IP Library Granted Patent US 9,573,923
Granted Patent B2
US 9,573,923 · App. 14/907,034 · Granted Feb 21, 2017

Liquid crystal compound having 2, 6-difluorophenylether structure, and liquid crystal composition containing the same

Inventors: Kenta Tojo (Kita-adachi-gun, JP); Tetsuo Kusumoto (Kita-adachi-gun, JP)
Assignee: DIC CORPORATION
C07D319/06C07D309/06C09K19/04C09K19/20C09K19/3066C09K19/322C09K19/3402C09K2019/3422
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Quick Facts
Patent No.
US 9,573,923
App. No.
14/907,034
Granted
Feb 21, 2017
Kind
B2
Abstract

The present invention relates to a compound having a 2,6-difluorophenylether structure useful as organic electronic materials, pharmaceuticals and agrochemicals, and in particular, liquid crystal display device materials. Provided are a compound represented by general formula (1): and a liquid crystal composition containing the compound and a liquid crystal display device that uses the liquid crystal composition. Since the compound represented by general formula (1) is used as a component of a liquid crystal composition, a liquid crystal composition that exhibits low viscosity and a liquid crystal phase over a wide temperature range can be obtained. Thus, the compound is particularly useful as a component of a liquid crystal composition for high-response-speed liquid crystal display devices.

Claims (29)

1. A compound represented by general formula (1)

(where R represents an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms and one —CH 2 — or two or more non-adjacent —CH 2 — in the group may each be substituted with —O—, —S—, —COO—, —OCO—, or —CO—,

A 1 , A 2 , A 3 , A 4 , and A 5 each independently represent a group selected from the group consisting of

(a) a 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 — in the group may each be substituted with —O— or —S—),

(b) a 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═ in the group may each be substituted with —N═ and a hydrogen atom in the group may be substituted with a fluorine atom), and

(c) a naphthalene-2,6-diyl group (a hydrogen atom in the group may be substituted with a fluorine atom),

at least one group selected from A 1 , A 2 , and A 3 is a group represented by

(where X represents an oxygen atom),

Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 each independently represent —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CF 2 CF 2 —, —CH═CH—, —CF═CF—, —C—C—, or a single bond,

A 6 represents

(where W represents a fluorine atom, a chlorine atom, a cyano group, —CF 3 , —OCH 2 F, —OCHF 2 , or —OCF 3 , and Y 1 , Y 3 , Y 4 , and Y 5 each independently represent a fluorine atom, a chlorine atom, or a hydrogen atom), and

m, n, p, r, and s each independently represent 0 or 1, at least one selected from m, n, and p represents 1, m+n+p+r+s equals 1, 2, or 3, and at least one group selected from A 1 , A 2 , and A 3 corresponding to m, n, and p representing 1 is

(where X represents an oxygen atom)).

2. The compound according to claim 1 , wherein, A 1 , A 2 , A 3 , A 4 , and A 5 in general formula (1) each independently represent a group selected from below:

3. The compound according to claim 1 , wherein Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 in general formula (1) each independently represent —OCH 2 —, —CF 2 O—, —CH 2 CH 2 —, —C≡C—, or a single bond.

4. The compound according to claim 1 , wherein W in general formula (1) represents a fluorine atom, a cyano group, or —OCF 3 .

5. The compound according to claim 1 ,

wherein A 6 in general formula (1) represents below:

6. The compound according to claim 1 , wherein A 6 in general formula (1) represents below:

7. The compound according to claim 1 , wherein the compound is a compound selected from compounds represented by general formula (1a) to general formula (1f):

(where R, W, Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 are respectively the same as R, W, Y 1 , Y 2 , Y 3 , Y 4 , and Y 5 in general formula (1), A 1 , A 2 , A 3 , A 4 , and A 6 each independently represent a group selected from the group consisting of

(a) a 1,4-cyclohexylene group (one —CH 2 — or two or more non-adjacent —CH 2 — in the group may each be substituted with —O— or —S—) and

(b) a 1,4-phenylene group (one —CH═ or two or more non-adjacent —CH═ in the group may each be substituted with —N═ and a hydrogen atom in the group may be substituted with a fluorine atom),

at least one group selected from A 1 , A 2 and A 3 is

(where X represents an oxygen atom),

in general formula (1a) and general formula (1b), m, n, and p each independently represent 0 or 1 and at least one selected from m, n, and p represents 1, and

in general formula (1c) and general formula (1d), m and n each independently represent 0 or 1 and at least one selected from m and n represents 1).

8. A liquid crystal composition comprising one or more compounds according to claim 1 .

9. A liquid crystal display device that uses the liquid crystal composition according to claim 8 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 24, 2024
From: DIC CORPORATION
To: SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIAL CO., LTD.
Reel/Frame 067528/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2016
From: TOJO, KENTA; KUSUMOTO, TETSUO
To: DIC CORPORATION
Reel/Frame 037557/0825 →
Priority Claims (1)
JP 2013-208200 · Oct 3, 2013 · national
Continuity (1)
Related Publication 20160159765A1 · Jun 9, 2016