 6 ^ 99 ⁰ 9 ^/ ^s-- .. ·

⁽工 63 ⁾ 06009 ^| E-- ^, Example 26: Synthesis of Compound RD-26

Compound RD-26 was synthesized according to the scheme shown in FIGS. 6a and 6b.

(Synthesis of Compound 42-5)

Compound 15- of Example 1, except that Compound 32-5 (n = 6, m = 5) according to Example 11 was used instead of Compound 14-1 and Compound 35 according to Example 16 was used instead of Compound 6 About 60 g of compound 42-5 was obtained by the same method as the synthesis of 1.

Synthesis of Compound RD-26

About 50 g of Compound RD-26 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-5 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-26 is as follows.

H NMR (CDCI _3l Standard TMS) δ (ρρηη): 8.04 (2H, d), 7.56 (4Η, d), 7.55 (4Η, d), 7.51 (4Η, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s ), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m) Example 27: Synthesis of Compound RD-27

Compound RD-27 was synthesized according to the scheme shown in FIGS. 6a and 6b.

(Synthesis of Compound 42-6

Compound 15- of Example 1, except that Compound 32-6 (n = 6, m = 7) according to Example 12 was used instead of Compound 14-1 and Compound 35 according to Example 16 was used instead of Compound 6 About 60 g of compound 42-6 was obtained by the same method as the synthesis of 1.

(Synthesis of Compound RD-27)

About 50 g of Compound RD-27 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-6 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-27 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d) , 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H , s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (37H, m) Example 28: Synthesis of Compound RD-28

Compound RD-28 was synthesized according to the scheme shown in FIGS. 6a and 6b.

(Synthesis of Compound 42-7)

Compound 15- of Example 1, except that Compound 32-7 according to Example 13 (n = 8, m = 3) was used instead of Compound 14-1 and Compound 35 according to Example 16 was used instead of Compound 6. About 60 g of compound 42-7 was obtained by the same method as the synthesis of 1.

(Synthesis of Compound RD-28)

Example 1, except that compound 42-7 was used instead of compound 15-1

About 50 g of Compound RD-28 was obtained by the same method as the synthesis of Compound RD-01.

The NMR spectrum of the obtained Compound RD-28 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 6 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d) , 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H , s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m) Example 29: Synthesis of Compound RD-29

Compound RD-29 was synthesized according to the scheme shown in FIGS. 6a and 6b.

(Synthesis of Compound 42-8)

Compound 15- of Example 1, except that compound 32-8 (n = 8, m = 5) according to Example 14 was used instead of Compound 14-1 and Compound 35 according to Example 16 was used instead of Compound 6 In the same manner as in the synthesis of 1, about 60 g of compound 42-8 was obtained.

(Synthesis of Compound RD-29)

About 50 g of Compound RD-29 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-8 was used instead of Compound 15-1. ^'

The NMR spectrum of the obtained Compound RD-29 is as follows.

H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d), 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (37H, m) Example 30: Synthesis of Compound RD-30

Compound RD-30 was synthesized according to the scheme shown in FIGS. 6a and 6b.

(Synthesis of Compound 42-9)

Compound 15- of Example 1, except that Compound 32-9 (n = 8, m = 7) according to Example 15 was used instead of Compound 14-1 and Compound 35 according to Example 16 was used instead of Compound 6 In the same manner as in the synthesis of 1, about 60 g of compound 42-9 was obtained.

(Synthesis of Compound RD-30)

About 50 g of Compound RD-30 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-9 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-30 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.47 (2H, d) , 7.40 (2H, d), 7.21 (2H, d), 6.27 (1 H, dd), 6.05 (1 H, dd), 5.59 (1 H, dd), 4.13 (4H, t), 4.05 (1 H , s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (41H, m) Example 31 Synthesis of Compound RD-31

Compound RD-31 was synthesized according to the scheme shown in FIGS. 7a and 7b.

