Compounds having negative optical dispersion, negative optical dispersion composition comprising the compounds, and optically anisotropic body comprising the composition

Abstract

The present invention relates to a reverse wavelength dispersion compound, a reverse wavelength dispersion composition including the same, and an optically anisotropic body including the same. The reverse wavelength dispersion composition according to the present invention can provide a stronger and more stable reverse wavelength dispersion property, and makes it possible to provide an optically anisotropic body having excellent optical properties.

Claims

1. A reverse wavelength dispersion compound having Chemical Formula 1:
L.sup.1D.sup.1-G.sup.1.sub.mE.sup.1-A-E.sup.2G.sup.2-D.sup.2.sub.nL.sup.2  [Chemical Formula 1] wherein, in Chemical Formula 1, A is a C.sub.6-C.sub.20 aromatic group; E.sup.1, E.sup.2, D.sup.1, and D.sup.2 are independently a single bond, —COO—, or —OCO—; L.sup.1 and L.sup.2 are independently —H, C.sub.1-C.sub.20 alkyl or —S.sub.p—P, wherein at least one of said L.sup.1 and L.sup.2 is —S.sub.p—P, said P is CH.sub.2═CH—COO— or CH.sub.2═CH—OCO—, said S.sub.p is a C.sub.1-C.sub.20 alkylene; m and n are independently an integer of 1 to 5, wherein if said m or n is 2 or more, each repeating unit of -(D.sup.1-G.sup.1)- or -(G.sup.2-D.sup.2)- repeating twice or more may be the same as or different from each other; and G.sup.1 and G.sup.2 are independently a C.sub.5-C.sub.8 non-aromatic carbocyclic group or a C.sub.6-C.sub.20 aromatic group, wherein at least one of said G.sup.1 and G.sup.2 is the carbocyclic group and any one of hydrogens included in the carbocyclic group is substituted by the group represented by the following Chemical Formula 2:
*Q.sup.1.sub.pB.sup.1  [Chemical Formula 2] wherein, in Chemical Formula 2, p is an integer of 1 to 10, wherein if said p is 2 or more, each repeating unit of -(Q.sup.1)- repeating twice or more may be the same as or different from each other, -(Q.sup.1)- is ##STR00046## and B.sup.1 is —H or a C.sub.2-C.sub.6 alkynyl group.

2. The reverse wavelength dispersion compound according to claim 1, wherein G.sup.1, and G.sup.2 of Chemical Formula 1 are independently a cyclohexane ring, a cyclohexene ring, a benzene ring, a naphthalene ring, or a phenanthrene ring; and at least one of said G.sup.1 and G.sup.2 is a cyclohexane ring or a cyclohexene ring, and wherein A of Chemical Formula 1 is a benzene ring, a naphthalene ring, or a phenanthrene ring.

3. An optically anisotropic film includes the reverse wavelength dispersion compound according to claim 1 and satisfies the following Equations I and II:
Δn.sub.(450 nm)/Δn.sub.(550 nm)1.0  (Equation I)
Δn.sub.(650 nm)/Δn.sub.(550 nm)1.0  (Equation II) wherein, in Equations I and II, Δn(λ) means a specific birefringent index at wavelength λ.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIGS. 1a to 10 respectively illustrate the scheme of synthesis of the reverse wavelength dispersion compound according to the embodiments of the present invention.

DETAILED DESCRIPTION OF THE EMBODIMENTS

(2) Hereinafter, functions and effects of the invention are explained in more detail through concrete examples. However, these examples are only for the understanding of the present invention, and the scope of the present invention is not limited to or by them.

Example 1: Synthesis of Compound RD-01

(3) ##STR00003##

(4) Compound RD-01 was synthesized according to the scheme illustrated in FIGS. 1a to 1c.

Synthesis of Compound 2

(5) After dissolving about 100 g of Compound 1 ((1′s,4′r)-4′-pentyl-[1,1′-bi(cyclohexan)]-4-one) and about 60 g of tetramethylenediamine in tetrahydrofuran, about 300 ml of n-butyl lithium was slowly added thereto dropwise at about −78° C. After stirring the mixture for about 2 h, ethynyltrimethylsilane was added thereto and the mixture was additionally stirred for about 1 h. Then, about 120 g of Compound 2 was obtained by extracting the reacted product with dichloromethane and water, chemically drying the obtained organic layer, and refining the same with column chromatography.

Synthesis of Compound 3

(6) After dissolving about 120 g of Compound 2 and about 100 g of K.sub.2CO.sub.3 (potassium carbonate) in methanol, the mixture was stirred for about 24 h at room temperature. After eliminating extra K.sub.2CO.sub.3 therefrom by filtering the same, the obtained product was extracted with dichloromethane and water. Then, about 110 g of Compound 3 was obtained by chemically drying the extracted organic layer for eliminating the solvent therefrom, and refining the same with column chromatography.

Synthesis of Compound 5

(7) After dissolving about 100 g of Compound 4 (1,4-diethynylbenzene) in tetrahydrofuran, the mixture was stirred for about 20 min at about −78° C. About 500 ml of n-butyl lithium in 2.5M hexane was added thereto dropwise for about 2 h. After stirring the same for about 4 h, about 100 ml of chlorotrimethylsilane was added thereto and the mixture was stirred for about 24 h. Then, about 60 g of Compound 5 was obtained by extracting the reacted product with ethyl acetate and water, chemically drying the obtained organic layer, and refining the same with column chromatography.

