Liquid crystal compounds of cycloalkyl-containing dibenzofuran derivatives, preparation method therefor and use thereof

Patent metadata

Field	Value
Publication number	US-10351773-B2
Application number	US-201715782133-A
Country	US
Kind code	B2
Filing date	Oct 12, 2017
Priority date	Oct 21, 2016
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

Disclosed are liquid crystal compounds of cycloalkyl-containing dibenzofuran derivatives, a preparation method therefor and use thereof. The compounds are as represented by formula I. In the molecular structures of the compounds of formula I provided by the present invention, liquid crystal compounds of cycloalkyl terminal group-containing dibenzofuran derivatives, compared with those having flexible alkyl chains as terminal groups, exhibit better intersolubility, and thus the use of a compound as represented by formula I provided by the present invention can improve the intersolubility of a liquid crystal compound and extend the application range of a liquid crystal mixture, producing an important application value.

First claim

The invention claimed is:

1. Compounds as represented by formula I

wherein H represents one of cyclopropyl, cyclobutyl, cyclopentyl or 2-tetrahydrofuranyl; Z represents one of a single bond, —CH 2 —, —O—, —CH 2 CH 2 — or —CH 2 O—; and X represents a hydrogen atom, a fluorine atom, an alkyl group having 1-7 carbon atoms or an alkoxy group having 1-7 carbon atoms.

2. The compounds according to claim 1 , wherein the compounds as represented by said formula I are specifically compounds as represented by formulas I1 to I15:

wherein H each independently represents one of cyclopropyl, cyclobutyl or 2-tetrahydrofuranyl; and R each independently represents one of an alkyl group having 1-7 carbon atoms or an alkoxy group having 1-7 carbon atoms.

3. The compounds according to claim 1 , wherein the compounds as represented by said formula I are specifically the following compounds as represented by I1-1 to I15-2:

4. A liquid crystal medium, wherein said liquid crystal medium comprises one or more compounds as represented by formula I in claim 1 .

5. The liquid crystal medium according to claim 4 , wherein said liquid crystal medium further comprises one or more compounds as represented by formula IV:

in said formula TV, R 2 and R 3 each independently represent any one of groups as shown by (1) to (3) below:
(1) linear alkyl groups having 1-7 carbon atoms or linear alkoxy groups having 1-7 carbon atoms;
(2) groups formed by substituting one or more —CH 2 — in any one of the groups as shown by (1) with —O—, —COO—, —OOC— or —CH═CH—; and
(3) groups formed by substituting one or more —H in any one of the groups as represented by (1) with —F, —Cl, —CH═CH 2 or —CH═CH—CH 3 ;
rings B, C, D and E each independently represent the following groups:

and at least one of said rings B, C, D and E is selected from

m, n and o each independently represent 0 or 1;
Z 1 , Z 2 and Z 3 each independently represent a single bond, —C 2 H 4 —, —CH═CH—, , —COO—, —OOC—, —CH 2 O—, —OCH 2 —, —CF 2 O— or —OCF 2 —; wherein additionally, any H atom of these groups may be replaced with F.

6. The liquid crystal medium according to claim 5 , wherein said liquid crystal medium further comprises one or more compounds as represented by formula V:

in said formula V, R 4 and R 5 each independently represent an alkyl group having 1-10 carbon atoms or an alkenyl group having 2-10 carbon atoms; in addition, any —CH 2 — of these groups may be replaced with —CH 2 O—, —OCH 2 — or —C═C—, and any hydrogen may be replaced with F;
rings F, G, I and J each independently represent the following groups:

p, q and r each independently represent 0 or 1;
Z 4 , Z 5 and Z 6 each independently represent a single bond, —C 2 H 4 —, —CH═CH—, , —COO—, —OOC—, —CH 2 O—, —OCH 2 —, —CF 2 O—, or —OCF 2 —; wherein additionally, any H atom of these groups may be replaced with F.

7. The liquid crystal medium according to claim 6 , wherein in said liquid crystal medium, the total content in weight percentage of one or more compounds as represented by formula I is 1-24%, the total content in weight percentage of one or more compounds as represented by formula IV is 35-58%, and the total content in weight percentage of one or more compounds as represented by formula V is 30-46%.

8. The liquid crystal medium according to claim 5 , wherein said one or more compounds as represented by formula IV are one or more of the compounds as represented by formulas IVa- to IVo:

wherein R 2 and R 3 each independently represent any one of groups as shown by (1) to (3) below:
(1) linear alkyl groups having 1-7 carbon atoms or linear alkoxy groups having 1-7 carbon atoms;
(2) groups formed by substituting one or more —CH 2 — in any one of the groups as shown by (1) with —O—, —COO—, —OOC— or —CH═CH—; and
(3) groups formed by substituting one or more —H in any one of the groups as represented by (1) with —F, —Cl, —CH═CH 2 or —CH═CH—CH 3 ;

each independently represent any one of the following groups:

9. The liquid crystal medium according to claim 6 , wherein said one or more compounds as represented by formula V are one or more of the compounds as represented by formulas Va- to Vp:

wherein R 4 and R 5 each independently represent an alkyl group having 1-10 carbon atoms or an alkenyl group having 2-10 carbon atoms; in addition, any —CH 2 — of these groups may be replaced with —CH 2 O—, —OCH 2 — or —C═C—, and any hydrogen may be replaced with F; (F) each independently represents F or H.

Assignees

• Shijiazhuang Chengzhi Yonghua Display Materials Co Ltd

Inventors

• Li Ming
• Gao Hongru
• Zhang Fangmiao
• Meng Jingsong
• Yun Guoliang
• Zhang Xing
• Zhao Lei
• Deng Jia

Classifications

• C09K19/3405 Primary

  the heterocyclic ring being a five-membered ring · CPC title

• C09K2019/0407

  containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K2019/3063

  Cy-Ph-C≡C-Ph · CPC title