(Synthesis of Compound 44-1)

Compound 38 according to Example 16 was used instead of compound 10 and the compound 11-

Compound 43-1 [(1 r, 4r) -4-((4- instead of 1

About OOg Compound 44-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (methacryloyloxy) butoxy) carbonyl) cyclohexanecarboxylic acid was used.

(Synthesis of Compound 45-1)

About 30 g of Compound 45-1 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 44-1 was used instead of Compound 14_1.

(Synthesis of Compound RD-31)

Example, except that Compound 45-1 was used instead of Compound 15-1

About 20 g of Compound RD-31 was obtained by the same method as the synthesis of Compound RD-01.

The NMR spectrum of the obtained Compound RD-31 is as follows.

1 H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.48 (1 H, d) , 6.40 (1 H, d), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H, s), 2.01 (3H , s), 1.60-1.12 (48H, m) Example 32: Synthesis of Compound RD-32

Compound RD-32 was synthesized according to the scheme shown in FIGS. 7a and 7b.

(Synthesis of Compound 44-2)

Compound 38 according to Example 16 is used instead of compound 10, and compound 43-2 [(1 r, 4r) -4-(((6-

About 100 g of Compound 44-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (methacryloyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.

(Synthesis of Compound 45-2)

About 70 g of Compound 45-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 44-2 was used instead of Compound 14-1.

(Synthesis of Compound RD-32)

About 50 g of Compound RD-32 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 45-2 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-32 is as follows.

1 H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.56 (4H, d),

7.51 (4H, d), 7.40 (2H, d), 6.48 (1 H, d), 6.40 (1 H, d), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H, s), 2.01 (3H, s), 1.60-1 .12 (52H, m) Example 33: Synthesis of Compound RD-33

Compound RD-33 was synthesized according to the scheme shown in FIGS. 7a and 7b.

(Synthesis of Compound 44-3)

Compound 38 according to Example 16 is used instead of compound 10, and compound 43-3 [(1 r, 4r) -4-(((8-

About 100 g of Compound 44-3 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (methacryloyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic acid was used.

(Synthesis of Compound 45-3)

Compound 15-1 of Example 1, except that compound 44-3 was used instead of compound 14-1. About 70 g of Compound 45-3 was obtained by the same method as the synthesis.

(Synthesis of Compound RD-33)

About 50 g of Compound RD-33 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 45-3 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-33 is as follows.

H NMR (CDCI3, Standard TMS) δ (ρρηΊ): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.48 (1 H, d), 6.40 (1 H, d), 5.59 (1 H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 2.01 (3H, s), 1.60-1.12 (56H, m) Example 34: Synthesis of Compound RD-34

Compound RD-34 was synthesized according to the scheme shown in FIGS. 8a and 8b.

(Synthesis of Compound 47-1)

Compound 38 according to Example 16 was used instead of compound 10, and compound 46-1 [(1 r, 4r) -4-((4- (ci n na moyloxy) butoxy) ca rbo nyl) cyclo instead of compound 11-1 About 100 g of Compound 47-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that hexa neca rboxyl ic add] was used.

(Synthesis of Compound 48-1)

About 30 g of Compound 48-1 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 47-1 was used instead of Compound 14-1.

Synthesis of Compound RD-34

About 20 g of Compound RD-34 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 48-1 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-34 is as follows.

¹ H NMR (CDCI _3> standard TMS) 5 (ppm): 8.04 (2H, d), 7.60 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1 H, d), 7.40 (4H, d), 7.33 (1 H, t), 6.31 (1 H, d) 4.13 (2H, t) , 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1 .12 (48H, m) Example 35: Synthesis of Compound RD-35

Compound RD-35 was synthesized according to the scheme shown in FIGS. 8a and 8b.

(Synthesis of Compound 47-2)

Compound 38 according to Example 16 is used instead of compound 10, and compound 46-2 [(i r, 4r) -4-(((6-

About 100 g of Compound 47-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that (cinnamoyloxy) hexyl) oxy) carbonyl) cyclohexanecarboxylic acid] was used.

(Synthesis of Compound 48-2)

Example 1 except that compound 47-2 was used instead of compound 14-1.

