POLYMERIZABLE COMPOUND, POLYMERIZABLE COMPOSITION, POLYMER, AND OPTICALLY ANISOTROPIC PRODUCT

Abstract

The present invention is a polymerizable compound represented by a general formula (I), a polymerazable composition, a polymer, and an optically anisotropic product. In the formula: Q.sup.1 to Q.sup.4 represent hydrogen atoms, an alkyl group having 1 to 6 carbon atoms or the like; X represents a divalent aromatic group having 6 to 12 carbon atoms or the like; A.sup.x represents a group represented by a general formula (II); A.sup.yrepresents a group represented by a general formula (III); n represents 0 or 1; * indicates a bonding position; Y.sup.1x to Y.sup.6x and Y.sup.1y to Y.sup.8y represent a chemical single bond, O, S, OC(O), C(O)O, OC(O)O or the like; G.sup.1x, G.sup.2x, G.sup.1y and G.sup.2y represent a divalent aliphatic group having 1 to 20 carbon atoms or the like; Z.sup.1x, Z.sup.2x, Z.sup.1y and Z.sup.2y represent an alkenyl group having 2 to 10 carbon atoms or the like; A.sup.1x and A.sup.1y represent a trivalent aromatic group or the like; A.sup.2x, A.sup.3x, A.sup.4y and A.sup.5Y represent a divalent aromatic group having 4 to 30 carbon atoms or the like; and A.sup.2y and A.sup.3y represent a divalent alicyclic hydrocarbon group having 3 to 30 carbon atoms or the like.

##STR00001##

Claims

1. A polymerizable compound represented by a general formula (I), ##STR00027## wherein each of Q.sup.1 to Q.sup.4 independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, X represents a substituted or unsubstituted divalent aromatic group having 4 to 12 carbon atoms, A.sup.x represents a group represented by a general formula (II), ##STR00028## wherein * indicates a bonding position, each of Y.sup.1x to Y.sup.6x independently represents a chemical single bond, O, S, OC(O), C(O)O, OC(O)O, NR.sup.1C(O), C(O)NR.sup.1, OC(O)NR.sup.1, NR.sup.1C(O)O, NR.sup.1C(O)NR.sup.1, ONR.sup.1, or NR.sup.1O, R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, each of G.sup.1x and G.sup.2x independently represents a substituted or unsubstituted divalent aliphatic group having 1 to 20 carbon atoms that optionally includes O, S, OC(O), C(O)O, OC(O)O, NR.sup.2C(O), C(O)NR.sup.2, NR.sup.2, or C(O), provided that a case where the aliphatic group includes two or more contiguous O or S is excluded, R.sup.2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, each of Z.sup.1x and Z.sup.2x independently represents an alkenyl group having 2 to 10 carbon atoms that is substituted with a halogen atom, or unsubstituted, A.sup.1x represents a substituted or unsubstituted trivalent aromatic group, and each of A.sup.2x and A.sup.3x independently represents a substituted or unsubstituted divalent aromatic group having 4 to 30 carbon atoms, A.sup.y represents a group represented by a general formula (III), ##STR00029## wherein each of Y.sup.1y to Y.sup.8y independently represents a chemical single bond, O, S, OC(O), C(O)O, OC(O)O, NR.sup.3C(O), C(O)NR.sup.3, OC(O)NR.sup.3, NR.sup.3C(O)O, NR.sup.3C(O)NR.sup.3, ONR.sup.3, or NR.sup.3O, R.sup.3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, each of G.sup.1y and G.sup.2y independently represents a substituted or unsubstituted divalent aliphatic group having 1 to 20 carbon atoms that optionally includes O, S, OC(O), C(O)O, OC(O)O, NR.sup.4C(O), C(O)NR.sup.4, NR.sup.4, or C(O), provided that a case where the aliphatic group includes two or more contiguous O or S is excluded, R.sup.4 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, each of Z.sup.1y and Z.sup.2y independently represents an alkenyl group having 2 to 10 carbon atoms that is substituted with a halogen atom, or unsubstituted, A.sup.1y represents a substituted or unsubstituted trivalent aromatic group, each of A.sup.2y and A.sup.3y independently represents a substituted or unsubstituted divalent alicyclic hydrocarbon group having 3 to 30 carbon atoms, and each of A.sup.4y and A.sup.5y independently represents a substituted or unsubstituted aromatic group having 4 to 30 carbon atoms, and n represents 0 or 1.

