Monomer, liquid crystal composition, liquid crystal display device, and production method for liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9719018-B2
Application number	US-201314436514-A
Country	US
Kind code	B2
Filing date	Oct 17, 2013
Priority date	Oct 19, 2012
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

The present invention provides a liquid crystal composition for forming a polymer layer capable of keeping high voltage holding ratio. The liquid crystal composition in an aspect of the present invention contains a liquid crystal material and one or more kind monomers and, at least one of the monomers is a compound produced by further bonding a hydrocarbon group with 12 carbon atoms or more to a compound produced by bonding two polymerizable groups to a cyclic aliphatic compound or aromatic compound with 6 carbon atoms or more.

First claim

The invention claimed is:

1. A liquid crystal composition comprising a liquid crystal material and one or more kinds of monomers,
the one or more monomers including:
a first monomer produced by further bonding a hydrocarbon group with 12 carbon atoms or more to a compound produced by bonding two polymerizable groups to a cyclic aliphatic compound or aromatic compound with 6 carbon atoms or more; and
a second monomer having a structure for producing a radical by light irradiation; wherein
the first monomer produced by further bonding a hydrocarbon group with 12 carbon atoms or more to a compound produced by bonding two polymerizable groups to the cyclic aliphatic compound or aromatic compound with 6 carbon atoms or more is a compound represented by the following formula (2):

in the formula,
P and P are the same or different, and denote a (meth)acryloyloxy, (meth)acryloylamino, vinyl, or vinyloxy group;
A 3 denotes a trivalent, alicyclic, aromatic monocyclic, or condensed polycyclic hydrocarbon group;
the trivalent, alicyclic, aromatic monocyclic, or condensed polycyclic hydrocarbon group is selected from the group consisting of benzene-1,2,3-triyl, benzene-1,2,4-triyl, benzene-1,3,5-triyl, pyridine-2,3,4-triyl, pyridine-2,3,5-triyl, pyridine-2,4,6-triyl, naphthalene-1,2,5-triyl, naphthalene-1,2,6-triyl, naphthalene-1,2,7-triyl, naphthalene-1,2,8-triyl, naphthalene-1,3,5-triyl, naphthalene-1,3,6-triyl, naphthalene-1,3,7-triyl, naphthalene-1,3,8-triyl, naphthalene-1,4,5-triyl, naphthalene-1,4,6-triyl, naphthalene-1,4,7-triyl, naphthalene-1,6,7-triyl, naphthalene-1,6,8-triyl, naphthalene-2,3,6-triyl, cyclohexane-1,2,3-triyl, cyclohexane-1,2,4-triyl, cyclohexane-1,3,5-triyl, decahydronaphthalene-1,2,5-triyl, decahydronaphthalene-1,2,6-triyl, decahydronaphthalene-1,2,7-triyl, decahydronaphthalene-1,2,8-triyl, decahydronaphthalene-1,3,5-triyl, decahydronaphthalene-1,3,6-triyl, decahydronaphthalene-1,3,7-triyl, decahydronaphthalene-1,3,8-triyl, decahydronaphthalene-1,4,5-triyl, decahydronaphthalene-1,4,6-triyl, decahydronaphthalene-1,4,7-triyl, decahydronaphthalene-1,6,7-triyl, decahydronaphthalene-1,6,8-triyl, decahydronaphthalene-2,3,6-triyl, indan-1,1,5-triyl, indan-1,1,6-triyl, indan-1,3,5-triyl, indan-1,3,6-triyl, phenanthrene-1,2,6-triyl, phenanthrene-1,2,7-triyl, phenanthrene-1,2,8-triyl, phenanthrene-1,2,9-triyl, phenanthrene-1,3,6-triyl, phenanthrene-1,3,7-triyl, phenanthrene-1,3,8-triyl, phenanthrene-1,3,9-triyl, phenanthrene-1,6,7-triyl, phenanthrene-1,6,9-triyl, phenanthrene-1,7,9-triyl, phenanthrene-1,8,9-triyl, phenanthrene-1,9,10-triyl, phenanthrene-2,3,6-triyl, phenanthrene-2,3,7-triyl, phenanthrene-2,3,9-triyl, phenanthrene-2,7,9-triyl, phenanthrene-2,9,10-triyl, phenanthrene-3,6,7-triyl, phenanthrene-3,6,9-triyl, phenanthrene-3,9,10-triyl, anthracene-1,2,5-triyl, anthracene-1,2,6-triyl, anthracene-1,2,7-triyl, anthracene-1,2,8-triyl, anthracene-1,2,9-triyl, anthracene-1,2,10-triyl, anthracene-1,3,5-triyl, anthracene-1,3,6-triyl, anthracene-1,3,7-triyl, anthracene-1,3,8-triyl, anthracene-1,3,9-triyl, anthracene-1,3,10-triyl, anthracene-1,4,5-triyl, anthracene-1,4,6-triyl, anthracene-1,4,8-triyl, anthracene-1,4,9-triyl, anthracene-1,5,9-triyl, anthracene-1,6,7-triyl, anthracene-1,6,9-triyl, anthracene-1,7,9-triyl, anthracene-1,8,9-triyl, anthracene-1,9,10-triyl, anthracene-2,3,6-triyl, anthracene-2,3,9-triyl, anthracene-2,6,9-triyl, anthracene-2,7,9-triyl, anthracene-2,7,10-triyl, and anthracene-2,9,10-triyl group;
A 4 denotes a phenylene group;
a —CH 2 — group included in A 3 and A 4 may be substituted with an —O— or a —S— group unless neighboring each other;
a —CH═ group included in A 3 and A 4 may be substituted with a —N═ group unless neighboring each other;
a hydrogen atom included in A 3 and A 4 may be substituted with a fluorine atom, a chlorine atom, a —CN group, or a straight or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy group with 1 to 12 carbon atoms and further one or more of carbon atoms in these groups may be substituted with a silicon atom;
Z 4 and Z 5 may be same or different, and denote —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —NHCO—, —N(CH 3 )CO—, —N(C 2 H 5 )CO—, —N(C 3 H 7 )CO—, —N(C 4 H 9 )CO—, —CONH—, —CON(CH 3 )—, —CON(C 2 H 5 )—, —CON(C 3 H 7 )—, —CON(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— group, or a direct bond;
L 3 denotes an alkyl, alkenyl, or aralkyl with 12 carbon atoms or more, or a monovalent monocyclic or polycyclic hydrocarbon group with 12 carbon atoms or more, or a biphenyl group; the alkyl and alkenyl groups may be straight or branched; one or more hydrogen atoms included in the aralkyl and the monovalent monocyclic or polycyclic hydrocarbon groups may be substituted with a straight or branched alkyl or alkenyl group with 1 to 8 carbon atoms;
a —CH 2 — group included in the alkyl, the alkenyl, and the monovalent monocyclic or polycyclic hydrocarbon group for L 3 may be substituted with —O—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group unless oxygen atoms neighbor each other; and
n 3 denotes 0 or 1;
the second monomer having a structure for producing a radical by light irradiation is at least one of: a compound represented by the following formula (4) and having a structure for producing a radical by hydrogen abstraction reaction by light irradiation, and a compound represented by the following formula (5) and having a structure for producing a radical by self-cleavage reaction by light irradiation;
the formula (4) being:

