Piperidine derivative, liquid crystal composition and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-10053425-B2
Application number	US-201415034809-A
Country	US
Kind code	B2
Filing date	Oct 29, 2014
Priority date	Nov 19, 2013
Publication date	Aug 21, 2018
Grant date	Aug 21, 2018

Abstract

In formula (1), R1, R2, R3 and R4 are independently hydrogen or alkyl having 1 to 4 carbons; ring A1 and ring A2 are independently 1,4-cyclohexylene, 1,4-phenylene or the like; Z1, Z2 and Z3 are independently a single bond, alkylene or the like; and n is 0, 1 or 2.

First claim

What is claimed is:

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

wherein, in formula (1),
R 1 , R 2 , R 3 and R 4 are independently hydrogen or alkyl having 1 to 4 carbons;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, decahydronaphthalene-2,6-diyl, dihydropyrane-2,5-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl or pyridine-2,5-diyl, and in the rings, at least one piece of hydrogen may be replaced by halogen, alkyl having 1 to 5 carbons, alkoxy having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one piece of hydrogen is replaced by halogen;
Z 1 and Z 3 are independently a single bond, —O—, or alkylene having 2 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, at least one —CH 2 —CH 2 — may be replaced by —CH═CH— or —CH≡CH—, and at least one hydrogen may be replaced by fluorine,
Z 2 is a single bond, or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, at least one —CH 2 —CH 2 — may be replaced by —CH═CH— or —CH≡CH—, and at least one hydrogen may be replaced by fluorine; and
n is 0, 1 or 2.

2. The compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
R 1 , R 2 , R 3 and R 4 are independently hydrogen or alkyl having 1 to 4 carbons;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, pyridine-2,5-diyl, 1,3-dioxane-2,5-diyl, naphthalene-2,6-diyl, naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine, or decahydronaphthalene-2,6-diyl;
Z 1 and Z 3 are independently a single bond, —O—, or alkylene having 2 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O— and at least one —CH 2 —CH 2 — may be replaced by —CH═CH—,
Z 2 is a single bond, or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, at least one —CH 2 —CH 2 — may be replaced by —CH═CH—; and
n is 0, 1 or 2.

3. The compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
R 1 , R 2 , R 3 and R 4 are independently alkyl having 1 to 4 carbons;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, naphthalene-2,6-diyl, or naphthalene-2,6-diyl in which at least one hydrogen is replaced by fluorine;
Z 1 and Z 3 are independently a single bond, —O—, or alkylene having 2 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O— and at least one —CH 2 —CH 2 — may be replaced by —CH═CH—,
Z 2 is a single bond, or alkylene having 1 to 10 carbons, and in the alkylene, at least one —CH 2 — may be replaced by —O—, at least on —CH 2 —CH 2 — may be replaced by —CH═CH—; and
n is 0, 1 or 2.

4. The compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
R 1 , R 2 , R 3 and R 4 are methyl;
ring A 1 and ring A 2 are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one-hydrogen is replaced by fluorine;
Z 1 and Z 3 are single bonds, and Z 2 is a single bond, —CH 2 —, —CH 2 CH 2 —, —CH═CH—, —OCH 2 — or —CH 2 O—; and
n is 0 or 1.

5. The compound according to claim 1 , wherein, in formula (1) described in claim 1 ,
R 1 , R 2 , R 3 and R 4 are methyl;
ring A 1 and ring A 2 are independently 1,4-phenylene or 2-fluoro-1,4-phenylene;
Z 1 , Z 2 and Z 3 are single bonds; and
n is 0 or 1.

6. A liquid crystal composition, containing at least one compound according to claim 1 .

7. The liquid crystal composition according to claim 6 , further containing at least one compound selected from the group of compounds represented by formulas (2) to (4):

wherein, in formulas (2) to (4),
R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl or the alkenyl, at least one —CH 2 — may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;
ring B 1 , ring B 2 , ring B 3 and ring B 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; and
Z 11 , Z 12 and Z 13 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —COO—.

8. The liquid crystal composition according to claim 6 , further containing at least one compound selected from the group of compounds represented by formulas (5) to (7):

wherein, in formulas (5) to (7),
R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one —CH 2 — may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;
X 11 is fluorine, chlorine, —OCF 3 , —OCHF 2 , —CF 3 , —CHF 2 , —CH 2 F, —OCF 2 CHF 2 or —OCF 2 CHFCF 3 ;
ring C 1 , C 2 and C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;
Z 14 , Z 15 and Z 16 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —(CH 2 ) 4 —; and
L 11 and L 12 are independently hydrogen or fluorine.

9. The liquid crystal composition according to claim 6 , further containing at least one compound selected from the group of compounds represented by formula (8):

wherein, in formula (8),
R 14 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one —CH 2 — may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;
X 12 is —C≡N or —C≡C—C≡N;
ring D 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;
Z 17 is a single bond, —CH 2 CH 2 —, —C≡C—, —COO—, —CF 2 O—, —OCF 2 — or —CH 2 O—;
L 13 and L 14 are independently hydrogen or fluorine; and
i is 1, 2, 3 or 4.

10. The liquid crystal composition according to claim 6 , further containing at least one of a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent.

11. A liquid crystal display device, including at least one liquid crystal composition according to claim 6 .

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Gotoh Yasuyuki
• Hirata Kenji
• MATSUKUMA Maiko
• Kanadani Chikahide

Classifications

• C09K19/44

  containing compounds with benzene rings directly linked · CPC title

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C07D211/12 Primary

  with only hydrogen atoms attached to the ring nitrogen atom · CPC title

• C09K19/3483

  the heterocyclic ring being a non-aromatic ring · CPC title