2. The polymerizable compound according to claim 1, wherein each of A.sup.1x and A.sup.1y is independently a substituted or unsubstituted trivalent benzene ring group, or a substituted or unsubstituted trivalent naphthalene ring group, and each of A.sup.2x, A.sup.3x, A.sup.4y, and A.sup.5y is independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

3. The polymerizable compound according to claim 1, wherein each of Y.sup.1x to Y.sup.6x and Y.sup.1y to Y.sup.8y is independently a chemical single bond, O, OC(O), C(O)O, or OC(O)O.

4. The polymerizable compound according to claim 1, wherein each of Z.sup.1x, Z.sup.2x, Z.sup.1y, and Z.sup.2y is independently CH.sub.2CH, CH.sub.2C(CH.sub.3), or CH.sub.2C(Cl).

5. The polymerizable compound according to claim 1, wherein each of G.sup.1x, G.sup.2x, G.sup.1y, and G.sup.2y is independently a substituted or unsubstituted divalent aliphatic group having 1 to 12 carbon atoms that optionally includes O, OC(O), C(O)O, or C(O), provided that a case where the aliphatic group includes two or more contiguous O is excluded.

6. The polymerizable compound according to claim 1, wherein X is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

7. The polymerizable compound according to claim 1, wherein each of A.sup.1x and A.sup.1y is independently a substituted or unsubstituted trivalent benzene ring group, each of A.sup.2x, A.sup.3x, A.sup.4y, and A.sup.5y is independently a substituted or unsubstituted phenylene group, each of Y.sup.1x to Y.sup.6x and Y.sup.1y to Y.sup.8y is independently a chemical single bond, O, OC(O), C(O)O, or OC(O)O, each of Z.sup.1x, Z.sup.2x, Z.sup.1y, and Z.sup.2y is independently CH.sub.2CH, CH.sub.2C(CH.sub.3), or CH.sub.2C(Cl), and each of G.sup.1x, G.sup.2x, G.sup.1y, and G.sup.2y is independently a divalent alkylene group having 1 to 12 carbon atoms.

8. A polymerizable composition comprising at least one polymerizable compound according to claim 1, and an initiator.

9. A polymer obtained by polymerizing the polymerizable compound according to claim 1.

10. An optically anisotropic product comprising the polymer according to claim 9.

11. A polymer obtained by polymerizing the polymerizable composition according to claim 8.

12. An optically anisotropic product comprising the polymer according to claim 11.

13. The polymerizable compound according to claim 1, wherein the polymerizable compound is represented by a compound 1. ##STR00030##

14. A compound represented by a formula (5). ##STR00031## wherein A.sup.1y represents a substituted or unsubstituted trivalent aromatic group, each of Q.sup.1 to Q.sup.4 independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, X represents a substituted or unsubstituted divalent aromatic group having 4 to 12 carbon atoms, n represents 0 or 1 A.sup.x represents a group represented by a general formula (II), ##STR00032## wherein * indicates a bonding position, each of Y.sup.1x to Y.sup.6x independently represents a chemical single bond, O, S, OC(O), C(O)O, OC(O)O, NR.sup.1C(O), C(O)NR.sup.1, OC(O)NR.sup.1, NR.sup.1C(O)O, NR.sup.1C(O)NR.sup.1, ONR.sup.1, or NR.sup.1O, R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, each of G.sup.1x and G.sup.2x independently represents a substituted or unsubstituted divalent aliphatic group having 1 to 20 carbon atoms that optionally includes O, S, OC(O), C(O)O, OC(O)O, NR.sup.2C(O), C(O)NR.sup.2, NR.sup.2, or C(O), provided that a case where the aliphatic group includes two or more contiguous O or S is excluded, R.sup.2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, each of Z.sup.1x and Z.sup.2x independently represents an alkenyl group having 2 to 10 carbon atoms that is substituted with a halogen atom, or unsubstituted, A.sup.1x represents a substituted or unsubstituted trivalent aromatic group, and each of A.sup.2x and A.sup.3x independently represents a substituted or unsubstituted divalent aromatic group having 4 to 30 carbon atoms.