Synthesis of Compound 6

(8) After dissolving about 200 g of 1,4-diiodobenzene, about 3 g of Pd(PPh.sub.3).sub.2Cl.sub.2 (bis(triphenylphosphine)palladium(II) dichloride), about 5 g of CuI (copper iodide), and about 200 ml of N,N-diisopropylethylamine in tetrahydrofuran, about 50 g of Compound 5 dissolved in tetrahydrofuran was slowly added thereto dropwise. After refluxing and stirring the mixture for about 24 h, the produced salt was filtered and eliminated therefrom and the obtained product was extracted with dichloromethane and water. About 70 g of Compound 6 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 8

(9) After dissolving 100 g of Compound 7 (4-hydroxy-3-iodobenzoic acid) and about 400 g of N,N-diisopropylethylamine in dichloromethane, about 200 g of methylchloromethylether was slowly added thereto dropwise at about 0° C. After stirring the mixture for about 24 h, the product was washed with about 500 ml of ammonium chloride and extracted with dichloromethane and water. The extracted organic layer was chemically dried and the solvent was eliminated therefrom. The product obtained in this way and a potassium hydroxide aqueous solution were put in methanol and the solution was refluxed and stirred for about 3 h. The product was extracted by adding 6N hydrochloric acid thereto and then the solvent was eliminated therefrom by filtering the same. Then, about 110 g of Compound 8 was obtained by eliminating extra foreign substances therefrom by using hexane, and drying the same for about 48 h.

Synthesis of Compound 9

(10) After dissolving about 100 g of Compound 8, about 100 g of Compound 3, and about 70 g of 4-(dimethylamino)pyridine in dichloromethane, the mixture was stirred for about 30 min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 150 g of Compound 9 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 10

(11) After dissolving about 100 g of Compound 9 and about 300 ml of 6N hydrochloric acid in tetrahydrofuran, the mixture was stirred for about 24 h at about 40° C. The reacted product was extracted with dichloromethane and water. Then, about 80 g of Compound 10 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 12-1

(12) After dissolving about 80 g of Compound 10, about 50 g of Compound 11-1 ((1 r,4r)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexanecarboxylic acid), about 5 g of 4-(dimethylamino)pyridine, and about 50 g of N,N-diisopropylethylamine in dichloromethane, the mixture was stirred for about 30 min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and about 50 g of ethynyltrimethylsilane thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 100 g of Compound 12-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 13-1

(13) After dissolving about 80 g of Compound 12-1, about 20 g of ethynyltrimethylsilane, about 3 g of Pd(PPh.sub.3).sub.2Cl.sub.2 (bis(triphenylphosphine)palladium(II) dichloride), and about 5 g of CuI (copper iodide) in tetrahydrofuran, the solution was refluxed and stirred for about 24 h. The produced salt was filtered and eliminated therefrom and the obtained product was extracted with dichloromethane and water. About 70 g of Compound 13-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 14-1

(14) After dissolving about 70 g of Compound 13-1 and about 6 g of AgNO.sub.3 (silver nitrate) in the solvent mixture (water:dichloromethane:ethanol=1:6:3) and stirring the same for about 24 h, about 50 g of Compound 14-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 15-1

(15) After dissolving about 50 g of Compound 14-1, about 20 g of Compound 6, about 3 g of Pd(PPh.sub.3).sub.2Cl.sub.2 (bis(triphenylphosphine)palladium(II) dichloride), and about 5 g of CuI (copper iodide) in tetrahydrofuran, the solution was refluxed and stirred for about 24 h. The produced salt was filtered and eliminated therefrom and the obtained product was extracted with dichloromethane and water. About 30 g of Compound 15-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound RD-01

(16) After dissolving about 30 g of Compound 15-1 and about 6 g of AgNO.sub.3 (silver nitrate) in the solvent mixture (water:dichloromethane:ethanol=1:6:3) and stirring the same for about 24 h, about 20 g of Compound RD-01 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

(17) The NMR spectrum of the obtained Compound RD-01 is as follows.

(18) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (48H, m)

Example 2: Synthesis of Compound RD-02

(19) ##STR00004##

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

Synthesis of Compound 12-2

(21) About 100 g of Compound 12-2 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, 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.

Synthesis of Compound 13-2

(22) 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

(23) 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

(24) 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

(25) About 50 g of Compound RD-02 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 15-2 was used instead of Compound 15-1.

(26) The NMR spectrum of the obtained Compound RD-02 is as follows.

(27) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (52H, m)

Example 3: Synthesis of Compound RD-03

(28) ##STR00005##

(29) Compound RD-03 was synthesized according to the scheme shown in FIGS. 1a to 1c.

Synthesis of Compound 12-3

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

Synthesis of Compound 13-3

(31) 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

(32) About 70 g of Compound 14-3 was obtained by the same method as the synthesis of Compound 14-1 of Example 1, except that Compound 13-3 was used instead of Compound 13-1.

Synthesis of Compound 15-3

(33) 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

(34) About 50 g of Compound RD-03 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 15-3 was used instead of Compound 15-1.

(35) The NMR spectrum of the obtained Compound RD-03 is as follows.

(36) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (56H, m)

Example 4: Synthesis of Compound RD-04

(37) ##STR00006##

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

Synthesis of Compound 17

(39) After dissolving about 100 g of Compound 16 (4-(4-hydroxyphenyl)cyclohexanone) and about 120 g of N,N-diisopropylethylamine in dichloromethane, about 50 g of methylchloromethylether was slowly added thereto dropwise. After stirring the mixture for about 2 h, the product was extracted with dichloromethane and water. Then, about 120 g of Compound 17 was obtained by chemically drying the extracted organic layer for eliminating the solvent therefrom, and refining the same with column chromatography.

