Polysilsesquioxane-dendron liquid crystals and method for preparing the same

Patent metadata

Field	Value
Publication number	US-9670412-B2
Application number	US-201314650291-A
Country	US
Kind code	B2
Filing date	Dec 6, 2013
Priority date	Dec 7, 2012
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

Due to excellent processability of the POSS-dendron-structured liquid crystal compound according to the present invention, it is possible to coat and print on the compound and, also, to manufacture large size flexible devices.
According to the present invention, it is possible to maximize the physical bond strength between liquid crystals and, thus, to form higher-order structures by controlling the physical bond strength.
Since the POSS-dendron-structured liquid crystal compound of the present invention introduces non-functional groups to inorganic chemicals in contrast to the conventional liquid crystals, the compound disperses well into general types of solvents. In addition, the chemical and mechanical properties of the compound of the invention, such as increase of maximum allowable temperature, inhibition of oxidation, increase of surface hardness, etc., improves since polysilsesquioxane includes reactive or non-reactive organic compounds.
When the POSS-dendron-structured liquid crystal compound of the invention is used as an additive for liquid crystal layers, it can enhance the orientation of liquid crystal molecules. Moreover, the POSS part of the added liquid crystal compound of the invention may move to the lower surface of the liquid crystal layer and, then, improves the orientation.

First claim

The invention claimed is:

1. A liquid crystal compound of the formula 1 which has POSS-dendron structure:

where Ar is C 6 -C 20 aryl,
P is polysilsesquioxane,
Ar and P are linked with oxygen or NCO group,
R 1 and R 2 are independently C 1 -C 30 hydrocarbon,
M is mesogen of compound of the formula 6, and
m is 1-3

where A is —O—, —COO—, —OCO— or —NHCO—; B is S, O, N 2 or (CH 2 ) n ; and n is 1-20.

2. The liquid crystal compound of claim 1 , wherein the polysilsesquioxane is a POSS-dendron-structured liquid crystal compound of formula 2:
[R—SiO 1.5 ] n    [formula 2]

where R is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkenyl, C 3 -C 10 cycloalkyl, C 6 -C 15 aryl, hydrogen and hydroxyl; and n is an integer of 3-1,000.

3. The liquid crystal compound of claim 1 , wherein R 1 and R 2 are independently C 2 -C 30 linear or branched alkyl, or C 2 -C 30 alkenyl.

4. The liquid crystal compound of claim 1 , wherein R 1 and R 2 are independently C 1 -C 30 alkylene, C 1 -C 30 alkoxy, C 1 -C 30 fluoroalkylene, C 1 -C 30 ether, C 1 -C 30 fluoroether, or —OR 3 O—, where R 3 is C 1 -C 30 alkylene or C 1 -C 30 fluoroalkylene.

5. The liquid crystal compound of claim 1 , wherein the compound of formula 1 is selected from the compounds of the following formula 5:

where P is polysilsesquioxane, R 1 and R 2 are independently C 1 -C 20 hydrocarbon, M is mesogen, and m is 1-3.

6. The liquid crystal compound of claim 1 , wherein the liquid crystal compound of the POSS-dendron structure has a chemical structure of formula 7

7. The liquid crystal compound of claim 1 , wherein the liquid crystal compound of the POSS-dendron structure has a weight average molecular weight of 500-3,000 g/mol.

8. A method for preparing a liquid crystal compound of the following formula 9 which has POSS-dendron structure, comprising:
(i) reacting alkyl chain (R 1 ) with mesogen (M) in a weight ratio of 1:0.8-1.5;
(ii) reacting the R 1 -M obtained in the step (i) with R 2 in a weight ratio of 1:2-4;
(iii) reacting the R 1 -M-R 2 obtained in the step (ii) with benzoate in a certain weight ratio to form R 1 -M-R 2 —Ar; and
(iv) reacting the R 1 -M-R 2 —Ar with polysilsesquioxane,