15. A compound represented by a following formula. ##STR00033##

Description

EXAMPLES

[0174] The invention is further described below by way of examples. Note that the invention is not limited to the following examples.

Example 1

Synthesis of Compound 1

[0175] ##STR00019##

Step 1: Synthesis of Intermediate A

[0176] ##STR00020##

[0177] A four-necked reactor equipped with a thermometer was charged with 5.3 ml (109 mmol) of hydrazine monohydrate and 25 ml of 2-propanol under a nitrogen stream to prepare a solution. After the addition of 3.00 g (21.7 mmol) of 2,5-dihydroxybenzaldehyde to the solution, the mixture was stirred at 25 C. for 30 minutes. After completion of the reaction, a solid precipitate was filtered off by suction filtration. The solid was washed with 2-propanol, and air-dried to obtain 1.82 g of an intermediate A as a white solid (yield: 55.1%). The intermediate A was used directly for the subsequent reaction without purification.

[0178] The structure of the target product was identified by .sup.1H-NMR and .sup.13C-NMR.

[0179] The .sup.1H-NMR spectrum data and the .sup.13C-NMR spectrum data are shown below. .sup.1H-NMR (500 MHz, DMSO-d.sub.6, TMS, ppm): 10.59 (brs, 1H), 8.75 (brs, 1H), 7.82 (s, 1H), 6.81 (s, 2H), 6.617 (d, 1H, J=3.0 Hz), 6.615 (d, 1H, J=9.0 Hz), 6.54 (dd, 1H, J=3.0 Hz, 9.0 Hz)

[0180] .sup.13C-NMR (125 MHz, DMSO-d.sub.6, TMS, ppm): 149.5, 149.1, 141.4, 119.9, 116.1, 115.6, 113.6

Step 2: Synthesis of Intermediate B

[0181] ##STR00021##

[0182] A four-necked reactor equipped with a thermometer was charged with 20 g (144.8 mmol) of 2,5-dihydroxybenzaldehyde, 105.8 g (362.0 mmol) of 4-(6-acryloylhex-1-yloxy)benzoic acid (manufactured by DKSH Japan K.K.), 5.3 g (43.4 mmol) of 4-(dimethylamino)pyridine, and 200 ml of N-methylpyrrolidone under a nitrogen stream to prepare a homogeneous solution. After the addition of 83.3 g (434.4 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) to the solution, the mixture was stirred at 25 C. for 12 hours. After completion of the reaction, the reaction mixture was added to 1.5 l of water, followed by extraction with 500 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. Ethyl acetate was evaporated from the filtrate under reduced pressure using a rotary evaporator to obtain a light yellow solid. The light yellow solid was purified by silica gel column chromatography (toluene:ethyl acetate=9:1 (volume ratio (hereinafter the same))) to obtain 75 g of an intermediate B as a white solid (yield: 75.4%).

[0183] The structure of the target product was identified by .sup.1H-NMR.

[0184] .sup.1H-NMR (400 MHz, CDCl.sub.3, TMS, ppm): 10.20 (s, 1H), 8.18-8.12 (m, 4H), 7.78 (d, 1H, J=2.8 Hz), 7.52 (dd, 1H, J=2.8 Hz, 8.7 Hz), 7.38 (d, 1H, J=8.7 Hz), 7.00-6.96 (m, 4H), 6.40 (dd, 2H, J=1.4 Hz, 17.4 Hz), 6.12 (dd, 2H, J=10.6 Hz, 17.4 Hz), 5.82 (dd, 2H, J=1.4 Hz, 10.6 Hz), 4.18 (t, 4H, J=6.4 Hz), 4.08-4.04 (m, 4H), 1.88-1.81 (m, 4H), 1.76-1.69 (m, 4H), 1.58-1.42 (m, 8H)

Step 3: Synthesis of Intermediate C

[0185] ##STR00022##

[0186] A three-necked reactor equipped with a thermometer was charged with 17.98 g (104.42 mmol) of trans-1,4-cyclohexanedicarboxylic acid and 180 ml of tetrahydrofuran (THF) under a nitrogen stream. After the addition of 6.58 g (57.43 mmol) of methanesulfonyl chloride to the mixture, the reactor was immersed in a water bath to adjust the temperature of the reaction mixture to 20 C. 6.34 g (62.65 mmol) of triethylamine was added dropwise to the reaction mixture over 10 minutes while maintaining the temperature of the reaction mixture at 20 to 30 C. After the dropwise addition, the mixture was stirred at 25 C. for 2 hours.

