POLYMERIZABLE COMPOSITION AND FILM USING THE SAME

Abstract

It is an object of the present invention to provide a polymerizable liquid crystal composition that has an excellent storage stability and that enables a film formed by application of the composition to a base material and the subsequent exposure to heat or active energy rays to have a good adhesion to the base material. It is another object of the present invention to provide an optically anisotropic body that is produced using such a polymerizable composition and that has a good orientation. In particular, the present invention provides a polymerizable liquid crystal composition containing a polymerizable adhesion enhancer and a polymerizable liquid crystal compound. In addition, the present invention also provides an optically anisotropic body containing such a polymerizable liquid crystal composition.

Claims

1. A polymerizable liquid crystal composition comprising at least one polymerizable adhesion enhancer and at least one polymerizable liquid crystal compound.

2. The polymerizable liquid crystal composition according to claim 1, wherein the polymerizable adhesion enhancer is a compound (I) having at least one polymerizable functional group and a cyclic compound group having 1 to 4 rings.

3. The polymerizable liquid crystal composition according to claim 2, wherein the compound (I) is at least one compound selected from a group consisting of compounds represented by General Formula (I-1)
P.sup.1-Z.sup.A1-A.sup.1Z.sup.A2.sub.m(I-1) (where P.sup.1 represents a polymerizable functional group; Z.sup.A1 represents a single bond or an alkylene group having 1 to 16 carbon atoms; the alkylene group may be linear or branched; in the alkylene group, one or more CH.sub.2 groups are each independently optionally substituted with O, CO, COO, OCO, OCOO, CHCH, or CC such that oxygen atoms are not directly bonded to each other; A.sup.1 represents a cyclic compound group having 1 to 4 rings; Z.sup.A2 represents a hydroxyl group, a carboxy group, or an alkyl group having 1 to 16 carbon atoms; the alkyl group may be linear or branched; in the alkyl group, one or more CH.sub.2 groups are each independently optionally substituted with O, CO, COO, or OCO such that oxygen atoms are not directly bonded to each other; m represents 0, 1, 2, or 3; and in the case where m represents 2 or 3, the multiple Z.sup.A2's may be the same as or different from each other).

4. The polymerizable liquid crystal composition according to claim 3, wherein A.sup.1 in the compound (I-1) is at least one compound selected from the group consisting of compounds represented by General Formulae (I-1-1) to (I-1-11) ##STR00038## (where the symbol * represents a linkage to Z.sup.A1; in General Formulae (I-1-1) to (I-1-11), one or more methylene groups are each independently optionally substituted with an oxygen atom, a nitrogen atom, a sulfur atom, or CO such that oxygen atoms are not directly bonded to each other; in the case where the linking groups of Z.sup.A1 and/or Z.sup.A2 bonded to A.sup.1 are each an oxygen atom, the linking atom of A.sup.1 that is directly bonded to this oxygen atom is not an oxygen atom).

5. The polymerizable liquid crystal composition according to claim 1, wherein the polymerizable liquid crystal compound is a compound represented by General Formula (II)
P.sup.2(S.sup.1X.sup.1).sub.q1-MG-R.sup.2(II) (where P.sup.2 represents a polymerizable functional group; S.sup.1 represents an alkylene group having 1 to 18 carbon atoms (in the alkylene group, a hydrogen atom is optionally substituted with at least one halogen atom or CN; and one CH.sub.2 group or two or more CH.sub.2 groups not adjoining each other are each independently optionally substituted with O, COO, OCO, or OCOO); X.sup.1 represents O, S, OCH.sub.2, CH.sub.2O, CO, COO, OCO, COS, SCO, OCOO, CONH, NHCO, SCH.sub.2, CH.sub.2S, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, CHCHCOO, CHCHOCO, COOCHCH, OCOCHCH, COOCH.sub.2CH.sub.2, OCOCH.sub.2CH.sub.2, CH.sub.2CH.sub.2COO, CH.sub.2CH.sub.2OCO, COOCH.sub.2, OCOCH.sub.2, CH.sub.2COO, CH.sub.2OCO, CHCH, NN, CHNNCH, CFCF, CC, or a single bond (where P.sup.2S.sup.1 and SX.sup.1 exclude OO, ONH, SS, and OS); q1 represents 0 or 1; MG represents a mesogenic group; R.sup.2 represents a hydrogen atom, a halogen atom, a cyano group, or a linear or branched alkyl group having 1 to 12 carbon atoms; the alkyl group may be linear or branched; in the alkyl group, one CH.sub.2 or two or more CH.sub.2's not adjoining each other are each independently optionally substituted with O, S, CO, COO, OCO, COS, SCO, OCOO, CONH, NHCO, CHCHCOO, CHCHOCO, COOCHCH, OCOCHCH, CHCH, CFCF, or CC; and R.sup.2 alternatively represents a group represented by General Formula (II-a)
(X.sup.2S.sup.2).sub.q2P.sup.3(II-a) (where P.sup.3 represents a reactive functional group; S.sup.2 has the same definition as S.sup.1; X.sup.2 has the same definition as X.sup.1 (where P.sup.3S.sup.2 and S.sup.2X.sup.2 exclude OO, ONH, SS, and OS); and q.sup.2 represents 0 or 1).