Synthesis of Compound 18

(40) After dissolving about 120 g of Compound 17 and about 100 g of N,N,N′,N′-tetramethylethylenediamine in tetrahydrofuran, the mixture was stirred for about 20 min at about −78° C. About 500 ml of n-butyl lithium in 2.5M hexane was added thereto dropwise for about 2 h. After stirring the same for about 4 h, ethynyltrimethylsilane was added thereto and the mixture was additionally stirred for about 24 h. Then, the reacted product was extracted with ethyl acetate and water, and about 100 g of Compound 18 was obtained by chemically drying the obtained organic layer, and refining the same with column chromatography.

Synthesis of Compound 19

(41) After dissolving about 100 g of Compound 18 and about 10 g of tetrabutylammonium fluoride hydrate in tetrahydrofuran, the mixture was stirred for about 2 h. The reacted product was extracted with dichloromethane and water, and about 80 g of Compound 19 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 21

(42) After dissolving about 70 g of Compound 19, about 70 g of Compound [4-(methoxymethoxy)benzoic acid], and about 50 g of 4-(dimethylamino)pyridine in dichloromethane, the mixture was stirred for about min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 80 g of Compound 21 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 22

(43) After dissolving about 80 g of Compound 21 and about 300 ml of 6N hydrochloric acid in tetrahydrofuran, the mixture was stirred for about 24 h at about 40° C. Then, the reacted product was extracted with dichloromethane and water, and about 60 g of Compound 22 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 23-1

(44) After dissolving about 60 g of Compound 22, about 50 g of Compound 11-1 ((1 r,4r)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexanecarboxylic acid), about 5 g of 4-(dimethylamino)pyridine, and about 50 g of N,N-diisopropylethylamine in dichloromethane, the mixture was stirred for about 30 min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and about 50 g of ethynyltrimethylsilane thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 80 g of Compound 23-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 24-1

(45) After dissolving about 80 g of Compound 23-1, about 30 g of Compound 6 of Example 1, about 3 g of Pd(PPh.sub.3).sub.2Cl.sub.2 (bis(triphenylphosphine)palladium(II) dichloride), and about 5 g of CuI (copper iodide) in tetrahydrofuran, the solution was refluxed and stirred for about 24 h. The produced salt was filtered and eliminated therefrom and the obtained product was extracted with dichloromethane and water. About 70 g of Compound 24-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound RD-04

(46) After dissolving about 50 g of Compound 24-1 and about 10 g of AgNO.sub.3 (silver nitrate) in the solvent mixture (water:dichloromethane:ethanol=1:6:3) and stirring the same for about 24 h. About 30 g of Compound RD-04 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

(47) The NMR spectrum of the obtained Compound RD-04 is as follows.

(48) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, s), 3.97 (4H, t), 2.50 (1H, s), 1.60-1.12 (23H, m)

Example 5: Synthesis of Compound RD-05

(49) ##STR00007##

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

Synthesis of Compound 23-2

(51) About 100 g of Compound 23-2 was obtained by the same method as the synthesis of Compound 23-1 of Example 4, except that Compound 11-2 ((1 r,4r)-4-(((6-(acryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid) was used instead of Compound 11-1.

Synthesis of Compound 24-2

(52) 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

(53) 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.

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

(55) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, s), 3.97 (4H, t), 2.50 (1H, s), 1.60-1.12 (31H, m)

Example 6: Synthesis of Compound RD-06

(56) ##STR00008##

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

Synthesis of Compound 23-3

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

Synthesis of Compound 24-3

(59) 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

(60) 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.

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

(62) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, s), 3.97 (4H, t), 2.50 (1H, s), 1.60-1.12 (39H, m)

Example 7: Synthesis of Compound RD-07

(63) ##STR00009##

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

Synthesis of Compound 26

(65) After dissolving about 100 g of Compound 25 (4-hydroxybenzoic acid), about 100 g of N,N′-dicyclohexylcarbodiimide, about 10 g of 4-(dimethylamino)pyridine, and about 20 g of tert-butanol in tetrahydrofuran, the mixture was stirred for about 24 h. Then, the reacted product was extracted with dichloromethane and water, and about 80 g of Compound 26 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 28-1

(66) After dissolving 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 in dichloromethane, the mixture was stirred for about 30 min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and about 50 g of ethynyltrimethylsilane thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 80 g of Compound 28-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 29-1

(67) After dissolving about 80 g of Compound 28-1 and about 50 g of tetrafluoroacetic acid in dichloromethane, the mixture was stirred for about 24 h. Then, the reacted product was extracted with dichloromethane and water, and about 60 g of Compound 29-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 30-1

(68) After dissolving about 60 g of Compound 29-1, about 50 g of Compound of Example 4, and about 50 g of 4-(dimethylamino)pyridine in dichloromethane, the mixture was stirred for about 30 min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 80 g of Compound 30-1 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 31-1

(69) After dissolving about 80 g of Compound 30-1 and about 300 ml of 6N hydrochloric acid in tetrahydrofuran, the mixture was stirred for about 24 h at about 40° C. Then, the reacted product was extracted with dichloromethane and water, and about 60 g of Compound 31-1 (m=3) was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 32-1

(70) 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

(71) 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

(72) 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.

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

(74) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (25H, m)

Example 8: Synthesis of Compound RD-08

(75) ##STR00010##

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

Synthesis of Compound 28-2

(77) 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 Compound 27-2 [(1 r,4r)-4-((hexyloxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 27-1.

Synthesis of Compound 29-2

(78) About 70 g of Compound 29-2 was obtained by the same method as the synthesis of Compound 29-1 of Example 7, except that Compound 28-2 was used instead of Compound 28-1.

