Optically anisotropic film, optical film, polarizing plate, and image display device

Patent metadata

Field	Value
Publication number	US-11370970-B2
Application number	US-202016991202-A
Country	US
Kind code	B2
Filing date	Aug 12, 2020
Priority date	Feb 14, 2018
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

Provided are an optically anisotropic film which has excellent moisture-heat resistance and can have a reduction in the thickness, an optical film, a polarizing plate, and an image display device. The optically anisotropic film is obtained by polymerizing a polymerizable liquid crystal composition, in which the polymerizable liquid crystal composition contains a polymerizable liquid crystal compound represented by Formula (1): L1-SP1-(E3-A1)m-E1-G1-D1-Ar1-D2-G2-E2-(A2-E4)n-SP2-L2 and a polymerizable liquid crystal compound represented by Formula (2): L1-SP1-(E3-A1)m-E1-G1-D1-Ar2-D2-G2-E2-(A2-E4)n-SP2-L2, and the optically anisotropic film satisfies Formula (3): Re(450)/Re(550)<1 or Formula (4): Rth(450)/Rth(550)<1, and has a degree of alignment as measured by Raman spectroscopy of 0.4 or more.

First claim

What is claimed is:

1. An optically anisotropic film obtained by polymerizing a polymerizable liquid crystal composition,
wherein the polymerizable liquid crystal composition contains a polymerizable liquid crystal compound represented by Formula (1) and a polymerizable liquid crystal compound represented by Formula (2), and
the optically anisotropic film satisfies Formula (3) or (4) and has a degree of alignment of 0.4 or more as measured by Raman spectroscopy,
L 1 -SP 1 -(E 3 -A 1 ) m -E 1 -G 1 -D 1 -Ar 1 -D 2 -G 2 -E 2 -(A 2 -E 4 ) n -SP 2 -L 2   (1)

L 1 -SP 1 -(E 3 -A 1 ) m -E 1 -G 1 -D 1 -Ar 2 -D 2 -G 2 -E 2 -(A 2 -E 4 ) n -SP 2 -L 2   (2)

Re (450)/ Re (550)<1  (3)

Rth (450)/ Rth (550)<1  (4)

in Formulae (1) and (2), D 1 , D 2 , E 1 , E 2 , E 3 , and E 4 each independently represent a single bond, —CO—O—, —C(═S)O—, —CR 1 R 2 —, —CR 1 R 2 —CR 3 R 4 —, —O—CR 1 R 2 —, —CR 1 R 2 —O—CR 3 R 4 —, —CO—O—CR 1 R 2 —, —O—CO—CR 1 R 2 —, —CR 1 R 2 —O—CO—CR 3 R 4 —, —CR 1 R 2 —CO—O—CR 3 R 4 —, —NR 1 —CR 2 R 3 —, or —CO—NR 1 —, where R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms,
G 1 and G 2 each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, which may have a substituent, and one or more of —CH 2 —'s constituting the alicyclic hydrocarbon group may be substituted with —O—, —S—, or —NH,
A 1 and A 2 each independently represent a divalent aromatic hydrocarbon group having 6 to 12 carbon atoms or a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, each of which may have a substituent, and one or more of —CH 2 —'s constituting the alicyclic hydrocarbon group may be substituted with —O—, —S—, or —NH—,
SP 1 and SP 2 each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group in which one or more of —CH 2 —'s constituting the linear or branched alkylene group having 1 to 12 carbon atoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—, and Q represents a substituent,
L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 or L 2 represents a polymerizable group, provided that in a case where Ar 1 or Ar 2 is an aromatic ring represented by Formula (Ar-3), at least one of L 1 or L 2 , or L 3 or L 4 in Formula (Ar-3) represents a polymerizable group,
m represents an integer of 0 to 2, and in a case where m is 2, a plurality of E 3 's may be the same as or different from each other and a plurality of A 1 's may be the same as or different from each other,
n represents an integer of 0 to 2, and in a case where n is 2, a plurality of E 4 's may be the same as or different from each other and a plurality of A 2 's may be the same as or different from each other, and
Ar 1 represents any aromatic ring selected from the group consisting of the groups represented by Formulae (Ar-1) to (Ar-5), and Ar 2 represents any aromatic ring selected from the group consisting of the groups represented by Formulae (Ar-1) to (Ar-6),