6. The polymerizable liquid crystal composition according to claim 5, wherein the compound represented by General Formula (II) is a compound in which MG is represented by General Formula (II-b)
(B1-Z1).sub.r1B2-Z2-B3(II-b) (where B1, B2, and B3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo(2,2,2)octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2,7-diyl group and optionally have, as a substituent, at least one selected from F, Cl, CF.sub.3, OCF.sub.3, a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, an alkenoyloxy group having 2 to 8 carbon atoms, and/or General Formula (II-c)
(X.sup.3).sub.q4(S.sup.3).sub.q3P.sup.4(II-c) (where P.sup.4 represents a reactive functional group; S.sup.3 represents an alkylene group having 1 to 18 carbon atoms; X.sup.3 represents O, COO, OCO, OCH.sub.2, CH.sub.2O, CH.sub.2CH.sub.2OCO, or CH.sub.2CH.sub.2COO; q represents 0 or 1; q.sup.4 represents 0 or 1 (where P.sup.4S.sup.3 and S.sup.3X.sup.3 exclude OO, ONH, SS, and OS)); Z1 and Z2 each independently represent COO, OCO, CH.sub.2CH.sub.2, OCH.sub.2, CH.sub.2O, CHCH, CC, CHCHCOO, OCOCHCH, CH.sub.2CH.sub.2COO, CH.sub.2CH.sub.2OCO, COOCH.sub.2CH.sub.2, OCOCH.sub.2CH.sub.2, CONH, NHCO, an alkyl group having 2 to 10 carbon atoms and optionally a halogen atom, or a single bond; r1 represents 0, 1, or 2; and in the case where B1 and Z1 are multiple, corresponding ones of them may be the same as or different from each other).

7. The polymerizable liquid crystal composition according to claim 6, wherein the compound represented by General Formula (II) is at least one compound selected from the group consisting of compounds represented by General Formula (II-2-2-2)
P.sup.2(S.sup.1X.sup.1).sub.q1-B11-Z11-B2-Z2-B3-(X.sup.2S.sup.2).sub.q2P.sup.3(II-2-2-2) (where P.sup.2 and P.sup.3 each independently represent a polymerizable functional group; S.sup.1 and S.sup.2 each independently represent an alkylene group having 0 to 18 carbon atoms (in the alkylene group, a hydrogen atom is optionally substituted with at least one halogen atom, CN group, or alkyl group having 1 to 8 carbon atoms and a polymerizable functional group; and one CH.sub.2 group or two or more CH.sub.2 groups not adjoining each other are each independently optionally substituted with O, COO, OCO, or OCOO); X.sup.1 and X.sup.2 each independently represent O, S, OCH.sub.2, CH.sub.2O, CO, COO, OCO, COS, SCO, OCOO, CONH, NHCO, SCH.sub.2, CH.sub.2S, CF.sub.2O, OCF.sub.2, CF.sub.2S, SCF.sub.2, CHCHCOO, CHCHOCO, COOCHCH, OCOCHCH, COOCH.sub.2CH.sub.2, OCOCH.sub.2CH.sub.2, CH.sub.2CH.sub.2COO, CH.sub.2CH.sub.2OCO, COOCH.sub.2, OCOCH.sub.2, CH.sub.2COO, CH.sub.2OCO, CHCH, NN, CHNNCH, CFCF, CC, or a single bond (where P.sup.2S.sup.1 and S.sup.1X.sup.1 exclude OO, ONH, SS, and OS); q1 and q2 each independently represent 0 or 1; B11, B2, and B3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo(2,2,2)octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group-, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2,7-diyl group and optionally have, as a substituent, at least one selected from F, Cl, CF.sub.3, OCF.sub.3, a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkanoyl group having 1 to 8 carbon atoms, an alkanoyloxy group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group having 2 to 8 carbon atoms, an alkenoyl group having 2 to 8 carbon atoms, and an alkenoyloxy group having 2 to 8 carbon atoms; and Z11 and Z2 each independently represent COO, OCO, CH.sub.2CH.sub.2, OCH.sub.2, CH.sub.2O, CHCH, CC, CHCHCOO, OCOCHCH, CH.sub.2CH.sub.2COO, CH.sub.2CH.sub.2OCO, COOCH.sub.2CH.sub.2, OCOCH.sub.2CH.sub.2, CN, NC, CONH, NHCO, C(CF.sub.3).sub.2, an alkyl group having 2 to 10 carbon atoms and optionally a halogen atom, or a single bond).