About 70 g of Compound 48-2 was obtained by the same method as the synthesis of Compound 15-1 of 1.

(Synthesis of Compound RD-35)

About 50 g of Compound RD-35 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 48-2 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-35 is as follows.

¹ H NMR (CDCI _3> standard TMS) 5 (ppm): 8.04 (2H, d), 7.60 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1 H, d), 7.40 (4H, d), 7.33 (1 H, t), 6.31 (1 H, d) 4.13 (2H, t) , 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (52H, m) Example 36: Synthesis of Compound RD-36

Compound RD-36 was synthesized according to the scheme shown in FIGS. 8a and 8b.

(Synthesis of Compound 47-3)

Compound 38 according to Example 16 is used instead of compound 10, and compound 46-3 [(i r, 4r) -4-(((8-

(cinnamoyloxy) octyl) oxy) carbonyl) cyclohexanecarboxylic add] _. About 100 g of Compound 47-3 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that it was used.

(Synthesis of Compound 48-3)

Example, except that compound 47-3 was used instead of compound 14-1

About 70 g of Compound 48-3 was obtained by the same method as the synthesis of Compound 15-1 of 1.

Synthesis of Compound RD-36

About 50 g of Compound RD-36 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 48-3 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-36 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.04 (2H, d), 7.60 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1 H, d), 7.40 (4H, d), 7.33 (1 H, t), 6.31 (1 H, d) 4.13 (2H, t) , 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1 .12 (56H, m) Example 37: Synthesis of Compound RD-37

Compound RD-37 was synthesized according to the scheme shown in FIGS. 9a and 9b.

(Synthesis of Compound 50)

About 110 g of Compound 50 was obtained by the same method as the synthesis of Compound 8 of Example 1, except that Compound 49 (6-hydroxy-2-naphthoic acid) was used instead of Compound 7.

(Synthesis of Compound 51)

About 150 g of Compound 51 was obtained by the same method as the synthesis of Compound 9 of Example 1, except that Compound 50 was used instead of Compound 8.

(Synthesis of Compound 52)

About 80 g of Compound 52 was obtained by the same method as the synthesis of Compound 10 of Example 1, except that Compound 51 was used instead of Compound 9.

(Synthesis of Compound 53-1)

About 100 g of Compound 53-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that Compound 52 was used instead of Compound 10.

(Synthesis of Compound 54-1)

Example, except that Compound 53-1 was used instead of Compound 14-1

) ^{p) (() (p) (3 ,,> ,,} C dΗ N ^I ¾CD ^I m ^: 8.68 ¹ s 8HV TK ^l s 5 H.2 ¹¹

ΐ--. _"

6 £ rns-

LO o 1—1 1

(Synthesis of Compound 54-3)

About 70 g of Compound 54-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 53-3 was used instead of Compound 14-1.

Synthesis of Compound RD-39

About 50 g of Compound RD-39 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 54-3 was used instead of Compound 15-1.

The NMR spectrum of the obtained Compound RD-39 is as follows.

¹ H NMR (CDCI ₃ , Standard TMS) 5 (ppm): 8.68 (1 H, s), 8.21 (1 H, d), 8.18 (1 H, d), 7.98 (1 H, s), 7.97 ( 1 H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1 H, d), 6.27 (1 H, d), 6.05 (1 H, dd), 5.59 (1 H, d ), 4.13 (2H, t), 4.05 (1 H, s), 3.97 (2H, t), 3.52 (1 H, s), 1.60-1 .12 (56H, m)

Compound RD-40 was synthesized according to the scheme shown in FIG. 10. That is, the same as the synthesis of Compound 15-1 of Example 1, except that Compound 39-1 according to Example 16 was used instead of Compound 14-1, and about 10 g of iodobenzene was used instead of Compound 6. By method, about 30 g of compound RD-40 was obtained.

The NMR spectrum of the obtained Compound RD-40 is as follows.

