Fluorinated aromatic compound, method for its production, curable material, its cured product, and optical member
View Patent ↗To provide a novel fluorinated aromatic compound having at least two carbon-carbon unsaturated bonds, a method for its production, a curable material comprising the fluorinated aromatic compound, a cured product thereof, and an optical member. The fluorinated aromatic compound is represented by formula (A), wherein n is an integer of 0 to 6, a is an integer of 0 to 5, b is an integer of 0 to 4, c is an integer of 0 to 4, a+c+n is 2 to 6, a+b is 2 to 9, Z is a single bond, —O—, —S—, —CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —SO—, or —SO 2 —, Rf 1 is a C 1-8 fluoroalkyl group, Y 1 and Y 2 are each independently a group represented by formula (1) (s is 0 or 1, and R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom or a fluorine atom), and F in the aromatic ring indicates that hydrogen atoms in the aromatic ring are all substituted by fluorine atoms.
1. A fluorinated aromatic compound represented by formula (A):
wherein
n is an integer of from 0 to 6,
a is an integer of from 0 to 5,
b is an integer of from 0 to 4,
c is 0, or c is an integer of from 1 to 4 and Rf 1 is a C 1-8 perfluoroalkyl group,
a+c+n is from 2 to 6,
a+b is from 2 to 9,
Z is a single bond, —O—, —S—, —CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —SO— or —SO 2 —,
each of Y 1 and Y 2 which are independent of each other, is a group represented by formula (1), and
F in the aromatic ring represents that hydrogen atoms of the aromatic ring are all substituted by fluorine atoms:
wherein
s is 0 or 1, and
each of R 1 , R 2 , R 3 and R 4 is a hydrogen atom.
2. The fluorinated aromatic compound according to claim 1 , which has a molecular weight of from 300 to 2,000.
3. The fluorinated aromatic compound according to claim 1 , represented by formula (A-1) or (A-2):
4. A method for producing the fluorinated aromatic compound according to claim 1 , the method comprising:
subjecting an aromatic compound represented by formula (a1) and a fluorinated aromatic compound represented by formula (a2) to a condensation reaction in the presence of a HF elimination agent:
where
in the formula (a1),
s is 0 or 1,
each of R 1 , R 2 , R 3 and R 4 is a hydrogen atom, and
X is a hydrogen atom, CH 3 CO, CH 3 CH 2 CO, (CH 3 ) 3 C(CH 3 ) 2 Si or (CH 3 ) 3 Si; and
in the formula (a2),
n is an integer of from 0 to 6,
c is 0, or c is an integer of from 1 to 4 and Rf 1 is a C 1-8 perfluoroalkyl group,
c+n is from 0 to 6,
Z is a single bond, —O—, —S—, —CO—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —SO—, or —SO 2 —,
and
F in the aromatic ring represents that hydrogen atoms of the aromatic ring are all substituted by fluorine atoms.
5. The method according to claim 4 , wherein the aromatic compound represented by the formula (a1) is 4-ethenyl phenol or 4-ethenyl-1-acetoxy benzene.
6. The method according to claim 4 , wherein the fluorinated aromatic compound represented by the formula (a2) is perfluorobenzene, perfluorotoluene, perfluoroxylene, perfluorobiphenyl, perfluoroterphenyl, a perfluorotriphenyl benzene, a perfluorotetraphenyl benzene, a perfluoropentaphenyl benzene, a perfluorohexaphenyl benzene, a 1,1′-oxybis[2,3,4,5,6-pentafluorobenzene], a 1,1′-thiobis[2,3,4,5,6-pentafluorobenzene], a bis(2,3,4,5,6-pentafluorophenyl) methanone, a 1,1′-sulfonyl bis[2,3,4,5,6-pentafluoro benzene], or a 1,2,3,4,5-pentafluoro-6-[(2,3,4,5,6-pentafluorophenyl) sulfinyl] benzene.
7. The method for according to claim 4 , wherein the HF elimination agent is an alkali metal hydroxide.
8. A curable material, comprising:
the fluorinated aromatic compound according to claim 1 .