Polyhedral oligomeric silsesquioxane and preparation method thereof
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.
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.