IP Library Granted Patent US 10,053,425
Granted Patent B2
US 10,053,425 · App. 15/034,809 · Granted Aug 21, 2018

Piperidine derivative, liquid crystal composition and liquid crystal display device

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Quick Facts
Patent No.
US 10,053,425
App. No.
15/034,809
Granted
Aug 21, 2018
Kind
B2
Abstract

To provide a compound having an effect for preventing photolysis of a liquid crystal composition, and having a high solubility in the liquid crystal composition, a liquid crystal composition containing the compound, and a liquid crystal display device including the composition. The compound is represented by formula (1), the liquid crystal composition contains the compound, and the liquid crystal display device includes the composition. 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-phenylene or the like; Z 1 , Z 2 and Z 3 are independently a single bond, alkylene or the like; and n is 0, 1 or 2.

Claims (52)

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 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2025
From: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
To: JIANGSU HECHENG DISPLAY TECHNOLOGY CO., LTD.
Reel/Frame 072472/0384 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2017
From: GOTOH, YASUYUKI; HIRATA, KENJI; MATSUKUMA, MAIKO; KANADANI, CHIKAHIDE
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 041425/0900 →