¹ H NMR (CDCI3, Standard TMS) 5 (ppm): 8.04 (2H, d), 7.55 (2H, d), 7.43 (2H, d), 7.43 (2H, d), 7.40 (2H, d), 6.27 (1 H, d), 6.05 (1 H, dd), 5.59 (1 H, d), 4.13 (2H, t), 3.97 (2H, t), 1.60-1.12 (48 H, m)

4.13 (2H, t), 3.97 (2H, t), 1.60-1 .12 (56H, m) Preparation Example 1

(Production of Composition for Optical Device)

About 100 parts by weight of the RD-18 compound according to Example 18, about 12: 5 parts by weight of the mesogenic compound represented by Formula (a), about 37.5 parts by weight of the mesogenic compound represented by Formula (b), and initiator (Irgacure 907 , Ciba-Geigy) about 12.5 parts by weight, antioxidant (Irganox 1076, Ciba-Geigy) about 0.27 parts by weight, fluorine-based surfactant (FC-171, 3M) about 3.33 parts by weight, and about 1000 parts by weight of In combination, a composition for an optical device (solid content of about 21% by weight) was prepared.

[Formula a] ᅳ

^(Preparation of retardation film)

The composition, by the roll coating method, the norbornene-based photo-alignment material is coated

After coating on the TAC film, it was dried for 2 minutes at about 80 ^° C to align the liquid crystal molecules. Thereafter, a retardation film was prepared by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / citf as a light source to fix the alignment state of the liquid crystal.

The quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Arvd) was obtained from the obtained value. As a result, Arrd (450 nm), An d (550 nm) and Arvd (650 nm) were measured to be 103, 1 10, and 1 14, respectively. Therefore, An (450 nm) / An (550 nm) value is 0.94, An (650 nm) / An (550 nm) value is 1.0, it was confirmed that the conditions according to the formulas I and I I above. Preparation ^■ 2

(Production of Composition for Optical Device)

About 75 parts by weight of the RD-18 compound according to Example 18, about 12.5 parts by weight of the mesogenic compound represented by the formula (a), about 62.5 parts by weight of the mesogenic compound represented by the formula (b), an initiator (Irgacure 907, Ciba -Geigy) about 12.5 parts by weight, antioxidant (Irganox 1076, Ciba-Geigy) about 0.27 parts by weight, fluorine-based surfactants (FC-171, 3M) about 3.33 parts by weight, and about 1000 parts by weight of The composition for optical elements (solid content about 21 weight increase ⁰ /.) Was prepared.

(Manufacture of Retardation Film)

The composition is coated with a norbornene-based photo-alignment material, by the coating method

After coating on the TAC film, it was dried for 2 minutes at about 80 ^° C to align the liquid crystal molecules. Thereafter, a retardation film was prepared by a method of fixing non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to the film to fix the alignment state of the liquid crystal.

The quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Arvd) was obtained from the obtained value. As a result, zovd (450 nm), An d (550 nm), and An'd (650 nm) were measured to be 115, 120, and 124, respectively. Therefore, it was confirmed that the value of Δη (450ηηπ) / Δη (550ηιη) was 0.96, and the value of An (650nm) / An (550nm) was 1.03, which satisfies the conditions according to the above formulas I and II. Preparation Example 3

(Production of Composition for Optical Device)

About 100 parts by weight of the RD-40 compound according to Example 40, about 12.5 parts by weight of the mesogenic compound represented by Formula (a), represented by Formula (b) About 37.5 parts by weight of mesogenic compound, About 12.5 parts by weight of initiator (Irgacure 907, Ciba-Geigy), About 0.27 parts by weight of antioxidant (Irganox 1076, Ciba-Geigy), Fluorine-based surfactant (FC-rn, 3M) About 3.33 parts by weight and about 1000 parts by weight of toluene were mixed to prepare a composition for an optical device (solid content of about 21 weight ⁰ /.).

(Manufacture of Retardation Film)

The composition was coated on a TAC film coated with a norbornene-based photo-alignment material by a roll coating method, and then dried ^at about 80 ^° C. for 2 minutes to align the liquid crystal molecules. Thereafter, a retardation film was produced by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to fix the alignment state of the liquid crystal.

The quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Aird) was obtained from the obtained value. As a result, An'd (450 nm), An d (550 nm), and An d (650 nm) were measured to be 1 10, 1 13, and "5. Therefore, the value of An (450 nm) / An (550 nm) was 0.97 and An (650 nm) / An (550 nm) value of 1.0, which was confirmed to satisfy the conditions according to the formula (I) and formula (II).

(Production of Composition for Optical Device)

About 75 parts by weight of the RD-40 compound according to Example 40, about 12.5 parts by weight of the mesogenic compound represented by Formula (a), about 62.5 parts by weight of the mesogenic compound represented by Formula (b), and initiator (Irgacure 907, Ciba -Geigy) about 12.5 parts by weight, antioxidant (Irganox 1076, Ciba-Geigy) about 0.27 parts by weight, fluorine-based surfactants (FC-171, 3M) about 3.33 parts by weight, and about 1000 parts by weight of The composition for optical elements (solid content about 21 weight ⁰ /.) Was prepared.

(Manufacture of Retardation Film)

The composition was coated on a TAC film coated with a norbornene-based photoalignment material by a roll coating method, and then dried ^at about 80 ^° C. for 2 minutes to form a liquid crystal. The molecules were allowed to be oriented. Thereafter, a retardation film was produced by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to fix the alignment state of the liquid crystal.

The quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (Arvd) was obtained from the obtained value. As a result, An d (450 nm), An d (550 nm), and An d (650 nm) were measured to be 125, 126, and 127, respectively. Thus, the Δη (450ηηι) / Δη (550ηηι) values are 0.99 and the An (650 nm) / An (550 nm) values are

1. As, it was confirmed that the conditions according to the formula I and formula I. Comparative Preparation Example 1

(Production of Composition for Optical Device)

About 100 parts by weight of the mesogenic compound represented by the formula ( _a ), about 56.25 parts by weight of the mesogenic compound represented by the formula (b), about 7.8 parts by weight of an initiator (Irgacure 907, Ciba-Geigy), an antioxidant (Irganox 1076 _: Ciba-Geigy Co.) of about 0.17 parts by weight of a fluorine-based surface active agent (FC-171, 3M Co.) of about 2.08 parts by weight, and a toluene about 625 wt common combined parts of the composition for an optical element (a solid content of about 21 weight ^_0/0) Ready.

(Manufacture of Retardation Film)

The composition, by the coating method, the norbornene-based photo-alignment material is coated

After coating on the TAC film, it was dried for 2 minutes at about 80 ^° C to align the liquid crystal molecules. Thereafter, a retardation film was produced by irradiating non-polarized UV light having a high pressure mercury lamp of 200 mW / cuf as a light source to fix the alignment state of the liquid crystal.

The quantitative retardation value of the prepared retardation film was measured using Axoscan (manufactured by Axomatrix Co., Ltd.). At this time, the thickness was measured independently, and the retardation value (An.d) was obtained from the obtained value. As a result, Δη · εΙ (450ηηι), An d (550 nm), and An d (650 nm) were measured at 225, 210, and 203, respectively. Therefore, the An (450nm) / An (550nm) value is 1.07, and the An (650nm) / An (550nm) value is 0.96, and the positive wavelength that does not satisfy the conditions according to Equation & Equation It was confirmed to exhibit dispersion.

Claims

[Patent Claims]

[Claim 1]

Reverse wavelength dispersible compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

L ¹ and L ² are each independently —H, —F, —CI, —Br, —I, —CN, —NC, —NCO, —OCN, —SCN, —C (═O) NR ¹ R ² , -C (= O) R ¹ , -OC (= O) R ¹ , -NH ₂ , -SH, -SR ¹ , -S0 ₃ H, -S0 ₂ R ¹ ,-OH, -N0 _2> -CF ₃ , -SF ₃ , substituted or unsubstituted silyl, substituted or unsubstituted carbyl or hydrocarbyl having 1 to 40 carbon atoms, or -Sp-P, wherein at least one of L ¹ and L ² is -S _p -P , Wherein P is a polymerizable group, s _p is a spacer group or a single bond, and R ¹ and R ² are each independently —H or alkyl having 1 to 12 carbon atoms;

m and n are each independently an integer from 1 to 5; When m or n is 2 or more, each repeating unit of-(D ¹ -G ¹ )-or-(G ² -D ² )-which is repeated two or more times may be the same or different from each other;