8. A polymer produced through polymerization of the polymerizable liquid crystal composition according to claim 1.

9. An optically anisotropic body produced by using the polymerizable liquid crystal composition according to claim 1.

10. A retardation film produced by using the polymerizable liquid crystal composition according to claim 1.

11. A patterned retardation film produced by using the polymerizable liquid crystal composition according to claim 1.

12. A brightness-enhancing film produced by using the polymerizable liquid crystal composition according to claim 1.

13. An antireflection film produced by using the polymerizable liquid crystal composition according to claim 1.

Description

EXAMPLES

[0134] The present invention will now be described with reference to Synthesis Examples, Examples, and Comparative Examples but is apparently not limited thereto. The terms part and % are on a mass basis unless otherwise specified.

(Preparation of Polymerizable Liquid Crystal Composition)

[0135] Compounds were selected from compounds shown in Table 1 and represented by Formulae (A-1) to (A-6), (B-1) to (B-8), and (C-1) and (C-2) in the total amount of 100 parts by mass; and the selected compounds were mixed with any of compounds represented by Formulae (D-1) to (D-18), a compound represented by (E-1), a compound represented by (F-1), and any of compounds represented by (G-1) and (G-2) in the amounts shown in Table 1 (parts by mass). MEK (methyl ethyl ketone) (H-1) was used as an organic solvent such that the total amount of the compounds selected from the compounds represented by Formulae (A-1) to (A-6), (B-1) to (B-8), and (C-1) and (C-2); the compound selected from the compounds represented by Formulae (D-1) to (D-18); the compound represented by (E-1); the compound represented by (F-1); and the compound selected from the compounds represented by (G-1) and (G-2) was 25 mass % in a polymerizable liquid crystal composition, thereby preparing a polymerizable liquid crystal composition (MEK: 75 mass %).

(Preparation of Polymerizable Liquid Crystal Composition (1))

[0136] As shown in Table 1, 20 parts by mass of the compound represented by Formula (A-3), 20 parts by mass of the compound represented by Formula (A-5), 25 parts by mass of the compound represented by Formula (B-5), and 35 parts by mass of the compound represented by Formula (B-7) were prepared; and 5 parts by mass of the compound represented by Formula (D-1), 5 parts by mass of a polymerization initiator (E-1), and 0.1 part by mass of methylhydroquinone (MEHQ) (F-1) relative to 100 parts by mass of the total amount of the above compounds were prepared. The MEK (H-1) was used as an organic solvent such that the total amount of all of those compounds was 25 mass %. This mixture was stirred with a stirrer having a stirring propeller for an hour at a stirring rate of 300 rpm and a solution temperature of 80 C. The resulting product was then filtrated through a membrane filter of 0.2 m to produce a polymerizable liquid crystal composition (1).

