Compound, curable composition, cured product, optical member, and lens

Patent metadata

Field	Value
Publication number	US-10370473-B2
Application number	US-201816019922-A
Country	US
Kind code	B2
Filing date	Jun 27, 2018
Priority date	Dec 28, 2015
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

A cured product of a compound of the following formula has a low Abbe number and a high abnormal dispersibility. X and Y are O, S, N or S; Z and X—C═C—Y form 5 to 7-membered ring; R 1 and R 2 represents H, alkoxy, mercapto, thioalkoxy, amino, alkylamino, carboxy, alkylcarbonyloxy, carbamoyloxy or alkoxycarbonyloxy; and R 3 to R 6 represent substituent.

First claim

What is claimed is:

1. A compound represented by Formula (1),

in Formula (1), X and Y each independently represents an oxygen atom, a sulfur atom, a nitrogen atom, or a carbon atom, at least one of X or Y is an oxygen atom, a sulfur atom, or a nitrogen atom;
Z is an atomic group that forms a 5 to 7-membered ring together with X—C═C—Y and represents an atomic group including at least one selected from a carbon atom and a heteroatom;
R 1 and R 2 each independently represents a hydroxyl group, an alkoxy group having 2 to 6 carbon atoms that may have a substituent, a mercapto group, a thioalkoxy group having 2 to 6 carbon atoms that may have a substituent, an amino group, an alkylamino group having 1 to 6 carbon atoms that may have a substituent, a carboxy group, an alkylcarbonyloxy group having 1 to 6 carbon atoms that may have a substituent, a carbamoyloxy group that may have a substituent, or an alkoxycarbonyloxy group having 2 to 6 carbon atoms that may have a substituent;
R 3 to R 5 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
R 6 represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
m and n each independently represents an integer of 1 to 5, q and r each independently represents an integer of 0 to 4; here, 1≤m+q≤5, and 1≤n+r≤5 are satisfied;
v is an integer of 0 to 4, w is an integer of 0 or more, the maximum number of w is the maximum number of substituents that may be substituted with a ring formed by X—C═C—Y and Z;
in a case where q is an integer of 2 to 4, the plurality of R 3 's may be identical to or different from each other, and the plurality of R 3 's may be bonded to each other to form a ring;
in a case where r is an integer of 2 to 4, the plurality of R 4 's may be identical to or different from each other, and the plurality of R 4 's may be bonded to each other to form a ring;
in a case where v is an integer of 2 to 4, the plurality of R 5 's may be identical to or different from each other, but the plurality of R 5 's are not bonded to each other to form a ring; and
in a case where w is an integer of 2 to 5, the plurality of R 6 's may be identical to or different from each other, and the plurality of R 6 's may be bonded to each other to form a ring, provided that in a case where a plurality of R 6 's are bonded to each other and are groups for forming a fused ring together with a substituted ring, the number of rings for forming a fused ring is 2.

2. The compound according to claim 1 ,
wherein in Formula (1), R 1 and R 2 each independently represents a group having a hydroxyl group, a mercapto group, an amino group, a polymerizable unsaturated bond, an epoxy group, or an oxetanyl group.

3. The compound according to claim 1 ,
wherein in Formula (1), R 1 and R 2 each independently represents a group represented by Formula (2);
-L 1 Alkylene-L 2 n1 P  Formula (2)

in Formula (2), L 1 represents —O—, —S—, or —NH—, Alkylene represents an alkylene group having 2 to 6 carbon atoms, L 2 represents —O—, —S—, or —NH—, n1 represents an integer of 0 to 2, P is a hydrogen atom or a group represented by any one of Formulae (P1) to (P4); and

in Formulae (P) to (P4), R 511 , R 512 , R 513 , R 521 , R 522 , R 523 , R 531 , R 532 , R 533 , R 541 , R 542 , R 543 , R 544 , and R 545 each independently represents a hydrogen atom or an alkyl group, m represents an integer of 0 to 2, and R 11 and R 12 each independently represents a hydrogen atom, a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, a cyano group, an epoxy group, an oxetanyl group, a mercapto group, an amino group, or a (meth)acryloyl group.

4. The compound according to claim 1 ,
wherein, in Formula (1), at least one selected from X and Y is a nitrogen atom.

5. The compound according to claim 1 ,
wherein, in Formula (1), R 1 and R 2 are the same group.

6. The compound according to claim 1 , which is represented by Formula (3);

in Formula (3), R 1 and R 2 each independently represents a hydroxyl group, an alkoxy group having 2 to 6 carbon atoms that may have a substituent, a mercapto group, a thioalkoxy group having 2 to 6 carbon atoms that may have a substituent, an amino group, an alkylamino group having 1 to 6 carbon atoms that may have a substituent, a carboxy group, an alkylcarbonyloxy group having 1 to 6 carbon atoms that may have a substituent, a carbamoyloxy group that may have a substituent, or an alkoxycarbonyloxy group having 2 to 6 carbon atoms that may have a substituent;
R 3 to R 5 each independently represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
R 6 represents a halogen atom, a halogenated alkyl group, an alkyl group, an alkenyl group, an acyl group, a hydroxyl group, a hydroxyalkyl group, an alkoxy group, an aryl group, a heteroaryl group, an alicyclic group, or a cyano group;
m and n each independently represents an integer of 1 to 5, q and r each independently represents an integer of 0 to 4; here, 1≤m+q≤5, and 1≤n+r≤5 are satisfied;
v is an integer of 0 to 4, and w is an integer of 0 to 2;
in a case where q is an integer of 2 to 4, the plurality of R 3 's may be identical to or different from each other, and the plurality of R 3 's may be bonded to each other to form a ring;
in a case where r is an integer of 2 to 4, the plurality of R 4 's may be identical to or different from each other, and the plurality of R 4 's may be bonded to each other to form a ring;
in a case where v is an integer of 2 to 4, the plurality of R 5 's may be identical to or different from each other, but the plurality of R 5 's are not bonded to each other to form a ring; and
in a case where w is 2, the plurality of R 6 's may be identical to or different from each other, and the plurality of R 6 's may be bonded to each other to form a ring, provided that in a case where a plurality of R 6 's are bonded to each other and are groups for forming a fused ring together with a substituted ring, the number of rings for forming a fused ring is 2.

7. The compound according to claim 1 ,
wherein R 1 and R 2 are each independently represented by Formula (4);

in Formula (4), L represents —O—, —S—, or —NH—, Alkylene represents an alkylene group having 2 to 6 carbon atoms, and R 531 , R 532 , and R 533 each independently represents a hydrogen atom or an alkyl group.

8. A curable composition comprising the compound according to claim 1 .

9. The curable composition according to claim 8 ,
wherein the curable composition contains a (meth)acrylate mo

Assignees

• Fujifilm Corp

Inventors

• Nakayama Takafumi
• Uehira Shigeki
• Morooka Naoyuki

Classifications

• C08F220/382

  and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate · CPC title

• C08F220/301

  and one oxygen in the alcohol moiety · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C08F220/1811

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title

• C08F2/50

  with sensitising agents · CPC title