[Formula 2]

In Chemical Formula 2,

p is an integer of 1 to 10, and if p is 2 or more, each repeating unit of-(Q ¹ )-repeated two or more times may be the same or different from each other,

Q ¹ is independently a divalent group selected from the group consisting of —C≡C—, —CY═CY ² —, and a substituted or unsubstituted aromatic group or heteroaromatic group having 6 to 20 carbon atoms, wherein Y ¹ and Each Y ² is independently —H, —F, —cr —CN, or —R ¹ ,

B ¹ is -H, -F, -CI, -Br, -I, -CN, -NC, -NCO, -OCN, -SCN, -C (= 0) NR ¹ R ² ,-C (= O) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -SO ₂ R ¹ , -OH, -NO ₂ , -CF ₃ , -SF ₃ , a polymerizable group, alkenes having 2 to 6 carbon atoms An alkyl group, an alkynyl group of 2 to 6 carbon atoms, an acyl group of 2 to 4 carbon atoms, an alkynylene group of 2 to 6 carbon atoms in which an acyl group of 2 to 4 carbon atoms is bonded to a terminal, an alcohol group of 1 to 5 carbon atoms, or 1 to 5 carbon atoms An alkoxy group of 12, and R ¹ and R ² are each independently -H or alkyl having 1 to 12 carbon atoms.

[Claim 2] ^"

The method of claim 1,

A, G ¹ and G ² in Formula 1 are each independently a cyclonucleic acid ring, a cyclonuxene ring, a benzene ring, a naphthalene ring, or a phenanthrene ring;

At least one of G ¹ and ^' G ² is a cyclonucleic acid ring or a cyclonucleene ring.

[Claim 3]

The method of claim 1,

At least one hydrogen contained in A of Formula 1 is -F, -CI, -Br, -I,-

CN, -NC, -NCO, -OCN, -SCN, -C (= 0) NR ¹ R ² , -C (= 0) R ¹ , -NH ₂ , -SH, -SR ¹ , -SO ₃ H, -SO ₂ R ¹ , -OH, -NO ₂ , -CF ₃ , -SF _3> alkenyl group having 2 to 6 carbon atoms, 2 to

Alkynyl groups of 6, acyl groups of 2 to 4 carbon atoms, alkynylene groups of 2 to 6 carbon atoms in which acyl groups of 2 to 4 carbon atoms are bonded to terminals, alcohol groups of 1 to 5 carbon atoms, or alkoxy groups of 1 to 12 carbon atoms And R ¹ and

^ ÷ ¾ 【】 4- oo

Is selected from the group consisting of

R is 0, 1, 2, 3, or 4,

D is -F, -CI, -Br, -I, -CN, -NO ₂ , -NCO, -NCS, -OCN, -SCN, -C (= 0) NR ¹ R ² , -C (= 0 ) X, -C (= O) OR ¹ , -NR ¹ R ² , -OH, -SF ₅ , substituted or unsubstituted silyl, aryl of 6 to 12 carbon atoms, straight or branched chain alkyl of 1 to 12 carbon atoms, And alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy, wherein R ¹ and R ² are each independently -H or alkyl having 1 to 12 carbon atoms.

[Claim 8]

Obtained from a composition comprising a reverse wavelength dispersible compound according to claim 1, wherein the formula | And an optically anisotropic body satisfying equation || (Formula ᅵ)

A ri ( ₄ 50 nm) / ^Δ n (550 nm) <1

(Expression ID

Δ ri (650 nm) / ^Δ Π (550ηΓΤΐ)〉 1 · 0

In formulas (I) and (II), Δη (λ) means specific birefringence at wavelength λ.