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

Patent metadata

Field	Value
Publication number	US-9518222-B2
Application number	US-201514820229-A
Country	US
Kind code	B2
Filing date	Aug 6, 2015
Priority date	Aug 6, 2014
Publication date	Dec 13, 2016
Grant date	Dec 13, 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, large dielectric constant in a minor-axis direction, suitable elastic constant, excellent compatibility, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. The compound is represented by formula (1):

wherein, for example, R 1 is alkyl having 1 to 15 carbons, rings A 1 to A 4 are 1,4-cyclohexylene or 1,4-phenylene, at least one of Z 1 to Z 5 is —CF 2 O—, and X 1 is fluorine or —OCF 3 ;
W 1 is a group represented by formula (1a) or (1b);

wherein, Y 1 to Y 5 are fluorine;
W 2 is a group represented by formula (1c) or (1d);

wherein, L 1 to L 5 are fluorine; and a, b, c and d are independently 0 or 1.

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein, in formula (1),
R 1 is alkyl having 1 to 15 carbons, 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 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 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, chroman-2,6-diyl, 2,3-dihydro-1H-indene-2,5-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, and at least one of hydrogen directly bonded with the above rings may be 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 fluorine or chlorine, 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),
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),
when W 1 is represented by formula (1a) and W 2 is represented by formula (1c), at least one of ring A 1 , ring A 2 , ring A 3 and ring A 4 is naphthalene-2,6-diyl in which at least one of hydrogen may be replaced by halogen;
X 1 is fluorine, —C≡N, —N═C═S or alkyl having 1 to 10 carbons in which at least one of hydrogen is replaced by fluorine, alkenyl having 2 to 10 carbons in which at least one of hydrogen is replaced by fluorine, alkoxy having 1 to 9 carbons in which at least one of hydrogen was replaced by fluorine, or alkenyloxy having 2 to 9 carbons in which at least one of hydrogen is replaced by fluorine;
a, b, c and d are independently 0 or 1, and a sum of a, b, c and d is 0, 1, 2 or 3;
Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond or alkylene having 1-6 carbons, in the alkylene, at least one of —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, one or two of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one of hydrogen may be replaced by fluorine or chlorine; and
at least one of Z 1 in the case where a is 1, Z 2 in the case where b is 1, Z 3 in the case where c is 1, Z 4 in the case where d is 1, and Z 5 is —CF 2 O—.

2. The compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
R 1 is alkyl having 1 to 15 carbons, alkenyl having 2 to 15 carbons, alkoxy having 1 to 14 carbons or alkenyloxy having 2 to 14 carbons, and in the groups, at least one of hydrogen may be replaced by fluorine;
X 1 is fluorine, —C≡N, —N═C═S, —CHF, —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
Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —(CH 2 ) 2 COO—, —OCO(CH 2 ) 2 —, —(CH 2 ) 2 CF 2 O—, —OCF 2 (CH 2 ) 2 —, —(CH 2 ) 3 O— or —O(CH 2 ) 3 —.

3. The compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons, and in the groups, at least one of hydrogen may be replaced by fluorine; and
X 1 is fluorine, —C≡N, —CF 3 , —CHF 2 , —OCF 3 , —OCHF 2 , —CH═CHCF 3 , —CF═CHCF 3 or —CF═CFCF 3 .

4. The compound according to claim 1 , represented by any one of formulas (1-1) to (1-8):

wherein, in formulas (1-1) to (1-8),
R 1 is alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;
ring A 1 , ring A 2 , ring A 3 and ring A 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, or naphthalene-2,6-diyl in which at least one of hydrogen is replaced by fluorine;
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 fluorine, Y 3 , Y 4 and Y 5 are independently hydrogen or fluorine, and at least two of Y 3 , Y 4 and Y 5 is fluorine; and

in formulas (1-1) to (1-8),
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 or fluorine; and

in formulas (1-1) to (1-8),
when W 1 is represented by formula (1a) and W 2 is represented by formula (1c), at least one of ring A 1 , ring A 2 , ring A 3 and ring A 4 is naphthalene-2,6-diyl in which at least one of hydrogen may be replaced by halogen;
Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —CF═CF—, —C≡C—, —(CH 2 ) 2 COO—, —OCO(CH 2 ) 2 —, —(CH 2 ) 2 CF 2 O—, —OCF 2 (CH 2 ) 2 —, —(CH 2 ) 3 O— or —O(CH 2 ) 3 —, and at least one of Z 1 , Z 2 , Z 3 , Z 4 and Z 5 is —CF 2 O—; and
X 1 is fluorine, —CF 3 , —CHF 2 , —OCF 3 or —OCHF 2 .

5. The compound according to claim 1 , represented by any one of formulas (1-9) to (1-29):

wherein, in formulas (1-9) to (1-29),
R 1 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, or naphthalene-2,6-diyl in which at least one of hydrogen is replaced by fluorine;
Z 1 , Z 2 , Z 3 and Z 5 are independently a single bond, —(CH 2 ) 2 —, —(CH 2 ) 4 —, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, and at least one of Z 1 , Z 2 , Z 3 and Z 5 is —CF 2 O—;
X 1 is fluorine, —CF 3 or —OCF 3 ; and
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , L 8 , Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are independently hydrogen or fluorine.

6. The compound according to claim 1 , represented by any one of formulas (1-30) to (1-54):

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Goto Mayumi
• Tanaka Hiroyuki

Classifications

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07C255/54

  containing cyano groups and etherified hydroxy groups bound to the carbon skeleton · CPC title

• C09K19/3066

  in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C07C43/225

  containing halogen · CPC title