[0187] After the addition of 0.64 g (5.22 mmol) of 4-(dimethylamino)pyridine and 13.80 g (52.21 mmol) of 4-(6-acryloyloxyhex-1-yloxy)phenol (manufactured by DKSH) to the reaction mixture, the reactor was immersed in a water bath to adjust the temperature of the reaction mixture to 15 C. 6.34 g (62.65 mmol) of triethylamine was added dropwise to the reaction mixture over 10 minutes while maintaining the temperature of the reaction mixture at 20 to 30 C. After the dropwise addition, the mixture was stirred at 25 C. for 2 hours. After completion of the reaction, 1,000 ml of distilled water and 100 ml of a saturated sodium chloride solution were added to the reaction mixture, followed by extraction twice with 400 ml of ethyl acetate. The organic layer was collected, and dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. The solvent was evaporated from the filtrate using a rotary evaporator, and the residue was purified by silica gel column chromatography (THF:toluene=1:9) to obtain 14.11 g of an intermediate C as a white solid (yield: 65%).

[0188] The structure of the target product was identified by .sup.1H-NMR.

[0189] .sup.1H-NMR (500 MHz, DMSO-d.sub.6, TMS, ppm): 12.12 (s, 1H), 6.99 (d, 2H, J=9.0 Hz), 6.92 (d, 2H, J=9.0 Hz), 6.32 (dd, 1H, J=1.5 Hz, 17.5 Hz), 6.17 (dd, 1H, J=10.0 Hz, 17.5 Hz), 5.93 (dd, 1H, J=1.5 Hz, 10.0 Hz), 4.11 (t, 2H, J=6.5 Hz), 3.94 (t, 2H, J=6.5 Hz), 2.48-2.56 (m, 1H), 2.18-2.26 (m, 1H), 2.04-2.10 (m, 2H), 1.93-2.00 (m, 2H), 1.59-1.75 (m, 4H), 1.35-1.52 (m, 8H)

Step 4: Synthesis of Intermediate D

[0190] ##STR00023##

[0191] A four-necked reactor equipped with a thermometer was charged with 780 mg (6.49 mmol) of the intermediate A synthesized in the step 1, 4.55 g (6.18 mmol) of the intermediate B synthesized in the step 2, 3 ml of ethanol, and 20 ml of THF under a nitrogen stream to prepare a solution. After the addition of 69.7 mg (0.30 mmol) of ()-10-camphorsulfonic acid to the solution, the mixture was stirred at 25 C. for 1 hour. After completion of the reaction, the reaction mixture was added to 200 ml of water, followed by extraction with 400 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. Ethyl acetate was evaporated from the filtrate under reduced pressure using a rotary evaporator to obtain a yellow solid. The yellow solid was purified by silica gel column chromatography (toluene:ethyl acetate=90:10) to obtain 1.77 g of a intermediate D as a yellow solid (yield: 34.9%).

[0192] The structure of the target product was identified by .sup.1H-NMR.

[0193] .sup.1H-NMR (500 MHz, DMSO-d.sub.6, TMS, ppm): 10.17 (s, 1H), 9.03 (s, 1H), 8.71 (s, 1H), 8.68 (s, 1H), 8.15 (d, 2H, J=9.0 Hz), 8.12 (d, 2H, J=9.0 Hz), 7.94 (d, 1H, J=3.0 Hz), 7.55 (dd, 1H, J=3.0 Hz, 8.5 Hz), 7.51 (d, 1H, J=8.5 Hz), 7.15 (d, 2H, J=9.0 Hz), 7.14 (d, 2H, J=9.0 Hz), 7.02 (d, 1H, J=3.0 Hz), 6.81 (dd, 1H, J=3.0 Hz, 9.0 Hz), 6.75 (d, 1H, J=9.0 Hz), 6.33 (dd, 2H, J=1.5 Hz, 17.5 Hz), 6.18 (dd, 2H, J=10.5 Hz, 17.5 Hz), 5.94 (dd, 2H, J=1.5 Hz, 10.5 Hz), 4.13 (t, 4H, J=6.5 Hz), 4.11 (t, 4H, J=6.5 Hz), 1.74-1.81 (m, 4H), 1.63-1.68 (m, 4H), 1.38-1.50 (m, 8H)

