Liquid crystal compound, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9527870-B2
Application number	US-201514749158-A
Country	US
Kind code	B2
Filing date	Jun 24, 2015
Priority date	Jun 24, 2014
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

To provide a liquid crystal compound satisfying at least one physical property such as high stability to light, a high clearing point, low minimum temperature of a liquid-crystal phase, small viscosity, suitable optical anisotropy, large dielectric anisotropy, a large dielectric constant in a minor axis direction, a suitable elastic constant, excellent compatibility with other liquid crystal compounds. The compound is represented by formula (1-1):

for example, R is alkyl having 1 to 10 carbons or alkoxy having 1 to 9 carbons, rings A 1 to A 3 are 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced by halogen; X is halogen, —CF 3 or —OCF 3 ; l is 1, and m, n is 0 or 1; W 1 is a group represented by formula (1a) or (1b);

W 2 is a group represented by formula (1c) or (1d);

Y 1 to Y 2 are hydrogen, Y 3 to Y 5 and L 1 to L 5 are fluorine.

First claim

What is claimed is:

1. A compound represented by formula (1-1):

wherein, in formula (1-1),
R is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one of —CH 2 — may be replaced by —O— or —S—, at least one of —(CH 2 ) 2 — may be replaced by —CH═CH—, and in the groups, at least one of hydrogen may be replaced by halogen;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, or 1,4-phenylene in which at least one of hydrogen is replaced by halogen;
W 1 is a group represented by formula (1a) or formula (1b);

wherein, in formula (1a) and formula (1b),
Y 1 and Y 2 are independently hydrogen, chlorine or fluorine, Y 3 , Y 4 and Y 5 are independently hydrogen, fluorine or chlorine, and at least two of Y 3 , Y 4 and Y 5 is fluorine or chlorine; and

in formula (1-1),
W 2 is a group represented by formula (1c) or formula (1d);

wherein, in formula (1c) and formula (1d),
L 1 , L 2 , L 3 , L 4 and L 5 are independently hydrogen, fluorine or chlorine; and

in formula (1-1),
X is halogen, —C≡N, —N═C═S, —SF 5 , —CF 3 , —CF 2 H, —CFH 2 , —OCF 3 , —OCF 2 H, —OCFH 2 or alkyl having 1 to 10 carbons, and in the alkyl, at least one of —CH 2 — may be replaced by —O— or —S—, at least one of —(CH 2 ) 2 — may be replace by CH═CH—, and in the groups, at least one of hydrogen may be replaced by halogen; and
l, m and n are 0 or 1, and a sum of l, m and n is 0, 1 or 2;
in which, when a sum of l and m is 1 and n is 0, at least one of W 1 and W 2 is a group represented by formula (1b) or formula (1d), or at least one of l piece of ring A 1 and m pieces of ring A 2 is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 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.

2. The compound according to claim 1 , represented by formula (1-2):

wherein, in formula (1-2),
R is hydrogen, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene;
W 1 is a group represented by formula (1a) or formula (1b);

wherein, in formula (1a) and formula (1b),
Y 1 and Y 2 are independently hydrogen, chlorine or fluorine, Y 3 , Y 4 and Y 5 are independently hydrogen, fluorine or chlorine, and at least two of Y 3 , Y 4 and Y 5 is fluorine or chlorine; and

in formula (1-2),
W 2 is a group represented by formula (1c) or formula (1d);

wherein, in formula (1c) and formula (1d),
L 1 , L 2 , L 3 , L 4 and L 5 are independently hydrogen, fluorine or chlorine; and