in the formula,
A 5 denotes an aromatic ring;
A 6 denotes an aromatic ring same as or different from A 5 , or a straight or branched alkyl or alkenyl group with 1 to 12 carbon atoms;
at least one of A 5 and A 6 contains -Sp 3 -P group;
an aromatic ring included in at least one of A 5 and A 6 is a benzene ring or a biphenyl ring;
a hydrogen atom included in A 5 and A 6 may be substituted with -Sp 3 -P group, a halogen atom, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —SF 5 , or an alkyl, alkenyl or aralkyl group with 1 to 12 carbon atoms and the alkyl and alkenyl groups may be straight or branched;
two neighboring hydrogen atoms included in A 5 and A 6 may be substituted with a straight or branched alkylene or alkenylene group with 1 to 12 carbon atoms to form a ring structure;
a hydrogen atom included in the alkyl, the alkenyl, the alkylene, the alkenylene or the aralkyl group of A 5 and A 6 may be substituted with -Sp 3 -P group;
a —CH 2 — group included in the alkyl, the alkenyl, the alkylene, the alkenylene or the aralkyl group of A 5 and A 6 may be substituted with —O—, —S—, —NH—, —CO—, —COO—, —OCO—, —O—COO—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 H 7 )—, —N(C 4 H 9 )—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —N(CF 3 )—, —CH 2 CH 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, or —OCO—CH═CH— group unless an oxygen atom, a sulfur atom, and a nitrogen atom neighbor one another;
P denotes a radical polymerizable group;
Sp 3 denotes a straight, branched or cyclic alkylene or alkyleneoxy group with 1 to 6 carbon atoms, or a direct bond;
m 1 denotes 1 or 2;
a dotted line part connecting A 5 and Y and a dotted line part connecting A 6 and Y represent that a bond through Y may exist between A 5 and A 6 ; and
Y denotes —CH 2 —, —CH 2 CH 2 —, —CH═CH—, —O—, —S—, —NH—, —N(CH 3 )—, —N(C 2 H 5 )—, —N(C 3 F

Assignees

• Sharp Kk
• Toyo Gosei Co Ltd

Inventors

• Mizusaki Masanobu
• Nakanishi Youhei
• Noma Takeshi
• Enomoto Satoshi

Classifications

• C09K19/56 Primary

  Aligning agents · CPC title

• G02F1/133788

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

• C09K19/2028

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3 · CPC title

• C09K3/10

  {Materials in mouldable or extrudable form} for sealing or packing joints or covers (filling pastes C09D5/34) · CPC title

• C07J17/00

  Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton (cardanolide, bufanolide C07J19/00) · CPC title