Polyhedral oligomeric silsesquioxane and preparation method thereof

Patent metadata

Field	Value
Publication number	US-10683313-B2
Application number	US-201716070310-A
Country	US
Kind code	B2
Filing date	Mar 9, 2017
Priority date	Mar 17, 2016
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

Provided are a polyhedral oligomeric silsesquioxane and a preparation method thereof, more particularly, a polyhedral oligomeric silsesquioxane itself which has a low refractive property and enables formation of a coating layer with excellent chemical and mechanical properties, and provides excellent adhesive strength for the surfaces of various substrates, and a preparation method thereof.

First claim

The invention claimed is:

1. A polyhedral oligomeric silsesquioxane represented by the following Chemical Formula 1:
(R 1 SiO 1.5 ) x (R 2 SiO 1.5 ) y (R 3 SiO 1.5 ) z   [Chemical Formula 1]

wherein R 1 and R 2 are each independently a hydrocarbyl group having 1 to 10 carbon atoms, in which at least one hydrogen atom is substituted with a halogen atom, and R 1 has a substitution ratio of the halogen atom in the hydrocarbyl group of less than 50%, and R 2 has a substitution ratio of the halogen atom in the hydrocarbyl group of 50% or more,
R 3 is an unsaturated functional group;
x and y are each independently an integer of 1 to 12, and z is an integer of 2 to 12.

2. The polyhedral oligomeric silsesquioxane of claim 1 , wherein R 1 is a trifluoropropyl group, a trifluoropentyl group, a pentafluoropentyl group, a trifluorohexyl group, a pentafluorohexyl group, a trifluoroheptyl group, a pentafluoroheptyl group, a heptafluoroheptyl group, a chloropropyl group, or a dibromoethyl group, and R 2 is a trifluoromethyl group, a trifluoroethyl group, a pentafluorobutyl group, a heptafluoropentyl group, a heptafluorohexyl group, a nonafluorohexyl group, a nonafluoroheptyl group, or a dodecafluoroheptyl group.

3. The polyhedral oligomeric silsesquioxane of claim 1 , wherein x:y is 5:1 to 1:5.

4. The polyhedral oligomeric silsesquioxane of claim 1 , wherein R 3 is an ethylenic unsaturated functional group or an epoxide unsaturated functional group.

5. The polyhedral oligomeric silsesquioxane of claim 4 , wherein R 3 is a hydrocarbyl group or a hydrocarbyloxy group having 1 to 30 carbon atoms, which is substituted with one or more substituents selected from the group consisting of a (meth)acryloyl group, a (meth)acryloyloxy group, a glycidyl group, an epoxy group, and a vinyl group.

6. The polyhedral oligomeric silsesquioxane of claim 1 , satisfying 6≤x+y+z≤30.

7. The polyhedral oligomeric silsesquioxane of claim 1 , satisfying 0.2≤(x+y)/z≤3.

8. The polyhedral oligomeric silsesquioxane of claim 1 , wherein a refractive index is 1.20 to 1.50.

9. A coating composition comprising the polyhedral oligomeric silsesquioxane of claim 1 .

10. An anti-reflection film comprising a low refractive index layer which is formed by using the coating composition of claim 9 .

11. A method of preparing a polyhedral oligomeric silsesquioxane, the method comprising the step of reacting a reaction mixture including a first silane compound represented by the following Chemical Formula 1x, a second silane compound represented by the following Chemical Formula 1y, and a third silane compound represented by the following Chemical Formula 1z:
R 1 SiX 1 3   [Chemical Formula 1x]

R 2 SiX 2 3   [Chemical Formula 1y]

R 3 —SiX 3 3   [Chemical Formula 1z]

wherein R 1 and R 2 are each independently a hydrocarbyl group having 1 to 10 carbon atoms, in which at least one hydrogen atom is substituted with a halogen atom, and R 1 has a substitution ratio of the halogen atom in the hydrocarbyl group of less than 50%, and R 2 has a substitution ratio of the halogen atom in the hydrocarbyl group of 50% or more,
R 3 is an unsaturated functional group;
X 1 to X 3 are the same as or different from each other, and each independently a halogen atom or an alkoxy group having 1 to 5 carbon atoms.

12. The method of preparing the polyhedral oligomeric silsesquioxane of claim 11 , wherein R 1 is a trifluoropropyl group, a trifluorobutyl group, a trifluoropentyl group, a pentafluoropentyl group, a trifluorohexyl group, a pentafluorohexyl group, a trifluoroheptyl group, a pentafluoroheptyl group, a heptafluoroheptyl group, a chloropropyl group, or a dibromoethyl group, and R 2 is a trifluoromethyl group, a trifluoroethyl group, a pentafluorobutyl group, a heptafluoropentyl group, a heptafluorohexyl group, a nonafluorohexyl group, a nonafluoroheptyl group, or a dodecafluoroheptyl group.

13. The method of preparing the polyhedral oligomeric silsesquioxane of claim 11 , wherein R 3 is an ethylenic unsaturated functional group or an epoxide unsaturated functional group.

14. The method of preparing the polyhedral oligomeric silsesquioxane of claim 11 , wherein the reaction is allowed in the presence of a basic catalyst.

Assignees

• Lg Chemical Ltd

Inventors

• Choi Ji Young
• Choi Dai Seung
• Song Young Jee

Classifications

• C08J7/044

  Forming conductive coatings; Forming coatings having anti-static properties · CPC title

• C08J7/046

  Forming abrasion-resistant coatings; Forming surface-hardening coatings · CPC title

• C08J7/043

  Improving the adhesiveness of the coatings per se, e.g. forming primers (adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50) · CPC title

• C08J7/042

  with two or more layers, where at least one layer of a composition contains a polymer binder · CPC title

• C07F7/21 Primary

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