Optically anisotropic layer, method for producing the optically anisotropic layer, a laminate, polarizing plate, display device, liquid crystal compound, method for producing the liquid crystal compound, and carboxylic acid compound

Patent metadata

Field	Value
Publication number	US-11072741-B2
Application number	US-201816042224-A
Country	US
Kind code	B2
Filing date	Jul 23, 2018
Priority date	Oct 21, 2014
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

An optically anisotropic layer is formed by a liquid crystal compound represented by General Formula 1, in which the long axes of the molecules are oriented.

wherein L 1 and L 2 independently represent a linking group having a carbonyl group; F 1 and F 2 independently represent an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a halogen atom; n and m independently represent an integer from 0 to 4; a and b independently represent an integer from 1 to 4; T 1 and T 2 independently represent a spacer portion including a straight chain or branched alkylene or alkylene oxide group having 2 to 20 carbon atoms; and Ar represents a divalent group having at least one aromatic ring selected from a group consisting of aromatic hydrocarbon rings and aromatic heterocycles, the number of Π electrons in the Ar group being 8 or greater.

First claim

What is claimed is:

1. A method for producing an optically anisotropic layer, comprising:
spreading a composition containing a liquid crystal compound represented by General Formula 1 below or spreading a polymerizable composition containing a liquid crystal compound represented by General Formula 1 below,
applying heat to orient the long axes of the molecules of the liquid crystal compound represented by General Formula 1 below; and
curing the composition or the polymerizable composition

wherein each of L 1 and L 2 independently represents a linking group having a carbonyl group; each of F 1 and F 2 independently represents an alkyl group having a carbon number within a range from 1 to 4, an alkoxy group having a carbon number within a range from 1 to 4, or a halogen atom; each of n and m independently represents an integer within a range from 0 to 4; each of a and b independently represent an integer within a range from 1 to 4; T 1 and T 2 are represented by General Formula 3 below; and Ar represents a divalent group having at least one aromatic ring selected from a group consisting of aromatic hydrocarbon rings and aromatic heterocycles, the number of Π electrons contained in the Ar group being 8 or greater,

wherein each of Sp 1 and Sp 2 independently represents a straight chain or branched alkylene group having a carbon number within a range from 2 to 20, in the alkylene group, one or two or more —CH 2 — not adjacent to each other in the alkylene group may be substituted by —O—, —S—, —C(═O)—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —NR 1 C(═O)—, —C(═O)NR 2 —, —OC(═O)NR 3 —, —NR 4 C(═O)O—, —SC(═O)— or —C(═O)S—: each of R 1 , R 2 , R 3 and R 4 independently represents a hydrogen atom, a halogen atom or an alkyl group having a carbon number within a range from 1 to 4; and each of P 1 and P 2 independently represents a polymerizable group or a hydrogen atom, wherein at least one is a polymerizable group.

2. A method for producing an optically anisotropic layer as defined in claim 1 , wherein:
Ar of General Formula 1 is an aromatic ring represented by any one of General Formulae 2-1 to 2-4 below,

wherein Q 1 represents —S—, —O—, or NR 11 —, R 11 represents a hydrogen atom or an alkyl group having a carbon number within a range from 1 to 6; Y 1 represents an alkyl group having a carbon number within a range from 1 to 6, an aromatic hydrocarbon group having a carbon number within a range from 6 to 12, or an aromatic heterocyclic group having a carbon number within a range from 3 to 12; each of Z 1 , Z 2 , and, Z 3 independently represents a hydrogen atom, an aliphatic hydrocarbon or alkoxy group having a carbon number within a range from 1 to 20, an alicyclic hydrocarbon group having a carbon number within a range from 3 to 20, a monovalent aromatic hydrocarbon group having a carbon number within a range from 6 to 20, a halogen atom, a cyano group, a nitro group, —NR 12 R 13 or SR 12 , Z 1 and Z 2 may bond together to form an aromatic ring or an aromatic heterocyclic ring; each of R 12 and R 13 independently represents a hydrogen atom or an alkyl group having a carbon number within a range from 1 to 6; each of A 1 and A 2 independently represents a group selected from a group consisting of —O—, —NR 21 — (R 21 represents a hydrogen atom or a substituent), —S— and CO—; X is a group 14 to group 16 non metallic atom that may be bound to a hydrogen atom or a substituent group; Ax represents an organic group having a carbon number within a range from 2 to 30, having at least one aromatic ring selected from a group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings; Ay is a hydrogen atom, an alkyl group having a carbon number within a range from 1 to 6 which may have a substituent, or an organic group having a carbon number within a range from 2 to 30, having at least one aromatic ring selected from a group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings, the aromatic rings of Ax and Ay may have substituents, Ax and Ay may be bound to form a ring; and Q 2 represents a hydrogen atom or an alkyl group having a carbon number of 1 to 6 which may have a substituent.

