Liquid crystalline epoxy compound with terminal mesogen connected by flexible linkage and method for preparing the same

Patent metadata

Field	Value
Publication number	US-2018201835-A1
Application number	US-201815865259-A
Country	US
Kind code	A1
Filing date	Jan 9, 2018
Priority date	Jan 17, 2017
Publication date	Jul 19, 2018
Grant date	—

Abstract

Disclosed is a liquid crystalline epoxy compound wherein an epoxy group is positioned at a side chain of the longer direction of a mesogen group and each of the mesogen group and the epoxy group is connected to the center of the molecular structure through a flexible linkage. Since the liquid crystalline epoxy compound includes an epoxy group positioned at a side chain of the longer direction of a mesogen group and each of the mesogen group and the epoxy group is connected to the center of the molecular structure through a flexible linkage, the interaction between the mesogens in a cured resin product occurs significantly without weakening even after curing, thereby improving the heat conductivity of the resin compound through the active heat transfer between the mesogens.

First claim

What is claimed is:

1 . A liquid crystalline epoxy compound wherein an epoxy group is positioned at a side chain of the longer direction of a mesogen group and each of the mesogen group and the epoxy group is connected to the center of the molecular structure through a flexible linkage.

2 . The liquid crystalline epoxy compound according to claim 1 , which is represented by any one of the following Chemical Formula 1 to 3:

wherein L is a central aromatic hydrocarbon substituted with L1 and L2, wherein L1 is a flexible linkage represented by —(CH 2 ) m OCO—, L2 is a flexible linkage represented by —(CH 2 ) m O—, and R represents a mesogen group. m represents an integer of 1 or more.

3 . The liquid crystalline epoxy compound according to claim 1 , which is represented by any one of the following Chemical Formula 1-1, 2-1 and 3-1:

wherein R represents a mesogen group, and each of m and n independently represents an integer of 1 or more.

4 . The liquid crystalline epoxy compound according to claim 1 , wherein the mesogen group is represented by any one of the following chemical formula:

wherein

represents a site connected to another substituent.

5 . A method for preparing a liquid crystalline epoxy compound as defined in claim 1 , comprising the steps of: 1) preparing a liquid crystalline alkyl halide compound having a mesogen group; 2) preparing a liquid crystalline ester derivative from the liquid crystalline alkyl halide compound; 3) preparing a liquid crystalline carboxylic acid derivative from the liquid crystalline ester derivative; and 4) preparing a liquid crystalline epoxy compound represented by the following Chemical Formula 1-1 from the liquid crystalline carboxylic acid derivative:

wherein R represents a mesogen group, and each of m and n independently represents an integer of 1 or more.

6 . The method for preparing a liquid crystalline epoxy compound according to claim 5 , wherein the mesogen group is represented by any one of the following chemical formula:

wherein

represents a site connected to another substituent.

7 . The method for preparing a liquid crystalline epoxy compound according to claim 5 , wherein the liquid crystalline alkyl halide having a mesogen group is represented by the following Chemical Formula 4:
R—O—(CH 2 ) m —X  [Chemical Formula 4]
wherein R and m are the same as defined in Chemical Formula 1-1, and X represents a halogen group.

8 . The method for preparing a liquid crystalline epoxy compound according to claim 5 , wherein the liquid crystalline ester derivative is represented by the following Chemical Formula 5:

wherein R and m are the same defined in Chemical formula 1-1, and Alkyl represents a C1 or higher alkyl group.

9 . The method for preparing a liquid crystalline epoxy compound according to claim 5 , wherein the liquid crystalline carboxylic acid derivative is represented by the following Chemical Formula 6:

wherein R and m are the same defined in the above Chemical Formula 1-1.

10 . The method for preparing a liquid crystalline epoxy compound according to claim 5 , wherein the liquid crystalline ester derivative, 1,2-epoxy-(n+2)-alkyl alcohol (wherein n is the same as defined in the above Chemical Formula 1) and a dehydrating agent are allowed to react in a solvent, in step 4).

11 . The method for preparing a liquid crystalline epoxy compound according to claim 10 , wherein the dehydrating agent is at least one selected from the group consisting of N,N′-dicyclohexylcarbodiimide, N,N′-diisopropylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N-hydroxysuccinimide, 4-dimethylaminopyridine, N-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, 2-(1H-benzotriazol-1-yl)-1,1,3,3,-tetramethyluronium hexafluorophosphate, 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate, 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one, thionyl chloride and pyridine.

12 . The method for preparing a liquid crystalline epoxy compound according to claim 10 , wherein the solvent is at least one selected from the group consisting of diethyl ether, chloroform, 1,4-dioxane, dichloromethane, ethyl acetate, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, acetonitrile, methyl ethyl ketone and diethyl ketone.

13 . A method for preparing the liquid crystalline epoxy compound as defined in claim 1 , comprising the steps of: 1) preparing a liquid crystalline alcohol derivative having a mesogen group; 2) preparing a carboxylic acid derivative whose hydroxyl group is protected; 3) preparing a liquid crystalline ester derivative from the liquid crystalline alcohol derivative and the carboxylic acid derivative whose hydroxyl group is protected; 4) preparing a liquid crystalline ester derivative whose hydroxyl group is deprotected from the liquid crystalline ester derivative; and 5) preparing a liquid crystalline epoxy compound represented by the following Chemical Formula 2-1 or 3-1 from the liquid crystalline ester derivative whose hydroxyl group is deprotected:

wherein R represents a mesogen group, and each of m and n independently represents an integer of 1 or more.

14 . The method for preparing the liquid crystalline epoxy compound according to claim 13 , wherein the mesogen group is represented by any one of the following chemical formula:

wherein

represents a site connected to another substituent.

15 . The method for preparing the liquid crystalline epoxy compound according to claim 13 , wherein the liquid crystalline alcohol derivative having a mesogen group is represented by the following Chemical Formula 8:
R—O—(CH 2 ) m —OH  [Chemical Formula 8]
wherein R and m are the same as defined in Chemical Formula 2-1 and 3-1.

16 . The method for preparing the liquid crystalline epoxy compound according to claim 13 , wherein the carboxylic acid derivative whose hydroxyl group

Assignees

• Korea Inst Sci & Tech

Inventors

• Goh Munju
• Yeo Hyeonuk
• You Nam Ho
• Jang Se Gyu
• Ahn Seokhoon
• Kim Young Soo

Classifications

• C09K2019/3009

  Cy-Ph · CPC title

• C09K19/16

  the chain containing carbon-to-carbon double bonds, e.g. stilbenes · CPC title

• C09K19/388 Primary

  Polyepoxides · CPC title

• C09K19/12

  at least two benzene rings directly linked, e.g. biphenyls · CPC title

• C09K2019/122

  Ph-Ph · CPC title