Compound, composition for anisotropic dye films including the compound, anisotropic dye film, and optical element

Patent metadata

Field	Value
Publication number	US-12049583-B2
Application number	US-202318156670-A
Country	US
Kind code	B2
Filing date	Jan 19, 2023
Priority date	Aug 3, 2020
Publication date	Jul 30, 2024
Grant date	Jul 30, 2024

Abstract

A compound of formula (1) or (11):

X-A 1 -(N═N-A 2 ) n -N═N-A 3 -Y  (1)

X-A 41 -(N═N-A 42 ) n -N═N-A 43 -Y  (11),
-A 1 - and -A 2 - being independently a divalent group of an S-containing aromatic heterocyclic ring, with no adjacent non-carbons in the ring, a divalent group of a benzisothiazole ring, or a divalent group of an aromatic hydrocarbon ring, -A 3 - being a divalent group of an aromatic hydrocarbon ring, —X is a branched alkyl, alkoxy, or alkylsulfanyl group having 3 or more carbon atoms, —Y is a monovalent organic group, n is 1, 2, or 3, when n is 2 or 3, a plurality of -A 2 -s and/or -A 42 -s optionally differing, wherein -A 1 - and -A 2 - are not both a divalent group of an aromatic hydrocarbon ring, at least one -A 42 - is a divalent group of an S-containing aromatic heterocyclic ring, -A 41 - and -A 43 - are independently a divalent group of an aromatic hydrocarbon ring.

First claim

The invention claimed is:

1. A compound of formula (1) or (11):
X-A 1 -(N═N-A 2 ) n -N═N-A 3 -Y -  (1)

X-A 41 -(N═N-A 42 ) n -N═N-A 43 -Y  (11),

wherein
-A 1 - and -A 2 - are independently an unsubstituted or substituted divalent group of an aromatic heterocyclic ring comprising an S, atoms in the aromatic heterocyclic ring other than a carbon atom not being adjacent to one another, an unsubstituted or substituted divalent group of a benzisothiazole ring, or an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring,
-A 3 - is an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring,
—X is a branched alkyl, alkoxy, or alkylsulfanyl group having 3 or more carbon atoms,
—Y is a monovalent organic group,
n is 1, 2, or 3, when n is 2 or 3, a plurality of -A 2 -s and/or -A 42 -s optionally differing,
wherein -A 1 - and -A 2 - are not both an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring,
at least one -A 42 - is an unsubstituted or substituted divalent group of an aromatic heterocyclic ring comprising an S,
-A 41 - and -A 43 - are independently an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring.

2. The compound of claim 1 , wherein, in formula (1), the aromatic heterocyclic ring comprising an S is a thiophene ring, a benzothiophene ring, a thiazole ring, a thienopyrrole ring, a thienothiophene ring, a furothiazole ring, a thienofuran ring, a thienothiazole ring, or a benzothiazole ring.

3. The compound of claim 1 , wherein, in formula (1), -A 3 - is an unsubstituted or substituted phenylene group.

4. The compound of claim 1 , wherein, in formula (1), -A 2 - is an unsubstituted or substituted phenylene group.

5. The compound of claim 1 , wherein, in formula (1), —Y is —O—R x or —N(—R y )—R x ,
wherein —R x and —R y are independently a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 5 to 14 ring-forming atoms, or an aryl group having 5 to 14 ring-forming atoms, —R x and —R y optionally being bonded to each other to form a ring, the linear or branched alkyl group having 1 to 15 carbon atoms and the aryl group having 5 to 14 ring-forming atoms optionally being substituted, one or more methylene groups in the linear or branched alkyl group having 1 to 15 carbon atoms, the cycloalkyl group having 5 to 14 ring-forming atoms, or the ring formed by —R x and —R y being bended to each other may be replaced with —O—, —S—, —NH—, —N(R z )—, —C(═O)—, —C(═O)—O—, —C(═O)—NH—, —CHF—, —CF 2 —, —CHCl—, —CCl 2 —, an acryloyloxy group, a methacryloyloxy group, or a glycidyloxy group, and
wherein R z is a linear or branched alkyl group having 1 to 6 carbon atoms.

6. The compound of claim 1 , wherein, in formula (11), n is 2 or 3, and
wherein -A 42 -s are independently the unsubstituted or substituted divalent group of an aromatic hydrocarbon ring or the unsubstituted or substituted divalent group of an aromatic heterocyclic ring comprising an S.

7. The compound of claim 1 , wherein, in formula (11) above, the aromatic heterocyclic ring of -A 42 - is a thiophene ring, a benzothiophene ring, a thiazole ring, an isothiazole ring, a 1,3,4-thiadiazole ring, a thienopyrrole ring, a thienothiophene ring, a furothiazole ring, a thienofuran ring, a thienothiazole ring, a benzisothiazole ring, or a benzothiazole ring.

