Polymerizable monomer, liquid crystal composition using polymerizable monomer, and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-11312906-B2
Application number	US-201816611753-A
Country	US
Kind code	B2
Filing date	May 17, 2018
Priority date	Jun 1, 2017
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

A problem to be solved by the present invention is to provide a liquid crystal composition excellent in vertical alignment and compatibility and to provide a liquid crystal display device produced using the same. The problem is solved by a liquid crystal composition containing one or two or more kinds of self-aligning polymerizable monomers and one or two or more kinds of polymerizable monomers (or polymerizable compounds) having a specific chemical structure, and a liquid crystal display device produced using the same, specifically a liquid crystal composition containing a polymerizable monomer represented by General Formula (I) and a spontaneously aligning monomer which has a chemical structure different from that of the polymerizable monomer represented by General Formula (I), and has a polar group, and a liquid crystal display device containing the same.

First claim

The invention claimed is:

1. A liquid crystal composition for a liquid crystal display device, the liquid crystal composition comprising:
a polymerizable monomer represented by General Formula (I); and
a spontaneously aligning monomer selected from the group consisting of compounds represented by Formulae (P-1-1) to (P-1-15), (P-1-20) to (P-1-26), (P-J-10) to (P-J-50), and (P-1) to (P-18),
wherein the content of the polymerizable monomer represented by General Formula (I) is 0.02 to 2.5% by mass, and the content of the spontaneously aligning monomer is 0.02 to 2.5% by mass,

wherein R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108 , R 109 , and R 110 each independently represent any selected from the group consisting of P 11 —S 11 —, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a halogen atom, and a hydrogen atom, and P 11 represents any of the following Formula (R-I) to Formula (R-IX):

wherein
R 21 , R 31 , R 41 , R 51 , and R 61 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms,
W is a single bond, —O—, or a methylene group,
T is a single bond or —COO—,
p, t, and q are each independently 0, 1, or 2,
S 11 represents a single bond or an alkylene group having 1 to 15 carbon atoms, and one or two or more —CH 2 —'s in the alkylene group may be substituted with —O—, —OCO—, or —COO— so that an oxygen atom is not directly adjacent thereto,
n 11 represents 0, 1, or 2,
A 11 represents a group selected from the group consisting of a group (a), a group (b), and a group (c) as follows:
(a) 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 —'s present in this group may be substituted with —O—),
(b) 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═'s present in this group may be substituted with —N═), and
(c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or decahydronaphthalene-2,6-diyl group (one —CH═ or two or more non-adjacent —CH═'s present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═),
the group (a), the group (b), and the group (c) may be each independently substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, halogen atoms, a cyano group, a nitro group, or P 11 —S 11 —,
L 10 and L 11 each independently represent a single bond, —OCH 2 —, —CH 2 O—, —C 2 H 4 —, —OC 2 H 4 O—, —COO—, —OCO—, —CH═CR a —COO—, —CH═CR a —OCO—, —COO—CR a ═CH—, —OCO—CR a ═CH—, —(CH 2 ) z —COO—, —(CH 2 ) z —OCO—, —OCO—(CH 2 ) z —, —COO—(CH 2 ) z —, —CH═CH—, —CF 2 O—, —OCF 2 —, or —C≡C— (wherein, R a 's each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and z's each independently represent an integer of 1 to 4),
at least two or more P 11 —S 11 —'s are included in one molecule of General Formula (I), and
at least one alkyl group having 1 to 18 carbon atoms is included in the polymerizable monomer represented by General Formula (I), in which one —CH 2 — or two or more non-adjacent —CH 2 —'s in an alkylene group of said at least one alkyl group may be each independently substituted with —O—, and
in a case where there are a plurality of P 11 's, S 11 's, L 11 's, and A 11 's, those may be the same as or different from each other,

2. The liquid crystal composition according to claim 1 , wherein
in General Formula (I), n 11 is 0 or 1.

3. The liquid crystal composition according to claim 1 , wherein
in General Formula (I), L 10 and L 11 are single bonds.

4. The liquid crystal composition according to claim 1 , further comprising:
one or two or more kinds of compounds selected from the group consisting of compounds represented by General Formulae (N-1), (N-2), and (N-3):

wherein
R N11 , R N12 , R N21 , R N22 , R N31 , and R N32 each independently represent an alkyl group having 1 to 8 carbon atoms, and one —CH 2 — or two or more non-adjacent —CH 2 —'s in the alkyl group may be each independently substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—,
A N11 , A N12 , A N21 , A N22 , A N31 , and A N32 each independently represent a group selected from the group consisting of
(a) 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 —'s present in this group may be substituted with —O—),
(b) 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═'s present in this group may be substituted with —N═),
(c) naphthalene-2,6-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, or decahydronaphthalene-2,6-diyl group (one —CH═ or two or more non-adjacent —CH═'s present in the naphthalene-2,6-diyl group or the 1,2,3,4-tetrahydronaphthalene-2,6-diyl group may be substituted with —N═), and
(d) 1,4-cyclohexenylene group,
the group (a), the group (b), the group (c), and the group (d) may be each independently substituted with a cyano group, a fluorine atom, or a chlorine atom,
Z N11 , Z N12 , Z N21 , Z N22 , Z N31 , and Z N32 each independently represent a single bond, —CH 2 CH 2 —, —(CH 2 ) 4 —, —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —OCF 2 —, —CF 2 O—, —CH═N—N═CH—, —CH═CH—, —CF═CF—, or —C≡C—,
X N21 represents a hydrogen atom or a fluorine atom,
T N31 represents a —CH 2 — or an oxygen atom, and
n N11 , n N12 , n N21 , n N22 , n N31 , and n N32 each independently represent an integer of 0 to 3, wherein n N11 +n N12 , n N21 +n N22 , and n N31 +n N32 each independently represent 1, 2, or 3, and in a case where there are a plurality of A N11 's to A N32 's and Z N11 's to Z N32 's, those may be the same as or different from each other.

5. The liquid crystal composition according to claim 1 , further comprising:
one or two or more kinds of compounds selected from compounds represented by Gener

Assignees

• Dainippon Ink & Chemicals

Inventors

• Mamiya Junichi
• Inoue Yuichi
• Kimura Masaomi
• Yamamoto Junko
• Hayashi Masanao
• Sugiyama Hirokazu

Classifications

• C09K19/38

  Polymers · CPC title

• C09K19/12 Primary

  at least two benzene rings directly linked, e.g. biphenyls · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K2323/00

  Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition · CPC title

• G02F1/1337

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title