in Formulae (Ar-1) to (Ar-6), * represents a bonding position to D 1 or D 2 ,
Q 1 represents N or CH,
Q 2 represents —S—, —O—, or —N(R 5 )—, where R 5 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms, each of which may have a substituent,
Z 1 , Z 2 , Z 3 , Z 4 and each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, —OR 6 , —NR 7 R 8 , or —SR 9 , R 6 to R 9 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 may be bonded to each other to form an aromatic ring, provided that at least one of Z 1 or Z 2 in Ar 1 represents a group having a van der Waals volume of 0.3×10 2 Å 3 or more, and Z 1 , Z 2 , Z 3 , and Z 4 in Ar 2 each represent a group having a van der Waals volume of less than 0.3×10 2 Å 3 ,
A 3 and A 4 each independently represent a group selected from the group consisting of —O—, —N(R 10 )—, —S—, and —CO—, where R 10 represents a hydrogen atom or a substituent,
X represents a non-metal atom of Groups XIV to XVI to which a hydrogen atom or a substituent may be bonded,
D 3 and D 4 each independently represent a single bond, —CO—O—, —C(═S)O—, —CR 1 R 2 —, —CR 1 R 2 —CR 3 R 4 —, —O—CR 1 R 2 —, —CR 1 R 2 —O—CR 3 R 4 —, —CO—O—CR 1 R 2 —, —O—CO—CR 1 R 2 —, —CR 1 R 2 —O—CO—CR 3 R 4 —, —CR 1 R 2 —CO—O—CR 3 R 4 —, —NR 1 —CR 2 R 3 —, or —CO—NR 1 —, where R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms,
SP 3 and SP 4 each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group in which one or more of —CH 2 —'s constituting the linear or branched alkylene group having 1 to 12 carbon atoms are substituted with —O—, —S—, —NH—, —N(Q)-, or —CO—, and Q represents a substituent,
L 3 and L 4 each independently represent a monovalent organic group, and at least one of L 3 or L 4 , or L 1 or L 2 in Formula (1) or (2) represents a polymerizable group,
Ax represents an organic group having 2 to 30 carbon atoms, which has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring,
Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, which may have a substituent, or an organic group having 2 to 30 carbon atoms, which has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring,
the aromatic ring in each of Ax and Ay may have a substituent, and Ax and Ay may be bonded to each other to form a ring,
Q 3 represents a hydrogen atom, or an alkyl group having 1 to 6 carbon atoms, which may have a substituent,
in Formula (3), Re(450) represents an in-plane retardation of the optically anisotropic film at a wavelength of 450 nm, and Re(550) represents an in-plane retardation of the optically anisotropic film at a wavelength of 550 nm, and
in Formula (4), Rth(450) represents a thickness-direction retardation of the optically anisotropic film at a wavelength of 450 nm, and Rth(550) represents a thickness-direction retardation of the optically anisotropic film at a wavelength of 550 nm.

2. The optically anisotropic film according to claim 1 ,
wherein in Formula (1), m is 1, A 1 and G 1 are both a cyclohexylene group which may have a substituent, and E 1 is a single bond, and
in Formula (1), n is 1, A 2 and G 2 are both a cyclohexylene group which may have a substituent, and E 2 is a single bond.

3. The optically anisotropic film according to claim 1 ,
wherein Ar 1 in Formula (1) and Ar 2 in Formula (2) both represent a group represented by Formula (Ar-1) or (Ar-2).

4. The optically anisotropic film according to claim 1 ,
wherein the total number of the rings represented by G 1 , G 2 , A 1 , and A 2 in Formula (1) is the same as the total number of the rings represented by G 1 , G 2 , A 1 , and A 2 in Formula (2).

5. The optically anisotropic film according to claim 1 ,
wherein an I/O val

Assignees

• Fujifilm Corp

Inventors

• Muramatsu Ayako
• Satake Ryo
• Nojiri Mayumi
• Yoshida Aiko
• Takahashi Keita

Classifications

• H10K59/8794

  Arrangements for heating and cooling · CPC title

• H10K59/8793

  Arrangements for polarized light emission (H10K59/8791 takes precedence) · CPC title

• H10K59/8722

  Peripheral sealing arrangements, e.g. adhesives, sealants · CPC title

• C09K19/3861 Primary

  containing condensed ring systems · CPC title

• C09K19/02 Primary

  characterised by optical, electrical or physical properties of the components, in general · CPC title