in formula (1-2),
X is fluorine, chlorine, —C≡N, —N═C═S, —SF 5 , —CH 2 F, —CHF 2 , —CF 3 , —(CH 2 ) 2 —F, —CH 2 CF 3 , —CF 2 CF 3 , —(CH 2 ) 3 —F, —(CH 2 ) 2 —CF 3 , —(CF 2 ) 3 —F, —(CH 2 ) 4 —F, —(CH 2 ) 3 —CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —(CF 2 ) 6 —F, —(CF 2 ) 7 —F, —OCH 2 F, —OCHF 2 , —OCF 3 , —O—(CH 2 ) 2 —F, —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CH 2 ) 3 —F, —O—(CH 2 ) 2 —CF 3 , —O—(CF 2 ) 3 —F, —O(CH 2 ) 4 —F, —O—(CH 2 ) 3 —CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —O—(CF 2 ) 6 —F, —CH═CHF, —CH═CF 2 , —CF═CHF, —CH═CHCH 2 F, —CH═C—CF═CF 2 HCF 3 , —CF═CHCF 3 , —CF═CFCF 3 , —(CH 2 ) 2 —CH═CF 2 , —(CH 2 ) 2 —CF═CF 2 , —(CH 2 ) 2 —CH═CHCF 3 , —(CH 2 ) 2 —CF═CHCF 3 or —(CH 2 ) 2 —CF═CFCF 3 ; and
l and m are 0 or 1, and a sum of l and m is 0, 1 or 2;
in which, when a sum of l and m is 1, at least one of W 1 and W 2 is a group represented by formula (1b) or formula (1d), or at least one of ring A 1 and ring A 2 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene.

3. The compound according to claim 1 , represented by formula (1-3):

wherein, in formula (1-3),
R is hydrogen, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons or alkenyloxy having 2 to 9 carbons;
ring A 1 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene; ring A 3 is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,3-dioxane-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 3,5-difluoro-1,4-phenylene;
W 1 is a group represented by formula (1a) or formula (1b);

wherein, in formula (1a) and formula (1b),
Y 1 and Y 2 are independently hydrogen, chlorine or fluorine, Y 3 , Y 4 and Y 5 are independently hydrogen, fluorine or chlorine, and at least two of Y 3 , Y 4 and Y 5 is fluorine or chlorine; and

in formula (1-3),
W 2 is a group represented by formula (1c) or formula (1d);

wherein, in formula (1c) and formula (1d),
L 1 , L 2 , L 3 , L 4 and L 5 are independently hydrogen, fluorine or chlorine; and

in formula (1-3),
X is fluorine, chlorine, —C≡N, —N═C═S, —SF 5 , —CH 2 F, —CHF 2 , —CF 3 , —(CH 2 ) 2 —F, —CH 2 CF 3 , —CF 2 CF 3 , —(CH 2 ) 3 —F, —(CH 2 ) 2 —CF 3 , —(CF 2 ) 3 —F, —(CH 2 ) 4 —F, —(CH 2 ) 3 —CF 3 , —(CF 2 ) 4 —F, —(CF 2 ) 5 —F, —(CF 2 ) 6 —F, —(CF 2 ) 7 —F, —OCH 2 F, —OCHF 2 , —OCF 3 , —O—(CH 2 ) 2 —F, —OCH 2 CF 3 , —OCF 2 CF 3 , —O—(CH 2 ) 3 —F, —O—(CH 2 ) 2 —CF 3 , —O—(CF 2 ) 3 —F, —O(CH 2 ) 4 —F, —O—(CH 2 ) 3 —CF 3 , —O—(CF 2 ) 4 —F, —O—(CF 2 ) 5 —F, —O—(CF 2 ) 6 —F, —CH═CHF, —CH═CF 2 , —CF═CHF, —CF═CF 2 , —CH═CHCH 2 F, —CH═CHCF 3 , —CF═CHCF 3 , —CF═CFCF 3 , —(CH 2 ) 2 —CH═CF 2 , —(CH 2 ) 2 —CF═CF 2 , —(CH 2 ) 2 —CH═CHCF 3 , —(CH 2 ) 2 —CF═CHCF 3 or —(CH 2 ) 2 —CF═CFCF 3 ; and
l and n are 0 or 1, and a sum of l and n is 0, 1 or 2.

4. The compound according to claim 1 , represented by formula (1-4):

wherein, in formula (1-4),
R is hydrog

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Gotoh Yasuyuki
• Kobayashi Masahide

Classifications

• C09K19/3458

  Uncondensed pyrimidines · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C07C25/24

  Halogenated aromatic hydrocarbons with unsaturated side chains · CPC title

• C07C255/50

  to carbon atoms of non-condensed six-membered aromatic rings · CPC title

• C09K2019/326

  containing a decahydronaphthalene, e.g. -2,6-diyl (decalin) · CPC title