Polymer-stabilized liquid crystal composition, liquid crystal display device, method for producing liquid crystal display device

A polymer-stabilized liquid crystal composition comprising:

• a polymerizable compound (I) represented by general formula (I-a);
• a compound (II) represented by general formula (II-a) or (II-b);
• at least one polymerizable compound (III) selected from the group consisting of compounds represented by general formulas (III-a), (III-b), and (III-c);
• and
• a chiral compound (IV) represented by general formula (IV-a) or (IV-b), wherein
• the polymerizable compound (I) forms a polymer that has a glass transition temperature of −100° C. to 25° C.,
• the general formula (I-a):
• (in the formula (I-a), A1 represents a hydrogen atom or a methyl group,
• A2 represents a single bond or an alkylene group of 1 to 15 carbon atoms (one, or two or more methylene group(s) existing in the alkylene group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other, and one, or two or more hydrogen atom(s) existing in the alkylene group each independently may be substituted with a fluorine atom, a methyl group, or an ethyl group),
• A3 and A6 each independently represents a hydrogen atom or an alkyl group of 1 to 18 carbon atoms (one, or two or more methylene group(s) existing in the alkyl group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other, one, or two or more hydrogen atom(s) existing in the alkyl group each independently may be substituted with a halogen atom or an alkyl group of 1 to 17 carbon atoms),
• A4 and A7 each independently represents a hydrogen atom or an alkyl group of 1 to 10 carbon atoms (one, or two or more methylene group(s) existing in the alkyl group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other, and one, or two or more hydrogen atom(s) existing in the alkyl group each independently may be substituted with a halogen atom or an alkyl group of 1 to 9 carbon atoms),
• k represents 1 to 40, and
• B1, B2 and B3 each independently represents a hydrogen atom, or a linear or branched alkyl group of 1 to 10 carbon atoms (one, or two or more methylene group(s) existing in the alkyl group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other), or a group represented by general formula (I-b):
• (in the formula (I-b), A9 represents a hydrogen atom or a methyl group, and
• A8 represents a single bond or an alkylene group of 1 to 15 carbon atoms (one, or two or more methylene group(s) existing in the alkylene group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other, and one, or two or more hydrogen atom(s) existing in the alkylene group each independently may be substituted with a fluorine atom, a methyl group, or an ethyl group)), provided that the number of groups represented by the general formula (I-b) among B1, B2 and B3, a total number of which is 2k+1, is from 0 to 3);
• the general formula (II-a) or (II-b):
• (in the formulas (II-a) and (II-b), R1 and R2 each independently represents an alkyl group of 1 to 18 carbon atoms or an alkenyl group of 2 to 18 carbon atoms (one, or two or more methylene group(s) existing in the alkyl group or an alkenyl group each independently may be substituted with an oxygen atom in a manner that any oxygen atoms are not directly bonded to each other),
• C1 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, or a 1,3-dioxane-2,5-diyl group (the 1,4-phenylene group among these groups is unsubstituted, or can contain one, or two or more fluorine atom(s), chlorine atom(s), methyl group(s), trifluoromethyl group(s) or trifluoromethoxy group(s) as substituent(s)),
• C2 and C3 each independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyridazine-3,6-diyl group, a 1,3-dioxane-2,5-diyl group, a cyclohexene-1,4-diyl group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a 1,3,4-thiadiazole-2,5-diyl, or an indan-2,5-diyl group (the 1,4-phenylene group, the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, the 2,6-naphthylene group, and the indan-2,5-diyl group among these groups are unsubstituted, or can contain one, or two or more fluorine atom(s), chlorine atom(s), methyl group(s), trifluoromethyl group(s), or trifluoromethoxy group(s) as substituent(s)),
• Z1 and Z2 each independently represents a single bond, —CH2CH2—, —CH2O—, —OCH2—, —CH2CH2O—, —OCH2CH2—, —CH2CH2CH2O—, —OCH2CH2CH2—, —CH═CH—, —C≡C—, —CF2O—, —OCF2—, —COO—, or —OCO—,
• X1 represents a fluorine atom, a chlorine atom, a trifluoromethyl group, a trifluoromethoxy group, a difluoromethyl group, or an isocyanate group or cyano group, and
• n1 represents 0, 1, or 2, provided that plural C1 and Z1 may be the same or different when n1 represents 2);
• the general formula (III-a):
• (in the formula (III-a), R3 and R4 each independently represents a hydrogen atom or a methyl group,
• C4 and C5 each independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyridazine-3,6-diyl group, a 1,3-dioxane-2,5-diyl group, a cyclohexene-1,4-diyl group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, or an indan-2,5-diyl group (the 1,4-phenylene group, the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, the 2,6-naphthylene group, and the indan-2,5-diyl group among these groups are unsubstituted, or can contain one, or two or more fluorine atom(s), chlorine atom(s), methyl group(s), trifluoromethyl group(s), or trifluoromethoxy group(s) as substituent(s)),
