Composition for forming liquid crystal layer, liquid crystal display device, and method for producing liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9644146-B2
Application number	US-201113821412-A
Country	US
Kind code	B2
Filing date	Jul 14, 2011
Priority date	Sep 7, 2010
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

The present invention provides a composition for forming a liquid crystal layer which enables to achieve takt time reduction and high display quality. The liquid crystal display device according to the present invention includes a liquid crystal material, and a monomer, the monomer being a compound having a structure that generates ketyl radicals when undergoing a hydrogen abstraction reaction caused by exposure to light.

First claim

The invention claimed is:

1. A composition for forming a liquid crystal layer comprising:
a liquid crystal material; and
a first compound,
the first compound having a structure that generates ketyl radicals when undergoing a hydrogen abstraction reaction caused by exposure to light,
wherein the first compound is represented by the following chemical formula (1):

wherein A 1 and A 2 are each independently a benzene ring, a biphenyl ring, or a C1-C12 linear or branched alkyl or alkenyl group;
one of A 1 and A 2 is a benzene ring or a biphenyl ring;
at least one of A 1 and A 2 includes a -Sp 1 —P 1 group;
a hydrogen atom in A 1 and A 2 may be replaced by a -Sp 1 —P 1 group, a halogen atom, a —CN group, a —NO 2 group, a —NCO group, a —NCS group, a —OCN group, a —SCN group, a —SF 5 group, or a C1-C12 linear or branched alkyl, alkenyl, or aralkyl group;
two adjacent hydrogen atoms in A 1 or A 2 may be substituted with a C1-C12 linear or branched alkylene or alkenylene group to form a ring structure;
a hydrogen atom in the alkyl, alkenyl, alkylene, alkenylene, or aralkyl group of A 1 and A 2 may be replaced by a -Sp 1 —P 1 group;
a —CH 2 — group in the alkyl, alkenyl, alkylene, alkenylene, or aralkyl group of A 1 and A 2 may be substituted with an —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —O—COO— group, a —OCH 2 — group, a —CH 2 O— group, a —SCH 2 — group, —CH 2 S— group, —N(CH 3 )— group, a —N(C 2 H 5 )— group, a —N(C 3 H 7 )— group, a —N(C 4 H 9 )— group, a —CF 2 O— group, a —OCF 2 — group, a —CF 2 S— group, a —SCF 2 — group, a —N(CF 3 )— group, a —CH 2 CH 2 — group, a —CF 2 CH 2 — group, a —CH 2 CF 2 — group, a —CF 2 CF 2 — group, a —CH═CH— group, a —CF═CF— group, a —C≡C— group, a —CH═CH—COO— group, or a —OCO—CH═CH— group, provided that oxygen atoms, sulfur atoms and nitrogen atoms are mutually apart;
P 1 is a polymerizable group;
Sp 1 is a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond;
m is 1 or 2;
a dotted line connecting A 1 and Y, and a dotted line connecting A 2 and Y show an optional bond between A 1 and A 2 mediated by Y;
Y is a —CH 2 — group, a —CH 2 CH 2 — group, a —CH═CH— group, a —O— group, a —S— group, a —NH— group, a —N(CH 3 )— group, a —N(C 2 H 5 )— group, a —N(C 3 H 7 )— group, a —N(C 4 H 9 )— group, a —OCH 2 — group, a —CH 2 O— group, a —SCH 2 — group, a —CH 2 S— group, or a direct bond;
the composition further comprising a second compound that contains a monofunctional or polyfunctional polymerizable group having a ring structure;
wherein the second compound that contains a monofunctional or polyfunctional polymerizable group having a ring structure, is represented by the following formula (3):
P 2 —S p 2 —R 4 —A 3 —(Z—A 4 ) n —R 3   (3)

