Antioxidant having difluoromethoxy group, liquid crystal composition, and liquid crystal display device

Patent metadata

Field	Value
Publication number	US-2016130501-A1
Application number	US-201514934155-A
Country	US
Kind code	A1
Filing date	Nov 6, 2015
Priority date	Nov 10, 2014
Publication date	May 12, 2016
Grant date	—

Abstract

[Subject] One object of the invention is a compound useful as an antioxidant. Other objects include a liquid crystal composition having high stability to ultraviolet light and heat, and a device that hardly undergoes a decrease in voltage holding ratio even after a long-time use.
[Solution] The invention relates to a compound represented by formula (1), a liquid crystal composition to which the compound is added, and a liquid crystal display device containing the composition.

In formula (1), R 1 is hydrogen or alkyl having 1 to 20 carbons, or the like; R 2 and R 3 are independently methyl, ethyl, isopropyl, or t-butyl; ring A is 1,4-cyclohexylene, 1,4-phenylene or the like; Z is a single bond or alkylene having 1 to 6 carbons, or the like; and m is 0, 1, or 2.

First claim

1 . A compound represented by formula (1),

wherein in formula (1), R 1 is hydrogen or alkyl having 1 to 20 carbons, wherein at least one —CH 2 — in the alkyl is optionally replaced with —O—, —S—, —CO—, or —SiH 2 —, and at least one —CH 2 CH 2 — in the alkyl is optionally replaced with —CH═CH— or —C≡C—; R 2 and R 3 are independently methyl, ethyl, isopropyl, or t-butyl; ring A is 1,4-cyclohexylene, 1,4-cyclohexenylene, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,4-phenylene, or naphthalene-2,6-diyl, wherein at least one —CH 2 — in these groups is optionally replaced with —O—, —S—, —CO—, or —SiH 2 —, at least one —CH 2 CH 2 — in these groups is optionally replaced with —CH═CH— or —CH═N—, and at least one hydrogen in these divalent groups is optionally replaced with fluorine, chlorine, —C≡N, —CF 3 , —CHF 2 , —CH 2 F, —OCF 3 , —OCHF 2 , or —OCH 2 F; Z is a single bond or alkylene having 1 to 6 carbons, wherein at least one —CH 2 — in the alkylene is optionally replaced with —O—, —S—, —CO—, or —SiH 2 —, one or two —CH 2 CH 2 — in the alkylene are optionally replaced with —CH═CH— or —C═=—C—, and at least one hydrogen in these divalent groups is optionally replaced with fluorine or chlorine; and m is 0, 1, or 2, wherein when m=2, two rings A may be the same or different, and two Z's may be the same or different.

2 . The compound of claim 1 , wherein in formula (1), R 1 is hydrogen or alkyl having 1 to 20 carbons, wherein at least one —CH 2 — in the alkyl is optionally replaced with —O— or —S—; R 2 and R 3 are independently methyl, ethyl, isopropyl, or t-butyl; ring A is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced with fluorine or chlorine; Z is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF═CF—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CHF—, —CH 2 S—, or —SCH 2 —; and m is 0, 1, or 2, wherein when m=2, two rings A may be the same or different, and two Z's may be the same or different.

3 . The compound of claim 1 , wherein in formula (1), R 1 is alkyl having 2 to 20 carbons; R 2 and R 3 are independently methyl, ethyl, isopropyl, or t-butyl; ring A is 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is replaced with fluorine; Z is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CH 2 O—, or —OCH 2 —; and m is 1 or 2, wherein when m=2, two rings A may be the same or different, and two Z's may be the same or different.

4 . The compound of claim 1 , represented by formulae (1-1-a) to (1-1-e),

wherein in formulae (1-1-a) to (1-1-e), R 1 is alkyl having 2 to 20 carbons; R 2 and R 3 are independently methyl, ethyl, isopropyl, or t-butyl; Z is a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, —COO—, —OCO—, —CH 2 O—, or —OCH 2 —; and L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , and L 8 are independently hydrogen or fluorine.

5 . The compound of claim 1 , represented by formulae (1-2-a) to (1-2-e),

wherein in formulae (1-2-a) to (1-2-e), R 1 is alkyl having 2 to 20 carbons; R 2 and R 3 are independently methyl, ethyl, isopropyl, or t-butyl; and L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , and L 8 are independently hydrogen or fluorine.

6 . The compound of claim 5 , wherein in formulae (1-2-a) to (1-2-e), R 1 is alkyl having 2 to 15 carbons; R 2 and R 3 are independently methyl or t-butyl; and L 1 , L 2 , L 3 , L 4 , L 5 , L 6 , L 7 , and L 8 are independently hydrogen or fluorine, wherein a total amount of fluorine is an integer of 0 to 4.

7 . The compound of claim 1 , represented by formulae (1-3-a) to (1-3-1),

wherein in formulae (1-3-a) to (1-3-1), R 4 is alkyl having 2 to 9 carbons.

8 . A liquid crystal composition, containing the compound of claim 1 .

9 . The liquid crystal composition of claim 8 , further containing at least one compound selected from the group consisting of compounds represented by formulae (2) to (4),

wherein in formulae (2) to (4),
R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl or alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl or alkenyl is optionally replaced with 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-phenyl ene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; and
Z 11 , X 12 , and Z 13 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C—, or —COO—.

10 . The liquid crystal composition of claim 8 , further containing at least one compound selected from the group consisting of compounds represented by formulae (5) to (7),

wherein in formulae (5) to (7),
R 13 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, wherein at least one —CH 2 — in the alkyl and alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl and alkenyl is optionally replaced with 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 , ring C 2 and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen is optionally replaced with 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.

11 . The liquid crystal composition of claim 8 , further containing at least one compound selected from the group consisting 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, wherein at least one —CH 2 — in the alkyl and alkenyl is optionally replaced with —O—, and at least one hydrogen in the alkyl and alkenyl is optionally replaced with 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 is optionally replaced with 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.

12 . The liquid crystal composition of claim 8 , further containing at least one compound selected from the group consisting of compounds represented by formulae (9) to (15),

wherein in formulae (9) to (15),
R 15 and R 16 a

Assignees

• Jnc Corp
• Jnc Petrochemical Corp

Inventors

• Gotoh Yasuyuki
• Satou Teizi

Classifications

• C07C323/17

  having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C07C69/94

  of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C323/20

  with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title

• C09K2019/3425

  Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title