Optically anisotropic substance and liquid crystal display

Patent metadata

Field	Value
Publication number	US-9399736-B2
Application number	US-201414542957-A
Country	US
Kind code	B2
Filing date	Nov 17, 2014
Priority date	Nov 26, 2013
Publication date	Jul 26, 2016
Grant date	Jul 26, 2016

Abstract

To provide an optically anisotropic substance having a negative uniaxial phase difference film and a positive uniaxial phase difference film, and excellent heat resistance and sputtering resistance. The positive uniaxial phase difference film is formed in combination with a bifunctional polymerizable liquid crystal compound, the negative uniaxial phase difference film is formed in combination of the bifunctional polymerizable liquid crystal compound with an optically active compound having a polymerizable binaphthol moiety, and additional thermosetting treatment (postcure) is applied after the negative uniaxial phase difference film is photocured, and when glass transition temperature after the negative uniaxial phase difference film is cured is 85° C. or higher and 115° C. or lower, additional thermosetting treatment temperature is adjusted to 220° C. or higher and 250° C. or lower, and when the glass transition temperature is higher than 115° C., the additional thermosetting treatment temperature is adjusted to 200° C. or higher and 250° C. or lower.

First claim

What is claimed is:

1. An optically anisotropic substance in which an alignment film, a positive uniaxial phase difference film and a negative uniaxial phase difference film are formed on a substrate in the above order, wherein
the positive uniaxial phase difference film is formed of polymerizable liquid crystal composition (A) containing one kind or two or more kinds of achiral polymerizable liquid crystal compounds having two or more polymerizable groups,
the negative uniaxial phase difference film is formed of polymerizable liquid crystal composition (B) containing one kind or two or more kinds of achiral polymerizable liquid crystal compounds having two or more polymerizable groups, and one kind or two or more kinds of optically active compounds having a polymerizable binaphthol moiety, and
the optically anisotropic substance is formed according to an additional thermosetting treatment step after the negative uniaxial phase difference film is formed by photocuring, and
when a glass transition temperature after the negative uniaxial phase difference film is photocured is 85° C. or higher and 115° C. or lower, an additional thermosetting treatment temperature is adjusted to 220° C. or higher and 250° C. or lower, and when the glass transition temperature is higher than 115° C., the additional thermosetting treatment temperature is adjusted to 200° C. or higher and 250° C. or lower.

2. The optically anisotropic substance according to claim 1 , wherein polymerizable liquid crystal composition (A) contains one kind or two or more kinds of compounds selected from the group of achiral polymerizable liquid crystal compounds represented by formula (1) and formula (2):

wherein, in formula (1),
X 1 is independently hydrogen, methyl, fluorine or trifluoromethyl;
W 11 is independently hydrogen, fluorine, chlorine, methyl or ethyl, and at least one of hydrogen in the methyl and the ethyl may be replaced by halogen;
A 1 is independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one of hydrogen is replaced by halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons; and
Y 1 is independently a single bond or alkylene having 1 to 20 carbons, at least one of —CH 2 — may be replaced by —O—, —S—, —COO—, —OCO— or —OCOO—, excluding a case where —O— is adjacent, at least one of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one of hydrogen may be replaced by fluorine or chlorine; and
in formula (2),
X 2 is independently hydrogen, methyl, fluorine or trifluoromethyl;
W 21 is independently halogen, nitro, cyano, phenyl, benzyl, alkyl having 1 to 7 carbons, alkoxy having 1 to 7 carbons, alkoxycarbonyl (—COOR a ; R a is straight-chain alkyl having 1 to 7 carbons) or alkylcarbonyl (—COR b ; R b is straight-chain alkyl having 1 to 16 carbons), and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine;
W 22 is independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons, and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine;
s is an integer from 0 to 4;
n 21 is independently an integer from 2 to 12;
n 22 is an integer from 1 to 3;
Z 21 is independently a single bond, —O—, —CO—, —CH═CH—, —COO—, —OCO—, —OCO—CH═CH—COO— or —OCOO—; and
Z 22 is independently a single bond, —CH 2 CH 2 — or —CH═CH—.

