IP Library Granted Patent US 9,783,481
Granted Patent B2
US 9,783,481 · App. 14/615,159 · Granted Oct 10, 2017

Carbonyl derivative, liquid crystal composition containing compound thereof and liquid crystal display device

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Quick Facts
Patent No.
US 9,783,481
App. No.
14/615,159
Granted
Oct 10, 2017
Kind
B2
Abstract

To provide a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat, light and so forth, a high clearing point, a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant and an excellent compatibility with other liquid crystal compounds; a liquid crystal composition containing the compound; and a liquid crystal display device including the composition. The compound is represented by formula (1): wherein, for example, Ra and Rb are alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; A 1 , A 2 and A 3 are 1,4-cyclohexylene or 1,4-phenylene; Z 1 and Z 2 are single bonds, —(CH 2 ) 2 —, —CH═CH—, —COO—, —OCO—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —OCH 2 —; Y 1 is —CF 2 H or —CF 3 ; Y 2 is fluorine; and a, b and d are 0, 1, 2 or 3, and c is 1 or 3.

Claims (50)

1. A compound represented by any one of formulas (1-21) to (1-27):

wherein, in formulas (1-21) to (1-27),

Ra and Rb are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, fluorinated alkyl having 1 to 10 carbons or fluorinated alkoxy having 1 to 9 carbons;

A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, cyclohexene-1,4-diyl or tetrahydropyran-2,5-diyl;

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

Y 1 is —CF 2 H.

2. The compound according to claim 1 , wherein, in formulas (1-21) to (1-27) according to claim 1 , Ra and Rb are independently alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons;

A 1 and A 2 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or tetrahydropyran-2,5-diyl;

Z 1 is a single bond; and

Y 1 is —CF 2 H.

3. The compound according to claim 1 , wherein, in formulas (1-21) to (1-27) according to claim 1 , Ra and Rb are independently alkyl having 1 to 10 carbons or alkoxy having 1 to 9 carbons;

A 1 and A 2 are independently 1,4-cyclohexylene or 1,4-phenylene;

Z 1 is a single bond; and

Y 1 is CF 2 H.

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

5. The liquid crystal composition according to claim 4 , further containing at least one compound selected from the group of compounds represented by formulas (6) to (12):

wherein, in formulas (6) to (12),

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 of —CH 2 — may be replaced by —O— and at least one of hydrogen may be replaced by fluorine;

R 14 is alkyl having 1 to 10 carbons, and in the alkyl, at least one of —CH 2 — may be replaced by —O— and at least one of hydrogen may be replaced by fluorine;

R 15 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 of —CH 2 — may be replaced by —O—, and at least one of hydrogen may be replaced by fluorine;

S 11 is hydrogen or methyl;

X is —CF 2 —, —O— or —CHF—;

ring D 1 , ring D 2 , ring D 3 and ring D 4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;

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

Z 15 , Z 16 , Z 17 and Z 18 are independently a single bond, —CH 2 CH 2 —, —COO—, —CH 2 O—, —OCF 2 — or —OCF 2 CH 2 CH 2 —;

L 15 and L 16 are independently fluorine or chlorine; 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.

6. The liquid crystal composition according to claim 4 , further containing at least one compound selected from the group of compounds represented by formulas (13) to (15):

wherein, in formulas (13) to (15),

R 16 and R 17 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of —CH 2 — may be replaced by —O—, and at least one of 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-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; and

Z 19 , Z 20 and Z 21 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —C≡C— or —COO—.

7. The liquid crystal composition according to claim 4 , further containing at least one compound selected from the group of compounds represented by formulas (2) to (4):

wherein, in formulas (2), (3), and (4)

R 11 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine, and at least one of —CH 2 — may be replaced by —O—;

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 B 1 , ring B 2 and ring B 3 are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 11 , Z 12 and Z 13 are independently a single bond, —CH 2 CH 2 —, —CH═CH—, —COO—, —CF 2 O—, —OCF 2 —, —CH 2 O— or —(CH 2 )4-; and

L 11 and L 12 are independently hydrogen or fluorine.

8. The liquid crystal composition according to claim 4 , further containing at least one compound selected from the group of compounds represented by formula (5):

wherein, in formula (5),

R 12 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one of hydrogen may be replaced by fluorine, and at least one of —CH 2 — may be replaced by —O—;

X 12 is —C≡N or —C≡C—C≡N;

ring C 1 is 1,4-cyclohexylene, 1,4-phenylene in which at least one of hydrogen is replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z 14 is a single bond, —CH 2 CH 2 —, —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.

9. The liquid crystal composition according to claim 4 , further containing at least one optically active compound and/or at least one polymerizable compound.

10. The liquid crystal composition according to claim 4 , further containing at least one antioxidant and/or at least one ultraviolet light absorbent.

11. A liquid crystal display device, including the liquid crystal composition according to claim 4 .

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 Mar 18, 2015
From: GOTO, MAYUMI
To: JNC CORPORATION; JNC PETROCHEMICAL CORPORATION
Reel/Frame 035223/0722 →