Liquid crystal compound having a 3,6-dihydro-2H-pyran ring, negative dielectric anisotropy, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-9790427-B2
Application number	US-201615015955-A
Country	US
Kind code	B2
Filing date	Feb 4, 2016
Priority date	Feb 6, 2015
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

A liquid crystal compound is provided that satisfies at least one physical property, such as high stability to heat and light, a high clearing point (or high maximum temperature), a low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, a suitable elastic constant and good compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound, and a liquid crystal display device including the composition. The liquid crystal compound is represented by formula (1):

in which, R a and R b are alkyl having 1 to 10 carbons; ring A 1 , ring A 2 and ring A 3 are 1,4-cyclohexylene, 1,4-phenylene; and ring N 1 is 2,3-difluoro-1,4-phenylene; G is a divalent group represented by formula (pr-1) or (pr-2);

in which, Z 1 , Z 2 , Z 3 and Z 4 are a single bond; and a, b and c are 0, 1 or 2.

First claim

What is claimed is:

1. A compound represented by formula (1):

wherein, in formula (1),
R a and R b are independently hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one —CH 2 — may be replaced by —O— or —S—, —CO— or —SiH 2 —, at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine, and R b may be fluorine, chlorine, —C≡N or —C≡C—C≡N;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, decahydronaphthalene-2,6-diyl or 1,4-phenylene, and in the groups, at least one —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —CH═N—, and in the divalent groups, at least one hydrogen may be replaced by fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F; and
ring N 1 is 1,4-cyclohexylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, 1,4-phenylene, naphthalene-2,6-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 9H-xanthene-2,6-diyl or 9H-fluorene-2,7-diyl, and in the groups, at least one —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —CH═N—, and in the divalent groups, at least one hydrogen may be replaced by fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F;
G is a divalent group represented by formula (pr-1) or (pr-2);

wherein,
Z 1 and Z 2 are independently a single bond or alkylene having 1 to 6 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, one or two pieces of —CH 2 CH 2 — may be replaced by —C≡C—, and in the divalent groups, at least one hydrogen may be replaced by fluorine or chlorine;
Z 3 and Z 4 are independently a single bond or alkylene having 1 to 6 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, one or two pieces of —CH 2 CH 2 — may be replaced by —CH═CH— or —C≡C—, and in the divalent groups, at least one hydrogen may be replaced by fluorine or chlorine;
a, b and c are independently 0, 1 or 2, and a sum of a, b and c is an integer from 0 to 3;
when R a is —C 3 H 7 , R b is —OC 2 H 5 , a is 1, b and c are 0, ring A 1 is tetrahydropyran-2,5-diyl, Z 1 and Z 3 are a single bond and ring N 1 is 2,3-difluoro-1,4-phenylene, G is a divalent group represented by formula (pr-2);
when R a is —C 5 H 11 , R b is —OC 2 H 5 , a, b and c are 0, Z 3 is a single bond and ring N 1 is 2,3-difluoro-1,4-phenylene, G is a divalent group represented by formula (pr-2); and
when R a is —CH═CH 2 or —C 2 H 5 , R b is —OC 2 H 5 , a, b and c are 0, Z 3 is a single bond and ring N 1 is 2,3-difluoro-1,4-phenylene, G is a divalent group represented by formula (pr-1).

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

wherein, in formula (1-1),
R a and R b are independently hydrogen or alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons or alkenyloxy having 2 to 9 carbons, and R b may be fluorine, chlorine, —C≡N, —C≡C—C≡N, alkyl having 1 to 10 carbons in which at least one hydrogen is replaced by fluorine, or chlorine or alkoxy having 1 to 9 carbons in which at least one hydrogen is replaced by fluorine or chlorine;
ring A 1 , ring A 2 and ring A 3 are independently 1,4-cyclohexylene, decahydronaphthalene-2,6-diyl or 1,4-phenylene, and in the groups, at least one —CH 2 — may be replaced by —O—, —S—, —CO— or —SiH 2 —, at least one —CH 2 CH 2 — may be replaced by —CH═CH— or —CH═N—, and in the divalent groups, at least one hydrogen may be replaced by fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F;
G is a divalent group represented by formula (pr-1) or (pr-2);

wherein,
Z 1 , Z 2 , Z 3 and Z 4 are independently a single bond, —COO—, —COO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —CH 2 CH 2 —;
L 1 and L 2 are independently fluorine, chlorine, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 or —OCH 2 F;
a, b and c are independently 0, 1 or 2, and a sum of a, b and c is 0, 1 or 2;
when R a is —C 3 H 7 , R b is —OC 2 H 5 , a is 1, b and c are 0, ring A 1 is tetrahydropyran-2,5-diyl, Z 1 and Z 3 are a single bond and L 1 and L 2 are fluorine, G is a divalent group represented by formula (pr-2);
when R a is —C 5 H 11 , R b is —OC 2 H 5 , a, b and c are 0, Z 3 is a single bond and L 1 and L 2 are fluorine, G is a divalent group represented by formula (pr-2); and
when R a is —CH═CH 2 or —C 2 H 5 , R b is —OC 2 H 5 , a, b and c are 0, Z 3 is a single bond and L 1 and L 2 are fluorine, G is a divalent group represented by formula (pr-1).

3. The compound according to claim 1 , represented by formulas (1-2) or (1-3):

wherein, in formula (1-2) or (1-3),
R a and R b are independently hydrogen or alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons or alkenyloxy having 2 to 9 carbons;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 2,3-difluoro-1,4-phenylene;
G is a divalent group represented by formula (pr-1) or (pr-2);

wherein,
Z 1 , Z 2 and Z 3 are independently a single bond, —COO—, —COO—, —CH 2 O—, —OCH 2 — or —CH 2 CH 2 —.

4. The compound according to claim 1 , represented by any one of formulas (1-2-1) to (1-2-6) and formulas (1-3-1) to (1-3-6):

wherein, in formulas (1-2-1) to (1-2-6) and formulas (1-3-1) to (1-3-6),
R a and R b are independently hydrogen or alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons or alkenyloxy having 2 to 9 carbons.

5. The compound according to claim 4 , wherein, in formulas (1-2-1) to (1-2-6) and formulas (1-3-1) to (1-3-6) described in claim 4 , R a is alkyl having 1 to 10 carbons, and R b is alkoxy having carbons 1 to 9.

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

wherein, in formula (1-4),
R a and R b are independently hydrogen or alkyl having 1 to 10 carbons, alkoxy having carbons 1 to 9, alkoxyalkyl having 2 to 9 carbons, alkenyl having 2 to 10 carbons or alkenyloxy having carbons 2 to 9;
G is a divalent group represented by formula (pr-1) or (pr-2);

wherein,
Z 3 is a single bond, —COO—, —COO—, —CH 2 O—, —OCH 2 — or —CH 2 CH 2 —;
when R a is —C 5 H 11 , R b is —OC 2 H 5 and Z 3 is a single bond, G is a divalent group represented by formula (pr-2); and
when R a is —CH═CH 2 or —C 2 H 5 , R b is —O

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Satou Teizi
• TACHINAMI Sakura

Classifications

• C07D309/22

  Radicals substituted by oxygen atoms · CPC title

• C07F7/0896

  Compounds with a Si-H linkage · CPC title

• C09K2019/3422

  the heterocyclic ring being a six-membered ring · CPC title

• C07D407/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K19/3458 Primary

  Uncondensed pyrimidines · CPC title