Polymerizable liquid crystal composition and thin film using same

Patent metadata

Field	Value
Publication number	US-9469810-B2
Application number	US-201214348765-A
Country	US
Kind code	B2
Filing date	Nov 21, 2012
Priority date	Nov 30, 2011
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

The present invention relates to a polymerizable composition useful as a liquid crystal device, a display, an optical member, a coloring agent, a security marking, and a laser light emitting member and a thin film obtained from the polymerizable composition.
The present invention provides a polymerizable liquid crystal composition having excellent solubility into a solvent, exhibiting good adhesion to a base material, and being capable of realizing a thin film having low haze and no variations and, in addition, provides a thin film having excellent appearance by using the polymerizable liquid crystal composition.
The polymerizable liquid crystal composition according to the present invention is used and, thereby, a composition and a thin film having low haze and no variations and, at the same time, having excellent adhesion to a base material can be obtained at a low cost.

First claim

The invention claimed is:

1. A polymerizable liquid crystal composition characterized by comprising:
5 to 30 percent by mass of compound having at least two polymerizable functional groups as a first component, wherein at least one of the compound having at least two polymerizable functional groups is represented by General formula (1),
P 1 -E 1 -A 1 -Z 1 -A 2 -Z 2 -A 3 -E 2 -P 2   (1)

(in the formula, P 1 and P 2 represent independently an acrylate group or a methacrylate group,
E 1 and E 2 represent independently an alkylene group having the carbon atom number of 1 to 15, at least one methylene group present in the alkylene group may be substituted with an oxygen atom, —CO—, —OCO—, —COO—, or —CH═CH—, where oxygen atoms are not directly bonded to each other,
A 1 , A 2 , and A 3 represent independently a 1,4-phenylene group or a 2,6-naphthylene group, the 1,4-phenylene group or the 2,6-naphthylene group may be unsubstituted or have at least one fluorine atom, chlorine atom, or alkyl group having the carbon atom number of 1 to 3 (at least one methylene group in the alkyl group may be substituted with an oxygen atom, —CO—, —OCO—, or —COO—, where oxygen atoms are not directly bonded to each other) as a substituent, at least one of A 1 , A 2 , and A 3 has a substituent,
Z 1 and Z 2 represent independently —COO—, —OCO—, —CH 2 CH 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, or a single bond) and
at least one type of compound represented by General formula (2) as a second component
P 3 -E 3 -A 4 -Z 3 -A 5 -Z 4 -A 6 -R 1   (2)

(in the formula, P 3 represents independently an acrylate group or a methacrylate group,
E 3 represents an alkylene group having the carbon atom number of 1 to 15, at least one methylene group present in the alkylene group may be substituted with an oxygen atom, —CO—, —OCO—, —COO—, or —CH═CH—, where oxygen atoms are not directly bonded to each other,
A 4 , A 5 , and A 6 represent independently a 1,4-phenylene group or a 2,6-naphthylene group, the 1,4-phenylene group or the 2,6-naphthylene group may be unsubstituted or have at least one fluorine atom, chlorine atom, or alkyl group having the carbon atom number of 1 to 3 (at least one methylene group in the alkyl group may be substituted with an oxygen atom, —CO—, —OCO—, or —COO—, where oxygen atoms are not directly bonded to each other) as a substituent, at least one of A 4 , A 5 , and A 6 has a substituent,
Z 3 and Z 4 represent independently —COO—, —OCO—, —CH 2 CH 2 —, or a single bond,
R 1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, or an alkyl group having the carbon atom number of 1 to 15, and at least one methylene group present in the alkyl group may be substituted with an oxygen atom, —CO—, —OCO—, —COO—, or —CH═CH—, where oxygen atoms are not directly bonded to each other).

2. The polymerizable liquid crystal composition according to claim 1 , comprising at least one type of polymerization initiator as a third component and
a surfactant or a compound including a repeating unit represented by General formula (3) and having a weight average molecular weight of 100 or more as a fourth component,
CR 11 R 12 —CR 13 R 14   (3)

(in the formula, R 11 , R 12 , R 13 , and R 14 represent independently a hydrogen atom, a halogen atom, or a hydrocarbon group having the carbon atom number of 1 to 20, and hydrogen atoms in the hydrocarbon group may be substituted with at least one halogen atom).

3. The polymerizable liquid crystal composition according to claim 2 , comprising a chiral compound as a fifth component.

4. The polymerizable liquid crystal composition according to claim 1 , comprising a thiol compound as an additional component.

5. The polymerizable liquid crystal composition according to claim 1 , wherein the first component is represented by General formula (1-1),

(in the formula, Y 11 and Y 12 represent independently a hydrogen atom or a methyl group,
E 11 and E 12 represent independently an alkylene group having the carbon atom number of 1 to 13, at least one methylene group present in the alkylene group may be substituted with an oxygen atom, —CO—, —OCO—, —COO—, or —CH═CH—, where oxygen atoms are not directly bonded to each other,
X 1 to X 12 represent independently a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, one or more and three or less of them are a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, and
Z 11 and Z 12 represent independently —COO—, —OCO—, or a single bond).

6. The polymerizable liquid crystal composition according to claim 1 , wherein the second component includes at least one type of compound, in which A 4 , A 5 , and A 6 in General formula (2) are 1,4-phenylene groups, the 1,4-phenylene groups may independently be unsubstituted or have at least one fluorine atom, chlorine atom, methyl group, methoxy group, CF 3 group, or OCF 3 group as a substituent, and at least one of A 4 , A 5 , and A 6 has at least one substituent, and at least two types of compound, in which at least one of A 4 , A 5 , and A 6 in General formula (2) is a 2,6-naphthylene group and the other two are 1,4-phenylene groups, the 2,6-naphthylene group and the 1,4-phenylene groups may independently be unsubstituted or have at least one fluorine atom, chlorine atom, methyl group, methoxy group, CF 3 group, or OCF 3 group as a substituent, and at least one of A 4 , A 5 , and A 6 has at least one substituent.

7. The polymerizable liquid crystal composition according to claim 1 , wherein the second component includes at least one type of compound represented by General formula (2-1) and at least two types of compound selected from the group consisting of General formulae (2-2) to (2-4),

(in the formulae, Y 21 , Y 31 , Y 41 , and Y 51 represent independently a hydrogen atom or a methyl group,
E 21 , E 31 , E 41 , and E 51 represent independently an alkylene group having the carbon atom number of 1 to 13, at least one methylene group present in the alkylene group may be substituted with an oxygen atom, —CO—, —OCO—, —COO—, or —CH═CH—, where oxygen atoms are not directly bonded to each other,
Z 21 , Z 22 , Z 31 , Z 32 , Z 41 , Z 42 , Z 51 , and Z 52 represent independently —COO—, —OCO—, or a single bond,
X 13 to X 24 represent independently a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, one or more and three or less of them are a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group,
X 25 to X 39 represent independently a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, one or more and three or less of them are a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group,
X 40 to X 53 represent independently a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, one or more and three or less of them are a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group,
X 54 to X 68 represent independently a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a methoxy group, a CF 3 group, or an OCF 3 group, one or more and three or less of them are

Assignees

• Dainippon Ink & Chemicals

Inventors

• Nakata Hidetoshi
• Kuwana Yasuhiro
• Hasebe Hiroshi
• Kotani Kunihiko
• Nishiyama Isa

Classifications

• C09K2019/3408

  Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• C09K2019/3433

  Seven-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K19/322

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

• C09K2019/528

  Surfactants · CPC title