Polymerizable composition and film using the same

Patent metadata

Field	Value
Publication number	US-2017190819-A1
Application number	US-201515312884-A
Country	US
Kind code	A1
Filing date	Jun 16, 2015
Priority date	Jun 23, 2014
Publication date	Jul 6, 2017
Grant date	—

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.

First claim

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 1 -Z A1 -A 1 Z A2  m   (I-1)
(where P 1 represents a polymerizable functional group; Z 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 2 groups are each independently optionally substituted with —O—, —CO—, —COO—, —OCO—, —OCOO—, —CH═CH—, or —C≡C— such that oxygen atoms are not directly bonded to each other; A 1 represents a cyclic compound group having 1 to 4 rings; Z 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 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 A2 's may be the same as or different from each other).

4 . The polymerizable liquid crystal composition according to claim 3 , wherein A 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)

(where the symbol * represents a linkage to Z 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 A1 and/or Z A2 bonded to A 1 are each an oxygen atom, the linking atom of A 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 2 —(S 1 —X 1 ) q1 -MG-R 2   (II)
(where P 2 represents a polymerizable functional group; S 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 2 group or two or more CH 2 groups not adjoining each other are each independently optionally substituted with —O—, —COO—, —OCO—, or —OCO—O—); X 1 represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 , —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond (where P 2 —S 1 and S—X 1 exclude —O—O—, —O—NH—, —S—S—, and —O—S—); q1 represents 0 or 1; MG represents a mesogenic group; R 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 2 — or two or more —CH 2 —'s not adjoining each other are each independently optionally substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—; and R 2 alternatively represents a group represented by General Formula (II-a)
—(X 2 —S 2 ) q2 —P 3   (II-a)

(where P 3 represents a reactive functional group; S 2 has the same definition as S 1 ; X 2 has the same definition as X 1 (where P 3 —S 2 and S 2 —X 2 exclude —O—O—, —O—NH—, —S—S—, and —O—S—); and q 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) r1 —B2-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 3 , OCF 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 3 ) q4 —(S 3 ) q3 —P 4   (II-c)

(where P 4 represents a reactive functional group; S 3 represents an alkylene group having 1 to 18 carbon atoms; X 3 represents —O—, —COO—, —OCO—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 OCO—, or —CH 2 CH 2 COO—; q represents 0 or 1; q 4 represents 0 or 1 (where P 4 —S 3 and S 3 —X 3 exclude —O—O—, —O—NH—, —S—S—, and —O—S—)); Z1 and Z2 each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 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 2 —(S 1 —X 1 ) q1 -B11-Z11-B2-Z2-B3-(X 2 —S 2 ) q2 —P 3   (II-2-2-2)
(where P 2 and P 3 each independently represent a polymerizable functional group; S 1 and S 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 2 group or two or more CH 2 groups not adjoining each other are each independently optionally substituted with —O—, —COO—, —OCO—, or —OCO—O—); X 1 and X 2 each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OC

Assignees

• Dainippon Ink & Chemicals

Inventors

• Endo Kouichi
• Kuwana Yasuhiro
• Nakata Hidetoshi
• Yamamoto Mika
• Hatsusaka Kazuaki
• Nishiyama Isa

Classifications

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/2035

  Ph-COO-Ph · CPC title

• C09K19/54

  Additives having no specific mesophase {characterised by their chemical composition} · CPC title

• C08F220/1811

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title

• C08F220/283

  and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate · CPC title