Step 5: Synthesis of Compound 1

[0194] A three-necked reactor equipped with a thermometer was charged with 1.31 g (3.14 mmol) of the intermediate C synthesized in the step 3 and 20 ml of THF under a nitrogen stream. After the addition of 378 mg (0.786 mmol) of methanesulfonyl chloride to the mixture, the reactor was immersed in a water bath to adjust the temperature of the reaction mixture to 20 C. 334 mg (3.30 mmol) of triethylamine was slowly added dropwise to the reaction mixture while maintaining the temperature of the reaction mixture at 20 to 30 C. After the dropwise addition, the mixture was stirred at 25 C. for 2 hours.

[0195] After the addition of 48.0 mg (0.393 mmol) of 4-(dimethylamino)pyridine and 645 mg (0.786 mmol) of the intermediate D synthesized in the step 4 to the reaction mixture, the reactor was immersed in a water bath to adjust the temperature of the reaction mixture to 15 C. 239 mg (2.36 mmol) of triethylamine was slowly added dropwise to the reaction mixture while maintaining the temperature of the reaction mixture at 20 to 30 C. After the dropwise addition, the mixture was stirred at 25 C. for 2 hours. After completion of the reaction, 100 ml of distilled water was added to the reaction mixture, followed by extraction twice with 100 ml of ethyl acetate. The ethyl acetate layer was collected, and dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. Ethyl acetate was evaporated from the filtrate under reduced pressure using a rotary evaporator to obtain a light yellow solid. The light yellow solid was purified by silica gel column chromatography (toluene:ethyl acetate=90:10) to obtain 771 mg of a compound 1 as a white solid (yield: 60.5%).

[0196] The structure of the target product was identified by .sup.1H-NMR.

[0197] .sup.1H-NMR (500 MHz, CDCl.sub.3, TMS, ppm): 8.72 (s, 1H), 8.57 (s, 1H), 8.19 (d, 2H, J=9.0 Hz), 8.16 (d, 2H, J=9.0 Hz), 8.07 (d, 1H, J=3.0 Hz), 7.79 (d, 1H, J=3.0 Hz), 7.39 (dd, 1H, J=3.0 Hz, 9.0 Hz), 7.31 (d, 1H, J=9.0 Hz), 7.18 (dd, 1H, J=3.0 Hz, 8.5 Hz), 7.13 (d, 1H, J=8.5 Hz), 7.01 (d, 2H, J=8.5 Hz), 6.96-6.99 (m, 6H), 6.87 (d, 4H, J=9.0 Hz), 6.38-6.43 (m, 4H), 6.09-6.16 (m, 4H), 5.81-5.84 (m, 4H), 4.184 (t, 4H, J=6.5 Hz), 4.175 (t, 4H, J=6.5 Hz), 4.07 (t, 2H, J=6.5 Hz), 4.05 (t, 2H, J=6.5 Hz), 3.94 (t, 4H, J=6.5 Hz), 2.50-2.73 (m, 4H), 2.24-2.31 (m, 8H), 1.76-1.92 (m, 8H), 1.61-1.74 (m, 16H), 1.42-1.57 (m, 16H)