Synthesis of Compound 30-2

(79) 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

(80) About 70 g of Compound 31-2 (m=5) was obtained by the same method as the synthesis of Compound 31-1 of Example 7, except that Compound 30-2 was used instead of Compound 30-1.

Synthesis of Compound 32-2

(81) 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

(82) 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

(83) 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.

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

(85) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (29H, m)

Example 9: Synthesis of Compound RD-09

(86) ##STR00011##

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

Synthesis of Compound 28-3

(88) About 100 g of Compound 28-3 was obtained by the same method as the synthesis of Compound 28-1 of Example 7, except that Compound 27-3 [(1 r,4r)-4-((octyloxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 27-1.

Synthesis of Compound 29-3

(89) About 70 g of Compound 29-3 was obtained by the same method as the synthesis of Compound 29-1 of Example 7, except that Compound 28-3 was used instead of Compound 28-1.

Synthesis of Compound 30-3

(90) 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

(91) 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

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

Synthesis of Compound 33-3

(93) 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

(94) 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.

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

(96) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m)

Example 10: Synthesis of Compound RD-10

(97) ##STR00012##

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

Synthesis of Compound 32-4

(99) About 80 g of Compound 32-4 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 and Compound 11-2 (n=6) [(1r,4r)-4-(((6-(acryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 33-4

(100) 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

(101) 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 15-1.

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

(103) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (29H, m)

Example 11: Synthesis of Compound RD-11

(104) ##STR00013##

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

Synthesis of Compound 32-5

(106) 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 Compound 31-2 (m=5) was used instead of Compound 10 and Compound 11-2 (n=6) [(1r,4r)-4-(((6-(acryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 33-5

(107) 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

(108) 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.

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

(110) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m)

Example 12: Synthesis of Compound RD-12

(111) ##STR00014##

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

Synthesis of Compound 32-6

(113) 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 Compound 31-3 (m=7) was used instead of Compound 10 and Compound 11-2 (n=6) [(1r,4r)-4-(((6-(acryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 33-6

(114) 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

(115) 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.

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

(117) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (37H, m)

Example 13: Synthesis of Compound RD-13

(118) ##STR00015##

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

Synthesis of Compound 32-7

(120) About 80 g of Compound 32-7 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 and Compound 11-3 (n=8) [(1r,4r)-4-(((8-(acryloyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 33-7

(121) 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

(122) 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.

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

(124) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m)

Example 14: Synthesis of Compound RD-14

(125) ##STR00016##

(126) Compound RD-14 was synthesized according to the scheme shown in FIGS. 3a and 3b.

Synthesis of Compound 32-8

(127) About 80 g of Compound 32-8 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 and Compound 11-3 (n=8) [(1r,4r)-4-(((8-(acryloyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 33-8

(128) About 60 g of Compound 33-8 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-8 was used instead of Compound 14-1.

Synthesis of Compound RD-14

(129) About 50 g of Compound RD-14 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 33-8 was used instead of Compound 15-1.

(130) The NMR spectrum of the obtained Compound RD-14 is as follows.

(131) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (37H, m)

Example 15: Synthesis of Compound RD-15

(132) ##STR00017##

(133) Compound RD-15 was synthesized according to the scheme shown in FIGS. 3a and 3b.

Synthesis of Compound 32-9

(134) 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 Compound 31-3 (m=7) was used instead of Compound 10 and Compound 11-3 (n=8) [(1r,4r)-4-(((8-(acryloyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 33-9

(135) About 60 g of Compound 33-9 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-9 was used instead of Compound 14-1.

Synthesis of Compound RD-15

(136) 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.

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

(138) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (41H, m)

Example 16: Synthesis of Compound RD-16

(139) ##STR00018##

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

Synthesis of Compound 34

(141) After dissolving about 200 g of 1,4-diiodobenzene, about 3 g of Pd(PPh.sub.3).sub.2Cl.sub.2 (bis(triphenylphosphine)palladium(II) dichloride), about 5 g of CuI (copper iodide), and about 200 ml of N,N-diisopropylethylamine in tetrahydrofuran, about 50 g of Compound 4 (1,4-diethynylbenzene) dissolved in tetrahydrofuran was slowly added thereto dropwise. After refluxing and stirring the mixture for about 24 h, the produced salt was filtered and eliminated therefrom and the obtained product was extracted with dichloromethane and water. About 100 g of Compound 34 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 35

(142) After dissolving about 100 g of Compound 34 in tetrahydrofuran, the mixture was stirred for about 20 min at about −78° C. About 500 ml of n-butyl lithium in 2.5M hexane was added thereto dropwise for about 2 h. After stirring the same for about 4 h, about 100 ml of chlorotrimethylsilane was added thereto and the mixture was stirred for about 24 h. Then, the reacted product was extracted with ethyl acetate and water, and about 60 g of Compound 35 was obtained by chemically drying the obtained organic layer, and refining the same with column chromatography.

Synthesis of Compound 36

(143) After dissolving 100 g of Compound 25 (4-hydroxybenzoic acid) and about 400 g of N,N-diisopropylethylamine in dichloromethane, about 200 g of methylchloromethylether was slowly added thereto dropwise at about 0° C. After stirring the mixture for about 24 h, the product was washed with about 500 ml of ammonium chloride and extracted with dichloromethane and water. The extracted organic layer was chemically dried and the solvent was eliminated therefrom. The product obtained in this way and a potassium hydroxide aqueous solution were put in methanol and the solution was refluxed and stirred for about 3 h. The product was extracted by adding 6N hydrochloric acid thereto and then the solvent was eliminated therefrom by filtering the same. Then, about 110 g of Compound 36 was obtained by eliminating extra foreign substances therefrom by using hexane, and drying the same for about 48 h.