• Z3 and Z5 each independently represents a single bond or an alkylene group of 1 to 15 carbon atoms (one, or two or more methylene group(s) existing in the alkylene group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other, and one, or two or more hydrogen atom(s) existing in the alkylene group each independently may be substituted with a fluorine atom, a methyl group, or an ethyl group),
• Z4 represents a single bond, —CH2CH2—, —CH2O—, —OCH2—, —CH2CH2O—, —OCH2CH2—, —CH2CH2CH2O—, —OCH2CH2CH2—, —CH2CH2OCO—, —COOCH2CH2—, —CH2CH2COO—, —OCOCH2CH2—, —CH═CH—, —C≡C—, —CF2O—, —OCF2—, —COO—, or —OCO—, and
• n2 represents 0, 1, or 2, provided that plural C4 and Z4 may be the same or different when n2 represents 2);
• the general formula (III-b):
• (in the formula (III-b), R5 and R6 each independently represents a hydrogen atom or a methyl group,
• C6 represents a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyridazine-3,6-diyl group, a 1,3-dioxane-2,5-diyl group, a cyclohexene-1,4-diyl group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, or an indan-2,5-diyl group (the 1,4-phenylene group, the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, the 2,6-naphthylene group, and the indan-2,5-diyl group among these groups are unsubstituted, or can contain one, or two or more fluorine atom(s), chlorine atom(s), methyl group(s), trifluoromethyl group(s) or trifluoromethoxy group(s) as substituent(s)),
• C7 and C8 each independently represents a benzene-1,2,4-triyl group, a benzene-1,3,4-triyl group, a benzene-1,3,5-triyl group, a cyclohexane-1,2,4-triyl group, a cyclohexane-1,3,4-triyl group, or a cyclohexane-1,3,5-triyl group,
• Z6 and Z8 each independently represents a single bond or an alkylene group of 1 to 15 carbon atoms (one, or two or more methylene group(s) existing in the alkylene group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other, and one, or two or more hydrogen atom(s) existing in the alkylene group each independently may be substituted with a fluorine atom, a methyl group, or an ethyl group),
• Z7 and Z9 each independently represents a single bond, —CH2CH2—, —CH2O—, —OCH2—, —CH2CH2O—, —OCH2CH2—, —CH2CH2CH2O—, —OCH2CH2CH2—, —CH2CH2OCO—, —COOCH2CH2—, —CH2CH2COO—, —OCOCH2CH2—, —CH═CH—, —C≡C—, —CF2O—, —OCF2—, —COO—, or —OCO—,
• n3 represents 0, 1, or 2, provided that plural C6 and Z7 may be the same or different when n3 represents 2, and
• n5 and n6 each independently represents 1, 2, or 3);
• the general formula (III-c):
• (in the formula (III-c), R7 represents a hydrogen atom or a methyl group,
• 6-membered rings T1, T2 and T3 each independently represents any one of:
• (in which m represents an integer of 1 to 4),
• n4 represents an integer of 0 or 1,
• Y1 and Y2 each independently represents a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OCO—, —C≡C—, —CH═CH—, —CF═CF—, —(CH2)4—, —CH2CH2CH2O—, —OCH2CH2CH2—, —CH2═CHCH2CH2—, or —CH2CH2CH═CH—,
• Y3 represents a single bond, —COO—, or —OCO—, and
• R8 represents a hydrocarbon group of 1 to 18 carbon atoms);
• and
• the general formula (IV-a) or (IV-b):
• (in the formula (IV-a) and (IV-b), R9 represents an alkyl group of 1 to 18 carbon atoms or an alkenyl group of 2 to 18 carbon atoms (one, or two or more methylene group(s) existing in the alkyl group or an alkenyl group each independently may be substituted with an oxygen atom in a manner that any oxygen atoms are not directly bonded to each other),
• C8 and C9 each independently represents a 1,4-phenylene group, a 1,4-cyclohexylene group, or a pyrimidine-2,5-diyl group (the 1,4-phenylene group or the 1,4-cyclohexylene group among these groups is unsubstituted, or can contain one, or two or more fluorine atom(s), chlorine atom(s), methyl group(s), cyano group(s), trifluoromethyl group(s) or trifluoromethoxy group(s) as substituent(s)),
• Z9 represents a single bond, —CH2CH2—, —C≡C—, —CF2O—, —COO—, or —OCO—,
• Y4 and Y5 each independently represents a single bond, an oxygen atom, an alkylene group of 1 to 14 carbon atoms, —OCH2—, —COO—, —OCO—, —OCH2CH2—, or —OCOCH2—,
• n5 represents 0, 1, or 2, provided that plural C8 and Z9 may be the same or different when n5 represents 2, and
• X4 and X5 each independently represents a group represented by any of general formulas (IV-c) to (IV-h):
• (in the formulas (IV-c) to (IV-h), the symbol * represents that a carbon atom is an asymmetric carbon,
• Rc, Rd, Re, Rf, and Rg each independently represents an alkyl group of 2 to 20 carbon atoms (one, or two or more methylene group(s) existing in the alkyl group each independently may be substituted with an oxygen atom, —CO—, —COO—, or —OCO— in a manner that any oxygen atoms are not directly bonded to each other),
• Xc, Xd, and Yd each independently represents a fluorine atom, a chlorine atom, a methyl group, or a cyano group,
• Xe and Ye each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, or a cyano group,
• Xh and Yh each independently represents a fluorine atom, a chlorine atom, a methyl group, or a cyano group,
• Zd represents a single bond or methylene group,
• Ze represents an oxygen atom or a group represented by —OC(Re1)(Re2)O— (in which Re1 and Re2 each independently represents a hydrogen atom or an alkyl group of 1 to 10 carbon atoms),
• Zf represents a carbonyl group or a group represented by —CH(Rf1)— (in which Rf1 represents a hydrogen atom or an alkyl group of 1 to 10 carbon atoms), and
• Zg represents —OCO—, —COO—, —CH2O—, or —OCH2—)).