3. The optically anisotropic substance according to claim 2 , wherein polymerizable liquid crystal composition (B) contains one kind or two or more kinds of compounds selected from the group of achiral polymerizable liquid crystal compounds represented by formula (1) and formula (2), and one kind or two or more kinds of optically active compounds having a polymerizable binaphthol moiety as represented by formula (3):

wherein, in formula (3),
Y 3 is independently hydrogen, halogen or a group represented by formula (3-1), however, at least two in Y 3 are a group represented by formula (3-1); and
in formula (3-1),
R 3 is independently halogen, cyano, alkenyl having 2 to 20 carbons or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the group may be replaced by —O—, excluding a case where —O— is adjacent, at least one of hydrogen in the group may be replaced by halogen, and in one or two of Y 3 , one of hydrogen in R 3 is replaced by acryloyloxy, methacryloyloxy or trifluoromethylacryloyloxy;
A 3 is independently 1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one of hydrogen is replaced by halogen;
Z 3 is independently a single bond, —O—, —COO—, —OCO—, —OCF 2 — or —(CH 2 ) p —, and one of —CH 2 — of —(CH 2 ) p — may be replaced by —O—;
p is independently an integer from 1 to 20; and
r is independently an integer from 1 to 3.

4. The optically anisotropic substance according to claim 3 , wherein polymerizable liquid crystal compound (1) contained in polymerizable liquid crystal composition (A) or polymerizable liquid crystal composition (B) includes at least one compound selected from the group of compounds represented by formula (1-1), and optically active compound (3) contained in polymerizable liquid crystal composition (B) includes at least one compound selected from the group of compounds represented by formula (3-2):

wherein, in formula (1-1),
X 1 is independently hydrogen, methyl, fluorine or trifluoromethyl;
W 11 is independently hydrogen or methyl;
W 12 is independently hydrogen, halogen, nitro, cyano, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons; and
n 11 is independently an integer from 2 to 12; and
in formula (3-2),
Y 3 is independently a group represented by formula (3-1); and
in formula (3-1),
R 3 is independently alkenyl having 2 to 20 carbons or alkyl having 1 to 20 carbons, at least one of —CH 2 — in the group may be replaced by —O—, excluding a case where —O— is adjacent, at least one of hydrogen in the group may be replaced by halogen, and in one or two of Y 3 , one of hydrogen in R 3 is replaced by acryloyloxy, methacryloyloxy or trifluoromethylacryloyloxy;
A 3 is independently 1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or 1,4-phenylene in which at least one of hydrogen is replaced by halogen;
Z 3 is independently a single bond, —O—, —COO—, —OCO—, —OCF 2 — or —(CH 2 ) p —, and one of —CH 2 — of —(CH 2 ) p — may be replaced by —O—;
p is independently an integer from 1 to 20; and
r is independently an integer from 1 to 3.

5. The optically anisotropic substance according to claim 4 , wherein, in formula (1-1),
X 1 is independently hydrogen or methyl; and
W 12 is independently hydrogen, halogen, alkyl having 1 to 7 carbons or alkoxy having 1 to 7 carbons; and
in formula (2),
X 2 is independently hydrogen or methyl;
W 21 is independently halogen, phenyl, benzyl, alkyl having 1 to 7 carbons, alkoxy having 1 to 7 carbons, alkoxycarbonyl (—COOR a ; R a is straight-chain alkyl having 1 to 7 carbons) or alkylcarbonyl (—COR b ; R b is straight-chain alkyl having 1 to 16 carbons), and in the alkyl and the alkoxy, at least one of hydrogen may be replaced by fluorine; and
in formula (3-2),
Y 3 is independently a group represented by formula (3-1); and
in formula (3-1),
R 3 is independently alkeny

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Hirai Yoshiharu
• Miyagawa Nagahisa
• Ootsuki Daisuke
• Tanabe Mayumi
• Nara Kazumi

Classifications

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• G02F2413/06

  Two plates on one side of the LC cell · CPC title

• G02F1/13363

  Birefringent elements, e.g. for optical compensation · CPC title

• C09K2019/548

  stabilizing the alignment; Polymer stabilized alignment · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title