where M is mesogen of compound of the formula 6,

R 1 is CF 3 (CF 2 )nCH 2 CH 2 OH, CH 3 (CH 2 ) n Br, CH 3 (CH 2 ) n OH, CH 3 (OCH 2 CH 2 ) n OH, CH 3 (OCH 2 CH 2 ) n Br, CF 3 (CF 2 ) n Br, CF 3 (CF 2 ) n I, CF 3 (CF 2 ) n CH 2 I, CF 3 (CF 2 ) n CH 2 OH, CF 3 (CF 2 ) n CH 2 CH 2 I or CH 3 (CH 2 ) n Cl;
R 2 is Cl(CH 2 ) n Cl, Br(CH 2 ) n Br, HO(CH 2 ) n OH, ClCH 2 (CH 2 OCH 2 ) n CH 2 Cl, Cl(CF 2 ) n Cl, I(CF 2 ) n I, Br(CF 2 ) n Br, HOCH 2 (CH 2 OCH 2 ) n CH 2 OH, or HOCH 2 (CF 2 ) n CH 2 OH;
Ar is benzene; and
P is polysilsesquioxane.

9. The method of claim 8 , wherein the R 1 -M-R 2 —Ar is reacted with the polysilsesquioxane after introducing —NCO to the end group of the polysilsesquioxane at the step (iv).

10. A method for forming a liquid crystal display device comprising:
providing a liquid crystal material;
adding a liquid crystal compound to the liquid crystal material; and
using the liquid crystal material with the added liquid crystal compound to form a liquid crystal layer having an upper side and a lower side;
wherein the liquid crystal compound improves alignment of liquid crystal molecules of the liquid crystal layer, or enhances orientation of the liquid crystal molecules by being located at either or both of the upper side or lower side of the liquid crystal layer;
wherein the liquid crystal compound is of the formula 1 which has POSS-dendron structure:

where Ar is C 6 -C 20 aryl,
P is polysilsesquioxane,
Ar and P are linked with oxygen or NCO group,
R 1 and R 2 are independently C 1 -C 30 hydrocarbon,
M is mesogen of compound of the formula 6, and
m is 1-3

where A is —O—, —COO—, —OCO— or —NHCO—; B is S, O, N 2 or (CH 2 ) n ; and n is 1-20.

11. The method of claim 10 , wherein the polysilsesquioxane is a POSS-dendron-structured liquid crystal compound of formula 2:
[R—SiO 1.5 ] n    [formula 2]

where R is selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkenyl, C 3 -C 10 cycloalkyl, C 6 -C 15 aryl, hydrogen and hydroxyl; and n is an integer of 3-1,000.

12. The method of claim 10 , wherein R 1 and R 2 are independently C 2 -C 30 linear or branched alkyl, or C 2 -C 30 alkenyl.

13. The method of claim 10 , wherein R 1 and R 2 are independently C 1 -C 30 alkylene, C 1 -C 30 alkoxy, C 1 -C 30 fluoroalkylene, C 1 -C 30 ether, C 1 -C 30 fluoroether, or —OR 3 O—, where R 3 is C 1 -C 30 alkylene or C 1 -C 30 fluoroalkylene.

14. The method of claim 10 , wherein the compound of formula 1 is selected from the compounds of the following formula 5:

where P is polysilsesquioxane, R 1 and R 2 are independently C 1 -C 20 hydrocarbon, M is mesogen, and m is 1-3.

15. The method of claim 10 , wherein the liquid crystal compound of the POSS-dendron structure has a chemical structure of formula 7

16. The method of claim 10 , wherein the liquid crystal compound of the POSS-dendron structure has a weight average molecular weight of 500-3,000 g/mol.

Assignees

• Nat Univ Chonbuk Ind Coop Found

Inventors

• Jeong Kwang Un
• Kook Yun Bae
• Kim In Soo

Classifications

• G02F1/133 Primary

  Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements (arrangements or circuits for control of liquid crystal elements in a matrix, not structurally associated with these elements G09G3/36) · CPC title

• C07F7/21

  Cyclic compounds having at least one ring containing silicon, but no carbon in the ring · CPC title

• C09K19/406

  containing silicon · CPC title

• C09K19/56 Primary

  Aligning agents · CPC title

• C09K2019/0418

  containing a dendromer structure; Dendritic liquid crystals · CPC title