Polymerizable composition solution and optically anisotropic body including the same

Patent metadata

Field	Value
Publication number	US-9676959-B2
Application number	US-201414890453-A
Country	US
Kind code	B2
Filing date	May 23, 2014
Priority date	May 29, 2013
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

A polymerizable composition solution that has good storage stability and allows a polymerizable compound in the polymerizable composition to be aligned well with no defects after application to a base and removal of a solvent by a drying process and also an optically anisotropic body that includes the solution and has good alignment without any defects. A solution containing a polymerizable composition and an organic solvent, wherein the polymerizable composition contains 90 mass % or more of a polymerizable compound intramolecularly having a 2-methyl-1,4-phenylene group as represented by general formula (1) and an optically anisotropic body including the solution.

First claim

The invention claimed is:

1. A solution comprising a polymerizable composition and an organic solvent,
wherein the polymerizable composition contains 90 mass % or more of at least one polymerizable compound selected from polymerizable compounds represented by general formula (1-1) and general formula (1-2):

wherein in formula (1-1) P represents a polymerizable functional group; Sp represents a single bond or a spacer group, wherein the spacer group is an alkylene group having 1 to 18 carbon atoms, wherein the spacer group is optionally substituted with at least one halogen atom or CN, and one CH 2 group or at least two nonadjacent CH 2 groups are optionally each independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —SCO—, —COS—, or —C≡C—, as long as oxygen atoms are not directly bonded to each other; when at least two P are present, the at least two P are the same or different; and when at least two Sp are present, the at least two Sp are the same or different,
A 1 and A 2 each independently represent a
(b) a 1,4-phenylene group (one —CH═ or two or more nonadjacent —CH═ in this group may be substituted with —N═),
Z 1 and Z 2 each independently represent a single bond, —COO—, —OCO—, or —C≡C—; and
m 1 and n 1 each independently represent 0, 1, 2, 3, or 4, and m 1 +n 1 four or less; when m 1 is 2 to 4 and two or more A 1 and Z 1 are present, two or more A 1 and two or more Z 1 are each the same or different; when n 1 is 2 to 4 and two or more A 2 and Z 2 are present, two or more A 2 and two or more Z 2 are each the same or different,

wherein in formula (1-2) P represents a polymerizable functional group; Sp represents a single bond or a spacer group, wherein the spacer group is an alkylene group having 1 to 18 carbon atoms, wherein the spacer group is optionally substituted with at least one halogen atom or CN, and one CH 2 group or at least two nonadjacent CH 2 groups are optionally each independently substituted with —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —SCO—, —COS—, or —C≡C—, as long as oxygen atoms are not directly bonded to each other; when at least two P are present, the at least two P are the same or different and when at least two Sp are present, the at least two Sp can be the same or different,
A 1 and A 2 each independently represent a group selected from the group consisting of:
(a) 1,4-cyclohexylene group (one —CH 2 — or two or more nonadjacent —CH 2 — in this group may be substituted with —O— or —S—);
(b) a 1,4-phenylene group (one —CH═ or two or more nonadjacent —CH═ in this group is optionally substituted with —N═), and
(c) naphthalene-2,6-diyl group optionally substituted with a alkyl group having 1 carbon atom
Z 1 and Z 2 each independently represent a single bond, —COO—, —OCO—, or —C≡C—;
where one of R 4 and R 5 represents a hydrogen atom and the other represents a methyl group,
R 22 represents a hydrogen atom, a halogeno group, a cyano group, or aalkyl group having 1 to 8 carbon atoms, and one —CH 2 — or two or more nonadjacent —CH 2 — in the alkyl group is optionally each independently substituted with —CH═CH—, —C≡C—, —O—, —CO—, —COO—, or —OCO—, and at least one hydrogen atom in the alkyl group may be substituted with a fluorine atom or a chlorine atom, and
m 2 and n 2 each independently represent 0, 1, 2, 3, or 4, and m 2 +n 2 four or less; when m 2 is 2 to 4 and two or more A 1 and Z 1 are present, two or more A 1 and two or more Z 1 are each the same or different when n 2 is 2 to 4 and two or more A 2 and Z 2 are present, two or more A 2 and two or more Z 2 are each the same or different,
wherein the polymerizable composition comprises 30 to 90 mass % of the polymerizable compound represented by general formula (1-1).

2. The solution according to claim 1 , wherein the organic solvent is at least one of ketone solvents, ether solvents, ester solvents, and aromatic hydrocarbon solvents.

3. The solution according to claim 1 , further comprising a polymerization initiator.

4. The solution according to claim 1 , further comprising a polymerizable chiral compound.

5. The solution according to claim 1 , further comprising a polymerizable discotic compound.

6. The solution according to claim 1 , further comprising a surfactant.

7. An optically anisotropic body comprising a dried and cured product of the solution according to claim 1 .

8. A retardation film comprising a dried and cured product of the solution according to claim 1 .

9. An optical compensation film comprising a dried and cured product of the solution according to claim 1 .

10. A retardation patterned film comprising a dried and cured product of the solution according to claim 1 .

11. A homogeneously aligned liquid crystal film comprising a dried and cured product of the solution according to claim 1 .

12. A laminated optically anisotropic body having a laminate of a plurality of the optically anisotropic bodies according to claim 7 .

Assignees

• Dainippon Ink & Chemicals

Inventors

• Kuwana Yasuhiro
• Nakata Hidetoshi
• ENDOU Koichi
• Yamamoto Mika
• Kotani Kunihiko
• Hasebe Hiroshi
• Ono Yoshiyuki

Classifications

• G02B5/3083

  Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001) · CPC title

• C08F220/302

  and two or more oxygen atoms in the alcohol moiety · CPC title

• G02F2202/023

  curable · CPC title

• C09D135/02

  Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence) · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title