Synthesis of Compound 37

(144) After dissolving about 100 g of Compound 36, about 100 g of Compound 3 of Example 1, and about 70 g of 4-(dimethylamino)pyridine in dichloromethane, the mixture was stirred for about 30 min. After adding about 80 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide thereto and stirring the same for about 24 h, the obtained product was extracted with dichloromethane and water. Then, about 150 g of Compound 37 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 38

(145) After dissolving about 100 g of Compound 37 and about 300 ml of 6N hydrochloric acid in tetrahydrofuran, the mixture was stirred for about 24 h at about 40° C. Then, the reacted product was extracted with dichloromethane and water, and about 80 g of Compound 38 was obtained by chemically drying the extracted organic layer and refining the same with column chromatography.

Synthesis of Compound 39-1

(146) 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

(147) 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

(148) 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.

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

(150) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (48H, m)

Example 17: Synthesis of Compound RD-17

(151) ##STR00019##

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

Synthesis of Compound 39-2

(153) About 100 g of Compound 39-2 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 and Compound 11-2 (n=6) [(1r,4r)-4-(((6-(acryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 40-2

(154) 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

(155) 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.

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

(157) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (52H, m)

Example 18: Synthesis of Compound RD-18

(158) ##STR00020##

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

Synthesis of Compound 39-3

(160) 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 Compound 38 was used instead of Compound 10 and Compound 11-3 (n=8) [(1r,4r)-4-(((8-(acryloyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 40-3

(161) 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

(162) 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.

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

(164) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.55 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, 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

(165) ##STR00021##

(166) Compound RD-19 was synthesized according to the scheme shown in FIGS. 5a and 5b.

Synthesis of Compound 41-1

(167) 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 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-19

(168) 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.

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

(170) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, s), 3.97 (4H, t), 2.50 (1H, t), 1.60-1.12 (23H, m)

Example 20: Synthesis of Compound RD-20

(171) ##STR00022##

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

Synthesis of Compound 41-2

(173) 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 23-2 of Example 5 was used instead of Compound 23-1 and Compound 35 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-20

(174) 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.

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

(176) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, s), 3.97 (4H, t), 2.50 (1H, t), 1.60-1.12 (31H, m)

Example 21: Synthesis of Compound RD-21

(177) ##STR00023##

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

Synthesis of Compound 41-3

(179) About 70 g of Compound 41-3 was obtained by the same method as the synthesis of Compound 24-1 of Example 4, except that Compound 23-3 of Example 6 was used instead of Compound 23-1 and Compound 35 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-21

(180) About 50 g of Compound RD-21 was obtained by the same method as the synthesis of Compound RD-04 of Example 4, except that Compound 41-3 was used instead of Compound 24-1.

(181) The NMR spectrum of the obtained Compound RD-21 is as follows.

(182) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, s), 3.97 (4H, t), 2.50 (1H, t), 1.60-1.12 (39H, m)

Example 22: Synthesis of Compound RD-22

(183) ##STR00024##

(184) Compound RD-22 was synthesized according to the scheme shown in FIGS. 6a and 6b.

Synthesis of Compound 42-1

(185) About 70 g of Compound 42-1 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-1 (n=4, m=3) of Example 7 was used instead of Compound 14-1 and Compound 35 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-22

(186) About 30 g of Compound RD-22 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-1 was used instead of Compound 15-1.

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

(188) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (25H, m)

Example 23: Synthesis of Compound RD-23

(189) ##STR00025##

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

Synthesis of Compound 42-2

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

Synthesis of Compound RD-23

(192) 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.

(193) The NMR spectrum of the obtained Compound RD-23 is as follows.

(194) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (29H, m)

Example 24: Synthesis of Compound RD-24

(195) ##STR00026##

(196) Compound RD-24 was synthesized according to the scheme shown in FIGS. 6a and 6b.

Synthesis of Compound 42-3

(197) About 60 g of Compound 42-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-3 (n=4, m=7) of Example 9 was used instead of Compound 14-1 and Compound 35 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-24

(198) About 50 g of Compound RD-24 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-3 was used instead of Compound 15-1.

(199) The NMR spectrum of the obtained Compound RD-24 is as follows.

(200) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m)

Example 25: Synthesis of Compound RD-25

(201) ##STR00027##

(202) Compound RD-25 was synthesized according to the scheme shown in FIGS. 6a and 6b.

Synthesis of Compound 42-4

(203) About 60 g of Compound 42-4 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-4 (n=6, m=3) of Example 10 was used instead of Compound 14-1 and Compound 35 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-25

(204) About 50 g of Compound RD-25 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-4 was used instead of Compound 15-1.

(205) The NMR spectrum of the obtained Compound RD-25 is as follows.

(206) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (29H, m)

Example 26: Synthesis of Compound RD-26

(207) ##STR00028##

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

Synthesis of Compound 42-5

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

Synthesis of Compound RD-26

(210) 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.

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

(212) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m)

Example 27: Synthesis of Compound RD-27

(213) ##STR00029##

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

Synthesis of Compound 42-6

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

Synthesis of Compound RD-27

(216) 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.

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

(218) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (37H, m)

Example 28: Synthesis of Compound RD-28

(219) ##STR00030##

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

Synthesis of Compound 42-7

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

Synthesis of Compound RD-28

(222) About 50 g of Compound RD-28 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 42-7 was used instead of Compound 15-1.

