Curable composition, cured product, optical component, lens, and compound

Patent metadata

Field	Value
Publication number	US-9994661-B2
Application number	US-201715678614-A
Country	US
Kind code	B2
Filing date	Aug 16, 2017
Priority date	Mar 2, 2015
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

Disclosed herein are a curable composition which is capable of producing a cured product having a low Abbe's number and increased durability, and a curable composition with suppressed viscosity increase. Provided is a compound represented by General Formula (A). Also provided are a curable composition including a compound represented by General Formula (A), a predetermined (meth)acrylate monomer, and at least one selected from a photoradical polymerization initiator and a thermal radical polymerization initiator; a cured product formed by curing the curable composition; an optical component; and a lens.

First claim

What is claimed is:

1. A curable composition, comprising:
a compound represented by General Formula (A);
a (meth)acrylate monomer having a viscosity at 25° C. of less than 2,000 mPa·s; and
at least one selected from a photoradical polymerization initiator and a thermal radical polymerization initiator,

in General Formula (A), at least one of R 1 , R 2 , R 3 , or R 4 is a substituent having a Hammett substituent constant σ p value of smaller than −0.15, provided that R 1 to R 4 are each independently a substituent having no reactive group, and R 1 to R 4 substituents adjacent to each other are not bonded to each other to form a fused ring; R 5 to R 7 each independently represent a substituent; Ar 11 and Ar 12 each independently represent an aryl group containing a benzene ring surrounded by a broken line or a heteroaryl group containing a benzene ring surrounded by a broken line, and Ar 13 is an aromatic fused ring group containing a benzene ring surrounded by a broken line as one of the fused rings; R 12 and R 13 are each independently a hydroxyl group, a mercapto group, an amino group, or a group having a polymerizable unsaturated bond; c to e each independently represent an integer of 0 to 4; in a case where Ar 11 and Ar 12 are each independently an aromatic fused ring group containing a benzene ring surrounded by a broken line as one of the fused rings, R 5 , R 6 , R 12 , and R 13 may each independently be substituted with a benzene ring surrounded by a broken line or may be substituted with a fused ring other than a benzene ring surrounded by a broken line; and R 7 may be substituted with a benzene ring surrounded by a broken line or may be substituted with a fused ring other than a benzene ring surrounded by a broken line.

2. The curable composition according to claim 1 , wherein the compound is a compound represented by General Formula (1),

in General Formula (1), at least one of R 1 , R 2 , R 3 , or R 4 is a substituent having a Hammett substituent constant σ p value of smaller than −0.15, provided that R 1 to R 4 are each independently a substituent having no reactive group, and R 1 to R 4 substituents adjacent to each other are not bonded to each other to form a fused ring; R 5 to R 7 each independently represent a substituent; Ar 11 and Ar 12 each independently represent an aryl group containing a benzene ring surrounded by a broken line or a heteroaryl group containing a benzene ring surrounded by a broken line, and Ar 13 is an aromatic fused ring group containing a benzene ring surrounded by a broken line as one of the fused rings; L 1 and L 2 each independently represent a single bond, an oxygen atom, or a sulfur atom, R 8 and R 9 each independently represent a linking group containing at least one selected from an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond, a carbonate bond, and an alkylene group, or a single bond, L 3 and L 4 each independently represent a single bond, an ester bond, a thioester bond, or an amide bond, and R 10 and R 11 each independently represent a hydrogen atom or a methyl group; c to e each independently represent an integer of 0 to 4; in the case where Ar 11 and Ar 12 each independently represent an aromatic fused ring group containing a benzene ring surrounded by a broken line as one of the fused rings, a group having L 1 as a linking group, a group having L 2 as a linking group, R 5 , and R 6 may each independently be substituted with a benzene ring surrounded by a broken line or may be substituted with a fused ring other than a benzene ring surrounded by a broken line; and R 7 may be substituted with a benzene ring surrounded by a broken line or may be substituted with a fused ring other than a benzene ring surrounded by a broken line.

3. The curable composition according to claim 1 , wherein the compound is a compound represented by General Formula (2),

in General Formula (2), at least one of R 1 , R 2 , R 3 , or R 4 is a substituent having a Hammett substituent constant σ p value of smaller than −0.15, provided that R 1 to R 4 are each independently a substituent having no reactive group, and R 1 to R 4 substituents adjacent to each other are not bonded to each other to form a fused ring; R 5 to R 7 each independently represent a substituent; Ar 11 and Ar 12 each independently represent an aryl group containing a benzene ring surrounded by a broken line or a heteroaryl group containing a benzene ring surrounded by a broken line; L 1 and L 2 each independently represent a single bond, an oxygen atom, or a sulfur atom, R 8 and R 9 each independently represent a linking group containing at least one selected from an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond, a carbonate bond, and an alkylene group, or a single bond, L 3 and L 4 each independently represent a single bond, an ester bond, a thioester bond, or an amide bond, and R 10 and R 11 each independently represent a hydrogen atom or a methyl group; c to e each independently represent an integer of 0 to 4; and in the case where Ar 11 and Ar 12 are each independently an aromatic fused ring group containing a benzene ring surrounded by a broken line as one of the fused rings, a group having L 1 as a linking group, a group having L 2 as a linking group, R 5 , and R 6 may each independently be substituted with a benzene ring surrounded by a broken line or may be substituted with a fused ring other than a benzene ring surrounded by a broken line.

4. The curable composition according to claim 1 , wherein at least one of R 2 or R 4 is a substituent having a Hammett substituent constant σ p value of smaller than −0.15.

5. The curable composition according to claim 1 , wherein at least one of R 1 , R 2 , R 3 , or R 4 is an alkyl group, an alkoxy group, or a dialkylamino group.

6. The curable composition according to claim 1 , wherein at least one of R 1 , R 2 , R 3 , or R 4 is an alkoxy group.

7. The curable composition according to claim 1 , wherein at least one of R 2 or R 4 is an alkoxy group.

8. The curable composition according to claim 1 ,
wherein at least one of R 2 or R 4 is an alkoxy group, and
at least two of R 1 , R 2 , R 3 , or R 4 are alkoxy groups.

9. The curable composition according to claim 1 , wherein R 2 and R 3 are alkoxy groups.

10. The curable composition according to claim 5 , wherein the alkoxy group is a methoxy group.

11. The curable composition according to claim 1 , wherein the viscosity at 25° C. of the (meth)acrylate monomer is less than 500 mPa·s.

12. The curable composition according to claim 1 , wherein the (meth)acrylate monomer is a (meth)acrylate monomer containing an aryl group or a heteroaryl group.

13. The curable composition according to claim 1 ,
wherein the content of the compound in the curable composition is 20 to 94 mass %,
the content of the (meth)acrylate monomer is 5 to 80 mass %, and
the content of at least one selected from a photoradical polymerization initiator and a thermal radical polymerization initiator is 0.01 to 10 mass %.

14. A cured product of the curable composition according to claim 1 .

15. An optical component comprising the cured product according to claim 14 .

16. A lens comprising t

Assignees

• Fujifilm Corp

Inventors

• Morooka Naoyuki

Classifications

• C07C217/94

  having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton · CPC title

• C07C69/54

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C07C69/602

  Dicarboxylic acid esters having at least two carbon-to-carbon double bonds · CPC title

• C07C2603/40

  containing four condensed rings · CPC title

• G02B1/041

  Lenses · CPC title