(Preparation of Polymerizable Liquid Crystal Compositions (2) to (46) and (51) to (75) and Comparative Polymerizable Liquid Crystal Compositions (47) to (50))

[0137] The compounds represented by Formulae (A-1) to (A-6), compounds represented by Formulae (B-1) to (B-8), compounds represented by Formulae (C-1) and (C-2), compounds represented by Formulae (D-1) to (D-18), compound represented by (E-1), compound represented by (F-1), compound represented by (G-1), compound represented by (G-2), and compound represented by (J-1), which are all shown in Tables 1 to 4, were used as shown in Table 1. Except for this change, polymerizable liquid crystal compositions (2) to (46) and (51) to (75) and comparative polymerizable liquid crystal compositions (47) to (50) were produced as in the preparation of the polymerizable liquid crystal composition (1) of the present invention.

[0138] Tables 1 to 6 show the specific constitution of the polymerizable liquid crystal compositions (1) to (46) and (51) to (75) of the present invention and the specific constitution of the comparative polymerizable liquid crystal compositions (47) to (50).

TABLE-US-00001 TABLE 1 Composition (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (A-1) (A-2) (A-3) 20 20 20 20 20 20 20 20 20 20 20 20 20 20 (A-4) (A-5) 20 20 20 20 20 20 20 20 20 20 20 20 20 20 (A-6) (B-1) (B-2) (B-3) (B-4) (B-5) 25 25 25 25 25 25 25 25 25 25 25 25 25 25 (B-6) (B-7) 35 35 35 35 35 35 35 35 35 35 35 35 35 35 (B-8) (C-1) (C-2) (D-1) 5 8 (D-2) 5 (D-3) 5 (D-4) 5 10 (D-5) 5 5 5 (D-6) 5 (D-7) 5 (D-8) 5 (D-9) 5 (D-10) 5 (D-11) (D-12) (D-13) (D-14) (D-15) (D-16) (D-17) (E-1) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 (F-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (G-1) 0.6 (G-2) 2.5 (H-1) 75 75 75 75 75 75 75 75 75 75 75 75 75 75

TABLE-US-00002 TABLE 2 Composition (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (A-1) (A-2) (A-3) 20 20 20 20 20 40 40 40 40 40 10 10 40 40 (A-4) (A-5) 20 20 20 20 20 10 10 10 10 10 3 3 (A-6) (B-1) (B-2) (B-3) (B-4) (B-5) 25 25 25 25 25 25 25 25 25 25 20 20 (B-6) 25 25 25 25 25 (B-7) 35 35 35 35 35 5 5 40 40 (B-8) 80 80 (C-1) 2 2 (C-2) (D-1) 5 5 5 (D-2) 5 (D-3) 5 (D-4) (D-5) 5 5 5 5 (D-6) (D-7) (D-8) (D-9) (D-10) (D-11) 5 (D-12) 5 (D-13) 5 (D-14) 5 (D-15) 5 (D-16) (D-17) (E-1) 5 5 5 5 5 5 5 5 5 5 5 5 5 5 (F-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (G-1) (G-2) 2.5 2.5 2.5 2.5 (H-1) 75 75 75 75 75 75 75 75 75 75 75 75 75 75

TABLE-US-00003 TABLE 3 Composition (29) (30) (31) (32) (33) (34) (35) (36) (37) (38) (39) (40) (41) (42) (A-1) 42.5 42.5 42.5 42.5 42.5 42.5 42.5 37.5 37.5 35 35 15 15 (A-2) 42.5 42.5 42.5 42.5 42.5 42.5 42.5 37.5 37.5 35 35 45 45 (A-3) 35 (A-4) 35 (A-5) 10 10 15 15 (A-6) 40 40 (B-1) 15 15 15 15 15 15 15 15 15 (B-2) 15 15 (B-3) 15 (B-4) 15 (B-5) (B-6) (B-7) (B-8) (C-1) (C-2) (D-1) 5 5 8 5 5 5 5 (D-2) (D-3) (D-4) 5 (D-5) 5 5 5 5 5 5 (D-6) (D-7) (D-8) (D-9) (D-10) (D-11) (D-12) (D-13) (D-14) (D-15) (D-16) (D-17) (E-1) 3 3 3 3 3 3 3 3 3 3 3 3 3 3 (F-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (G-1) 0.6 (G-2) 2.5 2.5 2.5 2.5 (H-1) 75 75 75 75 75 75 75 75 75 75 75 75 75 75