3. A method for producing an optically anisotropic layer as defined in claim 2 , wherein:
Ar of General Formula 1 is an aromatic ring represented by General Formula 2-2.

4. A method for producing an optically anisotropic layer as defined in claim 1 , wherein:
the composition or the polymerizable composition is spread onto a substrate having a glass transition temperature higher than the orientation temperature of the liquid crystal compound.

5. A liquid crystal compounds represented by General Formula 1 below:

wherein each of L 1 and L 2 independently represents a linking group having a carbonyl group; each of F 1 and F 2 independently represents an alkyl group having a carbon number within a range from 1 to 4, an alkoxy group having a carbon number within a range from 1 to 4, or a halogen atom; each of n and m independently represents an integer within a range from 0 to 4; each of a and b independently represent an integer within a range from 1 to 4; T 1 and T 2 are represented by General Formula 3 below; and Ar represents any one of the aromatic rings represented by General Formulae 2-1 to 2-4 below:

wherein Q 1 represents —S—, —O—, or NR 11 , R 11 represents a hydrogen atom or an alkyl group having a carbon number within a range from 1 to 6; Y 1 represents an alkyl group having a carbon number within a range from 1 to 6, an aromatic hydrocarbon group having a carbon number within a range from 6 to 12, or an aromatic heterocyclic group having a carbon number within a range from 3 to 12; each of Z 1 , Z 2 , and, Z 3 independently represents a hydrogen atom, an aliphatic hydrocarbon or alkoxy group having a carbon number within a range from 1 to 20, an alicyclic hydrocarbon group having a carbon number within a range from 3 to 20, a monovalent aromatic hydrocarbon group having a carbon number within a range from 6 to 20, a halogen atom, a cyano group, a nitro group, —NR 12 R 13 or SR 12 , Z 1 and Z 2 may bond together to form an aromatic ring or an aromatic heterocyclic ring; each of R 12 and R 13 independently represents a hydrogen atom or an alkyl group having a carbon number within a range from 1 to 6; each of A 1 and A 2 independently represents a group selected from a group consisting of —O—, —NR 21 — (R 21 represents a hydrogen atom or a substituent), —S— and CO—; X is a group 14 to group 16 non metallic atom that may be bound to a hydrogen atom or a substituent group; Ax represents an organic group having a carbon number within a range from 2 to 30, having at least one aromatic ring selected from a group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings; Ay is a hydrogen atom, an alkyl group having a carbon number within a range from 1 to 6 which may have a substituent, or an organic group having a carbon number within a range from 2 to 30, having at least one aromatic ring selected from a group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings, the aromatic rings of Ax and Ay may have substituents, Ax and Ay may be bound to form a ring; and Q 2 represents a hydrogen atom or an alkyl group having a carbon n

Assignees

• Fujifilm Corp

Inventors

• Matsuyama Hiroshi
• Goto Ryoji
• Ishikawa Hiroyuki
• Takahashi Keita
• Katsumata Taiji

Classifications

• B32B2307/514

  Oriented · CPC title

• B32B2307/7246

  Water vapor barrier · CPC title

• C09K19/3491 Primary

  having sulfur as hetero atom · CPC title

• B32B27/308

  comprising acrylic (co)polymers · CPC title

• B32B2255/00

  Coating on the layer surface · CPC title