IP Library › Granted Patent US 12,492,342
Granted Patent B2
US 12,492,342 · App. 18/974,743 · Granted Dec 9, 2025

Liquid crystal composition and element

Inventors: Eiji Okabe (Chiba, JP); Takanori Mori (Chiba, JP); Kazushi Shiren (Chiba, JP); Yuko Katano (Chiba, JP); Yujiro Oguchi (Chiba, JP)
Assignees: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
C09K19/18C09K19/063C09K19/12C09K19/586G02F1/0063H01Q1/36H01Q15/0066C09K2019/123C09K2019/124C09K2019/181C09K2019/183C09K2019/185C09K2019/188
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Quick Facts
Patent No.
US 12,492,342
App. No.
18/974,743
Granted
Dec 9, 2025
Kind
B2
Abstract

A liquid crystal composition contains at least one compound selected from compounds represented by Formula (1), at least one compound selected from compounds represented by Formula (2), at least one compound selected from compounds represented by Formula (3), and at least one compound selected from compounds represented by Formula (4), and does not contain a compound represented by Formula(S).

Claims (76)

1 . A liquid crystal composition which comprises at least one compound selected from compounds represented by Formula (1), at least one compound selected from compounds represented by Formula (2), at least one compound selected from compounds represented by Formula (3), and at least one compound selected from compounds represented by Formula (4), and does not comprise a compound represented by Formula(S),

in Formula (1) to Formula (4),

R 1 , R 2 , R 3 , and R 4 are hydrogen, a halogen, or C1-12 linear alkyl in which at least one —CH 2 — may be substituted with —O— or —S—, at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—, and at least one hydrogen in these groups may be substituted with a halogen;

L 11 , L 12 , L 13 , L 21 , L 22 , L 23 , L 31 , L 32 , L 33 , L 41 , L 42 , L 43 , L 44 , and L 45 are hydrogen, a halogen, C1-3 alkyl, or C3-5 cycloalkyl;

Y 11 , Y 21 , Y 22 , Y 23 , Y 31 , Y 32 , Y 33 , Y 34 , Y 35 , Y 36 , and Y 41 are hydrogen or a halogen;

wherein at least one of L 11 , L 12 , and L 13 is C1-3 alkyl, at least one of L 31 , L 32 , and L 33 is C1-3 alkyl, and at least two of L 41, L 42, L 43, L 44, L 45, and Y 41 are not hydrogen,

in Formula(S),

R S1 is hydrogen, a halogen, or C1-12 alkyl in which at least one —CH 2 — may be substituted with —O— or —S—, at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—, and at least one hydrogen in these groups may be substituted with a halogen;

L S1 , L S2 , and L S3 are hydrogen or fluorine; and

Y S1 is hydrogen or fluorine.

2 . The liquid crystal composition according to claim 1 , which does not comprise a compound represented by Formula (T),

in Formula (T),

R T1 is hydrogen, a halogen, or C1-12 alkyl in which at least one —CH 2 — may be substituted with —O— or —S—, at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—, and at least one hydrogen in these groups may be substituted with a halogen;

Y T1 and Y T2 are hydrogen or fluorine; and

t is 0 or 1.

3 . The liquid crystal composition according to claim 1 , comprising, as the compound represented by Formula (1), at least one compound selected from a group of compounds represented by Formula (1-1) to Formula (1-10),

in Formula (1-1) to Formula (1-10),

R 1′ is C1-12 linear alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—.

4 . The liquid crystal composition according to claim 1 , comprising, as the compound represented by Formula (2), at least one compound selected from a group of compounds represented by Formula (2-1) to Formula (2-10),

in Formula (2-1) to Formula (2-10),

R 2′ is C1-12 linear alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—;

Y 22′ is hydrogen, fluorine, or chlorine; and

in Formula (2-10),

Y 21′ is hydrogen, fluorine, or chlorine.

5 . The liquid crystal composition according to claim 1 , comprising, as the compound represented by Formula (3), at least one compound selected from a group of compounds represented by Formula (3-1) to Formula (3-11),

in Formula (3-1) to Formula (3-11),

R 3′ is C1-12 linear alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—; and

Y 35′ is hydrogen, fluorine, or chlorine.

6 . The liquid crystal composition according to claim 1 , comprising, as the compound represented by Formula (4), at least one compound selected from a group of compounds represented by Formula (4-1) to Formula (4-7),

in Formula (4-1) to Formula (4-7),

R 4′ is C1-12 linear alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—;

L 44′ and L 45′ are hydrogen, fluorine, chlorine, methyl, or ethyl; and

Y 41′ is hydrogen, fluorine, or chlorine,

in Formula (4-1), Formula (4-6), and Formula (4-7),

at least one of L 44′ , L 45 ′, and Y 41 ′ is not hydrogen.

7 . The liquid crystal composition according to claim 1 , wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (1) is in a range from 15 weight % to 65 weight %, a proportion of the compound represented by Formula (2) is in a range from 5 weight % to 40 weight %, a proportion of the compound represented by Formula (3) is in a range from 10 weight % to 55 weight %, a proportion of the compound represented by Formula (4) is in a range from 5 weight % to 20 weight %.

