Polymerizable composition, film, and half mirror for displaying projection image

Patent metadata

Field	Value
Publication number	US-10703973-B2
Application number	US-201715685530-A
Country	US
Kind code	B2
Filing date	Aug 24, 2017
Priority date	Mar 12, 2015
Publication date	Jul 7, 2020
Grant date	Jul 7, 2020

Abstract

The present invention provides a polymerizable composition containing a polymerizable liquid crystal compound represented by Formula (I) and an oxime compound,

in the formula, A 1 and A 2 each represent a phenylene group or a trans-1,4-cyclohexylene group, L 1 and L 2 each represent single bond, —C(═O)O—, or —OC(═O)—, Q 1 and Q 2 each represent a polymerizable group or the like, m and n represent an integer of 0 to 2, X may represent —X 3 -Sp 3 -Q 3 or two X's may be bonded to each other to form a fused ring, X 3 represents —C(═O)O—, Sp 1 , Sp 2 , and Sp 3 each represent single bond, an alkylene group, or the like, Q 3 represents hydrogen atom, a cycloalkyl group, a polymerizable group, or the like, and l represents an integer of 0 to 4. The polymerizable composition hardly causes yellowing after curing and is useful for manufacturing a film and a half mirror for displaying a projection image.

First claim

What is claimed is:

1. A polymerizable composition, comprising:
a polymerizable liquid crystal compound represented by Formula (I); and
an oxime compound,

in the formula, A 1 and A 2 each independently represent a phenylene group which may have a substituent or a trans-1,4-cyclohexylene group which may have a substituent,
L 1 and L 2 each independently represent a single bond or a linking group selected from the group consisting of —CH 2 O—, —OCH 2 —, —(CH 2 ) 2 OC(═O)—, —C(═O)O(CH 2 ) 2 —, —C(═O)O—, —OC(═O)—, —OC(═O)O—, —CH═CH—C(═O)O—, and —OC(═O)—CH═CH—,
Sp 1 and Sp 2 each independently represent a single bond or a linking group selected from the group consisting of a linear alkylene group or a branched alkylene group having 1 to 20 carbon atoms, and a group in which one or two or more —CH 2 -'s in the linear alkylene group or the branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,
Q 1 and Q 2 each independently represent a hydrogen atom or a polymerizable group selected from the group consisting of groups represented by Formula Q-1 to Formula Q-5 and at least one of Q 1 and Q 2 represents a polymerizable group,

m and n each independently represent an integer of 0 to 2, when m represents 2, two A 1 's may be identical to each other or different from each other, and two L 1 's may be identical to each other or different from each other, and when n represents 2, two A 2, s may be identical to each other or different from each other, and two L 2 's may be identical to each other or different from each other,
X may represent a group represented by —X 3 —Sp 3 -Q 3 or two X's may be bonded to each other to form a fused ring with a benzene ring of a phenylene group to which two X's are bonded, wherein the fused ring is selected from the group consisting of naphthalene, chroman, isochroman, indoline, isoindoline, chromene, xanthene, phenoxathiin, thianthrene, quinoline, isoquinoline, phthalazine, quinoxaline, 1,3-benzodithiol-2-ylidene, and 1,3-benzothiazol-2-yl, and the fused ring may have a substituent,
X 3 represents a single bond, or a linking group selected from the group consisting of —O—, —C(═O), and —C(═O)O—,
Sp 3 represents a single bond or a linking group selected from the group consisting of a linear alkylene group or a branched alkylene group having 1 to 20 carbon atoms, and a group in which one or two or more —CH 2 -'s in the linear alkylene group or the branched alkylene group having 1 to 20 carbon atoms are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—,
Q 3 represents a hydrogen atom or any polymerizable group selected from the group consisting of a cycloalkyl group, a group in which one or two or more —CH 2 -'s in the cycloalkyl group are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, and groups represented by Formula Q-1 to Formula Q-5, and
l represents an integer of 0 to 4, and when l represents 2 to 4, 1 X's may be identical to each other or different from each other.

2. The polymerizable composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which in Formula (I), the phenylene group substituted with X is represented by Formula (IV) or Formula (V),

in Formula (IV) and Formula (V), * represents a bonding position with the remaining portion of the compound represented by Formula (I), and in Formula (V), Rz represents an alkyl group, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent.

3. The polymerizable composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which in Formula (I), X represents a group represented by —X-Sp 3 -Q 3 , X 3 represents —C(═O)O—, and l represents 1.

4. The polymerizable composition according to claim 3 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which in Formula (I), A 1 and A 2 each independently represent a 1,4-phenylene group which may have a substituent, m represents 1 or 2, and n represents 0 or 1.

5. The polymerizable composition according to claim 3 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which in Formula (I), both A 1 and A 2 represent an unsubstituted trans-1,4-cyclohexylene group, m represents 0 or 1, and n represents 1 or 2.

6. The polymerizable composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound represented by Formula (I-21),

in the formula, A 21 represents a 1,4-phenylene group which may have a substituent, A 22 represents an unsubstituted trans-1,4-cyclohexylene group, m 1 represents an integer of 0 to 1, and n 1 represents an integer of 0 to 1.

7. The polymerizable composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a compound represented by Formula (I-12),

in the formula, L 11 's each independently represent a single bond, or a linking group selected from the group consisting of —C(═O)O—, —OC(═O)—, and —OC(═O)O—.

8. The polymerizable composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a compound represented by Formula (I-22),

in the formula, L 22 's each independently represents a single bond or a linking group selected from the group consisting of —C(═O)O—, —OC(═O)—, and —OC(═O)O—.

9. The polymerizable composition according to claim 1 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which in Formula (I), m+n is greater than or equal to 2.

10. The polymerizable composition according to claim 2 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which in Formula (I), A 1 represents a 1,4-phenylene group which may have a substituent, m represents 1, n represents 2, and A 2 represents an unsubstituted trans-1,4-cyclohexylene group, and a 1,4-phenylene group which may have a substituent in this order from Q 1 side.

11. The polymerizable composition according to claim 10 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which, in Formula (I), the phenylene group substituted with X is represented by Formula (IV).

12. The polymerizable composition according to claim 10 ,
wherein the polymerizable liquid crystal compound is a polymerizable liquid crystal compound in which, in Formula (I), the phenylene group substituted with X is represented by Formula (V).

13. The polymerizable composition according to claim 1 , further comprising:
a chiral compound.

14. The polymerizable composition according to claim 1 , further comprising:
a cross-linking agent.

15. A film

Assignees

• Fujifilm Corp

Inventors

• Katoh Shunya
• Sakai Shinnosuke
• Saiki Yuki
• Anzai Akihiro

Classifications

• C08F222/30 Primary

  Nitriles · CPC title

• G02B5/3016

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title

• C09K19/3497

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• C09K19/3491

  having sulfur as hetero atom · CPC title

• C08F222/102

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