Synthesis Example 1

Synthesis of Compound

[0198] ##STR00024##

Step 1: Synthesis of Intermediate E

[0199] ##STR00025##

[0200] A four-necked reactor equipped with a thermometer was charged with 20 g (144.8 mmol) of 2,5-dihydroxybenzaldehyde, 105.8 g (362.0 mmol) of 4-(6-acryloylhex-1-yloxy)benzoic acid (manufactured by DKSH Japan K.K.), 5.3 g (43.4 mmol) of 4-(dimethylamino)pyridine, and 200 ml of N-methylpyrrolidone under a nitrogen stream to prepare a solution. After the addition of 83.3 g (434.4 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) to the solution, the mixture was stirred at 25 C. for 12 hours. After completion of the reaction, the reaction mixture was added to 1.5 l of water, followed by extraction with 500 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and sodium sulfate was filtered off. Ethyl acetate was evaporated from the filtrate under reduced pressure using a rotary evaporator to obtain a light yellow solid. The light yellow solid was purified by silica gel column chromatography (toluene:ethyl acetate=9:1) to obtain 75 g of an intermediate E as a white solid (yield: 75.4%).

[0201] The structure of the target product was identified by .sup.1H-NMR.

[0202] .sup.1H-NMR (400 MHz, CDCl.sub.3, TMS, ppm): 10.20 (s, 1H), 8.18-8.12 (m, 4H), 7.78 (d, 1H, J=2.8 Hz), 7.52 (dd, 1H, J=2.8 Hz, 8.7 Hz), 7.38 (d, 1H, J=8.7 Hz), 7.00-6.96 (m, 4H), 6.40 (dd, 2H, J=1.4 Hz, 17.4 Hz), 6.12 (dd, 2H, J=10.6 Hz, 17.4 Hz), 5.82 (dd, 2H, J=1.4 Hz, 10.6 Hz), 4.18 (t, 4H, J=6.4 Hz), 4.08-4.04 (m, 4H), 1.88-1.81 (m, 4H), 1.76-1.69 (m, 4H), 1.58-1.42 (m, 8H)

Step 2: Synthesis of Compound

[0203] A four-necked reactor equipped with a thermometer was charged with 1.5 g (2.18 mmol) of the intermediate E, 2 ml of 2-propanol, and 5 ml of THF under a nitrogen stream to prepare a solution. After the addition of 80 mg (1.59 mmol) of hydrazine monohydrate to the solution, the mixture was stirred at 25 C. for 21 hours. After completion of the reaction, 2-propanol and THF were evaporated from the reaction mixture under reduced pressure using a rotary evaporator to obtain a yellow solid. The yellow solid was recrystallized from a mixed solvent (toluene:hexane=1:1), and a solid precipitate was filtered off, and washed with a mixed solvent (toluene:hexane=1:1). The resulting solid was purified by silica gel column chromatography (toluene:ethyl acetate=90:10 to 85:15 (gradient)) to obtain 1.1 g of a compound as a light yellow solid (yield: 50.5%).

[0204] The structure of the target product was identified by .sup.1H-NMR.

[0205] .sup.1H-NMR (500 MHz, CDCl.sub.3, TMS, ppm): 8.68 (s, 2H), 8.15 (d, 4H, J=9.0 Hz), 8.12 (d, 4H, J=9.0 Hz), 7.98 (d, 2H, J=3.0 Hz), 7.35 (dd, 2H, J=3.0 Hz, 9.0 Hz), 7.29 (d, 2H, J=9.0 Hz), 6.964 (d, 4H, J=9.0 Hz), 6.957 (d, 4H, J=9.0 Hz), 6.410 (dd, 2H, J=1.5 Hz, 17.5 Hz), 6.407 (dd, 2H, J=1.5 Hz, 17.5 Hz), 6.132 (dd, 2H, J=10.5 Hz, 17.5 Hz), 6.128 (dd, 2H, J=10.5 Hz, 17.5 Hz), 5.829 (dd, 2H, J=1.5 Hz, 10.5 Hz), 5.825 (dd, 2H, J=1.5 Hz, 10.5 Hz), 4.188 (t, 4H, J=6.5 Hz), 4.182 (t, 4H, J=6.5 Hz), 4.048 (t, 4H, J=6.5 Hz), 4.045 (t, 4H, J=6.5 Hz), 1.87-1.81 (m, 8H), 1.76-1.70 (m, 8H), 1.59-1.43 (m, 16H)

Example 2

[0206] 0.4 g of the compound 1 obtained in Example 1, 0.6 g of a compound 1r (LC242 manufactured by BASF) (see below), 30 mg of a photoinitiator (Adekaoptomer N-1919 manufactured by Adeka Corporation), and 100 mg of a 1% cyclopentanone solution of a surfactant (KH-40 manufactured by AGC Seimi Chemical Co., Ltd.) were dissolved in 2.3 g of cyclopentanone. The solution was filtered through a disposable filter having a pore size of 0.45 m to prepare a polymerizable composition 1.

