IP Library › Granted Patent US 12,655,351
Granted Patent B2
US 12,655,351 · App. 19/289,125 · Granted Jun 16, 2026

Liquid crystalline compound, 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); Kosuke Mine (Chiba, JP)
Assignees: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
C09K19/3059C07C331/28C09K19/3001G02B30/28C07B2200/13C07C2601/14C09K2019/3065
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Quick Facts
Patent No.
US 12,655,351
App. No.
19/289,125
Granted
Jun 16, 2026
Kind
B2
Abstract

A compound is represented by Formula (1). For example, R 1 is alkyl having 1 to 12 carbon atoms; L 1 is fluorine; L 2 is hydrogen; L 3 is fluorine; L 4 is methyl; Y 1 is hydrogen; Y 2 is hydrogen; and n is 0.

Claims (41)

1 . A liquid crystalline compound, represented by Formula (1),

wherein in Formula (1),

R 1 is hydrogen, halogen, or alkyl having 1 to 12 carbon atoms, wherein, in the alkyl, 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—, wherein at least one hydrogen in the alkyl may be substituted with halogen;

L 1 , L 2 , L 3 , and L 4 are hydrogen, fluorine, chlorine, methyl, or ethyl;

Y 1 and Y 2 are hydrogen, fluorine, or chlorine; and

n is 0 or 1,

with the proviso that when n is 0, L 1 , L 2 , L 3 , and L 4 are not selected such that any two of L 1 , L 2 , L 3 , and L 4 are methyl and the remaining two are hydrogen, fluorine, chlorine, or ethyl.

2 . The liquid crystalline compound according to claim 1 , wherein the compound represented by Formula (1) is represented by any one of Formula (1-1) to Formula (1-18),

in Formula (1-1) to Formula (1-18),

R 1′ is alkyl having 1 to 12 carbon atoms, wherein, in the alkyl, 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—, wherein at least one hydrogen in the alkyl may be substituted with halogen;

L 1′ is fluorine or methyl, and L 2′ is hydrogen, fluorine, or methyl; and

Y 1′ is hydrogen or fluorine,

with the proviso that in Formula (1-1) Formula (1-2), Formula (1-5), Formula (1-6), and Formula (1-9), L 1′ and L 2′ are not simultaneously methyl; and

with the proviso that in Formula (1-3), Formula (1-4), Formula (1-7), and Formula (1-8), L 1′ and L 2′ are not selected such that only one of L 1′ and L 2′ is methyl.

3 . A liquid crystal composition comprising at least one liquid crystalline compound according to claim 1 .

4 . The liquid crystal composition according to claim 3 , further comprising at least one compound selected from compounds represented by Formula (2) and Formula (3),

wherein in Formula (2) and Formula (3),

R 2 and R 3 are hydrogen, halogen, or linear alkyl having 1 to 12 carbon atoms, wherein, in the linear alkyl, 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—, wherein at least one hydrogen in the linear alkyl may be substituted with halogen;

L 21 , L 22 , L 23 , L 31 , L 32 , and L 33 are hydrogen, halogen, alkyl having 1 to 3 carbon atoms, fluorinated alkyl having 1 to 3 carbon atoms, or cycloalkyl having 3 to 5 carbon atoms; and

Y 21 , Y 31 , Y 32 , Y 33 , Y 34 , Y 35 and Y 36 are hydrogen or halogen.

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

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

R 2′ is linear alkyl having 1 to 12 carbon atoms, wherein, in the linear alkyl, at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—.

6 . The liquid crystal composition according to claim 4 , comprising at least one compound selected from the group of compounds represented by Formula (3-1) to Formula (3-11) as the compound represented by Formula (3),

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

R 3′ is linear alkyl having 1 to 12 carbon atoms, wherein in the linear alkyl, at least one —(CH 2 ) 2 — may be substituted with —CH═CH— or —C≡C—; and

Y 35′ is hydrogen, fluorine, or chlorine.

7 . The liquid crystal composition according to claim 4 , wherein based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (1) is in a range from 5 weight % to 25 weight %, and a proportion of the compound represented by Formula (2) is in a range from 10 weight % to 55 weight %.

8 . The liquid crystal composition according to claim 4 , wherein based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (1) is in a range from 5 weight % to 25 weight %, and a proportion of the compound represented by Formula (3) is in a range from 20 weight % to 50 weight %.

9 . The liquid crystal composition according to claim 4 , wherein based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (1) is in a range from 5 weight % to 25 weight %, a proportion of the compound represented by Formula (2) is in a range from 10 weight % to 55 weight %, and a proportion of the compound represented by Formula (3) is in a range from 20 weight % to 50 weight %.

10 . The liquid crystal composition according to claim 3 , having a refractive index anisotropy at 25° C. at a wavelength of 589 nm of 0.40 or more.

11 . The liquid crystal composition according to claim 3 , having a dielectric anisotropy at 25° C. at a frequency of 1 kHz of 10 or more.

12 . The liquid crystal composition according to claim 3 , having a dielectric anisotropy of 1.0 to 3.0 at 25° C. in at least one frequency range from 1 GHz to 10 THz.

13 . The liquid crystal composition according to claim 3 , further comprising an optically active compound.

14 . The liquid crystal composition according to claim 3 , further comprising a polymerizable compound.

15 . The liquid crystal composition according to claim 3 , further comprising at least one of an antioxidant, an ultraviolet absorber, an antistatic agent, and a dichroic dye.

16 . An element comprising the liquid crystal composition according to claim 3 , the element being used for switching and capable of reversibly controlling a dielectric constant by reversibly changing an orientation direction of liquid crystal molecules.

17 . An element comprising the liquid crystal composition according to claim 3 and used for electromagnetic wave control in a frequency range from 1 GHz to 10 THz.

18 . A liquid crystal lens comprising the liquid crystal composition according to claim 3 .

19 . A birefringent lens for stereoscopic image display comprising the liquid crystal composition according to claim 3 .

20 . A light modulator comprising the liquid crystal composition according to claim 3 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2025
From: OKABE, EIJI; MORI, TAKANORI; SHIREN, KAZUSHI; KATANO, YUKO; OGUCHI, YUJIRO; MINE, KOSUKE
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 071929/0757 →
Priority Claims (2)
JP 2024-212994 · Dec 6, 2024 · national
JP 2025-098187 · Jun 12, 2025 · national
Continuity (1)
Related Publication 20260159758A1 · Jun 11, 2026
References Cited (9)
US 12252643B2 · Okabe · 2025 [cited by examiner]
CN 116332800A · 2023 [cited by examiner]
JP 2004285085 · 2004 [cited by applicant]
JP 2011074074 · 2011 [cited by applicant]
WO 2017201515 · 2017 [cited by applicant]
WO 2017208996 · 2017 [cited by applicant]
Machine translation of CN-116332800-A (Year: 2023). [cited by examiner]
Hiroshi Moritake, “Microwave / millimeter wave phase control device (1st) Microwave characteristics of liquid crystal display,” Ekisho, vol. 23, Jan. 2019, with partial English translation thereof, pp. 1-7. [cited by applicant]
Yoshio Inuishi, “Dielectric Phenomenon Theory,” Institute of Electrical Engineers of Japan, Ohmsha, Ltd., Jul. 1973, with partial English translation thereof, pp. 1-9. [cited by applicant]