IP Library Granted Patent US 9,994,770
Granted Patent B2
US 9,994,770 · App. 15/453,627 · Granted Jun 12, 2018

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

Inventors: Hiroyuki Tanaka (Ichihara, JP); Akihiro Takata (Ichihara, JP)
Assignees: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
C09K19/3402C09K19/3001C09K19/3003C09K19/3068C09K2019/301C09K2019/3004C09K2019/3006C09K2019/308C09K2019/3009C09K2019/3016C09K2019/3071C09K2019/3077C09K2019/3083C09K2019/3422
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Quick Facts
Patent No.
US 9,994,770
App. No.
15/453,627
Granted
Jun 12, 2018
Kind
B2
Abstract

Provided is a liquid crystal compound satisfying at least one of physical properties such as high stability to heat and light, a high clearing point (or high maximum temperature), low minimum temperature of a liquid crystal phase, small viscosity, suitable optical anisotropy, large dielectric anisotropy, a suitable elastic constant and excellent compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound and a liquid crystal display device including the composition. A compound, represented by formula (1): wherein, in formula (1), R 1 is alkoxy having 1 to 9 carbons or the like; R 2 is alkenyl having 2 to 10 carbons; Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH— or the like; and a and b are independently 0 or 1.

Claims (64)

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

wherein, in formula (1),

R 1 is a group in which at least one —CH 2 — of alkyl having 1 to 10 carbons is replaced by —O—, and in the group, at least one —CH 2 CH 2 — may be replaced by —CH═CH—, and at least one hydrogen may be replaced by fluorine;

R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine or chlorine;

Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —OCH 2 —, —CH 2 O—, —C≡C—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CF 2 CF 2 —, —CF═CF—, —(CH 2 ) 4 —, —CH═CH—(CH 2 ) 2 — or —(CH 2 ) 2 —CH═CH—; and

a and b are independently 0 or 1.

2. The compound according to claim 1 , wherein, in formula (1),

R 1 is alkoxy having 1 to 9 carbons, alkoxyalkyl having 1 to 9 carbons, alkenyloxy having 2 to 9 carbons or alkenyloxyalkyl having 2 to 9 carbons, and in the groups, at least one hydrogen may be replaced by fluorine;

R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine;

Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —OCH 2 — or —CH 2 O—; and

a and b are independently 0 or 1.

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

wherein, in formulas (1-1) to (1-4),

R 1 is alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons, and in the groups, at least one hydrogen may be replaced by fluorine;

R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine; and

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

4. The compound according to claim 1 , represented by any one of formulas (1-5) to (1-10):

wherein, in formulas (1-15) to (1-22), R 3 is alkyl having 1 to 9 carbons.

5. The compound according to claim 1 , represented by any one of formulas (1-11) to (1-14):

wherein, in formulas (1-11) to (1-14),

R 1 is alkoxy having 1 to 9 carbons; and

R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine.

6. The compound according to claim 1 , represented by any one of formulas (1-15) to (1-22):

Z 11 , Z 12 and Z 13 are independently a single bond, —COO—, —CH 2 CH 2 —, —CH═CH— or —C≡C—; and

in formula (3), when all of ring B 1 , ring B 2 and ring B 3 are 1,4-cyclohexylene, R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the monovalent groups, at least one hydrogen may be replaced by fluorine; and

in formula (4), when all of ring B 1 , ring B 2 , ring B 3 and ring B 4 are 1,4-cyclohexylene, R 11 and R 12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the monovalent groups, at least one hydrogen may be replaced by fluorine.

7. The compound according to claim 1 , represented by any one of formulas (1-23) to (1-26):

wherein, in formulas (1-23) to (1-26), R 3 is alkyl having 1 to 6 carbons.

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

9. The liquid crystal composition according to claim 8 , 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 groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, 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

wherein, in formulas (1-5) to (1-10),

R 1 is alkoxy having 1 to 9 carbons or alkenyloxy having 2 to 9 carbons; and

R 2 is alkenyl having 2 to 10 carbons, and in the group, at least one hydrogen bonding with carbon forming a double bond may be replaced by fluorine.

10. The liquid crystal composition according to claim 8 , 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 groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, 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 , ring C 2 and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is 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, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —(CH 2 ) 4 —; and

L 11 and L 12 are independently hydrogen or fluorine.

11. The liquid crystal composition according to claim 8 , 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 groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, 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, 1,4-phenylene in which at least one hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 17 is a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 — or —C≡C—;

L 13 and L 14 are independently hydrogen or fluorine; and

i is 1, 2, 3 or 4.

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

wherein, in formulas (9) to (15),

R 15 and R 16 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the groups, at least one —CH 2 — may be replaced by —O—, and in the monovalent groups, at least one hydrogen may be replaced by fluorine;

R 17 is hydrogen, fluorine, 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 in the monovalent groups, at least one hydrogen may be replaced by fluorine;

ring E 1 , ring E 2 , ring E 3 and ring E 4 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 or decahydronaphthalene-2,6-diyl;

ring E 5 and ring E 6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;

Z 18 , Z 19 , Z 20 and Z 21 are independently a single bond, —COO—, —OCO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 OCH 2 CH 2 — or —OCF 2 CH 2 CH 2 —;

L 15 and L 16 are independently fluorine or chlorine;

S 11 is hydrogen or methyl;

X is —CHF— or —CF 2 —; and

j, k, m, n, p, q, r and s are independently 0 or 1, a sum of k, m, n and p is 1 or 2, a sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3.

13. The liquid crystal composition according to claim 8 , further containing at least one additive selected from the group 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, a dye and an antifoaming agent.

14. A liquid crystal display device, wherein the device comprises the liquid crystal composition according to claim 8 .

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 072472/0393 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2017
From: TANAKA, HIROYUKI; TAKATA, AKIHIRO
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 042356/0628 →
Priority Claims (1)
JP 2016-046832 · Mar 10, 2016 · national
Continuity (1)
Related Publication 20170260453A1 · Sep 14, 2017