##STR00026##

Comparative Example 1

[0207] A polymerizable composition 2 was prepared substantially in the same manner as in Example 2, except that the compound at obtained in Synthesis Example 1 was used instead of the compound 1.

Comparative Example 2

[0208] A polymerizable composition 3 was prepared substantially in the same manner as in Example 2, except that 1.0 g of the compound obtained in Synthesis Example 1 was used instead of the compound 1 (0.4 g) and the compound 1r (0.6 g).

[0209] Each of the polymerizable compositions 1 to 3 was polymerized using the following method to obtain a polymer. The retardation was measured, and the wavelength dispersion was evaluated using the resulting polymers.

Measurement of Retardation and Evaluation of Wavelength Dispersion

(i) Formation of Liquid Crystal Layer Using Polymerizable Composition

[0210] Each of the polymerizable compositions 1 to 3 was applied to a transparent glass substrate provided with a polyimide alignment film subjected to a rubbing treatment (manufactured by E.H.C. Co., Ltd.) using a #4 wire bar. The resulting film was dried for 1 minute at the temperature shown in Table 1, and subjected to an alignment treatment for 1 minute at the temperature shown in Table 1 to form a liquid crystal layer. Ultraviolet rays were applied to the liquid crystal layer at a dose of 2,000 mJ/cm.sup.2 to effect polymerization to prepare a wavelength dispersion measurement sample.

(ii) Measurement of Retardation

[0211] The retardation between 400 nm and 800 nm was measured using the sample utilizing an ellipsometer (M2000U manufactured by J. A. Woollam).

(iii) Evaluation of Wavelength Dispersion

[0212] The wavelength dispersion was evaluated based on the values and that were calculated as described below using the measured retardation.

[0213] =(retardation at 449.9 nm)/(retardation at 548.5 nm)

[0214] =(retardation at 650.2 nm)/(retardation at 548.5 nm)

[0215] The value is smaller than 1, and the value is larger than 1 when ideal wideband wavelength dispersion (reverse wavelength dispersion) is achieved. The values and are almost identical to each other when flat wavelength dispersion is achieved. The value is larger than 1, and the value is smaller than 1 when normal dispersion is achieved.

[0216] Specifically, flat wavelength dispersion and reverse wavelength dispersion are preferable, and reverse wavelength dispersion is particularly preferable.

[0217] Table 1 shows the thickness (m) of the liquid crystal polymer films obtained by polymerizing the polymerizable compositions, the retardation (Re) at a wavelength of 548.5 nm, and the values and .

TABLE-US-00001 TABLE 1 Polymerizable Polymerizable compound Polymerizable compound Drying temperature composition Compound Ratio (%) Compound Ratio (%) ( C.) Example 2 1 1 40 1r 60 180 Comparative 2 40 1r 60 150 Example 1 Comparative 3 1r 100 80 Example 2 Alignment treatment Temperature during temperature exposure Thickness Re ( C.) ( C.) (m) (548.5 nm) Example 2 160 150 1.493 183.5 0.959 1.001 Comparative 130 130 1.503 205.6 1.035 0.988 Example 1 Comparative 23 23 1.479 222.9 1.086 0.970 Example 2

[0218] As is clear from the results of Comparative Example 2, the compound 1r had normal dispersion since >1 and <1.

[0219] When the compound 1 obtained in Example 1 was added to the compound 1r (Example 2), reverse wavelength dispersion was obtained (i.e., <1 and >1).

[0220] When the compound was added to the compound 1r (Comparative Example 1), reverse wavelength dispersion was not obtained (i.e., >1 and <1).

[0221] It was thus confirmed that a polymer that exhibits reverse wavelength dispersion can be obtained by polymerizing a polymerizable composition obtained by adding the compound according to one embodiment of the invention (compound 1) to a compound that exhibits normal wavelength dispersion.