IP Library › Granted Patent US 10,059,877
Granted Patent B2
US 10,059,877 · App. 14/887,858 · Granted Aug 28, 2018

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

Inventors: Hiroshi Matsuyama (Kanagawa-ken, JP); Ryoji Goto (Kanagawa-ken, JP); Hiroyuki Ishikawa (Kanagawa-ken, JP); Keita Takahashi (Kanagawa-ken, JP); Taiji Katsumata (Kanagawa-ken, JP)
Assignee: FUJIFILM Corporation
C09K19/3491B32B23/04B32B23/08B32B23/20B32B27/308C09K19/3068C09K19/348C09K19/3486C09K19/3494C09K19/3497C09K19/3823C09K19/3861G02B5/305B32B27/08B32B33/00B32B2250/24B32B2255/00B32B2255/10B32B2255/26B32B2305/55B32B2307/40B32B2307/4026B32B2307/42B32B2307/514B32B2307/706B32B2307/7246B32B2457/20C09K19/3001C09K19/3477C09K19/38C09K2019/0448C09K2019/3408G02B5/3016
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Quick Facts
Patent No.
US 10,059,877
App. No.
14/887,858
Granted
Aug 28, 2018
Kind
B2
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.

Claims (58)

1. An optically anisotropic layer, comprising a liquid crystal compound represented by General Formula 1 below, or is formed by curing a polymerizable composition containing a liquid crystal compound represented by General Formula 1 below, the long axes of the molecules of the liquid crystal compound of General Formula 1 being oriented:

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; each of T 1 and T 2 independently represents a spacer portion including a straight chain or branched alkylene or alkylene oxide group having a carbon number within a range from 2 to 20; 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, and

wherein T 1 and T 2 of General Formula 3 are represented by General Formula 3 below:

T

1

⁢

:

⁢

⁢

P

1

-

Sp

1

-

T

2

⁢

:

⁢

⁢

P

2

-

Sp

2

-

}

General

⁢

⁢

Formula

⁢

⁢

3

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, 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. 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 group, or an 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 sub 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. 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. An optically anisotropic layer as defined in claim 1 , wherein:

the oriented state is fixed in one of a nematic phase and a smectic phase.

5. An optically anisotropic layer as defined in claim 4 , wherein

the oriented state is fixed in the smectic phase.

6. An optically anisotropic layer as defined in claim 1 , wherein:

the long axes of the molecules are fixed in a homogeneous orientation; and

phase differences Re(450 nm), Re(550 nm), and Re(650 nm) for wavelengths 450 nm, 550 nm, and 650 nm, respectively, satisfying Formulae A and B below:

Re(450 nm)/Re(550 nm)<0.95  Formula A

Re(650 nm)/Re(550 nm)>1.02  Formula B.

7. A laminate, comprising:

a resin film; and

an optically anisotropic layer as defined in claim 1 laminated on the resin film either directly or with an orienting film interposed therebetween.

8. A polarizing plate, comprising:

the laminate as defined in claim 7 , wherein:

the resin film is a polarizer.

9. A display device, comprising: the polarizing plate as defined in claim 8 .

10. The optically anisotropic layer according to claim 1 , wherein each of Sp 1 and Sp 2 in General Formula 3 independently represents a branched alkylene group having a carbon number within a range from 2 to 20.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2015
From: MATSUYAMA, HIROSHI; GOTO, RYOJI; ISHIKAWA, HIROYUKI; TAKAHASHI, KEITA; KATSUMATA, TAIJI
To: FUJIFILM CORPORATION
Reel/Frame 036834/0966 →
Priority Claims (2)
JP 2014-214782 · Oct 21, 2014 · national
JP 2015-149996 · Jul 29, 2015 · national
Continuity (1)
Related Publication 20160108315A1 · Apr 21, 2016