Compound, polymerizable composition, cured product, optical film, polarizing plate, and image display device

Patent metadata

Field	Value
Publication number	US-11732191-B2
Application number	US-202117486096-A
Country	US
Kind code	B2
Filing date	Sep 27, 2021
Priority date	Mar 29, 2019
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

Provided is a compound which is capable of reducing a tilt angle of a liquid crystal molecule, and a polymerizable composition, a cured product, an optical film, a polarizing plate, and an image display device, each using the compound. The compound is represented, for example, by Formula (I), P-Sp-Z-G 1 -(X 1 -Cy 1 )n-(X 2 -A 1 )m-X 3 -A 2 .

First claim

What is claimed is:

1. A compound represented by Formula (I),
P - Sp - Z - G 1 -( X 1 - Cy 1 ) n -( X 2 - A 1 ) m - X 3 - A 2   (I)

in Formula (I),
Sp represents a single bond, a linear alkylene group having 1 to 12 carbon atoms, a branched alkylene group having 3 to 12 carbon atoms, or a divalent linking group obtained by substituting one or more of —CH 2 -'s constituting the linear or branched alkylene group with —O—, —S—, —NH—, —N(Q)-, —CO—, —COO—, —OCO—, —CO—NH—, or —NH—CO—, and Q represents a substituent,
Z represents a single bond, —O—, —S—, —NH—, —N(Q)-, —CO—, —COO—, —OCO—, —CO—NH—, or —NH—CO—, and Q represents a substituent,
X 1 , X 2 , and X 3 each independently represent a single bond, —COO—, —OCO—, —CO—NH—, or —NH—CO—,
G 1 represents an aromatic ring which may have a substituent or a 1,4-cyclohexylene group which may have a substituent,
Cy 1 represents a 1,4-cyclohexylene group which may have a substituent,
A 1 represents an aromatic ring which may have a substituent,
A 2 represents an aromatic ring which may have a substituent R, or an unsubstituted cyclohexane ring, the substituent R represents a linear alkoxy group having 1 to 11 carbon atoms, a branched alkoxy group having 3 to 11 carbon atoms, a linear alkyl group having 1 to 12 carbon atoms, a branched alkylene group having 3 to 12 carbon atoms, or -Z-Sp-P, and Z and Sp are each the same as described above, provided that in a case where A 2 is a 6-membered aromatic ring, A 2 has no substituent R at a para position with respect to a bonding position with X 3 , and in a case where the substituent R is -Z-Sp-P, two Z's, two Sp's, and two P's which are present in the formula may be the same as or different from each other,
n represents 0 or 1, m represents an integer of 0 to 2, and n+m represents an integer of 1 to 3, and in a case where m is 2, both of two X 2 's and two A 1 's which are present in the formula may be the same as or different from each other,
P represents a polymerizable group, provided that in a case where A 2 is an aromatic ring having -Z-Sp-P as the substituent R, one of the two P's which are present in the formula represents a polymerizable group and the other represents a hydrogen atom or a polymerizable group,
in a case where G 1 is the aromatic ring which may have a substituent, n is 0, and m is 1, X 3 represents —COO—, —OCO—, —CO—NH—, or —NH—CO—, and
in a case where G 1 is the aromatic ring which may have a substituent, n is 1, m is 0, and A 2 is the aromatic ring which may have the substituent R, Z represents a single bond, —S—, —NH—, —N(Q)-, —CO—, —COO—, —OCO—, —CO—NH—, or —NH—CO—, and Q represents a substituent, provided that in a case where Z is the single bond, an atom adjacent to G 1 among the divalent linking groups constituting Sp is not an oxygen atom.

2. The compound according to claim 1 ,
wherein A 1 in Formula (1) represents an unsubstituted aromatic ring.

3. The compound according to claim 1 ,
wherein A 1 in Formula (1) represents an aromatic ring having a substituent, and the substituent is an alkyl group, an alkoxy group or a halogen atom.

4. The compound according to claim 1 ,
wherein a total of n and m in Formula (1) is 1.

5. The compound according to claim 1 ,
wherein Sp in Formula (1) is a linear alkylene group having 1 to 3 carbon atoms or a branched alkylene group having 3 carbon atoms.

6. The compound according to claim 1 ,
wherein A 2 in Formula (1) is the aromatic ring which may have the substituent R.

7. The compound according to claim 1 ,
wherein A 2 in Formula (1) is a 6-membered aromatic ring having the substituent R at an ortho position or meta position with respect to a bonding position with X 3 .

8. The compound according to claim 1 ,
wherein the substituent R is -Z-Sp-P.

9. The compound according to claim 1 ,
wherein the substituent R is -Z-Sp-P, one of the two P's in the formula represents a polymerizable group, and another one represents a hydrogen atom.

10. The compound according to claim 1 ,
wherein A 2 in Formula (1) is an unsubstituted 6-membered aromatic ring.

11. The compound according to claim 1 ,
wherein A 2 in Formula (1) is a benzene ring which may have the substituent R.

12. The compound according to claim 1 ,
wherein m in Formula (1) is 0.

13. The compound according to claim 1 ,
wherein n in Formula (1) is 1.

14. The compound according to claim 1 ,
wherein n in Formula (1) is 0.

15. The compound according to claim 1 ,
wherein P in Formula (1) is a polymerizable group represented by any of Formulae (P-1) to (P-9),

16. The compound according to claim 1 ,
wherein G 1 in Formula (1) is a 1,4-cyclohexylene group which may have a substituent.

17. The compound according to claim 1 ,
wherein G 1 in Formula (1) is the aromatic ring which may have a substituent.

18. A polymerizable composition comprising the compound according to claim 1 .

19. The polymerizable composition according to claim 18 , comprising a polymerizable liquid crystal compound different from the compound.

20. The polymerizable composition according to claim 19 ,
wherein the compound and the polymerizable liquid crystal compound have polymerizable groups that are different from each other.

21. The polymerizable composition according to claim 18 , comprising a polymerization initiator.

22. A cured product obtained by curing the polymerizable composition according to claim 18 .

23. An optical film comprising the cured product according to claim 22 .

24. A polarizing plate comprising:
the optical film according to claim 23 ; and
a polarizer.

25. An image display device comprising the optical film according to claim 23 .

Assignees

• Fujifilm Corp

Inventors

• Fukushima Yuki
• Inada Hiroshi
• Sumi Toshikazu
• Katoh Shunya
• Ichihashi Mitsuyoshi

Classifications

• C09K19/3068 Primary

  chain containing -COO- or -OCO- groups · CPC title

• C09K19/3497

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• G02B5/3016 Primary

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

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K2019/3075

  Cy-COO-Ph · CPC title