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

(224) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (33H, m)

Example 29: Synthesis of Compound RD-29

(225) ##STR00031##

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

Synthesis of Compound 42-8

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

Synthesis of Compound RD-29

(228) 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.

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

(230) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (37H, m)

Example 30: Synthesis of Compound RD-30

(231) ##STR00032##

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

Synthesis of Compound 42-9

(233) About 60 g of Compound 42-9 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 32-9 (n=8, m=7) of Example 15 was used instead of Compound 14-1 and Compound 35 of Example 16 was used instead of Compound 6.

Synthesis of Compound RD-30

(234) 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.

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

(236) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(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 (1H, dd), 6.05 (1H, dd), 5.59 (1H, dd), 4.13 (4H, t), 4.05 (1H, s), 3.97 (2H, t), 2.50 (1H, t), 1.60-0.90 (41H, m)

Example 31: Synthesis of Compound RD-31

(237) ##STR00033##

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

Synthesis of Compound 44-1

(239) About 100 g of Compound 44-1 was obtained by the same method as the synthesis of Compound 12-1 of Example 1, except that Compound 38 of Example 16 was used instead of Compound 10 and Compound 43-1 [(1r,4r)-4-((4-(methacryloyloxy)butoxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 45-1

(240) 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

(241) About 20 g of Compound RD-31 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 45-1 was used instead of Compound 15-1.

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

(243) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.48 (1H, d), 6.40 (1H, d), 5.59 (1H, 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 (48H, m)

Example 32: Synthesis of Compound RD-32

(244) ##STR00034##

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

Synthesis of Compound 44-2

(246) 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 Compound 38 of Example 16 was used instead of Compound 10 and Compound 43-2 [(1r,4r)-4-(((6-(methacryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 45-2

(247) 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

(248) 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.

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

(250) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.48 (1H, d), 6.40 (1H, d), 5.59 (1H, 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 (52H, m)

Example 33: Synthesis of Compound RD-33

(251) ##STR00035##

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

Synthesis of Compound 44-3

(253) 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 Compound 38 of Example 16 was used instead of Compound 10 and Compound 43-3 [(1r,4r)-4-(((8-(methacryloyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 45-3

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

Synthesis of Compound RD-33

(255) 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.

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

(257) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.40 (2H, d), 6.48 (1H, d), 6.40 (1H, d), 5.59 (1H, 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

(258) ##STR00036##

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

Synthesis of Compound 47-1

(260) 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 Compound 38 of Example 16 was used instead of Compound 10 and Compound 46-1 [(1r,4r)-4-((4-(cinnamoyloxy)butoxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 48-1

(261) 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

(262) 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.

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

(264) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.60 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1H, d), 7.40 (4H, d), 7.33 (1H, t), 6.31 (1H, 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

(265) ##STR00037##

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

Synthesis of Compound 47-2

(267) 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 Compound 38 of Example 16 was used instead of Compound 10 and Compound 46-2 [(1r,4r)-4-(((6-(cinnamoyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 48-2

(268) About 70 g of Compound 48-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 47-2 was used instead of Compound 14-1.

Synthesis of Compound RD-35

(269) 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.

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

(271) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.60 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1H, d), 7.40 (4H, d), 7.33 (1H, t), 6.31 (1H, 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

(272) ##STR00038##

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

Synthesis of Compound 47-3

(274) 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 Compound 38 of Example 16 was used instead of Compound 10 and Compound 46-3 [(1r,4r)-4-(((8-(cinnamoyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 48-3

(275) About 70 g of Compound 48-3 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 47-3 was used instead of Compound 14-1.

Synthesis of Compound RD-36

(276) 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.

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

(278) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.60 (2H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1H, d), 7.40 (4H, d), 7.33 (1H, t), 6.31 (1H, 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

(279) ##STR00039##

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

Synthesis of Compound 50

(281) 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

(282) 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

(283) 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

(284) 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

(285) About 30 g of Compound 54-1 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 53-1 was used instead of Compound 14-1.

Synthesis of Compound RD-37

(286) About 20 g of Compound RD-37 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 54-1 was used instead of Compound 15-1.

(287) The NMR spectrum of the obtained Compound RD-37 is as follows.

(288) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.68 (1H, s), 8.21 (1H, d), 8.18 (1H, d), 7.98 (1H, s), 7.97 (1H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (48H, m)

Example 38: Synthesis of Compound RD-38

(289) ##STR00040##

(290) Compound RD-38 was synthesized according to the scheme shown in FIGS. 9a and 9b.

Synthesis of Compound 53-2

(291) About 100 g of Compound 53-2 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 and Compound 11-2 [(1r,4r)-4-(((6-(acryloyloxy)hexyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 54-2

(292) About 70 g of Compound 54-2 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 53-2 was used instead of Compound 14-1.

Synthesis of Compound RD-38

(293) About 50 g of Compound RD-38 was obtained by the same method as the synthesis of Compound RD-01 of Example 1, except that Compound 54-2 was used instead of Compound 15-1.

(294) The NMR spectrum of the obtained Compound RD-38 is as follows.

(295) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.68 (1H, s), 8.21 (1H, d), 8.18 (1H, d), 7.98 (1H, s), 7.97 (1H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (52H, m)

Example 39: Synthesis of Compound RD-39

(296) ##STR00041##

(297) Compound RD-39 was synthesized according to the scheme shown in FIGS. 9a and 9b.

Synthesis of Compound 53-3

(298) About 100 g of Compound 53-3 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 and Compound 11-3 [(1r,4r)-4-(((8-(acryloyloxy)octyl)oxy)carbonyl)cyclohexanecarboxylic acid] was used instead of Compound 11-1.

Synthesis of Compound 54-3

(299) 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

(300) 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.