wherein R 3 is a —R 4 —Sp 2 —P 2 group, a hydrogen atom, a halogen atom, a —CN group, a —NO 2 group, a —NCO group, a —NCS group, an —OCN group, a —SCN group, a —SF 5 group, or a C1-C12 linear or branched alkyl group;
P 2 is a polymerizable group;
Sp 2 is a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond;
a hydrogen atom in R 3 may be replaced by a fluorine atom or a chlorine atom;
a —CH 2 — group in R 3 may be substituted with an —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —O—COO— group, a —OCH 2 — group, a —CH 2 O— group, a —SCH 2 — group, a —CH 2 S— group, a —N(CH 3 )— group, a —N(C 2 H 5 )— group, a —N(C 3 H 7 )— group, a —N(C 4 H 9 )— group, a —CF 2 O— group, a —OCF 2 — group, a —CF 2 S— group, a —SCF 2 — group, a —N(CF 3 )— group, a —CH 2 CH 2 — group, a —CF 2 CH 2 — group, a —CH 2 CF 2 — group, a —CF 2 CF 2 — group, a —CH=CH— group, a —CF=CF— group, a —C≡C— group, a —CH=CH—COO— group, or a —OCO—CH=CH— group, provided that oxygen atoms, and sulfur atoms are mutually apart;
R 4 is a —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —O—COO— group, a —OCH 2 — group, a —CH 2 O— group, a —SCH 2 — group, a —CH 2 S— group, a —N(CH 3 )— group, a —N(C 2 H 5 )— group, a —N(C 3 H 7 )— group, a —N(C 4 H 9 )— group, a —CF 2 O— group, a —OCF 2 — group, a —CF 2 S— group, a —SCF 2 group, a —N(CF 3 )— group, a —CH 2 CH 2 — group, a —CF 2 CH 2 — group, a —CH 2 CF 2 — group, a —CF 2 CF 2 — group, a —CH=CH— group, a —CF=CF— group, a —C≡C— group, a —CH=CH—COO— group, a —OCO— CH=CH— group, or a direct bond;
A 3 and A 4 are each independently a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a naphthalene-1, 4-diyl group, a naphthalene-1,5-diyl group, a naphthalene-2,6-diyl group, a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group, a 1,4-bicyclo[2.2.2]octylene group, a piperidine-1,4-diyl group, a naphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, an indane-1,3-diyl group, an indane-1,5-diyl group, an indane-2,5-diyl group, a phenanthrene-1,6-diyl group, a phenanthrene-1,8-diyl group, a phenanthrene-2,7-diyl group, a phenanthrene-3,6-diyl group, an anthracene-1,5-diyl group, an anthracene-1,8-diyl group, an anthracene-2,6-diyl group, or an anthracene-2,7-diyl group;
—CH 2 — groups in A 3 and A 4 may be substituted with —O— groups or —S— groups, provided that they are mutually apart;
a hydrogen atom in A 3 and A 4 may be replaced by a fluorine atom, a chlorine atom, a —CN group, or a C1-C6 alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy group;
Z is a —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —O—COO— group, a —OCH 2 — group, a —CH 2 O— group, a —SCH 2 — group, a —CH 2 S— group, a —N(CH 3 )— group, a —N(C 2 H 5 )— group, a —N(C 3 H 7 )— group, a —N(C 4 H 9 )— group, a —CF 2 O— group, a —OCF 2 — group, a —CF 2 S— group, a —SCF 2 — group, a —N(CF 3 )— group, a —CH 2 CH 2 — group, a —CF 2 CH 2 — group, a —CH 2 CF 2 — group, a —CF 2 CF 2 — group, a —CH=CH— group, a —CF=CF— group, a —C≡C— group, a —CH=CH—COO— group, a —OCO—CH=CH— group, or a direct bond; and n is 0, 1, or 2.

2. The composition for forming a liquid crystal layer according to claim 1 , wherein the m is 1.

3. The composition for forming a liquid crystal layer according to claim 2 , wherein the first compound has any of structure represented by the following formulae (2-1) to (2-6):

wherein R 1 and R 2 are each independently a -Sp 1 —P 1 group, a hydrogen atom, a halogen atom, a —CN group, a —NO 2 group, a —NCO group, a —NCS group, a —OCN group, a —SCN group, a —SF 5 group, or a C1-C12 linear or branched alkyl, aralkyl, or phenyl group;
at least one of R 1 and R 2 includes a -Sp 1 —P 1 group;
P 1 is a polymerizable group;
Sp 1 is a C1-C6 linear, branched, or cyclic alkylene or alkyleneoxy group, or a direct bond;
a hydrogen atom in at least one of R 1 and R 2 , when the at least one of R 1 and R 2 is a C1-C12 linear or branched alkyl, aralkyl, or phenyl group, may be replaced by a fluorine atom, a chlorine atom, or a -Sp 1 —P 1 group; and
a —CH 2 — group in R 1 and R 2 may be substituted with an —O— group, a —S— group, a —NH— group, a —CO— group, a —COO— group, a —OCO— group, a —O—COO— group, a —OCH 2 — group, a —CH 2 O— group, a —SCH 2 — group, a —CH 2 S— group, a —N(CH 3 )— group, a —N(C 2 H 5 )— group, a —N(C 3 H 7 )— group, a —N(C 4 H 9 )— group, a —CF 2 O— group, a —OCF 2 — group, a —CF 2 S— group, a —SCF 2 — group, a —N(CF 3 )— group, a —CH 2 CH 2 — group, a —CF 2 CH 2 — group, a —CH 2 CF 2 — group, a —CF 2 CF 2 — group, a —CH═CH— group, a —CF═CF— group, a —C≡C— group, a —CH═CH—COO— group, or a —OCO—CH═CH— group, provided t

Assignees

• Mizusaki Masanobu
• Yamada Yuichiro
• Enomoto Satoshi
• Hara Yuki
• Kikuchi Hideo
• Sharp Kk
• Toyo Gosei Co Ltd

Inventors

• Mizusaki Masanobu
• Yamada Yuichiro
• Enomoto Satoshi
• Hara Yuki
• Kikuchi Hideo

Classifications

• G02F2001/133726

  Physics · mapped topic

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title

• G02F1/133365

  Cells in which the active layer comprises a liquid crystalline polymer · CPC title

• C08F220/30

  containing aromatic rings in the alcohol moiety · CPC title