TABLE-US-00004 TABLE 4 Composition (43) (44) (45) (46) (47) (48) (49) (50) (A-1) 42.5 (A-2) 42.5 (A-3) 35 35 40 40 20 20 20 (A-4) 35 35 34 34 (A-5) 20 20 20 (A-6) (B-1) 15 (B-2) (B-3) 15 15 (B-4) 15 15 18 18 (B-5) 25 25 25 (B-6) (B-7) 35 35 35 (B-8) (C-1) (C-2) 8 8 (D-1) 5 (D-2) (D-3) (D-4) (D-5) 5 5 5 (D-6) (D-7) (D-8) (D-9) (D-10) (D-11) (D-12) (D-13) (D-14) (D-15) (D-16) 0.5 (D-17) 2 (E-1) 3 3 3 3 5 5 5 3 (F-1) 0. 1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (G-1) (G-2) 2.5 2.5 (H-1) 75 75 75 75 75 75 75 75

TABLE-US-00005 TABLE 5 Composition (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (A-1) 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 (A-2) 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 42.5 (A-3) (A-4) (A-5) (A-6) (B-1) 15 15 15 15 15 15 15 15 15 15 15 15 (B-2) (B-3) (B-4) (B-5) (B-6) (B-7) (B-8) (C-1) (C-2) (D-1) 5 (D-2) 5 (D-3) 5 (D-4) 5 (D-5) 5 5 (D-6) 5 (D-7) 5 (D-8) 5 (D-9) 5 (D-10) 5 (D-11) 5 (D-12) (D-13) (D-14) (D-15) (D-16) (D-17) (E-1) 3 3 3 3 3 3 3 3 3 3 3 3 (F-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (G-1) 0.6 (G-2) (J-1) 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 (H-1) 75 75 75 75 75 75 75 75 75 75 75 75

TABLE-US-00006 TABLE 6 Composition (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (A-1) 42.5 42.5 42.5 42.5 25 25 25 25 25 25 50 50 (A-2) 42.5 42.5 42.5 42.5 25 25 25 25 25 25 50 50 (A-3) 20 (A-4) 15 15 15 15 15 15 (A-5) 20 20 20 20 20 20 20 (A-6) (B-1) 15 15 15 15 15 15 15 15 15 15 (B-2) (B-3) (B-4) (B-5) 25 (B-6) (B-7) 35 (B-8) (C-1) (C-2) (D-1) 5 5 (D-2) 5 (D-3) 5 (D-4) 5 (D-5) 5 5 (D-6) 5 (D-7) (D-8) (D-9) (D-10) (D-11) (D-12) 5 (D-13) 5 (D-14) 5 (D-15) 5 (D-16) (D-17) (D-18) 5 (E-1) 3 3 3 3 3 3 3 3 3 3 3 3 5 (F-1) 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 (J-1) 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 (H-1) 75 75 75 75 75 75 75 75 75 75 75 75 75

##STR00034## ##STR00035## ##STR00036##

[0139] n is from 0 to 6, and the molecular weight of (D-9) is from 150 to 550 g/mol.

##STR00037##

[0140] Laromer LR-9000 ((diacrylate having two isocyanate groups per molecule, manufactured by BASF Japan Ltd.) (D-17) Irgacure 907 (E-1)

MEHQ (F-1)

Triethylenetetramine (G-1)

[0141] Ketimine compounds (jERCURE H3) (G-2)
MEGAFAC F-554 (manufactured by DIC Corporation) (J-1)

Example 1

(Storage Stability)

[0142] The prepared polymerizable liquid crystal composition (1) was stored at 40 C. for a month and then subjected to measurement of an increase in the proportion of the polymer component in the composition (%). The amounts of the polymer component before and after the storage were measured, and the increase in the proportion of the polymer component (%) was calculated from the follow formula: {(amount of polymer component after storage)(amount of polymer component before storage)}/{amount of polymer component before storage)}100. The measurement of the polymer component was performed with a GPC apparatus.