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

(302) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.68 (1H, s), 8.21 (1H, d), 8.18 (1H, d), 7.98 (1H, s), 7.97 (1H, d), 7.56 (4H, d), 7.51 (4H, d), 7.48 (1H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 4.05 (1H, s), 3.97 (2H, t), 3.52 (1H, s), 1.60-1.12 (56H, m)

Example 40: Synthesis of Compound RD-40

(303) ##STR00042##

(304) Compound RD-40 was synthesized according to the scheme shown in FIG. 10.

(305) Namely, about 30 g of Compound RD-40 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-1 of Example 16 was used instead of Compound 14-1 and about 10 g of iodobenzene was used instead of Compound 6.

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

(307) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.55 (2H, d), 7.43 (2H, d), 7.43 (2H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 3.97 (2H, t), 1.60-1.12 (48H, m)

Example 41: Synthesis of Compound RD-41

(308) ##STR00043##

(309) Compound RD-41 was synthesized according to the scheme shown in FIG. 10.

(310) Namely, about 50 g of Compound RD-41 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-2 of Example 17 was used instead of Compound 14-1 and about 10 g of iodobenzene was used instead of Compound 6.

(311) The NMR spectrum of the obtained Compound RD-41 is as follows.

(312) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.55 (2H, d), 7.43 (2H, d), 7.43 (2H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 3.97 (2H, t), 1.60-1.12 (52H, m)

Example 42: Synthesis of Compound RD-42

(313) ##STR00044##

(314) Compound RD-42 was synthesized according to the scheme shown in FIG. 10.

(315) Namely, about 50 g of Compound RD-42 was obtained by the same method as the synthesis of Compound 15-1 of Example 1, except that Compound 39-3 of Example 18 was used instead of Compound 14-1 and about 10 g of iodobenzene was used instead of Compound 6.

(316) The NMR spectrum of the obtained Compound RD-42 is as follows.

(317) .sup.1H NMR (CDCl.sub.3, standard material TMS) δ(ppm): 8.04 (2H, d), 7.55 (2H, d), 7.43 (2H, d), 7.43 (2H, d), 7.40 (2H, d), 6.27 (1H, d), 6.05 (1H, dd), 5.59 (1H, d), 4.13 (2H, t), 3.97 (2H, t), 1.60-1.12 (56H, m)

Preparation Example 1

Preparation of Composition for Optical Elements

(318) About 112.5 parts by weight of a mesogenic compound represented by the following Chemical Formula a, about 37.5 parts by weight of a mesogenic compound represented by the following Chemical Formula b, about 12.5 parts by weight of an initiator (Irgacure 907, Ciba-Geigy Co.), about 0.27 parts by weight of an antioxidant (Irganox 1076, Ciba-Geigy Co.), about 3.33 parts by weight of a fluorine-based surfactant (FC-171, 3M Co.), and about 1000 parts by weight of toluene were mixed with 100 parts by weight of Compound RD-18 of Example 18 for preparing the composition for optical elements (solid content: about 21 wt %).

(319) ##STR00045##

Preparation of Retardation Film

(320) Said composition was coated by a roll coating method on a TAC film on which a norbornene-based light alignment material had been coated, and dried for 2 min at about 80° C. in order to align the liquid crystal molecules. Subsequently, the retardation film was prepared by the method of exposing the film to a non-polarized UV originated from a high pressure mercury lamp of 200 mW/cm.sup.2 for fixing the aligned state of the liquid crystal.

(321) The quantitative retardation value of the prepared retardation film was measured by using Axoscan equipment (product of Axomatrix Co.). At this time, the thickness of the film was measured independently and the retardation value (Δn.Math.d) was obtained from the obtained value. As the result, Δn.Math.d.sub.(450nm), Δn.Math.d.sub.(550nm), and Δn.Math.d.sub.(650nm) were measured as 103, 110, and 114, respectively. Therefore, the value of Δn.sub.(450nm)/Δn.sub.(550nm) was 0.94 and the value of Δn(650 nm)/Δn(550 nm) was 1.04, and thus it was recognized that the film satisfied the conditions according to Equations I and II disclosed above.

Preparation Example 2

Preparation of Composition for Optical Elements

(322) About 112.5 parts by weight of a mesogenic compound represented by Chemical Formula a, about 62.5 parts by weight of a mesogenic compound represented by Chemical Formula b, about 12.5 parts by weight of an initiator (Irgacure 907, Ciba-Geigy Co.), about 0.27 parts by weight of an antioxidant (Irganox 1076, Ciba-Geigy Co.), about 3.33 parts by weight of a fluorine-based surfactant (FC-171, 3M Co.), and about 1000 parts by weight of toluene were mixed with 75 parts by weight of Compound RD-18 of Example 18 for preparing the composition for optical elements (solid content: about 21 wt %).

Preparation of Retardation Film

(323) Said composition was coated by a roll coating method on a TAC film on which a norbornene-based light alignment material had been coated, and dried for 2 min at about 80° C. in order to align the liquid crystal molecules. Subsequently, the retardation film was prepared by the method of exposing the film to non-polarized UV originated from a high pressure mercury lamp of 200 mW/cm.sup.2 for fixing the aligned state of the liquid crystal.

(324) The quantitative retardation value of the prepared retardation film was measured by using Axoscan equipment (product of Axomatrix Co.). At this time, the thickness of the film was measured independently and the retardation value (Δn.Math.d) was obtained from the obtained value. As the result, Δn.Math.d.sub.(450 nm), Δn.Math.d.sub.(550 nm), and Δn.Math.d.sub.(650 nm) were measured as 115, 120, and 124, respectively. Therefore, the value of Δn.sub.(450 nm)/Δn.sub.(550 nm) was 0.96 and the value of Δn.sub.(650 nm)/Δn.sub.(550 nm) was 1.03, and thus it was recognized that the film satisfied the conditions according to Equations I and II disclosed above.