8 . The liquid crystal composition according to claim 1 , further comprising at least one compound selected from compounds represented by Formula (5), compounds represented by Formula (6), and compounds represented by Formula (7),

in Formula (5) to Formula (7),

R 5 , R 6 , R 71 , and R 72 are hydrogen, a halogen, or C1-12 alkyl in which at least one —CH 2 — may be substituted with —O— or —S—, at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—, and at least one hydrogen in these groups may be substituted with a halogen;

L 51 , L 52 , L 53 , L 61 , L 62 , L 63 , L 64 , L 71 , L 72 , L 73 , L 74 , L 75 , L 76 , and L 77 are hydrogen, a halogen, C1-3 alkyl, or C3-5 cycloalkyl;

Y 51 , Y 52 , and Y 61 are hydrogen or a halogen;

a ring A is 1,4-cyclohexylene, 1,4-cyclohexenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one hydrogen on these rings may be substituted with a halogen or C1-3 alkyl;

Z 61 and Z 62 are a single bond, —C≡C—, or —C≡C—C≡C—; and

a is 0, 1, or 2, b is 1, 2, or 3, a+b is 3, c and d are 0 or 1, and e is 0, 1, or 2.

9 . The liquid crystal composition according to claim 8 , comprising, as the compound represented by Formula (5), at least one compound selected from a group of compounds represented by Formula (5-1) to Formula (5-10),

in Formula (5-1) to Formula (5-10),

R 5′ is C1-12 alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—; and

Y 51′ is hydrogen, fluorine, or chlorine.

10 . The liquid crystal composition according to claim 8 , comprising, as the compound represented by Formula (6), at least one compound selected from a group of compounds represented by Formula (6-1) to Formula (6-8),

in Formula (6-1) to Formula (6-8),

R 6′ is C1-12 alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—;

L 61′ , L 62′ , L 63′ , and L 64′ are hydrogen, fluorine, chlorine, methyl, or ethyl; and

Y 61′ is hydrogen, fluorine, or chlorine.

11 . The liquid crystal composition according to claim 8 , comprising, as the compound represented by Formula (7), at least one compound selected from a group of compounds represented by Formula (7-1) to Formula (7-6),

in Formula (7-1) to Formula (7-6),

R 71′ and R 72′ are C1-12 alkyl in which at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—;

in Formula (7-1) and Formula (7-2),

L 75′ , L 76′ , and L 77′ are hydrogen, fluorine, chlorine, methyl, or ethyl;

in Formula (7-3),

L 72′ , L 74′ , L 75′ , L 76′ , and L 77′ are hydrogen, fluorine, chlorine, methyl, or ethyl;

in Formula (7-4),

L 71′ , L 73′ , L 75′ , L 76′ , and L 77′ are hydrogen, fluorine, chlorine, methyl, or ethyl; and

in Formula (7-5) and Formula (7-6),

L 71′ , L 72′ , L 73′ , L 74′ , L 75′ , L 76′ , and L 77′ are hydrogen, fluorine, chlorine, methyl, or ethyl.

12 . The liquid crystal composition according to claim 8 , wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (5) is in a range from 0 weight % to 30 weight %, a proportion of the compound represented by Formula (6) is in a range from 0 weight % to 25 weight %, a proportion of the compound represented by Formula (7) is in a range from 0 weight % to 50 weight %, and a total proportion of these compounds is in a range from 5 weight % to 50 weight %.

13 . The liquid crystal composition according to claim 1 , wherein a refractive index anisotropy at 25° C. at a wavelength of 589 nm is 0.40 or more.

14 . The liquid crystal composition according to claim 1 , wherein a dielectric anisotropy at 25° C. at a frequency of 1 kHz is 10 or more.

15 . The liquid crystal composition according to claim 1 , wherein a dielectric anisotropy at 25° C. at at least one frequency from 1 GHz to 10 THz is in a range from 1.0 to 3.0.

16 . The liquid crystal composition according to claim 1 , comprising an optically active compound.

17 . The liquid crystal composition according to claim 1 , comprising a polymerizable compound.

18 . The liquid crystal composition according to claim 1 , comprising at least one of an antioxidant, an ultraviolet absorber, an antistatic agent, and a dichroic dye.

19 . An element comprising the liquid crystal composition according to claim 1 , wherein the element is used for switching and is capable of reversibly controlling a dielectric constant by reversibly changing an orientation direction of liquid crystal molecules.

20 . An element comprising the liquid crystal composition according to claim 1 , wherein the element is used for controlling electromagnetic waves in a frequency range from 1 GHz to 10 THz.

21 . A liquid crystal lens comprising the liquid crystal composition according to claim 1 .

22 . A birefringent lens for stereoscopic image display, comprising the liquid crystal composition according to claim 1 .

23 . A light modulator comprising the liquid crystal composition according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2024
From: OKABE, EIJI; MORI, TAKANORI; SHIREN, KAZUSHI; KATANO, YUKO; OGUCHI, YUJIRO
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 069560/0061 →
Priority Claims (2)
JP 2024-029705 · Feb 29, 2024 · national
JP 2024-184926 · Oct 21, 2024 · national
Continuity (1)
Related Publication 20250277151A1 · Sep 4, 2025
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