(Adhesion)

[0143] <Production of Film Used for Evaluating Adhesion>

[0144] The polymerizable liquid crystal composition (1) and a silane coupling material used for forming a vertical alignment film (DMOAP manufactured by JNC CORPORATION) were applied to a COP film substrate at room temperature by spin coating and then baked at 100 C. for an hour to produce a base material. The base material was coated using a #5 bar coater and then dried at 80 C. for 2 minutes. The product was left to stand at room temperature for 5 minutes and irradiated with UV light with a conveyor-type high pressure mercury lamp at an intensity of 500 mJ/cm.sup.2 to produce a film of Example 1.

<Evaluation of Adhesion>

[0145] In order to evaluate the adhesion of the film produced as described above, the film was cut in with a cutter by a cross-cut method in accordance with JIS K5600-5-6 to form a grid of 2-mm squares.

Class 0: No square of grid was peeled off
Class 1: Coating film was slightly peeled off at intersection of cut lines (less than 5%)
Class 2: Coating film was peeled off along cut lines at intersection of cut lines (5% or more and less than 15%)
Class 3: Coating film was partially or completely peeled off along cut lines (15% or more and less than 35%)
Class 4: Coating film was partially or completely peeled off along cut lines to a larger extent (35% or more and less than 65%)
Class 5: More than Class 4

(Orientation)

[0146] The polymerizable liquid crystal composition (1) was applied onto a TAC (triacetylcellulose) film at room temperature with a #5 bar coater and then dried at 80 C. for 2 minutes. Then, the resulting product was left to stand at room temperature for 15 minutes and irradiated with UV rays with a conveyor-type high-pressure mercury lamp at the integral of light of 500 mJ/cm.sup.2.

Excellent: Problem was not found through visual observation and observation with polarizing microscope
Good: Problem was not found through visual observation, but non-orientation was found in some parts through observation with polarizing microscope
Bad: Problem was not found through visual observation, but non-orientation was entirely found through observation with polarizing microscope
Poor: Problem was found in some parts through visual observation, and non-orientation was entirely found through observation with polarizing microscope
The following tables show results of the evaluations.

TABLE-US-00007 TABLE 7 Solution Storage stability Adhesion Orientation Example 1 Solution (1) 2.0 0 Excellent Example 2 Solution (2) 1.5 0 Excellent Example 3 Solution (3) 2.0 0 Excellent Example 4 Solution (4) 2.0 0 Excellent Example 5 Solution (5) 2.5 0 Excellent Example 6 Solution (6) 1.5 0 Excellent Example 7 Solution (7) 2.0 1 Excellent Example 8 Solution (8) 4.0 0 Excellent Example 9 Solution (9) 2.5 0 Excellent Example 10 Solution (10) 1.0 2 Excellent Example 11 Solution (11) 1.5 2 Excellent Example 12 Solution (12) 1.0 2 Excellent Example 13 Solution (13) 1.0 2 Excellent Example 14 Solution (14) 2.0 2 Excellent

TABLE-US-00008 TABLE 8 Solution Storage stability Adhesion Orientation Example 15 Solution (15) 1.0 2 Excellent Example 16 Solution (16) 1.0 2 Excellent Example 17 Solution (17) 1.5 2 Excellent Example 18 Solution (18) 2.5 2 Excellent Example 19 Solution (19) 2.5 2 Excellent Example 20 Solution (20) 2.0 0 Excellent Example 21 Solution (21) 2.0 0 Excellent Example 22 Solution (22) 2.0 0 Excellent Example 23 Solution (23) 2.5 0 Excellent Example 24 Solution (24) 2.5 0 Excellent Example 25 Solution (25) 2.5 0 Excellent Example 26 Solution (26) 3.0 0 Excellent Example 27 Solution (27) 2.0 0 Excellent Example 28 Solution (28) 2.5 0 Excellent

TABLE-US-00009 TABLE 9 Solution Storage stability Adhesion Orientation Example 29 Solution (29) 2.0 0 Excellent Example 30 Solution (30) 2.0 0 Excellent Example 31 Solution (31) 1.5 0 Good Example 32 Solution (32) 2.5 0 Excellent Example 33 Solution (33) 2.0 1 Excellent Example 34 Solution (34) 4.0 0 Excellent Example 35 Solution (35) 2.5 0 Excellent Example 36 Solution (36) 2.5 0 Excellent Example 37 Solution (37) 2.5 0 Excellent Example 38 Solution (38) 2.0 0 Excellent Example 39 Solution (39) 2.5 0 Excellent Example 40 Solution (40) 2.5 0 Excellent Example 41 Solution (41) 2.5 0 Excellent Example 42 Solution (42) 2.0 0 Excellent