8. The compound of claim 1 , wherein, in formula (11) above, -A 43 - is an unsubstituted or substituted phenylene group.

9. The compound of claim 1 , wherein, in formula (11) above, -A 41 - is an unsubstituted or substituted phenylene group.

10. An anisotropic dye film-forming composition, comprising:
the compound of claim 1 ; and
a polymerizable liquid crystal compound.

11. An anisotropic dye film-forming composition, comprising:
a polymerizable liquid crystal compound; and
a compound of formula (21):
X-A 21 -(N═N-A 22 ) n -N═N-A 23 -Y  (21),

wherein
-A 21 - and -A 22 - are independently an unsubstituted or substituted divalent group of an aromatic heterocyclic ring comprising an S or an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring,
-A 23 - is an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring,
—X is a branched alkyl, alkoxy, or alkylsulfanyl group having 3 or more carbon atoms,
—Y represents is a monovalent organic group, group;
n is 1, 2, or 3, when n is 2 or 3, a plurality of -A 22 -s optionally differing, and
at least one of -A 21 - and -A 22 - is-being an unsubstituted or substituted divalent group of an aromatic heterocyclic ring comprising an S.

12. An anisotropic dye film-forming composition, comprising:
a polymerizable liquid crystal compound; and
a compound of formula (31):
A 31 -(N═N-A 32 ) n -N═N-A 33 -Y  (31),

wherein
-A 31 is an unsubstituted or substituted group of any one of formulae (a-2) to (a-7), with * being a linkage to —N and S 4 to S 14 being a position at which a substituent is attached to the group when the group is substituted:

-A 32 - is an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring or an unsubstituted or substituted divalent group of an aromatic heterocyclic ring,
-A 33 - is an unsubstituted or substituted phenylene group,
—Y is a monovalent organic group, and
n is 1, 2, or 3, and when n is 2 or 3, a plurality of -A 32 -s optionally differ.

13. The anisotropic dye film-forming composition of claim 12 , wherein, in formula (31), -A 32 - is an unsubstituted or substituted divalent group of an aromatic hydrocarbon ring.

14. The anisotropic dye film-forming composition of claim 12 , wherein, in formula (3), —Y is —O—R x or —N(—R y )—R x ,
wherein —R x and —R y are independently a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 5 to 14 ring-forming atoms, or an aryl group having 5 to 14 ring-forming atoms, —R x and —R y optionally being bonded to each other to form a ring,
wherein the linear or branched alkyl group having 1 to 15 carbon atoms and the aryl group having 5 to 14 ring-forming atoms are optionally substituted,
wherein one or more methylene groups in the linear or branched alkyl group having 1 to 15 carbon atoms, the cycloalkyl group having 5 to 14 ring-forming atoms, or the ring formed by —R x and —R y being bended to each other is optionally replaced with —O—, —S—, —NH—, —N(R z )—, —C(═O)—, —C(═O)—O—, —C(═O)—NH—, —CHF—, —CF 2 —, —CHCl—, —CCl 2 —, an acryloyloxy group, a methacryloyloxy group, or a glycidyloxy group, and
wherein R z is a linear or branched alkyl group having 1 to 6 carbon atoms.

15. The anisotropic dye film-forming composition of claim 10 , wherein an r n1 /r n2 ratio of a number, r n1 , of ring structures in the polymerizable liquid crystal compound to the number, r n2 , ring structures in the compound of formula (1), (11), (21), or (31) is in a range of from 0.7 to 1.5.

16. The anisotropic dye film-forming composition of claim 10 , wherein the polymerizable liquid crystal compound is a compound having a carbon-carbon triple bond.

17. The anisotropic dye film-forming composition of claim 10 , further comprising:
a dye,
wherein a wavelength at which an absorption curve of the dye is a maximum in a wavelength range of from 350 to 800 nm is smaller than a wavelength at which an absorption curve of the compound of formula (1), (11), (21), or (31) is a maximum in a wav

Assignees

• Mitsubishi Chem Corp

Inventors

• Takeshita Kei
• Shiga Yasushi
• Akiyama Seiji
• Kadowaki Masami
• Osawa Terutsune
• Oizumi Junichi
• Takami Yoshie
• Kojima Souya

Classifications

• 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

• C09K19/3895

  containing two or more mesogenic groups per monomer unit, e.g. polyitaconates, polymaleates · CPC title

• C09B31/043 Primary

  Amino-benzenes · CPC title

• C09B29/3608

  containing a five-membered heterocyclic ring with only one nitrogen as heteroatom · CPC title

• C08L101/12

  characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity (liquid crystal materials or compositions C09K19/00) · CPC title