Cycloheptane derivative and preparation method and use thereof

Patent metadata

Field	Value
Publication number	US-9493704-B2
Application number	US-201314430536-A
Country	US
Kind code	B2
Filing date	Sep 17, 2013
Priority date	Sep 24, 2012
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

A cycloheptane derivative as represented by formula (I), and preparation method and use thereof; the compound has photostability and thermostability, wide nematic phase and liquid crystalline state temperature range, and good low-temperature intersolubility, and particularly has low rotary viscosity γ 1 and good dielectric anisotropy (Δ∈>0).

First claim

The invention claimed is:

1. A compound represented by formula I,

in the formula I, both R 1 and R 2 are represented as groups shown in the following A, B or C:
A. at least one of group selected from H, —Cl, —F, —CN, —OCN, —OCF 3 , —CF 3 , —CHF 2 , —CH 2 F, —OCHF 2 , —SCN, —NCS, —SF 5 , C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl and C2-C15 alkenoxy;
B. groups obtained by substituting one or at least two non-adjacent —CH 2 — in A groups with at least one of following groups and to which oxygen atoms are not directly attached: —CH═CH—, —C≡C—, —COO—, —OOC—, cyclobutyl, —O— or —S—;
C. at least one of groups obtained by substituting at least one of hydrogen in A groups and B groups with fluorine or chlorine;

are at least one of a single bond or following groups:

Z 1 and Z 2 are same or different, both of them are selected from at least one of a single bond, —CH 2 —, —CH 2 —CH 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CH═CH—, —C≡C—, —COO—, —OOC—, —CF 2 O—, —OCH 2 —, —CH 2 O—, —OCF 2 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —C 2 F 4 — and —CF═CF—;
a, b and c are an integer from 0 to 3, and a+b+c≦5;
when a, b and c represents 2 or 3 respectively, the groups represented by

may be same or different, the groups represented by

may be same or different, and the groups represented by

may be same or different.

2. The compound according to claim 1 , characterized in that the compound represented by the formula I is any one of the compounds represented by the following formulas I-1 to 1-6:

wherein the definition of

is same as that of

3. A liquid crystal mixture comprising the compound represented by the formula I of claim 2 .

4. A liquid crystal mixture comprising any one of the compound represented by formula I and the compound represented by formulas II to IV of claim 2 ; or,
the liquid crystal mixture consisting of any one of the compound represented by formula I and the compound represented by formula II to formula IV of claim 2 :

in the formula II to formula IV, R 1 and R 2 are same or different, both of selected from any one of hydrogen, halogen, —CN, C1-C7 alkyl, C1-C7 alkoxy, C2-C7 alkenyl, C1-C5 fluoroalkoxy, cyclobutyl and cyclopentyl;
Z 2 are selected from any one of single bond, —CH 2 —CH 2 —, —CH═CH—, —C≡C—, —COO—, —OOC—, —OCH 2 —, —CH 2 O—, —CF 2 O— and —OCF 2 —;

are selected from at least one of a single bond and the following groups:

Y 1 and Y 2 are selected from any one of H and F;
d is an integer from 0 to 2.

5. The liquid crystal mixture according to claim 4 , characterized in that the mass ratio of any of the compound represented by formula I, the compound represented by formula II, formula III and formula IV of claim 3 is 0-30: 4-50: 5-50: 3-45; and the weight of the compound represented by formula I is not 0.

6. The liquid crystal mixture according to claim 5 , characterized in that the liquid crystal mixture is any one of the liquid crystal mixtures a-h:
the liquid crystal mixture a comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture b comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture c comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture d specifically comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture e comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture f specifically comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture g comprises or consists of the following components in the respective parts by weight thereof:

the liquid crystal mixture h specifically comprises or consists of the following components in the respective parts by weight thereof:

7. A method of using any one of the liquid crystal compound represented by formula I,

in the formula I, both R 1 and R 2 are represented as groups shown in the following A, B or C:
A. at least one of group selected from H, —Cl, —F, —CN, —OCN, —OCF 3 , —CF 3 , —CHF 2 , —CH 2 F, —OCHF 2 , —SCN, —NCS, —SF 5 , C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl and C2-C15 alkenoxy;
B. groups obtained by substituting one or at least two non-adjacent —CH 2 — in A groups with at least one of following groups and to which oxygen atoms are not directly attached: —CH═CH—, —C≡C—, —COO—, —OOC—, cyclobutyl, —O— or —S—;

Assignees

• Shijiazhuang Chengzhi Yonghua Display Materials Co Ltd

Inventors

• Han Yaohua
• Xia Zhiguo
• Hua Ruimao
• Yang Zengjia
• Wang Kui
• Li Hongfeng
• Zhang Jianli

Classifications

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K2019/0466

  the linking chain being a -CF2O- chain · CPC title

• C07C43/247

  containing halogen · CPC title

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C09K2019/3096

  Cyclobutane rings · CPC title