Polymerizable compound, polymer, polymerizable composition, film, and half mirror for displaying projection image

Patent metadata

Field	Value
Publication number	US-10012868-B2
Application number	US-201615273784-A
Country	US
Kind code	B2
Filing date	Sep 23, 2016
Priority date	Mar 28, 2014
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

The present invention provides a polymerizable compound denoted by Formula (I): in the formula, Z 1 and Z 2 represent an arylene group, and the like, m represents 1 or 2, n represents an integer of 0 or 1, and when m is 2, n is 0, L 1 , L 2 , L 3 , and L 4 each independently represent a linking group such as —C(═O)O— and —OC(═O)—, T 3 represents -Sp 4 -R 4 , X represents —O—, and the like, r represents 1 to 4, Sp 1 , Sp 2 , Sp 3 , Sp 4 , and Sp 5 each independently represent a single bond or a linking group, R 1 and R 2 each independently represent a polymerizable group, and R 3 , R 4 , and R 5 each independently represent a hydrogen atom, a polymerizable group, or the like; a polymerizable composition containing the polymerizable compound described above; a film formed of the polymerizable composition described above; and a half mirror for displaying a projection image including the film described above.

First claim

What is claimed is:

1. A polymerizable compound denoted by Formula (I);

in the formula, Z 1 and Z 2 each independently represent a trans-1,4-cyclohexylene group which may have a substituent group, an arylene group which may have a substituent group, or a heteroarylene group which may have a substituent group,
all of the substituent groups are each independently one to four substituent groups selected from the group consisting of —CO—X-Sp 3 -R 3 , an alkyl group, and an alkoxy group,
m represents an integer of 1 or 2, and n represents an integer of 0 or 1,
when m represents 2, n represents 0,
when m represents 2, two Z 1 's may be identical to each other or different from each other,
L 1 , L 2 , L 3 , and L 4 each independently represent a linking group selected from the group consisting of a single bond, —O—, —CH 2 O—, —OCH 2 —, —(CH 2 ) 2 OC(═O)—, —C(═O)O(CH 2 ) 2 —, —NH—, N(CH 3 )—, —S—, —C(═O)O—, —OC(═O)—, —OC(═O)O—, —C(═O)N(T 3 )-, —N(T 3 )C(═O)—, —C(═O)S—, —SC(═O)—, —CH 2 C(═O)O—, —OC(═O)CH 2 —, —CH═CH—C(═O)O—, —OC(═O)—CH═CH—, —CH═N—, —N═CH—, and —N═N—,
T 3 represents -Sp 4 -R 4 ,
X represents —O—, —S—, or —N(Sp 5 -R 5 )—, or represents a nitrogen atom forming a cyclic structure along with R 3 and Sp 3 ,
r represents an integer of 1 to 4,
Sp 1 , Sp 2 , Sp 3 , Sp 4 , and Sp 5 each independently represent a linking group selected from the group consisting of a single bond, a straight chain or branched alkylene group having 1 to 20 carbon atoms, and a group in which one or two or more —CH 2 —'s in a straight chain or 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—,
R 1 and R 2 each independently represent any one polymerizable group selected from the group consisting of groups denoted by Formula (Q-1) to Formula (Q-5) described below, and
R 3 , R 4 , and R 5 each independently represent a hydrogen atom, a cycloalkyl group, a group in which one or two or more —CH 2 —'s in a cycloalkyl group are substituted with —O—, —S—, —NH—, —N(CH 3 )—, —C(═O)—, —OC(═O)—, or —C(═O)O—, or any one polymerizable group selected from the group consisting of the groups denoted by Formula (Q-1) to Formula (Q-5) described below, and in a case in which X is a nitrogen atom forming a cyclic structure along with R 3 and Sp 3 , R 3 may represent a single bond, and when Sp 5 is a single bond, R 5 is not a hydrogen atom

2. The polymerizable compound according to claim 1 ,
wherein the arylene group is a 1,4-phenylene group.

3. The polymerizable compound according to claim 1 ,
wherein at least one of Z 1 or Z 2 is an arylene group which may have a substituent group or a heteroarylene group which may have a substituent group.

4. The polymerizable compound according to claim 1 ,
wherein m+n is 2.

5. The polymerizable compound according to claim 4 ,
wherein m is 2, and two Z 1 's are each a trans-1,4-cyclohexylene group which may have a substituent group and an arylene group which may have a substituent group from an R 1 direction, or
m is 1, n is 1, Z 1 is an arylene group which may have a substituent group, and Z 2 is an arylene group which may have a substituent group.

6. The polymerizable compound according to claim 1 ,
wherein R 1 and R 2 each independently represent the group denoted by Formula (Q-1) or the group denoted by Formula (Q-2).

7. The polymerizable compound according to claim 1 ,
wherein all of L 1 , L 2 , L 3 , and L 4 are —C(═O)O— or —OC(═O)—.

8. The polymerizable compound according to claim 6 ,
wherein all of L 1 , L 2 , L 3 , and L 4 are —C(═O)O— or —OC(═O)—.

9. The polymerizable compound according to claim 1 ,
wherein m is 1, n is 1, r is 1, Sp 3 is a straight chain or branched alkylene group having 1 to 20 carbon atoms, and R 3 is a hydrogen atom.

10. The polymerizable compound according to claim 1 ,
wherein m is 1, n is 1, and both of Z 1 and Z 2 are a trans-1,4-cyclohexylene group which may have a substituent group.

11. A polymerizable composition, containing: the polymerizable compound according to claim 1 .

12. The polymerizable composition according to claim 11 , further containing:
other liquid crystal compounds along with the polymerizable compound denoted by Formula (I).

13. The polymerizable composition according to claim 11 , further containing:
a chiral compound.

14. A film, comprising:
a layer obtained by curing the polymerizable composition according to claim 11 .

15. A film, comprising:
two or more layers obtained by curing the polymerizable composition according to claim 11 .

16. The film according to claim 14 ,
wherein the film has selective reflection, and
Δλ/λ which is a ratio of a half-width Δλ in a wavelength range of the selective reflection to a center wavelength λ of the selective reflection is less than or equal to 0.09.

17. A film, comprising:
at least three layers formed of the polymerizable composition according to claim 11 ,
wherein the three layers are a layer formed by immobilizing a cholesteric liquid crystalline phase having a center wavelength of selective reflection in a red light wavelength range, a layer formed by immobilizing a cholesteric liquid crystalline phase having a center wavelength of selective reflection in a green light wavelength range, and a layer formed by immobilizing a cholesteric liquid crystalline phase having a center wavelength of selective reflection in a blue light wavelength range.

18. A half mirror for displaying a projection image, comprising:
the film according to claim 17 .

19. The half mirror for displaying a projection image according to claim 18 , further comprising:
a substrate which is inorganic glass or an acrylic resin.

20. The half mirror for displaying a projection image according to claim 18 , further comprising:
an antireflection layer on an outermost surface.

Assignees

• Fujifilm Corp

Inventors

• Nakazawa Yuki
• Katoh Shunya
• Matsuyama Hiroshi
• Hayashi Daisuke
• Yoshikawa Masaru

Classifications

• C07D307/12

  Radicals substituted by oxygen atoms · CPC title

• C09K2219/03

  in the form of films, e.g. films after polymerisation of LC precursor · CPC title

• C07C235/60

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C09K2019/044

  the specific unit being a perfluoro chain used as an end group · CPC title

• C07C233/52

  with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring · CPC title