TABLE-US-00010 TABLE 10 Storage Solution stability Adhesion Orientation Example 43 Solution (43) 2.5 0 Excellent Example 44 Solution (44) 2.5 0 Excellent Example 45 Solution (45) 2.0 0 Excellent Example 46 Solution (46) 3.0 0 Excellent Comparative Solution (47) 1.0 5 Excellent Example 1 Comparative Solution (48) 8.0 1 Good Example 2 Comparative Solution (49) 10.0 0 Bad Example 3 Comparative Solution (50) 1.0 5 Excellent Example 4

TABLE-US-00011 TABLE 11 Solution Storage stability Adhesion Orientation Example 47 Solution (51) 2.0 0 Excellent Example 48 Solution (52) 2.5 0 Excellent Example 49 Solution (53) 2.0 1 Excellent Example 50 Solution (54) 4.0 0 Excellent Example 51 Solution (55) 1.0 0 Excellent Example 52 Solution (56) 1.0 0 Excellent Example 53 Solution (57) 1.0 0 Excellent Example 54 Solution (58) 1.5 0 Excellent Example 55 Solution (59) 1.0 0 Excellent Example 56 Solution (60) 1.0 0 Excellent Example 57 Solution (61) 1.5 0 Excellent Example 58 Solution (62) 1.0 0 Excellent

TABLE-US-00012 TABLE 12 Solution Storage stability Adhesion Orientation Example 59 Solution (63) 1.0 0 Excellent Example 60 Solution (64) 1.0 0 Excellent Example 61 Solution (65) 2.0 0 Excellent Example 62 Solution (66) 2.0 0 Excellent Example 63 Solution (67) 1.0 0 Excellent Example 64 Solution (68) 1.0 0 Excellent Example 65 Solution (69) 1.0 0 Excellent Example 66 Solution (70) 1.0 0 Excellent Example 67 Solution (71) 1.0 0 Excellent Example 68 Solution (72) 1.0 0 Excellent Example 69 Solution (73) 1.5 0 Excellent Example 70 Solution (74) 1.5 0 Excellent Example 71 Solution (75) 3.0 3 Bad

Examples 2 to 71 and Comparative Examples 1 to 4

[0147] As in Example 1, the polymerizable liquid crystal compositions (2) to (75) were used to measure storage stability, adhesion, and orientation. Results of the measurements are shown in the above tables in the name of Examples 2 to 71 and Comparative Examples 1 to 4. Each of the base materials of the films used for evaluating adhesion was the laminate including a COP film substrate and a silane-coupling vertical alignment film formed thereon as in Example 1 in Examples 2 to 19, 30, 63 to 68, and 71 and Comparative Examples 1 to 3; a TAC film substrate in Examples 20 to 23, Examples 25 to 28, and Example 42, 43, 45, 46, 69, and 70; a PMMA film substrate in Examples 24 and 44; and a COP film substrate (no vertical alignment film) in Examples 29, 31 to 41, and 47 to 62 and Comparative Example 4.

[0148] Each of the polymerizable liquid crystal compositions (Examples 1 to 71) containing any of the polymerizable adhesion enhancers represented by Formulae (D-1) to (D-15) had an excellent storage stability; in addition, it had an excellent adhesion to the base material and enabled production of an optically anisotropic body having an excellent orientation as compared with the polymerizable liquid crystal compositions (Comparative Examples 1 and 4) that were free from a polymerizable adhesion enhancer. The polymerizable liquid crystal composition (Example 71) containing the polymerizable adhesion enhancer represented by Formula (D-18) had two polymerizable groups and therefore had smaller storage stability, adhesion, and orientation than compositions containing the compounds represented by Formulae (D-1) to (D-15) and each having one polymerizable group. Each of the polymerizable liquid crystal compositions (Comparative Examples 2 and 3) not containing the polymerizable adhesion enhancer of the present invention but containing another polymerizable adhesion enhancer had an improved adhesion to the base material; however, it had and unsatisfactory storage stability and thus was inadequate to produce an optically anisotropic body having a good orientation.