Preparation Example 3

Preparation of Composition for Optical Elements

(325) About 112.5 parts by weight of a mesogenic compound represented by Chemical Formula a, about 37.5 parts by weight of a mesogenic compound represented by Chemical Formula b, about 12.5 parts by weight of an initiator (Irgacure 907, Ciba-Geigy Co.), about 0.27 parts by weight of an antioxidant (Irganox 1076, Ciba-Geigy Co.), about 3.33 parts by weight of a fluorine-based surfactant (FC-171, 3M Co.), and about 1000 parts by weight of toluene were mixed with 100 parts by weight of Compound RD-40 of Example 40 for preparing the composition for optical elements (solid content: about 21 wt %).

Preparation of Retardation Film

(326) Said composition was coated by a roll coating method on a TAC film on which a norbornene-based light alignment material had been coated, and dried for 2 min at about 80° C. in order to align the liquid crystal molecules. Subsequently, the retardation film was prepared by the method of exposing the film to non-polarized UV originated from a high pressure mercury lamp of 200 mW/cm.sup.2 for fixing the aligned state of the liquid crystal.

(327) The quantitative retardation value of the prepared retardation film was measured by using Axoscan equipment (product of Axomatrix Co.). At this time, the thickness of the film was measured independently and the retardation value (Δn.Math.d) was obtained from the obtained value. As the result, Δn.Math.d.sub.(450 nm), Δn.Math.d.sub.(550 nm), and Δn.Math.d.sub.(650 nm) were measured as 110, 113, and 115, respectively. Therefore, the value of Δn.sub.450 nm)/Δn.sub.(550 nm) was 0.97 and the value of Δn.sub.(650 nm)/Δn(550 nm) was 1.02, and thus it was recognized that the film satisfied the conditions according to Equations I and II disclosed above.

Preparation Example 4

Preparation of Composition for Optical Elements

(328) About 112.5 parts by weight of a mesogenic compound represented by Chemical Formula a, about 62.5 parts by weight of a mesogenic compound represented by Chemical Formula b, about 12.5 parts by weight of an initiator (Irgacure 907, Ciba-Geigy Co.), about 0.27 parts by weight of an antioxidant (Irganox 1076, Ciba-Geigy Co.), about 3.33 parts by weight of a fluorine-based surfactant (FC-171, 3M Co.), and about 1000 parts by weight of toluene were mixed with 75 parts by weight of Compound RD-40 of Example 40 for preparing the composition for optical elements (solid content: about 21 wt %).

Preparation of Retardation Film

(329) Said composition was coated by a roll coating method on a TAC film on which a norbornene-based light alignment material had been coated, and dried for 2 min at about 80° C. in order to align the liquid crystal molecules. Subsequently, the retardation film was prepared by the method of exposing the film to non-polarized UV originated from a high pressure mercury lamp of 200 mW/cm.sup.2 for fixing the aligned state of the liquid crystal.

(330) The quantitative retardation value of the prepared retardation film was measured by using Axoscan equipment (product of Axomatrix Co.). At this time, the thickness of the film was measured independently and the retardation value (Δn.Math.d) was obtained from the obtained value. As the result, Δn.Math.d.sub.(450nm), Δn.Math.d.sub.(550 nm), and Δn.Math.d.sub.(650 nm) were measured as 125, 126, and 127, respectively. Therefore, the value of Δn.sub.(450 nm)/Δn.sub.(550 nm) was 0.99 and the value of Δn.sub.(650 nm)/Δn.sub.(550 nm) was 1.01, and thus it was recognized that the film satisfied the conditions according to Equations I and II disclosed above.

Comparative Preparation Example 1

Preparation of Composition for Optical Elements

(331) About 56.25 parts by weight of a mesogenic compound represented by Chemical Formula b, about 7.8 parts by weight of an initiator (Irgacure 907, Ciba-Geigy Co.), about 0.17 parts by weight of an antioxidant (Irganox 1076, Ciba-Geigy Co.), about 2.08 parts by weight of a fluorine-based surfactant (FC-171, 3M Co.), and about 625 parts by weight of toluene were mixed with about 100 parts by weight of a mesogenic compound represented by Chemical Formula a for preparing the composition for optical elements (solid content: about 21 wt %).

Preparation of Retardation Film

(332) Said composition was coated by a roll coating method on a TAC film on which a norbornene-based light alignment material had been coated, and dried for 2 min at about 80° C. in order to align the liquid crystal molecules. Subsequently, the retardation film was prepared by the method of exposing the film to non-polarized UV originated from a high pressure mercury lamp of 200 mW/cm.sup.2 for fixing the aligned state of the liquid crystal.

(333) The quantitative retardation value of the prepared retardation film was measured by using Axoscan equipment (product of Axomatrix Co.). At this time, the thickness of the film was measured independently and the retardation value (Δn.Math.d) was obtained from the obtained value. As the result, Δn.Math.d.sub.(450 nm), Δn.Math.d.sub.(550 nm), and Δn.Math.d.sub.(650 nm) were measured as 225, 210, and 203, respectively. Therefore, the value of Δn.sub.(450 nm)/Δn.sub.(550 nm) was 1.07 and the value of Δn.sub.(650 nm)/Δn(550 nm) was 0.96, and thus it was recognized that the film did not satisfy the conditions according to Equations I and II disclosed above.